# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_x
_database_code_depnum_ccdc_archive 'CCDC 1526107'
_audit_update_record             
;
2017-01-08 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H23 Cl0 N O4'
_chemical_formula_weight         473.50

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   P212121

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

_cell_length_a                   9.9046(13)
_cell_length_b                   10.4946(12)
_cell_length_c                   23.736(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2467.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8563
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.23

_exptl_crystal_description       sheet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(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            22540
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.1078
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6107
_reflns_number_gt                2702
_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)+(0.0582P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(16)
_refine_ls_number_reflns         6107
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.001
_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
O1 O 0.4549(2) 0.93717(17) 0.10626(7) 0.0527(5) Uani 1 1 d . . .
N2 N 0.2010(3) 1.0946(2) 0.04734(10) 0.0523(6) Uani 1 1 d . . .
C3 C 0.5880(3) 1.0771(3) 0.15427(10) 0.0447(7) Uani 1 1 d . . .
C4 C 0.4133(3) 1.0609(3) 0.08665(11) 0.0473(7) Uani 1 1 d . . .
O5 O 0.4915(2) 1.26951(18) 0.11607(8) 0.0621(6) Uani 1 1 d . . .
C1 C 0.2955(3) 1.0942(3) 0.00287(11) 0.0462(7) Uani 1 1 d . . .
C2 C 0.5327(3) 1.0629(3) -0.01053(12) 0.0558(8) Uani 1 1 d . . .
H2 H 0.6185 1.0483 0.0041 0.067 Uiso 1 1 calc R . .
C9 C 0.6713(3) 1.2203(3) 0.23040(13) 0.0641(9) Uani 1 1 d . . .
H9 H 0.5835 1.2497 0.2352 0.077 Uiso 1 1 calc R . .
C36 C 0.6977(3) 1.1296(3) 0.18963(11) 0.0479(8) Uani 1 1 d . . .
C5 C 0.4234(3) 1.0718(3) 0.02411(11) 0.0468(7) Uani 1 1 d . . .
C6 C -0.0153(3) 0.9805(3) 0.03006(14) 0.0536(8) Uani 1 1 d . . .
C7 C 0.5553(3) 0.9538(3) 0.14500(11) 0.0480(7) Uani 1 1 d . . .
C8 C 0.0550(3) 1.1045(3) 0.04119(14) 0.0594(9) Uani 1 1 d . . .
H8A H 0.0354 1.1625 0.0104 0.071 Uiso 1 1 calc R . .
H8B H 0.0181 1.1415 0.0753 0.071 Uiso 1 1 calc R . .
O9 O 0.2077(2) 1.0623(2) 0.14310(8) 0.0733(7) Uani 1 1 d . . .
C10 C 0.3870(5) 1.1011(3) -0.08929(13) 0.0687(10) Uani 1 1 d . . .
H10 H 0.3758 1.1122 -0.1279 0.082 Uiso 1 1 calc R . .
C11 C 0.2615(3) 1.0726(3) 0.09788(13) 0.0539(8) Uani 1 1 d . . .
C12 C 0.7021(4) 0.7150(5) 0.24395(17) 0.0835(13) Uani 1 1 d . . .
H12 H 0.7458 0.7129 0.2786 0.100 Uiso 1 1 calc R . .
C13 C 0.8299(3) 1.0906(3) 0.18298(12) 0.0591(9) Uani 1 1 d . . .
H13 H 0.8508 1.0308 0.1554 0.071 Uiso 1 1 calc R . .
C14 C 0.4996(3) 1.1547(3) 0.12050(11) 0.0492(7) Uani 1 1 d . . .
C15 C 0.6011(3) 0.8331(3) 0.16910(12) 0.0502(8) Uani 1 1 d . . .
C16 C 0.6645(3) 0.8300(3) 0.22105(14) 0.0645(10) Uani 1 1 d . . .
H16 H 0.6817 0.9054 0.2404 0.077 Uiso 1 1 calc R . .
C17 C 0.9022(4) 1.2276(4) 0.25681(15) 0.0729(10) Uani 1 1 d . . .
H17 H 0.9707 1.2603 0.2793 0.087 Uiso 1 1 calc R . .
C18 C 0.2752(4) 1.1099(3) -0.05358(13) 0.0603(9) Uani 1 1 d . . .
H18 H 0.1895 1.1260 -0.0679 0.072 Uiso 1 1 calc R . .
C19 C -0.0039(4) 0.8807(3) 0.06729(17) 0.0787(11) Uani 1 1 d . . .
H19 H 0.0533 0.8875 0.0982 0.094 Uiso 1 1 calc R . .
O20 O 0.6293(3) 1.0667(3) -0.09933(10) 0.0999(9) Uani 1 1 d . . .
C21 C 0.9312(4) 1.1388(4) 0.21635(15) 0.0728(10) Uani 1 1 d . . .
H21 H 1.0195 1.1110 0.2114 0.087 Uiso 1 1 calc R . .
C22 C 0.5129(4) 1.0763(3) -0.06812(13) 0.0622(9) Uani 1 1 d . . .
C23 C 0.5753(4) 0.7201(3) 0.14118(15) 0.0787(11) Uani 1 1 d . . .
H23 H 0.5322 0.7208 0.1064 0.094 Uiso 1 1 calc R . .
C24 C -0.1614(5) 0.7607(5) 0.0127(3) 0.1140(18) Uani 1 1 d . . .
H24 H -0.2113 0.6867 0.0071 0.137 Uiso 1 1 calc R . .
C25 C 0.6138(5) 0.6063(4) 0.16536(18) 0.1001(15) Uani 1 1 d . . .
H25 H 0.5970 0.5303 0.1465 0.120 Uiso 1 1 calc R . .
C26 C -0.0775(6) 0.7703(4) 0.0588(2) 0.1101(16) Uani 1 1 d . . .
H26 H -0.0704 0.7029 0.0841 0.132 Uiso 1 1 calc R . .
C27 C 0.6754(5) 0.6038(4) 0.2160(2) 0.0959(14) Uani 1 1 d . . .
H27 H 0.6998 0.5262 0.2320 0.115 Uiso 1 1 calc R . .
C28 C -0.1721(5) 0.8582(4) -0.0248(2) 0.0941(14) Uani 1 1 d . . .
H28 H -0.2282 0.8507 -0.0560 0.113 Uiso 1 1 calc R . .
C29 C -0.0987(4) 0.9686(3) -0.01605(16) 0.0723(10) Uani 1 1 d . . .
H29 H -0.1058 1.0354 -0.0416 0.087 Uiso 1 1 calc R . .
C30 C 0.7725(4) 1.2679(4) 0.26397(15) 0.0738(11) Uani 1 1 d . . .
H30 H 0.7524 1.3277 0.2916 0.089 Uiso 1 1 calc R . .
C20 C 0.6214(6) 1.0618(6) -0.15637(16) 0.149(2) Uani 1 1 d . . .
H20A H 0.5595 0.9959 -0.1673 0.223 Uiso 1 1 calc R . .
H20B H 0.7090 1.0438 -0.1717 0.223 Uiso 1 1 calc R . .
H20C H 0.5901 1.1423 -0.1705 0.223 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.366(3) . ?
O1 C4 1.440(3) . ?
N2 C11 1.361(4) . ?
N2 C1 1.411(4) . ?
N2 C8 1.458(4) . ?
C3 C7 1.352(4) . ?
C3 C14 1.440(4) . ?
C3 C36 1.479(4) . ?
C4 C5 1.492(4) . ?
C4 C11 1.532(4) . ?
C4 C14 1.532(4) . ?
O5 C14 1.212(3) . ?
C1 C18 1.365(4) . ?
C1 C5 1.383(4) . ?
C2 C5 1.363(4) . ?
C2 C22 1.388(4) . ?
C9 C30 1.374(4) . ?
C9 C36 1.383(4) . ?
C36 C13 1.380(4) . ?
C6 C19 1.374(4) . ?
C6 C29 1.377(5) . ?
C6 C8 1.500(4) . ?
C7 C15 1.462(4) . ?
O9 C11 1.203(3) . ?
C10 C22 1.369(5) . ?
C10 C18 1.397(5) . ?
C12 C27 1.368(6) . ?
C12 C16 1.375(5) . ?
C13 C21 1.375(4) . ?
C15 C23 1.383(4) . ?
C15 C16 1.384(4) . ?
C17 C30 1.363(5) . ?
C17 C21 1.369(5) . ?
C19 C26 1.384(6) . ?
O20 C20 1.357(4) . ?
O20 C22 1.374(4) . ?
C23 C25 1.379(5) . ?
C24 C28 1.359(7) . ?
C24 C26 1.378(7) . ?
C25 C27 1.349(6) . ?
C28 C29 1.383(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
C7 O1 C4 108.1(2) . . ?
C11 N2 C1 111.6(3) . . ?
C11 N2 C8 122.5(3) . . ?
C1 N2 C8 125.7(3) . . ?
C7 C3 C14 107.8(3) . . ?
C7 C3 C36 128.7(3) . . ?
C14 C3 C36 123.5(2) . . ?
O1 C4 C5 111.8(2) . . ?
O1 C4 C11 107.3(2) . . ?
C5 C4 C11 103.5(2) . . ?
O1 C4 C14 104.5(2) . . ?
C5 C4 C14 115.8(2) . . ?
C11 C4 C14 113.9(2) . . ?
C18 C1 C5 120.9(3) . . ?
C18 C1 N2 129.5(3) . . ?
C5 C1 N2 109.6(2) . . ?
C5 C2 C22 118.4(3) . . ?
C30 C9 C36 121.2(3) . . ?
C13 C36 C9 117.6(3) . . ?
C13 C36 C3 121.4(3) . . ?
C9 C36 C3 121.0(3) . . ?
C2 C5 C1 121.3(3) . . ?
C2 C5 C4 130.4(3) . . ?
C1 C5 C4 108.3(3) . . ?
C19 C6 C29 119.4(3) . . ?
C19 C6 C8 120.6(3) . . ?
C29 C6 C8 119.8(3) . . ?
C3 C7 O1 114.0(2) . . ?
C3 C7 C15 133.7(3) . . ?
O1 C7 C15 112.3(3) . . ?
N2 C8 C6 114.6(2) . . ?
C22 C10 C18 120.8(3) . . ?
O9 C11 N2 127.4(3) . . ?
O9 C11 C4 125.6(3) . . ?
N2 C11 C4 107.0(2) . . ?
C27 C12 C16 120.4(4) . . ?
C21 C13 C36 121.2(3) . . ?
O5 C14 C3 130.6(3) . . ?
O5 C14 C4 123.8(3) . . ?
C3 C14 C4 105.5(2) . . ?
C23 C15 C16 119.4(3) . . ?
C23 C15 C7 119.9(3) . . ?
C16 C15 C7 120.7(3) . . ?
C12 C16 C15 119.7(4) . . ?
C30 C17 C21 119.8(4) . . ?
C1 C18 C10 118.1(3) . . ?
C6 C19 C26 120.0(4) . . ?
C20 O20 C22 119.5(4) . . ?
C17 C21 C13 120.1(4) . . ?
C10 C22 O20 125.5(3) . . ?
C10 C22 C2 120.6(3) . . ?
O20 C22 C2 113.9(3) . . ?
C25 C23 C15 119.5(3) . . ?
C28 C24 C26 120.7(4) . . ?
C27 C25 C23 120.9(4) . . ?
C24 C26 C19 119.6(4) . . ?
C25 C27 C12 120.1(4) . . ?
C24 C28 C29 119.5(4) . . ?
C6 C29 C28 120.7(4) . . ?
C17 C30 C9 120.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1502294'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 N O3'
_chemical_formula_weight         443.48

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           Monoclinic
_symmetry_space_group_name_H-M   P21/N

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

_cell_length_a                   9.2630(19)
_cell_length_b                   16.211(3)
_cell_length_c                   15.413(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.21(3)
_cell_angle_gamma                90.00
_cell_volume                     2313.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_T_max  0.9918
_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4514
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0761
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.36
_reflns_number_total             4240
_reflns_number_gt                2214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_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)+(0.0890P)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         4240
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
N N 0.3295(3) 0.15326(19) 0.10201(18) 0.0545(8) Uani 1 1 d . . .
O1 O 0.2555(3) 0.03237(17) 0.16337(16) 0.0651(8) Uani 1 1 d . . .
C1 C 0.1821(3) 0.1669(2) 0.22341(19) 0.0421(8) Uani 1 1 d . . .
O2 O 0.2247(2) 0.14696(15) 0.31109(13) 0.0487(6) Uani 1 1 d . . .
C2 C 0.2354(4) 0.2493(2) 0.1944(2) 0.0443(8) Uani 1 1 d . . .
O3 O 0.1187(2) 0.10004(16) 0.43000(14) 0.0569(7) Uani 1 1 d . . .
C3 C 0.2124(4) 0.3267(3) 0.2251(2) 0.0616(11) Uani 1 1 d . . .
H3A H 0.1583 0.3348 0.2745 0.074 Uiso 1 1 calc R . .
C4 C 0.2710(5) 0.3938(3) 0.1814(3) 0.0815(14) Uani 1 1 d . . .
H4A H 0.2560 0.4471 0.2016 0.098 Uiso 1 1 calc R . .
C5 C 0.3507(5) 0.3812(3) 0.1085(3) 0.0850(15) Uani 1 1 d . . .
H5A H 0.3888 0.4264 0.0798 0.102 Uiso 1 1 calc R . .
C6 C 0.3758(5) 0.3029(3) 0.0768(3) 0.0743(13) Uani 1 1 d . . .
H6A H 0.4299 0.2947 0.0274 0.089 Uiso 1 1 calc R . .
C7 C 0.3179(4) 0.2381(2) 0.1209(2) 0.0497(9) Uani 1 1 d . . .
C8 C 0.2592(4) 0.1068(3) 0.1606(2) 0.0480(9) Uani 1 1 d . . .
C9 C 0.0211(3) 0.1535(2) 0.2201(2) 0.0415(8) Uani 1 1 d . . .
C10 C -0.0222(3) 0.1270(2) 0.2974(2) 0.0399(8) Uani 1 1 d . . .
C11 C 0.1070(4) 0.1214(2) 0.3558(2) 0.0445(8) Uani 1 1 d . . .
C12 C 0.4128(4) 0.1191(3) 0.0320(2) 0.0681(12) Uani 1 1 d . . .
H12A H 0.4390 0.0629 0.0469 0.082 Uiso 1 1 calc R . .
H12B H 0.5016 0.1505 0.0276 0.082 Uiso 1 1 calc R . .
C13 C 0.3377(4) 0.1187(2) -0.0556(2) 0.0569(10) Uani 1 1 d . . .
C14 C 0.1966(5) 0.1430(3) -0.0682(3) 0.0742(13) Uani 1 1 d . . .
H14A H 0.1442 0.1622 -0.0215 0.089 Uiso 1 1 calc R . .
C15 C 0.1319(6) 0.1393(3) -0.1500(3) 0.0831(14) Uani 1 1 d . . .
H15A H 0.0369 0.1567 -0.1579 0.100 Uiso 1 1 calc R . .
C16 C 0.2068(6) 0.1101(3) -0.2193(3) 0.0875(15) Uani 1 1 d . . .
H16A H 0.1631 0.1074 -0.2741 0.105 Uiso 1 1 calc R . .
C17 C 0.3464(6) 0.0850(3) -0.2070(3) 0.0884(15) Uani 1 1 d . . .
H17A H 0.3977 0.0649 -0.2537 0.106 Uiso 1 1 calc R . .
C18 C 0.4124(5) 0.0893(3) -0.1258(3) 0.0723(12) Uani 1 1 d . . .
H18A H 0.5077 0.0722 -0.1184 0.087 Uiso 1 1 calc R . .
C19 C -0.0599(3) 0.1638(2) 0.1368(2) 0.0438(8) Uani 1 1 d . . .
C20 C -0.1056(4) 0.0948(3) 0.0911(2) 0.0644(11) Uani 1 1 d . . .
H20A H -0.0896 0.0425 0.1142 0.077 Uiso 1 1 calc R . .
C21 C -0.1747(5) 0.1032(3) 0.0116(3) 0.0813(14) Uani 1 1 d . . .
H21A H -0.2039 0.0566 -0.0194 0.098 Uiso 1 1 calc R . .
C22 C -0.2004(5) 0.1807(4) -0.0219(3) 0.0872(16) Uani 1 1 d . . .
H22A H -0.2474 0.1865 -0.0755 0.105 Uiso 1 1 calc R . .
C23 C -0.1574(5) 0.2490(3) 0.0232(3) 0.0880(15) Uani 1 1 d . . .
H23A H -0.1755 0.3012 0.0004 0.106 Uiso 1 1 calc R . .
C24 C -0.0873(4) 0.2409(3) 0.1021(3) 0.0679(12) Uani 1 1 d . . .
H24A H -0.0581 0.2878 0.1325 0.081 Uiso 1 1 calc R . .
C25 C -0.1692(3) 0.1076(2) 0.3271(2) 0.0429(8) Uani 1 1 d . . .
C26 C -0.1928(4) 0.0461(2) 0.3871(2) 0.0559(10) Uani 1 1 d . . .
H26A H -0.1152 0.0160 0.4095 0.067 Uiso 1 1 calc R . .
C27 C -0.3304(4) 0.0291(3) 0.4142(3) 0.0694(12) Uani 1 1 d . . .
H27A H -0.3449 -0.0128 0.4544 0.083 Uiso 1 1 calc R . .
C28 C -0.4459(4) 0.0731(3) 0.3825(3) 0.0726(13) Uani 1 1 d . . .
H28A H -0.5387 0.0617 0.4011 0.087 Uiso 1 1 calc R . .
C29 C -0.4231(4) 0.1345(3) 0.3229(3) 0.0751(13) Uani 1 1 d . . .
H29A H -0.5011 0.1646 0.3009 0.090 Uiso 1 1 calc R . .
C30 C -0.2859(4) 0.1520(2) 0.2954(3) 0.0624(11) Uani 1 1 d . . .
H30A H -0.2719 0.1939 0.2553 0.075 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N C8 1.354(4) . ?
N C7 1.410(4) . ?
N C12 1.450(4) . ?
O1 C8 1.207(4) . ?
C1 O2 1.437(3) . ?
C1 C2 1.496(5) . ?
C1 C9 1.507(4) . ?
C1 C8 1.557(5) . ?
O2 C11 1.366(4) . ?
C2 C3 1.360(5) . ?
C2 C7 1.391(5) . ?
O3 C11 1.198(4) . ?
C3 C4 1.395(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.368(5) . ?
C6 H6A 0.9300 . ?
C9 C10 1.336(4) . ?
C9 C19 1.484(4) . ?
C10 C25 1.480(4) . ?
C10 C11 1.484(4) . ?
C12 C13 1.505(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.375(5) . ?
C13 C18 1.382(5) . ?
C14 C15 1.386(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.370(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.365(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.382(6) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C24 1.381(5) . ?
C19 C20 1.383(5) . ?
C20 C21 1.378(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.378(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.361(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.374(5) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C30 1.379(5) . ?
C25 C26 1.380(5) . ?
C26 C27 1.378(5) . ?
C26 H26A 0.9300 . ?
C27 C28 1.368(6) . ?
C27 H27A 0.9300 . ?
C28 C29 1.373(6) . ?
C28 H28A 0.9300 . ?
C29 C30 1.378(5) . ?
C29 H29A 0.9300 . ?
C30 H30A 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
C8 N C7 111.4(3) . . ?
C8 N C12 123.7(3) . . ?
C7 N C12 124.7(3) . . ?
O2 C1 C2 113.3(3) . . ?
O2 C1 C9 104.5(2) . . ?
C2 C1 C9 116.8(3) . . ?
O2 C1 C8 108.9(3) . . ?
C2 C1 C8 102.4(3) . . ?
C9 C1 C8 110.8(3) . . ?
C11 O2 C1 109.7(2) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 131.7(3) . . ?
C7 C2 C1 108.5(3) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C7 C6 C5 117.3(4) . . ?
C7 C6 H6A 121.3 . . ?
C5 C6 H6A 121.3 . . ?
C6 C7 C2 122.2(4) . . ?
C6 C7 N 127.9(3) . . ?
C2 C7 N 109.9(3) . . ?
O1 C8 N 126.4(3) . . ?
O1 C8 C1 126.1(3) . . ?
N C8 C1 107.4(3) . . ?
C10 C9 C19 130.8(3) . . ?
C10 C9 C1 109.4(3) . . ?
C19 C9 C1 119.6(3) . . ?
C9 C10 C25 129.7(3) . . ?
C9 C10 C11 107.9(3) . . ?
C25 C10 C11 122.4(3) . . ?
O3 C11 O2 120.8(3) . . ?
O3 C11 C10 130.7(3) . . ?
O2 C11 C10 108.5(3) . . ?
N C12 C13 115.2(3) . . ?
N C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
N C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C18 118.6(4) . . ?
C14 C13 C12 123.0(3) . . ?
C18 C13 C12 118.3(4) . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C13 C18 C17 120.5(4) . . ?
C13 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C24 C19 C20 118.9(3) . . ?
C24 C19 C9 121.5(3) . . ?
C20 C19 C9 119.6(3) . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C24 120.2(4) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C23 C24 C19 120.5(4) . . ?
C23 C24 H24A 119.7 . . ?
C19 C24 H24A 119.7 . . ?
C30 C25 C26 118.7(3) . . ?
C30 C25 C10 119.9(3) . . ?
C26 C25 C10 121.4(3) . . ?
C27 C26 C25 120.6(4) . . ?
C27 C26 H26A 119.7 . . ?
C25 C26 H26A 119.7 . . ?
C28 C27 C26 120.5(4) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C27 C28 C29 119.1(4) . . ?
C27 C28 H28A 120.4 . . ?
C29 C28 H28A 120.4 . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29A 119.6 . . ?
C30 C29 H29A 119.6 . . ?
C29 C30 C25 120.3(4) . . ?
C29 C30 H30A 119.9 . . ?
C25 C30 H30A 119.9 . . ?

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
C2 C1 O2 C11 130.4(3) . . . . ?
C9 C1 O2 C11 2.1(3) . . . . ?
C8 C1 O2 C11 -116.3(3) . . . . ?
O2 C1 C2 C3 -60.1(5) . . . . ?
C9 C1 C2 C3 61.5(5) . . . . ?
C8 C1 C2 C3 -177.3(4) . . . . ?
O2 C1 C2 C7 122.4(3) . . . . ?
C9 C1 C2 C7 -116.0(3) . . . . ?
C8 C1 C2 C7 5.3(3) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 -176.5(3) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C2 0.7(6) . . . . ?
C5 C6 C7 N -179.4(4) . . . . ?
C3 C2 C7 C6 -1.1(5) . . . . ?
C1 C2 C7 C6 176.8(3) . . . . ?
C3 C2 C7 N 179.0(3) . . . . ?
C1 C2 C7 N -3.2(4) . . . . ?
C8 N C7 C6 179.3(4) . . . . ?
C12 N C7 C6 2.8(6) . . . . ?
C8 N C7 C2 -0.7(4) . . . . ?
C12 N C7 C2 -177.3(3) . . . . ?
C7 N C8 O1 -176.6(3) . . . . ?
C12 N C8 O1 0.1(6) . . . . ?
C7 N C8 C1 4.1(4) . . . . ?
C12 N C8 C1 -179.3(3) . . . . ?
O2 C1 C8 O1 54.8(4) . . . . ?
C2 C1 C8 O1 175.0(3) . . . . ?
C9 C1 C8 O1 -59.7(4) . . . . ?
O2 C1 C8 N -125.9(3) . . . . ?
C2 C1 C8 N -5.7(3) . . . . ?
C9 C1 C8 N 119.7(3) . . . . ?
O2 C1 C9 C10 -1.2(4) . . . . ?
C2 C1 C9 C10 -127.4(3) . . . . ?
C8 C1 C9 C10 115.9(3) . . . . ?
O2 C1 C9 C19 -176.5(3) . . . . ?
C2 C1 C9 C19 57.3(4) . . . . ?
C8 C1 C9 C19 -59.4(4) . . . . ?
C19 C9 C10 C25 -7.2(6) . . . . ?
C1 C9 C10 C25 178.2(3) . . . . ?
C19 C9 C10 C11 174.6(3) . . . . ?
C1 C9 C10 C11 -0.1(4) . . . . ?
C1 O2 C11 O3 178.5(3) . . . . ?
C1 O2 C11 C10 -2.2(3) . . . . ?
C9 C10 C11 O3 -179.4(4) . . . . ?
C25 C10 C11 O3 2.2(6) . . . . ?
C9 C10 C11 O2 1.4(4) . . . . ?
C25 C10 C11 O2 -177.0(3) . . . . ?
C8 N C12 C13 100.7(4) . . . . ?
C7 N C12 C13 -83.2(5) . . . . ?
N C12 C13 C14 -4.6(6) . . . . ?
N C12 C13 C18 178.1(4) . . . . ?
C18 C13 C14 C15 -1.0(6) . . . . ?
C12 C13 C14 C15 -178.3(4) . . . . ?
C13 C14 C15 C16 1.0(7) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C14 C13 C18 C17 0.4(6) . . . . ?
C12 C13 C18 C17 177.8(4) . . . . ?
C16 C17 C18 C13 0.3(7) . . . . ?
C10 C9 C19 C24 111.7(4) . . . . ?
C1 C9 C19 C24 -74.2(4) . . . . ?
C10 C9 C19 C20 -70.3(5) . . . . ?
C1 C9 C19 C20 103.9(4) . . . . ?
C24 C19 C20 C21 1.3(6) . . . . ?
C9 C19 C20 C21 -176.8(3) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C23 0.2(7) . . . . ?
C21 C22 C23 C24 0.4(7) . . . . ?
C22 C23 C24 C19 -0.1(7) . . . . ?
C20 C19 C24 C23 -0.7(6) . . . . ?
C9 C19 C24 C23 177.4(4) . . . . ?
C9 C10 C25 C30 -33.7(5) . . . . ?
C11 C10 C25 C30 144.4(3) . . . . ?
C9 C10 C25 C26 147.2(4) . . . . ?
C11 C10 C25 C26 -34.7(5) . . . . ?
C30 C25 C26 C27 0.6(5) . . . . ?
C10 C25 C26 C27 179.8(3) . . . . ?
C25 C26 C27 C28 -0.5(6) . . . . ?
C26 C27 C28 C29 0.3(7) . . . . ?
C27 C28 C29 C30 -0.3(7) . . . . ?
C28 C29 C30 C25 0.4(6) . . . . ?
C26 C25 C30 C29 -0.6(6) . . . . ?
C10 C25 C30 C29 -179.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.056
