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#$Date: 2022-11-07 07:14:17 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567750.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_1567750
loop_
_publ_author_name
'Bellas, Michael K.'
'Matzger, Adam J.'
_publ_section_title
;
 Discovery strategy leads to the first melt-castable cocrystal based on an
 energetic oxidizing salt
;
_journal_issue                   41
_journal_name_full               'Chemical Science'
_journal_page_first              12100
_journal_page_last               12106
_journal_paper_doi               10.1039/D2SC03015B
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'N3 O4, 2(C H4 N2 O), H4 N'
_chemical_formula_sum            'C2 H12 N8 O6'
_chemical_formula_weight         244.20
_chemical_melting_point          347
_chemical_name_common            'ammonium dinitramide urea cocrystal'
_chemical_name_systematic        'ammonium dinitramide urea cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.778(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6572(4)
_cell_length_b                   3.71857(12)
_cell_length_c                   20.3958(7)
_cell_measurement_reflns_used    3036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2460
_cell_measurement_theta_min      4.4830
_cell_volume                     1052.48(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         3.269
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       'abnormal rod'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0014(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_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)+(0.0691P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1616
_reflns_number_total             1873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03015b2.cif
_cod_data_source_block           ADN-Urea
_cod_depositor_comments
'Adding full bibliography for 1567748--1567754.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1567750
_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.
;
loop_
_space_group_symop_operation_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_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 0.30992(8) 0.1813(3) 0.58778(6) 0.0499(3) Uani 1 1 d . . . . .
O5 O 0.54614(8) 0.8665(4) 0.58411(6) 0.0507(3) Uani 1 1 d . . . . .
N12 N 0.65132(9) 0.5875(4) 0.87291(7) 0.0450(4) Uani 1 1 d . . . . .
N10 N 0.49938(9) 0.3477(4) 0.85189(7) 0.0468(4) Uani 1 1 d . . . . .
O9 O 0.51683(10) 0.2298(5) 0.90988(7) 0.0741(5) Uani 1 1 d . . . . .
N16 N 0.37033(12) 0.5882(5) 0.49541(8) 0.0476(4) Uani 1 1 d D . . . .
H16A H 0.3466(16) 0.440(6) 0.5205(11) 0.071 Uiso 1 1 d D U . . .
H16B H 0.3918(17) 0.446(6) 0.4697(11) 0.071 Uiso 1 1 d D U . . .
O14 O 0.70247(10) 0.7649(5) 0.84776(8) 0.0770(5) Uani 1 1 d . . . . .
N11 N 0.56124(9) 0.5397(4) 0.82743(7) 0.0479(4) Uani 1 1 d . . . . .
O15 O 0.68303(10) 0.4710(5) 0.93085(8) 0.0836(6) Uani 1 1 d . . . . .
N8 N 0.64485(10) 0.7023(5) 0.68960(8) 0.0568(4) Uani 1 1 d . . . . .
H8A H 0.690410 0.651430 0.673096 0.068 Uiso 1 1 calc R U . . .
H8B H 0.653615 0.674702 0.733061 0.068 Uiso 1 1 calc R U . . .
N7 N 0.49304(11) 0.8985(5) 0.67587(7) 0.0535(4) Uani 1 1 d . . . . .
H7A H 0.437781 0.977834 0.650618 0.064 Uiso 1 1 calc R U . . .
H7B H 0.504570 0.867351 0.719576 0.064 Uiso 1 1 calc R U . . .
O13 O 0.42105(9) 0.2982(6) 0.80748(8) 0.0833(6) Uani 1 1 d . . . . .
N4 N 0.25691(11) 0.4168(5) 0.67074(8) 0.0578(4) Uani 1 1 d . . . . .
H4A H 0.312689 0.393573 0.701520 0.069 Uiso 1 1 calc R U . . .
H4B H 0.209913 0.506855 0.681908 0.069 Uiso 1 1 calc R U . . .
N3 N 0.15529(10) 0.3513(5) 0.56068(8) 0.0605(5) Uani 1 1 d . . . . .
H3A H 0.143429 0.284806 0.518366 0.073 Uiso 1 1 calc R U . . .
H3B H 0.110161 0.442550 0.573871 0.073 Uiso 1 1 calc R U . . .
C2 C 0.24327(11) 0.3130(4) 0.60565(8) 0.0413(4) Uani 1 1 d . . . . .
C6 C 0.56014(11) 0.8247(4) 0.64755(8) 0.0400(4) Uani 1 1 d . . . . .
H16C H 0.4224(16) 0.714(6) 0.5221(11) 0.057(6) Uiso 1 1 d . . . . .
H16D H 0.326(2) 0.716(7) 0.4714(14) 0.078(8) 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 0.0181 0.0091 '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 0.0311 0.0180 '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
_geom_angle_publ_flag
O15 N12 O14 120.61(14) . . ?
O15 N12 N11 127.37(14) . . ?
O14 N12 N11 112.00(14) . . ?
O9 N10 O13 121.40(15) . . ?
O9 N10 N11 126.14(13) . . ?
O13 N10 N11 112.45(14) . . ?
H16A N16 H16B 105(2) . . ?
H16A N16 H16C 112(2) . . ?
H16B N16 H16C 106(2) . . ?
H16A N16 H16D 109(2) . . ?
H16B N16 H16D 111(2) . . ?
H16C N16 H16D 114(2) . . ?
N12 N11 N10 115.56(12) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
O1 C2 N3 121.20(15) . . ?
O1 C2 N4 121.58(15) . . ?
N3 C2 N4 117.22(15) . . ?
O5 C6 N7 121.92(14) . . ?
O5 C6 N8 120.84(15) . . ?
N7 C6 N8 117.23(14) . . ?
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 C2 1.2475(19) . ?
O5 C6 1.2527(19) . ?
N12 O15 1.2027(19) . ?
N12 O14 1.2281(19) . ?
N12 N11 1.3591(19) . ?
N10 O9 1.2090(19) . ?
N10 O13 1.2260(19) . ?
N10 N11 1.368(2) . ?
N16 H16A 0.895(16) . ?
N16 H16B 0.872(16) . ?
N16 H16C 0.91(2) . ?
N16 H16D 0.82(3) . ?
N8 C6 1.341(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N7 C6 1.320(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N4 C2 1.334(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N3 C2 1.328(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
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
O15 N12 N11 N10 2.5(3) . . . . ?
O14 N12 N11 N10 -179.27(16) . . . . ?
O9 N10 N11 N12 2.5(3) . . . . ?
O13 N10 N11 N12 -176.50(17) . . . . ?
