# 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_a16869
_database_code_depnum_ccdc_archive 'CCDC 1484056'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 O2'
_chemical_formula_sum            'C24 H21 N3 O2'
_chemical_formula_weight         383.44

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'

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                   10.813(3)
_cell_length_b                   20.064(9)
_cell_length_c                   8.964(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.695(9)
_cell_angle_gamma                90.00
_cell_volume                     1944.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1269
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      20.09

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13224
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.1244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.07
_reflns_number_total             3422
_reflns_number_gt                1697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0838P)²+0.7453P] 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         3422
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2088
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.0233(4) 0.0760(2) 0.7227(5) 0.0479(13) Uani 1 1 d . . .
C2 C 0.0035(4) 0.0931(2) 0.5655(5) 0.0435(12) Uani 1 1 d . . .
C3 C -0.0982(4) 0.1220(3) 0.4951(6) 0.0544(14) Uani 1 1 d . . .
H3 H -0.1680 0.1357 0.5507 0.065 Uiso 1 1 calc R . .
C4 C -0.0957(5) 0.1303(3) 0.3458(6) 0.0590(14) Uani 1 1 d . . .
H4 H -0.1643 0.1505 0.2964 0.071 Uiso 1 1 calc R . .
C5 C 0.0055(5) 0.1098(3) 0.2628(5) 0.0587(15) Uani 1 1 d . . .
H5 H 0.0043 0.1152 0.1575 0.070 Uiso 1 1 calc R . .
C6 C 0.1087(4) 0.0813(2) 0.3329(5) 0.0496(13) Uani 1 1 d . . .
H6 H 0.1780 0.0674 0.2769 0.060 Uiso 1 1 calc R . .
C7 C 0.1071(4) 0.0742(2) 0.4841(5) 0.0416(12) Uani 1 1 d . . .
C8 C 0.1979(4) 0.0456(2) 0.5889(5) 0.0365(11) Uani 1 1 d . . .
C9 C 0.1898(4) 0.0204(3) 0.8686(5) 0.0555(14) Uani 1 1 d . . .
H9A H 0.2718 0.0014 0.8513 0.083 Uiso 1 1 calc R . .
H9B H 0.1348 -0.0143 0.9070 0.083 Uiso 1 1 calc R . .
H9C H 0.1966 0.0566 0.9415 0.083 Uiso 1 1 calc R . .
C10 C 0.3106(4) 0.0237(2) 0.5530(5) 0.0403(11) Uani 1 1 d . . .
H10 H 0.3326 0.0291 0.4515 0.048 Uiso 1 1 calc R . .
C11 C 0.4060(4) -0.0078(2) 0.6509(4) 0.0348(11) Uani 1 1 d . . .
C12 C 0.4214(4) -0.0766(2) 0.6463(5) 0.0464(12) Uani 1 1 d . . .
H12 H 0.3724 -0.1019 0.5782 0.056 Uiso 1 1 calc R . .
C13 C 0.5054(4) -0.1094(2) 0.7373(5) 0.0460(12) Uani 1 1 d . . .
H13 H 0.5129 -0.1565 0.7333 0.055 Uiso 1 1 calc R . .
C14 C 0.5782(4) -0.0726(2) 0.8343(5) 0.0427(12) Uani 1 1 d . . .
H14 H 0.6351 -0.0947 0.8991 0.051 Uiso 1 1 calc R . .
C15 C 0.5690(4) -0.0041(2) 0.8377(4) 0.0397(11) Uani 1 1 d . . .
H15 H 0.6211 0.0205 0.9037 0.048 Uiso 1 1 calc R . .
C16 C 0.4844(4) 0.0300(2) 0.7460(4) 0.0350(11) Uani 1 1 d . . .
C17 C 0.5317(4) 0.1461(2) 0.8350(4) 0.0364(11) Uani 1 1 d . . .
C18 C 0.6593(4) 0.1421(2) 0.8612(4) 0.0422(12) Uani 1 1 d . . .
H18 H 0.7056 0.1076 0.8156 0.051 Uiso 1 1 calc R . .
C19 C 0.7189(5) 0.1878(3) 0.9527(5) 0.0504(13) Uani 1 1 d . . .
H19 H 0.8056 0.1840 0.9692 0.060 Uiso 1 1 calc R . .
C20 C 0.6548(5) 0.2385(3) 1.0201(5) 0.0513(13) Uani 1 1 d . . .
H20 H 0.6958 0.2689 1.0853 0.062 Uiso 1 1 calc R . .
C21 C 0.5291(5) 0.2444(2) 0.9910(5) 0.0462(13) Uani 1 1 d . . .
H21 H 0.4847 0.2801 1.0349 0.055 Uiso 1 1 calc R . .
C22 C 0.4659(4) 0.1994(2) 0.8992(4) 0.0340(11) Uani 1 1 d . . .
C23 C 0.3309(4) 0.2071(2) 0.8668(5) 0.0374(11) Uani 1 1 d . . .
C24 C 0.1261(4) 0.2394(3) 0.9529(5) 0.0536(14) Uani 1 1 d . . .
H24A H 0.0902 0.2571 1.0446 0.080 Uiso 1 1 calc R . .
H24B H 0.0878 0.1964 0.9289 0.080 Uiso 1 1 calc R . .
H24C H 0.1109 0.2707 0.8708 0.080 Uiso 1 1 calc R . .
N1 N 0.1399(3) 0.04598(19) 0.7303(4) 0.0427(10) Uani 1 1 d . . .
N2 N 0.4696(3) 0.09923(18) 0.7459(4) 0.0402(10) Uani 1 1 d . . .
H2 H 0.4147 0.1153 0.6822 0.048 Uiso 1 1 calc R . .
N3 N 0.2588(3) 0.23049(18) 0.9744(4) 0.0438(10) Uani 1 1 d . . .
H3A H 0.2924 0.2409 1.0612 0.053 Uiso 1 1 calc R . .
O1 O -0.0442(3) 0.08405(18) 0.8311(4) 0.0634(11) Uani 1 1 d . . .
O2 O 0.2853(3) 0.19204(15) 0.7423(3) 0.0442(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 O1 1.233(5) . ?
C1 N1 1.398(5) . ?
C1 C2 1.463(6) . ?
C2 C3 1.389(6) . ?
C2 C7 1.397(6) . ?
C3 C4 1.349(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.363(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.467(6) . ?
C8 C10 1.338(6) . ?
C8 N1 1.422(5) . ?
C9 N1 1.441(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.488(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(6) . ?
C11 C16 1.416(6) . ?
C12 C13 1.380(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(6) . ?
C15 H15 0.9500 . ?
C16 N2 1.398(5) . ?
C17 C18 1.399(6) . ?
C17 N2 1.400(5) . ?
C17 C22 1.411(6) . ?
C18 C19 1.384(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.492(6) . ?
C23 O2 1.252(5) . ?
C23 N3 1.333(5) . ?
C24 N3 1.457(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N2 H2 0.8800 . ?
N3 H3A 0.8800 . ?

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 124.0(4) . . ?
O1 C1 C2 130.3(5) . . ?
N1 C1 C2 105.6(4) . . ?
C3 C2 C7 120.8(4) . . ?
C3 C2 C1 129.9(4) . . ?
C7 C2 C1 109.3(4) . . ?
C4 C3 C2 118.5(5) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 120.7(4) . . ?
C6 C7 C8 131.4(4) . . ?
C2 C7 C8 107.9(4) . . ?
C10 C8 N1 129.0(4) . . ?
C10 C8 C7 125.4(4) . . ?
N1 C8 C7 105.6(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 128.7(4) . . ?
C8 C10 H10 115.7 . . ?
C11 C10 H10 115.7 . . ?
C12 C11 C16 118.6(4) . . ?
C12 C11 C10 119.1(4) . . ?
C16 C11 C10 122.2(4) . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.0(4) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
N2 C16 C15 124.0(4) . . ?
N2 C16 C11 117.7(4) . . ?
C15 C16 C11 118.3(4) . . ?
C18 C17 N2 121.5(4) . . ?
C18 C17 C22 118.4(4) . . ?
N2 C17 C22 120.1(4) . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 121.1(5) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 118.6(5) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 121.9(5) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C21 C22 C17 119.0(4) . . ?
C21 C22 C23 121.2(4) . . ?
C17 C22 C23 119.7(4) . . ?
O2 C23 N3 120.1(4) . . ?
O2 C23 C22 121.5(4) . . ?
N3 C23 C22 118.4(4) . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C8 111.5(4) . . ?
C1 N1 C9 121.6(3) . . ?
C8 N1 C9 126.9(4) . . ?
C16 N2 C17 127.8(4) . . ?
C16 N2 H2 116.1 . . ?
C17 N2 H2 116.1 . . ?
C23 N3 C24 122.1(4) . . ?
C23 N3 H3A 118.9 . . ?
C24 N3 H3A 118.9 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_a17131
_database_code_depnum_ccdc_archive 'CCDC 1484057'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 Br N2 O2'
_chemical_formula_sum            'C24 H19 Br N2 O2'
_chemical_formula_weight         447.32

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'

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

_cell_length_a                   7.2109(5)
_cell_length_b                   8.7771(5)
_cell_length_c                   16.7382(12)
_cell_angle_alpha                92.017(4)
_cell_angle_beta                 100.699(4)
_cell_angle_gamma                105.215(3)
_cell_volume                     1000.53(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1725
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.19

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7190
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7092
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3465
_reflns_number_gt                2427
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0496P)²+0.8355P] 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         3465
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_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 0.4753(6) 0.9211(5) 0.7090(2) 0.0252(10) Uani 1 1 d . . .
H1 H 0.3661 0.8700 0.7367 0.030 Uiso 1 1 calc R . .
C2 C 0.4092(6) 1.0383(5) 0.6559(2) 0.0242(10) Uani 1 1 d . . .
C3 C 0.3002(7) 1.0191(6) 0.5774(3) 0.0341(12) Uani 1 1 d . . .
H3 H 0.2587 0.9185 0.5469 0.041 Uiso 1 1 calc R . .
C4 C 0.2522(7) 1.1499(6) 0.5437(3) 0.0399(13) Uani 1 1 d . . .
H4 H 0.1765 1.1391 0.4899 0.048 Uiso 1 1 calc R . .
C5 C 0.3152(7) 1.2958(6) 0.5889(3) 0.0351(12) Uani 1 1 d . . .
H5 H 0.2829 1.3845 0.5651 0.042 Uiso 1 1 calc R . .
C6 C 0.4235(6) 1.3163(5) 0.6677(3) 0.0294(11) Uani 1 1 d . . .
H6 H 0.4649 1.4173 0.6978 0.035 Uiso 1 1 calc R . .
C7 C 0.4707(6) 1.1856(5) 0.7019(3) 0.0242(10) Uani 1 1 d . . .
C9 C 0.6481(6) 1.0241(5) 0.7753(2) 0.0207(9) Uani 1 1 d . . .
C10 C 0.6685(6) 0.9431(5) 0.8533(2) 0.0225(10) Uani 1 1 d . . .
C11 C 0.9648(6) 0.9869(5) 0.8092(3) 0.0256(10) Uani 1 1 d . . .
C12 C 0.8519(6) 0.9157(5) 0.8706(3) 0.0248(10) Uani 1 1 d . . .
C13 C 0.9063(7) 0.8366(5) 0.9376(3) 0.0333(11) Uani 1 1 d . . .
H13 H 1.0321 0.8178 0.9492 0.040 Uiso 1 1 calc R . .
C14 C 0.5896(7) 0.8165(5) 0.9689(3) 0.0369(12) Uani 1 1 d . . .
H14 H 0.5006 0.7837 1.0043 0.044 Uiso 1 1 calc R . .
C15 C 0.5333(7) 0.8924(5) 0.9019(3) 0.0287(11) Uani 1 1 d . . .
H15 H 0.4065 0.9091 0.8896 0.034 Uiso 1 1 calc R . .
C16 C 0.7723(7) 0.7859(5) 0.9869(3) 0.0362(12) Uani 1 1 d . . .
H16 H 0.8045 0.7304 1.0328 0.043 Uiso 1 1 calc R . .
C18 C 0.8974(6) 1.1235(5) 0.6839(3) 0.0276(11) Uani 1 1 d . . .
H18A H 0.7926 1.0743 0.6359 0.033 Uiso 1 1 calc R . .
H18B H 1.0187 1.0981 0.6755 0.033 Uiso 1 1 calc R . .
C19 C 0.9319(6) 1.3023(5) 0.6870(3) 0.0244(10) Uani 1 1 d . . .
C20 C 0.8728(7) 1.3690(6) 0.6166(3) 0.0365(12) Uani 1 1 d . . .
H20 H 0.8078 1.3027 0.5679 0.044 Uiso 1 1 calc R . .
C21 C 0.9077(8) 1.5322(6) 0.6162(3) 0.0451(13) Uani 1 1 d . . .
H21 H 0.8684 1.5773 0.5673 0.054 Uiso 1 1 calc R . .
C22 C 1.0586(7) 1.5634(6) 0.7570(3) 0.0431(13) Uani 1 1 d . . .
H22 H 1.1224 1.6298 0.8057 0.052 Uiso 1 1 calc R . .
C23 C 1.0251(6) 1.4007(5) 0.7565(3) 0.0323(11) Uani 1 1 d . . .
H23 H 1.0674 1.3562 0.8052 0.039 Uiso 1 1 calc R . .
C24 C 0.9990(7) 1.6283(6) 0.6865(4) 0.0437(13) Uani 1 1 d . . .
H24 H 1.0212 1.7398 0.6864 0.052 Uiso 1 1 calc R . .
C25 C 0.6610(6) 1.2835(5) 0.8460(3) 0.0246(10) Uani 1 1 d . . .
C26 C 0.5762(8) 1.4220(5) 0.8503(3) 0.0411(13) Uani 1 1 d . . .
H26A H 0.4778 1.4170 0.8006 0.062 Uiso 1 1 calc R . .
H26B H 0.6811 1.5209 0.8553 0.062 Uiso 1 1 calc R . .
H26C H 0.5144 1.4183 0.8979 0.062 Uiso 1 1 calc R . .
N1 N 0.8422(5) 1.0518(4) 0.7563(2) 0.0233(8) Uani 1 1 d . . .
N2 N 0.5867(5) 1.1737(4) 0.77843(19) 0.0195(8) Uani 1 1 d . . .
O1 O 1.1336(4) 0.9903(4) 0.80420(18) 0.0361(8) Uani 1 1 d . . .
O2 O 0.7857(5) 1.2631(3) 0.90075(18) 0.0338(8) Uani 1 1 d . . .
Br1 Br 0.54560(8) 0.75435(6) 0.65231(3) 0.03915(19) 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 1.497(6) . ?
C1 C9 1.558(6) . ?
C1 Br1 1.941(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.380(6) . ?
C2 C7 1.401(6) . ?
C3 C4 1.392(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(6) . ?
C6 H6 0.9500 . ?
C7 N2 1.418(5) . ?
C9 N1 1.454(5) . ?
C9 N2 1.494(5) . ?
C9 C10 1.509(6) . ?
C10 C15 1.380(6) . ?
C10 C12 1.386(6) . ?
C11 O1 1.228(5) . ?
C11 N1 1.379(5) . ?
C11 C12 1.483(6) . ?
C12 C13 1.388(6) . ?
C13 C16 1.381(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 C16 1.394(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 N1 1.458(5) . ?
C18 C19 1.521(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C23 1.373(6) . ?
C19 C20 1.381(6) . ?
C20 C21 1.388(6) . ?
C20 H20 0.9500 . ?
C21 C24 1.371(7) . ?
C21 H21 0.9500 . ?
C22 C24 1.374(7) . ?
C22 C23 1.385(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O2 1.213(5) . ?
C25 N2 1.387(5) . ?
C25 C26 1.502(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 104.4(3) . . ?
C2 C1 Br1 115.2(3) . . ?
C9 C1 Br1 113.1(3) . . ?
C2 C1 H1 108.0 . . ?
C9 C1 H1 108.0 . . ?
Br1 C1 H1 108.0 . . ?
C3 C2 C7 121.4(4) . . ?
C3 C2 C1 131.1(4) . . ?
C7 C2 C1 107.5(4) . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 118.5(4) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 119.6(4) . . ?
C6 C7 N2 130.5(4) . . ?
C2 C7 N2 109.7(4) . . ?
N1 C9 N2 111.5(3) . . ?
N1 C9 C10 102.7(3) . . ?
N2 C9 C10 116.8(3) . . ?
N1 C9 C1 115.8(3) . . ?
N2 C9 C1 99.8(3) . . ?
C10 C9 C1 111.0(3) . . ?
C15 C10 C12 121.1(4) . . ?
C15 C10 C9 129.5(4) . . ?
C12 C10 C9 109.3(4) . . ?
O1 C11 N1 125.0(4) . . ?
O1 C11 C12 128.6(4) . . ?
N1 C11 C12 106.4(3) . . ?
C10 C12 C13 121.2(4) . . ?
C10 C12 C11 108.6(4) . . ?
C13 C12 C11 130.2(4) . . ?
C16 C13 C12 118.1(4) . . ?
C16 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C16 122.5(4) . . ?
C15 C14 H14 118.7 . . ?
C16 C14 H14 118.7 . . ?
C14 C15 C10 117.2(4) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?
C13 C16 C14 119.8(4) . . ?
C13 C16 H16 120.1 . . ?
C14 C16 H16 120.1 . . ?
N1 C18 C19 115.0(3) . . ?
N1 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
N1 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C23 C19 C20 118.6(4) . . ?
C23 C19 C18 122.6(4) . . ?
C20 C19 C18 118.8(4) . . ?
C19 C20 C21 120.6(5) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C24 C21 C20 119.9(5) . . ?
C24 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C24 C22 C23 119.5(5) . . ?
C24 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C19 C23 C22 121.2(5) . . ?
C19 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C21 C24 C22 120.1(5) . . ?
C21 C24 H24 119.9 . . ?
C22 C24 H24 119.9 . . ?
O2 C25 N2 119.9(4) . . ?
O2 C25 C26 122.0(4) . . ?
N2 C25 C26 118.1(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 N1 C9 112.8(3) . . ?
C11 N1 C18 122.4(3) . . ?
C9 N1 C18 124.4(3) . . ?
C25 N2 C7 129.8(3) . . ?
C25 N2 C9 120.4(3) . . ?
C7 N2 C9 109.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_a17291
_database_code_depnum_ccdc_archive 'CCDC 1484058'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 Br2 Cl N2 O2'
_chemical_formula_sum            'C23 H15 Br2 Cl N2 O2'
_chemical_formula_weight         546.64

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'
Br Br -0.2901 2.4595 '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/n'

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

_cell_length_a                   9.6989(16)
_cell_length_b                   15.284(3)
_cell_length_c                   15.014(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.462(6)
_cell_angle_gamma                90.00
_cell_volume                     2173.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3539
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      24.12

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    3.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5112
_exptl_absorpt_correction_T_max  0.8926
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12408
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.22
_reflns_number_total             3834
_reflns_number_gt                2609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0626P)²+7.2741P] 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         3834
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_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 0.8622(7) 0.1027(4) 0.0815(4) 0.0253(15) Uani 1 1 d . . .
H1 H 0.8589 0.0409 0.1026 0.030 Uiso 1 1 calc R . .
C2 C 0.8278(7) 0.1012(4) -0.0188(5) 0.0305(17) Uani 1 1 d . . .
C3 C 0.9167(8) 0.0976(5) -0.0806(5) 0.0346(18) Uani 1 1 d . . .
H3 H 1.0164 0.0948 -0.0603 0.042 Uiso 1 1 calc R . .
C4 C 0.8534(9) 0.0984(5) -0.1727(6) 0.043(2) Uani 1 1 d . . .
C5 C 0.7094(9) 0.1030(5) -0.2042(6) 0.048(2) Uani 1 1 d . . .
H5 H 0.6702 0.1029 -0.2680 0.057 Uiso 1 1 calc R . .
C6 C 0.6206(9) 0.1077(5) -0.1420(6) 0.044(2) Uani 1 1 d . . .
H6 H 0.5210 0.1106 -0.1626 0.053 Uiso 1 1 calc R . .
C7 C 0.6824(7) 0.1081(4) -0.0492(5) 0.0302(17) Uani 1 1 d . . .
C8 C 0.4753(8) 0.1182(5) 0.0247(6) 0.0369(19) Uani 1 1 d . . .
C9 C 0.4223(8) 0.1474(5) 0.1058(6) 0.047(2) Uani 1 1 d . . .
H9A H 0.5020 0.1661 0.1539 0.070 Uiso 1 1 calc R . .
H9B H 0.3732 0.0988 0.1283 0.070 Uiso 1 1 calc R . .
H9C H 0.3568 0.1964 0.0887 0.070 Uiso 1 1 calc R . .
C10 C 0.7329(7) 0.1516(4) 0.1057(5) 0.0248(15) Uani 1 1 d . . .
C11 C 0.7227(7) 0.1331(4) 0.2030(5) 0.0265(16) Uani 1 1 d . . .
C12 C 0.7092(7) 0.0537(4) 0.2446(5) 0.0313(17) Uani 1 1 d . . .
H12 H 0.6947 0.0009 0.2105 0.038 Uiso 1 1 calc R . .
C13 C 0.7178(8) 0.0541(5) 0.3391(5) 0.0336(18) Uani 1 1 d . . .
H13 H 0.7081 0.0007 0.3695 0.040 Uiso 1 1 calc R . .
C14 C 0.7404(7) 0.1318(5) 0.3891(6) 0.0367(19) Uani 1 1 d . . .
C15 C 0.7561(7) 0.2115(4) 0.3471(5) 0.0276(16) Uani 1 1 d . . .
H15 H 0.7713 0.2645 0.3808 0.033 Uiso 1 1 calc R . .
C16 C 0.7484(7) 0.2097(4) 0.2537(5) 0.0257(15) Uani 1 1 d . . .
C17 C 0.7666(7) 0.2827(4) 0.1917(5) 0.0290(16) Uani 1 1 d . . .
C18 C 0.7472(7) 0.3013(4) 0.0264(5) 0.0246(15) Uani 1 1 d . . .
C19 C 0.8701(9) 0.3294(7) 0.0059(7) 0.070(3) Uani 1 1 d . . .
H19 H 0.9581 0.3133 0.0438 0.084 Uiso 1 1 calc R . .
C20 C 0.8667(10) 0.3810(7) -0.0697(8) 0.077(4) Uani 1 1 d . . .
H20 H 0.9528 0.4004 -0.0834 0.092 Uiso 1 1 calc R . .
C21 C 0.7421(9) 0.4048(5) -0.1251(6) 0.048(2) Uani 1 1 d . . .
H21 H 0.7407 0.4397 -0.1776 0.058 Uiso 1 1 calc R . .
C22 C 0.6199(10) 0.3777(6) -0.1039(7) 0.067(3) Uani 1 1 d . . .
H22 H 0.5318 0.3934 -0.1419 0.080 Uiso 1 1 calc R . .
C23 C 0.6238(8) 0.3267(6) -0.0261(6) 0.054(3) Uani 1 1 d . . .
H23 H 0.5379 0.3098 -0.0103 0.065 Uiso 1 1 calc R . .
N1 N 0.6204(6) 0.1225(4) 0.0287(4) 0.0307(14) Uani 1 1 d . . .
N2 N 0.7480(5) 0.2478(3) 0.1056(4) 0.0234(12) Uani 1 1 d . . .
O1 O 0.3961(5) 0.0915(4) -0.0445(4) 0.0461(14) Uani 1 1 d . . .
O2 O 0.7929(6) 0.3590(3) 0.2128(4) 0.0387(13) Uani 1 1 d . . .
Cl1 Cl 0.9644(3) 0.09640(17) -0.25167(16) 0.0609(7) Uani 1 1 d . . .
Br1 Br 1.04271(8) 0.14972(6) 0.14076(6) 0.0461(3) Uani 1 1 d . . .
Br2 Br 0.75845(10) 0.12772(6) 0.51681(6) 0.0479(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 C2 1.470(9) . ?
C1 C10 1.568(9) . ?
C1 Br1 1.924(7) . ?
C1 H1 1.0000 . ?
C2 C7 1.390(10) . ?
C2 C3 1.397(10) . ?
C3 C4 1.387(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(12) . ?
C4 Cl1 1.765(8) . ?
C5 C6 1.402(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(11) . ?
C6 H6 0.9500 . ?
C7 N1 1.443(9) . ?
C8 O1 1.221(9) . ?
C8 N1 1.397(9) . ?
C8 C9 1.489(11) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N1 1.476(8) . ?
C10 N2 1.478(8) . ?
C10 C11 1.513(10) . ?
C11 C12 1.384(9) . ?
C11 C16 1.389(9) . ?
C12 C13 1.402(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(10) . ?
C14 Br2 1.888(9) . ?
C15 C16 1.389(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.487(9) . ?
C17 O2 1.223(8) . ?
C17 N2 1.373(9) . ?
C18 C23 1.341(10) . ?
C18 C19 1.363(10) . ?
C18 N2 1.443(8) . ?
C19 C20 1.377(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.360(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.356(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(12) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 C10 103.2(5) . . ?
C2 C1 Br1 117.6(5) . . ?
C10 C1 Br1 114.1(4) . . ?
C2 C1 H1 107.1 . . ?
C10 C1 H1 107.1 . . ?
Br1 C1 H1 107.1 . . ?
C7 C2 C3 120.9(7) . . ?
C7 C2 C1 109.0(6) . . ?
C3 C2 C1 130.1(6) . . ?
C4 C3 C2 117.3(7) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C5 C4 C3 122.8(8) . . ?
C5 C4 Cl1 119.3(7) . . ?
C3 C4 Cl1 117.9(7) . . ?
C4 C5 C6 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 118.3(7) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C2 C7 C6 121.0(7) . . ?
C2 C7 N1 108.4(6) . . ?
C6 C7 N1 130.4(7) . . ?
O1 C8 N1 119.7(8) . . ?
O1 C8 C9 122.1(7) . . ?
N1 C8 C9 118.2(7) . . ?
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 . . ?
N1 C10 N2 110.9(5) . . ?
N1 C10 C11 120.6(6) . . ?
N2 C10 C11 102.3(5) . . ?
N1 C10 C1 99.7(5) . . ?
N2 C10 C1 112.9(5) . . ?
C11 C10 C1 110.9(5) . . ?
C12 C11 C16 121.0(7) . . ?
C12 C11 C10 129.2(6) . . ?
C16 C11 C10 109.3(6) . . ?
C11 C12 C13 117.5(6) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 121.1(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 121.2(7) . . ?
C15 C14 Br2 119.5(6) . . ?
C13 C14 Br2 119.2(6) . . ?
C16 C15 C14 116.9(6) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 C11 122.3(6) . . ?
C15 C16 C17 129.0(6) . . ?
C11 C16 C17 108.7(6) . . ?
O2 C17 N2 126.4(7) . . ?
O2 C17 C16 126.8(7) . . ?
N2 C17 C16 106.8(6) . . ?
C23 C18 C19 119.3(7) . . ?
C23 C18 N2 119.6(6) . . ?
C19 C18 N2 121.0(6) . . ?
C18 C19 C20 120.0(8) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.1(9) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 118.8(8) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 119.9(8) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.8(8) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C8 N1 C7 123.3(6) . . ?
C8 N1 C10 128.0(6) . . ?
C7 N1 C10 108.3(5) . . ?
C17 N2 C18 122.2(5) . . ?
C17 N2 C10 112.3(5) . . ?
C18 N2 C10 125.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.22
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.063
_refine_diff_density_min         -1.783
_refine_diff_density_rms         0.160
####################################################################### 
# 
# 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_a17746
_database_code_depnum_ccdc_archive 'CCDC 1484059'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 Br Cl N2 O2'
_chemical_formula_sum            'C23 H16 Br Cl N2 O2'
_chemical_formula_weight         467.74

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   17.3513(3)
_cell_length_b                   14.2331(2)
_cell_length_c                   15.8822(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3922.31(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6781
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      24.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_T_max  0.8766
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27566
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6579
_reflns_number_gt                5730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0512P)²+11.8844P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.485(11)
_refine_ls_number_reflns         6579
_refine_ls_number_parameters     523
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0035(4) 0.4465(4) 0.4203(4) 0.0242(13) Uani 1 1 d . . .
H1 H 0.0327 0.3965 0.4509 0.029 Uiso 1 1 calc R . .
C2 C -0.0416(4) 0.3980(4) 0.3535(4) 0.0212(13) Uani 1 1 d . . .
C3 C -0.1136(4) 0.3558(4) 0.3572(4) 0.0262(14) Uani 1 1 d . . .
H3 H -0.1445 0.3596 0.4064 0.031 Uiso 1 1 calc R . .
C4 C -0.1385(3) 0.3080(4) 0.2865(5) 0.0308(14) Uani 1 1 d . . .
C5 C -0.0939(4) 0.3012(4) 0.2149(4) 0.0283(15) Uani 1 1 d . . .
H5 H -0.1124 0.2670 0.1677 0.034 Uiso 1 1 calc R . .
C6 C -0.0220(4) 0.3440(4) 0.2115(4) 0.0272(15) Uani 1 1 d . . .
H6 H 0.0085 0.3409 0.1619 0.033 Uiso 1 1 calc R . .
C7 C 0.0041(3) 0.3914(4) 0.2826(4) 0.0208(13) Uani 1 1 d . . .
C8 C 0.1337(4) 0.4452(4) 0.2382(4) 0.0247(14) Uani 1 1 d . . .
C9 C 0.1973(4) 0.5148(5) 0.2515(4) 0.0377(18) Uani 1 1 d . . .
H9A H 0.1865 0.5520 0.3021 0.057 Uiso 1 1 calc R . .
H9B H 0.2007 0.5566 0.2026 0.057 Uiso 1 1 calc R . .
H9C H 0.2463 0.4814 0.2586 0.057 Uiso 1 1 calc R . .
C10 C 0.0645(3) 0.5050(4) 0.3699(4) 0.0180(12) Uani 1 1 d . . .
C11 C 0.1339(3) 0.5236(4) 0.4246(3) 0.0177(12) Uani 1 1 d . . .
C12 C 0.1826(3) 0.4593(4) 0.4641(4) 0.0212(13) Uani 1 1 d . . .
H12 H 0.1781 0.3935 0.4548 0.025 Uiso 1 1 calc R . .
C13 C 0.2383(3) 0.4965(4) 0.5178(4) 0.0280(14) Uani 1 1 d . . .
H13 H 0.2728 0.4551 0.5456 0.034 Uiso 1 1 calc R . .
C14 C 0.2446(4) 0.5927(4) 0.5319(4) 0.0303(15) Uani 1 1 d . . .
H14 H 0.2829 0.6156 0.5694 0.036 Uiso 1 1 calc R . .
C15 C 0.1962(3) 0.6553(4) 0.4924(4) 0.0247(14) Uani 1 1 d . . .
H15 H 0.2006 0.7210 0.5017 0.030 Uiso 1 1 calc R . .
C16 C 0.1406(3) 0.6194(4) 0.4383(4) 0.0193(13) Uani 1 1 d . . .
C17 C 0.0833(3) 0.6694(4) 0.3856(3) 0.0193(13) Uani 1 1 d . . .
C18 C -0.0265(3) 0.6202(4) 0.2965(4) 0.0244(13) Uani 1 1 d . . .
C19 C -0.0880(4) 0.6654(5) 0.3340(4) 0.0358(17) Uani 1 1 d . . .
H19 H -0.0849 0.6837 0.3914 0.043 Uiso 1 1 calc R . .
C20 C -0.1539(4) 0.6838(5) 0.2882(5) 0.0489(19) Uani 1 1 d . . .
H20 H -0.1961 0.7148 0.3143 0.059 Uiso 1 1 calc R . .
C21 C -0.1589(5) 0.6572(5) 0.2039(5) 0.047(2) Uani 1 1 d . . .
H21 H -0.2046 0.6689 0.1726 0.056 Uiso 1 1 calc R . .
C22 C -0.0967(5) 0.6140(5) 0.1666(4) 0.0424(19) Uani 1 1 d . . .
H22 H -0.0994 0.5961 0.1090 0.051 Uiso 1 1 calc R . .
C23 C -0.0295(4) 0.5960(5) 0.2126(4) 0.0299(16) Uani 1 1 d . . .
H23 H 0.0137 0.5673 0.1863 0.036 Uiso 1 1 calc R . .
C24 C 0.4891(4) 1.0373(4) 0.3608(4) 0.0213(13) Uani 1 1 d . . .
H24 H 0.5104 1.0883 0.3243 0.026 Uiso 1 1 calc R . .
C25 C 0.4468(3) 1.0850(4) 0.4315(4) 0.0212(13) Uani 1 1 d . . .
C26 C 0.3734(4) 1.1215(4) 0.4344(4) 0.0243(14) Uani 1 1 d . . .
H26 H 0.3375 1.1111 0.3902 0.029 Uiso 1 1 calc R . .
C27 C 0.3545(3) 1.1740(4) 0.5045(5) 0.0262(13) Uani 1 1 d . . .
C28 C 0.4045(4) 1.1867(5) 0.5710(4) 0.0307(15) Uani 1 1 d . . .
H28 H 0.3885 1.2217 0.6188 0.037 Uiso 1 1 calc R . .
C29 C 0.4787(4) 1.1481(5) 0.5682(4) 0.0265(14) Uani 1 1 d . . .
H29 H 0.5137 1.1570 0.6134 0.032 Uiso 1 1 calc R . .
C30 C 0.4996(3) 1.0972(4) 0.4981(4) 0.0184(12) Uani 1 1 d . . .
C31 C 0.6380(4) 1.0674(4) 0.5226(4) 0.0250(14) Uani 1 1 d . . .
C32 C 0.7106(4) 1.0161(5) 0.4969(5) 0.0361(17) Uani 1 1 d . . .
H32A H 0.6994 0.9753 0.4487 0.054 Uiso 1 1 calc R . .
H32B H 0.7291 0.9780 0.5441 0.054 Uiso 1 1 calc R . .
H32C H 0.7502 1.0619 0.4811 0.054 Uiso 1 1 calc R . .
C33 C 0.5594(3) 0.9889(4) 0.4040(4) 0.0199(13) Uani 1 1 d . . .
C34 C 0.6236(3) 0.9767(4) 0.3400(4) 0.0204(13) Uani 1 1 d . . .
C35 C 0.6615(3) 1.0441(4) 0.2937(4) 0.0251(13) Uani 1 1 d . . .
H35 H 0.6509 1.1091 0.3013 0.030 Uiso 1 1 calc R . .
C36 C 0.7158(4) 1.0140(5) 0.2356(4) 0.0316(15) Uani 1 1 d . . .
H36 H 0.7444 1.0590 0.2044 0.038 Uiso 1 1 calc R . .
C37 C 0.7293(4) 0.9171(5) 0.2222(4) 0.0304(15) Uani 1 1 d . . .
H37 H 0.7660 0.8975 0.1815 0.036 Uiso 1 1 calc R . .
C38 C 0.6891(4) 0.8511(4) 0.2683(4) 0.0301(15) Uani 1 1 d . . .
H38 H 0.6970 0.7858 0.2593 0.036 Uiso 1 1 calc R . .
C39 C 0.6368(3) 0.8827(4) 0.3283(4) 0.0208(13) Uani 1 1 d . . .
C40 C 0.5914(4) 0.8275(4) 0.3888(4) 0.0232(13) Uani 1 1 d . . .
C41 C 0.5003(4) 0.8644(4) 0.5045(5) 0.0255(13) Uani 1 1 d . . .
C42 C 0.4234(4) 0.8461(5) 0.4956(5) 0.0440(18) Uani 1 1 d . . .
H42 H 0.3987 0.8541 0.4427 0.053 Uiso 1 1 calc R . .
C43 C 0.3812(5) 0.8150(6) 0.5668(6) 0.058(2) Uani 1 1 d . . .
H43 H 0.3276 0.8024 0.5621 0.069 Uiso 1 1 calc R . .
C44 C 0.4176(6) 0.8033(6) 0.6422(5) 0.057(2) Uani 1 1 d . . .
H44 H 0.3892 0.7825 0.6898 0.068 Uiso 1 1 calc R . .
C45 C 0.4954(6) 0.8214(5) 0.6499(5) 0.048(2) Uani 1 1 d . . .
H45 H 0.5205 0.8116 0.7023 0.058 Uiso 1 1 calc R . .
C46 C 0.5363(5) 0.8534(5) 0.5823(5) 0.0401(18) Uani 1 1 d . . .
H46 H 0.5894 0.8683 0.5883 0.048 Uiso 1 1 calc R . .
N1 N 0.0737(3) 0.4438(3) 0.2939(3) 0.0182(9) Uani 1 1 d . . .
N2 N 0.0406(3) 0.6004(3) 0.3467(3) 0.0202(11) Uani 1 1 d . . .
N3 N 0.5710(3) 1.0522(3) 0.4779(3) 0.0195(11) Uani 1 1 d . . .
N4 N 0.5465(3) 0.8919(3) 0.4324(3) 0.0218(12) Uani 1 1 d . . .
O1 O 0.1352(3) 0.3895(3) 0.1790(3) 0.0358(12) Uani 1 1 d . . .
O2 O 0.0750(3) 0.7541(3) 0.3770(3) 0.0305(10) Uani 1 1 d . . .
O3 O 0.6397(3) 1.1225(4) 0.5808(3) 0.0394(12) Uani 1 1 d . . .
O4 O 0.5933(3) 0.7427(3) 0.4026(3) 0.0313(11) Uani 1 1 d . . .
Cl1 Cl -0.22780(9) 0.25091(12) 0.29013(15) 0.0470(5) Uani 1 1 d . . .
Cl2 Cl 0.26332(9) 1.22701(11) 0.50835(14) 0.0381(4) Uani 1 1 d . . .
Br1 Br -0.05073(4) 0.51733(4) 0.50479(4) 0.03123(16) Uani 1 1 d . . .
Br2 Br 0.43007(4) 0.95594(5) 0.28794(4) 0.03556(18) 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 1.488(8) . ?
C1 C10 1.568(8) . ?
C1 Br1 1.923(6) . ?
C1 H1 1.0000 . ?
C2 C7 1.380(9) . ?
C2 C3 1.387(9) . ?
C3 C4 1.383(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(10) . ?
C4 Cl1 1.750(6) . ?
C5 C6 1.389(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(9) . ?
C6 H6 0.9500 . ?
C7 N1 1.430(7) . ?
C8 O1 1.229(7) . ?
C8 N1 1.368(8) . ?
C8 C9 1.498(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N2 1.467(7) . ?
C10 N1 1.497(7) . ?
C10 C11 1.507(8) . ?
C11 C16 1.386(8) . ?
C11 C12 1.395(8) . ?
C12 C13 1.394(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.482(8) . ?
C17 O2 1.222(7) . ?
C17 N2 1.376(8) . ?
C18 C23 1.377(9) . ?
C18 C19 1.381(9) . ?
C18 N2 1.438(8) . ?
C19 C20 1.380(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(11) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(11) . ?
C21 H21 0.9500 . ?
C22 C23 1.401(10) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.503(8) . ?
C24 C33 1.561(8) . ?
C24 Br2 1.931(6) . ?
C24 H24 1.0000 . ?
C25 C26 1.376(8) . ?
C25 C30 1.410(9) . ?
C26 C27 1.381(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(10) . ?
C27 Cl2 1.754(6) . ?
C28 C29 1.400(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(9) . ?
C29 H29 0.9500 . ?
C30 N3 1.432(7) . ?
C31 O3 1.212(7) . ?
C31 N3 1.379(8) . ?
C31 C32 1.512(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 N4 1.470(7) . ?
C33 N3 1.493(7) . ?
C33 C34 1.517(8) . ?
C34 C39 1.370(8) . ?
C34 C35 1.377(8) . ?
C35 C36 1.387(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.415(10) . ?
C36 H36 0.9500 . ?
C37 C38 1.380(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.392(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.471(9) . ?
C40 O4 1.228(7) . ?
C40 N4 1.388(8) . ?
C41 C42 1.367(9) . ?
C41 C46 1.394(10) . ?
C41 N4 1.451(8) . ?
C42 C43 1.418(11) . ?
C42 H42 0.9500 . ?
C43 C44 1.363(13) . ?
C43 H43 0.9500 . ?
C44 C45 1.379(13) . ?
C44 H44 0.9500 . ?
C45 C46 1.365(10) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

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 C10 103.7(5) . . ?
C2 C1 Br1 118.9(4) . . ?
C10 C1 Br1 114.1(4) . . ?
C2 C1 H1 106.4 . . ?
C10 C1 H1 106.4 . . ?
Br1 C1 H1 106.4 . . ?
C7 C2 C3 121.5(6) . . ?
C7 C2 C1 108.1(5) . . ?
C3 C2 C1 130.1(6) . . ?
C4 C3 C2 117.4(6) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 Cl1 119.5(5) . . ?
C3 C4 Cl1 118.6(6) . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 118.2(6) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C2 C7 C6 120.5(6) . . ?
C2 C7 N1 110.3(5) . . ?
C6 C7 N1 129.0(6) . . ?
O1 C8 N1 120.1(6) . . ?
O1 C8 C9 121.3(6) . . ?
N1 C8 C9 118.6(5) . . ?
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 . . ?
N2 C10 N1 111.5(4) . . ?
N2 C10 C11 102.1(4) . . ?
N1 C10 C11 118.8(5) . . ?
N2 C10 C1 115.4(5) . . ?
N1 C10 C1 100.0(4) . . ?
C11 C10 C1 109.8(5) . . ?
C16 C11 C12 121.5(5) . . ?
C16 C11 C10 109.3(5) . . ?
C12 C11 C10 128.9(5) . . ?
C13 C12 C11 116.5(6) . . ?
C13 C12 H12 121.8 . . ?
C11 C12 H12 121.8 . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 121.1(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 117.9(6) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C11 C16 C15 121.3(5) . . ?
C11 C16 C17 109.1(5) . . ?
C15 C16 C17 129.7(5) . . ?
O2 C17 N2 126.1(6) . . ?
O2 C17 C16 128.1(6) . . ?
N2 C17 C16 105.8(5) . . ?
C23 C18 C19 120.3(6) . . ?
C23 C18 N2 121.2(6) . . ?
C19 C18 N2 118.5(6) . . ?
C20 C19 C18 120.1(7) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.4(7) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.1(7) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 120.7(6) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.4(6) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C33 104.6(5) . . ?
C25 C24 Br2 117.4(4) . . ?
C33 C24 Br2 114.5(4) . . ?
C25 C24 H24 106.5 . . ?
C33 C24 H24 106.5 . . ?
Br2 C24 H24 106.5 . . ?
C26 C25 C30 122.0(5) . . ?
C26 C25 C24 130.3(6) . . ?
C30 C25 C24 107.4(5) . . ?
C25 C26 C27 116.8(6) . . ?
C25 C26 H26 121.6 . . ?
C27 C26 H26 121.6 . . ?
C28 C27 C26 122.6(6) . . ?
C28 C27 Cl2 119.0(5) . . ?
C26 C27 Cl2 118.3(5) . . ?
C27 C28 C29 120.2(6) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 118.3(6) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C29 C30 C25 120.0(5) . . ?
C29 C30 N3 130.1(6) . . ?
C25 C30 N3 109.8(5) . . ?
O3 C31 N3 120.9(6) . . ?
O3 C31 C32 119.9(6) . . ?
N3 C31 C32 119.1(5) . . ?
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 . . ?
N4 C33 N3 110.2(5) . . ?
N4 C33 C34 102.1(5) . . ?
N3 C33 C34 119.8(5) . . ?
N4 C33 C24 115.5(5) . . ?
N3 C33 C24 100.7(4) . . ?
C34 C33 C24 109.2(5) . . ?
C39 C34 C35 121.8(6) . . ?
C39 C34 C33 109.0(5) . . ?
C35 C34 C33 129.0(5) . . ?
C34 C35 C36 117.7(6) . . ?
C34 C35 H35 121.2 . . ?
C36 C35 H35 121.2 . . ?
C35 C36 C37 120.9(6) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C38 C37 C36 120.0(6) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C39 118.2(6) . . ?
C37 C38 H38 120.9 . . ?
C39 C38 H38 120.9 . . ?
C34 C39 C38 121.3(6) . . ?
C34 C39 C40 110.1(5) . . ?
C38 C39 C40 128.6(5) . . ?
O4 C40 N4 125.1(6) . . ?
O4 C40 C39 128.9(6) . . ?
N4 C40 C39 105.9(5) . . ?
C42 C41 C46 120.5(7) . . ?
C42 C41 N4 120.7(7) . . ?
C46 C41 N4 118.8(6) . . ?
C41 C42 C43 118.8(8) . . ?
C41 C42 H42 120.6 . . ?
C43 C42 H42 120.6 . . ?
C44 C43 C42 119.9(8) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.6(7) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 H44 119.7 . . ?
C46 C45 C44 120.1(8) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C41 120.1(7) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?
C8 N1 C7 124.7(5) . . ?
C8 N1 C10 126.4(5) . . ?
C7 N1 C10 108.4(5) . . ?
C17 N2 C18 123.1(5) . . ?
C17 N2 C10 113.2(5) . . ?
C18 N2 C10 123.3(5) . . ?
C31 N3 C30 123.0(5) . . ?
C31 N3 C33 127.8(5) . . ?
C30 N3 C33 109.2(5) . . ?
C40 N4 C41 121.7(5) . . ?
C40 N4 C33 112.4(5) . . ?
C41 N4 C33 125.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.720
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_a17747
_database_code_depnum_ccdc_archive 'CCDC 1484060'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 Br Cl N2 O2'
_chemical_formula_sum            'C23 H16 Br Cl N2 O2'
_chemical_formula_weight         467.74

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.8972(3)
_cell_length_b                   15.0212(6)
_cell_length_c                   16.9789(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2014.13(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5059
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      24.81

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2827
_exptl_absorpt_correction_T_max  0.8439
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11832
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3489
_reflns_number_gt                3047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0327P)²+0.7014P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.1795(5) 0.00231(19) 0.77164(16) 0.0192(8) Uani 1 1 d . . .
H1 H 0.0958 0.0519 0.7772 0.023 Uiso 1 1 calc R . .
C2 C 0.3508(4) 0.0333(2) 0.81040(17) 0.0193(7) Uani 1 1 d . . .
C3 C 0.4987(4) 0.0451(2) 0.75499(19) 0.0216(8) Uani 1 1 d . . .
C4 C 0.5865(4) -0.0187(3) 0.71366(19) 0.0273(8) Uani 1 1 d . . .
H4 H 0.5590 -0.0801 0.7180 0.033 Uiso 1 1 calc R . .
C5 C 0.7175(5) 0.0103(2) 0.6651(2) 0.0324(9) Uani 1 1 d . . .
H5 H 0.7797 -0.0322 0.6356 0.039 Uiso 1 1 calc R . .
C6 C 0.7597(5) 0.0998(3) 0.6587(2) 0.0414(10) Uani 1 1 d . . .
H6 H 0.8474 0.1180 0.6239 0.050 Uiso 1 1 calc R . .
C7 C 0.6732(6) 0.1630(2) 0.7034(2) 0.0362(10) Uani 1 1 d . . .
H7 H 0.7036 0.2241 0.7012 0.043 Uiso 1 1 calc R . .
C8 C 0.5424(5) 0.1345(2) 0.7510(2) 0.0229(8) Uani 1 1 d . . .
C9 C 0.4326(5) 0.1856(2) 0.80543(19) 0.0261(9) Uani 1 1 d . . .
C10 C 0.1866(5) 0.1486(2) 0.88921(18) 0.0225(8) Uani 1 1 d . . .
C11 C 0.0635(5) 0.2065(2) 0.8599(2) 0.0351(10) Uani 1 1 d . . .
H11 H 0.0733 0.2296 0.8080 0.042 Uiso 1 1 calc R . .
C12 C -0.0719(6) 0.2298(2) 0.9064(2) 0.0392(11) Uani 1 1 d . . .
H12 H -0.1558 0.2690 0.8864 0.047 Uiso 1 1 calc R . .
C13 C -0.0870(5) 0.1966(2) 0.9822(2) 0.0351(10) Uani 1 1 d . . .
H13 H -0.1809 0.2132 1.0140 0.042 Uiso 1 1 calc R . .
C14 C 0.0322(5) 0.1405(2) 1.0109(2) 0.0304(9) Uani 1 1 d . . .
H14 H 0.0215 0.1177 1.0629 0.036 Uiso 1 1 calc R . .
C15 C 0.1702(5) 0.1160(2) 0.96490(19) 0.0270(9) Uani 1 1 d . . .
H15 H 0.2535 0.0768 0.9856 0.032 Uiso 1 1 calc R . .
C16 C 0.5125(5) -0.0351(3) 0.9269(2) 0.0318(9) Uani 1 1 d . . .
C17 C 0.6522(5) 0.0303(3) 0.9197(2) 0.0426(10) Uani 1 1 d . . .
H17A H 0.6299 0.0700 0.8750 0.064 Uiso 1 1 calc R . .
H17B H 0.7592 -0.0012 0.9110 0.064 Uiso 1 1 calc R . .
H17C H 0.6598 0.0655 0.9682 0.064 Uiso 1 1 calc R . .
C18 C 0.2341(4) -0.0896(2) 0.8812(2) 0.0215(8) Uani 1 1 d . . .
C19 C 0.1985(6) -0.1541(2) 0.9380(2) 0.0290(9) Uani 1 1 d . . .
H19 H 0.2752 -0.1647 0.9800 0.035 Uiso 1 1 calc R . .
C20 C 0.0501(5) -0.2023(3) 0.9321(2) 0.0329(10) Uani 1 1 d . . .
H20 H 0.0241 -0.2465 0.9702 0.039 Uiso 1 1 calc R . .
C21 C -0.0612(5) -0.1859(3) 0.8703(2) 0.0321(9) Uani 1 1 d . . .
C22 C -0.0292(5) -0.1219(2) 0.81466(19) 0.0259(9) Uani 1 1 d . . .
H22 H -0.1068 -0.1110 0.7730 0.031 Uiso 1 1 calc R . .
C23 C 0.1200(5) -0.0735(2) 0.82101(18) 0.0214(8) Uani 1 1 d . . .
N1 N 0.3268(4) 0.12425(15) 0.84137(16) 0.0223(6) Uani 1 1 d . . .
N2 N 0.3773(3) -0.03339(18) 0.87451(15) 0.0206(6) Uani 1 1 d . . .
O1 O 0.4332(4) 0.26572(15) 0.81881(14) 0.0357(7) Uani 1 1 d . . .
O2 O 0.5148(4) -0.0901(2) 0.97983(17) 0.0509(8) Uani 1 1 d . . .
Cl1 Cl -0.24455(14) -0.25056(8) 0.86267(6) 0.0557(3) Uani 1 1 d . . .
Br1 Br 0.19162(5) -0.02987(3) 0.659830(19) 0.03558(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C23 1.490(4) . ?
C1 C2 1.575(5) . ?
C1 Br1 1.961(3) . ?
C1 H1 1.0000 . ?
C2 N1 1.476(4) . ?
C2 N2 1.494(4) . ?
C2 C3 1.510(5) . ?
C3 C4 1.376(5) . ?
C3 C8 1.389(5) . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.482(5) . ?
C9 O1 1.225(4) . ?
C9 N1 1.386(4) . ?
C10 C15 1.381(4) . ?
C10 C11 1.396(5) . ?
C10 N1 1.421(5) . ?
C11 C12 1.375(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.355(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.220(4) . ?
C16 N2 1.390(4) . ?
C16 C17 1.483(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.384(5) . ?
C18 C19 1.395(5) . ?
C18 N2 1.416(4) . ?
C19 C20 1.380(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(5) . ?
C21 Cl1 1.748(4) . ?
C22 C23 1.388(5) . ?
C22 H22 0.9500 . ?

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
C23 C1 C2 105.2(3) . . ?
C23 C1 Br1 111.8(2) . . ?
C2 C1 Br1 115.8(2) . . ?
C23 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
Br1 C1 H1 107.9 . . ?
N1 C2 N2 112.3(2) . . ?
N1 C2 C3 102.3(3) . . ?
N2 C2 C3 115.1(3) . . ?
N1 C2 C1 108.2(3) . . ?
N2 C2 C1 103.1(2) . . ?
C3 C2 C1 116.0(2) . . ?
C4 C3 C8 121.6(3) . . ?
C4 C3 C2 128.8(3) . . ?
C8 C3 C2 109.6(3) . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 C9 130.0(3) . . ?
C3 C8 C9 109.0(3) . . ?
O1 C9 N1 125.1(3) . . ?
O1 C9 C8 128.5(3) . . ?
N1 C9 C8 106.4(3) . . ?
C15 C10 C11 119.2(4) . . ?
C15 C10 N1 120.9(3) . . ?
C11 C10 N1 119.9(3) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.2(4) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O2 C16 N2 119.7(3) . . ?
O2 C16 C17 119.9(3) . . ?
N2 C16 C17 120.4(3) . . ?
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 . . ?
C23 C18 C19 120.0(3) . . ?
C23 C18 N2 110.8(3) . . ?
C19 C18 N2 129.1(3) . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 Cl1 119.4(3) . . ?
C20 C21 Cl1 118.8(3) . . ?
C21 C22 C23 118.0(3) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?
C18 C23 C22 121.2(3) . . ?
C18 C23 C1 110.1(3) . . ?
C22 C23 C1 128.6(3) . . ?
C9 N1 C10 123.4(3) . . ?
C9 N1 C2 112.4(3) . . ?
C10 N1 C2 122.8(3) . . ?
C16 N2 C18 123.4(3) . . ?
C16 N2 C2 125.9(3) . . ?
C18 N2 C2 110.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_a17965
_database_code_depnum_ccdc_archive 'CCDC 1484061'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N2 O'
_chemical_formula_sum            'C28 H22 N2 O'
_chemical_formula_weight         402.48

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   9.8696(5)
_cell_length_b                   10.1071(5)
_cell_length_c                   10.6037(4)
_cell_angle_alpha                96.056(2)
_cell_angle_beta                 94.649(3)
_cell_angle_gamma                98.442(3)
_cell_volume                     1035.43(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4099
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.03

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8156
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3618
_reflns_number_gt                3038
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0465P)²+0.2293P] 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         3618
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.04447(14) 0.29514(13) 0.34630(12) 0.0263(3) Uani 1 1 d . . .
C2 C 0.18562(14) 0.31293(13) 0.41744(12) 0.0245(3) Uani 1 1 d . . .
C3 C 0.21379(16) 0.41762(14) 0.51712(13) 0.0313(3) Uani 1 1 d . . .
H3 H 0.1476 0.4755 0.5320 0.038 Uiso 1 1 calc R . .
C4 C 0.33615(16) 0.43858(15) 0.59446(13) 0.0363(4) Uani 1 1 d . . .
H4 H 0.3530 0.5094 0.6629 0.044 Uiso 1 1 calc R . .
C5 C 0.43414(16) 0.35668(15) 0.57251(13) 0.0357(4) Uani 1 1 d . . .
H5 H 0.5178 0.3702 0.6266 0.043 Uiso 1 1 calc R . .
C6 C 0.41030(14) 0.25485(14) 0.47153(13) 0.0303(3) Uani 1 1 d . . .
H6 H 0.4788 0.2000 0.4551 0.036 Uiso 1 1 calc R . .
C7 C 0.28673(14) 0.23245(13) 0.39416(11) 0.0235(3) Uani 1 1 d . . .
C8 C 0.23371(13) 0.13565(13) 0.16136(12) 0.0243(3) Uani 1 1 d . . .
C9 C 0.24557(14) 0.26453(14) 0.10787(12) 0.0259(3) Uani 1 1 d . . .
C10 C 0.35008(15) 0.37239(14) 0.15167(13) 0.0300(3) Uani 1 1 d . . .
H10 H 0.4122 0.3661 0.2233 0.036 Uiso 1 1 calc R . .
C11 C 0.36384(17) 0.48763(15) 0.09212(14) 0.0373(4) Uani 1 1 d . . .
H11 H 0.4353 0.5603 0.1228 0.045 Uiso 1 1 calc R . .
C12 C 0.27422(18) 0.49786(16) -0.01198(15) 0.0426(4) Uani 1 1 d . . .
H12 H 0.2850 0.5769 -0.0536 0.051 Uiso 1 1 calc R . .
C13 C 0.16918(18) 0.39353(16) -0.05562(15) 0.0442(4) Uani 1 1 d . . .
H13 H 0.1068 0.4012 -0.1266 0.053 Uiso 1 1 calc R . .
C14 C 0.15467(16) 0.27789(15) 0.00382(14) 0.0368(4) Uani 1 1 d . . .
H14 H 0.0818 0.2065 -0.0265 0.044 Uiso 1 1 calc R . .
C15 C 0.19891(14) 0.00907(14) 0.09819(12) 0.0270(3) Uani 1 1 d . . .
H15 H 0.1727 -0.0126 0.0094 0.032 Uiso 1 1 calc R . .
C16 C 0.20857(14) -0.08544(13) 0.18821(12) 0.0256(3) Uani 1 1 d . . .
C17 C 0.18342(15) -0.22635(14) 0.18065(14) 0.0328(3) Uani 1 1 d . . .
H17 H 0.1577 -0.2795 0.1006 0.039 Uiso 1 1 calc R . .
C18 C 0.19632(16) -0.28691(15) 0.29018(15) 0.0369(4) Uani 1 1 d . . .
H18 H 0.1777 -0.3823 0.2856 0.044 Uiso 1 1 calc R . .
C19 C 0.23660(15) -0.20965(15) 0.40844(14) 0.0354(4) Uani 1 1 d . . .
H19 H 0.2436 -0.2537 0.4830 0.042 Uiso 1 1 calc R . .
C20 C 0.26631(14) -0.07084(14) 0.41920(13) 0.0293(3) Uani 1 1 d . . .
H20 H 0.2956 -0.0189 0.4993 0.035 Uiso 1 1 calc R . .
C21 C 0.25159(13) -0.01006(13) 0.30806(12) 0.0237(3) Uani 1 1 d . . .
C22 C -0.15614(14) 0.11719(14) 0.26273(11) 0.0254(3) Uani 1 1 d . . .
C23 C -0.23956(15) 0.20112(16) 0.20938(13) 0.0347(4) Uani 1 1 d . . .
H23 H -0.2051 0.2937 0.2076 0.042 Uiso 1 1 calc R . .
C24 C -0.37256(16) 0.14890(18) 0.15914(14) 0.0419(4) Uani 1 1 d . . .
H24 H -0.4291 0.2060 0.1224 0.050 Uiso 1 1 calc R . .
C25 C -0.42397(15) 0.01550(18) 0.16166(14) 0.0420(4) Uani 1 1 d . . .
H25 H -0.5159 -0.0194 0.1279 0.050 Uiso 1 1 calc R . .
C26 C -0.34085(15) -0.06776(17) 0.21378(13) 0.0360(4) Uani 1 1 d . . .
H26 H -0.3765 -0.1602 0.2144 0.043 Uiso 1 1 calc R . .
C27 C -0.20617(14) -0.01943(14) 0.26533(12) 0.0269(3) Uani 1 1 d . . .
C28 C -0.11965(15) -0.11192(14) 0.32369(14) 0.0334(3) Uani 1 1 d . . .
H28A H -0.0415 -0.1213 0.2718 0.040 Uiso 1 1 d R . .
H28B H -0.1710 -0.2025 0.3205 0.040 Uiso 1 1 d R . .
H28C H -0.0902 -0.0803 0.4113 0.040 Uiso 1 1 d R . .
N1 N -0.01977(11) 0.16541(11) 0.31690(10) 0.0261(3) Uani 1 1 d . . .
H1 H 0.0304 0.1031 0.3339 0.031 Uiso 1 1 calc R . .
N2 N 0.26776(11) 0.12580(11) 0.29085(10) 0.0233(3) Uani 1 1 d . . .
O1 O -0.00894(11) 0.39267(10) 0.32506(11) 0.0450(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 O1 1.2168(16) . ?
C1 N1 1.3624(17) . ?
C1 C2 1.5065(18) . ?
C2 C3 1.3943(19) . ?
C2 C7 1.3980(19) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3890(18) . ?
C6 H6 0.9500 . ?
C7 N2 1.4336(16) . ?
C8 C15 1.3624(18) . ?
C8 N2 1.4042(16) . ?
C8 C9 1.4677(19) . ?
C9 C14 1.3953(19) . ?
C9 C10 1.398(2) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.4273(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4018(19) . ?
C16 C21 1.4103(18) . ?
C17 C18 1.374(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3923(18) . ?
C20 H20 0.9500 . ?
C21 N2 1.3920(17) . ?
C22 C23 1.3958(19) . ?
C22 C27 1.4006(19) . ?
C22 N1 1.4149(17) . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.5022(19) . ?
C28 H28A 0.9931 . ?
C28 H28B 0.9754 . ?
C28 H28C 0.9565 . ?
N1 H1 0.8800 . ?

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 123.77(13) . . ?
O1 C1 C2 120.53(12) . . ?
N1 C1 C2 115.55(11) . . ?
C3 C2 C7 118.42(12) . . ?
C3 C2 C1 115.69(12) . . ?
C7 C2 C1 125.87(11) . . ?
C4 C3 C2 121.09(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.05(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.87(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.30(13) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.21(12) . . ?
C6 C7 N2 117.90(12) . . ?
C2 C7 N2 121.89(11) . . ?
C15 C8 N2 108.75(11) . . ?
C15 C8 C9 128.07(12) . . ?
N2 C8 C9 123.05(11) . . ?
C14 C9 C10 118.19(13) . . ?
C14 C9 C8 119.07(13) . . ?
C10 C9 C8 122.62(12) . . ?
C11 C10 C9 120.67(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.20(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.11(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.96(14) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.87(15) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C8 C15 C16 108.36(11) . . ?
C8 C15 H15 125.8 . . ?
C16 C15 H15 125.8 . . ?
C17 C16 C21 118.72(12) . . ?
C17 C16 C15 134.42(12) . . ?
C21 C16 C15 106.85(11) . . ?
C18 C17 C16 119.36(13) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.78(14) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 121.52(13) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 117.39(13) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
N2 C21 C20 130.01(12) . . ?
N2 C21 C16 107.76(11) . . ?
C20 C21 C16 122.17(12) . . ?
C23 C22 C27 120.48(13) . . ?
C23 C22 N1 122.14(13) . . ?
C27 C22 N1 117.38(11) . . ?
C24 C23 C22 119.67(15) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 120.78(14) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.48(14) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.66(15) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C22 117.94(13) . . ?
C26 C27 C28 120.30(13) . . ?
C22 C27 C28 121.76(12) . . ?
C27 C28 H28A 108.6 . . ?
C27 C28 H28B 111.3 . . ?
H28A C28 H28B 105.7 . . ?
C27 C28 H28C 111.0 . . ?
H28A C28 H28C 112.7 . . ?
H28B C28 H28C 107.4 . . ?
C1 N1 C22 128.81(11) . . ?
C1 N1 H1 115.6 . . ?
C22 N1 H1 115.6 . . ?
C21 N2 C8 108.27(10) . . ?
C21 N2 C7 123.37(10) . . ?
C8 N2 C7 127.09(11) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.033
