#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032790.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_4032790
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            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.0134(6)
_cell_length_b                   9.5835(5)
_cell_length_c                   19.5390(10)
_cell_measurement_reflns_used    6235
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.78
_cell_volume                     2062.28(19)
_computing_cell_refinement       'SAINT 8.30C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.30C (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13722
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0346
_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)+(0.0415P)²+0.7680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                1884
_reflns_number_total             2273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           LB-8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4032790
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'
'-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 0.40366(11) 0.21477(12) 0.48404(6) 0.0151(3) Uani 1 1 d .
C2 C 0.51926(12) 0.27175(13) 0.47983(7) 0.0189(3) Uani 1 1 d .
H2 H 0.5907 0.2453 0.5038 0.023 Uiso 1 1 calc R
C3 C 0.50438(11) 0.37584(13) 0.43234(7) 0.0186(3) Uani 1 1 d .
H3 H 0.5656 0.4376 0.4164 0.022 Uiso 1 1 calc R
C4 C 0.32942(11) 0.47417(12) 0.36538(6) 0.0173(3) Uani 1 1 d .
H4A H 0.3900 0.5047 0.3311 0.021 Uiso 1 1 calc R
H4B H 0.3034 0.5575 0.3915 0.021 Uiso 1 1 calc R
C5 C 0.22027(11) 0.41268(13) 0.32860(7) 0.0184(3) Uani 1 1 d .
H5A H 0.2452 0.3287 0.3027 0.022 Uiso 1 1 calc R
H5B H 0.1580 0.3845 0.3624 0.022 Uiso 1 1 calc R
C6 C 0.16762(11) 0.51983(12) 0.28011(6) 0.0155(3) Uani 1 1 d .
C7 C 0.06842(11) 0.60099(13) 0.29909(6) 0.0165(3) Uani 1 1 d .
H7 H 0.0314 0.5869 0.3424 0.020 Uiso 1 1 calc R
C8 C 0.02307(11) 0.70243(12) 0.25522(7) 0.0187(3) Uani 1 1 d .
H8 H -0.0448 0.7571 0.2687 0.022 Uiso 1 1 calc R
C9 C 0.07652(12) 0.72410(13) 0.19187(6) 0.0195(3) Uani 1 1 d .
H9 H 0.0454 0.7934 0.1619 0.023 Uiso 1 1 calc R
C10 C 0.17558(12) 0.64423(13) 0.17243(6) 0.0204(3) Uani 1 1 d .
H10 H 0.2127 0.6592 0.1291 0.025 Uiso 1 1 calc R
C11 C 0.22070(12) 0.54249(13) 0.21609(6) 0.0184(3) Uani 1 1 d .
H11 H 0.2883 0.4877 0.2023 0.022 Uiso 1 1 calc R
N1 N 0.32149(9) 0.27557(10) 0.44387(5) 0.0154(2) Uani 1 1 d .
N2 N 0.38664(9) 0.37446(10) 0.41241(5) 0.0151(2) Uani 1 1 d .
N3 N 0.36706(9) 0.09842(10) 0.52597(5) 0.0159(2) Uani 1 1 d .
O1 O 0.44392(8) 0.05067(9) 0.56536(4) 0.0214(2) Uani 1 1 d .
O2 O 0.26348(8) 0.05278(10) 0.52096(5) 0.0253(2) 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'
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 114.59(11)
N1 C1 N3 118.91(11)
C2 C1 N3 126.49(11)
C3 C2 C1 102.51(11)
C3 C2 H2 128.7
C1 C2 H2 128.7
N2 C3 C2 107.56(11)
N2 C3 H3 126.2
C2 C3 H3 126.2
N2 C4 C5 112.54(10)
N2 C4 H4A 109.1
C5 C4 H4A 109.1
N2 C4 H4B 109.1
C5 C4 H4B 109.1
H4A C4 H4B 107.8
C6 C5 C4 109.64(10)
C6 C5 H5A 109.7
C4 C5 H5A 109.7
C6 C5 H5B 109.7
C4 C5 H5B 109.7
H5A C5 H5B 108.2
C7 C6 C11 118.69(11)
C7 C6 C5 120.90(11)
C11 C6 C5 120.38(11)
C8 C7 C6 120.61(11)
C8 C7 H7 119.7
C6 C7 H7 119.7
C9 C8 C7 120.21(12)
C9 C8 H8 119.9
C7 C8 H8 119.9
C10 C9 C8 119.75(11)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.11(12)
C9 C10 H10 119.9
C11 C10 H10 119.9
C10 C11 C6 120.64(12)
C10 C11 H11 119.7
C6 C11 H11 119.7
C1 N1 N2 102.48(10)
N1 N2 C3 112.85(10)
N1 N2 C4 121.22(10)
C3 N2 C4 125.79(10)
O2 N3 O1 123.83(10)
O2 N3 C1 119.41(10)
O1 N3 C1 116.76(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3321(15)
C1 C2 1.3877(18)
C1 N3 1.4412(15)
C2 C3 1.3721(17)
C2 H2 0.9500
C3 N2 1.3540(16)
C3 H3 0.9500
C4 N2 1.4679(15)
C4 C5 1.5195(17)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5127(16)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.3915(17)
C6 C11 1.3976(17)
C7 C8 1.3888(17)
C7 H7 0.9500
C8 C9 1.3863(18)
C8 H8 0.9500
C9 C10 1.3857(19)
C9 H9 0.9500
C10 C11 1.3876(18)
C10 H10 0.9500
C11 H11 0.9500
N1 N2 1.3382(14)
N3 O2 1.2257(14)
N3 O1 1.2322(13)
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 -0.34(15)
N3 C1 C2 C3 178.75(11)
C1 C2 C3 N2 0.13(13)
N2 C4 C5 C6 -178.86(10)
C4 C5 C6 C7 -97.52(13)
C4 C5 C6 C11 80.23(14)
C11 C6 C7 C8 0.03(18)
C5 C6 C7 C8 177.82(11)
C6 C7 C8 C9 -0.10(18)
C7 C8 C9 C10 -0.07(19)
C8 C9 C10 C11 0.32(19)
C9 C10 C11 C6 -0.39(19)
C7 C6 C11 C10 0.21(18)
C5 C6 C11 C10 -177.59(11)
C2 C1 N1 N2 0.40(14)
N3 C1 N1 N2 -178.77(10)
C1 N1 N2 C3 -0.30(13)
C1 N1 N2 C4 -176.32(10)
C2 C3 N2 N1 0.11(14)
C2 C3 N2 C4 175.91(11)
C5 C4 N2 N1 -30.53(15)
C5 C4 N2 C3 153.99(12)
N1 C1 N3 O2 4.17(16)
C2 C1 N3 O2 -174.88(12)
N1 C1 N3 O1 -175.76(10)
C2 C1 N3 O1 5.18(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 58709923
