# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1c
_audit_block_doi                 10.5517/cc1knqlj
_database_code_depnum_ccdc_archive 'CCDC 1449888'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H30 Cl N3 O4'
_chemical_formula_sum            'C37 H30 Cl N3 O4'
_chemical_formula_weight         616.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.044(3)
_cell_length_b                   11.653(3)
_cell_length_c                   13.855(4)
_cell_angle_alpha                65.562(6)
_cell_angle_beta                 75.046(7)
_cell_angle_gamma                87.930(7)
_cell_volume                     1563.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2793
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      24.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   sadabs

_exptl_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15424
_diffrn_reflns_av_R_equivalents  0.1556
_diffrn_reflns_av_sigmaI/netI    0.2438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         24.71
_reflns_number_total             5158
_reflns_number_gt                2228
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1644P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5158
_refine_ls_number_parameters     415
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2478
_refine_ls_R_factor_gt           0.1046
_refine_ls_wR_factor_ref         0.3222
_refine_ls_wR_factor_gt          0.2610
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5101(8) 0.4117(6) -0.0838(7) 0.084(2) Uani 1 1 d . . .
H1 H 0.4392 0.3857 -0.0240 0.101 Uiso 1 1 calc R . .
C2 C 0.5202(11) 0.5293(7) -0.1726(8) 0.102(3) Uani 1 1 d . . .
H2 H 0.4534 0.5803 -0.1727 0.123 Uiso 1 1 calc R . .
C3 C 0.6202(14) 0.5695(9) -0.2551(9) 0.119(4) Uani 1 1 d . . .
H3 H 0.6231 0.6483 -0.3128 0.143 Uiso 1 1 calc R . .
C4 C 0.7238(11) 0.4971(11) -0.2594(8) 0.117(4) Uani 1 1 d . . .
H4 H 0.7964 0.5263 -0.3174 0.141 Uiso 1 1 calc R . .
C5 C 0.7116(8) 0.3778(8) -0.1711(6) 0.098(3) Uani 1 1 d . . .
H5 H 0.7780 0.3264 -0.1712 0.117 Uiso 1 1 calc R . .
C6 C 0.6078(6) 0.3351(6) -0.0868(5) 0.0561(17) Uani 1 1 d . . .
C7 C 0.5988(6) 0.2037(6) 0.0052(6) 0.0643(19) Uani 1 1 d . . .
H7A H 0.6055 0.1429 -0.0266 0.077 Uiso 1 1 calc R . .
H7B H 0.6711 0.1979 0.0341 0.077 Uiso 1 1 calc R . .
C8 C 0.4878(6) 0.1416(4) 0.1996(5) 0.0429(15) Uani 1 1 d . . .
C9 C 0.3588(5) 0.0949(5) 0.2730(5) 0.0396(14) Uani 1 1 d . . .
H9 H 0.3228 0.1649 0.2895 0.048 Uiso 1 1 calc R . .
C10 C 0.2915(6) 0.0785(4) 0.1971(5) 0.0420(15) Uani 1 1 d . . .
C11 C 0.1737(6) 0.0243(5) 0.2174(5) 0.0548(17) Uani 1 1 d . . .
H11 H 0.1178 -0.0072 0.2871 0.066 Uiso 1 1 calc R . .
C12 C 0.1427(7) 0.0190(6) 0.1291(6) 0.066(2) Uani 1 1 d . . .
C13 C 0.2219(7) 0.0651(6) 0.0255(6) 0.065(2) Uani 1 1 d . . .
H13 H 0.1961 0.0602 -0.0316 0.078 Uiso 1 1 calc R . .
C14 C 0.3399(7) 0.1188(5) 0.0053(5) 0.0571(18) Uani 1 1 d . . .
H14 H 0.3957 0.1503 -0.0645 0.068 Uiso 1 1 calc R . .
C15 C 0.3711(6) 0.1234(5) 0.0942(5) 0.0425(15) Uani 1 1 d . . .
C16 C 0.3445(5) -0.0181(4) 0.3818(5) 0.0393(15) Uani 1 1 d . . .
C17 C 0.2989(5) -0.0224(5) 0.4825(5) 0.0407(15) Uani 1 1 d . . .
C18 C 0.2480(5) 0.0736(4) 0.5209(5) 0.0400(14) Uani 1 1 d . A .
C19 C 0.1475(5) 0.1392(5) 0.4898(5) 0.0491(16) Uani 1 1 d . . .
H19 H 0.1100 0.1208 0.4444 0.059 Uiso 1 1 calc R . .
C20 C 0.1022(6) 0.2306(6) 0.5244(6) 0.0650(19) Uani 1 1 d . A .
H20 H 0.0349 0.2740 0.5021 0.078 Uiso 1 1 calc R . .
C21 C 0.1558(7) 0.2582(5) 0.5917(5) 0.0622(19) Uani 1 1 d D . .
C23 C 0.2538(7) 0.1932(6) 0.6241(6) 0.067(2) Uani 1 1 d . A .
H23 H 0.2898 0.2113 0.6705 0.080 Uiso 1 1 calc R . .
C24 C 0.3004(6) 0.1020(5) 0.5901(5) 0.0553(17) Uani 1 1 d . . .
H24 H 0.3674 0.0589 0.6133 0.066 Uiso 1 1 calc R A .
C25 C 0.0944(8) -0.2582(8) 0.8872(8) 0.094(3) Uani 1 1 d . . .
H25 H 0.1720 -0.2133 0.8647 0.112 Uiso 1 1 calc R . .
C26 C 0.0240(12) -0.2965(12) 0.9937(10) 0.142(4) Uani 1 1 d . . .
H26 H 0.0540 -0.2774 1.0427 0.170 Uiso 1 1 calc R . .
C27 C -0.0948(13) -0.3655(11) 1.0299(10) 0.135(5) Uani 1 1 d . . .
H27 H -0.1438 -0.3933 1.1022 0.162 Uiso 1 1 calc R . .
C28 C -0.1336(12) -0.3890(10) 0.9533(14) 0.135(4) Uani 1 1 d . . .
H28 H -0.2108 -0.4339 0.9741 0.162 Uiso 1 1 calc R . .
C29 C -0.0631(9) -0.3488(8) 0.8484(11) 0.106(3) Uani 1 1 d . . .
H29 H -0.0935 -0.3648 0.7981 0.128 Uiso 1 1 calc R . .
C30 C 0.0538(7) -0.2841(6) 0.8142(7) 0.069(2) Uani 1 1 d . . .
C31 C 0.1194(7) -0.2422(5) 0.6995(6) 0.0613(19) Uani 1 1 d . . .
C32 C 0.3802(5) -0.1424(5) 0.3922(5) 0.0394(14) Uani 1 1 d . . .
C33 C 0.3502(5) -0.2197(5) 0.5015(5) 0.0435(16) Uani 1 1 d . . .
C34 C 0.3588(6) -0.3598(4) 0.5529(5) 0.0590(18) Uani 1 1 d . . .
H34A H 0.2880 -0.3997 0.6169 0.071 Uiso 1 1 calc R . .
H34B H 0.4357 -0.3789 0.5760 0.071 Uiso 1 1 calc R . .
C35 C 0.3579(7) -0.4080(5) 0.4667(6) 0.064(2) Uani 1 1 d . . .
H35A H 0.3770 -0.4959 0.4933 0.077 Uiso 1 1 calc R . .
H35B H 0.2745 -0.4039 0.4554 0.077 Uiso 1 1 calc R . .
C36 C 0.4510(7) -0.3332(5) 0.3595(6) 0.0621(19) Uani 1 1 d . . .
H36A H 0.4413 -0.3627 0.3057 0.075 Uiso 1 1 calc R . .
H36B H 0.5351 -0.3490 0.3686 0.075 Uiso 1 1 calc R . .
C37 C 0.4387(6) -0.1897(5) 0.3140(6) 0.0499(16) Uani 1 1 d . . .
Cl1 Cl -0.0041(2) -0.0521(2) 0.15164(19) 0.1273(11) Uani 1 1 d . . .
N1 N 0.4892(4) 0.1667(4) 0.0948(4) 0.0432(12) Uani 1 1 d . . .
N2 N 0.2433(5) -0.1951(4) 0.6658(4) 0.0500(14) Uani 1 1 d . . .
H2A H 0.2814 -0.1958 0.7128 0.060 Uiso 1 1 calc R . .
N3 N 0.3043(5) -0.1471(4) 0.5562(4) 0.0464(13) Uani 1 1 d . . .
O1 O 0.5820(4) 0.1610(3) 0.2265(4) 0.0703(14) Uani 1 1 d . . .
O3 O 0.0734(5) -0.2517(5) 0.6310(5) 0.0960(18) Uani 1 1 d . . .
O4 O 0.4833(5) -0.1233(4) 0.2161(4) 0.0760(15) Uani 1 1 d . . .
O2 O 0.090(3) 0.352(3) 0.614(3) 0.086(4) Uani 0.479(9) 1 d PD A 1
C22 C 0.1147(18) 0.3703(16) 0.7027(14) 0.102(4) Uani 0.479(9) 1 d PD A 1
H22A H 0.0899 0.2936 0.7687 0.153 Uiso 0.479(9) 1 calc PR A 1
H22B H 0.0679 0.4373 0.7128 0.153 Uiso 0.479(9) 1 calc PR A 1
H22C H 0.2029 0.3920 0.6866 0.153 Uiso 0.479(9) 1 calc PR A 1
O2' O 0.132(2) 0.342(3) 0.641(2) 0.086(4) Uani 0.521(9) 1 d PD A 2
C22' C 0.0234(13) 0.4071(14) 0.6232(15) 0.102(4) Uani 0.521(9) 1 d PD A 2
H22D H 0.0358 0.4585 0.5460 0.153 Uiso 0.521(9) 1 calc PR A 2
H22E H 0.0083 0.4599 0.6623 0.153 Uiso 0.521(9) 1 calc PR A 2
H22F H -0.0475 0.3468 0.6495 0.153 Uiso 0.521(9) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(9) . ?
C1 C2 1.396(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.300(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.340(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.519(8) . ?
C7 N1 1.419(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.249(6) . ?
C8 N1 1.353(7) . ?
C8 C9 1.486(8) . ?
C9 C10 1.508(7) . ?
C9 C16 1.510(7) . ?
C9 H9 0.9800 . ?
C10 C15 1.360(8) . ?
C10 C11 1.377(7) . ?
C11 C12 1.378(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(10) . ?
C12 Cl1 1.742(7) . ?
C13 C14 1.375(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(8) . ?
C14 H14 0.9300 . ?
C15 N1 1.418(7) . ?
C16 C17 1.335(7) . ?
C16 C32 1.446(7) . ?
C17 N3 1.399(6) . ?
C17 C18 1.463(7) . ?
C18 C19 1.384(7) . ?
C18 C24 1.388(7) . ?
C19 C20 1.370(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(9) . ?
C20 H20 0.9300 . ?
C21 C23 1.363(9) . ?
C21 O2 1.389(5) . ?
C21 O2' 1.389(5) . ?
C23 C24 1.367(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.345(10) . ?
C25 C26 1.367(13) . ?
C25 H25 0.9300 . ?
C26 C27 1.423(16) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(15) . ?
C27 H27 0.9300 . ?
C28 C29 1.348(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.442(10) . ?
C31 O3 1.230(7) . ?
C31 N2 1.380(8) . ?
C32 C33 1.360(7) . ?
C32 C37 1.415(8) . ?
C33 N3 1.359(7) . ?
C33 C34 1.497(7) . ?
C34 C35 1.519(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.493(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.538(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 O4 1.223(7) . ?
N2 N3 1.367(6) . ?
N2 H2A 0.8600 . ?
O2 C22 1.418(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O2' C22' 1.418(5) . ?
C22' H22D 0.9600 . ?
C22' H22E 0.9600 . ?
C22' H22F 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
C6 C1 C2 118.4(8) . . ?
C6 C1 H1 120.8 . . ?
C2 C1 H1 120.8 . . ?
C3 C2 C1 121.9(10) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 121.7(10) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 116.0(10) . . ?
C3 C4 H4 122.0 . . ?
C5 C4 H4 122.0 . . ?
C6 C5 C4 122.5(9) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 119.4(7) . . ?
C5 C6 C7 120.1(7) . . ?
C1 C6 C7 120.4(6) . . ?
N1 C7 C6 117.3(5) . . ?
N1 C7 H7A 108.0 . . ?
C6 C7 H7A 108.0 . . ?
N1 C7 H7B 108.0 . . ?
C6 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
O1 C8 N1 123.3(6) . . ?
O1 C8 C9 126.8(5) . . ?
N1 C8 C9 109.9(5) . . ?
C8 C9 C10 102.0(5) . . ?
C8 C9 C16 118.1(4) . . ?
C10 C9 C16 115.3(4) . . ?
C8 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C16 C9 H9 106.9 . . ?
C15 C10 C11 120.2(5) . . ?
C15 C10 C9 108.4(5) . . ?
C11 C10 C9 131.3(6) . . ?
C10 C11 C12 116.6(6) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
C13 C12 C11 123.2(6) . . ?
C13 C12 Cl1 118.6(5) . . ?
C11 C12 Cl1 118.2(6) . . ?
C12 C13 C14 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 116.5(6) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
C10 C15 C14 123.2(6) . . ?
C10 C15 N1 110.1(5) . . ?
C14 C15 N1 126.6(6) . . ?
C17 C16 C32 108.6(5) . . ?
C17 C16 C9 127.6(4) . . ?
C32 C16 C9 123.8(5) . . ?
C16 C17 N3 106.3(4) . . ?
C16 C17 C18 132.2(5) . . ?
N3 C17 C18 121.5(5) . . ?
C19 C18 C24 117.7(5) . . ?
C19 C18 C17 121.8(5) . . ?
C24 C18 C17 120.5(5) . . ?
C20 C19 C18 121.4(5) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 120.0(6) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C23 C21 C20 119.2(5) . . ?
C23 C21 O2 133.4(9) . . ?
C20 C21 O2 107.4(9) . . ?
C23 C21 O2' 106.6(7) . . ?
C20 C21 O2' 134.1(8) . . ?
O2 C21 O2' 26.7(9) . . ?
C21 C23 C24 121.5(5) . . ?
C21 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C18 120.1(5) . . ?
C23 C24 H24 119.9 . . ?
C18 C24 H24 119.9 . . ?
C30 C25 C26 121.5(9) . . ?
C30 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C27 120.2(11) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 116.8(13) . . ?
C28 C27 H27 121.6 . . ?
C26 C27 H27 121.6 . . ?
C29 C28 C27 121.9(13) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 121.1(11) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C25 C30 C29 118.6(9) . . ?
C25 C30 C31 124.9(7) . . ?
C29 C30 C31 116.4(8) . . ?
O3 C31 N2 118.0(7) . . ?
O3 C31 C30 123.8(7) . . ?
N2 C31 C30 118.1(6) . . ?
C33 C32 C37 120.3(5) . . ?
C33 C32 C16 107.0(5) . . ?
C37 C32 C16 132.7(5) . . ?
N3 C33 C32 107.1(4) . . ?
N3 C33 C34 125.9(5) . . ?
C32 C33 C34 126.9(5) . . ?
C33 C34 C35 107.3(5) . . ?
C33 C34 H34A 110.3 . . ?
C35 C34 H34A 110.3 . . ?
C33 C34 H34B 110.3 . . ?
C35 C34 H34B 110.3 . . ?
H34A C34 H34B 108.5 . . ?
C36 C35 C34 112.1(5) . . ?
C36 C35 H35A 109.2 . . ?
C34 C35 H35A 109.2 . . ?
C36 C35 H35B 109.2 . . ?
C34 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C35 C36 C37 114.2(6) . . ?
C35 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
C35 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
O4 C37 C32 124.0(5) . . ?
O4 C37 C36 119.8(6) . . ?
C32 C37 C36 116.1(6) . . ?
C8 N1 C15 108.9(5) . . ?
C8 N1 C7 124.7(5) . . ?
C15 N1 C7 125.0(5) . . ?
N3 N2 C31 118.8(5) . . ?
N3 N2 H2A 120.6 . . ?
C31 N2 H2A 120.6 . . ?
C33 N3 N2 123.8(4) . . ?
C33 N3 C17 110.9(5) . . ?
N2 N3 C17 123.4(5) . . ?
C21 O2 C22 113.9(12) . . ?
C21 O2' C22' 112.6(10) . . ?
O2' C22' H22D 109.5 . . ?
O2' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
O2' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.03 2.853(6) 159.6 2_656

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_1g
_audit_block_doi                 10.5517/cc1knqmk
_database_code_depnum_ccdc_archive 'CCDC 1449889'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H34 Cl N3 O3'
_chemical_formula_sum            'C39 H34 Cl N3 O3'
_chemical_formula_weight         628.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   32.879(4)
_cell_length_b                   11.2887(13)
_cell_length_c                   22.666(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.793(3)
_cell_angle_gamma                90.00
_cell_volume                     6648.0(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8517
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.83

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2640
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs

_exptl_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33612
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.58
_reflns_number_total             7656
_reflns_number_gt                4172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1488P)²+0.5924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7656
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2574
_refine_ls_wR_factor_gt          0.2093
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42260(19) 0.7870(3) 0.9313(2) 0.0912(13) Uani 1 1 d . . .
H1 H 0.4091 0.7603 0.9550 0.109 Uiso 1 1 calc R . .
C2 C 0.4703(3) 0.8447(5) 0.9721(3) 0.134(2) Uani 1 1 d . . .
H2A H 0.4890 0.8548 1.0234 0.161 Uiso 1 1 calc R . .
C3 C 0.4894(2) 0.8864(5) 0.9368(5) 0.138(3) Uani 1 1 d . . .
H3 H 0.5206 0.9267 0.9641 0.166 Uiso 1 1 calc R . .
C4 C 0.4634(2) 0.8696(4) 0.8627(4) 0.1121(17) Uani 1 1 d . . .
H4 H 0.4769 0.8964 0.8392 0.134 Uiso 1 1 calc R . .
C5 C 0.41653(15) 0.8120(3) 0.8223(2) 0.0807(11) Uani 1 1 d . . .
H5 H 0.3985 0.8012 0.7713 0.097 Uiso 1 1 calc R . .
C6 C 0.39590(13) 0.7703(2) 0.85588(19) 0.0606(8) Uani 1 1 d . . .
C7 C 0.34433(12) 0.7112(3) 0.81068(17) 0.0595(8) Uani 1 1 d . . .
H7A H 0.3402 0.6703 0.8443 0.071 Uiso 1 1 calc R . .
H7B H 0.3179 0.7717 0.7849 0.071 Uiso 1 1 calc R . .
C8 C 0.35864(10) 0.5144(2) 0.77235(15) 0.0417(6) Uani 1 1 d . . .
C9 C 0.39382(11) 0.4628(3) 0.84108(16) 0.0514(7) Uani 1 1 d . . .
H9 H 0.4054 0.5018 0.8850 0.062 Uiso 1 1 calc R . .
C10 C 0.41128(12) 0.3503(3) 0.84218(19) 0.0628(8) Uani 1 1 d . . .
H10 H 0.4347 0.3132 0.8880 0.075 Uiso 1 1 calc R . .
C11 C 0.39521(12) 0.2916(3) 0.7780(2) 0.0636(9) Uani 1 1 d . . .
C12 C 0.41558(16) 0.1659(3) 0.7823(2) 0.0861(12) Uani 1 1 d . . .
H12A H 0.4433 0.1470 0.8333 0.129 Uiso 1 1 calc R . .
H12B H 0.4278 0.1633 0.7532 0.129 Uiso 1 1 calc R . .
H12C H 0.3883 0.1094 0.7629 0.129 Uiso 1 1 calc R . .
C13 C 0.35954(11) 0.3463(2) 0.70917(17) 0.0526(7) Uani 1 1 d . . .
H13 H 0.3483 0.3081 0.6652 0.063 Uiso 1 1 calc R . .
C14 C 0.34129(10) 0.4567(2) 0.70691(15) 0.0411(6) Uani 1 1 d . . .
C15 C 0.30352(9) 0.5363(2) 0.64274(14) 0.0410(6) Uani 1 1 d . . .
H15 H 0.2694 0.5026 0.6197 0.049 Uiso 1 1 calc R . .
C16 C 0.30669(10) 0.6495(2) 0.68215(16) 0.0437(6) Uani 1 1 d . . .
C17 C 0.30868(9) 0.5474(2) 0.58191(14) 0.0406(6) Uani 1 1 d . . .
C18 C 0.27063(9) 0.5275(2) 0.50862(14) 0.0385(6) Uani 1 1 d . . .
C19 C 0.21633(9) 0.4963(2) 0.47020(14) 0.0409(6) Uani 1 1 d . . .
C20 C 0.20386(11) 0.3903(2) 0.48726(17) 0.0519(7) Uani 1 1 d . . .
H20 H 0.2299 0.3378 0.5207 0.062 Uiso 1 1 calc R . .
C21 C 0.15375(12) 0.3627(3) 0.45535(19) 0.0616(8) Uani 1 1 d . . .
H21 H 0.1458 0.2924 0.4677 0.074 Uiso 1 1 calc R . .
C22 C 0.11582(11) 0.4386(3) 0.4056(2) 0.0630(9) Uani 1 1 d . . .
C23 C 0.12635(11) 0.5427(3) 0.3859(2) 0.0670(9) Uani 1 1 d . . .
H23 H 0.0998 0.5927 0.3505 0.080 Uiso 1 1 calc R . .
C24 C 0.17685(11) 0.5717(3) 0.41945(17) 0.0561(8) Uani 1 1 d . . .
H24 H 0.1845 0.6431 0.4077 0.067 Uiso 1 1 calc R . .
C25 C 0.20588(14) 0.3397(3) 0.2371(2) 0.0672(9) Uani 1 1 d . . .
H25 H 0.2039 0.2721 0.2587 0.081 Uiso 1 1 calc R . .
C26 C 0.18029(16) 0.3440(4) 0.1611(2) 0.0816(11) Uani 1 1 d . . .
H26 H 0.1608 0.2795 0.1315 0.098 Uiso 1 1 calc R . .
C27 C 0.18343(14) 0.4432(3) 0.12909(19) 0.0703(10) Uani 1 1 d . . .
H27 H 0.1660 0.4456 0.0778 0.084 Uiso 1 1 calc R . .
C28 C 0.21148(12) 0.5365(3) 0.17137(18) 0.0576(8) Uani 1 1 d . . .
H28 H 0.2135 0.6034 0.1493 0.069 Uiso 1 1 calc R . .
C29 C 0.23755(11) 0.5337(2) 0.24787(16) 0.0491(7) Uani 1 1 d . . .
H29 H 0.2573 0.5984 0.2771 0.059 Uiso 1 1 calc R . .
C30 C 0.23424(10) 0.4351(2) 0.28088(15) 0.0435(7) Uani 1 1 d . . .
C31 C 0.26163(11) 0.4286(2) 0.36300(16) 0.0455(7) Uani 1 1 d . . .
C32 C 0.35454(10) 0.5750(2) 0.58975(15) 0.0444(7) Uani 1 1 d . . .
C33 C 0.34223(10) 0.5669(2) 0.51975(15) 0.0448(7) Uani 1 1 d . . .
C34 C 0.37925(11) 0.5738(3) 0.50265(17) 0.0573(8) Uani 1 1 d . . .
H34A H 0.3767 0.6509 0.4817 0.069 Uiso 1 1 calc R . .
H34B H 0.3708 0.5140 0.4660 0.069 Uiso 1 1 calc R . .
C35 C 0.43352(10) 0.5546(3) 0.57297(17) 0.0569(8) Uani 1 1 d . . .
C36 C 0.47231(12) 0.5799(3) 0.5594(2) 0.0720(10) Uani 1 1 d . . .
H36A H 0.4681 0.5238 0.5242 0.108 Uiso 1 1 calc R . .
H36B H 0.5065 0.5735 0.6056 0.108 Uiso 1 1 calc R . .
H36C H 0.4670 0.6586 0.5398 0.108 Uiso 1 1 calc R . .
C37 C 0.43964(16) 0.4217(3) 0.5958(3) 0.0876(12) Uani 1 1 d . . .
H37A H 0.4342 0.3729 0.5568 0.131 Uiso 1 1 calc R . .
H37B H 0.4148 0.4019 0.6035 0.131 Uiso 1 1 calc R . .
H37C H 0.4737 0.4085 0.6411 0.131 Uiso 1 1 calc R . .
C38 C 0.44377(12) 0.6273(3) 0.63672(19) 0.0650(9) Uani 1 1 d . . .
H38A H 0.4435 0.7104 0.6256 0.078 Uiso 1 1 calc R . .
H38B H 0.4780 0.6087 0.6814 0.078 Uiso 1 1 calc R . .
C39 C 0.40590(11) 0.6093(3) 0.65329(17) 0.0556(8) Uani 1 1 d . . .
Cl1 Cl 0.05188(4) 0.40366(12) 0.36348(8) 0.1115(5) Uani 1 1 d . . .
N1 N 0.33629(8) 0.62716(18) 0.75608(13) 0.0434(6) Uani 1 1 d . . .
N2 N 0.26481(8) 0.53281(19) 0.39485(12) 0.0430(5) Uani 1 1 d . . .
H2B H 0.2500 0.5946 0.3674 0.052 Uiso 1 1 calc R . .
N3 N 0.29151(8) 0.54114(19) 0.47095(12) 0.0422(5) Uani 1 1 d . . .
O1 O 0.28436(8) 0.74293(17) 0.65228(12) 0.0614(6) Uani 1 1 d . . .
O2 O 0.28035(10) 0.33727(18) 0.39900(13) 0.0727(7) Uani 1 1 d . . .
O3 O 0.41775(8) 0.6272(2) 0.71471(12) 0.0778(8) 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 1.375(5) . ?
C1 C2 1.400(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.353(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(5) . ?
C7 N1 1.449(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.377(4) . ?
C8 C14 1.383(4) . ?
C8 N1 1.401(3) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C13 1.396(4) . ?
C11 C12 1.547(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.500(4) . ?
C15 C17 1.494(4) . ?
C15 C16 1.526(4) . ?
C15 H15 0.9800 . ?
C16 O1 1.225(3) . ?
C16 N1 1.349(3) . ?
C17 C18 1.352(3) . ?
C17 C32 1.440(3) . ?
C18 N3 1.394(3) . ?
C18 C19 1.471(3) . ?
C19 C24 1.379(4) . ?
C19 C20 1.394(4) . ?
C20 C21 1.369(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(4) . ?
C22 Cl1 1.740(3) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.371(4) . ?
C25 C26 1.378(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.340(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.492(4) . ?
C31 O2 1.221(3) . ?
C31 N2 1.351(3) . ?
C32 C33 1.379(4) . ?
C32 C39 1.447(4) . ?
C33 N3 1.352(3) . ?
C33 C34 1.489(4) . ?
C34 C35 1.512(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C38 1.510(4) . ?
C35 C36 1.511(4) . ?
C35 C37 1.559(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.519(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 O3 1.211(3) . ?
N2 N3 1.378(3) . ?
N2 H2B 0.8600 . ?

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 119.2(5) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 120.8(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 120.6(3) . . ?
N1 C7 C6 114.4(2) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C14 121.5(3) . . ?
C9 C8 N1 128.6(3) . . ?
C14 C8 N1 109.9(2) . . ?
C8 C9 C10 117.3(3) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C13 119.0(3) . . ?
C10 C11 C12 120.3(3) . . ?
C13 C11 C12 120.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C11 C13 H13 120.2 . . ?
C13 C14 C8 120.3(3) . . ?
C13 C14 C15 131.6(2) . . ?
C8 C14 C15 108.1(2) . . ?
C17 C15 C14 116.8(2) . . ?
C17 C15 C16 117.6(2) . . ?
C14 C15 C16 102.4(2) . . ?
C17 C15 H15 106.4 . . ?
C14 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
O1 C16 N1 125.4(2) . . ?
O1 C16 C15 126.5(3) . . ?
N1 C16 C15 108.0(2) . . ?
C18 C17 C32 107.4(2) . . ?
C18 C17 C15 125.2(2) . . ?
C32 C17 C15 127.4(2) . . ?
C17 C18 N3 107.6(2) . . ?
C17 C18 C19 129.8(2) . . ?
N3 C18 C19 122.6(2) . . ?
C24 C19 C20 118.3(2) . . ?
C24 C19 C18 121.7(2) . . ?
C20 C19 C18 119.9(2) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.6(3) . . ?
C21 C22 Cl1 120.0(2) . . ?
C23 C22 Cl1 118.4(3) . . ?
C22 C23 C24 118.8(3) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C30 C25 C26 120.0(3) . . ?
C30 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C25 C30 C29 119.0(3) . . ?
C25 C30 C31 119.1(3) . . ?
C29 C30 C31 121.8(2) . . ?
O2 C31 N2 122.4(3) . . ?
O2 C31 C30 123.2(2) . . ?
N2 C31 C30 114.4(2) . . ?
C33 C32 C17 107.3(2) . . ?
C33 C32 C39 120.2(2) . . ?
C17 C32 C39 132.5(2) . . ?
N3 C33 C32 107.5(2) . . ?
N3 C33 C34 126.4(2) . . ?
C32 C33 C34 125.8(3) . . ?
C33 C34 C35 110.1(2) . . ?
C33 C34 H34A 109.6 . . ?
C35 C34 H34A 109.6 . . ?
C33 C34 H34B 109.6 . . ?
C35 C34 H34B 109.6 . . ?
H34A C34 H34B 108.2 . . ?
C38 C35 C36 111.7(3) . . ?
C38 C35 C34 111.0(2) . . ?
C36 C35 C34 110.9(3) . . ?
C38 C35 C37 107.3(3) . . ?
C36 C35 C37 107.2(3) . . ?
C34 C35 C37 108.5(3) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 C39 115.3(3) . . ?
C35 C38 H38A 108.4 . . ?
C39 C38 H38A 108.4 . . ?
C35 C38 H38B 108.4 . . ?
C39 C38 H38B 108.4 . . ?
H38A C38 H38B 107.5 . . ?
O3 C39 C32 123.1(3) . . ?
O3 C39 C38 121.8(3) . . ?
C32 C39 C38 115.0(3) . . ?
C16 N1 C8 111.1(2) . . ?
C16 N1 C7 123.6(2) . . ?
C8 N1 C7 125.3(2) . . ?
C31 N2 N3 120.7(2) . . ?
C31 N2 H2B 119.7 . . ?
N3 N2 H2B 119.7 . . ?
C33 N3 N2 124.0(2) . . ?
C33 N3 C18 110.3(2) . . ?
N2 N3 C18 125.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O1 0.86 2.06 2.837(3) 150.7 7_566

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.150
####################################################################### 
# 
# 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_2d
_audit_block_doi                 10.5517/cc1knqnl
_database_code_depnum_ccdc_archive 'CCDC 1449890'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-18 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         'C34 H32 F N3 O5'
_chemical_formula_sum            'C34 H32 F N3 O5'
_chemical_formula_weight         581.62

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                   11.0558(8)
_cell_length_b                   11.4753(8)
_cell_length_c                   13.2262(9)
_cell_angle_alpha                113.324(2)
_cell_angle_beta                 103.927(2)
_cell_angle_gamma                94.490(2)
_cell_volume                     1466.93(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3538
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      24.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             612
_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    0.093
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_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            13175
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         27.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6747
_reflns_number_gt                3770
_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)+(0.0761P)²+0.6146P] 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         6747
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1882
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.4319(5) -0.0490(4) -0.1942(4) 0.1125(17) Uani 1 1 d . . . . .
H1A H 0.4036 -0.0905 -0.1514 0.169 Uiso 1 1 calc R U . . .
H1B H 0.5016 -0.0842 -0.2181 0.169 Uiso 1 1 calc R U . . .
H1C H 0.3634 -0.0635 -0.2609 0.169 Uiso 1 1 calc R U . . .
C2 C 0.4755(4) 0.0969(3) -0.1178(3) 0.0810(11) Uani 1 1 d . . . . .
H2A H 0.5462 0.1105 -0.0520 0.097 Uiso 1 1 calc R U . . .
H2B H 0.5059 0.1374 -0.1613 0.097 Uiso 1 1 calc R U . . .
C3 C 0.3766(4) 0.1609(3) -0.0762(3) 0.0716(10) Uani 1 1 d . . . . .
H3A H 0.3522 0.1256 -0.0267 0.086 Uiso 1 1 calc R U . . .
H3B H 0.3026 0.1392 -0.1419 0.086 Uiso 1 1 calc R U . . .
C4 C 0.4108(3) 0.3049(3) -0.0110(2) 0.0481(7) Uani 1 1 d . . . . .
H4A H 0.4263 0.3416 -0.0625 0.058 Uiso 1 1 calc R U . . .
H4B H 0.3391 0.3364 0.0136 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5177(3) 0.3700(2) 0.1965(2) 0.0405(6) Uani 1 1 d . . . . .
C6 C 0.6535(3) 0.4102(2) 0.2767(2) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.6752 0.3341 0.2879 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7286(2) 0.4309(2) 0.2023(2) 0.0347(6) Uani 1 1 d . . . . .
C8 C 0.8548(3) 0.4786(2) 0.2266(2) 0.0432(7) Uani 1 1 d . . . . .
H8 H 0.9113 0.5052 0.2997 0.052 Uiso 1 1 calc R U . . .
C9 C 0.8943(3) 0.4854(3) 0.1369(2) 0.0494(7) Uani 1 1 d . . . . .
C10 C 0.8153(3) 0.4474(3) 0.0283(2) 0.0493(7) Uani 1 1 d . . . . .
H10 H 0.8468 0.4539 -0.0288 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6879(3) 0.3990(2) 0.0037(2) 0.0439(7) Uani 1 1 d . . . . .
H11 H 0.6320 0.3722 -0.0698 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6466(3) 0.3920(2) 0.0923(2) 0.0367(6) Uani 1 1 d . . . . .
C13 C 0.6751(2) 0.5178(2) 0.3948(2) 0.0369(6) Uani 1 1 d . . . . .
C14 C 0.7245(3) 0.5108(2) 0.4966(2) 0.0373(6) Uani 1 1 d . . . . .
C15 C 0.7710(3) 0.4080(2) 0.5249(2) 0.0389(6) Uani 1 1 d . . . . .
C16 C 0.7236(3) 0.3661(3) 0.5959(2) 0.0496(7) Uani 1 1 d . . . . .
H16 H 0.6579 0.4003 0.6227 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7733(3) 0.2745(3) 0.6267(3) 0.0566(8) Uani 1 1 d . . . . .
H17 H 0.7407 0.2472 0.6740 0.068 Uiso 1 1 calc R U . . .
C18 C 0.8709(3) 0.2226(3) 0.5881(3) 0.0573(8) Uani 1 1 d . . . . .
C19 C 1.0470(5) 0.1307(4) 0.6416(4) 0.0999(15) Uani 1 1 d . . . . .
H19A H 1.0623 0.0951 0.5679 0.150 Uiso 1 1 calc R U . . .
H19B H 1.0711 0.0776 0.6810 0.150 Uiso 1 1 calc R U . . .
H19C H 1.0963 0.2168 0.6867 0.150 Uiso 1 1 calc R U . . .
C20 C 0.9168(3) 0.2600(3) 0.5152(3) 0.0577(8) Uani 1 1 d . . . . .
H20 H 0.9807 0.2236 0.4867 0.069 Uiso 1 1 calc R U . . .
C21 C 0.8668(3) 0.3522(3) 0.4851(2) 0.0474(7) Uani 1 1 d . . . . .
H21 H 0.8985 0.3778 0.4364 0.057 Uiso 1 1 calc R U . . .
C22 C 0.9046(3) 0.7465(3) 0.9405(2) 0.0582(8) Uani 1 1 d . . . . .
H22 H 0.8233 0.6959 0.9068 0.070 Uiso 1 1 calc R U . . .
C23 C 0.9614(4) 0.7869(4) 1.0559(3) 0.0721(10) Uani 1 1 d . . . . .
H23 H 0.9199 0.7627 1.1000 0.086 Uiso 1 1 calc R U . . .
C24 C 1.0809(4) 0.8640(4) 1.1060(3) 0.0765(11) Uani 1 1 d . . . . .
H24 H 1.1192 0.8932 1.1848 0.092 Uiso 1 1 calc R U . . .
C25 C 1.1427(3) 0.8977(3) 1.0430(3) 0.0741(10) Uani 1 1 d . . . . .
H25 H 1.2232 0.9501 1.0786 0.089 Uiso 1 1 calc R U . . .
C26 C 1.0879(3) 0.8549(3) 0.9252(3) 0.0576(8) Uani 1 1 d . . . . .
C27 C 0.9656(3) 0.7793(2) 0.8724(2) 0.0424(6) Uani 1 1 d . . . . .
C28 C 0.9082(3) 0.7362(3) 0.7477(2) 0.0437(7) Uani 1 1 d . . . . .
C29 C 0.6876(3) 0.7139(3) 0.5390(2) 0.0429(6) Uani 1 1 d . . . . .
C30 C 0.6851(3) 0.8521(3) 0.6061(3) 0.0621(9) Uani 1 1 d . . . . .
H30A H 0.6523 0.8612 0.6700 0.075 Uiso 1 1 calc R U . . .
H30B H 0.7707 0.9029 0.6373 0.075 Uiso 1 1 calc R U . . .
C31 C 0.6051(5) 0.8992(4) 0.5320(3) 0.1092(17) Uani 1 1 d . . . . .
H31A H 0.6327 0.9924 0.5654 0.131 Uiso 1 1 calc R U . . .
H31B H 0.5192 0.8829 0.5356 0.131 Uiso 1 1 calc R U . . .
C32 C 0.5989(4) 0.8491(3) 0.4106(3) 0.0782(11) Uani 1 1 d . . . . .
H32A H 0.6712 0.8966 0.4045 0.094 Uiso 1 1 calc R U . . .
H32B H 0.5230 0.8680 0.3703 0.094 Uiso 1 1 calc R U . . .
C33 C 0.5973(3) 0.7060(3) 0.3479(2) 0.0492(7) Uani 1 1 d . . . . .
C34 C 0.6512(3) 0.6463(2) 0.4212(2) 0.0398(6) Uani 1 1 d . . . . .
F1 F 1.01977(17) 0.53326(19) 0.15954(17) 0.0769(6) Uani 1 1 d . . . . .
N1 N 0.5224(2) 0.35088(19) 0.08990(17) 0.0382(5) Uani 1 1 d . . . . .
N2 N 0.7865(2) 0.6702(2) 0.70027(16) 0.0435(6) Uani 1 1 d . . . . .
H2 H 0.7456 0.6522 0.7416 0.052 Uiso 1 1 calc R U . . .
N3 N 0.7295(2) 0.6324(2) 0.58427(17) 0.0423(5) Uani 1 1 d . . . . .
O1 O 0.4204(2) 0.3517(2) 0.22149(16) 0.0610(6) Uani 1 1 d . . . . .
O2 O 0.9169(3) 0.1344(2) 0.6259(2) 0.0869(8) Uani 1 1 d . . . . .
O3 O 1.1556(2) 0.8878(3) 0.8655(2) 0.0931(9) Uani 1 1 d . . . . .
H3 H 1.1124 0.8609 0.7981 0.140 Uiso 1 1 calc R U . . .
O4 O 0.9667(2) 0.7570(2) 0.68651(18) 0.0681(6) Uani 1 1 d . . . . .
O5 O 0.5547(2) 0.6485(2) 0.24346(18) 0.0682(7) 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 1.535(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.461(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.495(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.459(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.226(3) . ?
C5 N1 1.353(3) . ?
C5 C6 1.525(4) . ?
C6 C7 1.503(3) . ?
C6 C13 1.506(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.370(4) . ?
C7 C12 1.388(3) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(4) . ?
C9 F1 1.366(3) . ?
C10 C11 1.382(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 N1 1.406(3) . ?
C13 C14 1.362(3) . ?
C13 C34 1.436(3) . ?
C14 N3 1.404(3) . ?
C14 C15 1.466(4) . ?
C15 C21 1.385(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 O2 1.376(4) . ?
C18 C20 1.380(4) . ?
C19 O2 1.409(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.369(4) . ?
C22 C27 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.341(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(5) . ?
C25 H25 0.9300 . ?
C26 O3 1.343(4) . ?
C26 C27 1.397(4) . ?
C27 C28 1.472(4) . ?
C28 O4 1.230(3) . ?
C28 N2 1.355(3) . ?
C29 N3 1.350(3) . ?
C29 C34 1.373(3) . ?
C29 C30 1.486(4) . ?
C30 C31 1.454(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.456(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.514(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 O5 1.217(3) . ?
C33 C34 1.442(4) . ?
N2 N3 1.380(3) . ?
N2 H2 0.8600 . ?
O3 H3 0.8200 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 114.2(3) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 116.1(3) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
N1 C4 C3 113.9(3) . . ?
N1 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 N1 125.0(3) . . ?
O1 C5 C6 126.6(2) . . ?
N1 C5 C6 108.3(2) . . ?
C7 C6 C13 117.7(2) . . ?
C7 C6 C5 102.04(19) . . ?
C13 C6 C5 115.9(2) . . ?
C7 C6 H6 106.8 . . ?
C13 C6 H6 106.8 . . ?
C5 C6 H6 106.8 . . ?
C8 C7 C12 120.2(2) . . ?
C8 C7 C6 131.4(2) . . ?
C12 C7 C6 108.4(2) . . ?
C7 C8 C9 116.8(3) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 H8 121.6 . . ?
C10 C9 F1 118.5(2) . . ?
C10 C9 C8 123.8(3) . . ?
F1 C9 C8 117.7(3) . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 C7 122.1(2) . . ?
C11 C12 N1 128.3(2) . . ?
C7 C12 N1 109.6(2) . . ?
C14 C13 C34 107.6(2) . . ?
C14 C13 C6 125.5(2) . . ?
C34 C13 C6 126.8(2) . . ?
C13 C14 N3 106.5(2) . . ?
C13 C14 C15 132.9(2) . . ?
N3 C14 C15 120.6(2) . . ?
C21 C15 C16 117.7(3) . . ?
C21 C15 C14 120.9(2) . . ?
C16 C15 C14 121.3(2) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
O2 C18 C17 116.7(3) . . ?
O2 C18 C20 123.6(3) . . ?
C17 C18 C20 119.7(3) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 119.2(3) . . ?
C18 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C15 122.2(3) . . ?
C20 C21 H21 118.9 . . ?
C15 C21 H21 118.9 . . ?
C23 C22 C27 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C27 C22 H22 119.2 . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 120.7(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
O3 C26 C25 118.3(3) . . ?
O3 C26 C27 122.1(3) . . ?
C25 C26 C27 119.7(3) . . ?
C22 C27 C26 117.9(3) . . ?
C22 C27 C28 123.1(2) . . ?
C26 C27 C28 119.0(3) . . ?
O4 C28 N2 119.8(3) . . ?
O4 C28 C27 122.5(3) . . ?
N2 C28 C27 117.7(2) . . ?
N3 C29 C34 107.5(2) . . ?
N3 C29 C30 125.6(2) . . ?
C34 C29 C30 127.0(3) . . ?
C31 C30 C29 109.8(3) . . ?
C31 C30 H30A 109.7 . . ?
C29 C30 H30A 109.7 . . ?
C31 C30 H30B 109.7 . . ?
C29 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C30 C31 C32 119.7(3) . . ?
C30 C31 H31A 107.4 . . ?
C32 C31 H31A 107.4 . . ?
C30 C31 H31B 107.4 . . ?
C32 C31 H31B 107.4 . . ?
H31A C31 H31B 106.9 . . ?
C31 C32 C33 117.4(3) . . ?
C31 C32 H32A 107.9 . . ?
C33 C32 H32A 107.9 . . ?
C31 C32 H32B 107.9 . . ?
C33 C32 H32B 107.9 . . ?
H32A C32 H32B 107.2 . . ?
O5 C33 C34 123.8(3) . . ?
O5 C33 C32 121.5(3) . . ?
C34 C33 C32 114.7(2) . . ?
C29 C34 C13 107.7(2) . . ?
C29 C34 C33 120.8(2) . . ?
C13 C34 C33 131.5(2) . . ?
C5 N1 C12 110.8(2) . . ?
C5 N1 C4 124.0(2) . . ?
C12 N1 C4 125.0(2) . . ?
C28 N2 N3 118.6(2) . . ?
C28 N2 H2 120.7 . . ?
N3 N2 H2 120.7 . . ?
C29 N3 N2 123.9(2) . . ?
C29 N3 C14 110.7(2) . . ?
N2 N3 C14 124.8(2) . . ?
C18 O2 C19 117.2(3) . . ?
C26 O3 H3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86 2.01 2.760(3) 145.1 2_666
O3 H3 O4 0.82 1.83 2.557(3) 146.7 .

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_3c
_audit_block_doi                 10.5517/cc1knqpm
_database_code_depnum_ccdc_archive 'CCDC 1449891'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H33 Cl N4 O4'
_chemical_formula_sum            'C38 H33 Cl N4 O4'
_chemical_formula_weight         645.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.589(3)
_cell_length_b                   12.379(3)
_cell_length_c                   13.886(4)
_cell_angle_alpha                113.673(7)
_cell_angle_beta                 103.852(7)
_cell_angle_gamma                101.755(7)
_cell_volume                     1667.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4341
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      21.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs

_exptl_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_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21940
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5830
_reflns_number_gt                3017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1273P)²+1.0205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5830
_refine_ls_number_parameters     400
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.26736(19) 1.41440(18) 0.43489(17) 0.0597(10) Uani 1 1 d G . .
C2 C 0.2767(3) 1.53119(19) 0.4417(2) 0.0710(14) Uani 1 1 d G . .
H2 H 0.2318 1.5775 0.4777 0.085 Uiso 1 1 calc R . .
C3 C 0.3532(3) 1.57881(18) 0.3947(2) 0.0789(16) Uani 1 1 d G . .
H3 H 0.3595 1.6569 0.3993 0.095 Uiso 1 1 calc R . .
C4 C 0.4203(2) 1.5096(2) 0.3409(2) 0.096(2) Uani 1 1 d G . .
H4 H 0.4715 1.5415 0.3095 0.115 Uiso 1 1 calc R . .
C5 C 0.4110(2) 1.3929(2) 0.3341(2) 0.0795(16) Uani 1 1 d G . .
H5 H 0.4559 1.3466 0.2981 0.095 Uiso 1 1 calc R . .
C6 C 0.33447(17) 1.34523(15) 0.38108(14) 0.0515(11) Uani 1 1 d G . .
C7 C 0.3189(2) 1.22398(15) 0.37555(13) 0.0503(11) Uani 1 1 d G . .
C8 C 0.2755(2) 1.04786(16) 0.49568(19) 0.0535(11) Uani 1 1 d G . .
C9 C 0.3940(2) 1.13235(18) 0.59503(18) 0.0679(14) Uani 1 1 d G . .
H9A H 0.3945 1.2181 0.6240 0.081 Uiso 1 1 calc R . .
H9B H 0.4664 1.1284 0.5721 0.081 Uiso 1 1 calc R . .
C10 C 0.4033(3) 1.0942(2) 0.6861(2) 0.0694(14) Uani 1 1 d G . .
C11 C 0.5345(3) 1.1613(3) 0.7755(2) 0.116(2) Uani 1 1 d G . .
H11A H 0.5951 1.1372 0.7426 0.174 Uiso 1 1 calc R . .
H11B H 0.5382 1.1391 0.8347 0.174 Uiso 1 1 calc R . .
H11C H 0.5533 1.2502 0.8060 0.174 Uiso 1 1 calc R . .
C12 C 0.3083(6) 1.1354(5) 0.7432(5) 0.0924(18) Uani 1 1 d . . .
H12A H 0.3354 1.2252 0.7832 0.139 Uiso 1 1 calc R . .
H12B H 0.3049 1.1027 0.7949 0.139 Uiso 1 1 calc R . .
H12C H 0.2260 1.1037 0.6866 0.139 Uiso 1 1 calc R . .
C13 C 0.3696(5) 0.9514(5) 0.6373(5) 0.0794(16) Uani 1 1 d . . .
H13A H 0.4388 0.9289 0.6165 0.095 Uiso 1 1 calc R . .
H13B H 0.3638 0.9303 0.6965 0.095 Uiso 1 1 calc R . .
C14 C 0.2487(4) 0.8712(4) 0.5360(4) 0.0580(12) Uani 1 1 d . . .
C15 C 0.2097(4) 0.9259(4) 0.4640(4) 0.0522(11) Uani 1 1 d . . .
C16 C -0.3207(5) 0.2910(4) 0.2448(5) 0.0751(15) Uani 1 1 d . . .
H16 H -0.2772 0.2668 0.2937 0.090 Uiso 1 1 calc R . .
C17 C -0.4339(6) 0.2093(6) 0.1622(6) 0.103(2) Uani 1 1 d . . .
H17 H -0.4696 0.1321 0.1576 0.124 Uiso 1 1 calc R . .
C18 C -0.4936(6) 0.2414(8) 0.0873(6) 0.110(2) Uani 1 1 d . . .
H18 H -0.5679 0.1835 0.0284 0.132 Uiso 1 1 calc R . .
C19 C -0.4477(8) 0.3573(9) 0.0958(6) 0.125(3) Uani 1 1 d . . .
H19 H -0.4909 0.3795 0.0451 0.150 Uiso 1 1 calc R . .
C20 C -0.3332(6) 0.4414(6) 0.1837(5) 0.0945(19) Uani 1 1 d . . .
H20 H -0.3003 0.5209 0.1916 0.113 Uiso 1 1 calc R . .
C21 C -0.2698(5) 0.4086(4) 0.2569(4) 0.0637(13) Uani 1 1 d . . .
C22 C -0.1471(5) 0.4956(4) 0.3496(4) 0.0649(13) Uani 1 1 d . . .
H22A H -0.1636 0.5448 0.4161 0.078 Uiso 1 1 calc R . .
H22B H -0.0986 0.4466 0.3678 0.078 Uiso 1 1 calc R . .
C23 C -0.0619(4) 0.7035(4) 0.3610(4) 0.0524(11) Uani 1 1 d . . .
C24 C 0.0067(4) 0.7536(3) 0.2986(4) 0.0495(11) Uani 1 1 d . . .
H24 H -0.0585 0.7568 0.2410 0.059 Uiso 1 1 calc R . .
C25 C 0.0483(4) 0.6464(4) 0.2364(3) 0.0495(11) Uani 1 1 d . . .
C26 C 0.1208(4) 0.6356(4) 0.1705(4) 0.0650(13) Uani 1 1 d . . .
H26 H 0.1580 0.7031 0.1613 0.078 Uiso 1 1 calc R . .
C27 C 0.1370(5) 0.5212(5) 0.1179(4) 0.0750(16) Uani 1 1 d . . .
C28 C 0.0824(6) 0.4213(5) 0.1302(5) 0.095(2) Uani 1 1 d . . .
H28 H 0.0941 0.3453 0.0930 0.114 Uiso 1 1 calc R . .
C29 C 0.0092(5) 0.4315(5) 0.1980(5) 0.0806(16) Uani 1 1 d . . .
H29 H -0.0276 0.3641 0.2075 0.097 Uiso 1 1 calc R . .
C30 C -0.0060(4) 0.5461(4) 0.2503(4) 0.0559(12) Uani 1 1 d . . .
C31 C 0.1023(4) 0.8807(4) 0.3642(3) 0.0451(10) Uani 1 1 d . . .
C32 C 0.1035(4) 0.9761(4) 0.3382(4) 0.0486(11) Uani 1 1 d . . .
C33 C 0.0177(4) 0.9854(4) 0.2473(4) 0.0554(12) Uani 1 1 d . . .
C34 C -0.0151(5) 0.8979(5) 0.1366(5) 0.0801(16) Uani 1 1 d . . .
H34 H 0.0170 0.8323 0.1190 0.096 Uiso 1 1 calc R . .
C35 C -0.0967(6) 0.9077(7) 0.0506(6) 0.107(2) Uani 1 1 d . . .
H35 H -0.1192 0.8467 -0.0235 0.128 Uiso 1 1 calc R . .
C36 C -0.1429(7) 1.0002(9) 0.0707(9) 0.113(2) Uani 1 1 d U . .
C37 C -0.2560(10) 1.0931(8) -0.0256(10) 0.192(4) Uani 1 1 d DU . .
H37A H -0.3062 1.1073 0.0211 0.288 Uiso 1 1 calc R . .
H37B H -0.3039 1.0790 -0.0989 0.288 Uiso 1 1 calc R . .
H37C H -0.1813 1.1652 0.0077 0.288 Uiso 1 1 calc R . .
C38 C -0.1135(6) 1.0884(6) 0.1791(8) 0.096(2) Uani 1 1 d . . .
H38 H -0.1460 1.1537 0.1940 0.116 Uiso 1 1 calc R . .
C39 C -0.0338(5) 1.0810(5) 0.2687(5) 0.0711(14) Uani 1 1 d . . .
H39 H -0.0157 1.1402 0.3426 0.085 Uiso 1 1 calc R . .
Cl1 Cl 0.22825(16) 0.50315(17) 0.03353(14) 0.1184(7) Uani 1 1 d . . .
N1 N 0.2435(3) 1.1946(3) 0.4269(3) 0.0541(10) Uani 1 1 d . . .
H1 H 0.2146 1.2494 0.4646 0.065 Uiso 1 1 calc R . .
N2 N 0.2114(3) 1.0780(3) 0.4206(3) 0.0493(9) Uani 1 1 d . . .
N3 N -0.0725(4) 0.5796(3) 0.3218(3) 0.0585(10) Uani 1 1 d . . .
O1 O 0.3723(4) 1.1557(3) 0.3290(3) 0.0832(11) Uani 1 1 d . . .
O2 O 0.1896(3) 0.7673(3) 0.5179(3) 0.0730(10) Uani 1 1 d . . .
O3 O -0.1069(3) 0.7586(3) 0.4276(3) 0.0704(10) Uani 1 1 d . . .
O4 O -0.2220(5) 0.9882(6) -0.0355(6) 0.166(2) Uani 1 1 d DU . .


_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
N4 C2 1.3900 . ?
N4 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.4428 . ?
C7 O1 1.217(4) . ?
C7 N1 1.335(4) . ?
C8 N2 1.353(4) . ?
C8 C15 1.375(4) . ?
C8 C9 1.4938 . ?
C9 C10 1.5064 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.5156 . ?
C10 C13 1.538(6) . ?
C10 C12 1.557(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.514(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O2 1.219(5) . ?
C14 C15 1.455(6) . ?
C15 C31 1.432(6) . ?
C16 C17 1.367(8) . ?
C16 C21 1.380(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.348(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.406(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.492(7) . ?
C22 N3 1.448(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O3 1.209(5) . ?
C23 N3 1.373(5) . ?
C23 C24 1.526(6) . ?
C24 C31 1.480(6) . ?
C24 C25 1.510(6) . ?
C24 H24 0.9800 . ?
C25 C26 1.370(6) . ?
C25 C30 1.381(6) . ?
C26 C27 1.385(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.364(8) . ?
C27 Cl1 1.739(5) . ?
C28 C29 1.396(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(6) . ?
C29 H29 0.9300 . ?
C30 N3 1.384(5) . ?
C31 C32 1.364(6) . ?
C32 N2 1.406(5) . ?
C32 C33 1.469(6) . ?
C33 C34 1.377(7) . ?
C33 C39 1.391(6) . ?
C34 C35 1.399(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.319(10) . ?
C35 H35 0.9300 . ?
C36 C38 1.363(10) . ?
C36 O4 1.470(9) . ?
C37 O4 1.397(5) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.410(8) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
N1 N2 1.376(4) . ?
N1 H1 0.8600 . ?

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 N4 C6 120.0 . . ?
N4 C2 C3 120.0 . . ?
N4 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 N4 120.0 . . ?
C5 C6 C7 122.9 . . ?
N4 C6 C7 117.1 . . ?
O1 C7 N1 123.3(2) . . ?
O1 C7 C6 122.06(19) . . ?
N1 C7 C6 114.61(16) . . ?
N2 C8 C15 107.0(3) . . ?
N2 C8 C9 126.21(15) . . ?
C15 C8 C9 126.8(2) . . ?
C8 C9 C10 110.5 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 110.3 . . ?
C9 C10 C13 111.3(2) . . ?
C11 C10 C13 110.6(2) . . ?
C9 C10 C12 108.1(2) . . ?
C11 C10 C12 107.7(3) . . ?
C13 C10 C12 108.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C10 116.7(4) . . ?
C14 C13 H13A 108.1 . . ?
C10 C13 H13A 108.1 . . ?
C14 C13 H13B 108.1 . . ?
C10 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
O2 C14 C15 123.3(4) . . ?
O2 C14 C13 120.8(4) . . ?
C15 C14 C13 115.9(4) . . ?
C8 C15 C31 108.0(3) . . ?
C8 C15 C14 119.6(4) . . ?
C31 C15 C14 132.0(4) . . ?
C17 C16 C21 121.1(6) . . ?
C17 C16 H16 119.4 . . ?
C21 C16 H16 119.4 . . ?
C18 C17 C16 119.5(6) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.7(7) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 117.8(7) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
C21 C20 C19 121.1(6) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 118.7(5) . . ?
C20 C21 C22 122.0(5) . . ?
C16 C21 C22 119.3(5) . . ?
N3 C22 C21 113.3(4) . . ?
N3 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
N3 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
O3 C23 N3 125.1(4) . . ?
O3 C23 C24 127.2(4) . . ?
N3 C23 C24 107.5(4) . . ?
C31 C24 C25 117.8(3) . . ?
C31 C24 C23 117.7(3) . . ?
C25 C24 C23 102.1(3) . . ?
C31 C24 H24 106.1 . . ?
C25 C24 H24 106.1 . . ?
C23 C24 H24 106.1 . . ?
C26 C25 C30 120.8(4) . . ?
C26 C25 C24 131.0(4) . . ?
C30 C25 C24 108.1(4) . . ?
C25 C26 C27 117.9(5) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C28 C27 C26 121.6(5) . . ?
C28 C27 Cl1 118.8(4) . . ?
C26 C27 Cl1 119.6(5) . . ?
C27 C28 C29 120.9(5) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 117.0(5) . . ?
C30 C29 H29 121.5 . . ?
C28 C29 H29 121.5 . . ?
C29 C30 C25 121.7(4) . . ?
C29 C30 N3 127.9(4) . . ?
C25 C30 N3 110.4(3) . . ?
C32 C31 C15 107.8(4) . . ?
C32 C31 C24 125.1(4) . . ?
C15 C31 C24 127.1(4) . . ?
C31 C32 N2 106.1(4) . . ?
C31 C32 C33 132.4(4) . . ?
N2 C32 C33 121.5(4) . . ?
C34 C33 C39 117.5(5) . . ?
C34 C33 C32 120.4(4) . . ?
C39 C33 C32 122.1(4) . . ?
C33 C34 C35 120.0(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 122.5(7) . . ?
C36 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C35 C36 C38 119.4(7) . . ?
C35 C36 O4 110.3(9) . . ?
C38 C36 O4 130.2(8) . . ?
O4 C37 H37A 109.5 . . ?
O4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 C39 120.1(6) . . ?
C36 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C33 C39 C38 120.4(5) . . ?
C33 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C7 N1 N2 121.1(3) . . ?
C7 N1 H1 119.4 . . ?
N2 N1 H1 119.4 . . ?
C8 N2 N1 124.7(3) . . ?
C8 N2 C32 111.0(3) . . ?
N1 N2 C32 124.2(4) . . ?
C23 N3 C30 111.1(4) . . ?
C23 N3 C22 123.7(4) . . ?
C30 N3 C22 125.2(4) . . ?
C37 O4 C36 114.9(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.86 2.18 2.809(5) 129.3 2_576

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.055
#===================================================
