# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_9decb
_database_code_depnum_ccdc_archive 'CCDC 922005'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Cl N O4'
_chemical_formula_weight         399.86
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   10.6173(7)
_cell_length_b                   9.2220(6)
_cell_length_c                   10.9711(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.165(2)
_cell_angle_gamma                90.00
_cell_volume                     972.25(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4348
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.30
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7713
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4001
_reflns_number_gt                3556
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0304P)^2^+0.2758P] 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    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   0.01(5)
_refine_ls_number_reflns         4001
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.7035(2) 0.0563(3) 0.7614(2) 0.0248(5) Uani 1 1 d . . .
H1 H 0.6906 0.0090 0.8301 0.030 Uiso 1 1 calc R . .
C2 C 0.8303(3) 0.1167(3) 0.7873(2) 0.0271(6) Uani 1 1 d . . .
H2A H 0.9028 0.1095 0.8729 0.033 Uiso 1 1 calc R . .
C3 C 0.8504(2) 0.1882(2) 0.6864(2) 0.0246(5) Uani 1 1 d . . .
H3 H 0.9360 0.2298 0.7029 0.030 Uiso 1 1 calc R . .
C4 C 0.7402(2) 0.1965(2) 0.5601(2) 0.0202(5) Uani 1 1 d . . .
H4 H 0.7521 0.2440 0.4910 0.024 Uiso 1 1 calc R . .
C5 C 0.6129(2) 0.1355(2) 0.5349(2) 0.0165(4) Uani 1 1 d . . .
C6 C 0.4912(2) 0.1401(2) 0.3949(2) 0.0162(4) Uani 1 1 d . . .
C7 C 0.4544(2) -0.0110(2) 0.3356(2) 0.0181(4) Uani 1 1 d . . .
H7A H 0.4487 -0.0758 0.4027 0.022 Uiso 1 1 calc R . .
H7B H 0.5279 -0.0461 0.3129 0.022 Uiso 1 1 calc R . .
C8 C 0.3159(2) -0.0147(2) 0.20916(19) 0.0161(4) Uani 1 1 d . . .
H8 H 0.2824 -0.1149 0.2003 0.019 Uiso 1 1 calc R . .
C9 C 0.3323(2) 0.0190(2) 0.08022(19) 0.0161(4) Uani 1 1 d . . .
C10 C 0.4080(2) -0.0786(2) 0.0409(2) 0.0199(5) Uani 1 1 d . . .
H10 H 0.4445 -0.1615 0.0921 0.024 Uiso 1 1 calc R . .
C11 C 0.4297(2) -0.0544(3) -0.0728(2) 0.0219(5) Uani 1 1 d . . .
H11 H 0.4816 -0.1203 -0.0968 0.026 Uiso 1 1 calc R . .
C12 C 0.3748(2) 0.0671(3) -0.1513(2) 0.0205(5) Uani 1 1 d . . .
H12 H 0.3890 0.0844 -0.2280 0.025 Uiso 1 1 calc R . .
C13 C 0.2986(2) 0.1620(2) -0.1123(2) 0.0173(4) Uani 1 1 d . . .
C14 C 0.2762(2) 0.1406(2) 0.0022(2) 0.0170(4) Uani 1 1 d . . .
H14 H 0.2245 0.2069 0.0260 0.020 Uiso 1 1 calc R . .
C15 C 0.2106(2) 0.0764(2) 0.2327(2) 0.0152(4) Uani 1 1 d . . .
C16 C 0.2475(2) 0.1762(2) 0.3318(2) 0.0157(4) Uani 1 1 d . . .
C17 C 0.1487(2) 0.2679(2) 0.3627(2) 0.0186(5) Uani 1 1 d . . .
H17A H 0.1438 0.3632 0.3235 0.022 Uiso 1 1 calc R . .
H17B H 0.1851 0.2799 0.4596 0.022 Uiso 1 1 calc R . .
C18 C 0.0016(2) 0.2049(2) 0.3102(2) 0.0192(5) Uani 1 1 d . . .
C19 C 0.0011(2) 0.0807(3) 0.4022(2) 0.0230(5) Uani 1 1 d . . .
H19A H 0.0591 0.0034 0.3967 0.034 Uiso 1 1 calc R . .
H19B H -0.0923 0.0458 0.3742 0.034 Uiso 1 1 calc R . .
H19C H 0.0362 0.1148 0.4933 0.034 Uiso 1 1 calc R . .
C20 C -0.0995(2) 0.3222(3) 0.3104(2) 0.0253(5) Uani 1 1 d . . .
H20A H -0.0726 0.3563 0.4007 0.038 Uiso 1 1 calc R . .
H20B H -0.1919 0.2828 0.2761 0.038 Uiso 1 1 calc R . .
H20C H -0.0977 0.4014 0.2544 0.038 Uiso 1 1 calc R . .
C21 C -0.0409(2) 0.1517(3) 0.1658(2) 0.0199(5) Uani 1 1 d . . .
H21A H -0.1300 0.1028 0.1354 0.024 Uiso 1 1 calc R . .
H21B H -0.0533 0.2351 0.1080 0.024 Uiso 1 1 calc R . .
C22 C 0.0626(2) 0.0494(2) 0.14961(19) 0.0172(4) Uani 1 1 d . . .
N1 N 0.59584(18) 0.0647(2) 0.63626(17) 0.0190(4) Uani 1 1 d . . .
O1 O 0.47671(16) 0.00352(17) 0.61599(15) 0.0231(4) Uani 1 1 d . . .
O2 O 0.52198(16) 0.22666(16) 0.30821(14) 0.0196(3) Uani 1 1 d . . .
H2 H 0.5212 0.3121 0.3287 0.029 Uiso 1 1 calc R . .
O3 O 0.37993(14) 0.20825(16) 0.41735(14) 0.0177(3) Uani 1 1 d . . .
O4 O 0.02380(15) -0.04858(17) 0.06580(14) 0.0220(3) Uani 1 1 d . . .
Cl1 Cl 0.22572(5) 0.31454(6) -0.21224(5) 0.02552(13) 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
C1 0.0397(14) 0.0184(12) 0.0158(10) 0.0013(9) 0.0114(10) 0.0097(10)
C2 0.0322(13) 0.0228(13) 0.0156(10) -0.0049(9) -0.0001(10) 0.0117(10)
C3 0.0186(11) 0.0196(12) 0.0298(12) -0.0074(10) 0.0048(9) 0.0029(9)
C4 0.0208(11) 0.0210(12) 0.0202(11) -0.0027(9) 0.0102(9) 0.0015(9)
C5 0.0188(10) 0.0147(11) 0.0174(10) -0.0017(8) 0.0089(8) 0.0026(8)
C6 0.0161(10) 0.0174(11) 0.0181(10) 0.0027(9) 0.0102(8) 0.0019(9)
C7 0.0207(10) 0.0174(11) 0.0176(10) 0.0017(9) 0.0096(8) 0.0052(9)
C8 0.0188(10) 0.0140(11) 0.0157(10) -0.0009(8) 0.0074(8) 0.0006(8)
C9 0.0139(10) 0.0180(11) 0.0154(9) -0.0039(8) 0.0052(8) -0.0033(8)
C10 0.0183(11) 0.0190(12) 0.0203(10) -0.0013(9) 0.0061(9) 0.0025(9)
C11 0.0197(11) 0.0276(13) 0.0205(11) -0.0049(10) 0.0106(9) 0.0034(9)
C12 0.0180(10) 0.0292(12) 0.0154(10) -0.0032(9) 0.0081(8) -0.0038(9)
C13 0.0142(10) 0.0200(11) 0.0159(10) 0.0009(9) 0.0046(8) -0.0043(8)
C14 0.0153(10) 0.0193(11) 0.0165(10) -0.0045(9) 0.0070(8) -0.0018(8)
C15 0.0189(10) 0.0150(11) 0.0139(9) 0.0039(8) 0.0091(8) 0.0018(8)
C16 0.0177(10) 0.0133(11) 0.0172(10) 0.0063(8) 0.0085(8) 0.0013(8)
C17 0.0225(11) 0.0135(11) 0.0227(11) -0.0010(9) 0.0123(9) 0.0003(8)
C18 0.0200(11) 0.0187(11) 0.0208(11) 0.0012(9) 0.0106(9) 0.0018(9)
C19 0.0283(12) 0.0228(12) 0.0219(11) -0.0041(10) 0.0147(9) -0.0041(10)
C20 0.0227(11) 0.0265(12) 0.0289(11) -0.0030(11) 0.0130(9) 0.0034(11)
C21 0.0181(11) 0.0237(12) 0.0174(10) 0.0014(9) 0.0069(8) 0.0027(9)
C22 0.0197(11) 0.0226(12) 0.0103(9) 0.0043(9) 0.0074(8) 0.0016(9)
N1 0.0255(10) 0.0159(9) 0.0188(9) -0.0002(8) 0.0126(8) 0.0041(8)
O1 0.0286(9) 0.0197(8) 0.0275(8) 0.0040(7) 0.0182(7) 0.0011(7)
O2 0.0262(8) 0.0151(8) 0.0179(7) 0.0022(6) 0.0097(6) -0.0004(7)
O3 0.0162(7) 0.0161(7) 0.0212(7) -0.0032(6) 0.0082(6) 0.0010(6)
O4 0.0224(8) 0.0253(9) 0.0162(7) -0.0019(7) 0.0061(6) 0.0001(7)
Cl1 0.0258(3) 0.0279(3) 0.0240(3) 0.0093(3) 0.0117(2) 0.0044(3)
_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 N1 1.365(3) . ?
C1 C2 1.370(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.366(3) . ?
C5 C6 1.531(3) . ?
C6 O2 1.383(3) . ?
C6 O3 1.449(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.534(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.506(3) . ?
C8 C9 1.529(3) . ?
C8 H8 0.9800 . ?
C9 C14 1.382(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(3) . ?
C13 Cl1 1.749(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(3) . ?
C15 C22 1.464(3) . ?
C16 O3 1.350(2) . ?
C16 C17 1.495(3) . ?
C17 C18 1.531(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.525(3) . ?
C18 C19 1.528(3) . ?
C18 C21 1.531(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.515(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O4 1.229(3) . ?
N1 O1 1.315(2) . ?
O2 H2 0.8200 . ?
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
N1 C1 C2 120.9(2) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C4 119.34(18) . . ?
N1 C5 C6 118.86(18) . . ?
C4 C5 C6 121.77(19) . . ?
O2 C6 O3 108.34(17) . . ?
O2 C6 C7 109.18(17) . . ?
O3 C6 C7 113.06(17) . . ?
O2 C6 C5 111.13(17) . . ?
O3 C6 C5 104.02(16) . . ?
C7 C6 C5 111.02(17) . . ?
C6 C7 C8 112.42(17) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C15 C8 C9 115.47(17) . . ?
C15 C8 C7 109.19(16) . . ?
C9 C8 C7 112.92(17) . . ?
C15 C8 H8 106.2 . . ?
C9 C8 H8 106.2 . . ?
C7 C8 H8 106.2 . . ?
C14 C9 C10 119.10(19) . . ?
C14 C9 C8 123.35(19) . . ?
C10 C9 C8 117.55(19) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 117.99(19) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 122.7(2) . . ?
C12 C13 Cl1 118.52(16) . . ?
C14 C13 Cl1 118.79(17) . . ?
C9 C14 C13 118.8(2) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C22 119.00(18) . . ?
C16 C15 C8 122.43(18) . . ?
C22 C15 C8 118.48(17) . . ?
C15 C16 O3 124.73(18) . . ?
C15 C16 C17 125.28(18) . . ?
O3 C16 C17 109.99(17) . . ?
C16 C17 C18 113.69(17) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C20 C18 C19 109.32(18) . . ?
C20 C18 C21 109.30(17) . . ?
C19 C18 C21 111.13(18) . . ?
C20 C18 C17 109.64(18) . . ?
C19 C18 C17 108.99(17) . . ?
C21 C18 C17 108.44(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C18 114.27(17) . . ?
C22 C21 H21A 108.7 . . ?
C18 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C18 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
O4 C22 C15 121.37(19) . . ?
O4 C22 C21 121.08(18) . . ?
C15 C22 C21 117.48(18) . . ?
O1 N1 C1 118.66(18) . . ?
O1 N1 C5 121.22(16) . . ?
C1 N1 C5 120.12(19) . . ?
C6 O2 H2 109.5 . . ?
C16 O3 C6 118.02(15) . . ?
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
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 -178.3(2) . . . . ?
N1 C5 C6 O2 174.56(18) . . . . ?
C4 C5 C6 O2 -7.7(3) . . . . ?
N1 C5 C6 O3 58.2(2) . . . . ?
C4 C5 C6 O3 -124.0(2) . . . . ?
N1 C5 C6 C7 -63.7(2) . . . . ?
C4 C5 C6 C7 114.1(2) . . . . ?
O2 C6 C7 C8 -68.7(2) . . . . ?
O3 C6 C7 C8 52.0(2) . . . . ?
C5 C6 C7 C8 168.49(17) . . . . ?
C6 C7 C8 C15 -43.2(2) . . . . ?
C6 C7 C8 C9 86.7(2) . . . . ?
C15 C8 C9 C14 11.9(3) . . . . ?
C7 C8 C9 C14 -114.8(2) . . . . ?
C15 C8 C9 C10 -168.26(18) . . . . ?
C7 C8 C9 C10 65.1(2) . . . . ?
C14 C9 C10 C11 1.1(3) . . . . ?
C8 C9 C10 C11 -178.74(18) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 Cl1 -178.83(16) . . . . ?
C10 C9 C14 C13 -0.6(3) . . . . ?
C8 C9 C14 C13 179.28(18) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
Cl1 C13 C14 C9 179.15(15) . . . . ?
C9 C8 C15 C16 -110.6(2) . . . . ?
C7 C8 C15 C16 17.9(3) . . . . ?
C9 C8 C15 C22 73.0(2) . . . . ?
C7 C8 C15 C22 -158.53(18) . . . . ?
C22 C15 C16 O3 178.19(18) . . . . ?
C8 C15 C16 O3 1.7(3) . . . . ?
C22 C15 C16 C17 -2.2(3) . . . . ?
C8 C15 C16 C17 -178.60(19) . . . . ?
C15 C16 C17 C18 21.6(3) . . . . ?
O3 C16 C17 C18 -158.67(17) . . . . ?
C16 C17 C18 C20 -164.06(18) . . . . ?
C16 C17 C18 C19 76.3(2) . . . . ?
C16 C17 C18 C21 -44.8(2) . . . . ?
C20 C18 C21 C22 172.14(19) . . . . ?
C19 C18 C21 C22 -67.1(2) . . . . ?
C17 C18 C21 C22 52.7(2) . . . . ?
C16 C15 C22 O4 -173.8(2) . . . . ?
C8 C15 C22 O4 2.7(3) . . . . ?
C16 C15 C22 C21 9.2(3) . . . . ?
C8 C15 C22 C21 -174.26(18) . . . . ?
C18 C21 C22 O4 147.0(2) . . . . ?
C18 C21 C22 C15 -36.0(3) . . . . ?
C2 C1 N1 O1 179.2(2) . . . . ?
C2 C1 N1 C5 -0.8(3) . . . . ?
C4 C5 N1 O1 -179.14(19) . . . . ?
C6 C5 N1 O1 -1.3(3) . . . . ?
C4 C5 N1 C1 0.8(3) . . . . ?
C6 C5 N1 C1 178.65(19) . . . . ?
C15 C16 O3 C6 5.5(3) . . . . ?
C17 C16 O3 C6 -174.22(17) . . . . ?
O2 C6 O3 C16 88.7(2) . . . . ?
C7 C6 O3 C16 -32.4(2) . . . . ?
C5 C6 O3 C16 -152.96(17) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045


data_11deca_0m
_database_code_depnum_ccdc_archive 'CCDC 922006'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Br N O4 '
_chemical_formula_sum            'C22 H22 Br N O4'
_chemical_formula_weight         444.32
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1) '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   10.1531(9)
_cell_length_b                   9.1685(7)
_cell_length_c                   11.3968(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.669(2)
_cell_angle_gamma                90.00
_cell_volume                     992.63(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1903
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.39
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7749
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.1329
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.49
_reflns_number_total             4091
_reflns_number_gt                2878
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0000P)^2^+0.0000P] 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    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   0.030(10)
_refine_ls_number_reflns         4091
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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 1.0370(5) 0.5480(5) 0.7421(4) 0.0190(12) Uani 1 1 d . . .
H1 H 1.1136 0.5952 0.7999 0.023 Uiso 1 1 calc R . .
C2 C 0.9350(6) 0.4889(5) 0.7811(4) 0.0232(13) Uani 1 1 d . . .
H2 H 0.9417 0.4974 0.8643 0.028 Uiso 1 1 calc R . .
C3 C 0.8223(4) 0.4167(7) 0.6956(3) 0.0223(10) Uani 1 1 d . . .
H3 H 0.7524 0.3759 0.7204 0.027 Uiso 1 1 calc R . .
C4 C 0.8154(4) 0.4063(7) 0.5729(3) 0.0181(9) Uani 1 1 d . . .
H4 H 0.7398 0.3579 0.5149 0.022 Uiso 1 1 calc R . .
C5 C 0.9174(5) 0.4656(4) 0.5343(4) 0.0132(11) Uani 1 1 d . . .
C6 C 0.9135(5) 0.4520(4) 0.3991(4) 0.0148(12) Uani 1 1 d . . .
C7 C 0.8970(5) 0.5989(5) 0.3351(4) 0.0174(11) Uani 1 1 d . . .
H7A H 0.9627 0.6676 0.3902 0.021 Uiso 1 1 calc R . .
H7B H 0.8024 0.6353 0.3187 0.021 Uiso 1 1 calc R . .
C8 C 0.9243(5) 0.5873(5) 0.2102(4) 0.0163(11) Uani 1 1 d . . .
H8 H 0.9437 0.6867 0.1892 0.020 Uiso 1 1 calc R . .
C9 C 0.7969(5) 0.5346(4) 0.1000(4) 0.0105(10) Uani 1 1 d . . .
C10 C 0.6801(5) 0.6246(5) 0.0565(4) 0.0222(12) Uani 1 1 d . . .
H10 H 0.6803 0.7132 0.0963 0.027 Uiso 1 1 calc R . .
C11 C 0.5627(5) 0.5848(5) -0.0453(4) 0.0243(12) Uani 1 1 d . . .
H11 H 0.4846 0.6459 -0.0734 0.029 Uiso 1 1 calc R . .
C12 C 0.5630(5) 0.4540(5) -0.1043(4) 0.0209(14) Uani 1 1 d . . .
C13 C 0.6760(5) 0.3625(5) -0.0620(4) 0.0173(12) Uani 1 1 d . . .
H13 H 0.6746 0.2734 -0.1013 0.021 Uiso 1 1 calc R . .
C14 C 0.7928(4) 0.4030(7) 0.0402(3) 0.0146(10) Uani 1 1 d . . .
H14 H 0.8696 0.3404 0.0687 0.018 Uiso 1 1 calc R . .
C15 C 1.0566(5) 0.5026(4) 0.2321(4) 0.0137(11) Uani 1 1 d . . .
C16 C 1.1360(5) 0.5205(5) 0.1475(4) 0.0170(11) Uani 1 1 d . . .
C17 C 1.2615(4) 0.4264(7) 0.1675(4) 0.0228(11) Uani 1 1 d . . .
H17A H 1.3222 0.4734 0.1295 0.027 Uiso 1 1 calc R . .
H17B H 1.2305 0.3346 0.1243 0.027 Uiso 1 1 calc R . .
C18 C 1.3479(4) 0.3940(6) 0.3052(4) 0.0163(11) Uani 1 1 d . . .
C19 C 1.4146(6) 0.5370(5) 0.3710(5) 0.0283(13) Uani 1 1 d . . .
H19A H 1.4673 0.5177 0.4577 0.042 Uiso 1 1 calc R . .
H19B H 1.3417 0.6065 0.3647 0.042 Uiso 1 1 calc R . .
H19C H 1.4763 0.5758 0.3314 0.042 Uiso 1 1 calc R . .
C20 C 1.4620(5) 0.2840(6) 0.3175(5) 0.0272(13) Uani 1 1 d . . .
H20A H 1.5083 0.2595 0.4043 0.041 Uiso 1 1 calc R . .
H20B H 1.5293 0.3245 0.2849 0.041 Uiso 1 1 calc R . .
H20C H 1.4213 0.1977 0.2711 0.041 Uiso 1 1 calc R . .
C21 C 1.2465(5) 0.3343(5) 0.3653(4) 0.0190(11) Uani 1 1 d . . .
H21A H 1.2273 0.2328 0.3412 0.023 Uiso 1 1 calc R . .
H21B H 1.2926 0.3373 0.4557 0.023 Uiso 1 1 calc R . .
C22 C 1.1109(4) 0.4127(7) 0.3317(3) 0.0143(9) Uani 1 1 d . . .
N1 N 1.0275(4) 0.5383(4) 0.6196(3) 0.0180(10) Uani 1 1 d . . .
O1 O 1.1280(3) 0.5964(3) 0.5864(3) 0.0202(8) Uani 1 1 d . . .
O2 O 0.8047(3) 0.3632(3) 0.3290(3) 0.0182(8) Uani 1 1 d . . .
H2A H 0.8198 0.2794 0.3554 0.027 Uiso 1 1 calc R . .
O3 O 1.0464(3) 0.3817(3) 0.4143(2) 0.0150(8) Uani 1 1 d . . .
O4 O 1.0949(3) 0.6080(3) 0.0595(3) 0.0232(8) Uani 1 1 d . . .
Br1 Br 0.40838(5) 0.41142(6) -0.25386(4) 0.02889(14) 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
C1 0.023(3) 0.016(3) 0.014(3) -0.002(2) 0.002(2) 0.001(2)
C2 0.040(4) 0.019(3) 0.012(3) 0.005(2) 0.011(3) 0.014(3)
C3 0.030(3) 0.024(2) 0.018(2) 0.011(4) 0.015(2) 0.001(4)
C4 0.017(2) 0.018(2) 0.016(2) 0.006(3) 0.0023(17) -0.001(3)
C5 0.017(3) 0.009(2) 0.012(2) 0.0009(17) 0.003(2) 0.0036(19)
C6 0.012(3) 0.021(3) 0.011(2) 0.0012(19) 0.004(2) 0.007(2)
C7 0.020(3) 0.016(3) 0.014(3) -0.002(2) 0.003(2) 0.006(2)
C8 0.018(3) 0.018(3) 0.013(3) 0.006(2) 0.006(2) -0.001(2)
C9 0.012(3) 0.012(2) 0.007(2) 0.0039(19) 0.002(2) -0.001(2)
C10 0.031(4) 0.022(3) 0.016(3) -0.002(2) 0.011(2) 0.005(3)
C11 0.020(3) 0.031(3) 0.017(3) 0.008(2) 0.001(2) 0.009(3)
C12 0.025(3) 0.028(4) 0.008(2) 0.000(2) 0.005(2) -0.005(2)
C13 0.023(3) 0.017(3) 0.014(2) 0.0035(19) 0.009(2) 0.000(2)
C14 0.017(3) 0.016(2) 0.011(2) 0.005(3) 0.0045(18) 0.003(3)
C15 0.016(3) 0.015(2) 0.010(3) -0.001(2) 0.004(2) 0.000(2)
C16 0.023(3) 0.015(3) 0.012(3) -0.003(2) 0.004(2) -0.009(2)
C17 0.022(3) 0.026(3) 0.025(2) -0.003(3) 0.014(2) -0.002(3)
C18 0.016(3) 0.014(3) 0.019(2) -0.003(3) 0.0063(18) -0.003(3)
C19 0.027(4) 0.026(3) 0.029(3) 0.004(3) 0.007(3) -0.001(3)
C20 0.020(4) 0.037(3) 0.025(3) 0.000(3) 0.009(3) 0.000(3)
C21 0.020(3) 0.019(3) 0.017(3) -0.005(2) 0.006(2) 0.004(2)
C22 0.020(2) 0.013(2) 0.012(2) 0.001(3) 0.0073(17) -0.007(3)
N1 0.025(3) 0.016(2) 0.015(2) 0.0014(17) 0.008(2) 0.0072(19)
O1 0.021(2) 0.0208(19) 0.0209(19) -0.0010(15) 0.0097(16) -0.0027(16)
O2 0.023(2) 0.016(2) 0.0137(17) -0.0005(13) 0.0052(15) -0.0009(15)
O3 0.0201(19) 0.016(2) 0.0109(15) 0.0024(14) 0.0083(13) 0.0045(15)
O4 0.027(2) 0.026(2) 0.0161(19) 0.0040(16) 0.0081(16) -0.0049(17)
Br1 0.0237(3) 0.0382(3) 0.0188(2) 0.0064(4) 0.00004(18) -0.0077(4)
_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 N1 1.369(5) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.368(6) . ?
C5 C6 1.533(5) . ?
C6 O2 1.378(5) . ?
C6 O3 1.450(5) . ?
C6 C7 1.512(6) . ?
C7 C8 1.548(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.494(6) . ?
C8 C9 1.529(6) . ?
C8 H8 0.9800 . ?
C9 C14 1.380(7) . ?
C9 C10 1.385(6) . ?
C10 C11 1.387(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 Br1 1.906(5) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C22 1.353(6) . ?
C15 C16 1.469(5) . ?
C16 O4 1.236(5) . ?
C16 C17 1.488(6) . ?
C17 C18 1.532(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.505(6) . ?
C18 C21 1.526(5) . ?
C18 C19 1.543(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.479(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O3 1.353(4) . ?
N1 O1 1.319(4) . ?
O2 H2A 0.8200 . ?
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
N1 C1 C2 121.0(5) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C2 C3 119.5(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N1 C5 C4 119.1(4) . . ?
N1 C5 C6 118.6(4) . . ?
C4 C5 C6 122.3(4) . . ?
O2 C6 O3 109.2(3) . . ?
O2 C6 C7 108.5(4) . . ?
O3 C6 C7 113.2(3) . . ?
O2 C6 C5 111.2(3) . . ?
O3 C6 C5 102.9(3) . . ?
C7 C6 C5 111.8(3) . . ?
C6 C7 C8 110.9(3) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C15 C8 C9 115.0(4) . . ?
C15 C8 C7 109.0(3) . . ?
C9 C8 C7 113.7(4) . . ?
C15 C8 H8 106.1 . . ?
C9 C8 H8 106.1 . . ?
C7 C8 H8 106.1 . . ?
C14 C9 C10 118.1(4) . . ?
C14 C9 C8 123.5(4) . . ?
C10 C9 C8 118.4(4) . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.2(5) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 Br1 121.0(3) . . ?
C11 C12 Br1 118.2(4) . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 121.1(5) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C22 C15 C16 117.6(4) . . ?
C22 C15 C8 122.2(3) . . ?
C16 C15 C8 120.1(4) . . ?
O4 C16 C15 119.9(4) . . ?
O4 C16 C17 121.8(4) . . ?
C15 C16 C17 118.2(4) . . ?
C16 C17 C18 114.8(3) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.5 . . ?
C20 C18 C21 109.7(4) . . ?
C20 C18 C17 111.7(4) . . ?
C21 C18 C17 107.2(4) . . ?
C20 C18 C19 109.5(4) . . ?
C21 C18 C19 109.7(4) . . ?
C17 C18 C19 109.1(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C18 115.1(4) . . ?
C22 C21 H21A 108.5 . . ?
C18 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C18 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C15 C22 O3 123.9(4) . . ?
C15 C22 C21 125.4(3) . . ?
O3 C22 C21 110.6(4) . . ?
O1 N1 C5 120.9(4) . . ?
O1 N1 C1 118.9(4) . . ?
C5 N1 C1 120.1(4) . . ?
C6 O2 H2A 109.5 . . ?
C22 O3 C6 118.8(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
N1 C1 C2 C3 1.0(7) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C3 C4 C5 N1 -0.8(8) . . . . ?
C3 C4 C5 C6 178.5(5) . . . . ?
N1 C5 C6 O2 173.6(4) . . . . ?
C4 C5 C6 O2 -5.7(6) . . . . ?
N1 C5 C6 O3 56.8(4) . . . . ?
C4 C5 C6 O3 -122.5(5) . . . . ?
N1 C5 C6 C7 -64.9(5) . . . . ?
C4 C5 C6 C7 115.7(5) . . . . ?
O2 C6 C7 C8 -68.9(5) . . . . ?
O3 C6 C7 C8 52.5(5) . . . . ?
C5 C6 C7 C8 168.1(4) . . . . ?
C6 C7 C8 C15 -47.2(5) . . . . ?
C6 C7 C8 C9 82.5(5) . . . . ?
C15 C8 C9 C14 12.8(5) . . . . ?
C7 C8 C9 C14 -113.9(4) . . . . ?
C15 C8 C9 C10 -166.2(4) . . . . ?
C7 C8 C9 C10 67.2(5) . . . . ?
C14 C9 C10 C11 -0.8(6) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C10 C11 C12 Br1 -173.8(3) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
Br1 C12 C13 C14 173.8(3) . . . . ?
C10 C9 C14 C13 0.9(6) . . . . ?
C8 C9 C14 C13 -178.0(4) . . . . ?
C12 C13 C14 C9 0.1(6) . . . . ?
C9 C8 C15 C22 -108.8(5) . . . . ?
C7 C8 C15 C22 20.2(6) . . . . ?
C9 C8 C15 C16 74.1(5) . . . . ?
C7 C8 C15 C16 -156.8(4) . . . . ?
C22 C15 C16 O4 -175.8(5) . . . . ?
C8 C15 C16 O4 1.4(6) . . . . ?
C22 C15 C16 C17 7.0(7) . . . . ?
C8 C15 C16 C17 -175.8(4) . . . . ?
O4 C16 C17 C18 146.4(5) . . . . ?
C15 C16 C17 C18 -36.4(7) . . . . ?
C16 C17 C18 C20 173.0(4) . . . . ?
C16 C17 C18 C21 52.8(6) . . . . ?
C16 C17 C18 C19 -65.9(5) . . . . ?
C20 C18 C21 C22 -164.8(4) . . . . ?
C17 C18 C21 C22 -43.4(6) . . . . ?
C19 C18 C21 C22 75.0(5) . . . . ?
C16 C15 C22 O3 -177.3(4) . . . . ?
C8 C15 C22 O3 5.6(8) . . . . ?
C16 C15 C22 C21 2.2(8) . . . . ?
C8 C15 C22 C21 -174.9(4) . . . . ?
C18 C21 C22 C15 18.2(7) . . . . ?
C18 C21 C22 O3 -162.3(4) . . . . ?
C4 C5 N1 O1 179.7(4) . . . . ?
C6 C5 N1 O1 0.4(6) . . . . ?
C4 C5 N1 C1 1.7(6) . . . . ?
C6 C5 N1 C1 -177.6(3) . . . . ?
C2 C1 N1 O1 -179.9(4) . . . . ?
C2 C1 N1 C5 -1.8(6) . . . . ?
C15 C22 O3 C6 -2.3(7) . . . . ?
C21 C22 O3 C6 178.2(4) . . . . ?
O2 C6 O3 C22 93.4(4) . . . . ?
C7 C6 O3 C22 -27.6(5) . . . . ?
C5 C6 O3 C22 -148.4(4) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.086