#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:53:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179602 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/66/4506616.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_4506616
loop_
_publ_author_name
'Landenberger, Kira B.'
'Matzger, Adam J.'
_publ_section_title
;
 Cocrystals of 1,3,5,7-Tetranitro-1,3,5,7-tetrazacyclooctane (HMX)
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3603
_journal_paper_doi               10.1021/cg3004245
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C4 H8 N8 O8, 2(C6 H7 N O)'
_chemical_formula_sum            'C16 H22 N10 O10'
_chemical_formula_weight         514.44
_chemical_name_common            'HMX - 2-picoline-N-oxide'
_chemical_name_systematic
; 
 1,3,5,7-tetranitro-1,3,5,7-tetraza-cyclooctane - 2-picoline-N-oxide 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.604(13)
_cell_angle_beta                 80.885(14)
_cell_angle_gamma                86.334(14)
_cell_formula_units_Z            1
_cell_length_a                   6.0611(16)
_cell_length_b                   7.818(2)
_cell_length_c                   12.154(3)
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      63.18
_cell_measurement_theta_min      7.40
_cell_volume                     539.5(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      95(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1396
_diffrn_reflns_av_sigmaI/netI    0.2247
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4793
_diffrn_reflns_theta_full        63.62
_diffrn_reflns_theta_max         63.62
_diffrn_reflns_theta_min         7.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.153
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.8487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.2651
_refine_ls_R_factor_gt           0.1541
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3597
_refine_ls_wR_factor_ref         0.4490
_reflns_number_gt                637
_reflns_number_total             1730
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4506304
_cod_data_source_file            cg3004245_si_002.cif
_cod_data_source_block           HMX_2pNox
_cod_original_cell_volume        539.5(3)
_cod_database_code               4506616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.8255(12) 0.9999(10) 0.2597(6) 0.059(2) Uani 1 1 d .
O2 O 0.8176(12) 0.7214(11) 0.2529(6) 0.062(2) Uani 1 1 d .
O3 O 1.1050(14) 0.6121(10) -0.1484(6) 0.065(3) Uani 1 1 d .
O4 O 0.7433(16) 0.6418(10) -0.0997(6) 0.069(3) Uani 1 1 d .
O5 O 0.3391(12) 0.8724(9) 0.1942(6) 0.062(2) Uani 1 1 d .
N1 N 0.8218(15) 0.8851(15) 0.2114(8) 0.056(3) Uani 1 1 d .
N2 N 0.8243(14) 0.9555(12) 0.0891(8) 0.053(3) Uani 1 1 d .
N3 N 0.943(2) 0.6713(13) -0.0978(8) 0.067(3) Uani 1 1 d .
N4 N 0.9733(16) 0.7677(12) -0.0251(8) 0.056(3) Uani 1 1 d .
N5 N 0.3072(14) 0.8310(13) 0.3094(8) 0.054(3) Uani 1 1 d .
C1 C 0.7655(19) 0.8353(15) 0.0310(9) 0.055(3) Uani 1 1 d .
H1A H 0.6707 0.8994 -0.0290 0.066 Uiso 1 1 calc R
H1B H 0.6802 0.7330 0.0884 0.066 Uiso 1 1 calc R
C2 C 1.187(2) 0.8486(16) -0.0381(10) 0.064(4) Uani 1 1 d .
H2A H 1.2981 0.7983 -0.0889 0.077 Uiso 1 1 calc R
H2B H 1.2366 0.8180 0.0396 0.077 Uiso 1 1 calc R
C3 C 0.2838(18) 0.6552(15) 0.3760(10) 0.058(3) Uani 1 1 d .
C4 C 0.2466(19) 0.6204(17) 0.5001(10) 0.058(3) Uani 1 1 d .
H4 H 0.2307 0.5000 0.5508 0.070 Uiso 1 1 calc R
C5 C 0.2339(17) 0.7584(19) 0.5455(11) 0.064(4) Uani 1 1 d .
H5 H 0.2037 0.7330 0.6282 0.077 Uiso 1 1 calc R
C6 C 0.2632(19) 0.9328(17) 0.4765(10) 0.060(3) Uani 1 1 d .
H6 H 0.2611 1.0279 0.5097 0.072 Uiso 1 1 calc R
C7 C 0.2955(18) 0.9659(15) 0.3581(9) 0.058(3) Uani 1 1 d .
H7 H 0.3103 1.0869 0.3083 0.070 Uiso 1 1 calc R
C8 C 0.304(2) 0.5176(14) 0.3180(10) 0.067(4) Uani 1 1 d .
H8A H 0.2879 0.3984 0.3770 0.080 Uiso 1 1 calc R
H8B H 0.4510 0.5252 0.2697 0.080 Uiso 1 1 calc R
H8C H 0.1869 0.5364 0.2681 0.080 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 '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
O2 N1 O1 129.8(10) . .
O2 N1 N2 116.3(9) . .
O1 N1 N2 113.9(10) . .
N1 N2 C1 116.9(9) . .
N1 N2 C2 117.5(9) . 2_775
C1 N2 C2 122.5(10) . 2_775
O3 N3 O4 125.4(12) . .
O3 N3 N4 119.7(13) . .
O4 N3 N4 114.7(9) . .
N3 N4 C2 119.1(9) . .
N3 N4 C1 115.4(10) . .
C2 N4 C1 121.9(9) . .
O5 N5 C7 118.8(9) . .
O5 N5 C3 119.4(10) . .
C7 N5 C3 121.8(10) . .
N2 C1 N4 108.8(9) . .
N2 C1 H1A 109.9 . .
N4 C1 H1A 109.9 . .
N2 C1 H1B 109.9 . .
N4 C1 H1B 109.9 . .
H1A C1 H1B 108.3 . .
N4 C2 N2 111.8(10) . 2_775
N4 C2 H2A 109.3 . .
N2 C2 H2A 109.3 2_775 .
N4 C2 H2B 109.3 . .
N2 C2 H2B 109.3 2_775 .
H2A C2 H2B 107.9 . .
N5 C3 C4 116.4(11) . .
N5 C3 C8 118.8(11) . .
C4 C3 C8 124.8(11) . .
C5 C4 C3 120.2(11) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 122.1(11) . .
C4 C5 H5 119.0 . .
C6 C5 H5 119.0 . .
C5 C6 C7 117.6(11) . .
C5 C6 H6 121.2 . .
C7 C6 H6 121.2 . .
N5 C7 C6 121.9(11) . .
N5 C7 H7 119.0 . .
C6 C7 H7 119.0 . .
C3 C8 H8A 109.5 . .
C3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.221(10) .
O2 N1 1.218(10) .
O3 N3 1.219(11) .
O4 N3 1.252(11) .
O5 N5 1.318(10) .
N1 N2 1.411(12) .
N2 C1 1.431(13) .
N2 C2 1.461(12) 2_775
N3 N4 1.368(12) .
N4 C2 1.440(13) .
N4 C1 1.483(12) .
N5 C7 1.356(12) .
N5 C3 1.361(13) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 N2 1.461(12) 2_775
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.428(15) .
C3 C8 1.450(14) .
C4 C5 1.351(14) .
C4 H4 0.9500 .
C5 C6 1.362(14) .
C5 H5 0.9500 .
C6 C7 1.363(14) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
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_4
O2 N1 N2 C1 15.3(13) . .
O1 N1 N2 C1 -165.1(9) . .
O2 N1 N2 C2 175.8(9) . 2_775
O1 N1 N2 C2 -4.6(13) . 2_775
O3 N3 N4 C2 20.5(15) . .
O4 N3 N4 C2 -164.2(9) . .
O3 N3 N4 C1 179.3(8) . .
O4 N3 N4 C1 -5.3(13) . .
N1 N2 C1 N4 -100.2(10) . .
C2 N2 C1 N4 100.4(10) 2_775 .
N3 N4 C1 N2 -171.1(9) . .
C2 N4 C1 N2 -12.9(13) . .
N3 N4 C2 N2 108.0(11) . 2_775
C1 N4 C2 N2 -49.5(13) . 2_775
O5 N5 C3 C4 -179.1(9) . .
C7 N5 C3 C4 -0.1(16) . .
O5 N5 C3 C8 2.5(15) . .
C7 N5 C3 C8 -178.4(9) . .
N5 C3 C4 C5 0.7(16) . .
C8 C3 C4 C5 178.9(10) . .
C3 C4 C5 C6 -2.3(17) . .
C4 C5 C6 C7 3.1(17) . .
O5 N5 C7 C6 -179.9(10) . .
C3 N5 C7 C6 1.0(17) . .
C5 C6 C7 N5 -2.5(17) . .
