data_aje-01-190
_audit_creation_date 2016-06-20
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.05.11 svn.r3296 for OlexSys, GUI svn.r5177)
;
_publ_contact_author_address ?
_publ_contact_author_email ?
_publ_contact_author_name ''
_publ_contact_author_phone ?
_publ_section_references
'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790; Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984; Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575-580 Petricek,V., Dusek,M. & Palatinus,L.(2006). Jana2006. The crystallographic computing system. Institute of Physics, Praha, Czech Republic. Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. Bruker (2014). APEX2 Version 2014.11. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2013). SAINT-Plus V8.34A Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). SADABS Version 2008-1. Bruker AXS Inc., Madison, Wisconsin, USA.'
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C13 H14 O4'
_chemical_formula_sum 'C13 H14 O4'
_chemical_formula_weight 234.24
_chemical_absolute_configuration ad
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system 'monoclinic'
_space_group_IT_number 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 9.8776(16)
_cell_length_b 11.2114(17)
_cell_length_c 10.4484(16)
_cell_angle_alpha 90
_cell_angle_beta 94.542(2)
_cell_angle_gamma 90
_cell_volume 1153.4(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3970
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.547
_cell_measurement_theta_min 2.669
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.6894
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0918 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.9240.
The \l/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.349
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 496
_exptl_crystal_recrystallization_method 'THF:Pentane vapor diffusion'
_exptl_crystal_size_max 0.6
_exptl_crystal_size_mid 0.587
_exptl_crystal_size_min 0.17
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0300
_diffrn_reflns_av_unetI/netI 0.0434
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 11534
_diffrn_reflns_point_group_measured_fraction_full 0.868
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 30.731
_diffrn_reflns_theta_min 1.955
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_source_current 35
_diffrn_source_voltage 45
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.567
_reflns_Friedel_fraction_full 0.720
_reflns_Friedel_fraction_max 0.615
_reflns_number_gt 5192
_reflns_number_total 5811
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection 'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction 'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution 'SHELXT-2014/4 (Sheldrick, 2015)'
_refine_diff_density_max 0.402
_refine_diff_density_min -0.224
_refine_diff_density_rms 0.059
_refine_ls_abs_structure_details
;
Flack x determined using 1358 CuK\a quotients [(I+)-(I-)]/[(I+)+(I-)]
from a data set from the same crystal measured with a wavelength of
1.54178
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
_reflns_Friedel_coverage 0.839
_reflns_Friedel_fraction_full 0.902
_reflns_Friedel_fraction_max 0.926
;
_refine_ls_abs_structure_Flack 0.13(6)
_refine_ls_abs_structure_Flack_MoK\a 0.4(5)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 309
_refine_ls_number_reflns 5811
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0509
_refine_ls_R_factor_gt 0.0435
_refine_ls_restrained_S_all 1.031
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.0919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1043
_refine_ls_wR_factor_ref 0.1102
_refine_special_details ?
_olex2_refinement_description
;
1. Others
Fixed Uiso: H1'(0.027) H1(0.03) H2'(0.016) H6(0.017) H14'(0.023) H7'(0.015)
H10(0.021) H2(0.02) H7(0.017) H11(0.026) H12(0.026) H8'(0.017) H8(0.018)
H6'(0.016) H4'(0.024) H10'(0.025) H5'(0.021) H3A(0.024) H3B(0.024) H4(0.024)
H14(0.022) H3'A(0.023) H3'B(0.023) H12'(0.029) H5(0.022) H13(0.025)
H13'(0.028) H11'(0.032)
Fixed X: H1'(1.1374) H1(0.6015) H2'(1.0597) H6(0.6414) H14'(1.0835)
H7'(0.9371) H10(0.1614) H2(0.5437) H7(0.4295) H11(0.1582) H12(0.3585)
H8'(0.7929) H8(0.2713) H6'(1.1612) H4'(1.1256) H10'(0.6752) H5'(1.081)
H3A(0.7686) H3B(0.7584) H4(0.6519) H14(0.5684) H3'A(1.2764) H3'B(1.2643)
H12'(0.8627) H5(0.5944) H13(0.5638) H13'(1.0725) H11'(0.6638)
Fixed Y: H1'(0.8488) H1(0.5982) H2'(0.7997) H6(0.3147) H14'(0.6462)
H7'(0.6306) H10(0.4007) H2(0.5514) H7(0.3773) H11(0.4423) H12(0.4307)
H8'(0.5818) H8(0.328) H6'(0.558) H4'(0.4093) H10'(0.6042) H5'(0.3665)
H3A(0.3943) H3B(0.4924) H4(0.1654) H14(0.3438) H3'A(0.6303) H3'B(0.7296)
H12'(0.6837) H5(0.12) H13(0.3847) H13'(0.685) H11'(0.6467)
Fixed Z: H1'(0.5515) H1(0.5896) H2'(0.7322) H6(0.5734) H14'(0.2811)
H7'(0.6781) H10(0.3212) H2(0.7828) H7(0.7361) H11(0.1019) H12(-0.003)
H8'(0.4598) H8(0.5128) H6'(0.536) H4'(0.8568) H10'(0.2608) H5'(0.653)
H3A(0.7526) H3B(0.8625) H4(0.9007) H14(0.3339) H3'A(0.7182) H3'B(0.8265) H12'(-
0.0591) H5(0.6994) H13(0.114) H13'(0.0609) H11'(0.0402)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4' O 0.94161(14) 0.69918(14) 0.50179(14) 0.0145(3) Uani 1 1 d . . . . .
O4 O 0.41690(14) 0.44663(15) 0.55929(14) 0.0158(3) Uani 1 1 d . . . . .
O1' O 1.18605(14) 0.79817(15) 0.59277(15) 0.0182(3) Uani 1 1 d . . . . .
H1' H 1.1374 0.8488 0.5515 0.027 Uiso 1 1 calc GR . . . .
O1 O 0.65860(15) 0.55765(15) 0.63478(15) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.6015 0.5982 0.5896 0.030 Uiso 1 1 calc GR . . . .
O3' O 0.97484(15) 0.49907(14) 0.46987(14) 0.0166(3) Uani 1 1 d . . . . .
O3 O 0.45295(15) 0.24617(15) 0.53008(15) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.65828(17) 0.34244(17) 0.89416(15) 0.0233(4) Uani 1 1 d . . . . .
O2' O 1.15247(16) 0.58496(16) 0.85126(15) 0.0221(4) Uani 1 1 d . . . . .
C9 C 0.36489(19) 0.3677(2) 0.3488(2) 0.0144(4) Uani 1 1 d . . . . .
C2' C 1.10827(19) 0.7396(2) 0.68189(19) 0.0137(4) Uani 1 1 d . . . . .
H2' H 1.0597 0.7997 0.7322 0.016 Uiso 1 1 calc R . . . .
C9' C 0.8804(2) 0.62116(19) 0.29210(19) 0.0141(4) Uani 1 1 d . . . . .
C6 C 0.56038(18) 0.2919(2) 0.61950(19) 0.0140(4) Uani 1 1 d . . . . .
H6 H 0.6414 0.3147 0.5734 0.017 Uiso 1 1 calc R . . . .
C14' C 0.9982(2) 0.6455(2) 0.2322(2) 0.0195(5) Uani 1 1 d . . . . .
H14' H 1.0835 0.6462 0.2811 0.023 Uiso 1 1 calc R . . . .
C7' C 1.00682(19) 0.65177(19) 0.61755(19) 0.0121(4) Uani 1 1 d . . . . .
H7' H 0.9371 0.6306 0.6781 0.015 Uiso 1 1 calc R . . . .
C10 C 0.24321(19) 0.3972(2) 0.2792(2) 0.0173(4) Uani 1 1 d . . . . .
H10 H 0.1614 0.4007 0.3212 0.021 Uiso 1 1 calc R . . . .
C2 C 0.5920(2) 0.4944(2) 0.7286(2) 0.0164(4) Uani 1 1 d . . . . .
H2 H 0.5437 0.5514 0.7828 0.020 Uiso 1 1 calc R . . . .
C7 C 0.49298(18) 0.4017(2) 0.67088(19) 0.0140(4) Uani 1 1 d . . . . .
H7 H 0.4295 0.3773 0.7361 0.017 Uiso 1 1 calc R . . . .
C11 C 0.2412(2) 0.4216(2) 0.1488(2) 0.0216(5) Uani 1 1 d . . . . .
H11 H 0.1582 0.4423 0.1019 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3602(2) 0.4156(2) 0.0866(2) 0.0217(5) Uani 1 1 d . . . . .
H12 H 0.3585 0.4307 -0.0030 0.026 Uiso 1 1 calc R . . . .
C8' C 0.88625(19) 0.5984(2) 0.43361(19) 0.0139(4) Uani 1 1 d . . . . .
H8' H 0.7929 0.5818 0.4598 0.017 Uiso 1 1 calc R . . . .
C8 C 0.36586(19) 0.3449(2) 0.4902(2) 0.0153(4) Uani 1 1 d . . . . .
H8 H 0.2713 0.3280 0.5128 0.018 Uiso 1 1 calc R . . . .
C6' C 1.07251(19) 0.5390(2) 0.57129(19) 0.0133(4) Uani 1 1 d . . . . .
H6' H 1.1612 0.5580 0.5360 0.016 Uiso 1 1 calc R . . . .
C4' C 1.1231(2) 0.4744(2) 0.7985(2) 0.0197(4) Uani 1 1 d . . . . .
H4' H 1.1256 0.4093 0.8568 0.024 Uiso 1 1 calc R . . . .
C10' C 0.7559(2) 0.6210(2) 0.2204(2) 0.0211(5) Uani 1 1 d . . . . .
H10' H 0.6752 0.6042 0.2608 0.025 Uiso 1 1 calc R . . . .
C5' C 1.0918(2) 0.4482(2) 0.6757(2) 0.0173(4) Uani 1 1 d . . . . .
H5' H 1.0810 0.3665 0.6530 0.021 Uiso 1 1 calc R . . . .
C3 C 0.7061(2) 0.4320(2) 0.8102(2) 0.0197(4) Uani 1 1 d . . . . .
H3A H 0.7686 0.3943 0.7526 0.024 Uiso 1 1 calc R . . . .
H3B H 0.7584 0.4924 0.8625 0.024 Uiso 1 1 calc R . . . .
C4 C 0.6371(2) 0.2303(2) 0.8429(2) 0.0204(5) Uani 1 1 d . . . . .
H4 H 0.6519 0.1654 0.9007 0.024 Uiso 1 1 calc R . . . .
C14 C 0.4850(2) 0.3633(2) 0.2869(2) 0.0182(4) Uani 1 1 d . . . . .
H14 H 0.5684 0.3438 0.3339 0.022 Uiso 1 1 calc R . . . .
C3' C 1.2119(2) 0.6715(2) 0.7711(2) 0.0192(4) Uani 1 1 d . . . . .
H3'A H 1.2764 0.6303 0.7182 0.023 Uiso 1 1 calc R . . . .
H3'B H 1.2643 0.7296 0.8265 0.023 Uiso 1 1 calc R . . . .
C12' C 0.8671(3) 0.6683(2) 0.0305(2) 0.0245(5) Uani 1 1 d . . . . .
H12' H 0.8627 0.6837 -0.0591 0.029 Uiso 1 1 calc R . . . .
C5 C 0.5983(2) 0.2021(2) 0.7221(2) 0.0182(4) Uani 1 1 d . . . . .
H5 H 0.5944 0.1200 0.6994 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4821(2) 0.3874(2) 0.1562(2) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.5638 0.3847 0.1140 0.025 Uiso 1 1 calc R . . . .
C13' C 0.9918(2) 0.6688(2) 0.1016(2) 0.0229(5) Uani 1 1 d . . . . .
H13' H 1.0725 0.6850 0.0609 0.028 Uiso 1 1 calc R . . . .
C11' C 0.7491(3) 0.6456(3) 0.0891(2) 0.0269(5) Uani 1 1 d . . . . .
H11' H 0.6638 0.6467 0.0402 0.032 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4' 0.0169(6) 0.0111(8) 0.0147(6) -0.0007(6) -0.0030(5) 0.0017(5)
O4 0.0178(6) 0.0120(8) 0.0172(7) -0.0002(6) -0.0019(5) 0.0013(6)
O1' 0.0157(6) 0.0150(9) 0.0239(8) 0.0051(7) -0.0001(6) -0.0013(6)
O1 0.0205(7) 0.0160(9) 0.0243(8) 0.0045(7) 0.0021(6) -0.0045(6)
O3' 0.0228(7) 0.0094(8) 0.0169(7) -0.0013(6) -0.0034(6) 0.0014(6)
O3 0.0210(7) 0.0108(8) 0.0213(7) -0.0015(6) -0.0053(6) -0.0001(6)
O2 0.0337(8) 0.0197(9) 0.0164(7) 0.0009(7) 0.0006(6) -0.0016(7)
O2' 0.0315(8) 0.0182(9) 0.0159(7) 0.0017(7) -0.0019(6) -0.0010(7)
C9 0.0161(8) 0.0096(10) 0.0170(9) -0.0015(8) -0.0009(7) 0.0000(7)
C2' 0.0132(8) 0.0125(10) 0.0155(9) -0.0017(8) 0.0005(7) 0.0001(7)
C9' 0.0176(9) 0.0102(11) 0.0143(9) -0.0013(8) -0.0001(7) 0.0025(7)
C6 0.0127(8) 0.0130(11) 0.0163(9) -0.0020(8) 0.0008(7) -0.0001(7)
C14' 0.0190(9) 0.0208(12) 0.0189(10) 0.0006(9) 0.0026(8) 0.0019(8)
C7' 0.0120(8) 0.0118(10) 0.0124(8) -0.0007(8) 0.0004(7) 0.0009(7)
C10 0.0132(8) 0.0166(12) 0.0216(10) -0.0038(9) -0.0025(7) 0.0002(7)
C2 0.0189(9) 0.0143(11) 0.0163(9) -0.0016(8) 0.0027(8) -0.0012(8)
C7 0.0129(8) 0.0124(10) 0.0167(9) 0.0009(8) 0.0025(7) 0.0001(7)
C11 0.0198(9) 0.0212(13) 0.0225(10) -0.0052(9) -0.0067(8) 0.0027(9)
C12 0.0275(10) 0.0192(13) 0.0178(10) -0.0035(9) -0.0021(8) 0.0016(9)
C8' 0.0135(8) 0.0118(10) 0.0161(9) -0.0006(8) 0.0002(7) 0.0017(7)
C8 0.0141(8) 0.0119(11) 0.0198(9) -0.0009(9) 0.0006(7) -0.0003(7)
C6' 0.0139(8) 0.0108(10) 0.0148(9) -0.0008(8) -0.0006(7) 0.0017(7)
C4' 0.0250(10) 0.0147(12) 0.0191(10) 0.0038(9) 0.0006(8) 0.0024(8)
C10' 0.0179(9) 0.0226(14) 0.0222(11) -0.0019(9) -0.0029(8) -0.0021(8)
C5' 0.0200(9) 0.0114(11) 0.0205(10) 0.0021(8) 0.0014(8) 0.0032(8)
C3 0.0204(9) 0.0196(12) 0.0183(9) -0.0004(9) -0.0024(8) -0.0038(8)
C4 0.0227(10) 0.0163(12) 0.0220(10) 0.0050(9) 0.0007(8) 0.0014(8)
C14 0.0157(8) 0.0187(12) 0.0199(10) 0.0008(9) -0.0008(7) 0.0026(8)
C3' 0.0207(10) 0.0167(12) 0.0193(10) 0.0008(9) -0.0037(8) -0.0014(8)
C12' 0.0412(13) 0.0166(12) 0.0152(10) -0.0006(9) -0.0009(9) 0.0024(10)
C5 0.0170(9) 0.0136(11) 0.0239(10) 0.0010(9) 0.0014(8) 0.0014(8)
C13 0.0211(9) 0.0210(13) 0.0202(10) -0.0006(9) 0.0048(8) 0.0031(9)
C13' 0.0294(11) 0.0208(13) 0.0193(10) 0.0000(10) 0.0069(9) 0.0018(10)
C11' 0.0298(12) 0.0266(15) 0.0222(11) -0.0013(10) -0.0116(9) -0.0002(10)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4' C7' 1.427(2) . ?
O4' C8' 1.422(3) . ?
O4 C7 1.428(2) . ?
O4 C8 1.421(3) . ?
O1' H1' 0.8400 . ?
O1' C2' 1.415(2) . ?
O1 H1 0.8400 . ?
O1 C2 1.414(2) . ?
O3' C8' 1.448(3) . ?
O3' C6' 1.446(2) . ?
O3 C6 1.451(3) . ?
O3 C8 1.443(3) . ?
O2 C3 1.437(3) . ?
O2 C4 1.376(3) . ?
O2' C4' 1.378(3) . ?
O2' C3' 1.437(3) . ?
C9 C10 1.395(3) . ?
C9 C8 1.499(3) . ?
C9 C14 1.396(3) . ?
C2' H2' 1.0000 . ?
C2' C7' 1.523(3) . ?
C2' C3' 1.532(3) . ?
C9' C14' 1.392(3) . ?
C9' C8' 1.497(3) . ?
C9' C10' 1.388(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.518(3) . ?
C6 C5 1.496(3) . ?
C14' H14' 0.9500 . ?
C14' C13' 1.386(3) . ?
C7' H7' 1.0000 . ?
C7' C6' 1.518(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C2 H2 1.0000 . ?
C2 C7 1.519(3) . ?
C2 C3 1.528(3) . ?
C7 H7 1.0000 . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C8' H8' 1.0000 . ?
C8 H8 1.0000 . ?
C6' H6' 1.0000 . ?
C6' C5' 1.494(3) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.328(3) . ?
C10' H10' 0.9500 . ?
C10' C11' 1.396(3) . ?
C5' H5' 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.328(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.391(3) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C12' H12' 0.9500 . ?
C12' C13' 1.387(3) . ?
C12' C11' 1.383(4) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13' H13' 0.9500 . ?
C11' H11' 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8' O4' C7' 104.97(16) . . ?
C8 O4 C7 105.91(16) . . ?
C2' O1' H1' 109.5 . . ?
C2 O1 H1 109.5 . . ?
C6' O3' C8' 107.94(16) . . ?
C8 O3 C6 107.70(16) . . ?
C4 O2 C3 116.57(17) . . ?
C4' O2' C3' 117.16(17) . . ?
C10 C9 C8 119.51(17) . . ?
C10 C9 C14 119.73(19) . . ?
C14 C9 C8 120.73(18) . . ?
O1' C2' H2' 109.9 . . ?
O1' C2' C7' 112.47(16) . . ?
O1' C2' C3' 105.09(16) . . ?
C7' C2' H2' 109.9 . . ?
C7' C2' C3' 109.33(18) . . ?
C3' C2' H2' 109.9 . . ?
C14' C9' C8' 120.63(18) . . ?
C10' C9' C14' 119.61(19) . . ?
C10' C9' C8' 119.74(18) . . ?
O3 C6 H6 110.7 . . ?
O3 C6 C7 101.27(15) . . ?
O3 C6 C5 110.64(18) . . ?
C7 C6 H6 110.7 . . ?
C5 C6 H6 110.7 . . ?
C5 C6 C7 112.61(17) . . ?
C9' C14' H14' 119.8 . . ?
C13' C14' C9' 120.4(2) . . ?
C13' C14' H14' 119.8 . . ?
O4' C7' C2' 111.74(17) . . ?
O4' C7' H7' 109.7 . . ?
O4' C7' C6' 102.48(15) . . ?
C2' C7' H7' 109.7 . . ?
C6' C7' C2' 113.34(16) . . ?
C6' C7' H7' 109.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.21(18) . . ?
C11 C10 H10 119.9 . . ?
O1 C2 H2 109.9 . . ?
O1 C2 C7 112.86(17) . . ?
O1 C2 C3 104.69(16) . . ?
C7 C2 H2 109.9 . . ?
C7 C2 C3 109.37(19) . . ?
C3 C2 H2 109.9 . . ?
O4 C7 C6 102.40(16) . . ?
O4 C7 C2 111.31(18) . . ?
O4 C7 H7 109.6 . . ?
C6 C7 C2 114.11(16) . . ?
C6 C7 H7 109.6 . . ?
C2 C7 H7 109.6 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
O4' C8' O3' 106.24(15) . . ?
O4' C8' C9' 110.01(17) . . ?
O4' C8' H8' 109.7 . . ?
O3' C8' C9' 111.41(16) . . ?
O3' C8' H8' 109.7 . . ?
C9' C8' H8' 109.7 . . ?
O4 C8 O3 106.83(15) . . ?
O4 C8 C9 109.78(18) . . ?
O4 C8 H8 109.4 . . ?
O3 C8 C9 111.88(17) . . ?
O3 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
O3' C6' C7' 102.35(15) . . ?
O3' C6' H6' 110.4 . . ?
O3' C6' C5' 111.32(18) . . ?
C7' C6' H6' 110.4 . . ?
C5' C6' C7' 111.60(16) . . ?
C5' C6' H6' 110.4 . . ?
O2' C4' H4' 116.2 . . ?
C5' C4' O2' 127.7(2) . . ?
C5' C4' H4' 116.2 . . ?
C9' C10' H10' 119.9 . . ?
C9' C10' C11' 120.1(2) . . ?
C11' C10' H10' 119.9 . . ?
C6' C5' H5' 117.9 . . ?
C4' C5' C6' 124.2(2) . . ?
C4' C5' H5' 117.9 . . ?
O2 C3 C2 113.36(17) . . ?
O2 C3 H3A 108.9 . . ?
O2 C3 H3B 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O2 C4 H4 116.1 . . ?
C5 C4 O2 127.7(2) . . ?
C5 C4 H4 116.1 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.69(19) . . ?
C13 C14 H14 120.2 . . ?
O2' C3' C2' 114.02(17) . . ?
O2' C3' H3'A 108.7 . . ?
O2' C3' H3'B 108.7 . . ?
C2' C3' H3'A 108.7 . . ?
C2' C3' H3'B 108.7 . . ?
H3'A C3' H3'B 107.6 . . ?
C13' C12' H12' 119.7 . . ?
C11' C12' H12' 119.7 . . ?
C11' C12' C13' 120.5(2) . . ?
C6 C5 H5 118.1 . . ?
C4 C5 C6 123.9(2) . . ?
C4 C5 H5 118.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.48(19) . . ?
C14 C13 H13 119.8 . . ?
C14' C13' C12' 119.7(2) . . ?
C14' C13' H13' 120.1 . . ?
C12' C13' H13' 120.1 . . ?
C10' C11' H11' 120.2 . . ?
C12' C11' C10' 119.7(2) . . ?
C12' C11' H11' 120.2 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4' C7' C6' O3' -34.93(18) . . . . ?
O4' C7' C6' C5' -154.08(16) . . . . ?
O1' C2' C7' O4' -41.8(2) . . . . ?
O1' C2' C7' C6' 73.4(2) . . . . ?
O1' C2' C3' O2' -166.95(18) . . . . ?
O1 C2 C7 O4 -41.7(2) . . . . ?
O1 C2 C7 C6 73.6(2) . . . . ?
O1 C2 C3 O2 -167.38(18) . . . . ?
O3' C6' C5' C4' -149.27(19) . . . . ?
O3 C6 C7 O4 -38.09(18) . . . . ?
O3 C6 C7 C2 -158.49(16) . . . . ?
O3 C6 C5 C4 -145.6(2) . . . . ?
O2 C4 C5 C6 -4.6(3) . . . . ?
O2' C4' C5' C6' -4.8(3) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C9 C14 C13 C12 -0.2(4) . . . . ?
C2' C7' C6' O3' -155.51(16) . . . . ?
C2' C7' C6' C5' 85.3(2) . . . . ?
C9' C14' C13' C12' 0.3(4) . . . . ?
C9' C10' C11' C12' 0.9(4) . . . . ?
C6 O3 C8 O4 -2.64(19) . . . . ?
C6 O3 C8 C9 117.53(18) . . . . ?
C14' C9' C8' O4' 59.8(3) . . . . ?
C14' C9' C8' O3' -57.8(3) . . . . ?
C14' C9' C10' C11' -0.2(4) . . . . ?
C7' O4' C8' O3' -30.00(17) . . . . ?
C7' O4' C8' C9' -150.72(15) . . . . ?
C7' C2' C3' O2' -46.0(2) . . . . ?
C7' C6' C5' C4' -35.6(3) . . . . ?
C10 C9 C8 O4 -101.6(2) . . . . ?
C10 C9 C8 O3 140.0(2) . . . . ?
C10 C9 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 -1.3(4) . . . . ?
C7 O4 C8 O3 -22.71(18) . . . . ?
C7 O4 C8 C9 -144.22(15) . . . . ?
C7 C6 C5 C4 -33.1(3) . . . . ?
C7 C2 C3 O2 -46.2(2) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C8' O4' C7' C2' 161.88(15) . . . . ?
C8' O4' C7' C6' 40.20(17) . . . . ?
C8' O3' C6' C7' 17.15(19) . . . . ?
C8' O3' C6' C5' 136.49(16) . . . . ?
C8' C9' C14' C13' -178.8(2) . . . . ?
C8' C9' C10' C11' 178.2(2) . . . . ?
C8 O4 C7 C6 37.83(17) . . . . ?
C8 O4 C7 C2 160.16(15) . . . . ?
C8 O3 C6 C7 24.89(19) . . . . ?
C8 O3 C6 C5 144.48(16) . . . . ?
C8 C9 C10 C11 178.4(2) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C6' O3' C8' O4' 6.92(19) . . . . ?
C6' O3' C8' C9' 126.73(17) . . . . ?
C4' O2' C3' C2' 83.6(2) . . . . ?
C10' C9' C14' C13' -0.4(4) . . . . ?
C10' C9' C8' O4' -118.6(2) . . . . ?
C10' C9' C8' O3' 123.9(2) . . . . ?
C3 O2 C4 C5 -31.5(3) . . . . ?
C3 C2 C7 O4 -157.83(15) . . . . ?
C3 C2 C7 C6 -42.5(2) . . . . ?
C4 O2 C3 C2 85.9(2) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C14 C9 C8 O4 76.5(3) . . . . ?
C14 C9 C8 O3 -42.0(3) . . . . ?
C3' O2' C4' C5' -28.7(3) . . . . ?
C3' C2' C7' O4' -158.11(16) . . . . ?
C3' C2' C7' C6' -42.9(2) . . . . ?
C5 C6 C7 O4 -156.27(16) . . . . ?
C5 C6 C7 C2 83.3(2) . . . . ?
C13' C12' C11' C10' -1.0(4) . . . . ?
C11' C12' C13' C14' 0.4(4) . . . . ?
_shelx_SHELXL_version_number '2014/7'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'