# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_001
_database_code_depnum_ccdc_archive 'CCDC 1542637'
_audit_update_record             
;
2017-04-06 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 Br N3 O'
_chemical_formula_sum            'C29 H20 Br N3 O'
_chemical_formula_weight         506.38

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   8.6727(5)
_cell_length_b                   21.9456(14)
_cell_length_c                   12.5567(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.984(2)
_cell_angle_gamma                90.00
_cell_volume                     2380.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    7244
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20655
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4198
_reflns_number_gt                2943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0730P)²+3.0208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4185
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1431
_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
Br1 Br 0.09002(6) 0.26883(3) -0.25685(4) 0.0764(2) Uani 1 1 d . . .
O1 O 0.5726(4) 0.44311(15) 0.0793(2) 0.0663(9) Uani 1 1 d . . .
C3 C 0.6099(5) 0.31372(18) 0.3528(3) 0.0487(10) Uani 1 1 d . . .
C4 C 0.7097(5) 0.31571(18) 0.1756(3) 0.0485(10) Uani 1 1 d . . .
C5 C 0.4871(4) 0.37801(17) 0.2109(3) 0.0431(9) Uani 1 1 d . . .
C6 C 0.3764(4) 0.39965(19) 0.2764(3) 0.0468(10) Uani 1 1 d . . .
N1 N 0.7164(5) 0.27170(17) 0.3878(3) 0.0685(11) Uani 1 1 d . . .
H1A H 0.7809 0.2580 0.3454 0.082 Uiso 1 1 calc R . .
H1B H 0.7196 0.2587 0.4525 0.082 Uiso 1 1 calc R . .
C8 C 0.4882(5) 0.40134(19) 0.0973(3) 0.0465(9) Uani 1 1 d . . .
C9 C 0.2135(5) 0.3098(2) -0.1472(3) 0.0537(11) Uani 1 1 d . . .
C10 C 0.6003(4) 0.33644(18) 0.2474(3) 0.0435(9) Uani 1 1 d . . .
C11 C 0.2540(5) 0.4426(2) 0.2308(3) 0.0529(11) Uani 1 1 d . . .
C12 C 0.3052(6) 0.3183(2) 0.0352(3) 0.0614(12) Uani 1 1 d . . .
H12 H 0.3087 0.3037 0.1049 0.074 Uiso 1 1 calc R . .
C13 C 0.2861(6) 0.4059(2) 0.4624(4) 0.0587(12) Uani 1 1 d . . .
N3 N 0.7960(5) 0.30003(19) 0.1176(3) 0.0633(10) Uani 1 1 d . . .
C15 C 0.3895(4) 0.37013(17) 0.0130(3) 0.0433(9) Uani 1 1 d . . .
C16 C 0.5030(5) 0.33889(19) 0.4204(3) 0.0506(10) Uani 1 1 d . . .
C17 C 0.5151(6) 0.3205(2) 0.5309(4) 0.0595(12) Uani 1 1 d . . .
C18 C 0.2855(5) 0.5034(2) 0.2198(3) 0.0587(11) Uani 1 1 d . . .
H18 H 0.3819 0.5187 0.2448 0.070 Uiso 1 1 calc R . .
C19 C 0.3888(5) 0.38055(19) 0.3836(3) 0.0497(10) Uani 1 1 d . . .
C20 C 0.0315(6) 0.5185(3) 0.1340(4) 0.0712(14) Uani 1 1 d . . .
H20 H -0.0439 0.5439 0.1007 0.085 Uiso 1 1 calc R . .
C21 C 0.3825(5) 0.3908(2) -0.0916(3) 0.0565(11) Uani 1 1 d . . .
H21 H 0.4372 0.4256 -0.1079 0.068 Uiso 1 1 calc R . .
C22 C 0.2955(5) 0.3605(2) -0.1714(3) 0.0624(12) Uani 1 1 d . . .
H22 H 0.2923 0.3743 -0.2416 0.075 Uiso 1 1 calc R . .
N2 N 0.5282(6) 0.3058(2) 0.6181(3) 0.0800(13) Uani 1 1 d . . .
C24 C 0.1092(5) 0.4207(2) 0.1923(4) 0.0644(12) Uani 1 1 d . . .
H24 H 0.0872 0.3794 0.1990 0.077 Uiso 1 1 calc R . .
C25 C -0.0019(6) 0.4589(3) 0.1446(4) 0.0759(15) Uani 1 1 d . . .
H25 H -0.0987 0.4438 0.1200 0.091 Uiso 1 1 calc R . .
C26 C 0.2164(6) 0.2884(2) -0.0453(4) 0.0671(13) Uani 1 1 d . . .
H26 H 0.1595 0.2541 -0.0300 0.081 Uiso 1 1 calc R . .
C27 C 0.1708(7) 0.5431(2) 0.1699(4) 0.0677(14) Uani 1 1 d . . .
C28 C 0.1323(6) 0.3891(2) 0.4601(4) 0.0708(14) Uani 1 1 d . . .
H28 H 0.0905 0.3614 0.4095 0.085 Uiso 1 1 calc R . .
C29 C 0.0392(6) 0.4146(3) 0.5359(5) 0.0818(18) Uani 1 1 d . . .
C31 C 0.3445(7) 0.4467(2) 0.5384(4) 0.0755(15) Uani 1 1 d . . .
H31 H 0.4486 0.4572 0.5413 0.091 Uiso 1 1 calc R . .
C32 C 0.1010(10) 0.4564(3) 0.6079(5) 0.096(2) Uani 1 1 d . . .
H32 H 0.0380 0.4740 0.6558 0.115 Uiso 1 1 calc R . .
C33 C 0.2509(9) 0.4727(3) 0.6114(5) 0.094(2) Uani 1 1 d . . .
H33 H 0.2917 0.5008 0.6616 0.113 Uiso 1 1 calc R . .
C34 C 0.2070(8) 0.6087(3) 0.1559(6) 0.100(2) Uani 1 1 d . . .
H34A H 0.2634 0.6137 0.0940 0.150 Uiso 1 1 calc R . .
H34B H 0.2685 0.6232 0.2180 0.150 Uiso 1 1 calc R . .
H34C H 0.1124 0.6315 0.1467 0.150 Uiso 1 1 calc R . .
C35 C -0.1197(8) 0.3975(4) 0.5372(6) 0.126(3) Uani 1 1 d . . .
H35A H -0.1265 0.3599 0.5757 0.189 Uiso 1 1 calc R . .
H35B H -0.1646 0.3922 0.4652 0.189 Uiso 1 1 calc R . .
H35C H -0.1746 0.4288 0.5716 0.189 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.896(4) . ?
O1 C8 1.206(5) . ?
C3 N1 1.351(5) . ?
C3 C10 1.410(5) . ?
C3 C16 1.422(6) . ?
C4 N3 1.141(5) . ?
C4 C10 1.438(6) . ?
C5 C10 1.389(5) . ?
C5 C6 1.400(5) . ?
C5 C8 1.517(5) . ?
C6 C19 1.406(6) . ?
C6 C11 1.497(6) . ?
C8 C15 1.471(6) . ?
C9 C26 1.362(6) . ?
C9 C22 1.369(6) . ?
C11 C18 1.371(6) . ?
C11 C24 1.392(6) . ?
C12 C26 1.382(6) . ?
C12 C15 1.392(6) . ?
C13 C31 1.373(7) . ?
C13 C28 1.382(7) . ?
C13 C19 1.495(6) . ?
C15 C21 1.386(5) . ?
C16 C19 1.397(6) . ?
C16 C17 1.440(6) . ?
C17 N2 1.137(6) . ?
C18 C27 1.427(7) . ?
C20 C25 1.348(8) . ?
C20 C27 1.365(8) . ?
C21 C22 1.373(6) . ?
C24 C25 1.375(7) . ?
C27 C34 1.486(7) . ?
C28 C29 1.416(7) . ?
C29 C32 1.364(9) . ?
C29 C35 1.430(8) . ?
C31 C33 1.398(7) . ?
C32 C33 1.346(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C3 C10 122.0(4) . . ?
N1 C3 C16 122.2(4) . . ?
C10 C3 C16 115.8(4) . . ?
N3 C4 C10 178.9(5) . . ?
C10 C5 C6 122.0(3) . . ?
C10 C5 C8 118.0(3) . . ?
C6 C5 C8 119.9(3) . . ?
C5 C6 C19 117.5(4) . . ?
C5 C6 C11 119.3(3) . . ?
C19 C6 C11 123.2(3) . . ?
O1 C8 C15 122.9(4) . . ?
O1 C8 C5 119.1(4) . . ?
C15 C8 C5 117.9(4) . . ?
C26 C9 C22 121.4(4) . . ?
C26 C9 Br1 118.8(4) . . ?
C22 C9 Br1 119.7(3) . . ?
C5 C10 C3 121.6(3) . . ?
C5 C10 C4 119.2(3) . . ?
C3 C10 C4 119.2(4) . . ?
C18 C11 C24 118.9(4) . . ?
C18 C11 C6 120.7(4) . . ?
C24 C11 C6 120.2(4) . . ?
C26 C12 C15 120.7(4) . . ?
C31 C13 C28 119.1(4) . . ?
C31 C13 C19 119.8(5) . . ?
C28 C13 C19 121.1(5) . . ?
C21 C15 C12 118.4(4) . . ?
C21 C15 C8 120.3(4) . . ?
C12 C15 C8 121.3(4) . . ?
C19 C16 C3 122.5(4) . . ?
C19 C16 C17 119.5(4) . . ?
C3 C16 C17 118.0(4) . . ?
N2 C17 C16 178.4(5) . . ?
C11 C18 C27 120.1(5) . . ?
C16 C19 C6 120.3(4) . . ?
C16 C19 C13 118.1(4) . . ?
C6 C19 C13 121.5(4) . . ?
C25 C20 C27 122.9(5) . . ?
C22 C21 C15 120.6(4) . . ?
C9 C22 C21 119.7(4) . . ?
C25 C24 C11 121.1(5) . . ?
C20 C25 C24 119.1(5) . . ?
C9 C26 C12 119.1(4) . . ?
C20 C27 C18 117.8(5) . . ?
C20 C27 C34 122.4(5) . . ?
C18 C27 C34 119.8(5) . . ?
C13 C28 C29 119.1(6) . . ?
C32 C29 C28 119.9(6) . . ?
C32 C29 C35 119.5(6) . . ?
C28 C29 C35 120.6(7) . . ?
C13 C31 C33 121.4(6) . . ?
C33 C32 C29 121.5(6) . . ?
C32 C33 C31 119.0(7) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_001_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1547900'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H18 Cl N3 O2'
_chemical_formula_sum            'C28 H18 Cl N3 O2'
_chemical_formula_weight         463.90

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   11.579(3)
_cell_length_b                   12.312(3)
_cell_length_c                   17.454(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.948(10)
_cell_angle_gamma                90.00
_cell_volume                     2367.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    5381
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            cololess
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11690
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.45
_reflns_number_total             5391
_reflns_number_gt                3763
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0515P)²+0.7546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5233
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cl1 Cl 0.44098(6) 1.11692(6) 0.11036(5) 0.0953(3) Uani 1 1 d . . .
C3 C 0.90379(14) 0.61531(13) 0.30386(10) 0.0333(4) Uani 1 1 d . . .
C22 C 0.72293(15) 0.87514(12) 0.24491(10) 0.0344(4) Uani 1 1 d . . .
C4 C 0.81953(14) 0.68936(13) 0.25722(10) 0.0328(4) Uani 1 1 d . . .
C16 C 0.73824(15) 0.66286(13) 0.17438(10) 0.0347(4) Uani 1 1 d . . .
C10 C 0.85436(14) 0.41022(13) 0.28925(10) 0.0350(4) Uani 1 1 d . . .
N1 N 1.05008(16) 0.77126(13) 0.48900(9) 0.0599(5) Uani 1 1 d . . .
H1A H 1.1011 0.7243 0.5166 0.072 Uiso 1 1 calc R . .
H1B H 1.0464 0.8349 0.5084 0.072 Uiso 1 1 calc R . .
C2 C 0.97874(15) 0.64169(13) 0.38124(10) 0.0365(4) Uani 1 1 d . . .
O1 O 0.99413(14) 0.49535(11) 0.23436(10) 0.0613(4) Uani 1 1 d . . .
C5 C 0.81325(14) 0.79242(12) 0.29015(10) 0.0327(4) Uani 1 1 d . . .
C9 C 0.92158(15) 0.50442(13) 0.27159(10) 0.0368(4) Uani 1 1 d . . .
C11 C 0.77106(15) 0.42179(14) 0.33149(11) 0.0422(4) Uani 1 1 d . . .
H11 H 0.7563 0.4900 0.3494 0.051 Uiso 1 1 calc R . .
O2 O 0.51834(16) 0.62154(13) -0.06292(8) 0.0736(5) Uani 1 1 d . . .
C27 C 0.63355(16) 0.91097(14) 0.27696(11) 0.0421(4) Uani 1 1 d . . .
H27 H 0.6317 0.8847 0.3265 0.050 Uiso 1 1 calc R . .
C14 C 0.8169(2) 0.21819(15) 0.28056(14) 0.0595(6) Uani 1 1 d . . .
H14 H 0.8326 0.1494 0.2641 0.071 Uiso 1 1 calc R . .
C6 C 0.89106(15) 0.81941(13) 0.36682(10) 0.0352(4) Uani 1 1 d . . .
N3 N 0.89222(16) 1.01245(13) 0.42347(10) 0.0578(5) Uani 1 1 d . . .
C21 C 0.61255(16) 0.66663(14) 0.15651(10) 0.0395(4) Uani 1 1 d . . .
H21 H 0.5792 0.6786 0.1979 0.047 Uiso 1 1 calc R . .
C1 C 0.97538(15) 0.74490(14) 0.41494(10) 0.0390(4) Uani 1 1 d . . .
C23 C 0.72519(16) 0.91530(15) 0.17118(11) 0.0441(4) Uani 1 1 d . . .
H23 H 0.7848 0.8919 0.1494 0.053 Uiso 1 1 calc R . .
C8 C 0.88994(16) 0.92790(14) 0.39692(10) 0.0414(4) Uani 1 1 d . . .
C25 C 0.55077(17) 1.02403(15) 0.16294(13) 0.0527(5) Uani 1 1 d . . .
N2 N 1.13342(19) 0.50403(16) 0.46693(11) 0.0703(6) Uani 1 1 d . . .
C26 C 0.54731(17) 0.98552(15) 0.23560(13) 0.0495(5) Uani 1 1 d . . .
H26 H 0.4875 1.0092 0.2571 0.059 Uiso 1 1 calc R . .
C7 C 1.06444(17) 0.56394(15) 0.42806(11) 0.0460(4) Uani 1 1 d . . .
C20 C 0.53550(17) 0.65293(15) 0.07826(11) 0.0467(4) Uani 1 1 d . . .
H20 H 0.4518 0.6556 0.0677 0.056 Uiso 1 1 calc R . .
C15 C 0.87742(18) 0.30723(14) 0.26411(12) 0.0494(5) Uani 1 1 d . . .
H15 H 0.9336 0.2986 0.2363 0.059 Uiso 1 1 calc R . .
C13 C 0.73297(19) 0.23085(16) 0.32142(13) 0.0577(6) Uani 1 1 d . . .
H13 H 0.6917 0.1705 0.3317 0.069 Uiso 1 1 calc R . .
C17 C 0.78511(18) 0.64247(17) 0.11141(11) 0.0511(5) Uani 1 1 d . . .
H17 H 0.8687 0.6376 0.1218 0.061 Uiso 1 1 calc R . .
C19 C 0.58431(19) 0.63546(16) 0.01673(11) 0.0511(5) Uani 1 1 d . . .
C12 C 0.70976(18) 0.33135(16) 0.34697(13) 0.0539(5) Uani 1 1 d . . .
H12 H 0.6532 0.3391 0.3746 0.065 Uiso 1 1 calc R . .
C24 C 0.63905(19) 0.99019(16) 0.12972(13) 0.0547(5) Uani 1 1 d . . .
H24 H 0.6405 1.0173 0.0803 0.066 Uiso 1 1 calc R . .
C18 C 0.7091(2) 0.6294(2) 0.03378(12) 0.0618(6) Uani 1 1 d . . .
H18 H 0.7421 0.6163 -0.0077 0.074 Uiso 1 1 calc R . .
C28 C 0.3923(2) 0.6423(2) -0.08670(15) 0.0876(9) Uani 1 1 d . . .
H28A H 0.3536 0.5914 -0.0608 0.131 Uiso 1 1 calc R . .
H28B H 0.3592 0.6347 -0.1441 0.131 Uiso 1 1 calc R . .
H28C H 0.3783 0.7148 -0.0714 0.131 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C25 1.746(2) . ?
C3 C2 1.400(2) . ?
C3 C4 1.399(2) . ?
C3 C9 1.515(2) . ?
C22 C23 1.386(2) . ?
C22 C27 1.391(2) . ?
C22 C5 1.498(2) . ?
C4 C5 1.404(2) . ?
C4 C16 1.498(2) . ?
C16 C17 1.390(2) . ?
C16 C21 1.392(2) . ?
C10 C11 1.390(2) . ?
C10 C15 1.394(2) . ?
C10 C9 1.481(2) . ?
N1 C1 1.355(2) . ?
C2 C1 1.406(2) . ?
C2 C7 1.438(2) . ?
O1 C9 1.215(2) . ?
C5 C6 1.404(2) . ?
C11 C12 1.391(3) . ?
O2 C19 1.375(2) . ?
O2 C28 1.413(3) . ?
C27 C26 1.384(3) . ?
C14 C15 1.378(3) . ?
C14 C13 1.380(3) . ?
C6 C1 1.412(2) . ?
C6 C8 1.437(2) . ?
N3 C8 1.137(2) . ?
C21 C20 1.392(2) . ?
C23 C24 1.387(3) . ?
C25 C26 1.366(3) . ?
C25 C24 1.386(3) . ?
N2 C7 1.144(2) . ?
C20 C19 1.376(3) . ?
C13 C12 1.370(3) . ?
C17 C18 1.379(3) . ?
C19 C18 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C3 C4 121.61(14) . . ?
C2 C3 C9 116.92(14) . . ?
C4 C3 C9 121.42(14) . . ?
C23 C22 C27 119.29(16) . . ?
C23 C22 C5 121.45(15) . . ?
C27 C22 C5 119.25(15) . . ?
C3 C4 C5 117.75(14) . . ?
C3 C4 C16 122.54(14) . . ?
C5 C4 C16 119.71(14) . . ?
C17 C16 C21 117.69(16) . . ?
C17 C16 C4 121.34(15) . . ?
C21 C16 C4 120.76(15) . . ?
C11 C10 C15 119.44(17) . . ?
C11 C10 C9 121.68(15) . . ?
C15 C10 C9 118.87(16) . . ?
C3 C2 C1 121.63(15) . . ?
C3 C2 C7 120.51(15) . . ?
C1 C2 C7 117.84(15) . . ?
C6 C5 C4 120.35(15) . . ?
C6 C5 C22 118.69(14) . . ?
C4 C5 C22 120.95(14) . . ?
O1 C9 C10 122.25(15) . . ?
O1 C9 C3 118.50(15) . . ?
C10 C9 C3 119.20(14) . . ?
C12 C11 C10 120.00(17) . . ?
C19 O2 C28 118.45(19) . . ?
C26 C27 C22 120.47(17) . . ?
C15 C14 C13 120.14(18) . . ?
C5 C6 C1 122.42(14) . . ?
C5 C6 C8 119.56(15) . . ?
C1 C6 C8 117.96(15) . . ?
C20 C21 C16 121.69(16) . . ?
N1 C1 C2 121.60(16) . . ?
N1 C1 C6 122.20(15) . . ?
C2 C1 C6 116.20(15) . . ?
C24 C23 C22 120.35(18) . . ?
N3 C8 C6 177.34(19) . . ?
C26 C25 C24 121.37(18) . . ?
C26 C25 Cl1 119.38(17) . . ?
C24 C25 Cl1 119.25(17) . . ?
C25 C26 C27 119.44(18) . . ?
N2 C7 C2 178.2(2) . . ?
C19 C20 C21 119.43(18) . . ?
C14 C15 C10 119.92(19) . . ?
C12 C13 C14 120.69(19) . . ?
C18 C17 C16 120.76(18) . . ?
O2 C19 C20 125.08(19) . . ?
O2 C19 C18 115.36(18) . . ?
C20 C19 C18 119.55(17) . . ?
C13 C12 C11 119.8(2) . . ?
C23 C24 C25 119.09(19) . . ?
C17 C18 C19 120.84(18) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.041
