#------------------------------------------------------------------------------
#$Date: 2019-01-30 01:08:36 +0200 (Wed, 30 Jan 2019) $
#$Revision: 213370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/29/7122906.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_7122906
loop_
_publ_author_name
'Snyder, Christopher'
'Wells, Lucille'
'Chavez, David'
'Imler, Gregory H.'
'Parrish, Damon A.'
_publ_section_title
;
 Polycyclic N-Oxides: High Performing, Low Sensitivity Energetic Materials
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09653H
_journal_year                    2019
_chemical_formula_moiety         'C8 H4 N16 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C14 H18 N18 O8'
_chemical_formula_weight         566.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-02-06 deposited with the CCDC.
2019-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3283(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8361(4)
_cell_length_b                   11.0288(4)
_cell_length_c                   17.3634(6)
_cell_measurement_reflns_used    5789
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.965
_cell_measurement_theta_min      2.348
_cell_volume                     2264.71(14)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_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  0.0197
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13128
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_min         2.525
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0495P)²+1.5726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2682
_reflns_number_total             3186
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc09653h2.cif
_cod_data_source_block           chav137b
_cod_database_code               7122906
_shelx_shelxl_version_number     2014/7
_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_min   0.964
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.51583(8) 0.67870(9) 0.44340(6) 0.0221(2) Uani 1 1 d . .
N2 N 0.56331(8) 0.56863(8) 0.43829(5) 0.0206(2) Uani 1 1 d . .
O3 O 0.52144(8) 0.49347(8) 0.38978(5) 0.0287(2) Uani 1 1 d . .
C4 C 0.65350(10) 0.53300(10) 0.48411(6) 0.0203(2) Uani 1 1 d . .
N5 N 0.70199(9) 0.42577(9) 0.47714(6) 0.0236(2) Uani 1 1 d . .
H5A H 0.6761 0.3744 0.4419 0.028 Uiso 1 1 calc R U
H5B H 0.7601 0.4058 0.5078 0.028 Uiso 1 1 calc R U
N6 N 0.69272(8) 0.61366(8) 0.53891(5) 0.0202(2) Uani 1 1 d . .
O7 O 0.77408(8) 0.58139(8) 0.58307(5) 0.0282(2) Uani 1 1 d . .
N8 N 0.65054(8) 0.72501(9) 0.54562(6) 0.0213(2) Uani 1 1 d . .
C9 C 0.56477(9) 0.74960(10) 0.49650(6) 0.0200(2) Uani 1 1 d . .
N10 N 0.52117(8) 0.86791(9) 0.50086(5) 0.0212(2) Uani 1 1 d . .
C11 C 0.54141(9) 0.94241(10) 0.56521(6) 0.0210(2) Uani 1 1 d . .
N12 N 0.57752(10) 0.90938(10) 0.63354(6) 0.0300(2) Uani 1 1 d . .
O13 O 0.58086(9) 1.01594(9) 0.67621(5) 0.0340(2) Uani 1 1 d . .
N14 N 0.54568(10) 1.11529(10) 0.63211(6) 0.0290(2) Uani 1 1 d . .
C15 C 0.52100(9) 1.07022(10) 0.56433(6) 0.0207(2) Uani 1 1 d . .
C16 C 0.67155(11) 0.29692(13) 0.77890(7) 0.0303(3) Uani 1 1 d . .
H16A H 0.6230 0.3634 0.7599 0.046 Uiso 1 1 calc R U
H16B H 0.7107 0.3213 0.8273 0.046 Uiso 1 1 calc R U
H16C H 0.6251 0.2251 0.7879 0.046 Uiso 1 1 calc R U
N17 N 0.75453(8) 0.26862(9) 0.72185(5) 0.0227(2) Uani 1 1 d . .
C18 C 0.83526(13) 0.17308(13) 0.74082(8) 0.0367(3) Uani 1 1 d . .
H18A H 0.7957 0.0952 0.7429 0.055 Uiso 1 1 calc R U
H18B H 0.8726 0.1900 0.7911 0.055 Uiso 1 1 calc R U
H18C H 0.8920 0.1696 0.7013 0.055 Uiso 1 1 calc R U
C19 C 0.75003(10) 0.32179(10) 0.65363(7) 0.0230(2) Uani 1 1 d . .
H19 H 0.6943 0.3829 0.6452 0.028 Uiso 1 1 calc R U
O20 O 0.81227(8) 0.29899(8) 0.59931(5) 0.0273(2) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 N1 N2 114.05(10) . .
O3 N2 N1 118.80(10) . .
O3 N2 C4 118.35(9) . .
N1 N2 C4 122.84(9) . .
N5 C4 N2 122.48(10) . .
N5 C4 N6 120.55(11) . .
N2 C4 N6 116.97(10) . .
C4 N5 H5A 120.0 . .
C4 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
O7 N6 N8 119.19(9) . .
O7 N6 C4 117.99(9) . .
N8 N6 C4 122.79(10) . .
C9 N8 N6 114.31(9) . .
N1 C9 N8 128.93(10) . .
N1 C9 N10 115.73(10) . .
N8 C9 N10 115.33(10) . .
C15 N10 C11 113.84(9) 5_676 .
C15 N10 C9 121.98(9) 5_676 .
C11 N10 C9 122.44(9) . .
N12 C11 N10 127.21(11) . .
N12 C11 C15 109.63(10) . .
N10 C11 C15 123.14(10) . .
C11 N12 O13 104.56(10) . .
N12 O13 N14 111.81(9) . .
C15 N14 O13 104.39(9) . .
N14 C15 N10 127.36(10) . 5_676
N14 C15 C11 109.61(10) . .
N10 C15 C11 123.02(10) 5_676 .
N17 C16 H16A 109.5 . .
N17 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
N17 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C19 N17 C18 121.88(10) . .
C19 N17 C16 120.73(10) . .
C18 N17 C16 117.19(10) . .
N17 C18 H18A 109.5 . .
N17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O20 C19 N17 125.86(11) . .
O20 C19 H19 117.1 . .
N17 C19 H19 117.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.3243(15) .
N1 N2 1.3422(13) .
N2 O3 1.2682(13) .
N2 C4 1.3631(15) .
C4 N5 1.3222(14) .
C4 N6 1.3697(15) .
N5 H5A 0.8800 .
N5 H5B 0.8800 .
N6 O7 1.2577(13) .
N6 N8 1.3326(13) .
N8 C9 1.3271(15) .
C9 N10 1.4063(14) .
N10 C15 1.3965(14) 5_676
N10 C11 1.3997(14) .
C11 N12 1.2969(15) .
C11 C15 1.4301(15) .
N12 O13 1.3891(13) .
O13 N14 1.3908(14) .
N14 C15 1.2998(15) .
C15 N10 1.3965(14) 5_676
C16 N17 1.4569(15) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
N17 C19 1.3207(15) .
N17 C18 1.4513(16) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 O20 1.2458(14) .
C19 H19 0.9500 .
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
N5 H5A O20 0.88 2.05 2.8138(13) 144.9 7_656
N5 H5B O20 0.88 2.05 2.8167(14) 144.5 .
C19 H19 O7 0.95 2.63 3.1317(15) 113.2 .
C18 H18C O3 0.98 2.63 3.4214(16) 138.0 7_656
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
C9 N1 N2 O3 179.05(9) . .
C9 N1 N2 C4 0.38(14) . .
O3 N2 C4 N5 3.44(15) . .
N1 N2 C4 N5 -177.88(10) . .
O3 N2 C4 N6 -176.35(9) . .
N1 N2 C4 N6 2.33(15) . .
N5 C4 N6 O7 -1.54(15) . .
N2 C4 N6 O7 178.25(9) . .
N5 C4 N6 N8 176.46(10) . .
N2 C4 N6 N8 -3.75(15) . .
O7 N6 N8 C9 -179.78(10) . .
C4 N6 N8 C9 2.24(15) . .
N2 N1 C9 N8 -2.16(17) . .
N2 N1 C9 N10 176.79(9) . .
N6 N8 C9 N1 0.89(17) . .
N6 N8 C9 N10 -178.07(9) . .
N1 C9 N10 C15 -33.44(15) . 5_676
N8 C9 N10 C15 145.67(11) . 5_676
N1 C9 N10 C11 162.56(10) . .
N8 C9 N10 C11 -18.34(15) . .
C15 N10 C11 N12 178.09(12) 5_676 .
C9 N10 C11 N12 -16.71(18) . .
C15 N10 C11 C15 -0.10(17) 5_676 .
C9 N10 C11 C15 165.09(10) . .
N10 C11 N12 O13 -178.74(11) . .
C15 C11 N12 O13 -0.34(13) . .
C11 N12 O13 N14 0.04(14) . .
N12 O13 N14 C15 0.29(14) . .
O13 N14 C15 N10 178.37(11) . 5_676
O13 N14 C15 C11 -0.49(13) . .
N12 C11 C15 N14 0.55(14) . .
N10 C11 C15 N14 179.03(11) . .
N12 C11 C15 N10 -178.36(11) . 5_676
N10 C11 C15 N10 0.11(18) . 5_676
C18 N17 C19 O20 -0.74(19) . .
C16 N17 C19 O20 -175.44(12) . .
