# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Xu, Xiaoying'
_publ_contact_author_email       wlxioc@cioc.ac.cn

_publ_section_title              
;
Highly Organocatalytic Asymmetric Michael-Ketone Aldol-Dehydration
Domino Reaction: Straightforward Approach to Construct Six-Membered
Spirocyclic Oxindoles
;
loop_
_publ_author_name
'Liang-Liang Wang'
'Lin Peng'
'Jian-Fei Bai'
'Qing-Chun Huang'
;
Xiaoying Xu
;
'Li-xin Wang'

# Attachment '- 4b.cif'

data_y2834
_database_code_depnum_ccdc_archive 'CCDC 780462'
#TrackingRef '- 4b.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Br N O2'
_chemical_formula_weight         472.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   14.772(2)
_cell_length_b                   11.1689(17)
_cell_length_c                   13.281(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2191.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6813
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.51

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.4707
_exptl_absorpt_correction_T_max  0.5170
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17366
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5018
_reflns_number_gt                4072
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of 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^)+(0.0031P)^2^+0.0600P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(5)
_refine_ls_number_reflns         5018
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0418
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Br1 Br 0.580917(18) 0.18228(2) 0.091808(18) 0.03458(7) Uani 1 1 d . . .
O1 O 0.31690(9) 0.54989(12) 0.41474(12) 0.0202(4) Uani 1 1 d . . .
O2 O 0.35858(10) 0.33249(16) 0.72595(10) 0.0276(4) Uani 1 1 d . . .
N1 N 0.21965(12) 0.47487(16) 0.29570(13) 0.0174(5) Uani 1 1 d . . .
C1 C 0.17005(15) 0.3682(2) 0.28089(17) 0.0171(5) Uani 1 1 d . . .
C2 C 0.11367(14) 0.3391(2) 0.20152(15) 0.0227(6) Uani 1 1 d . . .
H2 H 0.1047 0.3926 0.1468 0.027 Uiso 1 1 calc R . .
C3 C 0.07079(16) 0.2288(2) 0.20481(16) 0.0247(6) Uani 1 1 d . . .
H3 H 0.0313 0.2065 0.1515 0.030 Uiso 1 1 calc R . .
C4 C 0.08423(16) 0.15109(19) 0.28370(15) 0.0219(5) Uani 1 1 d . . .
H4 H 0.0550 0.0753 0.2834 0.026 Uiso 1 1 calc R . .
C5 C 0.14005(13) 0.1820(2) 0.36395(15) 0.0179(5) Uani 1 1 d . . .
H5 H 0.1487 0.1289 0.4190 0.022 Uiso 1 1 calc R . .
C6 C 0.18266(14) 0.29250(19) 0.36146(15) 0.0145(5) Uani 1 1 d . . .
C7 C 0.24456(14) 0.35180(17) 0.43793(14) 0.0131(5) Uani 1 1 d . . .
C8 C 0.26694(15) 0.4715(2) 0.38413(17) 0.0173(6) Uani 1 1 d . . .
C9 C 0.19305(14) 0.37968(19) 0.53517(17) 0.0154(5) Uani 1 1 d . . .
C10 C 0.23125(15) 0.37135(19) 0.62529(16) 0.0171(6) Uani 1 1 d . . .
H10 H 0.1943 0.3854 0.6827 0.020 Uiso 1 1 calc R . .
C11 C 0.32687(15) 0.3419(2) 0.64201(16) 0.0189(6) Uani 1 1 d . . .
C12 C 0.38382(13) 0.3288(2) 0.54858(13) 0.0175(5) Uani 1 1 d . . .
H12A H 0.4357 0.2756 0.5636 0.021 Uiso 1 1 calc R . .
H12B H 0.4083 0.4082 0.5298 0.021 Uiso 1 1 calc R . .
C13 C 0.33141(14) 0.27784(19) 0.45964(14) 0.0139(5) Uani 1 1 d . . .
H13 H 0.3104 0.1965 0.4808 0.017 Uiso 1 1 calc R . .
C14 C 0.39074(14) 0.25904(19) 0.36748(15) 0.0143(5) Uani 1 1 d . . .
C15 C 0.37164(13) 0.1671(2) 0.29937(15) 0.0192(5) Uani 1 1 d . . .
H15 H 0.3195 0.1189 0.3098 0.023 Uiso 1 1 calc R . .
C16 C 0.42667(15) 0.14440(18) 0.21707(15) 0.0199(5) Uani 1 1 d . . .
H16 H 0.4123 0.0815 0.1716 0.024 Uiso 1 1 calc R . .
C17 C 0.50226(15) 0.2139(2) 0.20195(15) 0.0193(6) Uani 1 1 d . . .
C18 C 0.52344(14) 0.3057(2) 0.26734(16) 0.0246(6) Uani 1 1 d . . .
H18 H 0.5756 0.3536 0.2563 0.030 Uiso 1 1 calc R . .
C19 C 0.46765(13) 0.3271(2) 0.34934(15) 0.0196(5) Uani 1 1 d . . .
H19 H 0.4825 0.3901 0.3944 0.024 Uiso 1 1 calc R . .
C20 C 0.22350(15) 0.5722(2) 0.22307(16) 0.0234(6) Uani 1 1 d . . .
H20A H 0.2584 0.6393 0.2525 0.028 Uiso 1 1 calc R . .
H20B H 0.1613 0.6013 0.2102 0.028 Uiso 1 1 calc R . .
C21 C 0.26621(16) 0.5370(2) 0.12422(16) 0.0211(6) Uani 1 1 d . . .
C22 C 0.23791(18) 0.5904(2) 0.03593(18) 0.0358(8) Uani 1 1 d . . .
H22 H 0.1897 0.6466 0.0376 0.043 Uiso 1 1 calc R . .
C23 C 0.27865(19) 0.5632(3) -0.05476(19) 0.0442(9) Uani 1 1 d . . .
H23 H 0.2589 0.6013 -0.1149 0.053 Uiso 1 1 calc R . .
C24 C 0.3484(2) 0.4803(3) -0.0579(2) 0.0457(8) Uani 1 1 d . . .
H24 H 0.3759 0.4603 -0.1203 0.055 Uiso 1 1 calc R . .
C25 C 0.37768(19) 0.4269(2) 0.02992(19) 0.0409(8) Uani 1 1 d . . .
H25 H 0.4262 0.3711 0.0284 0.049 Uiso 1 1 calc R . .
C26 C 0.33608(17) 0.4551(2) 0.12017(17) 0.0299(7) Uani 1 1 d . . .
H26 H 0.3559 0.4174 0.1804 0.036 Uiso 1 1 calc R . .
C27 C 0.09660(14) 0.42140(18) 0.52404(15) 0.0232(6) Uani 1 1 d . . .
H27A H 0.0596 0.3562 0.4967 0.028 Uiso 1 1 calc R . .
H27B H 0.0945 0.4900 0.4781 0.028 Uiso 1 1 calc R . .
H27C H 0.0729 0.4451 0.5900 0.028 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
Br1 0.03729(14) 0.03450(14) 0.03195(13) -0.00296(15) 0.02006(14) -0.00080(15)
O1 0.0245(9) 0.0150(8) 0.0210(9) -0.0034(9) -0.0015(8) -0.0061(7)
O2 0.0289(10) 0.0388(11) 0.0152(9) 0.0002(10) -0.0037(7) 0.0000(9)
N1 0.0186(11) 0.0175(11) 0.0160(11) 0.0034(9) -0.0018(9) -0.0026(9)
C1 0.0137(13) 0.0196(14) 0.0179(13) -0.0015(11) 0.0000(10) -0.0019(10)
C2 0.0220(14) 0.0294(16) 0.0168(13) 0.0057(12) -0.0018(10) -0.0015(11)
C3 0.0167(14) 0.0351(15) 0.0221(13) -0.0075(12) -0.0041(12) -0.0089(12)
C4 0.0173(12) 0.0231(14) 0.0252(12) -0.0046(11) 0.0039(12) -0.0083(12)
C5 0.0133(11) 0.0192(12) 0.0212(12) 0.0028(13) 0.0037(9) -0.0005(12)
C6 0.0111(12) 0.0165(14) 0.0161(12) -0.0022(10) 0.0027(10) 0.0024(10)
C7 0.0115(12) 0.0139(13) 0.0138(12) -0.0014(9) 0.0001(9) -0.0006(9)
C8 0.0142(13) 0.0139(12) 0.0238(15) -0.0024(11) 0.0037(11) 0.0030(10)
C9 0.0134(13) 0.0122(13) 0.0205(14) -0.0024(11) 0.0031(11) -0.0007(10)
C10 0.0181(14) 0.0181(13) 0.0151(13) -0.0035(10) 0.0060(11) -0.0007(11)
C11 0.0230(13) 0.0136(14) 0.0200(13) -0.0019(11) -0.0023(11) -0.0021(11)
C12 0.0138(12) 0.0202(13) 0.0185(12) -0.0023(11) -0.0003(9) 0.0011(11)
C13 0.0142(12) 0.0146(13) 0.0129(12) -0.0017(10) 0.0005(10) 0.0009(10)
C14 0.0148(13) 0.0146(12) 0.0134(12) 0.0007(10) -0.0018(10) -0.0011(10)
C15 0.0123(12) 0.0205(14) 0.0247(13) 0.0001(12) 0.0016(10) -0.0022(11)
C16 0.0213(13) 0.0205(13) 0.0180(12) -0.0042(10) -0.0005(12) 0.0002(12)
C17 0.0210(14) 0.0216(15) 0.0154(12) 0.0000(11) 0.0082(11) 0.0032(10)
C18 0.0202(13) 0.0235(14) 0.0301(14) 0.0012(13) 0.0066(11) -0.0063(12)
C19 0.0205(13) 0.0173(13) 0.0211(12) -0.0024(12) 0.0017(10) -0.0057(12)
C20 0.0246(15) 0.0167(14) 0.0290(15) 0.0047(12) -0.0088(12) -0.0012(11)
C21 0.0256(14) 0.0209(14) 0.0166(13) 0.0025(11) -0.0052(11) -0.0098(12)
C22 0.0269(17) 0.052(2) 0.0287(17) 0.0188(15) -0.0098(14) -0.0073(15)
C23 0.040(2) 0.072(2) 0.0199(16) 0.0169(15) -0.0091(14) -0.0216(18)
C24 0.064(2) 0.051(2) 0.0220(16) -0.0083(15) 0.0074(15) -0.0170(18)
C25 0.065(2) 0.0297(17) 0.0276(17) 0.0023(14) 0.0147(15) 0.0074(15)
C26 0.0479(18) 0.0258(15) 0.0159(14) 0.0048(12) 0.0035(12) 0.0054(13)
C27 0.0227(15) 0.0234(14) 0.0235(13) -0.0061(11) 0.0028(12) -0.0003(12)

_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
Br1 C17 1.901(2) . ?
O1 C8 1.215(2) . ?
O2 C11 1.214(2) . ?
N1 C8 1.367(2) . ?
N1 C1 1.413(3) . ?
N1 C20 1.455(3) . ?
C1 C6 1.376(3) . ?
C1 C2 1.382(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.519(3) . ?
C7 C9 1.531(3) . ?
C7 C8 1.552(3) . ?
C7 C13 1.553(3) . ?
C9 C10 1.326(3) . ?
C9 C27 1.506(3) . ?
C10 C11 1.467(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.506(3) . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(3) . ?
C13 H13 1.0000 . ?
C14 C19 1.388(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.509(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C26 1.380(3) . ?
C21 C22 1.380(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.19(18) . . ?
C8 N1 C20 124.77(19) . . ?
C1 N1 C20 123.95(18) . . ?
C6 C1 C2 122.0(2) . . ?
C6 C1 N1 109.85(19) . . ?
C2 C1 N1 128.1(2) . . ?
C1 C2 C3 117.4(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 C7 109.49(19) . . ?
C5 C6 C7 130.2(2) . . ?
C6 C7 C9 110.71(17) . . ?
C6 C7 C8 101.31(16) . . ?
C9 C7 C8 108.61(17) . . ?
C6 C7 C13 112.94(16) . . ?
C9 C7 C13 111.23(16) . . ?
C8 C7 C13 111.58(17) . . ?
O1 C8 N1 125.3(2) . . ?
O1 C8 C7 126.6(2) . . ?
N1 C8 C7 108.09(18) . . ?
C10 C9 C27 120.8(2) . . ?
C10 C9 C7 122.38(19) . . ?
C27 C9 C7 116.76(18) . . ?
C9 C10 C11 124.2(2) . . ?
C9 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
O2 C11 C10 122.0(2) . . ?
O2 C11 C12 122.2(2) . . ?
C10 C11 C12 115.76(18) . . ?
C11 C12 C13 113.04(17) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 112.53(17) . . ?
C14 C13 C7 113.60(16) . . ?
C12 C13 C7 111.43(16) . . ?
C14 C13 H13 106.2 . . ?
C12 C13 H13 106.2 . . ?
C7 C13 H13 106.2 . . ?
C19 C14 C15 117.1(2) . . ?
C19 C14 C13 122.42(19) . . ?
C15 C14 C13 120.43(19) . . ?
C16 C15 C14 121.8(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 Br1 120.25(17) . . ?
C18 C17 Br1 118.94(17) . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C14 121.9(2) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N1 C20 C21 113.46(19) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C26 C21 C22 118.7(2) . . ?
C26 C21 C20 121.3(2) . . ?
C22 C21 C20 120.0(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 121.1(2) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C9 C27 H27A 109.5 . . ?
C9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 1.2(3) . . . . ?
C20 N1 C1 C6 177.9(2) . . . . ?
C8 N1 C1 C2 179.1(2) . . . . ?
C20 N1 C1 C2 -4.1(4) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C3 -178.8(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
N1 C1 C6 C5 179.66(18) . . . . ?
C2 C1 C6 C7 -177.42(19) . . . . ?
N1 C1 C6 C7 0.7(2) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C1 C6 C7 C9 113.1(2) . . . . ?
C5 C6 C7 C9 -65.8(3) . . . . ?
C1 C6 C7 C8 -2.0(2) . . . . ?
C5 C6 C7 C8 179.2(2) . . . . ?
C1 C6 C7 C13 -121.44(19) . . . . ?
C5 C6 C7 C13 59.7(3) . . . . ?
C1 N1 C8 O1 178.2(2) . . . . ?
C20 N1 C8 O1 1.5(4) . . . . ?
C1 N1 C8 C7 -2.4(2) . . . . ?
C20 N1 C8 C7 -179.16(19) . . . . ?
C6 C7 C8 O1 -178.0(2) . . . . ?
C9 C7 C8 O1 65.4(3) . . . . ?
C13 C7 C8 O1 -57.6(3) . . . . ?
C6 C7 C8 N1 2.6(2) . . . . ?
C9 C7 C8 N1 -113.98(19) . . . . ?
C13 C7 C8 N1 123.06(18) . . . . ?
C6 C7 C9 C10 144.1(2) . . . . ?
C8 C7 C9 C10 -105.5(2) . . . . ?
C13 C7 C9 C10 17.6(3) . . . . ?
C6 C7 C9 C27 -37.9(3) . . . . ?
C8 C7 C9 C27 72.5(2) . . . . ?
C13 C7 C9 C27 -164.29(17) . . . . ?
C27 C9 C10 C11 -174.34(19) . . . . ?
C7 C9 C10 C11 3.7(4) . . . . ?
C9 C10 C11 O2 -178.3(2) . . . . ?
C9 C10 C11 C12 4.0(4) . . . . ?
O2 C11 C12 C13 149.1(2) . . . . ?
C10 C11 C12 C13 -33.3(3) . . . . ?
C11 C12 C13 C14 -177.02(19) . . . . ?
C11 C12 C13 C7 54.1(2) . . . . ?
C6 C7 C13 C14 61.1(2) . . . . ?
C9 C7 C13 C14 -173.68(17) . . . . ?
C8 C7 C13 C14 -52.2(2) . . . . ?
C6 C7 C13 C12 -170.52(17) . . . . ?
C9 C7 C13 C12 -45.3(2) . . . . ?
C8 C7 C13 C12 76.1(2) . . . . ?
C12 C13 C14 C19 -27.5(3) . . . . ?
C7 C13 C14 C19 100.3(2) . . . . ?
C12 C13 C14 C15 149.41(19) . . . . ?
C7 C13 C14 C15 -82.8(2) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 -177.13(19) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C15 C16 C17 Br1 178.30(16) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
Br1 C17 C18 C19 -178.27(16) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C13 C14 C19 C18 177.1(2) . . . . ?
C8 N1 C20 C21 113.4(2) . . . . ?
C1 N1 C20 C21 -62.9(3) . . . . ?
N1 C20 C21 C26 -34.3(3) . . . . ?
N1 C20 C21 C22 148.2(2) . . . . ?
C26 C21 C22 C23 -0.3(4) . . . . ?
C20 C21 C22 C23 177.2(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C23 C24 C25 C26 1.2(4) . . . . ?
C22 C21 C26 C25 0.4(4) . . . . ?
C20 C21 C26 C25 -177.1(2) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.052