# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 2095544'
loop_
_audit_author_name
_audit_author_address
'Huang Bo'
;Yunnan Normal University
China
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2015-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(Cl8 Mn2), 2(C10 H16 N)'
_chemical_formula_sum            'C20 H32 Cl4 Mn N2'
_chemical_formula_weight         497.22
_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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z'

_cell_length_a                   7.2244(4)
_cell_length_b                   7.3495(4)
_cell_length_c                   23.8121(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 88.3110(10)
_cell_angle_gamma                90.00
_cell_volume                     1263.77(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.26
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  0.9107
_exptl_absorpt_correction_T_min  0.8703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8294
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1938
_reflns_number_total             2477
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C1-C2 = C2-C3 = C3-C4 = C4-C5
 1.48 with sigma of 0.02
 C1-C2' = C2'-C3' = C3'-C4' = C4'-C5'
 1.48 with sigma of 0.02
 C4'-C6' \\sim C4'-C10'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C2' \\sim C3 \\sim C3' \\sim C4 \\sim C4' \\sim C5 \\sim C6
\\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C5' \\sim C6' \\sim C7' \\sim C8'
\\sim C9' \\sim C10': within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2')=Sof(H2'A)=Sof(H2'B)=Sof(C3')=Sof(H3'A)=Sof(H3'B)=
 Sof(C4')=Sof(H4'A)=Sof(H4'B)=Sof(C5')=Sof(C6')=Sof(H6')=Sof(C7')=Sof(H7')=
 Sof(C8')=Sof(H8')=Sof(C9')=Sof(H9')=Sof(C10')=Sof(H10')=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=
 Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2A,H2B), C2'(H2'A,H2'B), C3(H3A,H3B),
 C3'(H3'A,H3'B), C4(H4A,H4B), C4'(H4'A,H4'B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6'(H6'), C7'(H7'), C8'(H8'),
 C9'(H9'), C10'(H10')
5.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C5'(C6',C7',C8',C9',C10')
5.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Mn1 Mn -0.5000 1.0000 0.5000 0.03049(15) Uani 1 d . . 2 S T P
Cl1 Cl -0.50073(8) 1.04156(8) 0.39625(2) 0.04498(17) Uani 1 d . . 1 . . .
Cl2 Cl -0.23560(6) 0.76370(7) 0.48948(2) 0.03956(16) Uani 1 d . . 1 . . .
N1 N -0.4709(3) 1.4854(3) 0.40370(7) 0.0477(5) Uani 1 d A . 1 . . .
H1A H -0.4847 1.3651 0.4052 0.057 Uiso 1 calc . . 1 GR . .
H1B H -0.5473 1.5376 0.4289 0.057 Uiso 1 calc . . 1 GR . .
H1C H -0.3545 1.5141 0.4112 0.057 Uiso 1 calc . . 1 GR . .
C1 C -0.5138(5) 1.5500(5) 0.34738(12) 0.0784(9) Uani 1 d . . 1 D U .
H1AA H -0.6440 1.5273 0.3414 0.094 Uiso 0.689(7) calc A 1 1 R . .
H1AB H -0.4955 1.6807 0.3464 0.094 Uiso 0.689(7) calc A 1 1 R . .
H1BC H -0.6035 1.6471 0.3527 0.094 Uiso 0.311(7) calc A 2 1 R . .
H1BD H -0.4014 1.6065 0.3324 0.094 Uiso 0.311(7) calc A 2 1 R . .
C2 C -0.4091(8) 1.4715(8) 0.30155(17) 0.0775(17) Uani 0.689(7) d A 1 1 D U .
H2A H -0.4091 1.3402 0.3059 0.093 Uiso 0.689(7) calc A 1 1 R . .
H2B H -0.2818 1.5127 0.3033 0.093 Uiso 0.689(7) calc A 1 1 R . .
C2' C -0.576(2) 1.4477(18) 0.3071(4) 0.094(4) Uani 0.311(7) d A 2 1 D U .
H2'A H -0.6947 1.3983 0.3193 0.112 Uiso 0.311(7) calc A 2 1 R . .
H2'B H -0.4914 1.3461 0.3016 0.112 Uiso 0.311(7) calc A 2 1 R . .
C3 C -0.4831(12) 1.5191(9) 0.2432(2) 0.090(2) Uani 0.689(7) d A 1 1 D U .
H3A H -0.3887 1.4845 0.2154 0.108 Uiso 0.689(7) calc A 1 1 R . .
H3B H -0.4950 1.6504 0.2414 0.108 Uiso 0.689(7) calc A 1 1 R . .
C3' C -0.5984(19) 1.541(2) 0.2513(4) 0.084(4) Uani 0.311(7) d A 2 1 D U .
H3'A H -0.7090 1.6160 0.2509 0.101 Uiso 0.311(7) calc A 2 1 R . .
H3'B H -0.4910 1.6138 0.2405 0.101 Uiso 0.311(7) calc A 2 1 R . .
C4 C -0.6751(16) 1.4336(17) 0.2240(4) 0.143(4) Uani 0.689(7) d A 1 1 D U .
H4A H -0.6748 1.3037 0.2313 0.172 Uiso 0.689(7) calc A 1 1 R . .
H4B H -0.7759 1.4870 0.2461 0.172 Uiso 0.689(7) calc A 1 1 R . .
C4' C -0.615(3) 1.381(3) 0.2169(7) 0.104(6) Uani 0.311(7) d A 2 1 D U .
H4'A H -0.6902 1.2899 0.2363 0.125 Uiso 0.311(7) calc A 2 1 R . .
H4'B H -0.4936 1.3293 0.2085 0.125 Uiso 0.311(7) calc A 2 1 R . .
C5 C -0.7088(15) 1.4660(16) 0.1614(2) 0.101(3) Uani 0.689(7) d A 1 1 D U .
C6 C -0.6001(14) 1.3777(16) 0.1207(3) 0.108(3) Uani 0.689(7) d A 1 1 G U .
H6 H -0.5057 1.3001 0.1313 0.130 Uiso 0.689(7) calc A 1 1 R . .
C7 C -0.6326(11) 1.4055(12) 0.0641(3) 0.113(3) Uani 0.689(7) d A 1 1 G U .
H7 H -0.5600 1.3464 0.0368 0.135 Uiso 0.689(7) calc A 1 1 R . .
C8 C -0.7738(12) 1.5215(10) 0.0482(2) 0.114(3) Uani 0.689(7) d A 1 1 G U .
H8 H -0.7955 1.5400 0.0103 0.137 Uiso 0.689(7) calc A 1 1 R . .
C9 C -0.8824(11) 1.6097(10) 0.0889(4) 0.128(3) Uani 0.689(7) d A 1 1 G U .
H9 H -0.9768 1.6873 0.0783 0.153 Uiso 0.689(7) calc A 1 1 R . .
C10 C -0.8499(12) 1.5820(12) 0.1455(3) 0.122(3) Uani 0.689(7) d A 1 1 G U .
H10 H -0.9226 1.6410 0.1728 0.146 Uiso 0.689(7) calc A 1 1 R . .
C5' C -0.703(3) 1.439(3) 0.1647(5) 0.104(6) Uani 0.311(7) d A 2 1 D U .
C6' C -0.620(3) 1.402(3) 0.1126(6) 0.096(6) Uani 0.311(7) d A 2 1 DG U .
H6' H -0.5091 1.3381 0.1103 0.115 Uiso 0.311(7) calc A 2 1 R . .
C7' C -0.702(3) 1.461(3) 0.0638(5) 0.100(5) Uani 0.311(7) d A 2 1 G U .
H7' H -0.6465 1.4367 0.0289 0.119 Uiso 0.311(7) calc A 2 1 R . .
C8' C -0.868(3) 1.558(2) 0.0671(6) 0.107(6) Uani 0.311(7) d A 2 1 G U .
H8' H -0.9231 1.5970 0.0345 0.129 Uiso 0.311(7) calc A 2 1 R . .
C9' C -0.951(2) 1.594(2) 0.1192(7) 0.145(7) Uani 0.311(7) d A 2 1 G U .
H9' H -1.0622 1.6588 0.1215 0.174 Uiso 0.311(7) calc A 2 1 R . .
C10' C -0.869(3) 1.535(3) 0.1680(5) 0.133(6) Uani 0.311(7) d A 2 1 DG U .
H10' H -0.9248 1.5601 0.2029 0.159 Uiso 0.311(7) calc A 2 1 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
Mn1 Cl1 2.4894(5) 3_476 ?
Mn1 Cl1 2.4894(5) . ?
Mn1 Cl2 2.5963(5) 2_456 ?
Mn1 Cl2 2.5883(5) . ?
Mn1 Cl2 2.5883(5) 3_476 ?
Mn1 Cl2 2.5963(5) 4_575 ?
Cl2 Mn1 2.5963(5) 2_446 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.465(3) . ?
C1 H1AA 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1BC 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 C2 1.431(6) . ?
C1 C2' 1.307(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.543(6) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' C3' 1.510(13) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.602(12) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.441(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.534(9) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' C5' 1.479(15) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C5' C6' 1.3900 . ?
C5' C10' 1.3900 . ?
C6' H6' 0.9300 . ?
C6' C7' 1.3900 . ?
C7' H7' 0.9300 . ?
C7' C8' 1.3900 . ?
C8' H8' 0.9300 . ?
C8' C9' 1.3900 . ?
C9' H9' 0.9300 . ?
C9' C10' 1.3900 . ?
C10' H10' 0.9300 . ?

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 Cl1 180.0 3_476 . ?
Cl1 Mn1 Cl2 90.540(18) . . ?
Cl1 Mn1 Cl2 91.416(17) 3_476 4_575 ?
Cl1 Mn1 Cl2 90.541(18) 3_476 3_476 ?
Cl1 Mn1 Cl2 91.416(17) . 2_456 ?
Cl1 Mn1 Cl2 89.459(18) . 3_476 ?
Cl1 Mn1 Cl2 88.584(17) . 4_575 ?
Cl1 Mn1 Cl2 89.460(18) 3_476 . ?
Cl1 Mn1 Cl2 88.584(17) 3_476 2_456 ?
Cl2 Mn1 Cl2 180.0 2_456 4_575 ?
Cl2 Mn1 Cl2 88.501(5) 3_476 2_456 ?
Cl2 Mn1 Cl2 88.501(5) . 4_575 ?
Cl2 Mn1 Cl2 180.00(2) 3_476 . ?
Cl2 Mn1 Cl2 91.499(5) 3_476 4_575 ?
Cl2 Mn1 Cl2 91.499(5) . 2_456 ?
Mn1 Cl2 Mn1 167.31(2) . 2_446 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1AA 108.2 . . ?
N1 C1 H1AB 108.2 . . ?
N1 C1 H1BC 106.1 . . ?
N1 C1 H1BD 106.1 . . ?
H1AA C1 H1AB 107.3 . . ?
H1AA C1 H1BC 59.9 . . ?
H1AA C1 H1BD 145.5 . . ?
H1AB C1 H1BC 50.5 . . ?
H1AB C1 H1BD 57.0 . . ?
H1BC C1 H1BD 106.3 . . ?
C2 C1 N1 116.5(3) . . ?
C2 C1 H1AA 108.2 . . ?
C2 C1 H1AB 108.2 . . ?
C2 C1 H1BC 137.1 . . ?
C2 C1 H1BD 58.3 . . ?
C2' C1 N1 124.8(6) . . ?
C2' C1 H1AA 55.9 . . ?
C2' C1 H1AB 126.9 . . ?
C2' C1 H1BC 106.1 . . ?
C2' C1 H1BD 106.1 . . ?
C2' C1 C2 52.7(7) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(5) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2' H2'A 108.4 . . ?
C1 C2' H2'B 108.4 . . ?
C1 C2' C3' 115.6(10) . . ?
H2'A C2' H2'B 107.4 . . ?
C3' C2' H2'A 108.4 . . ?
C3' C2' H2'B 108.4 . . ?
C2 C3 H3A 107.4 . . ?
C2 C3 H3B 107.4 . . ?
C2 C3 C4 119.7(5) . . ?
H3A C3 H3B 106.9 . . ?
C4 C3 H3A 107.4 . . ?
C4 C3 H3B 107.4 . . ?
C2' C3' H3'A 112.1 . . ?
C2' C3' H3'B 112.1 . . ?
H3'A C3' H3'B 109.8 . . ?
C4' C3' C2' 98.1(11) . . ?
C4' C3' H3'A 112.1 . . ?
C4' C3' H3'B 112.1 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 112.3(8) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3' C4' H4'A 110.4 . . ?
C3' C4' H4'B 110.4 . . ?
C3' C4' C5' 106.6(15) . . ?
H4'A C4' H4'B 108.6 . . ?
C5' C4' H4'A 110.4 . . ?
C5' C4' H4'B 110.4 . . ?
C6 C5 C4 120.2(7) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 119.8(7) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?
C6' C5' C4' 120.5(7) . . ?
C6' C5' C10' 120.0 . . ?
C10' C5' C4' 119.5(7) . . ?
C5' C6' H6' 120.0 . . ?
C5' C6' C7' 120.0 . . ?
C7' C6' H6' 120.0 . . ?
C6' C7' H7' 120.0 . . ?
C8' C7' C6' 120.0 . . ?
C8' C7' H7' 120.0 . . ?
C7' C8' H8' 120.0 . . ?
C9' C8' C7' 120.0 . . ?
C9' C8' H8' 120.0 . . ?
C8' C9' H9' 120.0 . . ?
C10' C9' C8' 120.0 . . ?
C10' C9' H9' 120.0 . . ?
C5' C10' H10' 120.0 . . ?
C9' C10' C5' 120.0 . . ?
C9' C10' H10' 120.0 . . ?

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
Cl1 Mn1 Cl2 Mn1 25.30(10) 3_476 . . 2_446 ?
Cl1 Mn1 Cl2 Mn1 -154.70(10) . . . 2_446 ?
Cl2 Mn1 Cl2 Mn1 113.87(11) 2_456 . . 2_446 ?
Cl2 Mn1 Cl2 Mn1 -66.13(11) 4_575 . . 2_446 ?
Cl2 Mn1 Cl2 Mn1 -156(100) 3_476 . . 2_446 ?
N1 C1 C2 C3 169.8(4) . . . . ?
N1 C1 C2' C3' -176.1(7) . . . . ?
C1 C2 C3 C4 -70.4(10) . . . . ?
C1 C2' C3' C4' 164.7(14) . . . . ?
C2 C1 C2' C3' -77.4(10) . . . . ?
C2 C3 C4 C5 -169.2(7) . . . . ?
C2' C1 C2 C3 54.8(8) . . . . ?
C2' C3' C4' C5' 160.3(14) . . . . ?
C3 C4 C5 C6 69.2(11) . . . . ?
C3 C4 C5 C10 -111.7(10) . . . . ?
C3' C4' C5' C6' 125.6(15) . . . . ?
C3' C4' C5' C10' -53(2) . . . . ?
C4 C5 C6 C7 179.1(11) . . . . ?
C4 C5 C10 C9 -179.1(11) . . . . ?
C4' C5' C6' C7' -179(2) . . . . ?
C4' C5' C10' C9' 179(2) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C5 0.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?
C5' C6' C7' C8' 0.0 . . . . ?
C6' C5' C10' C9' 0.0 . . . . ?
C6' C7' C8' C9' 0.0 . . . . ?
C7' C8' C9' C10' 0.0 . . . . ?
C8' C9' C10' C5' 0.0 . . . . ?
C10' C5' C6' C7' 0.0 . . . . ?

_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_345K
_database_code_depnum_ccdc_archive 'CCDC 2095547'
loop_
_audit_author_name
_audit_author_address
'Huang Bo'
;Yunnan Normal University
China
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2015-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl2 Mn0.5), 2(C10 H16 N)'
_chemical_formula_sum            'C20 H32 Cl4 Mn N2'
_chemical_formula_weight         497.21
_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'
Mn Mn 0.3368 0.7283 '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      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'B m m m'
_space_group_name_Hall           '-B 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, z'
'x, -y, -z'
'x+1/2, y, z+1/2'
'-x+1/2, y, -z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'x, y, -z'
'-x, y, z'
'-x+1/2, -y, -z+1/2'
'x+1/2, -y, z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y, z+1/2'

_cell_length_a                   5.1706(4)
_cell_length_b                   5.1534(4)
_cell_length_c                   47.8420(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1274.81(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1616
_cell_measurement_temperature    623(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.39
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            4301
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.407
_diffrn_ambient_temperature      623(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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                569
_reflns_number_total             907
_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    ?
_refine_diff_density_max         2.336
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         907
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      0.959
_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)+(0.1160P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1726
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(10) 0(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Restrained distances
 N1-C1
 1.45 with sigma of 0.02
 C5-C4 = C4-C3 = C3-C2 = C2-C1
 1.45 with sigma of 0.02
 N1-C2 = C1-C3 = C2-C4 = C3-C5
 2.45 with sigma of 0.02
 C4-C6 \\sim C4-C10
 with sigma of 0.02
4. Restrained planarity
 C4, C5, C6, C10
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C9 \\sim C10: within 1.7A with sigma of 0.04 and sigma for terminal atoms
of 0.08
Uanis(N1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.05
6. Others
 Fixed Sof: N1(0.25) H1A(0.25) H1B(0.25) H1C(0.25) C1(0.25) H1D(0.25)
 H1E(0.25) C2(0.25) H2A(0.25) H2B(0.25) C3(0.25) H3A(0.25) H3B(0.25) C4(0.25)
 H4A(0.25) H4B(0.25) C5(0.25) C6(0.25) H6(0.25) C7(0.25) H7(0.25) C8(0.25)
 H8(0.25) C9(0.25) H9(0.25) C10(0.25) H10(0.25)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
7.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10)
7.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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
Mn1 Mn 0.0000 0.0000 0.0000 0.0612(5) Uani 1 8 d S T P . .
Cl1 Cl 0.0000 0.0000 0.05130(4) 0.1023(7) Uani 1 4 d S T P . .
Cl2 Cl 0.0000 0.5000 0.0000 0.0808(8) Uani 1 8 d S T P . .
Cl3 Cl -0.5000 0.0000 0.0000 0.0832(8) Uani 1 8 d S T P . .
N1 N 0.467(8) 0.535(5) 0.04760(15) 0.070(7) Uani 0.25 1 d D U . A -1
H1A H 0.5855 0.5951 0.0357 0.084 Uiso 0.25 1 calc GR . . A -1
H1B H 0.3214 0.6249 0.0456 0.084 Uiso 0.25 1 calc GR . . A -1
H1C H 0.4373 0.3683 0.0441 0.084 Uiso 0.25 1 calc GR . . A -1
C1 C 0.560(4) 0.563(3) 0.0755(2) 0.094(8) Uani 0.25 1 d D U . A -1
H1D H 0.5500 0.7443 0.0808 0.113 Uiso 0.25 1 calc R . . A -1
H1E H 0.7405 0.5118 0.0761 0.113 Uiso 0.25 1 calc R . . A -1
C2 C 0.416(4) 0.409(3) 0.0956(2) 0.127(9) Uani 0.25 1 d D U . A -1
H2A H 0.2327 0.4284 0.0917 0.153 Uiso 0.25 1 calc R . . A -1
H2B H 0.4590 0.2274 0.0928 0.153 Uiso 0.25 1 calc R . . A -1
C3 C 0.458(9) 0.470(8) 0.1245(3) 0.249(13) Uani 0.25 1 d D U . A -1
H3A H 0.4228 0.3161 0.1355 0.299 Uiso 0.25 1 calc R . . A -1
H3B H 0.6400 0.5112 0.1269 0.299 Uiso 0.25 1 calc R . . A -1
C4 C 0.312(8) 0.677(8) 0.1358(6) 0.36(2) Uani 0.25 1 d D U . A -1
H4A H 0.3900 0.8351 0.1287 0.435 Uiso 0.25 1 calc R . . A -1
H4B H 0.1423 0.6657 0.1272 0.435 Uiso 0.25 1 calc R . . A -1
C5 C 0.267(7) 0.723(6) 0.1640(5) 0.43(2) Uani 0.25 1 d D U . A -1
C6 C 0.451(8) 0.658(9) 0.1840(6) 0.45(2) Uani 0.25 1 d DG U . A -1
H6 H 0.6049 0.5800 0.1786 0.536 Uiso 0.25 1 calc R . . A -1
C7 C 0.404(10) 0.709(8) 0.2120(5) 0.47(3) Uani 0.25 1 d G U . A -1
H7 H 0.5267 0.6660 0.2254 0.559 Uiso 0.25 1 calc R . . A -1
C8 C 0.173(11) 0.826(8) 0.2201(5) 0.47(3) Uani 0.25 1 d G U . A -1
H8 H 0.1416 0.8602 0.2389 0.563 Uiso 0.25 1 calc R . . A -1
C9 C -0.011(10) 0.891(11) 0.2001(7) 0.49(3) Uani 0.25 1 d G U . A -1
H9 H -0.1654 0.9685 0.2055 0.591 Uiso 0.25 1 calc R . . A -1
C10 C 0.036(8) 0.839(9) 0.1720(7) 0.46(2) Uani 0.25 1 d DG U . A -1
H10 H -0.0872 0.8825 0.1587 0.550 Uiso 0.25 1 calc R . . A -1


_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 2.4544(19) 9 ?
Mn1 Cl1 2.4545(19) . ?
Mn1 Cl2 2.5767(2) 1_545 ?
Mn1 Cl2 2.5767(2) . ?
Mn1 Cl3 2.5853(2) 1_655 ?
Mn1 Cl3 2.5853(2) . ?
Cl2 Mn1 2.5767(2) 1_565 ?
Cl3 Mn1 2.5853(2) 1_455 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.426(15) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.455(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.435(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.417(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.386(18) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?

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 Cl1 180.0 9 . ?
Cl1 Mn1 Cl2 90.0 . 1_545 ?
Cl1 Mn1 Cl2 90.0 . . ?
Cl1 Mn1 Cl2 90.0 9 1_545 ?
Cl1 Mn1 Cl2 90.0 9 . ?
Cl1 Mn1 Cl3 90.0 9 1_655 ?
Cl1 Mn1 Cl3 90.0 . . ?
Cl1 Mn1 Cl3 90.0 9 . ?
Cl1 Mn1 Cl3 90.0 . 1_655 ?
Cl2 Mn1 Cl2 180.0 1_545 . ?
Cl2 Mn1 Cl3 90.0 . . ?
Cl2 Mn1 Cl3 90.0 . 1_655 ?
Cl2 Mn1 Cl3 90.0 1_545 1_655 ?
Cl2 Mn1 Cl3 90.0 1_545 . ?
Cl3 Mn1 Cl3 180.0 1_655 . ?
Mn1 Cl2 Mn1 180.0 1_565 . ?
Mn1 Cl3 Mn1 180.0 1_455 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.0 . . ?
N1 C1 H1E 109.0 . . ?
N1 C1 C2 113.1(16) . . ?
H1D C1 H1E 107.8 . . ?
C2 C1 H1D 109.0 . . ?
C2 C1 H1E 109.0 . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 C1 116(2) . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C2 C3 H3A 108.1 . . ?
C2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 C2 117(2) . . ?
C4 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C3 C4 H4A 105.8 . . ?
C3 C4 H4B 105.8 . . ?
H4A C4 H4B 106.2 . . ?
C5 C4 C3 126(2) . . ?
C5 C4 H4A 105.8 . . ?
C5 C4 H4B 105.8 . . ?
C4 C5 C6 120.9(8) . . ?
C4 C5 C10 119.1(8) . . ?
C6 C5 C10 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?

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 C3 -166(2) . . . . ?
C1 C2 C3 C4 84(5) . . . . ?
C2 C3 C4 C5 161(3) . . . . ?
C3 C4 C5 C6 32(5) . . . . ?
C3 C4 C5 C10 -149(5) . . . . ?
C4 C5 C6 C7 179(2) . . . . ?
C4 C5 C10 C9 -179(2) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C5 0.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(10)
2 0(10)

####################################################################### 
# 
# 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_373K
_database_code_depnum_ccdc_archive 'CCDC 2095550'
loop_
_audit_author_name
_audit_author_address
'Huang Bo'
;Yunnan Normal University
China
;
_audit_update_record             
;
2021-07-09 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2015-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Cl2 Mn0.5), 2(C10 H16 N)'
_chemical_formula_sum            'C20 H32 Cl4 Mn N2'
_chemical_formula_weight         497.22
_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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           123
_space_group_name_H-M_alt        'P 4/m m m'
_space_group_name_Hall           '-P 4 2'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 '-y, x, z'
4 'y, -x, z'
5 '-x, y, -z'
6 'x, -y, -z'
7 'y, x, -z'
8 '-y, -x, -z'
9 '-x, -y, -z'
10 'x, y, -z'
11 'y, -x, -z'
12 '-y, x, -z'
13 'x, -y, z'
14 '-x, y, z'
15 '-y, -x, z'
16 'y, x, z'

_cell_length_a                   5.2046(4)
_cell_length_b                   5.2046(4)
_cell_length_c                   24.0612(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     651.77(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    373(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.97
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       yellow
_exptl_crystal_F_000             259
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            3461
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_temperature      373
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                325
_reflns_number_total             467
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         467
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0709P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C1-N1
 1.45 with sigma of 0.01
 C5-C4 = C4-C3 = C3-C2 = C2-C1
 1.48 with sigma of 0.01
 C5-C3 = C3-C1 = C4-C2 = C2-N1
 2.45 with sigma of 0.02
 C4-C6 \\sim C4-C10
 with sigma of 0.02
3. Restrained planarity
 C4, C5, C6, C10
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8
\\sim C9 \\sim C10: within 1.7A with sigma of 0.04 and sigma for terminal atoms
of 0.08
Uanis(N1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.05
5. Others
 Fixed Sof: N1(0.125) H1A(0.125) H1B(0.125) H1C(0.125) C1(0.125) H1D(0.125)
 H1E(0.125) C2(0.125) H2A(0.125) H2B(0.125) C3(0.125) H3A(0.125) H3B(0.125)
 C4(0.125) H4A(0.125) H4B(0.125) C5(0.125) C6(0.125) H6(0.125) C7(0.125)
 H7(0.125) C8(0.125) H8(0.125) C9(0.125) H9(0.125) C10(0.125) H10(0.125)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
6.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10)
6.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Mn1 Mn 0.0000 0.0000 0.0000 0.0736(6) Uani 1 d . . 16 S T P
Cl2 Cl -0.5000 0.0000 0.0000 0.1005(8) Uani 1 d . . 8 S T P
Cl1 Cl 0.0000 0.0000 0.10233(10) 0.1194(9) Uani 1 d . . 8 S T P
N1 N 0.541(13) 0.520(13) 0.0943(5) 0.097(13) Uani 0.125 d A -1 1 D U .
H1A H 0.6931 0.5931 0.0886 0.117 Uiso 0.125 calc A -1 1 GR . .
H1B H 0.4169 0.6344 0.0885 0.117 Uiso 0.125 calc A -1 1 GR . .
H1C H 0.5215 0.3885 0.0709 0.117 Uiso 0.125 calc A -1 1 GR . .
C1 C 0.526(19) 0.427(8) 0.1511(6) 0.122(10) Uani 0.125 d A -1 1 D U .
H1D H 0.6868 0.3419 0.1603 0.147 Uiso 0.125 calc A -1 1 R . .
H1E H 0.3906 0.2997 0.1535 0.147 Uiso 0.125 calc A -1 1 R . .
C2 C 0.477(11) 0.629(5) 0.1926(7) 0.155(12) Uani 0.125 d A -1 1 D U .
H2A H 0.3034 0.6928 0.1881 0.186 Uiso 0.125 calc A -1 1 R . .
H2B H 0.5941 0.7715 0.1861 0.186 Uiso 0.125 calc A -1 1 R . .
C3 C 0.511(9) 0.537(10) 0.2502(7) 0.304(14) Uani 0.125 d A -1 1 D U .
H3A H 0.5552 0.6803 0.2740 0.365 Uiso 0.125 calc A -1 1 R . .
H3B H 0.6515 0.4146 0.2513 0.365 Uiso 0.125 calc A -1 1 R . .
C4 C 0.276(9) 0.412(15) 0.2717(15) 0.35(2) Uani 0.125 d A -1 1 D U .
H4A H 0.2497 0.2516 0.2520 0.420 Uiso 0.125 calc A -1 1 R . .
H4B H 0.1296 0.5221 0.2638 0.420 Uiso 0.125 calc A -1 1 R . .
C5 C 0.282(7) 0.359(10) 0.3321(13) 0.38(3) Uani 0.125 d A -1 1 D U .
C6 C 0.297(8) 0.561(10) 0.370(2) 0.38(3) Uani 0.125 d A -1 1 DG U .
H6 H 0.3133 0.7286 0.3572 0.462 Uiso 0.125 calc A -1 1 R . .
C7 C 0.287(9) 0.511(16) 0.4266(18) 0.41(3) Uani 0.125 d A -1 1 G U .
H7 H 0.2968 0.6456 0.4519 0.486 Uiso 0.125 calc A -1 1 R . .
C8 C 0.262(9) 0.260(19) 0.4455(14) 0.40(3) Uani 0.125 d A -1 1 G U .
H8 H 0.2556 0.2265 0.4834 0.482 Uiso 0.125 calc A -1 1 R . .
C9 C 0.248(10) 0.058(14) 0.408(2) 0.40(3) Uani 0.125 d A -1 1 G U .
H9 H 0.2310 -0.1097 0.4204 0.478 Uiso 0.125 calc A -1 1 R . .
C10 C 0.257(9) 0.108(10) 0.351(2) 0.39(3) Uani 0.125 d A -1 1 DG U .
H10 H 0.2476 -0.0268 0.3257 0.473 Uiso 0.125 calc A -1 1 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
Mn1 Cl2 2.6023(2) . ?
Mn1 Cl2 2.6023(2) 3_565 ?
Mn1 Cl2 2.6023(2) 1_655 ?
Mn1 Cl2 2.6023(2) 3 ?
Mn1 Cl1 2.462(2) 9 ?
Mn1 Cl1 2.462(2) . ?
Cl2 Mn1 2.6023(2) 1_455 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.453(11) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.475(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.477(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.478(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.479(11) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?

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
Cl2 Mn1 Cl2 180.0 . 1_655 ?
Cl2 Mn1 Cl2 90.0 1_655 3_565 ?
Cl2 Mn1 Cl2 90.0 . 3_565 ?
Cl2 Mn1 Cl2 90.0 . 3 ?
Cl2 Mn1 Cl2 90.0 1_655 3 ?
Cl2 Mn1 Cl2 180.0 3 3_565 ?
Cl1 Mn1 Cl2 90.0 9 3 ?
Cl1 Mn1 Cl2 90.0 . 3_565 ?
Cl1 Mn1 Cl2 90.0 . 1_655 ?
Cl1 Mn1 Cl2 90.0 . 3 ?
Cl1 Mn1 Cl2 90.0 9 1_655 ?
Cl1 Mn1 Cl2 90.0 9 . ?
Cl1 Mn1 Cl2 90.0 . . ?
Cl1 Mn1 Cl2 90.0 9 3_565 ?
Cl1 Mn1 Cl1 180.0 9 . ?
Mn1 Cl2 Mn1 180.0 1_455 . ?
N1 C1 H1D 108.7 . . ?
N1 C1 H1E 108.7 . . ?
N1 C1 C2 114.1(16) . . ?
H1D C1 H1E 107.6 . . ?
C2 C1 H1D 108.7 . . ?
C2 C1 H1E 108.7 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.4(17) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.0(17) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C3 C4 C5 114.0(16) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C6 C5 C4 120.2(9) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 119.7(9) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?

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
Cl2 Mn1 Cl2 Mn1 0.0 1_655 . . 1_455 ?
Cl2 Mn1 Cl2 Mn1 0.0 3_565 . . 1_455 ?
Cl2 Mn1 Cl2 Mn1 0.0 3 . . 1_455 ?
Cl1 Mn1 Cl2 Mn1 0.0 . . . 1_455 ?
Cl1 Mn1 Cl2 Mn1 0.0 9 . . 1_455 ?
N1 C1 C2 C3 -170(6) . . . . ?
C1 C2 C3 C4 -85(6) . . . . ?
C2 C3 C4 C5 -169(3) . . . . ?
C3 C4 C5 C6 64(6) . . . . ?
C3 C4 C5 C10 -120(5) . . . . ?
C4 C5 C6 C7 176(2) . . . . ?
C4 C5 C10 C9 -176(2) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C5 0.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?

_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_120
_database_code_depnum_ccdc_archive 'CCDC 2095542'
loop_
_audit_author_name
_audit_author_address
'Bo Huang'
;CCDC
China
;
_audit_update_record             
;
2021-09-06 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Cl8 Mn2), 2(C10 H16 N)'
_chemical_formula_sum            'C20 H32 Cl4 Mn N2'
_chemical_formula_weight         497.21
_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'
Mn Mn 0.3368 0.7283 '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/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.1398(5)
_cell_length_b                   7.3173(6)
_cell_length_c                   22.8922(16)
_cell_angle_alpha                90
_cell_angle_beta                 82.472(2)
_cell_angle_gamma                90
_cell_volume                     1185.67(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_T_max  0.9053
_exptl_absorpt_correction_T_min  0.8626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ABSCOR
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.457
_diffrn_reflns_theta_min         3.313
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_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                2247
_reflns_number_total             2694
_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    ?
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.034
_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)+(0.0490P)²+0.2913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1058
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
2.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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
Mn1 Mn -0.500000 1.000000 0.500000 0.01977(15) Uani 1 2 d S T P . .
Cl1 Cl -0.46841(8) 1.05002(8) 0.39058(2) 0.02413(16) Uani 1 1 d . . . . .
Cl2 Cl -0.22258(7) 0.77242(8) 0.48782(2) 0.02299(15) Uani 1 1 d . . . . .
N1 N -0.4280(3) 1.4876(3) 0.39812(9) 0.0256(4) Uani 1 1 d . . . . .
H1A H -0.457375 1.369356 0.399189 0.031 Uiso 1 1 calc GR . . . .
H1B H -0.492792 1.544059 0.428784 0.031 Uiso 1 1 calc GR . . . .
H1C H -0.304807 1.500610 0.399673 0.031 Uiso 1 1 calc GR . . . .
C1 C -0.4770(3) 1.5700(4) 0.34200(10) 0.0276(5) Uani 1 1 d . . . . .
H1D H -0.451989 1.700305 0.341906 0.033 Uiso 1 1 calc R . . . .
H1E H -0.610544 1.552702 0.339782 0.033 Uiso 1 1 calc R . . . .
C2 C -0.3622(4) 1.4824(4) 0.28865(11) 0.0302(6) Uani 1 1 d . . . . .
H2A H -0.375691 1.350613 0.291374 0.036 Uiso 1 1 calc R . . . .
H2B H -0.229657 1.511484 0.288744 0.036 Uiso 1 1 calc R . . . .
C3 C -0.4250(4) 1.5480(4) 0.23050(11) 0.0322(6) Uani 1 1 d . . . . .
H3A H -0.415835 1.680217 0.228632 0.039 Uiso 1 1 calc R . . . .
H3B H -0.339391 1.498756 0.197892 0.039 Uiso 1 1 calc R . . . .
C4 C -0.6273(4) 1.4912(4) 0.22335(11) 0.0310(6) Uani 1 1 d . . . . .
H4A H -0.713471 1.566416 0.249399 0.037 Uiso 1 1 calc R . . . .
H4B H -0.645250 1.365746 0.236542 0.037 Uiso 1 1 calc R . . . .
C5 C -0.6836(2) 1.5051(2) 0.16087(5) 0.0296(6) Uani 1 1 d . . . . .
C6 C -0.5804(2) 1.6097(2) 0.11727(7) 0.0315(6) Uani 1 1 d G . . . .
H6 H -0.477717 1.677905 0.125985 0.038 Uiso 1 1 calc R . . . .
C7 C -0.6308(2) 1.6124(2) 0.06064(6) 0.0348(6) Uani 1 1 d G . . . .
H7 H -0.561720 1.682380 0.031469 0.042 Uiso 1 1 calc R . . . .
C8 C -0.7843(3) 1.5105(3) 0.04761(6) 0.0362(6) Uani 1 1 d G . . . .
H8 H -0.817954 1.512288 0.009725 0.043 Uiso 1 1 calc R . . . .
C9 C -0.8875(2) 1.4059(2) 0.09121(7) 0.0407(7) Uani 1 1 d G . . . .
H9 H -0.990187 1.337719 0.082498 0.049 Uiso 1 1 calc R . . . .
C10 C -0.8371(2) 1.4032(2) 0.14784(6) 0.0365(6) Uani 1 1 d G . . . .
H10 H -0.906186 1.333242 0.177014 0.044 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
Mn1 Cl1 2.5121(6) . ?
Mn1 Cl1 2.5121(6) 3_476 ?
Mn1 Cl2 2.5871(6) 2_456 ?
Mn1 Cl2 2.5871(6) 4_575 ?
Mn1 Cl2 2.5747(5) 3_476 ?
Mn1 Cl2 2.5748(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.501(3) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.521(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.536(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.532(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.539(3) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?

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 Cl1 180.00(3) . 3_476 ?
Cl1 Mn1 Cl2 88.917(17) 3_476 . ?
Cl1 Mn1 Cl2 91.093(18) . 2_456 ?
Cl1 Mn1 Cl2 88.917(18) . 3_476 ?
Cl1 Mn1 Cl2 91.093(18) 3_476 4_575 ?
Cl1 Mn1 Cl2 91.082(17) 3_476 3_476 ?
Cl1 Mn1 Cl2 88.907(17) 3_476 2_456 ?
Cl1 Mn1 Cl2 91.084(17) . . ?
Cl1 Mn1 Cl2 88.907(18) . 4_575 ?
Cl2 Mn1 Cl2 87.976(7) . 4_575 ?
Cl2 Mn1 Cl2 92.024(7) 3_476 4_575 ?
Cl2 Mn1 Cl2 87.976(7) 3_476 2_456 ?
Cl2 Mn1 Cl2 92.024(7) . 2_456 ?
Cl2 Mn1 Cl2 180.0 3_476 . ?
Cl2 Mn1 Cl2 180.00(2) 4_575 2_456 ?
Mn1 Cl2 Mn1 164.02(2) . 2_446 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
N1 C1 C2 110.9(2) . . ?
H1D C1 H1E 108.0 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 112.1(2) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 113.2(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
C3 C4 C5 116.51(19) . . ?
H4A C4 H4B 107.3 . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C6 C5 C4 121.68(14) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 118.26(14) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?

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 C3 173.5(2) . . . . ?
C1 C2 C3 C4 -64.7(3) . . . . ?
C2 C3 C4 C5 -164.2(2) . . . . ?
C3 C4 C5 C6 -17.7(3) . . . . ?
C3 C4 C5 C10 159.44(19) . . . . ?
C4 C5 C6 C7 177.13(19) . . . . ?
C4 C5 C10 C9 -177.22(18) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C5 0.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
