# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Liuzhu Gong'
_publ_contact_author_email       GONGLZ@USTC.EDU.CN

_publ_section_title              
;
Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition:
A Straightforward Approach to Access Multiply Substituted
Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in High Optical
Purity
;
loop_
_publ_author_name
'Liuzhu Gong'
'Xiao-Hua Chen'
'Nan Li'
'Bin Liu'
'Jin Song'
'Xi-Feng Tu'

# Attachment '091204.cif'

data_091204
_database_code_depnum_ccdc_archive 'CCDC 759560'
#TrackingRef '091204.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Cl N O5'
_chemical_formula_weight         415.86
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   9.6104(10)
_cell_length_b                   6.8695(13)
_cell_length_c                   15.6735(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.706(11)
_cell_angle_gamma                90.00
_cell_volume                     1033.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2786
_cell_measurement_theta_min      2.8258
_cell_measurement_theta_max      59.9926

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    1.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6480
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         60.01
_reflns_number_total             2778
_reflns_number_gt                2219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0703P)^2^+0.9815P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         2778
_refine_ls_number_parameters     267
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6567(2) 0.3723(4) 0.44512(13) 0.1035(7) Uani 1 1 d . . .
O1 O 0.1574(4) 1.1285(6) -0.0031(2) 0.0713(12) Uani 1 1 d . . .
O3 O 0.0606(4) 0.8430(6) 0.3913(2) 0.0637(10) Uani 1 1 d . . .
O4 O -0.1017(4) 0.8697(8) 0.2279(3) 0.0847(14) Uani 1 1 d . . .
N1 N 0.2929(5) 1.0969(7) 0.2549(3) 0.0573(13) Uani 1 1 d . . .
O2 O 0.1083(5) 1.1561(7) 0.3718(3) 0.0757(12) Uani 1 1 d . . .
C8 C 0.1393(5) 0.8262(8) 0.2038(3) 0.0494(13) Uani 1 1 d . . .
H8 H 0.1918 0.7146 0.1834 0.059 Uiso 1 1 calc R . .
C7 C 0.2236(5) 0.9211(8) 0.2861(3) 0.0497(13) Uani 1 1 d . . .
O5 O -0.0145(5) 0.5686(8) 0.2235(3) 0.0956(14) Uani 1 1 d DU . .
C3 C 0.2970(6) 0.5898(9) 0.3503(3) 0.0573(15) Uani 1 1 d . . .
H3 H 0.2060 0.5459 0.3410 0.069 Uiso 1 1 calc R . .
C4 C 0.3309(6) 0.7805(8) 0.3255(3) 0.0526(14) Uani 1 1 d . . .
C21 C 0.1239(6) 0.9909(10) 0.3541(3) 0.0548(14) Uani 1 1 d . . .
C9 C 0.1466(5) 0.9930(8) 0.1391(3) 0.0494(13) Uani 1 1 d . . .
H9 H 0.0772 1.0914 0.1527 0.059 Uiso 1 1 calc R . .
C10 C 0.2897(5) 1.0731(9) 0.1619(3) 0.0518(13) Uani 1 1 d . . .
H10 H 0.3582 0.9734 0.1485 0.062 Uiso 1 1 calc R . .
C13 C 0.1335(6) 0.9503(9) 0.0440(4) 0.0621(16) Uani 1 1 d . . .
H13A H 0.2012 0.8525 0.0294 0.074 Uiso 1 1 calc R . .
H13B H 0.0412 0.9003 0.0290 0.074 Uiso 1 1 calc R . .
C2 C 0.3955(6) 0.4659(9) 0.3880(4) 0.0620(15) Uani 1 1 d . . .
H2 H 0.3707 0.3415 0.4052 0.074 Uiso 1 1 calc R . .
C11 C 0.3189(6) 1.2503(8) 0.1105(3) 0.0516(14) Uani 1 1 d . . .
C12 C 0.2543(6) 1.2609(9) 0.0275(4) 0.0562(14) Uani 1 1 d . . .
C18 C -0.0062(7) 0.7638(11) 0.2190(4) 0.0695(14) Uani 1 1 d U . .
C5 C 0.4699(6) 0.8341(11) 0.3386(4) 0.0720(18) Uani 1 1 d . . .
H5 H 0.4969 0.9582 0.3223 0.086 Uiso 1 1 calc R . .
C6 C 0.5689(7) 0.7113(13) 0.3747(5) 0.086(2) Uani 1 1 d . . .
H6 H 0.6612 0.7513 0.3821 0.103 Uiso 1 1 calc R . .
C14 C 0.2847(7) 1.4152(11) -0.0259(4) 0.0723(19) Uani 1 1 d . . .
H14 H 0.2404 1.4239 -0.0798 0.087 Uiso 1 1 calc R . .
C17 C 0.4111(6) 1.3925(9) 0.1365(4) 0.0610(15) Uani 1 1 d . . .
H17 H 0.4541 1.3855 0.1908 0.073 Uiso 1 1 calc R . .
C16 C 0.4422(6) 1.5489(10) 0.0829(5) 0.0722(18) Uani 1 1 d . . .
H16 H 0.5032 1.6465 0.1018 0.087 Uiso 1 1 calc R . .
C15 C 0.3795(7) 1.5550(11) 0.0002(5) 0.0733(18) Uani 1 1 d . . .
H15 H 0.4023 1.6542 -0.0370 0.088 Uiso 1 1 calc R . .
C22 C -0.0451(6) 0.8991(11) 0.4495(4) 0.0770(19) Uani 1 1 d . . .
H22A H -0.0026 0.9706 0.4965 0.116 Uiso 1 1 calc R . .
H22B H -0.0892 0.7846 0.4707 0.116 Uiso 1 1 calc R . .
H22C H -0.1136 0.9793 0.4200 0.116 Uiso 1 1 calc R . .
C1 C 0.5299(7) 0.5295(11) 0.3997(4) 0.0713(18) Uani 1 1 d . . .
C20 C -0.1961(10) 0.3309(15) 0.1955(6) 0.127(3) Uani 1 1 d DU . .
H20A H -0.2422 0.3826 0.1448 0.190 Uiso 1 1 calc R . .
H20B H -0.2602 0.2523 0.2256 0.190 Uiso 1 1 calc R . .
H20C H -0.1184 0.2526 0.1801 0.190 Uiso 1 1 calc R . .
C19 C -0.1465(9) 0.4908(13) 0.2503(6) 0.117(2) Uani 1 1 d DU . .
H19A H -0.2156 0.5938 0.2487 0.140 Uiso 1 1 calc R . .
H19B H -0.1351 0.4450 0.3087 0.140 Uiso 1 1 calc R . .
H1 H 0.229(10) 1.184(16) 0.263(6) 0.140 Uiso 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 0.0811(11) 0.1290(18) 0.0999(13) 0.0342(13) -0.0020(9) 0.0290(12)
O1 0.082(3) 0.066(3) 0.065(3) 0.009(2) -0.007(2) -0.005(2)
O3 0.068(2) 0.060(3) 0.065(2) 0.005(2) 0.0176(19) -0.006(2)
O4 0.057(2) 0.104(4) 0.093(3) 0.016(3) 0.007(2) -0.003(3)
N1 0.068(3) 0.056(4) 0.048(2) 0.004(2) 0.004(2) -0.015(2)
O2 0.095(3) 0.055(3) 0.081(3) -0.005(2) 0.034(2) -0.004(3)
C8 0.051(3) 0.048(4) 0.050(3) -0.001(2) 0.004(2) 0.001(2)
C7 0.055(3) 0.049(4) 0.046(3) -0.002(2) 0.009(2) -0.006(3)
O5 0.098(2) 0.090(2) 0.100(2) -0.0052(18) 0.0136(17) -0.0145(18)
C3 0.060(3) 0.051(4) 0.061(3) -0.007(3) 0.001(3) -0.008(3)
C4 0.056(3) 0.056(4) 0.046(3) -0.005(3) 0.005(2) -0.005(3)
C21 0.061(3) 0.052(4) 0.051(3) -0.001(3) 0.006(3) -0.007(3)
C9 0.051(3) 0.050(3) 0.048(3) 0.001(2) 0.005(2) -0.003(2)
C10 0.052(3) 0.055(4) 0.050(3) -0.001(3) 0.011(2) -0.001(3)
C13 0.061(3) 0.068(5) 0.057(3) -0.007(3) -0.002(3) -0.006(3)
C2 0.071(4) 0.051(4) 0.064(3) 0.003(3) 0.005(3) 0.005(3)
C11 0.051(3) 0.050(4) 0.055(3) 0.002(3) 0.015(2) 0.003(3)
C12 0.053(3) 0.055(4) 0.061(3) 0.004(3) 0.010(3) 0.006(3)
C18 0.068(4) 0.088(2) 0.053(3) -0.002(3) 0.003(3) 0.005(3)
C5 0.055(3) 0.074(5) 0.087(4) 0.015(4) 0.002(3) -0.013(3)
C6 0.047(3) 0.114(7) 0.098(5) 0.018(5) 0.003(3) 0.003(4)
C14 0.070(4) 0.082(5) 0.067(4) 0.024(4) 0.021(3) 0.027(4)
C17 0.055(3) 0.057(4) 0.072(3) 0.004(3) 0.015(3) 0.006(3)
C16 0.063(4) 0.064(5) 0.093(5) 0.012(4) 0.031(3) 0.000(3)
C15 0.069(4) 0.063(5) 0.091(5) 0.014(4) 0.031(4) 0.008(4)
C22 0.072(4) 0.080(5) 0.081(4) 0.002(4) 0.030(3) -0.010(4)
C1 0.068(4) 0.083(5) 0.062(4) 0.005(3) -0.005(3) 0.007(4)
C20 0.123(4) 0.128(4) 0.129(4) -0.003(2) 0.006(2) -0.003(2)
C19 0.111(3) 0.117(3) 0.124(3) -0.001(2) 0.023(2) -0.026(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
Cl1 C1 1.754(7) . ?
O1 C12 1.371(7) . ?
O1 C13 1.454(7) . ?
O3 C21 1.333(7) . ?
O3 C22 1.450(7) . ?
O4 C18 1.185(8) . ?
N1 C10 1.466(7) . ?
N1 C7 1.474(7) . ?
N1 H1 0.87(10) . ?
O2 C21 1.180(7) . ?
C8 C18 1.492(8) . ?
C8 C9 1.534(7) . ?
C8 C7 1.626(7) . ?
C8 H8 0.9800 . ?
C7 C4 1.522(8) . ?
C7 C21 1.543(8) . ?
O5 C18 1.345(8) . ?
O5 C19 1.457(7) . ?
C3 C2 1.385(8) . ?
C3 C4 1.409(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(8) . ?
C9 C10 1.508(7) . ?
C9 C13 1.519(7) . ?
C9 H9 0.9800 . ?
C10 C11 1.494(8) . ?
C10 H10 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 C1 1.367(9) . ?
C2 H2 0.9300 . ?
C11 C17 1.368(8) . ?
C11 C12 1.417(8) . ?
C12 C14 1.389(9) . ?
C5 C6 1.374(9) . ?
C5 H5 0.9300 . ?
C6 C1 1.367(10) . ?
C6 H6 0.9300 . ?
C14 C15 1.373(9) . ?
C14 H14 0.9300 . ?
C17 C16 1.405(9) . ?
C17 H17 0.9300 . ?
C16 C15 1.403(9) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 C19 1.460(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C12 O1 C13 120.1(4) . . ?
C21 O3 C22 114.9(5) . . ?
C10 N1 C7 104.5(4) . . ?
C10 N1 H1 104(7) . . ?
C7 N1 H1 101(7) . . ?
C18 C8 C9 113.1(5) . . ?
C18 C8 C7 115.1(4) . . ?
C9 C8 C7 100.8(4) . . ?
C18 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
N1 C7 C4 110.3(4) . . ?
N1 C7 C21 106.2(5) . . ?
C4 C7 C21 110.3(4) . . ?
N1 C7 C8 106.3(4) . . ?
C4 C7 C8 111.7(4) . . ?
C21 C7 C8 111.7(4) . . ?
C18 O5 C19 115.8(7) . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.0(5) . . ?
C5 C4 C7 121.3(5) . . ?
C3 C4 C7 122.7(5) . . ?
O2 C21 O3 124.4(6) . . ?
O2 C21 C7 123.5(6) . . ?
O3 C21 C7 112.1(6) . . ?
C10 C9 C13 109.6(4) . . ?
C10 C9 C8 100.7(4) . . ?
C13 C9 C8 120.0(5) . . ?
C10 C9 H9 108.6 . . ?
C13 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
N1 C10 C11 116.7(5) . . ?
N1 C10 C9 104.6(4) . . ?
C11 C10 C9 111.2(5) . . ?
N1 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
O1 C13 C9 109.1(5) . . ?
O1 C13 H13A 109.9 . . ?
C9 C13 H13A 109.9 . . ?
O1 C13 H13B 109.9 . . ?
C9 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C1 C2 C3 118.9(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C17 C11 C12 119.1(5) . . ?
C17 C11 C10 123.8(5) . . ?
C12 C11 C10 116.9(5) . . ?
O1 C12 C14 117.0(5) . . ?
O1 C12 C11 123.2(5) . . ?
C14 C12 C11 119.7(6) . . ?
O4 C18 O5 123.9(7) . . ?
O4 C18 C8 125.4(7) . . ?
O5 C18 C8 110.7(6) . . ?
C6 C5 C4 122.7(7) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C1 C6 C5 119.0(6) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C15 C14 C12 120.7(6) . . ?
C15 C14 H14 119.7 . . ?
C12 C14 H14 119.7 . . ?
C11 C17 C16 121.4(6) . . ?
C11 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C15 C16 C17 118.7(7) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C14 C15 C16 120.3(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6 C1 C2 121.6(6) . . ?
C6 C1 Cl1 118.9(5) . . ?
C2 C1 Cl1 119.4(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C19 C20 111.8(8) . . ?
O5 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
O5 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C7 C4 104.6(5) . . . . ?
C10 N1 C7 C21 -135.9(4) . . . . ?
C10 N1 C7 C8 -16.7(5) . . . . ?
C18 C8 C7 N1 -134.7(5) . . . . ?
C9 C8 C7 N1 -12.6(5) . . . . ?
C18 C8 C7 C4 105.0(6) . . . . ?
C9 C8 C7 C4 -132.9(4) . . . . ?
C18 C8 C7 C21 -19.1(7) . . . . ?
C9 C8 C7 C21 102.9(5) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
C2 C3 C4 C7 -178.3(5) . . . . ?
N1 C7 C4 C5 8.3(7) . . . . ?
C21 C7 C4 C5 -108.8(6) . . . . ?
C8 C7 C4 C5 126.3(5) . . . . ?
N1 C7 C4 C3 -171.3(4) . . . . ?
C21 C7 C4 C3 71.6(6) . . . . ?
C8 C7 C4 C3 -53.3(6) . . . . ?
C22 O3 C21 O2 7.4(8) . . . . ?
C22 O3 C21 C7 -173.9(4) . . . . ?
N1 C7 C21 O2 2.5(7) . . . . ?
C4 C7 C21 O2 122.0(6) . . . . ?
C8 C7 C21 O2 -113.1(6) . . . . ?
N1 C7 C21 O3 -176.2(4) . . . . ?
C4 C7 C21 O3 -56.7(6) . . . . ?
C8 C7 C21 O3 68.3(6) . . . . ?
C18 C8 C9 C10 159.2(5) . . . . ?
C7 C8 C9 C10 35.8(5) . . . . ?
C18 C8 C9 C13 -80.6(7) . . . . ?
C7 C8 C9 C13 156.0(5) . . . . ?
C7 N1 C10 C11 164.6(4) . . . . ?
C7 N1 C10 C9 41.2(5) . . . . ?
C13 C9 C10 N1 -176.6(5) . . . . ?
C8 C9 C10 N1 -49.2(5) . . . . ?
C13 C9 C10 C11 56.5(6) . . . . ?
C8 C9 C10 C11 -176.1(4) . . . . ?
C12 O1 C13 C9 36.2(7) . . . . ?
C10 C9 C13 O1 -58.8(6) . . . . ?
C8 C9 C13 O1 -174.5(4) . . . . ?
C4 C3 C2 C1 -1.5(9) . . . . ?
N1 C10 C11 C17 34.8(8) . . . . ?
C9 C10 C11 C17 154.7(5) . . . . ?
N1 C10 C11 C12 -150.3(5) . . . . ?
C9 C10 C11 C12 -30.4(7) . . . . ?
C13 O1 C12 C14 171.9(5) . . . . ?
C13 O1 C12 C11 -10.4(8) . . . . ?
C17 C11 C12 O1 -177.9(5) . . . . ?
C10 C11 C12 O1 6.9(8) . . . . ?
C17 C11 C12 C14 -0.3(8) . . . . ?
C10 C11 C12 C14 -175.5(5) . . . . ?
C19 O5 C18 O4 -7.0(10) . . . . ?
C19 O5 C18 C8 171.5(6) . . . . ?
C9 C8 C18 O4 -43.0(8) . . . . ?
C7 C8 C18 O4 72.2(8) . . . . ?
C9 C8 C18 O5 138.5(5) . . . . ?
C7 C8 C18 O5 -106.3(6) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C7 C4 C5 C6 179.4(6) . . . . ?
C4 C5 C6 C1 -0.7(11) . . . . ?
O1 C12 C14 C15 179.4(5) . . . . ?
C11 C12 C14 C15 1.7(8) . . . . ?
C12 C11 C17 C16 0.4(8) . . . . ?
C10 C11 C17 C16 175.2(5) . . . . ?
C11 C17 C16 C15 -1.7(9) . . . . ?
C12 C14 C15 C16 -3.0(9) . . . . ?
C17 C16 C15 C14 3.0(9) . . . . ?
C5 C6 C1 C2 1.3(11) . . . . ?
C5 C6 C1 Cl1 179.6(6) . . . . ?
C3 C2 C1 C6 -0.3(10) . . . . ?
C3 C2 C1 Cl1 -178.5(5) . . . . ?
C18 O5 C19 C20 133.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        60.01
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.053