# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1551420'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H35 Cl6 N2 W'
_chemical_formula_weight         760.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.5610(5)
_cell_length_b                   15.4452(8)
_cell_length_c                   19.6813(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.790(2)
_cell_angle_gamma                90
_cell_volume                     2879.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.2595
_cell_measurement_theta_max      28.8495

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             1500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.586
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.657
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2001
_exptl_absorpt_correction_T_max  0.3348
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1172 (selected reflections only, before parameter refinement)
 R(int) =  0.0548 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34360
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.682
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5108
_reflns_number_gt                4457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

 The anion, two Et and one Me groups of the cation are 
 disordered- Disordered atomic positions have were split
 and refined using one occupancy parameter per disordered
 group.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+20.6729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5108
_refine_ls_number_parameters     385
_refine_ls_number_restraints     317
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5522(7) 0.5578(5) 0.7230(4) 0.0397(16) Uani 1 1 d . U . . .
C2 C 0.5044(7) 0.5115(5) 0.6565(4) 0.0382(15) Uani 1 1 d . U . . .
C3 C 0.5647(8) 0.6531(5) 0.7259(4) 0.0463(19) Uani 1 1 d . U . . .
H3A H 0.6288 0.6724 0.6941 0.069 Uiso 1 1 calc R U . . .
H3B H 0.6022 0.6709 0.7726 0.069 Uiso 1 1 calc R U . . .
H3C H 0.4715 0.6792 0.7129 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4714(7) 0.5628(5) 0.5928(4) 0.0404(17) Uani 1 1 d . U . . .
H4A H 0.3981 0.6054 0.5987 0.061 Uiso 1 1 calc R U . . .
H4B H 0.4376 0.5241 0.5546 0.061 Uiso 1 1 calc R U . . .
H4C H 0.5568 0.5928 0.5830 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6453(9) 0.5338(6) 0.8430(4) 0.0514(18) Uani 1 1 d . U . . .
C6 C 0.5590(10) 0.5583(7) 0.8894(5) 0.073(2) Uani 1 1 d D U . . .
C7 C 0.6239(12) 0.5803(7) 0.9552(5) 0.080(3) Uani 1 1 d . U . . .
H7 H 0.5679 0.5996 0.9885 0.096 Uiso 1 1 calc R U . . .
C8 C 0.7651(12) 0.5743(7) 0.9718(5) 0.070(2) Uani 1 1 d D U . . .
H8 H 0.8082 0.5894 1.0166 0.084 Uiso 0.707(17) 1 calc R U P A 1
C108 C 0.819(4) 0.590(3) 1.0481(11) 0.088(9) Uani 0.293(17) 1 d D U P A 2
H10A H 0.9217 0.5848 1.0559 0.131 Uiso 0.293(17) 1 calc R U P A 2
H10B H 0.7917 0.6487 1.0608 0.131 Uiso 0.293(17) 1 calc R U P A 2
H10C H 0.7767 0.5476 1.0761 0.131 Uiso 0.293(17) 1 calc R U P A 2
C9 C 0.8450(11) 0.5468(7) 0.9246(5) 0.073(2) Uani 1 1 d . U . . .
H9 H 0.9443 0.5431 0.9371 0.088 Uiso 1 1 calc R U . . .
C10 C 0.7881(9) 0.5238(6) 0.8584(4) 0.063(2) Uani 1 1 d D U . . .
C11 C 0.3977(15) 0.5468(12) 0.8740(9) 0.074(3) Uani 0.658(16) 1 d D U P B 1
H11A H 0.3704 0.5354 0.8245 0.089 Uiso 0.658(16) 1 calc R U P B 1
H11B H 0.3681 0.4966 0.9000 0.089 Uiso 0.658(16) 1 calc R U P B 1
C12 C 0.325(2) 0.6269(14) 0.8941(11) 0.101(5) Uani 0.658(16) 1 d D U P B 1
H12C H 0.2228 0.6192 0.8842 0.151 Uiso 0.658(16) 1 calc R U P B 1
H12D H 0.3516 0.6376 0.9432 0.151 Uiso 0.658(16) 1 calc R U P B 1
H12E H 0.3538 0.6763 0.8679 0.151 Uiso 0.658(16) 1 calc R U P B 1
C111 C 0.423(2) 0.606(2) 0.8612(15) 0.076(4) Uani 0.342(16) 1 d D U P B 2
H11F H 0.4295 0.6683 0.8731 0.091 Uiso 0.342(16) 1 calc R U P B 2
H11G H 0.4028 0.6000 0.8107 0.091 Uiso 0.342(16) 1 calc R U P B 2
C112 C 0.311(4) 0.563(3) 0.8951(19) 0.089(6) Uani 0.342(16) 1 d D U P B 2
H11H H 0.2199 0.5898 0.8797 0.133 Uiso 0.342(16) 1 calc R U P B 2
H11I H 0.3074 0.5012 0.8830 0.133 Uiso 0.342(16) 1 calc R U P B 2
H11J H 0.3339 0.5690 0.9449 0.133 Uiso 0.342(16) 1 calc R U P B 2
C13 C 0.892(3) 0.5049(16) 0.8094(13) 0.075(4) Uani 0.45(2) 1 d D U P C 1
H13A H 0.9793 0.5389 0.8226 0.090 Uiso 0.45(2) 1 calc R U P C 1
H13B H 0.8513 0.5224 0.7625 0.090 Uiso 0.45(2) 1 calc R U P C 1
C14 C 0.928(3) 0.4068(17) 0.8102(16) 0.100(6) Uani 0.45(2) 1 d D U P C 1
H14A H 0.9961 0.3955 0.7780 0.150 Uiso 0.45(2) 1 calc R U P C 1
H14B H 0.9700 0.3897 0.8565 0.150 Uiso 0.45(2) 1 calc R U P C 1
H14C H 0.8422 0.3732 0.7965 0.150 Uiso 0.45(2) 1 calc R U P C 1
C113 C 0.8610(18) 0.4748(16) 0.8060(10) 0.074(4) Uani 0.55(2) 1 d D U P C 2
H11K H 0.8054 0.4224 0.7913 0.089 Uiso 0.55(2) 1 calc R U P C 2
H11L H 0.8634 0.5119 0.7651 0.089 Uiso 0.55(2) 1 calc R U P C 2
C114 C 1.009(2) 0.4486(19) 0.8338(12) 0.096(6) Uani 0.55(2) 1 d D U P C 2
H11M H 1.0514 0.4174 0.7983 0.144 Uiso 0.55(2) 1 calc R U P C 2
H11N H 1.0652 0.5003 0.8474 0.144 Uiso 0.55(2) 1 calc R U P C 2
H11O H 1.0073 0.4109 0.8737 0.144 Uiso 0.55(2) 1 calc R U P C 2
C15 C 0.4716(8) 0.3737(5) 0.6033(4) 0.0429(16) Uani 1 1 d . U . . .
C16 C 0.5836(9) 0.3398(6) 0.5746(5) 0.0561(19) Uani 1 1 d D U . . .
C17 C 0.5572(10) 0.2787(6) 0.5227(4) 0.056(2) Uani 1 1 d . U . . .
H17 H 0.6339 0.2546 0.5030 0.067 Uiso 1 1 calc R U . . .
C18 C 0.4227(10) 0.2529(6) 0.4995(4) 0.0547(19) Uani 1 1 d D U . . .
H18 H 0.4059 0.2104 0.4645 0.066 Uiso 0.293(17) 1 calc R U P A 2
C118 C 0.4221(13) 0.1891(8) 0.4414(6) 0.055(4) Uani 0.707(17) 1 d D U P A 1
H11P H 0.5195 0.1764 0.4342 0.083 Uiso 0.707(17) 1 calc R U P A 1
H11Q H 0.3757 0.1354 0.4528 0.083 Uiso 0.707(17) 1 calc R U P A 1
H11R H 0.3708 0.2139 0.3994 0.083 Uiso 0.707(17) 1 calc R U P A 1
C19 C 0.3127(9) 0.2885(6) 0.5270(4) 0.0522(19) Uani 1 1 d . U . . .
H19 H 0.2191 0.2720 0.5095 0.063 Uiso 1 1 calc R U . . .
C20 C 0.3342(8) 0.3488(5) 0.5804(4) 0.0476(17) Uani 1 1 d D U . . .
C21 C 0.7350(10) 0.3718(7) 0.5959(5) 0.073(3) Uani 1 1 d D U . . .
H21A H 0.7827 0.3787 0.5546 0.088 Uiso 1 1 calc R U . . .
H21B H 0.7326 0.4292 0.6182 0.088 Uiso 1 1 calc R U . . .
C22 C 0.8145(12) 0.3117(8) 0.6429(7) 0.105(4) Uani 1 1 d D U . . .
H22A H 0.9106 0.3337 0.6556 0.157 Uiso 1 1 calc R U . . .
H22B H 0.7683 0.3056 0.6841 0.157 Uiso 1 1 calc R U . . .
H22C H 0.8183 0.2552 0.6206 0.157 Uiso 1 1 calc R U . . .
C23 C 0.2097(8) 0.3847(6) 0.6104(4) 0.055(2) Uani 1 1 d D U . . .
H23A H 0.2440 0.4159 0.6534 0.066 Uiso 1 1 calc R U . . .
H23B H 0.1494 0.3363 0.6220 0.066 Uiso 1 1 calc R U . . .
C24 C 0.1217(9) 0.4461(6) 0.5617(5) 0.060(2) Uani 1 1 d D U . . .
H24A H 0.0422 0.4677 0.5834 0.091 Uiso 1 1 calc R U . . .
H24B H 0.1803 0.4949 0.5508 0.091 Uiso 1 1 calc R U . . .
H24C H 0.0858 0.4152 0.5194 0.091 Uiso 1 1 calc R U . . .
N1 N 0.5845(6) 0.5085(4) 0.7749(3) 0.0451(15) Uani 1 1 d . U . . .
H1 H 0.5678 0.4529 0.7683 0.054 Uiso 1 1 calc R U . . .
N2 N 0.5022(7) 0.4299(4) 0.6616(3) 0.0429(14) Uani 1 1 d . U . . .
W1 W 0.46007(17) 0.20338(11) 0.82308(8) 0.0315(3) Uani 0.680(5) 1 d D . P D 1
Cl1 Cl 0.6362(7) 0.1046(3) 0.8639(4) 0.0384(12) Uani 0.680(5) 1 d D U P D 1
Cl2 Cl 0.3902(11) 0.2093(7) 0.9300(3) 0.0582(11) Uani 0.680(5) 1 d D U P D 1
Cl3 Cl 0.3068(8) 0.0865(4) 0.7962(4) 0.0456(11) Uani 0.680(5) 1 d D U P D 1
Cl4 Cl 0.2873(7) 0.3020(5) 0.7822(3) 0.0790(15) Uani 0.680(5) 1 d D U P D 1
Cl5 Cl 0.6142(5) 0.3170(3) 0.8522(3) 0.0799(14) Uani 0.680(5) 1 d D U P D 1
Cl6 Cl 0.5273(4) 0.1969(3) 0.71563(17) 0.0562(9) Uani 0.680(5) 1 d D U P D 1
W11 W 0.4554(4) 0.2234(3) 0.8399(2) 0.0434(7) Uani 0.320(5) 1 d D . P D 2
Cl11 Cl 0.6395(16) 0.1263(9) 0.8734(9) 0.0384(12) Uani 0.320(5) 1 d D U P D 2
Cl12 Cl 0.378(3) 0.2007(16) 0.9440(8) 0.0582(11) Uani 0.320(5) 1 d D U P D 2
Cl13 Cl 0.325(2) 0.1053(10) 0.7913(9) 0.0456(11) Uani 0.320(5) 1 d D U P D 2
Cl14 Cl 0.2664(16) 0.3100(11) 0.8047(7) 0.0790(15) Uani 0.320(5) 1 d D U P D 2
Cl15 Cl 0.5932(12) 0.3347(6) 0.8896(5) 0.0799(14) Uani 0.320(5) 1 d D U P D 2
Cl16 Cl 0.5482(9) 0.2411(6) 0.7372(4) 0.0562(9) Uani 0.320(5) 1 d D U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.277(9) . ?
C1 C3 1.477(11) . ?
C1 C2 1.508(10) . ?
C2 N2 1.266(10) . ?
C2 C4 1.480(10) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.365(13) . ?
C5 C10 1.366(12) . ?
C5 N1 1.441(10) . ?
C6 C7 1.400(12) . ?
C6 C111 1.534(18) . ?
C6 C11 1.541(15) . ?
C7 C8 1.348(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.349(15) . ?
C8 C108 1.539(18) . ?
C8 H8 0.9500 . ?
C108 H10A 0.9800 . ?
C108 H10B 0.9800 . ?
C108 H10C 0.9800 . ?
C9 C10 1.388(13) . ?
C9 H9 0.9500 . ?
C10 C13 1.505(17) . ?
C10 C113 1.522(16) . ?
C11 C12 1.496(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12C 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C111 C112 1.49(2) . ?
C111 H11F 0.9900 . ?
C111 H11G 0.9900 . ?
C112 H11H 0.9800 . ?
C112 H11I 0.9800 . ?
C112 H11J 0.9800 . ?
C13 C14 1.554(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C113 C114 1.503(17) . ?
C113 H11K 0.9900 . ?
C113 H11L 0.9900 . ?
C114 H11M 0.9800 . ?
C114 H11N 0.9800 . ?
C114 H11O 0.9800 . ?
C15 C16 1.379(11) . ?
C15 C20 1.384(11) . ?
C15 N2 1.437(10) . ?
C16 C17 1.388(12) . ?
C16 C21 1.534(11) . ?
C17 C18 1.364(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.362(12) . ?
C18 C118 1.511(11) . ?
C18 H18 0.9500 . ?
C118 H11P 0.9800 . ?
C118 H11Q 0.9800 . ?
C118 H11R 0.9800 . ?
C19 C20 1.398(11) . ?
C19 H19 0.9500 . ?
C20 C23 1.505(10) . ?
C21 C22 1.450(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.519(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 H1 0.8800 . ?
W1 Cl6 2.294(3) . ?
W1 Cl2 2.295(5) . ?
W1 Cl4 2.310(5) . ?
W1 Cl5 2.313(4) . ?
W1 Cl1 2.333(5) . ?
W1 Cl3 2.340(4) . ?
W11 Cl14 2.280(11) . ?
W11 Cl12 2.299(11) . ?
W11 Cl15 2.302(8) . ?
W11 Cl16 2.331(7) . ?
W11 Cl11 2.338(11) . ?
W11 Cl13 2.341(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C3 123.7(7) . . ?
N1 C1 C2 115.0(7) . . ?
C3 C1 C2 121.3(7) . . ?
N2 C2 C4 126.6(7) . . ?
N2 C2 C1 114.2(7) . . ?
C4 C2 C1 119.1(7) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 124.0(8) . . ?
C6 C5 N1 119.6(7) . . ?
C10 C5 N1 116.2(8) . . ?
C5 C6 C7 117.0(9) . . ?
C5 C6 C111 116.9(13) . . ?
C7 C6 C111 117.8(15) . . ?
C5 C6 C11 121.1(9) . . ?
C7 C6 C11 121.0(11) . . ?
C8 C7 C6 120.8(11) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.8(9) . . ?
C7 C8 C108 114.5(19) . . ?
C9 C8 C108 125(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C108 H10A 109.5 . . ?
C8 C108 H10B 109.5 . . ?
H10A C108 H10B 109.5 . . ?
C8 C108 H10C 109.5 . . ?
H10A C108 H10C 109.5 . . ?
H10B C108 H10C 109.5 . . ?
C8 C9 C10 122.7(10) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
C5 C10 C9 115.7(9) . . ?
C5 C10 C13 127.3(14) . . ?
C9 C10 C13 116.3(14) . . ?
C5 C10 C113 116.1(10) . . ?
C9 C10 C113 127.3(11) . . ?
C12 C11 C6 109.9(14) . . ?
C12 C11 H11A 109.7 . . ?
C6 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C6 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12D 109.5 . . ?
H12C C12 H12D 109.5 . . ?
C11 C12 H12E 109.5 . . ?
H12C C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
C112 C111 C6 104(2) . . ?
C112 C111 H11F 110.9 . . ?
C6 C111 H11F 110.9 . . ?
C112 C111 H11G 110.9 . . ?
C6 C111 H11G 110.9 . . ?
H11F C111 H11G 108.9 . . ?
C111 C112 H11H 109.5 . . ?
C111 C112 H11I 109.5 . . ?
H11H C112 H11I 109.5 . . ?
C111 C112 H11J 109.5 . . ?
H11H C112 H11J 109.5 . . ?
H11I C112 H11J 109.5 . . ?
C10 C13 C14 110.5(19) . . ?
C10 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C10 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C114 C113 C10 112.5(16) . . ?
C114 C113 H11K 109.1 . . ?
C10 C113 H11K 109.1 . . ?
C114 C113 H11L 109.1 . . ?
C10 C113 H11L 109.1 . . ?
H11K C113 H11L 107.8 . . ?
C113 C114 H11M 109.5 . . ?
C113 C114 H11N 109.5 . . ?
H11M C114 H11N 109.5 . . ?
C113 C114 H11O 109.5 . . ?
H11M C114 H11O 109.5 . . ?
H11N C114 H11O 109.5 . . ?
C16 C15 C20 121.2(8) . . ?
C16 C15 N2 118.1(7) . . ?
C20 C15 N2 120.6(7) . . ?
C15 C16 C17 119.0(8) . . ?
C15 C16 C21 121.5(8) . . ?
C17 C16 C21 119.4(8) . . ?
C18 C17 C16 120.9(8) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.6(8) . . ?
C19 C18 C118 129.8(9) . . ?
C17 C18 C118 110.5(8) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C118 H11P 109.5 . . ?
C18 C118 H11Q 109.5 . . ?
H11P C118 H11Q 109.5 . . ?
C18 C118 H11R 109.5 . . ?
H11P C118 H11R 109.5 . . ?
H11Q C118 H11R 109.5 . . ?
C18 C19 C20 121.6(8) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 117.7(7) . . ?
C15 C20 C23 122.5(7) . . ?
C19 C20 C23 119.8(7) . . ?
C22 C21 C16 111.2(9) . . ?
C22 C21 H21A 109.4 . . ?
C16 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C16 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 C24 112.5(7) . . ?
C20 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
C20 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C5 127.2(7) . . ?
C1 N1 H1 116.4 . . ?
C5 N1 H1 116.4 . . ?
C2 N2 C15 122.9(6) . . ?
Cl6 W1 Cl2 179.3(3) . . ?
Cl6 W1 Cl4 89.09(16) . . ?
Cl2 W1 Cl4 90.6(3) . . ?
Cl6 W1 Cl5 90.73(16) . . ?
Cl2 W1 Cl5 89.9(3) . . ?
Cl4 W1 Cl5 89.3(2) . . ?
Cl6 W1 Cl1 90.6(2) . . ?
Cl2 W1 Cl1 89.8(3) . . ?
Cl4 W1 Cl1 179.4(3) . . ?
Cl5 W1 Cl1 90.3(2) . . ?
Cl6 W1 Cl3 90.2(2) . . ?
Cl2 W1 Cl3 89.2(3) . . ?
Cl4 W1 Cl3 91.9(3) . . ?
Cl5 W1 Cl3 178.5(2) . . ?
Cl1 W1 Cl3 88.5(3) . . ?
Cl14 W11 Cl12 91.2(7) . . ?
Cl14 W11 Cl15 94.3(6) . . ?
Cl12 W11 Cl15 88.3(7) . . ?
Cl14 W11 Cl16 92.7(4) . . ?
Cl12 W11 Cl16 176.1(7) . . ?
Cl15 W11 Cl16 91.1(4) . . ?
Cl14 W11 Cl11 176.0(7) . . ?
Cl12 W11 Cl11 88.5(7) . . ?
Cl15 W11 Cl11 89.6(5) . . ?
Cl16 W11 Cl11 87.7(5) . . ?
Cl14 W11 Cl13 88.6(7) . . ?
Cl12 W11 Cl13 91.5(7) . . ?
Cl15 W11 Cl13 177.1(6) . . ?
Cl16 W11 Cl13 89.0(5) . . ?
Cl11 W11 Cl13 87.4(6) . . ?

_refine_diff_density_max         1.416
_refine_diff_density_min         -1.482
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1814756'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cl5 Mo N2'
_chemical_formula_weight         495.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.7612(17)
_cell_length_b                   21.413(3)
_cell_length_c                   8.0173(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.973(2)
_cell_angle_gamma                90
_cell_volume                     1819.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.704
_cell_measurement_theta_max      28.6575

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.453
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7310
_exptl_absorpt_correction_T_max  0.8449
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1266 (selected reflections only, before parameter refinement)
 R(int) =  0.0450 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20835
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4330
_reflns_number_gt                3993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+1.1616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4330
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0527
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.11207(2) 0.13203(2) 0.40955(2) 0.01373(5) Uani 1 1 d . . . . .
Cl2 Cl 0.15344(4) 0.23605(2) 0.50072(6) 0.02028(9) Uani 1 1 d . . . . .
Cl4 Cl 0.29998(4) 0.13174(2) 0.31507(6) 0.02018(9) Uani 1 1 d . . . . .
Cl3 Cl 0.07899(5) 0.02840(2) 0.32121(6) 0.02333(10) Uani 1 1 d . . . . .
Cl5 Cl -0.05764(4) 0.16384(2) 0.22487(5) 0.01936(9) Uani 1 1 d . . . . .
Cl1 Cl 0.07723(4) 0.08905(2) 0.92153(5) 0.01794(9) Uani 1 1 d . . . . .
C1 C 0.09041(16) 0.10661(8) 0.7177(2) 0.0157(3) Uani 1 1 d . . . . .
N1 N 0.19462(14) 0.10169(7) 0.65219(18) 0.0155(3) Uani 1 1 d . . . . .
N2 N -0.00318(14) 0.12378(7) 0.59667(19) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.31711(16) 0.08660(8) 0.7377(2) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.38610(17) 0.04187(8) 0.6661(2) 0.0188(4) Uani 1 1 d . . . . .
H3 H 0.3496 0.0207 0.5654 0.023 Uiso 1 1 calc R U . . .
C4 C 0.50848(18) 0.02872(9) 0.7436(2) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.5550 -0.0023 0.6964 0.025 Uiso 1 1 calc R U . . .
C5 C 0.56482(17) 0.06016(9) 0.8896(2) 0.0212(4) Uani 1 1 d . . . . .
C6 C 0.49323(18) 0.10390(9) 0.9602(2) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.5295 0.1248 1.0615 0.025 Uiso 1 1 calc R U . . .
C7 C 0.37027(17) 0.11765(8) 0.8858(2) 0.0189(4) Uani 1 1 d . . . . .
H7 H 0.3229 0.1478 0.9351 0.023 Uiso 1 1 calc R U . . .
C8 C 0.70031(18) 0.04798(10) 0.9662(3) 0.0284(4) Uani 1 1 d . . . . .
H8A H 0.7552 0.0749 0.9120 0.043 Uiso 1 1 calc R U . . .
H8B H 0.7207 0.0041 0.9487 0.043 Uiso 1 1 calc R U . . .
H8C H 0.7133 0.0569 1.0879 0.043 Uiso 1 1 calc R U . . .
C9 C -0.12445(16) 0.14430(8) 0.6190(2) 0.0160(3) Uani 1 1 d . . . . .
C10 C -0.23025(17) 0.12379(8) 0.5062(2) 0.0183(4) Uani 1 1 d . . . . .
H10 H -0.2218 0.0936 0.4222 0.022 Uiso 1 1 calc R U . . .
C11 C -0.34760(17) 0.14811(9) 0.5184(2) 0.0192(4) Uani 1 1 d . . . . .
H11 H -0.4199 0.1339 0.4426 0.023 Uiso 1 1 calc R U . . .
C12 C -0.36193(17) 0.19329(9) 0.6404(2) 0.0188(4) Uani 1 1 d . . . . .
C13 C -0.25560(18) 0.21127(9) 0.7547(2) 0.0209(4) Uani 1 1 d . . . . .
H13 H -0.2641 0.2406 0.8409 0.025 Uiso 1 1 calc R U . . .
C14 C -0.13703(17) 0.18715(8) 0.7452(2) 0.0186(4) Uani 1 1 d . . . . .
H14 H -0.0653 0.1999 0.8243 0.022 Uiso 1 1 calc R U . . .
C15 C -0.48793(18) 0.22351(9) 0.6428(3) 0.0239(4) Uani 1 1 d . . . . .
H15A H -0.4833 0.2488 0.7457 0.036 Uiso 1 1 calc R U . . .
H15B H -0.5524 0.1911 0.6414 0.036 Uiso 1 1 calc R U . . .
H15C H -0.5101 0.2503 0.5430 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 N1 2.0969(15) . ?
Mo1 N2 2.1130(15) . ?
Mo1 Cl5 2.2484(5) . ?
Mo1 Cl4 2.2789(5) . ?
Mo1 Cl3 2.3377(6) . ?
Mo1 Cl2 2.3625(5) . ?
Cl1 C1 1.7063(17) . ?
C1 N1 1.322(2) . ?
C1 N2 1.324(2) . ?
N1 C2 1.414(2) . ?
N2 C9 1.417(2) . ?
C2 C7 1.394(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 C8 1.504(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.390(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 C15 1.506(2) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Mo1 N2 61.44(6) . . ?
N1 Mo1 Cl5 150.47(4) . . ?
N2 Mo1 Cl5 89.03(4) . . ?
N1 Mo1 Cl4 92.85(4) . . ?
N2 Mo1 Cl4 154.09(4) . . ?
Cl5 Mo1 Cl4 116.63(2) . . ?
N1 Mo1 Cl3 90.28(4) . . ?
N2 Mo1 Cl3 93.35(4) . . ?
Cl5 Mo1 Cl3 91.392(18) . . ?
Cl4 Mo1 Cl3 89.658(17) . . ?
N1 Mo1 Cl2 88.75(4) . . ?
N2 Mo1 Cl2 87.79(4) . . ?
Cl5 Mo1 Cl2 90.354(18) . . ?
Cl4 Mo1 Cl2 88.564(17) . . ?
Cl3 Mo1 Cl2 177.929(18) . . ?
N1 Mo1 C1 30.70(5) . . ?
N2 Mo1 C1 30.77(6) . . ?
Cl5 Mo1 C1 119.79(4) . . ?
Cl4 Mo1 C1 123.39(4) . . ?
Cl3 Mo1 C1 93.19(4) . . ?
Cl2 Mo1 C1 86.91(4) . . ?
N1 C1 N2 108.71(15) . . ?
N1 C1 Cl1 125.43(13) . . ?
N2 C1 Cl1 125.75(14) . . ?
N1 C1 Mo1 54.04(9) . . ?
N2 C1 Mo1 54.75(9) . . ?
Cl1 C1 Mo1 179.33(10) . . ?
C1 N1 C2 127.53(15) . . ?
C1 N1 Mo1 95.26(11) . . ?
C2 N1 Mo1 136.90(11) . . ?
C1 N2 C9 126.41(15) . . ?
C1 N2 Mo1 94.48(11) . . ?
C9 N2 Mo1 136.92(12) . . ?
C7 C2 C3 120.58(16) . . ?
C7 C2 N1 120.96(16) . . ?
C3 C2 N1 118.40(16) . . ?
C4 C3 C2 119.19(17) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.34(17) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.33(17) . . ?
C6 C5 C8 121.06(18) . . ?
C4 C5 C8 120.59(18) . . ?
C7 C6 C5 121.48(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 119.03(17) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 120.52(16) . . ?
C14 C9 N2 120.31(16) . . ?
C10 C9 N2 119.06(16) . . ?
C11 C10 C9 119.15(17) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.33(17) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.22(17) . . ?
C13 C12 C15 120.84(17) . . ?
C11 C12 C15 120.88(17) . . ?
C14 C13 C12 121.29(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C9 C14 C13 119.40(17) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N2 C1 N1 C2 177.67(16) . . . . ?
Cl1 C1 N1 C2 -6.0(3) . . . . ?
Mo1 C1 N1 C2 174.5(2) . . . . ?
N2 C1 N1 Mo1 3.13(15) . . . . ?
Cl1 C1 N1 Mo1 179.48(12) . . . . ?
N1 C1 N2 C9 -168.59(16) . . . . ?
Cl1 C1 N2 C9 15.1(3) . . . . ?
Mo1 C1 N2 C9 -165.48(19) . . . . ?
N1 C1 N2 Mo1 -3.11(15) . . . . ?
Cl1 C1 N2 Mo1 -179.44(12) . . . . ?
C1 N1 C2 C7 -49.8(3) . . . . ?
Mo1 N1 C2 C7 122.20(17) . . . . ?
C1 N1 C2 C3 133.11(19) . . . . ?
Mo1 N1 C2 C3 -54.9(2) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
N1 C2 C3 C4 176.84(16) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C3 C4 C5 C8 -176.37(17) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C8 C5 C6 C7 176.80(18) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
N1 C2 C7 C6 -176.34(16) . . . . ?
C1 N2 C9 C14 44.9(3) . . . . ?
Mo1 N2 C9 C14 -113.61(18) . . . . ?
C1 N2 C9 C10 -138.95(18) . . . . ?
Mo1 N2 C9 C10 62.5(2) . . . . ?
C14 C9 C10 C11 1.9(3) . . . . ?
N2 C9 C10 C11 -174.23(16) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -2.8(3) . . . . ?
C10 C11 C12 C15 174.61(17) . . . . ?
C11 C12 C13 C14 2.4(3) . . . . ?
C15 C12 C13 C14 -174.99(17) . . . . ?
C10 C9 C14 C13 -2.3(3) . . . . ?
N2 C9 C14 C13 173.81(16) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1814757'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H30 Cl6 N3 W'
_chemical_formula_weight         805.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.3116(4)
_cell_length_b                   18.5141(9)
_cell_length_c                   22.4919(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.532(3)
_cell_angle_gamma                90
_cell_volume                     3431.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.382
_cell_measurement_theta_max      27.1315

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             1580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.855
_shelx_estimated_absorpt_T_min   0.484
_shelx_estimated_absorpt_T_max   0.655
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3634
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1520 (selected reflections only, before parameter refinement)
 R(int) =  0.0726 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60561
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.430
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8263
_reflns_number_gt                6907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
 
 The largest peak is reported at 1.8 and it is close to 
 C26 in a chemically impossible position.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+4.2858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8263
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.90635(2) 0.11228(2) 0.79083(2) 0.02238(5) Uani 1 1 d . . . . .
Cl1 Cl 1.17943(10) 0.13876(5) 0.78510(4) 0.02607(17) Uani 1 1 d . . . . .
Cl2 Cl 0.83262(10) 0.20006(5) 0.71810(4) 0.03005(19) Uani 1 1 d . . . . .
Cl6 Cl 0.63431(11) 0.08779(7) 0.79658(4) 0.0434(3) Uani 1 1 d . . . . .
Cl4 Cl 0.98336(12) 0.02786(5) 0.86614(4) 0.0354(2) Uani 1 1 d . . . . .
Cl3 Cl 0.90493(12) 0.19828(5) 0.86547(4) 0.0339(2) Uani 1 1 d . . . . .
Cl5 Cl 0.90985(14) 0.02555(5) 0.71829(4) 0.0402(2) Uani 1 1 d . . . . .
N3 N 0.3773(3) 0.73986(16) 0.89185(13) 0.0254(6) Uani 1 1 d . . . . .
N2 N 0.4006(3) 0.89845(15) 0.87989(12) 0.0210(6) Uani 1 1 d . . . . .
N1 N 0.2972(3) 0.88651(14) 0.78695(12) 0.0203(5) Uani 1 1 d . . . . .
C4 C 0.3463(4) 0.77080(18) 0.84154(15) 0.0210(7) Uani 1 1 d . . . . .
H4 H 0.3211 0.7427 0.8062 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3490(4) 0.84952(18) 0.83736(14) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.3150(4) 0.95917(19) 0.79752(16) 0.0265(7) Uani 1 1 d . . . . .
H2 H 0.2869 0.9971 0.7696 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3804(4) 0.96611(19) 0.85551(16) 0.0282(8) Uani 1 1 d . . . . .
H3 H 0.4077 1.0103 0.8758 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3730(4) 0.6626(2) 0.89427(15) 0.0271(7) Uani 1 1 d . . . . .
C22 C 0.2332(5) 0.6227(2) 0.87224(17) 0.0312(8) Uani 1 1 d . . . . .
C23 C 0.2387(6) 0.5481(2) 0.87940(19) 0.0432(10) Uani 1 1 d . . . . .
H23 H 0.1463 0.5199 0.8649 0.052 Uiso 1 1 calc R U . . .
C24 C 0.3784(6) 0.5140(2) 0.90766(19) 0.0460(11) Uani 1 1 d . . . . .
H24 H 0.3814 0.4629 0.9113 0.055 Uiso 1 1 calc R U . . .
C25 C 0.5111(6) 0.5542(2) 0.93017(18) 0.0426(10) Uani 1 1 d . . . . .
H25 H 0.6042 0.5305 0.9501 0.051 Uiso 1 1 calc R U . . .
C26 C 0.5123(5) 0.6294(2) 0.92447(17) 0.0327(8) Uani 1 1 d . . . . .
C27 C 0.0780(5) 0.6582(2) 0.8450(2) 0.0412(10) Uani 1 1 d . . . . .
H27A H 0.0886 0.6739 0.8041 0.062 Uiso 1 1 calc R U . . .
H27B H 0.0560 0.7002 0.8692 0.062 Uiso 1 1 calc R U . . .
H27C H -0.0117 0.6237 0.8440 0.062 Uiso 1 1 calc R U . . .
C28 C 0.6578(5) 0.6724(2) 0.94899(18) 0.0417(10) Uani 1 1 d . . . . .
H28A H 0.7325 0.6418 0.9753 0.063 Uiso 1 1 calc R U . . .
H28B H 0.6240 0.7134 0.9720 0.063 Uiso 1 1 calc R U . . .
H28C H 0.7125 0.6903 0.9159 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4799(4) 0.88503(18) 0.94038(15) 0.0224(7) Uani 1 1 d . . . . .
C18 C 0.6477(4) 0.8747(2) 0.94775(17) 0.0301(8) Uani 1 1 d . . . . .
C17 C 0.7240(5) 0.8662(2) 1.00585(19) 0.0375(9) Uani 1 1 d . . . . .
H17 H 0.8383 0.8597 1.0129 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6350(5) 0.8671(2) 1.05396(18) 0.0369(9) Uani 1 1 d . . . . .
H16 H 0.6889 0.8612 1.0936 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4709(5) 0.8764(2) 1.04475(17) 0.0345(9) Uani 1 1 d . . . . .
H15 H 0.4119 0.8759 1.0782 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3872(4) 0.8866(2) 0.98728(16) 0.0284(8) Uani 1 1 d . . . . .
C20 C 0.7404(5) 0.8712(3) 0.89447(19) 0.0402(10) Uani 1 1 d . . . . .
H20A H 0.8561 0.8641 0.9084 0.060 Uiso 1 1 calc R U . . .
H20B H 0.7255 0.9165 0.8718 0.060 Uiso 1 1 calc R U . . .
H20 H 0.7000 0.8308 0.8686 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2075(5) 0.8974(3) 0.97667(19) 0.0455(11) Uani 1 1 d . . . . .
H19A H 0.1833 0.9456 0.9599 0.068 Uiso 1 1 calc R U . . .
H19B H 0.1629 0.8928 1.0147 0.068 Uiso 1 1 calc R U . . .
H19C H 0.1585 0.8608 0.9484 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2284(4) 0.85550(18) 0.72985(15) 0.0232(7) Uani 1 1 d . . . . .
C6 C 0.0660(4) 0.8352(2) 0.72329(16) 0.0282(7) Uani 1 1 d . . . . .
C7 C 0.0034(5) 0.8070(2) 0.66719(18) 0.0387(9) Uani 1 1 d . . . . .
H7 H -0.1064 0.7914 0.6604 0.046 Uiso 1 1 calc R U . . .
C8 C 0.0984(6) 0.8015(2) 0.62182(19) 0.0438(11) Uani 1 1 d . . . . .
H8 H 0.0523 0.7830 0.5840 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2576(5) 0.8220(2) 0.62983(17) 0.0397(10) Uani 1 1 d . . . . .
H9 H 0.3203 0.8172 0.5976 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3303(5) 0.8502(2) 0.68484(16) 0.0303(8) Uani 1 1 d . . . . .
C11 C -0.0380(4) 0.8442(2) 0.77281(18) 0.0331(8) Uani 1 1 d . . . . .
H11A H 0.0042 0.8137 0.8069 0.050 Uiso 1 1 calc R U . . .
H11B H -0.1498 0.8300 0.7582 0.050 Uiso 1 1 calc R U . . .
H11C H -0.0361 0.8949 0.7855 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5031(5) 0.8724(2) 0.69560(19) 0.0400(10) Uani 1 1 d . . . . .
H12A H 0.5105 0.9223 0.7102 0.060 Uiso 1 1 calc R U . . .
H12B H 0.5507 0.8690 0.6581 0.060 Uiso 1 1 calc R U . . .
H12C H 0.5623 0.8405 0.7257 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
W1 Cl5 2.2921(10) . ?
W1 Cl3 2.3149(9) . ?
W1 Cl6 2.3263(9) . ?
W1 Cl2 2.3302(9) . ?
W1 Cl4 2.3319(9) . ?
W1 Cl1 2.3420(8) . ?
N3 C4 1.264(4) . ?
N3 C21 1.432(4) . ?
N2 C1 1.346(4) . ?
N2 C3 1.369(4) . ?
N2 C13 1.453(4) . ?
N1 C1 1.346(4) . ?
N1 C2 1.371(4) . ?
N1 C5 1.454(4) . ?
C4 C1 1.461(4) . ?
C4 H4 0.9500 . ?
C2 C3 1.352(5) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C21 C26 1.405(5) . ?
C21 C22 1.411(5) . ?
C22 C23 1.392(5) . ?
C22 C27 1.504(6) . ?
C23 C24 1.399(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(5) . ?
C25 H25 0.9500 . ?
C26 C28 1.491(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C13 C14 1.386(5) . ?
C13 C18 1.395(5) . ?
C18 C17 1.385(5) . ?
C18 C20 1.509(5) . ?
C17 C16 1.389(6) . ?
C17 H17 0.9500 . ?
C16 C15 1.364(6) . ?
C16 H16 0.9500 . ?
C15 C14 1.398(5) . ?
C15 H15 0.9500 . ?
C14 C19 1.495(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 C6 1.390(5) . ?
C5 C10 1.406(5) . ?
C6 C7 1.402(5) . ?
C6 C11 1.506(5) . ?
C7 C8 1.374(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.366(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(5) . ?
C9 H9 0.9500 . ?
C10 C12 1.483(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
Cl5 W1 Cl3 178.89(4) . . ?
Cl5 W1 Cl6 90.35(4) . . ?
Cl3 W1 Cl6 89.79(4) . . ?
Cl5 W1 Cl2 90.89(4) . . ?
Cl3 W1 Cl2 90.21(4) . . ?
Cl6 W1 Cl2 90.40(3) . . ?
Cl5 W1 Cl4 91.13(4) . . ?
Cl3 W1 Cl4 87.77(4) . . ?
Cl6 W1 Cl4 90.30(4) . . ?
Cl2 W1 Cl4 177.86(3) . . ?
Cl5 W1 Cl1 90.27(4) . . ?
Cl3 W1 Cl1 89.60(3) . . ?
Cl6 W1 Cl1 179.16(4) . . ?
Cl2 W1 Cl1 89.02(3) . . ?
Cl4 W1 Cl1 90.26(3) . . ?
C4 N3 C21 118.9(3) . . ?
C1 N2 C3 108.7(3) . . ?
C1 N2 C13 127.8(3) . . ?
C3 N2 C13 123.2(3) . . ?
C1 N1 C2 109.7(3) . . ?
C1 N1 C5 126.1(3) . . ?
C2 N1 C5 124.2(3) . . ?
N3 C4 C1 120.4(3) . . ?
N3 C4 H4 119.8 . . ?
C1 C4 H4 119.8 . . ?
N1 C1 N2 107.0(3) . . ?
N1 C1 C4 123.8(3) . . ?
N2 C1 C4 129.2(3) . . ?
C3 C2 N1 106.3(3) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
N2 C3 H3 125.9 . . ?
C26 C21 C22 122.0(4) . . ?
C26 C21 N3 115.6(3) . . ?
C22 C21 N3 122.2(3) . . ?
C23 C22 C21 117.8(4) . . ?
C23 C22 C27 119.6(4) . . ?
C21 C22 C27 122.5(3) . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.5(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 117.7(4) . . ?
C25 C26 C28 120.8(4) . . ?
C21 C26 C28 121.5(4) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C14 C13 C18 124.0(3) . . ?
C14 C13 N2 118.7(3) . . ?
C18 C13 N2 117.3(3) . . ?
C17 C18 C13 117.1(4) . . ?
C17 C18 C20 121.7(4) . . ?
C13 C18 C20 121.2(3) . . ?
C18 C17 C16 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C13 C14 C15 116.2(4) . . ?
C13 C14 C19 121.7(3) . . ?
C15 C14 C19 122.1(4) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20 109.5 . . ?
H20A C20 H20 109.5 . . ?
H20B C20 H20 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C5 C10 124.9(3) . . ?
C6 C5 N1 117.7(3) . . ?
C10 C5 N1 117.3(3) . . ?
C5 C6 C7 115.9(3) . . ?
C5 C6 C11 122.3(3) . . ?
C7 C6 C11 121.7(3) . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 115.5(4) . . ?
C9 C10 C12 122.8(4) . . ?
C5 C10 C12 121.7(3) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C21 N3 C4 C1 179.8(3) . . . . ?
C2 N1 C1 N2 -0.3(4) . . . . ?
C5 N1 C1 N2 -178.8(3) . . . . ?
C2 N1 C1 C4 179.8(3) . . . . ?
C5 N1 C1 C4 1.3(5) . . . . ?
C3 N2 C1 N1 0.0(4) . . . . ?
C13 N2 C1 N1 -174.3(3) . . . . ?
C3 N2 C1 C4 179.8(3) . . . . ?
C13 N2 C1 C4 5.5(5) . . . . ?
N3 C4 C1 N1 -171.0(3) . . . . ?
N3 C4 C1 N2 9.2(5) . . . . ?
C1 N1 C2 C3 0.5(4) . . . . ?
C5 N1 C2 C3 179.1(3) . . . . ?
N1 C2 C3 N2 -0.5(4) . . . . ?
C1 N2 C3 C2 0.3(4) . . . . ?
C13 N2 C3 C2 175.0(3) . . . . ?
C4 N3 C21 C26 127.5(3) . . . . ?
C4 N3 C21 C22 -57.7(5) . . . . ?
C26 C21 C22 C23 -2.3(5) . . . . ?
N3 C21 C22 C23 -176.8(3) . . . . ?
C26 C21 C22 C27 174.1(4) . . . . ?
N3 C21 C22 C27 -0.5(5) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C27 C22 C23 C24 -176.3(4) . . . . ?
C22 C23 C24 C25 1.7(6) . . . . ?
C23 C24 C25 C26 -1.5(6) . . . . ?
C24 C25 C26 C21 -0.6(6) . . . . ?
C24 C25 C26 C28 -179.8(4) . . . . ?
C22 C21 C26 C25 2.5(5) . . . . ?
N3 C21 C26 C25 177.4(3) . . . . ?
C22 C21 C26 C28 -178.3(4) . . . . ?
N3 C21 C26 C28 -3.5(5) . . . . ?
C1 N2 C13 C14 -98.7(4) . . . . ?
C3 N2 C13 C14 87.8(4) . . . . ?
C1 N2 C13 C18 84.3(4) . . . . ?
C3 N2 C13 C18 -89.2(4) . . . . ?
C14 C13 C18 C17 -0.6(5) . . . . ?
N2 C13 C18 C17 176.3(3) . . . . ?
C14 C13 C18 C20 178.1(4) . . . . ?
N2 C13 C18 C20 -5.1(5) . . . . ?
C13 C18 C17 C16 0.9(6) . . . . ?
C20 C18 C17 C16 -177.8(4) . . . . ?
C18 C17 C16 C15 0.0(6) . . . . ?
C17 C16 C15 C14 -1.3(6) . . . . ?
C18 C13 C14 C15 -0.6(5) . . . . ?
N2 C13 C14 C15 -177.4(3) . . . . ?
C18 C13 C14 C19 -179.5(4) . . . . ?
N2 C13 C14 C19 3.7(5) . . . . ?
C16 C15 C14 C13 1.5(5) . . . . ?
C16 C15 C14 C19 -179.6(4) . . . . ?
C1 N1 C5 C6 80.1(4) . . . . ?
C2 N1 C5 C6 -98.2(4) . . . . ?
C1 N1 C5 C10 -101.6(4) . . . . ?
C2 N1 C5 C10 80.1(4) . . . . ?
C10 C5 C6 C7 0.6(5) . . . . ?
N1 C5 C6 C7 178.7(3) . . . . ?
C10 C5 C6 C11 -178.3(3) . . . . ?
N1 C5 C6 C11 -0.1(5) . . . . ?
C5 C6 C7 C8 -1.2(6) . . . . ?
C11 C6 C7 C8 177.6(4) . . . . ?
C6 C7 C8 C9 1.2(7) . . . . ?
C7 C8 C9 C10 -0.5(6) . . . . ?
C8 C9 C10 C5 -0.1(6) . . . . ?
C8 C9 C10 C12 179.3(4) . . . . ?
C6 C5 C10 C9 0.1(5) . . . . ?
N1 C5 C10 C9 -178.1(3) . . . . ?
C6 C5 C10 C12 -179.4(4) . . . . ?
N1 C5 C10 C12 2.4(5) . . . . ?

_refine_diff_density_max         1.773
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.111



