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

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

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 2043832'
loop_
_audit_author_name
_audit_author_address
'Hang Peng'
;Nanchang University
China
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(Cl), C6 H18 N3'
_chemical_formula_sum            'C6 H18 Cl3 N3'
_chemical_formula_weight         238.58
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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_reflns_used    10179
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.7030
_cell_measurement_theta_min      2.6780
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.792
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14107
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.691
_diffrn_reflns_theta_min         2.692
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.792
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4393
_reflns_number_total             5391
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.546
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.090
_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)+(0.0835P)²+0.7200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1507
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), N1(H1C,H1D), N2(H2C,H2D), N3(H3C,H3D), N4(H4C,H4D), N5(H5C,
 H5D), N6(H6C,H6D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.88747(5) 0.70485(8) 0.44228(2) 0.02987(16) Uani 1 1 d . . . . .
Cl2 Cl 0.86892(5) 0.23974(8) 0.32337(2) 0.02998(16) Uani 1 1 d . . . . .
Cl3 Cl 0.15488(5) 0.22685(7) 0.18699(2) 0.02707(15) Uani 1 1 d . . . . .
Cl4 Cl 0.51670(8) 0.16567(13) 0.24687(3) 0.0612(3) Uani 1 1 d . . . . .
Cl5 Cl 0.07719(5) 0.67858(8) 0.06119(2) 0.03172(16) Uani 1 1 d . . . . .
Cl6 Cl 0.73232(6) 0.72354(8) 0.01521(3) 0.03376(17) Uani 1 1 d . . . . .
C1 C 0.2274(2) 0.1291(3) 0.31396(9) 0.0283(5) Uani 1 1 d . . . . .
H1A H 0.153223 0.105248 0.293426 0.034 Uiso 1 1 calc R U . . .
H1B H 0.294720 0.085943 0.293861 0.034 Uiso 1 1 calc R U . . .
C2 C 0.2411(2) 0.3187(3) 0.31777(9) 0.0253(5) Uani 1 1 d . . . . .
H2A H 0.296325 0.344729 0.347481 0.030 Uiso 1 1 calc R U . . .
H2B H 0.278218 0.359065 0.285623 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1118(2) 0.5035(3) 0.37648(9) 0.0275(5) Uani 1 1 d . . . . .
H3A H 0.032207 0.556593 0.376500 0.033 Uiso 1 1 calc R U . . .
H3B H 0.172368 0.592380 0.378573 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1258(2) 0.3951(3) 0.42539(8) 0.0250(5) Uani 1 1 d . . . . .
H4A H 0.126388 0.466870 0.456643 0.030 Uiso 1 1 calc R U . . .
H4B H 0.203733 0.337746 0.424751 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0673(2) 0.0875(3) 0.43740(8) 0.0265(5) Uani 1 1 d . . . . .
H5A H 0.002630 0.025499 0.454139 0.032 Uiso 1 1 calc R U . . .
H5B H 0.137200 0.086801 0.461908 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1013(2) -0.0063(3) 0.38766(10) 0.0297(5) Uani 1 1 d . . . . .
H6A H 0.098510 -0.126076 0.395315 0.036 Uiso 1 1 calc R U . . .
H6B H 0.039238 0.016311 0.360327 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9165(2) 0.0810(3) 0.05433(8) 0.0266(5) Uani 1 1 d . . . . .
H7A H 0.869921 0.093020 0.021126 0.032 Uiso 1 1 calc R U . . .
H7B H 0.985315 0.008513 0.047475 0.032 Uiso 1 1 calc R U . . .
C8 C 0.9643(2) 0.2515(3) 0.07035(9) 0.0251(5) Uani 1 1 d . . . . .
H8A H 1.023796 0.286717 0.044857 0.030 Uiso 1 1 calc R U . . .
H8B H 1.005988 0.241801 0.104789 0.030 Uiso 1 1 calc R U . . .
C9 C 0.8542(2) 0.4664(3) 0.12690(9) 0.0280(5) Uani 1 1 d . . . . .
H9A H 0.807746 0.569459 0.121924 0.034 Uiso 1 1 calc R U . . .
H9B H 0.934443 0.497783 0.140726 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7930(2) 0.3607(3) 0.16843(9) 0.0280(5) Uani 1 1 d . . . . .
H10A H 0.756505 0.436123 0.193807 0.034 Uiso 1 1 calc R U . . .
H10B H 0.727339 0.297965 0.150959 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8421(2) 0.0537(3) 0.19335(9) 0.0283(5) Uani 1 1 d . . . . .
H11A H 0.754215 0.043447 0.190116 0.034 Uiso 1 1 calc R U . . .
H11B H 0.867979 -0.002927 0.225985 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8964(2) -0.0385(3) 0.14734(8) 0.0258(5) Uani 1 1 d . . . . .
H12A H 0.981971 -0.008883 0.146055 0.031 Uiso 1 1 calc R U . . .
H12B H 0.891906 -0.158560 0.154346 0.031 Uiso 1 1 calc R U . . .
N1 N 0.22318(17) 0.0320(2) 0.36486(7) 0.0233(4) Uani 1 1 d . . . . .
H1C H 0.266553 0.088734 0.389406 0.028 Uiso 1 1 calc R U . . .
H1D H 0.261116 -0.065613 0.359941 0.028 Uiso 1 1 calc R U . . .
N2 N 0.12439(17) 0.4123(2) 0.32496(7) 0.0255(4) Uani 1 1 d . . . . .
H2C H 0.115837 0.486776 0.298636 0.031 Uiso 1 1 calc R U . . .
H2D H 0.063220 0.339129 0.321489 0.031 Uiso 1 1 calc R U . . .
N3 N 0.02647(18) 0.2656(2) 0.43017(8) 0.0250(4) Uani 1 1 d . . . . .
H3C H -0.018602 0.293516 0.457671 0.030 Uiso 1 1 calc R U . . .
H3D H -0.021401 0.270959 0.401009 0.030 Uiso 1 1 calc R U . . .
N4 N 0.83816(18) -0.0050(2) 0.09355(7) 0.0245(4) Uani 1 1 d . . . . .
H4C H 0.813662 -0.102960 0.079659 0.029 Uiso 1 1 calc R U . . .
H4D H 0.772084 0.057742 0.097953 0.029 Uiso 1 1 calc R U . . .
N5 N 0.86827(18) 0.3858(2) 0.07367(7) 0.0251(4) Uani 1 1 d . . . . .
H5C H 0.885056 0.466261 0.050313 0.030 Uiso 1 1 calc R U . . .
H5D H 0.797009 0.340833 0.063604 0.030 Uiso 1 1 calc R U . . .
N6 N 0.87308(18) 0.2375(2) 0.19892(7) 0.0240(4) Uani 1 1 d . . . . .
H6C H 0.949272 0.251902 0.188708 0.029 Uiso 1 1 calc R U . . .
H6D H 0.871354 0.264189 0.233292 0.029 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.514(3) . ?
C1 N1 1.495(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N2 1.497(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.505(3) . ?
C3 N2 1.493(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N3 1.506(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.511(3) . ?
C5 N3 1.492(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.503(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.501(3) . ?
C7 N4 1.493(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 N5 1.504(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(3) . ?
C9 N5 1.495(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 N6 1.508(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.506(3) . ?
C11 N6 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 N4 1.502(3) . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
N3 H3C 0.8900 . ?
N3 H3D 0.8900 . ?
N4 H4C 0.8900 . ?
N4 H4D 0.8900 . ?
N5 H5C 0.8900 . ?
N5 H5D 0.8900 . ?
N6 H6C 0.8900 . ?
N6 H6D 0.8900 . ?

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
H1A C1 H1B 107.2 . . ?
C2 C1 H1A 107.9 . . ?
C2 C1 H1B 107.9 . . ?
N1 C1 H1A 107.9 . . ?
N1 C1 H1B 107.9 . . ?
N1 C1 C2 117.59(18) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
N2 C2 C1 114.61(19) . . ?
N2 C2 H2A 108.6 . . ?
N2 C2 H2B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N2 C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
N2 C3 C4 114.89(18) . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 N3 113.49(19) . . ?
H4A C4 H4B 107.7 . . ?
N3 C4 H4A 108.9 . . ?
N3 C4 H4B 108.9 . . ?
H5A C5 H5B 107.3 . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
N3 C5 H5A 108.2 . . ?
N3 C5 H5B 108.2 . . ?
N3 C5 C6 116.53(18) . . ?
C5 C6 H6A 107.9 . . ?
C5 C6 H6B 107.9 . . ?
H6A C6 H6B 107.2 . . ?
N1 C6 C5 117.44(19) . . ?
N1 C6 H6A 107.9 . . ?
N1 C6 H6B 107.9 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
N4 C7 H7A 108.3 . . ?
N4 C7 H7B 108.3 . . ?
N4 C7 C8 116.05(18) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C7 C8 N5 114.39(19) . . ?
H8A C8 H8B 107.6 . . ?
N5 C8 H8A 108.7 . . ?
N5 C8 H8B 108.7 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
N5 C9 H9A 108.3 . . ?
N5 C9 H9B 108.3 . . ?
N5 C9 C10 116.11(19) . . ?
C9 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
N6 C10 C9 116.42(19) . . ?
N6 C10 H10A 108.2 . . ?
N6 C10 H10B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
N6 C11 H11A 108.1 . . ?
N6 C11 H11B 108.1 . . ?
N6 C11 C12 116.68(18) . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
N4 C12 C11 115.91(19) . . ?
N4 C12 H12A 108.3 . . ?
N4 C12 H12B 108.3 . . ?
C1 N1 C6 118.77(18) . . ?
C1 N1 H1C 107.6 . . ?
C1 N1 H1D 107.6 . . ?
C6 N1 H1C 107.6 . . ?
C6 N1 H1D 107.6 . . ?
H1C N1 H1D 107.1 . . ?
C2 N2 H2C 108.2 . . ?
C2 N2 H2D 108.2 . . ?
C3 N2 C2 116.56(18) . . ?
C3 N2 H2C 108.2 . . ?
C3 N2 H2D 108.2 . . ?
H2C N2 H2D 107.3 . . ?
C4 N3 H3C 108.3 . . ?
C4 N3 H3D 108.3 . . ?
C5 N3 C4 116.11(18) . . ?
C5 N3 H3C 108.3 . . ?
C5 N3 H3D 108.3 . . ?
H3C N3 H3D 107.4 . . ?
C7 N4 C12 115.89(18) . . ?
C7 N4 H4C 108.3 . . ?
C7 N4 H4D 108.3 . . ?
C12 N4 H4C 108.3 . . ?
C12 N4 H4D 108.3 . . ?
H4C N4 H4D 107.4 . . ?
C8 N5 H5C 108.2 . . ?
C8 N5 H5D 108.2 . . ?
C9 N5 C8 116.37(18) . . ?
C9 N5 H5C 108.2 . . ?
C9 N5 H5D 108.2 . . ?
H5C N5 H5D 107.3 . . ?
C10 N6 H6C 108.0 . . ?
C10 N6 H6D 108.0 . . ?
C11 N6 C10 117.02(19) . . ?
C11 N6 H6C 108.0 . . ?
C11 N6 H6D 108.0 . . ?
H6C N6 H6D 107.3 . . ?

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
_geom_hbond_publ_flag
C1 H1A Cl3 0.97 2.84 3.356(2) 113.9 . yes
C1 H1B Cl3 0.97 2.94 3.444(2) 113.5 2_545 yes
C1 H1B Cl4 0.97 2.81 3.653(3) 145.4 . yes
C2 H2A Cl5 0.97 2.96 3.756(2) 140.4 2_545 yes
C2 H2B Cl3 0.97 2.98 3.470(2) 112.6 . yes
C3 H3A Cl1 0.97 2.61 3.406(2) 139.7 1_455 yes
C3 H3B Cl3 0.97 2.76 3.535(2) 136.9 2 yes
C4 H4A Cl1 0.97 2.89 3.425(2) 115.8 3_666 yes
C4 H4B Cl5 0.97 2.73 3.694(2) 171.6 2_545 yes
C5 H5A Cl1 0.97 2.85 3.626(2) 137.3 1_445 yes
C5 H5B Cl1 0.97 2.94 3.466(2) 115.2 3_666 yes
C5 H5B Cl6 0.97 2.98 3.604(2) 123.4 4_566 yes
C6 H6A Cl1 0.97 2.95 3.584(2) 123.6 1_445 yes
C6 H6B Cl2 0.97 2.72 3.562(3) 145.5 1_455 yes
C7 H7A Cl5 0.97 2.82 3.476(2) 125.3 3_665 yes
C7 H7B Cl5 0.97 2.82 3.650(2) 143.7 1_645 yes
C8 H8A Cl5 0.97 2.87 3.369(2) 113.1 3_665 yes
C8 H8B Cl3 0.97 2.60 3.556(2) 169.1 1_655 yes
C9 H9A Cl2 0.97 2.76 3.529(2) 136.3 2_655 yes
C9 H9B Cl5 0.97 2.95 3.435(2) 112.2 1_655 yes
C10 H10A Cl2 0.97 2.80 3.503(2) 129.8 2_655 yes
C10 H10B Cl1 0.97 2.73 3.587(3) 147.7 2_645 yes
C11 H11A Cl2 0.97 2.78 3.420(2) 124.2 2_645 yes
C11 H11B Cl4 0.97 2.99 3.742(2) 135.4 2_645 yes
C12 H12A Cl3 0.97 2.84 3.649(2) 141.9 1_655 yes
N1 H1C Cl5 0.89 2.21 3.0608(19) 160.8 2_545 yes
N1 H1D Cl3 0.89 2.24 3.0755(19) 156.2 2_545 yes
N2 H2C Cl4 0.89 2.31 3.0878(19) 145.7 2 yes
N2 H2D Cl2 0.89 2.28 3.121(2) 158.3 1_455 yes
N3 H3C Cl1 0.89 2.86 3.322(2) 114.0 3_666 yes
N3 H3C Cl6 0.89 2.53 3.211(2) 134.3 2_545 yes
N3 H3D Cl2 0.89 2.28 3.156(2) 170.1 1_455 yes
N4 H4C Cl6 0.89 2.29 3.1186(19) 155.5 1_545 yes
N4 H4D Cl1 0.89 2.31 3.097(2) 146.9 2_645 yes
N5 H5C Cl5 0.89 2.71 3.287(2) 123.8 1_655 yes
N5 H5C Cl6 0.89 2.77 3.382(2) 127.1 . yes
N5 H5D Cl1 0.89 2.30 3.169(2) 166.8 2_645 yes
N6 H6C Cl3 0.89 2.27 3.120(2) 159.9 1_655 yes
N6 H6D Cl2 0.89 2.27 3.1287(19) 161.3 . yes

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
C1 C2 N2 C3 114.6(2) . . . . ?
C2 C1 N1 C6 93.1(3) . . . . ?
C3 C4 N3 C5 126.4(2) . . . . ?
C4 C3 N2 C2 -57.1(3) . . . . ?
C5 C6 N1 C1 -108.5(2) . . . . ?
C6 C5 N3 C4 -81.1(3) . . . . ?
C7 C8 N5 C9 119.1(2) . . . . ?
C8 C7 N4 C12 -59.5(3) . . . . ?
C9 C10 N6 C11 -118.1(2) . . . . ?
C10 C9 N5 C8 -73.9(3) . . . . ?
C11 C12 N4 C7 115.1(2) . . . . ?
C12 C11 N6 C10 87.1(3) . . . . ?
N1 C1 C2 N2 -83.6(3) . . . . ?
N2 C3 C4 N3 -65.6(2) . . . . ?
N3 C5 C6 N1 77.2(3) . . . . ?
N4 C7 C8 N5 -67.5(3) . . . . ?
N5 C9 C10 N6 83.4(3) . . . . ?
N6 C11 C12 N4 -76.0(3) . . . . ?

_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_R-3M2
_database_code_depnum_ccdc_archive 'CCDC 2043839'
loop_
_audit_author_name
_audit_author_address
'Hang Peng'
;Nanchang University
China
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-11-26 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 :H'
_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                   8.0160(5)
_cell_length_b                   8.0160(5)
_cell_length_c                   15.1863(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     845.08(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    403(2)
_cell_measurement_reflns_used    650
_cell_measurement_theta_min      3.9670
_cell_measurement_theta_max      29.7600

_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            1081
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_av_R_equivalents  0.0089
_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       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.227
_diffrn_reflns_theta_max         30.312
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             290
_reflns_number_gt                219
_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)+(0.1130P)²+3.1066P] 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         290
_refine_ls_number_parameters     23
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2461
_refine_ls_wR_factor_gt          0.2290
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.0000 0.0000 0.0000 0.144(2) Uani 1 12 d S T P . .
N1 N 0.2061(13) 0.7939(13) 0.2046(16) 0.188(7) Uani 0.5 2 d S TU P . .
H1C H 0.1689 0.8845 0.2143 0.226 Uiso 0.25 1 d R U P . .
H1D H 0.1869 0.7240 0.2599 0.226 Uiso 0.25 1 d R U P . .
C2 C 0.2075(7) 0.7925(7) 0.1283(7) 0.102(4) Uani 0.5 2 d S TU P . .
H2A H 0.1879 0.8991 0.1448 0.123 Uiso 0.25 1 d R U P . .
H2B H 0.1648 0.7668 0.0683 0.123 Uiso 0.25 1 d R U P . .
Cl1 Cl 0.6667 0.3333 0.05311(17) 0.0954(13) Uani 1 6 d S T P . .
C1 C 0.0794(12) 0.6667 0.1667 0.095(4) Uani 0.5 2 d S TU P . .
H1A H -0.0331 0.6667 0.1667 0.114 Uiso 0.5 2 d R U P . .
H1B H 0.1074 0.6577 0.2233 0.114 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 1.16(2) . ?
N1 C1 1.169(13) 26_455 ?
N1 C1 1.169(13) . ?
N1 C2 1.757(10) 27 ?
N1 C2 1.757(10) 26_455 ?
C2 C1 1.173(7) . ?
C2 C1 1.173(7) 26_455 ?
C2 N1 1.757(10) 26_455 ?
C2 N1 1.757(10) 27 ?
C1 N1 1.169(13) 27 ?
C1 C2 1.172(7) 27 ?

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 C1 60.5(10) . 26_455 ?
C2 N1 C1 60.5(10) . . ?
C1 N1 C1 121(2) 26_455 . ?
C2 N1 C2 89.7(11) . 27 ?
C1 N1 C2 138.6(18) 26_455 27 ?
C2 N1 C2 89.7(11) . 26_455 ?
C1 N1 C2 138.6(18) . 26_455 ?
C2 N1 C2 118.9(13) 27 26_455 ?
N1 C2 C1 60.2(5) . . ?
N1 C2 C1 60.2(5) . 26_455 ?
C1 C2 C1 120.4(9) . 26_455 ?
N1 C2 N1 90.2(11) . 26_455 ?
C1 C2 N1 139.5(12) . 26_455 ?
N1 C2 N1 90.2(11) . 27 ?
C1 C2 N1 139.5(12) 26_455 27 ?
N1 C2 N1 121.1(13) 26_455 27 ?
N1 C1 N1 129(2) 27 . ?
N1 C1 C2 59.3(10) 27 27 ?
N1 C1 C2 97.2(12) . 27 ?
N1 C1 C2 97.3(12) 27 . ?
N1 C1 C2 59.3(10) . . ?
C2 C1 C2 127.1(14) 27 . ?
N1 C1 C1 116.0(11) 27 26_455 ?
C2 C1 C1 115.0(6) 27 26_455 ?
N1 C1 C1 116.0(11) . 27 ?
C2 C1 C1 115.0(6) . 27 ?
C1 C1 C1 120.0 26_455 27 ?

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
C1 N1 C2 C1 -179.4(16) 26_455 . . . ?
C2 N1 C2 C1 30.9(8) 27 . . . ?
C2 N1 C2 C1 149.8(12) 26_455 . . . ?
C1 N1 C2 C1 179.4(16) . . . 26_455 ?
C2 N1 C2 C1 -149.8(12) 27 . . 26_455 ?
C2 N1 C2 C1 -30.9(8) 26_455 . . 26_455 ?
C1 N1 C2 N1 29.8(12) 26_455 . . 26_455 ?
C1 N1 C2 N1 -150.9(8) . . . 26_455 ?
C2 N1 C2 N1 -120.00(3) 27 . . 26_455 ?
C2 N1 C2 N1 -1.1(13) 26_455 . . 26_455 ?
C1 N1 C2 N1 150.9(8) 26_455 . . 27 ?
C1 N1 C2 N1 -29.8(12) . . . 27 ?
C2 N1 C2 N1 1.1(13) 27 . . 27 ?
C2 N1 C2 N1 120.00(3) 26_455 . . 27 ?
C2 N1 C1 N1 73.2(9) . . . 27 ?
C1 N1 C1 N1 73.8(18) 26_455 . . 27 ?
C2 N1 C1 N1 -56.0(8) 27 . . 27 ?
C2 N1 C1 N1 24(2) 26_455 . . 27 ?
C2 N1 C1 C2 129.2(13) . . . 27 ?
C1 N1 C1 C2 129.9(17) 26_455 . . 27 ?
C2 N1 C1 C2 80(2) 26_455 . . 27 ?
C1 N1 C1 C2 0.6(17) 26_455 . . . ?
C2 N1 C1 C2 -129.2(13) 27 . . . ?
C2 N1 C1 C2 -50(2) 26_455 . . . ?
C2 N1 C1 C1 -0.6(17) . . . 26_455 ?
C2 N1 C1 C1 -129.9(17) 27 . . 26_455 ?
C2 N1 C1 C1 -50(2) 26_455 . . 26_455 ?
C2 N1 C1 C1 104.9(10) . . . 27 ?
C1 N1 C1 C1 105.5(19) 26_455 . . 27 ?
C2 N1 C1 C1 -24.3(7) 27 . . 27 ?
C2 N1 C1 C1 55(3) 26_455 . . 27 ?
N1 C2 C1 N1 -131(2) . . . 27 ?
C1 C2 C1 N1 -131.8(13) 26_455 . . 27 ?
N1 C2 C1 N1 -82.7(18) 26_455 . . 27 ?
C1 C2 C1 N1 -0.6(16) 26_455 . . . ?
N1 C2 C1 N1 48.5(15) 26_455 . . . ?
N1 C2 C1 N1 131(2) 27 . . . ?
N1 C2 C1 C2 -74.6(12) . . . 27 ?
C1 C2 C1 C2 -75.2(11) 26_455 . . 27 ?
N1 C2 C1 C2 -26.0(16) 26_455 . . 27 ?
N1 C2 C1 C2 56.6(11) 27 . . 27 ?
N1 C2 C1 C1 0.6(16) . . . 26_455 ?
N1 C2 C1 C1 49.2(16) 26_455 . . 26_455 ?
N1 C2 C1 C1 131.8(13) 27 . . 26_455 ?
N1 C2 C1 C1 -106.6(13) . . . 27 ?
C1 C2 C1 C1 -107.2(11) 26_455 . . 27 ?
N1 C2 C1 C1 -58.0(18) 26_455 . . 27 ?
N1 C2 C1 C1 24.6(11) 27 . . 27 ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.083

