#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:27:47 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/78/7057874.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_7057874
loop_
_publ_author_name
'Wang, Bohan'
'Xiong, Hualin'
'Cheng, Guangbin'
'Zhang, Zaichao'
'Yang, Hongwei'
_publ_section_title
;
 An unexpected method to synthesise 1,2,4-oxadiazolone derivatives: a
 class of insensitive energetic materials
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19671
_journal_paper_doi               10.1039/C8NJ04428G
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C4 H3 N5 O3, H2 O'
_chemical_formula_sum            'C4 H5 N5 O4'
_chemical_formula_weight         187.13
_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
;
2018-04-04 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.095(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6418(10)
_cell_length_b                   4.9850(5)
_cell_length_c                   17.235(2)
_cell_measurement_reflns_used    1157
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      4.27
_cell_volume                     720.12(14)
_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 0.991
_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  0.0547
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         3.867
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0431
_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)+(0.0366P)²+0.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                922
_reflns_number_total             1293
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj04428g2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7057873--7057875.cif.'
_cod_original_cell_volume        720.13(14)
_cod_database_code               7057874
_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   0.971
_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 0.2085(3) 0.7099(5) 0.90417(13) 0.0146(5) Uani 1 1 d .
C2 C 0.1514(3) 0.9510(5) 0.79436(14) 0.0172(6) Uani 1 1 d .
C3 C 0.3017(3) 0.4923(5) 1.04387(14) 0.0175(5) Uani 1 1 d .
C4 C 0.2008(3) 0.5117(5) 0.96458(13) 0.0154(5) Uani 1 1 d .
N1 N 0.3225(2) 0.8859(4) 0.91588(11) 0.0189(5) Uani 1 1 d .
N2 N 0.1024(2) 0.7389(4) 0.83206(11) 0.0171(5) Uani 1 1 d .
H2A H 0.019(3) 0.637(5) 0.8105(14) 0.021 Uiso 1 1 d U
N3 N 0.2560(2) 0.2841(4) 1.07915(12) 0.0224(5) Uani 1 1 d .
N4 N 0.0953(2) 0.3203(4) 0.95272(12) 0.0206(5) Uani 1 1 d .
N5 N 0.4222(3) 0.6564(5) 1.07829(14) 0.0279(6) Uani 1 1 d .
H5A H 0.487(3) 0.610(6) 1.1271(17) 0.033 Uiso 1 1 d U
H5B H 0.446(3) 0.790(6) 1.0511(17) 0.033 Uiso 1 1 d U
O1 O 0.28749(18) 1.0448(3) 0.84539(9) 0.0198(4) Uani 1 1 d .
O2 O 0.12564(19) 0.1758(3) 1.02236(10) 0.0230(4) Uani 1 1 d .
O3 O 0.0952(2) 1.0528(3) 0.73021(10) 0.0233(5) Uani 1 1 d .
O4 O 0.8255(2) 0.5019(4) 0.73857(11) 0.0241(4) Uani 1 1 d .
H4C H 0.790(3) 0.370(6) 0.7590(16) 0.029 Uiso 1 1 d U
H4D H 0.827(3) 0.459(6) 0.6917(17) 0.029 Uiso 1 1 d U
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
N1 C1 N2 112.8(2)
N1 C1 C4 121.0(2)
N2 C1 C4 126.2(2)
O3 C2 N2 131.5(2)
O3 C2 O1 122.4(2)
N2 C2 O1 106.1(2)
N3 C3 N5 124.5(2)
N3 C3 C4 108.3(2)
N5 C3 C4 127.3(2)
N4 C4 C3 109.9(2)
N4 C4 C1 122.7(2)
C3 C4 C1 127.4(2)
C1 N1 O1 104.40(17)
C1 N2 C2 107.5(2)
C1 N2 H2A 128.3(16)
C2 N2 H2A 124.2(16)
C3 N3 O2 105.16(18)
C4 N4 O2 105.72(18)
C3 N5 H5A 119.0(18)
C3 N5 H5B 119.2(18)
H5A N5 H5B 121(3)
C2 O1 N1 109.26(17)
N4 O2 N3 110.93(17)
H4C O4 H4D 107(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.298(3)
C1 N2 1.361(3)
C1 C4 1.449(3)
C2 O3 1.206(3)
C2 N2 1.361(3)
C2 O1 1.368(3)
C3 N3 1.311(3)
C3 N5 1.343(3)
C3 C4 1.434(3)
C4 N4 1.300(3)
N1 O1 1.420(2)
N2 H2A 0.88(3)
N3 O2 1.408(2)
N4 O2 1.370(3)
N5 H5A 0.92(3)
N5 H5B 0.87(3)
O4 H4C 0.84(3)
O4 H4D 0.84(3)
