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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/4/03/27/4032787.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_4032787
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            'C12 H8 F3 N3 O3'
_chemical_formula_weight         299.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8424(2)
_cell_length_b                   9.2176(4)
_cell_length_c                   27.5310(11)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.3
_cell_measurement_theta_min      6.88
_cell_volume                     1228.85(9)
_computing_cell_refinement       'SAINT 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23195
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.8184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0348P)²+0.2407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1915
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           LB-13-13
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4032787
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7402(5) 0.4925(2) 0.57460(7) 0.0248(5) Uani 1 1 d .
C2 C 0.5921(5) 0.6199(2) 0.58132(8) 0.0299(5) Uani 1 1 d .
H2 H 0.6134 0.6903 0.6062 0.036 Uiso 1 1 calc R
C3 C 0.4083(5) 0.6200(2) 0.54361(8) 0.0266(5) Uani 1 1 d .
H3 H 0.2749 0.6926 0.5367 0.032 Uiso 1 1 calc R
C4 C 0.3129(5) 0.4502(2) 0.47408(7) 0.0225(5) Uani 1 1 d .
H4A H 0.1190 0.4842 0.4748 0.027 Uiso 1 1 calc R
H4B H 0.3117 0.3430 0.4723 0.027 Uiso 1 1 calc R
C5 C 0.4579(5) 0.5117(2) 0.42953(7) 0.0223(4) Uani 1 1 d .
C6 C 0.3300(5) 0.4805(2) 0.38107(7) 0.0216(5) Uani 1 1 d .
C7 C 0.1183(5) 0.3805(2) 0.37541(8) 0.0233(5) Uani 1 1 d .
H7 H 0.0458 0.3320 0.4030 0.028 Uiso 1 1 calc R
C8 C 0.0113(5) 0.3508(2) 0.32960(8) 0.0231(5) Uani 1 1 d .
H8 H -0.1327 0.2819 0.3255 0.028 Uiso 1 1 calc R
C9 C 0.1203(4) 0.4245(2) 0.28983(8) 0.0224(5) Uani 1 1 d .
C10 C 0.3296(5) 0.5254(2) 0.29523(8) 0.0243(5) Uani 1 1 d .
H10 H 0.3997 0.5750 0.2676 0.029 Uiso 1 1 calc R
C11 C 0.4363(5) 0.5538(2) 0.34060(8) 0.0235(5) Uani 1 1 d .
H11 H 0.5807 0.6227 0.3444 0.028 Uiso 1 1 calc R
C12 C 0.0081(5) 0.3945(2) 0.24010(8) 0.0272(5) Uani 1 1 d .
N1 N 0.4532(4) 0.49619(17) 0.51802(6) 0.0213(4) Uani 1 1 d .
N2 N 0.6604(4) 0.41593(18) 0.53605(6) 0.0218(4) Uani 1 1 d .
N3 N 0.9593(4) 0.4360(2) 0.60455(7) 0.0311(5) Uani 1 1 d .
O1 O 1.0887(4) 0.32902(18) 0.59014(6) 0.0357(4) Uani 1 1 d .
O2 O 1.0059(4) 0.5004(2) 0.64265(6) 0.0506(5) Uani 1 1 d .
O3 O 0.6665(3) 0.58334(15) 0.43359(5) 0.0281(4) Uani 1 1 d .
F1 F -0.2478(3) 0.33997(14) 0.24063(4) 0.0314(3) Uani 1 1 d .
F2 F 0.1640(3) 0.29787(15) 0.21566(5) 0.0388(4) Uani 1 1 d .
F3 F -0.0005(3) 0.51422(14) 0.21251(5) 0.0404(4) 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'
F F 0.0727 0.0534 '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
N2 C1 C2 113.9(2)
N2 C1 N3 118.6(2)
C2 C1 N3 127.58(19)
C3 C2 C1 103.64(19)
N1 C3 C2 106.8(2)
N1 C4 C5 110.31(18)
O3 C5 C6 122.08(19)
O3 C5 C4 120.85(19)
C6 C5 C4 117.07(18)
C7 C6 C11 120.18(19)
C7 C6 C5 122.20(19)
C11 C6 C5 117.60(19)
C6 C7 C8 120.5(2)
C7 C8 C9 118.4(2)
C10 C9 C8 121.38(19)
C10 C9 C12 119.18(19)
C8 C9 C12 119.43(19)
C11 C10 C9 120.04(19)
C10 C11 C6 119.4(2)
F1 C12 F3 106.68(19)
F1 C12 F2 106.02(17)
F3 C12 F2 106.18(17)
F1 C12 C9 113.27(17)
F3 C12 C9 112.17(17)
F2 C12 C9 112.0(2)
N2 N1 C3 113.02(18)
N2 N1 C4 119.85(16)
C3 N1 C4 127.06(18)
C1 N2 N1 102.68(17)
O2 N3 O1 124.6(2)
O2 N3 C1 116.8(2)
O1 N3 C1 118.61(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.332(3)
C1 C2 1.388(3)
C1 N3 1.441(3)
C2 C3 1.367(3)
C3 N1 1.358(3)
C4 N1 1.451(3)
C4 C5 1.523(3)
C5 O3 1.212(3)
C5 C6 1.499(3)
C6 C7 1.387(3)
C6 C11 1.401(3)
C7 C8 1.391(3)
C8 C9 1.392(3)
C9 C10 1.383(3)
C9 C12 1.499(3)
C10 C11 1.377(3)
C12 F1 1.337(3)
C12 F3 1.340(2)
C12 F2 1.348(3)
N1 N2 1.342(2)
N3 O2 1.226(3)
N3 O1 1.234(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
N2 C1 C2 C3 -0.1(3)
N3 C1 C2 C3 -178.9(2)
C1 C2 C3 N1 0.9(2)
N1 C4 C5 O3 2.6(3)
N1 C4 C5 C6 -177.02(17)
O3 C5 C6 C7 169.58(19)
C4 C5 C6 C7 -10.8(3)
O3 C5 C6 C11 -9.0(3)
C4 C5 C6 C11 170.64(19)
C11 C6 C7 C8 0.7(3)
C5 C6 C7 C8 -177.80(19)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C10 -0.2(3)
C7 C8 C9 C12 -179.91(19)
C8 C9 C10 C11 0.6(3)
C12 C9 C10 C11 -179.68(19)
C9 C10 C11 C6 -0.3(3)
C7 C6 C11 C10 -0.3(3)
C5 C6 C11 C10 178.29(19)
C10 C9 C12 F1 -156.88(17)
C8 C9 C12 F1 22.9(3)
C10 C9 C12 F3 -36.0(3)
C8 C9 C12 F3 143.7(2)
C10 C9 C12 F2 83.3(2)
C8 C9 C12 F2 -97.0(2)
C2 C3 N1 N2 -1.4(2)
C2 C3 N1 C4 -178.3(2)
C5 C4 N1 N2 -89.0(2)
C5 C4 N1 C3 87.7(3)
C2 C1 N2 N1 -0.7(2)
N3 C1 N2 N1 178.20(17)
C3 N1 N2 C1 1.3(2)
C4 N1 N2 C1 178.39(18)
N2 C1 N3 O2 -171.8(2)
C2 C1 N3 O2 6.9(3)
N2 C1 N3 O1 9.2(3)
C2 C1 N3 O1 -172.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 50999764
