#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/73/7157320.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_7157320
loop_
_publ_author_name
'Motornov, Vladimir A.'
'Tabolin, Andrey A.'
'Nelyubina, Yulia V.'
'Nenajdenko, Valentine G.'
'Ioffe, Sema L.'
_publ_section_title
;
 Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and
 pyridinium imines: efficient synthesis of 3-fluoro- and
 3-nitro-pyrazolo[1,5-a]pyridines.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1436
_journal_page_last               1448
_journal_paper_doi               10.1039/c9ob02668a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C13 H8 Br F N2'
_chemical_formula_sum            'C13 H8 Br F N2'
_chemical_formula_weight         291.12
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-30 deposited with the CCDC.	2020-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 138.9436(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5420(12)
_cell_length_b                   4.0333(3)
_cell_length_c                   22.2351(15)
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.21
_cell_volume                     1092.17(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23407
_diffrn_reflns_theta_full        28.9828
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.752
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.7412.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7704
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.5856
_refine_diff_density_min         -0.3679
_refine_diff_density_rms         0.0884
_refine_ls_d_res_high            0.7334
_refine_ls_d_res_low             10.8223
_refine_ls_goodness_of_fit_ref   1.0206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0206
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0281P)²+0.7264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0573
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -25
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                2551
_reflns_number_total             2911
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob02668a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7157320--7157321.cif.'
_cod_database_code               7157320
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Br1 Br 0.643310(12) -0.12609(4) 0.931269(11) 0.01964(6) Uani 1.000000 .
F1 F 0.25018(8) 0.7726(3) 0.85941(6) 0.0228(2) Uani 1.000000 .
N1 N 0.12687(11) 0.5841(3) 0.64028(9) 0.0154(3) Uani 1.000000 .
N2 N 0.04943(11) 0.7636(4) 0.62097(9) 0.0142(3) Uani 1.000000 .
C1 C 0.21280(13) 0.5655(4) 0.73342(10) 0.0142(3) Uani 1.000000 .
C2 C -0.05162(13) 0.8430(4) 0.53394(11) 0.0170(3) Uani 1.000000 .
H2 H -0.07211(13) 0.7705(4) 0.48198(11) 0.0204(4) Uiso 1.000000 R
C3 C -0.12178(13) 1.0280(4) 0.52381(11) 0.0182(3) Uani 1.000000 .
H3 H -0.19162(13) 1.0871(4) 0.46416(11) 0.0218(4) Uiso 1.000000 R
C4 C -0.09147(14) 1.1342(4) 0.60194(12) 0.0196(3) Uani 1.000000 .
H4 H -0.14159(14) 1.2604(4) 0.59383(12) 0.0235(4) Uiso 1.000000 R
C5 C 0.00921(14) 1.0549(4) 0.68816(12) 0.0175(3) Uani 1.000000 .
H5 H 0.03003(14) 1.1272(4) 0.74028(12) 0.0210(4) Uiso 1.000000 R
C6 C 0.08206(13) 0.8631(4) 0.69854(11) 0.0153(3) Uani 1.000000 .
C7 C 0.18651(13) 0.7324(4) 0.76997(11) 0.0153(3) Uani 1.000000 .
C8 C 0.31441(13) 0.3949(4) 0.78016(11) 0.0147(3) Uani 1.000000 .
C9 C 0.39550(13) 0.3229(4) 0.87417(11) 0.0171(3) Uani 1.000000 .
H9 H 0.38378(13) 0.3818(4) 0.90767(11) 0.0205(4) Uiso 1.000000 R
C10 C 0.49273(13) 0.1666(4) 0.91878(11) 0.0176(3) Uani 1.000000 .
H10 H 0.54755(13) 0.1206(4) 0.98247(11) 0.0212(4) Uiso 1.000000 R
C11 C 0.50869(13) 0.0786(4) 0.86907(11) 0.0158(3) Uani 1.000000 .
C12 C 0.42975(13) 0.1433(4) 0.77585(11) 0.0184(3) Uani 1.000000 .
H12 H 0.44153(13) 0.0803(4) 0.74260(11) 0.0221(4) Uiso 1.000000 R
C13 C 0.33313(13) 0.3019(4) 0.73207(11) 0.0173(3) Uani 1.000000 .
H13 H 0.27886(13) 0.3481(4) 0.66841(11) 0.0208(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 104.83(13)
C2 N2 N1 124.32(13)
C6 N2 N1 113.28(13)
C6 N2 C2 122.39(14)
C7 C1 N1 109.68(14)
C8 C1 N1 120.53(14)
C8 C1 C7 129.77(14)
H2 C2 N2 120.72(9)
C3 C2 N2 118.57(15)
C3 C2 H2 120.72(10)
H3 C3 C2 119.62(10)
C4 C3 C2 120.76(15)
C4 C3 H3 119.62(10)
H4 C4 C3 119.86(10)
C5 C4 C3 120.28(15)
C5 C4 H4 119.86(10)
H5 C5 C4 120.56(10)
C6 C5 C4 118.87(15)
C6 C5 H5 120.56(9)
C5 C6 N2 119.12(14)
C7 C6 N2 103.73(14)
C7 C6 C5 137.14(15)
C1 C7 F1 127.76(14)
C6 C7 F1 123.77(14)
C6 C7 C1 108.46(14)
C9 C8 C1 120.86(14)
C13 C8 C1 120.65(14)
C13 C8 C9 118.49(15)
H9 C9 C8 119.60(9)
C10 C9 C8 120.79(15)
C10 C9 H9 119.60(10)
H10 C10 C9 120.40(10)
C11 C10 C9 119.20(15)
C11 C10 H10 120.40(9)
C10 C11 Br1 118.85(12)
C12 C11 Br1 119.66(12)
C12 C11 C10 121.48(15)
H12 C12 C11 120.59(10)
C13 C12 C11 118.83(15)
C13 C12 H12 120.59(9)
C12 C13 C8 121.21(15)
H13 C13 C8 119.40(9)
H13 C13 C12 119.40(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.9022(16)
F1 C7 1.3544(18)
N1 N2 1.3564(19)
N1 C1 1.363(2)
N2 C2 1.375(2)
N2 C6 1.389(2)
C1 C7 1.396(2)
C1 C8 1.466(2)
C2 H2 0.9500
C2 C3 1.363(2)
C3 H3 0.9500
C3 C4 1.430(2)
C4 H4 0.9500
C4 C5 1.366(2)
C5 H5 0.9500
C5 C6 1.416(2)
C6 C7 1.383(2)
C8 C9 1.405(2)
C8 C13 1.402(2)
C9 H9 0.9500
C9 C10 1.391(2)
C10 H10 0.9500
C10 C11 1.389(2)
C11 C12 1.390(2)
C12 H12 0.9500
C12 C13 1.392(2)
C13 H13 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353253
