Antisolvent addition at extreme conditions
Ward, Martin R.; Oswald, Iain D. H.; CrystEngComm 21 (2019) 4437–; doi:10.1039/C9CE00365G

data_7232756
_publ_section_title
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 Antisolvent addition at extreme conditions
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4437
_journal_paper_doi               10.1039/C9CE00365G
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C H4 O, C8 H9 N O2'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_name_common            'paracetamol:methanol solvate, (1:1)'
_chemical_name_systematic        'acetaminophen:methanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
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2019-04-24 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.032(8)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.9717(15)
_cell_length_b                   17.1881(9)
_cell_length_c                   13.0437(19)
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      22.360
_cell_measurement_theta_min      2.370
_cell_volume                     2613.2(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.349
_diffrn_measured_fraction_theta_max 0.349
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9591
_diffrn_reflns_point_group_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.349
_diffrn_reflns_theta_full        23.297
_diffrn_reflns_theta_max         23.297
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0848 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9145. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method
'Compresion of a 0.05 g/g solution in 64% aqueous methanol. Compression to 1.5 GPa to initiate the crystallisation followed by decompression 0.7 GPa and heat treatment'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.552
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.552
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.1291
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3349
_refine_ls_wR_factor_ref         0.4172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                765
_reflns_number_total             1319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00365g1.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7232755--7232759.cif.'
_cod_database_code               7232756
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N1C(H1CA), N1A(H1AA), N1B(H1BA), C5A(H5A), C6A(H6A), C2A(H2A), C3A(H3A),
 C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B)
3.b Fitted hexagon refined as free rotating group:
 C4A(C5A,C6A,C1A,C2A,C3A), C1C(C2C,C3C,C4C,C5C,C6C), C1B(C2B,C3B,C4B,C5B,C6B)
3.c Tetrahedral OH refined with riding coordinates:
 O3C(H3CA), O3A(H3AA), O3B(H3BA)
3.d Idealised Me refined as rotating group:
 C9C(H9CA,H9CB,H9CC), C8C(H8CA,H8CB,H8CC), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,
 H8AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
3.e Idealised tetrahedral OH refined as rotating group:
 O1C(H1C), O1B(H1B), O1A(H1A)
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_olex2_submission_special_instructions 'No special instructions were received'