# 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_ab_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N O4'
_chemical_formula_sum            'C20 H25 N O4'
_chemical_formula_weight         343.41

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   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'


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

_cell_length_a                   9.6382(7)
_cell_length_b                   12.5190(9)
_cell_length_c                   16.1542(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.439(2)
_cell_angle_gamma                90.00
_cell_volume                     1910.5(2)
_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       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7168
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         20.36
_reflns_number_total             1469
_reflns_number_gt                1166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0669P)²+0.0905P] 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         1469
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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
C7 C 0.1680(3) 0.3566(2) 0.30690(17) 0.0475(8) Uani 1 1 d . . .
H7 H 0.2139 0.2907 0.2937 0.057 Uiso 1 1 calc R . .
C2 C -0.0852(4) 0.4128(3) 0.25961(17) 0.0456(8) Uani 1 1 d . . .
C14 C 0.1918(3) 0.4403(2) 0.24159(19) 0.0484(8) Uani 1 1 d . . .
C1 C 0.0114(4) 0.3347(3) 0.29096(17) 0.0449(8) Uani 1 1 d . . .
C8 C 0.2351(3) 0.3859(2) 0.39936(18) 0.0524(8) Uani 1 1 d . . .
H8 H 0.3350 0.4019 0.4007 0.063 Uiso 1 1 calc R . .
C13 C 0.1717(3) 0.4844(2) 0.43333(18) 0.0643(10) Uani 1 1 d . . .
H13A H 0.1841 0.5455 0.3987 0.077 Uiso 1 1 calc R . .
H13B H 0.0709 0.4734 0.4290 0.077 Uiso 1 1 calc R . .
C6 C -0.0435(4) 0.2354(3) 0.30562(18) 0.0608(9) Uani 1 1 d . . .
H6 H 0.0177 0.1794 0.3251 0.073 Uiso 1 1 calc R . .
C9 C 0.2314(3) 0.2921(2) 0.45867(19) 0.0697(9) Uani 1 1 d . . .
H9A H 0.1337 0.2724 0.4574 0.084 Uiso 1 1 calc R . .
H9B H 0.2780 0.2313 0.4388 0.084 Uiso 1 1 calc R . .
C4 C -0.2797(4) 0.2998(4) 0.2629(2) 0.0705(10) Uani 1 1 d . . .
H4 H -0.3769 0.2887 0.2552 0.085 Uiso 1 1 calc R . .
C3 C -0.2288(4) 0.3978(3) 0.24527(17) 0.0589(9) Uani 1 1 d . . .
H3 H -0.2905 0.4528 0.2240 0.071 Uiso 1 1 calc R . .
C11 C 0.2350(3) 0.4125(3) 0.5812(2) 0.0770(10) Uani 1 1 d . . .
H11A H 0.2844 0.4292 0.6381 0.092 Uiso 1 1 calc R . .
H11B H 0.1375 0.3960 0.5833 0.092 Uiso 1 1 calc R . .
C5 C -0.1888(5) 0.2189(3) 0.2915(2) 0.0716(10) Uani 1 1 d . . .
H5 H -0.2241 0.1521 0.3018 0.086 Uiso 1 1 calc R . .
C10 C 0.3030(4) 0.3169(3) 0.5489(2) 0.0842(11) Uani 1 1 d . . .
H10A H 0.2956 0.2556 0.5845 0.101 Uiso 1 1 calc R . .
H10B H 0.4027 0.3311 0.5513 0.101 Uiso 1 1 calc R . .
C12 C 0.2393(3) 0.5084(3) 0.5249(2) 0.0757(10) Uani 1 1 d . . .
H12A H 0.3369 0.5299 0.5281 0.091 Uiso 1 1 calc R . .
H12B H 0.1896 0.5674 0.5449 0.091 Uiso 1 1 calc R . .
C15 C 0.0958(4) 0.5382(3) 0.23909(17) 0.0516(9) Uani 1 1 d . . .
C17 C 0.2341(4) 0.4020(2) 0.0330(2) 0.0621(9) Uani 1 1 d . . .
C19 C 0.1197(4) 0.3268(3) -0.0093(2) 0.0980(12) Uani 1 1 d . . .
H19A H 0.1021 0.2743 0.0308 0.147 Uiso 1 1 calc R . .
H19B H 0.1496 0.2917 -0.0556 0.147 Uiso 1 1 calc R . .
H19C H 0.0346 0.3663 -0.0299 0.147 Uiso 1 1 calc R . .
C16 C 0.3401(5) 0.4761(3) 0.25643(19) 0.0655(10) Uani 1 1 d . . .
C18 C 0.3701(4) 0.3448(3) 0.0690(2) 0.1046(13) Uani 1 1 d . . .
H18A H 0.4390 0.3954 0.0963 0.157 Uiso 1 1 calc R . .
H18B H 0.4050 0.3099 0.0242 0.157 Uiso 1 1 calc R . .
H18C H 0.3531 0.2925 0.1093 0.157 Uiso 1 1 calc R . .
C20 C 0.2570(4) 0.4925(3) -0.0252(2) 0.1037(13) Uani 1 1 d . . .
H20A H 0.1690 0.5290 -0.0448 0.156 Uiso 1 1 calc R . .
H20B H 0.2912 0.4642 -0.0726 0.156 Uiso 1 1 calc R . .
H20C H 0.3252 0.5416 0.0050 0.156 Uiso 1 1 calc R . .
O3 O 0.15730(19) 0.38535(14) 0.16255(13) 0.0595(6) Uani 1 1 d . . .
O1 O -0.0406(2) 0.51643(16) 0.24161(11) 0.0555(6) Uani 1 1 d . . .
O4 O 0.1831(2) 0.46230(15) 0.09831(12) 0.0672(7) Uani 1 1 d . . .
O2 O 0.1305(2) 0.62822(19) 0.23225(13) 0.0719(8) Uani 1 1 d . . .
N1 N 0.4568(3) 0.5002(2) 0.26886(19) 0.0972(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C7 0.053(2) 0.0437(19) 0.051(2) 0.0051(16) 0.0206(17) 0.0076(15)
C2 0.047(3) 0.048(3) 0.045(2) -0.0016(17) 0.0157(17) -0.003(2)
C14 0.040(2) 0.058(2) 0.050(2) -0.0004(19) 0.0170(16) -0.0013(19)
C1 0.054(3) 0.044(2) 0.041(2) -0.0012(16) 0.0198(17) -0.003(2)
C8 0.0469(19) 0.064(2) 0.048(2) 0.0016(18) 0.0129(16) 0.0085(16)
C13 0.080(2) 0.058(2) 0.053(3) 0.0000(17) 0.0092(19) 0.0070(18)
C6 0.077(3) 0.052(3) 0.056(2) 0.0012(17) 0.0191(19) -0.003(2)
C9 0.090(2) 0.066(2) 0.055(2) 0.011(2) 0.0191(19) 0.0256(18)
C4 0.063(3) 0.086(3) 0.066(2) -0.003(2) 0.021(2) -0.019(3)
C3 0.053(3) 0.071(3) 0.055(2) 0.0028(17) 0.0148(18) -0.002(2)
C11 0.085(3) 0.089(3) 0.054(2) -0.001(2) 0.0090(19) 0.017(2)
C5 0.099(4) 0.060(3) 0.059(2) -0.006(2) 0.025(2) -0.027(3)
C10 0.104(3) 0.095(3) 0.052(3) 0.009(2) 0.013(2) 0.037(2)
C12 0.088(3) 0.076(3) 0.059(3) -0.014(2) 0.0035(19) 0.0030(19)
C15 0.046(3) 0.060(3) 0.051(2) 0.0081(18) 0.0146(16) -0.002(2)
C17 0.076(3) 0.067(2) 0.053(2) -0.009(2) 0.034(2) -0.002(2)
C19 0.108(3) 0.107(3) 0.087(3) -0.028(2) 0.038(2) -0.029(2)
C16 0.062(3) 0.077(3) 0.062(2) 0.0104(17) 0.022(2) 0.003(2)
C18 0.082(3) 0.139(3) 0.102(3) -0.002(3) 0.040(2) 0.030(3)
C20 0.159(4) 0.095(3) 0.072(3) -0.001(2) 0.060(2) -0.022(2)
O3 0.0725(15) 0.0627(14) 0.0493(15) 0.0033(12) 0.0262(11) -0.0043(10)
O1 0.0512(17) 0.0474(16) 0.0698(15) 0.0090(11) 0.0162(11) 0.0041(12)
O4 0.0890(16) 0.0636(14) 0.0562(15) 0.0126(12) 0.0316(12) 0.0069(11)
O2 0.0804(18) 0.0505(15) 0.0882(18) 0.0114(13) 0.0253(13) -0.0102(13)
N1 0.062(2) 0.118(3) 0.112(3) 0.0151(19) 0.021(2) -0.012(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
C7 C1 1.505(4) . ?
C7 C14 1.536(4) . ?
C7 C8 1.549(3) . ?
C2 C3 1.371(4) . ?
C2 C1 1.376(4) . ?
C2 O1 1.414(3) . ?
C14 O3 1.430(3) . ?
C14 C16 1.472(5) . ?
C14 C15 1.531(4) . ?
C1 C6 1.390(4) . ?
C8 C9 1.521(3) . ?
C8 C13 1.525(3) . ?
C13 C12 1.523(4) . ?
C6 C5 1.389(4) . ?
C9 C10 1.516(4) . ?
C4 C5 1.359(4) . ?
C4 C3 1.372(4) . ?
C11 C10 1.507(4) . ?
C11 C12 1.511(4) . ?
C15 O2 1.187(3) . ?
C15 O1 1.351(3) . ?
C17 O4 1.460(3) . ?
C17 C18 1.506(4) . ?
C17 C19 1.507(4) . ?
C17 C20 1.516(4) . ?
C16 N1 1.144(4) . ?
O3 O4 1.473(2) . ?

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
C1 C7 C14 106.7(2) . . ?
C1 C7 C8 114.9(2) . . ?
C14 C7 C8 114.2(2) . . ?
C3 C2 C1 123.5(3) . . ?
C3 C2 O1 115.4(3) . . ?
C1 C2 O1 121.1(3) . . ?
O3 C14 C16 109.8(2) . . ?
O3 C14 C15 109.2(2) . . ?
C16 C14 C15 108.8(3) . . ?
O3 C14 C7 104.2(2) . . ?
C16 C14 C7 111.6(3) . . ?
C15 C14 C7 113.1(2) . . ?
C2 C1 C6 116.5(3) . . ?
C2 C1 C7 121.1(3) . . ?
C6 C1 C7 122.5(3) . . ?
C9 C8 C13 109.7(2) . . ?
C9 C8 C7 111.5(2) . . ?
C13 C8 C7 114.7(2) . . ?
C12 C13 C8 112.6(2) . . ?
C5 C6 C1 120.7(3) . . ?
C10 C9 C8 112.6(2) . . ?
C5 C4 C3 120.3(3) . . ?
C2 C3 C4 118.6(3) . . ?
C10 C11 C12 110.9(3) . . ?
C4 C5 C6 120.4(3) . . ?
C11 C10 C9 110.4(2) . . ?
C11 C12 C13 111.7(2) . . ?
O2 C15 O1 119.2(3) . . ?
O2 C15 C14 125.6(3) . . ?
O1 C15 C14 115.1(3) . . ?
O4 C17 C18 111.0(3) . . ?
O4 C17 C19 109.3(3) . . ?
C18 C17 C19 112.4(3) . . ?
O4 C17 C20 99.9(2) . . ?
C18 C17 C20 111.9(3) . . ?
C19 C17 C20 111.7(3) . . ?
N1 C16 C14 177.5(4) . . ?
C14 O3 O4 105.82(18) . . ?
C15 O1 C2 121.9(3) . . ?
C17 O4 O3 107.42(18) . . ?

_diffrn_measured_fraction_theta_max 0.782
_diffrn_reflns_theta_full        20.36
_diffrn_measured_fraction_theta_full 0.782
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1011614'
#######################################################################
#
#                 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_ab_160514_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.28

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.518(2)
_cell_length_b                   26.082(10)
_cell_length_c                   8.581(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.23(4)
_cell_angle_gamma                90.00
_cell_volume                     1231.6(10)
_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       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4345
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2174
_reflns_number_gt                1684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0472P)²+0.6491P] 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         2174
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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 -0.0109(3) 0.47356(6) 0.7929(2) 0.0447(5) Uani 1 1 d . . .
O2 O -0.3303(3) 0.50191(7) 0.6503(2) 0.0557(5) Uani 1 1 d . . .
O3 O -0.2946(3) 0.42966(7) 0.4265(2) 0.0525(5) Uani 1 1 d . . .
H3 H -0.3896 0.4536 0.4331 0.079 Uiso 1 1 calc R . .
C1 C 0.1800(4) 0.43938(9) 0.8181(3) 0.0382(6) Uani 1 1 d . . .
C9 C -0.1659(4) 0.47084(9) 0.6638(3) 0.0405(6) Uani 1 1 d . . .
C6 C 0.2202(4) 0.40096(9) 0.7089(3) 0.0360(5) Uani 1 1 d . . .
C7 C 0.0544(4) 0.39593(9) 0.5695(3) 0.0370(6) Uani 1 1 d . . .
C8 C -0.1280(4) 0.43045(9) 0.5509(3) 0.0386(6) Uani 1 1 d . . .
C10 C 0.0810(4) 0.35182(10) 0.4557(3) 0.0422(6) Uani 1 1 d . . .
H10 H 0.2295 0.3334 0.4917 0.051 Uiso 1 1 calc R . .
C5 C 0.4246(4) 0.36988(10) 0.7455(3) 0.0426(6) Uani 1 1 d . . .
H5 H 0.4598 0.3437 0.6772 0.051 Uiso 1 1 calc R . .
C14 C 0.1414(5) 0.32267(12) 0.1816(3) 0.0591(8) Uani 1 1 d . . .
H14A H 0.1489 0.3345 0.0748 0.071 Uiso 1 1 calc R . .
H14B H 0.2928 0.3053 0.2122 0.071 Uiso 1 1 calc R . .
C12 C -0.0987(6) 0.26805(11) 0.3547(3) 0.0640(8) Uani 1 1 d . . .
H12A H 0.0419 0.2482 0.3930 0.077 Uiso 1 1 calc R . .
H12B H -0.2407 0.2461 0.3555 0.077 Uiso 1 1 calc R . .
C15 C 0.1131(5) 0.36864(11) 0.2881(3) 0.0539(7) Uani 1 1 d . . .
H15A H -0.0270 0.3886 0.2494 0.065 Uiso 1 1 calc R . .
H15B H 0.2556 0.3903 0.2864 0.065 Uiso 1 1 calc R . .
C2 C 0.3236(5) 0.44625(10) 0.9544(3) 0.0477(6) Uani 1 1 d . . .
H2 H 0.2868 0.4716 1.0250 0.057 Uiso 1 1 calc R . .
C4 C 0.5741(5) 0.37706(10) 0.8793(3) 0.0493(7) Uani 1 1 d . . .
H4 H 0.7101 0.3563 0.8989 0.059 Uiso 1 1 calc R . .
C11 C -0.1287(6) 0.31362(10) 0.4626(3) 0.0566(8) Uani 1 1 d . . .
H11A H -0.1354 0.3015 0.5691 0.068 Uiso 1 1 calc R . .
H11B H -0.2809 0.3308 0.4327 0.068 Uiso 1 1 calc R . .
C13 C -0.0668(5) 0.28537(11) 0.1891(3) 0.0548(7) Uani 1 1 d . . .
H13A H -0.0371 0.2557 0.1251 0.066 Uiso 1 1 calc R . .
H13B H -0.2156 0.3015 0.1465 0.066 Uiso 1 1 calc R . .
C3 C 0.5229(5) 0.41501(11) 0.9847(3) 0.0520(7) Uani 1 1 d . . .
H3A H 0.6228 0.4194 1.0759 0.062 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0510(10) 0.0384(10) 0.0442(10) -0.0107(8) 0.0000(8) 0.0059(8)
O2 0.0623(12) 0.0441(11) 0.0600(13) -0.0100(9) -0.0009(9) 0.0183(10)
O3 0.0544(11) 0.0517(11) 0.0497(12) -0.0139(9) -0.0088(9) 0.0178(9)
C1 0.0413(13) 0.0351(12) 0.0387(14) -0.0014(10) 0.0068(10) -0.0023(11)
C9 0.0459(14) 0.0337(13) 0.0419(15) -0.0032(11) 0.0038(11) 0.0012(11)
C6 0.0401(12) 0.0334(12) 0.0354(13) -0.0003(10) 0.0081(10) -0.0023(10)
C7 0.0418(13) 0.0343(12) 0.0354(13) -0.0039(10) 0.0072(10) 0.0002(11)
C8 0.0410(13) 0.0372(13) 0.0374(14) -0.0045(11) 0.0021(10) 0.0012(11)
C10 0.0425(13) 0.0440(14) 0.0395(14) -0.0095(11) -0.0013(10) 0.0091(11)
C5 0.0459(14) 0.0414(14) 0.0411(15) -0.0007(11) 0.0071(11) 0.0036(11)
C14 0.0661(18) 0.0652(19) 0.0481(17) -0.0215(14) 0.0185(13) -0.0070(15)
C12 0.095(2) 0.0376(15) 0.0602(19) -0.0101(14) 0.0091(16) -0.0063(16)
C15 0.0658(17) 0.0502(16) 0.0480(17) -0.0136(13) 0.0181(13) -0.0144(14)
C2 0.0578(16) 0.0454(15) 0.0399(15) -0.0085(12) 0.0021(12) -0.0040(13)
C4 0.0475(15) 0.0505(16) 0.0488(16) 0.0065(13) -0.0027(12) 0.0035(12)
C11 0.084(2) 0.0378(14) 0.0506(17) -0.0035(13) 0.0196(14) -0.0067(14)
C13 0.0676(18) 0.0462(15) 0.0502(17) -0.0154(13) 0.0022(13) -0.0014(14)
C3 0.0567(16) 0.0571(17) 0.0406(16) -0.0004(13) -0.0078(12) -0.0056(14)

_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 C9 1.350(3) . ?
O1 C1 1.385(3) . ?
O2 C9 1.215(3) . ?
O3 C8 1.357(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.401(3) . ?
C9 C8 1.457(3) . ?
C6 C5 1.405(3) . ?
C6 C7 1.457(3) . ?
C7 C8 1.351(3) . ?
C7 C10 1.523(3) . ?
C10 C15 1.527(4) . ?
C10 C11 1.531(4) . ?
C5 C4 1.376(4) . ?
C14 C13 1.510(4) . ?
C14 C15 1.523(4) . ?
C12 C13 1.514(4) . ?
C12 C11 1.523(4) . ?
C2 C3 1.378(4) . ?
C4 C3 1.384(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
C9 O1 C1 121.52(18) . . ?
C2 C1 O1 115.7(2) . . ?
C2 C1 C6 123.5(2) . . ?
O1 C1 C6 120.8(2) . . ?
O2 C9 O1 117.8(2) . . ?
O2 C9 C8 124.2(2) . . ?
O1 C9 C8 118.1(2) . . ?
C1 C6 C5 115.3(2) . . ?
C1 C6 C7 119.5(2) . . ?
C5 C6 C7 125.2(2) . . ?
C8 C7 C6 117.0(2) . . ?
C8 C7 C10 122.2(2) . . ?
C6 C7 C10 120.7(2) . . ?
C7 C8 O3 122.6(2) . . ?
C7 C8 C9 123.1(2) . . ?
O3 C8 C9 114.3(2) . . ?
C7 C10 C15 114.2(2) . . ?
C7 C10 C11 111.0(2) . . ?
C15 C10 C11 111.3(2) . . ?
C4 C5 C6 122.0(2) . . ?
C13 C14 C15 111.7(2) . . ?
C13 C12 C11 111.3(2) . . ?
C14 C15 C10 111.3(2) . . ?
C1 C2 C3 119.0(2) . . ?
C5 C4 C3 120.3(3) . . ?
C12 C11 C10 111.6(2) . . ?
C14 C13 C12 111.9(2) . . ?
C2 C3 C4 119.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1011615'
#######################################################################
#
#                 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_ab_come

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 Cl O5'
_chemical_formula_sum            'C21 H27 Cl O5'
_chemical_formula_weight         394.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   17.6306(4)
_cell_length_b                   6.5284(2)
_cell_length_c                   18.1875(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.7010(10)
_cell_angle_gamma                90.00
_cell_volume                     2079.07(9)
_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       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20249
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3560
_reflns_number_gt                2960
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0346P)²+1.2846P] 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         3560
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
Cl1 Cl -0.00224(3) 0.14465(10) 1.09669(3) 0.05410(18) Uani 1 1 d . . .
C9 C 0.23752(10) 0.3351(3) 0.96411(10) 0.0314(4) Uani 1 1 d . . .
H9 H 0.2521 0.1951 0.9792 0.038 Uiso 1 1 calc R . .
C10 C 0.21361(10) 0.3297(3) 0.87889(10) 0.0341(4) Uani 1 1 d . . .
H10 H 0.2587 0.2883 0.8557 0.041 Uiso 1 1 calc R . .
C6 C 0.12117(10) 0.2572(3) 1.03050(10) 0.0357(4) Uani 1 1 d . . .
H6 H 0.1244 0.1198 1.0177 0.043 Uiso 1 1 calc R . .
C1 C 0.17361(10) 0.3978(3) 1.00836(10) 0.0322(4) Uani 1 1 d . . .
C5 C 0.06421(11) 0.3224(3) 1.07152(11) 0.0397(5) Uani 1 1 d . . .
C8 C 0.30666(10) 0.4750(3) 0.99090(10) 0.0345(4) Uani 1 1 d . . .
C11 C 0.15260(11) 0.1645(3) 0.86041(11) 0.0408(5) Uani 1 1 d . . .
H11A H 0.1726 0.0335 0.8789 0.049 Uiso 1 1 calc R . .
H11B H 0.1084 0.1965 0.8855 0.049 Uiso 1 1 calc R . .
C2 C 0.16720(11) 0.5993(3) 1.02974(10) 0.0369(5) Uani 1 1 d . . .
C7 C 0.28433(12) 0.7019(3) 0.98342(11) 0.0412(5) Uani 1 1 d . . .
C15 C 0.18612(12) 0.5336(3) 0.84393(11) 0.0429(5) Uani 1 1 d . . .
H15A H 0.2272 0.6330 0.8516 0.051 Uiso 1 1 calc R . .
H15B H 0.1439 0.5841 0.8685 0.051 Uiso 1 1 calc R . .
C13 C 0.09962(12) 0.3502(4) 0.74451(12) 0.0486(6) Uani 1 1 d . . .
H13A H 0.0871 0.3361 0.6914 0.058 Uiso 1 1 calc R . .
H13B H 0.0537 0.3908 0.7653 0.058 Uiso 1 1 calc R . .
C12 C 0.12758(12) 0.1463(4) 0.77735(12) 0.0474(5) Uani 1 1 d . . .
H12A H 0.1703 0.0990 0.7527 0.057 Uiso 1 1 calc R . .
H12B H 0.0870 0.0457 0.7689 0.057 Uiso 1 1 calc R . .
C16 C 0.37688(11) 0.4196(3) 0.95155(12) 0.0421(5) Uani 1 1 d . . .
C4 C 0.05904(12) 0.5240(4) 1.09273(12) 0.0481(6) Uani 1 1 d . . .
H4 H 0.0208 0.5656 1.1206 0.058 Uiso 1 1 calc R . .
C14 C 0.16038(13) 0.5137(4) 0.76083(12) 0.0518(6) Uani 1 1 d . . .
H14A H 0.1403 0.6443 0.7419 0.062 Uiso 1 1 calc R . .
H14B H 0.2041 0.4799 0.7354 0.062 Uiso 1 1 calc R . .
C3 C 0.11136(12) 0.6629(4) 1.07210(12) 0.0472(5) Uani 1 1 d . . .
H3 H 0.1092 0.7992 1.0866 0.057 Uiso 1 1 calc R . .
C17 C 0.43116(13) 0.2646(4) 0.98814(14) 0.0579(6) Uani 1 1 d . . .
H17A H 0.4688 0.2313 0.9559 0.087 Uiso 1 1 calc R . .
H17B H 0.4036 0.1431 0.9984 0.087 Uiso 1 1 calc R . .
H17C H 0.4560 0.3198 1.0336 0.087 Uiso 1 1 calc R . .
O5 O 0.31992(7) 0.4330(2) 1.06860(7) 0.0397(3) Uani 1 1 d . . .
C18 C 0.37919(13) 0.6033(4) 1.17598(12) 0.0544(6) Uani 1 1 d . . .
C19 C 0.44436(17) 0.7553(5) 1.19369(15) 0.0812(9) Uani 1 1 d . . .
H19A H 0.4906 0.6982 1.1794 0.122 Uiso 1 1 calc R . .
H19B H 0.4509 0.7832 1.2459 0.122 Uiso 1 1 calc R . .
H19C H 0.4326 0.8803 1.1670 0.122 Uiso 1 1 calc R . .
C21 C 0.3972(2) 0.3985(5) 1.21254(16) 0.0902(10) Uani 1 1 d . . .
H21A H 0.3559 0.3052 1.1989 0.135 Uiso 1 1 calc R . .
H21B H 0.4040 0.4154 1.2653 0.135 Uiso 1 1 calc R . .
H21C H 0.4433 0.3446 1.1966 0.135 Uiso 1 1 calc R . .
C20 C 0.30377(18) 0.6875(7) 1.19349(18) 0.1066(13) Uani 1 1 d . . .
H20A H 0.2924 0.8116 1.1660 0.160 Uiso 1 1 calc R . .
H20B H 0.3066 0.7159 1.2455 0.160 Uiso 1 1 calc R . .
H20C H 0.2642 0.5887 1.1800 0.160 Uiso 1 1 calc R . .
O1 O 0.21633(8) 0.7513(2) 1.00909(8) 0.0445(4) Uani 1 1 d . . .
O4 O 0.37934(8) 0.5839(2) 1.09674(8) 0.0497(4) Uani 1 1 d . . .
O2 O 0.32035(9) 0.8370(2) 0.96047(9) 0.0580(4) Uani 1 1 d . . .
O3 O 0.38372(9) 0.4926(3) 0.89225(9) 0.0635(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0425(3) 0.0675(4) 0.0550(3) 0.0086(3) 0.0173(2) -0.0050(3)
C9 0.0306(9) 0.0283(11) 0.0354(10) -0.0005(8) 0.0043(7) 0.0003(8)
C10 0.0289(9) 0.0372(12) 0.0364(10) -0.0049(8) 0.0053(8) 0.0008(8)
C6 0.0377(10) 0.0361(12) 0.0334(10) 0.0006(8) 0.0044(8) -0.0007(8)
C1 0.0322(9) 0.0333(12) 0.0305(9) 0.0011(8) 0.0017(7) 0.0015(8)
C5 0.0354(10) 0.0497(14) 0.0342(10) 0.0072(9) 0.0055(8) 0.0026(9)
C8 0.0348(10) 0.0371(12) 0.0309(10) 0.0017(8) 0.0013(8) -0.0037(8)
C11 0.0428(11) 0.0368(12) 0.0420(11) -0.0044(9) 0.0011(9) -0.0038(9)
C2 0.0411(11) 0.0329(12) 0.0365(10) 0.0032(8) 0.0033(8) 0.0020(8)
C7 0.0433(11) 0.0388(13) 0.0399(11) -0.0001(9) -0.0017(9) -0.0082(10)
C15 0.0480(12) 0.0405(13) 0.0394(11) 0.0025(9) 0.0019(9) -0.0056(9)
C13 0.0407(11) 0.0652(16) 0.0387(11) -0.0031(10) -0.0007(9) 0.0013(11)
C12 0.0419(11) 0.0531(15) 0.0461(12) -0.0125(10) 0.0008(9) -0.0040(10)
C16 0.0343(10) 0.0466(13) 0.0452(12) -0.0027(10) 0.0031(9) -0.0097(9)
C4 0.0455(12) 0.0578(16) 0.0433(12) 0.0035(10) 0.0151(9) 0.0137(11)
C14 0.0550(13) 0.0596(16) 0.0396(12) 0.0085(10) 0.0007(10) -0.0047(11)
C3 0.0564(13) 0.0377(13) 0.0484(12) -0.0039(10) 0.0099(10) 0.0131(10)
C17 0.0477(13) 0.0562(16) 0.0715(16) 0.0029(13) 0.0137(11) 0.0075(11)
O5 0.0381(7) 0.0440(9) 0.0355(7) 0.0008(6) -0.0022(6) -0.0082(6)
C18 0.0560(13) 0.0675(17) 0.0372(11) -0.0078(11) -0.0044(10) -0.0036(12)
C19 0.094(2) 0.086(2) 0.0574(16) -0.0124(15) -0.0173(15) -0.0269(18)
C21 0.112(3) 0.088(2) 0.0622(17) 0.0199(16) -0.0240(17) -0.0161(19)
C20 0.085(2) 0.162(4) 0.072(2) -0.049(2) 0.0054(17) 0.020(2)
O1 0.0523(8) 0.0291(8) 0.0529(9) -0.0003(6) 0.0100(7) -0.0004(6)
O4 0.0479(8) 0.0606(10) 0.0389(8) -0.0068(7) -0.0026(6) -0.0205(7)
O2 0.0594(10) 0.0411(10) 0.0738(11) 0.0071(8) 0.0089(8) -0.0161(8)
O3 0.0509(9) 0.0917(14) 0.0500(10) 0.0140(9) 0.0154(7) -0.0015(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.747(2) . ?
C9 C1 1.516(2) . ?
C9 C8 1.556(3) . ?
C9 C10 1.558(3) . ?
C10 C15 1.529(3) . ?
C10 C11 1.533(3) . ?
C6 C5 1.386(3) . ?
C6 C1 1.395(3) . ?
C1 C2 1.380(3) . ?
C5 C4 1.378(3) . ?
C8 O5 1.432(2) . ?
C8 C7 1.535(3) . ?
C8 C16 1.543(3) . ?
C11 C12 1.528(3) . ?
C2 C3 1.383(3) . ?
C2 O1 1.397(2) . ?
C7 O2 1.190(2) . ?
C7 O1 1.375(2) . ?
C15 C14 1.532(3) . ?
C13 C14 1.517(3) . ?
C13 C12 1.518(3) . ?
C16 O3 1.198(2) . ?
C16 C17 1.495(3) . ?
C4 C3 1.377(3) . ?
O5 O4 1.4846(18) . ?
C18 O4 1.447(3) . ?
C18 C20 1.507(4) . ?
C18 C21 1.511(4) . ?
C18 C19 1.524(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
C1 C9 C8 106.20(15) . . ?
C1 C9 C10 113.74(14) . . ?
C8 C9 C10 115.84(15) . . ?
C15 C10 C11 109.95(16) . . ?
C15 C10 C9 115.46(16) . . ?
C11 C10 C9 109.58(15) . . ?
C5 C6 C1 120.0(2) . . ?
C2 C1 C6 117.84(17) . . ?
C2 C1 C9 119.84(17) . . ?
C6 C1 C9 122.30(18) . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 Cl1 119.52(16) . . ?
C6 C5 Cl1 119.17(17) . . ?
O5 C8 C7 106.43(15) . . ?
O5 C8 C16 111.43(15) . . ?
C7 C8 C16 113.36(17) . . ?
O5 C8 C9 103.21(14) . . ?
C7 C8 C9 110.83(15) . . ?
C16 C8 C9 111.02(15) . . ?
C12 C11 C10 112.68(17) . . ?
C1 C2 C3 122.04(19) . . ?
C1 C2 O1 121.85(17) . . ?
C3 C2 O1 116.11(19) . . ?
O2 C7 O1 117.9(2) . . ?
O2 C7 C8 127.2(2) . . ?
O1 C7 C8 114.91(17) . . ?
C10 C15 C14 112.30(18) . . ?
C14 C13 C12 110.53(17) . . ?
C13 C12 C11 111.35(18) . . ?
O3 C16 C17 122.9(2) . . ?
O3 C16 C8 119.66(19) . . ?
C17 C16 C8 117.30(18) . . ?
C3 C4 C5 119.00(19) . . ?
C13 C14 C15 111.94(18) . . ?
C4 C3 C2 119.8(2) . . ?
C8 O5 O4 103.93(13) . . ?
O4 C18 C20 110.3(2) . . ?
O4 C18 C21 109.6(2) . . ?
C20 C18 C21 112.1(3) . . ?
O4 C18 C19 100.29(19) . . ?
C20 C18 C19 112.3(3) . . ?
C21 C18 C19 111.6(2) . . ?
C7 O1 C2 121.14(16) . . ?
C18 O4 O5 108.56(14) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 1011616'
