Mining predicted crystal structure landscapes with high throughput crystallisation: old molecules, new insights
Cui, Peng; McMahon, David P.; Spackman, Peter R.; Alston, Ben M.; Little, Marc A.; Day, Graeme M.; Cooper, Andrew I.; Chemical Science 10 (2019) 9988–; doi:10.1039/C9SC02832C

data_1555265
_publ_section_title
;
 Mining predicted crystal structure landscapes with high throughput
 crystallisation: old molecules, new insights
;
_journal_issue                   43
_journal_name_full               'Chemical Science'
_journal_page_first              9988
_journal_paper_doi               10.1039/C9SC02832C
_journal_volume                  10
_journal_year                    2019
_chemical_formula_moiety         'C9 H6 O6, C6 H10 O'
_chemical_formula_sum            'C15 H16 O7'
_chemical_formula_weight         308.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.207(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.254(3)
_cell_length_b                   16.7260(16)
_cell_length_c                   6.7365(6)
_cell_measurement_reflns_used    4792
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.390
_cell_measurement_theta_min      2.436
_cell_volume                     3022.2(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         1.435
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0862 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.6902. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0731
_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^)+(0.1529P)^2^+3.7273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2250
_refine_ls_wR_factor_ref         0.2492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2261
_reflns_number_total             3117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           TMA_3-31_EtOH-cyclohexanone_publ
_cod_original_cell_volume        3022.3(5)
_cod_database_code               1555265
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.991
_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,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C13-C14 = C15-C14 = C10-C15 = C11-C10 = C12-C11 = C16-C11 = C13-C12 = C17-C16
 = C17-C18 = C19-C18 = C19-C10
 1.52 with sigma of 0.02
 O9-C19
 1.23 with sigma of 0.02
 C10-C18
 2.56 with sigma of 0.04
 C17-C11
 2.56 with sigma of 0.04
 C15-C13
 2.56 with sigma of 0.04
 C12-C10
 2.56 with sigma of 0.04
 C19-C17
 2.56 with sigma of 0.04
 C10-O9 \\sim O9-C18
 with sigma of 0.02
3. Restrained planarity
 H5, O5, C8, O6, H6
 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C13, O8, C14, C15, C10, C12, O7, C11, C19, C16, C18, C17, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H5(0.5) H6(0.5) O8(0.6) O7(0.25) C14(0.75) C15(0.75) H15A(0.75)
 H15B(0.75) H10A(0.75) H10B(0.75) H11A(0.75) H11B(0.75) H11C(0.25) H11D(0.25)
 C12(0.75) H12A(0.75) H12B(0.75) C13(0.75) H13A(0.75) H13B(0.75) C18(0.25)
 H18A(0.25) H18B(0.25) C19(0.25) C17(0.25) H17A(0.25) H17B(0.25) C16(0.25)
 H16A(0.25) H16B(0.25) O9(0.15)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C11(H11A,H11B), C11(H11C,H11D), C12(H12A,
 H12B), C13(H13A,H13B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C5(H5A)
6.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5), O6(H6)
;
_shelx_res_checksum              17080
_olex2_submission_special_instructions 'No special instructions were received'