Monohalogenated carbamates where hydrogen bonding rules without halogen bonding: is there a link between poor carbamate crystal growth and Z′ > 1?
Mocilac, Pavle; Gallagher, John F.; CrystEngComm 21 (2019) 4048–; doi:10.1039/C9CE00318E

data_7232851
_publ_section_title
;
 Monohalogenated carbamates where hydrogen bonding rules without halogen
 bonding: is there a link between poor carbamate crystal growth and
 Z&#x2032; &gt; 1?
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              4048
_journal_paper_doi               10.1039/C9CE00318E
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 Br N2 O2'
_chemical_formula_sum            'C12 H9 Br N2 O2'
_chemical_formula_weight         293.12
_chemical_melting_point          427
_chemical_name_common            CmmBr
_chemical_name_systematic        3-Bromophenyl-N-3-pyridylcarbamate
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-12 deposited with the CCDC.    2019-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.789(14)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   3.8827(5)
_cell_length_b                   24.756(2)
_cell_length_c                   17.742(2)
_cell_measurement_reflns_used    1096
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      3.28
_cell_volume                     1704.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(1)
_diffrn_detector_area_resol_mean 16.056
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.4197
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10527
_diffrn_reflns_point_group_measured_fraction_full 0.812
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.931
_diffrn_reflns_theta_min         4.598
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         99999
_exptl_absorpt_coefficient_mu    3.607
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical SCALE3 ABSPACK'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_description       Trapezoid
_exptl_crystal_F_000             876
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform:acetonitrile'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.008(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.630
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      0.630
_refine_ls_R_factor_all          0.2284
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0185P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.694
_reflns_Friedel_fraction_max     0.606
_reflns_number_gt                1546
_reflns_number_total             5993
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c9ce00318e2.cif
_cod_data_source_block           CmmBr_[13-022]
_cod_depositor_comments
'Adding full bibliography for 7232844--7232852.cif.'
_cod_database_code               7232851
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.411
_shelx_estimated_absorpt_t_max   0.737
_shelx_res_checksum              80955