# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_70627b
_database_code_depnum_ccdc_archive 'CCDC 1854485'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.914(5)
_cell_length_b                   21.762(10)
_cell_length_c                   5.713(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.119(9)
_cell_angle_gamma                90
_cell_volume                     1356.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    1334
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      27.21

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3878
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_point_group_measured_fraction_full 0.761
_reflns_number_total             2306
_reflns_number_gt                1912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_max     0.483
_reflns_Friedel_fraction_full    0.525

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2306
_refine_ls_number_parameters     191
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0798(3) 0.32829(15) 0.1629(6) 0.0212(7) Uani 1 1 d . . . . .
O1 O -0.2419(3) 0.43729(14) -0.0522(6) 0.0332(8) Uani 1 1 d . . . . .
O2 O -0.3133(3) 0.40646(18) -0.4051(6) 0.0418(9) Uani 1 1 d . . . . .
O3 O 0.2817(3) 0.30560(13) 0.1621(5) 0.0241(7) Uani 1 1 d . . . . .
C1 C -0.2273(5) 0.4190(2) -0.2763(7) 0.0295(10) Uani 1 1 d . . . . .
C2 C -0.0990(5) 0.4155(2) -0.3445(9) 0.0310(10) Uani 1 1 d . . . . .
H2 H -0.0818 0.4143 -0.5068 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0059(4) 0.41387(18) -0.1940(8) 0.0256(9) Uani 1 1 d . . . . .
H3 H -0.0230 0.4156 -0.0317 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1244(4) 0.40956(18) -0.2638(8) 0.0247(9) Uani 1 1 d . . . . .
C5 C 0.1620(4) 0.4426(2) -0.4632(8) 0.0270(10) Uani 1 1 d . . . . .
H5 H 0.1030 0.4658 -0.5499 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2816(5) 0.44220(19) -0.5354(8) 0.0322(11) Uani 1 1 d . . . . .
H6 H 0.3044 0.4647 -0.6702 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3677(4) 0.4090(2) -0.4112(8) 0.0308(10) Uani 1 1 d . . . . .
H7 H 0.4505 0.4090 -0.4599 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3352(4) 0.37537(19) -0.2145(8) 0.0267(10) Uani 1 1 d . . . . .
H8 H 0.3956 0.3523 -0.1308 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2123(4) 0.37540(17) -0.1389(7) 0.0201(8) Uani 1 1 d . . . . .
C10 C 0.1836(4) 0.33735(17) 0.0632(6) 0.0200(8) Uani 1 1 d . . . . .
C11 C 0.1071(4) 0.28732(17) 0.3471(7) 0.0211(8) Uani 1 1 d . . . . .
C12 C 0.0338(4) 0.26202(19) 0.5189(8) 0.0274(10) Uani 1 1 d . . . . .
H12 H -0.0512 0.2711 0.5253 0.033 Uiso 1 1 calc R U . . .
C13 C 0.0895(4) 0.2233(2) 0.6792(8) 0.0281(10) Uani 1 1 d . . . . .
H13 H 0.0416 0.2057 0.7991 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2131(4) 0.2094(2) 0.6710(8) 0.0274(10) Uani 1 1 d . . . . .
H14 H 0.2467 0.1817 0.7835 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2911(4) 0.2347(2) 0.5019(8) 0.0286(10) Uani 1 1 d . . . . .
H15 H 0.3764 0.2264 0.4960 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2292(4) 0.27348(18) 0.3437(7) 0.0228(9) Uani 1 1 d . . . . .
C17 C -0.3651(5) 0.4388(2) 0.0284(9) 0.0351(11) Uani 1 1 d . . . . .
H17A H -0.4075 0.4746 -0.0380 0.053 Uiso 1 1 calc R U . . .
H17B H -0.3644 0.4414 0.1996 0.053 Uiso 1 1 calc R U . . .
H17C H -0.4078 0.4012 -0.0213 0.053 Uiso 1 1 calc R U . . .


_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
N1 C10 1.293(5) . ?
N1 C11 1.407(6) . ?
O1 C1 1.353(5) . ?
O1 C17 1.430(6) . ?
O2 C1 1.212(6) . ?
O3 C16 1.385(5) . ?
O3 C10 1.386(5) . ?
C1 C2 1.463(7) . ?
C2 C3 1.319(6) . ?
C3 C4 1.487(6) . ?
C4 C9 1.398(6) . ?
C4 C5 1.415(7) . ?
C5 C6 1.377(7) . ?
C6 C7 1.372(7) . ?
C7 C8 1.393(6) . ?
C8 C9 1.418(5) . ?
C9 C10 1.460(6) . ?
C11 C16 1.367(6) . ?
C11 C12 1.391(6) . ?
C12 C13 1.376(7) . ?
C13 C14 1.385(7) . ?
C14 C15 1.412(7) . ?
C15 C16 1.400(6) . ?

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 N1 C11 104.6(3) . . ?
C1 O1 C17 116.1(4) . . ?
C16 O3 C10 103.2(3) . . ?
O2 C1 O1 122.5(5) . . ?
O2 C1 C2 124.1(4) . . ?
O1 C1 C2 113.5(4) . . ?
C3 C2 C1 123.9(4) . . ?
C2 C3 C4 123.7(4) . . ?
C9 C4 C5 118.3(4) . . ?
C9 C4 C3 123.1(4) . . ?
C5 C4 C3 118.6(4) . . ?
C6 C5 C4 122.0(4) . . ?
C7 C6 C5 119.5(4) . . ?
C6 C7 C8 120.8(4) . . ?
C7 C8 C9 120.2(4) . . ?
C4 C9 C8 119.3(4) . . ?
C4 C9 C10 123.3(4) . . ?
C8 C9 C10 117.3(3) . . ?
N1 C10 O3 114.9(3) . . ?
N1 C10 C9 129.6(3) . . ?
O3 C10 C9 115.4(3) . . ?
C16 C11 C12 119.8(4) . . ?
C16 C11 N1 108.7(3) . . ?
C12 C11 N1 131.5(4) . . ?
C13 C12 C11 117.4(4) . . ?
C12 C13 C14 121.9(4) . . ?
C13 C14 C15 122.6(4) . . ?
C16 C15 C14 112.8(4) . . ?
C11 C16 O3 108.5(3) . . ?
C11 C16 C15 125.6(4) . . ?
O3 C16 C15 125.9(4) . . ?

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
C17 O1 C1 O2 2.5(6) . . . . ?
C17 O1 C1 C2 -177.1(4) . . . . ?
O2 C1 C2 C3 -162.3(5) . . . . ?
O1 C1 C2 C3 17.3(6) . . . . ?
C1 C2 C3 C4 179.2(4) . . . . ?
C2 C3 C4 C9 -142.9(4) . . . . ?
C2 C3 C4 C5 38.5(6) . . . . ?
C9 C4 C5 C6 -0.4(6) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C5 C4 C9 C8 0.5(6) . . . . ?
C3 C4 C9 C8 -178.2(4) . . . . ?
C5 C4 C9 C10 -177.2(4) . . . . ?
C3 C4 C9 C10 4.1(6) . . . . ?
C7 C8 C9 C4 0.0(6) . . . . ?
C7 C8 C9 C10 177.8(4) . . . . ?
C11 N1 C10 O3 0.4(4) . . . . ?
C11 N1 C10 C9 179.6(4) . . . . ?
C16 O3 C10 N1 0.1(4) . . . . ?
C16 O3 C10 C9 -179.2(3) . . . . ?
C4 C9 C10 N1 -0.6(6) . . . . ?
C8 C9 C10 N1 -178.4(4) . . . . ?
C4 C9 C10 O3 178.6(3) . . . . ?
C8 C9 C10 O3 0.8(5) . . . . ?
C10 N1 C11 C16 -0.8(4) . . . . ?
C10 N1 C11 C12 178.1(4) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
N1 C11 C12 C13 -179.1(4) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 1.4(7) . . . . ?
C13 C14 C15 C16 -1.5(6) . . . . ?
C12 C11 C16 O3 -178.2(4) . . . . ?
N1 C11 C16 O3 0.9(4) . . . . ?
C12 C11 C16 C15 0.1(6) . . . . ?
N1 C11 C16 C15 179.2(4) . . . . ?
C10 O3 C16 C11 -0.6(4) . . . . ?
C10 O3 C16 C15 -178.9(4) . . . . ?
C14 C15 C16 C11 0.8(6) . . . . ?
C14 C15 C16 O3 178.8(4) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_171107b_0m
_database_code_depnum_ccdc_archive 'CCDC 1854502'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Cl N O3'
_chemical_formula_weight         313.73

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.986(7)
_cell_length_b                   11.502(8)
_cell_length_c                   13.713(9)
_cell_angle_alpha                111.941(8)
_cell_angle_beta                 101.876(7)
_cell_angle_gamma                104.589(8)
_cell_volume                     1466.1(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1839
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      22.70

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ??
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7498
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.05
_reflns_number_total             5065
_reflns_number_gt                3076
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_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)+(0.1835P)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         5065
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2791
_refine_ls_wR_factor_gt          0.2322
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.03802(13) 0.67137(13) 0.91600(14) 0.0935(5) Uani 1 1 d . . .
Cl2 Cl 1.18102(13) 0.54973(14) 0.42792(14) 0.0945(5) Uani 1 1 d . . .
C1 C 0.1377(4) 0.3536(4) 0.8800(3) 0.0548(9) Uani 1 1 d . . .
C2 C 0.0622(4) 0.4331(4) 0.8830(4) 0.0657(11) Uani 1 1 d . . .
H2 H -0.0300 0.3977 0.8642 0.079 Uiso 1 1 calc R . .
C3 C 0.1286(4) 0.5671(4) 0.9150(3) 0.0600(10) Uani 1 1 d . . .
C4 C 0.2659(4) 0.6222(5) 0.9442(4) 0.0721(12) Uani 1 1 d . . .
H4 H 0.3067 0.7132 0.9652 0.087 Uiso 1 1 calc R . .
C5 C 0.3426(4) 0.5446(5) 0.9427(4) 0.0741(13) Uani 1 1 d . . .
H5 H 0.4350 0.5805 0.9630 0.089 Uiso 1 1 calc R . .
C6 C 0.2747(4) 0.4100(4) 0.9093(3) 0.0551(9) Uani 1 1 d . . .
C7 C 0.2123(4) 0.1954(4) 0.8559(3) 0.0556(10) Uani 1 1 d . . .
C8 C 0.2368(4) 0.0694(4) 0.8271(3) 0.0574(10) Uani 1 1 d . . .
C9 C 0.3657(5) 0.0746(5) 0.8660(4) 0.0722(12) Uani 1 1 d . . .
H9 H 0.4338 0.1582 0.9092 0.087 Uiso 1 1 calc R . .
C10 C 0.3968(5) -0.0381(6) 0.8434(5) 0.0799(14) Uani 1 1 d . . .
H10 H 0.4842 -0.0311 0.8719 0.096 Uiso 1 1 calc R . .
C11 C 0.2965(5) -0.1629(6) 0.7772(5) 0.0807(14) Uani 1 1 d . . .
H11 H 0.3159 -0.2409 0.7608 0.097 Uiso 1 1 calc R . .
C12 C 0.1677(5) -0.1707(5) 0.7360(4) 0.0720(12) Uani 1 1 d . . .
H12 H 0.1013 -0.2549 0.6906 0.086 Uiso 1 1 calc R . .
C13 C 0.1338(4) -0.0578(4) 0.7597(3) 0.0591(10) Uani 1 1 d . . .
C14 C -0.0056(4) -0.0735(4) 0.7138(3) 0.0620(10) Uani 1 1 d . . .
H14 H -0.0204 0.0002 0.7081 0.074 Uiso 1 1 calc R . .
C15 C -0.1108(5) -0.1802(5) 0.6802(4) 0.0688(12) Uani 1 1 d . . .
H15 H -0.0995 -0.2561 0.6840 0.083 Uiso 1 1 calc R . .
C16 C -0.2460(4) -0.1846(4) 0.6366(4) 0.0634(11) Uani 1 1 d . . .
C17 C -0.4750(5) -0.3131(6) 0.5763(5) 0.0920(16) Uani 1 1 d . . .
H17A H -0.4880 -0.2352 0.6246 0.138 Uiso 1 1 calc R . .
H17B H -0.5323 -0.3920 0.5754 0.138 Uiso 1 1 calc R . .
H17C H -0.4961 -0.3207 0.5021 0.138 Uiso 1 1 calc R . .
C18 C 0.8588(4) 0.6460(4) 0.3822(3) 0.0593(10) Uani 1 1 d . . .
C19 C 0.9389(4) 0.5732(4) 0.3910(4) 0.0684(12) Uani 1 1 d . . .
H19 H 0.9037 0.4847 0.3793 0.082 Uiso 1 1 calc R . .
C20 C 1.0753(4) 0.6382(4) 0.4182(4) 0.0648(11) Uani 1 1 d . . .
C21 C 1.1301(4) 0.7695(5) 0.4368(4) 0.0683(11) Uani 1 1 d . . .
H21 H 1.2219 0.8089 0.4555 0.082 Uiso 1 1 calc R . .
C22 C 1.0507(4) 0.8431(5) 0.4280(4) 0.0708(12) Uani 1 1 d . . .
H22 H 1.0862 0.9316 0.4398 0.085 Uiso 1 1 calc R . .
C23 C 0.9172(4) 0.7788(4) 0.4010(3) 0.0591(10) Uani 1 1 d . . .
C24 C 0.7000(4) 0.7161(4) 0.3541(3) 0.0597(10) Uani 1 1 d . . .
C25 C 0.5742(4) 0.7389(5) 0.3262(4) 0.0627(11) Uani 1 1 d . . .
C26 C 0.5792(5) 0.8706(5) 0.3629(4) 0.0771(13) Uani 1 1 d . . .
H26 H 0.6613 0.9403 0.4047 0.093 Uiso 1 1 calc R . .
C27 C 0.4680(6) 0.9015(5) 0.3401(5) 0.0846(15) Uani 1 1 d . . .
H27 H 0.4742 0.9907 0.3675 0.102 Uiso 1 1 calc R . .
C28 C 0.3458(5) 0.7982(6) 0.2754(5) 0.0834(15) Uani 1 1 d . . .
H28 H 0.2690 0.8170 0.2574 0.100 Uiso 1 1 calc R . .
C29 C 0.3398(5) 0.6674(5) 0.2384(4) 0.0767(13) Uani 1 1 d . . .
H29 H 0.2573 0.5987 0.1951 0.092 Uiso 1 1 calc R . .
C30 C 0.4506(4) 0.6325(5) 0.2623(4) 0.0632(11) Uani 1 1 d . . .
C31 C 0.4355(4) 0.4915(5) 0.2207(4) 0.0648(11) Uani 1 1 d . . .
H31 H 0.5141 0.4739 0.2262 0.078 Uiso 1 1 calc R . .
C32 C 0.3251(4) 0.3864(5) 0.1764(4) 0.0683(12) Uani 1 1 d . . .
H32 H 0.2440 0.3992 0.1678 0.082 Uiso 1 1 calc R . .
C33 C 0.3251(4) 0.2501(5) 0.1400(4) 0.0653(11) Uani 1 1 d . . .
C34 C 0.1867(6) 0.0215(5) 0.0671(5) 0.0932(16) Uani 1 1 d . . .
H34A H 0.2181 -0.0080 0.0051 0.140 Uiso 1 1 calc R . .
H34B H 0.0946 -0.0331 0.0453 0.140 Uiso 1 1 calc R . .
H34C H 0.2386 0.0132 0.1279 0.140 Uiso 1 1 calc R . .
N1 N 0.1024(3) 0.2174(3) 0.8479(3) 0.0613(9) Uani 1 1 d . . .
N2 N 0.7218(3) 0.6121(4) 0.3544(3) 0.0641(9) Uani 1 1 d . . .
O1 O 0.3244(3) 0.3097(3) 0.8949(2) 0.0640(8) Uani 1 1 d . . .
O2 O -0.2732(3) -0.0975(4) 0.6213(3) 0.0956(12) Uani 1 1 d . . .
O3 O -0.3390(3) -0.3001(3) 0.6160(3) 0.0791(9) Uani 1 1 d . . .
O4 O 0.8151(3) 0.8239(3) 0.3817(2) 0.0679(8) Uani 1 1 d . . .
O5 O 0.4205(3) 0.2193(4) 0.1416(3) 0.0916(11) Uani 1 1 d . . .
O6 O 0.1996(3) 0.1594(3) 0.1013(3) 0.0796(9) 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
Cl1 C3 1.738(4) . ?
Cl2 C20 1.742(5) . ?
C1 C2 1.376(6) . ?
C1 N1 1.381(5) . ?
C1 C6 1.383(5) . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(6) . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 O1 1.364(5) . ?
C7 N1 1.287(5) . ?
C7 O1 1.385(5) . ?
C7 C8 1.463(6) . ?
C8 C9 1.384(6) . ?
C8 C13 1.415(6) . ?
C9 C10 1.363(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.467(6) . ?
C14 C15 1.303(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.463(6) . ?
C15 H15 0.9300 . ?
C16 O2 1.191(5) . ?
C16 O3 1.344(5) . ?
C17 O3 1.429(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.376(6) . ?
C18 N2 1.386(5) . ?
C18 C23 1.399(6) . ?
C19 C20 1.393(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(6) . ?
C21 C22 1.377(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(6) . ?
C22 H22 0.9300 . ?
C23 O4 1.367(5) . ?
C24 N2 1.279(5) . ?
C24 O4 1.394(5) . ?
C24 C25 1.472(6) . ?
C25 C26 1.388(7) . ?
C25 C30 1.408(6) . ?
C26 C27 1.364(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.386(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.389(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.455(6) . ?
C31 C32 1.308(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.458(6) . ?
C32 H32 0.9300 . ?
C33 O5 1.186(5) . ?
C33 O6 1.353(5) . ?
C34 O6 1.435(6) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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 N1 131.7(4) . . ?
C2 C1 C6 119.6(4) . . ?
N1 C1 C6 108.6(3) . . ?
C1 C2 C3 117.4(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 122.3(4) . . ?
C2 C3 Cl1 119.5(3) . . ?
C4 C3 Cl1 118.2(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 116.2(4) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
O1 C6 C5 128.6(4) . . ?
O1 C6 C1 107.9(3) . . ?
C5 C6 C1 123.5(4) . . ?
N1 C7 O1 114.1(4) . . ?
N1 C7 C8 130.4(4) . . ?
O1 C7 C8 115.4(3) . . ?
C9 C8 C13 118.6(4) . . ?
C9 C8 C7 119.0(4) . . ?
C13 C8 C7 122.4(4) . . ?
C10 C9 C8 122.6(5) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 122.3(5) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C8 117.9(4) . . ?
C12 C13 C14 119.5(4) . . ?
C8 C13 C14 122.7(4) . . ?
C15 C14 C13 126.6(4) . . ?
C15 C14 H14 116.7 . . ?
C13 C14 H14 116.7 . . ?
C14 C15 C16 122.1(4) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
O2 C16 O3 122.8(4) . . ?
O2 C16 C15 125.4(4) . . ?
O3 C16 C15 111.8(4) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N2 131.8(4) . . ?
C19 C18 C23 119.2(4) . . ?
N2 C18 C23 109.0(4) . . ?
C18 C19 C20 116.9(4) . . ?
C18 C19 H19 121.6 . . ?
C20 C19 H19 121.6 . . ?
C21 C20 C19 122.7(4) . . ?
C21 C20 Cl2 118.5(3) . . ?
C19 C20 Cl2 118.8(3) . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 116.2(4) . . ?
C23 C22 H22 121.9 . . ?
C21 C22 H22 121.9 . . ?
C22 C23 O4 129.1(4) . . ?
C22 C23 C18 124.2(4) . . ?
O4 C23 C18 106.7(3) . . ?
N2 C24 O4 114.0(4) . . ?
N2 C24 C25 130.8(4) . . ?
O4 C24 C25 115.1(4) . . ?
C26 C25 C30 119.3(4) . . ?
C26 C25 C24 118.3(4) . . ?
C30 C25 C24 122.4(4) . . ?
C27 C26 C25 122.5(5) . . ?
C27 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C26 C27 C28 119.1(5) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C29 C28 C27 118.9(5) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 123.4(5) . . ?
C28 C29 H29 118.3 . . ?
C30 C29 H29 118.3 . . ?
C29 C30 C25 116.8(4) . . ?
C29 C30 C31 120.0(4) . . ?
C25 C30 C31 123.2(4) . . ?
C32 C31 C30 128.0(4) . . ?
C32 C31 H31 116.0 . . ?
C30 C31 H31 116.0 . . ?
C31 C32 C33 122.1(4) . . ?
C31 C32 H32 118.9 . . ?
C33 C32 H32 118.9 . . ?
O5 C33 O6 123.1(4) . . ?
O5 C33 C32 125.8(4) . . ?
O6 C33 C32 111.1(4) . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C7 N1 C1 105.4(3) . . ?
C24 N2 C18 105.5(4) . . ?
C6 O1 C7 104.0(3) . . ?
C16 O3 C17 116.4(4) . . ?
C23 O4 C24 104.7(3) . . ?
C33 O6 C34 116.5(4) . . ?

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
N1 C1 C2 C3 -177.0(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C1 C2 C3 Cl1 177.9(3) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
Cl1 C3 C4 C5 -178.5(4) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 O1 176.5(4) . . . . ?
C4 C5 C6 C1 -0.9(7) . . . . ?
C2 C1 C6 O1 -177.6(3) . . . . ?
N1 C1 C6 O1 0.3(4) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
N1 C1 C6 C5 178.3(4) . . . . ?
N1 C7 C8 C9 -165.9(4) . . . . ?
O1 C7 C8 C9 16.3(5) . . . . ?
N1 C7 C8 C13 15.0(7) . . . . ?
O1 C7 C8 C13 -162.8(4) . . . . ?
C13 C8 C9 C10 -1.2(7) . . . . ?
C7 C8 C9 C10 179.7(4) . . . . ?
C8 C9 C10 C11 1.2(8) . . . . ?
C9 C10 C11 C12 -0.1(8) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
C11 C12 C13 C8 1.2(7) . . . . ?
C11 C12 C13 C14 -179.4(4) . . . . ?
C9 C8 C13 C12 -0.1(6) . . . . ?
C7 C8 C13 C12 179.0(4) . . . . ?
C9 C8 C13 C14 -179.5(4) . . . . ?
C7 C8 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 22.2(7) . . . . ?
C8 C13 C14 C15 -158.4(4) . . . . ?
C13 C14 C15 C16 179.4(4) . . . . ?
C14 C15 C16 O2 4.7(8) . . . . ?
C14 C15 C16 O3 -174.7(4) . . . . ?
N2 C18 C19 C20 178.2(4) . . . . ?
C23 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 0.5(7) . . . . ?
C18 C19 C20 Cl2 -178.8(3) . . . . ?
C19 C20 C21 C22 -0.6(7) . . . . ?
Cl2 C20 C21 C22 178.7(3) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C21 C22 C23 O4 -176.7(4) . . . . ?
C21 C22 C23 C18 -0.1(6) . . . . ?
C19 C18 C23 C22 0.0(6) . . . . ?
N2 C18 C23 C22 -178.7(4) . . . . ?
C19 C18 C23 O4 177.2(4) . . . . ?
N2 C18 C23 O4 -1.5(5) . . . . ?
N2 C24 C25 C26 161.7(4) . . . . ?
O4 C24 C25 C26 -20.6(5) . . . . ?
N2 C24 C25 C30 -19.4(7) . . . . ?
O4 C24 C25 C30 158.3(4) . . . . ?
C30 C25 C26 C27 0.3(7) . . . . ?
C24 C25 C26 C27 179.3(4) . . . . ?
C25 C26 C27 C28 -1.7(8) . . . . ?
C26 C27 C28 C29 1.5(8) . . . . ?
C27 C28 C29 C30 0.0(8) . . . . ?
C28 C29 C30 C25 -1.2(7) . . . . ?
C28 C29 C30 C31 179.5(5) . . . . ?
C26 C25 C30 C29 1.1(6) . . . . ?
C24 C25 C30 C29 -177.8(4) . . . . ?
C26 C25 C30 C31 -179.7(4) . . . . ?
C24 C25 C30 C31 1.4(6) . . . . ?
C29 C30 C31 C32 -12.4(7) . . . . ?
C25 C30 C31 C32 168.4(4) . . . . ?
C30 C31 C32 C33 -178.8(4) . . . . ?
C31 C32 C33 O5 -3.4(8) . . . . ?
C31 C32 C33 O6 177.5(4) . . . . ?
O1 C7 N1 C1 1.6(4) . . . . ?
C8 C7 N1 C1 -176.2(4) . . . . ?
C2 C1 N1 C7 176.4(4) . . . . ?
C6 C1 N1 C7 -1.2(4) . . . . ?
O4 C24 N2 C18 -0.7(5) . . . . ?
C25 C24 N2 C18 177.1(4) . . . . ?
C19 C18 N2 C24 -177.1(4) . . . . ?
C23 C18 N2 C24 1.4(5) . . . . ?
C5 C6 O1 C7 -177.2(4) . . . . ?
C1 C6 O1 C7 0.6(4) . . . . ?
N1 C7 O1 C6 -1.4(4) . . . . ?
C8 C7 O1 C6 176.7(3) . . . . ?
O2 C16 O3 C17 -1.3(7) . . . . ?
C15 C16 O3 C17 178.2(4) . . . . ?
C22 C23 O4 C24 178.1(4) . . . . ?
C18 C23 O4 C24 1.1(4) . . . . ?
N2 C24 O4 C23 -0.2(4) . . . . ?
C25 C24 O4 C23 -178.4(3) . . . . ?
O5 C33 O6 C34 3.3(7) . . . . ?
C32 C33 O6 C34 -177.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.140
