#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:56:28 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230664 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/65/7156507.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_7156507
loop_
_publ_author_name
'Sun, Qi'
'Li, Xin'
'Lin, Qiuhan'
'Lu, Ming'
_publ_section_title
;
 Tetracyclic pyrazine-fused furazans as insensitive energetic materials:
 syntheses, structures, and properties.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8034
_journal_page_last               8037
_journal_paper_doi               10.1039/c8ob02155d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C6 H2 N8 O2'
_chemical_formula_sum            'C6 H2 N8 O2'
_chemical_formula_weight         218.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-30 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.280(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7793(6)
_cell_length_b                   11.6585(15)
_cell_length_c                   5.7805(6)
_cell_measurement_reflns_used    636
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      4.59
_cell_volume                     383.23(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2200
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.303
_diffrn_reflns_theta_min         3.986
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0448
_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)+(0.0328P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                470
_reflns_number_total             688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob02155d2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7156506--7156508.cif.'
_cod_database_code               7156507
_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   0.980
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_adp
C1 C 0.8267(5) 0.3833(2) 0.6672(5) 0.0165(6) Uani 1 1 d .
C2 C 1.0701(5) 0.3925(2) 0.6661(5) 0.0162(6) Uani 1 1 d .
C3 C 1.1292(5) 0.5030(2) 0.9949(5) 0.0148(6) Uani 1 1 d .
N1 N 0.7308(4) 0.4357(2) 0.8397(4) 0.0183(6) Uani 1 1 d .
H1 H 0.582(5) 0.435(3) 0.839(5) 0.022 Uiso 1 1 d U
N2 N 0.7221(4) 0.3234(2) 0.4887(4) 0.0237(6) Uani 1 1 d .
N3 N 1.1213(4) 0.3399(2) 0.4822(4) 0.0212(6) Uani 1 1 d .
N4 N 1.2242(4) 0.4515(2) 0.8322(4) 0.0164(6) Uani 1 1 d .
O1 O 0.9066(3) 0.29503(17) 0.3690(3) 0.0238(5) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C1 N1 128.7(2) . .
N2 C1 C2 111.1(2) . .
N1 C1 C2 120.2(2) . .
N3 C2 N4 126.3(2) . .
N3 C2 C1 109.8(2) . .
N4 C2 C1 123.9(2) . .
N4 C3 N1 118.5(2) . 3_767
N4 C3 C3 123.4(3) . 3_767
N1 C3 C3 118.1(3) 3_767 3_767
C3 N1 C1 119.1(2) 3_767 .
C3 N1 H1 119.1(19) 3_767 .
C1 N1 H1 121.7(19) . .
C1 N2 O1 103.3(2) . .
C2 N3 O1 104.2(2) . .
C3 N4 C2 115.3(2) . .
N3 O1 N2 111.63(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.302(3) .
C1 N1 1.369(3) .
C1 C2 1.412(4) .
C2 N3 1.306(3) .
C2 N4 1.372(3) .
C3 N4 1.315(3) .
C3 N1 1.343(4) 3_767
C3 C3 1.507(5) 3_767
N1 C3 1.343(4) 3_767
N1 H1 0.86(3) .
N2 O1 1.410(3) .
N3 O1 1.397(3) .
