# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1867250'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_date             2017-12-23T17:14:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 3-(3-methylimidazolium-1-yl)propanoate dihydrate
;
_chemical_formula_moiety         'C7 H10 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C7 H14 N2 O4'
_chemical_formula_weight         190.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3825(4)
_cell_length_b                   8.4170(4)
_cell_length_c                   8.8371(4)
_cell_angle_alpha                113.2550(10)
_cell_angle_beta                 105.1800(10)
_cell_angle_gamma                95.990(2)
_cell_volume                     473.36(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    13851
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.7
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             204
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_number            13851
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.659
_diffrn_reflns_theta_max         25.737
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             1801
_reflns_number_gt                1662
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.1858P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.159(12)
_refine_ls_number_reflns         1801
_refine_ls_number_parameters     136
_refine_ls_number_restraints     4
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23604(13) 0.45046(13) 0.06392(13) 0.0328(3) Uani 1 d . .
O2 O 0.34737(14) 0.32497(13) 0.23593(13) 0.0348(3) Uani 1 d . .
O3 O 0.13499(16) 0.72619(14) 0.00112(14) 0.0362(3) Uani 1 d . .
H31 H 0.185(3) 0.647(2) 0.026(3) 0.060(6) Uiso 1 d . .
H32 H 0.010(2) 0.686(3) -0.022(3) 0.059(6) Uiso 1 d . .
O4 O 0.36723(17) 0.02869(16) 0.30529(15) 0.0398(3) Uani 1 d . .
H41 H 0.283(3) -0.062(2) 0.211(2) 0.063(6) Uiso 1 d . .
H42 H 0.376(3) 0.119(2) 0.281(3) 0.056(6) Uiso 1 d . .
N1 N 1.12861(15) 0.87703(14) 0.65812(13) 0.0222(3) Uani 1 d . .
N2 N 0.89710(15) 0.66252(14) 0.45035(14) 0.0228(3) Uani 1 d . .
C1 C 0.96837(18) 0.76169(16) 0.62178(16) 0.0226(3) Uani 1 d . .
H1 H 0.9137 0.7517 0.7047 0.027 Uiso 1 calc . .
C2 C 1.16106(19) 0.85154(18) 0.50477(17) 0.0269(3) Uani 1 d . .
H2 H 1.2656 0.916 0.4927 0.032 Uiso 1 calc . .
C3 C 1.01609(19) 0.71747(18) 0.37472(17) 0.0279(3) Uani 1 d . .
H3 H 0.9992 0.6698 0.2536 0.034 Uiso 1 calc . .
C4 C 1.2469(2) 1.01091(19) 0.83415(17) 0.0331(3) Uani 1 d . .
H4A H 1.2009 1.1207 0.8608 0.05 Uiso 1 calc . .
H4B H 1.3819 1.0353 0.84 0.05 Uiso 1 calc . .
H4C H 1.2369 0.9662 0.9193 0.05 Uiso 1 calc . .
C5 C 0.71750(18) 0.52213(17) 0.35899(17) 0.0265(3) Uani 1 d . .
H5A H 0.6804 0.4888 0.4442 0.032 Uiso 1 calc . .
H5B H 0.7401 0.4155 0.2718 0.032 Uiso 1 calc . .
C6 C 0.55414(18) 0.58129(17) 0.26804(17) 0.0253(3) Uani 1 d . .
H6A H 0.5879 0.6073 0.1776 0.03 Uiso 1 calc . .
H6B H 0.537 0.6923 0.3539 0.03 Uiso 1 calc . .
C7 C 0.36527(18) 0.44035(16) 0.18307(16) 0.0226(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C7 1.2601(16) . ?
O2 C7 1.2420(16) . ?
O3 H31 0.869(15) . ?
O3 H32 0.890(15) . ?
O4 H41 0.888(16) . ?
O4 H42 0.869(15) . ?
N1 C1 1.3267(16) . ?
N1 C2 1.3752(16) . ?
N1 C4 1.4667(16) . ?
N2 C1 1.3270(17) . ?
N2 C3 1.3781(17) . ?
N2 C5 1.4715(16) . ?
C1 H1 0.95 . ?
C2 C3 1.3488(19) . ?
C2 H2 0.95 . ?
C3 H3 0.95 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C6 1.5107(17) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.5226(17) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?

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
H31 O3 H32 102.1(19) . . ?
H41 O4 H42 106.9(19) . . ?
C1 N1 C2 108.81(10) . . ?
C1 N1 C4 124.59(11) . . ?
C2 N1 C4 126.59(11) . . ?
C1 N2 C3 108.46(11) . . ?
C1 N2 C5 124.88(11) . . ?
C3 N2 C5 126.64(11) . . ?
N1 C1 N2 108.65(11) . . ?
N1 C1 H1 125.7 . . ?
N2 C1 H1 125.7 . . ?
C3 C2 N1 106.88(11) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 107.20(11) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 111.91(10) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 111.90(10) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O2 C7 O1 124.36(11) . . ?
O2 C7 C6 118.53(11) . . ?
O1 C7 C6 117.10(11) . . ?

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 C1 N2 0.22(14) . . . . ?
C4 N1 C1 N2 179.08(11) . . . . ?
C3 N2 C1 N1 -0.29(14) . . . . ?
C5 N2 C1 N1 -178.50(11) . . . . ?
C1 N1 C2 C3 -0.06(15) . . . . ?
C4 N1 C2 C3 -178.90(12) . . . . ?
N1 C2 C3 N2 -0.11(15) . . . . ?
C1 N2 C3 C2 0.25(15) . . . . ?
C5 N2 C3 C2 178.41(12) . . . . ?
C1 N2 C5 C6 104.23(14) . . . . ?
C3 N2 C5 C6 -73.65(16) . . . . ?
N2 C5 C6 C7 -176.44(10) . . . . ?
C5 C6 C7 O2 20.80(17) . . . . ?
C5 C6 C7 O1 -159.94(12) . . . . ?


# END of CIF
_chemical_melting_point          334
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/diethyl ether'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1867251'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_date             2017-12-16T09:25:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 3-(3-methylimidazolium-1-yl)propanoate
;
_chemical_formula_moiety         'C7 H10 N2 O2'
_chemical_formula_sum            'C7 H10 N2 O2'
_chemical_formula_weight         154.17
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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                   6.6643(4)
_cell_length_b                   8.7065(5)
_cell_length_c                   12.8000(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     742.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      26.6
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'Bruker (SADABS-2014/5)'
_exptl_absorpt_special_details   ?


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_number            20701
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             1534
_reflns_number_gt                1492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.0914P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.083(10)
_refine_ls_number_reflns         1534
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0712
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69120(18) 0.53113(14) 0.12432(8) 0.0318(3) Uani 1 d . .
O2 O 0.77476(18) 0.45977(13) 0.28655(9) 0.0326(3) Uani 1 d . .
N1 N 0.30245(18) 0.46631(14) 0.47753(9) 0.0229(3) Uani 1 d . .
N2 N 0.46821(19) 0.64811(14) 0.40251(9) 0.0214(3) Uani 1 d . .
C1 C 0.4791(2) 0.53625(17) 0.47306(10) 0.0222(3) Uani 1 d . .
H1 H 0.594 0.5108 0.5134 0.027 Uiso 1 calc . .
C2 C 0.1740(2) 0.53530(17) 0.40689(12) 0.0262(3) Uani 1 d . .
H2 H 0.0385 0.5076 0.3937 0.031 Uiso 1 calc . .
C3 C 0.2776(2) 0.64952(17) 0.36005(11) 0.0249(3) Uani 1 d . .
H3 H 0.2287 0.7177 0.308 0.03 Uiso 1 calc . .
C4 C 0.2561(3) 0.33568(18) 0.54571(14) 0.0334(4) Uani 1 d . .
H4A H 0.2608 0.2404 0.505 0.05 Uiso 1 calc . .
H4B H 0.1217 0.3487 0.5754 0.05 Uiso 1 calc . .
H4C H 0.355 0.3306 0.6023 0.05 Uiso 1 calc . .
C5 C 0.6391(2) 0.74359(17) 0.37006(12) 0.0250(3) Uani 1 d . .
H5A H 0.7584 0.7159 0.4121 0.03 Uiso 1 calc . .
H5B H 0.6078 0.8529 0.3836 0.03 Uiso 1 calc . .
C6 C 0.6864(2) 0.72244(16) 0.25520(12) 0.0264(3) Uani 1 d . .
H6A H 0.8082 0.7827 0.2385 0.032 Uiso 1 calc . .
H6B H 0.5744 0.7658 0.2138 0.032 Uiso 1 calc . .
C7 C 0.7207(2) 0.55582(17) 0.22000(11) 0.0227(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1 C7 1.2588(18) . ?
O2 C7 1.2470(18) . ?
N1 C1 1.327(2) . ?
N1 C2 1.3823(19) . ?
N1 C4 1.466(2) . ?
N2 C1 1.3302(18) . ?
N2 C3 1.3819(19) . ?
N2 C5 1.4700(19) . ?
C1 H1 0.95 . ?
C2 C3 1.351(2) . ?
C2 H2 0.95 . ?
C3 H3 0.95 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 C6 1.515(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.536(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?

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
C1 N1 C2 108.77(12) . . ?
C1 N1 C4 124.64(13) . . ?
C2 N1 C4 126.58(13) . . ?
C1 N2 C3 108.89(13) . . ?
C1 N2 C5 124.30(12) . . ?
C3 N2 C5 126.60(12) . . ?
N1 C1 N2 108.47(12) . . ?
N1 C1 H1 125.8 . . ?
N2 C1 H1 125.8 . . ?
C3 C2 N1 107.10(13) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 N2 106.77(13) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 111.51(12) . . ?
N2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108 . . ?
C5 C6 C7 115.49(12) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
O2 C7 O1 126.52(14) . . ?
O2 C7 C6 118.42(12) . . ?
O1 C7 C6 115.06(13) . . ?

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 C1 N2 0.34(15) . . . . ?
C4 N1 C1 N2 179.37(12) . . . . ?
C3 N2 C1 N1 -0.16(15) . . . . ?
C5 N2 C1 N1 -175.20(12) . . . . ?
C1 N1 C2 C3 -0.38(16) . . . . ?
C4 N1 C2 C3 -179.39(13) . . . . ?
N1 C2 C3 N2 0.28(15) . . . . ?
C1 N2 C3 C2 -0.08(16) . . . . ?
C5 N2 C3 C2 174.81(13) . . . . ?
C1 N2 C5 C6 117.25(15) . . . . ?
C3 N2 C5 C6 -56.90(19) . . . . ?
N2 C5 C6 C7 -53.98(18) . . . . ?
C5 C6 C7 O2 -23.8(2) . . . . ?
C5 C6 C7 O1 156.56(13) . . . . ?


# END of CIF
_chemical_melting_point          445
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dry DMSO'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1867252'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_date             2017-12-23T17:03:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 3-(3-methylimidazolium-1-yl)propanoate monohydrate
;
_chemical_formula_moiety         'C7 H10 N2 O2, H2 O'
_chemical_formula_sum            'C7 H12 N2 O3'
_chemical_formula_weight         172.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7258(7)
_cell_length_b                   12.6758(12)
_cell_length_c                   8.8421(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.550(10)
_cell_angle_gamma                90
_cell_volume                     834.22(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1709
_cell_measurement_theta_min      4.1910
_cell_measurement_theta_max      28.1060
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_T_min  0.88000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.879
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3575
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_number            4951
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.505
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             1521
_reflns_number_gt                1286
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.2429P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.019(3)
_refine_ls_number_reflns         1521
_refine_ls_number_parameters     119
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O -0.08141(13) 0.21211(9) 0.86729(13) 0.0282(3) Uani 1 d . .
H32 H -0.153(2) 0.2445(15) 0.785(2) 0.055(6) Uiso 1 d . .
H31 H -0.144(2) 0.2070(15) 0.936(2) 0.050(6) Uiso 1 d . .
O1 O 0.71795(13) 0.19440(8) 1.08448(11) 0.0272(3) Uani 1 d . .
O2 O 0.43637(14) 0.17665(9) 1.09999(12) 0.0321(3) Uani 1 d . .
N2 N 0.26731(15) 0.05814(9) 0.64044(13) 0.0220(3) Uani 1 d . .
N1 N 0.18360(15) 0.04186(9) 0.38867(13) 0.0212(3) Uani 1 d . .
C6 C 0.50221(18) 0.12799(11) 0.86139(16) 0.0228(3) Uani 1 d . .
H6A H 0.536 0.1808 0.7919 0.027 Uiso 1 calc . .
H6B H 0.5721 0.0631 0.8575 0.027 Uiso 1 calc . .
C7 C 0.55363(18) 0.17006(10) 1.02860(16) 0.0210(3) Uani 1 d . .
C5 C 0.30540(19) 0.10337(13) 0.79922(17) 0.0286(4) Uani 1 d . .
H5A H 0.269 0.0527 0.8702 0.034 Uiso 1 calc . .
H5B H 0.2345 0.1687 0.7963 0.034 Uiso 1 calc . .
C1 C 0.19194(18) 0.10771(12) 0.50719(16) 0.0238(3) Uani 1 d . .
H1 H 0.1507 0.1786 0.4979 0.029 Uiso 1 calc . .
C2 C 0.2580(2) -0.05241(11) 0.44910(17) 0.0259(3) Uani 1 d . .
H2 H 0.2698 -0.1136 0.3907 0.031 Uiso 1 calc . .
C3 C 0.3111(2) -0.04249(11) 0.60584(17) 0.0269(4) Uani 1 d . .
H3 H 0.3681 -0.095 0.679 0.032 Uiso 1 calc . .
C4 C 0.1115(2) 0.06558(13) 0.22152(16) 0.0302(4) Uani 1 d . .
H4A H 0.0788 -0.0003 0.1629 0.045 Uiso 1 calc . .
H4B H 0.2027 0.1027 0.1832 0.045 Uiso 1 calc . .
H4C H 0.0048 0.1103 0.2066 0.045 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O3 H32 0.889(15) . ?
O3 H31 0.877(15) . ?
O1 C7 1.271(2) . ?
O2 C7 1.2381(19) . ?
N2 C1 1.324(2) . ?
N2 C3 1.3749(19) . ?
N2 C5 1.471(2) . ?
N1 C1 1.328(2) . ?
N1 C2 1.3707(19) . ?
N1 C4 1.464(2) . ?
C6 C5 1.504(2) . ?
C6 C7 1.521(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C1 H1 0.95 . ?
C2 C3 1.342(2) . ?
C2 H2 0.95 . ?
C3 H3 0.95 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?

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
H32 O3 H31 105.7(17) . . ?
C1 N2 C3 108.53(12) . . ?
C1 N2 C5 126.28(13) . . ?
C3 N2 C5 125.15(12) . . ?
C1 N1 C2 108.29(13) . . ?
C1 N1 C4 126.33(13) . . ?
C2 N1 C4 125.37(12) . . ?
C5 C6 C7 113.76(11) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O2 C7 O1 125.22(14) . . ?
O2 C7 C6 118.89(13) . . ?
O1 C7 C6 115.88(12) . . ?
N2 C5 C6 110.70(11) . . ?
N2 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N2 C1 N1 108.70(14) . . ?
N2 C1 H1 125.7 . . ?
N1 C1 H1 125.7 . . ?
C3 C2 N1 107.53(13) . . ?
C3 C2 H2 126.2 . . ?
N1 C2 H2 126.2 . . ?
C2 C3 N2 106.94(13) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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 C6 C7 O2 2.72(19) . . . . ?
C5 C6 C7 O1 -178.31(12) . . . . ?
C1 N2 C5 C6 -103.63(16) . . . . ?
C3 N2 C5 C6 73.72(18) . . . . ?
C7 C6 C5 N2 -177.13(12) . . . . ?
C3 N2 C1 N1 0.88(15) . . . . ?
C5 N2 C1 N1 178.59(12) . . . . ?
C2 N1 C1 N2 -0.59(15) . . . . ?
C4 N1 C1 N2 -179.32(12) . . . . ?
C1 N1 C2 C3 0.08(16) . . . . ?
C4 N1 C2 C3 178.81(12) . . . . ?
N1 C2 C3 N2 0.45(16) . . . . ?
C1 N2 C3 C2 -0.82(16) . . . . ?
C5 N2 C3 C2 -178.57(12) . . . . ?

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
O3 H32 O1 0.889(15) 1.945(16) 2.825(2) 170.4(18) 4_465
O3 H31 O1 0.877(15) 1.904(15) 2.782(2) 179(2) 1_455


# END of CIF
_chemical_melting_point          363
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO/water mixture'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_sc101
_database_code_depnum_ccdc_archive 'CCDC 1867253'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1 (2 carboxyethyl)-3-methylimidazolium chloride
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N2 O2, Cl'
_chemical_formula_sum            'C7 H11 Cl N2 O2'
_chemical_formula_weight         190.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.1911(9)
_cell_length_b                   7.9146(3)
_cell_length_c                   22.5627(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.268(2)
_cell_angle_gamma                90
_cell_volume                     3602.8(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      50.7

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'Bruker (SADABS-2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4

_diffrn_reflns_number            52787
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.656
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3347
_reflns_number_gt                3106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex II'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+3.2175P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.67153(2) 0.58868(4) 0.20601(2) 0.02890(11) Uani 1 1 d . . . . .
Cl2 Cl 0.92370(2) 0.69992(4) 0.53758(2) 0.02745(11) Uani 1 1 d . . . . .
O1 O 0.58589(5) 0.34394(13) 0.31766(5) 0.0357(3) Uani 1 1 d . . . . .
O2 O 0.56631(6) 0.61382(13) 0.29544(5) 0.0367(3) Uani 1 1 d . . . . .
O3 O 0.78491(7) 0.86992(14) 0.44657(6) 0.0505(3) Uani 1 1 d . . . . .
O4 O 0.83317(5) 0.62041(13) 0.43444(5) 0.0287(2) Uani 1 1 d . . . . .
N1 N 0.40213(6) 0.05572(14) 0.28321(5) 0.0284(3) Uani 1 1 d . . . . .
N2 N 0.45789(6) 0.18814(15) 0.35210(5) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.65281(5) 0.30200(14) 0.47376(5) 0.0245(3) Uani 1 1 d . . . . .
N4 N 0.71137(5) 0.39364(13) 0.40284(5) 0.0205(2) Uani 1 1 d . . . . .
C1 C 0.41026(7) 0.20369(17) 0.31005(6) 0.0251(3) Uani 1 1 d . . . . .
H1 H 0.3861 0.3039 0.3008 0.030 Uiso 1 1 calc R U . . .
C2 C 0.44578(8) -0.05750(19) 0.30912(8) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.4506 -0.1729 0.2986 0.051 Uiso 1 1 calc R U . . .
C3 C 0.48044(8) 0.0252(2) 0.35225(8) 0.0399(4) Uani 1 1 d . . . . .
H3 H 0.5142 -0.0209 0.3780 0.048 Uiso 1 1 calc R U . . .
C4 C 0.35500(8) 0.0201(2) 0.23352(7) 0.0365(4) Uani 1 1 d . . . . .
H4A H 0.3228 0.1124 0.2296 0.055 Uiso 1 1 calc R U . . .
H4B H 0.3318 -0.0860 0.2410 0.055 Uiso 1 1 calc R U . . .
H4C H 0.3790 0.0103 0.1968 0.055 Uiso 1 1 calc R U . . .
C5 C 0.48113(8) 0.3206(2) 0.39372(6) 0.0366(4) Uani 1 1 d . . . . .
H5A H 0.5215 0.2804 0.4157 0.044 Uiso 1 1 calc R U . . .
H5B H 0.4467 0.3408 0.4229 0.044 Uiso 1 1 calc R U . . .
C6 C 0.49648(7) 0.48560(18) 0.36320(6) 0.0287(3) Uani 1 1 d . . . . .
H6A H 0.4568 0.5230 0.3396 0.034 Uiso 1 1 calc R U . . .
H6B H 0.5066 0.5729 0.3936 0.034 Uiso 1 1 calc R U . . .
C7 C 0.55381(6) 0.47107(17) 0.32324(6) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.66849(6) 0.43860(17) 0.44318(6) 0.0230(3) Uani 1 1 d . . . . .
H8 H 0.6519 0.5494 0.4491 0.028 Uiso 1 1 calc R U . . .
C9 C 0.68663(7) 0.16595(17) 0.45229(6) 0.0289(3) Uani 1 1 d . . . . .
H9 H 0.6846 0.0529 0.4662 0.035 Uiso 1 1 calc R U . . .
C10 C 0.72312(7) 0.22306(17) 0.40777(6) 0.0260(3) Uani 1 1 d . . . . .
H10 H 0.7516 0.1578 0.3842 0.031 Uiso 1 1 calc R U . . .
C11 C 0.60872(8) 0.2989(2) 0.52388(7) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.6353 0.2955 0.5611 0.056 Uiso 1 1 calc R U . . .
H11B H 0.5804 0.1984 0.5210 0.056 Uiso 1 1 calc R U . . .
H11C H 0.5810 0.4006 0.5230 0.056 Uiso 1 1 calc R U . . .
C12 C 0.73827(7) 0.50032(17) 0.35598(6) 0.0256(3) Uani 1 1 d . . . . .
H12A H 0.7110 0.4847 0.3190 0.031 Uiso 1 1 calc R U . . .
H12B H 0.7839 0.4626 0.3483 0.031 Uiso 1 1 calc R U . . .
C13 C 0.73972(7) 0.68643(17) 0.37179(6) 0.0275(3) Uani 1 1 d . . . . .
H13A H 0.7511 0.7512 0.3361 0.033 Uiso 1 1 calc R U . . .
H13B H 0.6946 0.7208 0.3824 0.033 Uiso 1 1 calc R U . . .
C14 C 0.78741(7) 0.73599(17) 0.42194(6) 0.0246(3) Uani 1 1 d . . . . .
H4O H 0.8565(10) 0.652(3) 0.4599(9) 0.048(6) Uiso 1 1 d . . . . .
H2O H 0.5989(11) 0.600(3) 0.2729(10) 0.064(7) Uiso 1 1 d . . . . .


_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
O1 C7 1.2059(17) . ?
O2 C7 1.3215(17) . ?
O2 H2O 0.85(2) . ?
O3 C14 1.1988(18) . ?
O4 C14 1.3226(17) . ?
O4 H4O 0.77(2) . ?
N1 C1 1.3257(18) . ?
N1 C2 1.3714(19) . ?
N1 C4 1.4687(18) . ?
N2 C1 1.3298(18) . ?
N2 C3 1.367(2) . ?
N2 C5 1.4720(18) . ?
N3 C8 1.3275(17) . ?
N3 C9 1.3735(18) . ?
N3 C11 1.4669(18) . ?
N4 C8 1.3293(17) . ?
N4 C10 1.3745(17) . ?
N4 C12 1.4736(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.346(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.514(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4996(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8 0.9500 . ?
C9 C10 1.347(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5156(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5084(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C7 O2 H2O 109.9(15) . . ?
C14 O4 H4O 109.8(15) . . ?
C1 N1 C2 108.46(12) . . ?
C1 N1 C4 125.65(12) . . ?
C2 N1 C4 125.88(13) . . ?
C1 N2 C3 108.69(12) . . ?
C1 N2 C5 126.34(13) . . ?
C3 N2 C5 124.93(13) . . ?
C8 N3 C9 108.85(11) . . ?
C8 N3 C11 125.37(12) . . ?
C9 N3 C11 125.73(12) . . ?
C8 N4 C10 108.82(11) . . ?
C8 N4 C12 127.33(11) . . ?
C10 N4 C12 123.61(11) . . ?
N1 C1 N2 108.49(12) . . ?
N1 C1 H1 125.8 . . ?
N2 C1 H1 125.8 . . ?
C3 C2 N1 107.31(14) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.06(13) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 112.95(12) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 112.59(12) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
O1 C7 O2 123.39(12) . . ?
O1 C7 C6 123.87(13) . . ?
O2 C7 C6 112.73(12) . . ?
N3 C8 N4 108.24(11) . . ?
N3 C8 H8 125.9 . . ?
N4 C8 H8 125.9 . . ?
C10 C9 N3 107.10(12) . . ?
C10 C9 H9 126.4 . . ?
N3 C9 H9 126.4 . . ?
C9 C10 N4 106.98(12) . . ?
C9 C10 H10 126.5 . . ?
N4 C10 H10 126.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 C13 113.09(11) . . ?
N4 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N4 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 115.80(11) . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
O3 C14 O4 123.68(13) . . ?
O3 C14 C13 122.71(13) . . ?
O4 C14 C13 113.57(12) . . ?

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 C1 N2 0.20(17) . . . . ?
C4 N1 C1 N2 -178.94(13) . . . . ?
C3 N2 C1 N1 -0.38(16) . . . . ?
C5 N2 C1 N1 -177.89(12) . . . . ?
C1 N1 C2 C3 0.06(19) . . . . ?
C4 N1 C2 C3 179.19(15) . . . . ?
N1 C2 C3 N2 -0.3(2) . . . . ?
C1 N2 C3 C2 0.41(18) . . . . ?
C5 N2 C3 C2 177.96(14) . . . . ?
C1 N2 C5 C6 -49.65(19) . . . . ?
C3 N2 C5 C6 133.23(15) . . . . ?
N2 C5 C6 C7 -65.41(16) . . . . ?
C5 C6 C7 O1 -2.66(19) . . . . ?
C5 C6 C7 O2 178.47(12) . . . . ?
C9 N3 C8 N4 -0.03(15) . . . . ?
C11 N3 C8 N4 177.61(12) . . . . ?
C10 N4 C8 N3 0.23(14) . . . . ?
C12 N4 C8 N3 174.74(11) . . . . ?
C8 N3 C9 C10 -0.18(16) . . . . ?
C11 N3 C9 C10 -177.81(13) . . . . ?
N3 C9 C10 N4 0.32(15) . . . . ?
C8 N4 C10 C9 -0.34(15) . . . . ?
C12 N4 C10 C9 -175.10(11) . . . . ?
C8 N4 C12 C13 26.92(18) . . . . ?
C10 N4 C12 C13 -159.33(12) . . . . ?
N4 C12 C13 C14 67.46(15) . . . . ?
C12 C13 C14 O3 -165.22(14) . . . . ?
C12 C13 C14 O4 16.98(17) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.041

