#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:14:17 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567748.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_1567748
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         'C3 H6 N2 O'
_chemical_formula_sum            'C3 H6 N2 O'
_chemical_formula_weight         86.10
_chemical_name_common            2-imidizolidinone
_chemical_name_systematic        2-imidizolidinone
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   9.9700(4)
_cell_length_b                   11.8236(5)
_cell_length_c                   13.3559(5)
_cell_measurement_reflns_used    1173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9170
_cell_measurement_theta_min      6.6760
_cell_volume                     1574.41(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.969
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1497
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.509
_diffrn_reflns_theta_min         6.688
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58733
_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    1.453
_exptl_crystal_description       irregular
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0169(16)
_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   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     30
_refine_ls_number_reflns         404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0636P)²+1.7705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                385
_reflns_number_total             404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03015b2.cif
_cod_data_source_block           2-imidizolidinone
_cod_depositor_comments
'Adding full bibliography for 1567748--1567754.cif.'
_cod_original_cell_volume        1574.40(11)
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               1567748
_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_res_file
;
TITL mkb-4-160_a.res in Fddd
    mkb-4-160.res
    created by SHELXL-2018/3 at 10:54:18 on 29-Nov-2021
REM Old TITL MKB-4-160 in Fddd
REM SHELXT solution in Fddd: R1 0.260, Rweak 0.395, Alpha 0.037
REM <I/s> 0.387 for 53 systematic absences, Orientation as input
REM Formula found by SHELXT: C5 O
CELL 1.54184 9.969953 11.823642 13.355855 90 90 90
ZERR 16 0.000419 0.000474 0.000482 0 0 0
LATT 4
SYMM 0.75-X,0.75-Y,+Z
SYMM 0.75-X,+Y,0.75-Z
SYMM +X,0.75-Y,0.75-Z
SFAC C H N O
UNIT 48 96 32 16

L.S. 4
PLAN  5
CONF
BOND $H
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\MKB-4-160.hkl">
REM </olex2.extras>

WGHT    0.063600    1.770500
EXTI    0.016933
FVAR       7.52792
O4    4    0.375000    0.375000    0.767856    10.50000    0.07280    0.05202 =
         0.03618    0.00000    0.00000   -0.00347
N1    3    0.439401    0.301292    0.616339    11.00000    0.08814    0.06786 =
         0.04114    0.00589    0.00657    0.03564
AFIX  43
H1    2    0.484686    0.244799    0.638750    11.00000   -1.20000
AFIX   0
C3    1    0.375000    0.375000    0.675772    10.50000    0.04641    0.03973 =
         0.03779    0.00000    0.00000   -0.00545
C2    1    0.425207    0.326081    0.511809    11.00000    0.06556    0.05307 =
         0.03938   -0.00258    0.00406    0.00541
AFIX  23
H2A   2    0.390446    0.261420    0.475412    11.00000   -1.20000
H2B   2    0.510122    0.348753    0.482588    11.00000   -1.20000
AFIX   0
HKLF 4




REM  mkb-4-160_a.res in Fddd
REM wR2 = 0.1285, GooF = S = 1.136, Restrained GooF = 1.136 for all data
REM R1 = 0.0524 for 385 Fo > 4sig(Fo) and 0.0535 for all 404 data
REM 30 parameters refined using 0 restraints

END

WGHT      0.0636      1.7705

REM Highest difference peak  0.187,  deepest hole -0.276,  1-sigma level  0.080
Q1    1   0.6477  0.3480  0.5059  11.00000  0.05    0.19
Q2    1   0.6250  0.3400  0.6250  10.50000  0.05    0.18
Q3    1   0.5893  0.3393  0.6664  11.00000  0.05    0.17
Q4    1   0.4961  0.3441  0.5909  11.00000  0.05    0.16
Q5    1   0.4869  0.3544  0.6240  11.00000  0.05    0.15
;
_shelx_res_checksum              73128
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'
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
O4 O 0.375000 0.375000 0.76786(11) 0.0537(6) Uani 1 2 d S T P . .
N1 N 0.43940(18) 0.30129(14) 0.61634(10) 0.0657(7) Uani 1 1 d . . . . .
H1 H 0.484686 0.244799 0.638750 0.079 Uiso 1 1 calc R U . . .
C3 C 0.375000 0.375000 0.67577(15) 0.0413(6) Uani 1 2 d S T P . .
C2 C 0.42521(19) 0.32608(15) 0.51181(11) 0.0527(6) Uani 1 1 d . . . . .
H2A H 0.390446 0.261420 0.475412 0.063 Uiso 1 1 calc R U . . .
H2B H 0.510122 0.348753 0.482588 0.063 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0728(12) 0.0520(10) 0.0362(9) 0.000 0.000 -0.0035(8)
N1 0.0881(12) 0.0679(10) 0.0411(9) 0.0059(6) 0.0066(7) 0.0356(8)
C3 0.0464(11) 0.0397(10) 0.0378(11) 0.000 0.000 -0.0055(8)
C2 0.0656(11) 0.0531(10) 0.0394(9) -0.0026(7) 0.0041(7) 0.0054(8)
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
C3 N1 C2 113.32(14) . . ?
C3 N1 H1 123.3 . . ?
C2 N1 H1 123.3 . . ?
O4 C3 N1 126.25(9) . 2 ?
O4 C3 N1 126.25(9) . . ?
N1 C3 N1 107.50(19) 2 . ?
N1 C2 C2 102.66(9) . 2 ?
N1 C2 H2A 111.2 . . ?
C2 C2 H2A 111.2 2 . ?
N1 C2 H2B 111.2 . . ?
C2 C2 H2B 111.2 2 . ?
H2A C2 H2B 109.1 . . ?
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
O4 C3 1.230(3) . ?
N1 C3 1.3423(19) . ?
N1 C2 1.434(2) . ?
N1 H1 0.8600 . ?
C2 C2 1.530(3) 2 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
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
C2 N1 C3 O4 -177.39(10) . . . . ?
C2 N1 C3 N1 2.61(10) . . . 2 ?
C3 N1 C2 C2 -6.2(2) . . . 2 ?
