# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_16nov29b
_database_code_depnum_ccdc_archive 'CCDC 1560125'
_audit_update_record             
;
2017-07-04 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C69 H46 Cl3 N O'
_chemical_formula_weight         1011.42

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   13.1358(8)
_cell_length_b                   14.0526(6)
_cell_length_c                   28.8957(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.657(6)
_cell_angle_gamma                90.00
_cell_volume                     5286.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180
_cell_measurement_reflns_used    3697
_cell_measurement_theta_min      3.3700
_cell_measurement_theta_max      26.8720

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2104
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15922
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.02
_reflns_number_total             5175
_reflns_number_gt                3480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+4.2183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5175
_refine_ls_number_parameters     362
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16819(19) 0.72735(16) 0.22047(9) 0.0468(6) Uani 1 1 d . . .
H1 H 0.1991 0.6767 0.2391 0.056 Uiso 1 1 calc R . .
C2 C 0.2261(2) 0.77884(18) 0.19300(9) 0.0545(7) Uani 1 1 d . . .
H2 H 0.2959 0.7623 0.1920 0.065 Uiso 1 1 calc R . .
C3 C 0.1831(2) 0.85439(19) 0.16693(9) 0.0600(8) Uani 1 1 d . . .
H3 H 0.2232 0.8897 0.1479 0.072 Uiso 1 1 calc R . .
C4 C 0.0820(2) 0.87869(17) 0.16856(8) 0.0554(7) Uani 1 1 d . . .
H4 H 0.0530 0.9317 0.1512 0.066 Uiso 1 1 calc R . .
C5 C 0.0229(2) 0.82636(15) 0.19532(8) 0.0454(6) Uani 1 1 d . . .
H5 H -0.0469 0.8433 0.1961 0.054 Uiso 1 1 calc R . .
C6 C 0.06474(19) 0.74861(14) 0.22132(7) 0.0392(5) Uani 1 1 d . . .
C7 C 0.0000 0.6920(2) 0.2500 0.0372(7) Uani 1 2 d S . .
C8 C 0.0000 0.59569(19) 0.2500 0.0346(7) Uani 1 2 d S . .
C9 C 0.05642(17) 0.53872(13) 0.21794(7) 0.0353(5) Uani 1 1 d . . .
C10 C 0.13097(18) 0.47354(14) 0.23591(8) 0.0378(5) Uani 1 1 d . . .
H10 H 0.1411 0.4612 0.2685 0.045 Uiso 1 1 calc R . .
C11 C 0.19030(17) 0.42659(15) 0.20744(8) 0.0384(5) Uani 1 1 d . . .
H11 H 0.2422 0.3839 0.2208 0.046 Uiso 1 1 calc R . .
C12 C 0.17524(17) 0.44086(14) 0.15933(8) 0.0370(5) Uani 1 1 d . . .
C13 C 0.09694(19) 0.50157(16) 0.14091(8) 0.0444(6) Uani 1 1 d . . .
H13 H 0.0831 0.5101 0.1081 0.053 Uiso 1 1 calc R . .
C14 C 0.03866(19) 0.54989(16) 0.16987(8) 0.0433(6) Uani 1 1 d . . .
H14 H -0.0144 0.5914 0.1566 0.052 Uiso 1 1 calc R . .
C15 C 0.24427(17) 0.39332(15) 0.12903(7) 0.0372(5) Uani 1 1 d . . .
C16 C 0.24202(18) 0.29407(15) 0.12353(8) 0.0407(5) Uani 1 1 d . . .
C17 C 0.1741(2) 0.23551(17) 0.14568(9) 0.0569(7) Uani 1 1 d . . .
H17 H 0.1286 0.2640 0.1646 0.068 Uiso 1 1 calc R . .
C18 C 0.1735(3) 0.13953(19) 0.14013(11) 0.0813(11) Uani 1 1 d . . .
H18 H 0.1282 0.1016 0.1554 0.098 Uiso 1 1 calc R . .
C19 C 0.2393(3) 0.09614(19) 0.11204(11) 0.0782(10) Uani 1 1 d . . .
H19 H 0.2377 0.0289 0.1084 0.094 Uiso 1 1 calc R . .
C20 C 0.3046(2) 0.14784(17) 0.09009(9) 0.0572(7) Uani 1 1 d . . .
H20 H 0.3483 0.1165 0.0713 0.069 Uiso 1 1 calc R . .
C21 C 0.30922(19) 0.24885(15) 0.09465(8) 0.0413(6) Uani 1 1 d . . .
C22 C 0.37628(18) 0.30386(16) 0.07184(7) 0.0395(5) Uani 1 1 d . . .
C23 C 0.37889(18) 0.40317(15) 0.07737(7) 0.0391(5) Uani 1 1 d . . .
C24 C 0.4490(2) 0.46098(17) 0.05605(8) 0.0495(6) Uani 1 1 d . . .
H24 H 0.4923 0.4321 0.0362 0.059 Uiso 1 1 calc R . .
C25 C 0.4551(2) 0.55606(18) 0.06349(9) 0.0604(8) Uani 1 1 d . . .
H25 H 0.5024 0.5931 0.0490 0.072 Uiso 1 1 calc R . .
C26 C 0.3911(2) 0.60050(18) 0.09280(9) 0.0615(8) Uani 1 1 d . . .
H26 H 0.3966 0.6671 0.0981 0.074 Uiso 1 1 calc R . .
C27 C 0.3219(2) 0.54900(16) 0.11346(8) 0.0486(6) Uani 1 1 d . . .
H27 H 0.2793 0.5803 0.1328 0.058 Uiso 1 1 calc R . .
C28 C 0.31233(18) 0.44823(15) 0.10650(7) 0.0375(5) Uani 1 1 d . . .
C29 C 0.4467(2) 0.25621(16) 0.04233(8) 0.0436(6) Uani 1 1 d . A .
C30 C 0.5447(2) 0.2288(2) 0.06118(9) 0.0643(8) Uani 1 1 d . . .
H30 H 0.5668 0.2407 0.0933 0.077 Uiso 1 1 calc R . .
C31 C 0.6113(2) 0.1849(2) 0.03484(10) 0.0721(9) Uani 1 1 d . A .
H31 H 0.6786 0.1680 0.0486 0.087 Uiso 1 1 calc R . .
C32 C 0.5793(3) 0.16572(19) -0.01163(9) 0.0607(7) Uani 1 1 d . . .
C33 C 0.4819(3) 0.1905(2) -0.03088(9) 0.0663(8) Uani 1 1 d . A .
H33 H 0.4595 0.1768 -0.0628 0.080 Uiso 1 1 calc R . .
C34 C 0.4157(2) 0.23540(19) -0.00423(8) 0.0571(7) Uani 1 1 d . . .
H34 H 0.3484 0.2520 -0.0181 0.069 Uiso 1 1 calc R A .
C35 C 0.6452(2) 0.1212(2) -0.04027(9) 0.0823(8) Uani 0.50 1 d P A 1
N1 N 0.6889(7) 0.1010(5) -0.0663(3) 0.127(3) Uani 0.50 1 d P A 1
O1 O 0.6452(2) 0.1212(2) -0.04027(9) 0.0823(8) Uani 0.50 1 d P A 2
C36 C 0.7486(5) 0.0864(5) -0.0183(3) 0.087(2) Uani 0.50 1 d P A 2
H36A H 0.7849 0.0576 -0.0423 0.131 Uiso 0.50 1 calc PR A 2
H36B H 0.7397 0.0389 0.0057 0.131 Uiso 0.50 1 calc PR A 2
H36C H 0.7887 0.1401 -0.0039 0.131 Uiso 0.50 1 calc PR A 2
C37 C -0.0002(5) 0.1176(4) 0.26793(19) 0.0641(15) Uani 0.50 1 d PU B -1
H37 H -0.0307 0.1071 0.2974 0.077 Uiso 0.50 1 calc PR B -1
Cl1 Cl 0.0019(10) 0.23928(10) 0.2440(4) 0.1029(18) Uani 0.50 1 d PU B -1
Cl2 Cl 0.11061(7) 0.06307(6) 0.26117(4) 0.0685(3) Uani 0.89 1 d PU B -1
Cl3 Cl -0.0772(6) 0.0731(6) 0.2077(3) 0.0753(19) Uani 0.11 1 d PU B -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
C1 C2 1.376(3) . ?
C1 C6 1.395(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(3) . ?
C7 C8 1.353(4) . ?
C7 C6 1.494(3) 2 ?
C8 C9 1.494(3) . ?
C8 C9 1.494(3) 2 ?
C9 C14 1.386(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 C15 1.499(3) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.404(3) . ?
C15 C28 1.405(3) . ?
C16 C17 1.427(3) . ?
C16 C21 1.441(3) . ?
C17 C18 1.358(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.402(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.346(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.426(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.401(3) . ?
C22 C23 1.405(3) . ?
C22 C29 1.497(3) . ?
C23 C24 1.428(3) . ?
C23 C28 1.439(3) . ?
C24 C25 1.354(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.415(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.361(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.433(3) . ?
C27 H27 0.9500 . ?
C29 C30 1.383(4) . ?
C29 C34 1.384(3) . ?
C30 C31 1.380(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.370(4) . ?
C32 C35 1.421(3) . ?
C33 C34 1.388(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 N1 1.044(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 Cl2 1.680(6) . ?
C37 Cl1 1.845(7) . ?
C37 Cl3 1.993(10) . ?
C37 H37 1.0000 . ?
C32 O1 1.421(4) . ?
O1 C36 1.503(7) . ?


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 C7 121.59(19) . . ?
C5 C6 C7 120.2(2) . . ?
C8 C7 C6 122.19(12) . . ?
C8 C7 C6 122.19(12) . 2 ?
C6 C7 C6 115.6(2) . 2 ?
C7 C8 C9 122.41(12) . . ?
C7 C8 C9 122.41(12) . 2 ?
C9 C8 C9 115.2(2) . 2 ?
C14 C9 C10 117.7(2) . . ?
C14 C9 C8 121.97(18) . . ?
C10 C9 C8 120.30(18) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 C15 121.69(19) . . ?
C11 C12 C15 120.2(2) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C16 C15 C28 119.9(2) . . ?
C16 C15 C12 120.24(19) . . ?
C28 C15 C12 119.85(18) . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 C21 119.9(2) . . ?
C17 C16 C21 118.3(2) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 121.8(2) . . ?
C22 C21 C16 120.08(19) . . ?
C20 C21 C16 118.1(2) . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 C29 119.7(2) . . ?
C23 C22 C29 120.1(2) . . ?
C22 C23 C24 121.6(2) . . ?
C22 C23 C28 119.8(2) . . ?
C24 C23 C28 118.6(2) . . ?
C25 C24 C23 121.4(2) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.8(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C15 C28 C27 121.8(2) . . ?
C15 C28 C23 120.21(19) . . ?
C27 C28 C23 117.9(2) . . ?
C30 C29 C34 117.5(2) . . ?
C30 C29 C22 120.9(2) . . ?
C34 C29 C22 121.6(2) . . ?
C31 C30 C29 122.2(2) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C32 C31 C30 119.4(3) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C33 C32 C31 119.5(3) . . ?
C33 C32 C35 119.0(3) . . ?
C31 C32 C35 121.5(3) . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C29 C34 C33 120.7(3) . . ?
C29 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
N1 C35 C32 167.3(5) . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl2 C37 Cl1 108.8(5) . . ?
Cl2 C37 Cl3 95.9(3) . . ?
Cl1 C37 Cl3 89.8(5) . . ?
Cl2 C37 H37 118.9 . . ?
Cl1 C37 H37 118.9 . . ?
Cl3 C37 H37 118.9 . . ?
C32 O1 C36 118.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.041
