Substituent-oriented C-N bond formation via N-H insertion or Wolff rearrangement of 5-aryl-1H-pyrazoles and diazo compounds
Shang, Yongjia; Zuo, Youpeng; He, Xinwei; Ning, Yi; Tang, Qiang; Xie, Mengqing; Hu, Wangcheng; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB01868A

data_7157174
_publ_section_title
;
 Substituent-oriented C-N bond formation via N-H insertion or Wolff
 rearrangement of 5-aryl-1H-pyrazoles and diazo compounds
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB01868A
_journal_year                    2019
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0547(13)
_cell_length_b                   19.198(3)
_cell_length_c                   8.7595(13)
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      3.15
_cell_volume                     1690.8(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10996
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.646
_diffrn_reflns_theta_min         3.774
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0507P)^2^+0.2444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.708
_reflns_Friedel_fraction_max     0.681
_reflns_number_gt                2997
_reflns_number_total             3330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01868a2.cif
_cod_data_source_block           Op
_cod_database_code               7157174
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              21245