#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:08:48 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245906.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245906
loop_
_publ_author_name
'Popa, Marcel Mirel'
'Shova, Sergiu'
'Dascalu, Mihaela'
'Caira, Mino R.'
'Dumitrascu, Florea'
_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         'C16 H16 Br2 N2 O4'
_chemical_formula_sum            'C16 H16 Br2 N2 O4'
_chemical_formula_weight         460.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-06
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0434(8)
_cell_length_b                   12.0064(8)
_cell_length_c                   21.0629(13)
_cell_measurement_reflns_used    1982
_cell_measurement_temperature    250.05(10)
_cell_measurement_theta_max      22.2580
_cell_measurement_theta_min      2.4140
_cell_volume                     3551.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  13.00   1.00   30.00    --   17.63-107.00-162.00   27
  2  ω      7.00  83.00   1.00   30.00    --   17.63  76.00  49.00   76
  3  ω    -84.00 -44.00   1.00   30.00    --  -15.21-178.00-150.00   40
  4  ω     -8.00  30.00   1.00   30.00    --   17.63  77.00-180.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0413787000
_diffrn_orient_matrix_UB_12      0.0252029000
_diffrn_orient_matrix_UB_13      0.0128274000
_diffrn_orient_matrix_UB_21      0.0101193000
_diffrn_orient_matrix_UB_22      -0.0240928000
_diffrn_orient_matrix_UB_23      0.0300080000
_diffrn_orient_matrix_UB_31      0.0270963000
_diffrn_orient_matrix_UB_32      0.0476964000
_diffrn_orient_matrix_UB_33      0.0083567000
_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  0.0635
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.934
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (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    1.721
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2106
_reflns_number_total             3133
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01355j2.cif
_cod_data_source_block           shi_4748_fldu
_cod_depositor_comments
'Adding full bibliography for 7245901--7245906.cif.'
_cod_database_code               7245906
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H15N3O4Br2
_chemical_oxdiff_usercomment     I-490
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.546
_shelx_estimated_absorpt_t_min   0.492
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.915
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.70624(3) 0.71750(5) 0.15528(2) 0.04888(17) Uani 1 1 d . . . . .
Br2 Br 0.41752(3) 0.55830(4) 0.39876(2) 0.04298(15) Uani 1 1 d . . . . .
O1 O 0.5974(3) 0.0841(3) 0.42500(16) 0.0688(12) Uani 1 1 d . . . . .
O2 O 0.62089(18) 0.1740(3) 0.51652(14) 0.0378(8) Uani 1 1 d . . . . .
O3 O 0.35775(19) 0.3924(3) 0.51287(14) 0.0454(9) Uani 1 1 d . . . . .
O4 O 0.41261(19) 0.2163(3) 0.51117(13) 0.0388(8) Uani 1 1 d . . . . .
N1 N 0.5731(2) 0.4209(3) 0.37030(15) 0.0273(9) Uani 1 1 d . . . . .
N2 N 0.6176(2) 0.3225(3) 0.38335(16) 0.0298(9) Uani 1 1 d . . . . .
C1 C 0.6051(3) 0.4893(4) 0.31869(19) 0.0268(11) Uani 1 1 d . . . . .
C2 C 0.6778(3) 0.5651(4) 0.3298(2) 0.0318(12) Uani 1 1 d . . . . .
H2 H 0.705637 0.570403 0.370232 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7090(3) 0.6326(4) 0.2809(2) 0.0348(12) Uani 1 1 d . . . . .
H3 H 0.758888 0.683638 0.287264 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6653(3) 0.6234(4) 0.2229(2) 0.0312(12) Uani 1 1 d . . . . .
C5 C 0.5932(3) 0.5490(4) 0.21170(19) 0.0301(11) Uani 1 1 d . . . . .
H5 H 0.564797 0.545618 0.171322 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5616(3) 0.4784(4) 0.2598(2) 0.0265(11) Uani 1 1 d . . . . .
C7 C 0.4855(3) 0.3918(4) 0.24651(19) 0.0329(12) Uani 1 1 d . . . . .
H7 H 0.470827 0.353928 0.287084 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5210(3) 0.3041(4) 0.2004(2) 0.0655(17) Uani 1 1 d . . . . .
H8A H 0.534808 0.338684 0.159769 0.098 Uiso 1 1 calc R U . . .
H8B H 0.472548 0.247444 0.194804 0.098 Uiso 1 1 calc R U . . .
H8C H 0.578520 0.270193 0.217057 0.098 Uiso 1 1 calc R U . . .
C9 C 0.3936(3) 0.4459(4) 0.2228(2) 0.0535(15) Uani 1 1 d . . . . .
H9A H 0.372013 0.500582 0.253471 0.080 Uiso 1 1 calc R U . . .
H9B H 0.345092 0.389232 0.217351 0.080 Uiso 1 1 calc R U . . .
H9C H 0.405457 0.482305 0.182409 0.080 Uiso 1 1 calc R U . . .
C10 C 0.4964(3) 0.4355(4) 0.40810(18) 0.0271(11) Uani 1 1 d . . . . .
C11 C 0.4895(3) 0.3450(4) 0.44788(18) 0.0252(11) Uani 1 1 d . . . . .
C12 C 0.5672(3) 0.2780(4) 0.43000(19) 0.0254(11) Uani 1 1 d . . . . .
C13 C 0.5955(3) 0.1670(4) 0.4560(2) 0.0334(12) Uani 1 1 d . . . . .
C14 C 0.6468(3) 0.0692(4) 0.5462(2) 0.0468(14) Uani 1 1 d . . . . .
H14A H 0.701765 0.037967 0.524632 0.070 Uiso 1 1 calc R U . . .
H14B H 0.593861 0.017576 0.543193 0.070 Uiso 1 1 calc R U . . .
H14C H 0.662225 0.081870 0.590467 0.070 Uiso 1 1 calc R U . . .
C15 C 0.4125(3) 0.3232(4) 0.4943(2) 0.0309(12) Uani 1 1 d . . . . .
C16 C 0.3368(3) 0.1853(4) 0.5544(2) 0.0496(14) Uani 1 1 d . . . . .
H16A H 0.276125 0.189441 0.532532 0.074 Uiso 1 1 calc R U . . .
H16B H 0.336394 0.235929 0.590312 0.074 Uiso 1 1 calc R U . . .
H16C H 0.347138 0.109852 0.569350 0.074 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 115.2(4) . . ?
C15 O4 C16 114.5(3) . . ?
N2 N1 C1 120.3(3) . . ?
C10 N1 N2 111.0(3) . . ?
C10 N1 C1 128.5(4) . . ?
C12 N2 N1 104.7(3) . . ?
C2 C1 N1 118.6(4) . . ?
C2 C1 C6 122.4(4) . . ?
C6 C1 N1 119.0(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 Br1 118.8(4) . . ?
C5 C4 Br1 118.7(3) . . ?
C5 C4 C3 122.4(4) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 116.9(4) . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C7 120.4(4) . . ?
C6 C7 H7 107.6 . . ?
C6 C7 C8 111.2(3) . . ?
C6 C7 C9 111.3(4) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C9 111.3(4) . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 Br2 121.1(3) . . ?
N1 C10 C11 108.2(4) . . ?
C11 C10 Br2 130.6(3) . . ?
C10 C11 C12 103.5(3) . . ?
C10 C11 C15 126.4(4) . . ?
C12 C11 C15 129.9(4) . . ?
N2 C12 C11 112.5(4) . . ?
N2 C12 C13 119.3(4) . . ?
C11 C12 C13 128.2(4) . . ?
O1 C13 O2 125.0(5) . . ?
O1 C13 C12 123.4(4) . . ?
O2 C13 C12 111.6(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 125.6(4) . . ?
O3 C15 C11 124.2(4) . . ?
O4 C15 C11 110.3(4) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.906(4) . ?
Br2 C10 1.855(4) . ?
O1 C13 1.191(5) . ?
O2 C13 1.327(5) . ?
O2 C14 1.451(4) . ?
O3 C15 1.199(5) . ?
O4 C15 1.332(5) . ?
O4 C16 1.450(4) . ?
N1 N2 1.366(4) . ?
N1 C1 1.434(5) . ?
N1 C10 1.350(4) . ?
N2 C12 1.324(5) . ?
C1 C2 1.387(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9400 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9400 . ?
C3 C4 1.372(5) . ?
C4 C5 1.371(5) . ?
C5 H5 0.9400 . ?
C5 C6 1.393(5) . ?
C6 C7 1.517(5) . ?
C7 H7 0.9900 . ?
C7 C8 1.517(5) . ?
C7 C9 1.529(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.375(5) . ?
C11 C12 1.406(5) . ?
C11 C15 1.481(5) . ?
C12 C13 1.494(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9C O1 0.97 2.57 3.529(5) 169.2 3_655 yes
C14 H14A O3 0.97 2.47 3.245(5) 136.3 4_556 yes
C16 H16C O1 0.97 2.46 3.392(6) 161.4 5_656 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 179.7(3) . . . . ?
Br2 C10 C11 C12 176.6(3) . . . . ?
Br2 C10 C11 C15 0.9(7) . . . . ?
N1 N2 C12 C11 0.3(5) . . . . ?
N1 N2 C12 C13 179.1(4) . . . . ?
N1 C1 C2 C3 -179.3(3) . . . . ?
N1 C1 C6 C5 178.1(3) . . . . ?
N1 C1 C6 C7 -4.0(6) . . . . ?
N1 C10 C11 C12 -0.2(4) . . . . ?
N1 C10 C11 C15 -175.9(4) . . . . ?
N2 N1 C1 C2 -86.6(5) . . . . ?
N2 N1 C1 C6 94.2(4) . . . . ?
N2 N1 C10 Br2 -176.8(3) . . . . ?
N2 N1 C10 C11 0.4(5) . . . . ?
N2 C12 C13 O1 -61.2(6) . . . . ?
N2 C12 C13 O2 116.7(4) . . . . ?
C1 N1 N2 C12 -175.9(4) . . . . ?
C1 N1 C10 Br2 -1.7(6) . . . . ?
C1 N1 C10 C11 175.4(4) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C6 C7 C8 -112.2(5) . . . . ?
C1 C6 C7 C9 123.0(4) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 176.9(4) . . . . ?
C2 C3 C4 Br1 179.1(3) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 C7 -176.7(4) . . . . ?
C5 C6 C7 C8 65.6(5) . . . . ?
C5 C6 C7 C9 -59.1(5) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C10 N1 N2 C12 -0.4(5) . . . . ?
C10 N1 C1 C2 98.7(5) . . . . ?
C10 N1 C1 C6 -80.4(6) . . . . ?
C10 C11 C12 N2 -0.1(5) . . . . ?
C10 C11 C12 C13 -178.8(4) . . . . ?
C10 C11 C15 O3 -17.0(7) . . . . ?
C10 C11 C15 O4 162.1(4) . . . . ?
C11 C12 C13 O1 117.4(6) . . . . ?
C11 C12 C13 O2 -64.7(6) . . . . ?
C12 C11 C15 O3 168.4(4) . . . . ?
C12 C11 C15 O4 -12.5(6) . . . . ?
C14 O2 C13 O1 -4.0(6) . . . . ?
C14 O2 C13 C12 178.2(3) . . . . ?
C15 C11 C12 N2 175.4(4) . . . . ?
C15 C11 C12 C13 -3.3(7) . . . . ?
C16 O4 C15 O3 1.8(7) . . . . ?
C16 O4 C15 C11 -177.3(3) . . . . ?
