#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240371.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_7240371
loop_
_publ_author_name
'Popa, Marcel Mirel'
'Shova, Sergiu'
'Hrubaru, Madalina'
'Barbu, Loredana'
'Draghici, Constantin'
'Dumitrascu, Florea'
'Dumitrescu, Denisa E.'
_publ_section_title
;
 Introducing chirality in halogenated 3-arylsydnones and their
 corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              15656
_journal_page_last               15664
_journal_paper_doi               10.1039/D0RA02368J
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C11 H10 Br2 N2 O2'
_chemical_formula_sum            'C11 H10 Br2 N2 O2'
_chemical_formula_weight         362.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.771(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0273(13)
_cell_length_b                   9.0598(6)
_cell_length_c                   16.3781(16)
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0590
_cell_measurement_theta_min      3.6150
_cell_volume                     1315.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -19.0000  -30.0000 119

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   57.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  -86.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000  -90.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0740785000
_diffrn_orient_matrix_UB_12      -0.0031426000
_diffrn_orient_matrix_UB_13      -0.0239756000
_diffrn_orient_matrix_UB_21      0.0253548000
_diffrn_orient_matrix_UB_22      0.0362058000
_diffrn_orient_matrix_UB_23      -0.0332381000
_diffrn_orient_matrix_UB_31      0.0165519000
_diffrn_orient_matrix_UB_32      -0.0692853000
_diffrn_orient_matrix_UB_33      -0.0162839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8750
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         3.214
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.827
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0385
_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)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1600
_reflns_number_total             2311
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra02368j2.cif
_cod_data_source_block           shc_544_fldu
_cod_depositor_comments
'Adding full bibliography for 7240370--7240372.cif.'
_cod_database_code               7240371
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N4O2Cl1
_chemical_oxdiff_usercomment     I_191
_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   0.345
_shelx_estimated_absorpt_t_min   0.222
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H8A,H8B,H8C} of C8
 At 1.5 times of:
  {H9A,H9B,H9C} of C9
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 1518679427.4
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.22682(7) 1.40744(4) 0.40567(3) 0.0780(2) Uani 1 1 d . U . . .
Br2 Br 0.25077(7) 1.05700(5) 0.12680(3) 0.0699(2) Uani 1 1 d . . . . .
O1 O 0.1694(3) 0.6025(3) 0.1944(2) 0.0579(9) Uani 1 1 d . . . . .
O2 O 0.3860(4) 0.4867(3) 0.1817(2) 0.0728(10) Uani 1 1 d . . . . .
N1 N 0.2479(4) 0.8021(3) 0.2521(2) 0.0379(8) Uani 1 1 d . . . . .
N2 N 0.1221(4) 0.7328(3) 0.2240(2) 0.0569(10) Uani 1 1 d . . . . .
C1 C 0.2330(4) 1.2176(4) 0.3582(3) 0.0412(10) Uani 1 1 d . . . . .
C2 C 0.2362(4) 1.2085(4) 0.2748(3) 0.0418(10) Uani 1 1 d . . . . .
H2 H 0.234502 1.293135 0.242518 0.050 Uiso 1 1 calc R . . . .
C3 C 0.2418(4) 1.0706(4) 0.2406(3) 0.0382(10) Uani 1 1 d . . . . .
C4 C 0.2393(4) 0.9459(4) 0.2892(3) 0.0350(10) Uani 1 1 d . . . . .
C5 C 0.2345(4) 0.9534(4) 0.3730(3) 0.0381(10) Uani 1 1 d . . . . .
C6 C 0.2320(4) 1.0945(4) 0.4080(3) 0.0470(11) Uani 1 1 d . . . . .
H6 H 0.229699 1.105139 0.464184 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2357(5) 0.8172(4) 0.4280(3) 0.0507(12) Uani 1 1 d . . . . .
H7 H 0.224255 0.730707 0.391439 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3851(6) 0.8029(5) 0.4862(3) 0.0797(16) Uani 1 1 d . . . . .
H8A H 0.464570 0.799451 0.454562 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.386205 0.713869 0.518045 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.400007 0.886260 0.522970 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.1045(6) 0.8168(5) 0.4737(3) 0.0830(18) Uani 1 1 d . . . . .
H9A H 0.112648 0.900095 0.510524 0.125 Uiso 1 1 calc GR . . . .
H9B H 0.106233 0.727366 0.505330 0.125 Uiso 1 1 calc GR . . . .
H9C H 0.011546 0.822663 0.434303 0.125 Uiso 1 1 calc GR . . . .
C10 C 0.3721(5) 0.7301(4) 0.2433(3) 0.0512(12) Uani 1 1 d . . . . .
H10 H 0.470672 0.763279 0.259850 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3279(5) 0.5961(4) 0.2050(3) 0.0479(11) Uani 1 1 d . . . . .
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
N2 O1 C11 111.6(3) . . ?
N2 N1 C4 118.1(3) . . ?
N2 N1 C10 115.0(3) . . ?
C10 N1 C4 126.9(3) . . ?
N1 N2 O1 103.4(3) . . ?
C2 C1 Br1 118.1(3) . . ?
C2 C1 C6 122.8(3) . . ?
C6 C1 Br1 119.2(3) . . ?
C1 C2 C3 118.0(3) . . ?
C2 C3 Br2 118.3(3) . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 Br2 121.6(3) . . ?
C3 C4 N1 119.0(4) . . ?
C5 C4 N1 118.4(3) . . ?
C5 C4 C3 122.6(3) . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 C7 123.2(3) . . ?
C6 C5 C7 119.7(4) . . ?
C1 C6 C5 119.5(4) . . ?
C8 C7 C5 110.5(3) . . ?
C8 C7 C9 112.2(4) . . ?
C9 C7 C5 112.0(3) . . ?
N1 C10 C11 107.5(4) . . ?
O2 C11 O1 118.9(4) . . ?
O2 C11 C10 138.5(5) . . ?
C10 C11 O1 102.6(3) . . ?
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 C1 1.892(3) . ?
Br2 C3 1.884(4) . ?
O1 N2 1.374(4) . ?
O1 C11 1.410(5) . ?
O2 C11 1.215(4) . ?
N1 N2 1.304(4) . ?
N1 C4 1.446(4) . ?
N1 C10 1.328(4) . ?
C1 C2 1.374(5) . ?
C1 C6 1.383(5) . ?
C2 C3 1.374(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.402(5) . ?
C5 C7 1.526(5) . ?
C7 C8 1.505(6) . ?
C7 C9 1.515(5) . ?
C10 C11 1.392(5) . ?
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
C2 H2 O2 0.93 2.54 3.359(5) 147.1 1_565 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341269
