#------------------------------------------------------------------------------
#$Date: 2021-09-09 01:53:06 +0300 (Thu, 09 Sep 2021) $
#$Revision: 269052 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/82/7708241.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_7708241
loop_
_publ_author_name
'Lei, Caijin'
'Yang, Hongwei'
'Zhang, Qinghua'
'Cheng, Guangbin'
_publ_section_title
;
 Synthesis of nitrogen-rich and thermostable energetic materials based on
 hetarenecarboxylic acids
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT02854E
_journal_year                    2021
_chemical_formula_moiety         'C5 H6 N10 O'
_chemical_formula_sum            'C5 H6 N10 O'
_chemical_formula_weight         222.20
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-19 deposited with the CCDC.	2021-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                108.619(5)
_cell_angle_beta                 109.314(5)
_cell_angle_gamma                92.750(5)
_cell_formula_units_Z            2
_cell_length_a                   6.8113(9)
_cell_length_b                   8.2072(10)
_cell_length_c                   8.5119(12)
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.381
_cell_measurement_theta_min      2.659
_cell_volume                     419.23(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4856
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.421
_diffrn_reflns_theta_min         2.658
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0670 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.9101. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0461
_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)+(0.0474P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1207
_reflns_number_total             1710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt02854e2.cif
_cod_data_source_block           mo_2021278_0m
_cod_database_code               7708241
_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 N(H,H) groups
2.a Rotating group:
 N9(H9A,H9B), N10(H10A,H10B)
;
_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
O1 O 0.4003(3) 0.0561(2) 0.8228(2) 0.0315(4) Uani 1 1 d . . . . .
N6 N 0.2390(3) 0.2496(2) 0.3927(2) 0.0214(4) Uani 1 1 d . . . . .
N4 N 0.5932(3) 0.2858(2) 0.4659(2) 0.0211(4) Uani 1 1 d . . . . .
N5 N 0.4922(3) 0.3354(2) 0.3221(2) 0.0197(4) Uani 1 1 d . . . . .
N8 N 0.3547(3) 0.4257(2) 0.1016(2) 0.0246(5) Uani 1 1 d . . . . .
N9 N 0.7360(3) 0.4581(2) 0.2198(2) 0.0250(5) Uani 1 1 d . . . . .
H9A H 0.811005 0.374996 0.230827 0.030 Uiso 1 1 d GR . . . .
H9B H 0.730001 0.477491 0.122337 0.030 Uiso 1 1 d GR . . . .
N7 N 0.1848(3) 0.3680(2) 0.1454(2) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.8593(3) 0.2043(3) 0.7786(3) 0.0312(5) Uani 1 1 d . . . . .
N3 N 0.3084(3) 0.1053(2) 0.6804(3) 0.0273(5) Uani 1 1 d . . . . .
N10 N 0.0360(3) 0.2199(3) 0.3943(3) 0.0328(5) Uani 1 1 d . . . . .
H10A H -0.001770 0.107560 0.369641 0.039 Uiso 1 1 d GR . . . .
H10B H 0.036004 0.279144 0.500915 0.039 Uiso 1 1 d GR . . . .
N1 N 0.6214(3) 0.0893(3) 0.8792(3) 0.0297(5) Uani 1 1 d . . . . .
C4 C 0.2805(3) 0.3157(3) 0.2760(3) 0.0208(5) Uani 1 1 d . . . . .
C3 C 0.4335(3) 0.2345(3) 0.5032(3) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.6611(3) 0.1592(3) 0.7722(3) 0.0234(5) Uani 1 1 d . . . . .
C2 C 0.4640(3) 0.1686(3) 0.6476(3) 0.0205(5) Uani 1 1 d . . . . .
C5 C 0.5355(3) 0.4054(3) 0.2079(3) 0.0214(5) Uani 1 1 d . . . . .
H2A H 0.961(4) 0.231(3) 0.886(4) 0.045(8) Uiso 1 1 d . . . . .
H2B H 0.869(4) 0.276(3) 0.721(4) 0.041(8) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 O1 N1 111.03(16) . . ?
C4 N6 N10 122.63(17) . . ?
C4 N6 C3 105.74(17) . . ?
C3 N6 N10 131.49(18) . . ?
C3 N4 N5 101.96(16) . . ?
C4 N5 N4 113.42(17) . . ?
C4 N5 C5 105.56(17) . . ?
C5 N5 N4 140.99(18) . . ?
C5 N8 N7 109.80(17) . . ?
H9A N9 H9B 109.2 . . ?
C5 N9 H9A 109.1 . . ?
C5 N9 H9B 109.5 . . ?
C4 N7 N8 102.99(17) . . ?
C1 N2 H2A 114.4(18) . . ?
C1 N2 H2B 114.5(17) . . ?
H2A N2 H2B 115(2) . . ?
C2 N3 O1 105.79(17) . . ?
N6 N10 H10A 109.2 . . ?
N6 N10 H10B 109.4 . . ?
H10A N10 H10B 109.2 . . ?
C1 N1 O1 105.27(17) . . ?
N5 C4 N6 105.23(17) . . ?
N7 C4 N6 140.8(2) . . ?
N7 C4 N5 113.91(19) . . ?
N6 C3 C2 124.53(19) . . ?
N4 C3 N6 113.65(18) . . ?
N4 C3 C2 121.83(18) . . ?
N2 C1 C2 128.0(2) . . ?
N1 C1 N2 123.6(2) . . ?
N1 C1 C2 108.4(2) . . ?
N3 C2 C3 123.40(19) . . ?
N3 C2 C1 109.54(19) . . ?
C1 C2 C3 127.1(2) . . ?
N5 C5 N9 123.90(19) . . ?
N8 C5 N5 107.75(19) . . ?
N8 C5 N9 128.1(2) . . ?
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
O1 N3 1.364(2) . ?
O1 N1 1.404(2) . ?
N6 N10 1.398(2) . ?
N6 C4 1.370(3) . ?
N6 C3 1.386(3) . ?
N4 N5 1.387(2) . ?
N4 C3 1.316(3) . ?
N5 C4 1.350(3) . ?
N5 C5 1.376(3) . ?
N8 N7 1.430(3) . ?
N8 C5 1.320(3) . ?
N9 H9A 0.8820 . ?
N9 H9B 0.8821 . ?
N9 C5 1.373(3) . ?
N7 C4 1.303(3) . ?
N2 C1 1.362(3) . ?
N2 H2A 0.90(3) . ?
N2 H2B 0.89(3) . ?
N3 C2 1.306(3) . ?
N10 H10A 0.8819 . ?
N10 H10B 0.8820 . ?
N1 C1 1.308(3) . ?
C3 C2 1.453(3) . ?
C1 C2 1.433(3) . ?
