# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_P21n
_database_code_depnum_ccdc_archive 'CCDC 2144613'
loop_
_audit_author_name
_audit_author_address
'Ji-Xing Gao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H18 N3, 3(Cl)'
_chemical_formula_sum            'C6 H18 Cl3 N3'
_chemical_formula_weight         238.58

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9842(3)
_cell_length_b                   7.9342(2)
_cell_length_c                   25.1271(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.717(2)
_cell_angle_gamma                90
_cell_volume                     2188.86(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10179
_cell_measurement_theta_min      2.6780
_cell_measurement_theta_max      30.7030

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12574
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4302
_reflns_number_gt                3721
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0758P)²+2.0933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4302
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_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 0.88751(6) 0.70491(9) 0.44229(2) 0.02923(18) Uani 1 1 d . . . . .
Cl2 Cl 0.86897(6) 0.23975(9) 0.32336(2) 0.02938(18) Uani 1 1 d . . . . .
Cl3 Cl 0.15487(6) 0.22685(8) 0.18698(2) 0.02656(17) Uani 1 1 d . . . . .
Cl4 Cl 0.51671(8) 0.16571(14) 0.24687(4) 0.0606(3) Uani 1 1 d . . . . .
Cl5 Cl 0.07713(6) 0.67860(9) 0.06118(3) 0.03126(19) Uani 1 1 d . . . . .
Cl6 Cl 0.73227(6) 0.72355(9) 0.01522(3) 0.03320(19) Uani 1 1 d . . . . .
C1 C 0.2275(3) 0.1293(3) 0.31388(10) 0.0274(6) Uani 1 1 d . . . . .
H1A H 0.1533 0.1054 0.2933 0.033 Uiso 1 1 calc R U . . .
H1B H 0.2948 0.0862 0.2938 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2411(2) 0.3185(3) 0.31759(10) 0.0248(5) Uani 1 1 d . . . . .
H2A H 0.2966 0.3447 0.3472 0.030 Uiso 1 1 calc R U . . .
H2B H 0.2779 0.3588 0.2854 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1119(2) 0.5034(3) 0.37656(10) 0.0271(6) Uani 1 1 d . . . . .
H3A H 0.0323 0.5565 0.3766 0.032 Uiso 1 1 calc R U . . .
H3B H 0.1725 0.5922 0.3787 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1258(2) 0.3953(3) 0.42528(9) 0.0242(5) Uani 1 1 d . . . . .
H4A H 0.1264 0.4671 0.4565 0.029 Uiso 1 1 calc R U . . .
H4B H 0.2038 0.3380 0.4246 0.029 Uiso 1 1 calc R U . . .
C5 C 0.0674(2) 0.0876(3) 0.43736(9) 0.0262(5) Uani 1 1 d . . . . .
H5A H 0.0029 0.0255 0.4542 0.031 Uiso 1 1 calc R U . . .
H5B H 0.1375 0.0872 0.4618 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1012(2) -0.0064(3) 0.38765(11) 0.0291(6) Uani 1 1 d . . . . .
H6A H 0.0984 -0.1261 0.3953 0.035 Uiso 1 1 calc R U . . .
H6B H 0.0391 0.0163 0.3603 0.035 Uiso 1 1 calc R U . . .
C7 C 0.9163(2) 0.0812(3) 0.05430(9) 0.0266(5) Uani 1 1 d . . . . .
H7A H 0.8694 0.0934 0.0212 0.032 Uiso 1 1 calc R U . . .
H7B H 0.9850 0.0086 0.0473 0.032 Uiso 1 1 calc R U . . .
C8 C 0.9643(2) 0.2514(3) 0.07031(10) 0.0243(5) Uani 1 1 d . . . . .
H8A H 1.0239 0.2866 0.0448 0.029 Uiso 1 1 calc R U . . .
H8B H 1.0060 0.2417 0.1047 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8541(3) 0.4663(3) 0.12689(10) 0.0273(5) Uani 1 1 d . . . . .
H9A H 0.8077 0.5694 0.1220 0.033 Uiso 1 1 calc R U . . .
H9B H 0.9344 0.4976 0.1407 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7929(2) 0.3606(3) 0.16842(10) 0.0274(6) Uani 1 1 d . . . . .
H10A H 0.7566 0.4360 0.1938 0.033 Uiso 1 1 calc R U . . .
H10B H 0.7272 0.2980 0.1510 0.033 Uiso 1 1 calc R U . . .
C11 C 0.8425(3) 0.0537(3) 0.19338(10) 0.0276(6) Uani 1 1 d . . . . .
H11A H 0.7546 0.0430 0.1904 0.033 Uiso 1 1 calc R U . . .
H11B H 0.8689 -0.0027 0.2260 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8962(2) -0.0383(3) 0.14737(9) 0.0253(5) Uani 1 1 d . . . . .
H12A H 0.9818 -0.0091 0.1461 0.030 Uiso 1 1 calc R U . . .
H12B H 0.8915 -0.1583 0.1544 0.030 Uiso 1 1 calc R U . . .
N1 N 0.22319(19) 0.0321(3) 0.36485(8) 0.0230(4) Uani 1 1 d . . . . .
H1C H 0.2666 0.0887 0.3894 0.028 Uiso 1 1 calc R U . . .
H1D H 0.2611 -0.0656 0.3599 0.028 Uiso 1 1 calc R U . . .
N2 N 0.12439(19) 0.4124(3) 0.32499(8) 0.0246(5) Uani 1 1 d . . . . .
H2C H 0.1158 0.4871 0.2987 0.030 Uiso 1 1 calc R U . . .
H2D H 0.0632 0.3394 0.3215 0.030 Uiso 1 1 calc R U . . .
N3 N 0.0263(2) 0.2655(3) 0.43010(8) 0.0239(5) Uani 1 1 d . . . . .
H3C H -0.0188 0.2934 0.4576 0.029 Uiso 1 1 calc R U . . .
H3D H -0.0216 0.2707 0.4009 0.029 Uiso 1 1 calc R U . . .
N4 N 0.8384(2) -0.0050(3) 0.09355(8) 0.0238(4) Uani 1 1 d . . . . .
H4C H 0.8141 -0.1030 0.0797 0.029 Uiso 1 1 calc R U . . .
H4D H 0.7722 0.0575 0.0979 0.029 Uiso 1 1 calc R U . . .
N5 N 0.8682(2) 0.3861(3) 0.07364(8) 0.0245(5) Uani 1 1 d . . . . .
H5C H 0.8851 0.4666 0.0503 0.029 Uiso 1 1 calc R U . . .
H5D H 0.7969 0.3412 0.0635 0.029 Uiso 1 1 calc R U . . .
N6 N 0.8731(2) 0.2375(3) 0.19877(8) 0.0230(5) Uani 1 1 d . . . . .
H6C H 0.9492 0.2520 0.1885 0.028 Uiso 1 1 calc R U . . .
H6D H 0.8715 0.2643 0.2331 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.497(3) . ?
C1 C2 1.511(4) . ?
C2 N2 1.499(3) . ?
C3 N2 1.493(3) . ?
C3 C4 1.499(3) . ?
C4 N3 1.509(3) . ?
C5 N3 1.492(3) . ?
C5 C6 1.511(3) . ?
C6 N1 1.504(3) . ?
C7 N4 1.491(3) . ?
C7 C8 1.501(4) . ?
C8 N5 1.506(3) . ?
C9 N5 1.494(3) . ?
C9 C10 1.512(3) . ?
C10 N6 1.507(3) . ?
C11 N6 1.502(3) . ?
C11 C12 1.503(3) . ?
C12 N4 1.500(3) . ?

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
N1 C1 C2 117.7(2) . . ?
N2 C2 C1 114.7(2) . . ?
N2 C3 C4 115.0(2) . . ?
C3 C4 N3 113.5(2) . . ?
N3 C5 C6 116.5(2) . . ?
N1 C6 C5 117.3(2) . . ?
N4 C7 C8 116.1(2) . . ?
C7 C8 N5 114.3(2) . . ?
N5 C9 C10 116.2(2) . . ?
N6 C10 C9 116.3(2) . . ?
N6 C11 C12 116.7(2) . . ?
N4 C12 C11 116.3(2) . . ?
C1 N1 C6 118.8(2) . . ?
C3 N2 C2 116.7(2) . . ?
C5 N3 C4 116.0(2) . . ?
C7 N4 C12 116.2(2) . . ?
C9 N5 C8 116.32(19) . . ?
C11 N6 C10 117.3(2) . . ?

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
N1 C1 C2 N2 -83.3(3) . . . . ?
N2 C3 C4 N3 -65.6(3) . . . . ?
N3 C5 C6 N1 77.3(3) . . . . ?
N4 C7 C8 N5 -67.8(3) . . . . ?
N5 C9 C10 N6 83.3(3) . . . . ?
N6 C11 C12 N4 -75.5(3) . . . . ?
C2 C1 N1 C6 93.1(3) . . . . ?
C5 C6 N1 C1 -108.5(3) . . . . ?
C4 C3 N2 C2 -57.1(3) . . . . ?
C1 C2 N2 C3 114.3(2) . . . . ?
C6 C5 N3 C4 -81.2(3) . . . . ?
C3 C4 N3 C5 126.4(2) . . . . ?
C8 C7 N4 C12 -59.2(3) . . . . ?
C11 C12 N4 C7 114.8(3) . . . . ?
C10 C9 N5 C8 -73.8(3) . . . . ?
C7 C8 N5 C9 119.0(2) . . . . ?
C12 C11 N6 C10 86.9(3) . . . . ?
C9 C10 N6 C11 -118.2(3) . . . . ?

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
C1 H1A Cl3 0.97 2.84 3.354(3) 113.9 .
C1 H1B Cl3 0.97 2.94 3.445(3) 113.5 2_545
C1 H1B Cl4 0.97 2.81 3.651(3) 145.4 .
C2 H2A Cl5 0.97 2.96 3.759(3) 140.3 2_545
C2 H2B Cl3 0.97 2.97 3.466(3) 112.8 .
C3 H3A Cl1 0.97 2.61 3.406(3) 139.8 1_455
C3 H3B Cl3 0.97 2.76 3.536(3) 136.9 2
C4 H4A Cl1 0.97 2.89 3.429(2) 115.8 3_666
C4 H4B Cl5 0.97 2.73 3.695(3) 171.6 2_545
C5 H5A Cl1 0.97 2.85 3.626(3) 137.2 1_445
C5 H5B Cl1 0.97 2.94 3.466(3) 115.2 3_666
C5 H5B Cl6 0.97 2.98 3.604(3) 123.2 4_566
C6 H6A Cl1 0.97 2.95 3.583(3) 123.7 1_445
C6 H6B Cl2 0.97 2.72 3.562(3) 145.5 1_455
C7 H7A Cl5 0.97 2.82 3.474(3) 125.2 3_665
C7 H7B Cl5 0.97 2.83 3.652(3) 143.7 1_645
C8 H8A Cl5 0.97 2.87 3.368(3) 113.1 3_665
C8 H8B Cl3 0.97 2.60 3.556(3) 169.1 1_655
C9 H9A Cl2 0.97 2.76 3.530(3) 136.3 2_655
C9 H9B Cl5 0.97 2.95 3.436(3) 112.2 1_655
C10 H10A Cl2 0.97 2.80 3.504(3) 129.7 2_655
C10 H10B Cl1 0.97 2.73 3.586(3) 147.7 2_645
C11 H11A Cl2 0.97 2.78 3.423(3) 124.5 2_645
C11 H11B Cl4 0.97 2.99 3.739(3) 135.4 2_645
C12 H12A Cl3 0.97 2.84 3.649(3) 141.7 1_655
N1 H1C Cl5 0.89 2.21 3.062(2) 160.8 2_545
N1 H1D Cl3 0.89 2.24 3.075(2) 156.2 2_545
N2 H2C Cl4 0.89 2.31 3.088(2) 145.8 2
N2 H2D Cl2 0.89 2.28 3.121(2) 158.4 1_455
N3 H3C Cl1 0.89 2.86 3.324(2) 114.0 3_666
N3 H3C Cl6 0.89 2.52 3.209(2) 134.3 2_545
N3 H3D Cl2 0.89 2.27 3.154(2) 170.2 1_455
N4 H4C Cl6 0.89 2.29 3.120(2) 155.4 1_545
N4 H4D Cl1 0.89 2.31 3.100(2) 147.1 2_645
N5 H5C Cl5 0.89 2.71 3.285(2) 123.9 1_655
N5 H5C Cl6 0.89 2.77 3.380(2) 127.0 .
N5 H5D Cl1 0.89 2.30 3.170(2) 166.6 2_645
N6 H6C Cl3 0.89 2.27 3.120(2) 159.7 1_655
N6 H6D Cl2 0.89 2.28 3.132(2) 161.3 .

_refine_diff_density_max         1.410
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_R-3m
_database_code_depnum_ccdc_archive 'CCDC 2144614'
loop_
_audit_author_name
_audit_author_address
'Ji-Xing Gao'
;Fuyang Normal University
China
;
_audit_update_record             
;
2022-01-26 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H18 N3, 3(Cl)'
_chemical_formula_sum            'C6 H18 Cl3 N3'
_chemical_formula_weight         238.58

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

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m '
_space_group_name_Hall           '-R 3 2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   8.0176(6)
_cell_length_b                   8.0176(6)
_cell_length_c                   15.1832(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     845.24(14)
_cell_formula_units_Z            3
_cell_measurement_temperature    403(2)
_cell_measurement_reflns_used    626
_cell_measurement_theta_min      3.9670
_cell_measurement_theta_max      28.8560

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             378
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      403(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1013
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_av_R_equivalents  0.0087
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         26.743
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             246
_reflns_number_gt                210
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.2143P)²+5.0860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         246
_refine_ls_number_parameters     23
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.1164
_refine_ls_wR_factor_ref         0.3539
_refine_ls_wR_factor_gt          0.3415
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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 0.6667 0.3333 0.0532(2) 0.0970(19) Uani 1 6 d S T P . .
Cl2 Cl 0.0000 0.0000 0.0000 0.145(3) Uani 1 12 d S T P . .
N1 N 0.0810(15) 0.6667 0.1667 0.095(4) Uani 0.5 2 d DS TU P . .
H1C H -0.0302 0.6667 0.1667 0.114 Uiso 0.5 2 d R U P . .
H1D H 0.0648 0.5483 0.1585 0.114 Uiso 0.25 1 d R U P . .
C1 C 0.207(4) 0.793(4) 0.2275(17) 0.223(14) Uani 0.5 2 d DS TU P . .
H1A H 0.1855 0.8688 0.2628 0.268 Uiso 0.25 1 d R U P . .
H1B H 0.2884 0.7124 0.2529 0.268 Uiso 0.5 2 d R U P . .
C2 C 0.2055(10) 0.7945(10) 0.1304(10) 0.082(4) Uani 0.5 2 d S TU P . .
H2A H 0.2878 0.7619 0.0963 0.099 Uiso 0.25 1 d R U P . .
H2B H 0.1857 0.8912 0.1060 0.099 Uiso 0.25 1 d R U P . .


_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
N1 C2 1.152(8) . ?
N1 C2 1.152(8) 27 ?
N1 C1 1.370(17) 27 ?
N1 C1 1.370(17) . ?
C1 N1 1.370(17) 26_455 ?
C1 C2 1.47(3) . ?
C1 C2 1.80(3) 27 ?
C1 C2 1.80(3) 26_455 ?
C2 N1 1.152(8) 26_455 ?
C2 C1 1.80(3) 27 ?
C2 C1 1.80(3) 26_455 ?

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
C2 N1 C2 130.1(19) . 27 ?
C2 N1 C1 90.7(19) . 27 ?
C2 N1 C1 71.0(11) 27 27 ?
C2 N1 C1 71.0(11) . . ?
C2 N1 C1 90.7(19) 27 . ?
C1 N1 C1 136(4) 27 . ?
N1 C1 N1 95.2(17) 26_455 . ?
N1 C1 C2 47.6(8) 26_455 . ?
N1 C1 C2 47.6(8) . . ?
N1 C1 C2 119(2) 26_455 27 ?
N1 C1 C2 39.7(8) . 27 ?
C2 C1 C2 78.5(12) . 27 ?
N1 C1 C2 39.7(8) 26_455 26_455 ?
N1 C1 C2 119(2) . 26_455 ?
C2 C1 C2 78.5(12) . 26_455 ?
C2 C1 C2 117(3) 27 26_455 ?
N1 C2 N1 122.9(13) . 26_455 ?
N1 C2 C1 61.5(7) . . ?
N1 C2 C1 61.4(7) 26_455 . ?
N1 C2 C1 49.5(12) . 27 ?
N1 C2 C1 145.9(17) 26_455 27 ?
C1 C2 C1 101.5(13) . 27 ?
N1 C2 C1 145.9(17) . 26_455 ?
N1 C2 C1 49.5(12) 26_455 26_455 ?
C1 C2 C1 101.5(13) . 26_455 ?
C1 C2 C1 114(3) 27 26_455 ?

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 N1 -1(2) . . . 26_455 ?
C2 N1 C1 N1 131(2) 27 . . 26_455 ?
C1 N1 C1 N1 69(2) 27 . . 26_455 ?
C2 N1 C1 C2 132.6(19) 27 . . . ?
C1 N1 C1 C2 70.0(10) 27 . . . ?
C2 N1 C1 C2 -132.6(19) . . . 27 ?
C1 N1 C1 C2 -62.6(10) 27 . . 27 ?
C2 N1 C1 C2 -34(2) . . . 26_455 ?
C2 N1 C1 C2 98(3) 27 . . 26_455 ?
C1 N1 C1 C2 36(2) 27 . . 26_455 ?
C2 N1 C2 N1 -72.6(17) 27 . . 26_455 ?
C1 N1 C2 N1 -138(2) 27 . . 26_455 ?
C1 N1 C2 N1 2(3) . . . 26_455 ?
C2 N1 C2 C1 -74(2) 27 . . . ?
C1 N1 C2 C1 -140(4) 27 . . . ?
C2 N1 C2 C1 65.4(16) 27 . . 27 ?
C1 N1 C2 C1 140(4) . . . 27 ?
C2 N1 C2 C1 -8(3) 27 . . 26_455 ?
C1 N1 C2 C1 -73(4) 27 . . 26_455 ?
C1 N1 C2 C1 66(2) . . . 26_455 ?
N1 C1 C2 N1 179(3) 26_455 . . . ?
C2 C1 C2 N1 28.7(11) 27 . . . ?
C2 C1 C2 N1 150(2) 26_455 . . . ?
N1 C1 C2 N1 -179(3) . . . 26_455 ?
C2 C1 C2 N1 -150(2) 27 . . 26_455 ?
C2 C1 C2 N1 -28.7(11) 26_455 . . 26_455 ?
N1 C1 C2 C1 148.3(14) 26_455 . . 27 ?
N1 C1 C2 C1 -30(3) . . . 27 ?
C2 C1 C2 C1 -1(3) 27 . . 27 ?
C2 C1 C2 C1 119.6(7) 26_455 . . 27 ?
N1 C1 C2 C1 30(3) 26_455 . . 26_455 ?
N1 C1 C2 C1 -148.3(14) . . . 26_455 ?
C2 C1 C2 C1 -119.6(7) 27 . . 26_455 ?
C2 C1 C2 C1 1(3) 26_455 . . 26_455 ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.109

