# 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_a12599

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 O3'
_chemical_formula_sum            'C19 H14 O3'
_chemical_formula_weight         290.30

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.3228(8)
_cell_length_b                   8.8321(9)
_cell_length_c                   10.8845(11)
_cell_angle_alpha                86.924(3)
_cell_angle_beta                 69.716(2)
_cell_angle_gamma                76.474(3)
_cell_volume                     729.33(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5654
_diffrn_reflns_av_R_equivalents  0.1362
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2524
_reflns_number_gt                2123
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1004P)²+0.0237P] 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         2524
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2365(3) 0.4236(2) 1.21174(18) 0.0517(5) Uani 1 1 d . . .
H1A H 0.1690 0.4408 1.3056 0.078 Uiso 1 1 calc R . .
H1B H 0.3574 0.4327 1.1950 0.078 Uiso 1 1 calc R . .
H1C H 0.2381 0.3192 1.1844 0.078 Uiso 1 1 calc R . .
C2 C 0.23497(19) 0.53100(19) 1.00852(16) 0.0328(4) Uani 1 1 d . . .
C3 C 0.14588(19) 0.65779(18) 0.94276(14) 0.0298(4) Uani 1 1 d . . .
C4 C -0.01184(19) 0.75691(19) 1.00824(15) 0.0314(4) Uani 1 1 d . . .
H4 H -0.0672 0.7457 1.0995 0.038 Uiso 1 1 calc R . .
C5 C -0.09371(19) 0.87573(19) 0.94224(16) 0.0315(4) Uani 1 1 d . . .
C6 C -0.2554(2) 0.9790(2) 1.01110(18) 0.0398(5) Uani 1 1 d . . .
H6 H -0.3111 0.9675 1.1023 0.048 Uiso 1 1 calc R . .
C7 C -0.3319(2) 1.0953(2) 0.9470(2) 0.0477(5) Uani 1 1 d . . .
H7 H -0.4396 1.1652 0.9939 0.057 Uiso 1 1 calc R . .
C8 C -0.2519(2) 1.1116(2) 0.8125(2) 0.0463(5) Uani 1 1 d . . .
H8 H -0.3058 1.1928 0.7689 0.056 Uiso 1 1 calc R . .
C9 C -0.0973(2) 1.0124(2) 0.74260(18) 0.0388(4) Uani 1 1 d . . .
H9 H -0.0457 1.0249 0.6511 0.047 Uiso 1 1 calc R . .
C10 C -0.01315(19) 0.89140(19) 0.80538(15) 0.0309(4) Uani 1 1 d . . .
C11 C 0.15260(19) 0.78612(19) 0.73875(15) 0.0302(4) Uani 1 1 d . . .
C12 C 0.22846(19) 0.67516(18) 0.80758(14) 0.0304(4) Uani 1 1 d . . .
H12 H 0.3395 0.6083 0.7630 0.036 Uiso 1 1 calc R . .
C13 C 0.2386(2) 0.7832(2) 0.59285(15) 0.0353(4) Uani 1 1 d . . .
C14 C 0.43330(19) 0.76628(19) 0.53704(14) 0.0326(4) Uani 1 1 d . . .
C15 C 0.5221(2) 0.8305(2) 0.60050(15) 0.0354(4) Uani 1 1 d . . .
H15 H 0.4593 0.8830 0.6831 0.043 Uiso 1 1 calc R . .
C16 C 0.7019(2) 0.8181(2) 0.54371(16) 0.0413(5) Uani 1 1 d . . .
H16 H 0.7613 0.8646 0.5864 0.050 Uiso 1 1 calc R . .
C17 C 0.7947(2) 0.7387(2) 0.42560(18) 0.0475(5) Uani 1 1 d . . .
H17 H 0.9182 0.7286 0.3878 0.057 Uiso 1 1 calc R . .
C18 C 0.7087(2) 0.6739(2) 0.36240(18) 0.0504(5) Uani 1 1 d . . .
H18 H 0.7732 0.6186 0.2812 0.060 Uiso 1 1 calc R . .
C19 C 0.5275(2) 0.6890(2) 0.41663(16) 0.0415(5) Uani 1 1 d . . .
H19 H 0.4682 0.6464 0.3714 0.050 Uiso 1 1 calc R . .
O1 O 0.15550(15) 0.53904(15) 1.13837(11) 0.0430(4) Uani 1 1 d . . .
O2 O 0.36398(15) 0.43249(15) 0.95112(12) 0.0470(4) Uani 1 1 d . . .
O3 O 0.15269(16) 0.78879(18) 0.52080(11) 0.0546(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
C1 O1 1.448(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.2068(19) . ?
C2 O1 1.3344(19) . ?
C2 C3 1.486(2) . ?
C3 C4 1.370(2) . ?
C3 C12 1.409(2) . ?
C4 C5 1.416(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.416(2) . ?
C5 C10 1.420(2) . ?
C6 C7 1.369(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.366(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.415(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.440(2) . ?
C11 C12 1.371(2) . ?
C11 C13 1.497(2) . ?
C12 H12 0.9500 . ?
C13 O3 1.2232(18) . ?
C13 C14 1.494(2) . ?
C14 C15 1.392(2) . ?
C14 C19 1.390(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.05(15) . . ?
O2 C2 C3 123.92(14) . . ?
O1 C2 C3 112.03(13) . . ?
C4 C3 C12 119.36(15) . . ?
C4 C3 C2 122.67(14) . . ?
C12 C3 C2 117.97(13) . . ?
C3 C4 C5 121.17(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.76(15) . . ?
C6 C5 C10 119.53(15) . . ?
C4 C5 C10 119.71(14) . . ?
C7 C6 C5 120.34(16) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.12(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 121.08(17) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.59(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 118.33(14) . . ?
C9 C10 C11 123.53(14) . . ?
C5 C10 C11 118.12(14) . . ?
C12 C11 C10 119.96(14) . . ?
C12 C11 C13 117.88(13) . . ?
C10 C11 C13 121.91(14) . . ?
C11 C12 C3 121.65(14) . . ?
C11 C12 H12 119.2 . . ?
C3 C12 H12 119.2 . . ?
O3 C13 C14 120.63(14) . . ?
O3 C13 C11 120.91(14) . . ?
C14 C13 C11 118.40(12) . . ?
C15 C14 C19 119.08(14) . . ?
C15 C14 C13 121.65(14) . . ?
C19 C14 C13 119.23(14) . . ?
C16 C15 C14 120.32(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.15(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.06(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.38(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.97(16) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C2 O1 C1 116.17(14) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 972525'
#######################################################################
#
#                 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_a12825

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   9.5269(6)
_cell_length_b                   10.7294(7)
_cell_length_c                   17.4823(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1787.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9535
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6346
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.08
_reflns_number_total             2173
_reflns_number_gt                2021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0443P)²+0.1823P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(13)
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.99175(19) 1.14980(17) 1.05843(12) 0.0329(4) Uani 1 1 d . . .
C2 C 1.0872(2) 1.06176(18) 1.08517(12) 0.0397(5) Uani 1 1 d . . .
H2 H 1.0798 0.9775 1.0691 0.048 Uiso 1 1 calc R . .
C3 C 1.1919(2) 1.0963(2) 1.13476(14) 0.0462(5) Uani 1 1 d . . .
H3 H 1.2573 1.0359 1.1524 0.055 Uiso 1 1 calc R . .
C4 C 1.2029(2) 1.2182(2) 1.15904(14) 0.0496(6) Uani 1 1 d . . .
H4 H 1.2758 1.2419 1.1931 0.060 Uiso 1 1 calc R . .
C5 C 1.1077(2) 1.3050(2) 1.13366(14) 0.0487(6) Uani 1 1 d . . .
H5 H 1.1145 1.3886 1.1512 0.058 Uiso 1 1 calc R . .
C6 C 1.0029(2) 1.27316(17) 1.08339(13) 0.0399(5) Uani 1 1 d . . .
H6 H 0.9386 1.3344 1.0657 0.048 Uiso 1 1 calc R . .
C7 C 0.8877(2) 1.11493(17) 1.00385(14) 0.0362(5) Uani 1 1 d . . .
C8 C 0.8046(2) 1.07983(18) 0.95699(13) 0.0368(5) Uani 1 1 d . . .
C9 C 0.71039(19) 1.03140(18) 0.90052(12) 0.0365(5) Uani 1 1 d . . .
C10 C 0.6280(2) 1.1123(2) 0.85797(14) 0.0469(5) Uani 1 1 d . . .
H10 H 0.6329 1.1994 0.8674 0.056 Uiso 1 1 calc R . .
C11 C 0.5392(2) 1.0677(2) 0.80235(14) 0.0537(6) Uani 1 1 d . . .
H11 H 0.4833 1.1239 0.7734 0.064 Uiso 1 1 calc R . .
C12 C 0.5314(2) 0.9412(2) 0.78868(13) 0.0504(6) Uani 1 1 d . . .
H12 H 0.4709 0.9104 0.7498 0.061 Uiso 1 1 calc R . .
C13 C 0.61133(19) 0.8591(2) 0.83123(13) 0.0422(5) Uani 1 1 d . . .
H13 H 0.6045 0.7722 0.8214 0.051 Uiso 1 1 calc R . .
C14 C 0.70168(19) 0.90134(18) 0.88817(12) 0.0341(5) Uani 1 1 d . . .
C15 C 0.79027(19) 0.82084(17) 0.93565(12) 0.0341(4) Uani 1 1 d . . .
H15 H 0.8684 0.8620 0.9580 0.041 Uiso 1 1 calc R . .
C16 C 0.7808(2) 0.69951(16) 0.95316(11) 0.0342(5) Uani 1 1 d . . .
C17 C 0.8840(2) 0.64582(17) 1.00781(13) 0.0374(5) Uani 1 1 d . . .
C18 C 1.0846(2) 0.6794(2) 1.08350(17) 0.0578(7) Uani 1 1 d . . .
H18A H 1.1559 0.7434 1.0931 0.087 Uiso 1 1 calc R . .
H18B H 1.1303 0.6033 1.0649 0.087 Uiso 1 1 calc R . .
H18C H 1.0341 0.6612 1.1310 0.087 Uiso 1 1 calc R . .
C19 C 0.6709(2) 0.60958(18) 0.92576(13) 0.0392(5) Uani 1 1 d . . .
H19A H 0.6509 0.5479 0.9664 0.047 Uiso 1 1 calc R . .
H19B H 0.5830 0.6553 0.9145 0.047 Uiso 1 1 calc R . .
C20 C 0.6328(2) 0.4861(2) 0.81035(14) 0.0450(5) Uani 1 1 d . . .
C21 C 0.6990(2) 0.4215(2) 0.74313(16) 0.0555(6) Uani 1 1 d . . .
H21A H 0.8012 0.4309 0.7457 0.083 Uiso 1 1 calc R . .
H21B H 0.6643 0.4588 0.6956 0.083 Uiso 1 1 calc R . .
H21C H 0.6747 0.3328 0.7442 0.083 Uiso 1 1 calc R . .
O1 O 0.98731(15) 0.72370(12) 1.02685(10) 0.0482(4) Uani 1 1 d . . .
O2 O 0.87480(16) 0.54247(13) 1.03378(11) 0.0560(5) Uani 1 1 d . . .
N1 N 0.71862(16) 0.54524(15) 0.85702(12) 0.0394(4) Uani 1 1 d . . .
H1 H 0.8088 0.5459 0.8462 0.047 Uiso 1 1 calc R . .
O3 O 0.50724(18) 0.4850(3) 0.81979(14) 0.0956(8) 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
C1 C2 1.392(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.426(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.200(3) . ?
C8 C9 1.432(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.415(3) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.465(3) . ?
C15 C16 1.340(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.487(3) . ?
C16 C19 1.502(3) . ?
C17 O2 1.202(2) . ?
C17 O1 1.333(2) . ?
C18 O1 1.438(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N1 1.458(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O3 1.208(2) . ?
C20 N1 1.318(3) . ?
C20 C21 1.503(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 H1 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.21(19) . . ?
C2 C1 C7 120.05(17) . . ?
C6 C1 C7 120.69(18) . . ?
C3 C2 C1 120.24(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C1 176.4(2) . . ?
C7 C8 C9 176.6(2) . . ?
C10 C9 C14 120.2(2) . . ?
C10 C9 C8 119.83(19) . . ?
C14 C9 C8 120.00(17) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C9 117.84(19) . . ?
C13 C14 C15 124.69(18) . . ?
C9 C14 C15 117.47(18) . . ?
C16 C15 C14 131.54(18) . . ?
C16 C15 H15 114.2 . . ?
C14 C15 H15 114.2 . . ?
C15 C16 C17 118.59(17) . . ?
C15 C16 C19 126.71(18) . . ?
C17 C16 C19 114.65(16) . . ?
O2 C17 O1 122.56(19) . . ?
O2 C17 C16 123.49(19) . . ?
O1 C17 C16 113.93(16) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C16 110.46(15) . . ?
N1 C19 H19A 109.6 . . ?
C16 C19 H19A 109.6 . . ?
N1 C19 H19B 109.6 . . ?
C16 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O3 C20 N1 122.3(2) . . ?
O3 C20 C21 121.2(2) . . ?
N1 C20 C21 116.49(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 O1 C18 116.15(16) . . ?
C20 N1 C19 123.01(15) . . ?
C20 N1 H1 118.5 . . ?
C19 N1 H1 118.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 978566'
#######################################################################
#
#                 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_ch15710a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H32 I2 N2 O12'
_chemical_formula_sum            'C38 H32 I2 N2 O12'
_chemical_formula_weight         962.46

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   5.8687(3)
_cell_length_b                   10.7289(6)
_cell_length_c                   27.8199(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.947(3)
_cell_angle_gamma                90.00
_cell_volume                     1742.24(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    1.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5850
_exptl_absorpt_correction_T_max  0.9120
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9825
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         0.74
_diffrn_reflns_theta_max         25.04
_reflns_number_total             5302
_reflns_number_gt                4666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1247P)²+81.6874P] 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     SHELXL
_refine_ls_extinction_coef       0.038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.40(13)
_refine_ls_number_reflns         5302
_refine_ls_number_parameters     226
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1087
_refine_ls_wR_factor_ref         0.3290
_refine_ls_wR_factor_gt          0.3129
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.012

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
C1 C 0.443(5) 0.519(3) 0.4266(10) 0.045(7) Uiso 1 1 d . A 1
C2 C 0.274(3) 0.399(2) 0.4247(7) 0.032(5) Uiso 1 1 d D A 1
C3 C 0.326(5) 0.313(2) 0.3991(9) 0.044(7) Uiso 1 1 d D A 1
H3 H 0.4634 0.3112 0.3838 0.053 Uiso 1 1 calc R A 1
C4 C 0.156(5) 0.213(3) 0.3943(9) 0.046(7) Uiso 1 1 d D A 1
H4 H 0.1826 0.1424 0.3751 0.056 Uiso 1 1 calc R A 1
C5 C -0.017(6) 0.218(4) 0.4141(10) 0.055(8) Uiso 1 1 d D A 1
H5 H -0.1189 0.1493 0.4092 0.066 Uiso 1 1 calc R A 1
C6 C -0.079(5) 0.311(3) 0.4423(10) 0.050(8) Uiso 1 1 d D A 1
H6 H -0.2191 0.3078 0.4568 0.061 Uiso 1 1 calc R A 1
C7 C 0.086(5) 0.422(5) 0.4503(10) 0.063(8) Uiso 1 1 d D A 1
H7 H 0.0639 0.4937 0.4693 0.075 Uiso 1 1 calc R A 1
C8 C 0.537(5) 0.565(4) 0.3962(9) 0.036(6) Uiso 1 1 d . A 1
C9 C 0.720(5) 0.650(3) 0.3900(10) 0.045(7) Uiso 1 1 d . A 1
C10 C 0.863(5) 0.728(3) 0.4257(10) 0.038(6) Uiso 1 1 d . A 1
H10 H 0.8348 0.7322 0.4587 0.046 Uiso 1 1 calc R A 1
C11 C 1.053(5) 0.802(3) 0.4067(11) 0.044(7) Uiso 1 1 d . A 1
H11 H 1.1398 0.8584 0.4276 0.053 Uiso 1 1 calc R A 1
C12 C 1.102(5) 0.789(3) 0.3631(11) 0.043(7) Uiso 1 1 d . A 1
C13 C 0.965(7) 0.715(4) 0.3285(15) 0.071(11) Uiso 1 1 d . A 1
H13 H 1.0036 0.7068 0.2963 0.086 Uiso 1 1 calc R A 1
C14 C 0.781(5) 0.656(3) 0.3427(9) 0.034(6) Uiso 1 1 d . A 1
C15 C 0.611(5) 0.583(3) 0.3130(9) 0.039(6) Uiso 1 1 d . A 1
H15 H 0.5252 0.6364 0.2878 0.046 Uiso 1 1 calc R A 1
C16 C 0.719(5) 0.463(3) 0.2891(10) 0.037(6) Uiso 1 1 d . A 1
C17 C 0.937(6) 0.405(5) 0.3041(13) 0.068(9) Uiso 1 1 d . A 1
H17A H 0.9891 0.3376 0.2861 0.082 Uiso 1 1 calc R A 1
H17B H 1.0282 0.4352 0.3318 0.082 Uiso 1 1 calc R A 1
C18 C 0.576(4) 0.416(5) 0.2460(9) 0.040(5) Uiso 1 1 d . A 1
C19 C 0.231(5) 0.427(5) 0.1969(11) 0.058(8) Uiso 1 1 d . A 1
H19A H 0.0792 0.4620 0.1995 0.088 Uiso 1 1 calc R A 1
H19B H 0.2191 0.3362 0.1929 0.088 Uiso 1 1 calc R A 1
H19C H 0.2952 0.4629 0.1688 0.088 Uiso 1 1 calc R A 1
C20 C 0.558(4) 0.978(3) 0.0641(9) 0.033(6) Uiso 1 1 d . B 1
C21 C 0.714(4) 1.073(3) 0.0722(8) 0.041(6) Uiso 1 1 d D B 1
C22 C 0.682(5) 1.185(2) 0.1051(9) 0.044(7) Uiso 1 1 d D B 1
H22 H 0.5529 1.1845 0.1231 0.053 Uiso 1 1 calc R B 1
C23 C 0.836(5) 1.293(3) 0.1105(10) 0.047(7) Uiso 1 1 d D B 1
H23 H 0.8141 1.3621 0.1309 0.056 Uiso 1 1 calc R B 1
C24 C 1.029(5) 1.283(4) 0.0805(10) 0.054(8) Uiso 1 1 d D B 1
H24 H 1.1389 1.3480 0.0814 0.065 Uiso 1 1 calc R B 1
C25 C 1.053(5) 1.180(3) 0.0512(9) 0.050(7) Uiso 1 1 d D B 1
H25 H 1.1801 1.1778 0.0326 0.061 Uiso 1 1 calc R B 1
C26 C 0.917(4) 1.092(3) 0.0483(8) 0.033(5) Uiso 1 1 d D B 1
H26 H 0.9513 1.0271 0.0271 0.039 Uiso 1 1 calc R B 1
C27 C 0.442(4) 0.921(5) 0.1065(10) 0.050(6) Uiso 1 1 d . B 1
C28 C 0.262(5) 0.834(3) 0.1088(10) 0.035(6) Uiso 1 1 d . B 1
C29 C 0.102(6) 0.764(4) 0.0796(12) 0.056(8) Uiso 1 1 d . B 1
H29 H 0.1235 0.7660 0.0462 0.068 Uiso 1 1 calc R B 1
C30 C -0.046(5) 0.705(3) 0.0881(11) 0.043(7) Uiso 1 1 d . B 1
H30 H -0.1385 0.6606 0.0638 0.051 Uiso 1 1 calc R B 1
C31 C -0.086(6) 0.701(4) 0.1379(12) 0.054(8) Uiso 1 1 d . B 1
C32 C 0.044(4) 0.765(3) 0.1733(9) 0.031(5) Uiso 1 1 d . B 1
H32 H 0.0174 0.7620 0.2064 0.037 Uiso 1 1 calc R B 1
C33 C 0.229(7) 0.838(4) 0.1556(15) 0.065(10) Uiso 1 1 d . B 1
C34 C 0.385(4) 0.933(4) 0.1861(9) 0.039(6) Uiso 1 1 d . B 1
H34 H 0.4797 0.8832 0.2113 0.047 Uiso 1 1 calc R B 1
C35 C 0.282(5) 1.026(4) 0.2101(11) 0.045(7) Uiso 1 1 d . B 1
C36 C 0.078(4) 1.067(3) 0.1984(9) 0.034(6) Uiso 1 1 d . B 1
H36A H -0.0132 1.0327 0.1714 0.041 Uiso 1 1 calc R B 1
H36B H 0.0180 1.1316 0.2168 0.041 Uiso 1 1 calc R B 1
C37 C 0.401(6) 1.090(4) 0.2542(11) 0.050(8) Uiso 1 1 d . B 1
C38 C 0.768(5) 1.089(4) 0.3023(10) 0.047(7) Uiso 1 1 d . B 1
H38A H 0.9217 1.0522 0.3034 0.070 Uiso 1 1 calc R B 1
H38B H 0.6955 1.0624 0.3308 0.070 Uiso 1 1 calc R B 1
H38C H 0.7797 1.1797 0.3018 0.070 Uiso 1 1 calc R B 1
O1 O 1.408(4) 0.926(4) 0.3768(9) 0.079(7) Uiso 1 1 d D A 1
O2 O 1.330(4) 0.852(3) 0.3032(8) 0.062(7) Uiso 1 1 d D A 1
O3 O 0.377(4) 0.454(2) 0.2392(7) 0.044(5) Uiso 1 1 d . A 1
O4 O 0.667(4) 0.332(3) 0.2158(8) 0.048(5) Uiso 1 1 d . A 1
O5 O 0.459(4) 0.538(3) 0.3484(8) 0.057(6) Uiso 1 1 d . A 1
O6 O -0.336(5) 0.648(3) 0.1946(10) 0.081(8) Uiso 1 1 d D B 1
O7 O -0.417(4) 0.578(3) 0.1225(8) 0.059(6) Uiso 1 1 d D B 1
O8 O 0.342(4) 1.159(3) 0.2782(8) 0.055(6) Uiso 1 1 d . B 1
O9 O 0.632(4) 1.047(3) 0.2593(7) 0.050(5) Uiso 1 1 d . B 1
O10 O 0.532(3) 0.968(2) 0.1518(7) 0.039(5) Uiso 1 1 d . B 1
I1 I 0.5359(4) 0.5741(14) 0.50465(7) 0.0655(9) Uani 1 1 d . A 1
I2 I 0.4649(2) 0.9175(14) -0.00112(4) 0.0305(5) Uani 1 1 d . B 1
N1 N 1.290(5) 0.859(3) 0.3457(9) 0.054(7) Uiso 1 1 d D A 1
N2 N -0.287(5) 0.639(3) 0.1511(10) 0.064(8) Uiso 1 1 d D B 1
O11 O 0.966(3) 0.759(2) 0.5031(6) 0.036 Uiso 1 1 d . C 2
O12 O 0.030(3) 0.571(2) 0.4964(5) 0.034 Uiso 1 1 d . D 2


_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
C1 C8 1.16(4) . ?
C1 C2 1.62(4) . ?
C1 I1 2.26(3) . ?
C2 C3 1.23(4) . ?
C2 C7 1.40(4) . ?
C3 C4 1.46(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.20(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.34(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.54(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O5 1.39(3) . ?
C8 C9 1.43(4) . ?
C9 C14 1.40(4) . ?
C9 C10 1.49(4) . ?
C10 C11 1.51(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.28(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.43(5) . ?
C12 N1 1.46(4) . ?
C13 C14 1.35(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.45(4) . ?
C15 O5 1.48(3) . ?
C15 C16 1.61(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.44(5) . ?
C16 C18 1.48(4) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C18 O3 1.24(3) . ?
C18 O4 1.38(4) . ?
C19 O3 1.41(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.37(4) . ?
C20 C27 1.55(4) . ?
C20 I2 1.95(3) . ?
C21 C26 1.44(4) . ?
C21 C22 1.53(4) . ?
C22 C23 1.47(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.48(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.38(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.24(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O10 1.41(4) . ?
C27 C28 1.42(5) . ?
C28 C33 1.34(5) . ?
C28 C29 1.39(5) . ?
C29 C30 1.12(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.43(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.37(4) . ?
C31 N2 1.43(4) . ?
C32 C33 1.46(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.56(5) . ?
C34 C35 1.38(4) . ?
C34 O10 1.40(3) . ?
C34 H34 1.0000 . ?
C35 C36 1.29(4) . ?
C35 C37 1.51(5) . ?
C36 H36A 0.9500 . ?
C36 H36B 0.9500 . ?
C37 O8 1.08(4) . ?
C37 O9 1.43(4) . ?
C38 O9 1.44(4) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O1 N1 1.27(3) . ?
O2 N1 1.23(3) . ?
O6 N2 1.27(3) . ?
O7 N2 1.23(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 130(3) . . ?
C8 C1 I1 120(2) . . ?
C2 C1 I1 109.0(16) . . ?
C3 C2 C7 133(3) . . ?
C3 C2 C1 116(2) . . ?
C7 C2 C1 111(3) . . ?
C2 C3 C4 114(3) . . ?
C2 C3 H3 123.2 . . ?
C4 C3 H3 123.2 . . ?
C5 C4 C3 122(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 126(4) . . ?
C4 C5 H5 116.8 . . ?
C6 C5 H5 116.8 . . ?
C5 C6 C7 117(3) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.6 . . ?
C2 C7 C6 108(3) . . ?
C2 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
C1 C8 O5 118(3) . . ?
C1 C8 C9 141(3) . . ?
O5 C8 C9 101(2) . . ?
C14 C9 C8 114(3) . . ?
C14 C9 C10 115(3) . . ?
C8 C9 C10 131(3) . . ?
C9 C10 C11 117(3) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C12 C11 C10 122(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 122(3) . . ?
C11 C12 N1 121(3) . . ?
C13 C12 N1 117(3) . . ?
C14 C13 C12 118(3) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C9 126(3) . . ?
C13 C14 C15 127(3) . . ?
C9 C14 C15 106(3) . . ?
C14 C15 O5 103(2) . . ?
C14 C15 C16 113(2) . . ?
O5 C15 C16 107(2) . . ?
C14 C15 H15 111.0 . . ?
O5 C15 H15 111.1 . . ?
C16 C15 H15 111.1 . . ?
C17 C16 C18 120(3) . . ?
C17 C16 C15 127(3) . . ?
C18 C16 C15 113(3) . . ?
C16 C17 H17A 120.2 . . ?
C16 C17 H17B 119.8 . . ?
H17A C17 H17B 120.0 . . ?
O3 C18 O4 123(3) . . ?
O3 C18 C16 117(3) . . ?
O4 C18 C16 120(2) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.4 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C27 120(3) . . ?
C21 C20 I2 121.2(19) . . ?
C27 C20 I2 118(2) . . ?
C20 C21 C26 127(3) . . ?
C20 C21 C22 124(2) . . ?
C26 C21 C22 109(3) . . ?
C23 C22 C21 125(3) . . ?
C23 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
C22 C23 C24 112(3) . . ?
C22 C23 H23 123.8 . . ?
C24 C23 H23 123.7 . . ?
C25 C24 C23 122(3) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C24 123(3) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C21 130(3) . . ?
C25 C26 H26 115.1 . . ?
C21 C26 H26 115.1 . . ?
O10 C27 C28 114(2) . . ?
O10 C27 C20 113(3) . . ?
C28 C27 C20 133(3) . . ?
C33 C28 C29 115(3) . . ?
C33 C28 C27 102(3) . . ?
C29 C28 C27 142(3) . . ?
C30 C29 C28 132(4) . . ?
C30 C29 H29 113.9 . . ?
C28 C29 H29 113.9 . . ?
C29 C30 C31 116(3) . . ?
C29 C30 H30 122.2 . . ?
C31 C30 H30 122.2 . . ?
C32 C31 N2 118(3) . . ?
C32 C31 C30 123(3) . . ?
N2 C31 C30 119(3) . . ?
C31 C32 C33 114(3) . . ?
C31 C32 H32 123.0 . . ?
C33 C32 H32 123.0 . . ?
C28 C33 C32 120(3) . . ?
C28 C33 C34 114(3) . . ?
C32 C33 C34 126(3) . . ?
C35 C34 O10 118(3) . . ?
C35 C34 C33 118(3) . . ?
O10 C34 C33 100(2) . . ?
C35 C34 H34 106.6 . . ?
O10 C34 H34 106.6 . . ?
C33 C34 H34 106.6 . . ?
C36 C35 C34 125(3) . . ?
C36 C35 C37 113(3) . . ?
C34 C35 C37 122(3) . . ?
C35 C36 H36A 120.1 . . ?
C35 C36 H36B 119.9 . . ?
H36A C36 H36B 120.0 . . ?
O8 C37 O9 122(3) . . ?
O8 C37 C35 132(3) . . ?
O9 C37 C35 107(3) . . ?
O9 C38 H38A 109.4 . . ?
O9 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O9 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C18 O3 C19 123(3) . . ?
C8 O5 C15 114(2) . . ?
C38 O9 C37 115(3) . . ?
C27 O10 C34 108(2) . . ?
O2 N1 O1 123(3) . . ?
O2 N1 C12 121(3) . . ?
O1 N1 C12 116(3) . . ?
O7 N2 O6 118(3) . . ?
O7 N2 C31 124(3) . . ?
O6 N2 C31 119(3) . . ?

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
C8 C1 C2 C3 38(4) . . . . ?
I1 C1 C2 C3 -131.4(14) . . . . ?
C8 C1 C2 C7 -138(3) . . . . ?
I1 C1 C2 C7 53.5(18) . . . . ?
C7 C2 C3 C4 0.02(18) . . . . ?
C1 C2 C3 C4 -173.7(18) . . . . ?
C2 C3 C4 C5 0.01(17) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 173.9(17) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C2 C1 C8 O5 19(5) . . . . ?
I1 C1 C8 O5 -174(2) . . . . ?
C2 C1 C8 C9 -164(4) . . . . ?
I1 C1 C8 C9 4(7) . . . . ?
C1 C8 C9 C14 171(5) . . . . ?
O5 C8 C9 C14 -11(4) . . . . ?
C1 C8 C9 C10 -6(7) . . . . ?
O5 C8 C9 C10 172(3) . . . . ?
C14 C9 C10 C11 -1(4) . . . . ?
C8 C9 C10 C11 176(3) . . . . ?
C9 C10 C11 C12 -5(4) . . . . ?
C10 C11 C12 C13 6(5) . . . . ?
C10 C11 C12 N1 -178(3) . . . . ?
C11 C12 C13 C14 0(5) . . . . ?
N1 C12 C13 C14 -176(3) . . . . ?
C12 C13 C14 C9 -7(6) . . . . ?
C12 C13 C14 C15 175(3) . . . . ?
C8 C9 C14 C13 -171(3) . . . . ?
C10 C9 C14 C13 7(5) . . . . ?
C8 C9 C14 C15 8(4) . . . . ?
C10 C9 C14 C15 -175(3) . . . . ?
C13 C14 C15 O5 178(3) . . . . ?
C9 C14 C15 O5 -1(3) . . . . ?
C13 C14 C15 C16 62(4) . . . . ?
C9 C14 C15 C16 -116(3) . . . . ?
C14 C15 C16 C17 18(4) . . . . ?
O5 C15 C16 C17 -95(3) . . . . ?
C14 C15 C16 C18 -158(3) . . . . ?
O5 C15 C16 C18 89(3) . . . . ?
C17 C16 C18 O3 169(3) . . . . ?
C15 C16 C18 O3 -15(4) . . . . ?
C17 C16 C18 O4 -10(5) . . . . ?
C15 C16 C18 O4 166(3) . . . . ?
C27 C20 C21 C26 144(2) . . . . ?
I2 C20 C21 C26 -40(3) . . . . ?
C27 C20 C21 C22 -43(3) . . . . ?
I2 C20 C21 C22 133.0(16) . . . . ?
C20 C21 C22 C23 -174(2) . . . . ?
C26 C21 C22 C23 0.01(12) . . . . ?
C21 C22 C23 C24 -0.01(12) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C24 C25 C26 C21 0.1(5) . . . . ?
C20 C21 C26 C25 174(2) . . . . ?
C22 C21 C26 C25 0.0(3) . . . . ?
C21 C20 C27 O10 -7(4) . . . . ?
I2 C20 C27 O10 177(2) . . . . ?
C21 C20 C27 C28 172(4) . . . . ?
I2 C20 C27 C28 -4(5) . . . . ?
O10 C27 C28 C33 6(4) . . . . ?
C20 C27 C28 C33 -173(4) . . . . ?
O10 C27 C28 C29 175(4) . . . . ?
C20 C27 C28 C29 -4(8) . . . . ?
C33 C28 C29 C30 -3(7) . . . . ?
C27 C28 C29 C30 -172(5) . . . . ?
C28 C29 C30 C31 1(7) . . . . ?
C29 C30 C31 C32 0(5) . . . . ?
C29 C30 C31 N2 173(4) . . . . ?
N2 C31 C32 C33 -173(3) . . . . ?
C30 C31 C32 C33 0(5) . . . . ?
C29 C28 C33 C32 4(5) . . . . ?
C27 C28 C33 C32 176(3) . . . . ?
C29 C28 C33 C34 -171(3) . . . . ?
C27 C28 C33 C34 2(4) . . . . ?
C31 C32 C33 C28 -2(5) . . . . ?
C31 C32 C33 C34 172(3) . . . . ?
C28 C33 C34 C35 121(3) . . . . ?
C32 C33 C34 C35 -53(5) . . . . ?
C28 C33 C34 O10 -8(4) . . . . ?
C32 C33 C34 O10 177(3) . . . . ?
O10 C34 C35 C36 97(4) . . . . ?
C33 C34 C35 C36 -23(5) . . . . ?
O10 C34 C35 C37 -83(4) . . . . ?
C33 C34 C35 C37 156(3) . . . . ?
C36 C35 C37 O8 4(6) . . . . ?
C34 C35 C37 O8 -175(4) . . . . ?
C36 C35 C37 O9 -173(3) . . . . ?
C34 C35 C37 O9 7(4) . . . . ?
O4 C18 O3 C19 -8(6) . . . . ?
C16 C18 O3 C19 174(3) . . . . ?
C1 C8 O5 C15 -171(3) . . . . ?
C9 C8 O5 C15 11(3) . . . . ?
C14 C15 O5 C8 -7(3) . . . . ?
C16 C15 O5 C8 112(3) . . . . ?
O8 C37 O9 C38 8(5) . . . . ?
C35 C37 O9 C38 -174(3) . . . . ?
C28 C27 O10 C34 -12(4) . . . . ?
C20 C27 O10 C34 167(3) . . . . ?
C35 C34 O10 C27 -118(3) . . . . ?
C33 C34 O10 C27 11(3) . . . . ?
C11 C12 N1 O2 -176(3) . . . . ?
C13 C12 N1 O2 0(5) . . . . ?
C11 C12 N1 O1 3(5) . . . . ?
C13 C12 N1 O1 179(3) . . . . ?
C32 C31 N2 O7 -180(3) . . . . ?
C30 C31 N2 O7 7(5) . . . . ?
C32 C31 N2 O6 1(5) . . . . ?
C30 C31 N2 O6 -172(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         2.578
_refine_diff_density_min         -5.367
_refine_diff_density_rms         0.396
_database_code_depnum_ccdc_archive 'CCDC 973915'
#######################################################################
#
#                 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_ch16312a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 I O2'
_chemical_formula_sum            'C19 H15 I O2'
_chemical_formula_weight         402.21

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.2342(2)
_cell_length_b                   37.9905(8)
_cell_length_c                   10.4703(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5910(10)
_cell_angle_gamma                90.00
_cell_volume                     3275.16(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_type   multi-san
_exptl_absorpt_correction_T_min  0.3492
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23291
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.07
_diffrn_reflns_theta_max         25.19
_reflns_number_total             5837
_reflns_number_gt                5417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0465P)²+3.7269P] 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         5837
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_restrained_S_all      1.321
_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
C1 C 0.6600(4) 0.09068(10) 0.7067(4) 0.0284(8) Uani 1 1 d . . .
H1A H 0.5743 0.0832 0.6454 0.034 Uiso 1 1 calc R . .
H1B H 0.6120 0.1082 0.7652 0.034 Uiso 1 1 calc R . .
C2 C 0.7951(4) 0.10722(10) 0.6357(4) 0.0251(8) Uani 1 1 d . . .
C3 C 0.8948(4) 0.13260(10) 0.7123(4) 0.0276(8) Uani 1 1 d . . .
C4 C 1.1009(5) 0.17556(12) 0.7109(4) 0.0395(10) Uani 1 1 d . . .
H4A H 1.1761 0.1869 0.6517 0.059 Uiso 1 1 calc R . .
H4B H 1.1628 0.1636 0.7787 0.059 Uiso 1 1 calc R . .
H4C H 1.0302 0.1934 0.7488 0.059 Uiso 1 1 calc R . .
C5 C 0.8305(4) 0.10275(10) 0.5111(4) 0.0259(8) Uani 1 1 d . . .
H5 H 0.9190 0.1164 0.4810 0.031 Uiso 1 1 calc R . .
C6 C 0.7526(4) 0.07998(10) 0.4154(3) 0.0247(8) Uani 1 1 d . . .
C7 C 0.6744(5) 0.04844(11) 0.4415(4) 0.0321(9) Uani 1 1 d . . .
H7 H 0.6674 0.0406 0.5274 0.038 Uiso 1 1 calc R . .
C8 C 0.6065(5) 0.02819(11) 0.3452(4) 0.0362(10) Uani 1 1 d . . .
H8 H 0.5544 0.0066 0.3656 0.043 Uiso 1 1 calc R . .
C9 C 0.6139(5) 0.03906(12) 0.2200(4) 0.0398(11) Uani 1 1 d . . .
H9 H 0.5645 0.0253 0.1545 0.048 Uiso 1 1 calc R . .
C10 C 0.6930(5) 0.06984(12) 0.1897(4) 0.0369(10) Uani 1 1 d . . .
H10 H 0.6996 0.0770 0.1030 0.044 Uiso 1 1 calc R . .
C11 C 0.7641(5) 0.09076(10) 0.2858(4) 0.0278(8) Uani 1 1 d . . .
C12 C 0.8519(5) 0.12208(11) 0.2526(4) 0.0310(9) Uani 1 1 d . . .
C13 C 0.9331(5) 0.14702(11) 0.2264(4) 0.0328(9) Uani 1 1 d . . .
C14 C 1.0377(5) 0.17602(10) 0.1960(4) 0.0314(9) Uani 1 1 d . . .
C15 C 1.0540(5) 0.18755(11) 0.0696(4) 0.0348(9) Uani 1 1 d . . .
H15 H 0.9915 0.1769 0.0033 0.042 Uiso 1 1 calc R . .
C16 C 1.1610(6) 0.21438(12) 0.0414(5) 0.0442(11) Uani 1 1 d . . .
H16 H 1.1703 0.2223 -0.0443 0.053 Uiso 1 1 calc R . .
C17 C 1.2543(6) 0.22983(13) 0.1358(6) 0.0551(14) Uani 1 1 d . . .
H17 H 1.3276 0.2483 0.1156 0.066 Uiso 1 1 calc R . .
C18 C 1.2400(6) 0.21822(14) 0.2603(6) 0.0570(14) Uani 1 1 d . . .
H18 H 1.3059 0.2284 0.3255 0.068 Uiso 1 1 calc R . .
C19 C 1.1323(6) 0.19222(14) 0.2910(5) 0.0482(12) Uani 1 1 d . . .
H19 H 1.1216 0.1851 0.3775 0.058 Uiso 1 1 calc R . .
C20 C 0.1553(5) 0.08908(10) 0.0425(4) 0.0293(8) Uani 1 1 d . . .
H20A H 0.1057 0.1049 -0.0219 0.035 Uiso 1 1 calc R . .
H20B H 0.0707 0.0830 0.1053 0.035 Uiso 1 1 calc R . .
C21 C 0.2895(4) 0.10776(10) 0.1088(4) 0.0253(8) Uani 1 1 d . . .
C22 C 0.3871(5) 0.13157(10) 0.0254(4) 0.0281(8) Uani 1 1 d . . .
C23 C 0.5936(6) 0.17485(12) 0.0177(4) 0.0427(11) Uani 1 1 d . . .
H23A H 0.6713 0.1867 0.0748 0.064 Uiso 1 1 calc R . .
H23B H 0.5219 0.1924 -0.0218 0.064 Uiso 1 1 calc R . .
H23C H 0.6526 0.1622 -0.0490 0.064 Uiso 1 1 calc R . .
C24 C 0.3285(4) 0.10643(9) 0.2336(4) 0.0241(8) Uani 1 1 d . . .
H24 H 0.4147 0.1217 0.2581 0.029 Uiso 1 1 calc R . .
C25 C 0.2621(4) 0.08571(10) 0.3383(3) 0.0231(8) Uani 1 1 d . . .
C26 C 0.1823(5) 0.05362(10) 0.3227(4) 0.0288(8) Uani 1 1 d . . .
H26 H 0.1633 0.0448 0.2389 0.035 Uiso 1 1 calc R . .
C27 C 0.1298(5) 0.03424(11) 0.4272(4) 0.0341(9) Uani 1 1 d . . .
H27 H 0.0764 0.0123 0.4144 0.041 Uiso 1 1 calc R . .
C28 C 0.1553(5) 0.04684(11) 0.5499(4) 0.0326(9) Uani 1 1 d . . .
H28 H 0.1180 0.0337 0.6211 0.039 Uiso 1 1 calc R . .
C29 C 0.2346(4) 0.07836(10) 0.5687(4) 0.0269(8) Uani 1 1 d . . .
H29 H 0.2518 0.0869 0.6530 0.032 Uiso 1 1 calc R . .
C30 C 0.2902(4) 0.09790(9) 0.4642(3) 0.0229(8) Uani 1 1 d . . .
C31 C 0.3817(4) 0.12944(10) 0.4892(4) 0.0266(8) Uani 1 1 d . . .
C32 C 0.4648(5) 0.15455(10) 0.5148(4) 0.0288(8) Uani 1 1 d . . .
C33 C 0.5670(5) 0.18311(10) 0.5530(4) 0.0273(8) Uani 1 1 d . . .
C34 C 0.5625(5) 0.19523(11) 0.6779(4) 0.0347(9) Uani 1 1 d . . .
H34 H 0.4887 0.1850 0.7364 0.042 Uiso 1 1 calc R . .
C35 C 0.6648(6) 0.22207(12) 0.7179(5) 0.0430(11) Uani 1 1 d . . .
H35 H 0.6611 0.2300 0.8039 0.052 Uiso 1 1 calc R . .
C36 C 0.7713(5) 0.23725(11) 0.6346(5) 0.0428(11) Uani 1 1 d . . .
H36 H 0.8406 0.2558 0.6624 0.051 Uiso 1 1 calc R . .
C37 C 0.7772(5) 0.22549(12) 0.5100(5) 0.0435(11) Uani 1 1 d . . .
H37 H 0.8516 0.2359 0.4525 0.052 Uiso 1 1 calc R . .
C38 C 0.6760(5) 0.19866(11) 0.4674(4) 0.0368(10) Uani 1 1 d . . .
H38 H 0.6803 0.1909 0.3813 0.044 Uiso 1 1 calc R . .
O1 O 0.8800(4) 0.13672(8) 0.8258(3) 0.0399(7) Uani 1 1 d . . .
O2 O 1.0032(3) 0.15018(8) 0.6427(3) 0.0345(7) Uani 1 1 d . . .
O3 O 0.3680(4) 0.13400(8) -0.0892(3) 0.0404(7) Uani 1 1 d . . .
O4 O 0.4980(3) 0.15019(8) 0.0900(3) 0.0365(7) Uani 1 1 d . . .
I1 I 0.74240(3) 0.045248(7) 0.81665(3) 0.03543(11) Uani 1 1 d . . .
I2 I 0.23814(4) 0.041148(7) -0.05151(3) 0.03781(11) 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
C1 C2 1.484(5) . ?
C1 I1 2.179(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C5 1.350(5) . ?
C2 C3 1.494(5) . ?
C3 O1 1.206(5) . ?
C3 O2 1.337(5) . ?
C4 O2 1.441(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.467(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(6) . ?
C6 C11 1.422(5) . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.437(6) . ?
C12 C13 1.193(6) . ?
C13 C14 1.436(6) . ?
C14 C19 1.400(6) . ?
C14 C15 1.402(6) . ?
C15 C16 1.381(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.368(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.480(5) . ?
C20 I2 2.183(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C24 1.344(5) . ?
C21 C22 1.497(5) . ?
C22 O3 1.212(5) . ?
C22 O4 1.334(5) . ?
C23 O4 1.443(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.460(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(5) . ?
C25 C30 1.413(5) . ?
C26 C27 1.392(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.385(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.377(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.403(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.438(5) . ?
C31 C32 1.203(5) . ?
C32 C33 1.428(5) . ?
C33 C34 1.387(6) . ?
C33 C38 1.404(6) . ?
C34 C35 1.384(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.371(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.387(6) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 111.6(2) . . ?
C2 C1 H1A 109.3 . . ?
I1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
I1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C5 C2 C1 126.9(4) . . ?
C5 C2 C3 118.5(3) . . ?
C1 C2 C3 114.5(3) . . ?
O1 C3 O2 123.2(4) . . ?
O1 C3 C2 123.5(4) . . ?
O2 C3 C2 113.3(3) . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 C6 129.6(4) . . ?
C2 C5 H5 115.2 . . ?
C6 C5 H5 115.2 . . ?
C7 C6 C11 118.2(4) . . ?
C7 C6 C5 125.1(4) . . ?
C11 C6 C5 116.7(3) . . ?
C8 C7 C6 121.5(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 119.3(4) . . ?
C10 C11 C12 120.2(4) . . ?
C6 C11 C12 120.6(3) . . ?
C13 C12 C11 176.1(4) . . ?
C12 C13 C14 177.2(4) . . ?
C19 C14 C15 118.4(4) . . ?
C19 C14 C13 120.7(4) . . ?
C15 C14 C13 120.8(4) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.3(5) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.9(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 I2 112.1(2) . . ?
C21 C20 H20A 109.2 . . ?
I2 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
I2 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C24 C21 C20 127.4(4) . . ?
C24 C21 C22 117.8(3) . . ?
C20 C21 C22 114.8(3) . . ?
O3 C22 O4 122.9(4) . . ?
O3 C22 C21 123.9(4) . . ?
O4 C22 C21 113.2(3) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 C25 131.5(3) . . ?
C21 C24 H24 114.2 . . ?
C25 C24 H24 114.2 . . ?
C26 C25 C30 117.9(3) . . ?
C26 C25 C24 124.2(3) . . ?
C30 C25 C24 117.7(3) . . ?
C27 C26 C25 121.3(4) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 120.0(4) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.4(4) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.2(3) . . ?
C29 C30 C31 118.2(3) . . ?
C25 C30 C31 121.5(3) . . ?
C32 C31 C30 175.8(4) . . ?
C31 C32 C33 176.0(4) . . ?
C34 C33 C38 119.0(4) . . ?
C34 C33 C32 119.6(4) . . ?
C38 C33 C32 121.3(4) . . ?
C35 C34 C33 120.5(4) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 120.5(4) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 119.7(4) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C36 C37 C38 121.0(4) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C37 C38 C33 119.3(4) . . ?
C37 C38 H38 120.3 . . ?
C33 C38 H38 120.3 . . ?
C3 O2 C4 115.9(3) . . ?
C22 O4 C23 116.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.161
_database_code_depnum_ccdc_archive 'CCDC 1009697'
