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#$Date: 2016-03-22 13:49:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178979 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/02/4120295.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_4120295
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         'C4 Cl4 N8 O8'
_chemical_formula_sum            'C4 Cl4 N8 O8'
_chemical_formula_weight         429.92
_chemical_name_common            FOXCl4
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.392(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8266(10)
_cell_length_b                   7.0676(9)
_cell_length_c                   12.7622(16)
_cell_measurement_temperature    150(2)
_cell_volume                     692.04(15)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.8596
_exptl_absorpt_correction_T_min  0.7884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.1654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                2302
_reflns_number_total             2524
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja406629g_si_002_2.cif
_cod_data_source_block           shrv203
_cod_database_code               4120295
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
N1 N -0.04097(10) 0.95653(10) 0.53022(6) 0.01604(14) Uani 1 1 d
C2 C 0.05621(10) 0.80601(12) 0.58718(7) 0.01424(14) Uani 1 1 d
N3 N -0.00245(10) 0.70299(11) 0.65429(6) 0.01748(14) Uani 1 1 d
Cl4 Cl -0.20668(3) 0.75082(4) 0.67300(2) 0.02486(7) Uani 1 1 d
C5 C 0.24420(11) 0.76602(12) 0.57833(7) 0.01471(14) Uani 1 1 d
Cl6 Cl 0.38212(3) 0.95067(3) 0.624856(19) 0.02253(6) Uani 1 1 d
N7 N 0.30543(10) 0.58086(12) 0.64167(7) 0.02060(15) Uani 1 1 d
O8 O 0.25206(11) 0.43495(10) 0.59638(7) 0.02891(17) Uani 1 1 d
O9 O 0.39669(11) 0.59900(14) 0.72924(7) 0.0354(2) Uani 1 1 d
N10 N 0.25901(10) 0.71301(11) 0.46302(6) 0.01786(14) Uani 1 1 d
O11 O 0.12322(10) 0.67965(11) 0.40150(6) 0.02431(15) Uani 1 1 d
O12 O 0.40609(10) 0.70305(13) 0.44603(7) 0.03062(17) 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'
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
_geom_angle_site_symmetry_1
N1 N1 C2 113.17(9) 3_576
N3 C2 N1 122.88(8) .
N3 C2 C5 115.11(7) .
N1 C2 C5 121.86(7) .
C2 N3 Cl4 117.04(6) .
C2 C5 N10 111.76(7) .
C2 C5 N7 108.59(7) .
N10 C5 N7 102.51(7) .
C2 C5 Cl6 112.47(6) .
N10 C5 Cl6 110.63(6) .
N7 C5 Cl6 110.41(6) .
O9 N7 O8 127.94(9) .
O9 N7 C5 117.03(8) .
O8 N7 C5 115.02(8) .
O11 N10 O12 127.80(9) .
O11 N10 C5 116.28(7) .
O12 N10 C5 115.86(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 N1 1.2567(15) 3_576
N1 C2 1.4213(11) .
C2 N3 1.2767(11) .
C2 C5 1.5242(12) .
N3 Cl4 1.6962(8) .
C5 N10 1.5448(12) .
C5 N7 1.5629(11) .
C5 Cl6 1.7227(9) .
N7 O9 1.2084(12) .
N7 O8 1.2152(12) .
N10 O11 1.2132(11) .
N10 O12 1.2148(11) .
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
_geom_torsion_site_symmetry_1
N1 N1 C2 N3 178.52(10) 3_576
N1 N1 C2 C5 3.24(13) 3_576
N1 C2 N3 Cl4 0.70(12) .
C5 C2 N3 Cl4 176.27(6) .
N3 C2 C5 N10 122.19(8) .
N1 C2 C5 N10 -62.19(10) .
N3 C2 C5 N7 9.84(10) .
N1 C2 C5 N7 -174.55(7) .
N3 C2 C5 Cl6 -112.67(8) .
N1 C2 C5 Cl6 62.95(9) .
C2 C5 N7 O9 -101.60(9) .
N10 C5 N7 O9 140.02(9) .
Cl6 C5 N7 O9 22.14(10) .
C2 C5 N7 O8 77.33(10) .
N10 C5 N7 O8 -41.04(9) .
Cl6 C5 N7 O8 -158.93(7) .
C2 C5 N10 O11 -11.83(11) .
N7 C5 N10 O11 104.29(8) .
Cl6 C5 N10 O11 -137.99(7) .
C2 C5 N10 O12 170.78(8) .
N7 C5 N10 O12 -73.11(9) .
Cl6 C5 N10 O12 44.62(10) .
