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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032798.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_4032798
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_absolute_configuration ad
_chemical_formula_sum            'C8 H5 N5 O4'
_chemical_formula_weight         235.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.6126(8)
_cell_length_b                   26.1321(12)
_cell_length_c                   8.1858(4)
_cell_measurement_reflns_used    16740
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      5.83
_cell_volume                     3981.5(3)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.991
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18531
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.631
_diffrn_reflns_theta_min         5.837
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0373
_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)+(0.0765P)²+1.1906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                1580
_reflns_number_total             1639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           Lab27-13
_cod_database_code               4032798
_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   0.806
_shelx_estimated_absorpt_t_max   0.978
_refine_ls_abs_structure_hooft   -0.06(12)
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 0.32131(14) 0.58483(11) 0.6523(4) 0.0266(7) Uani 1 1 d . .
C2 C 0.34657(15) 0.56996(11) 0.8064(4) 0.0297(7) Uani 1 1 d . .
H2 H 0.3598 0.5912 0.8958 0.036 Uiso 1 1 calc R U
C3 C 0.34771(16) 0.51829(11) 0.7979(4) 0.0310(7) Uani 1 1 d . .
H3 H 0.3619 0.4954 0.8822 0.037 Uiso 1 1 calc R U
C4 C 0.31500(14) 0.45500(10) 0.5829(4) 0.0255(6) Uani 1 1 d . .
C5 C 0.33543(14) 0.44101(11) 0.4256(4) 0.0248(6) Uani 1 1 d . .
C6 C 0.30248(15) 0.35841(11) 0.4595(4) 0.0292(6) Uani 1 1 d . .
H6 H 0.2990 0.3245 0.4184 0.035 Uiso 1 1 calc R U
C7 C 0.27990(15) 0.36810(11) 0.6178(4) 0.0291(7) Uani 1 1 d . .
H7 H 0.2610 0.3412 0.6831 0.035 Uiso 1 1 calc R U
C8 C 0.28510(15) 0.41723(11) 0.6801(4) 0.0288(7) Uani 1 1 d . .
H8 H 0.2685 0.4248 0.7872 0.035 Uiso 1 1 calc R U
N1 N 0.30755(12) 0.54633(8) 0.5526(3) 0.0260(6) Uani 1 1 d . .
N2 N 0.32438(13) 0.50516(9) 0.6438(3) 0.0263(6) Uani 1 1 d . .
N3 N 0.32910(12) 0.39512(9) 0.3618(3) 0.0281(6) Uani 1 1 d . .
N4 N 0.30822(13) 0.63657(9) 0.6008(3) 0.0295(6) Uani 1 1 d . .
N5 N 0.36964(12) 0.47901(8) 0.3166(3) 0.0280(6) Uani 1 1 d . .
O1 O 0.28667(13) 0.64464(9) 0.4618(3) 0.0387(6) Uani 1 1 d . .
O2 O 0.32001(12) 0.67043(8) 0.7021(3) 0.0368(6) Uani 1 1 d . .
O3 O 0.33826(12) 0.48997(9) 0.1893(3) 0.0362(6) Uani 1 1 d . .
O4 O 0.42748(10) 0.49584(9) 0.3594(3) 0.0375(6) 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 114.2(3)
N1 C1 N4 120.2(3)
C2 C1 N4 125.6(3)
C3 C2 C1 103.7(3)
C3 C2 H2 128.2
C1 C2 H2 128.2
C2 C3 N2 106.9(3)
C2 C3 H3 126.5
N2 C3 H3 126.5
C8 C4 C5 117.0(3)
C8 C4 N2 120.6(3)
C5 C4 N2 122.4(3)
N3 C5 C4 125.7(3)
N3 C5 N5 114.3(3)
C4 C5 N5 120.0(3)
N3 C6 C7 122.6(3)
N3 C6 H6 118.7
C7 C6 H6 118.7
C8 C7 C6 119.5(3)
C8 C7 H7 120.2
C6 C7 H7 120.2
C4 C8 C7 118.5(3)
C4 C8 H8 120.7
C7 C8 H8 120.7
C1 N1 N2 102.8(2)
N1 N2 C3 112.5(2)
N1 N2 C4 121.1(3)
C3 N2 C4 126.4(3)
C5 N3 C6 116.6(3)
O1 N4 O2 124.0(3)
O1 N4 C1 119.4(3)
O2 N4 C1 116.6(3)
O4 N5 O3 125.6(3)
O4 N5 C5 116.8(3)
O3 N5 C5 117.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.321(4)
C1 C2 1.401(4)
C1 N4 1.437(4)
C2 C3 1.352(4)
C2 H2 0.9500
C3 N2 1.378(4)
C3 H3 0.9500
C4 C8 1.384(4)
C4 C5 1.392(4)
C4 N2 1.413(4)
C5 N3 1.313(4)
C5 N5 1.479(4)
C6 N3 1.344(4)
C6 C7 1.385(5)
C6 H6 0.9500
C7 C8 1.385(4)
C7 H7 0.9500
C8 H8 0.9500
N1 N2 1.347(3)
N4 O1 1.225(4)
N4 O2 1.232(3)
N5 O4 1.214(3)
N5 O3 1.229(3)
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 -0.2(3)
N4 C1 C2 C3 177.9(3)
C1 C2 C3 N2 0.4(3)
C8 C4 C5 N3 -0.3(4)
N2 C4 C5 N3 179.2(3)
C8 C4 C5 N5 -178.2(2)
N2 C4 C5 N5 1.3(4)
N3 C6 C7 C8 -0.5(4)
C5 C4 C8 C7 2.3(4)
N2 C4 C8 C7 -177.2(3)
C6 C7 C8 C4 -1.9(4)
C2 C1 N1 N2 -0.1(3)
N4 C1 N1 N2 -178.4(2)
C1 N1 N2 C3 0.4(3)
C1 N1 N2 C4 178.0(2)
C2 C3 N2 N1 -0.6(3)
C2 C3 N2 C4 -178.0(3)
C8 C4 N2 N1 -136.2(3)
C5 C4 N2 N1 44.3(4)
C8 C4 N2 C3 41.0(4)
C5 C4 N2 C3 -138.5(3)
C4 C5 N3 C6 -2.1(4)
N5 C5 N3 C6 175.9(2)
C7 C6 N3 C5 2.5(4)
N1 C1 N4 O1 -2.6(4)
C2 C1 N4 O1 179.3(3)
N1 C1 N4 O2 177.6(3)
C2 C1 N4 O2 -0.4(4)
N3 C5 N5 O4 -114.6(3)
C4 C5 N5 O4 63.5(3)
N3 C5 N5 O3 63.7(3)
C4 C5 N5 O3 -118.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095367
