Crystal structures of 5-bromo-1-arylpyrazoles and their halogen bonding features
Popa, Marcel Mirel; Shova, Sergiu; Dascalu, Mihaela; Caira, Mino R.; Dumitrascu, Florea; CrystEngComm 25 (2023) 86–94; doi:10.1039/D2CE01355J

data_7245903
_publ_section_title
;
 Crystal structures of 5-bromo-1-arylpyrazoles and their halogen bonding
 features
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              86
_journal_page_last               94
_journal_paper_doi               10.1039/D2CE01355J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C14 H12 Br Cl N2 O4'
_chemical_formula_sum            'C14 H12 Br Cl N2 O4'
_chemical_formula_weight         387.62
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-02-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-08 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.144(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3058(5)
_cell_length_b                   10.0452(9)
_cell_length_c                   28.782(2)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      23.9750
_cell_measurement_theta_min      2.1620
_cell_volume                     1533.7(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2682
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.147
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0964
_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^)+(0.0546P)^2^+12.6017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1796
_reflns_number_total             2682
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01355j2.cif
_cod_data_source_block           shi_4865_fldu_auto_tw
_cod_depositor_comments
'Adding full bibliography for 7245901--7245906.cif.'
_cod_database_code               7245903
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.597
_shelx_estimated_absorpt_t_min   0.479
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.848(9)
 0.152(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              34230
_shelx_hkl_checksum              50980
_olex2_submission_special_instructions 'No special instructions were received'