# 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_ic17175
_database_code_depnum_ccdc_archive 'CCDC 1420364'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Br N O5'
_chemical_formula_weight         332.15
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   5.8370(4)
_cell_length_b                   9.2077(6)
_cell_length_c                   25.6068(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1376.25(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3523
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      21.90

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    3.002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3152
_exptl_absorpt_correction_T_max  0.8174
_exptl_absorpt_process_details   'SADABS (BRUKER, 2001)'

_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 SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12428
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3154
_reflns_number_gt                2789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(12)
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.46849(5) 0.24991(4) 0.239968(13) 0.04089(12) Uani 1 1 d . . .
O1 O 0.8821(6) 0.3253(3) 0.04778(15) 0.0664(9) Uani 1 1 d . . .
O2 O 1.2243(6) 0.2801(3) 0.07152(14) 0.0708(10) Uani 1 1 d . . .
O3 O 0.4016(4) -0.1692(3) 0.07016(11) 0.0441(6) Uani 1 1 d . . .
O4 O 0.6545(5) -0.3452(3) 0.08524(10) 0.0414(6) Uani 1 1 d . . .
O5 O 0.8522(5) 0.0773(3) 0.28481(9) 0.0400(6) Uani 1 1 d . . .
N1 N 1.0420(5) 0.2436(3) 0.05359(11) 0.0406(7) Uani 1 1 d . . .
C1 C 0.6795(5) 0.1295(3) 0.20409(12) 0.0273(7) Uani 1 1 d . . .
C2 C 0.6644(5) 0.1168(3) 0.15071(12) 0.0273(7) Uani 1 1 d . . .
H2 H 0.5474 0.1673 0.1324 0.033 Uiso 1 1 calc R . .
C3 C 0.8184(5) 0.0309(3) 0.12320(12) 0.0281(7) Uani 1 1 d . . .
C4 C 0.9847(6) -0.0425(4) 0.15134(13) 0.0339(7) Uani 1 1 d . . .
H4 H 1.0912 -0.1021 0.1332 0.041 Uiso 1 1 calc R . .
C5 C 0.9999(7) -0.0314(4) 0.20523(14) 0.0365(8) Uani 1 1 d . . .
H5 H 1.1148 -0.0835 0.2236 0.044 Uiso 1 1 calc R . .
C6 C 0.8469(6) 0.0561(3) 0.23210(12) 0.0296(7) Uani 1 1 d . . .
C7 C 0.8050(5) 0.0199(3) 0.06426(12) 0.0275(7) Uani 1 1 d . . .
H7 H 0.6650 0.0727 0.0522 0.033 Uiso 1 1 calc R . .
C8 C 1.0137(6) 0.0884(3) 0.03827(13) 0.0319(7) Uani 1 1 d . . .
H8A H 1.1527 0.0335 0.0483 0.038 Uiso 1 1 calc R . .
H8B H 0.9971 0.0819 -0.0001 0.038 Uiso 1 1 calc R . .
C9 C 0.7921(6) -0.1368(3) 0.04476(13) 0.0327(7) Uani 1 1 d . . .
H9A H 0.7774 -0.1371 0.0062 0.039 Uiso 1 1 calc R . .
H9B H 0.9354 -0.1883 0.0540 0.039 Uiso 1 1 calc R . .
C10 C 0.5935(6) -0.2144(3) 0.06817(12) 0.0292(7) Uani 1 1 d . . .
C11 C 0.4740(7) -0.4287(4) 0.10985(17) 0.0538(11) Uani 1 1 d . . .
H11A H 0.4260 -0.3803 0.1421 0.081 Uiso 1 1 calc R . .
H11B H 0.5309 -0.5262 0.1180 0.081 Uiso 1 1 calc R . .
H11C H 0.3431 -0.4361 0.0860 0.081 Uiso 1 1 calc R . .
C12 C 1.0192(7) -0.0014(5) 0.31402(14) 0.0490(10) Uani 1 1 d . . .
H12A H 0.9933 -0.1059 0.3096 0.074 Uiso 1 1 calc R . .
H12B H 1.0062 0.0240 0.3511 0.074 Uiso 1 1 calc R . .
H12C H 1.1728 0.0235 0.3014 0.074 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03824(19) 0.0435(2) 0.0409(2) -0.01119(16) 0.00435(13) 0.00959(19)
O1 0.071(2) 0.0370(15) 0.091(2) 0.0022(16) -0.025(2) 0.0087(16)
O2 0.0610(19) 0.061(2) 0.090(2) -0.0055(17) -0.0242(17) -0.0233(16)
O3 0.0294(13) 0.0468(15) 0.0562(17) -0.0035(13) 0.0064(12) -0.0025(12)
O4 0.0420(15) 0.0350(13) 0.0474(15) 0.0045(11) 0.0006(13) -0.0059(12)
O5 0.0437(15) 0.0489(15) 0.0273(13) -0.0020(11) -0.0017(11) 0.0047(12)
N1 0.0495(16) 0.0362(15) 0.0361(15) 0.0097(14) -0.0035(12) -0.009(2)
C1 0.0269(16) 0.0214(15) 0.0338(17) -0.0054(12) 0.0038(13) 0.0013(12)
C2 0.0280(16) 0.0234(15) 0.0307(17) 0.0012(12) 0.0006(13) -0.0006(13)
C3 0.0284(16) 0.0240(15) 0.0320(17) 0.0019(12) -0.0004(13) -0.0023(12)
C4 0.0325(18) 0.0351(17) 0.0341(17) -0.0046(13) 0.0048(16) 0.0089(15)
C5 0.037(2) 0.0397(18) 0.0322(17) 0.0028(14) -0.0051(17) 0.0074(16)
C6 0.0282(16) 0.0321(16) 0.0287(18) -0.0009(13) 0.0017(13) -0.0051(13)
C7 0.0248(15) 0.0304(16) 0.0275(16) -0.0004(13) 0.0001(12) 0.0001(13)
C8 0.0328(18) 0.0296(16) 0.0333(17) 0.0025(13) 0.0024(14) -0.0026(14)
C9 0.0339(18) 0.0335(17) 0.0306(17) -0.0040(14) 0.0086(15) -0.0057(15)
C10 0.0314(16) 0.0332(18) 0.0231(15) -0.0110(12) 0.0016(12) -0.0061(13)
C11 0.059(3) 0.054(2) 0.048(2) 0.0161(18) -0.002(2) -0.023(2)
C12 0.036(2) 0.081(3) 0.0299(19) 0.0019(18) -0.0066(18) 0.011(2)

_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 C1 1.895(3) . ?
O1 N1 1.209(4) . ?
O2 N1 1.206(4) . ?
O3 C10 1.196(4) . ?
O4 C10 1.330(4) . ?
O4 C11 1.449(4) . ?
O5 C6 1.364(4) . ?
O5 C12 1.427(4) . ?
N1 C8 1.491(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.385(4) . ?
C3 C7 1.515(4) . ?
C4 C5 1.387(5) . ?
C5 C6 1.386(5) . ?
C7 C8 1.525(4) . ?
C7 C9 1.529(4) . ?
C9 C10 1.488(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
C10 O4 C11 115.4(3) . . ?
C6 O5 C12 117.5(3) . . ?
O2 N1 O1 123.7(4) . . ?
O2 N1 C8 117.7(3) . . ?
O1 N1 C8 118.6(3) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 Br1 119.4(2) . . ?
C6 C1 Br1 119.5(2) . . ?
C1 C2 C3 120.8(3) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 C7 121.4(3) . . ?
C2 C3 C7 120.7(3) . . ?
C3 C4 C5 121.8(3) . . ?
C6 C5 C4 119.7(3) . . ?
O5 C6 C5 124.1(3) . . ?
O5 C6 C1 117.2(3) . . ?
C5 C6 C1 118.7(3) . . ?
C3 C7 C8 111.5(3) . . ?
C3 C7 C9 113.0(3) . . ?
C8 C7 C9 106.7(3) . . ?
N1 C8 C7 111.7(3) . . ?
C10 C9 C7 111.1(3) . . ?
O3 C10 O4 123.5(3) . . ?
O3 C10 C9 125.4(3) . . ?
O4 C10 C9 111.0(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.161
####################################################################### 
# 
# 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_ic17390
_database_code_depnum_ccdc_archive 'CCDC 1420368'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl N O'
_chemical_formula_weight         249.73
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   7.6652(6)
_cell_length_b                   7.8614(6)
_cell_length_c                   20.6346(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1243.42(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1514
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      18.08

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8686
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   'SADABS (BRUKER, 2001)'

_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 SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11248
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2854
_reflns_number_gt                2410
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0461P)²+0.4119P] 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(11)
_refine_ls_number_reflns         2854
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.56506(10) 0.77939(9) -0.00482(4) 0.0370(2) Uani 1 1 d . . .
O1 O 0.3438(4) 0.8186(4) 0.21917(13) 0.0582(8) Uani 1 1 d . . .
N1 N 0.6240(3) 0.7850(4) 0.18307(12) 0.0351(6) Uani 1 1 d . . .
C1 C 0.4510(4) 0.7561(4) 0.18231(15) 0.0379(8) Uani 1 1 d . . .
C2 C 0.4136(4) 0.6298(4) 0.12867(15) 0.0312(7) Uani 1 1 d . . .
H2A H 0.3726 0.6882 0.0890 0.037 Uiso 1 1 calc R . .
H2B H 0.3247 0.5458 0.1423 0.037 Uiso 1 1 calc R . .
C3 C 0.5922(3) 0.5434(4) 0.11734(14) 0.0259(6) Uani 1 1 d . . .
H3 H 0.5993 0.4471 0.1489 0.031 Uiso 1 1 calc R . .
C4 C 0.7252(4) 0.6771(4) 0.14021(14) 0.0264(7) Uani 1 1 d . . .
H4 H 0.7708 0.7440 0.1026 0.032 Uiso 1 1 calc R . .
C5 C 0.8743(4) 0.6194(5) 0.18381(17) 0.0397(8) Uani 1 1 d . . .
H5A H 0.8422 0.5159 0.2084 0.048 Uiso 1 1 calc R . .
H5B H 0.9810 0.5962 0.1583 0.048 Uiso 1 1 calc R . .
C6 C 0.9003(5) 0.7687(6) 0.22852(19) 0.0644(12) Uani 1 1 d . . .
H6A H 0.9832 0.8510 0.2093 0.077 Uiso 1 1 calc R . .
H6B H 0.9473 0.7302 0.2707 0.077 Uiso 1 1 calc R . .
C7 C 0.7239(5) 0.8501(5) 0.23754(17) 0.0493(10) Uani 1 1 d . . .
H7A H 0.6708 0.8159 0.2793 0.059 Uiso 1 1 calc R . .
H7B H 0.7323 0.9757 0.2360 0.059 Uiso 1 1 calc R . .
C8 C 0.6272(4) 0.4679(4) 0.05117(15) 0.0264(6) Uani 1 1 d . . .
C9 C 0.6169(4) 0.5632(4) -0.00585(16) 0.0298(6) Uani 1 1 d . . .
C10 C 0.6487(5) 0.4950(5) -0.06638(16) 0.0415(9) Uani 1 1 d . . .
H10 H 0.6401 0.5636 -0.1041 0.050 Uiso 1 1 calc R . .
C11 C 0.6934(5) 0.3247(6) -0.07114(18) 0.0507(10) Uani 1 1 d . . .
H11 H 0.7150 0.2748 -0.1123 0.061 Uiso 1 1 calc R . .
C12 C 0.7061(4) 0.2285(5) -0.01559(18) 0.0470(9) Uani 1 1 d . . .
H12 H 0.7373 0.1119 -0.0191 0.056 Uiso 1 1 calc R . .
C13 C 0.6750(4) 0.2964(5) 0.04530(16) 0.0352(7) Uani 1 1 d . . .
C14 C 0.6906(5) 0.1797(5) 0.10384(18) 0.0472(9) Uani 1 1 d . . .
H14A H 0.7317 0.0676 0.0898 0.071 Uiso 1 1 calc R . .
H14B H 0.5763 0.1682 0.1247 0.071 Uiso 1 1 calc R . .
H14C H 0.7739 0.2283 0.1348 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0421(4) 0.0339(4) 0.0349(4) 0.0084(3) -0.0010(3) 0.0011(4)
O1 0.0564(18) 0.0626(19) 0.0557(16) -0.0126(15) 0.0185(14) 0.0191(15)
N1 0.0411(15) 0.0353(14) 0.0290(13) -0.0068(12) 0.0015(11) 0.0015(13)
C1 0.0420(19) 0.035(2) 0.0364(17) 0.0027(14) 0.0025(15) 0.0096(16)
C2 0.0251(16) 0.0372(17) 0.0314(15) 0.0010(13) 0.0032(13) 0.0019(14)
C3 0.0222(15) 0.0260(14) 0.0295(15) 0.0042(12) 0.0032(12) 0.0015(13)
C4 0.0293(16) 0.0263(17) 0.0234(15) 0.0004(12) 0.0010(12) -0.0022(13)
C5 0.0330(18) 0.048(2) 0.0377(19) 0.0018(16) -0.0077(14) -0.0030(16)
C6 0.053(3) 0.091(3) 0.049(2) -0.019(2) -0.0145(18) -0.008(3)
C7 0.064(3) 0.050(2) 0.0342(19) -0.0120(17) 0.0027(17) -0.013(2)
C8 0.0187(14) 0.0283(16) 0.0321(16) -0.0039(13) 0.0012(12) -0.0045(13)
C9 0.0271(14) 0.0296(14) 0.0327(16) -0.0058(14) -0.0024(13) -0.0054(12)
C10 0.040(2) 0.055(2) 0.0292(17) -0.0047(16) 0.0004(15) -0.0157(18)
C11 0.055(2) 0.057(3) 0.040(2) -0.021(2) 0.0100(18) -0.012(2)
C12 0.047(2) 0.0345(18) 0.059(2) -0.0165(18) 0.0093(17) 0.0003(17)
C13 0.0287(16) 0.0299(17) 0.0469(19) -0.0064(16) 0.0034(14) 0.0003(15)
C14 0.054(2) 0.0240(19) 0.063(2) 0.0034(17) 0.0006(19) 0.0098(16)

_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 C9 1.745(3) . ?
O1 C1 1.222(4) . ?
N1 C1 1.346(4) . ?
N1 C4 1.450(4) . ?
N1 C7 1.453(4) . ?
C1 C2 1.514(4) . ?
C2 C3 1.546(4) . ?
C3 C8 1.513(4) . ?
C3 C4 1.539(4) . ?
C4 C5 1.524(4) . ?
C5 C6 1.506(5) . ?
C6 C7 1.507(6) . ?
C8 C9 1.397(4) . ?
C8 C13 1.402(5) . ?
C9 C10 1.381(5) . ?
C10 C11 1.385(6) . ?
C11 C12 1.377(5) . ?
C12 C13 1.386(5) . ?
C13 C14 1.522(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
C1 N1 C4 114.9(3) . . ?
C1 N1 C7 126.0(3) . . ?
C4 N1 C7 113.3(3) . . ?
O1 C1 N1 126.0(3) . . ?
O1 C1 C2 126.3(3) . . ?
N1 C1 C2 107.8(3) . . ?
C1 C2 C3 103.4(2) . . ?
C8 C3 C4 115.3(2) . . ?
C8 C3 C2 117.7(2) . . ?
C4 C3 C2 103.9(2) . . ?
N1 C4 C5 102.4(2) . . ?
N1 C4 C3 103.4(2) . . ?
C5 C4 C3 118.3(3) . . ?
C6 C5 C4 103.2(3) . . ?
C5 C6 C7 106.7(3) . . ?
N1 C7 C6 103.1(3) . . ?
C9 C8 C13 117.2(3) . . ?
C9 C8 C3 122.7(3) . . ?
C13 C8 C3 120.1(3) . . ?
C10 C9 C8 122.9(3) . . ?
C10 C9 Cl1 115.4(3) . . ?
C8 C9 Cl1 121.7(2) . . ?
C9 C10 C11 118.9(3) . . ?
C12 C11 C10 119.3(3) . . ?
C11 C12 C13 122.1(3) . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 C14 118.3(3) . . ?
C8 C13 C14 122.1(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053
