#------------------------------------------------------------------------------
#$Date: 2025-08-20 18:06:18 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301834 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/02/4120294.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_4120294
loop_
_publ_author_name
'Thao T. Vo'
'Jiaheng Zhang'
'Damon A. Parrish'
'Brendan Twamley'
'Jean'ne M. Shreeve'
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       damon.parrish@nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_publ_section_title
;
 New Roles for 1,1-Diamino-2,2-dinitroethene (FOX-7): Halogenated FOX-7
 and Azo-bis(diahaloFOX) as Energetic Materials and Oxidizers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11787
_journal_page_last               11790
_journal_paper_doi               10.1021/ja406629g
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C2 H2 Cl2 N4 O4'
_chemical_formula_sum            'C2 H2 Cl2 N4 O4'
_chemical_formula_weight         216.98
_chemical_name_common            FOXCl2
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.7378(12)
_cell_length_b                   10.5173(13)
_cell_length_c                   14.3679(17)
_cell_measurement_temperature    100(2)
_cell_volume                     1471.5(3)
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19982
_diffrn_reflns_theta_full        28.85
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_correction_T_min  0.7077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0274P)²+1.1722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                1289
_reflns_number_total             1938
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja406629g_si_002_1.cif
_cod_data_source_block           shrv213
_cod_database_code               4120294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.12794(7) 0.47627(6) 0.15889(4) 0.01904(15) Uani 1 1 d .
N2 N 0.2243(2) 0.4771(2) 0.25970(13) 0.0146(4) Uani 1 1 d .
C3 C 0.2472(3) 0.3639(2) 0.29002(16) 0.0140(5) Uani 1 1 d .
N4 N 0.2043(2) 0.2523(2) 0.25691(14) 0.0224(5) Uani 1 1 d .
H4A H 0.1521 0.2496 0.2070 0.027 Uiso 1 1 calc R
H4B H 0.2282 0.1813 0.2850 0.027 Uiso 1 1 calc R
C5 C 0.3331(3) 0.3600(2) 0.37818(17) 0.0171(5) Uani 1 1 d .
Cl6 Cl 0.45794(8) 0.24391(8) 0.37650(5) 0.0335(2) Uani 1 1 d .
N7 N 0.4013(2) 0.4916(2) 0.39396(14) 0.0236(5) Uani 1 1 d .
O8 O 0.3419(2) 0.56430(19) 0.44578(13) 0.0331(5) Uani 1 1 d .
O9 O 0.5070(2) 0.5116(2) 0.35188(14) 0.0402(6) Uani 1 1 d .
N10 N 0.2405(2) 0.34257(19) 0.46512(14) 0.0176(5) Uani 1 1 d .
O11 O 0.2951(2) 0.30221(18) 0.53510(12) 0.0257(5) Uani 1 1 d .
O12 O 0.1215(2) 0.37369(18) 0.45542(12) 0.0254(4) 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'
Cl Cl 0.1484 0.1585 '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
C3 N2 Cl1 111.96(17)
N2 C3 N4 129.7(2)
N2 C3 C5 113.8(2)
N4 C3 C5 116.5(2)
C3 N4 H4A 120.0
C3 N4 H4B 120.0
H4A N4 H4B 120.0
C3 C5 N10 110.8(2)
C3 C5 N7 109.5(2)
N10 C5 N7 103.68(18)
C3 C5 Cl6 113.33(17)
N10 C5 Cl6 109.72(17)
N7 C5 Cl6 109.44(18)
O9 N7 O8 127.0(2)
O9 N7 C5 116.4(2)
O8 N7 C5 116.6(2)
O12 N10 O11 127.4(2)
O12 N10 C5 115.55(19)
O11 N10 C5 117.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 N2 1.726(2)
N2 C3 1.287(3)
C3 N4 1.334(3)
C3 C5 1.519(3)
N4 H4A 0.8800
N4 H4B 0.8800
C5 N10 1.552(3)
C5 N7 1.552(3)
C5 Cl6 1.723(2)
N7 O9 1.213(3)
N7 O8 1.214(3)
N10 O12 1.213(3)
N10 O11 1.214(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B N2 0.88 2.23 2.977(3) 142.9 8_655
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
Cl1 N2 C3 N4 -2.5(4)
Cl1 N2 C3 C5 179.37(17)
N2 C3 C5 N10 99.3(2)
N4 C3 C5 N10 -79.1(3)
N2 C3 C5 N7 -14.4(3)
N4 C3 C5 N7 167.1(2)
N2 C3 C5 Cl6 -136.9(2)
N4 C3 C5 Cl6 44.7(3)
C3 C5 N7 O9 -83.1(3)
N10 C5 N7 O9 158.6(2)
Cl6 C5 N7 O9 41.6(3)
C3 C5 N7 O8 95.7(3)
N10 C5 N7 O8 -22.6(3)
Cl6 C5 N7 O8 -139.6(2)
C3 C5 N10 O12 -21.9(3)
N7 C5 N10 O12 95.4(2)
Cl6 C5 N10 O12 -147.77(19)
C3 C5 N10 O11 159.5(2)
N7 C5 N10 O11 -83.1(2)
Cl6 C5 N10 O11 33.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12191170
