#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:27:47 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230160 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/78/7057873.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_7057873
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 H N5 O5, H2 O'
_chemical_formula_sum            'C4 H3 N5 O6'
_chemical_formula_weight         217.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc20811d
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7552(8)
_cell_length_b                   8.1840(6)
_cell_length_c                   22.4827(17)
_cell_measurement_reflns_used    2293
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.95
_cell_volume                     1610.9(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0786
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8681
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_min         3.526
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1476
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0433
_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)+(0.0396P)²+0.5049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1018
_reflns_number_total             1476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj04428g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7057873--7057875.cif.'
_cod_database_code               7057873
_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   0.956
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.5450(3) 0.7021(3) 0.69565(10) 0.0245(6) Uani 1 1 d . .
C2 C 0.5091(3) 0.7954(3) 0.64435(10) 0.0226(6) Uani 1 1 d . .
C3 C 0.5542(3) 0.9575(3) 0.62313(10) 0.0215(6) Uani 1 1 d . .
C4 C 0.5467(3) 1.1805(3) 0.56996(10) 0.0240(6) Uani 1 1 d . .
N1 N 0.4735(3) 0.5638(2) 0.69490(9) 0.0335(6) Uani 1 1 d . .
N2 N 0.4131(3) 0.7108(2) 0.61251(9) 0.0316(5) Uani 1 1 d . .
N3 N 0.6466(3) 0.7382(3) 0.74532(9) 0.0300(5) Uani 1 1 d . .
N4 N 0.6690(3) 1.0396(2) 0.64303(9) 0.0286(5) Uani 1 1 d . .
N5 N 0.4749(2) 1.0363(2) 0.57960(8) 0.0213(5) Uani 1 1 d . .
H5 H 0.396(3) 1.005(3) 0.5580(10) 0.026 Uiso 1 1 d . U
O1 O 0.3918(2) 0.5661(2) 0.64296(8) 0.0374(5) Uani 1 1 d . .
O2 O 0.6173(3) 0.6745(3) 0.79289(8) 0.0517(6) Uani 1 1 d . .
O3 O 0.7534(2) 0.8288(2) 0.73531(7) 0.0354(5) Uani 1 1 d . .
O4 O 0.6649(2) 1.18671(18) 0.60904(7) 0.0293(5) Uani 1 1 d . .
O5 O 0.5189(2) 1.28873(19) 0.53475(8) 0.0322(5) Uani 1 1 d . .
O6 O 0.2633(2) 1.4766(2) 0.50722(8) 0.0278(4) Uani 1 1 d D .
H6A H 0.314(3) 1.555(3) 0.4951(11) 0.033 Uiso 1 1 d D U
H6B H 0.327(3) 1.410(3) 0.5156(11) 0.033 Uiso 1 1 d 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 C2 110.7(2)
N1 C1 N3 118.9(2)
C2 C1 N3 130.5(2)
N2 C2 C1 107.7(2)
N2 C2 C3 118.4(2)
C1 C2 C3 133.9(2)
N4 C3 N5 113.6(2)
N4 C3 C2 124.7(2)
N5 C3 C2 121.7(2)
O5 C4 N5 130.4(2)
O5 C4 O4 123.2(2)
N5 C4 O4 106.40(19)
C1 N1 O1 104.62(19)
C2 N2 O1 105.72(19)
O3 N3 O2 125.9(2)
O3 N3 C1 116.85(19)
O2 N3 C1 117.2(2)
C3 N4 O4 103.55(18)
C4 N5 C3 106.9(2)
C4 N5 H5 122.0(15)
C3 N5 H5 130.9(15)
N1 O1 N2 111.30(18)
C4 O4 N4 109.54(17)
H6A O6 H6B 104(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.294(3)
C1 C2 1.418(3)
C1 N3 1.458(3)
C2 N2 1.303(3)
C2 C3 1.463(3)
C3 N4 1.289(3)
C3 N5 1.363(3)
C4 O5 1.212(3)
C4 N5 1.354(3)
C4 O4 1.358(3)
N1 O1 1.370(3)
N2 O1 1.381(2)
N3 O3 1.214(3)
N3 O2 1.217(2)
N4 O4 1.427(2)
N5 H5 0.88(3)
O6 H6A 0.828(17)
O6 H6B 0.799(17)
