# 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_1b
_audit_block_doi                 10.5517/cc11npq3
_database_code_depnum_ccdc_archive 'CCDC 973205'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H29 N3 O3'
_chemical_formula_sum            'C37 H29 N3 O3'
_chemical_formula_weight         563.63

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'

_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                   9.4485(9)
_cell_length_b                   12.2794(12)
_cell_length_c                   12.7142(12)
_cell_angle_alpha                101.186(3)
_cell_angle_beta                 96.606(3)
_cell_angle_gamma                94.608(3)
_cell_volume                     1429.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8164
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.980
_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            28848
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_min       -11
_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         2.11
_diffrn_reflns_theta_max         27.56
_reflns_number_total             6605
_reflns_number_gt                4097
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0432P)²+0.4727P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6571
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.2080(3) -0.1782(2) 0.12397(19) 0.0640(6) Uani 1 1 d . . .
H1 H 0.1899 -0.1053 0.1217 0.077 Uiso 1 1 calc R . .
C2 C 0.1375(3) -0.2654(3) 0.0454(2) 0.0828(8) Uani 1 1 d . . .
H2 H 0.0723 -0.2506 -0.0094 0.099 Uiso 1 1 calc R . .
C3 C 0.1625(3) -0.3730(2) 0.0471(2) 0.0824(8) Uani 1 1 d . . .
H3 H 0.1153 -0.4313 -0.0065 0.099 Uiso 1 1 calc R . .
C4 C 0.2570(3) -0.3945(2) 0.1280(2) 0.0769(8) Uani 1 1 d . . .
H4 H 0.2735 -0.4676 0.1303 0.092 Uiso 1 1 calc R . .
C5 C 0.3278(3) -0.30796(18) 0.20601(19) 0.0621(6) Uani 1 1 d . . .
H5 H 0.3928 -0.3235 0.2604 0.075 Uiso 1 1 calc R . .
C6 C 0.3047(2) -0.19841(16) 0.20556(15) 0.0434(5) Uani 1 1 d . . .
C7 C 0.3848(2) -0.10811(15) 0.29499(17) 0.0492(5) Uani 1 1 d . . .
H7A H 0.3675 -0.1259 0.3638 0.059 Uiso 1 1 calc R . .
H7B H 0.4865 -0.1091 0.2908 0.059 Uiso 1 1 calc R . .
C8 C 0.2653(2) 0.05803(15) 0.36460(15) 0.0387(4) Uani 1 1 d . . .
C9 C 0.26595(19) 0.18013(14) 0.35011(14) 0.0360(4) Uani 1 1 d . . .
C10 C 0.3689(2) 0.18444(15) 0.26754(15) 0.0394(4) Uani 1 1 d . . .
C11 C 0.4276(2) 0.27124(18) 0.22721(17) 0.0496(5) Uani 1 1 d . . .
H11 H 0.4009 0.3428 0.2475 0.059 Uiso 1 1 calc R . .
C12 C 0.5275(2) 0.2503(2) 0.1557(2) 0.0647(6) Uani 1 1 d . . .
H12 H 0.5685 0.3086 0.1284 0.078 Uiso 1 1 calc R . .
C13 C 0.5665(3) 0.1447(2) 0.1249(2) 0.0708(7) Uani 1 1 d . . .
H13 H 0.6321 0.1322 0.0758 0.085 Uiso 1 1 calc R . .
C14 C 0.5099(3) 0.0565(2) 0.16566(19) 0.0642(6) Uani 1 1 d . . .
H14 H 0.5363 -0.0150 0.1448 0.077 Uiso 1 1 calc R . .
C15 C 0.4131(2) 0.07854(16) 0.23819(16) 0.0448(5) Uani 1 1 d . . .
C16 C 0.11076(19) 0.20593(14) 0.31904(14) 0.0344(4) Uani 1 1 d . . .
H16 H 0.0551 0.1936 0.3769 0.041 Uiso 1 1 calc R . .
C17 C 0.0405(2) 0.12813(15) 0.21404(14) 0.0370(4) Uani 1 1 d . . .
C18 C -0.06169(19) 0.03079(15) 0.21456(14) 0.0361(4) Uani 1 1 d . . .
C19 C -0.1050(2) 0.00196(16) 0.30781(15) 0.0410(5) Uani 1 1 d . . .
H19 H -0.0751 0.0493 0.3745 0.049 Uiso 1 1 calc R . .
C20 C -0.1906(2) -0.09484(16) 0.30270(16) 0.0454(5) Uani 1 1 d . . .
H20 H -0.2191 -0.1124 0.3656 0.054 Uiso 1 1 calc R . .
C21 C -0.2347(2) -0.16670(16) 0.20391(17) 0.0458(5) Uani 1 1 d . . .
C22 C -0.3418(3) -0.3483(2) 0.1122(2) 0.0908(9) Uani 1 1 d . . .
H22A H -0.4060 -0.3237 0.0596 0.136 Uiso 1 1 calc R . .
H22B H -0.3849 -0.4154 0.1286 0.136 Uiso 1 1 calc R . .
H22C H -0.2539 -0.3627 0.0837 0.136 Uiso 1 1 calc R . .
C23 C -0.1997(2) -0.13780(17) 0.10994(16) 0.0503(5) Uani 1 1 d . . .
H23 H -0.2334 -0.1839 0.0432 0.060 Uiso 1 1 calc R . .
C24 C -0.1144(2) -0.04022(17) 0.11600(15) 0.0457(5) Uani 1 1 d . . .
H24 H -0.0912 -0.0209 0.0524 0.055 Uiso 1 1 calc R . .
C25 C 0.3242(2) 0.25689(15) 0.45739(15) 0.0396(4) Uani 1 1 d . . .
C26 C 0.2842(2) 0.37275(15) 0.47312(15) 0.0396(4) Uani 1 1 d . . .
C27 C 0.3553(2) 0.43894(16) 0.57391(17) 0.0508(5) Uani 1 1 d . . .
C28 C 0.1917(2) 0.41031(14) 0.40152(15) 0.0372(4) Uani 1 1 d . . .
C29 C 0.10607(19) 0.32779(14) 0.30801(14) 0.0361(4) Uani 1 1 d . . .
H29 H 0.1458 0.3365 0.2419 0.043 Uiso 1 1 calc R . .
C30 C -0.0499(2) 0.35406(16) 0.29564(18) 0.0496(5) Uani 1 1 d . . .
H30A H -0.1054 0.2994 0.2370 0.060 Uiso 1 1 calc R . .
H30B H -0.0903 0.3497 0.3617 0.060 Uiso 1 1 calc R . .
C31 C -0.0583(3) 0.46957(18) 0.2722(2) 0.0614(6) Uani 1 1 d . . .
H31A H -0.0356 0.4692 0.1997 0.074 Uiso 1 1 calc R . .
H31B H -0.1556 0.4889 0.2747 0.074 Uiso 1 1 calc R . .
C32 C 0.0417(2) 0.55625(16) 0.35084(18) 0.0509(5) Uani 1 1 d . . .
C33 C 0.0160(3) 0.66782(19) 0.3625(2) 0.0647(7) Uani 1 1 d . . .
H33 H -0.0666 0.6857 0.3251 0.078 Uiso 1 1 calc R . .
C34 C 0.1087(3) 0.75183(19) 0.4275(2) 0.0688(7) Uani 1 1 d . . .
H34 H 0.0884 0.8256 0.4347 0.083 Uiso 1 1 calc R . .
C35 C 0.2316(3) 0.72667(17) 0.4817(2) 0.0645(7) Uani 1 1 d . . .
H35 H 0.2961 0.7836 0.5246 0.077 Uiso 1 1 calc R . .
C36 C 0.2601(3) 0.61677(16) 0.47298(17) 0.0532(5) Uani 1 1 d . . .
H36 H 0.3443 0.6008 0.5097 0.064 Uiso 1 1 calc R . .
C37 C 0.1644(2) 0.52899(15) 0.40992(16) 0.0432(5) Uani 1 1 d . . .
N1 N 0.34773(18) 0.00439(13) 0.29390(13) 0.0452(4) Uani 1 1 d . . .
N2 N 0.4067(2) 0.21938(16) 0.52450(16) 0.0622(5) Uani 1 1 d . . .
N3 N 0.4154(2) 0.47935(16) 0.65704(17) 0.0748(6) Uani 1 1 d . . .
O1 O 0.20074(15) 0.01656(11) 0.42652(11) 0.0487(4) Uani 1 1 d . . .
O2 O 0.07533(16) 0.14727(12) 0.12926(10) 0.0542(4) Uani 1 1 d . . .
O3 O -0.31286(18) -0.26391(12) 0.20819(13) 0.0670(5) Uani 1 1 d . . .
H2A H 0.440(3) 0.273(2) 0.585(2) 0.098(10) Uiso 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(3) . ?
C1 C2 1.380(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 N1 1.454(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.211(2) . ?
C8 N1 1.365(2) . ?
C8 C9 1.545(2) . ?
C9 C25 1.516(2) . ?
C9 C10 1.516(3) . ?
C9 C16 1.548(2) . ?
C10 C11 1.375(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.404(3) . ?
C16 C17 1.528(2) . ?
C16 C29 1.533(2) . ?
C16 H16 0.9800 . ?
C17 O2 1.222(2) . ?
C17 C18 1.477(3) . ?
C18 C24 1.393(2) . ?
C18 C19 1.396(3) . ?
C19 C20 1.369(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9300 . ?
C21 O3 1.366(2) . ?
C21 C23 1.378(3) . ?
C22 O3 1.423(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.267(2) . ?
C25 C26 1.483(3) . ?
C26 C28 1.360(3) . ?
C26 C27 1.437(3) . ?
C27 N3 1.140(3) . ?
C28 C37 1.486(3) . ?
C28 C29 1.508(2) . ?
C29 C30 1.531(3) . ?
C29 H29 0.9800 . ?
C30 C31 1.511(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.495(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.393(3) . ?
C32 C37 1.407(3) . ?
C33 C34 1.368(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.401(3) . ?
C36 H36 0.9300 . ?
N2 H2A 0.92(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
C6 C1 C2 120.5(2) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 123.75(18) . . ?
C5 C6 C7 118.42(18) . . ?
N1 C7 C6 115.49(16) . . ?
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 . . ?
O1 C8 N1 125.91(17) . . ?
O1 C8 C9 125.98(17) . . ?
N1 C8 C9 108.10(16) . . ?
C25 C9 C10 111.20(15) . . ?
C25 C9 C8 108.58(14) . . ?
C10 C9 C8 102.08(14) . . ?
C25 C9 C16 107.53(14) . . ?
C10 C9 C16 117.32(15) . . ?
C8 C9 C16 109.79(14) . . ?
C11 C10 C15 119.55(18) . . ?
C11 C10 C9 132.04(17) . . ?
C15 C10 C9 108.23(16) . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 127.75(19) . . ?
C10 C15 N1 110.34(17) . . ?
C17 C16 C29 109.77(14) . . ?
C17 C16 C9 111.19(14) . . ?
C29 C16 C9 111.49(14) . . ?
C17 C16 H16 108.1 . . ?
C29 C16 H16 108.1 . . ?
C9 C16 H16 108.1 . . ?
O2 C17 C18 120.88(16) . . ?
O2 C17 C16 117.55(16) . . ?
C18 C17 C16 121.53(16) . . ?
C24 C18 C19 117.31(17) . . ?
C24 C18 C17 118.18(17) . . ?
C19 C18 C17 124.45(16) . . ?
C20 C19 C18 121.14(17) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.04(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
O3 C21 C23 124.42(18) . . ?
O3 C21 C20 115.50(19) . . ?
C23 C21 C20 120.08(18) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 119.26(18) . . ?
C24 C23 H23 120.4 . . ?
C21 C23 H23 120.4 . . ?
C23 C24 C18 121.99(19) . . ?
C23 C24 H24 119.0 . . ?
C18 C24 H24 119.0 . . ?
N2 C25 C26 125.11(17) . . ?
N2 C25 C9 118.28(17) . . ?
C26 C25 C9 116.55(16) . . ?
C28 C26 C27 124.92(17) . . ?
C28 C26 C25 124.14(16) . . ?
C27 C26 C25 110.94(17) . . ?
N3 C27 C26 171.6(2) . . ?
C26 C28 C37 124.46(17) . . ?
C26 C28 C29 119.31(15) . . ?
C37 C28 C29 116.21(16) . . ?
C28 C29 C30 109.76(15) . . ?
C28 C29 C16 113.49(15) . . ?
C30 C29 C16 109.36(15) . . ?
C28 C29 H29 108.0 . . ?
C30 C29 H29 108.0 . . ?
C16 C29 H29 108.0 . . ?
C31 C30 C29 110.29(17) . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30B 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
C32 C31 C30 112.46(18) . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C37 119.0(2) . . ?
C33 C32 C31 119.0(2) . . ?
C37 C32 C31 121.90(17) . . ?
C34 C33 C32 121.9(2) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 119.6(2) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 121.3(2) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C36 C37 C32 117.91(18) . . ?
C36 C37 C28 122.03(19) . . ?
C32 C37 C28 120.03(18) . . ?
C8 N1 C15 111.08(15) . . ?
C8 N1 C7 122.65(17) . . ?
C15 N1 C7 125.06(17) . . ?
C25 N2 H2A 111.8(18) . . ?
C21 O3 C22 117.96(19) . . ?

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 N3 0.92(3) 2.56(3) 3.298(3) 138(2) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.230
_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_1c
_audit_block_doi                 10.5517/cc11npr4
_database_code_depnum_ccdc_archive 'CCDC 973206'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H29 N3 O2, C H2 Cl2'
_chemical_formula_sum            'C38 H31 Cl2 N3 O2'
_chemical_formula_weight         632.56

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                   11.1264(14)
_cell_length_b                   12.6065(15)
_cell_length_c                   13.9086(18)
_cell_angle_alpha                115.208(3)
_cell_angle_beta                 104.177(4)
_cell_angle_gamma                100.747(4)
_cell_volume                     1614.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.953
_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            33994
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.54
_reflns_number_total             7416
_reflns_number_gt                4873
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0909P)²+1.0094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7416
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1722
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8941(3) -0.0417(3) 0.0842(3) 0.0606(7) Uani 1 1 d . . .
H1 H 0.9150 0.0166 0.0615 0.073 Uiso 1 1 calc R . .
C2 C 0.9857(3) -0.0945(3) 0.1112(3) 0.0712(9) Uani 1 1 d . . .
H2 H 1.0673 -0.0721 0.1059 0.085 Uiso 1 1 calc R . .
C3 C 0.9570(3) -0.1797(3) 0.1456(3) 0.0679(8) Uani 1 1 d . . .
H3 H 1.0180 -0.2169 0.1619 0.082 Uiso 1 1 calc R . .
C4 C 0.8382(3) -0.2097(3) 0.1558(3) 0.0664(8) Uani 1 1 d . . .
H4 H 0.8193 -0.2657 0.1814 0.080 Uiso 1 1 calc R . .
C5 C 0.7457(3) -0.1573(2) 0.1283(2) 0.0536(7) Uani 1 1 d . . .
H5 H 0.6649 -0.1786 0.1354 0.064 Uiso 1 1 calc R . .
C6 C 0.7721(2) -0.0741(2) 0.0905(2) 0.0452(6) Uani 1 1 d . . .
C7 C 0.6674(3) -0.0250(2) 0.0504(2) 0.0507(6) Uani 1 1 d . . .
H7A H 0.6583 -0.0407 -0.0260 0.061 Uiso 1 1 calc R . .
H7B H 0.5841 -0.0707 0.0463 0.061 Uiso 1 1 calc R . .
C8 C 0.7513(2) 0.1961(2) 0.1022(2) 0.0397(5) Uani 1 1 d . . .
C9 C 0.7607(2) 0.3232(2) 0.19575(19) 0.0350(5) Uani 1 1 d . . .
C10 C 0.7047(2) 0.2889(2) 0.27188(19) 0.0359(5) Uani 1 1 d . . .
C11 C 0.6810(2) 0.3583(2) 0.3684(2) 0.0402(5) Uani 1 1 d . . .
H11 H 0.7053 0.4442 0.4003 0.048 Uiso 1 1 calc R . .
C12 C 0.6206(2) 0.3003(2) 0.4187(2) 0.0450(6) Uani 1 1 d . . .
C13 C 0.5930(3) 0.3757(3) 0.5231(3) 0.0607(7) Uani 1 1 d . . .
H13A H 0.5037 0.3742 0.5009 0.091 Uiso 1 1 calc R . .
H13B H 0.6512 0.4600 0.5622 0.091 Uiso 1 1 calc R . .
H13C H 0.6066 0.3412 0.5729 0.091 Uiso 1 1 calc R . .
C14 C 0.5859(3) 0.1730(3) 0.3690(3) 0.0540(7) Uani 1 1 d . . .
H14 H 0.5468 0.1340 0.4026 0.065 Uiso 1 1 calc R . .
C15 C 0.6067(3) 0.1005(2) 0.2708(3) 0.0522(7) Uani 1 1 d . . .
H15 H 0.5814 0.0145 0.2382 0.063 Uiso 1 1 calc R . .
C16 C 0.6661(2) 0.1602(2) 0.2234(2) 0.0399(5) Uani 1 1 d . . .
C17 C 0.9035(2) 0.4138(2) 0.24879(19) 0.0346(5) Uani 1 1 d . . .
H17 H 0.9258 0.4232 0.1883 0.042 Uiso 1 1 calc R . .
C18 C 1.0004(2) 0.3618(2) 0.2981(2) 0.0403(5) Uani 1 1 d . . .
C19 C 1.1067(2) 0.3339(2) 0.2551(2) 0.0411(5) Uani 1 1 d . . .
C20 C 1.1466(3) 0.3778(3) 0.1885(2) 0.0525(6) Uani 1 1 d . . .
H20 H 1.0999 0.4197 0.1615 0.063 Uiso 1 1 calc R . .
C21 C 1.2559(3) 0.3597(3) 0.1618(3) 0.0699(9) Uani 1 1 d . . .
H21 H 1.2843 0.3919 0.1193 0.084 Uiso 1 1 calc R . .
C22 C 1.3224(3) 0.2942(3) 0.1981(3) 0.0753(10) Uani 1 1 d . . .
H22 H 1.3954 0.2818 0.1797 0.090 Uiso 1 1 calc R . .
C23 C 1.2817(3) 0.2470(3) 0.2615(3) 0.0753(10) Uani 1 1 d . . .
H23 H 1.3259 0.2013 0.2847 0.090 Uiso 1 1 calc R . .
C24 C 1.1751(3) 0.2673(3) 0.2909(3) 0.0581(7) Uani 1 1 d . . .
H24 H 1.1487 0.2363 0.3349 0.070 Uiso 1 1 calc R . .
C25 C 0.6724(2) 0.3785(2) 0.14287(19) 0.0357(5) Uani 1 1 d . . .
C26 C 0.6983(2) 0.5123(2) 0.21595(19) 0.0355(5) Uani 1 1 d . . .
C27 C 0.6007(2) 0.5586(2) 0.1737(2) 0.0428(5) Uani 1 1 d . . .
C28 C 0.8039(2) 0.5863(2) 0.31462(19) 0.0337(5) Uani 1 1 d . . .
C29 C 0.8197(2) 0.7128(2) 0.40000(19) 0.0385(5) Uani 1 1 d . . .
C30 C 0.7094(3) 0.7470(3) 0.4153(2) 0.0510(6) Uani 1 1 d . . .
H30 H 0.6255 0.6903 0.3680 0.061 Uiso 1 1 calc R . .
C31 C 0.7241(3) 0.8631(3) 0.4991(3) 0.0630(8) Uani 1 1 d . . .
H31 H 0.6505 0.8851 0.5074 0.076 Uiso 1 1 calc R . .
C32 C 0.8484(3) 0.9468(3) 0.5708(3) 0.0638(8) Uani 1 1 d . . .
H32 H 0.8585 1.0255 0.6272 0.077 Uiso 1 1 calc R . .
C33 C 0.9575(3) 0.9142(3) 0.5590(2) 0.0587(7) Uani 1 1 d . . .
H33 H 1.0407 0.9710 0.6086 0.070 Uiso 1 1 calc R . .
C34 C 0.9456(2) 0.7976(2) 0.4742(2) 0.0440(6) Uani 1 1 d . . .
C35 C 1.0675(2) 0.7648(2) 0.4665(2) 0.0498(6) Uani 1 1 d . . .
H35A H 1.1114 0.7636 0.5354 0.060 Uiso 1 1 calc R . .
H35B H 1.1268 0.8292 0.4633 0.060 Uiso 1 1 calc R . .
C36 C 1.0415(2) 0.6410(2) 0.3645(2) 0.0450(6) Uani 1 1 d . . .
H36A H 1.1167 0.6134 0.3774 0.054 Uiso 1 1 calc R . .
H36B H 1.0306 0.6506 0.2976 0.054 Uiso 1 1 calc R . .
C37 C 0.9182(2) 0.5420(2) 0.34204(19) 0.0348(5) Uani 1 1 d . . .
H37 H 0.9270 0.5388 0.4125 0.042 Uiso 1 1 calc R . .
C38 C 0.3022(5) 0.7408(4) 0.1585(4) 0.0999(14) Uani 1 1 d . . .
H38A H 0.3818 0.7248 0.1493 0.120 Uiso 1 1 calc R . .
H38B H 0.2862 0.7972 0.1303 0.120 Uiso 1 1 calc R . .
Cl1 Cl 0.3239(2) 0.8095(2) 0.30069(15) 0.1763(8) Uani 1 1 d . . .
Cl2 Cl 0.17045(17) 0.60132(16) 0.07825(17) 0.1487(6) Uani 1 1 d . . .
N1 N 0.6949(2) 0.10726(18) 0.12366(18) 0.0434(5) Uani 1 1 d . . .
N2 N 0.5813(2) 0.3069(2) 0.04599(19) 0.0510(6) Uani 1 1 d . . .
N3 N 0.5221(3) 0.5893(2) 0.1332(2) 0.0658(7) Uani 1 1 d . . .
O1 O 0.79107(19) 0.17786(16) 0.02470(15) 0.0512(4) Uani 1 1 d . . .
O2 O 0.98920(19) 0.3459(2) 0.37611(18) 0.0639(6) Uani 1 1 d . . .
H2A H 0.535(3) 0.349(3) 0.028(3) 0.067(9) Uiso 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 1.379(4) . ?
C1 C6 1.379(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 N1 1.457(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.213(3) . ?
C8 N1 1.361(3) . ?
C8 C9 1.538(3) . ?
C9 C10 1.520(3) . ?
C9 C25 1.527(3) . ?
C9 C17 1.551(3) . ?
C10 C11 1.377(3) . ?
C10 C16 1.391(3) . ?
C11 C12 1.398(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.377(4) . ?
C12 C13 1.503(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.407(3) . ?
C17 C37 1.527(3) . ?
C17 C18 1.531(3) . ?
C17 H17 0.9800 . ?
C18 O2 1.215(3) . ?
C18 C19 1.484(3) . ?
C19 C20 1.381(4) . ?
C19 C24 1.393(3) . ?
C20 C21 1.387(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.270(3) . ?
C25 C26 1.475(3) . ?
C26 C28 1.358(3) . ?
C26 C27 1.443(3) . ?
C27 N3 1.141(3) . ?
C28 C29 1.471(3) . ?
C28 C37 1.512(3) . ?
C29 C34 1.402(3) . ?
C29 C30 1.408(3) . ?
C30 C31 1.375(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.377(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.393(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.505(4) . ?
C35 C36 1.510(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.536(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37 0.9800 . ?
C38 Cl1 1.717(5) . ?
C38 Cl2 1.747(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
N2 H2A 0.87(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(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 120.9(2) . . ?
C1 C6 C7 120.7(2) . . ?
N1 C7 C6 113.9(2) . . ?
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 125.5(2) . . ?
O1 C8 C9 126.2(2) . . ?
N1 C8 C9 108.2(2) . . ?
C10 C9 C25 109.51(17) . . ?
C10 C9 C8 102.41(17) . . ?
C25 C9 C8 109.52(17) . . ?
C10 C9 C17 118.39(18) . . ?
C25 C9 C17 107.25(17) . . ?
C8 C9 C17 109.53(18) . . ?
C11 C10 C16 119.6(2) . . ?
C11 C10 C9 132.5(2) . . ?
C16 C10 C9 107.81(19) . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 118.2(2) . . ?
C14 C12 C13 121.3(2) . . ?
C11 C12 C13 120.4(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.7(2) . . ?
C12 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C10 121.4(2) . . ?
C15 C16 N1 128.1(2) . . ?
C10 C16 N1 110.4(2) . . ?
C37 C17 C18 109.44(18) . . ?
C37 C17 C9 111.69(17) . . ?
C18 C17 C9 110.86(17) . . ?
C37 C17 H17 108.2 . . ?
C18 C17 H17 108.2 . . ?
C9 C17 H17 108.2 . . ?
O2 C18 C19 120.3(2) . . ?
O2 C18 C17 117.6(2) . . ?
C19 C18 C17 122.07(19) . . ?
C20 C19 C24 118.8(2) . . ?
C20 C19 C18 123.3(2) . . ?
C24 C19 C18 117.7(2) . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.0(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
N2 C25 C26 126.4(2) . . ?
N2 C25 C9 118.8(2) . . ?
C26 C25 C9 114.66(18) . . ?
C28 C26 C27 122.4(2) . . ?
C28 C26 C25 123.64(19) . . ?
C27 C26 C25 113.99(19) . . ?
N3 C27 C26 175.5(3) . . ?
C26 C28 C29 124.81(19) . . ?
C26 C28 C37 120.24(19) . . ?
C29 C28 C37 114.93(19) . . ?
C34 C29 C30 119.0(2) . . ?
C34 C29 C28 120.0(2) . . ?
C30 C29 C28 120.8(2) . . ?
C31 C30 C29 120.9(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C34 121.2(3) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C29 118.8(2) . . ?
C33 C34 C35 119.4(2) . . ?
C29 C34 C35 121.7(2) . . ?
C34 C35 C36 113.9(2) . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C35 C36 C37 111.8(2) . . ?
C35 C36 H36A 109.3 . . ?
C37 C36 H36A 109.3 . . ?
C35 C36 H36B 109.3 . . ?
C37 C36 H36B 109.3 . . ?
H36A C36 H36B 107.9 . . ?
C28 C37 C17 114.03(17) . . ?
C28 C37 C36 106.53(17) . . ?
C17 C37 C36 111.02(18) . . ?
C28 C37 H37 108.4 . . ?
C17 C37 H37 108.4 . . ?
C36 C37 H37 108.4 . . ?
Cl1 C38 Cl2 111.5(2) . . ?
Cl1 C38 H38A 109.3 . . ?
Cl2 C38 H38A 109.3 . . ?
Cl1 C38 H38B 109.3 . . ?
Cl2 C38 H38B 109.3 . . ?
H38A C38 H38B 108.0 . . ?
C8 N1 C16 111.15(19) . . ?
C8 N1 C7 123.3(2) . . ?
C16 N1 C7 125.5(2) . . ?
C25 N2 H2A 109(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 H2A N3 0.87(3) 2.65(3) 3.343(3) 137(3) 2_665

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_1d
_audit_block_doi                 10.5517/cc11nps5
_database_code_depnum_ccdc_archive 'CCDC 973207'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H28 Cl N3 O2'
_chemical_formula_sum            'C37 H28 Cl N3 O2'
_chemical_formula_weight         582.07

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                   9.762(3)
_cell_length_b                   12.247(3)
_cell_length_c                   12.796(4)
_cell_angle_alpha                102.081(3)
_cell_angle_beta                 97.905(4)
_cell_angle_gamma                93.279(4)
_cell_volume                     1475.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2674
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.970
_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            12956
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.41
_reflns_number_total             6732
_reflns_number_gt                4021
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0438P)²+0.4244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6494
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.6944(3) 0.3181(2) 0.6285(2) 0.0676(7) Uani 1 1 d . . .
H1 H 0.6783 0.3919 0.6266 0.081 Uiso 1 1 calc R . .
C2 C 0.6213(3) 0.2314(3) 0.5504(2) 0.0852(9) Uani 1 1 d . . .
H2 H 0.5560 0.2471 0.4967 0.102 Uiso 1 1 calc R . .
C3 C 0.6446(3) 0.1230(3) 0.5517(3) 0.0825(9) Uani 1 1 d . . .
H3A H 0.5957 0.0649 0.4986 0.099 Uiso 1 1 calc R . .
C4 C 0.7399(3) 0.0998(2) 0.6312(2) 0.0704(8) Uani 1 1 d . . .
H4 H 0.7559 0.0259 0.6325 0.084 Uiso 1 1 calc R . .
C5 C 0.8118(3) 0.18588(19) 0.7087(2) 0.0550(6) Uani 1 1 d . . .
H5 H 0.8764 0.1695 0.7625 0.066 Uiso 1 1 calc R . .
C6 C 0.7905(2) 0.29646(18) 0.70897(18) 0.0478(5) Uani 1 1 d . . .
C7 C 0.8737(3) 0.38625(18) 0.7976(2) 0.0579(6) Uani 1 1 d . . .
H7A H 0.8600 0.3704 0.8668 0.070 Uiso 1 1 calc R . .
H7B H 0.9713 0.3820 0.7918 0.070 Uiso 1 1 calc R . .
C8 C 0.7603(2) 0.55736(17) 0.86567(17) 0.0422(5) Uani 1 1 d . . .
C9 C 0.7604(2) 0.67920(15) 0.84939(16) 0.0362(5) Uani 1 1 d . . .
C10 C 0.8549(2) 0.67841(17) 0.76516(16) 0.0396(5) Uani 1 1 d . . .
C11 C 0.9060(2) 0.76236(19) 0.72035(17) 0.0452(5) Uani 1 1 d . . .
H11 H 0.8780 0.8343 0.7391 0.054 Uiso 1 1 calc R . .
C12 C 0.9998(2) 0.7399(2) 0.64686(19) 0.0551(6) Uani 1 1 d . . .
C13 C 1.0552(3) 0.8312(2) 0.5971(2) 0.0771(8) Uani 1 1 d . . .
H13A H 1.1236 0.8806 0.6494 0.116 Uiso 1 1 calc R . .
H13B H 0.9804 0.8728 0.5745 0.116 Uiso 1 1 calc R . .
H13C H 1.0969 0.7983 0.5355 0.116 Uiso 1 1 calc R . .
C14 C 1.0391(3) 0.6314(3) 0.6210(2) 0.0695(8) Uani 1 1 d . . .
H14 H 1.1006 0.6155 0.5716 0.083 Uiso 1 1 calc R . .
C15 C 0.9905(3) 0.5461(2) 0.6659(2) 0.0669(7) Uani 1 1 d . . .
H15 H 1.0188 0.4742 0.6479 0.080 Uiso 1 1 calc R . .
C16 C 0.8988(2) 0.57157(19) 0.73825(18) 0.0502(6) Uani 1 1 d . . .
C17 C 0.6094(2) 0.70751(15) 0.82059(15) 0.0351(4) Uani 1 1 d . . .
H17 H 0.5582 0.6956 0.8786 0.042 Uiso 1 1 calc R . .
C18 C 0.5388(2) 0.62959(17) 0.71512(16) 0.0392(5) Uani 1 1 d . . .
C19 C 0.4378(2) 0.53326(16) 0.71404(16) 0.0377(5) Uani 1 1 d . . .
C20 C 0.3990(2) 0.50481(18) 0.80610(17) 0.0440(5) Uani 1 1 d . . .
H20 H 0.4316 0.5510 0.8735 0.053 Uiso 1 1 calc R . .
C21 C 0.3130(2) 0.40925(19) 0.79931(19) 0.0496(6) Uani 1 1 d . . .
H21 H 0.2876 0.3910 0.8614 0.060 Uiso 1 1 calc R . .
C22 C 0.2656(2) 0.34155(19) 0.6993(2) 0.0502(6) Uani 1 1 d . . .
C23 C 0.2968(2) 0.3690(2) 0.6058(2) 0.0577(6) Uani 1 1 d . . .
H23 H 0.2612 0.3236 0.5386 0.069 Uiso 1 1 calc R . .
C24 C 0.3822(2) 0.46525(19) 0.61360(18) 0.0500(6) Uani 1 1 d . . .
H24 H 0.4029 0.4851 0.5509 0.060 Uiso 1 1 calc R . .
C25 C 0.6020(2) 0.82959(15) 0.81113(16) 0.0360(5) Uani 1 1 d . . .
H25 H 0.6343 0.8372 0.7436 0.043 Uiso 1 1 calc R . .
C26 C 0.4509(2) 0.85821(17) 0.80455(19) 0.0479(6) Uani 1 1 d . . .
H26A H 0.3934 0.8034 0.7473 0.057 Uiso 1 1 calc R . .
H26B H 0.4182 0.8550 0.8722 0.057 Uiso 1 1 calc R . .
C27 C 0.4376(2) 0.97386(19) 0.7825(2) 0.0575(6) Uani 1 1 d . . .
H27A H 0.4509 0.9723 0.7085 0.069 Uiso 1 1 calc R . .
H27B H 0.3445 0.9947 0.7902 0.069 Uiso 1 1 calc R . .
C28 C 0.5406(2) 1.06037(18) 0.85729(19) 0.0482(6) Uani 1 1 d . . .
C29 C 0.5155(3) 1.1725(2) 0.8689(2) 0.0619(7) Uani 1 1 d . . .
H29 H 0.4332 1.1907 0.8334 0.074 Uiso 1 1 calc R . .
C30 C 0.6086(3) 1.2571(2) 0.9311(2) 0.0672(8) Uani 1 1 d . . .
H30 H 0.5888 1.3315 0.9383 0.081 Uiso 1 1 calc R . .
C31 C 0.7315(3) 1.23110(19) 0.9827(2) 0.0634(7) Uani 1 1 d . . .
H31 H 0.7958 1.2879 1.0244 0.076 Uiso 1 1 calc R . .
C32 C 0.7592(3) 1.12061(18) 0.97252(19) 0.0518(6) Uani 1 1 d . . .
H32 H 0.8435 1.1040 1.0064 0.062 Uiso 1 1 calc R . .
C33 C 0.6634(2) 1.03260(16) 0.91238(17) 0.0418(5) Uani 1 1 d . . .
C34 C 0.6907(2) 0.91276(16) 0.90300(16) 0.0361(5) Uani 1 1 d . . .
C35 C 0.7868(2) 0.87522(16) 0.97141(16) 0.0384(5) Uani 1 1 d . . .
C36 C 0.8655(3) 0.94324(18) 1.06902(19) 0.0495(6) Uani 1 1 d . . .
C37 C 0.8239(2) 0.75772(16) 0.95517(17) 0.0398(5) Uani 1 1 d . . .
Cl1 Cl 0.16439(8) 0.21741(6) 0.69037(6) 0.0822(3) Uani 1 1 d . . .
N1 N 0.8393(2) 0.50042(15) 0.79667(15) 0.0515(5) Uani 1 1 d . . .
N2 N 0.9339(3) 0.98536(18) 1.14872(18) 0.0748(7) Uani 1 1 d . . .
N3 N 0.9084(2) 0.72011(19) 1.02039(19) 0.0623(6) Uani 1 1 d . . .
O1 O 0.69902(17) 0.51954(12) 0.92862(12) 0.0531(4) Uani 1 1 d . . .
O2 O 0.56960(18) 0.64687(13) 0.63071(12) 0.0575(4) Uani 1 1 d . . .
H3B H 0.939(3) 0.769(3) 1.077(3) 0.100(12) Uiso 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 1.374(3) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(3) . ?
C7 N1 1.459(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.216(2) . ?
C8 N1 1.361(3) . ?
C8 C9 1.549(3) . ?
C9 C10 1.511(3) . ?
C9 C37 1.516(3) . ?
C9 C17 1.547(3) . ?
C10 C11 1.379(3) . ?
C10 C16 1.389(3) . ?
C11 C12 1.398(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.390(4) . ?
C12 C13 1.507(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.410(3) . ?
C17 C18 1.529(3) . ?
C17 C25 1.530(3) . ?
C17 H17 0.9800 . ?
C18 O2 1.217(2) . ?
C18 C19 1.490(3) . ?
C19 C20 1.390(3) . ?
C19 C24 1.396(3) . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C22 Cl1 1.739(2) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C34 1.512(3) . ?
C25 C26 1.531(3) . ?
C25 H25 0.9800 . ?
C26 C27 1.510(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.496(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.389(3) . ?
C28 C33 1.402(3) . ?
C29 C30 1.372(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.403(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.490(3) . ?
C34 C35 1.360(3) . ?
C35 C36 1.439(3) . ?
C35 C37 1.484(3) . ?
C36 N2 1.143(3) . ?
C37 N3 1.266(3) . ?
N3 H3B 0.84(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
C6 C1 C2 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 C7 123.9(2) . . ?
C5 C6 C7 118.2(2) . . ?
N1 C7 C6 115.06(19) . . ?
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 126.3(2) . . ?
O1 C8 C9 125.66(19) . . ?
N1 C8 C9 108.06(18) . . ?
C10 C9 C37 110.63(17) . . ?
C10 C9 C17 117.53(16) . . ?
C37 C9 C17 108.11(15) . . ?
C10 C9 C8 102.23(16) . . ?
C37 C9 C8 108.31(16) . . ?
C17 C9 C8 109.64(16) . . ?
C11 C10 C16 119.7(2) . . ?
C11 C10 C9 131.91(18) . . ?
C16 C10 C9 108.30(18) . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C14 C12 C11 118.0(2) . . ?
C14 C12 C13 121.4(2) . . ?
C11 C12 C13 120.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 122.7(2) . . ?
C15 C14 H14 118.6 . . ?
C12 C14 H14 118.6 . . ?
C16 C15 C14 117.5(2) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C10 121.7(2) . . ?
C15 C16 N1 127.8(2) . . ?
C10 C16 N1 110.39(19) . . ?
C18 C17 C25 109.62(16) . . ?
C18 C17 C9 110.60(15) . . ?
C25 C17 C9 112.15(16) . . ?
C18 C17 H17 108.1 . . ?
C25 C17 H17 108.1 . . ?
C9 C17 H17 108.1 . . ?
O2 C18 C19 120.17(19) . . ?
O2 C18 C17 117.91(18) . . ?
C19 C18 C17 121.90(17) . . ?
C20 C19 C24 118.12(19) . . ?
C20 C19 C18 124.45(18) . . ?
C24 C19 C18 117.40(18) . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 118.9(2) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 121.7(2) . . ?
C21 C22 Cl1 119.27(19) . . ?
C23 C22 Cl1 118.98(18) . . ?
C22 C23 C24 118.7(2) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 121.1(2) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C34 C25 C17 113.76(16) . . ?
C34 C25 C26 109.43(16) . . ?
C17 C25 C26 109.39(16) . . ?
C34 C25 H25 108.0 . . ?
C17 C25 H25 108.0 . . ?
C26 C25 H25 108.0 . . ?
C27 C26 C25 110.79(18) . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 112.44(19) . . ?
C28 C27 H27A 109.1 . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C33 119.1(2) . . ?
C29 C28 C27 118.5(2) . . ?
C33 C28 C27 122.38(19) . . ?
C30 C29 C28 122.0(3) . . ?
C30 C29 H29 119.0 . . ?
C28 C29 H29 119.0 . . ?
C29 C30 C31 119.5(2) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 121.7(2) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C28 C33 C32 117.88(19) . . ?
C28 C33 C34 119.92(19) . . ?
C32 C33 C34 122.2(2) . . ?
C35 C34 C33 124.45(19) . . ?
C35 C34 C25 119.46(17) . . ?
C33 C34 C25 116.08(18) . . ?
C34 C35 C36 124.92(19) . . ?
C34 C35 C37 124.18(18) . . ?
C36 C35 C37 110.90(18) . . ?
N2 C36 C35 171.7(2) . . ?
N3 C37 C35 125.1(2) . . ?
N3 C37 C9 118.19(19) . . ?
C35 C37 C9 116.68(17) . . ?
C8 N1 C16 110.96(17) . . ?
C8 N1 C7 123.0(2) . . ?
C16 N1 C7 125.35(19) . . ?
C37 N3 H3B 112(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
N3 H3B N2 0.84(3) 2.62(3) 3.297(3) 138(3) .

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_1e
_audit_block_doi                 10.5517/cc11npt6
_database_code_depnum_ccdc_archive 'CCDC 973208'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H28 F N3 O2'
_chemical_formula_sum            'C37 H28 F N3 O2'
_chemical_formula_weight         565.62

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'
F F 0.0171 0.0103 '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'

_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                   21.4770(17)
_cell_length_b                   19.1094(15)
_cell_length_c                   15.1357(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.428(3)
_cell_angle_gamma                90.00
_cell_volume                     5610.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2368
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_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            47165
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.42
_reflns_number_total             6404
_reflns_number_gt                3662
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0438P)²+3.3817P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6391
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.15742(12) 0.29509(13) 0.60133(17) 0.0633(7) Uani 1 1 d . . .
H1 H -0.1448 0.2845 0.6668 0.076 Uiso 1 1 calc R . .
C2 C -0.20804(14) 0.34409(14) 0.5548(2) 0.0760(8) Uani 1 1 d . . .
H2 H -0.2295 0.3663 0.5890 0.091 Uiso 1 1 calc R . .
C3 C -0.22705(13) 0.36039(12) 0.45896(19) 0.0644(7) Uani 1 1 d . . .
H3 H -0.2617 0.3930 0.4277 0.077 Uiso 1 1 calc R . .
C4 C -0.19495(12) 0.32855(13) 0.40952(17) 0.0633(6) Uani 1 1 d . . .
H4 H -0.2072 0.3399 0.3444 0.076 Uiso 1 1 calc R . .
C5 C -0.14420(12) 0.27932(12) 0.45576(16) 0.0580(6) Uani 1 1 d . . .
H5 H -0.1225 0.2579 0.4214 0.070 Uiso 1 1 calc R . .
C6 C -0.12548(10) 0.26171(11) 0.55156(14) 0.0435(5) Uani 1 1 d . . .
C7 C -0.07163(11) 0.20724(13) 0.60548(16) 0.0583(6) Uani 1 1 d . . .
H7A H -0.0425 0.2250 0.6702 0.070 Uiso 1 1 calc R . .
H7B H -0.0947 0.1658 0.6136 0.070 Uiso 1 1 calc R . .
C8 C 0.03575(10) 0.21416(11) 0.58392(14) 0.0426(5) Uani 1 1 d . . .
C9 C 0.06688(9) 0.17952(10) 0.52030(13) 0.0362(4) Uani 1 1 d . . .
C10 C 0.01184(9) 0.12684(10) 0.46215(13) 0.0366(4) Uani 1 1 d . . .
C11 C 0.00884(10) 0.07644(10) 0.39530(15) 0.0462(5) Uani 1 1 d . . .
H11 H 0.0451 0.0698 0.3780 0.055 Uiso 1 1 calc R . .
C12 C -0.05001(12) 0.03638(12) 0.35530(16) 0.0550(6) Uani 1 1 d . . .
C13 C -0.10463(11) 0.04405(12) 0.37749(17) 0.0589(6) Uani 1 1 d . . .
H13 H -0.1436 0.0162 0.3474 0.071 Uiso 1 1 calc R . .
C14 C -0.10123(11) 0.09386(12) 0.44542(17) 0.0555(6) Uani 1 1 d . . .
H14 H -0.1377 0.1000 0.4624 0.067 Uiso 1 1 calc R . .
C15 C -0.04282(9) 0.13416(10) 0.48738(14) 0.0419(5) Uani 1 1 d . . .
C16 C 0.08412(9) 0.23770(9) 0.46257(13) 0.0349(4) Uani 1 1 d . . .
H16 H 0.1163 0.2703 0.5105 0.042 Uiso 1 1 calc R . .
C17 C 0.02012(9) 0.27945(10) 0.39687(13) 0.0367(4) Uani 1 1 d . . .
C18 C 0.01883(9) 0.35646(10) 0.39786(13) 0.0379(4) Uani 1 1 d . . .
C19 C 0.07536(11) 0.39800(11) 0.45193(15) 0.0515(5) Uani 1 1 d . . .
H19 H 0.1168 0.3771 0.4934 0.062 Uiso 1 1 calc R . .
C20 C 0.07099(12) 0.46991(11) 0.44498(17) 0.0570(6) Uani 1 1 d . . .
H20 H 0.1098 0.4967 0.4813 0.068 Uiso 1 1 calc R . .
C21 C 0.01058(12) 0.50303(11) 0.38565(16) 0.0510(5) Uani 1 1 d . . .
C22 C 0.00700(14) 0.58150(12) 0.38015(19) 0.0741(7) Uani 1 1 d . . .
H22A H -0.0377 0.5956 0.3322 0.111 Uiso 1 1 calc R . .
H22B H 0.0418 0.5989 0.3619 0.111 Uiso 1 1 calc R . .
H22C H 0.0146 0.6002 0.4429 0.111 Uiso 1 1 calc R . .
C23 C -0.04574(11) 0.46178(11) 0.33223(16) 0.0545(6) Uani 1 1 d . . .
H23 H -0.0872 0.4830 0.2915 0.065 Uiso 1 1 calc R . .
C24 C -0.04213(10) 0.39023(11) 0.33783(15) 0.0482(5) Uani 1 1 d . . .
H24 H -0.0811 0.3638 0.3009 0.058 Uiso 1 1 calc R . .
C25 C 0.13512(9) 0.14375(10) 0.58484(14) 0.0370(4) Uani 1 1 d . . .
C26 C 0.17740(9) 0.12365(9) 0.53406(13) 0.0364(4) Uani 1 1 d . . .
C27 C 0.23351(11) 0.07704(11) 0.58917(15) 0.0467(5) Uani 1 1 d . . .
C28 C 0.16792(9) 0.14969(9) 0.44562(13) 0.0338(4) Uani 1 1 d . . .
C29 C 0.11917(9) 0.20956(9) 0.40053(13) 0.0345(4) Uani 1 1 d . . .
H29 H 0.0835 0.1944 0.3371 0.041 Uiso 1 1 calc R . .
C30 C 0.16108(10) 0.26862(10) 0.38327(14) 0.0394(5) Uani 1 1 d . . .
H30A H 0.1312 0.3086 0.3554 0.047 Uiso 1 1 calc R . .
H30B H 0.1974 0.2829 0.4456 0.047 Uiso 1 1 calc R . .
C31 C 0.19276(10) 0.24716(10) 0.31585(14) 0.0423(5) Uani 1 1 d . . .
H31A H 0.1579 0.2504 0.2488 0.051 Uiso 1 1 calc R . .
H31B H 0.2291 0.2800 0.3233 0.051 Uiso 1 1 calc R . .
C32 C 0.22209(9) 0.17472(10) 0.33328(13) 0.0380(4) Uani 1 1 d . . .
C33 C 0.26280(10) 0.15325(12) 0.28760(15) 0.0497(5) Uani 1 1 d . . .
H33 H 0.2755 0.1857 0.2524 0.060 Uiso 1 1 calc R . .
C34 C 0.28469(11) 0.08540(13) 0.29323(16) 0.0566(6) Uani 1 1 d . . .
H34 H 0.3123 0.0723 0.2627 0.068 Uiso 1 1 calc R . .
C35 C 0.26578(11) 0.03671(12) 0.34403(16) 0.0568(6) Uani 1 1 d . . .
H35 H 0.2785 -0.0099 0.3451 0.068 Uiso 1 1 calc R . .
C36 C 0.22805(10) 0.05724(11) 0.39321(15) 0.0485(5) Uani 1 1 d . . .
H36 H 0.2163 0.0243 0.4287 0.058 Uiso 1 1 calc R . .
C37 C 0.20699(9) 0.12654(10) 0.39104(13) 0.0371(4) Uani 1 1 d . . .
F1 F -0.05374(8) -0.01367(8) 0.28902(12) 0.0890(5) Uani 1 1 d . . .
N1 N -0.02799(8) 0.18694(9) 0.55844(12) 0.0472(4) Uani 1 1 d . . .
N2 N 0.15683(10) 0.12853(10) 0.67479(13) 0.0535(5) Uani 1 1 d . . .
N3 N 0.27832(11) 0.04172(12) 0.63573(16) 0.0786(7) Uani 1 1 d . . .
O1 O 0.06335(8) 0.25841(8) 0.64616(11) 0.0602(4) Uani 1 1 d . . .
O2 O -0.02996(7) 0.24641(7) 0.34050(10) 0.0525(4) Uani 1 1 d . . .
H2A H 0.1286(12) 0.1424(12) 0.7006(17) 0.068(8) Uiso 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 1.374(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(3) . ?
C7 N1 1.452(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(2) . ?
C8 N1 1.356(2) . ?
C8 C9 1.538(3) . ?
C9 C10 1.514(3) . ?
C9 C25 1.530(3) . ?
C9 C16 1.554(2) . ?
C10 C11 1.378(3) . ?
C10 C15 1.389(2) . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(3) . ?
C12 F1 1.363(2) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.408(3) . ?
C16 C17 1.530(2) . ?
C16 C29 1.531(2) . ?
C16 H16 0.9800 . ?
C17 O2 1.223(2) . ?
C17 C18 1.472(3) . ?
C18 C19 1.386(3) . ?
C18 C24 1.391(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.378(3) . ?
C21 C22 1.502(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.370(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N2 1.269(2) . ?
C25 C26 1.471(3) . ?
C26 C28 1.359(2) . ?
C26 C27 1.442(3) . ?
C27 N3 1.138(2) . ?
C28 C37 1.476(2) . ?
C28 C29 1.502(2) . ?
C29 C30 1.534(2) . ?
C29 H29 0.9800 . ?
C30 C31 1.506(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.497(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.389(3) . ?
C32 C37 1.400(3) . ?
C33 C34 1.369(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.372(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.395(3) . ?
C36 H36 0.9300 . ?
N2 H2A 0.89(2) . ?

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 120.3(2) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 123.40(18) . . ?
C1 C6 C7 118.08(19) . . ?
N1 C7 C6 115.16(17) . . ?
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 125.77(18) . . ?
O1 C8 C9 125.93(18) . . ?
N1 C8 C9 108.29(17) . . ?
C10 C9 C25 111.65(15) . . ?
C10 C9 C8 102.10(15) . . ?
C25 C9 C8 110.32(15) . . ?
C10 C9 C16 117.64(15) . . ?
C25 C9 C16 106.53(14) . . ?
C8 C9 C16 108.46(15) . . ?
C11 C10 C15 119.59(18) . . ?
C11 C10 C9 132.09(17) . . ?
C15 C10 C9 108.31(16) . . ?
C12 C11 C10 117.16(19) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
C13 C12 F1 118.24(19) . . ?
C13 C12 C11 123.9(2) . . ?
F1 C12 C11 117.8(2) . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 121.90(19) . . ?
C14 C15 N1 128.12(18) . . ?
C10 C15 N1 109.98(17) . . ?
C17 C16 C29 109.00(14) . . ?
C17 C16 C9 111.97(14) . . ?
C29 C16 C9 113.09(14) . . ?
C17 C16 H16 107.5 . . ?
C29 C16 H16 107.5 . . ?
C9 C16 H16 107.5 . . ?
O2 C17 C18 120.57(17) . . ?
O2 C17 C16 117.37(17) . . ?
C18 C17 C16 122.02(16) . . ?
C19 C18 C24 117.40(18) . . ?
C19 C18 C17 124.27(18) . . ?
C24 C18 C17 118.28(17) . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C23 117.7(2) . . ?
C20 C21 C22 120.5(2) . . ?
C23 C21 C22 121.8(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 121.5(2) . . ?
C24 C23 H23 119.2 . . ?
C21 C23 H23 119.2 . . ?
C23 C24 C18 121.1(2) . . ?
C23 C24 H24 119.5 . . ?
C18 C24 H24 119.5 . . ?
N2 C25 C26 118.42(18) . . ?
N2 C25 C9 126.68(18) . . ?
C26 C25 C9 114.86(15) . . ?
C28 C26 C27 122.06(17) . . ?
C28 C26 C25 123.65(16) . . ?
C27 C26 C25 114.17(16) . . ?
N3 C27 C26 177.4(2) . . ?
C26 C28 C37 124.11(16) . . ?
C26 C28 C29 120.45(16) . . ?
C37 C28 C29 115.27(15) . . ?
C28 C29 C16 114.77(15) . . ?
C28 C29 C30 106.99(14) . . ?
C16 C29 C30 108.97(15) . . ?
C28 C29 H29 108.7 . . ?
C16 C29 H29 108.7 . . ?
C30 C29 H29 108.7 . . ?
C31 C30 C29 112.57(15) . . ?
C31 C30 H30A 109.1 . . ?
C29 C30 H30A 109.1 . . ?
C31 C30 H30B 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C30 114.25(15) . . ?
C32 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C33 C32 C37 118.72(18) . . ?
C33 C32 C31 119.51(17) . . ?
C37 C32 C31 121.70(16) . . ?
C34 C33 C32 121.4(2) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C35 120.0(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 119.7(2) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C35 C36 C37 121.3(2) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C36 C37 C32 118.63(17) . . ?
C36 C37 C28 121.87(17) . . ?
C32 C37 C28 119.48(17) . . ?
C8 N1 C15 111.20(15) . . ?
C8 N1 C7 122.90(18) . . ?
C15 N1 C7 125.74(18) . . ?
C25 N2 H2A 113.3(15) . . ?

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 0.89(2) 2.56(2) 3.103(2) 119.8(18) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_1h
_audit_block_doi                 10.5517/cc11npv7
_database_code_depnum_ccdc_archive 'CCDC 973209'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H28 Cl N3 O2'
_chemical_formula_sum            'C37 H28 Cl N3 O2'
_chemical_formula_weight         582.07

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                   10.0199(14)
_cell_length_b                   11.7340(17)
_cell_length_c                   14.518(2)
_cell_angle_alpha                113.413(4)
_cell_angle_beta                 100.127(4)
_cell_angle_gamma                100.250(4)
_cell_volume                     1482.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4802
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      21.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.957
_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            29277
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6816
_reflns_number_gt                3483
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0832P)²+0.5052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6796
_refine_ls_number_parameters     393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.5622(4) 0.5206(3) 0.1766(3) 0.0811(11) Uani 1 1 d . . .
H1 H 0.4920 0.4430 0.1484 0.097 Uiso 1 1 calc R . .
C2 C 0.6575(5) 0.5381(4) 0.1209(3) 0.1024(15) Uani 1 1 d . . .
H2 H 0.6526 0.4719 0.0569 0.123 Uiso 1 1 calc R . .
C3 C 0.7585(4) 0.6535(4) 0.1611(4) 0.0864(12) Uani 1 1 d . . .
H3 H 0.8220 0.6661 0.1242 0.104 Uiso 1 1 calc R . .
C4 C 0.7659(4) 0.7496(4) 0.2549(3) 0.0820(11) Uani 1 1 d . . .
H4 H 0.8331 0.8286 0.2814 0.098 Uiso 1 1 calc R . .
C5 C 0.6744(3) 0.7299(3) 0.3103(3) 0.0674(9) Uani 1 1 d . . .
H5 H 0.6823 0.7951 0.3755 0.081 Uiso 1 1 calc R . .
C6 C 0.5704(3) 0.6149(3) 0.2712(2) 0.0484(7) Uani 1 1 d . . .
C7 C 0.4682(3) 0.6023(3) 0.3333(2) 0.0553(8) Uani 1 1 d . . .
H7A H 0.5201 0.6388 0.4061 0.066 Uiso 1 1 calc R . .
H7B H 0.4032 0.6530 0.3276 0.066 Uiso 1 1 calc R . .
C8 C 0.2494(3) 0.4215(3) 0.2440(2) 0.0438(7) Uani 1 1 d . . .
C9 C 0.2013(2) 0.2790(2) 0.22630(18) 0.0347(6) Uani 1 1 d . . .
C10 C 0.3307(2) 0.2679(3) 0.29012(18) 0.0369(6) Uani 1 1 d . . .
C11 C 0.3544(3) 0.1658(3) 0.30901(19) 0.0420(6) Uani 1 1 d . . .
H11 H 0.2845 0.0882 0.2819 0.050 Uiso 1 1 calc R . .
C12 C 0.4870(3) 0.1835(3) 0.3701(2) 0.0496(7) Uani 1 1 d . . .
C13 C 0.5919(3) 0.2980(3) 0.4104(2) 0.0504(7) Uani 1 1 d . . .
H13 H 0.6793 0.3069 0.4513 0.061 Uiso 1 1 calc R . .
C14 C 0.5676(3) 0.3989(3) 0.3904(2) 0.0486(7) Uani 1 1 d . . .
H14 H 0.6381 0.4760 0.4168 0.058 Uiso 1 1 calc R . .
C15 C 0.4370(3) 0.3831(2) 0.33064(19) 0.0393(6) Uani 1 1 d . . .
C16 C 0.1707(3) 0.1925(3) 0.10977(19) 0.0394(6) Uani 1 1 d . . .
C17 C 0.0359(2) 0.1855(2) 0.04518(18) 0.0369(6) Uani 1 1 d . . .
C18 C 0.0214(3) 0.1259(2) -0.0655(2) 0.0379(6) Uani 1 1 d . . .
C19 C -0.0687(2) 0.2257(2) 0.08453(18) 0.0363(6) Uani 1 1 d . . .
C20 C -0.2004(3) 0.2244(3) 0.01915(19) 0.0417(6) Uani 1 1 d . . .
C21 C -0.2005(3) 0.2543(3) -0.0643(2) 0.0634(9) Uani 1 1 d . . .
H21 H -0.1156 0.2808 -0.0773 0.076 Uiso 1 1 calc R . .
C22 C -0.3251(4) 0.2453(4) -0.1279(3) 0.0919(14) Uani 1 1 d . . .
H22 H -0.3241 0.2657 -0.1835 0.110 Uiso 1 1 calc R . .
C23 C -0.4496(4) 0.2066(5) -0.1096(3) 0.0988(15) Uani 1 1 d . . .
H23 H -0.5339 0.1973 -0.1543 0.119 Uiso 1 1 calc R . .
C24 C -0.4514(3) 0.1814(4) -0.0258(3) 0.0802(12) Uani 1 1 d . . .
H24 H -0.5374 0.1552 -0.0140 0.096 Uiso 1 1 calc R . .
C25 C -0.3266(3) 0.1940(3) 0.0428(2) 0.0539(8) Uani 1 1 d . . .
C26 C -0.3290(3) 0.1820(4) 0.1405(2) 0.0748(10) Uani 1 1 d . . .
H26A H -0.3566 0.2547 0.1861 0.090 Uiso 1 1 calc R . .
H26B H -0.4015 0.1043 0.1233 0.090 Uiso 1 1 calc R . .
C27 C -0.2019(3) 0.1770(5) 0.1968(3) 0.0898(13) Uani 1 1 d . . .
H27A H -0.1971 0.0883 0.1679 0.108 Uiso 1 1 calc R . .
H27B H -0.2048 0.2018 0.2685 0.108 Uiso 1 1 calc R . .
C28 C -0.0632(3) 0.2645(3) 0.19752(19) 0.0470(7) Uani 1 1 d . . .
H28 H -0.0644 0.3551 0.2306 0.056 Uiso 1 1 calc R . .
C29 C 0.0663(2) 0.2476(3) 0.25959(18) 0.0367(6) Uani 1 1 d . . .
H29 H 0.0459 0.1570 0.2470 0.044 Uiso 1 1 calc R . .
C30 C 0.0937(3) 0.3309(3) 0.37683(19) 0.0363(6) Uani 1 1 d . . .
C31 C 0.0320(3) 0.2783(3) 0.44185(19) 0.0384(6) Uani 1 1 d . . .
C32 C 0.0302(3) 0.3654(3) 0.5403(2) 0.0488(7) Uani 1 1 d . . .
H32 H 0.0714 0.4531 0.5642 0.059 Uiso 1 1 calc R . .
C33 C -0.0318(3) 0.3230(3) 0.6023(2) 0.0601(9) Uani 1 1 d . . .
H33 H -0.0328 0.3828 0.6674 0.072 Uiso 1 1 calc R . .
C34 C -0.0919(3) 0.1949(3) 0.5704(2) 0.0545(8) Uani 1 1 d . . .
C35 C -0.1615(4) 0.1492(4) 0.6379(3) 0.0838(11) Uani 1 1 d . . .
H35A H -0.1264 0.2137 0.7091 0.126 Uiso 1 1 calc R . .
H35B H -0.1410 0.0703 0.6325 0.126 Uiso 1 1 calc R . .
H35C H -0.2616 0.1343 0.6151 0.126 Uiso 1 1 calc R . .
C36 C -0.0877(3) 0.1079(3) 0.4738(2) 0.0601(8) Uani 1 1 d . . .
H36 H -0.1265 0.0201 0.4515 0.072 Uiso 1 1 calc R . .
C37 C -0.0273(3) 0.1483(3) 0.4098(2) 0.0527(8) Uani 1 1 d . . .
H37 H -0.0263 0.0879 0.3448 0.063 Uiso 1 1 calc R . .
Cl1 Cl 0.52022(10) 0.05911(10) 0.39881(8) 0.0872(4) Uani 1 1 d . . .
N1 N 0.3875(2) 0.4711(2) 0.30112(16) 0.0435(6) Uani 1 1 d . . .
N2 N 0.2516(3) 0.1302(3) 0.0657(2) 0.0596(7) Uani 1 1 d . . .
N3 N 0.0121(3) 0.0774(2) -0.15260(19) 0.0558(7) Uani 1 1 d . . .
O1 O 0.1805(2) 0.47769(19) 0.20933(15) 0.0585(6) Uani 1 1 d . . .
O2 O 0.16406(19) 0.44286(18) 0.41465(13) 0.0488(5) Uani 1 1 d . . .
H2A H 0.331(4) 0.141(3) 0.115(3) 0.073(10) Uiso 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 1.356(4) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(4) . ?
C7 N1 1.447(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.212(3) . ?
C8 N1 1.367(3) . ?
C8 C9 1.556(4) . ?
C9 C10 1.513(3) . ?
C9 C16 1.526(3) . ?
C9 C29 1.547(3) . ?
C10 C11 1.382(4) . ?
C10 C15 1.394(3) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 Cl1 1.738(3) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.398(3) . ?
C16 N2 1.274(3) . ?
C16 C17 1.471(3) . ?
C17 C19 1.349(3) . ?
C17 C18 1.443(4) . ?
C18 N3 1.139(3) . ?
C19 C20 1.478(3) . ?
C19 C28 1.506(3) . ?
C20 C21 1.390(4) . ?
C20 C25 1.390(4) . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.358(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.399(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.485(4) . ?
C26 C27 1.411(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.570(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.536(3) . ?
C28 H28 0.9800 . ?
C29 C30 1.532(3) . ?
C29 H29 0.9800 . ?
C30 O2 1.219(3) . ?
C30 C31 1.479(4) . ?
C31 C37 1.383(4) . ?
C31 C32 1.393(4) . ?
C32 C33 1.373(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(4) . ?
C33 H33 0.9300 . ?
C34 C36 1.381(4) . ?
C34 C35 1.502(4) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.380(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
N2 H2A 0.92(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
C6 C1 C2 120.9(3) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 123.1(3) . . ?
C5 C6 C7 118.6(3) . . ?
N1 C7 C6 114.5(2) . . ?
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 . . ?
O1 C8 N1 125.3(3) . . ?
O1 C8 C9 126.8(2) . . ?
N1 C8 C9 107.8(2) . . ?
C10 C9 C16 112.5(2) . . ?
C10 C9 C29 113.5(2) . . ?
C16 C9 C29 107.84(19) . . ?
C10 C9 C8 101.5(2) . . ?
C16 C9 C8 107.6(2) . . ?
C29 C9 C8 113.9(2) . . ?
C11 C10 C15 120.5(2) . . ?
C11 C10 C9 130.4(2) . . ?
C15 C10 C9 109.0(2) . . ?
C10 C11 C12 117.4(2) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 121.9(3) . . ?
C13 C12 Cl1 119.1(2) . . ?
C11 C12 Cl1 119.0(2) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 N1 128.8(2) . . ?
C10 C15 N1 109.8(2) . . ?
N2 C16 C17 119.1(2) . . ?
N2 C16 C9 125.9(2) . . ?
C17 C16 C9 115.0(2) . . ?
C19 C17 C18 122.1(2) . . ?
C19 C17 C16 123.5(2) . . ?
C18 C17 C16 114.3(2) . . ?
N3 C18 C17 178.5(3) . . ?
C17 C19 C20 122.8(2) . . ?
C17 C19 C28 121.5(2) . . ?
C20 C19 C28 115.5(2) . . ?
C21 C20 C25 119.5(3) . . ?
C21 C20 C19 121.5(2) . . ?
C25 C20 C19 119.1(2) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 121.3(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C20 C25 C24 118.0(3) . . ?
C20 C25 C26 121.3(3) . . ?
C24 C25 C26 120.6(3) . . ?
C27 C26 C25 116.4(3) . . ?
C27 C26 H26A 108.2 . . ?
C25 C26 H26A 108.2 . . ?
C27 C26 H26B 108.2 . . ?
C25 C26 H26B 108.2 . . ?
H26A C26 H26B 107.3 . . ?
C26 C27 C28 115.8(3) . . ?
C26 C27 H27A 108.3 . . ?
C28 C27 H27A 108.3 . . ?
C26 C27 H27B 108.3 . . ?
C28 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
C19 C28 C29 114.0(2) . . ?
C19 C28 C27 105.6(2) . . ?
C29 C28 C27 110.2(2) . . ?
C19 C28 H28 109.0 . . ?
C29 C28 H28 109.0 . . ?
C27 C28 H28 109.0 . . ?
C30 C29 C28 110.74(19) . . ?
C30 C29 C9 109.39(19) . . ?
C28 C29 C9 113.1(2) . . ?
C30 C29 H29 107.8 . . ?
C28 C29 H29 107.8 . . ?
C9 C29 H29 107.8 . . ?
O2 C30 C31 120.8(2) . . ?
O2 C30 C29 118.3(2) . . ?
C31 C30 C29 120.9(2) . . ?
C37 C31 C32 118.1(2) . . ?
C37 C31 C30 123.9(2) . . ?
C32 C31 C30 118.0(2) . . ?
C33 C32 C31 120.7(3) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 121.4(3) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C36 118.1(3) . . ?
C33 C34 C35 121.2(3) . . ?
C36 C34 C35 120.7(3) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C34 121.5(3) . . ?
C37 C36 H36 119.2 . . ?
C34 C36 H36 119.2 . . ?
C36 C37 C31 120.1(3) . . ?
C36 C37 H37 119.9 . . ?
C31 C37 H37 119.9 . . ?
C8 N1 C15 111.7(2) . . ?
C8 N1 C7 123.5(2) . . ?
C15 N1 C7 124.6(2) . . ?
C16 N2 H2A 110(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_1f
_audit_block_doi                 10.5517/cc1k7zsk
_database_code_depnum_ccdc_archive 'CCDC 1437649'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 Cl N3 O2, C3 H7 N O '
_chemical_formula_sum            'C33 H29 Cl N4 O3'
_chemical_formula_weight         565.05

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                   11.0332(12)
_cell_length_b                   11.9112(13)
_cell_length_c                   13.6221(14)
_cell_angle_alpha                115.242(3)
_cell_angle_beta                 92.285(3)
_cell_angle_gamma                115.031(3)
_cell_volume                     1413.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7397
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colroless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.955
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19740
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6510
_reflns_number_gt                4436
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0772P)²+1.2507P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6466
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1888
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.6508(3) 1.0192(2) 0.3910(2) 0.0331(5) Uani 1 1 d . . .
C2 C 0.6280(3) 1.0578(3) 0.3116(2) 0.0437(7) Uani 1 1 d . . .
H2 H 0.5998 0.9920 0.2353 0.052 Uiso 1 1 calc R . .
C3 C 0.6465(3) 1.1920(3) 0.3443(3) 0.0532(8) Uani 1 1 d . . .
H3 H 0.6317 1.2166 0.2905 0.064 Uiso 1 1 calc R . .
C4 C 0.6869(3) 1.2890(3) 0.4571(3) 0.0565(8) Uani 1 1 d . . .
H4 H 0.6980 1.3790 0.4798 0.068 Uiso 1 1 calc R . .
C5 C 0.7109(3) 1.2533(3) 0.5358(3) 0.0519(8) Uani 1 1 d . . .
H5 H 0.7379 1.3201 0.6118 0.062 Uiso 1 1 calc R . .
C6 C 0.6962(3) 1.1198(3) 0.5060(2) 0.0373(6) Uani 1 1 d . . .
C7 C 0.7363(3) 1.0919(3) 0.5954(2) 0.0428(6) Uani 1 1 d . . .
H7A H 0.6891 1.1169 0.6530 0.051 Uiso 1 1 calc R . .
H7B H 0.8354 1.1531 0.6303 0.051 Uiso 1 1 calc R . .
C8 C 0.7025(3) 0.9392(3) 0.5531(2) 0.0393(6) Uani 1 1 d . . .
H8A H 0.6050 0.8822 0.5455 0.047 Uiso 1 1 calc R . .
H8B H 0.7568 0.9346 0.6077 0.047 Uiso 1 1 calc R . .
C9 C 0.7339(3) 0.8780(2) 0.43881(19) 0.0303(5) Uani 1 1 d . . .
H9 H 0.8305 0.9414 0.4464 0.036 Uiso 1 1 calc R . .
C10 C 0.6406(2) 0.8790(2) 0.3554(2) 0.0300(5) Uani 1 1 d . . .
C11 C 0.5571(3) 0.7587(3) 0.2571(2) 0.0325(5) Uani 1 1 d . . .
C12 C 0.4481(3) 0.7463(3) 0.1850(2) 0.0409(6) Uani 1 1 d . . .
C13 C 0.5705(3) 0.6284(2) 0.2129(2) 0.0331(5) Uani 1 1 d . . .
C14 C 0.6975(3) 0.6436(2) 0.2774(2) 0.0314(5) Uani 1 1 d . . .
C15 C 0.7172(2) 0.7308(2) 0.4052(2) 0.0307(5) Uani 1 1 d . . .
H15 H 0.6347 0.6788 0.4244 0.037 Uiso 1 1 calc R . .
C16 C 0.8437(3) 0.7487(3) 0.4734(2) 0.0348(6) Uani 1 1 d . . .
C17 C 0.8323(3) 0.6947(3) 0.5542(2) 0.0329(5) Uani 1 1 d . . .
C18 C 0.9470(3) 0.6901(3) 0.5950(2) 0.0411(6) Uani 1 1 d . . .
H18 H 1.0233 0.7119 0.5658 0.049 Uiso 1 1 calc R . .
C19 C 0.9484(3) 0.6538(3) 0.6779(2) 0.0465(7) Uani 1 1 d . . .
H19 H 1.0247 0.6485 0.7025 0.056 Uiso 1 1 calc R . .
C20 C 0.8382(3) 0.6249(3) 0.7256(2) 0.0446(7) Uani 1 1 d . . .
C21 C 0.8461(4) 0.5953(4) 0.8223(3) 0.0655(9) Uani 1 1 d . . .
H21A H 0.9063 0.5549 0.8175 0.098 Uiso 1 1 calc R . .
H21B H 0.7550 0.5297 0.8185 0.098 Uiso 1 1 calc R . .
H21C H 0.8822 0.6824 0.8924 0.098 Uiso 1 1 calc R . .
C22 C 0.7229(3) 0.6263(3) 0.6837(2) 0.0423(6) Uani 1 1 d . . .
H22 H 0.6471 0.6050 0.7135 0.051 Uiso 1 1 calc R . .
C23 C 0.7190(3) 0.6589(3) 0.5980(2) 0.0380(6) Uani 1 1 d . . .
H23 H 0.6396 0.6568 0.5695 0.046 Uiso 1 1 calc R . .
C24 C 0.6761(3) 0.4951(3) 0.2496(2) 0.0378(6) Uani 1 1 d . . .
C25 C 0.8173(3) 0.6961(3) 0.2295(2) 0.0328(5) Uani 1 1 d . . .
C26 C 0.8846(3) 0.8193(3) 0.2232(2) 0.0383(6) Uani 1 1 d . . .
H26 H 0.8618 0.8913 0.2560 0.046 Uiso 1 1 calc R . .
C27 C 0.9870(3) 0.8326(3) 0.1670(2) 0.0429(6) Uani 1 1 d . . .
C28 C 1.0239(3) 0.7281(3) 0.1178(2) 0.0488(7) Uani 1 1 d . . .
H28 H 1.0938 0.7408 0.0811 0.059 Uiso 1 1 calc R . .
C29 C 0.9559(3) 0.6040(3) 0.1237(2) 0.0493(7) Uani 1 1 d . . .
H29 H 0.9797 0.5326 0.0918 0.059 Uiso 1 1 calc R . .
C30 C 0.8523(3) 0.5893(3) 0.1780(2) 0.0386(6) Uani 1 1 d . . .
C31 C 0.7711(4) 1.1041(4) 1.0819(3) 0.0631(9) Uani 1 1 d . . .
H31 H 0.8267 1.1092 1.1385 0.076 Uiso 1 1 calc R . .
C32 C 0.6817(6) 0.8510(5) 0.9921(5) 0.1103(18) Uani 1 1 d . . .
H32A H 0.7464 0.8755 1.0566 0.165 Uiso 1 1 calc R . .
H32B H 0.7046 0.8034 0.9248 0.165 Uiso 1 1 calc R . .
H32C H 0.5894 0.7894 0.9896 0.165 Uiso 1 1 calc R . .
C33 C 0.6017(5) 0.9569(6) 0.9029(4) 0.0973(15) Uani 1 1 d . . .
H33A H 0.6139 1.0467 0.9141 0.146 Uiso 1 1 calc R . .
H33B H 0.5062 0.8962 0.8944 0.146 Uiso 1 1 calc R . .
H33C H 0.6277 0.9131 0.8362 0.146 Uiso 1 1 calc R . .
Cl1 Cl 1.07067(11) 0.98758(9) 0.15820(9) 0.0734(3) Uani 1 1 d . . .
N1 N 0.3555(3) 0.7240(3) 0.1245(2) 0.0631(8) Uani 1 1 d . . .
N2 N 0.4939(3) 0.5129(2) 0.1230(2) 0.0485(6) Uani 1 1 d . . .
N3 N 0.7690(3) 0.4734(2) 0.1924(2) 0.0465(6) Uani 1 1 d . . .
H3A H 0.7759 0.3974 0.1680 0.056 Uiso 1 1 calc R . .
N4 N 0.6892(3) 0.9794(2) 1.0001(2) 0.0479(6) Uani 1 1 d . . .
O1 O 0.9570(2) 0.8120(2) 0.46101(19) 0.0544(6) Uani 1 1 d . . .
O2 O 0.5946(2) 0.4167(2) 0.27833(19) 0.0520(5) Uani 1 1 d . . .
O3 O 0.7851(3) 1.2172(2) 1.0946(2) 0.0669(7) Uani 1 1 d . . .
H2A H 0.428(4) 0.522(4) 0.088(3) 0.061(10) Uiso 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 1.395(4) . ?
C1 C6 1.403(4) . ?
C1 C10 1.477(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(4) . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.538(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.509(3) . ?
C9 C15 1.534(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.357(3) . ?
C11 C12 1.438(4) . ?
C11 C13 1.482(3) . ?
C12 N1 1.145(3) . ?
C13 N2 1.267(3) . ?
C13 C14 1.523(3) . ?
C14 C25 1.511(3) . ?
C14 C15 1.547(3) . ?
C14 C24 1.548(3) . ?
C15 C16 1.527(3) . ?
C15 H15 0.9800 . ?
C16 O1 1.220(3) . ?
C16 C17 1.479(4) . ?
C17 C23 1.388(4) . ?
C17 C18 1.393(4) . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C22 1.383(4) . ?
C20 C21 1.511(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O2 1.209(3) . ?
C24 N3 1.356(4) . ?
C25 C26 1.378(3) . ?
C25 C30 1.392(3) . ?
C26 C27 1.381(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.380(4) . ?
C27 Cl1 1.740(3) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(4) . ?
C29 H29 0.9300 . ?
C30 N3 1.401(4) . ?
C31 O3 1.221(4) . ?
C31 N4 1.280(4) . ?
C31 H31 0.9300 . ?
C32 N4 1.451(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 N4 1.461(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N2 H2A 0.92(3) . ?
N3 H3A 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 C1 C6 119.2(2) . . ?
C2 C1 C10 120.8(2) . . ?
C6 C1 C10 119.7(2) . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.0(3) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 122.5(2) . . ?
C6 C7 C8 114.0(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 111.2(2) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C15 114.16(19) . . ?
C10 C9 C8 107.34(19) . . ?
C15 C9 C8 110.20(19) . . ?
C10 C9 H9 108.3 . . ?
C15 C9 H9 108.3 . . ?
C8 C9 H9 108.3 . . ?
C11 C10 C1 125.1(2) . . ?
C11 C10 C9 120.8(2) . . ?
C1 C10 C9 114.1(2) . . ?
C10 C11 C12 123.0(2) . . ?
C10 C11 C13 123.5(2) . . ?
C12 C11 C13 113.5(2) . . ?
N1 C12 C11 174.0(3) . . ?
N2 C13 C11 125.9(2) . . ?
N2 C13 C14 118.6(2) . . ?
C11 C13 C14 115.2(2) . . ?
C25 C14 C13 108.4(2) . . ?
C25 C14 C15 118.1(2) . . ?
C13 C14 C15 108.87(19) . . ?
C25 C14 C24 102.22(19) . . ?
C13 C14 C24 109.94(19) . . ?
C15 C14 C24 109.07(19) . . ?
C16 C15 C9 109.06(19) . . ?
C16 C15 C14 110.69(19) . . ?
C9 C15 C14 112.14(18) . . ?
C16 C15 H15 108.3 . . ?
C9 C15 H15 108.3 . . ?
C14 C15 H15 108.3 . . ?
O1 C16 C17 120.0(2) . . ?
O1 C16 C15 117.9(2) . . ?
C17 C16 C15 122.1(2) . . ?
C23 C17 C18 118.2(2) . . ?
C23 C17 C16 123.9(2) . . ?
C18 C17 C16 117.6(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C22 C20 C19 118.4(3) . . ?
C22 C20 C21 121.3(3) . . ?
C19 C20 C21 120.3(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C20 C22 H22 119.6 . . ?
C22 C23 C17 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C17 C23 H23 119.7 . . ?
O2 C24 N3 127.1(2) . . ?
O2 C24 C14 125.3(2) . . ?
N3 C24 C14 107.5(2) . . ?
C26 C25 C30 119.5(2) . . ?
C26 C25 C14 132.0(2) . . ?
C30 C25 C14 108.4(2) . . ?
C25 C26 C27 118.1(2) . . ?
C25 C26 H26 120.9 . . ?
C27 C26 H26 120.9 . . ?
C28 C27 C26 122.5(3) . . ?
C28 C27 Cl1 119.5(2) . . ?
C26 C27 Cl1 118.0(2) . . ?
C27 C28 C29 119.4(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 118.3(3) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 H29 120.9 . . ?
C29 C30 C25 122.1(3) . . ?
C29 C30 N3 128.1(2) . . ?
C25 C30 N3 109.7(2) . . ?
O3 C31 N4 127.8(4) . . ?
O3 C31 H31 116.1 . . ?
N4 C31 H31 116.1 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N4 C33 H33A 109.5 . . ?
N4 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N4 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C13 N2 H2A 110(2) . . ?
C24 N3 C30 112.1(2) . . ?
C24 N3 H3A 124.0 . . ?
C30 N3 H3A 124.0 . . ?
C31 N4 C32 123.6(3) . . ?
C31 N4 C33 121.6(3) . . ?
C32 N4 C33 114.7(3) . . ?

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
N3 H3A O3 0.86 1.99 2.851(3) 173.9 1_544

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_1j
_audit_block_doi                 10.5517/cc1k7ztl
_database_code_depnum_ccdc_archive 'CCDC 1437650'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 Cl N3 O2'
_chemical_formula_sum            'C34 H30 Cl N3 O2'
_chemical_formula_weight         548.06

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'

_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                   9.6977(16)
_cell_length_b                   12.259(2)
_cell_length_c                   12.290(2)
_cell_angle_alpha                97.229(5)
_cell_angle_beta                 102.017(5)
_cell_angle_gamma                92.943(5)
_cell_volume                     1413.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4560
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      22.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.966
_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            14861
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.1196
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.59
_reflns_number_total             6534
_reflns_number_gt                2999
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0586P)²+0.4315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6333
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1926
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1344
_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 0.6248(5) -0.3555(4) 0.0742(4) 0.1017(16) Uani 1 1 d . . .
H1A H 0.5363 -0.3442 0.0956 0.153 Uiso 1 1 calc R . .
H1B H 0.6404 -0.4325 0.0692 0.153 Uiso 1 1 calc R . .
H1C H 0.6224 -0.3313 0.0026 0.153 Uiso 1 1 calc R . .
C2 C 0.7425(4) -0.2906(3) 0.1607(3) 0.0661(11) Uani 1 1 d . . .
H2A H 0.8316 -0.3039 0.1393 0.079 Uiso 1 1 calc R . .
H2B H 0.7458 -0.3172 0.2323 0.079 Uiso 1 1 calc R . .
C3 C 0.7275(4) -0.1678(3) 0.1755(3) 0.0606(10) Uani 1 1 d . . .
H3A H 0.7302 -0.1402 0.1053 0.073 Uiso 1 1 calc R . .
H3B H 0.6361 -0.1546 0.1927 0.073 Uiso 1 1 calc R . .
C4 C 0.8420(4) -0.1047(3) 0.2676(3) 0.0568(10) Uani 1 1 d . . .
H4A H 0.8398 -0.1327 0.3377 0.068 Uiso 1 1 calc R . .
H4B H 0.9334 -0.1174 0.2501 0.068 Uiso 1 1 calc R . .
C5 C 0.7537(3) 0.0640(3) 0.3557(3) 0.0427(8) Uani 1 1 d . . .
C6 C 0.7547(3) 0.1875(2) 0.3434(2) 0.0349(7) Uani 1 1 d . . .
C7 C 0.8446(3) 0.1966(3) 0.2570(2) 0.0383(8) Uani 1 1 d . . .
C8 C 0.8963(3) 0.2855(3) 0.2154(3) 0.0451(8) Uani 1 1 d . . .
H8 H 0.8697 0.3555 0.2364 0.054 Uiso 1 1 calc R . .
C9 C 0.9883(4) 0.2718(3) 0.1418(3) 0.0535(9) Uani 1 1 d . . .
C10 C 1.0431(4) 0.3691(3) 0.0964(3) 0.0776(13) Uani 1 1 d . . .
H10A H 1.1101 0.3462 0.0522 0.116 Uiso 1 1 calc R . .
H10B H 1.0885 0.4243 0.1576 0.116 Uiso 1 1 calc R . .
H10C H 0.9659 0.3990 0.0502 0.116 Uiso 1 1 calc R . .
C11 C 1.0259(4) 0.1656(4) 0.1135(3) 0.0641(11) Uani 1 1 d . . .
H11 H 1.0874 0.1554 0.0650 0.077 Uiso 1 1 calc R . .
C12 C 0.9763(4) 0.0750(3) 0.1538(3) 0.0613(10) Uani 1 1 d . . .
H12 H 1.0030 0.0050 0.1329 0.074 Uiso 1 1 calc R . .
C13 C 0.8858(3) 0.0915(3) 0.2262(3) 0.0455(8) Uani 1 1 d . . .
C14 C 0.6004(3) 0.2193(2) 0.3130(2) 0.0350(7) Uani 1 1 d . . .
H14 H 0.5541 0.2023 0.3733 0.042 Uiso 1 1 calc R . .
C15 C 0.5198(3) 0.1490(2) 0.2035(3) 0.0394(8) Uani 1 1 d . . .
C16 C 0.4243(3) 0.0514(2) 0.2056(2) 0.0372(7) Uani 1 1 d . . .
C17 C 0.3767(3) -0.0201(3) 0.1055(3) 0.0471(9) Uani 1 1 d . . .
H17 H 0.4015 -0.0026 0.0403 0.057 Uiso 1 1 calc R . .
C18 C 0.2942(3) -0.1157(3) 0.1010(3) 0.0495(9) Uani 1 1 d . . .
H18 H 0.2648 -0.1630 0.0338 0.059 Uiso 1 1 calc R . .
C19 C 0.2559(3) -0.1402(3) 0.1963(3) 0.0443(8) Uani 1 1 d . . .
C20 C 0.2968(3) -0.0708(3) 0.2970(3) 0.0501(9) Uani 1 1 d . . .
H20 H 0.2677 -0.0875 0.3609 0.060 Uiso 1 1 calc R . .
C21 C 0.3818(3) 0.0239(3) 0.3004(3) 0.0460(9) Uani 1 1 d . . .
H21 H 0.4114 0.0706 0.3680 0.055 Uiso 1 1 calc R . .
C22 C 0.8262(3) 0.2556(3) 0.4540(3) 0.0384(8) Uani 1 1 d . . .
C23 C 0.7898(3) 0.3720(2) 0.4712(2) 0.0364(7) Uani 1 1 d . . .
C24 C 0.8763(4) 0.4313(3) 0.5729(3) 0.0474(9) Uani 1 1 d . . .
C25 C 0.6885(3) 0.4164(2) 0.4002(2) 0.0347(7) Uani 1 1 d . . .
C26 C 0.6606(3) 0.5357(2) 0.4107(3) 0.0387(8) Uani 1 1 d . . .
C27 C 0.7643(4) 0.6177(3) 0.4721(3) 0.0476(9) Uani 1 1 d . . .
H27 H 0.8525 0.5976 0.5060 0.057 Uiso 1 1 calc R . .
C28 C 0.7368(4) 0.7281(3) 0.4828(3) 0.0560(10) Uani 1 1 d . . .
H28 H 0.8062 0.7814 0.5238 0.067 Uiso 1 1 calc R . .
C29 C 0.6075(4) 0.7583(3) 0.4328(3) 0.0584(10) Uani 1 1 d . . .
H29 H 0.5881 0.8320 0.4413 0.070 Uiso 1 1 calc R . .
C30 C 0.5069(4) 0.6801(3) 0.3703(3) 0.0562(10) Uani 1 1 d . . .
H30 H 0.4198 0.7019 0.3362 0.067 Uiso 1 1 calc R . .
C31 C 0.5309(4) 0.5683(3) 0.3562(3) 0.0458(8) Uani 1 1 d . . .
C32 C 0.4197(4) 0.4883(3) 0.2803(3) 0.0542(9) Uani 1 1 d . . .
H32A H 0.4227 0.4942 0.2028 0.065 Uiso 1 1 calc R . .
H32B H 0.3275 0.5077 0.2915 0.065 Uiso 1 1 calc R . .
C33 C 0.4382(3) 0.3707(3) 0.3006(3) 0.0483(9) Uani 1 1 d . . .
H33A H 0.3751 0.3214 0.2410 0.058 Uiso 1 1 calc R . .
H33B H 0.4128 0.3601 0.3711 0.058 Uiso 1 1 calc R . .
C34 C 0.5909(3) 0.3420(2) 0.3049(2) 0.0348(7) Uani 1 1 d . . .
H34 H 0.6159 0.3564 0.2345 0.042 Uiso 1 1 calc R . .
Cl1 Cl 0.15409(10) -0.26219(8) 0.19206(8) 0.0688(3) Uani 1 1 d . . .
N1 N 0.8268(3) 0.0141(2) 0.2826(2) 0.0494(7) Uani 1 1 d . . .
N2 N 0.9146(4) 0.2105(3) 0.5224(3) 0.0577(9) Uani 1 1 d . . .
N3 N 0.9518(4) 0.4665(3) 0.6558(3) 0.0707(10) Uani 1 1 d . . .
O1 O 0.6955(2) 0.01869(17) 0.41773(19) 0.0517(6) Uani 1 1 d . . .
O2 O 0.5386(3) 0.17496(18) 0.11528(18) 0.0569(7) Uani 1 1 d . . .
H2C H 0.955(4) 0.254(3) 0.583(3) 0.070(13) Uiso 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 1.501(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.512(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.511(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.464(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.209(4) . ?
C5 N1 1.363(4) . ?
C5 C6 1.540(4) . ?
C6 C22 1.513(4) . ?
C6 C7 1.518(4) . ?
C6 C14 1.548(4) . ?
C7 C8 1.375(4) . ?
C7 C13 1.398(4) . ?
C8 C9 1.399(4) . ?
C8 H8 0.9300 . ?
C9 C11 1.390(5) . ?
C9 C10 1.497(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 N1 1.408(4) . ?
C14 C34 1.527(4) . ?
C14 C15 1.539(4) . ?
C14 H14 0.9800 . ?
C15 O2 1.213(3) . ?
C15 C16 1.482(4) . ?
C16 C21 1.387(4) . ?
C16 C17 1.394(4) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(4) . ?
C19 Cl1 1.738(3) . ?
C20 C21 1.380(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N2 1.270(4) . ?
C22 C23 1.488(4) . ?
C23 C25 1.356(4) . ?
C23 C24 1.437(5) . ?
C24 N3 1.143(4) . ?
C25 C26 1.496(4) . ?
C25 C34 1.510(4) . ?
C26 C31 1.399(4) . ?
C26 C27 1.407(4) . ?
C27 C28 1.388(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.397(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.496(4) . ?
C32 C33 1.507(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.532(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34 0.9800 . ?
N2 H2C 0.86(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 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 . . ?
C1 C2 C3 113.7(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 112.9(3) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 112.9(3) . . ?
N1 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O1 C5 N1 125.9(3) . . ?
O1 C5 C6 126.0(3) . . ?
N1 C5 C6 108.1(3) . . ?
C22 C6 C7 110.1(2) . . ?
C22 C6 C5 109.7(2) . . ?
C7 C6 C5 102.5(2) . . ?
C22 C6 C14 107.9(2) . . ?
C7 C6 C14 117.4(2) . . ?
C5 C6 C14 109.1(2) . . ?
C8 C7 C13 119.6(3) . . ?
C8 C7 C6 132.3(3) . . ?
C13 C7 C6 107.9(3) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C11 C9 C8 117.5(3) . . ?
C11 C9 C10 122.2(3) . . ?
C8 C9 C10 120.3(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 123.2(3) . . ?
C12 C11 H11 118.4 . . ?
C9 C11 H11 118.4 . . ?
C11 C12 C13 117.8(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C12 C13 C7 121.2(3) . . ?
C12 C13 N1 128.6(3) . . ?
C7 C13 N1 110.1(3) . . ?
C34 C14 C15 110.7(2) . . ?
C34 C14 C6 112.8(2) . . ?
C15 C14 C6 110.4(2) . . ?
C34 C14 H14 107.5 . . ?
C15 C14 H14 107.5 . . ?
C6 C14 H14 107.5 . . ?
O2 C15 C16 121.0(3) . . ?
O2 C15 C14 118.0(3) . . ?
C16 C15 C14 121.0(3) . . ?
C21 C16 C17 117.5(3) . . ?
C21 C16 C15 124.9(3) . . ?
C17 C16 C15 117.6(3) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.7(3) . . ?
C18 C19 Cl1 119.5(3) . . ?
C20 C19 Cl1 118.8(3) . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 C16 121.7(3) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
N2 C22 C23 125.5(3) . . ?
N2 C22 C6 118.0(3) . . ?
C23 C22 C6 116.4(3) . . ?
C25 C23 C24 124.4(3) . . ?
C25 C23 C22 124.5(3) . . ?
C24 C23 C22 111.1(3) . . ?
N3 C24 C23 171.6(4) . . ?
C23 C25 C26 124.9(3) . . ?
C23 C25 C34 119.4(3) . . ?
C26 C25 C34 115.7(3) . . ?
C31 C26 C27 118.5(3) . . ?
C31 C26 C25 120.2(3) . . ?
C27 C26 C25 121.3(3) . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 122.0(4) . . ?
C29 C30 H30 119.0 . . ?
C31 C30 H30 119.0 . . ?
C30 C31 C26 118.6(3) . . ?
C30 C31 C32 119.1(3) . . ?
C26 C31 C32 122.3(3) . . ?
C31 C32 C33 112.7(3) . . ?
C31 C32 H32A 109.1 . . ?
C33 C32 H32A 109.1 . . ?
C31 C32 H32B 109.1 . . ?
C33 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C34 111.3(3) . . ?
C32 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C25 C34 C14 113.8(2) . . ?
C25 C34 C33 109.3(2) . . ?
C14 C34 C33 109.2(2) . . ?
C25 C34 H34 108.1 . . ?
C14 C34 H34 108.1 . . ?
C33 C34 H34 108.1 . . ?
C5 N1 C13 111.2(3) . . ?
C5 N1 C4 123.3(3) . . ?
C13 N1 C4 125.5(3) . . ?
C22 N2 H2C 114(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 H2C N3 0.86(4) 2.65(4) 3.318(4) 135(3) .

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_2b
_audit_block_doi                 10.5517/cc1k7zvm
_database_code_depnum_ccdc_archive 'CCDC 1437651'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H29 N3 O3'
_chemical_formula_sum            'C33 H29 N3 O3'
_chemical_formula_weight         515.59

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   24.966(7)
_cell_length_b                   14.424(4)
_cell_length_c                   7.728(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.871(3)
_cell_angle_gamma                90.00
_cell_volume                     2762.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8755
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.981
_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            22916
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         0.82
_diffrn_reflns_theta_max         27.55
_reflns_number_total             6373
_reflns_number_gt                4865
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0643P)²+0.8889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6205
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.48099(10) 0.10728(19) 0.9206(4) 0.0902(8) Uani 1 1 d . . .
H1 H 0.5007 0.0954 0.8282 0.108 Uiso 1 1 calc R . .
C2 C 0.50592(14) 0.1473(2) 1.0688(5) 0.1186(12) Uani 1 1 d . . .
H2A H 0.5425 0.1616 1.0778 0.142 Uiso 1 1 calc R . .
C3 C 0.47706(17) 0.1661(2) 1.2035(5) 0.1246(14) Uani 1 1 d . . .
H3 H 0.4938 0.1947 1.3035 0.150 Uiso 1 1 calc R . .
C4 C 0.42315(15) 0.1430(2) 1.1922(4) 0.1154(11) Uani 1 1 d . . .
H4 H 0.4037 0.1555 1.2850 0.138 Uiso 1 1 calc R . .
C5 C 0.39779(10) 0.10091(18) 1.0419(3) 0.0807(7) Uani 1 1 d . . .
H5 H 0.3616 0.0844 1.0343 0.097 Uiso 1 1 calc R . .
C6 C 0.42672(8) 0.08414(14) 0.9057(3) 0.0623(5) Uani 1 1 d . . .
C7 C 0.40305(7) 0.03565(18) 0.7413(3) 0.0715(6) Uani 1 1 d . . .
H7A H 0.4140 0.0689 0.6423 0.086 Uiso 1 1 calc R . .
H7B H 0.4184 -0.0261 0.7404 0.086 Uiso 1 1 calc R . .
C8 C 0.31886(6) -0.04921(13) 0.7730(2) 0.0489(4) Uani 1 1 d . . .
C9 C 0.25774(6) -0.03683(10) 0.71560(18) 0.0395(3) Uani 1 1 d . . .
C10 C 0.25644(6) 0.05312(11) 0.61237(19) 0.0433(3) Uani 1 1 d . . .
C11 C 0.21406(7) 0.10182(12) 0.5244(2) 0.0500(4) Uani 1 1 d . . .
H11 H 0.1793 0.0777 0.5161 0.060 Uiso 1 1 calc R . .
C12 C 0.22319(10) 0.18771(14) 0.4471(2) 0.0660(5) Uani 1 1 d . . .
C13 C 0.17632(12) 0.24221(17) 0.3573(3) 0.0959(8) Uani 1 1 d . . .
H13A H 0.1891 0.3003 0.3175 0.144 Uiso 1 1 calc R . .
H13B H 0.1506 0.2535 0.4377 0.144 Uiso 1 1 calc R . .
H13C H 0.1595 0.2075 0.2595 0.144 Uiso 1 1 calc R . .
C14 C 0.27530(11) 0.22099(16) 0.4613(3) 0.0794(7) Uani 1 1 d . . .
H14 H 0.2817 0.2777 0.4104 0.095 Uiso 1 1 calc R . .
C15 C 0.31856(10) 0.17334(16) 0.5484(3) 0.0737(6) Uani 1 1 d . . .
H15 H 0.3533 0.1974 0.5564 0.088 Uiso 1 1 calc R . .
C16 C 0.30852(7) 0.08839(13) 0.6234(2) 0.0532(4) Uani 1 1 d . . .
C17 C 0.23322(6) -0.12179(10) 0.61482(18) 0.0374(3) Uani 1 1 d . . .
H17 H 0.2432 -0.1766 0.6865 0.045 Uiso 1 1 calc R . .
C18 C 0.25635(6) -0.13489(11) 0.4413(2) 0.0426(3) Uani 1 1 d . . .
C19 C 0.33603(8) -0.14711(17) 0.3035(3) 0.0683(6) Uani 1 1 d . . .
H19A H 0.3279 -0.2084 0.2557 0.082 Uiso 1 1 calc R . .
H19B H 0.3232 -0.1015 0.2160 0.082 Uiso 1 1 calc R . .
C20 C 0.39322(10) -0.1372(3) 0.3498(4) 0.1237(13) Uani 1 1 d . . .
H20A H 0.4017 -0.0732 0.3745 0.186 Uiso 1 1 calc R . .
H20B H 0.4117 -0.1576 0.2547 0.186 Uiso 1 1 calc R . .
H20C H 0.4045 -0.1740 0.4511 0.186 Uiso 1 1 calc R . .
C21 C 0.23065(6) -0.02078(10) 0.88065(18) 0.0401(3) Uani 1 1 d . . .
C22 C 0.17213(6) -0.04014(10) 0.86722(18) 0.0394(3) Uani 1 1 d . . .
C23 C 0.14833(6) -0.01547(13) 1.0224(2) 0.0494(4) Uani 1 1 d . . .
C24 C 0.14331(6) -0.07675(10) 0.72321(18) 0.0370(3) Uani 1 1 d . . .
C25 C 0.17141(6) -0.11957(10) 0.57980(18) 0.0365(3) Uani 1 1 d . . .
H25 H 0.1613 -0.0842 0.4726 0.044 Uiso 1 1 calc R . .
C26 C 0.14877(6) -0.21843(11) 0.5522(2) 0.0434(3) Uani 1 1 d . . .
H26A H 0.1679 -0.2505 0.4680 0.052 Uiso 1 1 calc R . .
H26B H 0.1545 -0.2523 0.6613 0.052 Uiso 1 1 calc R . .
C27 C 0.08913(7) -0.21654(14) 0.4877(2) 0.0553(4) Uani 1 1 d . . .
H27A H 0.0844 -0.1983 0.3660 0.066 Uiso 1 1 calc R . .
H27B H 0.0746 -0.2786 0.4951 0.066 Uiso 1 1 calc R . .
C28 C 0.05784(6) -0.15121(13) 0.5892(2) 0.0499(4) Uani 1 1 d . . .
C29 C 0.00161(7) -0.15723(18) 0.5724(3) 0.0701(6) Uani 1 1 d . . .
H29 H -0.0157 -0.2038 0.5036 0.084 Uiso 1 1 calc R . .
C30 C -0.02869(8) -0.0954(2) 0.6560(3) 0.0793(7) Uani 1 1 d . . .
H30 H -0.0660 -0.1015 0.6455 0.095 Uiso 1 1 calc R . .
C31 C -0.00386(8) -0.02498(18) 0.7546(3) 0.0717(6) Uani 1 1 d . . .
H31 H -0.0244 0.0181 0.8071 0.086 Uiso 1 1 calc R . .
C32 C 0.05170(7) -0.01821(14) 0.7756(2) 0.0561(4) Uani 1 1 d . . .
H32 H 0.0683 0.0297 0.8425 0.067 Uiso 1 1 calc R . .
C33 C 0.08363(6) -0.08269(12) 0.69736(19) 0.0433(3) Uani 1 1 d . . .
N1 N 0.34472(6) 0.02745(11) 0.71819(19) 0.0564(4) Uani 1 1 d . . .
N2 N 0.25890(6) 0.01348(12) 1.01247(19) 0.0565(4) Uani 1 1 d . . .
N3 N 0.13375(6) 0.00367(15) 1.1523(2) 0.0747(5) Uani 1 1 d . . .
O1 O 0.33999(5) -0.11439(10) 0.85308(17) 0.0633(4) Uani 1 1 d . . .
O2 O 0.22965(5) -0.14557(11) 0.30350(16) 0.0685(4) Uani 1 1 d . . .
O3 O 0.30940(5) -0.13356(10) 0.46073(16) 0.0606(3) Uani 1 1 d . . .
H2B H 0.2392(9) 0.0226(15) 1.101(3) 0.074(6) Uiso 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 1.364(4) . ?
C1 C6 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 N1 1.451(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.211(2) . ?
C8 N1 1.373(2) . ?
C8 C9 1.548(2) . ?
C9 C10 1.521(2) . ?
C9 C21 1.5312(19) . ?
C9 C17 1.539(2) . ?
C10 C11 1.380(2) . ?
C10 C16 1.389(2) . ?
C11 C12 1.406(2) . ?
C11 H11 0.9300 . ?
C12 C14 1.379(3) . ?
C12 C13 1.508(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 N1 1.403(2) . ?
C17 C18 1.534(2) . ?
C17 C25 1.5349(19) . ?
C17 H17 0.9800 . ?
C18 O2 1.1971(19) . ?
C18 O3 1.3151(19) . ?
C19 C20 1.437(3) . ?
C19 O3 1.466(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.268(2) . ?
C21 C22 1.479(2) . ?
C22 C24 1.358(2) . ?
C22 C23 1.445(2) . ?
C23 N3 1.142(2) . ?
C24 C33 1.482(2) . ?
C24 C25 1.5126(19) . ?
C25 C26 1.539(2) . ?
C25 H25 0.9800 . ?
C26 C27 1.513(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.504(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.397(2) . ?
C28 C33 1.401(2) . ?
C29 C30 1.379(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.381(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.407(2) . ?
C32 H32 0.9300 . ?
N2 H2B 0.90(2) . ?

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 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 122.76(18) . . ?
C1 C6 C7 117.5(2) . . ?
N1 C7 C6 115.33(16) . . ?
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 . . ?
O1 C8 N1 126.22(16) . . ?
O1 C8 C9 126.16(16) . . ?
N1 C8 C9 107.61(15) . . ?
C10 C9 C21 108.92(12) . . ?
C10 C9 C17 115.56(12) . . ?
C21 C9 C17 110.69(12) . . ?
C10 C9 C8 101.95(12) . . ?
C21 C9 C8 107.30(12) . . ?
C17 C9 C8 111.83(12) . . ?
C11 C10 C16 120.05(16) . . ?
C11 C10 C9 131.28(14) . . ?
C16 C10 C9 108.61(14) . . ?
C10 C11 C12 120.29(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C14 C12 C11 118.2(2) . . ?
C14 C12 C13 121.9(2) . . ?
C11 C12 C13 119.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C15 122.65(19) . . ?
C12 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C16 118.07(19) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C10 C16 C15 120.74(19) . . ?
C10 C16 N1 110.02(15) . . ?
C15 C16 N1 129.24(18) . . ?
C18 C17 C25 108.91(11) . . ?
C18 C17 C9 111.84(12) . . ?
C25 C17 C9 113.78(12) . . ?
C18 C17 H17 107.3 . . ?
C25 C17 H17 107.3 . . ?
C9 C17 H17 107.3 . . ?
O2 C18 O3 123.31(14) . . ?
O2 C18 C17 124.48(14) . . ?
O3 C18 C17 112.21(13) . . ?
C20 C19 O3 108.43(18) . . ?
C20 C19 H19A 110.0 . . ?
O3 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
O3 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 125.44(14) . . ?
N2 C21 C9 118.01(14) . . ?
C22 C21 C9 116.37(12) . . ?
C24 C22 C23 123.09(14) . . ?
C24 C22 C21 123.58(13) . . ?
C23 C22 C21 113.33(13) . . ?
N3 C23 C22 174.30(17) . . ?
C22 C24 C33 123.96(13) . . ?
C22 C24 C25 120.84(13) . . ?
C33 C24 C25 115.13(12) . . ?
C24 C25 C17 115.08(12) . . ?
C24 C25 C26 106.56(12) . . ?
C17 C25 C26 110.48(12) . . ?
C24 C25 H25 108.2 . . ?
C17 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C27 C26 C25 111.08(13) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C28 C27 C26 113.06(14) . . ?
C28 C27 H27A 109.0 . . ?
C26 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C33 118.97(16) . . ?
C29 C28 C27 119.46(16) . . ?
C33 C28 C27 121.55(14) . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C31 C30 C29 120.13(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 119.88(19) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 121.02(18) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C28 C33 C32 118.63(15) . . ?
C28 C33 C24 120.28(14) . . ?
C32 C33 C24 121.05(15) . . ?
C8 N1 C16 111.62(14) . . ?
C8 N1 C7 122.00(17) . . ?
C16 N1 C7 126.00(17) . . ?
C21 N2 H2B 111.4(14) . . ?
C18 O3 C19 117.00(13) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_2c
_audit_block_doi                 10.5517/cc1k7zwn
_database_code_depnum_ccdc_archive 'CCDC 1437652'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 Cl N3 O3'
_chemical_formula_sum            'C32 H26 Cl N3 O3'
_chemical_formula_weight         536.01

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.837(2)
_cell_length_b                   11.2462(16)
_cell_length_c                   20.714(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.956(8)
_cell_angle_gamma                90.00
_cell_volume                     2649.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5393
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.964
_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            26637
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6111
_reflns_number_gt                3181
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0590P)²+0.0859P] 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         6074
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58121(19) 0.2009(2) 0.95472(15) 0.0552(6) Uani 1 1 d . . .
H1 H 0.5582 0.1303 0.9245 0.066 Uiso 1 1 calc R . .
C2 C 0.6496(2) 0.1971(3) 1.04102(19) 0.0739(8) Uani 1 1 d . . .
H2A H 0.6745 0.1244 1.0689 0.089 Uiso 1 1 calc R . .
C3 C 0.6805(2) 0.2994(4) 1.08509(18) 0.0826(9) Uani 1 1 d . . .
H3 H 0.7269 0.2968 1.1434 0.099 Uiso 1 1 calc R . .
C4 C 0.6437(2) 0.4068(3) 1.04441(18) 0.0750(8) Uani 1 1 d . . .
H4 H 0.6642 0.4768 1.0750 0.090 Uiso 1 1 calc R . .
C5 C 0.5759(2) 0.4111(2) 0.95775(16) 0.0586(6) Uani 1 1 d . . .
H5 H 0.5503 0.4840 0.9301 0.070 Uiso 1 1 calc R . .
C6 C 0.54634(17) 0.3079(2) 0.91245(13) 0.0438(5) Uani 1 1 d . . .
C7 C 0.48153(19) 0.3087(2) 0.81907(13) 0.0555(6) Uani 1 1 d . . .
H7A H 0.5384 0.3153 0.8105 0.067 Uiso 1 1 calc R . .
H7B H 0.4409 0.2334 0.7953 0.067 Uiso 1 1 calc R . .
C8 C 0.29130(17) 0.41083(18) 0.76054(12) 0.0402(5) Uani 1 1 d . . .
C9 C 0.25037(19) 0.33289(19) 0.78784(13) 0.0480(5) Uani 1 1 d . . .
H9 H 0.2927 0.2650 0.8180 0.058 Uiso 1 1 calc R . .
C10 C 0.1442(2) 0.35838(19) 0.76913(13) 0.0500(6) Uani 1 1 d . . .
H10 H 0.1150 0.3076 0.7872 0.060 Uiso 1 1 calc R . .
C11 C 0.08242(18) 0.45870(19) 0.72386(13) 0.0449(5) Uani 1 1 d . . .
C12 C 0.12250(17) 0.53642(18) 0.69540(12) 0.0418(5) Uani 1 1 d . . .
H12 H 0.0793 0.6036 0.6644 0.050 Uiso 1 1 calc R . .
C13 C 0.22866(16) 0.51169(17) 0.71421(12) 0.0369(5) Uani 1 1 d . . .
C14 C 0.30126(16) 0.57967(17) 0.69787(12) 0.0372(5) Uani 1 1 d . . .
C15 C 0.41198(18) 0.50148(19) 0.74242(13) 0.0451(5) Uani 1 1 d . . .
C16 C 0.24462(16) 0.59766(16) 0.60467(12) 0.0354(5) Uani 1 1 d . . .
H16 H 0.3007 0.6414 0.6036 0.042 Uiso 1 1 calc R . .
C17 C 0.21909(18) 0.48055(17) 0.55998(13) 0.0393(5) Uani 1 1 d . . .
C18 C 0.2862(2) 0.3363(2) 0.51612(18) 0.0748(8) Uani 1 1 d . . .
H18A H 0.2041 0.3190 0.4698 0.090 Uiso 1 1 calc R . .
H18B H 0.3169 0.2751 0.5586 0.090 Uiso 1 1 calc R . .
C19 C 0.3532(3) 0.3385(3) 0.48589(17) 0.0851(9) Uani 1 1 d . . .
H19A H 0.3148 0.3903 0.4380 0.128 Uiso 1 1 calc R . .
H19B H 0.3569 0.2596 0.4700 0.128 Uiso 1 1 calc R . .
H19C H 0.4314 0.3669 0.5300 0.128 Uiso 1 1 calc R . .
C20 C 0.33153(18) 0.70280(19) 0.73768(13) 0.0419(5) Uani 1 1 d . . .
C21 C 0.23434(18) 0.78989(17) 0.68840(12) 0.0381(5) Uani 1 1 d . . .
C22 C 0.25138(19) 0.8947(2) 0.73527(14) 0.0493(6) Uani 1 1 d . . .
C23 C 0.13585(16) 0.77079(16) 0.60691(12) 0.0351(5) Uani 1 1 d . . .
C24 C 0.13220(16) 0.67097(16) 0.55705(11) 0.0343(5) Uani 1 1 d . . .
H24 H 0.0678 0.6175 0.5395 0.041 Uiso 1 1 calc R . .
C25 C 0.10187(18) 0.72687(18) 0.47771(12) 0.0428(5) Uani 1 1 d . . .
H25A H 0.1584 0.7887 0.4936 0.051 Uiso 1 1 calc R . .
H25B H 0.1062 0.6668 0.4462 0.051 Uiso 1 1 calc R . .
C26 C -0.02051(18) 0.77939(18) 0.42310(12) 0.0455(5) Uani 1 1 d . . .
H26A H -0.0284 0.8355 0.3842 0.055 Uiso 1 1 calc R . .
H26B H -0.0772 0.7162 0.3901 0.055 Uiso 1 1 calc R . .
C27 C -0.04970(18) 0.84169(16) 0.47179(13) 0.0401(5) Uani 1 1 d . . .
C28 C -0.15744(19) 0.89910(18) 0.42801(15) 0.0519(6) Uani 1 1 d . . .
H28 H -0.2077 0.9018 0.3695 0.062 Uiso 1 1 calc R . .
C29 C -0.1914(2) 0.95194(19) 0.46928(18) 0.0590(7) Uani 1 1 d . . .
H29 H -0.2639 0.9898 0.4387 0.071 Uiso 1 1 calc R . .
C30 C -0.1183(2) 0.94886(19) 0.55569(18) 0.0574(6) Uani 1 1 d . . .
H30 H -0.1411 0.9846 0.5837 0.069 Uiso 1 1 calc R . .
C31 C -0.01098(19) 0.89245(18) 0.60062(15) 0.0484(6) Uani 1 1 d . . .
H31 H 0.0378 0.8894 0.6591 0.058 Uiso 1 1 calc R . .
C32 C 0.02569(17) 0.83966(16) 0.55966(13) 0.0377(5) Uani 1 1 d . . .
Cl1 Cl -0.05022(5) 0.49012(6) 0.70174(4) 0.0715(2) Uani 1 1 d . . .
N1 N 0.39670(14) 0.40452(15) 0.77402(10) 0.0455(4) Uani 1 1 d . . .
N2 N 0.43085(16) 0.71961(18) 0.80927(12) 0.0676(6) Uani 1 1 d . . .
H2B H 0.4407 0.7915 0.8308 0.081 Uiso 1 1 d R . .
N3 N 0.27304(19) 0.97519(19) 0.77680(13) 0.0708(6) Uani 1 1 d . . .
O1 O 0.49583(13) 0.51982(14) 0.74619(10) 0.0633(5) Uani 1 1 d . . .
O2 O 0.13748(15) 0.41897(14) 0.53556(13) 0.0803(6) Uani 1 1 d . . .
O3 O 0.29724(13) 0.45289(13) 0.55192(11) 0.0632(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 1.377(3) . ?
C1 C6 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(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 1.403(2) . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 Cl1 1.746(2) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.526(3) . ?
C14 C20 1.524(3) . ?
C14 C15 1.542(3) . ?
C14 C16 1.546(3) . ?
C15 O1 1.213(2) . ?
C15 N1 1.364(3) . ?
C16 C17 1.512(3) . ?
C16 C24 1.524(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.190(2) . ?
C17 O3 1.311(2) . ?
C18 O3 1.462(3) . ?
C18 C19 1.477(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.265(2) . ?
C20 C21 1.480(3) . ?
C21 C23 1.365(3) . ?
C21 C22 1.442(3) . ?
C22 N3 1.144(3) . ?
C23 C32 1.475(3) . ?
C23 C24 1.503(3) . ?
C24 C25 1.533(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.512(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.502(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.390(3) . ?
C27 C32 1.396(3) . ?
C28 C29 1.375(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.400(3) . ?
C31 H31 0.9300 . ?
N2 H2B 0.8898 . ?

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 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 122.1(2) . . ?
C1 C6 C7 119.3(2) . . ?
N1 C7 C6 113.84(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 . . ?
C9 C8 C13 121.86(19) . . ?
C9 C8 N1 127.96(19) . . ?
C13 C8 N1 110.18(17) . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 120.01(19) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.88(19) . . ?
C10 C11 Cl1 119.40(16) . . ?
C12 C11 Cl1 118.72(17) . . ?
C11 C12 C13 118.36(19) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C8 119.59(18) . . ?
C12 C13 C14 132.36(18) . . ?
C8 C13 C14 107.95(16) . . ?
C20 C14 C13 109.87(15) . . ?
C20 C14 C15 111.34(16) . . ?
C13 C14 C15 102.36(15) . . ?
C20 C14 C16 106.96(15) . . ?
C13 C14 C16 116.58(15) . . ?
C15 C14 C16 109.75(15) . . ?
O1 C15 N1 125.79(19) . . ?
O1 C15 C14 126.59(19) . . ?
N1 C15 C14 107.56(17) . . ?
C17 C16 C24 109.60(15) . . ?
C17 C16 C14 111.85(15) . . ?
C24 C16 C14 111.74(15) . . ?
C17 C16 H16 107.8 . . ?
C24 C16 H16 107.8 . . ?
C14 C16 H16 107.8 . . ?
O2 C17 O3 123.36(19) . . ?
O2 C17 C16 123.64(18) . . ?
O3 C17 C16 112.99(17) . . ?
O3 C18 C19 108.3(2) . . ?
O3 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O3 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 126.5(2) . . ?
N2 C20 C14 119.12(19) . . ?
C21 C20 C14 114.20(17) . . ?
C23 C21 C22 123.15(19) . . ?
C23 C21 C20 122.96(17) . . ?
C22 C21 C20 113.86(18) . . ?
N3 C22 C21 175.1(3) . . ?
C21 C23 C32 126.03(17) . . ?
C21 C23 C24 120.33(17) . . ?
C32 C23 C24 113.63(16) . . ?
C23 C24 C16 114.71(16) . . ?
C23 C24 C25 106.66(15) . . ?
C16 C24 C25 111.20(15) . . ?
C23 C24 H24 108.0 . . ?
C16 C24 H24 108.0 . . ?
C25 C24 H24 108.0 . . ?
C26 C25 C24 110.31(16) . . ?
C26 C25 H25A 109.6 . . ?
C24 C25 H25A 109.6 . . ?
C26 C25 H25B 109.6 . . ?
C24 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 113.90(17) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C32 118.75(19) . . ?
C28 C27 C26 119.02(19) . . ?
C32 C27 C26 122.18(18) . . ?
C29 C28 C27 121.5(2) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 119.6(2) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 121.0(2) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C27 C32 C31 119.03(19) . . ?
C27 C32 C23 119.50(17) . . ?
C31 C32 C23 121.11(19) . . ?
C15 N1 C8 111.83(16) . . ?
C15 N1 C7 124.01(18) . . ?
C8 N1 C7 124.12(18) . . ?
C20 N2 H2B 114.6 . . ?
C17 O3 C18 117.17(17) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_2cc
_audit_block_doi                 10.5517/cc1k7zxp
_database_code_depnum_ccdc_archive 'CCDC 1437653'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 Cl N3 O3'
_chemical_formula_sum            'C32 H26 Cl N3 O3'
_chemical_formula_weight         536.01

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                   10.113(4)
_cell_length_b                   12.254(4)
_cell_length_c                   12.833(4)
_cell_angle_alpha                109.262(9)
_cell_angle_beta                 105.103(10)
_cell_angle_gamma                96.708(10)
_cell_volume                     1413.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2622
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      20.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.970
_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            21399
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_sigmaI/netI    0.1846
_diffrn_reflns_limit_h_min       -13
_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       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6503
_reflns_number_gt                2322
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0643P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6377
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2129
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.892
_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 0.6566(4) 0.2284(3) 0.6629(3) 0.0660(10) Uani 1 1 d . . .
H1 H 0.6528 0.2866 0.7298 0.079 Uiso 1 1 calc R . .
C2 C 0.7633(5) 0.1699(4) 0.6700(4) 0.0908(14) Uani 1 1 d . . .
H2A H 0.8293 0.1865 0.7421 0.109 Uiso 1 1 calc R . .
C3 C 0.7747(4) 0.0871(4) 0.5725(5) 0.0886(14) Uani 1 1 d . . .
H3 H 0.8485 0.0484 0.5775 0.106 Uiso 1 1 calc R . .
C4 C 0.6758(5) 0.0626(3) 0.4680(4) 0.0748(11) Uani 1 1 d . . .
H4 H 0.6832 0.0077 0.4007 0.090 Uiso 1 1 calc R . .
C5 C 0.5653(4) 0.1182(3) 0.4609(3) 0.0581(9) Uani 1 1 d . . .
H5 H 0.4966 0.0986 0.3894 0.070 Uiso 1 1 calc R . .
C6 C 0.5554(3) 0.2028(3) 0.5591(3) 0.0449(8) Uani 1 1 d . . .
C7 C 0.4367(3) 0.2644(3) 0.5593(2) 0.0518(9) Uani 1 1 d . . .
H7A H 0.3719 0.2271 0.5879 0.062 Uiso 1 1 calc R . .
H7B H 0.4735 0.3460 0.6133 0.062 Uiso 1 1 calc R . .
C8 C 0.4127(3) 0.3194(2) 0.3824(3) 0.0382(7) Uani 1 1 d . . .
C9 C 0.5472(3) 0.3835(2) 0.4098(3) 0.0484(9) Uani 1 1 d . . .
H9 H 0.6163 0.3955 0.4790 0.058 Uiso 1 1 calc R . .
C10 C 0.5756(3) 0.4290(2) 0.3309(3) 0.0510(9) Uani 1 1 d . . .
H10 H 0.6654 0.4719 0.3465 0.061 Uiso 1 1 calc R . .
C11 C 0.4718(4) 0.4115(2) 0.2289(3) 0.0474(8) Uani 1 1 d . . .
C12 C 0.3374(3) 0.3481(2) 0.2025(3) 0.0448(8) Uani 1 1 d . . .
H12 H 0.2682 0.3364 0.1335 0.054 Uiso 1 1 calc R . .
C13 C 0.3088(3) 0.3029(2) 0.2806(3) 0.0367(7) Uani 1 1 d . . .
C14 C 0.1768(3) 0.2264(2) 0.2745(2) 0.0345(7) Uani 1 1 d . . .
C15 C 0.2180(3) 0.2151(2) 0.3950(3) 0.0417(8) Uani 1 1 d . . .
C16 C 0.0439(3) 0.2749(2) 0.2485(2) 0.0342(7) Uani 1 1 d . . .
H16 H 0.0269 0.2794 0.1714 0.041 Uiso 1 1 calc R . .
C17 C 0.0699(3) 0.4001(2) 0.3363(3) 0.0395(8) Uani 1 1 d . . .
C18 C 0.0192(4) 0.5901(3) 0.3707(3) 0.0658(10) Uani 1 1 d . . .
H18A H 0.1141 0.6338 0.3889 0.079 Uiso 1 1 calc R . .
H18B H 0.0040 0.5922 0.4428 0.079 Uiso 1 1 calc R . .
C19 C -0.0836(4) 0.6436(3) 0.3108(3) 0.0759(11) Uani 1 1 d . . .
H19A H -0.0641 0.6453 0.2419 0.114 Uiso 1 1 calc R . .
H19B H -0.0768 0.7230 0.3619 0.114 Uiso 1 1 calc R . .
H19C H -0.1766 0.5974 0.2895 0.114 Uiso 1 1 calc R . .
C20 C 0.1490(3) 0.1012(2) 0.1838(2) 0.0392(8) Uani 1 1 d . . .
C21 C 0.0130(3) 0.0244(2) 0.1601(2) 0.0339(7) Uani 1 1 d . . .
C22 C 0.0002(3) -0.0988(3) 0.0920(3) 0.0391(8) Uani 1 1 d . . .
C23 C -0.0926(3) 0.0639(2) 0.1957(2) 0.0353(7) Uani 1 1 d . . .
C24 C -0.0884(3) 0.1957(2) 0.2451(2) 0.0387(7) Uani 1 1 d . . .
H24 H -0.0931 0.2172 0.3245 0.046 Uiso 1 1 calc R . .
C25 C -0.2209(3) 0.2149(3) 0.1686(3) 0.0539(9) Uani 1 1 d . . .
H25A H -0.2203 0.2989 0.1948 0.065 Uiso 1 1 calc R . .
H25B H -0.2201 0.1889 0.0887 0.065 Uiso 1 1 calc R . .
C26 C -0.3533(3) 0.1477(3) 0.1730(3) 0.0605(9) Uani 1 1 d . . .
H26A H -0.3680 0.1895 0.2462 0.073 Uiso 1 1 calc R . .
H26B H -0.4325 0.1471 0.1107 0.073 Uiso 1 1 calc R . .
C27 C -0.3509(3) 0.0215(3) 0.1617(3) 0.0470(8) Uani 1 1 d . . .
C28 C -0.4745(4) -0.0581(3) 0.1382(3) 0.0652(10) Uani 1 1 d . . .
H28 H -0.5597 -0.0350 0.1232 0.078 Uiso 1 1 calc R . .
C29 C -0.4724(4) -0.1704(3) 0.1368(3) 0.0746(11) Uani 1 1 d . . .
H29 H -0.5562 -0.2238 0.1181 0.089 Uiso 1 1 calc R . .
C30 C -0.3469(4) -0.2043(3) 0.1631(3) 0.0659(10) Uani 1 1 d . . .
H30 H -0.3454 -0.2790 0.1659 0.079 Uiso 1 1 calc R . .
C31 C -0.2235(3) -0.1274(3) 0.1853(3) 0.0519(9) Uani 1 1 d . . .
H31 H -0.1387 -0.1503 0.2039 0.062 Uiso 1 1 calc R . .
C32 C -0.2238(3) -0.0146(2) 0.1802(2) 0.0395(8) Uani 1 1 d . . .
Cl1 Cl 0.51243(10) 0.47004(8) 0.13232(8) 0.0824(4) Uani 1 1 d . . .
N1 N 0.3599(3) 0.2640(2) 0.4472(2) 0.0424(6) Uani 1 1 d . . .
N2 N 0.2329(3) 0.0598(3) 0.1329(3) 0.0609(9) Uani 1 1 d . . .
N3 N -0.0038(3) -0.1938(2) 0.0374(2) 0.0595(8) Uani 1 1 d . . .
O1 O 0.1424(2) 0.16801(17) 0.43414(18) 0.0524(6) Uani 1 1 d . . .
O2 O 0.1470(2) 0.43450(17) 0.43475(19) 0.0574(6) Uani 1 1 d . . .
O3 O -0.0001(2) 0.46708(17) 0.29227(17) 0.0552(6) Uani 1 1 d . . .
H2B H 0.299(3) 0.116(3) 0.143(3) 0.070(13) Uiso 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 1.364(5) . ?
C1 C6 1.364(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(4) . ?
C7 N1 1.444(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.382(4) . ?
C8 C13 1.383(4) . ?
C8 N1 1.399(3) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 Cl1 1.733(3) . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.507(4) . ?
C14 C20 1.529(4) . ?
C14 C16 1.535(4) . ?
C14 C15 1.549(4) . ?
C15 O1 1.208(3) . ?
C15 N1 1.378(4) . ?
C16 C17 1.517(4) . ?
C16 C24 1.541(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.200(3) . ?
C17 O3 1.314(3) . ?
C18 O3 1.467(3) . ?
C18 C19 1.476(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N2 1.255(3) . ?
C20 C21 1.470(4) . ?
C21 C23 1.347(4) . ?
C21 C22 1.444(4) . ?
C22 N3 1.133(3) . ?
C23 C32 1.471(4) . ?
C23 C24 1.518(4) . ?
C24 C25 1.535(4) . ?
C24 H24 0.9800 . ?
C25 C26 1.513(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.508(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.389(4) . ?
C27 C32 1.395(4) . ?
C28 C29 1.374(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.374(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.405(4) . ?
C31 H31 0.9300 . ?
N2 H2B 0.85(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 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.9(4) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 117.9(3) . . ?
C5 C6 C7 123.7(3) . . ?
N1 C7 C6 114.8(2) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 121.5(3) . . ?
C9 C8 N1 128.1(3) . . ?
C13 C8 N1 110.4(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 Cl1 119.7(3) . . ?
C10 C11 Cl1 118.9(3) . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C8 120.6(3) . . ?
C12 C13 C14 130.7(3) . . ?
C8 C13 C14 108.6(3) . . ?
C13 C14 C20 111.0(2) . . ?
C13 C14 C16 115.0(2) . . ?
C20 C14 C16 108.4(2) . . ?
C13 C14 C15 102.3(2) . . ?
C20 C14 C15 106.3(2) . . ?
C16 C14 C15 113.5(2) . . ?
O1 C15 N1 126.1(3) . . ?
O1 C15 C14 126.9(3) . . ?
N1 C15 C14 106.9(3) . . ?
C17 C16 C14 109.3(2) . . ?
C17 C16 C24 111.1(2) . . ?
C14 C16 C24 113.5(2) . . ?
C17 C16 H16 107.5 . . ?
C14 C16 H16 107.5 . . ?
C24 C16 H16 107.5 . . ?
O2 C17 O3 123.7(3) . . ?
O2 C17 C16 123.7(3) . . ?
O3 C17 C16 112.6(3) . . ?
O3 C18 C19 107.6(3) . . ?
O3 C18 H18A 110.2 . . ?
C19 C18 H18A 110.2 . . ?
O3 C18 H18B 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 119.2(3) . . ?
N2 C20 C14 125.7(3) . . ?
C21 C20 C14 115.1(3) . . ?
C23 C21 C22 122.1(3) . . ?
C23 C21 C20 123.9(3) . . ?
C22 C21 C20 113.9(3) . . ?
N3 C22 C21 176.5(3) . . ?
C21 C23 C32 123.5(3) . . ?
C21 C23 C24 120.9(2) . . ?
C32 C23 C24 115.3(2) . . ?
C23 C24 C25 106.4(2) . . ?
C23 C24 C16 113.9(2) . . ?
C25 C24 C16 110.3(2) . . ?
C23 C24 H24 108.7 . . ?
C25 C24 H24 108.7 . . ?
C16 C24 H24 108.7 . . ?
C26 C25 C24 111.7(3) . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C27 C26 C25 114.1(3) . . ?
C27 C26 H26A 108.7 . . ?
C25 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C32 119.5(3) . . ?
C28 C27 C26 120.1(3) . . ?
C32 C27 C26 120.3(3) . . ?
C29 C28 C27 120.7(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 120.9(3) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C27 C32 C31 118.5(3) . . ?
C27 C32 C23 120.9(3) . . ?
C31 C32 C23 120.6(3) . . ?
C15 N1 C8 111.2(2) . . ?
C15 N1 C7 122.5(2) . . ?
C8 N1 C7 126.1(3) . . ?
C20 N2 H2B 110(2) . . ?
C17 O3 C18 116.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 1.000 131 36 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# 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_3a
_audit_block_doi                 10.5517/cc1k7zyq
_database_code_depnum_ccdc_archive 'CCDC 1437654'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N3 O3'
_chemical_formula_sum            'C25 H19 N3 O3'
_chemical_formula_weight         409.43

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'

_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                   8.1518(11)
_cell_length_b                   10.9237(15)
_cell_length_c                   11.5922(16)
_cell_angle_alpha                98.582(4)
_cell_angle_beta                 92.039(4)
_cell_angle_gamma                96.410(4)
_cell_volume                     1012.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8071
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.982
_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            14781
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.57
_reflns_number_total             4596
_reflns_number_gt                3599
_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)+(0.1017P)²+0.3867P] 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         4596
_refine_ls_number_parameters     292
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.080
_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 0.3036(2) 0.73499(18) -0.19194(17) 0.0340(4) Uani 1 1 d . . .
C2 C 0.3003(3) 0.8236(2) -0.26704(19) 0.0431(5) Uani 1 1 d . . .
H2A H 0.3545 0.9035 -0.2437 0.052 Uiso 1 1 calc R . .
C3 C 0.2177(3) 0.7943(3) -0.3754(2) 0.0591(7) Uani 1 1 d . . .
H3A H 0.2161 0.8542 -0.4245 0.071 Uiso 1 1 calc R . .
C4 C 0.1377(4) 0.6762(3) -0.4103(2) 0.0688(8) Uani 1 1 d . . .
H4 H 0.0860 0.6551 -0.4845 0.083 Uiso 1 1 calc R . .
C5 C 0.1342(3) 0.5891(3) -0.3356(2) 0.0600(7) Uani 1 1 d . . .
H5 H 0.0774 0.5101 -0.3594 0.072 Uiso 1 1 calc R . .
C6 C 0.2138(2) 0.61706(19) -0.22532(19) 0.0412(5) Uani 1 1 d . . .
C7 C 0.2014(3) 0.52734(19) -0.1389(2) 0.0457(5) Uani 1 1 d . . .
H7A H 0.2981 0.4829 -0.1411 0.055 Uiso 1 1 calc R . .
H7B H 0.1044 0.4668 -0.1590 0.055 Uiso 1 1 calc R . .
C8 C 0.1895(2) 0.59847(19) -0.0169(2) 0.0402(5) Uani 1 1 d . . .
H8A H 0.0892 0.6387 -0.0134 0.048 Uiso 1 1 calc R . .
H8B H 0.1849 0.5411 0.0395 0.048 Uiso 1 1 calc R . .
C9 C 0.3379(2) 0.69527(17) 0.01256(17) 0.0327(4) Uani 1 1 d . . .
C10 C 0.3973(2) 0.75871(16) -0.07752(16) 0.0299(4) Uani 1 1 d . . .
C11 C 0.5489(2) 0.83525(16) -0.05642(15) 0.0291(4) Uani 1 1 d . . .
C12 C 0.6276(3) 0.8912(2) -0.14823(17) 0.0399(5) Uani 1 1 d . . .
C13 C 0.6369(2) 0.85232(15) 0.05295(15) 0.0269(4) Uani 1 1 d . . .
C14 C 0.9340(2) 0.86803(16) 0.09611(16) 0.0292(4) Uani 1 1 d . . .
C15 C 0.8204(2) 0.82388(17) 0.28053(16) 0.0323(4) Uani 1 1 d . . .
C16 C 0.8938(3) 0.8420(2) 0.39272(19) 0.0448(5) Uani 1 1 d . . .
H16 H 1.0067 0.8383 0.4031 0.054 Uiso 1 1 calc R . .
C17 C 0.8009(3) 0.8654(2) 0.48856(19) 0.0511(6) Uani 1 1 d . . .
H17 H 0.8504 0.8751 0.5634 0.061 Uiso 1 1 calc R . .
C18 C 0.6346(3) 0.8744(2) 0.47353(19) 0.0466(5) Uani 1 1 d . . .
H18 H 0.5722 0.8921 0.5383 0.056 Uiso 1 1 calc R . .
C19 C 0.5604(2) 0.85713(19) 0.36243(17) 0.0383(5) Uani 1 1 d . . .
H19 H 0.4485 0.8650 0.3531 0.046 Uiso 1 1 calc R . .
C20 C 0.6505(2) 0.82799(17) 0.26374(16) 0.0301(4) Uani 1 1 d . . .
C21 C 0.5681(2) 0.80001(16) 0.14544(15) 0.0277(4) Uani 1 1 d . . .
C22 C 0.4185(2) 0.72028(17) 0.12206(17) 0.0321(4) Uani 1 1 d . A .
C23 C 0.3445(2) 0.65521(19) 0.21659(19) 0.0376(5) Uani 1 1 d . . .
N1 N 0.6942(3) 0.9358(2) -0.21894(18) 0.0659(7) Uani 1 1 d . . .
N2 N 0.79463(17) 0.92106(14) 0.06637(13) 0.0298(3) Uani 1 1 d . . .
H2B H 0.8049 0.9978 0.0559 0.036 Uiso 1 1 calc R . .
N3 N 0.92215(19) 0.79937(15) 0.18543(14) 0.0347(4) Uani 1 1 d . . .
H3B H 0.9797 0.7378 0.1837 0.042 Uiso 1 1 calc R . .
O1 O 1.06139(16) 0.88130(13) 0.04547(14) 0.0428(4) Uani 1 1 d . . .
O2 O 0.21379(17) 0.67135(15) 0.25686(14) 0.0463(4) Uani 1 1 d . A .
O3 O 0.4472(4) 0.5820(3) 0.2561(3) 0.0464(7) Uani 0.751(6) 1 d PDU A 1
C24 C 0.4068(6) 0.5263(4) 0.3604(4) 0.0800(14) Uani 0.751(6) 1 d PDU A 1
H24A H 0.3358 0.5765 0.4078 0.096 Uiso 0.751(6) 1 calc PR A 1
H24B H 0.5071 0.5229 0.4068 0.096 Uiso 0.751(6) 1 calc PR A 1
C25 C 0.3209(9) 0.3980(5) 0.3232(7) 0.125(2) Uani 0.751(6) 1 d PDU A 1
H25A H 0.2228 0.4019 0.2762 0.187 Uiso 0.751(6) 1 calc PR A 1
H25B H 0.2913 0.3613 0.3909 0.187 Uiso 0.751(6) 1 calc PR A 1
H25C H 0.3931 0.3482 0.2784 0.187 Uiso 0.751(6) 1 calc PR A 1
O3' O 0.4152(13) 0.5463(9) 0.2123(8) 0.0464(7) Uani 0.249(6) 1 d PDU A 2
C24' C 0.3590(19) 0.4715(15) 0.3003(13) 0.0800(14) Uani 0.249(6) 1 d PDU A 2
H24C H 0.3097 0.5202 0.3640 0.096 Uiso 0.249(6) 1 calc PR A 2
H24D H 0.4473 0.4310 0.3310 0.096 Uiso 0.249(6) 1 calc PR A 2
C25' C 0.231(2) 0.3787(15) 0.2249(19) 0.125(2) Uani 0.249(6) 1 d PDU A 2
H25D H 0.1329 0.4175 0.2130 0.187 Uiso 0.249(6) 1 calc PR A 2
H25E H 0.2040 0.3076 0.2633 0.187 Uiso 0.249(6) 1 calc PR A 2
H25F H 0.2749 0.3523 0.1507 0.187 Uiso 0.249(6) 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 C2 1.397(3) . ?
C1 C6 1.402(3) . ?
C1 C10 1.480(3) . ?
C2 C3 1.380(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(3) . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.509(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C22 1.384(3) . ?
C9 C10 1.408(3) . ?
C10 C11 1.404(2) . ?
C11 C13 1.411(2) . ?
C11 C12 1.440(3) . ?
C12 N1 1.138(3) . ?
C13 C21 1.395(2) . ?
C13 N2 1.406(2) . ?
C14 O1 1.216(2) . ?
C14 N3 1.366(2) . ?
C14 N2 1.387(2) . ?
C15 C16 1.389(3) . ?
C15 C20 1.399(3) . ?
C15 N3 1.415(2) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.480(2) . ?
C21 C22 1.410(2) . ?
C22 C23 1.501(3) . ?
C23 O2 1.199(2) . ?
C23 O3 1.335(3) . ?
C23 O3' 1.374(10) . ?
N2 H2B 0.8600 . ?
N3 H3B 0.8600 . ?
O3 C24 1.464(3) . ?
C24 C25 1.489(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
O3' C24' 1.455(5) . ?
C24' C25' 1.522(5) . ?
C24' H24C 0.9700 . ?
C24' H24D 0.9700 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 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
C2 C1 C6 118.99(18) . . ?
C2 C1 C10 123.44(17) . . ?
C6 C1 C10 117.57(18) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 122.29(19) . . ?
C1 C6 C7 118.82(18) . . ?
C6 C7 C8 109.52(17) . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 109.63(16) . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C22 C9 C10 119.86(16) . . ?
C22 C9 C8 122.64(17) . . ?
C10 C9 C8 117.47(17) . . ?
C11 C10 C9 118.00(16) . . ?
C11 C10 C1 123.19(16) . . ?
C9 C10 C1 118.68(15) . . ?
C10 C11 C13 121.41(15) . . ?
C10 C11 C12 121.32(16) . . ?
C13 C11 C12 117.08(15) . . ?
N1 C12 C11 177.9(2) . . ?
C21 C13 N2 120.91(15) . . ?
C21 C13 C11 120.00(15) . . ?
N2 C13 C11 119.09(15) . . ?
O1 C14 N3 121.04(17) . . ?
O1 C14 N2 122.05(17) . . ?
N3 C14 N2 116.91(15) . . ?
C16 C15 C20 120.29(18) . . ?
C16 C15 N3 117.97(17) . . ?
C20 C15 N3 121.74(17) . . ?
C17 C16 C15 120.56(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 121.17(19) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 117.91(17) . . ?
C19 C20 C21 121.02(16) . . ?
C15 C20 C21 121.06(16) . . ?
C13 C21 C22 117.77(16) . . ?
C13 C21 C20 120.61(15) . . ?
C22 C21 C20 121.61(15) . . ?
C9 C22 C21 122.37(16) . . ?
C9 C22 C23 117.61(16) . . ?
C21 C22 C23 119.99(17) . . ?
O2 C23 O3 123.5(2) . . ?
O2 C23 O3' 124.3(4) . . ?
O3 C23 O3' 26.5(4) . . ?
O2 C23 C22 124.86(18) . . ?
O3 C23 C22 111.50(18) . . ?
O3' C23 C22 106.2(4) . . ?
C14 N2 C13 121.55(14) . . ?
C14 N2 H2B 119.2 . . ?
C13 N2 H2B 119.2 . . ?
C14 N3 C15 123.64(16) . . ?
C14 N3 H3B 118.2 . . ?
C15 N3 H3B 118.2 . . ?
C23 O3 C24 119.0(3) . . ?
O3 C24 C25 108.8(4) . . ?
O3 C24 H24A 109.9 . . ?
C25 C24 H24A 109.9 . . ?
O3 C24 H24B 109.9 . . ?
C25 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C23 O3' C24' 113.7(9) . . ?
O3' C24' C25' 98.9(9) . . ?
O3' C24' H24C 112.0 . . ?
C25' C24' H24C 112.0 . . ?
O3' C24' H24D 112.0 . . ?
C25' C24' H24D 112.0 . . ?
H24C C24' H24D 109.7 . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 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 H2B O1 0.86 2.13 2.8456(19) 140.1 2_775
N3 H3B O2 0.86 2.29 3.040(2) 145.1 1_655

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_4d
_audit_block_doi                 10.5517/cc1k7zzr
_database_code_depnum_ccdc_archive 'CCDC 1437655'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H21 F N2 O3, C2 H6 O '
_chemical_formula_sum            'C32 H27 F N2 O4'
_chemical_formula_weight         522.56

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'

_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                   9.690(4)
_cell_length_b                   10.994(4)
_cell_length_c                   14.661(6)
_cell_angle_alpha                111.644(12)
_cell_angle_beta                 92.109(13)
_cell_angle_gamma                107.964(12)
_cell_volume                     1360.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8422
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.982
_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            18197
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.45
_reflns_number_total             6110
_reflns_number_gt                4261
_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)+(0.1427P)²+0.2383P] 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         6110
_refine_ls_number_parameters     355
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2412
_refine_ls_wR_factor_gt          0.2123
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0792(2) 0.7986(2) 0.37472(17) 0.0469(5) Uani 1 1 d . . .
C2 C -0.1588(3) 0.8844(3) 0.4156(2) 0.0659(8) Uani 1 1 d . . .
H2 H -0.1957 0.8875 0.4737 0.079 Uiso 1 1 calc R . .
C3 C -0.1821(3) 0.9651(3) 0.3680(2) 0.0755(9) Uani 1 1 d . . .
H3 H -0.2344 1.0245 0.3942 0.091 Uiso 1 1 calc R . .
C4 C -0.1276(4) 0.9575(3) 0.2820(2) 0.0709(8) Uani 1 1 d . . .
C5 C -0.0490(3) 0.8719(3) 0.23880(19) 0.0541(6) Uani 1 1 d . . .
H5 H -0.0140 0.8681 0.1799 0.065 Uiso 1 1 calc R . .
C6 C -0.0251(2) 0.7926(2) 0.28738(16) 0.0403(5) Uani 1 1 d . . .
C7 C 0.0519(2) 0.68718(19) 0.26004(15) 0.0347(4) Uani 1 1 d . . .
C8 C 0.0395(2) 0.6422(2) 0.34938(17) 0.0406(5) Uani 1 1 d . . .
C9 C 0.20992(19) 0.74101(18) 0.24208(14) 0.0324(4) Uani 1 1 d . . .
H9 H 0.2063 0.7661 0.1847 0.039 Uiso 1 1 calc R . .
C10 C 0.2988(2) 0.8731(2) 0.33281(15) 0.0370(5) Uani 1 1 d . . .
C11 C 0.4038(2) 0.9953(2) 0.32147(16) 0.0387(5) Uani 1 1 d . . .
C12 C 0.4978(2) 1.1020(2) 0.40595(18) 0.0482(6) Uani 1 1 d . . .
H12 H 0.4888 1.0981 0.4678 0.058 Uiso 1 1 calc R . .
C13 C 0.6043(3) 1.2136(2) 0.3992(2) 0.0620(7) Uani 1 1 d . . .
H13 H 0.6661 1.2842 0.4566 0.074 Uiso 1 1 calc R . .
C14 C 0.6205(3) 1.2221(2) 0.3084(2) 0.0636(8) Uani 1 1 d . . .
C15 C 0.7398(4) 1.3427(4) 0.3011(4) 0.1078(14) Uani 1 1 d . . .
H15A H 0.7678 1.3133 0.2366 0.162 Uiso 1 1 calc R . .
H15B H 0.8237 1.3737 0.3515 0.162 Uiso 1 1 calc R . .
H15C H 0.7037 1.4179 0.3107 0.162 Uiso 1 1 calc R . .
C16 C 0.5267(3) 1.1183(3) 0.2256(2) 0.0659(8) Uani 1 1 d . . .
H16 H 0.5358 1.1235 0.1641 0.079 Uiso 1 1 calc R . .
C17 C 0.4180(3) 1.0055(2) 0.23056(19) 0.0530(6) Uani 1 1 d . . .
H17 H 0.3548 0.9366 0.1730 0.064 Uiso 1 1 calc R . .
C18 C -0.0340(2) 0.5588(2) 0.16674(16) 0.0401(5) Uani 1 1 d . . .
C19 C 0.0422(2) 0.46043(19) 0.12058(15) 0.0356(4) Uani 1 1 d . . .
C20 C -0.0569(2) 0.3339(2) 0.04383(17) 0.0456(5) Uani 1 1 d . . .
C21 C 0.1879(2) 0.4868(2) 0.14786(14) 0.0356(4) Uani 1 1 d . . .
C22 C 0.2856(2) 0.6312(2) 0.21889(15) 0.0359(5) Uani 1 1 d . . .
H22 H 0.3156 0.6262 0.2816 0.043 Uiso 1 1 calc R . .
C23 C 0.4247(2) 0.6750(3) 0.1746(2) 0.0562(6) Uani 1 1 d . . .
H23A H 0.3966 0.6768 0.1110 0.067 Uiso 1 1 calc R . .
H23B H 0.4875 0.7686 0.2187 0.067 Uiso 1 1 calc R . .
C24 C 0.5090(3) 0.5777(3) 0.1599(3) 0.0682(8) Uani 1 1 d . . .
H24A H 0.5834 0.5976 0.1199 0.082 Uiso 1 1 calc R . .
H24B H 0.5593 0.5947 0.2243 0.082 Uiso 1 1 calc R . .
C25 C 0.4138(3) 0.4273(3) 0.11047(19) 0.0516(6) Uani 1 1 d . . .
C26 C 0.4791(4) 0.3283(3) 0.0668(2) 0.0697(8) Uani 1 1 d . . .
H26 H 0.5801 0.3574 0.0671 0.084 Uiso 1 1 calc R . .
C27 C 0.3986(4) 0.1904(4) 0.0238(3) 0.0836(10) Uani 1 1 d . . .
H27 H 0.4435 0.1263 -0.0081 0.100 Uiso 1 1 calc R . .
C28 C 0.2502(4) 0.1449(3) 0.0273(3) 0.0905(11) Uani 1 1 d . . .
H28 H 0.1959 0.0499 0.0002 0.109 Uiso 1 1 calc R . .
C29 C 0.1822(3) 0.2401(3) 0.0710(2) 0.0690(8) Uani 1 1 d . . .
H29 H 0.0830 0.2086 0.0755 0.083 Uiso 1 1 calc R . .
C30 C 0.2611(2) 0.3838(2) 0.10854(16) 0.0442(5) Uani 1 1 d . . .
C31 C 0.1939(8) 0.2945(6) 0.3563(5) 0.153(2) Uani 1 1 d D . .
H31A H 0.1415 0.2685 0.2905 0.184 Uiso 1 1 calc R . .
H31B H 0.1980 0.2106 0.3622 0.184 Uiso 1 1 calc R . .
C32 C 0.3494(7) 0.3958(7) 0.3707(6) 0.194(3) Uani 1 1 d D . .
H32A H 0.3445 0.4774 0.3629 0.292 Uiso 1 1 calc R . .
H32B H 0.4014 0.3516 0.3220 0.292 Uiso 1 1 calc R . .
H32C H 0.4001 0.4222 0.4363 0.292 Uiso 1 1 calc R . .
F1 F -0.1523(3) 1.0368(2) 0.23491(17) 0.1093(8) Uani 1 1 d . . .
N1 N -0.0413(2) 0.7075(2) 0.40833(15) 0.0487(5) Uani 1 1 d . . .
H1 H -0.0667 0.6947 0.4606 0.058 Uiso 1 1 calc R . .
N2 N -0.1431(3) 0.2386(2) -0.01596(18) 0.0697(7) Uani 1 1 d . . .
O1 O 0.08807(17) 0.55762(16) 0.36011(13) 0.0510(4) Uani 1 1 d . . .
O2 O 0.28356(18) 0.87416(17) 0.41479(12) 0.0562(5) Uani 1 1 d . . .
O3 O -0.15901(17) 0.53649(19) 0.13338(16) 0.0715(6) Uani 1 1 d . . .
O4 O 0.1191(4) 0.3607(3) 0.4307(2) 0.1180(11) Uani 1 1 d . . .
H4 H 0.1002 0.4212 0.4182 0.177 Uiso 1 1 calc R . .


_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 1.382(3) . ?
C1 C6 1.388(3) . ?
C1 N1 1.399(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 F1 1.362(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 C18 1.524(3) . ?
C7 C9 1.533(3) . ?
C7 C8 1.558(3) . ?
C8 O1 1.218(3) . ?
C8 N1 1.347(3) . ?
C9 C10 1.530(3) . ?
C9 C22 1.540(3) . ?
C9 H9 0.9800 . ?
C10 O2 1.213(3) . ?
C10 C11 1.484(3) . ?
C11 C17 1.386(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C16 1.364(4) . ?
C14 C15 1.508(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.205(3) . ?
C18 C19 1.471(3) . ?
C19 C21 1.362(3) . ?
C19 C20 1.437(3) . ?
C20 N2 1.137(3) . ?
C21 C30 1.471(3) . ?
C21 C22 1.511(3) . ?
C22 C23 1.538(3) . ?
C22 H22 0.9800 . ?
C23 C24 1.498(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.495(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.392(3) . ?
C25 C30 1.403(3) . ?
C26 C27 1.354(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.379(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.402(4) . ?
C29 H29 0.9300 . ?
C31 O4 1.429(5) . ?
C31 C32 1.524(2) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 H1 0.8600 . ?
O4 H4 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 C6 121.0(2) . . ?
C2 C1 N1 129.2(2) . . ?
C6 C1 N1 109.76(18) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
F1 C4 C3 119.2(3) . . ?
F1 C4 C5 117.3(3) . . ?
C3 C4 C5 123.5(3) . . ?
C6 C5 C4 116.5(3) . . ?
C6 C5 H5 121.8 . . ?
C4 C5 H5 121.8 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 C7 130.3(2) . . ?
C1 C6 C7 108.62(19) . . ?
C6 C7 C18 110.99(16) . . ?
C6 C7 C9 115.03(16) . . ?
C18 C7 C9 107.44(16) . . ?
C6 C7 C8 101.77(16) . . ?
C18 C7 C8 107.29(16) . . ?
C9 C7 C8 114.08(16) . . ?
O1 C8 N1 126.9(2) . . ?
O1 C8 C7 125.53(19) . . ?
N1 C8 C7 107.47(18) . . ?
C10 C9 C7 109.15(16) . . ?
C10 C9 C22 110.70(15) . . ?
C7 C9 C22 112.86(15) . . ?
C10 C9 H9 108.0 . . ?
C7 C9 H9 108.0 . . ?
C22 C9 H9 108.0 . . ?
O2 C10 C11 120.67(19) . . ?
O2 C10 C9 118.00(17) . . ?
C11 C10 C9 121.30(18) . . ?
C17 C11 C12 118.28(19) . . ?
C17 C11 C10 123.59(19) . . ?
C12 C11 C10 118.1(2) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C16 C14 C13 118.3(2) . . ?
C16 C14 C15 120.9(3) . . ?
C13 C14 C15 120.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 121.8(3) . . ?
C14 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C11 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
C11 C17 H17 120.1 . . ?
O3 C18 C19 121.29(19) . . ?
O3 C18 C7 122.18(19) . . ?
C19 C18 C7 116.50(16) . . ?
C21 C19 C20 124.88(19) . . ?
C21 C19 C18 123.96(17) . . ?
C20 C19 C18 111.16(17) . . ?
N2 C20 C19 174.8(2) . . ?
C19 C21 C30 124.00(18) . . ?
C19 C21 C22 119.83(18) . . ?
C30 C21 C22 116.10(17) . . ?
C21 C22 C23 108.33(18) . . ?
C21 C22 C9 113.73(16) . . ?
C23 C22 C9 110.37(16) . . ?
C21 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C9 C22 H22 108.1 . . ?
C24 C23 C22 111.9(2) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 113.1(2) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C30 119.4(2) . . ?
C26 C25 C24 118.9(2) . . ?
C30 C25 C24 121.7(2) . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 120.1(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.7(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C25 118.0(2) . . ?
C29 C30 C21 121.4(2) . . ?
C25 C30 C21 120.5(2) . . ?
O4 C31 C32 108.8(5) . . ?
O4 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
O4 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C8 N1 C1 112.22(19) . . ?
C8 N1 H1 123.9 . . ?
C1 N1 H1 123.9 . . ?
C31 O4 H4 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
O4 H4 O1 0.82 2.01 2.807(3) 164.7 .
N1 H1 O4 0.86 1.94 2.791(3) 171.4 2_566

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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_4h
_audit_block_doi                 10.5517/cc1k800v
_database_code_depnum_ccdc_archive 'CCDC 1437656'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H27 Cl N2 O3'
_chemical_formula_sum            'C37 H27 Cl N2 O3'
_chemical_formula_weight         583.06

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'

_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                   9.952(2)
_cell_length_b                   11.806(3)
_cell_length_c                   14.493(3)
_cell_angle_alpha                113.309(5)
_cell_angle_beta                 99.794(6)
_cell_angle_gamma                100.840(6)
_cell_volume                     1478.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5388
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.977
_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            16290
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5025
_reflns_number_gt                2989
_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)+(0.1037P)²+0.1273P] 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         5025
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.1918
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 -0.1733(4) 0.2688(4) 0.1920(3) 0.0679(11) Uani 1 1 d . . .
H1 H -0.1796 0.2030 0.1276 0.081 Uiso 1 1 calc R . .
C2 C -0.2675(4) 0.2495(5) 0.2468(4) 0.0819(13) Uani 1 1 d . . .
H2 H -0.3345 0.1702 0.2210 0.098 Uiso 1 1 calc R . .
C3 C -0.2626(5) 0.3466(6) 0.3388(4) 0.0877(14) Uani 1 1 d . . .
H3 H -0.3281 0.3346 0.3753 0.105 Uiso 1 1 calc R . .
C4 C -0.1621(6) 0.4612(5) 0.3777(4) 0.1007(17) Uani 1 1 d . . .
H4 H -0.1585 0.5277 0.4408 0.121 Uiso 1 1 calc R . .
C5 C -0.0644(5) 0.4788(4) 0.3227(3) 0.0795(13) Uani 1 1 d . . .
H5 H 0.0050 0.5571 0.3500 0.095 Uiso 1 1 calc R . .
C6 C -0.0691(3) 0.3839(3) 0.2304(3) 0.0477(9) Uani 1 1 d . . .
C7 C 0.0355(4) 0.3966(3) 0.1689(3) 0.0549(9) Uani 1 1 d . . .
H7A H 0.1014 0.3478 0.1763 0.066 Uiso 1 1 calc R . .
H7B H -0.0156 0.3586 0.0956 0.066 Uiso 1 1 calc R . .
C8 C 0.2545(4) 0.5785(3) 0.2576(2) 0.0426(8) Uani 1 1 d . . .
C9 C 0.3014(3) 0.7196(3) 0.2739(2) 0.0347(7) Uani 1 1 d . . .
C10 C 0.1704(3) 0.7301(3) 0.2119(2) 0.0358(7) Uani 1 1 d . . .
C11 C 0.1450(3) 0.8307(3) 0.1929(2) 0.0422(8) Uani 1 1 d . . .
H11 H 0.2143 0.9090 0.2207 0.051 Uiso 1 1 calc R . .
C12 C 0.0121(3) 0.8107(3) 0.1310(2) 0.0463(8) Uani 1 1 d . . .
C13 C -0.0921(3) 0.6957(4) 0.0895(2) 0.0482(9) Uani 1 1 d . . .
H13 H -0.1801 0.6856 0.0483 0.058 Uiso 1 1 calc R . .
C14 C -0.0665(3) 0.5954(3) 0.1089(2) 0.0459(9) Uani 1 1 d . . .
H14 H -0.1361 0.5172 0.0813 0.055 Uiso 1 1 calc R . .
C15 C 0.0647(3) 0.6144(3) 0.1703(2) 0.0390(8) Uani 1 1 d . . .
C16 C 0.4372(3) 0.7530(3) 0.2399(2) 0.0362(7) Uani 1 1 d . . .
H16 H 0.4563 0.8429 0.2518 0.043 Uiso 1 1 calc R . .
C17 C 0.4096(3) 0.6699(3) 0.1231(2) 0.0351(7) Uani 1 1 d . . .
C18 C 0.4699(3) 0.7223(3) 0.0566(2) 0.0374(8) Uani 1 1 d . . .
C19 C 0.4722(4) 0.6364(3) -0.0409(2) 0.0480(9) Uani 1 1 d . . .
H19 H 0.4314 0.5489 -0.0644 0.058 Uiso 1 1 calc R . .
C20 C 0.5349(4) 0.6793(4) -0.1036(3) 0.0606(11) Uani 1 1 d . . .
H20 H 0.5367 0.6197 -0.1684 0.073 Uiso 1 1 calc R . .
C21 C 0.5940(4) 0.8070(4) -0.0729(3) 0.0530(9) Uani 1 1 d . . .
C22 C 0.6652(5) 0.8529(5) -0.1404(3) 0.0885(15) Uani 1 1 d . . .
H22A H 0.7653 0.8626 -0.1206 0.133 Uiso 1 1 calc R . .
H22B H 0.6504 0.9342 -0.1316 0.133 Uiso 1 1 calc R . .
H22C H 0.6254 0.7913 -0.2123 0.133 Uiso 1 1 calc R . .
C23 C 0.5884(4) 0.8926(4) 0.0231(3) 0.0581(10) Uani 1 1 d . . .
H23 H 0.6267 0.9801 0.0452 0.070 Uiso 1 1 calc R . .
C24 C 0.5276(4) 0.8519(3) 0.0875(2) 0.0498(9) Uani 1 1 d . . .
H24 H 0.5255 0.9119 0.1520 0.060 Uiso 1 1 calc R . .
C25 C 0.3331(3) 0.8050(3) 0.3907(2) 0.0401(8) Uani 1 1 d . . .
C26 C 0.4714(3) 0.8180(3) 0.4551(2) 0.0352(7) Uani 1 1 d . . .
C27 C 0.4847(3) 0.8781(3) 0.5653(3) 0.0389(8) Uani 1 1 d . . .
C28 C 0.5769(3) 0.7782(3) 0.4153(2) 0.0357(7) Uani 1 1 d . . .
C29 C 0.5692(3) 0.7392(3) 0.3016(2) 0.0447(8) Uani 1 1 d . . .
H29 H 0.5699 0.6491 0.2692 0.054 Uiso 1 1 calc R . .
C30 C 0.7084(4) 0.8242(5) 0.2999(3) 0.0792(14) Uani 1 1 d . . .
H30A H 0.7085 0.8005 0.2277 0.095 Uiso 1 1 calc R . .
H30B H 0.7068 0.9132 0.3308 0.095 Uiso 1 1 calc R . .
C31 C 0.8373(4) 0.8153(5) 0.3530(3) 0.0729(12) Uani 1 1 d . . .
H31A H 0.9132 0.8901 0.3677 0.087 Uiso 1 1 calc R . .
H31B H 0.8594 0.7401 0.3066 0.087 Uiso 1 1 calc R . .
C32 C 0.8357(3) 0.8068(4) 0.4522(2) 0.0543(10) Uani 1 1 d . . .
C33 C 0.9625(4) 0.8189(5) 0.5196(3) 0.0832(14) Uani 1 1 d . . .
H33 H 1.0484 0.8411 0.5050 0.100 Uiso 1 1 calc R . .
C34 C 0.9625(5) 0.7990(6) 0.6056(3) 0.1051(19) Uani 1 1 d . . .
H34 H 1.0479 0.8079 0.6493 0.126 Uiso 1 1 calc R . .
C35 C 0.8386(5) 0.7660(5) 0.6276(3) 0.0957(16) Uani 1 1 d . . .
H35 H 0.8390 0.7494 0.6853 0.115 Uiso 1 1 calc R . .
C36 C 0.7125(4) 0.7568(4) 0.5660(3) 0.0631(11) Uani 1 1 d . . .
H36 H 0.6280 0.7339 0.5820 0.076 Uiso 1 1 calc R . .
C37 C 0.7099(3) 0.7814(3) 0.4793(2) 0.0406(8) Uani 1 1 d . . .
Cl1 Cl -0.02349(11) 0.93423(11) 0.10333(10) 0.0898(4) Uani 1 1 d . . .
N1 N 0.1158(3) 0.5274(2) 0.19996(19) 0.0439(7) Uani 1 1 d . . .
N2 N 0.4905(3) 0.9272(3) 0.6516(2) 0.0553(8) Uani 1 1 d . . .
O1 O 0.3250(3) 0.5250(2) 0.29323(18) 0.0571(7) Uani 1 1 d . . .
O2 O 0.3403(2) 0.5579(2) 0.08604(15) 0.0486(6) Uani 1 1 d . . .
O3 O 0.2472(2) 0.8551(3) 0.42846(17) 0.0667(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 C2 1.370(5) . ?
C1 C6 1.381(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.350(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(5) . ?
C7 N1 1.446(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.208(4) . ?
C8 N1 1.365(4) . ?
C8 C9 1.552(4) . ?
C9 C10 1.508(4) . ?
C9 C25 1.526(4) . ?
C9 C16 1.550(4) . ?
C10 C11 1.377(4) . ?
C10 C15 1.389(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(4) . ?
C12 Cl1 1.739(3) . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 N1 1.403(4) . ?
C16 C17 1.526(4) . ?
C16 C29 1.532(4) . ?
C16 H16 0.9800 . ?
C17 O2 1.217(3) . ?
C17 C18 1.483(4) . ?
C18 C24 1.382(4) . ?
C18 C19 1.383(4) . ?
C19 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(5) . ?
C20 H20 0.9300 . ?
C21 C23 1.376(5) . ?
C21 C22 1.506(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 O3 1.214(3) . ?
C25 C26 1.470(4) . ?
C26 C28 1.354(4) . ?
C26 C27 1.438(4) . ?
C27 N2 1.138(4) . ?
C28 C37 1.467(4) . ?
C28 C29 1.508(4) . ?
C29 C30 1.561(5) . ?
C29 H29 0.9800 . ?
C30 C31 1.424(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.483(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C37 1.390(4) . ?
C32 C33 1.403(5) . ?
C33 C34 1.356(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.352(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.369(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.394(4) . ?
C36 H36 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 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 123.1(3) . . ?
C1 C6 C7 118.7(3) . . ?
N1 C7 C6 114.4(3) . . ?
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 . . ?
O1 C8 N1 125.9(3) . . ?
O1 C8 C9 126.6(3) . . ?
N1 C8 C9 107.3(3) . . ?
C10 C9 C25 112.2(2) . . ?
C10 C9 C16 113.8(2) . . ?
C25 C9 C16 107.7(2) . . ?
C10 C9 C8 102.1(2) . . ?
C25 C9 C8 106.7(2) . . ?
C16 C9 C8 114.2(2) . . ?
C11 C10 C15 120.2(3) . . ?
C11 C10 C9 130.8(3) . . ?
C15 C10 C9 109.0(3) . . ?
C10 C11 C12 117.5(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 Cl1 118.8(3) . . ?
C11 C12 Cl1 119.0(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 N1 128.5(3) . . ?
C10 C15 N1 109.6(3) . . ?
C17 C16 C29 110.6(2) . . ?
C17 C16 C9 109.3(2) . . ?
C29 C16 C9 113.5(2) . . ?
C17 C16 H16 107.7 . . ?
C29 C16 H16 107.7 . . ?
C9 C16 H16 107.7 . . ?
O2 C17 C18 120.5(3) . . ?
O2 C17 C16 118.3(3) . . ?
C18 C17 C16 121.1(3) . . ?
C24 C18 C19 118.0(3) . . ?
C24 C18 C17 123.9(3) . . ?
C19 C18 C17 118.1(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C23 117.6(3) . . ?
C20 C21 C22 121.4(4) . . ?
C23 C21 C22 121.0(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 121.7(4) . . ?
C21 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C18 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C18 C24 H24 119.8 . . ?
O3 C25 C26 122.1(3) . . ?
O3 C25 C9 122.0(3) . . ?
C26 C25 C9 115.8(3) . . ?
C28 C26 C27 122.9(3) . . ?
C28 C26 C25 123.7(3) . . ?
C27 C26 C25 113.4(3) . . ?
N2 C27 C26 177.2(3) . . ?
C26 C28 C37 123.3(3) . . ?
C26 C28 C29 120.8(3) . . ?
C37 C28 C29 115.6(2) . . ?
C28 C29 C16 114.3(2) . . ?
C28 C29 C30 105.9(3) . . ?
C16 C29 C30 111.2(3) . . ?
C28 C29 H29 108.4 . . ?
C16 C29 H29 108.4 . . ?
C30 C29 H29 108.4 . . ?
C31 C30 C29 115.5(3) . . ?
C31 C30 H30A 108.4 . . ?
C29 C30 H30A 108.4 . . ?
C31 C30 H30B 108.4 . . ?
C29 C30 H30B 108.4 . . ?
H30A C30 H30B 107.5 . . ?
C30 C31 C32 115.2(3) . . ?
C30 C31 H31A 108.5 . . ?
C32 C31 H31A 108.5 . . ?
C30 C31 H31B 108.5 . . ?
C32 C31 H31B 108.5 . . ?
H31A C31 H31B 107.5 . . ?
C37 C32 C33 118.0(3) . . ?
C37 C32 C31 121.8(3) . . ?
C33 C32 C31 120.2(3) . . ?
C34 C33 C32 121.5(4) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C35 C34 C33 120.0(4) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.7(4) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C37 120.4(4) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 119.1(3) . . ?
C32 C37 C28 119.6(3) . . ?
C36 C37 C28 121.3(3) . . ?
C8 N1 C15 111.9(3) . . ?
C8 N1 C7 123.2(3) . . ?
C15 N1 C7 124.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_B3
_audit_block_doi                 10.5517/cc1k802x
_database_code_depnum_ccdc_archive 'CCDC 1437658'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 F N3 O3'
_chemical_formula_sum            'C32 H26 F N3 O3'
_chemical_formula_weight         519.56

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'

_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                   8.8879(14)
_cell_length_b                   10.2517(15)
_cell_length_c                   15.125(2)
_cell_angle_alpha                87.979(5)
_cell_angle_beta                 74.042(5)
_cell_angle_gamma                88.220(5)
_cell_volume                     1323.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4873
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_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            26999
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.59
_reflns_number_total             6142
_reflns_number_gt                3257
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0688P)²+0.3424P] 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         6103
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.015
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3939(3) 0.2671(2) -0.24962(16) 0.0500(6) Uani 1 1 d . . .
H1 H 0.3573 0.1870 -0.2230 0.060 Uiso 1 1 calc R . .
C2 C 0.5226(3) 0.2712(3) -0.32505(17) 0.0619(7) Uani 1 1 d . . .
H2 H 0.5727 0.1939 -0.3489 0.074 Uiso 1 1 calc R . .
C3 C 0.5773(3) 0.3888(3) -0.36510(18) 0.0651(7) Uani 1 1 d . . .
H3 H 0.6641 0.3915 -0.4162 0.078 Uiso 1 1 calc R . .
C4 C 0.5034(3) 0.5029(3) -0.32957(18) 0.0628(7) Uani 1 1 d . . .
H4 H 0.5407 0.5828 -0.3564 0.075 Uiso 1 1 calc R . .
C5 C 0.3740(3) 0.4991(2) -0.25424(16) 0.0501(6) Uani 1 1 d . . .
H5 H 0.3237 0.5765 -0.2310 0.060 Uiso 1 1 calc R . .
C6 C 0.3184(2) 0.3812(2) -0.21292(14) 0.0404(5) Uani 1 1 d . . .
C7 C 0.1805(3) 0.3744(2) -0.12854(15) 0.0458(6) Uani 1 1 d . . .
H7A H 0.1056 0.4436 -0.1326 0.055 Uiso 1 1 calc R . .
H7B H 0.1294 0.2916 -0.1264 0.055 Uiso 1 1 calc R . .
C8 C 0.2794(3) 0.2831(2) -0.00016(15) 0.0436(5) Uani 1 1 d . . .
C9 C 0.3442(3) 0.3371(2) 0.07460(14) 0.0393(5) Uani 1 1 d . . .
H9 H 0.4583 0.3263 0.0541 0.047 Uiso 1 1 calc R . .
C10 C 0.3072(2) 0.4803(2) 0.06984(14) 0.0376(5) Uani 1 1 d . . .
C11 C 0.3247(3) 0.5799(2) 0.12456(15) 0.0438(6) Uani 1 1 d . . .
H11 H 0.3693 0.5652 0.1730 0.053 Uiso 1 1 calc R . .
C12 C 0.2732(3) 0.7026(2) 0.10420(17) 0.0478(6) Uani 1 1 d . . .
C13 C 0.2069(3) 0.7294(2) 0.03411(17) 0.0486(6) Uani 1 1 d . . .
H13 H 0.1741 0.8141 0.0234 0.058 Uiso 1 1 calc R . .
C14 C 0.1888(2) 0.6285(2) -0.02126(15) 0.0441(6) Uani 1 1 d . . .
H14 H 0.1446 0.6440 -0.0698 0.053 Uiso 1 1 calc R . .
C15 C 0.2386(2) 0.5050(2) -0.00171(14) 0.0378(5) Uani 1 1 d . . .
C16 C 0.2896(2) 0.27611(19) 0.17199(14) 0.0374(5) Uani 1 1 d . . .
H16 H 0.3561 0.3097 0.2077 0.045 Uiso 1 1 calc R . .
C17 C 0.1227(3) 0.3191(2) 0.21823(15) 0.0410(5) Uani 1 1 d . . .
C18 C -0.0441(3) 0.4067(3) 0.3556(2) 0.0805(9) Uani 1 1 d . . .
H18A H -0.1230 0.3858 0.3252 0.097 Uiso 1 1 calc R . .
H18B H -0.0703 0.3632 0.4157 0.097 Uiso 1 1 calc R . .
C19 C -0.0442(5) 0.5447(4) 0.3662(4) 0.1425(18) Uani 1 1 d . . .
H19A H 0.0251 0.5645 0.4024 0.214 Uiso 1 1 calc R . .
H19B H -0.1483 0.5750 0.3966 0.214 Uiso 1 1 calc R . .
H19C H -0.0096 0.5872 0.3068 0.214 Uiso 1 1 calc R . .
C20 C 0.2618(2) 0.07420(19) 0.27358(14) 0.0385(5) Uani 1 1 d . . .
C21 C 0.1381(3) -0.0047(2) 0.30616(16) 0.0460(6) Uani 1 1 d . . .
C22 C 0.0311(3) -0.0313(2) 0.2539(2) 0.0588(7) Uani 1 1 d . . .
C23 C 0.1116(3) -0.0803(2) 0.39104(19) 0.0551(7) Uani 1 1 d . . .
C24 C 0.3044(3) 0.12561(19) 0.17538(15) 0.0407(5) Uani 1 1 d . . .
H24 H 0.2331 0.0895 0.1438 0.049 Uiso 1 1 calc R . .
C25 C 0.4710(3) 0.0727(2) 0.13169(15) 0.0453(6) Uani 1 1 d . . .
H25A H 0.4703 -0.0219 0.1340 0.054 Uiso 1 1 calc R . .
H25B H 0.5037 0.1011 0.0675 0.054 Uiso 1 1 calc R . .
C26 C 0.5878(3) 0.1181(2) 0.17951(16) 0.0475(6) Uani 1 1 d . . .
H26A H 0.6791 0.0603 0.1641 0.057 Uiso 1 1 calc R . .
H26B H 0.6211 0.2047 0.1558 0.057 Uiso 1 1 calc R . .
C27 C 0.5276(3) 0.1222(2) 0.28200(15) 0.0416(5) Uani 1 1 d . . .
C28 C 0.6283(3) 0.1487(2) 0.33445(19) 0.0565(7) Uani 1 1 d . . .
H28 H 0.7346 0.1567 0.3057 0.068 Uiso 1 1 calc R . .
C29 C 0.5745(4) 0.1632(3) 0.4279(2) 0.0669(8) Uani 1 1 d . . .
H29 H 0.6445 0.1796 0.4618 0.080 Uiso 1 1 calc R . .
C30 C 0.4172(4) 0.1536(3) 0.47170(18) 0.0664(7) Uani 1 1 d . . .
H30 H 0.3806 0.1666 0.5346 0.080 Uiso 1 1 calc R . .
C31 C 0.3150(3) 0.1248(2) 0.42238(16) 0.0525(6) Uani 1 1 d . . .
H31 H 0.2089 0.1177 0.4520 0.063 Uiso 1 1 calc R . .
C32 C 0.3694(3) 0.1058(2) 0.32734(15) 0.0405(5) Uani 1 1 d . . .
F1 F 0.28925(18) 0.80199(13) 0.15798(11) 0.0708(4) Uani 1 1 d . . .
N1 N 0.2272(2) 0.38706(17) -0.04407(11) 0.0406(4) Uani 1 1 d . . .
N2 N -0.0572(3) -0.0546(3) 0.2151(2) 0.0927(9) Uani 1 1 d . . .
N3 N 0.0903(3) -0.1457(2) 0.45529(17) 0.0766(7) Uani 1 1 d . . .
O1 O 0.2805(2) 0.17026(16) -0.02221(11) 0.0616(5) Uani 1 1 d . . .
O2 O 0.0169(2) 0.31539(18) 0.18347(11) 0.0627(5) Uani 1 1 d . . .
O3 O 0.10836(19) 0.36009(18) 0.30161(11) 0.0614(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 1.376(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 N1 1.459(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.214(3) . ?
C8 N1 1.371(3) . ?
C8 C9 1.529(3) . ?
C9 C10 1.498(3) . ?
C9 C16 1.535(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.375(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 F1 1.360(3) . ?
C12 C13 1.364(3) . ?
C13 C14 1.394(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.407(3) . ?
C16 C17 1.515(3) . ?
C16 C24 1.545(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.199(3) . ?
C17 O3 1.315(3) . ?
C18 C19 1.429(5) . ?
C18 O3 1.453(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.355(3) . ?
C20 C32 1.464(3) . ?
C20 C24 1.508(3) . ?
C21 C22 1.431(4) . ?
C21 C23 1.442(4) . ?
C22 N2 1.137(3) . ?
C23 N3 1.136(3) . ?
C24 C25 1.536(3) . ?
C24 H24 0.9800 . ?
C25 C26 1.511(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.496(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.387(3) . ?
C27 C32 1.397(3) . ?
C28 C29 1.374(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.369(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.404(3) . ?
C31 H31 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 120.7(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 121.7(2) . . ?
C1 C6 C7 119.7(2) . . ?
N1 C7 C6 112.03(17) . . ?
N1 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 N1 124.5(2) . . ?
O1 C8 C9 127.7(2) . . ?
N1 C8 C9 107.68(18) . . ?
C10 C9 C8 102.77(17) . . ?
C10 C9 C16 113.75(17) . . ?
C8 C9 C16 118.12(18) . . ?
C10 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C16 C9 H9 107.2 . . ?
C11 C10 C15 120.31(19) . . ?
C11 C10 C9 130.83(19) . . ?
C15 C10 C9 108.80(18) . . ?
C10 C11 C12 116.9(2) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
F1 C12 C13 118.6(2) . . ?
F1 C12 C11 117.5(2) . . ?
C13 C12 C11 123.9(2) . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 N1 128.8(2) . . ?
C10 C15 N1 109.33(18) . . ?
C17 C16 C9 110.38(17) . . ?
C17 C16 C24 109.98(17) . . ?
C9 C16 C24 113.95(17) . . ?
C17 C16 H16 107.4 . . ?
C9 C16 H16 107.4 . . ?
C24 C16 H16 107.4 . . ?
O2 C17 O3 124.3(2) . . ?
O2 C17 C16 124.3(2) . . ?
O3 C17 C16 111.40(19) . . ?
C19 C18 O3 110.7(3) . . ?
C19 C18 H18A 109.5 . . ?
O3 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C32 123.0(2) . . ?
C21 C20 C24 120.9(2) . . ?
C32 C20 C24 115.86(18) . . ?
C20 C21 C22 122.4(2) . . ?
C20 C21 C23 123.6(2) . . ?
C22 C21 C23 113.7(2) . . ?
N2 C22 C21 177.6(3) . . ?
N3 C23 C21 176.3(3) . . ?
C20 C24 C25 105.43(17) . . ?
C20 C24 C16 110.66(17) . . ?
C25 C24 C16 113.75(17) . . ?
C20 C24 H24 109.0 . . ?
C25 C24 H24 109.0 . . ?
C16 C24 H24 109.0 . . ?
C26 C25 C24 112.61(18) . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 114.64(19) . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C32 118.1(2) . . ?
C28 C27 C26 120.1(2) . . ?
C32 C27 C26 121.8(2) . . ?
C29 C28 C27 121.5(2) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 120.2(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.4(2) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 119.8(2) . . ?
C27 C32 C20 119.0(2) . . ?
C31 C32 C20 121.1(2) . . ?
C8 N1 C15 111.19(17) . . ?
C8 N1 C7 122.82(18) . . ?
C15 N1 C7 125.77(18) . . ?
C17 O3 C18 118.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.045
#=============================================================


