#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:26:59 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223512 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/29/7232997.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_7232997
loop_
_publ_author_name
'Tang, Jie'
'Cheng, Guangbin'
'Zhao, Ying'
'Yang, Pengju'
'Ju, Xuehai'
'Yang, Hongwei'
_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         'C9 H6 N8 O4'
_chemical_formula_sum            'C9 H6 N8 O4'
_chemical_formula_weight         290.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-19 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.149(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5895(8)
_cell_length_b                   9.8629(10)
_cell_length_c                   14.7226(17)
_cell_measurement_reflns_used    1007
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      3.40
_cell_volume                     1097.6(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5162
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.409
_diffrn_reflns_theta_min         3.396
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0599
_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)+(0.0365P)²+0.5939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1128
_reflns_number_total             1989
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00782b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7232997--7233000.cif.'
_cod_database_code               7232997
_shelx_shelxl_version_number     2014/7
_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   0.975
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.3184(5) -0.0917(3) -0.0745(3) 0.0313(9) Uani 1 1 d . .
H1 H 0.3600 -0.1498 -0.1194 0.038 Uiso 1 1 calc R U
C2 C 0.3154(4) 0.0526(3) -0.0802(3) 0.0244(8) Uani 1 1 d . .
C3 C 0.2455(4) 0.0966(3) -0.0005(2) 0.0244(9) Uani 1 1 d . .
C4 C 0.2225(4) 0.2322(3) 0.0215(2) 0.0288(9) Uani 1 1 d . .
H4 H 0.1747 0.2597 0.0760 0.035 Uiso 1 1 calc R U
C5 C 0.2741(5) 0.3230(3) -0.0413(3) 0.0302(9) Uani 1 1 d . .
C6 C 0.3389(5) 0.2882(3) -0.1238(3) 0.0301(9) Uani 1 1 d . .
H6 H 0.3691 0.3560 -0.1656 0.036 Uiso 1 1 calc R U
C7 C 0.3579(4) 0.1534(3) -0.1427(2) 0.0252(8) Uani 1 1 d . .
C8 C 0.1372(4) -0.0289(3) 0.1307(2) 0.0265(9) Uani 1 1 d . .
C9 C 0.0519(5) -0.1065(3) 0.2549(3) 0.0338(10) Uani 1 1 d . .
H9 H 0.0292 -0.1657 0.3034 0.041 Uiso 1 1 calc R U
N1 N 0.2112(4) -0.0192(3) 0.0475(2) 0.0267(7) Uani 1 1 d . .
N2 N 0.2557(4) -0.1340(3) 0.0014(2) 0.0310(8) Uani 1 1 d . .
N3 N 0.0105(4) 0.0222(3) 0.2510(2) 0.0369(8) Uani 1 1 d . .
N4 N 0.0650(4) 0.0733(3) 0.1700(2) 0.0323(8) Uani 1 1 d . .
N5 N 0.1320(4) -0.1438(3) 0.1798(2) 0.0294(8) Uani 1 1 d . .
N6 N 0.2183(4) -0.2694(3) 0.1684(2) 0.0382(9) Uani 1 1 d D .
H6A H 0.215(5) -0.284(4) 0.1068(19) 0.046 Uiso 1 1 d D U
H6B H 0.145(4) -0.334(3) 0.188(3) 0.046 Uiso 1 1 d D U
N7 N 0.2611(4) 0.4678(3) -0.0185(2) 0.0406(9) Uani 1 1 d . .
N8 N 0.4285(4) 0.1146(3) -0.2279(2) 0.0321(8) Uani 1 1 d . .
O2 O 0.1855(4) 0.4977(3) 0.0481(2) 0.0671(11) Uani 1 1 d . .
O3 O 0.3271(4) 0.5501(2) -0.0675(2) 0.0557(9) Uani 1 1 d . .
O4 O 0.4167(4) 0.1956(3) -0.2907(2) 0.0471(8) Uani 1 1 d . .
O5 O 0.4959(4) 0.0015(2) -0.23020(18) 0.0433(8) 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
N2 C1 C2 111.1(3)
N2 C1 H1 124.5
C2 C1 H1 124.5
C3 C2 C7 117.0(3)
C3 C2 C1 105.4(3)
C7 C2 C1 137.6(3)
N1 C3 C4 130.0(3)
N1 C3 C2 106.0(3)
C4 C3 C2 124.0(3)
C5 C4 C3 115.0(3)
C5 C4 H4 122.5
C3 C4 H4 122.5
C4 C5 C6 124.9(3)
C4 C5 N7 116.9(3)
C6 C5 N7 118.3(3)
C7 C6 C5 118.0(3)
C7 C6 H6 121.0
C5 C6 H6 121.0
C6 C7 C2 121.2(3)
C6 C7 N8 118.9(3)
C2 C7 N8 119.9(3)
N4 C8 N5 112.2(3)
N4 C8 N1 123.6(3)
N5 C8 N1 124.2(3)
N3 C9 N5 110.5(3)
N3 C9 H9 124.7
N5 C9 H9 124.7
N2 N1 C3 111.2(3)
N2 N1 C8 120.8(3)
C3 N1 C8 127.9(3)
C1 N2 N1 106.3(3)
C9 N3 N4 107.5(3)
C8 N4 N3 105.6(3)
C8 N5 C9 104.2(3)
C8 N5 N6 129.5(3)
C9 N5 N6 125.3(3)
N5 N6 H6A 107(2)
N5 N6 H6B 106(2)
H6A N6 H6B 103(3)
O2 N7 O3 124.3(3)
O2 N7 C5 117.7(3)
O3 N7 C5 118.0(3)
O4 N8 O5 125.2(3)
O4 N8 C7 118.2(3)
O5 N8 C7 116.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.321(4)
C1 C2 1.425(4)
C1 H1 0.9500
C2 C3 1.400(5)
C2 C7 1.412(5)
C3 N1 1.380(4)
C3 C4 1.391(4)
C4 C5 1.369(5)
C4 H4 0.9500
C5 C6 1.394(5)
C5 N7 1.472(4)
C6 C7 1.368(4)
C6 H6 0.9500
C7 N8 1.459(4)
C8 N4 1.307(4)
C8 N5 1.347(4)
C8 N1 1.397(4)
C9 N3 1.309(4)
C9 N5 1.359(4)
C9 H9 0.9500
N1 N2 1.377(4)
N3 N4 1.391(4)
N5 N6 1.418(4)
N6 H6A 0.92(3)
N6 H6B 0.91(3)
N7 O2 1.215(4)
N7 O3 1.223(4)
N8 O4 1.219(4)
N8 O5 1.229(3)
