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_7245904
_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         'C15 H15 Br N2 O4'
_chemical_formula_sum            'C15 H15 Br N2 O4'
_chemical_formula_weight         367.20
_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
;
2022-03-06 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 84.574(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6908(2)
_cell_length_b                   10.0921(4)
_cell_length_c                   27.4423(9)
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3980
_cell_measurement_theta_min      2.1450
_cell_volume                     1569.01(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -47.00 -16.00   1.00   60.00    --  -15.29 145.00  49.00   31
  2  \w    -60.00 -35.00   1.00   60.00    --  -15.29 126.00-118.00   25
  3  \w     13.00  38.00   1.00   60.00    --   17.79-126.00 164.00   25
  4  \w     48.00  80.00   1.00   60.00    --   17.79-145.00  -3.00   32
  5  \w    -41.00  38.00   1.00   60.00    --  -15.29  77.00 -90.00   79
  6  \w    -23.00  50.00   1.00   60.00    --  -15.29  57.00   0.00   73
  7  \w     31.00  56.00   1.00   60.00    --   17.79 -99.00-120.00   25
  8  \w    -16.00  14.00   1.00   60.00    --   17.79 -99.00-120.00   30
  9  \w     -9.00  39.00   1.00   60.00    --   17.79  77.00  90.00   48
 10  \w      2.00  62.00   1.00   60.00    --   17.79  57.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428412521
_diffrn_orient_matrix_UB_12      0.0645899832
_diffrn_orient_matrix_UB_13      -0.0059048115
_diffrn_orient_matrix_UB_21      -0.1090986504
_diffrn_orient_matrix_UB_22      0.0272892938
_diffrn_orient_matrix_UB_23      0.0098965896
_diffrn_orient_matrix_UB_31      0.0440099793
_diffrn_orient_matrix_UB_32      0.0047730198
_diffrn_orient_matrix_UB_33      0.0232681012
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12050
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67364
_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_density_diffrn    1.554
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0320P)^2^+1.0956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             2767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01355j2.cif
_cod_data_source_block           as_4851_duc
_cod_depositor_comments
'Adding full bibliography for 7245901--7245906.cif.'
_cod_original_cell_volume        1569.00(10)
_cod_database_code               7245904
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H12O2Cl2N2
_chemical_oxdiff_usercomment     DC-56
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              23939
_shelx_hkl_checksum              48222
_olex2_date_sample_data_collection 2021-02-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.767