# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sp1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N2 O3'
_chemical_formula_weight         420.45

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   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   18.6306(7)
_cell_length_b                   9.8545(4)
_cell_length_c                   23.3346(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2290(10)
_cell_angle_gamma                90.00
_cell_volume                     4228.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29234
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         31.92
_reflns_number_total             6380
_reflns_number_gt                3616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0762P)²+0.4242P] 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         6380
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.21048(7) 1.00241(13) 0.99311(5) 0.0541(3) Uani 1 1 d . . .
O2 O -0.02691(6) 0.91694(11) 0.93120(5) 0.0455(3) Uani 1 1 d . . .
O3 O 0.09274(6) 0.83818(13) 0.75190(5) 0.0509(3) Uani 1 1 d . . .
N1 N 0.10197(7) 0.89854(12) 0.95588(5) 0.0377(3) Uani 1 1 d . . .
N2 N 0.16240(7) 0.62970(13) 0.93684(6) 0.0404(3) Uani 1 1 d . . .
H2 H 0.2019 0.5891 0.9515 0.048 Uiso 1 1 calc R . .
C1 C 0.11496(12) 1.30234(18) 0.85934(10) 0.0657(6) Uani 1 1 d . . .
H1 H 0.1335 1.3852 0.8495 0.079 Uiso 1 1 calc R . .
C2 C 0.04812(12) 1.25970(18) 0.83100(10) 0.0671(6) Uani 1 1 d . . .
H2A H 0.0222 1.3149 0.8026 0.081 Uiso 1 1 calc R . .
C3 C 0.01871(10) 1.13644(18) 0.84387(9) 0.0569(5) Uani 1 1 d . . .
H3 H -0.0259 1.1071 0.8240 0.068 Uiso 1 1 calc R . .
C4 C 0.05774(9) 1.05886(15) 0.88705(7) 0.0400(4) Uani 1 1 d . . .
C5 C 0.04070(8) 0.92010(14) 0.90865(7) 0.0361(4) Uani 1 1 d . . .
C6 C 0.03309(8) 0.81034(14) 0.85966(6) 0.0330(3) Uani 1 1 d . . .
H6 H 0.0129 0.8580 0.8238 0.040 Uiso 1 1 calc R . .
C7 C 0.10214(8) 0.74702(14) 0.84798(6) 0.0331(3) Uani 1 1 d . . .
C8 C 0.12454(8) 0.76937(15) 0.79187(7) 0.0365(4) Uani 1 1 d . . .
C9 C 0.19482(8) 0.69509(15) 0.79193(7) 0.0378(4) Uani 1 1 d . . .
C10 C 0.23660(10) 0.67691(18) 0.74939(8) 0.0488(4) Uani 1 1 d . . .
H10 H 0.2243 0.7177 0.7132 0.059 Uiso 1 1 calc R . .
C11 C 0.29848(10) 0.59492(19) 0.76208(9) 0.0555(5) Uani 1 1 d . . .
H11 H 0.3280 0.5813 0.7340 0.067 Uiso 1 1 calc R . .
C12 C 0.31613(10) 0.53417(19) 0.81564(9) 0.0521(5) Uani 1 1 d . . .
H12 H 0.3569 0.4786 0.8229 0.063 Uiso 1 1 calc R . .
C13 C 0.10531(10) 0.79016(16) 0.99837(7) 0.0447(4) Uani 1 1 d . . .
H13A H 0.0633 0.7973 1.0180 0.054 Uiso 1 1 calc R . .
H13B H 0.1484 0.8030 1.0273 0.054 Uiso 1 1 calc R . .
C14 C 0.10730(9) 0.64775(15) 0.97319(7) 0.0407(4) Uani 1 1 d . . .
H14A H 0.1158 0.5831 1.0049 0.049 Uiso 1 1 calc R . .
H14B H 0.0601 0.6276 0.9506 0.049 Uiso 1 1 calc R . .
C15 C 0.15595(8) 0.67213(14) 0.88160(6) 0.0336(3) Uani 1 1 d . . .
C16 C 0.21319(8) 0.63634(15) 0.84671(7) 0.0352(4) Uani 1 1 d . . .
C17 C 0.27398(9) 0.55452(16) 0.85914(8) 0.0434(4) Uani 1 1 d . . .
H17 H 0.2864 0.5143 0.8954 0.052 Uiso 1 1 calc R . .
C18 C 0.15273(9) 0.99818(16) 0.95918(7) 0.0394(4) Uani 1 1 d . . .
C19 C 0.12444(9) 1.10160(15) 0.91530(7) 0.0409(4) Uani 1 1 d . . .
C20 C 0.15457(10) 1.22412(18) 0.90194(9) 0.0556(5) Uani 1 1 d . . .
H20 H 0.1998 1.2522 0.9211 0.067 Uiso 1 1 calc R . .
C21 C -0.06111(8) 0.79421(15) 0.91463(7) 0.0386(4) Uani 1 1 d . . .
C22 C -0.02802(8) 0.72451(14) 0.87498(7) 0.0343(3) Uani 1 1 d . . .
C23 C -0.05583(9) 0.60150(15) 0.85381(7) 0.0414(4) Uani 1 1 d . . .
H23 H -0.0339 0.5546 0.8266 0.050 Uiso 1 1 calc R . .
C24 C -0.11682(10) 0.54739(17) 0.87316(8) 0.0489(4) Uani 1 1 d . . .
C25 C -0.14831(12) 0.4126(2) 0.85026(12) 0.0760(7) Uani 1 1 d . . .
H25A H -0.1139 0.3416 0.8624 0.114 Uiso 1 1 calc R . .
H25B H -0.1585 0.4155 0.8086 0.114 Uiso 1 1 calc R . .
H25C H -0.1925 0.3953 0.8653 0.114 Uiso 1 1 calc R . .
C26 C -0.14820(9) 0.62099(18) 0.91306(9) 0.0507(5) Uani 1 1 d . . .
H26 H -0.1889 0.5854 0.9262 0.061 Uiso 1 1 calc R . .
C27 C -0.12156(9) 0.74572(18) 0.93439(8) 0.0494(4) Uani 1 1 d . . .
H27 H -0.1438 0.7942 0.9609 0.059 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 C18 1.2300(19) . ?
O2 C21 1.3925(18) . ?
O2 C5 1.441(2) . ?
O3 C8 1.2262(18) . ?
N1 C18 1.357(2) . ?
N1 C13 1.452(2) . ?
N1 C5 1.4695(19) . ?
N2 C15 1.3420(19) . ?
N2 C14 1.444(2) . ?
N2 H2 0.8600 . ?
C1 C20 1.375(3) . ?
C1 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9300 . ?
C4 C19 1.376(2) . ?
C4 C5 1.509(2) . ?
C5 C6 1.564(2) . ?
C6 C7 1.494(2) . ?
C6 C22 1.507(2) . ?
C6 H6 0.9800 . ?
C7 C15 1.383(2) . ?
C7 C8 1.453(2) . ?
C8 C9 1.500(2) . ?
C9 C10 1.368(2) . ?
C9 C16 1.395(2) . ?
C10 C11 1.400(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.394(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.524(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.484(2) . ?
C16 C17 1.383(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.480(2) . ?
C19 C20 1.388(2) . ?
C20 H20 0.9300 . ?
C21 C27 1.370(2) . ?
C21 C22 1.375(2) . ?
C22 C23 1.378(2) . ?
C23 C24 1.394(2) . ?
C23 H23 0.9300 . ?
C24 C26 1.382(3) . ?
C24 C25 1.514(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9300 . ?
C27 H27 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
C21 O2 C5 107.77(11) . . ?
C18 N1 C13 122.72(13) . . ?
C18 N1 C5 112.85(12) . . ?
C13 N1 C5 124.17(13) . . ?
C15 N2 C14 124.29(13) . . ?
C15 N2 H2 117.9 . . ?
C14 N2 H2 117.9 . . ?
C20 C1 C2 120.97(17) . . ?
C20 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C2 C3 121.44(17) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 117.70(17) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C19 C4 C3 120.75(15) . . ?
C19 C4 C5 109.86(13) . . ?
C3 C4 C5 129.30(14) . . ?
O2 C5 N1 110.02(13) . . ?
O2 C5 C4 112.62(12) . . ?
N1 C5 C4 101.64(12) . . ?
O2 C5 C6 105.66(11) . . ?
N1 C5 C6 114.63(12) . . ?
C4 C5 C6 112.46(13) . . ?
C7 C6 C22 120.97(12) . . ?
C7 C6 C5 116.27(12) . . ?
C22 C6 C5 101.43(12) . . ?
C7 C6 H6 105.6 . . ?
C22 C6 H6 105.6 . . ?
C5 C6 H6 105.6 . . ?
C15 C7 C8 107.76(13) . . ?
C15 C7 C6 133.37(14) . . ?
C8 C7 C6 118.76(13) . . ?
O3 C8 C7 126.55(15) . . ?
O3 C8 C9 125.86(15) . . ?
C7 C8 C9 107.57(13) . . ?
C10 C9 C16 121.74(15) . . ?
C10 C9 C8 131.41(15) . . ?
C16 C9 C8 106.81(13) . . ?
C9 C10 C11 117.85(17) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C12 C11 C10 120.76(18) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C17 121.19(17) . . ?
C11 C12 H12 119.4 . . ?
C17 C12 H12 119.4 . . ?
N1 C13 C14 114.52(13) . . ?
N1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
N2 C14 C13 113.80(14) . . ?
N2 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N2 C15 C7 131.00(15) . . ?
N2 C15 C16 119.43(13) . . ?
C7 C15 C16 109.57(13) . . ?
C17 C16 C9 120.44(15) . . ?
C17 C16 C15 131.29(15) . . ?
C9 C16 C15 108.16(13) . . ?
C16 C17 C12 117.99(16) . . ?
C16 C17 H17 121.0 . . ?
C12 C17 H17 121.0 . . ?
O1 C18 N1 126.21(15) . . ?
O1 C18 C19 126.83(15) . . ?
N1 C18 C19 106.94(13) . . ?
C4 C19 C20 121.70(16) . . ?
C4 C19 C18 108.33(14) . . ?
C20 C19 C18 129.96(15) . . ?
C1 C20 C19 117.41(16) . . ?
C1 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C27 C21 C22 122.26(15) . . ?
C27 C21 O2 125.02(15) . . ?
C22 C21 O2 112.72(14) . . ?
C21 C22 C23 119.82(15) . . ?
C21 C22 C6 108.46(13) . . ?
C23 C22 C6 131.57(15) . . ?
C22 C23 C24 119.94(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C26 C24 C23 118.19(16) . . ?
C26 C24 C25 121.09(18) . . ?
C23 C24 C25 120.72(19) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 C27 122.76(16) . . ?
C24 C26 H26 118.6 . . ?
C27 C26 H26 118.6 . . ?
C21 C27 C26 117.02(17) . . ?
C21 C27 H27 121.5 . . ?
C26 C27 H27 121.5 . . ?

_diffrn_measured_fraction_theta_max 0.874
_diffrn_reflns_theta_full        31.92
_diffrn_measured_fraction_theta_full 0.874
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 994163'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sp1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N2 O3'
_chemical_formula_weight         434.48

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   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   18.825(4)
_cell_length_b                   10.152(2)
_cell_length_c                   23.818(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.299(3)
_cell_angle_gamma                90.00
_cell_volume                     4447.3(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15340
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.57
_reflns_number_total             4256
_reflns_number_gt                2908
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0918P)²+1.0329P] 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         4256
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.90059(8) 0.60264(16) 0.24607(6) 0.0548(4) Uani 1 1 d . . .
O2 O 1.02376(8) 0.55502(15) 0.07730(6) 0.0521(4) Uani 1 1 d . . .
O3 O 0.78785(8) 0.48858(17) -0.00230(7) 0.0648(5) Uani 1 1 d . . .
N1 N 0.89535(10) 0.58135(17) 0.04580(7) 0.0479(5) Uani 1 1 d . . .
N2 N 0.83655(10) 0.83816(17) 0.06937(7) 0.0470(5) Uani 1 1 d . . .
H2 H 0.7972 0.8790 0.0540 0.056 Uiso 1 1 calc R . .
C1 C 0.87367(16) 0.1754(3) 0.12586(14) 0.0806(8) Uani 1 1 d . . .
H1 H 0.8533 0.0945 0.1318 0.097 Uiso 1 1 calc R . .
C2 C 0.94030(16) 0.2114(3) 0.15979(14) 0.0803(9) Uani 1 1 d . . .
H2A H 0.9642 0.1534 0.1878 0.096 Uiso 1 1 calc R . .
C3 C 0.97173(13) 0.3308(2) 0.15290(11) 0.0663(7) Uani 1 1 d . . .
H3 H 1.0159 0.3553 0.1763 0.080 Uiso 1 1 calc R . .
C4 C 0.93554(11) 0.4136(2) 0.10998(9) 0.0486(5) Uani 1 1 d . . .
C5 C 0.95517(11) 0.5501(2) 0.09469(9) 0.0445(5) Uani 1 1 d . . .
C6 C 0.96258(10) 0.64896(19) 0.14587(8) 0.0398(5) Uani 1 1 d . . .
H6 H 0.9820 0.5974 0.1805 0.048 Uiso 1 1 calc R . .
C7 C 0.89388(10) 0.70911(19) 0.15547(8) 0.0387(5) Uani 1 1 d . . .
C8 C 0.87031(11) 0.6775(2) 0.20814(8) 0.0408(5) Uani 1 1 d . . .
C9 C 0.80126(11) 0.7517(2) 0.20705(8) 0.0417(5) Uani 1 1 d . . .
C10 C 0.75915(12) 0.7637(2) 0.24694(9) 0.0514(6) Uani 1 1 d . . .
H10 H 0.7703 0.7173 0.2814 0.062 Uiso 1 1 calc R . .
C11 C 0.69918(13) 0.8471(3) 0.23468(10) 0.0590(6) Uani 1 1 d . . .
H11 H 0.6699 0.8570 0.2613 0.071 Uiso 1 1 calc R . .
C12 C 0.83737(14) 0.2581(2) 0.08356(12) 0.0661(7) Uani 1 1 d . . .
H12 H 0.7929 0.2342 0.0605 0.079 Uiso 1 1 calc R . .
C13 C 0.86938(12) 0.3782(2) 0.07643(9) 0.0494(6) Uani 1 1 d . . .
C14 C 0.84393(11) 0.4856(2) 0.03504(9) 0.0489(6) Uani 1 1 d . . .
C15 C 0.84179(11) 0.78790(19) 0.12234(8) 0.0395(5) Uani 1 1 d . . .
C16 C 0.89277(12) 0.8280(2) 0.03652(9) 0.0489(6) Uani 1 1 d . . .
H16 H 0.9399 0.8428 0.0626 0.059 Uiso 1 1 calc R . .
C17 C 0.89463(14) 0.6932(2) 0.00820(9) 0.0573(6) Uani 1 1 d . . .
H17A H 0.8525 0.6859 -0.0232 0.069 Uiso 1 1 calc R . .
H17B H 0.9375 0.6890 -0.0082 0.069 Uiso 1 1 calc R . .
C18 C 0.88284(17) 0.9306(3) -0.00973(12) 0.0807(9) Uani 1 1 d . . .
H18A H 0.8356 0.9210 -0.0344 0.121 Uiso 1 1 calc R . .
H18B H 0.9195 0.9199 -0.0319 0.121 Uiso 1 1 calc R . .
H18C H 0.8870 1.0166 0.0074 0.121 Uiso 1 1 calc R . .
C19 C 0.78442(10) 0.8186(2) 0.15492(8) 0.0410(5) Uani 1 1 d . . .
C20 C 0.72493(12) 0.9016(2) 0.14240(9) 0.0486(5) Uani 1 1 d . . .
H20 H 0.7134 0.9469 0.1077 0.058 Uiso 1 1 calc R . .
C21 C 0.68280(13) 0.9150(2) 0.18359(10) 0.0572(6) Uani 1 1 d . . .
H21 H 0.6428 0.9710 0.1764 0.069 Uiso 1 1 calc R . .
C22 C 1.02419(11) 0.7339(2) 0.13664(8) 0.0411(5) Uani 1 1 d . . .
C23 C 1.05837(11) 0.6718(2) 0.09865(9) 0.0456(5) Uani 1 1 d . . .
C24 C 1.11974(12) 0.7212(2) 0.08443(11) 0.0577(6) Uani 1 1 d . . .
H24 H 1.1427 0.6776 0.0589 0.069 Uiso 1 1 calc R . .
C25 C 1.14615(13) 0.8392(3) 0.10977(11) 0.0624(7) Uani 1 1 d . . .
H25 H 1.1879 0.8748 0.1009 0.075 Uiso 1 1 calc R . .
C26 C 1.11314(12) 0.9062(2) 0.14767(10) 0.0547(6) Uani 1 1 d . . .
C27 C 1.05148(11) 0.8515(2) 0.16137(9) 0.0474(5) Uani 1 1 d . . .
H27 H 1.0285 0.8941 0.1872 0.057 Uiso 1 1 calc R . .
C28 C 1.14357(15) 1.0340(3) 0.17447(14) 0.0805(8) Uani 1 1 d . . .
H28A H 1.1905 1.0490 0.1660 0.121 Uiso 1 1 calc R . .
H28B H 1.1481 1.0295 0.2153 0.121 Uiso 1 1 calc R . .
H28C H 1.1115 1.1049 0.1591 0.121 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 C8 1.225(2) . ?
O2 C23 1.396(3) . ?
O2 C5 1.438(3) . ?
O3 C14 1.227(2) . ?
N1 C14 1.357(3) . ?
N1 C17 1.445(3) . ?
N1 C5 1.472(3) . ?
N2 C15 1.345(2) . ?
N2 C16 1.448(3) . ?
N2 H2 0.8600 . ?
C1 C12 1.376(4) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C13 1.377(3) . ?
C4 C5 1.499(3) . ?
C5 C6 1.562(3) . ?
C6 C7 1.491(3) . ?
C6 C22 1.499(3) . ?
C6 H6 0.9800 . ?
C7 C15 1.376(3) . ?
C7 C8 1.453(3) . ?
C8 C9 1.498(3) . ?
C9 C10 1.366(3) . ?
C9 C19 1.391(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.9300 . ?
C11 C21 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.480(3) . ?
C15 C19 1.491(3) . ?
C16 C18 1.498(3) . ?
C16 C17 1.530(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.383(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 C27 1.381(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(3) . ?
C26 C28 1.504(3) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C23 O2 C5 107.60(15) . . ?
C14 N1 C17 122.27(17) . . ?
C14 N1 C5 112.95(17) . . ?
C17 N1 C5 124.36(18) . . ?
C15 N2 C16 124.34(18) . . ?
C15 N2 H2 117.8 . . ?
C16 N2 H2 117.8 . . ?
C12 C1 C2 120.8(3) . . ?
C12 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 117.8(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C13 C4 C3 120.8(2) . . ?
C13 C4 C5 109.88(19) . . ?
C3 C4 C5 129.22(19) . . ?
O2 C5 N1 110.33(16) . . ?
O2 C5 C4 112.63(17) . . ?
N1 C5 C4 101.80(16) . . ?
O2 C5 C6 105.44(15) . . ?
N1 C5 C6 113.90(16) . . ?
C4 C5 C6 112.94(17) . . ?
C7 C6 C22 120.70(17) . . ?
C7 C6 C5 116.52(15) . . ?
C22 C6 C5 101.43(16) . . ?
C7 C6 H6 105.6 . . ?
C22 C6 H6 105.6 . . ?
C5 C6 H6 105.6 . . ?
C15 C7 C8 108.17(18) . . ?
C15 C7 C6 133.27(18) . . ?
C8 C7 C6 118.45(17) . . ?
O1 C8 C7 126.5(2) . . ?
O1 C8 C9 126.22(19) . . ?
C7 C8 C9 107.32(17) . . ?
C10 C9 C19 121.4(2) . . ?
C10 C9 C8 131.51(19) . . ?
C19 C9 C8 107.02(18) . . ?
C9 C10 C11 118.2(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C21 C11 C10 120.6(2) . . ?
C21 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C1 C12 C13 117.7(2) . . ?
C1 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C4 C13 C12 121.5(2) . . ?
C4 C13 C14 108.58(19) . . ?
C12 C13 C14 130.0(2) . . ?
O3 C14 N1 126.0(2) . . ?
O3 C14 C13 127.4(2) . . ?
N1 C14 C13 106.58(17) . . ?
N2 C15 C7 131.2(2) . . ?
N2 C15 C19 119.51(18) . . ?
C7 C15 C19 109.25(17) . . ?
N2 C16 C18 110.92(19) . . ?
N2 C16 C17 112.95(19) . . ?
C18 C16 C17 107.97(19) . . ?
N2 C16 H16 108.3 . . ?
C18 C16 H16 108.3 . . ?
C17 C16 H16 108.3 . . ?
N1 C17 C16 115.35(17) . . ?
N1 C17 H17A 108.4 . . ?
C16 C17 H17A 108.4 . . ?
N1 C17 H17B 108.4 . . ?
C16 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C9 120.7(2) . . ?
C20 C19 C15 131.18(19) . . ?
C9 C19 C15 108.06(17) . . ?
C19 C20 C21 117.6(2) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C11 C21 C20 121.4(2) . . ?
C11 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C27 119.7(2) . . ?
C23 C22 C6 108.63(18) . . ?
C27 C22 C6 131.6(2) . . ?
C24 C23 C22 122.4(2) . . ?
C24 C23 O2 125.1(2) . . ?
C22 C23 O2 112.51(18) . . ?
C23 C24 C25 116.9(2) . . ?
C23 C24 H24 121.5 . . ?
C25 C24 H24 121.5 . . ?
C26 C25 C24 122.8(2) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C27 118.3(2) . . ?
C25 C26 C28 121.3(2) . . ?
C27 C26 C28 120.5(2) . . ?
C22 C27 C26 120.0(2) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        26.57
_diffrn_measured_fraction_theta_full 0.914
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 994164'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sp2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 Cl N2 O3'
_chemical_formula_weight         508.98

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

loop_
_symmetry_equiv_pos_as_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'
'-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                   19.479(3)
_cell_length_b                   10.6597(18)
_cell_length_c                   24.687(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.835(2)
_cell_angle_gamma                90.00
_cell_volume                     4906.3(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2128
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16810
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.29
_reflns_number_total             4418
_reflns_number_gt                3275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0648P)²+4.3903P] 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         4418
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.63172(4) 1.02557(7) 0.20343(4) 0.0876(3) Uani 1 1 d . . .
O1 O 0.38484(8) 0.58422(15) 0.24287(6) 0.0479(4) Uani 1 1 d . . .
O2 O 0.28957(9) 0.47302(16) -0.00661(7) 0.0605(5) Uani 1 1 d . . .
O3 O 0.51431(8) 0.56091(15) 0.09050(7) 0.0487(4) Uani 1 1 d . . .
N1 N 0.38623(9) 0.57732(16) 0.05235(7) 0.0399(4) Uani 1 1 d . . .
N2 N 0.33750(10) 0.83572(17) 0.07647(7) 0.0416(4) Uani 1 1 d . . .
H2 H 0.3032 0.8876 0.0623 0.050 Uiso 1 1 calc R . .
C1 C 0.70300(14) 0.8877(3) 0.12448(14) 0.0843(10) Uani 1 1 d . . .
H1A H 0.6984 0.9774 0.1224 0.126 Uiso 1 1 calc R . .
H1B H 0.7092 0.8562 0.0898 0.126 Uiso 1 1 calc R . .
H1C H 0.7439 0.8654 0.1554 0.126 Uiso 1 1 calc R . .
C2 C 0.63592(12) 0.8312(3) 0.13376(11) 0.0574(7) Uani 1 1 d . . .
C3 C 0.60042(13) 0.8861(2) 0.16890(11) 0.0538(7) Uani 1 1 d . . .
C4 C 0.53964(11) 0.8335(2) 0.17821(9) 0.0454(6) Uani 1 1 d . . .
H4 H 0.5167 0.8724 0.2019 0.054 Uiso 1 1 calc R . .
C5 C 0.51426(10) 0.7227(2) 0.15167(9) 0.0380(5) Uani 1 1 d . . .
C6 C 0.45309(10) 0.64000(19) 0.15422(8) 0.0357(5) Uani 1 1 d . . .
H6 H 0.4713 0.5882 0.1881 0.043 Uiso 1 1 calc R . .
C7 C 0.38563(10) 0.69766(19) 0.15930(8) 0.0343(5) Uani 1 1 d . . .
C8 C 0.33935(10) 0.78327(19) 0.12639(8) 0.0345(5) Uani 1 1 d . . .
C9 C 0.28372(10) 0.8169(2) 0.15446(8) 0.0369(5) Uani 1 1 d . . .
C10 C 0.23092(12) 0.9076(2) 0.14199(9) 0.0465(6) Uani 1 1 d . . .
H10 H 0.2244 0.9597 0.1107 0.056 Uiso 1 1 calc R . .
C11 C 0.18765(12) 0.9186(2) 0.17786(10) 0.0519(6) Uani 1 1 d . . .
H11 H 0.1520 0.9796 0.1706 0.062 Uiso 1 1 calc R . .
C12 C 0.44621(11) 0.5503(2) 0.10305(9) 0.0391(5) Uani 1 1 d . . .
C13 C 0.37784(12) 0.6866(2) 0.01435(9) 0.0442(5) Uani 1 1 d . . .
H13 H 0.3280 0.6849 -0.0097 0.053 Uiso 1 1 calc R . .
C14 C 0.38820(12) 0.8131(2) 0.04401(9) 0.0425(5) Uani 1 1 d . . .
H14 H 0.4368 0.8157 0.0702 0.051 Uiso 1 1 calc R . .
C15 C 0.29408(10) 0.7412(2) 0.20205(9) 0.0369(5) Uani 1 1 d . . .
C16 C 0.35924(11) 0.66248(19) 0.20646(8) 0.0355(5) Uani 1 1 d . . .
C17 C 0.25050(11) 0.7505(2) 0.23668(9) 0.0446(5) Uani 1 1 d . . .
H17 H 0.2567 0.6980 0.2678 0.054 Uiso 1 1 calc R . .
C18 C 0.19674(12) 0.8409(2) 0.22369(10) 0.0517(6) Uani 1 1 d . . .
H18 H 0.1664 0.8489 0.2465 0.062 Uiso 1 1 calc R . .
C19 C 0.38128(13) 0.9187(2) 0.00143(9) 0.0484(6) Uani 1 1 d . . .
H19A H 0.3321 0.9230 -0.0224 0.058 Uiso 1 1 calc R . .
H19B H 0.3926 0.9978 0.0215 0.058 Uiso 1 1 calc R . .
C20 C 0.43078(14) 0.9002(2) -0.03546(11) 0.0579(7) Uani 1 1 d . . .
H20A H 0.4244 0.9687 -0.0623 0.070 Uiso 1 1 calc R . .
H20B H 0.4802 0.9012 -0.0119 0.070 Uiso 1 1 calc R . .
C21 C 0.41572(16) 0.7790(3) -0.06675(11) 0.0625(7) Uani 1 1 d . . .
H21A H 0.4484 0.7685 -0.0895 0.075 Uiso 1 1 calc R . .
H21B H 0.3671 0.7794 -0.0919 0.075 Uiso 1 1 calc R . .
C22 C 0.42472(14) 0.6714(2) -0.02545(10) 0.0548(6) Uani 1 1 d . . .
H22A H 0.4746 0.6661 -0.0032 0.066 Uiso 1 1 calc R . .
H22B H 0.4123 0.5935 -0.0463 0.066 Uiso 1 1 calc R . .
C23 C 0.34257(12) 0.4755(2) 0.03479(10) 0.0448(5) Uani 1 1 d . . .
C24 C 0.37169(13) 0.3737(2) 0.07516(10) 0.0462(6) Uani 1 1 d . . .
C25 C 0.43224(12) 0.4163(2) 0.11514(9) 0.0432(5) Uani 1 1 d . . .
C26 C 0.46987(14) 0.3411(2) 0.15902(11) 0.0558(6) Uani 1 1 d . . .
H26 H 0.5105 0.3704 0.1861 0.067 Uiso 1 1 calc R . .
C27 C 0.44501(17) 0.2202(3) 0.16133(13) 0.0693(8) Uani 1 1 d . . .
H27 H 0.4694 0.1674 0.1905 0.083 Uiso 1 1 calc R . .
C28 C 0.38507(18) 0.1769(3) 0.12132(13) 0.0738(8) Uani 1 1 d . . .
H28 H 0.3698 0.0950 0.1239 0.089 Uiso 1 1 calc R . .
C29 C 0.34683(16) 0.2521(2) 0.07731(12) 0.0641(7) Uani 1 1 d . . .
H29 H 0.3062 0.2226 0.0503 0.077 Uiso 1 1 calc R . .
C30 C 0.54820(11) 0.6688(2) 0.11587(9) 0.0429(5) Uani 1 1 d . . .
C31 C 0.60821(12) 0.7201(3) 0.10602(11) 0.0537(6) Uani 1 1 d . . .
H31 H 0.6299 0.6816 0.0814 0.064 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
Cl1 C3 1.734(3) . ?
O1 C16 1.222(2) . ?
O2 C23 1.225(3) . ?
O3 C30 1.382(3) . ?
O3 C12 1.451(3) . ?
N1 C23 1.370(3) . ?
N1 C12 1.472(3) . ?
N1 C13 1.475(3) . ?
N2 C8 1.344(3) . ?
N2 C14 1.461(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.515(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.386(4) . ?
C2 C31 1.396(4) . ?
C3 C4 1.388(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C30 1.374(3) . ?
C5 C6 1.498(3) . ?
C6 C7 1.489(3) . ?
C6 C12 1.559(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.372(3) . ?
C7 C16 1.451(3) . ?
C8 C9 1.489(3) . ?
C9 C10 1.380(3) . ?
C9 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C18 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C25 1.500(3) . ?
C13 C14 1.520(3) . ?
C13 C22 1.531(3) . ?
C13 H13 0.9800 . ?
C14 C19 1.520(3) . ?
C14 H14 0.9800 . ?
C15 C17 1.372(3) . ?
C15 C16 1.499(3) . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.519(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.490(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.471(3) . ?
C24 C25 1.377(3) . ?
C24 C29 1.391(3) . ?
C25 C26 1.376(3) . ?
C26 C27 1.383(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.373(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.374(3) . ?
C31 H31 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
C30 O3 C12 108.33(16) . . ?
C23 N1 C12 112.40(17) . . ?
C23 N1 C13 118.71(18) . . ?
C12 N1 C13 127.58(17) . . ?
C8 N2 C14 126.26(18) . . ?
C8 N2 H2 116.9 . . ?
C14 N2 H2 116.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C31 118.3(2) . . ?
C3 C2 C1 122.3(3) . . ?
C31 C2 C1 119.4(3) . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 Cl1 120.1(2) . . ?
C4 C3 Cl1 117.4(2) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C30 119.6(2) . . ?
C4 C5 C6 131.9(2) . . ?
C30 C5 C6 108.51(19) . . ?
C7 C6 C5 119.52(18) . . ?
C7 C6 C12 116.79(16) . . ?
C5 C6 C12 102.11(16) . . ?
C7 C6 H6 105.8 . . ?
C5 C6 H6 105.8 . . ?
C12 C6 H6 105.8 . . ?
C8 C7 C16 108.81(17) . . ?
C8 C7 C6 132.04(19) . . ?
C16 C7 C6 119.15(18) . . ?
N2 C8 C7 131.17(19) . . ?
N2 C8 C9 119.78(18) . . ?
C7 C8 C9 109.05(18) . . ?
C10 C9 C15 120.74(19) . . ?
C10 C9 C8 131.3(2) . . ?
C15 C9 C8 107.85(18) . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C18 C11 C10 121.1(2) . . ?
C18 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O3 C12 N1 110.65(17) . . ?
O3 C12 C25 110.28(17) . . ?
N1 C12 C25 102.15(17) . . ?
O3 C12 C6 104.81(16) . . ?
N1 C12 C6 115.44(16) . . ?
C25 C12 C6 113.63(18) . . ?
N1 C13 C14 114.81(17) . . ?
N1 C13 C22 110.34(18) . . ?
C14 C13 C22 112.48(19) . . ?
N1 C13 H13 106.2 . . ?
C14 C13 H13 106.2 . . ?
C22 C13 H13 106.2 . . ?
N2 C14 C19 108.57(18) . . ?
N2 C14 C13 113.21(18) . . ?
C19 C14 C13 110.58(17) . . ?
N2 C14 H14 108.1 . . ?
C19 C14 H14 108.1 . . ?
C13 C14 H14 108.1 . . ?
C17 C15 C9 121.3(2) . . ?
C17 C15 C16 131.2(2) . . ?
C9 C15 C16 107.37(18) . . ?
O1 C16 C7 127.06(19) . . ?
O1 C16 C15 126.31(19) . . ?
C7 C16 C15 106.63(17) . . ?
C15 C17 C18 117.8(2) . . ?
C15 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C11 C18 C17 121.1(2) . . ?
C11 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C14 111.9(2) . . ?
C20 C19 H19A 109.2 . . ?
C14 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C14 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 111.1(2) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 110.0(2) . . ?
C20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 C13 112.2(2) . . ?
C21 C22 H22A 109.2 . . ?
C13 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C13 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O2 C23 N1 125.3(2) . . ?
O2 C23 C24 128.0(2) . . ?
N1 C23 C24 106.72(19) . . ?
C25 C24 C29 121.0(2) . . ?
C25 C24 C23 108.9(2) . . ?
C29 C24 C23 130.0(2) . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 C12 128.7(2) . . ?
C24 C25 C12 109.8(2) . . ?
C25 C26 C27 117.5(3) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
C28 C27 C26 121.2(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 121.6(3) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C28 C29 C24 117.2(3) . . ?
C28 C29 H29 121.4 . . ?
C24 C29 H29 121.4 . . ?
C5 C30 C31 122.6(2) . . ?
C5 C30 O3 112.58(18) . . ?
C31 C30 O3 124.8(2) . . ?
C30 C31 C2 118.6(2) . . ?
C30 C31 H31 120.7 . . ?
C2 C31 H31 120.7 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 994165'
