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

data_7232755
_publ_section_title
;
 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         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_name_common            paracetamol
_chemical_name_systematic        acetaminophen
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-24 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.143(8)
_cell_length_b                   11.806(6)
_cell_length_c                   7.399(10)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      3.45
_cell_volume                     1497(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker, Apex3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.278
_diffrn_measured_fraction_theta_max 0.278
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1289
_diffrn_reflns_av_unetI/netI     0.1386
_diffrn_reflns_Laue_measured_fraction_full 0.278
_diffrn_reflns_Laue_measured_fraction_max 0.278
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            866
_diffrn_reflns_point_group_measured_fraction_full 0.278
_diffrn_reflns_point_group_measured_fraction_max 0.278
_diffrn_reflns_theta_full        23.355
_diffrn_reflns_theta_max         23.355
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0969 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.7071. 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    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'crystallization at approx 0.21 GPa pressure in MeOH:H2O solution'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         304
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1041P)^2^+1.2679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.2071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                161
_reflns_number_total             304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00365g1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7232755--7232759.cif.'
_cod_database_code               7232755
_shelx_shelxl_version_number     2014/7
_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:
 N1(H1A), C6(H6), C2(H2), C3(H3), C5(H5)
3.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Crystal in diamond anvil cell in MeOH:H2O paracetamol solution'
_olex2_submission_special_instructions 'No special instructions were received'