Regioselective Synthesis, NMR, and Crystallographic Analysis of N1-Substituted Pyrazoles.
Huang, Adrian; Wo, Kellie; Lee, So Yeun Christine; Kneitschel, Nika; Chang, Jennifer; Zhu, Kathleen; Mello, Tatsiana; Bancroft, Laura; Norman, Natalie J.; Zheng, Shao-Liang; The Journal of organic chemistry 82 (2017) 8864–8872; doi:10.1021/acs.joc.7b01006

data_4032798
_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/[\s^2^(Fo^2^)+(0.0765P)^2^+1.1906P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            jo7b01006_si_001.cif
_cod_data_source_block           Lab27-13
_cod_database_code               4032798
_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
_shelx_res_checksum              21293
_shelx_hkl_checksum              66432