#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:42:16 +0100 (vie 06 de nov de 2020) $
#$Revision: 258892 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/99/7059935.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_7059935
loop_
_publ_author_name
'Tang, Jie'
'Chen, Jieyi'
'Yang, Pengju'
'Yang, Hongwei'
'Cheng, Guangbin'
_publ_section_title
;
 An efficient strategy for the preparation of insensitive energetic
 materials: intramolecular cyclization of picrylhydrazone into an indazole
 derivative
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15849
_journal_page_last               15856
_journal_paper_doi               10.1039/D0NJ03476B
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         '2(C3 H7 N O), C16 H8 N14 O12'
_chemical_formula_sum            'C22 H22 N16 O14'
_chemical_formula_weight         734.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-14 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                81.816(2)
_cell_angle_beta                 80.771(2)
_cell_angle_gamma                80.036(2)
_cell_formula_units_Z            1
_cell_length_a                   7.8751(4)
_cell_length_b                   8.0958(3)
_cell_length_c                   12.3520(5)
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.322
_cell_measurement_theta_min      2.572
_cell_volume                     760.25(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8624
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_min         2.572
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0661 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.9163. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             378
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0404
_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)+(0.0337P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2335
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj03476b2.cif
_cod_data_source_block           mo_22020288_0m
_cod_depositor_comments
'Adding full bibliography for 7059934--7059936.cif.'
_cod_database_code               7059935
_shelx_shelxl_version_number     2018/3
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-N3 \\sim O8-N3
 with sigma of 0.02
3. Others
 Fixed Sof: O8(0.75) O6(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C1(H1), C10(H10), C7(H7), C5(H5A)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.49748(16) 0.14734(15) 0.82901(12) 0.0388(3) Uani 1 1 d . . . . .
O4 O 0.10479(17) 0.88495(18) 0.20758(12) 0.0436(4) Uani 1 1 d . . . . .
O1 O 0.34779(18) 0.75608(16) 0.63570(12) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.07412(19) 0.84929(18) 0.62526(12) 0.0508(4) Uani 1 1 d . . . . .
O3 O 0.20425(19) 0.65231(18) 0.13496(11) 0.0452(4) Uani 1 1 d . . . . .
N6 N 0.11546(19) 0.35511(18) 1.01139(12) 0.0299(3) Uani 1 1 d . . . . .
O5 O 0.3115(2) 0.13812(17) 0.36674(13) 0.0496(4) Uani 1 1 d . . . . .
N4 N 0.18264(19) 0.46235(17) 0.72317(12) 0.0284(3) Uani 1 1 d . . . . .
N7 N 0.01148(19) 0.40333(18) 1.10024(12) 0.0307(4) Uani 1 1 d . . . . .
N5 N 0.21044(19) 0.39393(18) 0.82653(12) 0.0309(4) Uani 1 1 d . . . . .
H5 H 0.298497 0.312849 0.836673 0.037 Uiso 1 1 calc R . . . .
N8 N 0.42013(18) -0.11346(17) 0.87946(12) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.2121(2) 0.76105(18) 0.59840(13) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.16636(19) 0.7353(2) 0.21365(13) 0.0348(4) Uani 1 1 d . . . . .
N3 N 0.2836(2) 0.2068(2) 0.44955(15) 0.0442(4) Uani 1 1 d D . . . .
C8 C 0.1000(2) 0.4522(2) 0.91535(14) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.2156(2) 0.6555(2) 0.50975(15) 0.0277(4) Uani 1 1 d . . . . .
O8 O 0.2494(4) 0.1323(4) 0.5418(3) 0.0580(8) Uani 0.75 1 d D . P A 1
C1 C 0.1847(2) 0.7413(2) 0.40926(15) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.156502 0.860957 0.399540 0.035 Uiso 1 1 calc R . . . .
C4 C 0.2578(2) 0.3931(2) 0.43898(16) 0.0316(4) Uani 1 1 d . . . . .
C10 C 0.5334(2) -0.0074(2) 0.85375(16) 0.0324(4) Uani 1 1 d . . . . .
H10 H 0.652872 -0.053125 0.854187 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2535(2) 0.4783(2) 0.53116(15) 0.0290(4) Uani 1 1 d . . . . .
C6 C 0.1962(2) 0.6475(2) 0.32251(15) 0.0294(4) Uani 1 1 d . . . . .
C7 C 0.2823(2) 0.3976(2) 0.64236(15) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.369949 0.302780 0.653734 0.037 Uiso 1 1 calc R . . . .
C5 C 0.2307(2) 0.4740(2) 0.33592(15) 0.0328(4) Uani 1 1 d . . . . .
H5A H 0.235812 0.411558 0.275642 0.039 Uiso 1 1 calc R . . . .
C11 C 0.4762(3) -0.2937(2) 0.90266(17) 0.0394(5) Uani 1 1 d . . . . .
H11A H 0.442005 -0.352543 0.847436 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.421368 -0.334122 0.976366 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.603068 -0.316194 0.899837 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.2351(2) -0.0538(2) 0.8789(2) 0.0442(5) Uani 1 1 d . . . . .
H9A H 0.191182 0.014877 0.939689 0.066 Uiso 1 1 calc GR . . . .
H9B H 0.172703 -0.150719 0.888287 0.066 Uiso 1 1 calc GR . . . .
H9C H 0.216780 0.014748 0.808527 0.066 Uiso 1 1 calc GR . . . .
O6 O 0.3556(13) 0.1291(11) 0.5377(8) 0.067(3) Uani 0.25 1 d D . P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 N6 C8 117.74(14) . . ?
C7 N4 N5 117.40(15) . . ?
N6 N7 C8 116.05(15) . 2_567 ?
N4 N5 H5 120.3 . . ?
N4 N5 C8 119.34(14) . . ?
C8 N5 H5 120.3 . . ?
C10 N8 C11 121.26(15) . . ?
C10 N8 C9 120.60(15) . . ?
C11 N8 C9 118.04(15) . . ?
O1 N2 C2 117.55(14) . . ?
O2 N2 O1 126.03(15) . . ?
O2 N2 C2 116.38(15) . . ?
O4 N1 O3 124.79(17) . . ?
O4 N1 C6 117.88(15) . . ?
O3 N1 C6 117.33(16) . . ?
O5 N3 O8 123.1(2) . . ?
O5 N3 C4 118.67(18) . . ?
O5 N3 O6 118.5(4) . . ?
O8 N3 C4 117.3(2) . . ?
O6 N3 C4 115.1(4) . . ?
N6 C8 N7 126.21(16) . 2_567 ?
N6 C8 N5 114.66(15) . . ?
N7 C8 N5 119.13(16) 2_567 . ?
C1 C2 N2 115.71(15) . . ?
C1 C2 C3 124.46(16) . . ?
C3 C2 N2 119.81(16) . . ?
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.51(16) . . ?
C6 C1 H1 121.2 . . ?
C3 C4 N3 120.74(17) . . ?
C5 C4 N3 115.61(16) . . ?
C5 C4 C3 123.58(16) . . ?
O7 C10 N8 125.52(17) . . ?
O7 C10 H10 117.2 . . ?
N8 C10 H10 117.2 . . ?
C2 C3 C7 120.42(16) . . ?
C4 C3 C2 114.06(17) . . ?
C4 C3 C7 125.52(16) . . ?
C1 C6 N1 118.95(16) . . ?
C5 C6 N1 118.98(16) . . ?
C5 C6 C1 122.05(18) . . ?
N4 C7 C3 116.25(16) . . ?
N4 C7 H7 121.9 . . ?
C3 C7 H7 121.9 . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 C4 118.30(17) . . ?
C6 C5 H5A 120.9 . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N8 C9 H9A 109.5 . . ?
N8 C9 H9B 109.5 . . ?
N8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C10 1.240(2) . ?
O4 N1 1.221(2) . ?
O1 N2 1.2220(19) . ?
O2 N2 1.2184(19) . ?
O3 N1 1.2285(19) . ?
N6 N7 1.323(2) . ?
N6 C8 1.337(2) . ?
O5 N3 1.204(2) . ?
N4 N5 1.353(2) . ?
N4 C7 1.282(2) . ?
N7 C8 1.345(2) 2_567 ?
N5 H5 0.8800 . ?
N5 C8 1.372(2) . ?
N8 C10 1.316(2) . ?
N8 C11 1.451(2) . ?
N8 C9 1.454(2) . ?
N2 C2 1.476(2) . ?
N1 C6 1.463(2) . ?
N3 O8 1.223(3) . ?
N3 C4 1.477(2) . ?
N3 O6 1.335(9) . ?
C2 C1 1.370(2) . ?
C2 C3 1.409(2) . ?
C1 H1 0.9500 . ?
C1 C6 1.382(2) . ?
C4 C3 1.405(2) . ?
C4 C5 1.377(3) . ?
C10 H10 0.9500 . ?
C3 C7 1.469(3) . ?
C6 C5 1.375(3) . ?
C7 H7 0.9500 . ?
C5 H5A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
