# 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_1d
_audit_block_doi                 10.5517/cc1jmfyj
_database_code_depnum_ccdc_archive 'CCDC 1418868'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N2 O3'
_chemical_formula_sum            'C28 H24 N2 O3'
_chemical_formula_weight         436.49

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                   9.3414(12)
_cell_length_b                   11.5761(15)
_cell_length_c                   12.5780(15)
_cell_angle_alpha                116.110(4)
_cell_angle_beta                 106.926(4)
_cell_angle_gamma                96.199(4)
_cell_volume                     1123.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6915
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.983
_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            15875
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.56
_reflns_number_total             5086
_reflns_number_gt                3348
_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)+(0.0954P)²+0.0223P] 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         5086
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1803
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 1.0830(2) 0.7391(2) -0.0379(2) 0.0558(5) Uani 1 1 d . . .
H1A H 1.1624 0.7868 0.0479 0.067 Uiso 1 1 calc R . .
H1B H 1.1144 0.7697 -0.0902 0.067 Uiso 1 1 calc R . .
C2 C 1.0602(3) 0.5898(2) -0.0943(2) 0.0655(6) Uani 1 1 d . . .
H2A H 1.1068 0.5567 -0.1577 0.079 Uiso 1 1 calc R . .
H2B H 1.1062 0.5680 -0.0281 0.079 Uiso 1 1 calc R . .
C3 C 0.8868(2) 0.5308(2) -0.1549(2) 0.0556(5) Uani 1 1 d . . .
C4 C 0.6725(2) 0.62990(17) -0.11413(17) 0.0452(4) Uani 1 1 d . . .
H4 H 0.6378 0.5434 -0.1203 0.054 Uiso 1 1 calc R . .
C5 C 0.5429(2) 0.64097(17) -0.21212(16) 0.0449(4) Uani 1 1 d . . .
C6 C 0.5594(2) 0.6414(2) -0.31632(19) 0.0599(5) Uani 1 1 d . . .
H6 H 0.6524 0.6349 -0.3283 0.072 Uiso 1 1 calc R . .
C7 C 0.4384(3) 0.6513(2) -0.4047(2) 0.0694(6) Uani 1 1 d . . .
H7 H 0.4524 0.6514 -0.4749 0.083 Uiso 1 1 calc R . .
C8 C 0.3001(2) 0.6610(2) -0.39096(19) 0.0632(6) Uani 1 1 d . . .
C9 C 0.1707(3) 0.6760(4) -0.4853(3) 0.1070(10) Uani 1 1 d . . .
H9A H 0.2107 0.6968 -0.5389 0.160 Uiso 1 1 calc R . .
H9B H 0.1306 0.7469 -0.4395 0.160 Uiso 1 1 calc R . .
H9C H 0.0888 0.5938 -0.5373 0.160 Uiso 1 1 calc R . .
C10 C 0.2827(2) 0.6572(2) -0.28742(19) 0.0638(6) Uani 1 1 d . . .
H10 H 0.1888 0.6618 -0.2767 0.077 Uiso 1 1 calc R . .
C11 C 0.4002(2) 0.6467(2) -0.19988(18) 0.0560(5) Uani 1 1 d . . .
H11 H 0.3845 0.6433 -0.1315 0.067 Uiso 1 1 calc R . .
C12 C 0.9036(2) 0.77517(17) 0.07885(17) 0.0421(4) Uani 1 1 d . . .
H12 H 0.9364 0.7053 0.0958 0.051 Uiso 1 1 calc R . .
C13 C 0.99113(19) 0.90913(17) 0.19596(16) 0.0407(4) Uani 1 1 d . . .
C14 C 1.0202(2) 1.02515(19) 0.18913(19) 0.0521(5) Uani 1 1 d . . .
H14 H 0.9880 1.0206 0.1098 0.063 Uiso 1 1 calc R . .
C15 C 1.0960(2) 1.1468(2) 0.2985(2) 0.0573(5) Uani 1 1 d . . .
H15 H 1.1125 1.2235 0.2916 0.069 Uiso 1 1 calc R . .
C16 C 1.1483(2) 1.1584(2) 0.41796(19) 0.0557(5) Uani 1 1 d . . .
C17 C 1.2314(3) 1.2937(2) 0.5368(2) 0.0830(7) Uani 1 1 d . . .
H17A H 1.3418 1.3086 0.5595 0.125 Uiso 1 1 calc R . .
H17B H 1.2054 1.2959 0.6060 0.125 Uiso 1 1 calc R . .
H17C H 1.1997 1.3623 0.5204 0.125 Uiso 1 1 calc R . .
C18 C 1.1222(2) 1.0426(2) 0.42413(18) 0.0573(5) Uani 1 1 d . . .
H18 H 1.1575 1.0472 0.5035 0.069 Uiso 1 1 calc R . .
C19 C 1.0450(2) 0.9200(2) 0.31558(18) 0.0510(5) Uani 1 1 d . . .
H19 H 1.0289 0.8435 0.3229 0.061 Uiso 1 1 calc R . .
C20 C 0.6565(2) 0.68944(17) 0.10294(17) 0.0432(4) Uani 1 1 d . . .
C21 C 0.72135(19) 0.74059(16) 0.02847(16) 0.0396(4) Uani 1 1 d . . .
C22 C 0.6648(2) 0.86660(17) 0.05169(16) 0.0413(4) Uani 1 1 d . . .
C23 C 0.5841(2) 0.88732(17) 0.14006(16) 0.0431(4) Uani 1 1 d . . .
C24 C 0.5172(2) 0.9897(2) 0.19189(19) 0.0573(5) Uani 1 1 d . . .
H24 H 0.5230 1.0600 0.1747 0.069 Uiso 1 1 calc R . .
C25 C 0.4421(3) 0.9837(2) 0.2693(2) 0.0707(6) Uani 1 1 d . . .
H25 H 0.3980 1.0519 0.3058 0.085 Uiso 1 1 calc R . .
C26 C 0.4307(3) 0.8783(3) 0.2943(2) 0.0685(6) Uani 1 1 d . . .
H26 H 0.3781 0.8764 0.3462 0.082 Uiso 1 1 calc R . .
C27 C 0.4963(2) 0.7766(2) 0.24304(19) 0.0551(5) Uani 1 1 d . . .
H27 H 0.4881 0.7054 0.2589 0.066 Uiso 1 1 calc R . .
C28 C 0.57457(19) 0.78324(17) 0.16753(16) 0.0423(4) Uani 1 1 d . . .
N1 N 0.81985(17) 0.63490(14) -0.13384(14) 0.0471(4) Uani 1 1 d . . .
N2 N 0.93009(17) 0.76190(14) -0.03533(14) 0.0448(4) Uani 1 1 d . . .
O1 O 0.8137(2) 0.41377(15) -0.21469(17) 0.0794(5) Uani 1 1 d . . .
O2 O 0.67227(17) 0.58980(14) 0.10823(14) 0.0623(4) Uani 1 1 d . . .
O3 O 0.68410(15) 0.93561(13) 0.00502(12) 0.0555(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.487(2) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.501(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.214(2) . ?
C3 N1 1.375(2) . ?
C4 N1 1.468(2) . ?
C4 C5 1.518(3) . ?
C4 C21 1.563(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.365(3) . ?
C5 C11 1.391(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.363(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.377(3) . ?
C8 C9 1.513(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 N2 1.472(2) . ?
C12 C13 1.502(2) . ?
C12 C21 1.569(2) . ?
C12 H12 0.9800 . ?
C13 C19 1.383(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C18 1.376(3) . ?
C16 C17 1.514(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.206(2) . ?
C20 C28 1.480(2) . ?
C20 C21 1.528(2) . ?
C21 C22 1.541(2) . ?
C22 O3 1.2078(19) . ?
C22 C23 1.468(3) . ?
C23 C24 1.392(3) . ?
C23 C28 1.393(2) . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.378(2) . ?
C27 H27 0.9300 . ?
N1 N2 1.444(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
N2 C1 C2 106.06(15) . . ?
N2 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
N2 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C3 C2 C1 104.61(16) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O1 C3 N1 124.05(19) . . ?
O1 C3 C2 128.37(19) . . ?
N1 C3 C2 107.57(17) . . ?
N1 C4 C5 114.19(14) . . ?
N1 C4 C21 103.30(13) . . ?
C5 C4 C21 116.22(14) . . ?
N1 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C21 C4 H4 107.6 . . ?
C6 C5 C11 117.77(18) . . ?
C6 C5 C4 121.99(16) . . ?
C11 C5 C4 120.21(16) . . ?
C5 C6 C7 120.71(19) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C10 117.4(2) . . ?
C7 C8 C9 121.4(2) . . ?
C10 C8 C9 121.2(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 121.73(19) . . ?
C11 C10 H10 119.1 . . ?
C8 C10 H10 119.1 . . ?
C10 C11 C5 120.72(18) . . ?
C10 C11 H11 119.6 . . ?
C5 C11 H11 119.6 . . ?
N2 C12 C13 112.98(13) . . ?
N2 C12 C21 100.71(13) . . ?
C13 C12 C21 116.52(13) . . ?
N2 C12 H12 108.7 . . ?
C13 C12 H12 108.7 . . ?
C21 C12 H12 108.7 . . ?
C19 C13 C14 117.73(17) . . ?
C19 C13 C12 120.19(15) . . ?
C14 C13 C12 122.08(16) . . ?
C15 C14 C13 120.64(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.85(18) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C18 C16 C15 117.33(18) . . ?
C18 C16 C17 121.9(2) . . ?
C15 C16 C17 120.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 C19 121.58(18) . . ?
C16 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C13 120.85(18) . . ?
C18 C19 H19 119.6 . . ?
C13 C19 H19 119.6 . . ?
O2 C20 C28 126.54(16) . . ?
O2 C20 C21 124.89(16) . . ?
C28 C20 C21 108.56(14) . . ?
C20 C21 C22 103.21(13) . . ?
C20 C21 C4 111.85(14) . . ?
C22 C21 C4 116.50(14) . . ?
C20 C21 C12 111.84(13) . . ?
C22 C21 C12 111.39(13) . . ?
C4 C21 C12 102.35(13) . . ?
O3 C22 C23 126.42(16) . . ?
O3 C22 C21 125.64(16) . . ?
C23 C22 C21 107.93(14) . . ?
C24 C23 C28 120.09(17) . . ?
C24 C23 C22 129.15(17) . . ?
C28 C23 C22 110.73(15) . . ?
C25 C24 C23 117.97(19) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C24 C25 C26 121.6(2) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 118.14(19) . . ?
C26 C27 H27 120.9 . . ?
C28 C27 H27 120.9 . . ?
C27 C28 C23 121.51(17) . . ?
C27 C28 C20 129.08(17) . . ?
C23 C28 C20 109.41(15) . . ?
C3 N1 N2 111.84(15) . . ?
C3 N1 C4 121.66(15) . . ?
N2 N1 C4 108.64(12) . . ?
N1 N2 C12 101.35(12) . . ?
N1 N2 C1 103.58(13) . . ?
C12 N2 C1 114.30(14) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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/cc1jmfzk
_database_code_depnum_ccdc_archive 'CCDC 1418869'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 Cl N2 O3, C3 H7 N O'
_chemical_formula_sum            'C30 H28 Cl N3 O4'
_chemical_formula_weight         530.00

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                   8.7245(12)
_cell_length_b                   10.1071(15)
_cell_length_c                   15.532(2)
_cell_angle_alpha                88.142(4)
_cell_angle_beta                 85.263(4)
_cell_angle_gamma                75.777(4)
_cell_volume                     1323.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9778
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_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    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_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            19939
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.58
_reflns_number_total             6053
_reflns_number_gt                4606
_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)+(0.0598P)²+0.3713P] 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         6053
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 -0.13903(19) 0.58657(18) 0.43644(10) 0.0415(4) Uani 1 1 d . . .
C2 C -0.2114(2) 0.4660(2) 0.43320(11) 0.0504(4) Uani 1 1 d . . .
H2A H -0.2041 0.4155 0.4875 0.060 Uiso 1 1 calc R . .
H2B H -0.3220 0.4952 0.4209 0.060 Uiso 1 1 calc R . .
C3 C -0.1142(2) 0.38029(19) 0.36099(11) 0.0491(4) Uani 1 1 d . . .
H3A H -0.0281 0.3111 0.3832 0.059 Uiso 1 1 calc R . .
H3B H -0.1795 0.3359 0.3300 0.059 Uiso 1 1 calc R . .
C4 C 0.11908(17) 0.43566(15) 0.27767(9) 0.0341(3) Uani 1 1 d . . .
H4 H 0.1732 0.3904 0.3274 0.041 Uiso 1 1 calc R . .
C5 C 0.15167(17) 0.33525(15) 0.20478(9) 0.0329(3) Uani 1 1 d . . .
C6 C 0.05601(19) 0.35169(16) 0.13601(10) 0.0383(3) Uani 1 1 d . . .
H6 H -0.0292 0.4276 0.1338 0.046 Uiso 1 1 calc R . .
C7 C 0.0861(2) 0.25688(18) 0.07120(10) 0.0434(4) Uani 1 1 d . . .
H7 H 0.0214 0.2705 0.0254 0.052 Uiso 1 1 calc R . .
C8 C 0.2104(2) 0.14191(19) 0.07268(11) 0.0464(4) Uani 1 1 d . . .
C9 C 0.2397(3) 0.0385(3) 0.00120(16) 0.0791(7) Uani 1 1 d . . .
H9A H 0.1934 -0.0357 0.0194 0.119 Uiso 1 1 calc R . .
H9B H 0.3518 0.0043 -0.0116 0.119 Uiso 1 1 calc R . .
H9C H 0.1926 0.0812 -0.0496 0.119 Uiso 1 1 calc R . .
C10 C 0.3040(2) 0.12510(19) 0.14198(12) 0.0506(4) Uani 1 1 d . . .
H10 H 0.3879 0.0482 0.1448 0.061 Uiso 1 1 calc R . .
C11 C 0.27549(18) 0.21979(17) 0.20678(11) 0.0418(4) Uani 1 1 d . . .
H11 H 0.3403 0.2059 0.2525 0.050 Uiso 1 1 calc R . .
C12 C 0.03529(18) 0.91220(17) 0.27337(11) 0.0409(4) Uani 1 1 d . . .
H12 H 0.1415 0.8983 0.2839 0.049 Uiso 1 1 calc R . .
C13 C -0.04456(19) 1.03635(17) 0.24011(11) 0.0422(4) Uani 1 1 d . . .
H13 H 0.0072 1.1058 0.2280 0.051 Uiso 1 1 calc R . .
C14 C -0.20194(19) 1.05547(16) 0.22517(10) 0.0384(3) Uani 1 1 d . . .
C15 C -0.28109(19) 0.95453(18) 0.24273(11) 0.0435(4) Uani 1 1 d . . .
H15 H -0.3877 0.9693 0.2328 0.052 Uiso 1 1 calc R . .
C16 C -0.19977(19) 0.83106(17) 0.27527(11) 0.0420(4) Uani 1 1 d . . .
H16 H -0.2520 0.7618 0.2868 0.050 Uiso 1 1 calc R . .
C17 C -0.04123(18) 0.80841(16) 0.29110(9) 0.0352(3) Uani 1 1 d . . .
C18 C 0.04876(19) 0.67293(16) 0.32745(10) 0.0376(3) Uani 1 1 d . . .
H18 H 0.1090 0.6911 0.3744 0.045 Uiso 1 1 calc R . .
C19 C 0.15813(18) 0.62534(15) 0.16678(9) 0.0345(3) Uani 1 1 d . . .
C20 C 0.16545(18) 0.57516(15) 0.26118(9) 0.0339(3) Uani 1 1 d . . .
C21 C 0.34093(19) 0.55930(16) 0.27757(10) 0.0383(3) Uani 1 1 d . . .
C22 C 0.42588(19) 0.59089(16) 0.19668(10) 0.0385(3) Uani 1 1 d . . .
C23 C 0.5860(2) 0.58856(19) 0.17988(13) 0.0504(4) Uani 1 1 d . . .
H23 H 0.6571 0.5622 0.2223 0.060 Uiso 1 1 calc R . .
C24 C 0.6349(2) 0.6264(2) 0.09883(15) 0.0623(5) Uani 1 1 d . . .
H24 H 0.7408 0.6271 0.0863 0.075 Uiso 1 1 calc R . .
C25 C 0.5294(2) 0.6637(2) 0.03492(14) 0.0620(5) Uani 1 1 d . . .
H25 H 0.5665 0.6879 -0.0197 0.074 Uiso 1 1 calc R . .
C26 C 0.3709(2) 0.66586(19) 0.05077(11) 0.0496(4) Uani 1 1 d . . .
H26 H 0.3005 0.6911 0.0079 0.060 Uiso 1 1 calc R . .
C27 C 0.32026(18) 0.62885(15) 0.13314(10) 0.0371(3) Uani 1 1 d . . .
C28 C 0.5566(3) 0.1707(3) 0.58492(17) 0.0756(7) Uani 1 1 d . . .
H28 H 0.4573 0.2316 0.5869 0.091 Uiso 1 1 calc R . .
C29 C 0.5446(3) 0.1854(3) 0.43019(16) 0.0865(8) Uani 1 1 d . . .
H29A H 0.4433 0.2455 0.4462 0.130 Uiso 1 1 calc R . .
H29B H 0.5298 0.1101 0.3985 0.130 Uiso 1 1 calc R . .
H29C H 0.6083 0.2342 0.3948 0.130 Uiso 1 1 calc R . .
C30 C 0.7778(3) 0.0433(4) 0.4977(2) 0.1190(12) Uani 1 1 d . . .
H30A H 0.8547 0.0937 0.4787 0.178 Uiso 1 1 calc R . .
H30B H 0.7782 -0.0246 0.4558 0.178 Uiso 1 1 calc R . .
H30C H 0.8040 -0.0005 0.5522 0.178 Uiso 1 1 calc R . .
Cl1 Cl -0.30429(5) 1.21249(5) 0.18459(3) 0.05618(15) Uani 1 1 d . . .
N1 N -0.05536(18) 0.58875(14) 0.36116(8) 0.0442(3) Uani 1 1 d . . .
N2 N -0.05196(16) 0.47969(14) 0.30379(8) 0.0385(3) Uani 1 1 d . . .
N3 N 0.6238(2) 0.13451(19) 0.50741(12) 0.0644(5) Uani 1 1 d . . .
O1 O -0.15502(16) 0.67037(15) 0.49315(8) 0.0592(4) Uani 1 1 d . . .
O2 O 0.04003(13) 0.65715(13) 0.12762(7) 0.0456(3) Uani 1 1 d . . .
O3 O 0.39656(15) 0.52493(15) 0.34575(8) 0.0583(4) Uani 1 1 d . . .
O4 O 0.6093(2) 0.1338(2) 0.65424(12) 0.1017(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.218(2) . ?
C1 N1 1.329(2) . ?
C1 C2 1.508(3) . ?
C2 C3 1.507(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.491(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.475(2) . ?
C4 C5 1.507(2) . ?
C4 C20 1.567(2) . ?
C4 H4 0.9800 . ?
C5 C11 1.383(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.386(3) . ?
C8 C9 1.513(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.384(2) . ?
C12 C17 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 Cl1 1.7449(16) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.518(2) . ?
C18 N1 1.448(2) . ?
C18 C20 1.572(2) . ?
C18 H18 0.9800 . ?
C19 O2 1.2095(18) . ?
C19 C27 1.475(2) . ?
C19 C20 1.537(2) . ?
C20 C21 1.541(2) . ?
C21 O3 1.2066(19) . ?
C21 C22 1.472(2) . ?
C22 C27 1.386(2) . ?
C22 C23 1.394(2) . ?
C23 C24 1.369(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(2) . ?
C26 H26 0.9300 . ?
C28 O4 1.217(3) . ?
C28 N3 1.317(3) . ?
C28 H28 0.9300 . ?
C29 N3 1.450(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 N3 1.430(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N1 N2 1.4328(19) . ?

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
O1 C1 N1 124.95(17) . . ?
O1 C1 C2 129.16(15) . . ?
N1 C1 C2 105.84(14) . . ?
C3 C2 C1 104.19(13) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N2 C3 C2 104.34(14) . . ?
N2 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
N2 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
N2 C4 C5 111.45(12) . . ?
N2 C4 C20 102.31(12) . . ?
C5 C4 C20 118.18(12) . . ?
N2 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C20 C4 H4 108.1 . . ?
C11 C5 C6 117.98(14) . . ?
C11 C5 C4 120.14(13) . . ?
C6 C5 C4 121.82(13) . . ?
C7 C6 C5 120.73(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.42(15) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C10 117.59(16) . . ?
C7 C8 C9 120.37(17) . . ?
C10 C8 C9 122.03(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 121.39(16) . . ?
C11 C10 H10 119.3 . . ?
C8 C10 H10 119.3 . . ?
C10 C11 C5 120.87(15) . . ?
C10 C11 H11 119.6 . . ?
C5 C11 H11 119.6 . . ?
C13 C12 C17 120.70(14) . . ?
C13 C12 H12 119.6 . . ?
C17 C12 H12 119.6 . . ?
C14 C13 C12 118.94(15) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.57(15) . . ?
C15 C14 Cl1 119.18(12) . . ?
C13 C14 Cl1 119.25(13) . . ?
C14 C15 C16 118.86(14) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 121.05(15) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 118.87(14) . . ?
C12 C17 C18 119.82(14) . . ?
C16 C17 C18 121.30(14) . . ?
N1 C18 C17 112.52(13) . . ?
N1 C18 C20 102.24(12) . . ?
C17 C18 C20 116.01(12) . . ?
N1 C18 H18 108.6 . . ?
C17 C18 H18 108.6 . . ?
C20 C18 H18 108.6 . . ?
O2 C19 C27 126.38(14) . . ?
O2 C19 C20 125.89(14) . . ?
C27 C19 C20 107.73(12) . . ?
C19 C20 C21 103.03(12) . . ?
C19 C20 C4 113.85(12) . . ?
C21 C20 C4 110.14(12) . . ?
C19 C20 C18 114.38(12) . . ?
C21 C20 C18 112.62(12) . . ?
C4 C20 C18 103.09(11) . . ?
O3 C21 C22 126.94(15) . . ?
O3 C21 C20 124.54(15) . . ?
C22 C21 C20 108.52(12) . . ?
C27 C22 C23 121.09(15) . . ?
C27 C22 C21 109.65(14) . . ?
C23 C22 C21 129.25(15) . . ?
C24 C23 C22 117.71(17) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C25 121.29(17) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.45(17) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 117.52(17) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C22 C27 C26 120.93(15) . . ?
C22 C27 C19 110.98(13) . . ?
C26 C27 C19 128.09(15) . . ?
O4 C28 N3 127.5(2) . . ?
O4 C28 H28 116.2 . . ?
N3 C28 H28 116.2 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 N1 N2 115.72(13) . . ?
C1 N1 C18 132.50(14) . . ?
N2 N1 C18 111.44(12) . . ?
N1 N2 C4 101.06(12) . . ?
N1 N2 C3 102.95(11) . . ?
C4 N2 C3 114.30(13) . . ?
C28 N3 C30 120.3(2) . . ?
C28 N3 C29 121.30(19) . . ?
C30 N3 C29 118.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.264
_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_1j
_audit_block_doi                 10.5517/cc1jmg0m
_database_code_depnum_ccdc_archive 'CCDC 1418870'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 Cl N2 O4'
_chemical_formula_sum            'C27 H21 Cl N2 O4'
_chemical_formula_weight         472.91

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                   14.070(4)
_cell_length_b                   8.4364(19)
_cell_length_c                   20.473(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.990(15)
_cell_angle_gamma                90.00
_cell_volume                     2268.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5163
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      22.84

_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    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.960
_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            24507
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.63
_reflns_number_total             5254
_reflns_number_gt                2712
_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)+(0.0570P)²+0.2311P] 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         5254
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.35157(16) 0.6925(2) 0.92844(10) 0.0336(5) Uani 1 1 d . . .
C2 C 0.43198(18) 0.6437(3) 0.90976(12) 0.0470(6) Uani 1 1 d . . .
H2 H 0.4745 0.7169 0.8999 0.056 Uiso 1 1 calc R . .
C3 C 0.4473(2) 0.4829(3) 0.90615(13) 0.0574(7) Uani 1 1 d . . .
H3 H 0.5004 0.4471 0.8930 0.069 Uiso 1 1 calc R . .
C4 C 0.3849(2) 0.3740(3) 0.92171(13) 0.0596(7) Uani 1 1 d . . .
H4 H 0.3980 0.2663 0.9201 0.072 Uiso 1 1 calc R . .
C5 C 0.30439(19) 0.4215(3) 0.93936(12) 0.0480(6) Uani 1 1 d . . .
H5 H 0.2621 0.3478 0.9491 0.058 Uiso 1 1 calc R . .
C6 C 0.28773(17) 0.5832(2) 0.94236(10) 0.0361(5) Uani 1 1 d . . .
C7 C 0.20571(18) 0.6667(2) 0.95718(11) 0.0371(5) Uani 1 1 d . . .
C8 C 0.22413(15) 0.8456(2) 0.95618(10) 0.0298(5) Uani 1 1 d . . .
C9 C 0.31889(16) 0.8554(2) 0.93638(10) 0.0313(5) Uani 1 1 d . . .
C10 C 0.13190(16) 0.9410(2) 0.90594(10) 0.0326(5) Uani 1 1 d . . .
H10 H 0.0700 0.8839 0.9032 0.039 Uiso 1 1 calc R . .
C11 C 0.12907(16) 0.9617(2) 0.83193(10) 0.0339(5) Uani 1 1 d . . .
C12 C 0.13887(17) 1.1083(2) 0.80463(10) 0.0395(6) Uani 1 1 d . . .
H12 H 0.1507 1.1983 0.8327 0.047 Uiso 1 1 calc R . .
C13 C 0.13093(19) 1.1206(3) 0.73552(11) 0.0481(6) Uani 1 1 d . . .
C14 C 0.1613(3) 1.4011(3) 0.74326(14) 0.0775(9) Uani 1 1 d . . .
H14A H 0.2282 1.3911 0.7781 0.116 Uiso 1 1 calc R . .
H14B H 0.1128 1.4183 0.7657 0.116 Uiso 1 1 calc R . .
H14C H 0.1600 1.4893 0.7133 0.116 Uiso 1 1 calc R . .
C15 C 0.1127(2) 0.9878(3) 0.69397(12) 0.0623(8) Uani 1 1 d . . .
H15 H 0.1063 0.9966 0.6473 0.075 Uiso 1 1 calc R . .
C16 C 0.1040(2) 0.8430(3) 0.72104(12) 0.0635(8) Uani 1 1 d . . .
H16 H 0.0932 0.7530 0.6930 0.076 Uiso 1 1 calc R . .
C17 C 0.1111(2) 0.8297(3) 0.78956(11) 0.0500(6) Uani 1 1 d . . .
H17 H 0.1037 0.7310 0.8074 0.060 Uiso 1 1 calc R . .
C18 C 0.05070(18) 1.1431(2) 0.95603(11) 0.0330(5) Uani 1 1 d . . .
C19 C 0.08569(17) 1.2353(2) 1.02258(11) 0.0409(6) Uani 1 1 d . . .
H19A H 0.0492 1.2027 1.0525 0.049 Uiso 1 1 calc R . .
H19B H 0.0751 1.3479 1.0133 0.049 Uiso 1 1 calc R . .
C20 C 0.19715(18) 1.1986(3) 1.05619(11) 0.0471(6) Uani 1 1 d . . .
H20A H 0.2368 1.2955 1.0643 0.056 Uiso 1 1 calc R . .
H20B H 0.2107 1.1459 1.1007 0.056 Uiso 1 1 calc R . .
C21 C 0.23521(16) 0.9231(2) 1.02733(10) 0.0323(5) Uani 1 1 d . . .
H21 H 0.1755 0.8933 1.0385 0.039 Uiso 1 1 calc R . .
C22 C 0.32825(16) 0.8876(2) 1.09027(10) 0.0328(5) Uani 1 1 d . . .
C23 C 0.31740(19) 0.7959(3) 1.14319(12) 0.0522(7) Uani 1 1 d . . .
H23 H 0.2537 0.7551 1.1381 0.063 Uiso 1 1 calc R . .
C24 C 0.3993(2) 0.7639(3) 1.20338(13) 0.0638(8) Uani 1 1 d . . .
H24 H 0.3912 0.7011 1.2384 0.077 Uiso 1 1 calc R . .
C25 C 0.49212(19) 0.8256(3) 1.21090(12) 0.0487(6) Uani 1 1 d . . .
C26 C 0.50580(18) 0.9162(3) 1.15963(11) 0.0415(6) Uani 1 1 d . . .
H26 H 0.5698 0.9563 1.1652 0.050 Uiso 1 1 calc R . .
C27 C 0.42339(17) 0.9474(2) 1.09933(11) 0.0374(5) Uani 1 1 d . . .
H27 H 0.4322 1.0096 1.0644 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.59577(6) 0.78886(11) 1.28697(4) 0.0900(3) Uani 1 1 d . . .
N1 N 0.13430(13) 1.08873(19) 0.94445(8) 0.0326(4) Uani 1 1 d . . .
N2 N 0.22488(13) 1.09297(19) 1.00737(8) 0.0328(4) Uani 1 1 d . . .
O1 O 0.13506(13) 0.60709(18) 0.96843(9) 0.0598(5) Uani 1 1 d . . .
O2 O 0.35997(12) 0.97591(16) 0.92796(8) 0.0437(4) Uani 1 1 d . . .
O3 O 0.13616(17) 1.2601(2) 0.70286(8) 0.0729(6) Uani 1 1 d . . .
O4 O -0.03680(12) 1.11922(17) 0.91596(8) 0.0451(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(3) . ?
C1 C6 1.387(3) . ?
C1 C9 1.477(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(3) . ?
C7 O1 1.207(2) . ?
C7 C8 1.533(3) . ?
C8 C9 1.528(3) . ?
C8 C21 1.553(3) . ?
C8 C10 1.560(3) . ?
C9 O2 1.212(2) . ?
C10 N1 1.468(2) . ?
C10 C11 1.511(3) . ?
C10 H10 0.9800 . ?
C11 C17 1.378(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.369(3) . ?
C13 C15 1.374(3) . ?
C14 O3 1.419(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O4 1.227(2) . ?
C18 N1 1.360(3) . ?
C18 C19 1.491(3) . ?
C19 C20 1.502(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N2 1.491(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N2 1.483(2) . ?
C21 C22 1.502(3) . ?
C21 H21 0.9800 . ?
C22 C27 1.380(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.379(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(3) . ?
C25 Cl1 1.738(2) . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
N1 N2 1.452(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 120.93(19) . . ?
C2 C1 C9 128.79(19) . . ?
C6 C1 C9 110.27(18) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 C7 109.69(18) . . ?
C5 C6 C7 129.5(2) . . ?
O1 C7 C6 126.8(2) . . ?
O1 C7 C8 124.6(2) . . ?
C6 C7 C8 108.62(18) . . ?
C9 C8 C7 103.00(16) . . ?
C9 C8 C21 114.96(16) . . ?
C7 C8 C21 111.27(15) . . ?
C9 C8 C10 113.31(15) . . ?
C7 C8 C10 114.35(17) . . ?
C21 C8 C10 100.45(15) . . ?
O2 C9 C1 125.58(19) . . ?
O2 C9 C8 126.11(18) . . ?
C1 C9 C8 108.31(16) . . ?
N1 C10 C11 115.31(16) . . ?
N1 C10 C8 103.32(15) . . ?
C11 C10 C8 115.94(17) . . ?
N1 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C8 C10 H10 107.2 . . ?
C17 C11 C12 119.35(19) . . ?
C17 C11 C10 118.08(19) . . ?
C12 C11 C10 122.50(18) . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O3 C13 C15 115.4(2) . . ?
O3 C13 C12 124.4(2) . . ?
C15 C13 C12 120.1(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C11 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C11 C17 H17 119.8 . . ?
O4 C18 N1 123.44(19) . . ?
O4 C18 C19 128.4(2) . . ?
N1 C18 C19 108.19(19) . . ?
C18 C19 C20 105.07(17) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N2 C20 C19 107.28(17) . . ?
N2 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
N2 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
N2 C21 C22 113.49(16) . . ?
N2 C21 C8 100.46(14) . . ?
C22 C21 C8 118.98(17) . . ?
N2 C21 H21 107.8 . . ?
C22 C21 H21 107.8 . . ?
C8 C21 H21 107.8 . . ?
C27 C22 C23 118.3(2) . . ?
C27 C22 C21 123.22(19) . . ?
C23 C22 C21 118.5(2) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 119.1(2) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.3(2) . . ?
C24 C25 Cl1 119.72(19) . . ?
C26 C25 Cl1 119.0(2) . . ?
C25 C26 C27 119.2(2) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 120.9(2) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C18 N1 N2 112.09(15) . . ?
C18 N1 C10 121.67(18) . . ?
N2 N1 C10 109.95(14) . . ?
N1 N2 C21 100.89(14) . . ?
N1 N2 C20 104.60(15) . . ?
C21 N2 C20 114.57(16) . . ?
C13 O3 C14 118.81(17) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1n
_audit_block_doi                 10.5517/cc1jmg3q
_database_code_depnum_ccdc_archive 'CCDC 1418873'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Br2 N2 O3'
_chemical_formula_sum            'C26 H18 Br2 N2 O3'
_chemical_formula_weight         566.24

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'
Br Br -0.2901 2.4595 '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                   9.345(3)
_cell_length_b                   11.391(4)
_cell_length_c                   12.452(4)
_cell_angle_alpha                115.544(10)
_cell_angle_beta                 102.578(10)
_cell_angle_gamma                97.067(11)
_cell_volume                     1131.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6860
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    3.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_T_max  0.562
_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            15454
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.61
_reflns_number_total             5119
_reflns_number_gt                3340
_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)+(0.1495P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5119
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2407
_refine_ls_wR_factor_gt          0.2127
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Br1 Br 0.29598(6) 0.19390(6) 0.43742(6) 0.0763(3) Uani 1 1 d . . .
Br2 Br 1.29189(9) 0.82529(10) 1.50227(7) 0.0989(4) Uani 1 1 d . . .
C1 C 0.5817(5) 0.9631(5) 1.1425(5) 0.0440(11) Uani 1 1 d . . .
C2 C 0.4155(6) 0.8994(5) 1.0854(6) 0.0539(13) Uani 1 1 d . . .
H2A H 0.3730 0.9197 1.0189 0.065 Uiso 1 1 calc R . .
H2B H 0.3628 0.9306 1.1476 0.065 Uiso 1 1 calc R . .
C3 C 0.4036(5) 0.7505(5) 1.0345(5) 0.0486(11) Uani 1 1 d . . .
H3A H 0.3690 0.7189 1.0877 0.058 Uiso 1 1 calc R . .
H3B H 0.3326 0.7009 0.9510 0.058 Uiso 1 1 calc R . .
C4 C 0.5960(4) 0.7251(4) 0.9208(4) 0.0350(9) Uani 1 1 d . . .
H4 H 0.5649 0.7975 0.9064 0.042 Uiso 1 1 calc R . .
C5 C 0.5193(4) 0.5944(4) 0.8048(4) 0.0348(9) Uani 1 1 d . . .
C6 C 0.5022(5) 0.4731(5) 0.8070(5) 0.0490(12) Uani 1 1 d . . .
H6 H 0.5340 0.4718 0.8825 0.059 Uiso 1 1 calc R . .
C7 C 0.4381(6) 0.3538(5) 0.6972(6) 0.0561(13) Uani 1 1 d . . .
H7 H 0.4324 0.2720 0.6978 0.067 Uiso 1 1 calc R . .
C8 C 0.3831(5) 0.3573(5) 0.5875(5) 0.0494(12) Uani 1 1 d . . .
C9 C 0.3922(5) 0.4768(5) 0.5843(5) 0.0490(11) Uani 1 1 d . . .
H9 H 0.3521 0.4781 0.5097 0.059 Uiso 1 1 calc R . .
C10 C 0.4613(5) 0.5947(5) 0.6931(5) 0.0451(11) Uani 1 1 d . . .
H10 H 0.4691 0.6760 0.6913 0.054 Uiso 1 1 calc R . .
C11 C 1.0665(5) 0.8527(5) 1.1927(5) 0.0479(11) Uani 1 1 d . . .
H11 H 1.0894 0.8566 1.1251 0.058 Uiso 1 1 calc R . .
C12 C 1.1758(5) 0.8435(5) 1.2816(5) 0.0521(12) Uani 1 1 d . . .
H12 H 1.2725 0.8415 1.2741 0.063 Uiso 1 1 calc R . .
C13 C 1.1412(6) 0.8373(5) 1.3804(5) 0.0551(13) Uani 1 1 d . . .
C14 C 1.0018(7) 0.8424(7) 1.3965(5) 0.0638(15) Uani 1 1 d . . .
H14 H 0.9803 0.8387 1.4646 0.077 Uiso 1 1 calc R . .
C15 C 0.8926(6) 0.8535(6) 1.3075(5) 0.0534(12) Uani 1 1 d . . .
H15 H 0.7976 0.8592 1.3177 0.064 Uiso 1 1 calc R . .
C16 C 0.9221(5) 0.8560(4) 1.2045(4) 0.0388(10) Uani 1 1 d . . .
C17 C 0.8034(5) 0.8696(4) 1.1089(4) 0.0376(9) Uani 1 1 d . . .
H17 H 0.8372 0.9580 1.1154 0.045 Uiso 1 1 calc R . .
C18 C 0.8438(4) 0.8170(4) 0.8958(4) 0.0358(9) Uani 1 1 d . . .
C19 C 0.7720(4) 0.7615(4) 0.9699(4) 0.0335(9) Uani 1 1 d . . .
C20 C 0.8350(4) 0.6364(4) 0.9487(4) 0.0375(10) Uani 1 1 d . . .
C21 C 0.9201(5) 0.6192(4) 0.8583(4) 0.0397(10) Uani 1 1 d . . .
C22 C 0.9936(5) 0.5176(5) 0.8075(5) 0.0512(12) Uani 1 1 d . . .
H22 H 0.9913 0.4478 0.8276 0.061 Uiso 1 1 calc R . .
C23 C 1.0694(7) 0.5254(6) 0.7268(6) 0.0664(16) Uani 1 1 d . . .
H23 H 1.1176 0.4585 0.6906 0.080 Uiso 1 1 calc R . .
C24 C 1.0760(6) 0.6300(6) 0.6977(6) 0.0615(14) Uani 1 1 d . . .
H24 H 1.1287 0.6321 0.6430 0.074 Uiso 1 1 calc R . .
C25 C 1.0059(5) 0.7305(5) 0.7485(5) 0.0468(11) Uani 1 1 d . . .
H25 H 1.0110 0.8011 0.7294 0.056 Uiso 1 1 calc R . .
C26 C 0.9268(4) 0.7241(4) 0.8294(4) 0.0365(9) Uani 1 1 d . . .
N1 N 0.5573(4) 0.7315(3) 1.0323(4) 0.0385(8) Uani 1 1 d . . .
N2 N 0.6544(4) 0.8605(3) 1.1278(4) 0.0396(8) Uani 1 1 d . . .
O1 O 0.6451(4) 1.0803(3) 1.1942(4) 0.0592(10) Uani 1 1 d . . .
O2 O 0.8328(4) 0.9223(3) 0.8968(4) 0.0515(9) Uani 1 1 d . . .
O3 O 0.8155(4) 0.5659(3) 0.9962(3) 0.0493(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
Br1 C8 1.893(5) . ?
Br2 C13 1.898(5) . ?
C1 O1 1.202(6) . ?
C1 N2 1.387(6) . ?
C1 C2 1.498(7) . ?
C2 C3 1.512(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.483(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.484(6) . ?
C4 C5 1.499(6) . ?
C4 C19 1.558(6) . ?
C4 H4 0.9800 . ?
C5 C10 1.380(6) . ?
C5 C6 1.384(6) . ?
C6 C7 1.384(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(7) . ?
C9 C10 1.375(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.383(7) . ?
C11 C16 1.392(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(8) . ?
C14 C15 1.394(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.516(6) . ?
C17 N2 1.461(6) . ?
C17 C19 1.566(6) . ?
C17 H17 0.9800 . ?
C18 O2 1.212(5) . ?
C18 C26 1.460(6) . ?
C18 C19 1.539(6) . ?
C19 C20 1.548(6) . ?
C20 O3 1.203(5) . ?
C20 C21 1.476(7) . ?
C21 C26 1.387(6) . ?
C21 C22 1.401(6) . ?
C22 C23 1.376(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(7) . ?
C25 H25 0.9300 . ?
N1 N2 1.446(5) . ?

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
O1 C1 N2 124.4(4) . . ?
O1 C1 C2 128.4(4) . . ?
N2 C1 C2 107.1(4) . . ?
C1 C2 C3 104.6(4) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 106.5(4) . . ?
N1 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
N1 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
N1 C4 C5 113.2(3) . . ?
N1 C4 C19 100.7(3) . . ?
C5 C4 C19 117.4(3) . . ?
N1 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
C19 C4 H4 108.4 . . ?
C10 C5 C6 118.9(4) . . ?
C10 C5 C4 119.4(4) . . ?
C6 C5 C4 121.8(4) . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.2(5) . . ?
C7 C8 Br1 119.3(4) . . ?
C9 C8 Br1 119.5(4) . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C5 121.1(4) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C12 C11 C16 119.9(5) . . ?
C12 C11 H11 120.0 . . ?
C16 C11 H11 120.0 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 122.2(5) . . ?
C14 C13 Br2 118.3(4) . . ?
C12 C13 Br2 119.5(4) . . ?
C13 C14 C15 117.9(5) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C16 C15 C14 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 118.7(4) . . ?
C15 C16 C17 121.3(4) . . ?
C11 C16 C17 119.9(4) . . ?
N2 C17 C16 113.7(4) . . ?
N2 C17 C19 103.9(3) . . ?
C16 C17 C19 115.5(3) . . ?
N2 C17 H17 107.8 . . ?
C16 C17 H17 107.8 . . ?
C19 C17 H17 107.8 . . ?
O2 C18 C26 127.4(4) . . ?
O2 C18 C19 123.9(4) . . ?
C26 C18 C19 108.7(3) . . ?
C18 C19 C20 102.9(3) . . ?
C18 C19 C4 111.5(3) . . ?
C20 C19 C4 112.3(3) . . ?
C18 C19 C17 112.5(3) . . ?
C20 C19 C17 116.4(3) . . ?
C4 C19 C17 101.7(3) . . ?
O3 C20 C21 126.9(4) . . ?
O3 C20 C19 125.9(4) . . ?
C21 C20 C19 107.1(3) . . ?
C26 C21 C22 120.8(4) . . ?
C26 C21 C20 111.0(4) . . ?
C22 C21 C20 128.1(4) . . ?
C23 C22 C21 117.3(5) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C24 122.0(5) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C25 C24 C23 120.9(5) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 118.2(5) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C21 C26 C25 120.8(4) . . ?
C21 C26 C18 109.9(4) . . ?
C25 C26 C18 129.3(4) . . ?
N2 N1 C3 102.9(3) . . ?
N2 N1 C4 100.5(3) . . ?
C3 N1 C4 114.2(3) . . ?
C1 N2 N1 111.5(4) . . ?
C1 N2 C17 120.8(3) . . ?
N1 N2 C17 108.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.881
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.144
####################################################################### 
# 
# 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_2a
_audit_block_doi                 10.5517/cc1jmg4r
_database_code_depnum_ccdc_archive 'CCDC 1418874'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H31 N3 O3'
_chemical_formula_sum            'C35 H31 N3 O3'
_chemical_formula_weight         541.63

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           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                   9.773(2)
_cell_length_b                   11.353(3)
_cell_length_c                   26.233(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.260(8)
_cell_angle_gamma                90.00
_cell_volume                     2864.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2587
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      19.67

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs

_exptl_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            27887
_diffrn_reflns_av_R_equivalents  0.1894
_diffrn_reflns_av_sigmaI/netI    0.2779
_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       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.57
_reflns_number_total             6585
_reflns_number_gt                2237
_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)+(0.1092P)²+8.0983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0112(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6585
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3245
_refine_ls_R_factor_gt           0.1198
_refine_ls_wR_factor_ref         0.3689
_refine_ls_wR_factor_gt          0.3040
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.6887(8) 0.3003(7) 0.0142(3) 0.066(2) Uani 1 1 d . . .
H1 H 0.7132 0.2890 0.0498 0.079 Uiso 1 1 calc R . .
C2 C 0.6538(9) 0.4117(8) -0.0050(4) 0.078(3) Uani 1 1 d . . .
H2 H 0.6548 0.4753 0.0174 0.094 Uiso 1 1 calc R . .
C3 C 0.6174(10) 0.4279(9) -0.0581(5) 0.088(3) Uani 1 1 d . . .
H3 H 0.5933 0.5026 -0.0713 0.105 Uiso 1 1 calc R . .
C4 C 0.6166(9) 0.3358(10) -0.0907(4) 0.081(3) Uani 1 1 d . . .
H4 H 0.5916 0.3475 -0.1262 0.097 Uiso 1 1 calc R . .
C5 C 0.6522(7) 0.2261(8) -0.0720(3) 0.059(2) Uani 1 1 d . . .
H5 H 0.6530 0.1636 -0.0949 0.071 Uiso 1 1 calc R . .
C6 C 0.6877(7) 0.2068(6) -0.0184(3) 0.0467(18) Uani 1 1 d . . .
C7 C 0.7175(8) 0.0814(6) 0.0004(3) 0.057(2) Uani 1 1 d . . .
H7A H 0.6354 0.0340 -0.0115 0.068 Uiso 1 1 calc R . .
H7B H 0.7919 0.0503 -0.0157 0.068 Uiso 1 1 calc R . .
C8 C 0.6643(8) 0.0403(5) 0.0872(3) 0.0414(17) Uani 1 1 d . . .
C9 C 0.7453(6) 0.0061(5) 0.1404(3) 0.0362(16) Uani 1 1 d . . .
C10 C 0.8928(6) 0.0178(5) 0.1333(3) 0.0378(16) Uani 1 1 d . . .
C11 C 1.0155(7) 0.0005(6) 0.1663(3) 0.0459(18) Uani 1 1 d . . .
H11 H 1.0149 -0.0261 0.1997 0.055 Uiso 1 1 calc R . .
C12 C 1.1428(7) 0.0222(6) 0.1504(3) 0.053(2) Uani 1 1 d . . .
C13 C 1.2771(8) 0.0083(10) 0.1878(3) 0.091(3) Uani 1 1 d . . .
H13A H 1.3536 0.0249 0.1705 0.136 Uiso 1 1 calc R . .
H13B H 1.2847 -0.0711 0.2007 0.136 Uiso 1 1 calc R . .
H13C H 1.2788 0.0619 0.2162 0.136 Uiso 1 1 calc R . .
C14 C 1.1393(8) 0.0602(7) 0.0998(3) 0.060(2) Uani 1 1 d . . .
H14 H 1.2229 0.0756 0.0889 0.072 Uiso 1 1 calc R . .
C15 C 1.0166(8) 0.0758(6) 0.0654(3) 0.054(2) Uani 1 1 d . . .
H15 H 1.0174 0.0993 0.0314 0.064 Uiso 1 1 calc R . .
C16 C 0.8943(7) 0.0562(5) 0.0820(3) 0.0400(17) Uani 1 1 d . . .
C17 C 0.7037(7) -0.1172(6) 0.1592(3) 0.054(2) Uani 1 1 d . . .
H17 H 0.6102 -0.1377 0.1411 0.065 Uiso 1 1 calc R . .
C18 C 0.8072(8) -0.2144(6) 0.1495(4) 0.057(2) Uani 1 1 d . . .
C19 C 0.8205(8) -0.2452(6) 0.0961(3) 0.054(2) Uani 1 1 d . . .
C20 C 0.7141(8) -0.2275(6) 0.0526(3) 0.059(2) Uani 1 1 d . . .
H20 H 0.6311 -0.1918 0.0566 0.071 Uiso 1 1 calc R . .
C21 C 0.7340(9) -0.2635(7) 0.0043(4) 0.068(2) Uani 1 1 d . . .
H21 H 0.6615 -0.2540 -0.0236 0.082 Uiso 1 1 calc R . .
C22 C 0.8555(11) -0.3125(7) -0.0045(4) 0.068(2) Uani 1 1 d . . .
C23 C 0.8775(12) -0.3550(9) -0.0572(4) 0.107(4) Uani 1 1 d . . .
H23A H 0.7999 -0.3317 -0.0830 0.160 Uiso 1 1 calc R . .
H23B H 0.8854 -0.4393 -0.0568 0.160 Uiso 1 1 calc R . .
H23C H 0.9612 -0.3209 -0.0651 0.160 Uiso 1 1 calc R . .
C24 C 0.9629(10) -0.3265(7) 0.0382(5) 0.082(3) Uani 1 1 d . . .
H24 H 1.0472 -0.3586 0.0334 0.098 Uiso 1 1 calc R . .
C25 C 0.9460(9) -0.2936(7) 0.0872(4) 0.074(3) Uani 1 1 d . . .
H25 H 1.0190 -0.3038 0.1149 0.089 Uiso 1 1 calc R . .
C26 C 0.8890(8) 0.2390(6) 0.2093(3) 0.0492(19) Uani 1 1 d . . .
H26 H 0.9445 0.1825 0.2286 0.059 Uiso 1 1 calc R . .
C27 C 0.9408(9) 0.3520(7) 0.2061(3) 0.070(2) Uani 1 1 d . . .
H27 H 1.0293 0.3711 0.2236 0.084 Uiso 1 1 calc R . .
C28 C 0.8594(12) 0.4366(7) 0.1766(4) 0.078(3) Uani 1 1 d . . .
H28 H 0.8945 0.5118 0.1732 0.093 Uiso 1 1 calc R . .
C29 C 0.7291(11) 0.4089(7) 0.1528(3) 0.073(3) Uani 1 1 d . . .
H29 H 0.6737 0.4662 0.1340 0.087 Uiso 1 1 calc R . .
C30 C 0.6775(8) 0.2973(7) 0.1560(3) 0.057(2) Uani 1 1 d . . .
H30 H 0.5879 0.2800 0.1390 0.068 Uiso 1 1 calc R . .
C31 C 0.7578(7) 0.2083(6) 0.1846(2) 0.0403(17) Uani 1 1 d . . .
C32 C 0.7020(7) 0.0874(6) 0.1828(3) 0.0460(18) Uani 1 1 d . . .
H32 H 0.6003 0.0909 0.1779 0.055 Uiso 1 1 calc R . .
C33 C 0.6907(10) 0.0432(8) 0.2760(3) 0.075(3) Uani 1 1 d . . .
H33A H 0.7629 0.0572 0.3059 0.090 Uiso 1 1 calc R . .
H33B H 0.6323 0.1127 0.2701 0.090 Uiso 1 1 calc R . .
C34 C 0.6089(12) -0.0580(11) 0.2847(4) 0.117(4) Uani 1 1 d . . .
H34A H 0.5144 -0.0344 0.2863 0.141 Uiso 1 1 calc R . .
H34B H 0.6485 -0.0957 0.3171 0.141 Uiso 1 1 calc R . .
C35 C 0.6100(9) -0.1392(9) 0.2414(3) 0.075(3) Uani 1 1 d . . .
N1 N 0.7567(6) 0.0679(5) 0.0565(2) 0.0434(14) Uani 1 1 d . . .
N2 N 0.7542(6) 0.0167(5) 0.2289(2) 0.0469(15) Uani 1 1 d . . .
N3 N 0.7007(6) -0.0979(5) 0.2129(2) 0.0549(17) Uani 1 1 d . . .
O1 O 0.5384(5) 0.0410(4) 0.0749(2) 0.0618(15) Uani 1 1 d . . .
O2 O 0.8762(7) -0.2626(5) 0.1863(2) 0.0790(18) Uani 1 1 d . . .
O3 O 0.5440(7) -0.2329(7) 0.2294(3) 0.113(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.362(10) . ?
C1 C2 1.382(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.517(10) . ?
C7 N1 1.463(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.215(7) . ?
C8 N1 1.348(8) . ?
C8 C9 1.528(9) . ?
C9 C10 1.491(9) . ?
C9 C17 1.562(9) . ?
C9 C32 1.562(9) . ?
C10 C11 1.362(9) . ?
C10 C16 1.418(9) . ?
C11 C12 1.403(9) . ?
C11 H11 0.9300 . ?
C12 C14 1.388(10) . ?
C12 C13 1.501(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.379(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(9) . ?
C15 H15 0.9300 . ?
C16 N1 1.397(8) . ?
C17 N3 1.433(9) . ?
C17 C18 1.548(10) . ?
C17 H17 0.9800 . ?
C18 O2 1.206(9) . ?
C18 C19 1.472(11) . ?
C19 C25 1.401(11) . ?
C19 C20 1.415(11) . ?
C20 C21 1.377(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(11) . ?
C21 H21 0.9300 . ?
C22 C24 1.401(12) . ?
C22 C23 1.516(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.376(12) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.375(9) . ?
C26 C27 1.387(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.352(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.372(11) . ?
C29 H29 0.9300 . ?
C30 C31 1.411(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.474(9) . ?
C32 N2 1.465(9) . ?
C32 H32 0.9800 . ?
C33 C34 1.441(12) . ?
C33 N2 1.507(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.463(13) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 O3 1.256(10) . ?
C35 N3 1.342(10) . ?
N2 N3 1.437(8) . ?

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 120.7(8) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 119.4(9) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.3(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(9) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.7(7) . . ?
C1 C6 C7 123.3(7) . . ?
C5 C6 C7 118.0(7) . . ?
N1 C7 C6 115.2(6) . . ?
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 126.6(6) . . ?
O1 C8 C9 125.3(7) . . ?
N1 C8 C9 108.1(6) . . ?
C10 C9 C8 102.6(5) . . ?
C10 C9 C17 115.5(5) . . ?
C8 C9 C17 113.3(5) . . ?
C10 C9 C32 115.2(5) . . ?
C8 C9 C32 109.8(5) . . ?
C17 C9 C32 100.7(5) . . ?
C11 C10 C16 119.3(6) . . ?
C11 C10 C9 132.0(6) . . ?
C16 C10 C9 108.6(6) . . ?
C10 C11 C12 120.9(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C14 C12 C11 117.8(7) . . ?
C14 C12 C13 121.9(7) . . ?
C11 C12 C13 120.3(7) . . ?
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 122.5(7) . . ?
C15 C14 H14 118.8 . . ?
C12 C14 H14 118.8 . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 N1 131.0(7) . . ?
C15 C16 C10 120.9(6) . . ?
N1 C16 C10 108.1(6) . . ?
N3 C17 C18 113.5(6) . . ?
N3 C17 C9 103.0(5) . . ?
C18 C17 C9 111.9(6) . . ?
N3 C17 H17 109.4 . . ?
C18 C17 H17 109.4 . . ?
C9 C17 H17 109.4 . . ?
O2 C18 C19 121.6(7) . . ?
O2 C18 C17 118.7(8) . . ?
C19 C18 C17 119.7(8) . . ?
C25 C19 C20 117.4(8) . . ?
C25 C19 C18 118.7(8) . . ?
C20 C19 C18 123.9(7) . . ?
C21 C20 C19 119.8(8) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 122.9(9) . . ?
C22 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
C21 C22 C24 117.5(8) . . ?
C21 C22 C23 123.4(10) . . ?
C24 C22 C23 119.0(9) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C22 121.2(8) . . ?
C25 C24 H24 119.4 . . ?
C22 C24 H24 119.4 . . ?
C24 C25 C19 121.1(9) . . ?
C24 C25 H25 119.5 . . ?
C19 C25 H25 119.5 . . ?
C31 C26 C27 121.8(7) . . ?
C31 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 119.6(8) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 119.6(8) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.9(8) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C31 121.2(8) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C26 C31 C30 116.9(6) . . ?
C26 C31 C32 124.0(6) . . ?
C30 C31 C32 118.9(6) . . ?
N2 C32 C31 114.3(6) . . ?
N2 C32 C9 99.6(5) . . ?
C31 C32 C9 115.3(5) . . ?
N2 C32 H32 109.1 . . ?
C31 C32 H32 109.1 . . ?
C9 C32 H32 109.1 . . ?
C34 C33 N2 106.9(7) . . ?
C34 C33 H33A 110.3 . . ?
N2 C33 H33A 110.3 . . ?
C34 C33 H33B 110.3 . . ?
N2 C33 H33B 110.3 . . ?
H33A C33 H33B 108.6 . . ?
C33 C34 C35 107.4(7) . . ?
C33 C34 H34A 110.2 . . ?
C35 C34 H34A 110.2 . . ?
C33 C34 H34B 110.2 . . ?
C35 C34 H34B 110.2 . . ?
H34A C34 H34B 108.5 . . ?
O3 C35 N3 121.0(9) . . ?
O3 C35 C34 131.0(9) . . ?
N3 C35 C34 108.0(8) . . ?
C8 N1 C16 112.5(5) . . ?
C8 N1 C7 122.8(6) . . ?
C16 N1 C7 123.3(6) . . ?
N3 N2 C32 101.5(5) . . ?
N3 N2 C33 103.8(5) . . ?
C32 N2 C33 115.7(6) . . ?
C35 N3 C17 128.8(7) . . ?
C35 N3 N2 113.2(7) . . ?
C17 N3 N2 110.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_2f
_audit_block_doi                 10.5517/cc1jmg5s
_database_code_depnum_ccdc_archive 'CCDC 1418875'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H27 Cl2 N3 O3'
_chemical_formula_sum            'C34 H27 Cl2 N3 O3'
_chemical_formula_weight         596.49

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                   8.4099(10)
_cell_length_b                   9.1196(12)
_cell_length_c                   19.621(2)
_cell_angle_alpha                101.049(4)
_cell_angle_beta                 95.152(4)
_cell_angle_gamma                104.173(4)
_cell_volume                     1417.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7279
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.948
_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            21772
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.62
_reflns_number_total             6485
_reflns_number_gt                4346
_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)+(0.0493P)²+0.4299P] 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         6485
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1026
_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 0.7924(3) 0.0011(3) 0.09873(11) 0.0485(5) Uani 1 1 d . . .
H1 H 0.8372 -0.0616 0.1226 0.058 Uiso 1 1 calc R . .
C2 C 0.7932(3) -0.0166(3) 0.02746(13) 0.0647(7) Uani 1 1 d . . .
H2 H 0.8403 -0.0902 0.0039 0.078 Uiso 1 1 calc R . .
C3 C 0.7266(3) 0.0716(3) -0.00873(13) 0.0648(7) Uani 1 1 d . . .
H3 H 0.7277 0.0589 -0.0568 0.078 Uiso 1 1 calc R . .
C4 C 0.6576(3) 0.1796(3) 0.02631(14) 0.0637(7) Uani 1 1 d . . .
H4 H 0.6107 0.2401 0.0018 0.076 Uiso 1 1 calc R . .
C5 C 0.6570(3) 0.1995(3) 0.09789(12) 0.0518(6) Uani 1 1 d . . .
H5 H 0.6099 0.2733 0.1212 0.062 Uiso 1 1 calc R . .
C6 C 0.7256(2) 0.1108(2) 0.13482(10) 0.0357(4) Uani 1 1 d . . .
C7 C 0.7324(2) 0.1331(3) 0.21367(11) 0.0421(5) Uani 1 1 d . . .
H7A H 0.7472 0.0401 0.2273 0.051 Uiso 1 1 calc R . .
H7B H 0.8279 0.2180 0.2362 0.051 Uiso 1 1 calc R . .
C8 C 0.5832(2) 0.3036(2) 0.28017(10) 0.0328(4) Uani 1 1 d . . .
C9 C 0.4070(2) 0.2879(2) 0.29882(9) 0.0277(4) Uani 1 1 d . . .
C10 C 0.3157(2) 0.1242(2) 0.26013(9) 0.0281(4) Uani 1 1 d . . .
C11 C 0.1557(2) 0.0362(2) 0.25856(9) 0.0315(4) Uani 1 1 d . . .
H11 H 0.0785 0.0790 0.2803 0.038 Uiso 1 1 calc R . .
C12 C 0.1144(2) -0.1181(2) 0.22350(10) 0.0353(4) Uani 1 1 d . . .
C13 C 0.2264(3) -0.1834(2) 0.19097(11) 0.0429(5) Uani 1 1 d . . .
H13 H 0.1944 -0.2873 0.1678 0.051 Uiso 1 1 calc R . .
C14 C 0.3869(3) -0.0954(2) 0.19250(10) 0.0413(5) Uani 1 1 d . . .
H14 H 0.4637 -0.1384 0.1706 0.050 Uiso 1 1 calc R . .
C15 C 0.4289(2) 0.0572(2) 0.22743(9) 0.0309(4) Uani 1 1 d . . .
C16 C 0.4011(2) 0.3168(2) 0.37961(9) 0.0291(4) Uani 1 1 d . . .
H16 H 0.5050 0.3891 0.4050 0.035 Uiso 1 1 calc R . .
C17 C 0.3676(2) 0.1677(2) 0.40662(9) 0.0310(4) Uani 1 1 d . . .
C18 C 0.5003(2) 0.0865(2) 0.40874(9) 0.0306(4) Uani 1 1 d . . .
C19 C 0.4561(2) -0.0689(2) 0.41154(11) 0.0403(5) Uani 1 1 d . . .
H19 H 0.3459 -0.1184 0.4127 0.048 Uiso 1 1 calc R . .
C20 C 0.5738(3) -0.1508(2) 0.41268(11) 0.0442(5) Uani 1 1 d . . .
H20 H 0.5412 -0.2549 0.4144 0.053 Uiso 1 1 calc R . .
C21 C 0.7399(3) -0.0813(2) 0.41134(10) 0.0383(5) Uani 1 1 d . . .
C22 C 0.8668(3) -0.1718(3) 0.41431(12) 0.0527(6) Uani 1 1 d . . .
H22A H 0.9718 -0.1100 0.4075 0.079 Uiso 1 1 calc R . .
H22B H 0.8325 -0.2649 0.3781 0.079 Uiso 1 1 calc R . .
H22C H 0.8771 -0.1983 0.4593 0.079 Uiso 1 1 calc R . .
C23 C 0.7842(2) 0.0742(2) 0.40940(11) 0.0395(5) Uani 1 1 d . . .
H23 H 0.8947 0.1236 0.4088 0.047 Uiso 1 1 calc R . .
C24 C 0.6665(2) 0.1580(2) 0.40833(10) 0.0353(4) Uani 1 1 d . . .
H24 H 0.6992 0.2625 0.4073 0.042 Uiso 1 1 calc R . .
C25 C 0.1420(3) 0.3496(3) 0.16671(11) 0.0460(5) Uani 1 1 d . . .
H25 H 0.0581 0.3003 0.1889 0.055 Uiso 1 1 calc R . .
C26 C 0.1079(3) 0.3519(3) 0.09670(11) 0.0521(6) Uani 1 1 d . . .
H26 H 0.0015 0.3068 0.0724 0.063 Uiso 1 1 calc R . .
C27 C 0.2322(3) 0.4211(2) 0.06367(10) 0.0421(5) Uani 1 1 d . . .
C28 C 0.3889(3) 0.4911(3) 0.09940(12) 0.0469(5) Uani 1 1 d . . .
H28 H 0.4727 0.5383 0.0766 0.056 Uiso 1 1 calc R . .
C29 C 0.4203(2) 0.4905(2) 0.16953(11) 0.0404(5) Uani 1 1 d . . .
H29 H 0.5258 0.5392 0.1940 0.049 Uiso 1 1 calc R . .
C30 C 0.2978(2) 0.4188(2) 0.20425(10) 0.0304(4) Uani 1 1 d . . .
C31 C 0.3374(2) 0.4206(2) 0.28048(9) 0.0290(4) Uani 1 1 d . . .
H31 H 0.4175 0.5197 0.3030 0.035 Uiso 1 1 calc R . .
C32 C 0.1311(2) 0.5439(2) 0.33686(10) 0.0365(5) Uani 1 1 d . . .
H32A H 0.0306 0.5348 0.3061 0.044 Uiso 1 1 calc R . .
H32B H 0.2140 0.6367 0.3341 0.044 Uiso 1 1 calc R . .
C33 C 0.0976(3) 0.5473(2) 0.41181(11) 0.0405(5) Uani 1 1 d . . .
H33A H 0.1154 0.6529 0.4380 0.049 Uiso 1 1 calc R . .
H33B H -0.0150 0.4892 0.4129 0.049 Uiso 1 1 calc R . .
C34 C 0.2218(2) 0.4717(2) 0.44120(10) 0.0327(4) Uani 1 1 d . . .
Cl1 Cl -0.08477(7) -0.23570(6) 0.22257(3) 0.05320(17) Uani 1 1 d . . .
Cl2 Cl 0.18887(9) 0.41743(8) -0.02526(3) 0.0677(2) Uani 1 1 d . . .
N1 N 0.58471(18) 0.16599(18) 0.23858(8) 0.0351(4) Uani 1 1 d . . .
N2 N 0.19288(18) 0.40342(17) 0.31833(7) 0.0293(3) Uani 1 1 d . . .
N3 N 0.26690(19) 0.39013(18) 0.38551(8) 0.0336(4) Uani 1 1 d . . .
O1 O 0.69881(16) 0.41868(16) 0.29804(8) 0.0456(4) Uani 1 1 d . . .
O2 O 0.23235(16) 0.11521(17) 0.42272(7) 0.0446(4) Uani 1 1 d . . .
O3 O 0.27203(17) 0.47842(16) 0.50240(7) 0.0432(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.376(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(3) . ?
C7 N1 1.451(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.211(2) . ?
C8 N1 1.363(2) . ?
C8 C9 1.537(2) . ?
C9 C10 1.515(2) . ?
C9 C31 1.553(3) . ?
C9 C16 1.564(2) . ?
C10 C11 1.382(2) . ?
C10 C15 1.392(2) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C12 Cl1 1.7501(19) . ?
C13 C14 1.386(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.407(2) . ?
C16 N3 1.448(2) . ?
C16 C17 1.524(3) . ?
C16 H16 0.9800 . ?
C17 O2 1.216(2) . ?
C17 C18 1.484(3) . ?
C18 C19 1.388(3) . ?
C18 C24 1.392(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 C23 1.384(3) . ?
C21 C22 1.504(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C30 1.378(3) . ?
C25 C26 1.383(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.373(3) . ?
C27 Cl2 1.742(2) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.499(3) . ?
C31 N2 1.472(2) . ?
C31 H31 0.9800 . ?
C32 N2 1.492(2) . ?
C32 C33 1.518(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.515(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 O3 1.222(2) . ?
C34 N3 1.339(2) . ?
N2 N3 1.446(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 120.4(2) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.47(19) . . ?
C5 C6 C7 121.88(18) . . ?
C1 C6 C7 119.64(18) . . ?
N1 C7 C6 113.20(16) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 126.21(17) . . ?
O1 C8 C9 126.11(17) . . ?
N1 C8 C9 107.67(15) . . ?
C10 C9 C8 102.74(14) . . ?
C10 C9 C31 116.83(14) . . ?
C8 C9 C31 111.04(14) . . ?
C10 C9 C16 113.09(14) . . ?
C8 C9 C16 113.20(14) . . ?
C31 C9 C16 100.41(13) . . ?
C11 C10 C15 119.99(16) . . ?
C11 C10 C9 131.73(16) . . ?
C15 C10 C9 107.96(15) . . ?
C10 C11 C12 117.66(17) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C13 C12 C11 122.07(18) . . ?
C13 C12 Cl1 118.65(15) . . ?
C11 C12 Cl1 119.25(15) . . ?
C12 C13 C14 120.40(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 117.81(18) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C14 C15 C10 122.07(17) . . ?
C14 C15 N1 127.88(17) . . ?
C10 C15 N1 110.00(15) . . ?
N3 C16 C17 112.39(15) . . ?
N3 C16 C9 101.41(13) . . ?
C17 C16 C9 112.89(14) . . ?
N3 C16 H16 110.0 . . ?
C17 C16 H16 110.0 . . ?
C9 C16 H16 110.0 . . ?
O2 C17 C18 121.97(17) . . ?
O2 C17 C16 119.77(16) . . ?
C18 C17 C16 118.18(16) . . ?
C19 C18 C24 118.27(17) . . ?
C19 C18 C17 118.16(17) . . ?
C24 C18 C17 123.57(17) . . ?
C20 C19 C18 120.71(19) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 121.58(19) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C23 C21 C20 117.70(18) . . ?
C23 C21 C22 121.57(19) . . ?
C20 C21 C22 120.70(19) . . ?
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 121.18(19) . . ?
C21 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C18 120.54(18) . . ?
C23 C24 H24 119.7 . . ?
C18 C24 H24 119.7 . . ?
C30 C25 C26 121.38(19) . . ?
C30 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C27 C26 C25 119.3(2) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C28 120.9(2) . . ?
C26 C27 Cl2 118.69(17) . . ?
C28 C27 Cl2 120.37(16) . . ?
C27 C28 C29 119.15(19) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C28 C29 C30 121.35(19) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C25 C30 C29 117.90(18) . . ?
C25 C30 C31 122.51(17) . . ?
C29 C30 C31 119.58(17) . . ?
N2 C31 C30 114.20(14) . . ?
N2 C31 C9 100.31(13) . . ?
C30 C31 C9 117.26(14) . . ?
N2 C31 H31 108.2 . . ?
C30 C31 H31 108.2 . . ?
C9 C31 H31 108.2 . . ?
N2 C32 C33 103.46(15) . . ?
N2 C32 H32A 111.1 . . ?
C33 C32 H32A 111.1 . . ?
N2 C32 H32B 111.1 . . ?
C33 C32 H32B 111.1 . . ?
H32A C32 H32B 109.0 . . ?
C34 C33 C32 103.71(15) . . ?
C34 C33 H33A 111.0 . . ?
C32 C33 H33A 111.0 . . ?
C34 C33 H33B 111.0 . . ?
C32 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?
O3 C34 N3 125.15(18) . . ?
O3 C34 C33 128.99(17) . . ?
N3 C34 C33 105.84(16) . . ?
C8 N1 C15 111.55(15) . . ?
C8 N1 C7 123.80(16) . . ?
C15 N1 C7 124.50(16) . . ?
N3 N2 C31 100.51(13) . . ?
N3 N2 C32 102.97(13) . . ?
C31 N2 C32 116.07(14) . . ?
C34 N3 N2 114.76(14) . . ?
C34 N3 C16 131.23(15) . . ?
N2 N3 C16 112.63(13) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.047

#======================================================================
