# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1424483'
loop_
_audit_author_name
_audit_author_address
'Romain Gautier'
;CNRS
France
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl2 Cu0.5, C3 H8 N'
_chemical_formula_sum            'C3 H8 Cl2 Cu0.50 N'
_chemical_formula_weight         160.77
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.5625(5)
_cell_length_b                   14.5977(5)
_cell_length_c                   5.93490(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.284(2)
_cell_angle_gamma                90
_cell_volume                     1204.66(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    112
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.660
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0637 before and 0.0430 after correction. The Ratio of minimum to maximum transmission is 0.8283. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.595
_diffrn_reflns_theta_min         6.502
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1353
_reflns_number_total             1519
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         1519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0163
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+0.5772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3C,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cu1 Cu 0.500000 0.08853(2) 0.250000 0.02262(7) Uani 1 2 d S T P . .
Cl1 Cl 0.33014(2) 0.08833(2) 0.11949(5) 0.02647(8) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 -0.06741(3) 0.250000 0.02418(10) Uani 1 2 d S T P . .
Cl3 Cl 0.500000 0.24315(3) 0.250000 0.02972(10) Uani 1 2 d S T P . .
C3 C 0.36523(13) 0.40903(11) 0.4962(4) 0.0503(4) Uani 1 1 d . . . . .
H3A H 0.334112 0.454120 0.381056 0.075 Uiso 1 1 calc GR . . . .
H3C H 0.429842 0.399799 0.491048 0.075 Uiso 1 1 calc GR . . . .
H3B H 0.366529 0.429877 0.650551 0.075 Uiso 1 1 calc GR . . . .
C4 C 0.31071(9) 0.32021(9) 0.4429(2) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.318516 0.294908 0.296779 0.035 Uiso 1 1 calc R . . . .
N1 N 0.29384(7) 0.16421(8) 0.59146(19) 0.0295(2) Uani 1 1 d . . . . .
H1A H 0.316895 0.126086 0.712073 0.035 Uiso 1 1 calc R . . . .
H1B H 0.301518 0.138087 0.462769 0.035 Uiso 1 1 calc R . . . .
C2 C 0.34885(9) 0.25157(10) 0.6387(2) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.415986 0.239246 0.655235 0.038 Uiso 1 1 calc R . . . .
H2B H 0.344956 0.277363 0.786215 0.038 Uiso 1 1 calc R . . . .

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
Cu1 0.01851(10) 0.01894(11) 0.02948(12) 0.000 0.00572(8) 0.000
Cl1 0.02119(13) 0.03328(16) 0.02437(14) 0.00113(11) 0.00589(10) 0.00253(11)
Cl2 0.02094(17) 0.01887(19) 0.0313(2) 0.000 0.00563(14) 0.000
Cl3 0.0316(2) 0.0218(2) 0.0379(2) 0.000 0.01367(17) 0.000
C3 0.0415(8) 0.0367(8) 0.0739(12) 0.0028(8) 0.0189(8) 0.0039(6)
C4 0.0255(6) 0.0338(7) 0.0287(6) 0.0044(5) 0.0103(5) 0.0091(5)
N1 0.0269(5) 0.0334(6) 0.0279(5) 0.0080(4) 0.0077(4) 0.0131(4)
C2 0.0250(6) 0.0373(7) 0.0284(6) 0.0033(5) 0.0023(5) 0.0088(5)

_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
Cu1 Cl1 2.3623(3) 2_655 ?
Cu1 Cl1 2.3623(3) . ?
Cu1 Cl2 2.2765(4) . ?
Cu1 Cl3 2.2570(5) . ?
C3 C4 1.504(2) . ?
C4 N1 1.4922(15) 7_556 ?
C4 C2 1.5096(17) . ?
N1 C4 1.4922(15) 7_556 ?
N1 C2 1.4876(18) . ?

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
Cl1 Cu1 Cl1 179.859(17) . 2_655 ?
Cl2 Cu1 Cl1 89.930(9) . 2_655 ?
Cl2 Cu1 Cl1 89.929(9) . . ?
Cl3 Cu1 Cl1 90.071(9) . . ?
Cl3 Cu1 Cl1 90.070(9) . 2_655 ?
Cl3 Cu1 Cl2 180.0 . . ?
C3 C4 C2 111.09(12) . . ?
N1 C4 C3 110.53(11) 7_556 . ?
N1 C4 C2 109.48(10) 7_556 . ?
C2 N1 C4 111.45(10) . 7_556 ?
N1 C2 C4 111.69(10) . . ?

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
C3 C4 C2 N1 178.44(11) . . . . ?
C4 N1 C2 C4 -57.19(14) 7_556 . . . ?
N1 C4 C2 N1 56.08(14) 7_556 . . . ?

_shelx_res_file                  
;
TITL shelx in C 2/c
 shelx.res created by SHELXL-2016/4 at 16:40:41 on 30-Apr-2020
CELL 0.71073 14.5625 14.5977 5.9349 90 107.284 90
ZERR 8 0.0005 0.0005 0.0001 0 0.002 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl Cu N
UNIT 24 64 16 4 8

L.S. 5
PLAN  25
MORE -1
CONF
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\shelx.hkl">
REM </olex2.extras>

WGHT    0.018600    0.577200
EXTI    0.003634
FVAR       0.33103
CU1   4    0.500000    0.088534    0.250000    10.50000    0.01851    0.01894 =
         0.02948    0.00000    0.00572    0.00000
CL1   3    0.330136    0.088332    0.119486    11.00000    0.02119    0.03328 =
         0.02437    0.00113    0.00589    0.00253
CL2   3    0.500000   -0.067414    0.250000    10.50000    0.02094    0.01887 =
         0.03132    0.00000    0.00563    0.00000
CL3   3    0.500000    0.243148    0.250000    10.50000    0.03163    0.02179 =
         0.03790    0.00000    0.01367    0.00000
C3    1    0.365229    0.409035    0.496218    11.00000    0.04148    0.03674 =
         0.07391    0.00278    0.01890    0.00387
AFIX 137
H3A   2    0.334112    0.454120    0.381056    11.00000   -1.50000
H3C   2    0.429842    0.399799    0.491048    11.00000   -1.50000
H3B   2    0.366529    0.429877    0.650551    11.00000   -1.50000
AFIX   0
C4    1    0.310714    0.320210    0.442943    11.00000    0.02547    0.03383 =
         0.02873    0.00444    0.01034    0.00907
AFIX  13
H4    2    0.318516    0.294908    0.296779    11.00000   -1.20000
AFIX   0
N1    5    0.293836    0.164214    0.591462    11.00000    0.02685    0.03337 =
         0.02791    0.00800    0.00767    0.01314
AFIX  23
H1A   2    0.316895    0.126086    0.712073    11.00000   -1.20000
H1B   2    0.301518    0.138087    0.462769    11.00000   -1.20000
AFIX   0
C2    1    0.348848    0.251571    0.638702    11.00000    0.02500    0.03733 =
         0.02842    0.00334    0.00225    0.00882
AFIX  23
H2A   2    0.415986    0.239246    0.655235    11.00000   -1.20000
H2B   2    0.344956    0.277363    0.786215    11.00000   -1.20000
AFIX   0
HKLF 4




REM  shelx in C 2/c
REM R1 =  0.0163 for    1353 Fo > 4sig(Fo)  and  0.0212 for all    1519 data
REM     63 parameters refined using      0 restraints

END

WGHT      0.0185      0.5772

REM Highest difference peak  0.301,  deepest hole -0.280,  1-sigma level  0.048
Q1    1   0.3257  0.2847  0.5380  11.00000  0.05    0.30
Q2    1   0.2639  0.3295  0.4272  11.00000  0.05    0.29
Q3    1   0.3335  0.3578  0.4805  11.00000  0.05    0.23
Q4    1   0.3250  0.2052  0.6039  11.00000  0.05    0.19
Q5    1   0.2780  0.2875  0.2320  11.00000  0.05    0.16
Q6    1   0.5225  0.0043  0.2121  11.00000  0.05    0.15
Q7    1   0.2992  0.2937  0.3361  11.00000  0.05    0.14
Q8    1   0.2383  0.3441  0.0883  11.00000  0.05    0.14
Q9    1   0.5000  0.2335  0.7500  10.50000  0.05    0.14
Q10   1   0.5000  0.1793  0.2500  10.50000  0.05    0.14
Q11   1   0.5393  0.1646  0.2253  11.00000  0.05    0.14
Q12   1   0.4108  0.5054  0.7321  11.00000  0.05    0.13
Q13   1   0.3559  0.4583  0.5438  11.00000  0.05    0.13
Q14   1   0.3416  0.4548  0.4904  11.00000  0.05    0.13
Q15   1   0.3186  0.1670  0.6918  11.00000  0.05    0.12
Q16   1   0.4151  0.1497  0.3889  11.00000  0.05    0.12
Q17   1   0.3780  0.4046  0.6067  11.00000  0.05    0.12
Q18   1   0.3033  0.1806  0.5340  11.00000  0.05    0.12
Q19   1   0.3189  0.5011  0.4976  11.00000  0.05    0.12
Q20   1   0.4230  0.1391  0.5588  11.00000  0.05    0.12
Q21   1   0.4619  0.3413  0.2095  11.00000  0.05    0.12
Q22   1   0.4664  0.0207  0.1599  11.00000  0.05    0.12
Q23   1   0.4270  0.1808  0.1586  11.00000  0.05    0.12
Q24   1   0.2720  0.4721  0.5742  11.00000  0.05    0.11
Q25   1   0.5000  0.4941  0.7500  10.50000  0.05    0.11
;
_shelx_res_checksum              17870
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 1424484'
loop_
_audit_author_name
_audit_author_address
'Romain Gautier'
;CNRS
France
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-08-04 downloaded from the CCDC.
;
_audit_creation_date             2020-04-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cd0.5 Cl2, C3 H8 N'
_chemical_formula_sum            'C3 H8 Cd0.50 Cl2 N'
_chemical_formula_weight         185.20
_chemical_melting_point          ?
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'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   15.2462(10)
_cell_length_b                   15.1744(9)
_cell_length_c                   5.7267(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.733(4)
_cell_angle_gamma                90
_cell_volume                     1275.25(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    85
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0622 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.8220.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11969
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.090
_diffrn_reflns_theta_min         6.425
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1235
_reflns_number_total             1393
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         1393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0161
_refine_ls_restrained_S_all      1.067
_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)+(0.0152P)²+0.3473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0324
_refine_ls_wR_factor_ref         0.0341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2B,H2A)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cd1 Cd 0.000000 0.09457(2) 0.250000 0.02659(6) Uani 1 2 d S T P . .
Cl1 Cl 0.000000 0.07748(3) -0.250000 0.02366(12) Uani 1 2 d S T P . .
Cl2 Cl 0.17741(3) 0.08773(3) 0.38394(7) 0.02919(10) Uani 1 1 d . . . . .
Cl3 Cl 0.000000 0.25817(4) 0.250000 0.03240(13) Uani 1 2 d S T P . .
C3 C 0.31017(12) 0.18150(12) -0.0500(3) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.321854 0.204605 -0.198493 0.037 Uiso 1 1 calc R . . . .
C4 C 0.36035(16) 0.09537(13) 0.0142(5) 0.0521(5) Uani 1 1 d . . . . .
H4A H 0.355766 0.075878 0.169937 0.078 Uiso 1 1 calc GR . . . .
H4B H 0.423321 0.103494 0.019670 0.078 Uiso 1 1 calc GR . . . .
H4C H 0.333894 0.051934 -0.106181 0.078 Uiso 1 1 calc GR . . . .
N1 N 0.20958(10) 0.16758(9) -0.0942(3) 0.0301(3) Uani 1 1 d . . . . .
H1A H 0.190085 0.130348 -0.217490 0.036 Uiso 1 1 calc R . . . .
H1B H 0.198816 0.143306 0.036789 0.036 Uiso 1 1 calc R . . . .
C2 C 0.15803(12) 0.25154(12) -0.1503(3) 0.0328(4) Uani 1 1 d . . . . .
H2B H 0.093676 0.239931 -0.173347 0.039 Uiso 1 1 calc R . . . .
H2A H 0.165679 0.275533 -0.300556 0.039 Uiso 1 1 calc R . . . .

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
Cd1 0.02245(9) 0.02403(10) 0.03265(10) 0.000 0.00641(7) 0.000
Cl1 0.0261(3) 0.0219(3) 0.0230(3) 0.000 0.0067(2) 0.000
Cl2 0.0248(2) 0.0395(2) 0.02351(19) -0.00133(16) 0.00691(16) -0.00120(16)
Cl3 0.0340(3) 0.0268(3) 0.0381(3) 0.000 0.0125(3) 0.000
C3 0.0295(9) 0.0360(10) 0.0297(9) -0.0029(7) 0.0130(8) -0.0099(7)
C4 0.0461(12) 0.0411(12) 0.0707(15) -0.0006(11) 0.0188(11) -0.0039(9)
N1 0.0306(8) 0.0356(8) 0.0244(7) -0.0078(6) 0.0081(6) -0.0153(6)
C2 0.0284(9) 0.0398(10) 0.0272(8) -0.0023(7) 0.0025(7) -0.0100(7)

_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
Cd1 Cl1 2.87507(11) . ?
Cd1 Cl1 2.6108(6) 5 ?
Cd1 Cl1 2.87508(11) 1_556 ?
Cd1 Cl2 2.6057(4) . ?
Cd1 Cl2 2.6058(4) 2 ?
Cd1 Cl3 2.4824(6) . ?
Cl1 Cd1 2.6109(6) 5 ?
Cl1 Cd1 2.87508(11) 1_554 ?
C3 C4 1.509(3) . ?
C3 N1 1.500(2) . ?
C3 C2 1.510(2) 7 ?
N1 C2 1.486(2) . ?
C2 C3 1.510(2) 7 ?

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
Cl1 Cd1 Cl1 169.65(2) . 1_556 ?
Cl1 Cd1 Cl1 84.823(11) 5 1_556 ?
Cl1 Cd1 Cl1 84.824(10) 5 . ?
Cl2 Cd1 Cl1 90.530(9) 2 1_556 ?
Cl2 Cd1 Cl1 89.058(9) . 1_556 ?
Cl2 Cd1 Cl1 90.531(9) . . ?
Cl2 Cd1 Cl1 89.058(9) 2 . ?
Cl2 Cd1 Cl1 87.717(10) . 5 ?
Cl2 Cd1 Cl1 87.717(10) 2 5 ?
Cl2 Cd1 Cl2 175.43(2) . 2 ?
Cl3 Cd1 Cl1 95.177(10) . 1_556 ?
Cl3 Cd1 Cl1 180.0 . 5 ?
Cl3 Cd1 Cl1 95.176(10) . . ?
Cl3 Cd1 Cl2 92.283(10) . . ?
Cl3 Cd1 Cl2 92.283(10) . 2 ?
Cd1 Cl1 Cd1 95.176(10) 5 . ?
Cd1 Cl1 Cd1 169.65(2) . 1_554 ?
Cd1 Cl1 Cd1 95.177(10) 5 1_554 ?
C4 C3 C2 111.14(16) . 7 ?
N1 C3 C4 110.30(15) . . ?
N1 C3 C2 109.02(13) . 7 ?
C2 N1 C3 111.87(13) . . ?
N1 C2 C3 111.76(14) . 7 ?

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
C3 N1 C2 C3 -57.43(18) . . . 7 ?
C4 C3 N1 C2 178.18(16) . . . . ?
C2 C3 N1 C2 55.88(19) 7 . . . ?

_shelx_res_file                  
;
TITL shelx in P2
 shelx.res created by SHELXL-2016/4 at 16:30:17 on 30-Apr-2020
CELL 0.71073 15.2462 15.1744 5.7267 90 105.733 90
ZERR 8 0.001 0.0009 0.0002 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cd Cl N
UNIT 24 64 4 16 8

L.S. 5
PLAN  25
MORE -1
CONF
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\shelx.hkl">
REM </olex2.extras>

WGHT    0.015200    0.347300
FVAR       0.26654
CD1   3    0.000000    0.094574    0.250000    10.50000    0.02245    0.02403 =
         0.03265    0.00000    0.00641    0.00000
CL1   4    0.000000    0.077483   -0.250000    10.50000    0.02611    0.02186 =
         0.02304    0.00000    0.00672    0.00000
CL2   4    0.177407    0.087734    0.383942    11.00000    0.02481    0.03946 =
         0.02351   -0.00133    0.00691   -0.00120
CL3   4    0.000000    0.258168    0.250000    10.50000    0.03397    0.02677 =
         0.03809    0.00000    0.01254    0.00000
C3    1    0.310172    0.181496   -0.049958    11.00000    0.02947    0.03601 =
         0.02971   -0.00295    0.01303   -0.00993
AFIX  13
H3    2    0.321854    0.204605   -0.198493    11.00000   -1.20000
AFIX   0
C4    1    0.360350    0.095371    0.014200    11.00000    0.04605    0.04114 =
         0.07071   -0.00063    0.01879   -0.00387
AFIX 137
H4A   2    0.355766    0.075878    0.169937    11.00000   -1.50000
H4B   2    0.423321    0.103494    0.019670    11.00000   -1.50000
H4C   2    0.333894    0.051934   -0.106181    11.00000   -1.50000
AFIX   0
N1    5    0.209577    0.167578   -0.094211    11.00000    0.03063    0.03564 =
         0.02445   -0.00779    0.00814   -0.01532
AFIX  23
H1A   2    0.190085    0.130348   -0.217490    11.00000   -1.20000
H1B   2    0.198816    0.143306    0.036789    11.00000   -1.20000
AFIX   0
C2    1    0.158031    0.251538   -0.150310    11.00000    0.02841    0.03983 =
         0.02721   -0.00230    0.00254   -0.00997
AFIX  23
H2B   2    0.093676    0.239931   -0.173347    11.00000   -1.20000
H2A   2    0.165679    0.275533   -0.300556    11.00000   -1.20000
AFIX   0
HKLF 4




REM  shelx in P2
REM R1 =  0.0161 for    1235 Fo > 4sig(Fo)  and  0.0216 for all    1393 data
REM     62 parameters refined using      0 restraints

END

WGHT      0.0152      0.3473

REM Highest difference peak  0.256,  deepest hole -0.375,  1-sigma level  0.060
Q1    1   0.1798  0.2830 -0.0481  11.00000  0.05    0.26
Q2    1  -0.0337  0.0397 -0.0698  11.00000  0.05    0.22
Q3    1   0.0000  0.2825 -0.2500  10.50000  0.05    0.22
Q4    1   0.0063  0.1377  0.1470  11.00000  0.05    0.20
Q5    1   0.0989  0.2044 -0.2377  11.00000  0.05    0.19
Q6    1   0.0776  0.1752 -0.3993  11.00000  0.05    0.19
Q7    1   0.4612  0.1805 -0.0520  11.00000  0.05    0.19
Q8    1   0.3019  0.2262 -0.2246  11.00000  0.05    0.18
Q9    1   0.1094  0.1358 -0.2418  11.00000  0.05    0.18
Q10   1   0.1793 -0.0026  0.4222  11.00000  0.05    0.18
Q11   1   0.2665  0.1790 -0.0714  11.00000  0.05    0.18
Q12   1   0.2311  0.0178 -0.2341  11.00000  0.05    0.18
Q13   1   0.1094  0.0434  0.5782  11.00000  0.05    0.18
Q14   1   0.3134  0.1988 -0.1480  11.00000  0.05    0.17
Q15   1   0.3120  0.1262 -0.0793  11.00000  0.05    0.17
Q16   1   0.1357  0.3059 -0.3563  11.00000  0.05    0.17
Q17   1   0.4061  0.1416  0.3479  11.00000  0.05    0.17
Q18   1   0.1858  0.1917 -0.1819  11.00000  0.05    0.17
Q19   1   0.3973  0.1638 -0.2414  11.00000  0.05    0.16
Q20   1   0.0948  0.0715  0.0367  11.00000  0.05    0.16
Q21   1   0.0802  0.1323  0.0271  11.00000  0.05    0.16
Q22   1   0.4227  0.1158  0.1732  11.00000  0.05    0.16
Q23   1   0.2001  0.2641 -0.3373  11.00000  0.05    0.16
Q24   1   0.1910  0.2004 -0.0261  11.00000  0.05    0.16
Q25   1   0.4520  0.0379  0.4668  11.00000  0.05    0.16
;
_shelx_res_checksum              69087
_olex2_submission_special_instructions 'No special instructions were received'
