# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_yd1-40-4
_database_code_depnum_ccdc_archive 'CCDC 1960297'
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan University
China
;
_audit_update_record             
;
2019-10-19 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Mn, 2(C7 H13 N2)'
_chemical_formula_sum            'C14 H26 Cl4 Mn N4'
_chemical_formula_weight         447.13
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3865(5)
_cell_length_b                   9.30665(16)
_cell_length_c                   15.4932(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.249(3)
_cell_angle_gamma                90
_cell_volume                     2154.29(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5464
_cell_measurement_temperature    293.11(10)
_cell_measurement_theta_max      72.5440
_cell_measurement_theta_min      4.7730
_shelx_estimated_absorpt_T_max   0.393
_shelx_estimated_absorpt_T_min   0.130
_exptl_absorpt_coefficient_mu    9.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         5.601
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.11(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega   10.00  104.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega  -35.00   66.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -19.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   90.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   90.00  175.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  175.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   98.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   98.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega   70.00  178.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
 17 omega   10.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   60.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0924072000
_diffrn_orient_matrix_UB_12      -0.0072544000
_diffrn_orient_matrix_UB_13      -0.0039216000
_diffrn_orient_matrix_UB_21      -0.0329703000
_diffrn_orient_matrix_UB_22      -0.1246306000
_diffrn_orient_matrix_UB_23      -0.0714348000
_diffrn_orient_matrix_UB_31      -0.0318120000
_diffrn_orient_matrix_UB_32      0.1086647000
_diffrn_orient_matrix_UB_33      -0.0822383000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3291
_reflns_number_total             3845
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.023
_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)+(0.1039P)²+0.4750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1535
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C14(H14A,H14B,H14C)
;
_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
Mn1 Mn 0.24653(3) 0.49808(5) 0.77107(3) 0.04019(19) Uani 1 1 d . . . . .
Cl1 Cl 0.15491(7) 0.38485(11) 0.62791(6) 0.0688(3) Uani 1 1 d . . . . .
Cl2 Cl 0.36665(6) 0.61521(11) 0.75353(7) 0.0667(3) Uani 1 1 d . . . . .
Cl3 Cl 0.17418(6) 0.67943(9) 0.81898(7) 0.0644(3) Uani 1 1 d . . . . .
Cl4 Cl 0.29116(8) 0.31619(11) 0.88650(7) 0.0797(3) Uani 1 1 d . . . . .
N1 N 0.0738(3) 0.8526(3) 0.5809(2) 0.0683(9) Uani 1 1 d . . . . .
N2 N 0.0534(2) 1.0012(3) 0.6753(2) 0.0516(7) Uani 1 1 d . . . . .
C1 C 0.2109(4) 0.9833(5) 0.6903(5) 0.0914(16) Uani 1 1 d . . . . .
H1A H 0.2184 1.0788 0.6712 0.137 Uiso 1 1 calc GR . . . .
H1B H 0.2424 0.9164 0.6678 0.137 Uiso 1 1 calc GR . . . .
H1C H 0.2345 0.9788 0.7581 0.137 Uiso 1 1 calc GR . . . .
C2 C 0.1159(3) 0.9468(4) 0.6504(3) 0.0573(8) Uani 1 1 d . . . . .
C3 C 0.1182(5) 0.7633(6) 0.5342(4) 0.112(2) Uani 1 1 d . . . . .
H3A H 0.1668 0.7114 0.5813 0.168 Uiso 1 1 calc GR . . . .
H3B H 0.1409 0.8238 0.4989 0.168 Uiso 1 1 calc GR . . . .
H3C H 0.0759 0.6965 0.4921 0.168 Uiso 1 1 calc GR . . . .
C4 C -0.0142(4) 0.8471(4) 0.5641(3) 0.0721(12) Uani 1 1 d . . . . .
H4 H -0.0574 0.7893 0.5196 0.087 Uiso 1 1 calc R . . . .
C5 C -0.0274(3) 0.9387(4) 0.6224(3) 0.0599(9) Uani 1 1 d . . . . .
H5 H -0.0814 0.9571 0.6267 0.072 Uiso 1 1 calc R . . . .
C6 C 0.0684(3) 1.1015(4) 0.7538(3) 0.0638(9) Uani 1 1 d . . . . .
H6A H 0.0220 1.1743 0.7333 0.077 Uiso 1 1 calc R . . . .
H6B H 0.1256 1.1492 0.7709 0.077 Uiso 1 1 calc R . . . .
C7 C 0.0678(3) 1.0259(5) 0.8378(3) 0.0740(12) Uani 1 1 d . . . . .
H7A H 0.0077 0.9981 0.8257 0.111 Uiso 1 1 calc GR . . . .
H7B H 0.0905 1.0889 0.8916 0.111 Uiso 1 1 calc GR . . . .
H7C H 0.1049 0.9419 0.8504 0.111 Uiso 1 1 calc GR . . . .
N3 N 0.4427(2) 0.4213(3) 0.61621(19) 0.0518(7) Uani 1 1 d . . . . .
N4 N 0.4553(2) 0.6298(3) 0.5631(2) 0.0555(7) Uani 1 1 d . . . . .
C8 C 0.3004(3) 0.5294(4) 0.5040(3) 0.0642(10) Uani 1 1 d . . . . .
H8A H 0.2833 0.4489 0.4615 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.2836 0.6169 0.4682 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.2707 0.5236 0.5459 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.3976(3) 0.5276(4) 0.5594(2) 0.0502(8) Uani 1 1 d . . . . .
C10 C 0.4036(3) 0.2922(4) 0.6365(3) 0.0627(9) Uani 1 1 d . . . . .
H10A H 0.3852 0.3115 0.6868 0.094 Uiso 1 1 calc GR . . . .
H10B H 0.4471 0.2164 0.6554 0.094 Uiso 1 1 calc GR . . . .
H10C H 0.3525 0.2635 0.5809 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.5320(3) 0.4580(4) 0.6577(3) 0.0596(9) Uani 1 1 d . . . . .
H11 H 0.5781 0.4028 0.7007 0.072 Uiso 1 1 calc R . . . .
C12 C 0.5401(3) 0.5863(5) 0.6252(3) 0.0636(9) Uani 1 1 d . . . . .
H12 H 0.5930 0.6378 0.6411 0.076 Uiso 1 1 calc R . . . .
C13 C 0.4367(3) 0.7693(4) 0.5143(3) 0.0710(11) Uani 1 1 d . . . . .
H13A H 0.3854 0.7598 0.4540 0.085 Uiso 1 1 calc R . . . .
H13B H 0.4877 0.7978 0.5018 0.085 Uiso 1 1 calc R . . . .
C14 C 0.4181(4) 0.8824(4) 0.5715(4) 0.0936(16) Uani 1 1 d . . . . .
H14A H 0.4049 0.9713 0.5371 0.140 Uiso 1 1 calc GR . . . .
H14B H 0.4695 0.8947 0.6302 0.140 Uiso 1 1 calc GR . . . .
H14C H 0.3677 0.8543 0.5842 0.140 Uiso 1 1 calc GR . . . .


_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
Mn1 Cl1 2.3556(9) . ?
Mn1 Cl2 2.3613(9) . ?
Mn1 Cl3 2.3511(9) . ?
Mn1 Cl4 2.3503(10) . ?
N1 C2 1.339(5) . ?
N1 C3 1.476(6) . ?
N1 C4 1.356(6) . ?
N2 C2 1.333(5) . ?
N2 C5 1.368(5) . ?
N2 C6 1.472(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.460(7) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.324(6) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.483(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N3 C9 1.328(4) . ?
N3 C10 1.456(5) . ?
N3 C11 1.377(5) . ?
N4 C9 1.326(5) . ?
N4 C12 1.386(5) . ?
N4 C13 1.470(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C9 1.467(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.323(6) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.486(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 Mn1 Cl2 109.70(4) . . ?
Cl3 Mn1 Cl1 114.17(4) . . ?
Cl3 Mn1 Cl2 104.90(4) . . ?
Cl4 Mn1 Cl1 105.84(4) . . ?
Cl4 Mn1 Cl2 113.98(5) . . ?
Cl4 Mn1 Cl3 108.45(4) . . ?
C2 N1 C3 124.5(5) . . ?
C2 N1 C4 109.7(3) . . ?
C4 N1 C3 125.7(5) . . ?
C2 N2 C5 109.6(3) . . ?
C2 N2 C6 126.3(3) . . ?
C5 N2 C6 123.8(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 127.0(4) . . ?
N2 C2 N1 106.1(4) . . ?
N2 C2 C1 127.0(4) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 126.2 . . ?
C5 C4 N1 107.6(4) . . ?
C5 C4 H4 126.2 . . ?
N2 C5 H5 126.5 . . ?
C4 C5 N2 107.0(4) . . ?
C4 C5 H5 126.5 . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
N2 C6 C7 111.5(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 N3 C10 125.6(3) . . ?
C9 N3 C11 108.7(3) . . ?
C11 N3 C10 125.6(3) . . ?
C9 N4 C12 108.4(3) . . ?
C9 N4 C13 128.1(3) . . ?
C12 N4 C13 123.5(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
N3 C9 C8 124.9(4) . . ?
N4 C9 N3 108.2(3) . . ?
N4 C9 C8 126.9(3) . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11 126.3 . . ?
C12 C11 N3 107.5(3) . . ?
C12 C11 H11 126.3 . . ?
N4 C12 H12 126.3 . . ?
C11 C12 N4 107.3(3) . . ?
C11 C12 H12 126.3 . . ?
N4 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
N4 C13 C14 111.7(3) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_date_sample_data_collection 2019-03-08
_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_yd1-5-9
_database_code_depnum_ccdc_archive 'CCDC 1960298'
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan University
China
;
_audit_update_record             
;
2019-11-08 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_audit_creation_date             2019-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br3 Pb, C6 H11 N2'
_chemical_formula_sum            'C6 H11 Br3 N2 Pb'
_chemical_formula_weight         558.09
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -4.0753 8.5060 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.19366(13)
_cell_length_b                   9.78266(16)
_cell_length_c                   15.4593(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1239.15(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2359
_cell_measurement_temperature    295.11(10)
_cell_measurement_theta_max      72.4750
_cell_measurement_theta_min      5.3350
_shelx_estimated_absorpt_T_max   0.117
_shelx_estimated_absorpt_T_min   0.021
_exptl_absorpt_coefficient_mu    37.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3634
_diffrn_reflns_point_group_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.034
_diffrn_reflns_theta_max         67.034
_diffrn_reflns_theta_min         5.351
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.11(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -18.00   1.00    8.00    --  -36.42 -38.00   0.00   88
  2  ω   -104.00 -20.00   1.00    8.00    --  -36.42 -57.00-120.00   84
  3  ω      1.00  75.00   1.00    8.00    --   36.42 -99.00-150.00   74
  4  ω    -31.00  53.00   1.00    8.00    --   36.42 -57.00 -60.00   84
  5  ω     39.00 130.00   1.00   25.00    --  108.71 -30.00 120.00   91
  6  ω     39.00 115.00   1.00   25.00    --  108.71-111.00   0.00   76
  7  ω     68.00  94.00   1.00   25.00    --  108.71 -94.00-180.00   26
  8  ω     47.00 109.00   1.00   25.00    --  108.71 -94.00-120.00   62
  9  ω     72.00 159.00   1.00   25.00    --  108.71  15.00 150.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0274132000
_diffrn_orient_matrix_UB_12      0.1447275000
_diffrn_orient_matrix_UB_13      0.0365906000
_diffrn_orient_matrix_UB_21      0.0118663000
_diffrn_orient_matrix_UB_22      -0.0569369000
_diffrn_orient_matrix_UB_23      0.0926989000
_diffrn_orient_matrix_UB_31      0.1855341000
_diffrn_orient_matrix_UB_32      0.0251640000
_diffrn_orient_matrix_UB_33      -0.0005082000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.573
_reflns_Friedel_fraction_full    0.810
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                1984
_reflns_number_total             2039
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.786
_refine_diff_density_min         -1.511
_refine_diff_density_rms         0.345
_refine_ls_abs_structure_details 
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.069(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.122
_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)+(0.0968P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C2(H2)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_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
Pb1 Pb 0.35759(8) 0.75734(6) 0.50211(4) 0.0424(3) Uani 1 1 d . . . . .
Br1 Br 0.5669(2) 0.55081(17) 0.42828(12) 0.0512(5) Uani 1 1 d . . . . .
Br2 Br 0.1258(2) 0.7165(2) 0.35614(12) 0.0539(5) Uani 1 1 d . . . . .
Br3 Br 0.1838(3) 0.5623(2) 0.59621(14) 0.0610(5) Uani 1 1 d . . . . .
N2 N 0.5877(17) 0.2466(15) 0.6510(10) 0.047(3) Uani 1 1 d . . . . .
N1 N 0.8312(19) 0.2811(16) 0.6930(9) 0.048(3) Uani 1 1 d . . . . .
C1 C 1.000(2) 0.258(2) 0.7184(14) 0.060(5) Uani 1 1 d . . . . .
H1A H 1.0081 0.2618 0.7803 0.090 Uiso 1 1 calc GR . . . .
H1B H 1.0676 0.3276 0.6934 0.090 Uiso 1 1 calc GR . . . .
H1C H 1.0344 0.1700 0.6984 0.090 Uiso 1 1 calc GR . . . .
C3 C 0.604(2) 0.385(2) 0.6606(12) 0.056(4) Uani 1 1 d . . . . .
H3 H 0.5253 0.4507 0.6490 0.067 Uiso 1 1 calc R . . . .
C4 C 0.725(2) 0.1848(17) 0.6696(10) 0.046(4) Uani 1 1 d . . . . .
H4 H 0.7442 0.0913 0.6670 0.055 Uiso 1 1 calc R . . . .
C2 C 0.758(3) 0.4063(18) 0.6905(12) 0.056(4) Uani 1 1 d . . . . .
H2 H 0.8034 0.4896 0.7062 0.067 Uiso 1 1 calc R . . . .
C6 C 0.403(3) 0.202(3) 0.5304(15) 0.075(7) Uani 1 1 d . . . . .
H6A H 0.4924 0.1731 0.4951 0.112 Uiso 1 1 calc GR . . . .
H6B H 0.3860 0.2989 0.5229 0.112 Uiso 1 1 calc GR . . . .
H6C H 0.3057 0.1542 0.5136 0.112 Uiso 1 1 calc GR . . . .
C5 C 0.438(3) 0.174(3) 0.6195(14) 0.068(5) Uani 1 1 d . . . . .
H5A H 0.4529 0.0767 0.6268 0.082 Uiso 1 1 calc R . . . .
H5B H 0.3458 0.2020 0.6546 0.082 Uiso 1 1 calc R . . . .


_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
Pb1 Br1 2.8853(19) . ?
Pb1 Br1 3.218(2) 3_466 ?
Pb1 Br2 2.9766(19) . ?
Pb1 Br2 3.114(2) 3_566 ?
Pb1 Br3 2.790(2) . ?
Pb1 Br3 42.665(2) 3_534 ?
Br1 Pb1 3.218(2) 3_566 ?
Br2 Pb1 3.114(2) 3_466 ?
N2 C3 1.37(3) . ?
N2 C4 1.31(2) . ?
N2 C5 1.50(2) . ?
N1 C1 1.45(2) . ?
N1 C4 1.33(2) . ?
N1 C2 1.37(2) . ?
C3 C2 1.36(3) . ?
C6 C5 1.43(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
Br1 Pb1 Br1 168.71(6) . 3_466 ?
Br1 Pb1 Br2 85.22(6) . 3_566 ?
Br1 Pb1 Br2 89.16(6) . . ?
Br1 Pb1 Br3 37.75(4) . 3_534 ?
Br1 Pb1 Br3 132.67(3) 3_466 3_534 ?
Br2 Pb1 Br1 103.83(5) 3_566 3_466 ?
Br2 Pb1 Br1 81.92(5) . 3_466 ?
Br2 Pb1 Br2 174.20(5) . 3_566 ?
Br2 Pb1 Br3 51.44(4) . 3_534 ?
Br2 Pb1 Br3 122.96(4) 3_566 3_534 ?
Br3 Pb1 Br1 81.18(6) . 3_466 ?
Br3 Pb1 Br1 91.76(6) . . ?
Br3 Pb1 Br2 88.73(6) . . ?
Br3 Pb1 Br2 92.83(6) . 3_566 ?
Br3 Pb1 Br3 89.22(5) . 3_534 ?
Pb1 Br1 Pb1 84.22(4) . 3_566 ?
Pb1 Br2 Pb1 84.59(5) . 3_466 ?
C3 N2 C5 125.6(17) . . ?
C4 N2 C3 110.5(16) . . ?
C4 N2 C5 123.9(17) . . ?
C4 N1 C1 125.9(17) . . ?
C4 N1 C2 109.7(16) . . ?
C2 N1 C1 124.4(17) . . ?
C2 C3 N2 106.3(17) . . ?
N2 C4 N1 107.2(15) . . ?
C3 C2 N1 106.2(17) . . ?
C6 C5 N2 112.9(18) . . ?

_olex2_date_sample_data_collection 2018-11-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.669
