<i>meta</i>-Non-flat substituents: a novel molecular design to improve aqueous solubility in small molecule drug discovery.
Ichikawa, Yuki; Hiramatsu, Michiaki; Mita, Yusuke; Makishima, Makoto; Matsumoto, Yotaro; Masumoto, Yui; Muranaka, Atsuya; Uchiyama, Masanobu; Hashimoto, Yuichi; Ishikawa, Minoru; Organic & biomolecular chemistry 19 (2021) 446–456; doi:10.1039/d0ob02083d

data_7157816
_publ_section_title
;
 <i>meta</i>-Non-flat substituents: a novel molecular design to improve
 aqueous solubility in small molecule drug discovery.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              446
_journal_page_last               456
_journal_paper_doi               10.1039/d0ob02083d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C7 H4 Br N'
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02
_chemical_melting_point          385
_chemical_name_systematic        4-Bromobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-03-08 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2214(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4437(1)
_cell_length_b                   8.5227(1)
_cell_length_c                   4.0482(1)
_cell_measurement_reflns_used    4004
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.334
_cell_measurement_theta_min      3.220
_cell_volume                     325.749(10)
_computing_cell_refinement       HKL2000
_computing_data_collection       CrystalClear
_computing_data_reduction        HKL2000
_computing_molecular_graphics    SV
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4004
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.334
_diffrn_reflns_theta_min         3.220
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    6.203
_exptl_absorpt_correction_T_max  0.67326
_exptl_absorpt_correction_T_min  0.63685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 MULABS - Empirical Correction for Absorption Anisotropy.
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_description       needle
_exptl_crystal_F_000             176
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1031
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0209
_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^)+(0.0300P)^2^+0.1262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0520
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1031
_reflns_number_total             1031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02083d2.cif
_cod_data_source_block           CY013
_cod_depositor_comments
'Adding full bibliography for 7157808--7157819.cif.'
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               7157816
_shelx_estimated_absorpt_t_min   0.671
_shelx_estimated_absorpt_t_max   0.836
_shelxl_version_number           2014-3
_shelx_res_checksum              11947
_shelx_hkl_checksum              79252