#------------------------------------------------------------------------------
#$Date: 2017-09-11 17:09:03 +0300 (Mon, 11 Sep 2017) $
#$Revision: 200456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032789.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_4032789
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            'C6 H9 N3 O2'
_chemical_formula_weight         155.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_space_group_name_H-M   'C 1 m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.9002(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6930(2)
_cell_length_b                   6.6662(2)
_cell_length_c                   7.3655(2)
_cell_measurement_reflns_used    4237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      6.14
_cell_volume                     369.608(18)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0221
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4234
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.480
_diffrn_reflns_theta_min         6.140
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(17)
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         638
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0232
_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)+(0.0381P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0606
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.825
_reflns_number_gt                636
_reflns_number_total             638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           lab5-12
_cod_original_cell_volume        369.607(18)
_cod_database_code               4032789
_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   0.899
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C -0.5505(4) -0.5000 -0.6232(4) 0.0156(6) Uani 1 2 d S T P
C2 C -0.4293(4) -0.5000 -0.7403(4) 0.0166(6) Uani 1 2 d S T P
H2 H -0.4523 -0.5000 -0.8721 0.020 Uiso 1 2 calc R U P
C3 C -0.2681(4) -0.5000 -0.6173(4) 0.0172(6) Uani 1 2 d S T P
H3 H -0.1541 -0.5000 -0.6481 0.021 Uiso 1 2 calc R U P
C4 C -0.1729(4) -0.5000 -0.2646(4) 0.0177(6) Uani 1 2 d S T P
H4 H -0.0505 -0.5000 -0.2910 0.021 Uiso 1 2 calc R U P
C5 C -0.1952(3) -0.3106(3) -0.1573(3) 0.0204(5) Uani 1 1 d . . .
H5A H -0.1079 -0.3100 -0.0397 0.031 Uiso 1 1 calc R U .
H5B H -0.3153 -0.3067 -0.1321 0.031 Uiso 1 1 calc R U .
H5C H -0.1766 -0.1930 -0.2307 0.031 Uiso 1 1 calc R U .
N1 N -0.4766(3) -0.5000 -0.4441(3) 0.0161(6) Uani 1 2 d S T P
N2 N -0.3024(3) -0.5000 -0.4441(3) 0.0151(5) Uani 1 2 d S T P
N3 N -0.7417(3) -0.5000 -0.6787(3) 0.0165(6) Uani 1 2 d S T P
O1 O -0.8062(3) -0.5000 -0.8458(3) 0.0233(5) Uani 1 2 d S T P
O2 O -0.8300(3) -0.5000 -0.5571(3) 0.0230(6) Uani 1 2 d S T P
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 114.3(3) . .
N1 C1 N3 119.0(2) . .
C2 C1 N3 126.7(2) . .
C3 C2 C1 102.7(3) . .
C3 C2 H2 128.7 . .
C1 C2 H2 128.7 . .
N2 C3 C2 107.2(3) . .
N2 C3 H3 126.4 . .
C2 C3 H3 126.4 . .
N2 C4 C5 109.71(15) . .
N2 C4 C5 109.71(15) . 2_545
C5 C4 C5 112.5(2) . 2_545
N2 C4 H4 108.3 . .
C5 C4 H4 108.3 . .
C5 C4 H4 108.3 2_545 .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C1 N1 N2 102.9(2) . .
N1 N2 C3 112.9(2) . .
N1 N2 C4 119.2(2) . .
C3 N2 C4 127.9(2) . .
O1 N3 O2 124.0(2) . .
O1 N3 C1 117.5(2) . .
O2 N3 C1 118.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.325(4) .
C1 C2 1.394(4) .
C1 N3 1.443(3) .
C2 C3 1.377(4) .
C2 H2 0.9500 .
C3 N2 1.355(4) .
C3 H3 0.9500 .
C4 N2 1.482(3) .
C4 C5 1.518(2) .
C4 C5 1.518(2) 2_545
C4 H4 1.0000 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
N1 N2 1.340(3) .
N3 O1 1.229(3) .
N3 O2 1.231(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
_geom_torsion_site_symmetry_1
N1 C1 C2 C3 0.000(1) .
N3 C1 C2 C3 180.000(1) .
C1 C2 C3 N2 0.000(1) .
C2 C1 N1 N2 0.000(1) .
N3 C1 N1 N2 180.000(1) .
C1 N1 N2 C3 0.000(1) .
C1 N1 N2 C4 180.000(0) .
C2 C3 N2 N1 0.000(1) .
C2 C3 N2 C4 180.000(1) .
C5 C4 N2 N1 -62.06(16) .
C5 C4 N2 N1 62.06(16) 2_545
C5 C4 N2 C3 117.94(16) .
C5 C4 N2 C3 -117.94(16) 2_545
N1 C1 N3 O1 180.000(1) .
C2 C1 N3 O1 0.000(1) .
N1 C1 N3 O2 0.000(1) .
C2 C1 N3 O2 180.000(1) .
