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#$Date: 2017-09-11 17:09:03 +0300 (Mon, 11 Sep 2017) $
#$Revision: 200456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/28/4032807.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_4032807
loop_
_publ_author_name
'Huang, Adrian'
'Wo, Kellie'
'Lee, So Yeun Christine'
'Kneitschel, Nika'
'Chang, Jennifer'
'Zhu, Kathleen'
'Mello, Tatsiana'
'Bancroft, Laura'
'Norman, Natalie J.'
'Zheng, Shao-Liang'
_publ_section_title
;
 Regioselective Synthesis, NMR, and Crystallographic Analysis of
 N1-Substituted Pyrazoles.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8864
_journal_page_last               8872
_journal_paper_doi               10.1021/acs.joc.7b01006
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C9 H6 Br N3 O2'
_chemical_formula_weight         268.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.8833(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9252(10)
_cell_length_b                   11.1719(9)
_cell_length_c                   14.2655(12)
_cell_measurement_reflns_used    4902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.51
_cell_volume                     1866.4(3)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX3 v2015.5-2 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.106
_diffrn_reflns_theta_min         2.520
_exptl_absorpt_coefficient_mu    4.385
_exptl_absorpt_correction_T_max  0.4912
_exptl_absorpt_correction_T_min  0.2852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0210
_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)+(0.0351P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1847
_reflns_number_total             2067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           C3-13
_cod_database_code               4032807
_shelx_shelxl_version_number     2014/7
_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_min   0.579
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.39297(14) 0.22433(15) 0.31905(10) 0.0180(4) Uani 1 1 d . .
H1 H 0.4434 0.1608 0.3428 0.022 Uiso 1 1 calc R U
C2 C 0.28890(15) 0.21337(15) 0.26071(11) 0.0180(4) Uani 1 1 d . .
H2 H 0.2512 0.1423 0.2353 0.022 Uiso 1 1 calc R U
C3 C 0.25063(14) 0.33250(15) 0.24701(10) 0.0158(3) Uani 1 1 d . .
C4 C 0.51067(15) 0.39715(14) 0.39137(11) 0.0143(3) Uani 1 1 d . .
C5 C 0.53562(15) 0.51661(14) 0.37693(11) 0.0158(3) Uani 1 1 d . .
H5 H 0.4838 0.5642 0.3336 0.019 Uiso 1 1 calc R U
C6 C 0.63629(15) 0.56598(15) 0.42602(11) 0.0169(4) Uani 1 1 d . .
H6 H 0.6550 0.6471 0.4162 0.020 Uiso 1 1 calc R U
C7 C 0.70923(14) 0.49451(14) 0.48985(11) 0.0160(4) Uani 1 1 d . .
C8 C 0.68248(16) 0.37742(14) 0.50756(12) 0.0166(4) Uani 1 1 d . .
H8 H 0.7329 0.3312 0.5531 0.020 Uiso 1 1 calc R U
C9 C 0.58274(15) 0.32809(15) 0.45906(11) 0.0168(3) Uani 1 1 d . .
H9 H 0.5630 0.2480 0.4714 0.020 Uiso 1 1 calc R U
N1 N 0.41140(13) 0.34320(13) 0.33702(9) 0.0130(3) Uani 1 1 d . .
N2 N 0.32285(13) 0.41257(13) 0.29190(9) 0.0154(3) Uani 1 1 d . .
N3 N 0.82002(13) 0.54196(13) 0.53744(9) 0.0190(3) Uani 1 1 d . .
O1 O 0.88659(11) 0.47376(11) 0.58812(9) 0.0268(3) Uani 1 1 d . .
O2 O 0.84190(12) 0.64746(13) 0.52363(10) 0.0289(3) Uani 1 1 d . .
Br1 Br 0.11097(2) 0.38328(2) 0.17415(2) 0.01827(8) 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
N1 C1 C2 107.36(15)
N1 C1 H1 126.3
C2 C1 H1 126.3
C1 C2 C3 103.51(15)
C1 C2 H2 128.2
C3 C2 H2 128.2
N2 C3 C2 114.09(15)
N2 C3 Br1 119.55(13)
C2 C3 Br1 126.36(13)
C5 C4 C9 120.74(16)
C5 C4 N1 120.37(15)
C9 C4 N1 118.90(14)
C6 C5 C4 119.76(15)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C7 118.61(15)
C5 C6 H6 120.7
C7 C6 H6 120.7
C8 C7 C6 121.83(16)
C8 C7 N3 118.48(15)
C6 C7 N3 119.64(14)
C9 C8 C7 119.73(16)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C4 119.19(15)
C8 C9 H9 120.4
C4 C9 H9 120.4
C1 N1 N2 112.38(14)
C1 N1 C4 127.17(15)
N2 N1 C4 120.38(14)
C3 N2 N1 102.66(14)
O2 N3 O1 123.62(15)
O2 N3 C7 118.16(14)
O1 N3 C7 118.22(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.362(2)
C1 C2 1.363(2)
C1 H1 0.9500
C2 C3 1.409(2)
C2 H2 0.9500
C3 N2 1.321(2)
C3 Br1 1.8767(17)
C4 C5 1.391(2)
C4 C9 1.397(2)
C4 N1 1.421(2)
C5 C6 1.385(2)
C5 H5 0.9500
C6 C7 1.387(2)
C6 H6 0.9500
C7 C8 1.381(2)
C7 N3 1.466(2)
C8 C9 1.373(2)
C8 H8 0.9500
C9 H9 0.9500
N1 N2 1.369(2)
N3 O2 1.231(2)
N3 O1 1.2316(18)
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
N1 C1 C2 C3 0.16(17)
C1 C2 C3 N2 0.09(18)
C1 C2 C3 Br1 -179.37(11)
C9 C4 C5 C6 3.8(2)
N1 C4 C5 C6 -175.92(14)
C4 C5 C6 C7 -0.9(2)
C5 C6 C7 C8 -2.0(2)
C5 C6 C7 N3 175.57(14)
C6 C7 C8 C9 2.0(2)
N3 C7 C8 C9 -175.58(14)
C7 C8 C9 C4 0.9(2)
C5 C4 C9 C8 -3.8(2)
N1 C4 C9 C8 175.94(14)
C2 C1 N1 N2 -0.36(18)
C2 C1 N1 C4 -177.31(14)
C5 C4 N1 C1 157.07(15)
C9 C4 N1 C1 -22.7(2)
C5 C4 N1 N2 -19.7(2)
C9 C4 N1 N2 160.60(14)
C2 C3 N2 N1 -0.29(17)
Br1 C3 N2 N1 179.20(10)
C1 N1 N2 C3 0.40(16)
C4 N1 N2 C3 177.58(13)
C8 C7 N3 O2 -177.82(15)
C6 C7 N3 O2 4.6(2)
C8 C7 N3 O1 3.0(2)
C6 C7 N3 O1 -174.59(15)
