#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:08:48 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245903.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_7245903
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         '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       'ω 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/[σ²(Fo²)+(0.0546P)²+12.6017P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.597
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.8807(2) 0.51173(11) 0.55723(4) 0.0552(4) Uani 1 1 d . . . . .
Cl1 Cl 1.2285(6) 0.5094(4) 0.76315(10) 0.0712(10) Uani 1 1 d . . . . .
O1 O 0.2487(16) 0.0344(8) 0.5980(3) 0.065(2) Uani 1 1 d . . . . .
O2 O -0.0012(14) 0.1659(7) 0.6389(2) 0.0495(19) Uani 1 1 d . . . . .
O3 O 0.6467(16) 0.2732(10) 0.4923(3) 0.075(3) Uani 1 1 d . . . . .
O4 O 0.2794(16) 0.1844(8) 0.5125(2) 0.062(2) Uani 1 1 d . . . . .
N1 N 0.5900(15) 0.4229(7) 0.6318(3) 0.0335(18) Uani 1 1 d . . . . .
N2 N 0.4168(16) 0.3320(8) 0.6458(3) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.6932(18) 0.5183(10) 0.6632(3) 0.041(2) Uani 1 1 d . . . . .
C2 C 0.5935(19) 0.6448(10) 0.6665(3) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.698(2) 0.7277(11) 0.6999(4) 0.054(3) Uani 1 1 d . . . . .
H3 H 0.637625 0.814305 0.702263 0.065 Uiso 1 1 calc R U . . .
C4 C 0.891(2) 0.6865(11) 0.7304(4) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.956618 0.744553 0.752723 0.061 Uiso 1 1 calc R U . . .
C5 C 0.983(2) 0.5600(12) 0.7268(4) 0.048(3) Uani 1 1 d . . . . .
C6 C 0.8865(18) 0.4716(10) 0.6934(3) 0.038(2) Uani 1 1 d . . . . .
H6 H 0.947233 0.385032 0.691251 0.046 Uiso 1 1 calc R U . . .
C7 C 0.388(2) 0.6903(11) 0.6348(4) 0.058(3) Uani 1 1 d . . . . .
H7A H 0.424899 0.665140 0.603545 0.087 Uiso 1 1 calc R U . . .
H7B H 0.372827 0.785437 0.636699 0.087 Uiso 1 1 calc R U . . .
H7C H 0.231906 0.649983 0.643743 0.087 Uiso 1 1 calc R U . . .
C8 C 0.6456(18) 0.4054(10) 0.5857(3) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.5009(18) 0.2996(10) 0.5685(3) 0.039(2) Uani 1 1 d . . . . .
C10 C 0.3627(19) 0.2605(9) 0.6079(3) 0.035(2) Uani 1 1 d . . . . .
C11 C 0.1973(19) 0.1414(11) 0.6126(3) 0.040(2) Uani 1 1 d . . . . .
C12 C -0.160(2) 0.0547(11) 0.6483(4) 0.058(3) Uani 1 1 d . . . . .
H12A H -0.247960 0.028488 0.620280 0.087 Uiso 1 1 calc R U . . .
H12B H -0.280473 0.079119 0.671332 0.087 Uiso 1 1 calc R U . . .
H12C H -0.059651 -0.018227 0.659655 0.087 Uiso 1 1 calc R U . . .
C13 C 0.490(2) 0.2521(11) 0.5203(3) 0.041(2) Uani 1 1 d . . . . .
C14 C 0.246(3) 0.1225(13) 0.4672(4) 0.077(4) Uani 1 1 d . . . . .
H14A H 0.127666 0.173234 0.448862 0.115 Uiso 1 1 calc R U . . .
H14B H 0.183987 0.033491 0.470985 0.115 Uiso 1 1 calc R U . . .
H14C H 0.405147 0.119843 0.451876 0.115 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'
Cl Cl 0.1484 0.1585 '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
C11 O2 C12 116.1(8) . . ?
C13 O4 C14 117.3(9) . . ?
N2 N1 C1 121.1(7) . . ?
N2 N1 C8 111.1(8) . . ?
C8 N1 C1 127.8(8) . . ?
C10 N2 N1 104.7(7) . . ?
C2 C1 N1 121.5(9) . . ?
C2 C1 C6 122.5(10) . . ?
C6 C1 N1 115.8(9) . . ?
C1 C2 C7 121.4(10) . . ?
C3 C2 C1 117.0(10) . . ?
C3 C2 C7 121.6(10) . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.5(11) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(10) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.6(9) . . ?
C4 C5 C6 121.0(11) . . ?
C6 C5 Cl1 119.4(9) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.7(9) . . ?
C5 C6 H6 121.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 Br1 120.9(7) . . ?
N1 C8 C9 108.1(8) . . ?
C9 C8 Br1 131.0(7) . . ?
C8 C9 C10 102.6(7) . . ?
C8 C9 C13 126.3(9) . . ?
C10 C9 C13 131.0(9) . . ?
N2 C10 C9 113.5(8) . . ?
N2 C10 C11 118.5(8) . . ?
C9 C10 C11 127.5(8) . . ?
O1 C11 O2 123.9(10) . . ?
O1 C11 C10 123.7(10) . . ?
O2 C11 C10 112.1(9) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 125.2(10) . . ?
O3 C13 C9 124.7(11) . . ?
O4 C13 C9 110.0(9) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C8 1.846(9) . ?
Cl1 C5 1.728(12) . ?
O1 C11 1.188(12) . ?
O2 C11 1.333(11) . ?
O2 C12 1.429(12) . ?
O3 C13 1.186(12) . ?
O4 C13 1.325(13) . ?
O4 C14 1.452(12) . ?
N1 N2 1.362(10) . ?
N1 C1 1.420(12) . ?
N1 C8 1.377(11) . ?
N2 C10 1.333(11) . ?
C1 C2 1.381(14) . ?
C1 C6 1.412(14) . ?
C2 C3 1.380(15) . ?
C2 C7 1.481(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(15) . ?
C5 C6 1.399(14) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.395(13) . ?
C9 C10 1.418(12) . ?
C9 C13 1.469(13) . ?
C10 C11 1.491(14) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
C12 H12C Cl1 0.96 2.82 3.423(13) 121.8 2_646 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 C8 C9 C10 179.2(8) . . . . ?
Br1 C8 C9 C13 -4.6(16) . . . . ?
Cl1 C5 C6 C1 -177.5(7) . . . . ?
N1 N2 C10 C9 1.3(11) . . . . ?
N1 N2 C10 C11 173.4(8) . . . . ?
N1 C1 C2 C3 176.5(8) . . . . ?
N1 C1 C2 C7 -5.0(14) . . . . ?
N1 C1 C6 C5 -176.3(8) . . . . ?
N1 C8 C9 C10 0.1(10) . . . . ?
N1 C8 C9 C13 176.3(9) . . . . ?
N2 N1 C1 C2 -95.1(11) . . . . ?
N2 N1 C1 C6 79.2(11) . . . . ?
N2 N1 C8 Br1 -178.5(6) . . . . ?
N2 N1 C8 C9 0.7(11) . . . . ?
N2 C10 C11 O1 -129.6(11) . . . . ?
N2 C10 C11 O2 44.1(12) . . . . ?
C1 N1 N2 C10 179.8(9) . . . . ?
C1 N1 C8 Br1 0.4(13) . . . . ?
C1 N1 C8 C9 179.6(9) . . . . ?
C1 C2 C3 C4 -1.9(14) . . . . ?
C2 C1 C6 C5 -2.1(14) . . . . ?
C2 C3 C4 C5 0.7(15) . . . . ?
C3 C4 C5 Cl1 178.2(8) . . . . ?
C3 C4 C5 C6 -0.2(15) . . . . ?
C4 C5 C6 C1 0.9(15) . . . . ?
C6 C1 C2 C3 2.6(14) . . . . ?
C6 C1 C2 C7 -178.9(9) . . . . ?
C7 C2 C3 C4 179.6(9) . . . . ?
C8 N1 N2 C10 -1.2(10) . . . . ?
C8 N1 C1 C2 86.1(12) . . . . ?
C8 N1 C1 C6 -99.6(11) . . . . ?
C8 C9 C10 N2 -0.9(11) . . . . ?
C8 C9 C10 C11 -172.2(10) . . . . ?
C8 C9 C13 O3 20.4(17) . . . . ?
C8 C9 C13 O4 -158.6(10) . . . . ?
C9 C10 C11 O1 41.3(16) . . . . ?
C9 C10 C11 O2 -145.0(10) . . . . ?
C10 C9 C13 O3 -164.6(11) . . . . ?
C10 C9 C13 O4 16.4(15) . . . . ?
C12 O2 C11 O1 -1.7(15) . . . . ?
C12 O2 C11 C10 -175.4(9) . . . . ?
C13 C9 C10 N2 -176.8(10) . . . . ?
C13 C9 C10 C11 11.9(18) . . . . ?
C14 O4 C13 O3 5.0(17) . . . . ?
C14 O4 C13 C9 -176.0(9) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.848(9)
2 0.152(9)
