Optimizing the molecular structure and packing style of a crystal by intramolecular cyclization from picrylhydrazone to indazole
Tang, Jie; Cheng, Guangbin; Zhao, Ying; Yang, Pengju; Ju, Xuehai; Yang, Hongwei; CrystEngComm 21 (2019) 4701–; doi:10.1039/C9CE00782B

data_7232999
_publ_section_title
;
 Optimizing the molecular structure and packing style of a crystal by
 intramolecular cyclization from picrylhydrazone to indazole
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              4701
_journal_paper_doi               10.1039/C9CE00782B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'Cl, C9 H8 N9 O6'
_chemical_formula_sum            'C9 H8 Cl N9 O6'
_chemical_formula_weight         373.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-28 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                77.691(17)
_cell_angle_beta                 78.764(17)
_cell_angle_gamma                87.961(18)
_cell_formula_units_Z            2
_cell_length_a                   7.773(6)
_cell_length_b                   9.309(8)
_cell_length_c                   10.386(8)
_cell_measurement_reflns_used    1159
_cell_measurement_temperature    153
_cell_measurement_theta_max      25.526
_cell_measurement_theta_min      2.671
_cell_volume                     720.2(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.0
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.971
_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  0.0468
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5635
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.045
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0773 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.8320. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0601
_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^)+(0.1204P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2142
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00782b2.cif
_cod_data_source_block           mo_20181195-tj-sxszc_0m
_cod_depositor_comments
'Adding full bibliography for 7232997--7233000.cif.'
_cod_database_code               7232999
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N5(H5), C3(H3), C7(H7), C1(H1), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'