#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:51:41 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179026 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/24/4122416.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_4122416
loop_
_publ_author_name
'Vo, Thao T.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Tetranitroacetimidic Acid: A High Oxygen Oxidizer and Potential
 Replacement for Ammonium Perchlorate.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11934
_journal_paper_doi               10.1021/ja5074036
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C N3 O6, C5 H4 N'
_chemical_formula_sum            'C6 H4 N4 O6'
_chemical_formula_weight         228.13
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.944(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.416(4)
_cell_length_b                   8.646(4)
_cell_length_c                   12.186(5)
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.393
_cell_measurement_theta_min      2.890
_cell_volume                     886.6(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 1.013
_diffrn_measured_fraction_theta_max 0.996
_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  0.1700
_diffrn_reflns_av_unetI/netI     0.0983
_diffrn_reflns_Laue_measured_fraction_full 1.013
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13102
_diffrn_reflns_point_group_measured_fraction_full 1.013
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.100
_diffrn_reflns_theta_min         1.671
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4825
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1343 before and 0.0860 after correction.
The Ratio of minimum to maximum transmission is 0.6475.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0987
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2784
_refine_ls_wR_factor_ref         0.3233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1558
_reflns_number_total             2360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5074036_si_004.cif
_cod_data_source_block           tvo1922_0m
_cod_depositor_comments
'Adding full bibliography for 4122416--4122419.cif.'
_cod_original_cell_volume        886.7(6)
_cod_database_code               4122416
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-3
_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_max   0.989
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.5632(4) 0.8202(3) 0.0965(3) 0.0284(8) Uani 1 1 d .
O2 O 0.8716(5) 1.1154(4) -0.0503(3) 0.0284(8) Uani 1 1 d .
O3 O 0.6571(5) 0.8850(4) -0.0622(3) 0.0305(9) Uani 1 1 d .
O4 O 0.9415(4) 1.1768(3) 0.1184(3) 0.0270(8) Uani 1 1 d .
O5 O 0.8307(6) 0.9114(4) 0.2637(3) 0.0379(10) Uani 1 1 d .
O6 O 0.6470(5) 1.0864(4) 0.2546(3) 0.0371(10) Uani 1 1 d .
C1 C 0.6906(6) 0.4393(5) 0.2225(4) 0.0250(10) Uani 1 1 d .
N2 N 0.8108(5) 0.5391(4) 0.2313(3) 0.0270(9) Uani 1 1 d .
H2 H 0.8462 0.5638 0.2973 0.032 Uiso 1 1 calc R
N3 N 0.6535(5) 0.8987(4) 0.0385(3) 0.0222(9) Uani 1 1 d .
N4 N 0.8578(5) 1.0992(4) 0.0512(3) 0.0221(9) Uani 1 1 d .
C2 C 0.7045(6) 0.4618(6) 0.0286(4) 0.0302(11) Uani 1 1 d .
H2A H 0.6678 0.4334 -0.0428 0.036 Uiso 1 1 calc R
C3 C 0.6352(6) 0.3996(5) 0.1191(4) 0.0271(11) Uani 1 1 d .
H3 H 0.5491 0.3293 0.1108 0.033 Uiso 1 1 calc R
C4 C 0.8799(7) 0.6032(5) 0.1448(4) 0.0286(11) Uani 1 1 d .
H4 H 0.9649 0.6744 0.1550 0.034 Uiso 1 1 calc R
C5 C 0.8275(7) 0.5656(6) 0.0409(4) 0.0332(12) Uani 1 1 d .
C6 C 0.7505(6) 1.0007(6) 0.0939(3) 0.0238(9) Uani 1 1 d .
N7 N 0.7420(6) 0.9988(4) 0.2126(3) 0.0247(8) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 C3 118.6(4)
C1 N2 H2 118.4
C1 N2 C4 123.2(4)
C4 N2 H2 118.4
O1 N3 C6 115.8(3)
O3 N3 O1 122.4(4)
O3 N3 C6 121.8(4)
O2 N4 O4 121.4(4)
O2 N4 C6 121.6(4)
O4 N4 C6 117.0(4)
C3 C2 H2A 120.0
C3 C2 C5 120.0(5)
C5 C2 H2A 120.0
C1 C3 H3 120.1
C2 C3 C1 119.8(5)
C2 C3 H3 120.1
N2 C4 H4 120.2
N2 C4 C5 119.5(5)
C5 C4 H4 120.2
C4 C5 C2 118.9(5)
N3 C6 N7 116.4(4)
N4 C6 N3 127.7(4)
N4 C6 N7 115.8(4)
O5 N7 C6 118.3(4)
O6 N7 O5 124.7(4)
O6 N7 C6 117.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.247(5)
O2 N4 1.251(5)
O3 N3 1.234(5)
O4 N4 1.264(5)
O5 N7 1.224(6)
O6 N7 1.220(5)
C1 N2 1.332(6)
C1 C3 1.380(7)
N2 H2 0.8800
N2 C4 1.333(6)
N3 C6 1.371(6)
N4 C6 1.352(6)
C2 H2A 0.9500
C2 C3 1.366(7)
C2 C5 1.377(8)
C3 H3 0.9500
C4 H4 0.9500
C4 C5 1.373(8)
C6 N7 1.450(5)
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
O1 N3 C6 N4 -179.6(4)
O1 N3 C6 N7 3.2(7)
O2 N4 C6 N3 5.6(8)
O2 N4 C6 N7 -177.2(4)
O3 N3 C6 N4 1.0(9)
O3 N3 C6 N7 -176.2(4)
O4 N4 C6 N3 -175.9(4)
O4 N4 C6 N7 1.3(7)
C1 N2 C4 C5 -0.4(7)
N2 C1 C3 C2 0.5(7)
N2 C4 C5 C2 -0.2(7)
N3 C6 N7 O5 89.6(6)
N3 C6 N7 O6 -91.1(5)
N4 C6 N7 O5 -87.9(6)
N4 C6 N7 O6 91.4(6)
C3 C1 N2 C4 0.3(7)
C3 C2 C5 C4 0.9(7)
C5 C2 C3 C1 -1.0(7)
