#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/24/7052432.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_7052432
loop_
_publ_author_name
'Siri, Olivier'
'Braunstein, Pierre'
_publ_section_title
;
 Tuning the synthesis of a dinitroaromatic towards a new
 trinitroaromatic stabilized energetic material
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              75
_journal_paper_doi               10.1039/b412789g
_journal_volume                  29
_journal_year                    2005
_chemical_formula_moiety         'C6 H6 N4 O4'
_chemical_formula_sum            'C6 H6 N4 O4'
_chemical_formula_weight         198.15
_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_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                 98.504(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7780(10)
_cell_length_b                   5.6200(10)
_cell_length_c                   15.635(2)
_cell_measurement_reflns_used    3086
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     762.83(19)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5056
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0489
_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)+(0.0554P)²+0.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                1670
_reflns_number_total             2215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b412789g.txt
_cod_data_source_block           wel2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7052432
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.37490(16) 0.3345(3) 0.03682(9) 0.0198(3) Uani 1 1 d . . .
O2 O 0.11432(13) 0.6220(2) -0.18725(7) 0.0310(3) Uani 1 1 d . . .
N3 N 0.07343(14) 0.6539(2) -0.11617(8) 0.0210(3) Uani 1 1 d . . .
O1 O -0.04814(12) 0.75273(19) -0.10682(7) 0.0291(3) Uani 1 1 d . . .
C5 C 0.26946(15) 0.3805(2) -0.03609(9) 0.0181(3) Uani 1 1 d . . .
N4 N 0.24850(14) 0.1969(2) -0.10203(8) 0.0213(3) Uani 1 1 d . . .
C1 C 0.39021(16) 0.4847(3) 0.10838(9) 0.0208(3) Uani 1 1 d . . .
O4 O 0.11811(13) 0.1646(2) -0.14071(7) 0.0327(3) Uani 1 1 d . . .
C2 C 0.29339(16) 0.6884(3) 0.10610(9) 0.0207(3) Uani 1 1 d . . .
O3 O 0.36015(13) 0.07405(19) -0.11275(7) 0.0311(3) Uani 1 1 d . . .
C4 C 0.17562(15) 0.5818(2) -0.03900(9) 0.0184(3) Uani 1 1 d . . .
C3 C 0.18831(16) 0.7319(3) 0.03190(9) 0.0203(3) Uani 1 1 d . . .
N1 N 0.49463(17) 0.4347(3) 0.17934(9) 0.0308(3) Uani 1 1 d . . .
N2 N 0.29987(18) 0.8329(3) 0.17727(9) 0.0317(3) Uani 1 1 d . . .
H1 H 0.551(2) 0.313(4) 0.1753(13) 0.038(6) Uiso 1 1 d . . .
H2 H 0.501(2) 0.520(4) 0.2251(15) 0.048(6) Uiso 1 1 d . . .
H3 H 0.380(3) 0.839(4) 0.2090(15) 0.046(6) Uiso 1 1 d . . .
H4 H 0.241(3) 0.965(4) 0.1736(14) 0.047(6) Uiso 1 1 d . . .
H5 H 0.128(2) 0.864(3) 0.0310(11) 0.026(4) Uiso 1 1 d . . .
H6 H 0.434(2) 0.194(3) 0.0370(11) 0.031(5) Uiso 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'
H H 0.0000 0.0000 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 C1 121.51(13) . . ?
C5 C6 H6 117.4(11) . . ?
C1 C6 H6 121.1(11) . . ?
O2 N3 O1 123.16(12) . . ?
O2 N3 C4 118.91(11) . . ?
O1 N3 C4 117.88(12) . . ?
C6 C5 C4 119.88(13) . . ?
C6 C5 N4 116.89(12) . . ?
C4 C5 N4 122.74(12) . . ?
O4 N4 O3 123.61(12) . . ?
O4 N4 C5 117.83(12) . . ?
O3 N4 C5 118.43(12) . . ?
N1 C1 C6 120.23(14) . . ?
N1 C1 C2 120.99(13) . . ?
C6 C1 C2 118.77(13) . . ?
N2 C2 C3 120.99(14) . . ?
N2 C2 C1 120.19(13) . . ?
C3 C2 C1 118.77(12) . . ?
C3 C4 C5 119.37(13) . . ?
C3 C4 N3 117.55(12) . . ?
C5 C4 N3 122.87(12) . . ?
C4 C3 C2 121.69(13) . . ?
C4 C3 H5 120.4(11) . . ?
C2 C3 H5 118.0(11) . . ?
C1 N1 H1 115.7(14) . . ?
C1 N1 H2 121.2(15) . . ?
H1 N1 H2 123(2) . . ?
C2 N2 H3 117.1(16) . . ?
C2 N2 H4 118.8(14) . . ?
H3 N2 H4 117(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C5 1.382(2) . ?
C6 C1 1.392(2) . ?
C6 H6 0.946(19) . ?
O2 N3 1.2304(16) . ?
N3 O1 1.2307(16) . ?
N3 C4 1.4508(17) . ?
C5 C4 1.3964(19) . ?
C5 N4 1.4507(18) . ?
N4 O4 1.2264(16) . ?
N4 O3 1.2305(15) . ?
C1 N1 1.3599(18) . ?
C1 C2 1.423(2) . ?
C2 N2 1.3719(19) . ?
C2 C3 1.393(2) . ?
C4 C3 1.384(2) . ?
C3 H5 0.911(18) . ?
N1 H1 0.85(2) . ?
N1 H2 0.86(2) . ?
N2 H3 0.80(2) . ?
N2 H4 0.90(2) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C6 C5 C4 0.1(2) . . . . ?
C1 C6 C5 N4 -171.99(12) . . . . ?
C6 C5 N4 O4 143.02(13) . . . . ?
C4 C5 N4 O4 -28.86(19) . . . . ?
C6 C5 N4 O3 -33.04(18) . . . . ?
C4 C5 N4 O3 155.07(13) . . . . ?
C5 C6 C1 N1 179.80(14) . . . . ?
C5 C6 C1 C2 0.7(2) . . . . ?
N1 C1 C2 N2 -2.6(2) . . . . ?
C6 C1 C2 N2 176.51(13) . . . . ?
N1 C1 C2 C3 -179.99(13) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C5 C4 C3 -0.7(2) . . . . ?
N4 C5 C4 C3 170.91(13) . . . . ?
C6 C5 C4 N3 173.76(13) . . . . ?
N4 C5 C4 N3 -14.6(2) . . . . ?
O2 N3 C4 C3 139.34(14) . . . . ?
O1 N3 C4 C3 -37.98(19) . . . . ?
O2 N3 C4 C5 -35.25(19) . . . . ?
O1 N3 C4 C5 147.43(13) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
N3 C4 C3 C2 -174.26(12) . . . . ?
N2 C2 C3 C4 -177.08(14) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3641324
