#------------------------------------------------------------------------------
#$Date: 2020-09-22 03:48:14 +0200 (mar 22 de sep de 2020) $
#$Revision: 256611 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/12/7241283.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_7241283
loop_
_publ_author_name
'Zharkov, Mikhail'
'Kuchurov, Ilya'
'Zlotin, Sergei Grigorievich'
_publ_section_title
;
 Micronization of CL-20 using supercritical and liquefied gases
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01167C
_journal_year                    2020
_chemical_formula_moiety         'C6 H6 N12 O12, .5(C O2)'
_chemical_formula_sum            'C6.5 H6 N12 O13'
_chemical_formula_weight         460.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-20 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.61490(10)
_cell_length_b                   13.07830(10)
_cell_length_c                   23.3712(3)
_cell_measurement_reflns_used    9802
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.81
_cell_measurement_theta_min      2.74
_cell_volume                     2938.85(5)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_structure_solution
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            145739
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.325
_diffrn_reflns_theta_min         2.743
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2 (Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 2015, 48, 3-10).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         7114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0282
_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)+(0.0361P)²+0.8885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6553
_reflns_number_total             7114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01167c2.cif
_cod_data_source_block           MCL12
_cod_original_formula_sum        'C6.50 H6 N12 O13'
_cod_database_code               7241283
_shelx_shelxl_version_number     2018/3
_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_min   0.950
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69692(5) 0.42735(4) 0.25334(2) 0.01205(8) Uani 1 1 d . . . . .
O2 O 0.58529(6) 0.29222(4) 0.22259(2) 0.01584(9) Uani 1 1 d . . . . .
O3 O 0.45122(6) 0.11224(4) 0.26509(2) 0.01621(9) Uani 1 1 d . . . . .
O4 O 0.62842(6) 0.07401(4) 0.31899(3) 0.02050(10) Uani 1 1 d . . . . .
O5 O 0.87684(5) 0.21255(4) 0.37091(2) 0.01680(9) Uani 1 1 d . . . . .
O6 O 0.91219(5) 0.37551(5) 0.38408(3) 0.02058(11) Uani 1 1 d . . . . .
O7 O 0.70558(6) 0.50490(4) 0.48494(2) 0.01626(9) Uani 1 1 d . . . . .
O8 O 0.58971(6) 0.38910(4) 0.53260(2) 0.01513(9) Uani 1 1 d . . . . .
O9 O 0.30963(5) 0.25785(4) 0.50884(2) 0.01338(8) Uani 1 1 d . . . . .
O10 O 0.15642(5) 0.32248(4) 0.45038(2) 0.01252(8) Uani 1 1 d . . . . .
O11 O 0.17111(5) 0.51059(4) 0.36680(2) 0.01453(9) Uani 1 1 d . . . . .
O12 O 0.33821(6) 0.61007(4) 0.33712(2) 0.01531(9) Uani 1 1 d . . . . .
N1 N 0.49803(5) 0.38212(4) 0.29429(2) 0.00793(8) Uani 1 1 d . . . . .
N2 N 0.50238(5) 0.21289(4) 0.33911(2) 0.00874(8) Uani 1 1 d . . . . .
N3 N 0.69533(5) 0.31998(4) 0.36343(2) 0.00897(8) Uani 1 1 d . . . . .
N4 N 0.57550(5) 0.39256(4) 0.43789(2) 0.00942(8) Uani 1 1 d . . . . .
N5 N 0.37107(5) 0.29199(4) 0.41879(2) 0.00772(7) Uani 1 1 d . . . . .
N6 N 0.38902(5) 0.45193(4) 0.36872(2) 0.00806(8) Uani 1 1 d . . . . .
N7 N 0.60071(5) 0.36607(4) 0.25439(2) 0.00942(8) Uani 1 1 d . . . . .
N8 N 0.53070(6) 0.12727(4) 0.30454(2) 0.01215(9) Uani 1 1 d . . . . .
N9 N 0.84032(5) 0.30105(4) 0.37495(2) 0.01215(9) Uani 1 1 d . . . . .
N10 N 0.62922(6) 0.43011(4) 0.48858(2) 0.01038(8) Uani 1 1 d . . . . .
N11 N 0.27231(5) 0.29261(4) 0.46257(2) 0.00870(8) Uani 1 1 d . . . . .
N12 N 0.29157(6) 0.52998(4) 0.35527(2) 0.01008(8) Uani 1 1 d . . . . .
C1 C 0.41760(6) 0.29402(4) 0.31612(2) 0.00793(8) Uani 1 1 d . . . . .
H1 H 0.3584(12) 0.2672(8) 0.2874(5) 0.013(2) Uiso 1 1 d . . . . .
C2 C 0.33646(6) 0.34618(4) 0.36664(2) 0.00754(8) Uani 1 1 d . . . . .
H2 H 0.2377(12) 0.3448(9) 0.3611(5) 0.013(2) Uiso 1 1 d . . . . .
C3 C 0.59936(6) 0.23943(4) 0.38350(2) 0.00851(8) Uani 1 1 d . . . . .
H3 H 0.6476(12) 0.1806(9) 0.3937(5) 0.015(3) Uiso 1 1 d . . . . .
C4 C 0.51664(6) 0.28949(4) 0.43466(2) 0.00785(8) Uani 1 1 d . . . . .
H4 H 0.5277(12) 0.2531(9) 0.4696(5) 0.012(2) Uiso 1 1 d . . . . .
C5 C 0.52316(6) 0.45564(4) 0.34035(2) 0.00791(8) Uani 1 1 d . . . . .
H5 H 0.5430(12) 0.5223(9) 0.3259(5) 0.016(3) Uiso 1 1 d . . . . .
C6 C 0.64069(6) 0.41818(4) 0.38351(2) 0.00873(8) Uani 1 1 d . . . . .
H6 H 0.7115(12) 0.4681(9) 0.3865(5) 0.013(2) Uiso 1 1 d . . . . .
O13 O 0.00853(7) 0.56204(4) 0.46488(3) 0.02145(11) Uani 1 1 d . . . . .
C7 C 0.000000 0.500000 0.500000 0.01568(15) Uani 1 2 d S . P . .
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
_geom_angle_publ_flag
N7 N1 C5 118.75(5) . . ?
N7 N1 C1 119.40(5) . . ?
C5 N1 C1 110.14(4) . . ?
N8 N2 C3 118.75(5) . . ?
N8 N2 C1 118.74(5) . . ?
C3 N2 C1 117.26(5) . . ?
N9 N3 C6 115.96(5) . . ?
N9 N3 C3 114.99(5) . . ?
C6 N3 C3 107.43(4) . . ?
N10 N4 C6 120.35(5) . . ?
N10 N4 C4 121.04(5) . . ?
C6 N4 C4 109.47(4) . . ?
N11 N5 C4 118.02(4) . . ?
N11 N5 C2 117.23(4) . . ?
C4 N5 C2 116.64(4) . . ?
N12 N6 C5 117.46(5) . . ?
N12 N6 C2 116.17(5) . . ?
C5 N6 C2 108.74(4) . . ?
O1 N7 O2 126.46(5) . . ?
O1 N7 N1 117.16(5) . . ?
O2 N7 N1 116.37(5) . . ?
O3 N8 O4 127.17(6) . . ?
O3 N8 N2 116.31(5) . . ?
O4 N8 N2 116.44(6) . . ?
O6 N9 O5 127.93(6) . . ?
O6 N9 N3 116.49(5) . . ?
O5 N9 N3 115.43(5) . . ?
O8 N10 O7 126.53(6) . . ?
O8 N10 N4 116.73(5) . . ?
O7 N10 N4 116.60(5) . . ?
O10 N11 O9 126.46(5) . . ?
O10 N11 N5 117.00(5) . . ?
O9 N11 N5 116.43(5) . . ?
O12 N12 O11 127.47(5) . . ?
O12 N12 N6 116.93(5) . . ?
O11 N12 N6 115.42(5) . . ?
N2 C1 N1 113.98(5) . . ?
N2 C1 C2 108.67(4) . . ?
N1 C1 C2 100.41(4) . . ?
N2 C1 H1 109.3(7) . . ?
N1 C1 H1 111.0(7) . . ?
C2 C1 H1 113.3(7) . . ?
N5 C2 N6 110.66(4) . . ?
N5 C2 C1 107.80(4) . . ?
N6 C2 C1 105.19(4) . . ?
N5 C2 H2 109.3(7) . . ?
N6 C2 H2 111.2(7) . . ?
C1 C2 H2 112.5(7) . . ?
N2 C3 N3 110.40(5) . . ?
N2 C3 C4 108.66(4) . . ?
N3 C3 C4 105.04(4) . . ?
N2 C3 H3 108.0(7) . . ?
N3 C3 H3 111.1(7) . . ?
C4 C3 H3 113.6(7) . . ?
N5 C4 N4 111.47(5) . . ?
N5 C4 C3 107.60(4) . . ?
N4 C4 C3 103.08(4) . . ?
N5 C4 H4 109.8(7) . . ?
N4 C4 H4 111.9(7) . . ?
C3 C4 H4 112.8(7) . . ?
N6 C5 N1 99.64(4) . . ?
N6 C5 C6 109.34(4) . . ?
N1 C5 C6 112.40(4) . . ?
N6 C5 H5 111.7(7) . . ?
N1 C5 H5 111.9(7) . . ?
C6 C5 H5 111.3(7) . . ?
N4 C6 N3 103.43(4) . . ?
N4 C6 C5 108.56(4) . . ?
N3 C6 C5 108.75(4) . . ?
N4 C6 H6 113.9(7) . . ?
N3 C6 H6 111.8(7) . . ?
C5 C6 H6 110.2(7) . . ?
O13 C7 O13 180.0 5_566 . ?
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
O1 N7 1.2241(7) . ?
O2 N7 1.2277(7) . ?
O3 N8 1.2135(8) . ?
O4 N8 1.2174(8) . ?
O5 N9 1.2132(8) . ?
O6 N9 1.2130(8) . ?
O7 N10 1.2259(7) . ?
O8 N10 1.2210(7) . ?
O9 N11 1.2266(7) . ?
O10 N11 1.2146(7) . ?
O11 N12 1.2159(7) . ?
O12 N12 1.2158(7) . ?
N1 N7 1.3741(7) . ?
N1 C5 1.4636(7) . ?
N1 C1 1.4786(7) . ?
N2 N8 1.4075(7) . ?
N2 C3 1.4372(8) . ?
N2 C1 1.4419(8) . ?
N3 N9 1.4412(7) . ?
N3 C6 1.4648(8) . ?
N3 C3 1.4769(8) . ?
N4 N10 1.3825(7) . ?
N4 C6 1.4561(8) . ?
N4 C4 1.4639(8) . ?
N5 N11 1.3959(7) . ?
N5 C4 1.4483(7) . ?
N5 C2 1.4486(7) . ?
N6 N12 1.4208(7) . ?
N6 C5 1.4509(7) . ?
N6 C2 1.4732(8) . ?
C1 C2 1.5710(8) . ?
C1 H1 0.947(12) . ?
C2 H2 0.958(12) . ?
C3 C4 1.5783(8) . ?
C3 H3 0.930(12) . ?
C4 H4 0.952(11) . ?
C5 C6 1.5920(8) . ?
C5 H5 0.954(12) . ?
C6 H6 0.945(11) . ?
O13 C7 1.1570(6) . ?
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
C5 N1 N7 O1 -13.14(8) . . . . ?
C1 N1 N7 O1 -152.61(5) . . . . ?
C5 N1 N7 O2 168.05(5) . . . . ?
C1 N1 N7 O2 28.58(8) . . . . ?
C3 N2 N8 O3 -174.86(5) . . . . ?
C1 N2 N8 O3 -21.14(8) . . . . ?
C3 N2 N8 O4 8.27(8) . . . . ?
C1 N2 N8 O4 161.99(6) . . . . ?
C6 N3 N9 O6 -21.03(8) . . . . ?
C3 N3 N9 O6 -147.52(6) . . . . ?
C6 N3 N9 O5 163.18(5) . . . . ?
C3 N3 N9 O5 36.69(7) . . . . ?
C6 N4 N10 O8 -164.66(5) . . . . ?
C4 N4 N10 O8 -21.22(8) . . . . ?
C6 N4 N10 O7 19.32(8) . . . . ?
C4 N4 N10 O7 162.77(5) . . . . ?
C4 N5 N11 O10 160.31(5) . . . . ?
C2 N5 N11 O10 12.62(7) . . . . ?
C4 N5 N11 O9 -23.35(7) . . . . ?
C2 N5 N11 O9 -171.04(5) . . . . ?
C5 N6 N12 O12 -23.60(8) . . . . ?
C2 N6 N12 O12 -154.80(5) . . . . ?
C5 N6 N12 O11 160.84(5) . . . . ?
C2 N6 N12 O11 29.63(7) . . . . ?
N8 N2 C1 N1 -98.99(6) . . . . ?
C3 N2 C1 N1 55.12(6) . . . . ?
N8 N2 C1 C2 149.96(5) . . . . ?
C3 N2 C1 C2 -55.94(6) . . . . ?
N7 N1 C1 N2 54.23(7) . . . . ?
C5 N1 C1 N2 -88.40(5) . . . . ?
N7 N1 C1 C2 170.22(5) . . . . ?
C5 N1 C1 C2 27.58(5) . . . . ?
N11 N5 C2 N6 92.91(6) . . . . ?
C4 N5 C2 N6 -55.22(6) . . . . ?
N11 N5 C2 C1 -152.56(5) . . . . ?
C4 N5 C2 C1 59.31(6) . . . . ?
N12 N6 C2 N5 -129.44(5) . . . . ?
C5 N6 C2 N5 95.39(5) . . . . ?
N12 N6 C2 C1 114.39(5) . . . . ?
C5 N6 C2 C1 -20.78(5) . . . . ?
N2 C1 C2 N5 -2.12(6) . . . . ?
N1 C1 C2 N5 -122.00(5) . . . . ?
N2 C1 C2 N6 116.00(5) . . . . ?
N1 C1 C2 N6 -3.89(5) . . . . ?
N8 N2 C3 N3 96.76(6) . . . . ?
C1 N2 C3 N3 -57.34(6) . . . . ?
N8 N2 C3 C4 -148.55(5) . . . . ?
C1 N2 C3 C4 57.35(6) . . . . ?
N9 N3 C3 N2 -132.46(5) . . . . ?
C6 N3 C3 N2 96.79(5) . . . . ?
N9 N3 C3 C4 110.58(5) . . . . ?
C6 N3 C3 C4 -20.17(6) . . . . ?
N11 N5 C4 N4 -93.34(6) . . . . ?
C2 N5 C4 N4 54.54(6) . . . . ?
N11 N5 C4 C3 154.34(5) . . . . ?
C2 N5 C4 C3 -57.78(6) . . . . ?
N10 N4 C4 N5 118.77(6) . . . . ?
C6 N4 C4 N5 -94.27(5) . . . . ?
N10 N4 C4 C3 -126.09(5) . . . . ?
C6 N4 C4 C3 20.88(6) . . . . ?
N2 C3 C4 N5 -0.43(6) . . . . ?
N3 C3 C4 N5 117.71(5) . . . . ?
N2 C3 C4 N4 -118.33(5) . . . . ?
N3 C3 C4 N4 -0.19(5) . . . . ?
N12 N6 C5 N1 -98.10(5) . . . . ?
C2 N6 C5 N1 36.42(5) . . . . ?
N12 N6 C5 C6 143.91(5) . . . . ?
C2 N6 C5 C6 -81.57(5) . . . . ?
N7 N1 C5 N6 176.83(5) . . . . ?
C1 N1 C5 N6 -40.26(5) . . . . ?
N7 N1 C5 C6 -67.49(6) . . . . ?
C1 N1 C5 C6 75.42(6) . . . . ?
N10 N4 C6 N3 113.49(5) . . . . ?
C4 N4 C6 N3 -33.74(6) . . . . ?
N10 N4 C6 C5 -131.12(5) . . . . ?
C4 N4 C6 C5 81.65(5) . . . . ?
N9 N3 C6 N4 -97.37(5) . . . . ?
C3 N3 C6 N4 32.83(6) . . . . ?
N9 N3 C6 C5 147.38(5) . . . . ?
C3 N3 C6 C5 -82.42(5) . . . . ?
N6 C5 C6 N4 -0.25(6) . . . . ?
N1 C5 C6 N4 -109.92(5) . . . . ?
N6 C5 C6 N3 111.63(5) . . . . ?
N1 C5 C6 N3 1.96(6) . . . . ?
