# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1mhmgcl
_database_code_depnum_ccdc_archive 'CCDC 2010673'
loop_
_audit_author_name
_audit_author_address
'Jose Paixao'
;University of Coimbra
Portugal
;
_audit_update_record             
;
2020-06-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        1-methylimidazolidine-2,4-dione
_chemical_name_common            1-methylhydantoin
_chemical_melting_point          428.85
_chemical_formula_moiety         'C4 H6 N2 O2'
_chemical_formula_sum            'C4 H6 N2 O2'
_chemical_formula_weight         114.11

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8466(2)
_cell_length_b                   9.8257(3)
_cell_length_c                   20.3107(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1565.92(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5786
_cell_measurement_theta_min      5.769
_cell_measurement_theta_max      55.894

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8773
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  
;
Bruker APEXII CCD area-detector diffractometer  
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45996
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3888
_reflns_number_gt                2898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       'APEXIII (Bruker AXS, 2016)'
_computing_cell_refinement       'APEXIII (Bruker AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.1746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_number_reflns         3888
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1A N 0.5594(2) 0.4987(2) 0.48573(11) 0.0435(5) Uani 1 1 d . . . . .
N3A N 0.2989(2) 0.4161(2) 0.48715(10) 0.0397(5) Uani 1 1 d . . . . .
H8A H 0.228(3) 0.358(3) 0.4916(12) 0.048 Uiso 1 1 d . U . . .
O7A O 0.5256(2) 0.26703(18) 0.49530(10) 0.0520(5) Uani 1 1 d . . . . .
O9A O 0.1379(2) 0.60983(18) 0.47874(11) 0.0630(5) Uani 1 1 d . . . . .
C2A C 0.4711(3) 0.3828(2) 0.49033(11) 0.0359(5) Uani 1 1 d . . . . .
C4A C 0.2724(3) 0.5512(2) 0.48073(13) 0.0410(5) Uani 1 1 d . . . . .
C5A C 0.4481(3) 0.6142(2) 0.47587(14) 0.0439(6) Uani 1 1 d . . . . .
H10A H 0.466245 0.655267 0.433011 0.053 Uiso 1 1 calc R U . . .
H11A H 0.465099 0.682536 0.509714 0.053 Uiso 1 1 calc R U . . .
C6A C 0.7434(3) 0.5077(3) 0.48384(15) 0.0516(6) Uani 1 1 d . . . . .
H12A H 0.791468 0.418604 0.489360 0.077 Uiso 1 1 calc R U . . .
H13A H 0.782139 0.565992 0.518695 0.077 Uiso 1 1 calc R U . . .
H14A H 0.778527 0.544522 0.442225 0.077 Uiso 1 1 calc R U . . .
N1B N -0.0698(2) 0.7385(2) 0.33139(10) 0.0419(5) Uani 1 1 d . . . . .
N3B N 0.1830(2) 0.64396(19) 0.32064(10) 0.0389(4) Uani 1 1 d . . . . .
H8B H 0.259(3) 0.582(3) 0.3174(12) 0.047 Uiso 1 1 d . U . . .
O7B O -0.0562(2) 0.50869(17) 0.31127(11) 0.0545(5) Uani 1 1 d . . . . .
C4B C 0.2190(3) 0.7759(2) 0.33337(12) 0.0396(5) Uani 1 1 d . . . . .
O9B O 0.3592(2) 0.82506(19) 0.34004(11) 0.0648(6) Uani 1 1 d . . . . .
C2B C 0.0072(3) 0.6205(2) 0.32061(11) 0.0377(5) Uani 1 1 d . . . . .
C5B C 0.0514(3) 0.8487(2) 0.33773(13) 0.0416(6) Uani 1 1 d . . . . .
H10B H 0.038974 0.894962 0.379636 0.050 Uiso 1 1 calc R U . . .
H11B H 0.038601 0.914196 0.302343 0.050 Uiso 1 1 calc R U . . .
C6B C -0.2528(3) 0.7590(3) 0.33289(14) 0.0524(7) Uani 1 1 d . . . . .
H12B H -0.284245 0.824710 0.300087 0.079 Uiso 1 1 calc R U . . .
H13B H -0.285940 0.791540 0.375582 0.079 Uiso 1 1 calc R U . . .
H14B H -0.309377 0.674343 0.323997 0.079 Uiso 1 1 calc R U . . .
N1C N 0.4233(2) 0.2309(2) 0.33671(10) 0.0428(5) Uani 1 1 d . . . . .
N3C N 0.6824(2) 0.31467(19) 0.33074(10) 0.0402(5) Uani 1 1 d . . . . .
H8C H 0.758(4) 0.375(3) 0.3261(12) 0.048 Uiso 1 1 d . U . . .
O7C O 0.4539(2) 0.45993(17) 0.31755(11) 0.0564(5) Uani 1 1 d . . . . .
O9C O 0.8466(2) 0.12548(18) 0.34908(11) 0.0650(6) Uani 1 1 d . . . . .
C2C C 0.5097(3) 0.3463(2) 0.32720(12) 0.0376(5) Uani 1 1 d . . . . .
C4C C 0.7107(3) 0.1812(2) 0.34296(12) 0.0424(5) Uani 1 1 d . . . . .
C5C C 0.5358(3) 0.1165(2) 0.34718(15) 0.0467(6) Uani 1 1 d . . . . .
H10C H 0.520712 0.047826 0.313351 0.056 Uiso 1 1 calc R U . . .
H11C H 0.517036 0.075482 0.390016 0.056 Uiso 1 1 calc R U . . .
C6C C 0.2396(3) 0.2195(3) 0.34020(15) 0.0552(7) Uani 1 1 d . . . . .
H12C H 0.189085 0.306793 0.331901 0.083 Uiso 1 1 calc R U . . .
H13C H 0.207166 0.188535 0.383241 0.083 Uiso 1 1 calc R U . . .
H14C H 0.200785 0.155534 0.307765 0.083 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1A C2A 1.336(3) . ?
N1A C6A 1.446(3) . ?
N1A C5A 1.446(3) . ?
N3A C4A 1.349(3) . ?
N3A C2A 1.392(3) . ?
N3A H8A 0.80(3) . ?
O7A C2A 1.219(3) . ?
O9A C4A 1.203(3) . ?
C4A C5A 1.515(3) . ?
C5A H10A 0.9700 . ?
C5A H11A 0.9700 . ?
C6A H12A 0.9600 . ?
C6A H13A 0.9600 . ?
C6A H14A 0.9600 . ?
N1B C2B 1.326(3) . ?
N1B C5B 1.447(3) . ?
N1B C6B 1.451(3) . ?
N3B C4B 1.352(3) . ?
N3B C2B 1.398(3) . ?
N3B H8B 0.86(3) . ?
O7B C2B 1.220(3) . ?
C4B O9B 1.209(3) . ?
C4B C5B 1.500(3) . ?
C5B H10B 0.9700 . ?
C5B H11B 0.9700 . ?
C6B H12B 0.9600 . ?
C6B H13B 0.9600 . ?
C6B H14B 0.9600 . ?
N1C C2C 1.335(3) . ?
N1C C5C 1.445(3) . ?
N1C C6C 1.447(3) . ?
N3C C4C 1.353(3) . ?
N3C C2C 1.392(3) . ?
N3C H8C 0.84(3) . ?
O7C C2C 1.215(3) . ?
O9C C4C 1.205(3) . ?
C4C C5C 1.515(3) . ?
C5C H10C 0.9700 . ?
C5C H11C 0.9700 . ?
C6C H12C 0.9600 . ?
C6C H13C 0.9600 . ?
C6C H14C 0.9600 . ?

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
C2A N1A C6A 124.9(2) . . ?
C2A N1A C5A 111.41(18) . . ?
C6A N1A C5A 123.4(2) . . ?
C4A N3A C2A 112.66(18) . . ?
C4A N3A H8A 127(2) . . ?
C2A N3A H8A 120(2) . . ?
O7A C2A N1A 128.2(2) . . ?
O7A C2A N3A 124.3(2) . . ?
N1A C2A N3A 107.46(19) . . ?
O9A C4A N3A 127.6(2) . . ?
O9A C4A C5A 126.9(2) . . ?
N3A C4A C5A 105.56(18) . . ?
N1A C5A C4A 102.70(18) . . ?
N1A C5A H10A 111.2 . . ?
C4A C5A H10A 111.2 . . ?
N1A C5A H11A 111.2 . . ?
C4A C5A H11A 111.2 . . ?
H10A C5A H11A 109.1 . . ?
N1A C6A H12A 109.5 . . ?
N1A C6A H13A 109.5 . . ?
H12A C6A H13A 109.5 . . ?
N1A C6A H14A 109.5 . . ?
H12A C6A H14A 109.5 . . ?
H13A C6A H14A 109.5 . . ?
C2B N1B C5B 111.71(17) . . ?
C2B N1B C6B 125.2(2) . . ?
C5B N1B C6B 123.0(2) . . ?
C4B N3B C2B 111.40(19) . . ?
C4B N3B H8B 123.8(18) . . ?
C2B N3B H8B 124.4(18) . . ?
O9B C4B N3B 126.5(2) . . ?
O9B C4B C5B 127.0(2) . . ?
N3B C4B C5B 106.54(18) . . ?
O7B C2B N1B 128.8(2) . . ?
O7B C2B N3B 123.4(2) . . ?
N1B C2B N3B 107.76(19) . . ?
N1B C5B C4B 102.38(17) . . ?
N1B C5B H10B 111.3 . . ?
C4B C5B H10B 111.3 . . ?
N1B C5B H11B 111.3 . . ?
C4B C5B H11B 111.3 . . ?
H10B C5B H11B 109.2 . . ?
N1B C6B H12B 109.5 . . ?
N1B C6B H13B 109.5 . . ?
H12B C6B H13B 109.5 . . ?
N1B C6B H14B 109.5 . . ?
H12B C6B H14B 109.5 . . ?
H13B C6B H14B 109.5 . . ?
C2C N1C C5C 111.83(18) . . ?
C2C N1C C6C 125.4(2) . . ?
C5C N1C C6C 122.7(2) . . ?
C4C N3C C2C 112.67(19) . . ?
C4C N3C H8C 125.7(18) . . ?
C2C N3C H8C 121.6(18) . . ?
O7C C2C N1C 128.4(2) . . ?
O7C C2C N3C 124.3(2) . . ?
N1C C2C N3C 107.31(19) . . ?
O9C C4C N3C 127.2(2) . . ?
O9C C4C C5C 127.2(2) . . ?
N3C C4C C5C 105.58(19) . . ?
N1C C5C C4C 102.60(18) . . ?
N1C C5C H10C 111.2 . . ?
C4C C5C H10C 111.2 . . ?
N1C C5C H11C 111.2 . . ?
C4C C5C H11C 111.2 . . ?
H10C C5C H11C 109.2 . . ?
N1C C6C H12C 109.5 . . ?
N1C C6C H13C 109.5 . . ?
H12C C6C H13C 109.5 . . ?
N1C C6C H14C 109.5 . . ?
H12C C6C H14C 109.5 . . ?
H13C C6C H14C 109.5 . . ?

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
_geom_hbond_publ_flag
N3A H8A O7A 0.80(3) 2.03(3) 2.822(2) 172(3) 4_456 yes
N3B H8B O7C 0.86(3) 1.94(3) 2.792(2) 171(3) . yes
N3C H8C O7B 0.84(3) 1.99(3) 2.828(2) 176(2) 1_655 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.053

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
