#------------------------------------------------------------------------------
#$Date: 2019-04-27 01:11:38 +0300 (Sat, 27 Apr 2019) $
#$Revision: 214801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/33/7123340.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_7123340
loop_
_publ_author_name
'wang, qian'
'Shao, Yanli'
'Lu, Ming'
_publ_section_title
;
 Amino-tetrazole functionalized fused triazolo-triazine and
 tetrazolo-triazine energetic materials
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01777A
_journal_year                    2019
_chemical_formula_moiety         'C5 H3 N11 O2, C2 H6 O'
_chemical_formula_sum            'C7 H9 N11 O3'
_chemical_formula_weight         295.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc20f9j9
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-02 deposited with the CCDC.    2019-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.752(5)
_cell_length_b                   6.2922(14)
_cell_length_c                   6.9744(16)
_cell_measurement_reflns_used    758
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.78
_cell_measurement_theta_min      3.01
_cell_volume                     1217.9(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0774
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4659
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1229
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0721
_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)+(0.0655P)²+3.0145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                761
_reflns_number_total             1229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc01777a2.cif
_cod_data_source_block           1_CCDC1
_cod_database_code               7123340
_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   0.973
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
C1 C 0.39997(19) 0.7500 0.4914(9) 0.0296(15) Uani 1 2 d S T P . .
C2 C 0.32618(19) 0.7500 0.4461(8) 0.0195(12) Uani 1 2 d S T P . .
C3 C 0.2540(2) 0.7500 0.6910(8) 0.0231(13) Uani 1 2 d S T P . .
C4 C 0.30051(19) 0.7500 0.7753(8) 0.0239(13) Uani 1 2 d S T P . .
C5 C 0.2118(2) 0.7500 0.8132(8) 0.0225(13) Uani 1 2 d S T P . .
N1 N 0.36791(17) 0.7500 0.3469(7) 0.0266(12) Uani 1 2 d S T P . .
N3 N 0.33619(16) 0.7500 0.6388(6) 0.0228(11) Uani 1 2 d S T P . .
N4 N 0.28125(16) 0.7500 0.3742(6) 0.0245(12) Uani 1 2 d S T P . .
N5 N 0.24619(15) 0.7500 0.5017(6) 0.0202(11) Uani 1 2 d S T P . .
N6 N 0.4515(2) 0.7500 0.4556(9) 0.0499(17) Uani 1 2 d S T P . .
N7 N 0.16598(17) 0.7500 0.7520(7) 0.0259(12) Uani 1 2 d DS T P . .
H7D H 0.1528(19) 0.7500 0.639(6) 0.031 Uiso 1 2 d DS U P . .
N8 N 0.13706(17) 0.7500 0.9068(7) 0.0295(13) Uani 1 2 d S T P . .
N9 N 0.16512(17) 0.7500 1.0565(7) 0.0280(12) Uani 1 2 d S T P . .
N10 N 0.21286(17) 0.7500 1.0042(7) 0.0264(11) Uani 1 2 d S T P . .
N11 N 0.31240(16) 0.7500 0.9588(7) 0.0266(12) Uani 1 2 d DS T P . .
H11D H 0.2870(16) 0.7500 1.032(8) 0.032 Uiso 1 2 d DS U P . .
H11E H 0.3422(13) 0.7500 0.992(9) 0.032 Uiso 1 2 d DS U P . .
N2A N 0.38438(16) 0.7500 0.6727(7) 0.0294(13) Uani 1 2 d S T P . .
O1 O 0.4642(2) 0.6943(11) 0.2943(10) 0.053(2) Uiso 0.5 1 d . . P . .
O2 O 0.4785(2) 0.786(8) 0.5894(9) 0.063(10) Uani 0.5 1 d . . P . .
O3 O 0.12522(17) 0.700(2) 0.4224(8) 0.043(4) Uani 0.5 1 d . . P A -1
H3 H 0.1384 0.7149 0.3133 0.051 Uiso 0.5 1 d R U P A -1
C6 C 0.0738(3) 0.7034(14) 0.3980(12) 0.034(2) Uiso 0.5 1 d . . P A -1
H6A H 0.0611 0.5575 0.4136 0.041 Uiso 0.5 1 calc R U P A -1
H6B H 0.0662 0.7510 0.2661 0.041 Uiso 0.5 1 calc R U P A -1
C7 C 0.0495(4) 0.8462(18) 0.5371(17) 0.068(3) Uiso 0.5 1 d . . P A -1
H7A H 0.0570 0.8001 0.6680 0.102 Uiso 0.5 1 calc R U P A -1
H7B H 0.0146 0.8406 0.5169 0.102 Uiso 0.5 1 calc R U P A -1
H7C H 0.0609 0.9921 0.5184 0.102 Uiso 0.5 1 calc R U P A -1
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
N2A C1 N1 119.7(5) . .
N2A C1 N6 118.8(5) . .
N1 C1 N6 121.5(6) . .
N1 C2 N4 127.2(5) . .
N1 C2 N3 109.2(5) . .
N4 C2 N3 123.6(5) . .
N5 C3 C4 123.8(5) . .
N5 C3 C5 116.7(5) . .
C4 C3 C5 119.5(5) . .
N11 C4 N3 119.4(5) . .
N11 C4 C3 128.9(5) . .
N3 C4 C3 111.6(5) . .
N10 C5 N7 109.8(5) . .
N10 C5 C3 124.8(5) . .
N7 C5 C3 125.4(5) . .
C2 N1 C1 100.6(5) . .
N2A N3 C2 111.7(4) . .
N2A N3 C4 126.1(5) . .
C2 N3 C4 122.2(5) . .
N5 N4 C2 115.7(4) . .
N4 N5 C3 123.1(5) . .
O2 N6 O2 22(5) 7_575 .
O2 N6 O1 125.2(8) 7_575 7_575
O2 N6 O1 118.0(12) . 7_575
O2 N6 O1 118.0(12) 7_575 .
O2 N6 O1 125.2(8) . .
O1 N6 O1 33.1(7) 7_575 .
O2 N6 C1 118.3(6) 7_575 .
O2 N6 C1 118.3(6) . .
O1 N6 C1 116.2(6) 7_575 .
O1 N6 C1 116.2(6) . .
N8 N7 C5 108.1(5) . .
N8 N7 H7D 118(4) . .
C5 N7 H7D 133(4) . .
N9 N8 N7 106.7(4) . .
N8 N9 N10 111.3(4) . .
C5 N10 N9 104.2(5) . .
C4 N11 H11D 112(4) . .
C4 N11 H11E 120(4) . .
H11D N11 H11E 128(6) . .
C1 N2A N3 98.9(4) . .
O1 O1 N6 73.4(3) 7_575 .
O2 O2 N6 79(2) 7_575 .
C6 O3 H3 108.7 . .
O3 C6 C7 112.5(8) . .
O3 C6 H6A 109.1 . .
C7 C6 H6A 109.1 . .
O3 C6 H6B 109.1 . .
C7 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2A 1.336(8) .
C1 N1 1.344(8) .
C1 N6 1.451(7) .
C2 N1 1.349(7) .
C2 N4 1.344(7) .
C2 N3 1.372(7) .
C3 N5 1.338(7) .
C3 C4 1.418(8) .
C3 C5 1.448(8) .
C4 N11 1.322(7) .
C4 N3 1.373(7) .
C5 N10 1.332(7) .
C5 N7 1.342(7) .
N3 N2A 1.358(6) .
N4 N5 1.318(6) .
N6 O2 1.219(13) 7_575
N6 O2 1.219(13) .
N6 O1 1.230(8) 7_575
N6 O1 1.230(8) .
N7 N8 1.345(7) .
N7 H7D 0.87(4) .
N8 N9 1.302(7) .
N9 N10 1.374(7) .
N11 H11D 0.87(3) .
N11 H11E 0.86(3) .
O1 O1 0.701(14) 7_575
O2 O2 0.46(10) 7_575
O3 C6 1.437(8) .
O3 H3 0.8500 .
C6 C7 1.484(13) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
