data_aje-01-199
_audit_creation_date 2016-06-27
_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
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
(2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 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 2014.1-1. 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.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C13 H14 O4), H2 O'
_chemical_formula_sum 'C26 H30 O9'
_chemical_formula_weight 486.50
_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' 0.0181 0.0091 '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' 0.0492 0.0322 '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 5
_space_group_name_H-M_alt 'C 1 2 1'
_space_group_name_Hall 'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
_cell_length_a 8.7513(2)
_cell_length_b 6.9927(2)
_cell_length_c 19.1912(4)
_cell_angle_alpha 90
_cell_angle_beta 91.6770(10)
_cell_angle_gamma 90
_cell_volume 1173.91(5)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4490
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 66.993
_cell_measurement_theta_min 4.610
_shelx_estimated_absorpt_T_max 0.877
_shelx_estimated_absorpt_T_min 0.621
_exptl_absorpt_coefficient_mu 0.868
_exptl_absorpt_correction_T_max 0.7529
_exptl_absorpt_correction_T_min 0.6485
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0529 before and 0.0250 after correction.
The Ratio of minimum to maximum transmission is 0.8613.
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 1.376
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 516
_exptl_crystal_recrystallization_method
'vapor diffusion using THF as the solvent and pentane as the precipitant.'
_exptl_crystal_size_max 0.608
_exptl_crystal_size_mid 0.398
_exptl_crystal_size_min 0.156
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0144
_diffrn_reflns_av_unetI/netI 0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 4805
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full 66.988
_diffrn_reflns_theta_max 66.988
_diffrn_reflns_theta_min 2.303
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'sealed tube'
_diffrn_source_current 35
_diffrn_source_voltage 45
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.715
_reflns_Friedel_fraction_full 0.838
_reflns_Friedel_fraction_max 0.838
_reflns_number_gt 1904
_reflns_number_total 1938
_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, 2008)'
_computing_structure_solution 'XT (Sheldrick, 2015)'
_refine_diff_density_max 0.159
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.034
_refine_ls_abs_structure_details
;
Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.14(5)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.064
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 165
_refine_ls_number_reflns 1938
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0313
_refine_ls_R_factor_gt 0.0310
_refine_ls_restrained_S_all 1.072
_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^)+(0.0483P)^2^+0.4953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0819
_refine_ls_wR_factor_ref 0.0822
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
O1W-H1W
0.982 with sigma of 0.02
O4-H4
0.982 with sigma of 0.02
H4-O3_$1
2 with sigma of 0.02
H1W-O4
2 with sigma of 0.02
H1W_$2-H1W
1.55 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
C1(H1), C2(H2), C3(H3), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
C5(H5), C4(H4A), C9(H9), C13(H13), C12(H12), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_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
O1 O 0.29766(18) 0.6258(2) 0.27931(8) 0.0322(4) Uani 1 1 d . . . . .
O2 O 0.2783(2) 0.3698(2) 0.20456(8) 0.0366(4) Uani 1 1 d . . . . .
O3 O 0.2093(2) 0.1508(3) 0.41128(9) 0.0463(5) Uani 1 1 d D . . . .
O4 O 0.2771(2) 0.5709(3) 0.43646(9) 0.0474(5) Uani 1 1 d D . . . .
O1W O 0.5000 0.2878(5) 0.5000 0.0618(8) Uani 1 2 d DS T P . .
C8 C 0.2899(3) 0.6924(3) 0.15748(12) 0.0304(5) Uani 1 1 d . . . . .
C1 C 0.3437(2) 0.5572(3) 0.21363(12) 0.0308(5) Uani 1 1 d . . . . .
H1 H 0.4554 0.5479 0.2136 0.037 Uiso 1 1 calc R . . . .
C5 C 0.2338(3) 0.0506(4) 0.35180(14) 0.0383(6) Uani 1 1 d . . . . .
H5 H 0.2560 -0.0786 0.3575 0.046 Uiso 1 1 calc R . . . .
C4 C 0.2299(2) 0.1146(4) 0.28703(13) 0.0343(5) Uani 1 1 d . . . . .
H4A H 0.2442 0.0271 0.2513 0.041 Uiso 1 1 calc R . . . .
C9 C 0.3935(3) 0.7970(4) 0.11973(13) 0.0368(6) Uani 1 1 d . . . . .
H9 H 0.4979 0.7810 0.1282 0.044 Uiso 1 1 calc R . . . .
C2 C 0.2768(3) 0.4570(3) 0.32032(12) 0.0288(5) Uani 1 1 d . . . . .
H2 H 0.3766 0.4069 0.3360 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2035(2) 0.3214(3) 0.26760(11) 0.0292(5) Uani 1 1 d . . . . .
H3 H 0.0937 0.3473 0.2626 0.035 Uiso 1 1 calc R . . . .
C7 C 0.1795(3) 0.4946(4) 0.38260(13) 0.0361(6) Uani 1 1 d . . . . .
H7 H 0.1004 0.5887 0.3700 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1337(3) 0.7191(4) 0.14394(13) 0.0359(5) Uani 1 1 d . . . . .
H13 H 0.0631 0.6507 0.1693 0.043 Uiso 1 1 calc R . . . .
C12 C 0.0834(3) 0.8458(4) 0.09333(14) 0.0414(6) Uani 1 1 d . . . . .
H12 H -0.0209 0.8612 0.0843 0.050 Uiso 1 1 calc R . . . .
C6 C 0.1038(3) 0.3090(4) 0.40479(15) 0.0450(6) Uani 1 1 d . . . . .
H6A H 0.0562 0.3289 0.4492 0.054 Uiso 1 1 calc R . . . .
H6B H 0.0238 0.2762 0.3708 0.054 Uiso 1 1 calc R . . . .
C10 C 0.3415(3) 0.9259(4) 0.06911(14) 0.0448(7) Uani 1 1 d . . . . .
H10 H 0.4116 0.9961 0.0441 0.054 Uiso 1 1 calc R . . . .
C11 C 0.1872(3) 0.9506(4) 0.05576(14) 0.0445(6) Uani 1 1 d . . . . .
H11 H 0.1530 1.0367 0.0218 0.053 Uiso 1 1 calc R . . . .
H4 H 0.245(3) 0.618(5) 0.4812(10) 0.053 Uiso 1 1 d DR . . . .
H1W H 0.430(2) 0.371(4) 0.4742(13) 0.053 Uiso 1 1 d DR . . . .
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
O1 0.0423(8) 0.0244(8) 0.0301(9) -0.0010(7) 0.0018(6) -0.0063(7)
O2 0.0474(10) 0.0304(9) 0.0321(9) -0.0062(7) 0.0024(7) -0.0042(7)
O3 0.0615(11) 0.0355(11) 0.0418(10) 0.0068(8) 0.0005(8) -0.0066(9)
O4 0.0701(13) 0.0425(11) 0.0301(10) -0.0077(8) 0.0072(8) -0.0146(10)
O1W 0.087(2) 0.0499(18) 0.0481(18) 0.000 -0.0055(15) 0.000
C8 0.0322(11) 0.0289(12) 0.0301(12) -0.0059(9) 0.0011(9) -0.0034(9)
C1 0.0283(10) 0.0309(12) 0.0333(13) -0.0036(9) 0.0016(9) -0.0046(9)
C5 0.0376(12) 0.0282(12) 0.0490(15) 0.0015(11) -0.0029(11) -0.0042(10)
C4 0.0279(10) 0.0302(13) 0.0445(14) -0.0047(10) -0.0022(9) -0.0008(9)
C9 0.0342(12) 0.0396(14) 0.0367(13) -0.0038(11) 0.0037(9) -0.0043(10)
C2 0.0288(11) 0.0244(12) 0.0331(12) -0.0005(9) -0.0010(8) -0.0035(9)
C3 0.0285(10) 0.0262(12) 0.0329(12) -0.0017(10) -0.0005(8) -0.0012(9)
C7 0.0389(13) 0.0331(13) 0.0365(14) -0.0008(10) 0.0073(10) -0.0029(10)
C13 0.0344(12) 0.0321(12) 0.0413(14) -0.0004(10) 0.0016(10) -0.0030(10)
C12 0.0401(13) 0.0379(14) 0.0458(15) -0.0018(11) -0.0079(10) 0.0033(11)
C6 0.0484(15) 0.0415(15) 0.0461(15) -0.0009(12) 0.0170(11) -0.0088(12)
C10 0.0547(16) 0.0446(16) 0.0357(14) 0.0034(11) 0.0076(11) -0.0145(13)
C11 0.0604(17) 0.0364(15) 0.0362(14) 0.0039(11) -0.0058(11) 0.0000(12)
_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
O1 C1 1.418(3) . ?
O1 C2 1.433(3) . ?
O2 C1 1.438(3) . ?
O2 C3 1.433(3) . ?
O3 C5 1.362(3) . ?
O3 C6 1.444(4) . ?
O4 C7 1.425(3) . ?
O4 H4 0.966(19) . ?
O1W H1W 0.968(15) . ?
C8 C1 1.499(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.397(3) . ?
C1 H1 0.9800 . ?
C5 H5 0.9300 . ?
C5 C4 1.320(4) . ?
C4 H4A 0.9300 . ?
C4 C3 1.509(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.516(3) . ?
C2 C7 1.511(3) . ?
C3 H3 0.9800 . ?
C7 H7 0.9800 . ?
C7 C6 1.524(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.386(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9300 . ?
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
C1 O1 C2 104.69(16) . . ?
C3 O2 C1 107.66(17) . . ?
C5 O3 C6 116.0(2) . . ?
C7 O4 H4 126.2(18) . . ?
C9 C8 C1 120.8(2) . . ?
C9 C8 C13 119.0(2) . . ?
C13 C8 C1 120.2(2) . . ?
O1 C1 O2 107.06(17) . . ?
O1 C1 C8 109.52(18) . . ?
O1 C1 H1 109.5 . . ?
O2 C1 C8 111.85(18) . . ?
O2 C1 H1 109.5 . . ?
C8 C1 H1 109.5 . . ?
O3 C5 H5 116.0 . . ?
C4 C5 O3 127.9(3) . . ?
C4 C5 H5 116.0 . . ?
C5 C4 H4A 118.1 . . ?
C5 C4 C3 123.8(2) . . ?
C3 C4 H4A 118.1 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
O1 C2 H2 109.7 . . ?
O1 C2 C3 101.95(18) . . ?
O1 C2 C7 112.04(19) . . ?
C3 C2 H2 109.7 . . ?
C7 C2 H2 109.7 . . ?
C7 C2 C3 113.53(19) . . ?
O2 C3 C4 111.41(19) . . ?
O2 C3 C2 102.74(17) . . ?
O2 C3 H3 110.1 . . ?
C4 C3 C2 112.1(2) . . ?
C4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
O4 C7 C2 107.4(2) . . ?
O4 C7 H7 109.4 . . ?
O4 C7 C6 111.9(2) . . ?
C2 C7 H7 109.4 . . ?
C2 C7 C6 109.5(2) . . ?
C6 C7 H7 109.4 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
O3 C6 C7 113.2(2) . . ?
O3 C6 H6A 108.9 . . ?
O3 C6 H6B 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
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
O1 C2 C3 O2 35.9(2) . . . . ?
O1 C2 C3 C4 155.62(18) . . . . ?
O1 C2 C7 O4 -83.2(2) . . . . ?
O1 C2 C7 C6 155.2(2) . . . . ?
O3 C5 C4 C3 3.1(4) . . . . ?
O4 C7 C6 O3 -70.1(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C8 C13 C12 C11 -0.8(4) . . . . ?
C1 O1 C2 C3 -39.4(2) . . . . ?
C1 O1 C2 C7 -161.08(18) . . . . ?
C1 O2 C3 C4 -139.49(19) . . . . ?
C1 O2 C3 C2 -19.3(2) . . . . ?
C1 C8 C9 C10 -178.2(2) . . . . ?
C1 C8 C13 C12 178.8(2) . . . . ?
C5 O3 C6 C7 -86.6(3) . . . . ?
C5 C4 C3 O2 150.3(2) . . . . ?
C5 C4 C3 C2 35.8(3) . . . . ?
C9 C8 C1 O1 113.5(2) . . . . ?
C9 C8 C1 O2 -128.0(2) . . . . ?
C9 C8 C13 C12 0.7(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C2 O1 C1 O2 28.3(2) . . . . ?
C2 O1 C1 C8 149.71(17) . . . . ?
C2 C7 C6 O3 48.9(3) . . . . ?
C3 O2 C1 O1 -4.6(2) . . . . ?
C3 O2 C1 C8 -124.57(19) . . . . ?
C3 C2 C7 O4 162.0(2) . . . . ?
C3 C2 C7 C6 40.4(3) . . . . ?
C7 C2 C3 O2 156.62(19) . . . . ?
C7 C2 C3 C4 -83.7(3) . . . . ?
C13 C8 C1 O1 -64.6(3) . . . . ?
C13 C8 C1 O2 53.9(3) . . . . ?
C13 C8 C9 C10 -0.1(4) . . . . ?
C13 C12 C11 C10 0.4(4) . . . . ?
C6 O3 C5 C4 30.9(3) . . . . ?
_shelx_SHELXL_version_number '2014/7'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id AJE-01-199
_olex2_submission_special_instructions 'No special instructions were received'