# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_trya2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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           ?
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.8993(6)
_cell_length_b                   22.5466(14)
_cell_length_c                   8.1910(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.827(3)
_cell_angle_gamma                90.00
_cell_volume                     1555.58(17)
_cell_formula_units_Z            4
_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    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.081
_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            2226
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         23.26
_reflns_number_total             2226
_reflns_number_gt                1959
_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)+(0.0478P)²+0.5122P] 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         2226
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C8 C 0.86781(19) 0.48468(7) 0.79020(19) 0.0302(4) Uani 1 1 d . . .
H8 H 0.9769 0.4905 0.8215 0.036 Uiso 1 1 calc R . .
C15 C 0.43306(19) 0.35119(8) 0.4910(2) 0.0363(4) Uani 1 1 d . . .
H15A H 0.4327 0.3162 0.4240 0.054 Uiso 1 1 calc R . .
H15B H 0.3633 0.3803 0.4200 0.054 Uiso 1 1 calc R . .
H15C H 0.3974 0.3413 0.5864 0.054 Uiso 1 1 calc R . .
O2 O 0.71777(13) 0.29809(5) 0.47107(15) 0.0363(3) Uani 1 1 d . . .
C19 C 0.94259(18) 0.40177(7) 0.4927(2) 0.0302(4) Uani 1 1 d . . .
H19A H 1.0302 0.4288 0.5431 0.036 Uiso 1 1 calc R . .
H19B H 0.9851 0.3669 0.4536 0.036 Uiso 1 1 calc R . .
C16 C 0.82684(19) 0.43119(8) 0.3400(2) 0.0350(4) Uani 1 1 d . . .
H16 H 0.7746 0.4648 0.3596 0.042 Uiso 1 1 calc R . .
C1 C 1.21004(19) 0.28695(7) 1.0514(2) 0.0315(4) Uani 1 1 d . . .
H1 H 1.2813 0.2657 1.1403 0.038 Uiso 1 1 calc R . .
C2 C 1.04978(19) 0.28188(7) 1.0248(2) 0.0318(4) Uani 1 1 d . . .
H2 H 1.0141 0.2578 1.0969 0.038 Uiso 1 1 calc R . .
O1 O 0.78171(12) 0.30895(5) 0.86333(15) 0.0346(3) Uani 1 1 d . . .
H1A H 0.7618 0.2782 0.9056 0.052 Uiso 1 1 calc R . .
C11 C 0.6099(2) 0.51755(8) 0.7878(2) 0.0390(5) Uani 1 1 d . . .
H11 H 0.5475 0.5455 0.8192 0.047 Uiso 1 1 calc R . .
C12 C 0.7713(2) 0.52649(7) 0.8331(2) 0.0379(5) Uani 1 1 d . . .
H12 H 0.8162 0.5606 0.8928 0.045 Uiso 1 1 calc R . .
C5 C 1.15604(17) 0.35355(7) 0.81413(19) 0.0269(4) Uani 1 1 d . . .
H5 H 1.1925 0.3780 0.7435 0.032 Uiso 1 1 calc R . .
C10 C 0.5386(2) 0.46754(7) 0.6961(2) 0.0337(4) Uani 1 1 d . . .
H10 H 0.4296 0.4615 0.6653 0.040 Uiso 1 1 calc R . .
N1 N 0.59217(14) 0.37488(5) 0.55492(16) 0.0254(3) Uani 1 1 d . . .
C17 C 0.7938(2) 0.41290(9) 0.1804(2) 0.0485(5) Uani 1 1 d . . .
H17A H 0.8438 0.3794 0.1562 0.058 Uiso 1 1 calc R . .
H17B H 0.7204 0.4334 0.0914 0.058 Uiso 1 1 calc R . .
C7 C 0.79903(17) 0.43463(6) 0.70077(18) 0.0238(4) Uani 1 1 d . . .
C13 C 0.87171(17) 0.38268(7) 0.63513(19) 0.0238(4) Uani 1 1 d . . .
C4 C 0.99276(17) 0.34883(6) 0.78147(19) 0.0232(4) Uani 1 1 d . . .
C6 C 1.26729(18) 0.32330(7) 0.9477(2) 0.0283(4) Uani 1 1 d . . .
C18 C 1.44256(19) 0.32915(8) 0.9771(2) 0.0407(5) Uani 1 1 d . . .
H18A H 1.4763 0.2980 0.9168 0.061 Uiso 1 1 calc R . .
H18B H 1.4995 0.3262 1.0983 0.061 Uiso 1 1 calc R . .
H18C H 1.4637 0.3669 0.9350 0.061 Uiso 1 1 calc R . .
C9 C 0.63568(18) 0.42711(7) 0.65246(18) 0.0249(4) Uani 1 1 d . . .
C14 C 0.72219(18) 0.34512(7) 0.54629(19) 0.0258(4) Uani 1 1 d . . .
C3 C 0.94092(18) 0.31243(7) 0.8909(2) 0.0266(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 C7 1.377(2) . ?
C8 C12 1.395(2) . ?
C8 H8 0.9300 . ?
C15 N1 1.444(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2 C14 1.2204(18) . ?
C19 C16 1.495(2) . ?
C19 C13 1.555(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 C17 1.310(2) . ?
C16 H16 0.9300 . ?
C1 C2 1.376(2) . ?
C1 C6 1.390(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H2 0.9300 . ?
O1 C3 1.3631(18) . ?
O1 H1A 0.8200 . ?
C11 C12 1.378(3) . ?
C11 C10 1.389(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C5 C4 1.394(2) . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C10 C9 1.380(2) . ?
C10 H10 0.9300 . ?
N1 C14 1.359(2) . ?
N1 C9 1.405(2) . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C7 C9 1.388(2) . ?
C7 C13 1.518(2) . ?
C13 C4 1.532(2) . ?
C13 C14 1.547(2) . ?
C4 C3 1.399(2) . ?
C6 C18 1.505(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C7 C8 C12 118.96(16) . . ?
C7 C8 H8 120.5 . . ?
C12 C8 H8 120.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C19 C13 114.45(13) . . ?
C16 C19 H19A 108.6 . . ?
C13 C19 H19A 108.6 . . ?
C16 C19 H19B 108.6 . . ?
C13 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C17 C16 C19 124.57(18) . . ?
C17 C16 H16 117.7 . . ?
C19 C16 H16 117.7 . . ?
C2 C1 C6 121.18(14) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.46(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 O1 H1A 109.5 . . ?
C12 C11 C10 121.26(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C8 120.43(15) . . ?
C11 C12 H12 119.8 . . ?
C8 C12 H12 119.8 . . ?
C4 C5 C6 123.06(15) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C9 C10 C11 117.48(16) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C14 N1 C9 111.12(12) . . ?
C14 N1 C15 123.38(13) . . ?
C9 N1 C15 125.03(13) . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C8 C7 C9 119.78(14) . . ?
C8 C7 C13 130.84(14) . . ?
C9 C7 C13 109.36(12) . . ?
C7 C13 C4 112.32(12) . . ?
C7 C13 C14 100.89(12) . . ?
C4 C13 C14 112.11(12) . . ?
C7 C13 C19 111.99(12) . . ?
C4 C13 C19 111.83(12) . . ?
C14 C13 C19 107.11(12) . . ?
C5 C4 C3 117.43(14) . . ?
C5 C4 C13 122.58(13) . . ?
C3 C4 C13 119.98(13) . . ?
C1 C6 C5 117.42(15) . . ?
C1 C6 C18 121.28(14) . . ?
C5 C6 C18 121.30(15) . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C9 C7 122.06(14) . . ?
C10 C9 N1 128.33(14) . . ?
C7 C9 N1 109.60(13) . . ?
O2 C14 N1 124.47(14) . . ?
O2 C14 C13 126.57(14) . . ?
N1 C14 C13 108.83(13) . . ?
O1 C3 C2 121.68(14) . . ?
O1 C3 C4 117.88(13) . . ?
C2 C3 C4 120.43(14) . . ?

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
C13 C19 C16 C17 -123.29(18) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C10 C11 C12 C8 -1.1(3) . . . . ?
C7 C8 C12 C11 0.5(2) . . . . ?
C12 C11 C10 C9 0.1(2) . . . . ?
C12 C8 C7 C9 1.1(2) . . . . ?
C12 C8 C7 C13 179.10(15) . . . . ?
C8 C7 C13 C4 61.3(2) . . . . ?
C9 C7 C13 C4 -120.54(13) . . . . ?
C8 C7 C13 C14 -179.14(15) . . . . ?
C9 C7 C13 C14 -0.99(15) . . . . ?
C8 C7 C13 C19 -65.5(2) . . . . ?
C9 C7 C13 C19 112.64(14) . . . . ?
C16 C19 C13 C7 -57.12(17) . . . . ?
C16 C19 C13 C4 175.80(13) . . . . ?
C16 C19 C13 C14 52.60(17) . . . . ?
C6 C5 C4 C3 0.9(2) . . . . ?
C6 C5 C4 C13 179.51(14) . . . . ?
C7 C13 C4 C5 -105.28(16) . . . . ?
C14 C13 C4 C5 141.93(14) . . . . ?
C19 C13 C4 C5 21.61(19) . . . . ?
C7 C13 C4 C3 73.29(17) . . . . ?
C14 C13 C4 C3 -39.50(18) . . . . ?
C19 C13 C4 C3 -159.82(14) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
C2 C1 C6 C18 179.71(15) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C18 179.28(15) . . . . ?
C11 C10 C9 C7 1.5(2) . . . . ?
C11 C10 C9 N1 -177.10(14) . . . . ?
C8 C7 C9 C10 -2.2(2) . . . . ?
C13 C7 C9 C10 179.44(14) . . . . ?
C8 C7 C9 N1 176.69(13) . . . . ?
C13 C7 C9 N1 -1.70(16) . . . . ?
C14 N1 C9 C10 -177.08(15) . . . . ?
C15 N1 C9 C10 -4.8(2) . . . . ?
C14 N1 C9 C7 4.15(17) . . . . ?
C15 N1 C9 C7 176.40(14) . . . . ?
C9 N1 C14 O2 179.17(14) . . . . ?
C15 N1 C14 O2 6.8(2) . . . . ?
C9 N1 C14 C13 -4.75(16) . . . . ?
C15 N1 C14 C13 -177.16(13) . . . . ?
C7 C13 C14 O2 179.40(15) . . . . ?
C4 C13 C14 O2 -60.9(2) . . . . ?
C19 C13 C14 O2 62.14(19) . . . . ?
C7 C13 C14 N1 3.43(15) . . . . ?
C4 C13 C14 N1 123.14(13) . . . . ?
C19 C13 C14 N1 -113.84(14) . . . . ?
C1 C2 C3 O1 -178.94(14) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C5 C4 C3 O1 178.02(13) . . . . ?
C13 C4 C3 O1 -0.6(2) . . . . ?
C5 C4 C3 C2 -0.9(2) . . . . ?
C13 C4 C3 C2 -179.55(14) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 1007347'
#######################################################################
#
#                 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_platon

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cl3 N O2'
_chemical_formula_weight         434.72

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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.910(3)
_cell_length_b                   9.482(3)
_cell_length_c                   14.090(5)
_cell_angle_alpha                101.315(16)
_cell_angle_beta                 101.159(16)
_cell_angle_gamma                110.480(17)
_cell_volume                     1048.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(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             448
_exptl_absorpt_coefficient_mu    0.455
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3028
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.44
_reflns_number_total             3028
_reflns_number_gt                1930
_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)+(0.0100P)²+2.2853P] 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         3028
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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
O1 O 0.6648(4) 0.5489(3) 0.2747(2) 0.0379(8) Uani 1 1 d . . .
H1 H 0.6920 0.6346 0.3135 0.057 Uiso 1 1 d R . .
O3 O 0.8357(4) 0.8377(3) 0.4012(2) 0.0369(8) Uani 1 1 d . . .
N1 N 1.0657(5) 1.0301(4) 0.3856(3) 0.0340(10) Uani 1 1 d . . .
C19 C 0.5196(7) 0.9234(6) 0.1488(4) 0.0591(16) Uani 1 1 d . . .
H19 H 0.4748 0.9929 0.1740 0.071 Uiso 1 1 calc R . .
C20 C 0.6609(6) 0.9214(5) 0.2092(4) 0.0453(13) Uani 1 1 d . . .
H20 H 0.7106 0.9903 0.2741 0.054 Uiso 1 1 calc R . .
C21 C 0.4443(6) 0.8237(6) 0.0518(4) 0.0463(13) Uani 1 1 d . . .
H21 H 0.3509 0.8272 0.0112 0.056 Uiso 1 1 calc R . .
C22 C 0.5091(5) 0.7192(5) 0.0163(3) 0.0388(12) Uani 1 1 d . . .
H22 H 0.4585 0.6504 -0.0486 0.047 Uiso 1 1 calc R . .
C23 C 0.6506(5) 0.7158(5) 0.0771(3) 0.0305(10) Uani 1 1 d . . .
H23 H 0.6930 0.6441 0.0523 0.037 Uiso 1 1 calc R . .
C24 C 0.7291(5) 0.8175(5) 0.1738(3) 0.0249(10) Uani 1 1 d . . .
C25 C 0.9107(5) 0.6670(4) 0.2195(3) 0.0248(10) Uani 1 1 d . . .
C26 C 0.7976(5) 0.5412(5) 0.2403(3) 0.0302(10) Uani 1 1 d . . .
C27 C 0.8109(6) 0.3977(5) 0.2234(3) 0.0358(11) Uani 1 1 d . . .
H27 H 0.7352 0.3146 0.2382 0.043 Uiso 1 1 calc R . .
C28 C 1.0486(6) 0.4977(5) 0.1623(3) 0.0329(11) Uani 1 1 d . . .
C29 C 1.0360(5) 0.6422(5) 0.1820(3) 0.0287(10) Uani 1 1 d . . .
H29 H 1.1145 0.7260 0.1695 0.034 Uiso 1 1 calc R . .
C30 C 0.9353(6) 0.3764(5) 0.1849(3) 0.0375(12) Uani 1 1 d . . .
H30 H 0.9426 0.2794 0.1740 0.045 Uiso 1 1 calc R . .
C31 C 1.1362(5) 1.0681(5) 0.3082(3) 0.0285(10) Uani 1 1 d . . .
C32 C 1.0398(5) 0.9529(4) 0.2175(3) 0.0253(10) Uani 1 1 d . . .
C33 C 1.0789(5) 0.9694(5) 0.1290(3) 0.0280(10) Uani 1 1 d . . .
H33 H 1.0135 0.8956 0.0673 0.034 Uiso 1 1 calc R . .
C34 C 1.2187(5) 1.0993(5) 0.1350(4) 0.0356(11) Uani 1 1 d . . .
H34 H 1.2481 1.1117 0.0764 0.043 Uiso 1 1 calc R . .
C35 C 1.3156(5) 1.2111(5) 0.2263(4) 0.0388(12) Uani 1 1 d . . .
H35 H 1.4092 1.2964 0.2279 0.047 Uiso 1 1 calc R . .
C36 C 1.2753(5) 1.1978(5) 0.3151(4) 0.0381(12) Uani 1 1 d . . .
H36 H 1.3391 1.2729 0.3766 0.046 Uiso 1 1 calc R . .
C39 C 1.1826(7) 0.4776(6) 0.1162(4) 0.0520(14) Uani 1 1 d . . .
H39A H 1.2908 0.5422 0.1630 0.078 Uiso 1 1 calc R . .
H39B H 1.1744 0.5084 0.0550 0.078 Uiso 1 1 calc R . .
H39C H 1.1675 0.3694 0.1012 0.078 Uiso 1 1 calc R . .
C41 C 0.8969(5) 0.8270(4) 0.2359(3) 0.0243(10) Uani 1 1 d . . .
C42 C 0.9259(5) 0.8974(5) 0.3511(3) 0.0301(11) Uani 1 1 d . . .
Cl2 Cl 0.4214(3) 0.6884(3) 0.39719(15) 0.1196(8) Uani 1 1 d . . .
Cl7 Cl 0.2464(3) 0.5275(3) 0.51517(16) 0.1109(8) Uani 1 1 d . . .
Cl15 Cl 0.2400(3) 0.8191(3) 0.50787(17) 0.1307(9) Uani 1 1 d . . .
C37 C 0.2467(7) 0.6517(7) 0.4397(4) 0.0621(16) Uani 1 1 d . . .
H37 H 0.1469 0.5987 0.3814 0.075 Uiso 1 1 calc R . .
H1A H 1.098(6) 1.077(6) 0.442(4) 0.055(18) 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
O1 C26 1.382(5) . ?
O1 H1 0.8089 . ?
O3 C42 1.235(5) . ?
N1 C42 1.342(5) . ?
N1 C31 1.406(6) . ?
N1 H1A 0.77(5) . ?
C19 C21 1.381(7) . ?
C19 C20 1.384(6) . ?
C19 H19 0.9300 . ?
C20 C24 1.390(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(5) . ?
C23 H23 0.9300 . ?
C24 C41 1.542(5) . ?
C25 C26 1.391(5) . ?
C25 C29 1.394(6) . ?
C25 C41 1.541(5) . ?
C26 C27 1.386(6) . ?
C27 C30 1.383(6) . ?
C27 H27 0.9300 . ?
C28 C30 1.378(6) . ?
C28 C29 1.392(6) . ?
C28 C39 1.515(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C36 1.377(6) . ?
C31 C32 1.391(5) . ?
C32 C33 1.381(6) . ?
C32 C41 1.517(5) . ?
C33 C34 1.385(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.384(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C41 C42 1.562(6) . ?
Cl2 C37 1.722(6) . ?
Cl7 C37 1.734(6) . ?
Cl15 C37 1.714(6) . ?
C37 H37 0.9800 . ?

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
C26 O1 H1 110.1 . . ?
C42 N1 C31 112.1(4) . . ?
C42 N1 H1A 120(4) . . ?
C31 N1 H1A 127(4) . . ?
C21 C19 C20 120.9(5) . . ?
C21 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C24 120.7(4) . . ?
C19 C20 H20 119.7 . . ?
C24 C20 H20 119.7 . . ?
C22 C21 C19 119.1(4) . . ?
C22 C21 H21 120.4 . . ?
C19 C21 H21 120.4 . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 121.1(4) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C20 118.0(4) . . ?
C23 C24 C41 120.9(4) . . ?
C20 C24 C41 120.9(4) . . ?
C26 C25 C29 117.5(4) . . ?
C26 C25 C41 121.3(4) . . ?
C29 C25 C41 121.2(4) . . ?
O1 C26 C27 116.5(4) . . ?
O1 C26 C25 123.2(4) . . ?
C27 C26 C25 120.3(4) . . ?
C30 C27 C26 120.8(4) . . ?
C30 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C30 C28 C29 117.9(4) . . ?
C30 C28 C39 122.3(4) . . ?
C29 C28 C39 119.8(4) . . ?
C28 C29 C25 122.9(4) . . ?
C28 C29 H29 118.5 . . ?
C25 C29 H29 118.5 . . ?
C28 C30 C27 120.6(4) . . ?
C28 C30 H30 119.7 . . ?
C27 C30 H30 119.7 . . ?
C36 C31 C32 122.8(4) . . ?
C36 C31 N1 128.1(4) . . ?
C32 C31 N1 109.1(4) . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 C41 130.6(4) . . ?
C31 C32 C41 109.5(4) . . ?
C32 C33 C34 117.9(4) . . ?
C32 C33 H33 121.0 . . ?
C34 C33 H33 121.0 . . ?
C35 C34 C33 121.5(4) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C36 C35 C34 121.1(4) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C31 C36 C35 116.9(4) . . ?
C31 C36 H36 121.6 . . ?
C35 C36 H36 121.6 . . ?
C28 C39 H39A 109.5 . . ?
C28 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C28 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C32 C41 C25 113.5(3) . . ?
C32 C41 C24 109.4(3) . . ?
C25 C41 C24 113.5(3) . . ?
C32 C41 C42 100.5(3) . . ?
C25 C41 C42 108.4(3) . . ?
C24 C41 C42 110.8(3) . . ?
O3 C42 N1 126.5(4) . . ?
O3 C42 C41 124.9(4) . . ?
N1 C42 C41 108.6(4) . . ?
Cl15 C37 Cl2 112.9(4) . . ?
Cl15 C37 Cl7 109.0(3) . . ?
Cl2 C37 Cl7 108.4(3) . . ?
Cl15 C37 H37 108.8 . . ?
Cl2 C37 H37 108.8 . . ?
Cl7 C37 H37 108.8 . . ?

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
C21 C19 C20 C24 -0.7(8) . . . . ?
C20 C19 C21 C22 1.4(8) . . . . ?
C19 C21 C22 C23 -0.9(7) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C20 1.1(6) . . . . ?
C22 C23 C24 C41 -172.7(4) . . . . ?
C19 C20 C24 C23 -0.6(7) . . . . ?
C19 C20 C24 C41 173.2(4) . . . . ?
C29 C25 C26 O1 -177.9(4) . . . . ?
C41 C25 C26 O1 1.2(6) . . . . ?
C29 C25 C26 C27 -0.2(6) . . . . ?
C41 C25 C26 C27 178.9(4) . . . . ?
O1 C26 C27 C30 177.2(4) . . . . ?
C25 C26 C27 C30 -0.6(6) . . . . ?
C30 C28 C29 C25 -2.5(6) . . . . ?
C39 C28 C29 C25 176.7(4) . . . . ?
C26 C25 C29 C28 1.8(6) . . . . ?
C41 C25 C29 C28 -177.3(4) . . . . ?
C29 C28 C30 C27 1.6(6) . . . . ?
C39 C28 C30 C27 -177.6(4) . . . . ?
C26 C27 C30 C28 -0.1(7) . . . . ?
C42 N1 C31 C36 177.5(4) . . . . ?
C42 N1 C31 C32 -1.0(5) . . . . ?
C36 C31 C32 C33 -2.4(6) . . . . ?
N1 C31 C32 C33 176.2(4) . . . . ?
C36 C31 C32 C41 180.0(4) . . . . ?
N1 C31 C32 C41 -1.4(5) . . . . ?
C31 C32 C33 C34 2.4(6) . . . . ?
C41 C32 C33 C34 179.4(4) . . . . ?
C32 C33 C34 C35 -0.9(6) . . . . ?
C33 C34 C35 C36 -0.6(7) . . . . ?
C32 C31 C36 C35 0.8(6) . . . . ?
N1 C31 C36 C35 -177.5(4) . . . . ?
C34 C35 C36 C31 0.7(6) . . . . ?
C33 C32 C41 C25 70.1(5) . . . . ?
C31 C32 C41 C25 -112.6(4) . . . . ?
C33 C32 C41 C24 -57.8(5) . . . . ?
C31 C32 C41 C24 119.5(4) . . . . ?
C33 C32 C41 C42 -174.4(4) . . . . ?
C31 C32 C41 C42 2.9(4) . . . . ?
C26 C25 C41 C32 175.1(4) . . . . ?
C29 C25 C41 C32 -5.8(5) . . . . ?
C26 C25 C41 C24 -59.2(5) . . . . ?
C29 C25 C41 C24 119.9(4) . . . . ?
C26 C25 C41 C42 64.4(5) . . . . ?
C29 C25 C41 C42 -116.5(4) . . . . ?
C23 C24 C41 C32 91.2(4) . . . . ?
C20 C24 C41 C32 -82.3(5) . . . . ?
C23 C24 C41 C25 -36.6(5) . . . . ?
C20 C24 C41 C25 149.8(4) . . . . ?
C23 C24 C41 C42 -158.8(4) . . . . ?
C20 C24 C41 C42 27.6(5) . . . . ?
C31 N1 C42 O3 -178.2(4) . . . . ?
C31 N1 C42 C41 3.0(5) . . . . ?
C32 C41 C42 O3 177.7(4) . . . . ?
C25 C41 C42 O3 -63.1(5) . . . . ?
C24 C41 C42 O3 62.1(5) . . . . ?
C32 C41 C42 N1 -3.5(4) . . . . ?
C25 C41 C42 N1 115.7(4) . . . . ?
C24 C41 C42 N1 -119.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.44
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 1007348'
#######################################################################
#
#                 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_try_1_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H34 N2 O5'
_chemical_formula_sum            'C27 H34 N2 O5'
_chemical_formula_weight         466.56

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/c

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

_cell_length_a                   15.1024(9)
_cell_length_b                   14.8289(8)
_cell_length_c                   11.8933(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6680(17)
_cell_angle_gamma                90.00
_cell_volume                     2564.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3247
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      34.34

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1122
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   multi-scan

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5038
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.71
_reflns_number_total             2589
_reflns_number_gt                2267
_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)+(0.1000P)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_number_reflns         2589
_refine_ls_number_parameters     314
_refine_ls_number_restraints     95
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.291
_refine_ls_restrained_S_all      1.269
_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
O001 O 0.61469(11) 0.33430(9) 0.08194(13) 0.0664(5) Uani 1 1 d U . .
O002 O 0.76409(11) 0.34785(10) 0.18377(14) 0.0663(5) Uani 1 1 d U . .
O003 O 0.78419(12) 0.53041(10) 0.30515(12) 0.0702(5) Uani 1 1 d U . .
N004 N 0.69213(11) 0.45625(10) 0.05538(13) 0.0495(5) Uani 1 1 d U . .
N005 N 0.76056(13) 0.59822(10) 0.13376(16) 0.0612(5) Uani 1 1 d U . .
O006 O 0.75847(15) 0.68168(12) 0.29162(15) 0.0925(6) Uani 1 1 d U . .
O1 O 1.00871(12) 0.33822(14) -0.25411(17) 0.0956(6) Uani 1 1 d U . .
C22 C 0.63252(15) 0.47852(13) -0.05612(17) 0.0502(6) Uani 1 1 d U . .
C7 C 0.77329(14) 0.51406(13) 0.07746(17) 0.0509(6) Uani 1 1 d U . .
H7 H 0.8290 0.4823 0.1208 0.061 Uiso 1 1 calc R . .
C10 C 0.77970(15) 0.54470(13) -0.04558(17) 0.0546(6) Uani 1 1 d U . .
C23 C 0.69568(17) 0.37565(14) 0.1138(2) 0.0540(6) Uani 1 1 d U . .
C13 C 0.84312(14) 0.48830(13) -0.09581(17) 0.0515(6) Uani 1 1 d U . .
C11 C 0.68010(15) 0.53186(12) -0.11594(17) 0.0527(6) Uani 1 1 d U . .
C21 C 0.54110(16) 0.45640(15) -0.10439(19) 0.0612(6) Uani 1 1 d U . .
H21 H 0.5090 0.4216 -0.0636 0.073 Uiso 1 1 calc R . .
C6 C 0.76759(16) 0.60930(17) 0.2490(2) 0.0649(7) Uani 1 1 d U . .
C16 C 0.95307(16) 0.38295(17) -0.1993(2) 0.0658(7) Uani 1 1 d U . .
C12 C 0.63667(19) 0.56257(15) -0.2263(2) 0.0672(7) Uani 1 1 d U . .
H12 H 0.6682 0.5980 -0.2673 0.081 Uiso 1 1 calc R . .
C4 C 0.80915(17) 0.52749(17) 0.43317(18) 0.0689(7) Uani 1 1 d U . .
C25 C 0.59998(17) 0.24640(14) 0.1339(2) 0.0691(7) Uani 1 1 d U . .
C9 C 0.80601(18) 0.64471(14) -0.0275(2) 0.0678(7) Uani 1 1 d U . .
H9A H 0.8719 0.6517 0.0040 0.081 Uiso 1 1 calc R . .
H9B H 0.7864 0.6778 -0.1004 0.081 Uiso 1 1 calc R . .
C18 C 0.89215(18) 0.34339(16) -0.1486(2) 0.0796(8) Uani 1 1 d U . .
H18 H 0.8865 0.2809 -0.1487 0.095 Uiso 1 1 calc R . .
C8 C 0.75585(19) 0.67682(14) 0.0582(2) 0.0744(7) Uani 1 1 d U . .
H8A H 0.7862 0.7286 0.1020 0.089 Uiso 1 1 calc R . .
H8B H 0.6926 0.6925 0.0192 0.089 Uiso 1 1 calc R . .
C19 C 0.83889(17) 0.39609(15) -0.0971(2) 0.0744(8) Uani 1 1 d U . .
H19 H 0.7984 0.3678 -0.0618 0.089 Uiso 1 1 calc R . .
C30 C 0.5458(2) 0.54009(18) -0.2752(2) 0.0784(8) Uani 1 1 d U . .
H30 H 0.5158 0.5606 -0.3496 0.094 Uiso 1 1 calc R . .
C29 C 0.49951(18) 0.48768(18) -0.2147(2) 0.0754(7) Uani 1 1 d U . .
H29 H 0.4384 0.4729 -0.2494 0.090 Uiso 1 1 calc R . .
C14 C 0.90579(19) 0.52585(16) -0.1465(2) 0.0759(8) Uani 1 1 d U . .
H14 H 0.9116 0.5883 -0.1468 0.091 Uiso 1 1 calc R . .
C15 C 0.96013(19) 0.47449(19) -0.1967(2) 0.0827(8) Uani 1 1 d U . .
H15 H 1.0024 0.5025 -0.2294 0.099 Uiso 1 1 calc R . .
C5 C 0.88967(19) 0.58790(19) 0.4835(2) 0.0923(9) Uani 1 1 d U . .
H5A H 0.9381 0.5746 0.4478 0.138 Uiso 1 1 calc R . .
H5B H 0.9113 0.5781 0.5662 0.138 Uiso 1 1 calc R . .
H5C H 0.8712 0.6497 0.4688 0.138 Uiso 1 1 calc R . .
C24 C 0.6191(2) 0.25607(18) 0.2647(2) 0.0877(8) Uani 1 1 d U . .
H24A H 0.6836 0.2664 0.2982 0.132 Uiso 1 1 calc R . .
H24B H 0.6012 0.2018 0.2968 0.132 Uiso 1 1 calc R . .
H24C H 0.5848 0.3061 0.2823 0.132 Uiso 1 1 calc R . .
C27 C 0.6586(2) 0.17546(16) 0.0996(3) 0.0922(9) Uani 1 1 d U . .
H27A H 0.6432 0.1710 0.0160 0.138 Uiso 1 1 calc R . .
H27B H 0.6479 0.1184 0.1318 0.138 Uiso 1 1 calc R . .
H27C H 0.7223 0.1915 0.1290 0.138 Uiso 1 1 calc R . .
C3 C 0.8343(2) 0.42913(18) 0.4572(2) 0.0872(8) Uani 1 1 d U . .
H3A H 0.7816 0.3922 0.4233 0.131 Uiso 1 1 calc R . .
H3B H 0.8537 0.4192 0.5400 0.131 Uiso 1 1 calc R . .
H3C H 0.8833 0.4137 0.4236 0.131 Uiso 1 1 calc R . .
C2 C 0.7269(2) 0.5521(2) 0.4763(2) 0.1045(10) Uani 1 1 d U . .
H2A H 0.7104 0.6138 0.4571 0.157 Uiso 1 1 calc R . .
H2B H 0.7419 0.5444 0.5595 0.157 Uiso 1 1 calc R . .
H2C H 0.6760 0.5137 0.4398 0.157 Uiso 1 1 calc R . .
C26 C 0.4989(2) 0.2311(2) 0.0778(3) 0.1133(11) Uani 1 1 d U . .
H26A H 0.4639 0.2777 0.1021 0.170 Uiso 1 1 calc R . .
H26B H 0.4812 0.1735 0.1014 0.170 Uiso 1 1 calc R . .
H26C H 0.4874 0.2325 -0.0056 0.170 Uiso 1 1 calc R . .
C17 C 0.9946(3) 0.2462(2) -0.2747(4) 0.1302(13) Uani 1 1 d U . .
H17A H 1.0052 0.2150 -0.2016 0.195 Uiso 1 1 calc R . .
H17B H 1.0365 0.2243 -0.3165 0.195 Uiso 1 1 calc R . .
H17C H 0.9326 0.2360 -0.3203 0.195 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
O001 C23 1.329(3) . ?
O001 C25 1.485(3) . ?
O002 C23 1.211(2) . ?
O003 C6 1.337(3) . ?
O003 C4 1.467(3) . ?
N004 C23 1.376(3) . ?
N004 C22 1.426(3) . ?
N004 C7 1.460(3) . ?
N005 C6 1.356(3) . ?
N005 C7 1.453(3) . ?
N005 C8 1.462(3) . ?
O006 C6 1.211(3) . ?
O1 C16 1.367(3) . ?
O1 C17 1.392(4) . ?
C22 C21 1.384(3) . ?
C22 C11 1.387(3) . ?
C7 C10 1.560(3) . ?
C10 C13 1.511(3) . ?
C10 C11 1.523(3) . ?
C10 C9 1.535(3) . ?
C13 C19 1.369(3) . ?
C13 C14 1.370(3) . ?
C11 C12 1.377(3) . ?
C21 C29 1.373(3) . ?
C16 C18 1.361(3) . ?
C16 C15 1.361(3) . ?
C12 C30 1.378(4) . ?
C4 C5 1.499(3) . ?
C4 C2 1.512(4) . ?
C4 C3 1.515(4) . ?
C25 C27 1.501(3) . ?
C25 C26 1.508(4) . ?
C25 C24 1.511(4) . ?
C9 C8 1.502(3) . ?
C18 C19 1.378(3) . ?
C30 C29 1.372(4) . ?
C14 C15 1.369(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 O001 C25 121.08(17) . . ?
C6 O003 C4 120.34(17) . . ?
C23 N004 C22 126.83(17) . . ?
C23 N004 C7 120.18(17) . . ?
C22 N004 C7 108.64(16) . . ?
C6 N005 C7 125.86(18) . . ?
C6 N005 C8 120.16(17) . . ?
C7 N005 C8 113.08(17) . . ?
C16 O1 C17 118.4(2) . . ?
C21 C22 C11 121.3(2) . . ?
C21 C22 N004 129.7(2) . . ?
C11 C22 N004 108.95(18) . . ?
N005 C7 N004 112.20(17) . . ?
N005 C7 C10 103.39(15) . . ?
N004 C7 C10 105.31(15) . . ?
C13 C10 C11 110.56(17) . . ?
C13 C10 C9 114.99(18) . . ?
C11 C10 C9 112.18(17) . . ?
C13 C10 C7 114.60(16) . . ?
C11 C10 C7 100.17(16) . . ?
C9 C10 C7 103.25(16) . . ?
O002 C23 O001 126.01(19) . . ?
O002 C23 N004 123.5(2) . . ?
O001 C23 N004 110.4(2) . . ?
C19 C13 C14 115.9(2) . . ?
C19 C13 C10 121.66(18) . . ?
C14 C13 C10 122.41(19) . . ?
C12 C11 C22 119.9(2) . . ?
C12 C11 C10 128.9(2) . . ?
C22 C11 C10 111.17(17) . . ?
C29 C21 C22 117.6(2) . . ?
O006 C6 O003 126.5(2) . . ?
O006 C6 N005 122.9(2) . . ?
O003 C6 N005 110.60(19) . . ?
C18 C16 C15 118.6(2) . . ?
C18 C16 O1 125.3(2) . . ?
C15 C16 O1 116.1(2) . . ?
C11 C12 C30 119.0(2) . . ?
O003 C4 C5 110.5(2) . . ?
O003 C4 C2 109.9(2) . . ?
C5 C4 C2 111.9(2) . . ?
O003 C4 C3 101.86(18) . . ?
C5 C4 C3 111.4(2) . . ?
C2 C4 C3 110.8(2) . . ?
O001 C25 C27 109.68(19) . . ?
O001 C25 C26 101.27(19) . . ?
C27 C25 C26 112.1(2) . . ?
O001 C25 C24 109.67(19) . . ?
C27 C25 C24 112.5(2) . . ?
C26 C25 C24 111.0(2) . . ?
C8 C9 C10 104.03(18) . . ?
C16 C18 C19 119.9(2) . . ?
N005 C8 C9 102.39(17) . . ?
C13 C19 C18 122.7(2) . . ?
C29 C30 C12 120.4(2) . . ?
C30 C29 C21 121.7(2) . . ?
C15 C14 C13 122.2(2) . . ?
C16 C15 C14 120.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.71
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 1007349'
