# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Rietveld223c
_database_code_depnum_ccdc_archive 'CCDC 1464782'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
# CIF-file generated for Rietveld223c
_audit_creation_date             'Feb 17 23:25:48 2016'
_audit_creation_method           'PLATON <TABLE ACC> option'


_chemical_name_common            'methyl urea'
_chemical_melting_point          ?
_chemical_formula_sum            'C2 H6 N2 O'
_chemical_formula_weight         74.09

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   4.6147(6)
_cell_length_b                   6.5781(12)
_cell_length_c                   12.9004(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.418(9)
_cell_angle_gamma                90
_cell_volume                     391.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      13
_cell_measurement_theta_max      63

_exptl_crystal_description       'powder sample'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'Not Measured'

_diffrn_ambient_temperature      223(1)
_diffrn_radiation_wavelength     1.540562
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  'curved quartz'
_diffrn_measurement_device_type  'Inel CPS120'

_refine_ls_wR_factor_gt          0.0731

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uiso 0.4081(12) 0.5122(8) 0.1717(5) 1.000 0.0500 . .
N1 N Uiso 0.8270(13) 0.6830(10) 0.1970(8) 1.000 0.0500 . .
N2 N Uiso 0.8249(12) 0.3849(9) 0.1074(5) 1.000 0.0500 . .
C1 C Uiso 0.6756(12) 0.5251(8) 0.1595(5) 1.000 0.0500 . .
C2 C Uiso 0.6887(11) 0.2109(12) 0.0603(7) 1.000 0.0500 . .
H1 H Uiso 0.7336(13) 0.7701(12) 0.2389(10) 1.000 0.0500 . .
H2 H Uiso 1.0099(13) 0.6844(10) 0.1898(8) 1.000 0.0500 . .
H3 H Uiso 0.8187(11) 0.1179(13) 0.0350(9) 1.000 0.0500 . .
H4 H Uiso 0.6006(11) 0.2546(18) -0.0074(6) 1.000 0.0500 . .
H5 H Uiso 0.5438(11) 0.1477(10) 0.0981(8) 1.000 0.0500 . .
H6 H Uiso 0.9997(12) 0.4055(8) 0.1042(4) 1.000 0.0500 . .

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.249(8) . . yes
N1 C1 1.340(9) . . yes
N2 C1 1.336(8) . . yes
N2 C2 1.438(10) . . yes
N1 H1 0.900(13) . . no
N1 H2 0.850(9) . . no
N2 H6 0.819(8) . . no
C2 H3 0.918(10) . . no
C2 H4 1.003(12) . . no
C2 H5 0.929(10) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 122.5(5) . . . yes
C1 N1 H1 117.4(7) . . . no
C1 N1 H2 119.0(9) . . . no
H1 N1 H2 122.6(11) . . . no
C2 N2 H6 122.5(7) . . . no
C1 N2 H6 115.0(7) . . . no
O1 C1 N2 122.1(6) . . . yes
N1 C1 N2 116.6(6) . . . yes
O1 C1 N1 121.4(6) . . . yes
N2 C2 H3 113.3(7) . . . no
N2 C2 H4 108.2(9) . . . no
N2 C2 H5 116.7(10) . . . no
H3 C2 H4 98.2(12) . . . no
H3 C2 H5 111.3(10) . . . no
H4 C2 H5 107.3(8) . . . no

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 N2 C1 O1 1.0(11) . . . . no
C2 N2 C1 N1 -178.1(7) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N1 2.928(8) . 1_455 no
O1 N2 2.933(8) . 1_455 no
O1 C1 3.384(8) . 1_455 no
O1 N1 2.960(10) . 2_645 no
O1 H5 2.655(9) . . no
O1 H6 2.186(8) . 1_455 no
O1 H2 2.173(8) . 1_455 no
O1 H1 2.075(11) . 2_645 no
O1 H4 2.617(11) . 3_665 no
N1 O1 2.928(8) . 1_655 no
N1 O1 2.960(10) . 2_655 no
N1 N2 3.264(11) . 2_755 no
N2 O1 2.933(8) . 1_655 no
N2 N1 3.264(11) . 2_745 no
N2 H1 2.932(12) . 2_745 no
C1 O1 3.384(8) . 1_655 no
C1 H1 2.852(10) . 2_645 no
C1 H4 2.746(11) . 3_665 no
H1 O1 2.075(11) . 2_655 no
H1 N2 2.932(12) . 2_755 no
H1 C1 2.852(10) . 2_655 no
H1 H5 2.598(14) . 2_655 no
H1 H6 2.524(12) . 2_755 no
H2 O1 2.173(8) . 1_655 no
H2 H6 2.142(9) . . no
H3 H3 2.458(11) . 3_755 no
H4 O1 2.617(11) . 3_665 no
H4 C1 2.746(11) . 3_665 no
H5 O1 2.655(9) . . no
H5 H1 2.598(14) . 2_645 no
H6 O1 2.186(8) . 1_655 no
H6 H2 2.142(9) . . no
H6 H1 2.524(12) . 2_745 no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O1 0.900(13) 2.075(11) 2.960(10) 167.7(8) 2_655 yes
N1 H2 O1 0.850(9) 2.173(8) 2.928(8) 147.9(8) 1_655 yes
N2 H6 O1 0.819(8) 2.186(8) 2.933(8) 151.6(7) 1_655 yes
#END

#_vrf_ATOM007-PLAT201
#;
#PROBLEM: _atom_site_aniso_label is missing and isotropic non H-atoms in main residues
#REPLY :  Rigid Body Direct Space mehtod (X-ray powder diffraction data) providing a unique Global Isotropic Factor
#;
#_vrf_PLAT029-PLAT183
#;
#PROBLEM: _diffrn_measured_fraction_theta_full Low  and missing cell measurement reflns
#REPLY : Crystal structure determined from X-ray Powder diffraction data not from single crystal X-ray diffraction data
#;
#_vrf_PLAT090-PLAT091
#;
#PROBLEM: Deviating Methyl C2 H-C-H Bond Angle and  Deviating Methyl C2 X-C-H Bond Angle
#REPLY : Bond lengths and angles of methyl urea molecule have been taken from the crystal structure of the stable phase determined
#from single crystal X-ray diffraction data
#;
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# 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_Rietveld100
_database_code_depnum_ccdc_archive 'CCDC 1464783'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;
# CIF-file generated for Rietveld100

_audit_creation_date             'Feb 17 23:25:48 2016'
_audit_creation_method           'PLATON <TABLE ACC> option'

_chemical_name_common            'methyl urea'
_chemical_melting_point          ?
_chemical_formula_sum            'C2 H6 N2 O'
_chemical_formula_weight         74.09

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   4.6604(3)
_cell_length_b                   7.4079(7)
_cell_length_c                   10.4566(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.007(4)
_cell_angle_gamma                90
_cell_volume                     360.78(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      12
_cell_measurement_theta_max      63

_exptl_crystal_description       'powder sample'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'Not Measured'

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.540562
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a~1~
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  'curved quartz'
_diffrn_measurement_device_type  'Inel CPS120'

_refine_ls_wR_factor_gt          0.1058

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uiso 0.4115(8) 0.4494(5) 0.3371(3) 1.000 0.0500 . .
N1 N Uiso 0.8141(12) 0.5941(5) 0.2988(4) 1.000 0.0500 . .
N2 N Uiso 0.8238(9) 0.3291(5) 0.4066(3) 1.000 0.0500 . .
C1 C Uiso 0.6787(9) 0.4585(4) 0.3475(2) 1.000 0.0500 . .
C2 C Uiso 0.7141(13) 0.1849(5) 0.4670(5) 1.000 0.0500 . .
H1 H Uiso 0.7197(15) 0.6809(6) 0.2492(5) 1.000 0.0500 . .
H2 H Uiso 1.0155(12) 0.5980(7) 0.3050(4) 1.000 0.0500 . .
H3 H Uiso 0.8527(16) 0.0865(6) 0.4946(6) 1.000 0.0500 . .
H4 H Uiso 0.6368(14) 0.2165(7) 0.5548(4) 1.000 0.0500 . .
H5 H Uiso 0.5464(14) 0.1188(5) 0.4181(6) 1.000 0.0500 . .
H6 H Uiso 1.0236(9) 0.3480(7) 0.4079(3) 1.000 0.0500 . .

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.248(6) . . yes
N1 C1 1.300(5) . . yes
N2 C1 1.315(5) . . yes
N2 C2 1.351(6) . . yes
N1 H1 0.927(7) . . no
N1 H2 0.939(8) . . no
N2 H6 0.941(6) . . no
C2 H3 1.009(8) . . no
C2 H4 1.025(7) . . no
C2 H5 1.041(8) . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 126.8(4) . . . yes
C1 N1 H1 121.9(7) . . . no
C1 N1 H2 119.6(5) . . . no
H1 N1 H2 118.1(7) . . . no
C2 N2 H6 120.1(5) . . . no
C1 N2 H6 113.0(5) . . . no
O1 C1 N2 119.8(3) . . . yes
N1 C1 N2 119.9(4) . . . yes
O1 C1 N1 120.3(4) . . . yes
N2 C2 H3 117.1(7) . . . no
N2 C2 H4 112.9(5) . . . no
N2 C2 H5 115.6(5) . . . no
H3 C2 H4 98.6(6) . . . no
H3 C2 H5 105.2(5) . . . no
H4 C2 H5 105.4(7) . . . no

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 N2 C1 O1 -4.2(5) . . . . no
C2 N2 C1 N1 176.6(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N1 2.997(7) . 1_455 no
O1 N2 2.994(6) . 1_455 no
O1 N1 3.154(5) . 2_645 no
O1 C1 3.408(4) . 3_666 no
O1 H5 2.660(6) . . no
O1 H2 2.165(7) . 1_455 no
O1 H1 2.260(6) . 2_645 no
O1 H6 2.115(6) . 1_455 no
O1 H4 2.733(6) . 3_666 no
N1 O1 2.997(7) . 1_655 no
N1 O1 3.154(5) . 2_655 no
N1 N2 3.278(6) . 2_755 no
N2 O1 2.994(6) . 1_655 no
N2 N1 3.278(6) . 2_745 no
N1 H5 2.781(8) . 2_655 no
N2 H1 2.937(7) . 2_745 no
N2 H2 2.916(6) . 2_745 no
C1 O1 3.408(4) . 3_666 no
C2 C2 3.473(7) . 3_656 no
C1 H1 2.927(7) . 2_645 no
C1 H4 3.018(6) . 3_666 no
C2 H1 2.980(8) . 2_645 no
C2 H3 2.868(8) . 3_756 no
C2 H5 2.843(7) . 3_656 no
H1 O1 2.260(6) . 2_655 no
H1 N2 2.937(7) . 2_755 no
H1 C1 2.927(7) . 2_655 no
H1 C2 2.980(8) . 2_655 no
H1 H5 2.158(9) . 2_655 no
H1 H6 2.408(7) . 2_755 no
H2 O1 2.165(7) . 1_655 no
H2 H6 2.142(7) . . no
H2 N2 2.916(6) . 2_755 no
H2 H4 2.549(7) . 3_766 no
H3 C2 2.868(8) . 3_756 no
H3 H3 1.879(9) . 3_756 no
H3 H5 2.593(9) . 3_656 no
H4 O1 2.733(6) . 3_666 no
H4 C1 3.018(6) . 3_666 no
H4 H2 2.549(7) . 3_766 no
H5 O1 2.660(6) . . no
H5 N1 2.781(8) . 2_645 no
H5 H1 2.158(9) . 2_645 no
H5 C2 2.843(7) . 3_656 no
H5 H3 2.593(9) . 3_656 no
H5 H5 2.504(7) . 3_656 no
H6 O1 2.115(6) . 1_655 no
H6 H2 2.142(7) . . no
H6 H1 2.408(7) . 2_745 no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O1 0.927(7) 2.260(6) 3.154(5) 161.8(6) 2_655 yes
N1 H2 O1 0.939(8) 2.165(7) 2.997(7) 147.1(5) 1_655 yes
N2 H6 O1 0.941(6) 2.115(6) 2.994(6) 154.8(4) 1_655 yes
#END

#_vrf_ATOM007-PLAT201
#;
#PROBLEM: _atom_site_aniso_label is missing and isotropic non H-atoms in main residues
#REPLY :  Rigid Body Direct Space mehtod (X-ray powder diffraction data) providing a unique Global Isotropic Factor
#;
#_vrf_PLAT029-PLAT183
#;
#PROBLEM: _diffrn_measured_fraction_theta_full Low  and missing cell measurement reflns
#REPLY : Crystal structure determined from X-ray Powder diffraction data not from single crystal X-ray diffraction data
#;
#_vrf_PLAT413
#;
#PROBLEM: Short Inter XH3 .. XHn H3 .. H3
#REPLY : This defect in the crystal structure is attributed to the lower quality of the X-ray powder diffraction pattern measured
#at 100K. Furthermore, it concerns the positions of methyl hydrogen atoms which are hard to locate even using single crystal X-ray
#diffraction data
#;
#_vrf_PLAT090-PLAT091
#;
#PROBLEM: Deviating Methyl C2 H-C-H Bond Angle and  Deviating Methyl C2 X-C-H Bond Angle
#REPLY : Bond lengths and angles of methyl urea molecule have been taken from the crystal structure of the stable phase determined
#from single crystal X-ray diffraction data
#;
_exptl_crystal_recrystallization_method 'From the Melt'
