# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1406217'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N O4'
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.33

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           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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'
'-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                   16.874(3)
_cell_length_b                   10.8932(19)
_cell_length_c                   17.308(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3181.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3223
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.4

_exptl_crystal_description       block
_exptl_crystal_colour            white
_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    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.098
_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(2)
_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            26265
_diffrn_reflns_av_R_equivalents  0.1208
_diffrn_reflns_av_sigmaI/netI    0.1151
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.59
_reflns_number_total             3687
_reflns_number_gt                1651
_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)+(0.0753P)²+1.1845P] 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         3672
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1961
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_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
O4 O 0.10175(11) 0.90161(17) 1.01001(12) 0.0490(6) Uani 1 1 d . . .
C11 C 0.26315(16) 0.9253(2) 1.02482(15) 0.0382(7) Uani 1 1 d . . .
N1 N 0.36215(13) 0.8189(2) 0.97487(14) 0.0439(6) Uani 1 1 d . . .
C18 C 0.13192(17) 0.9896(2) 1.05935(17) 0.0399(7) Uani 1 1 d . . .
O1 O 0.11024(13) 0.7543(3) 0.92565(16) 0.0834(9) Uani 1 1 d . . .
O3 O 0.23628(15) 0.6669(2) 0.84164(15) 0.0802(8) Uani 1 1 d . . .
C10 C 0.23166(15) 0.8396(2) 0.97239(15) 0.0363(7) Uani 1 1 d . . .
C20 C 0.14696(18) 0.8248(3) 0.96438(19) 0.0476(8) Uani 1 1 d . . .
C9 C 0.29502(16) 0.7740(2) 0.94102(16) 0.0387(7) Uani 1 1 d . . .
C13 C 0.21273(16) 1.0062(2) 1.06850(16) 0.0382(7) Uani 1 1 d . . .
C7 C 0.44538(16) 0.7852(3) 0.95910(18) 0.0509(8) Uani 1 1 d . . .
H7A H 0.4484 0.6975 0.9499 0.061 Uiso 1 1 calc R . .
H7B H 0.4772 0.8036 1.0043 0.061 Uiso 1 1 calc R . .
O2 O 0.35137(17) 0.6001(2) 0.88153(16) 0.0925(9) Uani 1 1 d . . .
C12 C 0.34369(18) 0.9103(3) 1.02489(17) 0.0452(8) Uani 1 1 d . . .
H12 H 0.3796 0.9552 1.0542 0.054 Uiso 1 1 calc R . .
C5 C 0.53151(18) 0.7918(3) 0.84228(18) 0.0554(9) Uani 1 1 d . . .
H5 H 0.5426 0.7091 0.8504 0.067 Uiso 1 1 calc R . .
C4 C 0.47923(16) 0.8517(3) 0.89067(17) 0.0420(8) Uani 1 1 d . . .
C17 C 0.0780(2) 1.0589(3) 1.09979(19) 0.0546(9) Uani 1 1 d . . .
H17 H 0.0239 1.0458 1.0933 0.066 Uiso 1 1 calc R . .
C14 C 0.2378(2) 1.0980(3) 1.11891(17) 0.0524(8) Uani 1 1 d . . .
H14 H 0.2917 1.1122 1.1254 0.063 Uiso 1 1 calc R . .
C21 C 0.2987(2) 0.6733(3) 0.88556(18) 0.0478(8) Uani 1 1 d . . .
C3 C 0.46296(18) 0.9738(3) 0.8767(2) 0.0554(9) Uani 1 1 d . . .
H3 H 0.4277 1.0155 0.9087 0.067 Uiso 1 1 calc R . .
C2 C 0.4980(2) 1.0345(4) 0.8164(2) 0.0728(11) Uani 1 1 d . . .
H2 H 0.4862 1.1166 0.8074 0.087 Uiso 1 1 calc R . .
C15 C 0.1840(2) 1.1679(3) 1.15920(19) 0.0649(10) Uani 1 1 d . . .
H15 H 0.2016 1.2288 1.1927 0.078 Uiso 1 1 calc R . .
C1 C 0.5501(2) 0.9747(4) 0.7698(2) 0.0767(12) Uani 1 1 d . . .
H1 H 0.5742 1.0166 0.7292 0.092 Uiso 1 1 calc R . .
C16 C 0.1044(2) 1.1474(3) 1.1499(2) 0.0670(10) Uani 1 1 d . . .
H16 H 0.0681 1.1939 1.1777 0.080 Uiso 1 1 calc R . .
C6 C 0.5676(2) 0.8531(4) 0.7819(2) 0.0713(11) Uani 1 1 d . . .
H6 H 0.6033 0.8126 0.7498 0.086 Uiso 1 1 calc R . .
C22 C 0.2297(2) 0.5623(3) 0.7911(2) 0.0815(13) Uani 1 1 d . . .
H22A H 0.2701 0.5665 0.7522 0.122 Uiso 1 1 calc R . .
H22B H 0.1785 0.5624 0.7669 0.122 Uiso 1 1 calc R . .
H22C H 0.2360 0.4883 0.8206 0.122 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
O4 C20 1.380(3) . ?
O4 C18 1.381(3) . ?
C11 C12 1.369(4) . ?
C11 C10 1.406(4) . ?
C11 C13 1.439(4) . ?
N1 C12 1.356(4) . ?
N1 C9 1.366(3) . ?
N1 C7 1.477(4) . ?
C18 C17 1.374(4) . ?
C18 C13 1.384(4) . ?
O1 C20 1.193(3) . ?
O3 C21 1.300(4) . ?
O3 C22 1.441(4) . ?
C10 C9 1.396(4) . ?
C10 C20 1.445(4) . ?
C9 C21 1.459(4) . ?
C13 C14 1.393(4) . ?
C7 C4 1.501(4) . ?
O2 C21 1.196(4) . ?
C5 C4 1.380(4) . ?
C5 C6 1.383(4) . ?
C4 C3 1.380(4) . ?
C17 C16 1.371(5) . ?
C14 C15 1.374(4) . ?
C3 C2 1.370(5) . ?
C2 C1 1.360(5) . ?
C15 C16 1.371(5) . ?
C1 C6 1.373(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O4 C18 124.8(2) . . ?
C12 C11 C10 107.3(2) . . ?
C12 C11 C13 131.2(3) . . ?
C10 C11 C13 121.5(2) . . ?
C12 N1 C9 110.3(2) . . ?
C12 N1 C7 121.3(3) . . ?
C9 N1 C7 128.3(3) . . ?
C17 C18 C13 121.5(3) . . ?
C17 C18 O4 116.9(3) . . ?
C13 C18 O4 121.6(2) . . ?
C21 O3 C22 117.4(3) . . ?
C9 C10 C11 107.5(2) . . ?
C9 C10 C20 131.6(3) . . ?
C11 C10 C20 120.6(3) . . ?
O1 C20 O4 115.1(3) . . ?
O1 C20 C10 129.7(3) . . ?
O4 C20 C10 115.1(3) . . ?
N1 C9 C10 106.6(2) . . ?
N1 C9 C21 121.1(3) . . ?
C10 C9 C21 132.3(3) . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C11 116.2(3) . . ?
C14 C13 C11 126.1(3) . . ?
N1 C7 C4 112.8(2) . . ?
N1 C12 C11 108.3(3) . . ?
C4 C5 C6 120.8(3) . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 121.8(3) . . ?
C5 C4 C7 119.6(3) . . ?
C16 C17 C18 119.5(3) . . ?
C15 C14 C13 121.0(3) . . ?
O2 C21 O3 122.1(3) . . ?
O2 C21 C9 124.8(3) . . ?
O3 C21 C9 113.0(3) . . ?
C2 C3 C4 120.8(3) . . ?
C1 C2 C3 120.0(4) . . ?
C14 C15 C16 119.8(3) . . ?
C2 C1 C6 120.7(4) . . ?
C17 C16 C15 120.5(3) . . ?
C1 C6 C5 119.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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 1431800'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2015-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Cl N O4'
_chemical_formula_sum            'C20 H14 Cl N O4'
_chemical_formula_weight         367.77

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '


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

_cell_length_a                   7.9547(15)
_cell_length_b                   8.5268(16)
_cell_length_c                   14.076(3)
_cell_angle_alpha                85.276(5)
_cell_angle_beta                 82.284(5)
_cell_angle_gamma                63.553(5)
_cell_volume                     846.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    3810
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_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    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.252
_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            11386
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3913
_reflns_number_gt                2349
_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)+(0.0664P)²+0.2097P] 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         3814
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.30593(11) -0.09705(10) 1.03993(5) 0.0762(3) Uani 1 1 d . . .
O1 O 0.6530(2) 0.2409(2) 0.47618(11) 0.0469(4) Uani 1 1 d . . .
C4 C 0.9785(3) 0.2000(3) 0.44383(16) 0.0379(5) Uani 1 1 d . . .
O2 O 0.4611(2) 0.3684(2) 0.60260(12) 0.0568(5) Uani 1 1 d . . .
O3 O 0.5450(2) 0.4321(2) 0.78682(12) 0.0551(5) Uani 1 1 d . . .
C1 C 0.6179(3) 0.3219(3) 0.56192(17) 0.0409(5) Uani 1 1 d . . .
C3 C 0.9508(3) 0.2839(3) 0.53347(16) 0.0370(5) Uani 1 1 d . . .
C10 C 1.0648(3) 0.3289(3) 0.57880(16) 0.0417(5) Uani 1 1 d . . .
H10 H 1.1919 0.3050 0.5569 0.050 Uiso 1 1 calc R . .
N1 N 0.9656(2) 0.4129(2) 0.66001(13) 0.0399(5) Uani 1 1 d . . .
C18 C 1.3351(3) 0.0410(3) 0.86380(18) 0.0487(6) Uani 1 1 d . . .
H18 H 1.4457 -0.0653 0.8511 0.058 Uiso 1 1 calc R . .
C19 C 1.2770(3) 0.1707(3) 0.79389(17) 0.0467(6) Uani 1 1 d . . .
H19 H 1.3504 0.1543 0.7332 0.056 Uiso 1 1 calc R . .
O4 O 0.6329(3) 0.6459(2) 0.78193(16) 0.0778(6) Uani 1 1 d . . .
C6 C 0.8303(4) 0.1113(3) 0.33336(17) 0.0509(6) Uani 1 1 d . . .
H6 H 0.7224 0.1038 0.3167 0.061 Uiso 1 1 calc R . .
C5 C 0.8230(3) 0.1849(3) 0.41833(16) 0.0413(5) Uani 1 1 d . . .
C14 C 1.1133(3) 0.3248(3) 0.81038(16) 0.0400(5) Uani 1 1 d . . .
C9 C 1.1444(3) 0.1353(3) 0.38138(18) 0.0483(6) Uani 1 1 d . . .
H9 H 1.2527 0.1438 0.3969 0.058 Uiso 1 1 calc R . .
C11 C 0.7869(3) 0.4201(3) 0.67035(16) 0.0396(5) Uani 1 1 d . . .
C2 C 0.7755(3) 0.3411(3) 0.59111(15) 0.0363(5) Uani 1 1 d . . .
C20 C 1.0506(3) 0.4619(3) 0.73223(17) 0.0456(6) Uani 1 1 d . . .
H20A H 0.9571 0.5745 0.7605 0.055 Uiso 1 1 calc R . .
H20B H 1.1605 0.4789 0.7007 0.055 Uiso 1 1 calc R . .
C8 C 1.1527(4) 0.0595(3) 0.29750(18) 0.0546(7) Uani 1 1 d . . .
H8 H 1.2672 0.0139 0.2559 0.066 Uiso 1 1 calc R . .
C12 C 0.6488(3) 0.5132(3) 0.75060(17) 0.0447(6) Uani 1 1 d . . .
C15 C 1.0137(3) 0.3467(4) 0.89995(19) 0.0564(7) Uani 1 1 d . . .
H15 H 0.9025 0.4524 0.9132 0.068 Uiso 1 1 calc R . .
C7 C 0.9959(4) 0.0490(3) 0.27318(18) 0.0547(6) Uani 1 1 d . . .
H7 H 1.0024 -0.0017 0.2144 0.066 Uiso 1 1 calc R . .
C17 C 1.2322(4) 0.0670(3) 0.95125(17) 0.0498(6) Uani 1 1 d . . .
C16 C 1.0717(4) 0.2185(4) 0.97101(19) 0.0624(7) Uani 1 1 d . . .
H16 H 1.0015 0.2351 1.0326 0.075 Uiso 1 1 calc R . .
C13 C 0.3991(4) 0.5222(4) 0.86242(19) 0.0636(8) Uani 1 1 d . . .
H13A H 0.4536 0.5552 0.9113 0.095 Uiso 1 1 calc R . .
H13B H 0.3440 0.4448 0.8916 0.095 Uiso 1 1 calc R . .
H13C H 0.3006 0.6278 0.8358 0.095 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 C17 1.743(3) . ?
O1 C1 1.373(3) . ?
O1 C5 1.383(2) . ?
C4 C9 1.392(3) . ?
C4 C5 1.395(3) . ?
C4 C3 1.444(3) . ?
O2 C1 1.202(2) . ?
O3 C12 1.326(3) . ?
O3 C13 1.442(3) . ?
C1 C2 1.449(3) . ?
C3 C10 1.372(3) . ?
C3 C2 1.413(3) . ?
C10 N1 1.353(3) . ?
N1 C11 1.383(3) . ?
N1 C20 1.474(3) . ?
C18 C17 1.359(3) . ?
C18 C19 1.376(3) . ?
C19 C14 1.386(3) . ?
O4 C12 1.196(3) . ?
C6 C7 1.373(3) . ?
C6 C5 1.378(3) . ?
C14 C15 1.375(3) . ?
C14 C20 1.498(3) . ?
C9 C8 1.373(3) . ?
C11 C2 1.383(3) . ?
C11 C12 1.467(3) . ?
C8 C7 1.378(4) . ?
C15 C16 1.380(4) . ?
C17 C16 1.368(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 123.86(17) . . ?
C9 C4 C5 117.9(2) . . ?
C9 C4 C3 125.9(2) . . ?
C5 C4 C3 116.13(19) . . ?
C12 O3 C13 115.34(18) . . ?
O2 C1 O1 116.17(19) . . ?
O2 C1 C2 128.5(2) . . ?
O1 C1 C2 115.36(18) . . ?
C10 C3 C2 107.12(19) . . ?
C10 C3 C4 132.7(2) . . ?
C2 C3 C4 120.18(18) . . ?
N1 C10 C3 108.50(18) . . ?
C10 N1 C11 109.90(18) . . ?
C10 N1 C20 123.21(17) . . ?
C11 N1 C20 126.21(19) . . ?
C17 C18 C19 119.2(2) . . ?
C18 C19 C14 121.2(2) . . ?
C7 C6 C5 119.1(2) . . ?
C6 C5 O1 115.7(2) . . ?
C6 C5 C4 121.6(2) . . ?
O1 C5 C4 122.7(2) . . ?
C15 C14 C19 118.0(2) . . ?
C15 C14 C20 121.9(2) . . ?
C19 C14 C20 120.1(2) . . ?
C8 C9 C4 120.4(2) . . ?
C2 C11 N1 106.63(18) . . ?
C2 C11 C12 132.96(19) . . ?
N1 C11 C12 120.20(19) . . ?
C11 C2 C3 107.83(18) . . ?
C11 C2 C1 130.3(2) . . ?
C3 C2 C1 121.8(2) . . ?
N1 C20 C14 111.67(16) . . ?
C9 C8 C7 120.5(2) . . ?
O4 C12 O3 123.1(2) . . ?
O4 C12 C11 124.3(2) . . ?
O3 C12 C11 112.65(19) . . ?
C14 C15 C16 121.4(2) . . ?
C6 C7 C8 120.5(2) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 Cl1 119.2(2) . . ?
C16 C17 Cl1 119.3(2) . . ?
C17 C16 C15 118.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045
