#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:31:59 +0100 (dom 24 de nov de 2019) $
#$Revision: 237472 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/71/7237188.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_7237188
loop_
_publ_author_name
'Dalinger, Igor L.'
'Serushkina, Olga V.'
'Muravyev, Nikita V.'
'Meerov, Dmitry B.'
'Miroshnichenko, Evgeniy A.'
'Kon'kova, Tatyana S.'
'Suponitsky, Kyrill Yu.'
'Vener, Mikhail V.'
'Sheremetev, Aleksei B.'
_publ_section_title
;
 Azasydnone -- novel “green” building block for designing
 high energetic compounds
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              18669
_journal_paper_doi               10.1039/C8TA06895J
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C7 H4 N4 O4'
_chemical_formula_sum            'C7 H4 N4 O4'
_chemical_formula_weight         208.14
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-07-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.895(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3726(12)
_cell_length_b                   17.510(4)
_cell_length_c                   8.6127(19)
_cell_measurement_reflns_used    4043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.07
_cell_measurement_theta_min      2.33
_cell_volume                     808.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15218
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         2.326
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       prizm
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0350
_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)+(0.0429P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1562
_reflns_number_total             1943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ta06895j3.cif
_cod_data_source_block           sh330
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7237188
_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.
;
_shelxl_version_number           2014/6
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_posn
_atom_site_refinement_flags_adp
O1 O 0.13336(18) 0.12812(6) 0.59356(11) 0.0277(2) Uani 1 1 d . .
O2 O -0.01501(19) 0.04459(6) 0.76834(12) 0.0289(2) Uani 1 1 d . .
O3 O 0.0307(2) 0.23871(6) -0.08106(13) 0.0345(3) Uani 1 1 d . .
O4 O -0.2736(2) 0.20679(6) -0.24629(12) 0.0339(3) Uani 1 1 d . .
N1 N 0.0606(2) 0.14985(7) 0.44669(14) 0.0269(3) Uani 1 1 d . .
N2 N -0.1372(2) 0.10985(6) 0.41307(13) 0.0206(2) Uani 1 1 d . .
N3 N -0.2123(2) 0.06266(7) 0.52072(14) 0.0242(3) Uani 1 1 d . .
N4 N -0.1666(2) 0.20574(7) -0.11593(14) 0.0265(3) Uani 1 1 d . .
C1 C -0.0397(3) 0.07301(8) 0.64147(16) 0.0240(3) Uani 1 1 d . .
C2 C -0.2647(2) 0.11535(7) 0.26121(16) 0.0207(3) Uani 1 1 d . .
C3 C -0.1579(2) 0.15996(7) 0.15062(15) 0.0218(3) Uani 1 1 d . .
H3A H -0.0082 0.1878 0.1737 0.026 Uiso 1 1 calc R U
C4 C -0.2815(2) 0.16154(8) 0.00536(16) 0.0229(3) Uani 1 1 d . .
C5 C -0.5011(3) 0.12240(8) -0.03132(17) 0.0267(3) Uani 1 1 d . .
H5A H -0.5813 0.1253 -0.1329 0.032 Uiso 1 1 calc R U
C6 C -0.6019(3) 0.07882(8) 0.08318(17) 0.0273(3) Uani 1 1 d . .
H6A H -0.7534 0.0518 0.0603 0.033 Uiso 1 1 calc R U
C7 C -0.4830(2) 0.07436(8) 0.23093(17) 0.0240(3) Uani 1 1 d . .
H7A H -0.5497 0.0439 0.3094 0.029 Uiso 1 1 calc R 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 O1 C1 108.02(10)
N2 N1 O1 103.81(10)
N1 N2 N3 117.85(11)
N1 N2 C2 120.16(11)
N3 N2 C2 121.96(11)
N2 N3 C1 103.19(11)
O3 N4 O4 124.12(13)
O3 N4 C4 118.16(12)
O4 N4 C4 117.72(12)
O2 C1 N3 132.04(13)
O2 C1 O1 120.82(12)
N3 C1 O1 107.14(11)
C7 C2 C3 123.20(13)
C7 C2 N2 118.80(12)
C3 C2 N2 117.97(12)
C4 C3 C2 116.06(12)
C4 C3 H3A 122.0
C2 C3 H3A 122.0
C3 C4 C5 123.33(13)
C3 C4 N4 117.17(12)
C5 C4 N4 119.47(12)
C4 C5 C6 118.62(13)
C4 C5 H5A 120.7
C6 C5 H5A 120.7
C5 C6 C7 120.41(13)
C5 C6 H6A 119.8
C7 C6 H6A 119.8
C2 C7 C6 118.37(13)
C2 C7 H7A 120.8
C6 C7 H7A 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.3530(15)
O1 C1 1.4206(17)
O2 C1 1.1998(17)
O3 N4 1.2263(16)
O4 N4 1.2264(16)
N1 N2 1.2891(16)
N2 N3 1.3251(16)
N2 C2 1.4379(17)
N3 C1 1.3577(18)
N4 C4 1.4695(18)
C2 C7 1.3844(19)
C2 C3 1.3859(19)
C3 C4 1.3762(18)
C3 H3A 0.9500
C4 C5 1.382(2)
C5 C6 1.386(2)
C5 H5A 0.9500
C6 C7 1.387(2)
C6 H6A 0.9500
C7 H7A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 O1 N1 N2 -0.46(14)
O1 N1 N2 N3 0.40(15)
O1 N1 N2 C2 -177.67(11)
N1 N2 N3 C1 -0.16(15)
C2 N2 N3 C1 177.88(11)
N2 N3 C1 O2 -179.42(15)
N2 N3 C1 O1 -0.16(13)
N1 O1 C1 O2 179.76(12)
N1 O1 C1 N3 0.40(14)
N1 N2 C2 C7 -177.05(12)
N3 N2 C2 C7 4.96(18)
N1 N2 C2 C3 4.85(18)
N3 N2 C2 C3 -173.15(11)
C7 C2 C3 C4 -0.18(19)
N2 C2 C3 C4 177.83(11)
C2 C3 C4 C5 0.8(2)
C2 C3 C4 N4 -177.44(11)
O3 N4 C4 C3 -0.30(18)
O4 N4 C4 C3 179.15(12)
O3 N4 C4 C5 -178.61(12)
O4 N4 C4 C5 0.84(18)
C3 C4 C5 C6 -0.5(2)
N4 C4 C5 C6 177.71(12)
C4 C5 C6 C7 -0.5(2)
C3 C2 C7 C6 -0.7(2)
N2 C2 C7 C6 -178.70(12)
C5 C6 C7 C2 1.0(2)
