#------------------------------------------------------------------------------
#$Date: 2021-01-28 07:58:45 +0200 (Thu, 28 Jan 2021) $
#$Revision: 261293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/87/2108767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108767
loop_
_publ_author_name
'Liu, Yunzhang'
'Chen, Lizhen'
'Wang, Jianlong'
'Chen, Jun'
'Wang, Jingqi'
'Pan, Hongxia'
_publ_section_title
;
 The crystal structure and thermal decomposition kinetics of
 cis-hexanitrostilbene
;
_journal_coeditor_code           RA5090SUP1
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620015371
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C14 H6 N6 O12'
_chemical_formula_sum            'C14 H6 N6 O12'
_chemical_formula_weight         450.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 129.0870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.2210(6)
_cell_length_b                   10.3080(3)
_cell_length_c                   19.4134(5)
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.317
_cell_measurement_theta_min      2.235
_cell_volume                     3296.17(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17600
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.471
_diffrn_reflns_theta_min         2.234
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0842 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.9408. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+3.4414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2698
_reflns_number_total             3373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ra5090sup1.cif
_cod_data_source_block           cis-HNS
_cod_original_cell_volume        3296.17(16)
_cod_database_code               2108767
_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   0.992
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-N2 \\sim O0AA-N2
 with sigma of 0.02
 O0AA-N2 \\sim O3-N2
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O0AA) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: O3(0.75) O0AA(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C8(H8), C4(H4), C7(H7), C2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.75656(9) 0.74827(14) 0.40818(9) 0.0324(3) Uani 1 1 d . U . . .
O4 O 0.93226(9) 0.79655(13) 0.53960(9) 0.0317(3) Uani 1 1 d . U . . .
O7 O 0.91740(9) 0.33299(16) 0.39913(10) 0.0365(4) Uani 1 1 d . U . . .
O11 O 0.46780(9) 0.41969(15) 0.14686(10) 0.0353(4) Uani 1 1 d . U . . .
O10 O 0.72633(10) 0.53469(14) 0.09454(9) 0.0334(4) Uani 1 1 d . U . . .
O12 O 0.47955(9) 0.37459(15) 0.04638(9) 0.0361(4) Uani 1 1 d . U . . .
O8 O 0.79229(9) 0.29173(14) 0.34001(9) 0.0341(4) Uani 1 1 d . U . . .
O9 O 0.82602(9) 0.45615(16) 0.22315(10) 0.0362(4) Uani 1 1 d . U . . .
O1 O 0.83129(11) 0.21228(16) 0.62521(12) 0.0465(4) Uani 1 1 d . U . . .
O2 O 0.92088(11) 0.33393(18) 0.73719(11) 0.0474(5) Uani 1 1 d . U . . .
O5 O 0.70945(11) 0.58492(17) 0.43374(10) 0.0442(4) Uani 1 1 d . U . . .
N4 N 0.50520(10) 0.42001(15) 0.11851(11) 0.0247(4) Uani 1 1 d . U . . .
N6 N 0.85907(10) 0.33946(15) 0.39724(10) 0.0243(4) Uani 1 1 d . U . . .
N5 N 0.75780(10) 0.50229(15) 0.17035(11) 0.0241(4) Uani 1 1 d . U . . .
N2 N 0.93302(10) 0.72497(16) 0.58937(10) 0.0286(4) Uani 1 1 d D U . . .
N3 N 0.72232(10) 0.64347(16) 0.38901(10) 0.0249(4) Uani 1 1 d . U . . .
N1 N 0.87753(12) 0.30498(18) 0.65845(13) 0.0344(4) Uani 1 1 d . U . . .
C11 C 0.61741(11) 0.52981(17) 0.25466(12) 0.0205(4) Uani 1 1 d . U . . .
H11 H 0.586001 0.532172 0.274032 0.025 Uiso 1 1 calc R . . . .
C12 C 0.58702(11) 0.47618(17) 0.17417(12) 0.0207(4) Uani 1 1 d . U . . .
C13 C 0.63158(11) 0.47012(17) 0.14458(12) 0.0210(4) Uani 1 1 d . U . . .
H13 H 0.609220 0.435334 0.088014 0.025 Uiso 1 1 calc R . . . .
C9 C 0.74601(11) 0.57442(16) 0.28371(11) 0.0180(4) Uani 1 1 d . U . . .
O3 O 0.9443(2) 0.7628(4) 0.6570(2) 0.0451(9) Uani 0.75 1 d D U P A 1
C8 C 0.82967(11) 0.62663(17) 0.33614(11) 0.0198(4) Uani 1 1 d . U . . .
H8 H 0.840302 0.676894 0.303456 0.024 Uiso 1 1 calc R . . . .
C4 C 0.86181(11) 0.32986(19) 0.52342(12) 0.0241(4) Uani 1 1 d . U . . .
H4 H 0.843144 0.242830 0.507686 0.029 Uiso 1 1 calc R . . . .
C1 C 0.91002(11) 0.58709(18) 0.56482(12) 0.0216(4) Uani 1 1 d . U . . .
C7 C 0.89197(11) 0.61363(17) 0.42198(11) 0.0202(4) Uani 1 1 d . U . . .
H7 H 0.940985 0.656821 0.443962 0.024 Uiso 1 1 calc R . . . .
C6 C 0.89143(10) 0.53722(18) 0.48651(11) 0.0198(4) Uani 1 1 d . U . . .
C14 C 0.70953(11) 0.51666(17) 0.20068(11) 0.0193(4) Uani 1 1 d . U . . .
C10 C 0.69528(11) 0.58025(17) 0.30650(11) 0.0193(4) Uani 1 1 d . U . . .
C5 C 0.87004(11) 0.40667(18) 0.47128(12) 0.0212(4) Uani 1 1 d . U . . .
C3 C 0.88205(12) 0.38592(19) 0.59942(13) 0.0259(4) Uani 1 1 d . U . . .
C2 C 0.90706(12) 0.51313(19) 0.62216(12) 0.0255(4) Uani 1 1 d . U . . .
H2 H 0.921819 0.548945 0.675650 0.031 Uiso 1 1 calc R . . . .
O0AA O 0.9790(6) 0.7473(12) 0.6695(6) 0.041(3) Uani 0.25 1 d D U 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
O11 N4 O12 124.49(16) . . ?
O11 N4 C12 118.30(15) . . ?
O12 N4 C12 117.20(15) . . ?
O7 N6 O8 125.36(16) . . ?
O7 N6 C5 117.61(15) . . ?
O8 N6 C5 117.00(15) . . ?
O10 N5 O9 125.16(16) . . ?
O10 N5 C14 117.68(16) . . ?
O9 N5 C14 117.14(15) . . ?
O4 N2 O3 123.5(3) . . ?
O4 N2 C1 119.57(15) . . ?
O4 N2 O0AA 119.9(6) . . ?
O3 N2 C1 116.6(3) . . ?
O0AA N2 C1 115.1(6) . . ?
O6 N3 C10 118.21(15) . . ?
O5 N3 O6 125.23(16) . . ?
O5 N3 C10 116.55(16) . . ?
O1 N1 O2 124.80(18) . . ?
O1 N1 C3 117.25(19) . . ?
O2 N1 C3 117.94(19) . . ?
C12 C11 H11 121.1 . . ?
C12 C11 C10 117.81(16) . . ?
C10 C11 H11 121.1 . . ?
C11 C12 N4 119.00(16) . . ?
C11 C12 C13 122.43(17) . . ?
C13 C12 N4 118.54(16) . . ?
C12 C13 H13 121.5 . . ?
C14 C13 C12 116.90(16) . . ?
C14 C13 H13 121.5 . . ?
C14 C9 C8 119.73(15) . . ?
C10 C9 C8 126.44(15) . . ?
C10 C9 C14 113.78(16) . . ?
C9 C8 H8 115.2 . . ?
C7 C8 C9 129.67(16) . . ?
C7 C8 H8 115.2 . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C3 C4 C5 116.54(18) . . ?
C6 C1 N2 120.67(16) . . ?
C2 C1 N2 116.30(16) . . ?
C2 C1 C6 123.02(17) . . ?
C8 C7 H7 117.3 . . ?
C8 C7 C6 125.48(17) . . ?
C6 C7 H7 117.3 . . ?
C1 C6 C7 124.89(16) . . ?
C5 C6 C1 114.53(16) . . ?
C5 C6 C7 120.57(16) . . ?
C13 C14 N5 116.17(15) . . ?
C13 C14 C9 125.09(16) . . ?
C9 C14 N5 118.73(16) . . ?
C11 C10 N3 115.19(15) . . ?
C11 C10 C9 123.88(16) . . ?
C9 C10 N3 120.93(16) . . ?
C4 C5 N6 115.45(16) . . ?
C4 C5 C6 125.06(17) . . ?
C6 C5 N6 119.41(16) . . ?
C4 C3 N1 117.90(18) . . ?
C4 C3 C2 122.63(17) . . ?
C2 C3 N1 119.46(18) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.05(17) . . ?
C3 C2 H2 121.0 . . ?
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
O6 N3 1.222(2) . ?
O4 N2 1.208(2) . ?
O7 N6 1.217(2) . ?
O11 N4 1.218(2) . ?
O10 N5 1.218(2) . ?
O12 N4 1.231(2) . ?
O8 N6 1.224(2) . ?
O9 N5 1.225(2) . ?
O1 N1 1.222(3) . ?
O2 N1 1.224(2) . ?
O5 N3 1.221(2) . ?
N4 C12 1.467(2) . ?
N6 C5 1.476(2) . ?
N5 C14 1.476(2) . ?
N2 O3 1.240(4) . ?
N2 C1 1.481(2) . ?
N2 O0AA 1.229(9) . ?
N3 C10 1.470(2) . ?
N1 C3 1.469(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(2) . ?
C11 C10 1.384(3) . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(3) . ?
C9 C8 1.483(2) . ?
C9 C14 1.407(2) . ?
C9 C10 1.400(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.328(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C4 C3 1.377(3) . ?
C1 C6 1.405(2) . ?
C1 C2 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.486(2) . ?
C6 C5 1.391(3) . ?
C3 C2 1.379(3) . ?
C2 H2 0.9500 . ?

_cod_database_fobs_code 2108767
