# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_khc1225
_database_code_depnum_ccdc_archive 'CCDC 1529594'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Br1 N2 O1'
_chemical_formula_weight         315.16

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                   8.3615(14)
_cell_length_b                   8.6790(16)
_cell_length_c                   9.7121(16)
_cell_angle_alpha                87.261(14)
_cell_angle_beta                 86.850(13)
_cell_angle_gamma                74.088(13)
_cell_volume                     676.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6192
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    3.031
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4521
_exptl_absorpt_correction_T_max  0.8754
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6192
_diffrn_reflns_av_R_equivalents  0.1164
_diffrn_reflns_av_sigmaI/netI    0.1303
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2940
_reflns_number_gt                2841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (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)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
C1 C 0.5535(8) 0.6513(8) 0.6638(6) 0.0454(16) Uani 1 1 d . . .
C2 C 0.6805(8) 0.5519(8) 0.5850(7) 0.0487(17) Uani 1 1 d . . .
H2 H 0.7506 0.4612 0.6260 0.058 Uiso 1 1 calc R . .
C3 C 0.7035(9) 0.5861(9) 0.4476(7) 0.0521(18) Uani 1 1 d . . .
C4 C 0.8446(10) 0.4797(11) 0.3615(8) 0.072(2) Uani 1 1 d . . .
H4A H 0.8323 0.3729 0.3635 0.087 Uiso 1 1 calc R . .
H4B H 0.9492 0.4779 0.3986 0.087 Uiso 1 1 calc R . .
H4C H 0.8414 0.5212 0.2680 0.087 Uiso 1 1 calc R . .
C5 C 0.5953(9) 0.7210(9) 0.3879(7) 0.0517(18) Uani 1 1 d . . .
H5 H 0.6074 0.7445 0.2941 0.062 Uiso 1 1 calc R . .
C6 C 0.4698(8) 0.8203(8) 0.4671(6) 0.0481(17) Uani 1 1 d . . .
H6 H 0.3985 0.9097 0.4253 0.058 Uiso 1 1 calc R . .
C7 C 0.4475(8) 0.7896(8) 0.6078(6) 0.0402(15) Uani 1 1 d . . .
C8 C 0.3183(8) 0.9046(8) 0.6912(6) 0.0419(16) Uani 1 1 d . . .
C9 C 0.2218(8) 1.0582(8) 0.8774(6) 0.0427(16) Uani 1 1 d . . .
C10 C 0.2501(9) 1.1097(10) 1.0074(7) 0.063(2) Uani 1 1 d . . .
H10 H 0.3534 1.0696 1.0458 0.076 Uiso 1 1 calc R . .
C11 C 0.1277(10) 1.2170(12) 1.0764(8) 0.076(3) Uani 1 1 d . . .
H11 H 0.1479 1.2490 1.1623 0.091 Uiso 1 1 calc R . .
C12 C -0.0267(10) 1.2803(10) 1.0221(8) 0.070(2) Uani 1 1 d . . .
H12 H -0.1096 1.3536 1.0714 0.084 Uiso 1 1 calc R . .
C13 C -0.0573(9) 1.2346(9) 0.8952(7) 0.062(2) Uani 1 1 d . . .
H13 H -0.1608 1.2778 0.8578 0.075 Uiso 1 1 calc R . .
C14 C 0.0655(8) 1.1245(8) 0.8228(6) 0.0464(17) Uani 1 1 d . . .
C15 C 0.0357(9) 1.0754(9) 0.6873(7) 0.0538(19) Uani 1 1 d . . .
N1 N 0.3483(6) 0.9506(7) 0.8076(5) 0.0456(14) Uani 1 1 d . . .
N2 N 0.1677(6) 0.9634(6) 0.6307(5) 0.0484(15) Uani 1 1 d . . .
H2A H 0.1561 0.9272 0.5520 0.058 Uiso 1 1 calc R . .
O1 O -0.0934(6) 1.1283(7) 0.6281(5) 0.0824(19) Uani 1 1 d . . .
Br1 Br 0.52676(11) 0.58371(11) 0.84941(8) 0.0692(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C7 1.389(9) . ?
C1 C2 1.389(9) . ?
C1 Br1 1.889(6) . ?
C2 C3 1.368(9) . ?
C2 H2 0.9300 . ?
C3 C5 1.392(10) . ?
C3 C4 1.521(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.384(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.487(8) . ?
C8 N1 1.276(7) . ?
C8 N2 1.375(7) . ?
C9 N1 1.375(8) . ?
C9 C14 1.398(9) . ?
C9 C10 1.413(9) . ?
C10 C11 1.351(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.457(8) . ?
C15 O1 1.216(8) . ?
C15 N2 1.365(8) . ?
N2 H2A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 121.8(6) . . ?
C7 C1 Br1 121.7(5) . . ?
C2 C1 Br1 116.4(5) . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C5 118.7(6) . . ?
C2 C3 C4 120.9(7) . . ?
C5 C3 C4 120.5(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C3 C5 H5 119.8 . . ?
C5 C6 C7 121.6(6) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C1 C7 C6 116.7(6) . . ?
C1 C7 C8 123.2(5) . . ?
C6 C7 C8 120.0(5) . . ?
N1 C8 N2 122.8(5) . . ?
N1 C8 C7 122.0(5) . . ?
N2 C8 C7 115.1(5) . . ?
N1 C9 C14 122.6(5) . . ?
N1 C9 C10 119.6(6) . . ?
C14 C9 C10 117.7(6) . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.4(7) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 119.7(7) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.1(7) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.8(6) . . ?
C13 C14 C15 120.8(6) . . ?
C9 C14 C15 118.4(6) . . ?
O1 C15 N2 122.2(6) . . ?
O1 C15 C14 124.1(6) . . ?
N2 C15 C14 113.7(5) . . ?
C8 N1 C9 118.2(5) . . ?
C15 N2 C8 124.2(5) . . ?
C15 N2 H2A 117.9 . . ?
C8 N2 H2A 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3 -1.2(11) . . . . ?
Br1 C1 C2 C3 176.3(5) . . . . ?
C1 C2 C3 C5 -1.1(10) . . . . ?
C1 C2 C3 C4 178.7(7) . . . . ?
C2 C3 C5 C6 1.6(11) . . . . ?
C4 C3 C5 C6 -178.2(7) . . . . ?
C3 C5 C6 C7 0.1(11) . . . . ?
C2 C1 C7 C6 2.8(10) . . . . ?
Br1 C1 C7 C6 -174.5(5) . . . . ?
C2 C1 C7 C8 -175.5(6) . . . . ?
Br1 C1 C7 C8 7.2(9) . . . . ?
C5 C6 C7 C1 -2.3(10) . . . . ?
C5 C6 C7 C8 176.1(6) . . . . ?
C1 C7 C8 N1 44.6(10) . . . . ?
C6 C7 C8 N1 -133.7(7) . . . . ?
C1 C7 C8 N2 -138.5(7) . . . . ?
C6 C7 C8 N2 43.2(9) . . . . ?
N1 C9 C10 C11 179.1(8) . . . . ?
C14 C9 C10 C11 1.3(12) . . . . ?
C9 C10 C11 C12 -0.6(14) . . . . ?
C10 C11 C12 C13 -0.4(14) . . . . ?
C11 C12 C13 C14 0.7(13) . . . . ?
C12 C13 C14 C9 0.1(12) . . . . ?
C12 C13 C14 C15 -179.5(8) . . . . ?
N1 C9 C14 C13 -178.7(7) . . . . ?
C10 C9 C14 C13 -1.0(11) . . . . ?
N1 C9 C14 C15 0.9(11) . . . . ?
C10 C9 C14 C15 178.6(7) . . . . ?
C13 C14 C15 O1 1.8(13) . . . . ?
C9 C14 C15 O1 -177.8(8) . . . . ?
C13 C14 C15 N2 -178.6(7) . . . . ?
C9 C14 C15 N2 1.8(10) . . . . ?
N2 C8 N1 C9 2.9(10) . . . . ?
C7 C8 N1 C9 179.5(6) . . . . ?
C14 C9 N1 C8 -3.3(10) . . . . ?
C10 C9 N1 C8 179.1(7) . . . . ?
O1 C15 N2 C8 177.4(7) . . . . ?
C14 C15 N2 C8 -2.2(10) . . . . ?
N1 C8 N2 C15 -0.1(11) . . . . ?
C7 C8 N2 C15 -177.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_khd390
_database_code_depnum_ccdc_archive 'CCDC 1529593'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl2 N1 O4'
_chemical_formula_weight         352.16

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                   8.079(2)
_cell_length_b                   8.088(3)
_cell_length_c                   12.700(4)
_cell_angle_alpha                87.80(2)
_cell_angle_beta                 83.42(2)
_cell_angle_gamma                71.65(2)
_cell_volume                     782.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6859
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_T_max  0.8456
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6859
_diffrn_reflns_av_R_equivalents  0.0951
_diffrn_reflns_av_sigmaI/netI    0.1477
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3387
_reflns_number_gt                3030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1512
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.004

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 0.6339(16) 0.7441(14) 0.5166(8) 0.059(3) Uani 1 1 d . . .
C2 C 0.514(2) 0.7737(17) 0.6038(9) 0.079(4) Uani 1 1 d . . .
H2 H 0.5455 0.7940 0.6692 0.095 Uiso 1 1 calc R . .
C3 C 0.349(2) 0.7732(19) 0.5943(11) 0.084(4) Uani 1 1 d . . .
H3 H 0.2667 0.7883 0.6537 0.101 Uiso 1 1 calc R . .
C4 C 0.3038(18) 0.7504(17) 0.4976(11) 0.077(4) Uani 1 1 d . . .
H4 H 0.1896 0.7526 0.4914 0.093 Uiso 1 1 calc R . .
C5 C 0.4232(16) 0.7241(14) 0.4079(9) 0.062(3) Uani 1 1 d . . .
C6 C 0.5972(13) 0.7194(12) 0.4164(7) 0.050(2) Uani 1 1 d . . .
C7 C 0.7354(14) 0.6887(14) 0.3210(8) 0.054(3) Uani 1 1 d . . .
C8 C 0.9607(12) 0.5301(12) 0.2118(6) 0.042(2) Uani 1 1 d . . .
C9 C 1.0766(13) 0.3676(12) 0.1821(7) 0.047(2) Uani 1 1 d . . .
H9 H 1.0712 0.2690 0.2207 0.056 Uiso 1 1 calc R . .
C10 C 1.2000(12) 0.3528(12) 0.0952(7) 0.045(2) Uani 1 1 d . . .
C11 C 1.3089(17) 0.0488(15) 0.1075(10) 0.075(4) Uani 1 1 d . . .
H11A H 1.1949 0.0360 0.1066 0.090 Uiso 1 1 calc R . .
H11B H 1.3324 0.0537 0.1795 0.090 Uiso 1 1 calc R . .
H11C H 1.3960 -0.0489 0.0725 0.090 Uiso 1 1 calc R . .
C12 C 1.3533(13) 0.6247(13) -0.1028(7) 0.050(2) Uani 1 1 d . . .
H12A H 1.3833 0.6979 -0.0555 0.060 Uiso 1 1 calc R . .
H12B H 1.2446 0.6878 -0.1298 0.060 Uiso 1 1 calc R . .
H12C H 1.4443 0.5899 -0.1606 0.060 Uiso 1 1 calc R . .
C13 C 1.2120(12) 0.5038(12) 0.0348(7) 0.042(2) Uani 1 1 d . . .
C14 C 1.1005(14) 0.6656(12) 0.0702(7) 0.050(2) Uani 1 1 d . . .
H14 H 1.1111 0.7669 0.0370 0.060 Uiso 1 1 calc R . .
C15 C 0.9717(14) 0.6754(13) 0.1563(7) 0.051(3) Uani 1 1 d . . .
C16 C 0.8519(15) 0.8471(14) 0.1897(9) 0.064(3) Uani 1 1 d . . .
N1 N 0.8370(10) 0.5396(10) 0.3005(6) 0.0445(19) Uani 1 1 d . . .
O1 O 1.3140(9) 0.2028(8) 0.0547(5) 0.0541(18) Uani 1 1 d . . .
O2 O 1.3350(9) 0.4750(8) -0.0474(5) 0.0520(18) Uani 1 1 d . . .
O3 O 0.8492(13) 0.9847(10) 0.1537(7) 0.094(3) Uani 1 1 d . . .
O4 O 0.7305(10) 0.8430(9) 0.2757(6) 0.069(2) Uani 1 1 d . . .
Cl1 Cl 0.8455(5) 0.7392(7) 0.5344(3) 0.1195(18) Uani 1 1 d . . .
Cl2 Cl 0.3640(5) 0.6983(5) 0.2860(3) 0.0851(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 C2 1.359(15) . ?
C1 C6 1.375(15) . ?
C1 Cl1 1.738(13) . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(16) . ?
C5 Cl2 1.711(12) . ?
C6 C7 1.521(13) . ?
C7 N1 1.244(12) . ?
C7 O4 1.345(12) . ?
C8 C15 1.368(13) . ?
C8 C9 1.388(13) . ?
C8 N1 1.405(11) . ?
C9 C10 1.382(13) . ?
C9 H9 0.9300 . ?
C10 O1 1.350(11) . ?
C10 C13 1.441(13) . ?
C11 O1 1.402(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.416(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O2 1.329(10) . ?
C13 C14 1.392(13) . ?
C14 C15 1.407(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.466(14) . ?
C16 O3 1.181(12) . ?
C16 O4 1.389(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 124.2(12) . . ?
C2 C1 Cl1 117.1(10) . . ?
C6 C1 Cl1 118.7(8) . . ?
C1 C2 C3 119.2(12) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.5(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.8(13) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119.7(11) . . ?
C4 C5 Cl2 121.3(10) . . ?
C6 C5 Cl2 119.1(8) . . ?
C1 C6 C5 115.6(9) . . ?
C1 C6 C7 122.1(10) . . ?
C5 C6 C7 122.2(10) . . ?
N1 C7 O4 130.6(9) . . ?
N1 C7 C6 120.3(9) . . ?
O4 C7 C6 108.9(8) . . ?
C15 C8 C9 119.9(8) . . ?
C15 C8 N1 122.0(8) . . ?
C9 C8 N1 118.1(8) . . ?
C10 C9 C8 119.8(9) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O1 C10 C9 126.0(9) . . ?
O1 C10 C13 112.8(8) . . ?
C9 C10 C13 121.1(8) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.4 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 126.2(8) . . ?
O2 C13 C10 116.3(8) . . ?
C14 C13 C10 117.5(8) . . ?
C13 C14 C15 119.8(9) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C8 C15 C14 121.6(9) . . ?
C8 C15 C16 119.6(9) . . ?
C14 C15 C16 118.7(9) . . ?
O3 C16 O4 117.7(9) . . ?
O3 C16 C15 128.0(10) . . ?
O4 C16 C15 114.2(9) . . ?
C7 N1 C8 114.5(8) . . ?
C10 O1 C11 116.7(8) . . ?
C13 O2 C12 116.1(7) . . ?
C7 O4 C16 118.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.5(19) . . . . ?
Cl1 C1 C2 C3 -178.0(11) . . . . ?
C1 C2 C3 C4 -3(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 0.5(19) . . . . ?
C3 C4 C5 Cl2 -179.2(11) . . . . ?
C2 C1 C6 C5 -0.8(16) . . . . ?
Cl1 C1 C6 C5 179.7(8) . . . . ?
C2 C1 C6 C7 179.3(11) . . . . ?
Cl1 C1 C6 C7 -0.2(13) . . . . ?
C4 C5 C6 C1 -0.7(15) . . . . ?
Cl2 C5 C6 C1 179.0(8) . . . . ?
C4 C5 C6 C7 179.2(10) . . . . ?
Cl2 C5 C6 C7 -1.1(14) . . . . ?
C1 C6 C7 N1 84.6(13) . . . . ?
C5 C6 C7 N1 -95.3(13) . . . . ?
C1 C6 C7 O4 -91.2(12) . . . . ?
C5 C6 C7 O4 88.9(12) . . . . ?
C15 C8 C9 C10 -1.5(14) . . . . ?
N1 C8 C9 C10 179.8(9) . . . . ?
C8 C9 C10 O1 -176.4(9) . . . . ?
C8 C9 C10 C13 0.5(14) . . . . ?
O1 C10 C13 O2 -2.5(12) . . . . ?
C9 C10 C13 O2 -179.8(9) . . . . ?
O1 C10 C13 C14 -179.7(9) . . . . ?
C9 C10 C13 C14 3.0(14) . . . . ?
O2 C13 C14 C15 177.6(9) . . . . ?
C10 C13 C14 C15 -5.6(14) . . . . ?
C9 C8 C15 C14 -1.2(15) . . . . ?
N1 C8 C15 C14 177.4(9) . . . . ?
C9 C8 C15 C16 -178.4(10) . . . . ?
N1 C8 C15 C16 0.2(15) . . . . ?
C13 C14 C15 C8 4.8(16) . . . . ?
C13 C14 C15 C16 -177.9(10) . . . . ?
C8 C15 C16 O3 176.4(13) . . . . ?
C14 C15 C16 O3 -1(2) . . . . ?
C8 C15 C16 O4 -2.2(16) . . . . ?
C14 C15 C16 O4 -179.6(9) . . . . ?
O4 C7 N1 C8 -3.9(17) . . . . ?
C6 C7 N1 C8 -178.6(9) . . . . ?
C15 C8 N1 C7 2.7(14) . . . . ?
C9 C8 N1 C7 -178.6(9) . . . . ?
C9 C10 O1 C11 -1.7(15) . . . . ?
C13 C10 O1 C11 -178.8(9) . . . . ?
C14 C13 O2 C12 0.5(14) . . . . ?
C10 C13 O2 C12 -176.4(8) . . . . ?
N1 C7 O4 C16 1.8(18) . . . . ?
C6 C7 O4 C16 176.9(10) . . . . ?
O3 C16 O4 C7 -177.3(12) . . . . ?
C15 C16 O4 C7 1.5(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.135
