# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_18aq
_database_code_depnum_ccdc_archive 'CCDC 1555744'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
#2515GuillotICMMO

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 2(C41 H27 N O), C Cl2 '
_chemical_formula_sum            ' C83 H54 Cl2 N2 O2 '
_chemical_formula_weight         1182.18

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.6948(2)
_cell_length_b                   10.6078(3)
_cell_length_c                   14.8224(4)
_cell_angle_alpha                105.2660(10)
_cell_angle_beta                 103.770(2)
_cell_angle_gamma                93.623(2)
_cell_volume                     1415.34(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    6643
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.52

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24994
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.477
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4993
_reflns_number_gt                4092
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1300P)²+4.3219P] 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         4993
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2508
_refine_ls_wR_factor_gt          0.2379
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.022
_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
O1 O 0.2288(3) 0.6350(2) 1.00269(18) 0.0250(6) Uani 1 1 d . . . . .
N1 N 0.2776(3) 0.3384(3) 0.70825(19) 0.0157(6) Uani 1 1 d . . . . .
C25 C 0.1060(3) 0.3621(3) 0.7926(2) 0.0155(7) Uani 1 1 d . . . . .
C21 C 0.1639(3) 0.2257(3) 0.3532(2) 0.0170(7) Uani 1 1 d . . . . .
C26 C 0.2454(3) 0.4147(3) 0.7880(2) 0.0154(7) Uani 1 1 d . . . . .
C35 C 0.3067(4) 0.5264(3) 0.8629(2) 0.0167(7) Uani 1 1 d . . . . .
C10 C 0.0821(4) 0.3327(3) 0.3586(3) 0.0190(7) Uani 1 1 d . . . . .
C7 C 0.3148(3) 0.3377(3) 0.5167(2) 0.0163(7) Uani 1 1 d . . . . .
C1 C 0.4168(3) 0.3438(3) 0.6922(2) 0.0147(7) Uani 1 1 d . . . . .
C36 C 0.4412(4) 0.6113(3) 0.8773(2) 0.0168(7) Uani 1 1 d . . . . .
C20 C 0.2836(4) 0.2295(3) 0.4320(2) 0.0174(7) Uani 1 1 d . . . . .
C34 C 0.2098(4) 0.5497(3) 0.9265(2) 0.0194(7) Uani 1 1 d . . . . .
C2 C 0.5337(4) 0.3523(3) 0.7698(2) 0.0172(7) Uani 1 1 d . . . . .
H2 H 0.518873 0.344824 0.828024 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2317(4) 0.4402(3) 0.5198(2) 0.0188(7) Uani 1 1 d . . . . .
H8 H 0.251852 0.510964 0.575655 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2119(4) 0.0111(3) 0.2605(3) 0.0201(7) Uani 1 1 d . . . . .
C24 C 0.0541(4) 0.2556(3) 0.7175(3) 0.0203(7) Uani 1 1 d . . . . .
H24 H -0.033969 0.204919 0.704817 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6937(4) 0.3784(3) 0.6739(3) 0.0207(7) Uani 1 1 d . . . . .
H4 H 0.786409 0.392991 0.668110 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6722(4) 0.3717(3) 0.7613(3) 0.0200(7) Uani 1 1 d . . . . .
H3 H 0.750060 0.380230 0.814156 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1197(4) 0.4391(3) 0.4417(3) 0.0206(7) Uani 1 1 d . . . . .
H9 H 0.068735 0.510879 0.444887 0.025 Uiso 1 1 calc R U . . .
C22 C 0.1269(4) 0.1157(3) 0.2684(2) 0.0177(7) Uani 1 1 d . . . . .
C18 C 0.3326(4) 0.0177(3) 0.3401(3) 0.0209(7) Uani 1 1 d . . . . .
H18 H 0.388984 -0.050206 0.335445 0.025 Uiso 1 1 calc R U . . .
C41 C 0.4696(4) 0.6491(3) 0.7992(2) 0.0193(7) Uani 1 1 d . . . . .
H41 H 0.400810 0.624703 0.739894 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1583(3) 0.2283(3) 0.6553(2) 0.0174(7) Uani 1 1 d . . . . .
H23 H 0.114467 0.237668 0.591068 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3665(4) 0.1203(3) 0.4218(2) 0.0191(7) Uani 1 1 d . . . . .
H19 H 0.444645 0.120588 0.472366 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5776(4) 0.3635(3) 0.5949(3) 0.0204(7) Uani 1 1 d . . . . .
H5 H 0.593451 0.365401 0.535736 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4368(4) 0.3458(3) 0.6021(2) 0.0165(7) Uani 1 1 d . . . . .
C13 C 0.0061(4) 0.1111(4) 0.1912(3) 0.0218(8) Uani 1 1 d . . . . .
C11 C -0.0371(4) 0.3272(4) 0.2783(3) 0.0227(8) Uani 1 1 d . . . . .
H11 H -0.089734 0.397769 0.280849 0.027 Uiso 1 1 calc R U . . .
C27 C 0.2073(4) 0.0938(3) 0.6443(3) 0.0210(8) Uani 1 1 d . . . . .
C14 C -0.0292(4) 0.0016(4) 0.1093(3) 0.0261(8) Uani 1 1 d . . . . .
H14 H -0.110783 -0.004182 0.059520 0.031 Uiso 1 1 calc R U . . .
C33 C 0.0736(4) 0.4478(3) 0.8803(3) 0.0212(8) Uani 1 1 d . . . . .
H33A H 0.058265 0.397619 0.923937 0.025 Uiso 1 1 calc R U . . .
H33B H -0.010392 0.490267 0.862685 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0745(4) 0.2209(4) 0.1988(3) 0.0248(8) Uani 1 1 d . . . . .
H12 H -0.153558 0.218971 0.148348 0.030 Uiso 1 1 calc R U . . .
C37 C 0.5448(4) 0.6518(4) 0.9659(3) 0.0236(8) Uani 1 1 d . . . . .
H37 H 0.526907 0.630198 1.019370 0.028 Uiso 1 1 calc R U . . .
C40 C 0.5987(4) 0.7225(4) 0.8088(3) 0.0239(8) Uani 1 1 d . . . . .
H40 H 0.615721 0.747303 0.756334 0.029 Uiso 1 1 calc R U . . .
C28 C 0.1809(4) 0.0042(4) 0.5530(3) 0.0252(8) Uani 1 1 d . . . . .
H28 H 0.135171 0.027748 0.498380 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0559(4) -0.0980(4) 0.1016(3) 0.0254(8) Uani 1 1 d . . . . .
H15 H 0.032017 -0.169294 0.045915 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1759(4) -0.0940(4) 0.1751(3) 0.0235(8) Uani 1 1 d . . . . .
H16 H 0.233047 -0.161263 0.167878 0.028 Uiso 1 1 calc R U . . .
C38 C 0.6738(4) 0.7236(4) 0.9751(3) 0.0301(9) Uani 1 1 d . . . . .
H38 H 0.742450 0.748954 1.034516 0.036 Uiso 1 1 calc R U . . .
C32 C 0.2779(5) 0.0579(4) 0.7254(3) 0.0304(9) Uani 1 1 d . . . . .
H32 H 0.296370 0.117525 0.786781 0.037 Uiso 1 1 calc R U . . .
C39 C 0.7022(4) 0.7585(4) 0.8969(3) 0.0296(9) Uani 1 1 d . . . . .
H39 H 0.789895 0.805748 0.903426 0.035 Uiso 1 1 calc R U . . .
C29 C 0.2226(5) -0.1212(4) 0.5430(3) 0.0359(10) Uani 1 1 d . . . . .
H29 H 0.203473 -0.181605 0.481862 0.043 Uiso 1 1 calc R U . . .
C31 C 0.3207(5) -0.0663(4) 0.7151(3) 0.0396(11) Uani 1 1 d . . . . .
H31 H 0.368467 -0.089733 0.769338 0.048 Uiso 1 1 calc R U . . .
C30 C 0.2919(5) -0.1552(4) 0.6237(4) 0.0396(11) Uani 1 1 d . . . . .
H30 H 0.319826 -0.238771 0.616801 0.048 Uiso 1 1 calc R U . . .
Cl1A Cl 0.406(2) -0.0707(18) 0.0287(9) 0.124(4) Uani 0.5 1 d . . P . .
Cl2A Cl 0.436(2) -0.0552(18) 0.0745(9) 0.124(4) Uani 0.5 1 d . . P . .
C100 C 0.448(2) -0.0303(18) -0.0301(19) 0.124(4) Uani 0.5 1 d . . P . .


_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
O1 C34 1.212(4) . ?
N1 C26 1.361(4) . ?
N1 C1 1.426(4) . ?
N1 C23 1.493(4) . ?
C25 C24 1.330(5) . ?
C25 C26 1.454(5) . ?
C25 C33 1.491(5) . ?
C21 C10 1.421(5) . ?
C21 C22 1.425(5) . ?
C21 C20 1.427(5) . ?
C26 C35 1.376(5) . ?
C35 C34 1.471(5) . ?
C35 C36 1.475(5) . ?
C10 C9 1.388(5) . ?
C10 C11 1.434(5) . ?
C7 C8 1.391(5) . ?
C7 C20 1.415(5) . ?
C7 C6 1.492(5) . ?
C1 C2 1.388(5) . ?
C1 C6 1.399(5) . ?
C36 C37 1.393(5) . ?
C36 C41 1.399(5) . ?
C20 C19 1.447(5) . ?
C34 C33 1.543(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C17 C16 1.401(5) . ?
C17 C22 1.420(5) . ?
C17 C18 1.434(5) . ?
C24 C23 1.514(5) . ?
C24 H24 0.9300 . ?
C4 C3 1.378(5) . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C22 C13 1.417(5) . ?
C18 C19 1.352(5) . ?
C18 H18 0.9300 . ?
C41 C40 1.387(5) . ?
C41 H41 0.9300 . ?
C23 C27 1.513(5) . ?
C23 H23 0.9800 . ?
C19 H19 0.9300 . ?
C5 C6 1.399(5) . ?
C5 H5 0.9300 . ?
C13 C14 1.396(5) . ?
C13 C12 1.438(5) . ?
C11 C12 1.355(5) . ?
C11 H11 0.9300 . ?
C27 C28 1.388(5) . ?
C27 C32 1.393(5) . ?
C14 C15 1.380(6) . ?
C14 H14 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C12 H12 0.9300 . ?
C37 C38 1.381(5) . ?
C37 H37 0.9300 . ?
C40 C39 1.386(5) . ?
C40 H40 0.9300 . ?
C28 C29 1.395(6) . ?
C28 H28 0.9300 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C38 C39 1.387(6) . ?
C38 H38 0.9300 . ?
C32 C31 1.387(6) . ?
C32 H32 0.9300 . ?
C39 H39 0.9300 . ?
C29 C30 1.374(7) . ?
C29 H29 0.9300 . ?
C31 C30 1.385(7) . ?
C31 H31 0.9300 . ?
C30 H30 0.9300 . ?
Cl1A Cl2A 0.64(3) . ?
Cl1A C100 1.21(3) . ?
Cl1A C100 1.71(2) 2_655 ?
Cl2A C100 1.67(3) . ?
Cl2A C100 1.75(3) 2_655 ?
C100 C100 1.19(4) 2_655 ?

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
C26 N1 C1 124.1(3) . . ?
C26 N1 C23 109.5(3) . . ?
C1 N1 C23 124.7(3) . . ?
C24 C25 C26 108.9(3) . . ?
C24 C25 C33 143.1(3) . . ?
C26 C25 C33 108.0(3) . . ?
C10 C21 C22 119.7(3) . . ?
C10 C21 C20 120.0(3) . . ?
C22 C21 C20 120.3(3) . . ?
N1 C26 C35 137.9(3) . . ?
N1 C26 C25 109.3(3) . . ?
C35 C26 C25 112.9(3) . . ?
C26 C35 C34 107.0(3) . . ?
C26 C35 C36 127.8(3) . . ?
C34 C35 C36 125.2(3) . . ?
C9 C10 C21 119.0(3) . . ?
C9 C10 C11 122.0(3) . . ?
C21 C10 C11 119.1(3) . . ?
C8 C7 C20 119.3(3) . . ?
C8 C7 C6 119.2(3) . . ?
C20 C7 C6 121.4(3) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 N1 118.1(3) . . ?
C6 C1 N1 121.4(3) . . ?
C37 C36 C41 118.3(3) . . ?
C37 C36 C35 122.0(3) . . ?
C41 C36 C35 119.7(3) . . ?
C7 C20 C21 119.0(3) . . ?
C7 C20 C19 123.0(3) . . ?
C21 C20 C19 118.0(3) . . ?
O1 C34 C35 127.3(3) . . ?
O1 C34 C33 123.7(3) . . ?
C35 C34 C33 109.0(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C16 C17 C22 119.1(3) . . ?
C16 C17 C18 122.4(3) . . ?
C22 C17 C18 118.5(3) . . ?
C25 C24 C23 110.5(3) . . ?
C25 C24 H24 124.7 . . ?
C23 C24 H24 124.7 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C13 C22 C17 119.7(3) . . ?
C13 C22 C21 120.1(3) . . ?
C17 C22 C21 120.1(3) . . ?
C19 C18 C17 121.7(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C40 C41 C36 121.2(3) . . ?
C40 C41 H41 119.4 . . ?
C36 C41 H41 119.4 . . ?
N1 C23 C27 112.8(3) . . ?
N1 C23 C24 101.8(3) . . ?
C27 C23 C24 113.9(3) . . ?
N1 C23 H23 109.4 . . ?
C27 C23 H23 109.4 . . ?
C24 C23 H23 109.4 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C7 119.6(3) . . ?
C1 C6 C7 122.5(3) . . ?
C14 C13 C22 119.2(3) . . ?
C14 C13 C12 122.0(3) . . ?
C22 C13 C12 118.8(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C28 C27 C32 119.3(3) . . ?
C28 C27 C23 120.2(3) . . ?
C32 C27 C23 120.5(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C25 C33 C34 102.9(3) . . ?
C25 C33 H33A 111.2 . . ?
C34 C33 H33A 111.2 . . ?
C25 C33 H33B 111.2 . . ?
C34 C33 H33B 111.2 . . ?
H33A C33 H33B 109.1 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C38 C37 C36 120.5(3) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C39 C40 C41 119.7(3) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C27 C28 C29 120.2(4) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C37 C38 C39 120.9(3) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C31 C32 C27 120.3(4) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
C40 C39 C38 119.4(3) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
C30 C29 C28 119.8(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C30 C31 C32 119.7(4) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C29 C30 C31 120.7(4) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
Cl2A Cl1A C100 126(4) . . ?
Cl2A Cl1A C100 83(4) . 2_655 ?
C100 Cl1A C100 44(2) . 2_655 ?
Cl1A Cl2A C100 36(3) . . ?
Cl1A Cl2A C100 76(3) . 2_655 ?
C100 Cl2A C100 40.5(14) . 2_655 ?
C100 C100 Cl1A 91(3) 2_655 . ?
C100 C100 Cl2A 73(3) 2_655 . ?
Cl1A C100 Cl2A 18.1(16) . . ?
C100 C100 Cl1A 44.8(16) 2_655 2_655 ?
Cl1A C100 Cl1A 136(2) . 2_655 ?
Cl2A C100 Cl1A 118.1(17) . 2_655 ?
C100 C100 Cl2A 66.1(19) 2_655 2_655 ?
Cl1A C100 Cl2A 158(2) . 2_655 ?
Cl2A C100 Cl2A 139.5(14) . 2_655 ?
Cl1A C100 Cl2A 21.4(9) 2_655 2_655 ?

_refine_diff_density_max         0.834
_refine_diff_density_min         -1.694
_refine_diff_density_rms         0.103



####################################################################### 
# 
# 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_8ac
_database_code_depnum_ccdc_archive 'CCDC 1555745'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
#2454GuillotICMMO

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 N O3, C H2 Cl2 '
_chemical_formula_sum            'C34 H29 Cl2 N O3'
_chemical_formula_weight         570.48

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'

_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                   14.1223(5)
_cell_length_b                   10.4359(3)
_cell_length_c                   19.4476(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.282(2)
_cell_angle_gamma                90
_cell_volume                     2843.05(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5626
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.01

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36151
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         30.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8452
_reflns_number_gt                5090
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0555P)²+0.9585P] 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         8452
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.185
_refine_ls_shift/su_mean         0.011

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
O2 O 0.64601(9) 0.15622(11) 0.99693(6) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.85066(9) -0.05375(12) 0.86366(6) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.36451(10) 0.39089(12) 0.97055(7) 0.0304(3) Uani 1 1 d . . . . .
N1 N 0.58863(10) 0.17419(12) 0.84218(7) 0.0176(3) Uani 1 1 d . . . . .
C14 C 0.59315(12) 0.03767(15) 0.85138(8) 0.0175(3) Uani 1 1 d . . . . .
C23 C 0.34938(12) 0.17900(15) 0.86242(9) 0.0188(3) Uani 1 1 d . . . . .
C29 C 0.73346(13) 0.20893(16) 0.78118(9) 0.0224(4) Uani 1 1 d . . . . .
C18 C 0.55074(13) 0.37560(15) 0.86652(8) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.66897(12) -0.01877(15) 0.89393(8) 0.0176(3) Uani 1 1 d . . . . .
C10 C 0.66808(13) -0.15185(15) 0.90116(9) 0.0221(4) Uani 1 1 d . . . . .
H10 H 0.718838 -0.192625 0.929721 0.026 Uiso 1 1 calc R U . . .
C2 C 0.84313(13) 0.03622(16) 0.91392(9) 0.0211(4) Uani 1 1 d . . . . .
C1 C 0.75054(12) 0.05614(15) 0.92987(8) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.73734(13) 0.14541(15) 0.98160(9) 0.0197(3) Uani 1 1 d . . . . .
C22 C 0.52404(12) 0.25068(15) 0.87006(8) 0.0177(3) Uani 1 1 d . . . . .
C16 C 0.65836(12) 0.25444(15) 0.82030(9) 0.0195(3) Uani 1 1 d . . . . .
C19 C 0.48562(13) 0.46134(16) 0.90069(9) 0.0234(4) Uani 1 1 d . . . . .
H19A H 0.448189 0.517960 0.866568 0.028 Uiso 1 1 calc R U . . .
H19B H 0.521636 0.514423 0.937278 0.028 Uiso 1 1 calc R U . . .
C13 C 0.51914(13) -0.03594(16) 0.81811(9) 0.0217(4) Uani 1 1 d . . . . .
H13 H 0.467772 0.004254 0.789895 0.026 Uiso 1 1 calc R U . . .
C21 C 0.43915(12) 0.22541(15) 0.90620(9) 0.0195(3) Uani 1 1 d . . . . .
H21 H 0.456325 0.167102 0.946665 0.023 Uiso 1 1 calc R U . . .
C17 C 0.63575(13) 0.37934(16) 0.83511(9) 0.0217(4) Uani 1 1 d . . . . .
H17 H 0.670734 0.453830 0.825936 0.026 Uiso 1 1 calc R U . . .
C5 C 0.81413(14) 0.21456(17) 1.01499(9) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.804819 0.274825 1.050121 0.031 Uiso 1 1 calc R U . . .
C11 C 0.59498(14) -0.22565(16) 0.86768(10) 0.0261(4) Uani 1 1 d . . . . .
H11 H 0.596053 -0.316094 0.873254 0.031 Uiso 1 1 calc R U . . .
C20 C 0.42148(13) 0.36436(16) 0.93146(9) 0.0220(4) Uani 1 1 d . . . . .
C28 C 0.29113(14) 0.08828(17) 0.88793(10) 0.0286(4) Uani 1 1 d . . . . .
H28 H 0.308989 0.052239 0.932542 0.034 Uiso 1 1 calc R U . . .
C26 C 0.18005(15) 0.10208(18) 0.78395(11) 0.0331(5) Uani 1 1 d . . . . .
H26 H 0.122357 0.075597 0.757262 0.040 Uiso 1 1 calc R U . . .
C34 C 0.82072(15) 0.27391(18) 0.78741(11) 0.0329(5) Uani 1 1 d . . . . .
H34 H 0.832066 0.342636 0.819428 0.039 Uiso 1 1 calc R U . . .
C24 C 0.32143(13) 0.23108(17) 0.79723(9) 0.0250(4) Uani 1 1 d . . . . .
H24 H 0.360540 0.293637 0.779253 0.030 Uiso 1 1 calc R U . . .
C30 C 0.72041(15) 0.10658(18) 0.73498(9) 0.0274(4) Uani 1 1 d . . . . .
H30 H 0.662042 0.060277 0.730629 0.033 Uiso 1 1 calc R U . . .
C12 C 0.52015(14) -0.16780(16) 0.82602(10) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.469832 -0.218333 0.803023 0.031 Uiso 1 1 calc R U . . .
C4 C 0.90393(15) 0.19420(18) 0.99626(10) 0.0304(4) Uani 1 1 d . . . . .
H4 H 0.956187 0.242466 1.018340 0.036 Uiso 1 1 calc R U . . .
C8 C 0.62880(16) 0.25096(19) 1.04677(10) 0.0331(5) Uani 1 1 d . . . . .
H8A H 0.668235 0.232780 1.090862 0.050 Uiso 1 1 calc R U . . .
H8B H 0.561239 0.249433 1.053596 0.050 Uiso 1 1 calc R U . . .
H8C H 0.645111 0.335757 1.030077 0.050 Uiso 1 1 calc R U . . .
C3 C 0.91989(14) 0.10565(18) 0.94632(10) 0.0278(4) Uani 1 1 d . . . . .
H3 H 0.982321 0.092465 0.934353 0.033 Uiso 1 1 calc R U . . .
C31 C 0.79083(16) 0.0710(2) 0.69526(10) 0.0354(5) Uani 1 1 d . . . . .
H31 H 0.780743 0.000543 0.664236 0.042 Uiso 1 1 calc R U . . .
C25 C 0.23744(14) 0.19303(18) 0.75819(10) 0.0301(4) Uani 1 1 d . . . . .
H25 H 0.219185 0.229365 0.713697 0.036 Uiso 1 1 calc R U . . .
C33 C 0.89052(16) 0.2389(2) 0.74734(13) 0.0440(6) Uani 1 1 d . . . . .
H33 H 0.949223 0.284438 0.751724 0.053 Uiso 1 1 calc R U . . .
C7 C 0.94182(15) -0.0730(2) 0.84169(11) 0.0361(5) Uani 1 1 d . . . . .
H7A H 0.965208 0.008247 0.825014 0.054 Uiso 1 1 calc R U . . .
H7B H 0.936571 -0.136271 0.804161 0.054 Uiso 1 1 calc R U . . .
H7C H 0.986532 -0.104261 0.880742 0.054 Uiso 1 1 calc R U . . .
C27 C 0.20721(15) 0.0499(2) 0.84890(11) 0.0377(5) Uani 1 1 d . . . . .
H27 H 0.167998 -0.012717 0.866761 0.045 Uiso 1 1 calc R U . . .
C32 C 0.87596(17) 0.1382(2) 0.70088(11) 0.0411(5) Uani 1 1 d . . . . .
H32 H 0.923999 0.115492 0.673051 0.049 Uiso 1 1 calc R U . . .
Cl1A Cl 0.1250(4) 0.0993(4) 0.5880(4) 0.0645(12) Uani 0.586(6) 1 d . . P A 1
Cl2A Cl 0.12346(12) 0.1698(2) 0.44177(8) 0.0608(6) Uani 0.586(6) 1 d . . P A 1
C40A C 0.1493(5) 0.0489(6) 0.5040(3) 0.0384(14) Uani 0.586(6) 1 d . . P A 1
H40A H 0.217424 0.024897 0.506339 0.046 Uiso 0.586(6) 1 calc R U P A 1
H40B H 0.110504 -0.027860 0.489754 0.046 Uiso 0.586(6) 1 calc R U P A 1
Cl2B Cl 0.1061(2) 0.0842(6) 0.45028(14) 0.0940(17) Uani 0.414(6) 1 d . . P A 2
Cl1B Cl 0.1026(5) 0.0821(7) 0.5923(5) 0.0722(17) Uani 0.414(6) 1 d . . P A 2
C40B C 0.1702(7) 0.0471(10) 0.5343(4) 0.045(2) Uani 0.414(6) 1 d . . P A 2
H40C H 0.186877 -0.045093 0.536890 0.054 Uiso 0.414(6) 1 calc R U P A 2
H40D H 0.229979 0.097493 0.542016 0.054 Uiso 0.414(6) 1 calc R U P A 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
O2 C6 1.365(2) . ?
O2 C8 1.427(2) . ?
O1 C2 1.369(2) . ?
O1 C7 1.421(2) . ?
O3 C20 1.207(2) . ?
N1 C22 1.374(2) . ?
N1 C16 1.399(2) . ?
N1 C14 1.436(2) . ?
C14 C13 1.389(2) . ?
C14 C9 1.398(2) . ?
C23 C28 1.387(2) . ?
C23 C24 1.390(2) . ?
C23 C21 1.514(2) . ?
C29 C30 1.393(3) . ?
C29 C34 1.398(3) . ?
C29 C16 1.461(2) . ?
C18 C22 1.361(2) . ?
C18 C17 1.415(2) . ?
C18 C19 1.498(2) . ?
C9 C10 1.396(2) . ?
C9 C1 1.491(2) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C2 C3 1.387(3) . ?
C2 C1 1.397(2) . ?
C1 C6 1.401(2) . ?
C6 C5 1.393(2) . ?
C22 C21 1.488(2) . ?
C16 C17 1.381(2) . ?
C19 C20 1.530(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C13 C12 1.385(2) . ?
C13 H13 0.9500 . ?
C21 C20 1.561(2) . ?
C21 H21 1.0000 . ?
C17 H17 0.9500 . ?
C5 C4 1.379(3) . ?
C5 H5 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C28 C27 1.383(3) . ?
C28 H28 0.9500 . ?
C26 C25 1.383(3) . ?
C26 C27 1.384(3) . ?
C26 H26 0.9500 . ?
C34 C33 1.381(3) . ?
C34 H34 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C30 C31 1.385(3) . ?
C30 H30 0.9500 . ?
C12 H12 0.9500 . ?
C4 C3 1.380(3) . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 H3 0.9500 . ?
C31 C32 1.385(3) . ?
C31 H31 0.9500 . ?
C25 H25 0.9500 . ?
C33 C32 1.384(3) . ?
C33 H33 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C27 H27 0.9500 . ?
C32 H32 0.9500 . ?
Cl1A C40A 1.790(9) . ?
Cl2A C40A 1.754(6) . ?
C40A H40A 0.9900 . ?
C40A H40B 0.9900 . ?
Cl2B C40B 1.807(8) . ?
Cl1B C40B 1.611(13) . ?
C40B H40C 0.9900 . ?
C40B H40D 0.9900 . ?

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
C6 O2 C8 116.92(14) . . ?
C2 O1 C7 117.83(15) . . ?
C22 N1 C16 107.47(13) . . ?
C22 N1 C14 123.24(14) . . ?
C16 N1 C14 127.56(14) . . ?
C13 C14 C9 121.16(15) . . ?
C13 C14 N1 118.13(15) . . ?
C9 C14 N1 120.69(14) . . ?
C28 C23 C24 118.72(16) . . ?
C28 C23 C21 120.64(15) . . ?
C24 C23 C21 120.57(15) . . ?
C30 C29 C34 118.09(18) . . ?
C30 C29 C16 122.67(17) . . ?
C34 C29 C16 119.16(17) . . ?
C22 C18 C17 107.70(14) . . ?
C22 C18 C19 111.10(15) . . ?
C17 C18 C19 141.03(15) . . ?
C10 C9 C14 117.57(15) . . ?
C10 C9 C1 119.39(15) . . ?
C14 C9 C1 123.02(14) . . ?
C11 C10 C9 121.49(17) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
O1 C2 C3 123.76(17) . . ?
O1 C2 C1 114.84(15) . . ?
C3 C2 C1 121.39(16) . . ?
C2 C1 C6 118.16(16) . . ?
C2 C1 C9 120.47(15) . . ?
C6 C1 C9 121.35(15) . . ?
O2 C6 C5 123.84(16) . . ?
O2 C6 C1 115.30(15) . . ?
C5 C6 C1 120.84(17) . . ?
C18 C22 N1 109.53(15) . . ?
C18 C22 C21 116.01(14) . . ?
N1 C22 C21 134.28(14) . . ?
C17 C16 N1 108.13(15) . . ?
C17 C16 C29 128.16(15) . . ?
N1 C16 C29 123.31(15) . . ?
C18 C19 C20 101.87(13) . . ?
C18 C19 H19A 111.4 . . ?
C20 C19 H19A 111.4 . . ?
C18 C19 H19B 111.4 . . ?
C20 C19 H19B 111.4 . . ?
H19A C19 H19B 109.3 . . ?
C12 C13 C14 120.09(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C22 C21 C23 117.28(14) . . ?
C22 C21 C20 98.89(13) . . ?
C23 C21 C20 108.55(13) . . ?
C22 C21 H21 110.5 . . ?
C23 C21 H21 110.5 . . ?
C20 C21 H21 110.5 . . ?
C16 C17 C18 107.17(14) . . ?
C16 C17 H17 126.4 . . ?
C18 C17 H17 126.4 . . ?
C4 C5 C6 118.99(17) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C10 C11 C12 120.07(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
O3 C20 C19 124.72(16) . . ?
O3 C20 C21 123.86(16) . . ?
C19 C20 C21 111.42(14) . . ?
C27 C28 C23 120.50(17) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C25 C26 C27 119.57(18) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C33 C34 C29 120.5(2) . . ?
C33 C34 H34 119.8 . . ?
C29 C34 H34 119.8 . . ?
C25 C24 C23 120.87(16) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C31 C30 C29 121.33(19) . . ?
C31 C30 H30 119.3 . . ?
C29 C30 H30 119.3 . . ?
C13 C12 C11 119.62(17) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C5 C4 C3 121.79(18) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C3 C2 118.80(18) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C32 C31 C30 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C26 C25 C24 119.97(18) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C34 C33 C32 120.8(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C28 C27 C26 120.36(18) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C33 C32 C31 119.5(2) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
Cl2A C40A Cl1A 111.8(4) . . ?
Cl2A C40A H40A 109.2 . . ?
Cl1A C40A H40A 109.3 . . ?
Cl2A C40A H40B 109.2 . . ?
Cl1A C40A H40B 109.2 . . ?
H40A C40A H40B 107.9 . . ?
Cl1B C40B Cl2B 108.2(7) . . ?
Cl1B C40B H40C 110.1 . . ?
Cl2B C40B H40C 110.1 . . ?
Cl1B C40B H40D 109.9 . . ?
Cl2B C40B H40D 110.1 . . ?
H40C C40B H40D 108.4 . . ?

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
C22 N1 C14 C13 70.1(2) . . . . ?
C16 N1 C14 C13 -126.80(18) . . . . ?
C22 N1 C14 C9 -108.51(19) . . . . ?
C16 N1 C14 C9 54.6(2) . . . . ?
C13 C14 C9 C10 0.7(2) . . . . ?
N1 C14 C9 C10 179.21(14) . . . . ?
C13 C14 C9 C1 179.14(15) . . . . ?
N1 C14 C9 C1 -2.3(2) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C1 C9 C10 C11 -178.65(16) . . . . ?
C7 O1 C2 C3 -2.6(2) . . . . ?
C7 O1 C2 C1 176.05(15) . . . . ?
O1 C2 C1 C6 179.04(14) . . . . ?
C3 C2 C1 C6 -2.3(2) . . . . ?
O1 C2 C1 C9 0.7(2) . . . . ?
C3 C2 C1 C9 179.45(15) . . . . ?
C10 C9 C1 C2 61.9(2) . . . . ?
C14 C9 C1 C2 -116.56(18) . . . . ?
C10 C9 C1 C6 -116.35(18) . . . . ?
C14 C9 C1 C6 65.2(2) . . . . ?
C8 O2 C6 C5 4.6(2) . . . . ?
C8 O2 C6 C1 -176.80(15) . . . . ?
C2 C1 C6 O2 -177.15(14) . . . . ?
C9 C1 C6 O2 1.1(2) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C9 C1 C6 C5 179.79(15) . . . . ?
C17 C18 C22 N1 0.02(19) . . . . ?
C19 C18 C22 N1 -176.24(14) . . . . ?
C17 C18 C22 C21 175.89(14) . . . . ?
C19 C18 C22 C21 -0.4(2) . . . . ?
C16 N1 C22 C18 -0.06(18) . . . . ?
C14 N1 C22 C18 165.98(15) . . . . ?
C16 N1 C22 C21 -174.87(17) . . . . ?
C14 N1 C22 C21 -8.8(3) . . . . ?
C22 N1 C16 C17 0.07(18) . . . . ?
C14 N1 C16 C17 -165.18(15) . . . . ?
C22 N1 C16 C29 -173.19(15) . . . . ?
C14 N1 C16 C29 21.6(3) . . . . ?
C30 C29 C16 C17 -140.35(19) . . . . ?
C34 C29 C16 C17 36.4(3) . . . . ?
C30 C29 C16 N1 31.5(2) . . . . ?
C34 C29 C16 N1 -151.72(17) . . . . ?
C22 C18 C19 C20 5.36(19) . . . . ?
C17 C18 C19 C20 -169.0(2) . . . . ?
C9 C14 C13 C12 -0.9(3) . . . . ?
N1 C14 C13 C12 -179.44(15) . . . . ?
C18 C22 C21 C23 111.63(17) . . . . ?
N1 C22 C21 C23 -73.8(2) . . . . ?
C18 C22 C21 C20 -4.67(18) . . . . ?
N1 C22 C21 C20 169.89(18) . . . . ?
C28 C23 C21 C22 142.47(17) . . . . ?
C24 C23 C21 C22 -40.7(2) . . . . ?
C28 C23 C21 C20 -106.65(18) . . . . ?
C24 C23 C21 C20 70.2(2) . . . . ?
N1 C16 C17 C18 -0.06(19) . . . . ?
C29 C16 C17 C18 172.78(16) . . . . ?
C22 C18 C17 C16 0.02(19) . . . . ?
C19 C18 C17 C16 174.5(2) . . . . ?
O2 C6 C5 C4 178.71(16) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C18 C19 C20 O3 171.35(17) . . . . ?
C18 C19 C20 C21 -8.38(18) . . . . ?
C22 C21 C20 O3 -171.75(16) . . . . ?
C23 C21 C20 O3 65.4(2) . . . . ?
C22 C21 C20 C19 7.98(18) . . . . ?
C23 C21 C20 C19 -114.82(16) . . . . ?
C24 C23 C28 C27 0.5(3) . . . . ?
C21 C23 C28 C27 177.40(18) . . . . ?
C30 C29 C34 C33 1.6(3) . . . . ?
C16 C29 C34 C33 -175.30(17) . . . . ?
C28 C23 C24 C25 -0.3(3) . . . . ?
C21 C23 C24 C25 -177.25(16) . . . . ?
C34 C29 C30 C31 -1.1(3) . . . . ?
C16 C29 C30 C31 175.71(16) . . . . ?
C14 C13 C12 C11 0.5(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C6 C5 C4 C3 -1.2(3) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
O1 C2 C3 C4 179.88(16) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
C27 C26 C25 C24 0.1(3) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C29 C34 C33 C32 -0.7(3) . . . . ?
C23 C28 C27 C26 -0.3(3) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C34 C33 C32 C31 -0.8(3) . . . . ?
C30 C31 C32 C33 1.4(3) . . . . ?

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.059



