# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_4p
_database_code_depnum_ccdc_archive 'CCDC 1523300'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C40 H25 F2 N O2'
_chemical_formula_sum            'C40 H25 F2 N O2'
_chemical_formula_weight         589.61

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'
F F 0.0171 0.0103 '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                   9.1323(5)
_cell_length_b                   27.5891(14)
_cell_length_c                   12.2546(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.3282(16)
_cell_angle_gamma                90
_cell_volume                     3016.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7346
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      24.29

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            29844
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6914
_reflns_number_gt                3505
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0592P)²+0.4506P] 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         6914
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.1363(3) 0.72671(9) 0.4369(2) 0.0844(7) Uani 1 1 d . . . . .
H1 H 0.2074 0.7283 0.5036 0.101 Uiso 1 1 calc R U . . .
C2 C 0.0225(4) 0.76099(9) 0.4151(3) 0.0993(9) Uani 1 1 d . . . . .
H2 H 0.0163 0.7847 0.4678 0.119 Uiso 1 1 calc R U . . .
C3 C -0.0789(4) 0.75983(12) 0.3174(3) 0.1048(9) Uani 1 1 d . . . . .
H3 H -0.1552 0.7828 0.3032 0.126 Uiso 1 1 calc R U . . .
C4 C -0.0707(3) 0.72593(12) 0.2406(3) 0.1058(9) Uani 1 1 d . . . . .
H4 H -0.1392 0.7260 0.1725 0.127 Uiso 1 1 calc R U . . .
C5 C 0.0415(3) 0.69037(10) 0.2632(2) 0.0895(8) Uani 1 1 d . . . . .
H5 H 0.0451 0.6664 0.2104 0.107 Uiso 1 1 calc R U . . .
C6 C 0.1456(3) 0.69036(8) 0.36152(19) 0.0671(6) Uani 1 1 d . . . . .
C7 C 0.2647(3) 0.65181(9) 0.39064(18) 0.0768(7) Uani 1 1 d . . . . .
H7A H 0.3531 0.6662 0.4375 0.092 Uiso 1 1 calc R U . . .
H7B H 0.2287 0.6268 0.4341 0.092 Uiso 1 1 calc R U . . .
C8 C 0.3926(2) 0.65202(7) 0.22758(17) 0.0551(5) Uani 1 1 d . . . . .
C9 C 0.4334(3) 0.70008(8) 0.2266(2) 0.0723(6) Uani 1 1 d . . . . .
H9 H 0.4046 0.7224 0.2749 0.087 Uiso 1 1 calc R U . . .
C10 C 0.5185(3) 0.71405(8) 0.1512(2) 0.0829(7) Uani 1 1 d . . . . .
H10 H 0.5479 0.7462 0.1481 0.099 Uiso 1 1 calc R U . . .
C11 C 0.5591(3) 0.68048(9) 0.0814(2) 0.0766(7) Uani 1 1 d . . . . .
C12 C 0.5203(2) 0.63229(7) 0.08144(17) 0.0615(6) Uani 1 1 d . . . . .
H12 H 0.5505 0.6101 0.0334 0.074 Uiso 1 1 calc R U . . .
C13 C 0.4349(2) 0.61843(6) 0.15575(15) 0.0494(5) Uani 1 1 d . . . . .
C14 C 0.3641(2) 0.57018(6) 0.17080(15) 0.0487(5) Uani 1 1 d . . . . .
C15 C 0.2878(2) 0.58073(8) 0.26976(17) 0.0579(5) Uani 1 1 d . . . . .
C16 C 0.4593(2) 0.52486(6) 0.18864(15) 0.0488(5) Uani 1 1 d . . . . .
C17 C 0.4032(2) 0.49251(7) 0.10815(16) 0.0503(5) Uani 1 1 d . . . . .
C18 C 0.2742(2) 0.50938(7) 0.02884(15) 0.0512(5) Uani 1 1 d . . . . .
C19 C 0.1823(2) 0.49027(8) -0.06712(16) 0.0628(6) Uani 1 1 d . . . . .
H19 H 0.2003 0.4596 -0.0928 0.075 Uiso 1 1 calc R U . . .
C20 C 0.0643(2) 0.51791(9) -0.12311(17) 0.0662(6) Uani 1 1 d . . . . .
H20 H 0.0022 0.5052 -0.1868 0.079 Uiso 1 1 calc R U . . .
C21 C 0.0348(2) 0.56384(9) -0.08797(18) 0.0654(6) Uani 1 1 d . . . . .
C22 C -0.0973(3) 0.59269(10) -0.1498(2) 0.0918(8) Uani 1 1 d . . . . .
H22A H -0.0623 0.6193 -0.1877 0.138 Uiso 1 1 calc R U . . .
H22B H -0.1533 0.6049 -0.0976 0.138 Uiso 1 1 calc R U . . .
H22C H -0.1606 0.5722 -0.2034 0.138 Uiso 1 1 calc R U . . .
C23 C 0.1289(2) 0.58311(8) 0.00726(17) 0.0595(6) Uani 1 1 d . . . . .
H23 H 0.1121 0.6142 0.0314 0.071 Uiso 1 1 calc R U . . .
C24 C 0.2464(2) 0.55597(7) 0.06509(16) 0.0508(5) Uani 1 1 d . . . . .
C25 C 0.5809(2) 0.50086(6) 0.26299(15) 0.0467(5) Uani 1 1 d . . . . .
C26 C 0.5860(2) 0.45473(7) 0.21785(15) 0.0495(5) Uani 1 1 d . . . . .
C27 C 0.6879(2) 0.41796(7) 0.26173(16) 0.0517(5) Uani 1 1 d . . . . .
C28 C 0.6903(3) 0.37114(7) 0.21671(18) 0.0659(6) Uani 1 1 d . . . . .
H28 H 0.6188 0.3622 0.1539 0.079 Uiso 1 1 calc R U . . .
C29 C 0.7974(3) 0.33886(8) 0.2652(2) 0.0741(7) Uani 1 1 d . . . . .
H29 H 0.7976 0.3078 0.2358 0.089 Uiso 1 1 calc R U . . .
C30 C 0.9065(3) 0.35193(9) 0.3582(2) 0.0766(7) Uani 1 1 d . . . . .
H30 H 0.9810 0.3299 0.3890 0.092 Uiso 1 1 calc R U . . .
C31 C 0.9049(3) 0.39671(8) 0.40435(19) 0.0708(6) Uani 1 1 d . . . . .
H31 H 0.9780 0.4048 0.4669 0.085 Uiso 1 1 calc R U . . .
C32 C 0.7944(2) 0.43114(7) 0.35902(17) 0.0553(5) Uani 1 1 d . . . . .
C33 C 0.7875(2) 0.47762(7) 0.40793(16) 0.0594(6) Uani 1 1 d . . . . .
H33 H 0.8565 0.4849 0.4734 0.071 Uiso 1 1 calc R U . . .
C34 C 0.6848(2) 0.51218(7) 0.36364(15) 0.0508(5) Uani 1 1 d . . . . .
C35 C 0.6804(2) 0.55964(7) 0.42024(16) 0.0541(5) Uani 1 1 d . . . . .
C36 C 0.6366(3) 0.56175(8) 0.5218(2) 0.0745(7) Uani 1 1 d . . . . .
H36 H 0.6084 0.5336 0.5537 0.089 Uiso 1 1 calc R U . . .
C37 C 0.6346(3) 0.60576(11) 0.5757(2) 0.0908(8) Uani 1 1 d . . . . .
H37 H 0.6030 0.6076 0.6429 0.109 Uiso 1 1 calc R U . . .
C38 C 0.6794(3) 0.64588(9) 0.5291(3) 0.0873(9) Uani 1 1 d . . . . .
C39 C 0.7230(3) 0.64563(8) 0.4306(3) 0.0885(8) Uani 1 1 d . . . . .
H39 H 0.7526 0.6740 0.4006 0.106 Uiso 1 1 calc R U . . .
C40 C 0.7223(3) 0.60188(8) 0.37568(19) 0.0742(7) Uani 1 1 d . . . . .
H40 H 0.7508 0.6010 0.3072 0.089 Uiso 1 1 calc R U . . .
F1 F 0.6424(2) 0.69516(6) 0.00763(13) 0.1192(6) Uani 1 1 d . . . . .
F2 F 0.6799(2) 0.68871(6) 0.58440(16) 0.1419(8) Uani 1 1 d . . . . .
N1 N 0.3073(2) 0.62926(6) 0.29498(14) 0.0623(5) Uani 1 1 d . . . . .
O1 O 0.22295(19) 0.55204(6) 0.31660(13) 0.0802(5) Uani 1 1 d . . . . .
O2 O 0.47536(15) 0.44904(4) 0.12138(10) 0.0545(4) 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 C6 1.378(3) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.340(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 N1 1.452(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.378(3) . ?
C8 C13 1.388(3) . ?
C8 N1 1.400(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 F1 1.361(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.508(2) . ?
C14 C16 1.512(3) . ?
C14 C24 1.547(3) . ?
C14 C15 1.549(3) . ?
C15 O1 1.205(2) . ?
C15 N1 1.377(3) . ?
C16 C17 1.348(2) . ?
C16 C25 1.439(3) . ?
C17 O2 1.361(2) . ?
C17 C18 1.435(3) . ?
C18 C19 1.394(3) . ?
C18 C24 1.401(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.398(3) . ?
C21 C22 1.508(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.392(3) . ?
C25 C34 1.421(3) . ?
C26 O2 1.390(2) . ?
C26 C27 1.404(3) . ?
C27 C28 1.407(3) . ?
C27 C32 1.416(3) . ?
C28 C29 1.362(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.360(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.411(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.423(3) . ?
C33 C34 1.366(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.486(3) . ?
C35 C40 1.376(3) . ?
C35 C36 1.388(3) . ?
C36 C37 1.384(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.348(4) . ?
C37 H37 0.9300 . ?
C38 C39 1.350(4) . ?
C38 F2 1.361(3) . ?
C39 C40 1.381(3) . ?
C39 H39 0.9300 . ?
C40 H40 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
C6 C1 C2 121.2(3) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 117.4(2) . . ?
C5 C6 C7 122.6(2) . . ?
C1 C6 C7 120.0(2) . . ?
N1 C7 C6 114.53(18) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 121.6(2) . . ?
C9 C8 N1 128.5(2) . . ?
C13 C8 N1 109.85(17) . . ?
C8 C9 C10 117.8(2) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
F1 C11 C10 118.7(2) . . ?
F1 C11 C12 117.9(2) . . ?
C10 C11 C12 123.4(2) . . ?
C13 C12 C11 116.9(2) . . ?
C13 C12 H12 121.6 . . ?
C11 C12 H12 121.6 . . ?
C12 C13 C8 120.56(18) . . ?
C12 C13 C14 130.21(18) . . ?
C8 C13 C14 109.10(17) . . ?
C13 C14 C16 119.93(16) . . ?
C13 C14 C24 111.14(14) . . ?
C16 C14 C24 100.77(14) . . ?
C13 C14 C15 101.88(15) . . ?
C16 C14 C15 112.53(15) . . ?
C24 C14 C15 110.80(15) . . ?
O1 C15 N1 125.8(2) . . ?
O1 C15 C14 126.73(19) . . ?
N1 C15 C14 107.47(17) . . ?
C17 C16 C25 106.28(17) . . ?
C17 C16 C14 108.94(17) . . ?
C25 C16 C14 144.54(17) . . ?
C16 C17 O2 113.41(17) . . ?
C16 C17 C18 114.19(18) . . ?
O2 C17 C18 132.28(17) . . ?
C19 C18 C24 119.83(19) . . ?
C19 C18 C17 135.0(2) . . ?
C24 C18 C17 105.12(16) . . ?
C20 C19 C18 118.5(2) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 122.4(2) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C23 118.9(2) . . ?
C20 C21 C22 121.0(2) . . ?
C23 C21 C22 120.1(2) . . ?
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 . . ?
C24 C23 C21 119.7(2) . . ?
C24 C23 H23 120.1 . . ?
C21 C23 H23 120.1 . . ?
C23 C24 C18 120.72(18) . . ?
C23 C24 C14 128.31(18) . . ?
C18 C24 C14 110.96(16) . . ?
C26 C25 C34 118.22(17) . . ?
C26 C25 C16 104.81(16) . . ?
C34 C25 C16 136.95(17) . . ?
O2 C26 C25 111.18(16) . . ?
O2 C26 C27 123.09(16) . . ?
C25 C26 C27 125.73(18) . . ?
C26 C27 C28 125.31(19) . . ?
C26 C27 C32 114.65(17) . . ?
C28 C27 C32 120.04(19) . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.6(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 121.2(2) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C31 C32 C27 117.63(19) . . ?
C31 C32 C33 122.2(2) . . ?
C27 C32 C33 120.12(18) . . ?
C34 C33 C32 123.39(18) . . ?
C34 C33 H33 118.3 . . ?
C32 C33 H33 118.3 . . ?
C33 C34 C25 117.79(18) . . ?
C33 C34 C35 120.95(17) . . ?
C25 C34 C35 121.26(17) . . ?
C40 C35 C36 118.59(19) . . ?
C40 C35 C34 121.57(19) . . ?
C36 C35 C34 119.82(18) . . ?
C37 C36 C35 120.0(2) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 118.8(3) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 H37 120.6 . . ?
C37 C38 C39 123.3(2) . . ?
C37 C38 F2 118.1(3) . . ?
C39 C38 F2 118.6(3) . . ?
C38 C39 C40 118.0(2) . . ?
C38 C39 H39 121.0 . . ?
C40 C39 H39 121.0 . . ?
C35 C40 C39 121.3(2) . . ?
C35 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C15 N1 C8 111.44(17) . . ?
C15 N1 C7 123.62(19) . . ?
C8 N1 C7 124.29(18) . . ?
C17 O2 C26 104.31(13) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 1523296'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C40 H25 Cl2 N O2'
_chemical_formula_sum            'C40 H25 Cl2 N O2'
_chemical_formula_weight         622.51

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                   10.5661(18)
_cell_length_b                   13.057(2)
_cell_length_c                   13.553(2)
_cell_angle_alpha                65.881(5)
_cell_angle_beta                 81.281(5)
_cell_angle_gamma                75.729(5)
_cell_volume                     1651.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9572
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.73

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            22497
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6403
_reflns_number_gt                4571
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0938P)²+0.2887P] 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         6403
_refine_ls_number_parameters     407
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1663
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.053
_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 1.0478(2) 0.6937(2) -0.1156(2) 0.0586(6) Uani 1 1 d . . . . .
H1 H 0.9677 0.6947 -0.0761 0.070 Uiso 1 1 calc R U . . .
C2 C 1.0820(3) 0.6266(3) -0.1754(2) 0.0734(8) Uani 1 1 d . . . . .
H2 H 1.0253 0.5823 -0.1756 0.088 Uiso 1 1 calc R U . . .
C3 C 1.1984(4) 0.6245(3) -0.2344(2) 0.0829(9) Uani 1 1 d . . . . .
H3 H 1.2206 0.5798 -0.2755 0.100 Uiso 1 1 calc R U . . .
C4 C 1.2824(3) 0.6881(3) -0.2329(2) 0.0776(8) Uani 1 1 d . . . . .
H4 H 1.3625 0.6860 -0.2723 0.093 Uiso 1 1 calc R U . . .
C5 C 1.2485(3) 0.7557(2) -0.17291(19) 0.0577(6) Uani 1 1 d . . . . .
H5 H 1.3061 0.7991 -0.1727 0.069 Uiso 1 1 calc R U . . .
C6 C 1.1307(2) 0.75972(18) -0.11332(17) 0.0448(5) Uani 1 1 d . . . . .
C7 C 1.0962(2) 0.8379(2) -0.05271(19) 0.0502(5) Uani 1 1 d . . . . .
H7A H 1.1754 0.8398 -0.0260 0.060 Uiso 1 1 calc R U . . .
H7B H 1.0615 0.9150 -0.1026 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8824(2) 0.87309(17) 0.04727(16) 0.0388(5) Uani 1 1 d . . . . .
C9 C 0.8077(2) 0.80529(17) 0.15254(16) 0.0396(5) Uani 1 1 d . . . . .
C10 C 0.9107(2) 0.69750(17) 0.20110(16) 0.0406(5) Uani 1 1 d . U . . .
C11 C 0.9078(2) 0.60544(18) 0.29845(18) 0.0501(5) Uani 1 1 d . U . . .
H11 H 0.8349 0.6022 0.3469 0.060 Uiso 1 1 calc R U . . .
C12 C 1.0184(3) 0.51740(18) 0.32133(19) 0.0555(6) Uani 1 1 d . U . . .
C13 C 1.1273(3) 0.5216(2) 0.2519(2) 0.0584(6) Uani 1 1 d . U . . .
H13 H 1.1998 0.4616 0.2703 0.070 Uiso 1 1 calc R U . . .
C14 C 1.1303(2) 0.61483(19) 0.1545(2) 0.0515(5) Uani 1 1 d . U . . .
H14 H 1.2040 0.6190 0.1070 0.062 Uiso 1 1 calc R U . . .
C15 C 1.0201(2) 0.70127(17) 0.13043(17) 0.0419(5) Uani 1 1 d . U . . .
C16 C 0.7590(2) 0.87574(17) 0.22139(16) 0.0397(5) Uani 1 1 d . . . . .
C17 C 0.8146(2) 0.90606(18) 0.28759(17) 0.0436(5) Uani 1 1 d . . . . .
C18 C 0.9426(2) 0.88387(17) 0.32832(17) 0.0440(5) Uani 1 1 d . . . . .
C19 C 0.9542(3) 0.8960(2) 0.42368(19) 0.0571(6) Uani 1 1 d . . . . .
H19 H 0.8792 0.9199 0.4609 0.069 Uiso 1 1 calc R U . . .
C20 C 1.0734(3) 0.8735(2) 0.4638(2) 0.0615(7) Uani 1 1 d . . . . .
H20 H 1.0791 0.8826 0.5274 0.074 Uiso 1 1 calc R U . . .
C21 C 1.1842(3) 0.8375(2) 0.4103(2) 0.0582(6) Uani 1 1 d . . . . .
C22 C 1.1773(2) 0.8266(2) 0.3145(2) 0.0593(6) Uani 1 1 d . . . . .
H22 H 1.2530 0.8031 0.2777 0.071 Uiso 1 1 calc R U . . .
C23 C 1.0564(2) 0.8511(2) 0.27383(19) 0.0513(6) Uani 1 1 d . . . . .
H23 H 1.0514 0.8454 0.2084 0.062 Uiso 1 1 calc R U . . .
C24 C 0.6908(2) 0.78164(17) 0.11209(16) 0.0416(5) Uani 1 1 d . . . . .
C25 C 0.7197(2) 0.69983(19) 0.06670(18) 0.0471(5) Uani 1 1 d . . . . .
H25 H 0.8046 0.6573 0.0687 0.057 Uiso 1 1 calc R U . . .
C26 C 0.6274(2) 0.6790(2) 0.01870(19) 0.0525(6) Uani 1 1 d . . . . .
C27 C 0.6634(3) 0.5918(3) -0.0326(2) 0.0741(8) Uani 1 1 d . . . . .
H27A H 0.7535 0.5544 -0.0218 0.111 Uiso 1 1 calc R U . . .
H27B H 0.6504 0.6297 -0.1088 0.111 Uiso 1 1 calc R U . . .
H27C H 0.6092 0.5360 0.0001 0.111 Uiso 1 1 calc R U . . .
C28 C 0.5008(3) 0.7419(2) 0.0188(2) 0.0599(6) Uani 1 1 d . . . . .
H28 H 0.4366 0.7297 -0.0128 0.072 Uiso 1 1 calc R U . . .
C29 C 0.4685(2) 0.8220(2) 0.0647(2) 0.0548(6) Uani 1 1 d . . . . .
H29 H 0.3826 0.8623 0.0643 0.066 Uiso 1 1 calc R U . . .
C30 C 0.5616(2) 0.84419(18) 0.11195(17) 0.0444(5) Uani 1 1 d . . . . .
C31 C 0.5249(2) 0.92550(18) 0.16614(17) 0.0437(5) Uani 1 1 d . . . . .
C32 C 0.4050(2) 0.99104(19) 0.17576(19) 0.0501(5) Uani 1 1 d . . . . .
H32 H 0.3365 0.9921 0.1393 0.060 Uiso 1 1 calc R U . . .
C33 C 0.3813(2) 1.05801(19) 0.24010(19) 0.0502(6) Uani 1 1 d . . . . .
C34 C 0.2555(3) 1.1225(2) 0.2512(2) 0.0629(7) Uani 1 1 d . . . . .
H34 H 0.1878 1.1232 0.2141 0.076 Uiso 1 1 calc R U . . .
C35 C 0.2312(3) 1.1838(2) 0.3150(3) 0.0724(8) Uani 1 1 d . . . . .
H35 H 0.1477 1.2263 0.3205 0.087 Uiso 1 1 calc R U . . .
C36 C 0.3302(3) 1.1832(2) 0.3720(2) 0.0736(8) Uani 1 1 d . . . . .
H36 H 0.3119 1.2252 0.4156 0.088 Uiso 1 1 calc R U . . .
C37 C 0.4539(3) 1.1220(2) 0.3651(2) 0.0602(6) Uani 1 1 d . . . . .
H37 H 0.5193 1.1224 0.4037 0.072 Uiso 1 1 calc R U . . .
C38 C 0.4818(2) 1.05837(18) 0.29923(18) 0.0490(5) Uani 1 1 d . . . . .
C39 C 0.6039(2) 0.99121(18) 0.28473(17) 0.0435(5) Uani 1 1 d . . . . .
C40 C 0.6253(2) 0.93050(17) 0.22038(17) 0.0426(5) Uani 1 1 d . . . . .
Cl1 Cl 1.01569(9) 0.39730(5) 0.44110(6) 0.0827(3) Uani 1 1 d . . . . .
Cl2 Cl 1.33592(8) 0.80646(8) 0.46199(7) 0.0922(3) Uani 1 1 d . . . . .
N1 N 1.00078(17) 0.80390(14) 0.03849(14) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.84335(15) 0.96918(12) -0.01703(12) 0.0481(4) Uani 1 1 d . . . . .
O2 O 0.71818(15) 0.97730(12) 0.32895(12) 0.0485(4) 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 C2 1.375(4) . ?
C1 C6 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(3) . ?
C7 N1 1.462(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.210(2) . ?
C8 N1 1.371(3) . ?
C8 C9 1.554(3) . ?
C9 C10 1.518(3) . ?
C9 C16 1.518(3) . ?
C9 C24 1.567(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.381(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(4) . ?
C12 Cl1 1.739(2) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.403(3) . ?
C16 C17 1.368(3) . ?
C16 C40 1.416(3) . ?
C17 O2 1.415(3) . ?
C17 C18 1.456(3) . ?
C18 C23 1.382(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.365(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.366(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 Cl2 1.736(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 C30 1.407(3) . ?
C25 C26 1.384(3) . ?
C25 H25 0.9300 . ?
C26 C28 1.386(4) . ?
C26 C27 1.509(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.374(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.394(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.471(3) . ?
C31 C32 1.364(3) . ?
C31 C40 1.407(3) . ?
C32 C33 1.427(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.411(3) . ?
C33 C38 1.426(3) . ?
C34 C35 1.361(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.366(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.408(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.406(3) . ?
C39 C40 1.363(3) . ?
C39 O2 1.369(3) . ?

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 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C7 119.1(2) . . ?
C1 C6 C7 123.2(2) . . ?
N1 C7 C6 113.82(17) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 125.55(19) . . ?
O1 C8 C9 126.57(19) . . ?
N1 C8 C9 107.87(17) . . ?
C10 C9 C16 115.78(16) . . ?
C10 C9 C8 101.24(16) . . ?
C16 C9 C8 110.67(16) . . ?
C10 C9 C24 112.42(16) . . ?
C16 C9 C24 111.11(17) . . ?
C8 C9 C24 104.60(15) . . ?
C11 C10 C15 120.6(2) . . ?
C11 C10 C9 130.1(2) . . ?
C15 C10 C9 109.26(18) . . ?
C10 C11 C12 117.2(2) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C13 C12 C11 122.2(2) . . ?
C13 C12 Cl1 119.31(18) . . ?
C11 C12 Cl1 118.5(2) . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 128.0(2) . . ?
C10 C15 N1 110.07(18) . . ?
C17 C16 C40 105.79(18) . . ?
C17 C16 C9 135.56(19) . . ?
C40 C16 C9 118.61(18) . . ?
C16 C17 O2 109.62(18) . . ?
C16 C17 C18 138.1(2) . . ?
O2 C17 C18 112.31(17) . . ?
C23 C18 C19 117.7(2) . . ?
C23 C18 C17 121.58(19) . . ?
C19 C18 C17 120.7(2) . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 Cl2 120.2(2) . . ?
C22 C21 Cl2 119.2(2) . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C18 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
C25 C24 C30 118.87(19) . . ?
C25 C24 C9 117.30(19) . . ?
C30 C24 C9 123.65(18) . . ?
C26 C25 C24 122.8(2) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C28 117.5(2) . . ?
C25 C26 C27 121.3(2) . . ?
C28 C26 C27 121.3(2) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 121.2(2) . . ?
C29 C28 H28 119.4 . . ?
C26 C28 H28 119.4 . . ?
C28 C29 C30 121.5(2) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C24 118.1(2) . . ?
C29 C30 C31 121.2(2) . . ?
C24 C30 C31 120.53(19) . . ?
C32 C31 C40 116.2(2) . . ?
C32 C31 C30 128.4(2) . . ?
C40 C31 C30 115.25(19) . . ?
C31 C32 C33 122.0(2) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C34 C33 C38 117.5(2) . . ?
C34 C33 C32 120.9(2) . . ?
C38 C33 C32 121.5(2) . . ?
C35 C34 C33 121.2(3) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 120.5(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 121.1(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 125.9(2) . . ?
C39 C38 C33 114.1(2) . . ?
C37 C38 C33 120.1(2) . . ?
C40 C39 O2 109.40(18) . . ?
C40 C39 C38 123.5(2) . . ?
O2 C39 C38 127.11(19) . . ?
C39 C40 C31 122.6(2) . . ?
C39 C40 C16 108.83(19) . . ?
C31 C40 C16 128.6(2) . . ?
C8 N1 C15 111.23(17) . . ?
C8 N1 C7 123.35(18) . . ?
C15 N1 C7 125.32(18) . . ?
C39 O2 C17 106.34(15) . . ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.052


####################################################################### 
# 
# 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_4o
_database_code_depnum_ccdc_archive 'CCDC 1523299'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C40 H26 F N O2'
_chemical_formula_sum            'C40 H26 F N O2'
_chemical_formula_weight         571.62

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'
F F 0.0171 0.0103 '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                   10.0836(7)
_cell_length_b                   12.5395(10)
_cell_length_c                   13.2044(10)
_cell_angle_alpha                74.853(2)
_cell_angle_beta                 68.565(2)
_cell_angle_gamma                71.764(2)
_cell_volume                     1455.54(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6080
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            20183
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5668
_reflns_number_gt                3475
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0699P)²] 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         5668
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.8623(2) 0.69032(18) 0.82626(16) 0.0688(6) Uani 1 1 d . . . . .
H1 H 0.8798 0.6715 0.7581 0.083 Uiso 1 1 calc R U . . .
C2 C 0.9635(2) 0.6404(2) 0.8821(2) 0.0830(7) Uani 1 1 d . . . . .
H2 H 1.0486 0.5878 0.8518 0.100 Uiso 1 1 calc R U . . .
C3 C 0.9399(3) 0.6673(2) 0.9812(2) 0.0882(7) Uani 1 1 d . . . . .
H3 H 1.0093 0.6335 1.0182 0.106 Uiso 1 1 calc R U . . .
C4 C 0.8153(3) 0.7437(2) 1.0268(2) 0.0885(7) Uani 1 1 d . . . . .
H4 H 0.7991 0.7616 1.0950 0.106 Uiso 1 1 calc R U . . .
C5 C 0.7115(2) 0.79505(18) 0.97050(18) 0.0746(6) Uani 1 1 d . . . . .
H5 H 0.6265 0.8476 1.0013 0.090 Uiso 1 1 calc R U . . .
C6 C 0.7346(2) 0.76831(15) 0.87015(15) 0.0556(5) Uani 1 1 d . . . . .
C7 C 0.6268(2) 0.82565(15) 0.80651(16) 0.0606(5) Uani 1 1 d . . . . .
H7A H 0.5368 0.8659 0.8546 0.073 Uiso 1 1 calc R U . . .
H7B H 0.6671 0.8815 0.7461 0.073 Uiso 1 1 calc R U . . .
C8 C 0.50031(17) 0.67373(13) 0.82531(13) 0.0408(4) Uani 1 1 d . . . . .
C9 C 0.43108(19) 0.65934(16) 0.93760(13) 0.0531(5) Uani 1 1 d . . . . .
H9 H 0.4430 0.6994 0.9825 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3433(2) 0.58291(17) 0.98042(15) 0.0601(5) Uani 1 1 d . . . . .
H10 H 0.2944 0.5718 1.0558 0.072 Uiso 1 1 calc R U . . .
C11 C 0.32640(19) 0.52292(16) 0.91455(15) 0.0574(5) Uani 1 1 d . . . . .
H11 H 0.2667 0.4718 0.9457 0.069 Uiso 1 1 calc R U . . .
C12 C 0.39776(17) 0.53792(14) 0.80180(14) 0.0471(4) Uani 1 1 d . . . . .
H12 H 0.3873 0.4968 0.7571 0.057 Uiso 1 1 calc R U . . .
C13 C 0.48399(16) 0.61456(13) 0.75755(12) 0.0383(4) Uani 1 1 d . . . . .
C14 C 0.57866(16) 0.64576(13) 0.64061(12) 0.0420(4) Uani 1 1 d . . . . .
C15 C 0.64098(18) 0.73818(14) 0.65324(14) 0.0465(4) Uani 1 1 d . . . . .
C16 C 0.70319(17) 0.54330(14) 0.60005(13) 0.0450(4) Uani 1 1 d . . . . .
C17 C 0.80325(18) 0.47217(15) 0.65090(14) 0.0516(5) Uani 1 1 d . . . . .
H17 H 0.8016 0.4840 0.7180 0.062 Uiso 1 1 calc R U . . .
C18 C 0.90776(18) 0.38172(15) 0.60142(16) 0.0571(5) Uani 1 1 d . . . . .
C19 C 0.90651(19) 0.36614(15) 0.50272(16) 0.0621(5) Uani 1 1 d . . . . .
H19 H 0.9760 0.3061 0.4698 0.074 Uiso 1 1 calc R U . . .
C20 C 0.80576(19) 0.43626(15) 0.44993(15) 0.0579(5) Uani 1 1 d . . . . .
H20 H 0.8069 0.4233 0.3834 0.069 Uiso 1 1 calc R U . . .
C21 C 0.70376(18) 0.52586(14) 0.49909(13) 0.0471(4) Uani 1 1 d . . . . .
C22 C 1.0176(2) 0.30310(17) 0.65717(17) 0.0797(7) Uani 1 1 d . . . . .
H22A H 0.9860 0.2344 0.6946 0.120 Uiso 1 1 calc R U . . .
H22B H 1.0248 0.3399 0.7096 0.120 Uiso 1 1 calc R U . . .
H22C H 1.1118 0.2849 0.6028 0.120 Uiso 1 1 calc R U . . .
C23 C 0.58483(18) 0.61548(14) 0.47251(13) 0.0455(4) Uani 1 1 d . . . . .
C24 C 0.51170(17) 0.68372(14) 0.54847(12) 0.0424(4) Uani 1 1 d . . . . .
C25 C 0.40568(17) 0.77180(13) 0.50530(12) 0.0405(4) Uani 1 1 d . . . . .
C26 C 0.29993(17) 0.87243(14) 0.53839(12) 0.0421(4) Uani 1 1 d . . . . .
C27 C 0.22102(18) 0.93678(14) 0.46875(13) 0.0466(4) Uani 1 1 d . . . . .
H27 H 0.1520 1.0030 0.4892 0.056 Uiso 1 1 calc R U . . .
C28 C 0.23948(17) 0.90739(14) 0.36677(13) 0.0442(4) Uani 1 1 d . . . . .
C29 C 0.15381(19) 0.97422(15) 0.29792(14) 0.0533(5) Uani 1 1 d . . . . .
H29 H 0.0820 1.0385 0.3204 0.064 Uiso 1 1 calc R U . . .
C30 C 0.1741(2) 0.94674(17) 0.20037(15) 0.0623(5) Uani 1 1 d . . . . .
H30 H 0.1173 0.9926 0.1559 0.075 Uiso 1 1 calc R U . . .
C31 C 0.2799(2) 0.84965(18) 0.16564(15) 0.0679(6) Uani 1 1 d . . . . .
H31 H 0.2932 0.8316 0.0981 0.081 Uiso 1 1 calc R U . . .
C32 C 0.3637(2) 0.78144(16) 0.22929(14) 0.0587(5) Uani 1 1 d . . . . .
H32 H 0.4328 0.7165 0.2055 0.070 Uiso 1 1 calc R U . . .
C33 C 0.34641(17) 0.80843(14) 0.33098(12) 0.0431(4) Uani 1 1 d . . . . .
C34 C 0.42568(17) 0.74587(13) 0.40394(12) 0.0425(4) Uani 1 1 d . . . . .
C35 C 0.27708(17) 0.90750(14) 0.64395(13) 0.0440(4) Uani 1 1 d . . . . .
C36 C 0.3179(2) 1.00288(16) 0.64302(15) 0.0657(6) Uani 1 1 d . . . . .
H36 H 0.3613 1.0445 0.5760 0.079 Uiso 1 1 calc R U . . .
C37 C 0.2952(3) 1.03739(18) 0.74053(18) 0.0853(7) Uani 1 1 d . . . . .
H37 H 0.3245 1.1009 0.7401 0.102 Uiso 1 1 calc R U . . .
C38 C 0.2295(3) 0.97646(19) 0.83662(16) 0.0752(7) Uani 1 1 d . . . . .
C39 C 0.1854(2) 0.88380(18) 0.84160(14) 0.0654(6) Uani 1 1 d . . . . .
H39 H 0.1389 0.8446 0.9091 0.079 Uiso 1 1 calc R U . . .
C40 C 0.21079(19) 0.84822(16) 0.74393(13) 0.0542(5) Uani 1 1 d . . . . .
H40 H 0.1828 0.7836 0.7459 0.065 Uiso 1 1 calc R U . . .
F1 F 0.20598(19) 1.00949(12) 0.93312(10) 0.1292(6) Uani 1 1 d . . . . .
N1 N 0.59224(15) 0.74697(12) 0.76245(11) 0.0481(4) Uani 1 1 d . . . . .
O1 O 0.53723(12) 0.64806(9) 0.38209(8) 0.0503(3) Uani 1 1 d . . . . .
O2 O 0.72019(14) 0.79245(11) 0.58045(10) 0.0667(4) 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 C2 1.373(3) . ?
C1 C6 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.355(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(2) . ?
C7 N1 1.448(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.379(2) . ?
C8 C13 1.382(2) . ?
C8 N1 1.401(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.513(2) . ?
C14 C24 1.503(2) . ?
C14 C16 1.540(2) . ?
C14 C15 1.549(2) . ?
C15 O2 1.2093(19) . ?
C15 N1 1.365(2) . ?
C16 C17 1.372(2) . ?
C16 C21 1.404(2) . ?
C17 C18 1.400(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(2) . ?
C18 C22 1.508(2) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9300 . ?
C21 C23 1.443(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.340(2) . ?
C23 O1 1.3653(18) . ?
C24 C25 1.437(2) . ?
C25 C34 1.388(2) . ?
C25 C26 1.423(2) . ?
C26 C27 1.369(2) . ?
C26 C35 1.487(2) . ?
C27 C28 1.420(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.413(2) . ?
C28 C33 1.422(2) . ?
C29 C30 1.347(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.397(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.357(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.406(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.399(2) . ?
C34 O1 1.3917(18) . ?
C35 C40 1.377(2) . ?
C35 C36 1.377(2) . ?
C36 C37 1.383(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.352(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.347(3) . ?
C38 F1 1.358(2) . ?
C39 C40 1.384(2) . ?
C39 H39 0.9300 . ?
C40 H40 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
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.53(18) . . ?
C5 C6 C7 121.06(18) . . ?
C1 C6 C7 120.37(17) . . ?
N1 C7 C6 113.25(14) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 122.11(16) . . ?
C9 C8 N1 127.93(16) . . ?
C13 C8 N1 109.95(14) . . ?
C8 C9 C10 117.10(17) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C11 C10 C9 121.62(17) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.47(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.74(17) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 119.94(15) . . ?
C12 C13 C14 130.97(15) . . ?
C8 C13 C14 109.01(14) . . ?
C24 C14 C13 119.50(13) . . ?
C24 C14 C16 100.79(12) . . ?
C13 C14 C16 111.68(12) . . ?
C24 C14 C15 112.61(13) . . ?
C13 C14 C15 101.62(13) . . ?
C16 C14 C15 110.90(13) . . ?
O2 C15 N1 125.48(17) . . ?
O2 C15 C14 126.74(16) . . ?
N1 C15 C14 107.77(14) . . ?
C17 C16 C21 120.67(15) . . ?
C17 C16 C14 128.20(15) . . ?
C21 C16 C14 111.12(14) . . ?
C16 C17 C18 119.81(17) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 118.63(16) . . ?
C19 C18 C22 121.37(18) . . ?
C17 C18 C22 120.00(18) . . ?
C18 C19 C20 122.75(17) . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C21 C20 C19 118.14(17) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C20 C21 C16 120.00(16) . . ?
C20 C21 C23 135.37(17) . . ?
C16 C21 C23 104.63(14) . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 O1 113.55(14) . . ?
C24 C23 C21 113.94(15) . . ?
O1 C23 C21 132.40(14) . . ?
C23 C24 C25 106.42(14) . . ?
C23 C24 C14 109.51(14) . . ?
C25 C24 C14 143.77(14) . . ?
C34 C25 C26 118.63(14) . . ?
C34 C25 C24 104.80(13) . . ?
C26 C25 C24 136.50(15) . . ?
C27 C26 C25 117.56(14) . . ?
C27 C26 C35 121.07(14) . . ?
C25 C26 C35 121.37(14) . . ?
C26 C27 C28 123.21(15) . . ?
C26 C27 H27 118.4 . . ?
C28 C27 H27 118.4 . . ?
C29 C28 C27 121.84(15) . . ?
C29 C28 C33 117.92(15) . . ?
C27 C28 C33 120.24(14) . . ?
C30 C29 C28 121.37(17) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 120.29(17) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 120.81(17) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 120.31(17) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C34 C33 C32 126.02(16) . . ?
C34 C33 C28 114.68(14) . . ?
C32 C33 C28 119.29(15) . . ?
C25 C34 O1 111.31(13) . . ?
C25 C34 C33 125.63(14) . . ?
O1 C34 C33 123.06(14) . . ?
C40 C35 C36 118.67(16) . . ?
C40 C35 C26 121.13(16) . . ?
C36 C35 C26 120.17(15) . . ?
C35 C36 C37 120.75(18) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C38 C37 C36 118.4(2) . . ?
C38 C37 H37 120.8 . . ?
C36 C37 H37 120.8 . . ?
C39 C38 C37 123.03(19) . . ?
C39 C38 F1 117.9(2) . . ?
C37 C38 F1 119.1(2) . . ?
C38 C39 C40 118.45(18) . . ?
C38 C39 H39 120.8 . . ?
C40 C39 H39 120.8 . . ?
C35 C40 C39 120.72(19) . . ?
C35 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C15 N1 C8 111.49(14) . . ?
C15 N1 C7 123.96(15) . . ?
C8 N1 C7 124.51(15) . . ?
C23 O1 C34 103.91(11) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_3i
_database_code_depnum_ccdc_archive 'CCDC 1523297'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C41 H29 N O3'
_chemical_formula_sum            'C41 H29 N O3'
_chemical_formula_weight         583.65

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'

_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                   11.5428(13)
_cell_length_b                   13.0504(15)
_cell_length_c                   20.6374(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.573(5)
_cell_angle_gamma                90
_cell_volume                     2946.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4373
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.74

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            40344
_diffrn_reflns_av_unetI/netI     0.0983
_diffrn_reflns_av_R_equivalents  0.1190
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_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             5787
_reflns_number_gt                2724
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0679P)²] 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         5787
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1703
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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 0.7475(2) 0.68492(19) 0.43723(12) 0.0426(6) Uani 1 1 d . . . . .
C2 C 0.7760(2) 0.7303(2) 0.50187(13) 0.0558(8) Uani 1 1 d . . . . .
H2 H 0.8125 0.6915 0.5408 0.067 Uiso 1 1 calc R U . . .
C3 C 0.7507(3) 0.8306(2) 0.50807(15) 0.0665(9) Uani 1 1 d . . . . .
H3 H 0.7726 0.8605 0.5512 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6925(3) 0.8888(2) 0.45080(16) 0.0659(9) Uani 1 1 d . . . . .
H4 H 0.6733 0.9569 0.4559 0.079 Uiso 1 1 calc R U . . .
C5 C 0.6633(2) 0.8474(2) 0.38721(15) 0.0586(8) Uani 1 1 d . . . . .
H5 H 0.6244 0.8878 0.3494 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6908(2) 0.74379(19) 0.37736(13) 0.0426(7) Uani 1 1 d . . . . .
C7 C 0.6648(2) 0.70102(19) 0.31074(12) 0.0448(7) Uani 1 1 d . . . . .
H7 H 0.6283 0.7422 0.2729 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6918(2) 0.60086(18) 0.30052(11) 0.0349(6) Uani 1 1 d . . . . .
C9 C 0.67056(19) 0.54593(18) 0.23586(11) 0.0339(6) Uani 1 1 d . . . . .
C10 C 0.6106(2) 0.59290(19) 0.17256(12) 0.0412(6) Uani 1 1 d . . . . .
H10 H 0.5836 0.6601 0.1722 0.049 Uiso 1 1 calc R U . . .
C11 C 0.5907(2) 0.5433(2) 0.11186(12) 0.0451(7) Uani 1 1 d . . . . .
H11 H 0.5509 0.5766 0.0710 0.054 Uiso 1 1 calc R U . . .
C12 C 0.6303(2) 0.4430(2) 0.11138(12) 0.0448(7) Uani 1 1 d . . . . .
C13 C 0.6192(3) 0.2912(2) 0.04494(14) 0.0735(9) Uani 1 1 d . . . . .
H13A H 0.7038 0.2727 0.0640 0.110 Uiso 1 1 calc R U . . .
H13B H 0.5889 0.2694 -0.0019 0.110 Uiso 1 1 calc R U . . .
H13C H 0.5731 0.2585 0.0705 0.110 Uiso 1 1 calc R U . . .
C14 C 0.6896(2) 0.39460(19) 0.17240(11) 0.0428(7) Uani 1 1 d . . . . .
H14 H 0.7168 0.3276 0.1720 0.051 Uiso 1 1 calc R U . . .
C15 C 0.70958(19) 0.44476(18) 0.23487(11) 0.0340(6) Uani 1 1 d . . . . .
C16 C 0.7709(2) 0.58272(19) 0.42395(12) 0.0397(6) Uani 1 1 d . . . . .
C17 C 0.7462(2) 0.54303(18) 0.35981(11) 0.0342(6) Uani 1 1 d . . . . .
C18 C 0.5827(2) -0.0266(2) 0.18989(15) 0.0555(8) Uani 1 1 d . . . . .
H18 H 0.5460 -0.0457 0.2222 0.067 Uiso 1 1 calc R U . . .
C19 C 0.5474(3) -0.0745(2) 0.12722(15) 0.0641(8) Uani 1 1 d . . . . .
H19 H 0.4884 -0.1258 0.1178 0.077 Uiso 1 1 calc R U . . .
C20 C 0.5988(3) -0.0468(2) 0.07913(14) 0.0606(8) Uani 1 1 d . . . . .
H20 H 0.5752 -0.0794 0.0368 0.073 Uiso 1 1 calc R U . . .
C21 C 0.6851(3) 0.0287(2) 0.09266(14) 0.0611(8) Uani 1 1 d . . . . .
H21 H 0.7195 0.0481 0.0594 0.073 Uiso 1 1 calc R U . . .
C22 C 0.7214(2) 0.0764(2) 0.15574(14) 0.0558(7) Uani 1 1 d . . . . .
H22 H 0.7804 0.1276 0.1646 0.067 Uiso 1 1 calc R U . . .
C23 C 0.6708(2) 0.04895(19) 0.20613(12) 0.0420(6) Uani 1 1 d . . . . .
C24 C 0.7109(3) 0.09497(18) 0.27692(12) 0.0540(7) Uani 1 1 d . . . . .
H24A H 0.6421 0.0936 0.2943 0.065 Uiso 1 1 calc R U . . .
H24B H 0.7744 0.0519 0.3065 0.065 Uiso 1 1 calc R U . . .
C25 C 0.6932(2) 0.28134(19) 0.29361(11) 0.0375(6) Uani 1 1 d . . . . .
C26 C 0.7719(2) 0.37941(17) 0.30015(11) 0.0322(6) Uani 1 1 d . . . . .
C27 C 0.8925(2) 0.3337(2) 0.29896(11) 0.0379(6) Uani 1 1 d . . . . .
C28 C 1.0026(2) 0.3797(2) 0.30812(12) 0.0545(7) Uani 1 1 d . . . . .
H28 H 1.0121 0.4499 0.3157 0.065 Uiso 1 1 calc R U . . .
C29 C 1.1014(3) 0.3188(3) 0.30586(14) 0.0710(9) Uani 1 1 d . . . . .
H29 H 1.1773 0.3485 0.3118 0.085 Uiso 1 1 calc R U . . .
C30 C 1.0859(3) 0.2157(3) 0.29496(15) 0.0739(10) Uani 1 1 d . . . . .
H30 H 1.1523 0.1764 0.2937 0.089 Uiso 1 1 calc R U . . .
C31 C 0.9744(3) 0.1672(2) 0.28572(13) 0.0603(8) Uani 1 1 d . . . . .
H31 H 0.9651 0.0969 0.2783 0.072 Uiso 1 1 calc R U . . .
C32 C 0.8779(2) 0.22858(19) 0.28806(11) 0.0394(6) Uani 1 1 d . . . . .
C33 C 0.7827(2) 0.43850(18) 0.36480(11) 0.0351(6) Uani 1 1 d . . . . .
C34 C 0.8281(2) 0.41797(19) 0.43310(12) 0.0430(7) Uani 1 1 d . . . . .
C35 C 0.8768(2) 0.3318(2) 0.47837(12) 0.0461(7) Uani 1 1 d . . . . .
C36 C 0.9396(2) 0.3471(2) 0.54833(13) 0.0527(7) Uani 1 1 d . . . . .
H36 H 0.9542 0.4134 0.5655 0.063 Uiso 1 1 calc R U . . .
C37 C 0.9791(3) 0.2658(2) 0.59105(14) 0.0596(8) Uani 1 1 d . . . . .
H37 H 1.0200 0.2782 0.6370 0.072 Uiso 1 1 calc R U . . .
C38 C 0.9609(3) 0.1657(2) 0.56874(14) 0.0593(8) Uani 1 1 d . . . . .
C39 C 1.0028(3) 0.0760(2) 0.61697(15) 0.0967(12) Uani 1 1 d . . . . .
H39A H 1.0093 0.0161 0.5914 0.145 Uiso 1 1 calc R U . . .
H39B H 0.9446 0.0638 0.6405 0.145 Uiso 1 1 calc R U . . .
H39C H 1.0811 0.0913 0.6496 0.145 Uiso 1 1 calc R U . . .
C40 C 0.9008(3) 0.1506(2) 0.50016(15) 0.0782(10) Uani 1 1 d . . . . .
H40 H 0.8882 0.0841 0.4832 0.094 Uiso 1 1 calc R U . . .
C41 C 0.8590(3) 0.2315(2) 0.45591(14) 0.0722(9) Uani 1 1 d . . . . .
H41 H 0.8179 0.2183 0.4100 0.087 Uiso 1 1 calc R U . . .
N1 N 0.75688(19) 0.19986(15) 0.28164(9) 0.0416(5) Uani 1 1 d . . . . .
O1 O 0.60700(17) 0.39938(14) 0.04836(8) 0.0625(6) Uani 1 1 d . . . . .
O2 O 0.59098(16) 0.27705(13) 0.29812(9) 0.0553(5) Uani 1 1 d . . . . .
O3 O 0.82268(15) 0.50888(12) 0.47090(8) 0.0463(5) 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 C2 1.400(3) . ?
C1 C16 1.405(3) . ?
C1 C6 1.425(3) . ?
C2 C3 1.355(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.424(3) . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C17 1.404(3) . ?
C8 C9 1.465(3) . ?
C9 C15 1.397(3) . ?
C9 C10 1.409(3) . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 O1 1.366(3) . ?
C12 C14 1.380(3) . ?
C13 O1 1.423(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9300 . ?
C15 C26 1.563(3) . ?
C16 O3 1.362(3) . ?
C16 C17 1.364(3) . ?
C17 C33 1.422(3) . ?
C18 C19 1.376(3) . ?
C18 C23 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.357(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.392(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.510(3) . ?
C24 N1 1.460(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O2 1.214(3) . ?
C25 N1 1.359(3) . ?
C25 C26 1.550(3) . ?
C26 C33 1.511(3) . ?
C26 C27 1.522(3) . ?
C27 C28 1.363(3) . ?
C27 C32 1.392(3) . ?
C28 C29 1.402(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.392(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.385(3) . ?
C31 H31 0.9300 . ?
C32 N1 1.412(3) . ?
C33 C34 1.365(3) . ?
C34 O3 1.432(3) . ?
C34 C35 1.456(3) . ?
C35 C41 1.381(4) . ?
C35 C36 1.408(3) . ?
C36 C37 1.362(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.378(4) . ?
C37 H37 0.9300 . ?
C38 C40 1.378(4) . ?
C38 C39 1.512(4) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.379(4) . ?
C40 H40 0.9300 . ?
C41 H41 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
C2 C1 C16 125.9(2) . . ?
C2 C1 C6 120.1(2) . . ?
C16 C1 C6 114.0(2) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 C1 116.8(2) . . ?
C7 C6 C1 121.6(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C17 115.9(2) . . ?
C7 C8 C9 128.6(2) . . ?
C17 C8 C9 115.4(2) . . ?
C15 C9 C10 117.6(2) . . ?
C15 C9 C8 121.0(2) . . ?
C10 C9 C8 121.4(2) . . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O1 C12 C14 124.6(2) . . ?
O1 C12 C11 115.8(2) . . ?
C14 C12 C11 119.6(2) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 121.0(2) . . ?
C12 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C9 C15 C14 119.8(2) . . ?
C9 C15 C26 124.4(2) . . ?
C14 C15 C26 115.8(2) . . ?
O3 C16 C17 109.3(2) . . ?
O3 C16 C1 126.9(2) . . ?
C17 C16 C1 123.8(2) . . ?
C16 C17 C8 122.6(2) . . ?
C16 C17 C33 109.2(2) . . ?
C8 C17 C33 128.2(2) . . ?
C19 C18 C23 121.8(3) . . ?
C19 C18 H18 119.1 . . ?
C23 C18 H18 119.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C22 117.1(2) . . ?
C18 C23 C24 119.6(2) . . ?
C22 C23 C24 123.3(2) . . ?
N1 C24 C23 115.5(2) . . ?
N1 C24 H24A 108.4 . . ?
C23 C24 H24A 108.4 . . ?
N1 C24 H24B 108.4 . . ?
C23 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
O2 C25 N1 124.9(2) . . ?
O2 C25 C26 126.0(2) . . ?
N1 C25 C26 109.0(2) . . ?
C33 C26 C27 113.27(18) . . ?
C33 C26 C25 112.31(18) . . ?
C27 C26 C25 100.88(19) . . ?
C33 C26 C15 111.63(18) . . ?
C27 C26 C15 111.84(17) . . ?
C25 C26 C15 106.23(17) . . ?
C28 C27 C32 121.0(2) . . ?
C28 C27 C26 130.0(2) . . ?
C32 C27 C26 108.9(2) . . ?
C27 C28 C29 118.6(3) . . ?
C27 C28 H28 120.7 . . ?
C29 C28 H28 120.7 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 122.5(3) . . ?
C29 C30 H30 118.8 . . ?
C31 C30 H30 118.8 . . ?
C32 C31 C30 116.8(3) . . ?
C32 C31 H31 121.6 . . ?
C30 C31 H31 121.6 . . ?
C31 C32 C27 121.3(3) . . ?
C31 C32 N1 128.7(3) . . ?
C27 C32 N1 110.0(2) . . ?
C34 C33 C17 105.7(2) . . ?
C34 C33 C26 135.1(2) . . ?
C17 C33 C26 119.10(19) . . ?
C33 C34 O3 109.3(2) . . ?
C33 C34 C35 139.2(2) . . ?
O3 C34 C35 111.4(2) . . ?
C41 C35 C36 116.8(2) . . ?
C41 C35 C34 122.1(2) . . ?
C36 C35 C34 121.1(2) . . ?
C37 C36 C35 120.7(3) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 122.6(3) . . ?
C36 C37 H37 118.7 . . ?
C38 C37 H37 118.7 . . ?
C40 C38 C37 116.9(2) . . ?
C40 C38 C39 121.1(3) . . ?
C37 C38 C39 122.0(3) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 C41 121.8(3) . . ?
C38 C40 H40 119.1 . . ?
C41 C40 H40 119.1 . . ?
C40 C41 C35 121.3(3) . . ?
C40 C41 H41 119.3 . . ?
C35 C41 H41 119.3 . . ?
C25 N1 C32 110.6(2) . . ?
C25 N1 C24 122.7(2) . . ?
C32 N1 C24 125.7(2) . . ?
C12 O1 C13 117.9(2) . . ?
C16 O3 C34 106.51(17) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_E2
_database_code_depnum_ccdc_archive 'CCDC 1526533'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C39 H25 Cl N2 O4'
_chemical_formula_sum            'C39 H25 Cl N2 O4'
_chemical_formula_weight         621.06

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                   12.8383(18)
_cell_length_b                   13.0875(18)
_cell_length_c                   14.1034(19)
_cell_angle_alpha                71.229(4)
_cell_angle_beta                 69.868(4)
_cell_angle_gamma                65.226(3)
_cell_volume                     1975.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.044
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            17060
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.572
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             8603
_reflns_number_gt                3855
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1224P)²+0.0783P] 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         8603
_refine_ls_number_parameters     415
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2582
_refine_ls_wR_factor_gt          0.2187
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.112
_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 0.3241(4) 0.5482(3) -0.2046(3) 0.0718(7) Uani 1 1 d . U . . .
H1 H 0.4057 0.5271 -0.2305 0.086 Uiso 1 1 calc R U . . .
C2 C 0.2522(4) 0.6205(4) -0.2699(3) 0.0798(7) Uani 1 1 d . U . . .
H2 H 0.2848 0.6493 -0.3381 0.096 Uiso 1 1 calc R U . . .
C3 C 0.1340(4) 0.6494(4) -0.2339(3) 0.0870(8) Uani 1 1 d . U . . .
H3 H 0.0850 0.6960 -0.2784 0.104 Uiso 1 1 calc R U . . .
C4 C 0.0854(4) 0.6111(4) -0.1329(3) 0.0897(8) Uani 1 1 d . U . . .
H4 H 0.0036 0.6333 -0.1087 0.108 Uiso 1 1 calc R U . . .
C5 C 0.1576(4) 0.5388(4) -0.0658(3) 0.0838(7) Uani 1 1 d . U . . .
H5 H 0.1242 0.5126 0.0030 0.101 Uiso 1 1 calc R U . . .
C6 C 0.2798(4) 0.5059(3) -0.1023(3) 0.0715(7) Uani 1 1 d . U . . .
C7 C 0.3630(3) 0.4256(3) -0.0357(2) 0.0530(9) Uani 1 1 d . . . . .
H7A H 0.3903 0.3489 -0.0485 0.064 Uiso 1 1 calc R U . . .
H7B H 0.4314 0.4489 -0.0565 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3245(3) 0.4858(3) 0.1262(2) 0.0444(8) Uani 1 1 d . . . . .
C9 C 0.2677(3) 0.4525(2) 0.2406(2) 0.0440(8) Uani 1 1 d . . . . .
H9 H 0.1909 0.5139 0.2544 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2409(3) 0.3490(2) 0.2453(2) 0.0450(8) Uani 1 1 d . . . . .
C11 C 0.1970(3) 0.2731(3) 0.3266(3) 0.0563(9) Uani 1 1 d . . . . .
H11 H 0.1781 0.2815 0.3941 0.068 Uiso 1 1 calc R U . . .
C12 C 0.1815(3) 0.1850(3) 0.3064(3) 0.0621(10) Uani 1 1 d . . . . .
H12 H 0.1534 0.1327 0.3607 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2074(3) 0.1739(3) 0.2063(3) 0.0623(10) Uani 1 1 d . . . . .
H13 H 0.1963 0.1140 0.1940 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2493(3) 0.2495(3) 0.1240(3) 0.0553(9) Uani 1 1 d . . . . .
H14 H 0.2649 0.2425 0.0565 0.066 Uiso 1 1 calc R U . . .
C15 C 0.2673(3) 0.3359(3) 0.1447(2) 0.0447(8) Uani 1 1 d . . . . .
C16 C 0.3305(3) 0.4422(2) 0.3181(2) 0.0442(8) Uani 1 1 d . . . . .
C17 C 0.2950(3) 0.5242(3) 0.3740(2) 0.0489(8) Uani 1 1 d . . . . .
C18 C 0.2105(3) 0.6423(3) 0.3707(3) 0.0514(8) Uani 1 1 d . . . . .
C19 C 0.1522(3) 0.6825(3) 0.4613(3) 0.0675(10) Uani 1 1 d . . . . .
H19 H 0.1650 0.6333 0.5239 0.081 Uiso 1 1 calc R U . . .
C20 C 0.0759(4) 0.7935(4) 0.4604(3) 0.0781(12) Uani 1 1 d . . . . .
H20 H 0.0380 0.8199 0.5217 0.094 Uiso 1 1 calc R U . . .
C21 C 0.0559(3) 0.8653(3) 0.3684(4) 0.0730(11) Uani 1 1 d . . . . .
C22 C 0.1125(3) 0.8286(3) 0.2771(3) 0.0709(11) Uani 1 1 d . . . . .
H22 H 0.0987 0.8784 0.2150 0.085 Uiso 1 1 calc R U . . .
C23 C 0.1904(3) 0.7166(3) 0.2785(3) 0.0578(9) Uani 1 1 d . . . . .
H23 H 0.2296 0.6911 0.2168 0.069 Uiso 1 1 calc R U . . .
C24 C 0.4211(3) 0.3449(2) 0.3618(2) 0.0435(8) Uani 1 1 d . . . . .
C25 C 0.4277(3) 0.3753(3) 0.4444(2) 0.0477(8) Uani 1 1 d . . . . .
C26 C 0.4968(3) 0.3046(3) 0.5154(2) 0.0504(8) Uani 1 1 d . . . . .
C27 C 0.4952(3) 0.3376(3) 0.6014(3) 0.0615(9) Uani 1 1 d . . . . .
H27 H 0.4484 0.4111 0.6133 0.074 Uiso 1 1 calc R U . . .
C28 C 0.5636(4) 0.2598(4) 0.6678(3) 0.0710(11) Uani 1 1 d . . . . .
H28 H 0.5627 0.2808 0.7252 0.085 Uiso 1 1 calc R U . . .
C29 C 0.6346(4) 0.1495(4) 0.6498(3) 0.0713(11) Uani 1 1 d . . . . .
H29 H 0.6802 0.0975 0.6955 0.086 Uiso 1 1 calc R U . . .
C30 C 0.6373(3) 0.1178(3) 0.5662(3) 0.0609(9) Uani 1 1 d . . . . .
H30 H 0.6865 0.0447 0.5544 0.073 Uiso 1 1 calc R U . . .
C31 C 0.5674(3) 0.1933(3) 0.4970(2) 0.0507(8) Uani 1 1 d . . . . .
C32 C 0.5658(3) 0.1616(3) 0.4097(2) 0.0553(9) Uani 1 1 d . . . . .
H32 H 0.6140 0.0881 0.3985 0.066 Uiso 1 1 calc R U . . .
C33 C 0.4977(3) 0.2329(2) 0.3415(2) 0.0447(8) Uani 1 1 d . . . . .
C34 C 0.5144(3) 0.1940(2) 0.2479(2) 0.0435(8) Uani 1 1 d . . . . .
C35 C 0.5065(3) 0.0883(3) 0.2568(3) 0.0544(9) Uani 1 1 d . . . . .
H35 H 0.4801 0.0472 0.3218 0.065 Uiso 1 1 calc R U . . .
C36 C 0.5373(3) 0.0436(3) 0.1710(3) 0.0574(9) Uani 1 1 d . . . . .
H36 H 0.5324 -0.0272 0.1771 0.069 Uiso 1 1 calc R U . . .
C37 C 0.5757(3) 0.1068(3) 0.0758(2) 0.0511(9) Uani 1 1 d . . . . .
C38 C 0.5837(3) 0.2113(3) 0.0639(2) 0.0521(9) Uani 1 1 d . . . . .
H38 H 0.6098 0.2522 -0.0013 0.063 Uiso 1 1 calc R U . . .
C39 C 0.5521(3) 0.2549(3) 0.1508(2) 0.0474(8) Uani 1 1 d . . . . .
H39 H 0.5564 0.3262 0.1439 0.057 Uiso 1 1 calc R U . . .
Cl1 Cl -0.04081(12) 1.00685(10) 0.36701(12) 0.1206(5) Uani 1 1 d . . . . .
N1 N 0.3133(2) 0.4201(2) 0.07550(18) 0.0464(7) Uani 1 1 d . . . . .
N2 N 0.6153(3) 0.0574(3) -0.0162(3) 0.0769(10) Uani 1 1 d . . . . .
O1 O 0.3687(2) 0.56005(19) 0.08697(17) 0.0599(6) Uani 1 1 d . . . . .
O2 O 0.35234(19) 0.48463(17) 0.45225(16) 0.0524(6) Uani 1 1 d . . . . .
O3 O 0.6297(4) 0.1192(3) -0.1006(2) 0.1257(14) Uani 1 1 d . . . . .
O4 O 0.6298(3) -0.0436(3) -0.0025(2) 0.1127(12) 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 C2 1.373(5) . ?
C1 C6 1.378(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.348(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(5) . ?
C7 N1 1.466(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.213(4) . ?
C8 N1 1.357(4) . ?
C8 C9 1.526(4) . ?
C9 C10 1.509(4) . ?
C9 C16 1.511(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.382(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.405(4) . ?
C16 C17 1.367(4) . ?
C16 C24 1.449(4) . ?
C17 O2 1.379(4) . ?
C17 C18 1.466(4) . ?
C18 C23 1.382(5) . ?
C18 C19 1.384(4) . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(5) . ?
C21 Cl1 1.743(4) . ?
C22 C23 1.385(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.384(4) . ?
C24 C33 1.437(4) . ?
C25 O2 1.365(4) . ?
C25 C26 1.405(4) . ?
C26 C27 1.404(4) . ?
C26 C31 1.409(4) . ?
C27 C28 1.373(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.397(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.356(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.405(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.428(4) . ?
C32 C33 1.371(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.481(4) . ?
C34 C39 1.381(4) . ?
C34 C35 1.392(4) . ?
C35 C36 1.376(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.379(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.366(4) . ?
C37 N2 1.473(4) . ?
C38 C39 1.380(4) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
N2 O3 1.208(4) . ?
N2 O4 1.214(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
C2 C1 C6 122.3(4) . . ?
C2 C1 H1 118.8 . . ?
C6 C1 H1 118.8 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 117.6(4) . . ?
C1 C6 C7 119.7(3) . . ?
C5 C6 C7 122.7(3) . . ?
N1 C7 C6 115.2(3) . . ?
N1 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
N1 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 N1 125.9(3) . . ?
O1 C8 C9 126.3(3) . . ?
N1 C8 C9 107.8(3) . . ?
C10 C9 C16 117.5(3) . . ?
C10 C9 C8 102.7(2) . . ?
C16 C9 C8 117.9(3) . . ?
C10 C9 H9 105.9 . . ?
C16 C9 H9 105.9 . . ?
C8 C9 H9 105.9 . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 C9 132.5(3) . . ?
C15 C10 C9 107.9(3) . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 117.9(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 N1 128.9(3) . . ?
C10 C15 N1 109.7(3) . . ?
C17 C16 C24 105.8(3) . . ?
C17 C16 C9 123.1(3) . . ?
C24 C16 C9 130.4(3) . . ?
C16 C17 O2 111.3(3) . . ?
C16 C17 C18 135.2(3) . . ?
O2 C17 C18 113.5(2) . . ?
C23 C18 C19 118.7(3) . . ?
C23 C18 C17 121.6(3) . . ?
C19 C18 C17 119.6(3) . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 Cl1 119.4(3) . . ?
C22 C21 Cl1 119.4(3) . . ?
C21 C22 C23 119.1(4) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C33 117.5(3) . . ?
C25 C24 C16 105.7(3) . . ?
C33 C24 C16 136.7(3) . . ?
O2 C25 C24 110.8(3) . . ?
O2 C25 C26 122.7(3) . . ?
C24 C25 C26 126.5(3) . . ?
C27 C26 C25 124.2(3) . . ?
C27 C26 C31 120.7(3) . . ?
C25 C26 C31 115.1(3) . . ?
C28 C27 C26 119.1(3) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C29 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 121.2(3) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C30 C31 C26 117.8(3) . . ?
C30 C31 C32 122.7(3) . . ?
C26 C31 C32 119.5(3) . . ?
C33 C32 C31 124.0(3) . . ?
C33 C32 H32 118.0 . . ?
C31 C32 H32 118.0 . . ?
C32 C33 C24 117.3(3) . . ?
C32 C33 C34 118.4(3) . . ?
C24 C33 C34 124.1(3) . . ?
C39 C34 C35 118.8(3) . . ?
C39 C34 C33 120.5(3) . . ?
C35 C34 C33 120.1(3) . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 118.2(3) . . ?
C35 C36 H36 120.9 . . ?
C37 C36 H36 120.9 . . ?
C38 C37 C36 122.5(3) . . ?
C38 C37 N2 118.5(3) . . ?
C36 C37 N2 118.8(3) . . ?
C37 C38 C39 118.5(3) . . ?
C37 C38 H38 120.7 . . ?
C39 C38 H38 120.7 . . ?
C38 C39 C34 121.0(3) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
C8 N1 C15 111.4(2) . . ?
C8 N1 C7 122.6(3) . . ?
C15 N1 C7 125.2(3) . . ?
O3 N2 O4 123.5(3) . . ?
O3 N2 C37 118.8(4) . . ?
O4 N2 C37 117.7(4) . . ?
C25 O2 C17 106.3(2) . . ?

_refine_diff_density_max         0.640
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.049





#==========================================================================
####################################################################### 
# 
# 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_3k
_database_code_depnum_ccdc_archive 'CCDC 1523298'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C40 H25 Cl2 N O3, C H Cl3'
_chemical_formula_sum            'C41 H26 Cl5 N O3'
_chemical_formula_weight         757.88

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                   10.794(13)
_cell_length_b                   12.840(16)
_cell_length_c                   13.826(17)
_cell_angle_alpha                68.88(3)
_cell_angle_beta                 77.77(3)
_cell_angle_gamma                89.02(3)
_cell_volume                     1743(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.458
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            13177
_diffrn_reflns_av_unetI/netI     0.1755
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             6323
_reflns_number_gt                2858
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.2000P)²] 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         6323
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2459
_refine_ls_R_factor_gt           0.1424
_refine_ls_wR_factor_ref         0.3586
_refine_ls_wR_factor_gt          0.3160
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.4229(8) 0.8404(7) 0.0346(7) 0.057(2) Uani 1 1 d . . . . .
H1 H 0.4188 0.8097 0.1073 0.068 Uiso 1 1 calc R U . . .
C2 C 0.4932(9) 0.7928(8) -0.0293(9) 0.073(3) Uani 1 1 d . . . . .
H2 H 0.5370 0.7302 -0.0005 0.087 Uiso 1 1 calc R U . . .
C3 C 0.5000(9) 0.8362(9) -0.1357(10) 0.075(3) Uani 1 1 d . . . . .
H3 H 0.5484 0.8033 -0.1797 0.090 Uiso 1 1 calc R U . . .
C4 C 0.4349(10) 0.9294(10) -0.1785(7) 0.078(3) Uani 1 1 d . . . . .
H4 H 0.4402 0.9601 -0.2514 0.093 Uiso 1 1 calc R U . . .
C5 C 0.3631(8) 0.9759(8) -0.1130(7) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.3174 1.0373 -0.1413 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3575(7) 0.9327(6) -0.0049(6) 0.0422(18) Uani 1 1 d . . . . .
C7 C 0.2805(7) 0.9863(6) 0.0667(6) 0.048(2) Uani 1 1 d . . . . .
H7A H 0.3380 1.0153 0.0977 0.057 Uiso 1 1 calc R U . . .
H7B H 0.2413 1.0495 0.0235 0.057 Uiso 1 1 calc R U . . .
C8 C 0.1699(6) 0.9004(5) 0.2556(5) 0.0326(16) Uani 1 1 d . . . . .
C9 C 0.0385(6) 0.8400(5) 0.3196(4) 0.0270(15) Uani 1 1 d . . . . .
C10 C -0.0084(6) 0.8113(5) 0.2353(5) 0.0310(16) Uani 1 1 d . . . . .
C11 C -0.1168(6) 0.7494(5) 0.2429(5) 0.0310(16) Uani 1 1 d . . . . .
H11 H -0.1745 0.7160 0.3073 0.037 Uiso 1 1 calc R U . . .
C12 C -0.1352(7) 0.7396(6) 0.1511(6) 0.0408(19) Uani 1 1 d . . . . .
C13 C -0.0521(7) 0.7851(6) 0.0550(5) 0.0433(19) Uani 1 1 d . . . . .
H13 H -0.0678 0.7750 -0.0048 0.052 Uiso 1 1 calc R U . . .
C14 C 0.0573(7) 0.8473(6) 0.0478(5) 0.0383(18) Uani 1 1 d . . . . .
H14 H 0.1155 0.8802 -0.0165 0.046 Uiso 1 1 calc R U . . .
C15 C 0.0753(6) 0.8580(5) 0.1390(5) 0.0290(15) Uani 1 1 d . . . . .
C16 C 0.0482(6) 0.7414(5) 0.4174(5) 0.0284(15) Uani 1 1 d . . . . .
C17 C 0.1078(6) 0.6428(5) 0.4390(5) 0.0320(16) Uani 1 1 d . . . . .
C18 C 0.1912(6) 0.5853(5) 0.3821(5) 0.0329(16) Uani 1 1 d . . . . .
C19 C 0.2410(7) 0.4862(6) 0.4348(6) 0.049(2) Uani 1 1 d . . . . .
H19 H 0.2176 0.4548 0.5086 0.058 Uiso 1 1 calc R U . . .
C20 C 0.3225(8) 0.4339(7) 0.3819(7) 0.063(2) Uani 1 1 d . . . . .
H20 H 0.3530 0.3665 0.4194 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3610(7) 0.4797(7) 0.2726(7) 0.052(2) Uani 1 1 d . . . . .
C22 C 0.3093(8) 0.5756(7) 0.2172(6) 0.054(2) Uani 1 1 d . . . . .
H22 H 0.3307 0.6052 0.1433 0.065 Uiso 1 1 calc R U . . .
C23 C 0.2265(7) 0.6268(6) 0.2721(6) 0.049(2) Uani 1 1 d . . . . .
H23 H 0.1924 0.6920 0.2343 0.059 Uiso 1 1 calc R U . . .
C24 C -0.0130(6) 0.7458(5) 0.5186(5) 0.0279(15) Uani 1 1 d . . . . .
C25 C 0.0076(6) 0.6477(5) 0.5973(5) 0.0303(16) Uani 1 1 d . . . . .
C26 C -0.0377(6) 0.6224(6) 0.7035(5) 0.0377(18) Uani 1 1 d . . . . .
C27 C -0.0210(7) 0.5241(6) 0.7867(5) 0.046(2) Uani 1 1 d . . . . .
H27 H 0.0264 0.4689 0.7707 0.055 Uiso 1 1 calc R U . . .
C28 C -0.0720(8) 0.5082(7) 0.8886(6) 0.057(2) Uani 1 1 d . . . . .
H28 H -0.0578 0.4432 0.9420 0.069 Uiso 1 1 calc R U . . .
C29 C -0.1458(8) 0.5875(7) 0.9155(5) 0.054(2) Uani 1 1 d . . . . .
H29 H -0.1818 0.5750 0.9863 0.065 Uiso 1 1 calc R U . . .
C30 C -0.1653(7) 0.6835(7) 0.8377(5) 0.049(2) Uani 1 1 d . . . . .
H30 H -0.2133 0.7365 0.8572 0.059 Uiso 1 1 calc R U . . .
C31 C -0.1159(7) 0.7058(6) 0.7297(5) 0.0393(18) Uani 1 1 d . . . . .
C32 C -0.1359(6) 0.8057(6) 0.6461(5) 0.0358(17) Uani 1 1 d . . . . .
H32 H -0.1844 0.8589 0.6649 0.043 Uiso 1 1 calc R U . . .
C33 C -0.0887(6) 0.8271(5) 0.5422(5) 0.0302(16) Uani 1 1 d . . . . .
C34 C -0.1022(6) 0.9251(5) 0.4490(5) 0.0294(16) Uani 1 1 d . . . . .
C35 C -0.0464(6) 0.9288(5) 0.3462(5) 0.0287(15) Uani 1 1 d . . . . .
C36 C -0.0632(6) 1.0227(6) 0.2603(5) 0.0347(17) Uani 1 1 d . . . . .
H36 H -0.0239 1.0276 0.1920 0.042 Uiso 1 1 calc R U . . .
C37 C -0.1358(6) 1.1086(6) 0.2725(5) 0.0335(17) Uani 1 1 d . . . . .
C38 C -0.2214(8) 1.2815(6) 0.1888(6) 0.051(2) Uani 1 1 d . . . . .
H38A H -0.3063 1.2509 0.2251 0.077 Uiso 1 1 calc R U . . .
H38B H -0.2223 1.3342 0.1190 0.077 Uiso 1 1 calc R U . . .
H38C H -0.1886 1.3187 0.2281 0.077 Uiso 1 1 calc R U . . .
C39 C -0.1884(6) 1.1037(6) 0.3729(6) 0.0420(18) Uani 1 1 d . . . . .
H39 H -0.2351 1.1619 0.3829 0.050 Uiso 1 1 calc R U . . .
C40 C -0.1729(6) 1.0127(6) 0.4598(5) 0.0367(17) Uani 1 1 d . . . . .
H40 H -0.2111 1.0102 0.5276 0.044 Uiso 1 1 calc R U . . .
C41 C 0.4377(8) 0.7802(9) 0.4375(7) 0.078(3) Uani 1 1 d . . . . .
H41 H 0.3712 0.8264 0.4087 0.094 Uiso 1 1 calc R U . . .
Cl1 Cl -0.2707(2) 0.6589(2) 0.15978(18) 0.0733(8) Uani 1 1 d . . . . .
Cl2 Cl 0.4711(2) 0.4178(2) 0.2039(2) 0.0858(9) Uani 1 1 d . . . . .
Cl3 Cl 0.3671(2) 0.6700(3) 0.5505(2) 0.0922(9) Uani 1 1 d . . . . .
Cl4 Cl 0.5393(4) 0.8622(3) 0.4687(3) 0.1269(14) Uani 1 1 d . . . . .
Cl5 Cl 0.5222(3) 0.7318(3) 0.3416(3) 0.1204(12) Uani 1 1 d . . . . .
N1 N 0.1820(5) 0.9139(5) 0.1520(4) 0.0352(14) Uani 1 1 d . . . . .
O1 O 0.2467(4) 0.9346(4) 0.2926(4) 0.0455(13) Uani 1 1 d . . . . .
O2 O 0.0813(4) 0.5843(4) 0.5503(3) 0.0357(12) Uani 1 1 d . . . . .
O3 O -0.1432(5) 1.1941(4) 0.1801(4) 0.0490(14) 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 C2 1.348(12) . ?
C1 C6 1.367(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(10) . ?
C7 N1 1.449(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.222(7) . ?
C8 N1 1.356(8) . ?
C8 C9 1.552(9) . ?
C9 C16 1.505(8) . ?
C9 C10 1.522(8) . ?
C9 C35 1.549(9) . ?
C10 C15 1.372(9) . ?
C10 C11 1.390(9) . ?
C11 C12 1.374(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(10) . ?
C12 Cl1 1.765(7) . ?
C13 C14 1.404(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(9) . ?
C14 H14 0.9300 . ?
C15 N1 1.445(8) . ?
C16 C17 1.374(9) . ?
C16 C24 1.435(9) . ?
C17 O2 1.416(7) . ?
C17 C18 1.439(9) . ?
C18 C19 1.383(9) . ?
C18 C23 1.385(10) . ?
C19 C20 1.350(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.376(11) . ?
C21 Cl2 1.726(8) . ?
C22 C23 1.364(10) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.388(8) . ?
C24 C33 1.403(9) . ?
C25 O2 1.363(7) . ?
C25 C26 1.363(9) . ?
C26 C27 1.409(10) . ?
C26 C31 1.452(10) . ?
C27 C28 1.340(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.389(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.361(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.399(10) . ?
C30 H30 0.9300 . ?
C31 C32 1.434(9) . ?
C32 C33 1.346(9) . ?
C32 H32 0.9300 . ?
C33 C34 1.472(8) . ?
C34 C40 1.383(9) . ?
C34 C35 1.405(9) . ?
C35 C36 1.396(8) . ?
C36 C37 1.381(9) . ?
C36 H36 0.9300 . ?
C37 C39 1.362(9) . ?
C37 O3 1.368(7) . ?
C38 O3 1.417(9) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.380(9) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 Cl3 1.722(10) . ?
C41 Cl5 1.742(10) . ?
C41 Cl4 1.752(10) . ?
C41 H41 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
C2 C1 C6 121.6(8) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 120.1(9) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 119.9(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.4(9) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.7(9) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.2(8) . . ?
C1 C6 C7 121.4(7) . . ?
C5 C6 C7 120.4(7) . . ?
N1 C7 C6 115.6(6) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 126.1(6) . . ?
O1 C8 C9 124.9(6) . . ?
N1 C8 C9 108.9(5) . . ?
C16 C9 C10 115.1(5) . . ?
C16 C9 C35 112.4(5) . . ?
C10 C9 C35 108.0(5) . . ?
C16 C9 C8 112.4(5) . . ?
C10 C9 C8 101.0(5) . . ?
C35 C9 C8 107.0(5) . . ?
C15 C10 C11 119.6(5) . . ?
C15 C10 C9 109.8(6) . . ?
C11 C10 C9 130.6(6) . . ?
C12 C11 C10 117.2(6) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
C13 C12 C11 123.7(7) . . ?
C13 C12 Cl1 118.5(5) . . ?
C11 C12 Cl1 117.8(6) . . ?
C12 C13 C14 118.9(6) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C15 C14 C13 117.5(6) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C10 123.1(6) . . ?
C14 C15 N1 127.5(6) . . ?
C10 C15 N1 109.4(5) . . ?
C17 C16 C24 106.1(5) . . ?
C17 C16 C9 136.3(6) . . ?
C24 C16 C9 117.5(6) . . ?
C16 C17 O2 109.0(6) . . ?
C16 C17 C18 138.5(6) . . ?
O2 C17 C18 112.4(5) . . ?
C19 C18 C23 116.8(7) . . ?
C19 C18 C17 121.5(7) . . ?
C23 C18 C17 121.7(6) . . ?
C20 C19 C18 121.7(8) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.5(7) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.4(7) . . ?
C22 C21 Cl2 119.4(7) . . ?
C20 C21 Cl2 121.2(6) . . ?
C23 C22 C21 119.1(8) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 122.4(7) . . ?
C22 C23 H23 118.8 . . ?
C18 C23 H23 118.8 . . ?
C25 C24 C33 122.0(6) . . ?
C25 C24 C16 108.1(6) . . ?
C33 C24 C16 129.8(6) . . ?
O2 C25 C26 126.9(6) . . ?
O2 C25 C24 108.6(6) . . ?
C26 C25 C24 124.5(7) . . ?
C25 C26 C27 127.0(7) . . ?
C25 C26 C31 114.4(6) . . ?
C27 C26 C31 118.5(6) . . ?
C28 C27 C26 121.4(8) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C29 120.9(7) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 119.8(7) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 122.6(8) . . ?
C29 C30 H30 118.7 . . ?
C31 C30 H30 118.7 . . ?
C30 C31 C32 123.8(7) . . ?
C30 C31 C26 116.6(6) . . ?
C32 C31 C26 119.6(6) . . ?
C33 C32 C31 123.8(7) . . ?
C33 C32 H32 118.1 . . ?
C31 C32 H32 118.1 . . ?
C32 C33 C24 115.7(6) . . ?
C32 C33 C34 129.5(7) . . ?
C24 C33 C34 114.8(6) . . ?
C40 C34 C35 118.6(6) . . ?
C40 C34 C33 121.4(6) . . ?
C35 C34 C33 119.9(6) . . ?
C36 C35 C34 117.8(6) . . ?
C36 C35 C9 116.7(6) . . ?
C34 C35 C9 125.5(5) . . ?
C37 C36 C35 122.8(6) . . ?
C37 C36 H36 118.6 . . ?
C35 C36 H36 118.6 . . ?
C39 C37 O3 126.1(6) . . ?
C39 C37 C36 118.5(6) . . ?
O3 C37 C36 115.4(6) . . ?
O3 C38 H38A 109.5 . . ?
O3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 C40 120.4(7) . . ?
C37 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C34 121.9(6) . . ?
C39 C40 H40 119.0 . . ?
C34 C40 H40 119.0 . . ?
Cl3 C41 Cl5 110.7(6) . . ?
Cl3 C41 Cl4 109.9(5) . . ?
Cl5 C41 Cl4 110.0(5) . . ?
Cl3 C41 H41 108.7 . . ?
Cl5 C41 H41 108.7 . . ?
Cl4 C41 H41 108.7 . . ?
C8 N1 C15 110.4(5) . . ?
C8 N1 C7 123.6(6) . . ?
C15 N1 C7 125.6(5) . . ?
C25 O2 C17 108.1(5) . . ?
C37 O3 C38 117.2(5) . . ?

_refine_diff_density_max         0.846
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.180

####################################################################### 
# 
# 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_4t
_database_code_depnum_ccdc_archive 'CCDC 1523301'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C40 H26 N2 O4'
_chemical_formula_sum            'C40 H26 N2 O4'
_chemical_formula_weight         598.63

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'

_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                   22.5392(13)
_cell_length_b                   7.9506(5)
_cell_length_c                   23.0909(9)
_cell_angle_alpha                90
_cell_angle_beta                 120.813(4)
_cell_angle_gamma                90
_cell_volume                     3553.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      23.96

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            34729
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.052
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.856
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.856
_reflns_number_total             6053
_reflns_number_gt                3164
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1630P)²] 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         6053
_refine_ls_number_parameters     416
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.2685
_refine_ls_wR_factor_gt          0.2392
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      1.015
_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 0.1307(2) 0.2108(6) 0.7886(2) 0.0741(7) Uani 1 1 d . U . . .
H1 H 0.1686 0.2728 0.7949 0.089 Uiso 1 1 calc R U . . .
C2 C 0.0869(2) 0.1371(6) 0.7256(3) 0.0815(7) Uani 1 1 d . U . . .
H2 H 0.0950 0.1496 0.6901 0.098 Uiso 1 1 calc R U . . .
C3 C 0.0318(2) 0.0459(6) 0.7181(3) 0.0849(8) Uani 1 1 d . U . . .
H3 H 0.0030 -0.0088 0.6775 0.102 Uiso 1 1 calc R U . . .
C4 C 0.0186(2) 0.0342(6) 0.7692(3) 0.0832(8) Uani 1 1 d . U . . .
H4 H -0.0207 -0.0214 0.7625 0.100 Uiso 1 1 calc R U . . .
C5 C 0.0630(2) 0.1038(6) 0.8299(3) 0.0762(7) Uani 1 1 d . U . . .
H5 H 0.0547 0.0895 0.8651 0.091 Uiso 1 1 calc R U . . .
C6 C 0.1193(2) 0.1939(6) 0.8412(2) 0.0719(7) Uani 1 1 d . U . . .
C7 C 0.16636(18) 0.2694(5) 0.9100(2) 0.0566(10) Uani 1 1 d . . . . .
H7A H 0.1409 0.3554 0.9180 0.068 Uiso 1 1 calc R U . . .
H7B H 0.1784 0.1823 0.9436 0.068 Uiso 1 1 calc R U . . .
C8 C 0.23460(17) 0.5023(4) 0.89645(17) 0.0412(8) Uani 1 1 d . . . . .
C9 C 0.18340(19) 0.6167(5) 0.8604(2) 0.0574(10) Uani 1 1 d . . . . .
H9 H 0.1377 0.5921 0.8467 0.069 Uiso 1 1 calc R U . . .
C10 C 0.2008(2) 0.7688(5) 0.8447(2) 0.0615(10) Uani 1 1 d . . . . .
H10 H 0.1667 0.8477 0.8194 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2698(2) 0.8040(4) 0.8669(2) 0.0606(10) Uani 1 1 d . . . . .
H11 H 0.2814 0.9086 0.8575 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3211(2) 0.6881(4) 0.90237(18) 0.0496(9) Uani 1 1 d . . . . .
H12 H 0.3668 0.7121 0.9156 0.060 Uiso 1 1 calc R U . . .
C13 C 0.30376(17) 0.5365(4) 0.91790(16) 0.0394(7) Uani 1 1 d . . . . .
C14 C 0.34719(17) 0.3869(4) 0.95663(16) 0.0388(7) Uani 1 1 d . . . . .
C15 C 0.29355(18) 0.2730(4) 0.95944(17) 0.0452(8) Uani 1 1 d . . . . .
C16 C 0.41060(16) 0.4139(4) 1.02468(16) 0.0400(7) Uani 1 1 d . . . . .
C17 C 0.46494(17) 0.3374(4) 1.02682(17) 0.0420(8) Uani 1 1 d . . . . .
C18 C 0.44857(17) 0.2577(4) 0.96435(17) 0.0413(8) Uani 1 1 d . . . . .
C19 C 0.37731(17) 0.2884(4) 0.92072(16) 0.0408(8) Uani 1 1 d . . . . .
C20 C 0.3444(2) 0.2285(4) 0.85512(18) 0.0481(8) Uani 1 1 d . . . . .
H20 H 0.2979 0.2520 0.8258 0.058 Uiso 1 1 calc R U . . .
C21 C 0.3810(2) 0.1326(4) 0.8329(2) 0.0552(10) Uani 1 1 d . . . . .
C22 C 0.3448(3) 0.0655(6) 0.7617(2) 0.0831(15) Uani 1 1 d . . . . .
H22A H 0.3693 0.1009 0.7399 0.125 Uiso 1 1 calc R U . . .
H22B H 0.2985 0.1081 0.7373 0.125 Uiso 1 1 calc R U . . .
H22C H 0.3438 -0.0551 0.7627 0.125 Uiso 1 1 calc R U . . .
C23 C 0.4498(2) 0.1038(5) 0.8768(2) 0.0593(10) Uani 1 1 d . . . . .
H23 H 0.4743 0.0408 0.8620 0.071 Uiso 1 1 calc R U . . .
C24 C 0.4847(2) 0.1645(5) 0.9422(2) 0.0539(9) Uani 1 1 d . . . . .
H24 H 0.5315 0.1427 0.9707 0.065 Uiso 1 1 calc R U . . .
C25 C 0.28568(18) 0.5037(5) 1.0860(2) 0.0532(9) Uani 1 1 d . . . . .
H25 H 0.3017 0.4034 1.1097 0.064 Uiso 1 1 calc R U . . .
C26 C 0.2160(2) 0.5395(5) 1.0518(2) 0.0580(10) Uani 1 1 d . . . . .
H26 H 0.1848 0.4645 1.0526 0.070 Uiso 1 1 calc R U . . .
C27 C 0.19349(19) 0.6874(5) 1.01668(19) 0.0548(10) Uani 1 1 d . . . . .
C28 C 0.2374(2) 0.7997(5) 1.0147(2) 0.0596(10) Uani 1 1 d . . . . .
H28 H 0.2208 0.8997 0.9908 0.071 Uiso 1 1 calc R U . . .
C29 C 0.3076(2) 0.7643(5) 1.0487(2) 0.0535(9) Uani 1 1 d . . . . .
H29 H 0.3382 0.8398 1.0471 0.064 Uiso 1 1 calc R U . . .
C30 C 0.33188(17) 0.6172(4) 1.08497(16) 0.0391(8) Uani 1 1 d . . . . .
C31 C 0.40733(17) 0.5771(4) 1.12310(17) 0.0406(8) Uani 1 1 d . . . . .
C32 C 0.44998(18) 0.6224(4) 1.18802(17) 0.0453(8) Uani 1 1 d . . . . .
H32 H 0.4317 0.6861 1.2090 0.054 Uiso 1 1 calc R U . . .
C33 C 0.52014(18) 0.5795(4) 1.22579(17) 0.0482(9) Uani 1 1 d . . . . .
C34 C 0.5642(2) 0.6221(5) 1.2954(2) 0.0603(10) Uani 1 1 d . . . . .
H34 H 0.5462 0.6853 1.3168 0.072 Uiso 1 1 calc R U . . .
C35 C 0.6303(2) 0.5740(5) 1.3306(2) 0.0622(11) Uani 1 1 d . . . . .
H35 H 0.6570 0.5997 1.3762 0.075 Uiso 1 1 calc R U . . .
C36 C 0.6595(2) 0.4847(5) 1.2988(2) 0.0685(12) Uani 1 1 d . . . . .
H36 H 0.7059 0.4547 1.3233 0.082 Uiso 1 1 calc R U . . .
C37 C 0.62089(18) 0.4419(5) 1.23300(19) 0.0529(9) Uani 1 1 d . . . . .
H37 H 0.6412 0.3827 1.2129 0.063 Uiso 1 1 calc R U . . .
C38 C 0.55146(18) 0.4847(4) 1.19489(17) 0.0434(8) Uani 1 1 d . . . . .
C39 C 0.50556(17) 0.4428(4) 1.12702(17) 0.0401(8) Uani 1 1 d . . . . .
C40 C 0.43549(16) 0.4817(4) 1.08981(16) 0.0384(7) Uani 1 1 d . . . . .
N1 N 0.22990(14) 0.3437(3) 0.91967(15) 0.0478(7) Uani 1 1 d . . . . .
N2 N 0.1202(2) 0.7208(7) 0.9779(2) 0.0840(12) Uani 1 1 d . . . . .
O1 O 0.30431(14) 0.1417(3) 0.99064(13) 0.0585(7) Uani 1 1 d . . . . .
O2 O 0.0795(2) 0.6000(7) 0.9671(3) 0.1248(16) Uani 1 1 d . . . . .
O3 O 0.1013(2) 0.8616(6) 0.9579(3) 0.1290(17) Uani 1 1 d . . . . .
O4 O 0.52465(11) 0.3519(3) 1.08803(11) 0.0454(6) 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 C6 1.372(7) . ?
C1 C2 1.401(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(6) . ?
C7 N1 1.457(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.367(5) . ?
C8 N1 1.395(4) . ?
C8 C13 1.399(5) . ?
C9 C10 1.376(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.395(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.509(5) . ?
C14 C16 1.502(5) . ?
C14 C19 1.529(5) . ?
C14 C15 1.538(5) . ?
C15 O1 1.220(4) . ?
C15 N1 1.367(5) . ?
C16 C17 1.345(5) . ?
C16 C40 1.415(5) . ?
C17 O4 1.369(4) . ?
C17 C18 1.440(5) . ?
C18 C24 1.378(5) . ?
C18 C19 1.413(5) . ?
C19 C20 1.386(5) . ?
C20 C21 1.399(5) . ?
C20 H20 0.9300 . ?
C21 C23 1.370(6) . ?
C21 C22 1.509(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.384(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.378(5) . ?
C25 C30 1.387(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.351(6) . ?
C27 N2 1.445(5) . ?
C28 C29 1.389(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.378(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.495(5) . ?
C31 C32 1.351(5) . ?
C31 C40 1.438(5) . ?
C32 C33 1.402(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.431(5) . ?
C33 C38 1.446(5) . ?
C34 C35 1.337(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.404(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.352(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.388(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.406(5) . ?
C39 O4 1.384(4) . ?
C39 C40 1.392(4) . ?
N2 O3 1.202(6) . ?
N2 O2 1.262(6) . ?

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 C1 C2 121.8(5) . . ?
C6 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 117.6(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.4(5) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 C7 119.6(5) . . ?
C1 C6 C7 122.9(4) . . ?
N1 C7 C6 115.4(4) . . ?
N1 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 N1 129.0(3) . . ?
C9 C8 C13 121.8(3) . . ?
N1 C8 C13 109.2(3) . . ?
C8 C9 C10 118.7(4) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 C14 131.5(3) . . ?
C8 C13 C14 108.9(3) . . ?
C16 C14 C13 119.2(3) . . ?
C16 C14 C19 101.1(3) . . ?
C13 C14 C19 114.6(3) . . ?
C16 C14 C15 112.8(3) . . ?
C13 C14 C15 101.8(3) . . ?
C19 C14 C15 107.4(3) . . ?
O1 C15 N1 124.9(3) . . ?
O1 C15 C14 127.3(3) . . ?
N1 C15 C14 107.8(3) . . ?
C17 C16 C40 106.0(3) . . ?
C17 C16 C14 109.5(3) . . ?
C40 C16 C14 144.4(3) . . ?
C16 C17 O4 113.3(3) . . ?
C16 C17 C18 113.6(3) . . ?
O4 C17 C18 133.1(3) . . ?
C24 C18 C19 120.0(3) . . ?
C24 C18 C17 135.3(3) . . ?
C19 C18 C17 104.6(3) . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 C14 129.1(3) . . ?
C18 C19 C14 111.1(3) . . ?
C19 C20 C21 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C23 C21 C20 118.5(3) . . ?
C23 C21 C22 121.4(4) . . ?
C20 C21 C22 120.1(4) . . ?
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 . . ?
C21 C23 C24 122.9(3) . . ?
C21 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C18 C24 C23 118.6(4) . . ?
C18 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C26 C25 C30 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C30 C25 H25 120.0 . . ?
C27 C26 C25 119.0(4) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C28 C27 C26 122.1(3) . . ?
C28 C27 N2 118.8(4) . . ?
C26 C27 N2 119.0(4) . . ?
C27 C28 C29 119.3(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 119.9(4) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C25 119.6(3) . . ?
C29 C30 C31 121.1(3) . . ?
C25 C30 C31 119.3(3) . . ?
C32 C31 C40 118.4(3) . . ?
C32 C31 C30 123.0(3) . . ?
C40 C31 C30 118.5(3) . . ?
C31 C32 C33 124.1(3) . . ?
C31 C32 H32 118.0 . . ?
C33 C32 H32 118.0 . . ?
C32 C33 C34 123.6(4) . . ?
C32 C33 C38 120.0(3) . . ?
C34 C33 C38 116.4(3) . . ?
C35 C34 C33 122.1(4) . . ?
C35 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
C34 C35 C36 120.2(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C37 C36 C35 120.7(4) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 121.3(4) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C37 C38 C39 126.6(3) . . ?
C37 C38 C33 119.4(3) . . ?
C39 C38 C33 114.0(3) . . ?
O4 C39 C40 110.3(3) . . ?
O4 C39 C38 123.5(3) . . ?
C40 C39 C38 126.2(3) . . ?
C39 C40 C16 106.2(3) . . ?
C39 C40 C31 117.3(3) . . ?
C16 C40 C31 136.5(3) . . ?
C15 N1 C8 111.7(3) . . ?
C15 N1 C7 123.2(3) . . ?
C8 N1 C7 124.7(3) . . ?
O3 N2 O2 123.6(4) . . ?
O3 N2 C27 118.5(5) . . ?
O2 N2 C27 117.9(4) . . ?
C17 O4 C39 104.3(2) . . ?

_refine_diff_density_max         0.563
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 1523295'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-07-03 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         'C41 H29 N O2'
_chemical_formula_sum            'C41 H29 N O2'
_chemical_formula_weight         567.65

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'

_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                   11.3020(7)
_cell_length_b                   12.3396(7)
_cell_length_c                   13.4599(8)
_cell_angle_alpha                64.567(2)
_cell_angle_beta                 87.281(2)
_cell_angle_gamma                78.153(2)
_cell_volume                     1657.36(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7322
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_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            24584
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7557
_reflns_number_gt                4028
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1109P)²+0.1346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7557
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2239
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 1.0678(2) 0.3083(3) 0.0247(3) 0.0909(10) Uani 1 1 d . . . . .
H1A H 1.1391 0.2843 0.0726 0.109 Uiso 1 1 calc R U . . .
H1B H 1.0510 0.3970 -0.0145 0.109 Uiso 1 1 calc R U . . .
C2 C 1.0969(2) 0.2562(2) -0.0577(2) 0.0607(6) Uani 1 1 d . . . . .
C3 C 1.0344(2) 0.1774(3) -0.0706(2) 0.0772(8) Uani 1 1 d . . . . .
H3 H 0.9699 0.1547 -0.0262 0.093 Uiso 1 1 calc R U . . .
C4 C 1.0650(3) 0.1321(3) -0.1468(2) 0.0776(8) Uani 1 1 d . . . . .
H4 H 1.0214 0.0795 -0.1543 0.093 Uiso 1 1 calc R U . . .
C5 C 1.1600(3) 0.1643(3) -0.2121(2) 0.0880(9) Uani 1 1 d . . . . .
H5 H 1.1822 0.1328 -0.2634 0.106 Uiso 1 1 calc R U . . .
C6 C 1.2228(3) 0.2438(3) -0.2017(2) 0.0924(9) Uani 1 1 d . . . . .
H6 H 1.2873 0.2660 -0.2461 0.111 Uiso 1 1 calc R U . . .
C7 C 1.1907(2) 0.2895(2) -0.1267(2) 0.0688(7) Uani 1 1 d . . . . .
H7 H 1.2327 0.3445 -0.1216 0.083 Uiso 1 1 calc R U . . .
C8 C 0.9744(2) 0.1646(2) 0.1916(2) 0.0679(7) Uani 1 1 d . . . . .
C9 C 1.0733(3) 0.0679(4) 0.2371(4) 0.1043(12) Uani 1 1 d . . . . .
H9 H 1.1459 0.0662 0.2017 0.125 Uiso 1 1 calc R U . . .
C10 C 1.0577(5) -0.0269(4) 0.3393(4) 0.1272(18) Uani 1 1 d . . . . .
H10 H 1.1215 -0.0933 0.3728 0.153 Uiso 1 1 calc R U . . .
C11 C 0.9522(5) -0.0237(3) 0.3899(3) 0.1155(15) Uani 1 1 d . . . . .
H11 H 0.9448 -0.0886 0.4571 0.139 Uiso 1 1 calc R U . . .
C12 C 0.8543(3) 0.0735(2) 0.3451(2) 0.0811(8) Uani 1 1 d . . . . .
H12 H 0.7827 0.0754 0.3819 0.097 Uiso 1 1 calc R U . . .
C13 C 0.8667(2) 0.1677(2) 0.2438(2) 0.0598(6) Uani 1 1 d . . . . .
C14 C 0.85870(19) 0.3509(2) 0.08043(19) 0.0515(5) Uani 1 1 d . . . . .
C15 C 0.77944(18) 0.28606(19) 0.17564(17) 0.0482(5) Uani 1 1 d . . . . .
C16 C 0.67363(19) 0.2651(2) 0.12026(17) 0.0505(5) Uani 1 1 d . . . . .
C17 C 0.7030(2) 0.1851(2) 0.07113(18) 0.0552(6) Uani 1 1 d . . . . .
H17 H 0.7828 0.1434 0.0775 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6191(2) 0.1647(2) 0.01320(19) 0.0632(6) Uani 1 1 d . . . . .
C19 C 0.5004(2) 0.2284(2) 0.0043(2) 0.0696(7) Uani 1 1 d . . . . .
H19 H 0.4422 0.2174 -0.0351 0.083 Uiso 1 1 calc R U . . .
C20 C 0.4679(2) 0.3070(2) 0.0526(2) 0.0653(7) Uani 1 1 d . . . . .
H20 H 0.3875 0.3474 0.0459 0.078 Uiso 1 1 calc R U . . .
C21 C 0.5520(2) 0.3286(2) 0.11210(17) 0.0533(6) Uani 1 1 d . . . . .
C22 C 0.51613(19) 0.4094(2) 0.16633(17) 0.0527(6) Uani 1 1 d . . . . .
C23 C 0.4037(2) 0.4760(2) 0.16925(18) 0.0596(6) Uani 1 1 d . . . . .
H23 H 0.3391 0.4749 0.1295 0.071 Uiso 1 1 calc R U . . .
C24 C 0.38271(19) 0.5462(2) 0.23083(18) 0.0590(6) Uani 1 1 d . . . . .
C25 C 0.2650(2) 0.6154(2) 0.2318(2) 0.0710(7) Uani 1 1 d . . . . .
H25 H 0.2017 0.6165 0.1895 0.085 Uiso 1 1 calc R U . . .
C26 C 0.2445(3) 0.6791(3) 0.2931(2) 0.0801(8) Uani 1 1 d . . . . .
H26 H 0.1667 0.7219 0.2938 0.096 Uiso 1 1 calc R U . . .
C27 C 0.3377(3) 0.6818(3) 0.3554(2) 0.0772(8) Uani 1 1 d . . . . .
H27 H 0.3215 0.7265 0.3969 0.093 Uiso 1 1 calc R U . . .
C28 C 0.4524(2) 0.6195(2) 0.3563(2) 0.0670(7) Uani 1 1 d . . . . .
H28 H 0.5141 0.6222 0.3980 0.080 Uiso 1 1 calc R U . . .
C29 C 0.4774(2) 0.5515(2) 0.29435(18) 0.0559(6) Uani 1 1 d . . . . .
C30 C 0.59068(19) 0.4836(2) 0.28782(17) 0.0530(6) Uani 1 1 d . . . . .
C31 C 0.61027(19) 0.4183(2) 0.22610(17) 0.0511(5) Uani 1 1 d . . . . .
C32 C 0.73457(18) 0.36423(19) 0.23570(16) 0.0479(5) Uani 1 1 d . . . . .
C33 C 0.78661(19) 0.3998(2) 0.30346(17) 0.0499(5) Uani 1 1 d . . . . .
C34 C 0.90877(19) 0.38075(19) 0.34761(17) 0.0493(5) Uani 1 1 d . . . . .
C35 C 1.0104(2) 0.3670(2) 0.2901(2) 0.0654(7) Uani 1 1 d . . . . .
H35 H 1.0021 0.3696 0.2207 0.079 Uiso 1 1 calc R U . . .
C36 C 1.1245(2) 0.3494(3) 0.3341(2) 0.0709(7) Uani 1 1 d . . . . .
H36 H 1.1917 0.3386 0.2942 0.085 Uiso 1 1 calc R U . . .
C37 C 1.1412(2) 0.3474(2) 0.43555(19) 0.0610(6) Uani 1 1 d . . . . .
C38 C 1.0397(2) 0.3613(2) 0.49264(19) 0.0642(7) Uani 1 1 d . . . . .
H38 H 1.0485 0.3594 0.5618 0.077 Uiso 1 1 calc R U . . .
C39 C 0.9255(2) 0.3780(2) 0.45061(18) 0.0601(6) Uani 1 1 d . . . . .
H39 H 0.8587 0.3875 0.4914 0.072 Uiso 1 1 calc R U . . .
C40 C 1.2662(2) 0.3310(3) 0.4816(2) 0.0882(9) Uani 1 1 d . . . . .
H40A H 1.2678 0.3953 0.5035 0.132 Uiso 1 1 calc R U . . .
H40B H 1.3240 0.3343 0.4264 0.132 Uiso 1 1 calc R U . . .
H40C H 1.2862 0.2531 0.5444 0.132 Uiso 1 1 calc R U . . .
C41 C 0.6550(3) 0.0793(3) -0.0409(2) 0.0834(8) Uani 1 1 d . . . . .
H41A H 0.6005 0.0238 -0.0216 0.125 Uiso 1 1 d R U . . .
H41B H 0.7360 0.0336 -0.0163 0.125 Uiso 1 1 d R U . . .
H41C H 0.6515 0.1261 -0.1194 0.125 Uiso 1 1 d R U . . .
N1 N 0.96694(17) 0.2723(2) 0.09263(19) 0.0676(6) Uani 1 1 d . . . . .
O1 O 0.69872(13) 0.47238(14) 0.33732(11) 0.0552(4) Uani 1 1 d . . . . .
O2 O 0.83071(15) 0.45448(16) 0.00737(13) 0.0655(5) 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 N1 1.447(3) . ?
C1 C2 1.498(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.383(3) . ?
C2 C7 1.383(3) . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.357(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.378(4) . ?
C8 C9 1.393(4) . ?
C8 N1 1.411(3) . ?
C9 C10 1.404(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.347(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.514(3) . ?
C14 O2 1.219(3) . ?
C14 N1 1.363(3) . ?
C14 C15 1.546(3) . ?
C15 C32 1.507(3) . ?
C15 C16 1.559(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.419(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(4) . ?
C18 C41 1.503(4) . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.405(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.457(3) . ?
C22 C23 1.373(3) . ?
C22 C31 1.413(3) . ?
C23 C24 1.418(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.428(3) . ?
C24 C29 1.429(3) . ?
C25 C26 1.348(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.392(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.362(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.401(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.400(3) . ?
C30 C31 1.369(3) . ?
C30 O1 1.372(2) . ?
C31 C32 1.412(3) . ?
C32 C33 1.368(3) . ?
C33 O1 1.393(3) . ?
C33 C34 1.463(3) . ?
C34 C35 1.377(3) . ?
C34 C39 1.393(3) . ?
C35 C36 1.381(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.377(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.372(3) . ?
C37 C40 1.510(3) . ?
C38 C39 1.374(3) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?

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 C2 116.0(2) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C7 117.4(2) . . ?
C3 C2 C1 124.0(2) . . ?
C7 C2 C1 118.6(2) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C13 C8 C9 122.0(3) . . ?
C13 C8 N1 109.9(2) . . ?
C9 C8 N1 128.0(3) . . ?
C8 C9 C10 116.5(4) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 H9 121.8 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 122.1(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C8 C13 C12 120.3(2) . . ?
C8 C13 C15 109.1(2) . . ?
C12 C13 C15 130.5(2) . . ?
O2 C14 N1 125.5(2) . . ?
O2 C14 C15 126.4(2) . . ?
N1 C14 C15 108.1(2) . . ?
C32 C15 C13 114.11(17) . . ?
C32 C15 C14 110.41(17) . . ?
C13 C15 C14 101.57(18) . . ?
C32 C15 C16 112.06(17) . . ?
C13 C15 C16 112.42(17) . . ?
C14 C15 C16 105.40(16) . . ?
C17 C16 C21 119.13(19) . . ?
C17 C16 C15 117.27(19) . . ?
C21 C16 C15 123.5(2) . . ?
C18 C17 C16 123.0(2) . . ?
C18 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C17 C18 C19 117.5(2) . . ?
C17 C18 C41 121.4(2) . . ?
C19 C18 C41 121.0(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 122.1(2) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C16 117.1(2) . . ?
C20 C21 C22 121.9(2) . . ?
C16 C21 C22 120.98(19) . . ?
C23 C22 C31 115.7(2) . . ?
C23 C22 C21 129.1(2) . . ?
C31 C22 C21 115.13(19) . . ?
C22 C23 C24 122.1(2) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 C29 122.0(2) . . ?
C25 C24 C29 117.0(2) . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 125.8(2) . . ?
C30 C29 C24 113.9(2) . . ?
C28 C29 C24 120.2(2) . . ?
C31 C30 O1 108.69(19) . . ?
C31 C30 C29 123.6(2) . . ?
O1 C30 C29 127.7(2) . . ?
C30 C31 C32 108.65(19) . . ?
C30 C31 C22 122.6(2) . . ?
C32 C31 C22 128.7(2) . . ?
C33 C32 C31 105.77(19) . . ?
C33 C32 C15 135.25(19) . . ?
C31 C32 C15 118.98(18) . . ?
C32 C33 O1 109.94(18) . . ?
C32 C33 C34 136.2(2) . . ?
O1 C33 C34 113.88(18) . . ?
C35 C34 C39 117.5(2) . . ?
C35 C34 C33 122.4(2) . . ?
C39 C34 C33 120.1(2) . . ?
C34 C35 C36 121.0(2) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C37 C36 C35 121.6(2) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C38 C37 C36 117.3(2) . . ?
C38 C37 C40 121.5(2) . . ?
C36 C37 C40 121.2(2) . . ?
C37 C38 C39 121.9(2) . . ?
C37 C38 H38 119.0 . . ?
C39 C38 H38 119.0 . . ?
C38 C39 C34 120.7(2) . . ?
C38 C39 H39 119.6 . . ?
C34 C39 H39 119.6 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C18 C41 H41A 109.5 . . ?
C18 C41 H41B 109.4 . . ?
H41A C41 H41B 109.5 . . ?
C18 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C14 N1 C8 111.0(2) . . ?
C14 N1 C1 122.7(2) . . ?
C8 N1 C1 125.0(2) . . ?
C30 O1 C33 106.93(16) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042


