# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1869885'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_1                   
;
PROBLEM: Check Calcd Resid. Dens.  0.89A   From W1              2.97 eA-3
RESPONSE: This alert of levels B is due to a high value for the residual electron density. The maximum is located close to the W atom, in a position which is not realistic for any atom. This is a e series termination error due to absorption effects.
;
# Added during the CSD deposition process: Wednesday 26 September 2018 09:22 AM
# end Validation Reply Form


_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            'C19 H15 Cl5 O W'
_chemical_formula_weight         620.41

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'
O O 0.0106 0.0060 '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/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                   14.275(2)
_cell_length_b                   7.9205(11)
_cell_length_c                   18.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.080(2)
_cell_angle_gamma                90
_cell_volume                     2059.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5470
_cell_measurement_theta_min      2.2365
_cell_measurement_theta_max      27.8955

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    6.265
_shelx_estimated_absorpt_T_min   0.398
_shelx_estimated_absorpt_T_max   0.546
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3935
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1360 (selected reflections only, before parameter refinement)
 R(int) =  0.0657(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            16758
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.465
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_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             3654
_reflns_number_gt                3244
_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)+(0.0262P)²+14.2528P] 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         3654
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.002
_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 0.7783(5) 0.3966(9) 0.3549(3) 0.0189(14) Uani 1 1 d . . . . .
C2 C 0.7837(5) 0.2342(8) 0.3206(3) 0.0162(13) Uani 1 1 d . . . . .
C3 C 0.8706(4) 0.1445(8) 0.3325(3) 0.0157(13) Uani 1 1 d . . . . .
H3 H 0.9270 0.1920 0.3627 0.019 Uiso 1 1 calc R U . . .
C4 C 0.8751(6) -0.0060(10) 0.3022(4) 0.0317(18) Uani 1 1 d . . . . .
H4 H 0.9346 -0.0650 0.3117 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7930(5) -0.0807(9) 0.2558(4) 0.0248(16) Uani 1 1 d . . . . .
H5 H 0.7974 -0.1874 0.2336 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7062(5) 0.0050(8) 0.2435(4) 0.0232(15) Uani 1 1 d . . . . .
H6 H 0.6503 -0.0441 0.2133 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7005(5) 0.1613(8) 0.2749(3) 0.0178(14) Uani 1 1 d . . . . .
H7 H 0.6410 0.2201 0.2658 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6877(5) 0.4539(9) 0.3693(3) 0.0189(14) Uani 1 1 d . . . . .
C9 C 0.6244(5) 0.3410(9) 0.3925(3) 0.0209(14) Uani 1 1 d . . . . .
H9 H 0.6392 0.2240 0.3968 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5413(5) 0.4000(10) 0.4090(4) 0.0282(17) Uani 1 1 d . . . . .
H10 H 0.5002 0.3242 0.4267 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5169(5) 0.5686(10) 0.4000(4) 0.0290(18) Uani 1 1 d . . . . .
H11 H 0.4584 0.6070 0.4105 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5765(5) 0.6820(9) 0.3759(3) 0.0243(16) Uani 1 1 d . . . . .
H12 H 0.5585 0.7974 0.3688 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6629(5) 0.6264(9) 0.3620(3) 0.0218(15) Uani 1 1 d . . . . .
H13 H 0.7055 0.7048 0.3476 0.026 Uiso 1 1 calc R U . . .
C14 C 0.8624(5) 0.5012(8) 0.3776(3) 0.0186(14) Uani 1 1 d . . . . .
C15 C 0.8738(5) 0.6027(9) 0.4411(3) 0.0208(14) Uani 1 1 d . . . . .
H15 H 0.8242 0.6060 0.4674 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9549(5) 0.6955(8) 0.4650(3) 0.0198(14) Uani 1 1 d . . . . .
H16 H 0.9614 0.7617 0.5082 0.024 Uiso 1 1 calc R U . . .
C17 C 1.0285(5) 0.6953(9) 0.4274(4) 0.0244(15) Uani 1 1 d . . . . .
H17 H 1.0851 0.7602 0.4449 0.029 Uiso 1 1 calc R U . . .
C18 C 1.0184(5) 0.5986(9) 0.3635(4) 0.0247(15) Uani 1 1 d . . . . .
H18 H 1.0676 0.6000 0.3368 0.030 Uiso 1 1 calc R U . . .
C19 C 0.9375(5) 0.5014(8) 0.3391(4) 0.0208(15) Uani 1 1 d . . . . .
H19 H 0.9319 0.4341 0.2963 0.025 Uiso 1 1 calc R U . . .
Cl1 Cl 0.86998(12) 0.9311(2) 0.64722(9) 0.0264(4) Uani 1 1 d . . . . .
Cl2 Cl 0.70421(12) 0.6767(2) 0.56148(8) 0.0243(4) Uani 1 1 d . . . . .
Cl3 Cl 0.64426(14) 0.9482(2) 0.67353(9) 0.0289(4) Uani 1 1 d . . . . .
Cl4 Cl 0.72977(13) 1.2544(2) 0.59122(10) 0.0291(4) Uani 1 1 d . . . . .
Cl5 Cl 0.78616(12) 0.9874(2) 0.47279(8) 0.0230(4) Uani 1 1 d . . . . .
O1 O 0.6030(3) 0.9948(8) 0.5081(3) 0.0434(15) Uani 1 1 d D . . . .
W1 W 0.70594(2) 0.96874(3) 0.56799(2) 0.01860(11) Uani 1 1 d . . . . .


_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 C14 1.442(9) . ?
C1 C2 1.447(9) . ?
C1 C8 1.452(9) . ?
C2 C3 1.403(9) . ?
C2 C7 1.419(9) . ?
C3 C4 1.328(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.421(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.408(9) . ?
C8 C13 1.410(10) . ?
C9 C10 1.374(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(10) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.412(9) . ?
C14 C19 1.419(9) . ?
C15 C16 1.359(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
Cl1 W1 2.4893(17) . ?
Cl2 W1 2.3165(17) . ?
Cl3 W1 2.3414(16) . ?
Cl4 W1 2.3145(18) . ?
Cl5 W1 2.3292(16) . ?
O1 W1 1.647(4) . ?

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
C14 C1 C2 121.1(6) . . ?
C14 C1 C8 118.9(6) . . ?
C2 C1 C8 119.9(6) . . ?
C3 C2 C7 118.6(6) . . ?
C3 C2 C1 120.9(6) . . ?
C7 C2 C1 120.5(6) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.4(7) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.8(7) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 120.0(6) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 C13 118.7(6) . . ?
C9 C8 C1 121.3(6) . . ?
C13 C8 C1 120.0(6) . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.6(7) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.8(6) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.6(7) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 120.3(7) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C15 C14 C19 118.0(6) . . ?
C15 C14 C1 120.3(6) . . ?
C19 C14 C1 121.7(6) . . ?
C16 C15 C14 120.9(6) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.1(6) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 119.3(6) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.4(6) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.3(6) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O1 W1 Cl4 94.4(2) . . ?
O1 W1 Cl2 95.3(2) . . ?
Cl4 W1 Cl2 170.24(6) . . ?
O1 W1 Cl5 89.39(17) . . ?
Cl4 W1 Cl5 90.26(6) . . ?
Cl2 W1 Cl5 91.40(6) . . ?
O1 W1 Cl3 97.72(18) . . ?
Cl4 W1 Cl3 88.68(6) . . ?
Cl2 W1 Cl3 88.48(6) . . ?
Cl5 W1 Cl3 172.87(6) . . ?
O1 W1 Cl1 173.85(17) . . ?
Cl4 W1 Cl1 85.81(6) . . ?
Cl2 W1 Cl1 84.78(6) . . ?
Cl5 W1 Cl1 84.46(6) . . ?
Cl3 W1 Cl1 88.43(6) . . ?

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
C14 C1 C2 C3 24.3(9) . . . . ?
C8 C1 C2 C3 -153.4(6) . . . . ?
C14 C1 C2 C7 -156.5(6) . . . . ?
C8 C1 C2 C7 25.8(8) . . . . ?
C7 C2 C3 C4 -0.5(9) . . . . ?
C1 C2 C3 C4 178.7(6) . . . . ?
C2 C3 C4 C5 0.9(10) . . . . ?
C3 C4 C5 C6 -1.3(10) . . . . ?
C4 C5 C6 C7 1.1(10) . . . . ?
C5 C6 C7 C2 -0.7(9) . . . . ?
C3 C2 C7 C6 0.3(9) . . . . ?
C1 C2 C7 C6 -178.9(6) . . . . ?
C14 C1 C8 C9 -140.0(6) . . . . ?
C2 C1 C8 C9 37.8(8) . . . . ?
C14 C1 C8 C13 38.3(8) . . . . ?
C2 C1 C8 C13 -143.9(6) . . . . ?
C13 C8 C9 C10 -1.3(9) . . . . ?
C1 C8 C9 C10 177.1(6) . . . . ?
C8 C9 C10 C11 2.8(10) . . . . ?
C9 C10 C11 C12 -1.4(10) . . . . ?
C10 C11 C12 C13 -1.4(10) . . . . ?
C11 C12 C13 C8 2.8(9) . . . . ?
C9 C8 C13 C12 -1.5(9) . . . . ?
C1 C8 C13 C12 -179.9(6) . . . . ?
C2 C1 C14 C15 -145.6(6) . . . . ?
C8 C1 C14 C15 32.2(9) . . . . ?
C2 C1 C14 C19 32.1(9) . . . . ?
C8 C1 C14 C19 -150.2(6) . . . . ?
C19 C14 C15 C16 -1.0(9) . . . . ?
C1 C14 C15 C16 176.8(6) . . . . ?
C14 C15 C16 C17 0.8(10) . . . . ?
C15 C16 C17 C18 0.4(10) . . . . ?
C16 C17 C18 C19 -1.6(10) . . . . ?
C17 C18 C19 C14 1.4(10) . . . . ?
C15 C14 C19 C18 -0.2(10) . . . . ?
C1 C14 C19 C18 -177.9(6) . . . . ?

_refine_diff_density_max         2.845
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.165


####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1869886'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-11-23 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 H24'
_chemical_formula_weight         360.47

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'

_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                   11.0309(3)
_cell_length_b                   17.4337(5)
_cell_length_c                   11.3811(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.847(2)
_cell_angle_gamma                90
_cell_volume                     2031.50(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7813
_cell_measurement_theta_min      2.1955
_cell_measurement_theta_max      26.870

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5212
_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) =  0.1691 (selected reflections only, before parameter refinement)
 R(int) =  0.0523(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            34185
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         26.999
_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             4436
_reflns_number_gt                3301
_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)+(0.0429P)²+0.4476P] 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         4436
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.14192(12) 0.20087(8) 0.76604(12) 0.0401(3) Uani 1 1 d . . . . .
H1A H 0.1187 0.2490 0.7202 0.048 Uiso 1 1 calc R U . . .
H1B H 0.0862 0.1608 0.7145 0.048 Uiso 1 1 calc R U . . .
C5 C 0.12319(12) 0.20723(7) 0.89495(12) 0.0390(3) Uani 1 1 d . . . . .
C2 C 0.28880(12) 0.18147(7) 0.79462(11) 0.0376(3) Uani 1 1 d . . . . .
C4 C 0.23813(13) 0.16051(7) 0.98113(11) 0.0386(3) Uani 1 1 d . . . . .
C3 C 0.32967(12) 0.14667(7) 0.92687(11) 0.0386(3) Uani 1 1 d . . . . .
C23 C 0.30327(12) 0.12091(7) 0.70186(12) 0.0398(3) Uani 1 1 d . . . . .
C17 C 0.36424(12) 0.25548(7) 0.79298(12) 0.0394(3) Uani 1 1 d . . . . .
C9 C 0.26052(15) 0.13509(8) 1.10321(13) 0.0493(3) Uani 1 1 d . . . . .
H9 H 0.2001 0.1449 1.1405 0.059 Uiso 1 1 calc R U . . .
C11 C -0.00952(13) 0.17341(8) 0.87957(12) 0.0416(3) Uani 1 1 d . . . . .
C16 C -0.11956(15) 0.21828(9) 0.85842(15) 0.0557(4) Uani 1 1 d . . . . .
H16 H -0.1115 0.2714 0.8615 0.067 Uiso 1 1 calc R U . . .
C6 C 0.44288(14) 0.10590(8) 0.99270(13) 0.0497(3) Uani 1 1 d . . . . .
H6 H 0.5036 0.0960 0.9558 0.060 Uiso 1 1 calc R U . . .
C24 C 0.38279(14) 0.12999(9) 0.63304(14) 0.0508(4) Uani 1 1 d . . . . .
H24 H 0.4320 0.1745 0.6428 0.061 Uiso 1 1 calc R U . . .
C10 C 0.14016(15) 0.29041(8) 0.94339(15) 0.0545(4) Uani 1 1 d . . . . .
H10A H 0.1274 0.2927 1.0223 0.082 Uiso 1 1 calc R U . . .
H10B H 0.0771 0.3226 0.8824 0.082 Uiso 1 1 calc R U . . .
H10C H 0.2266 0.3079 0.9558 0.082 Uiso 1 1 calc R U . . .
C18 C 0.47123(14) 0.27989(9) 0.89553(14) 0.0506(3) Uani 1 1 d . . . . .
H18 H 0.5001 0.2508 0.9693 0.061 Uiso 1 1 calc R U . . .
C7 C 0.46414(16) 0.08026(9) 1.11388(14) 0.0578(4) Uani 1 1 d . . . . .
H7 H 0.5397 0.0530 1.1588 0.069 Uiso 1 1 calc R U . . .
C8 C 0.37368(16) 0.09506(9) 1.16833(13) 0.0563(4) Uani 1 1 d . . . . .
H8 H 0.3892 0.0778 1.2500 0.068 Uiso 1 1 calc R U . . .
C27 C 0.24219(17) -0.00373(9) 0.60358(15) 0.0585(4) Uani 1 1 d . . . . .
H27 H 0.1950 -0.0490 0.5948 0.070 Uiso 1 1 calc R U . . .
C12 C -0.02659(15) 0.09441(8) 0.87657(15) 0.0538(4) Uani 1 1 d . . . . .
H12 H 0.0454 0.0627 0.8916 0.065 Uiso 1 1 calc R U . . .
C22 C 0.32458(15) 0.30137(9) 0.68556(13) 0.0541(4) Uani 1 1 d . . . . .
H22 H 0.2524 0.2868 0.6152 0.065 Uiso 1 1 calc R U . . .
C15 C -0.24112(16) 0.18552(11) 0.83282(17) 0.0668(5) Uani 1 1 d . . . . .
H15 H -0.3135 0.2168 0.8181 0.080 Uiso 1 1 calc R U . . .
C28 C 0.23510(15) 0.05198(8) 0.68678(14) 0.0506(3) Uani 1 1 d . . . . .
H28 H 0.1835 0.0433 0.7341 0.061 Uiso 1 1 calc R U . . .
C21 C 0.38971(18) 0.36821(10) 0.68067(16) 0.0640(4) Uani 1 1 d . . . . .
H21 H 0.3614 0.3979 0.6075 0.077 Uiso 1 1 calc R U . . .
C25 C 0.38997(16) 0.07364(10) 0.54982(15) 0.0611(4) Uani 1 1 d . . . . .
H25 H 0.4439 0.0810 0.5045 0.073 Uiso 1 1 calc R U . . .
C26 C 0.31910(16) 0.00765(9) 0.53347(15) 0.0602(4) Uani 1 1 d . . . . .
H26 H 0.3226 -0.0292 0.4757 0.072 Uiso 1 1 calc R U . . .
C14 C -0.25565(16) 0.10750(11) 0.82900(16) 0.0653(5) Uani 1 1 d . . . . .
H14 H -0.3375 0.0857 0.8112 0.078 Uiso 1 1 calc R U . . .
C20 C 0.49629(16) 0.39097(9) 0.78370(16) 0.0608(4) Uani 1 1 d . . . . .
H20 H 0.5405 0.4359 0.7806 0.073 Uiso 1 1 calc R U . . .
C19 C 0.53632(16) 0.34722(10) 0.89009(16) 0.0616(4) Uani 1 1 d . . . . .
H19 H 0.6082 0.3625 0.9601 0.074 Uiso 1 1 calc R U . . .
C13 C -0.14760(16) 0.06165(10) 0.85185(17) 0.0633(4) Uani 1 1 d . . . . .
H13 H -0.1561 0.0086 0.8506 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C5 1.5599(17) . ?
C1 C2 1.5662(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 C4 1.5191(18) . ?
C5 C11 1.5266(18) . ?
C5 C10 1.5378(18) . ?
C2 C3 1.5270(17) . ?
C2 C17 1.5391(18) . ?
C2 C23 1.5427(18) . ?
C4 C3 1.3868(18) . ?
C4 C9 1.3900(18) . ?
C3 C6 1.3891(18) . ?
C23 C24 1.3854(19) . ?
C23 C28 1.3939(19) . ?
C17 C18 1.3824(18) . ?
C17 C22 1.3886(19) . ?
C9 C8 1.381(2) . ?
C9 H9 0.9300 . ?
C11 C16 1.3878(19) . ?
C11 C12 1.389(2) . ?
C16 C15 1.385(2) . ?
C16 H16 0.9300 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9300 . ?
C24 C25 1.387(2) . ?
C24 H24 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9300 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C27 C26 1.378(2) . ?
C27 C28 1.379(2) . ?
C27 H27 0.9300 . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C22 C21 1.381(2) . ?
C22 H22 0.9300 . ?
C15 C14 1.368(3) . ?
C15 H15 0.9300 . ?
C28 H28 0.9300 . ?
C21 C20 1.374(2) . ?
C21 H21 0.9300 . ?
C25 C26 1.364(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C14 C13 1.377(2) . ?
C14 H14 0.9300 . ?
C20 C19 1.358(2) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C13 H13 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
C5 C1 C2 107.99(10) . . ?
C5 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
C5 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
C4 C5 C11 113.65(10) . . ?
C4 C5 C10 108.25(11) . . ?
C11 C5 C10 112.89(11) . . ?
C4 C5 C1 101.44(10) . . ?
C11 C5 C1 108.76(10) . . ?
C10 C5 C1 111.29(11) . . ?
C3 C2 C17 112.48(10) . . ?
C3 C2 C23 109.56(10) . . ?
C17 C2 C23 111.80(10) . . ?
C3 C2 C1 101.16(10) . . ?
C17 C2 C1 109.79(10) . . ?
C23 C2 C1 111.60(10) . . ?
C3 C4 C9 120.11(13) . . ?
C3 C4 C5 112.14(11) . . ?
C9 C4 C5 127.70(12) . . ?
C4 C3 C6 120.41(12) . . ?
C4 C3 C2 111.91(11) . . ?
C6 C3 C2 127.68(12) . . ?
C24 C23 C28 117.06(12) . . ?
C24 C23 C2 123.86(12) . . ?
C28 C23 C2 119.07(12) . . ?
C18 C17 C22 117.14(13) . . ?
C18 C17 C2 122.92(12) . . ?
C22 C17 C2 119.94(11) . . ?
C8 C9 C4 119.12(14) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C16 C11 C12 116.93(13) . . ?
C16 C11 C5 122.79(12) . . ?
C12 C11 C5 120.09(12) . . ?
C15 C16 C11 121.33(15) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C7 C6 C3 119.19(14) . . ?
C7 C6 H6 120.4 . . ?
C3 C6 H6 120.4 . . ?
C23 C24 C25 120.94(14) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C18 C19 121.03(14) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C8 C7 C6 120.26(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.90(13) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C26 C27 C28 120.04(15) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C13 C12 C11 121.81(14) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C21 C22 C17 121.57(14) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
C14 C15 C16 120.62(15) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C27 C28 C23 121.74(14) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?
C20 C21 C22 120.13(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C26 C25 C24 121.00(15) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.17(14) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C15 C14 C13 119.21(15) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C19 C20 C21 119.31(14) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C19 C18 120.81(15) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C14 C13 C12 120.09(16) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 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
C2 C1 C5 C4 -22.46(12) . . . . ?
C2 C1 C5 C11 -142.53(11) . . . . ?
C2 C1 C5 C10 92.49(13) . . . . ?
C5 C1 C2 C3 22.05(12) . . . . ?
C5 C1 C2 C17 -96.97(11) . . . . ?
C5 C1 C2 C23 138.49(11) . . . . ?
C11 C5 C4 C3 130.99(12) . . . . ?
C10 C5 C4 C3 -102.74(13) . . . . ?
C1 C5 C4 C3 14.44(13) . . . . ?
C11 C5 C4 C9 -51.85(17) . . . . ?
C10 C5 C4 C9 74.42(16) . . . . ?
C1 C5 C4 C9 -168.40(13) . . . . ?
C9 C4 C3 C6 1.45(19) . . . . ?
C5 C4 C3 C6 178.86(12) . . . . ?
C9 C4 C3 C2 -178.08(11) . . . . ?
C5 C4 C3 C2 -0.68(15) . . . . ?
C17 C2 C3 C4 103.73(12) . . . . ?
C23 C2 C3 C4 -131.28(11) . . . . ?
C1 C2 C3 C4 -13.35(13) . . . . ?
C17 C2 C3 C6 -75.76(17) . . . . ?
C23 C2 C3 C6 49.23(17) . . . . ?
C1 C2 C3 C6 167.16(13) . . . . ?
C3 C2 C23 C24 -120.69(14) . . . . ?
C17 C2 C23 C24 4.70(17) . . . . ?
C1 C2 C23 C24 128.10(13) . . . . ?
C3 C2 C23 C28 58.04(15) . . . . ?
C17 C2 C23 C28 -176.57(11) . . . . ?
C1 C2 C23 C28 -53.16(15) . . . . ?
C3 C2 C17 C18 10.05(17) . . . . ?
C23 C2 C17 C18 -113.71(14) . . . . ?
C1 C2 C17 C18 121.87(13) . . . . ?
C3 C2 C17 C22 -169.25(12) . . . . ?
C23 C2 C17 C22 66.99(16) . . . . ?
C1 C2 C17 C22 -57.43(15) . . . . ?
C3 C4 C9 C8 -1.0(2) . . . . ?
C5 C4 C9 C8 -177.96(13) . . . . ?
C4 C5 C11 C16 149.43(13) . . . . ?
C10 C5 C11 C16 25.65(18) . . . . ?
C1 C5 C11 C16 -98.39(14) . . . . ?
C4 C5 C11 C12 -35.64(17) . . . . ?
C10 C5 C11 C12 -159.42(13) . . . . ?
C1 C5 C11 C12 76.54(15) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
C5 C11 C16 C15 173.73(14) . . . . ?
C4 C3 C6 C7 -1.0(2) . . . . ?
C2 C3 C6 C7 178.48(13) . . . . ?
C28 C23 C24 C25 2.1(2) . . . . ?
C2 C23 C24 C25 -179.11(13) . . . . ?
C22 C17 C18 C19 -0.5(2) . . . . ?
C2 C17 C18 C19 -179.84(13) . . . . ?
C3 C6 C7 C8 0.1(2) . . . . ?
C4 C9 C8 C7 0.1(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C5 C11 C12 C13 -174.28(14) . . . . ?
C18 C17 C22 C21 0.6(2) . . . . ?
C2 C17 C22 C21 179.91(14) . . . . ?
C11 C16 C15 C14 0.7(3) . . . . ?
C26 C27 C28 C23 0.6(2) . . . . ?
C24 C23 C28 C27 -2.4(2) . . . . ?
C2 C23 C28 C27 178.78(13) . . . . ?
C17 C22 C21 C20 -0.2(3) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C24 C25 C26 C27 -1.8(2) . . . . ?
C28 C27 C26 C25 1.5(2) . . . . ?
C16 C15 C14 C13 0.5(3) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C21 C20 C19 C18 0.3(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.028





