# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ja
_audit_block_doi                 10.5517/ccdc.csd.cc20bmjj
_database_code_depnum_ccdc_archive 'CCDC 1857257'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.53 H2.27 N0.13 O0.13'
_chemical_formula_weight         36.71

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   Pbca

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                   16.7527(11)
_cell_length_b                   9.2802(6)
_cell_length_c                   19.4280(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3020.4(3)
_cell_formula_units_Z            60
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3460
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      27.53

_exptl_crystal_description       bar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            44597
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3460
_reflns_number_gt                2552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0725P)²+0.6320P] 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         3460
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
N1 N 0.11960(7) 0.67978(13) 0.26288(6) 0.0472(3) Uani 1 1 d . . .
O1 O 0.05338(7) 0.78896(13) 0.17330(6) 0.0664(3) Uani 1 1 d . . .
C19 C 0.19787(8) 0.67609(15) 0.28878(7) 0.0443(3) Uani 1 1 d . . .
C18 C 0.01666(8) 0.69728(16) 0.35471(7) 0.0449(3) Uani 1 1 d . . .
C17 C 0.19805(8) 0.80835(14) 0.18814(7) 0.0446(3) Uani 1 1 d . . .
C16 C 0.11496(8) 0.76177(16) 0.20438(7) 0.0471(3) Uani 1 1 d . . .
C15 C 0.22709(10) 0.81017(16) 0.11233(8) 0.0527(4) Uani 1 1 d . . .
H15A H 0.2834 0.7845 0.1060 0.063 Uiso 1 1 calc R . .
C14 C 0.24772(9) 0.75340(14) 0.24483(7) 0.0437(3) Uani 1 1 d . . .
C13 C 0.05091(9) 0.61299(17) 0.29531(8) 0.0522(4) Uani 1 1 d . . .
H13A H 0.0662 0.5182 0.3117 0.063 Uiso 1 1 calc R . .
H13B H 0.0096 0.6000 0.2609 0.063 Uiso 1 1 calc R . .
C12 C 0.21343(11) 0.94699(16) 0.15012(8) 0.0614(4) Uani 1 1 d . . .
H12A H 0.1675 1.0044 0.1370 0.074 Uiso 1 1 calc R . .
H12B H 0.2600 1.0026 0.1634 0.074 Uiso 1 1 calc R . .
C11 C 0.01116(10) 0.84579(17) 0.35262(8) 0.0572(4) Uani 1 1 d . . .
H11A H 0.0331 0.8953 0.3155 0.069 Uiso 1 1 calc R . .
C10 C 0.32768(9) 0.76428(17) 0.25974(9) 0.0568(4) Uani 1 1 d . . .
H10A H 0.3616 0.8155 0.2308 0.068 Uiso 1 1 calc R . .
C9 C 0.22608(10) 0.6089(2) 0.34685(8) 0.0616(4) Uani 1 1 d . . .
H9A H 0.1923 0.5571 0.3757 0.074 Uiso 1 1 calc R . .
C8 C 0.35699(10) 0.6980(2) 0.31830(10) 0.0727(5) Uani 1 1 d . . .
H8A H 0.4109 0.7052 0.3290 0.087 Uiso 1 1 calc R . .
C7 C -0.01466(10) 0.6268(2) 0.41071(9) 0.0640(4) Uani 1 1 d . . .
H7A H -0.0113 0.5269 0.4134 0.077 Uiso 1 1 calc R . .
C6 C 0.17449(13) 0.76698(19) 0.05548(8) 0.0661(5) Uani 1 1 d . . .
H6A H 0.1216 0.7971 0.0570 0.079 Uiso 1 1 calc R . .
C5 C -0.02598(11) 0.9218(2) 0.40414(10) 0.0726(5) Uani 1 1 d . . .
H5A H -0.0298 1.0216 0.4014 0.087 Uiso 1 1 calc R . .
C4 C 0.30676(11) 0.6216(2) 0.36077(10) 0.0749(5) Uani 1 1 d . . .
H4A H 0.3275 0.5773 0.3998 0.090 Uiso 1 1 calc R . .
C3 C -0.05714(12) 0.8505(3) 0.45925(11) 0.0824(6) Uani 1 1 d . . .
H3A H -0.0824 0.9017 0.4942 0.099 Uiso 1 1 calc R . .
C2 C -0.05131(13) 0.7034(3) 0.46318(10) 0.0837(6) Uani 1 1 d . . .
H2A H -0.0720 0.6549 0.5011 0.100 Uiso 1 1 calc R . .
C1 C 0.1969(2) 0.6900(3) 0.00353(12) 0.0979(8) Uani 1 1 d D . .
H1A H 0.1592(13) 0.671(3) -0.0320(11) 0.117(8) Uiso 1 1 d D . .
H2C H 0.2516(12) 0.659(3) 0.0032(13) 0.112(9) Uiso 1 1 d 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
N1 C16 1.3700(19) . ?
N1 C19 1.4050(18) . ?
N1 C13 1.4509(17) . ?
O1 C16 1.2216(18) . ?
C19 C9 1.373(2) . ?
C19 C14 1.393(2) . ?
C18 C7 1.374(2) . ?
C18 C11 1.382(2) . ?
C18 C13 1.508(2) . ?
C17 C14 1.472(2) . ?
C17 C16 1.491(2) . ?
C17 C12 1.506(2) . ?
C17 C15 1.551(2) . ?
C15 C6 1.469(2) . ?
C15 C12 1.484(2) . ?
C14 C10 1.374(2) . ?
C11 C5 1.373(2) . ?
C10 C8 1.383(3) . ?
C9 C4 1.383(2) . ?
C8 C4 1.376(3) . ?
C7 C2 1.386(3) . ?
C6 C1 1.292(3) . ?
C5 C3 1.362(3) . ?
C3 C2 1.371(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 C19 111.32(11) . . ?
C16 N1 C13 123.55(12) . . ?
C19 N1 C13 125.05(12) . . ?
C9 C19 C14 122.08(14) . . ?
C9 C19 N1 128.80(14) . . ?
C14 C19 N1 109.11(12) . . ?
C7 C18 C11 118.22(14) . . ?
C7 C18 C13 120.30(14) . . ?
C11 C18 C13 121.35(13) . . ?
C14 C17 C16 105.60(12) . . ?
C14 C17 C12 124.50(13) . . ?
C16 C17 C12 120.75(13) . . ?
C14 C17 C15 122.48(12) . . ?
C16 C17 C15 119.79(12) . . ?
C12 C17 C15 58.08(10) . . ?
O1 C16 N1 124.94(14) . . ?
O1 C16 C17 128.59(14) . . ?
N1 C16 C17 106.47(12) . . ?
C6 C15 C12 120.85(15) . . ?
C6 C15 C17 121.53(14) . . ?
C12 C15 C17 59.43(10) . . ?
C10 C14 C19 119.54(14) . . ?
C10 C14 C17 133.11(14) . . ?
C19 C14 C17 107.35(12) . . ?
N1 C13 C18 114.37(12) . . ?
C15 C12 C17 62.49(10) . . ?
C5 C11 C18 121.38(16) . . ?
C14 C10 C8 119.12(16) . . ?
C19 C9 C4 117.29(16) . . ?
C4 C8 C10 120.36(16) . . ?
C18 C7 C2 120.49(17) . . ?
C1 C6 C15 124.3(2) . . ?
C3 C5 C11 119.82(19) . . ?
C8 C4 C9 121.61(17) . . ?
C5 C3 C2 119.98(18) . . ?
C3 C2 C7 120.09(18) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_ja_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc20bmkk
_database_code_depnum_ccdc_archive 'CCDC 1857258'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H46 Cl2 N4 O6'
_chemical_formula_weight         917.85

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                   8.9496(3)
_cell_length_b                   9.6224(3)
_cell_length_c                   14.1054(5)
_cell_angle_alpha                100.8225(11)
_cell_angle_beta                 90.1216(11)
_cell_angle_gamma                110.2565(10)
_cell_volume                     1116.34(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5119
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9096
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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            23598
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.52
_reflns_number_total             5119
_reflns_number_gt                4153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0611P)²+0.3542P] 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         5119
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.49702(5) 0.77986(5) 0.03682(3) 0.05307(15) Uani 1 1 d . . .
O3 O 0.05917(13) 1.06875(13) 0.12818(8) 0.0427(3) Uani 1 1 d . . .
N2 N 0.25740(13) 0.96837(13) 0.10679(9) 0.0300(3) Uani 1 1 d . . .
C6 C 0.41250(15) 1.00393(16) 0.14935(10) 0.0283(3) Uani 1 1 d . . .
C1 C 0.44864(16) 1.13265(16) 0.22380(10) 0.0290(3) Uani 1 1 d . . .
C19 C 0.22964(16) 1.20073(16) 0.32504(10) 0.0309(3) Uani 1 1 d . . .
H19 H 0.1244 1.2039 0.3092 0.037 Uiso 1 1 calc R . .
N1 N 0.22480(18) 1.42911(15) 0.44118(10) 0.0450(3) Uani 1 1 d . . .
C9 C 0.16069(17) 0.83984(17) 0.03179(11) 0.0344(3) Uani 1 1 d . . .
H9A H 0.2305 0.7966 -0.0056 0.041 Uiso 1 1 calc R . .
H9B H 0.1050 0.8755 -0.0118 0.041 Uiso 1 1 calc R . .
C15 C 0.04036(17) 0.71901(16) 0.07480(11) 0.0343(3) Uani 1 1 d . . .
C20 C 0.19978(18) 1.06924(17) 0.37518(11) 0.0352(3) Uani 1 1 d . . .
C2 C 0.59449(17) 1.19149(18) 0.27642(11) 0.0368(3) Uani 1 1 d . . .
H2 H 0.6164 1.2750 0.3268 0.044 Uiso 1 1 calc R . .
O2 O 0.09573(16) 1.41640(16) 0.40586(12) 0.0636(4) Uani 1 1 d . . .
C8 C 0.31030(16) 1.18811(16) 0.22778(10) 0.0293(3) Uani 1 1 d . . .
C7 C 0.19180(16) 1.07105(16) 0.14965(10) 0.0306(3) Uani 1 1 d . . .
C18 C 0.32847(18) 1.35873(16) 0.38130(11) 0.0344(3) Uani 1 1 d . . .
H18 H 0.4104 1.3511 0.4241 0.041 Uiso 1 1 calc R . .
C5 C 0.52755(18) 0.93870(17) 0.12773(11) 0.0341(3) Uani 1 1 d . . .
C4 C 0.67555(18) 1.00106(19) 0.17987(12) 0.0413(4) Uani 1 1 d . . .
H4 H 0.7532 0.9582 0.1646 0.050 Uiso 1 1 calc R . .
C16 C 0.34964(19) 1.34839(17) 0.20823(11) 0.0358(3) Uani 1 1 d . . .
H16A H 0.4306 1.3687 0.1620 0.043 Uiso 1 1 calc R . .
H16B H 0.2550 1.3604 0.1829 0.043 Uiso 1 1 calc R . .
C3 C 0.70827(18) 1.1250(2) 0.25349(13) 0.0432(4) Uani 1 1 d . . .
H3 H 0.8073 1.1648 0.2883 0.052 Uiso 1 1 calc R . .
C14 C -0.1199(2) 0.69865(19) 0.06542(14) 0.0474(4) Uani 1 1 d . . .
H14 H -0.1527 0.7597 0.0328 0.057 Uiso 1 1 calc R . .
C17 C 0.4112(2) 1.45487(17) 0.30636(12) 0.0403(4) Uani 1 1 d . . .
H17 H 0.5258 1.4737 0.3146 0.048 Uiso 1 1 calc R . .
O1 O 0.2788(2) 1.5014(2) 0.52165(11) 0.0809(5) Uani 1 1 d . . .
C10 C 0.0856(2) 0.6259(2) 0.12362(14) 0.0512(4) Uani 1 1 d . . .
H10 H 0.1930 0.6378 0.1308 0.061 Uiso 1 1 calc R . .
C23 C 0.1385(3) 0.8155(2) 0.45820(17) 0.0657(6) Uani 1 1 d . . .
H23 H 0.1186 0.7308 0.4857 0.079 Uiso 1 1 calc R . .
C13 C -0.2319(2) 0.5884(2) 0.10405(18) 0.0624(5) Uani 1 1 d . . .
H13 H -0.3394 0.5760 0.0974 0.075 Uiso 1 1 calc R . .
C26 C 0.3931(3) 1.6046(2) 0.31370(14) 0.0543(5) Uani 1 1 d . . .
H26 H 0.2896 1.6055 0.3128 0.065 Uiso 1 1 calc R . .
C21 C 0.3057(2) 1.0648(2) 0.44472(15) 0.0543(5) Uani 1 1 d . . .
H21 H 0.3995 1.1473 0.4639 0.065 Uiso 1 1 calc R . .
C25 C 0.0618(2) 0.9443(2) 0.34860(15) 0.0582(5) Uani 1 1 d . . .
H25 H -0.0126 0.9449 0.3027 0.070 Uiso 1 1 calc R . .
C12 C -0.1852(2) 0.4978(2) 0.15192(16) 0.0584(5) Uani 1 1 d . . .
H12 H -0.2608 0.4238 0.1779 0.070 Uiso 1 1 calc R . .
C11 C -0.0269(2) 0.5160(2) 0.16162(16) 0.0612(5) Uani 1 1 d . . .
H11 H 0.0048 0.4540 0.1940 0.073 Uiso 1 1 calc R . .
C22 C 0.2742(3) 0.9392(3) 0.48622(18) 0.0680(6) Uani 1 1 d . . .
H22 H 0.3463 0.9389 0.5337 0.082 Uiso 1 1 calc R . .
C27 C 0.5071(5) 1.7325(3) 0.3211(2) 0.0837(9) Uani 1 1 d . . .
C24 C 0.0330(3) 0.8181(2) 0.38950(18) 0.0732(7) Uani 1 1 d . . .
H24 H -0.0594 0.7343 0.3698 0.088 Uiso 1 1 calc R . .
H27A H 0.488(4) 1.820(4) 0.325(2) 0.108(10) Uiso 1 1 d . . .
H27B H 0.610(5) 1.725(4) 0.328(3) 0.137(15) Uiso 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 C5 1.7402(16) . ?
O3 C7 1.2161(17) . ?
N2 C7 1.3658(19) . ?
N2 C6 1.4123(17) . ?
N2 C9 1.4702(18) . ?
C6 C5 1.387(2) . ?
C6 C1 1.405(2) . ?
C1 C2 1.3790(19) . ?
C1 C8 1.5058(18) . ?
C19 C20 1.508(2) . ?
C19 C18 1.529(2) . ?
C19 C8 1.556(2) . ?
C19 H19 0.9800 . ?
N1 O1 1.214(2) . ?
N1 O2 1.2142(19) . ?
N1 C18 1.502(2) . ?
C9 C15 1.510(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 C14 1.381(2) . ?
C15 C10 1.386(2) . ?
C20 C21 1.379(2) . ?
C20 C25 1.383(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9300 . ?
C8 C7 1.520(2) . ?
C8 C16 1.537(2) . ?
C18 C17 1.555(2) . ?
C18 H18 0.9800 . ?
C5 C4 1.391(2) . ?
C4 C3 1.371(3) . ?
C4 H4 0.9300 . ?
C16 C17 1.531(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C3 H3 0.9300 . ?
C14 C13 1.382(3) . ?
C14 H14 0.9300 . ?
C17 C26 1.489(2) . ?
C17 H17 0.9800 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C23 C24 1.361(3) . ?
C23 C22 1.367(3) . ?
C23 H23 0.9300 . ?
C13 C12 1.365(3) . ?
C13 H13 0.9300 . ?
C26 C27 1.284(3) . ?
C26 H26 0.9300 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C25 C24 1.386(3) . ?
C25 H25 0.9300 . ?
C12 C11 1.369(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C27 H27A 0.90(3) . ?
C27 H27B 0.95(4) . ?
C24 H24 0.9300 . ?

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 N2 C6 110.34(11) . . ?
C7 N2 C9 118.96(12) . . ?
C6 N2 C9 130.60(12) . . ?
C5 C6 C1 118.95(13) . . ?
C5 C6 N2 131.61(13) . . ?
C1 C6 N2 109.40(12) . . ?
C2 C1 C6 120.80(13) . . ?
C2 C1 C8 130.53(14) . . ?
C6 C1 C8 108.61(12) . . ?
C20 C19 C18 118.07(12) . . ?
C20 C19 C8 115.67(12) . . ?
C18 C19 C8 103.78(11) . . ?
C20 C19 H19 106.1 . . ?
C18 C19 H19 106.1 . . ?
C8 C19 H19 106.1 . . ?
O1 N1 O2 123.62(16) . . ?
O1 N1 C18 117.34(16) . . ?
O2 N1 C18 118.98(14) . . ?
N2 C9 C15 111.88(12) . . ?
N2 C9 H9A 109.2 . . ?
C15 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C15 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C14 C15 C10 118.34(15) . . ?
C14 C15 C9 119.80(14) . . ?
C10 C15 C9 121.86(14) . . ?
C21 C20 C25 117.78(16) . . ?
C21 C20 C19 123.35(15) . . ?
C25 C20 C19 118.84(15) . . ?
C1 C2 C3 119.40(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C1 C8 C7 102.18(11) . . ?
C1 C8 C16 115.00(12) . . ?
C7 C8 C16 111.13(11) . . ?
C1 C8 C19 117.62(11) . . ?
C7 C8 C19 109.87(11) . . ?
C16 C8 C19 101.26(11) . . ?
O3 C7 N2 125.03(13) . . ?
O3 C7 C8 125.54(13) . . ?
N2 C7 C8 109.43(11) . . ?
N1 C18 C19 110.88(12) . . ?
N1 C18 C17 111.23(12) . . ?
C19 C18 C17 107.49(12) . . ?
N1 C18 H18 109.1 . . ?
C19 C18 H18 109.1 . . ?
C17 C18 H18 109.1 . . ?
C6 C5 C4 119.74(14) . . ?
C6 C5 Cl1 123.11(12) . . ?
C4 C5 Cl1 117.16(12) . . ?
C3 C4 C5 120.73(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C17 C16 C8 105.40(12) . . ?
C17 C16 H16A 110.7 . . ?
C8 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C8 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C4 C3 C2 120.36(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C15 C14 C13 120.69(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C26 C17 C16 113.76(14) . . ?
C26 C17 C18 117.05(14) . . ?
C16 C17 C18 104.21(12) . . ?
C26 C17 H17 107.1 . . ?
C16 C17 H17 107.1 . . ?
C18 C17 H17 107.1 . . ?
C11 C10 C15 120.58(17) . . ?
C11 C10 H10 119.7 . . ?
C15 C10 H10 119.7 . . ?
C24 C23 C22 119.06(19) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C12 C13 C14 120.20(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C27 C26 C17 126.1(3) . . ?
C27 C26 H26 116.9 . . ?
C17 C26 H26 116.9 . . ?
C20 C21 C22 120.84(19) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C20 C25 C24 120.8(2) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C13 C12 C11 119.90(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C11 C10 120.29(18) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C26 C27 H27A 122(2) . . ?
C26 C27 H27B 113(2) . . ?
H27A C27 H27B 125(3) . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?

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 N2 C6 C5 -176.37(14) . . . . ?
C9 N2 C6 C5 7.4(2) . . . . ?
C7 N2 C6 C1 1.10(15) . . . . ?
C9 N2 C6 C1 -175.12(13) . . . . ?
C5 C6 C1 C2 -1.6(2) . . . . ?
N2 C6 C1 C2 -179.45(13) . . . . ?
C5 C6 C1 C8 175.71(12) . . . . ?
N2 C6 C1 C8 -2.13(15) . . . . ?
C7 N2 C9 C15 -77.03(16) . . . . ?
C6 N2 C9 C15 98.92(17) . . . . ?
N2 C9 C15 C14 107.87(16) . . . . ?
N2 C9 C15 C10 -72.49(19) . . . . ?
C18 C19 C20 C21 -30.9(2) . . . . ?
C8 C19 C20 C21 92.90(19) . . . . ?
C18 C19 C20 C25 151.15(16) . . . . ?
C8 C19 C20 C25 -85.09(18) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C8 C1 C2 C3 -174.80(15) . . . . ?
C2 C1 C8 C7 179.19(15) . . . . ?
C6 C1 C8 C7 2.21(14) . . . . ?
C2 C1 C8 C16 58.7(2) . . . . ?
C6 C1 C8 C16 -118.29(13) . . . . ?
C2 C1 C8 C19 -60.5(2) . . . . ?
C6 C1 C8 C19 122.56(13) . . . . ?
C20 C19 C8 C1 -43.80(18) . . . . ?
C18 C19 C8 C1 87.14(14) . . . . ?
C20 C19 C8 C7 72.44(15) . . . . ?
C18 C19 C8 C7 -156.61(11) . . . . ?
C20 C19 C8 C16 -170.00(12) . . . . ?
C18 C19 C8 C16 -39.05(13) . . . . ?
C6 N2 C7 O3 -179.74(14) . . . . ?
C9 N2 C7 O3 -3.0(2) . . . . ?
C6 N2 C7 C8 0.39(15) . . . . ?
C9 N2 C7 C8 177.11(11) . . . . ?
C1 C8 C7 O3 178.55(14) . . . . ?
C16 C8 C7 O3 -58.30(19) . . . . ?
C19 C8 C7 O3 52.94(19) . . . . ?
C1 C8 C7 N2 -1.57(14) . . . . ?
C16 C8 C7 N2 121.58(13) . . . . ?
C19 C8 C7 N2 -127.18(12) . . . . ?
O1 N1 C18 C19 140.22(16) . . . . ?
O2 N1 C18 C19 -42.72(19) . . . . ?
O1 N1 C18 C17 -100.23(18) . . . . ?
O2 N1 C18 C17 76.83(18) . . . . ?
C20 C19 C18 N1 -85.78(16) . . . . ?
C8 C19 C18 N1 144.71(12) . . . . ?
C20 C19 C18 C17 152.44(13) . . . . ?
C8 C19 C18 C17 22.94(15) . . . . ?
C1 C6 C5 C4 0.2(2) . . . . ?
N2 C6 C5 C4 177.44(14) . . . . ?
C1 C6 C5 Cl1 -179.67(10) . . . . ?
N2 C6 C5 Cl1 -2.4(2) . . . . ?
C6 C5 C4 C3 1.0(2) . . . . ?
Cl1 C5 C4 C3 -179.13(13) . . . . ?
C1 C8 C16 C17 -86.43(15) . . . . ?
C7 C8 C16 C17 158.12(12) . . . . ?
C19 C8 C16 C17 41.48(14) . . . . ?
C5 C4 C3 C2 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C10 C15 C14 C13 0.2(3) . . . . ?
C9 C15 C14 C13 179.84(17) . . . . ?
C8 C16 C17 C26 -156.09(14) . . . . ?
C8 C16 C17 C18 -27.48(15) . . . . ?
N1 C18 C17 C26 7.5(2) . . . . ?
C19 C18 C17 C26 129.04(16) . . . . ?
N1 C18 C17 C16 -119.09(14) . . . . ?
C19 C18 C17 C16 2.46(16) . . . . ?
C14 C15 C10 C11 0.0(3) . . . . ?
C9 C15 C10 C11 -179.61(17) . . . . ?
C15 C14 C13 C12 -0.2(3) . . . . ?
C16 C17 C26 C27 -112.7(2) . . . . ?
C18 C17 C26 C27 125.5(2) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C21 C22 -178.02(18) . . . . ?
C21 C20 C25 C24 -1.1(3) . . . . ?
C19 C20 C25 C24 176.97(19) . . . . ?
C14 C13 C12 C11 -0.1(3) . . . . ?
C13 C12 C11 C10 0.3(3) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
C24 C23 C22 C21 -0.9(4) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C20 C25 C24 C23 1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.046
