Intermolecular head-to-head interaction of carbonyl groups in bicyclic hydrogen-bonded synthon based on β-hydroxy ketones
Fayzullin, Robert R.; Shteingolts, Sergey A.; Lodochnikova, Olga A.; Mamedova, Vera L.; Korshin, Dmitry E.; Mamedov, Vakhid A.; CrystEngComm 21 (2019) 1587–; doi:10.1039/C8CE02132E

data_7232275
_publ_section_title
;
 Intermolecular head-to-head interaction of carbonyl groups in bicyclic
 hydrogen-bonded synthon based on \b-hydroxy ketones
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1587
_journal_paper_doi               10.1039/C8CE02132E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C15 H11 Br Cl N O4'
_chemical_formula_sum            'C15 H11 Br Cl N O4'
_chemical_formula_weight         384.61
_chemical_melting_point          398
_chemical_name_systematic
(2RS,3RS)-2-bromo-1-(4-chlorophenyl)-3-hydroxy-3-(2-nitrophenyl)-propan-1-one
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-12-16 deposited with the CCDC.
2019-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.211(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.847(11)
_cell_length_b                   7.932(6)
_cell_length_c                   14.919(11)
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.78
_cell_measurement_theta_min      2.67
_cell_volume                     1548(2)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX2 v2014.11-0 (Bruker AXS)'
_computing_molecular_graphics
;
WinGX (Farrugia, 2012); Olex2 (Dolomanov et al., 2009);
ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009)
;
_computing_publication_material  'enCIFer (Allen, 2004)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         2.665
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'slow evaporation of an ethanol solution at r.t.'
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.068
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0674P)^2^+2.4189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2026
_reflns_number_total             2844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02132e2.cif
_cod_data_source_block           v600
_cod_depositor_comments
'Adding full bibliography for 7232272--7232275.cif.'
_cod_original_cell_volume        1548.1(19)
_cod_database_code               7232275
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.505
_shelx_estimated_absorpt_t_max   0.830
_shelx_res_checksum              28880
_shelx_hkl_checksum              56335