# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_Cambridge 0177
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Jian-Wu Xie'
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of
Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
;
?
;
'Li-Ping Fan'
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of
Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
.
'Xin-Sheng Li'
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of
Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
.
'Hong Su'
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of
Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
.
'Feng Wang'
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of
Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
.
;
Dong-Cheng Xu
;
'' ''
_publ_contact_author_name 'Jian-Wu Xie'
_publ_contact_author_email XIEJW@ZJNU.CN
_publ_section_title
;
Efficient Kinetic Resolution of Racemic 3-Nitro-2H-Chromene
Derivatives Catalyzed by Takemoto's Organocatalyst
;
_publ_contact_author_address
;
Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Department of Chemistry and Life Science, Zhejiang Normal University,Jinhua 321004, China
;
_publ_contact_author_fax 86-579-82282610
_publ_contact_author_phone 86-579-82283072
_publ_contact_letter
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;
_publ_requested_category ?
# Attachment '5c_cif.CIF'
data_s
_database_code_depnum_ccdc_archive 'CCDC 752804'
#TrackingRef '5c_cif.CIF'
_publ_section_related_literature ?
_publ_section_abstract
;
(type here to add abstract)
;
#Added by publCIF
_audit_update_record
;
2009-12-09 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C29 H27 Br N2 O7'
_chemical_formula_sum 'C29 H27 Br N2 O7'
_chemical_formula_weight 595.44
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)
_symmetry_space_group_name_Hall 'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 11.2327(3)
_cell_length_b 10.1083(3)
_cell_length_c 12.0414(3)
_cell_angle_alpha 90.00
_cell_angle_beta 102.797(2)
_cell_angle_gamma 90.00
_cell_volume 1333.26(6)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 7243
_cell_measurement_theta_min 1.73
_cell_measurement_theta_max 27.68
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max .25
_exptl_crystal_size_mid .07
_exptl_crystal_size_min .06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.483
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 612
_exptl_absorpt_coefficient_mu 1.593
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min .88
_exptl_absorpt_correction_T_max .91
_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 'Bruker APEXII'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time none
_diffrn_standards_decay_% 0
_diffrn_reflns_number 20445
_diffrn_reflns_av_R_equivalents 0.0338
_diffrn_reflns_av_sigmaI/netI 0.0501
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 1.73
_diffrn_reflns_theta_max 27.68
_reflns_number_total 6121
_reflns_number_gt 4748
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEXII (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 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^)+(0.0462P)^2^+0.0426P] 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 0.015(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns 6121
_refine_ls_number_parameters 352
_refine_ls_number_restraints 1
_refine_ls_R_factor_ref 0.0563
_refine_ls_R_factor_gt 0.0378
_refine_ls_wR_factor_ref 0.0935
_refine_ls_wR_factor_gt 0.0873
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_restrained_S_all 1.032
_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
Br1 Br 0.34075(4) 0.82855(3) 0.37704(3) 0.07387(14) Uani 1 1 d . . .
N1 N 0.0898(2) 0.4219(2) 0.72479(18) 0.0348(5) Uani 1 1 d . . .
N2 N 0.38598(19) 0.3467(2) 0.90555(18) 0.0352(5) Uani 1 1 d . . .
H2B H 0.4629 0.3613 0.9287 0.042 Uiso 1 1 calc R . .
O1 O 0.18968(19) 0.24708(17) 0.58068(15) 0.0422(4) Uani 1 1 d . . .
O2 O -0.00145(18) 0.3531(2) 0.71684(19) 0.0549(5) Uani 1 1 d . . .
O3 O 0.08729(19) 0.53918(17) 0.69963(17) 0.0461(5) Uani 1 1 d . . .
O4 O 0.2124(2) 0.1343(2) 1.04416(16) 0.0489(5) Uani 1 1 d . . .
O5 O 0.3947(2) 0.2244(3) 1.11883(18) 0.0659(6) Uani 1 1 d . . .
O6 O 0.46780(19) 0.13336(19) 0.80990(17) 0.0481(5) Uani 1 1 d . . .
O7 O 0.42013(19) 0.00425(18) 0.94443(19) 0.0521(5) Uani 1 1 d . . .
C1 C 0.3173(3) 0.6769(3) 0.4620(3) 0.0478(7) Uani 1 1 d . . .
C2 C 0.4069(3) 0.6402(3) 0.5544(3) 0.0494(7) Uani 1 1 d . . .
H2A H 0.4784 0.6894 0.5747 0.059 Uiso 1 1 calc R . .
C3 C 0.3899(3) 0.5296(3) 0.6171(2) 0.0424(6) Uani 1 1 d . . .
H3A H 0.4502 0.5045 0.6797 0.051 Uiso 1 1 calc R . .
C4 C 0.2828(2) 0.4561(2) 0.5867(2) 0.0338(5) Uani 1 1 d . . .
C5 C 0.1952(3) 0.4943(3) 0.4922(2) 0.0445(6) Uani 1 1 d . . .
H5A H 0.1241 0.4448 0.4701 0.053 Uiso 1 1 calc R . .
C6 C 0.2121(3) 0.6050(3) 0.4303(3) 0.0494(7) Uani 1 1 d . . .
H6A H 0.1523 0.6305 0.3674 0.059 Uiso 1 1 calc R . .
C7 C 0.2662(2) 0.3361(3) 0.65646(19) 0.0333(5) Uani 1 1 d . . .
H7A H 0.3462 0.2938 0.6814 0.040 Uiso 1 1 calc R . .
C8 C 0.2134(2) 0.35945(19) 0.7643(2) 0.0296(5) Uani 1 1 d . . .
C9 C 0.2061(2) 0.2258(2) 0.8238(2) 0.0293(5) Uani 1 1 d . . .
H9A H 0.1397 0.2318 0.8644 0.035 Uiso 1 1 calc R . .
C10 C 0.1788(2) 0.1098(2) 0.7424(2) 0.0332(5) Uani 1 1 d . . .
C11 C 0.1720(2) 0.1261(2) 0.6277(2) 0.0373(6) Uani 1 1 d . . .
C12 C 0.1416(3) 0.0213(3) 0.5519(2) 0.0457(7) Uani 1 1 d . . .
H12A H 0.1341 0.0347 0.4742 0.055 Uiso 1 1 calc R . .
C13 C 0.1226(3) -0.1021(3) 0.5924(3) 0.0481(7) Uani 1 1 d . . .
H13A H 0.1038 -0.1728 0.5420 0.058 Uiso 1 1 calc R . .
C14 C 0.1311(3) -0.1220(3) 0.7068(3) 0.0480(7) Uani 1 1 d . . .
H14A H 0.1195 -0.2059 0.7341 0.058 Uiso 1 1 calc R . .
C15 C 0.1574(3) -0.0156(2) 0.7814(2) 0.0402(6) Uani 1 1 d . . .
H15A H 0.1607 -0.0285 0.8585 0.048 Uiso 1 1 calc R . .
C16 C 0.2401(2) 0.5295(2) 0.9324(2) 0.0337(5) Uani 1 1 d . . .
C17 C 0.2802(3) 0.6598(2) 0.9513(2) 0.0423(6) Uani 1 1 d . . .
H17A H 0.3367 0.6935 0.9128 0.051 Uiso 1 1 calc R . .
C18 C 0.2365(3) 0.7393(3) 1.0268(3) 0.0549(8) Uani 1 1 d . . .
H18A H 0.2649 0.8255 1.0397 0.066 Uiso 1 1 calc R . .
C19 C 0.1517(3) 0.6918(3) 1.0825(3) 0.0581(9) Uani 1 1 d . . .
H19A H 0.1218 0.7459 1.1326 0.070 Uiso 1 1 calc R . .
C20 C 0.1111(3) 0.5644(3) 1.0641(3) 0.0559(8) Uani 1 1 d . . .
H20A H 0.0527 0.5325 1.1013 0.067 Uiso 1 1 calc R . .
C21 C 0.1559(3) 0.4825(3) 0.9908(2) 0.0437(6) Uani 1 1 d . . .
H21A H 0.1292 0.3953 0.9807 0.052 Uiso 1 1 calc R . .
C22 C 0.2984(2) 0.4470(2) 0.8522(2) 0.0318(5) Uani 1 1 d . . .
H22A H 0.3406 0.5078 0.8105 0.038 Uiso 1 1 calc R . .
C23 C 0.3292(2) 0.2203(2) 0.9152(2) 0.0331(5) Uani 1 1 d . . .
C24 C 0.3159(3) 0.1941(2) 1.0380(2) 0.0409(6) Uani 1 1 d . . .
C25 C 0.1976(4) 0.1013(4) 1.1592(3) 0.0658(9) Uani 1 1 d . . .
H25A H 0.1424 0.0268 1.1548 0.079 Uiso 1 1 calc R . .
H25B H 0.2760 0.0751 1.2057 0.079 Uiso 1 1 calc R . .
C26 C 0.1497(5) 0.2129(5) 1.2134(4) 0.1032(16) Uani 1 1 d . . .
H26A H 0.1414 0.1875 1.2881 0.155 Uiso 1 1 calc R . .
H26B H 0.0714 0.2381 1.1683 0.155 Uiso 1 1 calc R . .
H26C H 0.2050 0.2863 1.2193 0.155 Uiso 1 1 calc R . .
C27 C 0.4114(2) 0.1051(2) 0.8922(2) 0.0370(6) Uani 1 1 d . . .
C28 C 0.5470(3) 0.0332(3) 0.7773(3) 0.0578(8) Uani 1 1 d . . .
H28A H 0.6198 0.0749 0.7627 0.069 Uiso 1 1 calc R . .
H28B H 0.5720 -0.0294 0.8391 0.069 Uiso 1 1 calc R . .
C29 C 0.4830(4) -0.0359(5) 0.6758(4) 0.0887(13) Uani 1 1 d . . .
H29A H 0.5355 -0.1021 0.6553 0.133 Uiso 1 1 calc R . .
H29B H 0.4598 0.0261 0.6144 0.133 Uiso 1 1 calc R . .
H29C H 0.4112 -0.0774 0.6907 0.133 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 0.1108(3) 0.04953(16) 0.0685(2) 0.01514(16) 0.0354(2) -0.01314(19)
N1 0.0393(13) 0.0320(10) 0.0323(12) 0.0016(8) 0.0060(10) 0.0027(9)
N2 0.0291(11) 0.0311(11) 0.0421(11) -0.0014(9) 0.0009(9) -0.0034(9)
O1 0.0568(13) 0.0361(9) 0.0314(9) -0.0013(7) 0.0046(9) -0.0066(8)
O2 0.0354(11) 0.0520(13) 0.0725(14) 0.0103(10) 0.0016(10) -0.0039(9)
O3 0.0535(13) 0.0314(8) 0.0513(12) 0.0048(8) 0.0073(10) 0.0073(8)
O4 0.0530(13) 0.0557(11) 0.0389(11) 0.0111(9) 0.0119(10) -0.0057(10)
O5 0.0700(16) 0.0873(16) 0.0340(11) 0.0009(11) -0.0022(11) -0.0184(13)
O6 0.0576(13) 0.0435(10) 0.0459(11) 0.0034(8) 0.0173(10) 0.0180(9)
O7 0.0473(12) 0.0411(10) 0.0663(13) 0.0187(9) 0.0093(10) 0.0137(8)
C1 0.063(2) 0.0352(13) 0.0516(18) 0.0080(12) 0.0273(16) -0.0042(13)
C2 0.0480(18) 0.0480(15) 0.0552(18) -0.0013(13) 0.0177(16) -0.0129(13)
C3 0.0377(16) 0.0464(14) 0.0443(15) 0.0017(12) 0.0116(13) 0.0020(12)
C4 0.0363(15) 0.0350(12) 0.0313(13) 0.0016(10) 0.0100(12) 0.0012(11)
C5 0.0451(17) 0.0467(14) 0.0419(16) 0.0038(12) 0.0100(14) -0.0071(12)
C6 0.059(2) 0.0486(15) 0.0389(15) 0.0107(12) 0.0080(14) 0.0052(14)
C7 0.0375(13) 0.0305(10) 0.0321(11) -0.0012(11) 0.0085(10) 0.0001(11)
C8 0.0295(13) 0.0262(11) 0.0321(12) 0.0014(9) 0.0045(10) 0.0027(9)
C9 0.0321(14) 0.0240(10) 0.0305(12) -0.0001(9) 0.0043(11) -0.0008(9)
C10 0.0328(14) 0.0275(11) 0.0358(13) -0.0028(9) -0.0001(11) -0.0006(10)
C11 0.0392(15) 0.0309(11) 0.0395(15) -0.0024(10) 0.0037(12) 0.0006(10)
C12 0.0521(19) 0.0437(14) 0.0369(16) -0.0106(12) -0.0001(14) -0.0007(12)
C13 0.0452(17) 0.0370(14) 0.059(2) -0.0168(12) 0.0045(15) -0.0042(12)
C14 0.0462(17) 0.0284(11) 0.067(2) -0.0033(12) 0.0072(15) -0.0064(11)
C15 0.0409(16) 0.0330(12) 0.0446(15) 0.0026(11) 0.0047(13) -0.0033(11)
C16 0.0352(15) 0.0347(12) 0.0283(12) -0.0024(10) 0.0009(11) 0.0041(10)
C17 0.0551(18) 0.0312(12) 0.0399(15) -0.0032(10) 0.0092(14) 0.0002(11)
C18 0.077(2) 0.0344(13) 0.0507(17) -0.0091(13) 0.0094(17) 0.0068(14)
C19 0.074(2) 0.0557(17) 0.0462(17) -0.0143(14) 0.0160(17) 0.0180(16)
C20 0.0508(19) 0.0671(19) 0.0545(19) -0.0064(15) 0.0217(16) 0.0043(15)
C21 0.0461(17) 0.0401(13) 0.0467(16) -0.0051(12) 0.0143(14) -0.0018(12)
C22 0.0365(14) 0.0250(10) 0.0333(13) -0.0009(9) 0.0063(11) -0.0006(10)
C23 0.0353(15) 0.0297(11) 0.0324(13) -0.0023(10) 0.0033(11) -0.0005(10)
C24 0.0483(18) 0.0390(13) 0.0338(15) 0.0030(10) 0.0057(14) 0.0014(12)
C25 0.083(3) 0.068(2) 0.0507(19) 0.0188(16) 0.0249(19) -0.0054(19)
C26 0.147(5) 0.102(3) 0.082(3) 0.013(3) 0.071(3) 0.009(3)
C27 0.0341(15) 0.0336(12) 0.0378(14) -0.0019(10) -0.0039(12) 0.0018(11)
C28 0.062(2) 0.0566(17) 0.0559(19) -0.0024(14) 0.0161(16) 0.0249(15)
C29 0.086(3) 0.105(3) 0.075(3) -0.041(2) 0.015(2) 0.011(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
Br1 C1 1.893(3) . ?
N1 O3 1.222(3) . ?
N1 O2 1.225(3) . ?
N1 C8 1.503(3) . ?
N2 C23 1.444(3) . ?
N2 C22 1.459(3) . ?
N2 H2B 0.8600 . ?
O1 C11 1.381(3) . ?
O1 C7 1.426(3) . ?
O4 C24 1.327(4) . ?
O4 C25 1.469(4) . ?
O5 C24 1.201(3) . ?
O6 C27 1.321(3) . ?
O6 C28 1.458(3) . ?
O7 C27 1.190(3) . ?
C1 C6 1.368(4) . ?
C1 C2 1.376(5) . ?
C2 C3 1.385(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C7 1.511(3) . ?
C5 C6 1.381(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.561(3) . ?
C7 H7A 0.9800 . ?
C8 C22 1.539(3) . ?
C8 C9 1.539(3) . ?
C9 C10 1.516(3) . ?
C9 C23 1.566(4) . ?
C9 H9A 0.9800 . ?
C10 C11 1.376(4) . ?
C10 C15 1.391(3) . ?
C11 C12 1.391(4) . ?
C12 C13 1.373(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.375(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.390(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C21 1.382(4) . ?
C16 C17 1.395(4) . ?
C16 C22 1.529(3) . ?
C17 C18 1.381(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.368(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.384(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9800 . ?
C23 C24 1.542(4) . ?
C23 C27 1.549(3) . ?
C25 C26 1.464(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C28 C29 1.453(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
O3 N1 O2 124.0(2) . . ?
O3 N1 C8 117.0(2) . . ?
O2 N1 C8 118.95(19) . . ?
C23 N2 C22 112.6(2) . . ?
C23 N2 H2B 123.7 . . ?
C22 N2 H2B 123.7 . . ?
C11 O1 C7 114.67(19) . . ?
C24 O4 C25 116.0(2) . . ?
C27 O6 C28 118.3(2) . . ?
C6 C1 C2 121.0(3) . . ?
C6 C1 Br1 119.6(2) . . ?
C2 C1 Br1 119.4(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 121.9(2) . . ?
C3 C4 C7 119.2(2) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
O1 C7 C4 106.36(19) . . ?
O1 C7 C8 109.96(19) . . ?
C4 C7 C8 117.2(2) . . ?
O1 C7 H7A 107.6 . . ?
C4 C7 H7A 107.6 . . ?
C8 C7 H7A 107.6 . . ?
N1 C8 C22 111.41(17) . . ?
N1 C8 C9 112.05(18) . . ?
C22 C8 C9 105.90(19) . . ?
N1 C8 C7 107.16(18) . . ?
C22 C8 C7 111.5(2) . . ?
C9 C8 C7 108.86(18) . . ?
C10 C9 C8 113.74(19) . . ?
C10 C9 C23 116.57(19) . . ?
C8 C9 C23 103.24(18) . . ?
C10 C9 H9A 107.6 . . ?
C8 C9 H9A 107.6 . . ?
C23 C9 H9A 107.6 . . ?
C11 C10 C15 118.2(2) . . ?
C11 C10 C9 120.9(2) . . ?
C15 C10 C9 120.9(2) . . ?
C10 C11 O1 122.5(2) . . ?
C10 C11 C12 121.2(2) . . ?
O1 C11 C12 116.2(2) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15A 119.5 . . ?
C10 C15 H15A 119.5 . . ?
C21 C16 C17 118.3(2) . . ?
C21 C16 C22 124.8(2) . . ?
C17 C16 C22 116.7(2) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C16 C21 C20 120.4(3) . . ?
C16 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
N2 C22 C16 116.2(2) . . ?
N2 C22 C8 99.10(17) . . ?
C16 C22 C8 117.4(2) . . ?
N2 C22 H22A 107.8 . . ?
C16 C22 H22A 107.8 . . ?
C8 C22 H22A 107.8 . . ?
N2 C23 C24 111.6(2) . . ?
N2 C23 C27 111.1(2) . . ?
C24 C23 C27 103.4(2) . . ?
N2 C23 C9 104.38(19) . . ?
C24 C23 C9 115.0(2) . . ?
C27 C23 C9 111.7(2) . . ?
O5 C24 O4 124.7(3) . . ?
O5 C24 C23 121.5(3) . . ?
O4 C24 C23 113.8(2) . . ?
C26 C25 O4 112.0(3) . . ?
C26 C25 H25A 109.2 . . ?
O4 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
O4 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 O6 125.8(2) . . ?
O7 C27 C23 122.1(3) . . ?
O6 C27 C23 112.1(2) . . ?
C29 C28 O6 110.0(3) . . ?
C29 C28 H28A 109.7 . . ?
O6 C28 H28A 109.7 . . ?
C29 C28 H28B 109.7 . . ?
O6 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C6 C1 C2 C3 -0.7(4) . . . . ?
Br1 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C7 -179.9(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C7 C4 C5 C6 179.5(3) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
Br1 C1 C6 C5 179.9(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C11 O1 C7 C4 175.2(2) . . . . ?
C11 O1 C7 C8 -56.9(3) . . . . ?
C5 C4 C7 O1 28.3(3) . . . . ?
C3 C4 C7 O1 -150.8(2) . . . . ?
C5 C4 C7 C8 -95.1(3) . . . . ?
C3 C4 C7 C8 85.8(3) . . . . ?
O3 N1 C8 C22 45.9(3) . . . . ?
O2 N1 C8 C22 -135.9(2) . . . . ?
O3 N1 C8 C9 164.3(2) . . . . ?
O2 N1 C8 C9 -17.5(3) . . . . ?
O3 N1 C8 C7 -76.3(2) . . . . ?
O2 N1 C8 C7 101.9(2) . . . . ?
O1 C7 C8 N1 -62.0(2) . . . . ?
C4 C7 C8 N1 59.6(3) . . . . ?
O1 C7 C8 C22 175.87(19) . . . . ?
C4 C7 C8 C22 -62.5(3) . . . . ?
O1 C7 C8 C9 59.4(2) . . . . ?
C4 C7 C8 C9 -179.0(2) . . . . ?
N1 C8 C9 C10 85.2(2) . . . . ?
C22 C8 C9 C10 -153.1(2) . . . . ?
C7 C8 C9 C10 -33.1(3) . . . . ?
N1 C8 C9 C23 -147.53(19) . . . . ?
C22 C8 C9 C23 -25.9(2) . . . . ?
C7 C8 C9 C23 94.1(2) . . . . ?
C8 C9 C10 C11 4.9(3) . . . . ?
C23 C9 C10 C11 -115.0(3) . . . . ?
C8 C9 C10 C15 -173.6(2) . . . . ?
C23 C9 C10 C15 66.4(3) . . . . ?
C15 C10 C11 O1 178.9(3) . . . . ?
C9 C10 C11 O1 0.3(4) . . . . ?
C15 C10 C11 C12 1.5(4) . . . . ?
C9 C10 C11 C12 -177.1(3) . . . . ?
C7 O1 C11 C10 27.0(4) . . . . ?
C7 O1 C11 C12 -155.5(2) . . . . ?
C10 C11 C12 C13 -2.5(4) . . . . ?
O1 C11 C12 C13 179.9(3) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C10 -2.0(4) . . . . ?
C11 C10 C15 C14 0.8(4) . . . . ?
C9 C10 C15 C14 179.3(3) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
C22 C16 C17 C18 -176.9(3) . . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C17 C16 C21 C20 1.4(4) . . . . ?
C22 C16 C21 C20 178.1(3) . . . . ?
C19 C20 C21 C16 -1.8(5) . . . . ?
C23 N2 C22 C16 90.2(3) . . . . ?
C23 N2 C22 C8 -36.6(3) . . . . ?
C21 C16 C22 N2 -70.6(3) . . . . ?
C17 C16 C22 N2 106.2(3) . . . . ?
C21 C16 C22 C8 46.4(4) . . . . ?
C17 C16 C22 C8 -136.8(2) . . . . ?
N1 C8 C22 N2 159.10(18) . . . . ?
C9 C8 C22 N2 37.0(2) . . . . ?
C7 C8 C22 N2 -81.2(2) . . . . ?
N1 C8 C22 C16 33.2(3) . . . . ?
C9 C8 C22 C16 -88.9(2) . . . . ?
C7 C8 C22 C16 152.8(2) . . . . ?
C22 N2 C23 C24 -103.6(3) . . . . ?
C22 N2 C23 C27 141.7(2) . . . . ?
C22 N2 C23 C9 21.2(3) . . . . ?
C10 C9 C23 N2 129.5(2) . . . . ?
C8 C9 C23 N2 4.1(2) . . . . ?
C10 C9 C23 C24 -107.9(2) . . . . ?
C8 C9 C23 C24 126.6(2) . . . . ?
C10 C9 C23 C27 9.4(3) . . . . ?
C8 C9 C23 C27 -116.0(2) . . . . ?
C25 O4 C24 O5 -1.6(4) . . . . ?
C25 O4 C24 C23 177.2(2) . . . . ?
N2 C23 C24 O5 -39.5(4) . . . . ?
C27 C23 C24 O5 79.9(3) . . . . ?
C9 C23 C24 O5 -158.1(3) . . . . ?
N2 C23 C24 O4 141.6(2) . . . . ?
C27 C23 C24 O4 -99.0(2) . . . . ?
C9 C23 C24 O4 23.0(3) . . . . ?
C24 O4 C25 C26 84.7(4) . . . . ?
C28 O6 C27 O7 0.9(4) . . . . ?
C28 O6 C27 C23 -179.0(2) . . . . ?
N2 C23 C27 O7 142.1(3) . . . . ?
C24 C23 C27 O7 22.3(3) . . . . ?
C9 C23 C27 O7 -101.9(3) . . . . ?
N2 C23 C27 O6 -38.1(3) . . . . ?
C24 C23 C27 O6 -157.8(2) . . . . ?
C9 C23 C27 O6 78.0(3) . . . . ?
C27 O6 C28 C29 99.4(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O7 0.86 2.29 2.966(3) 135.2 2_657
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 27.68
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.342
_refine_diff_density_min -0.664
_refine_diff_density_rms 0.053
_publ_section_references
;
Sheldrick, G. M. (1996). SADABS, Absorption Correction Program,
University of Goeltingen, German Siemens(1994), SAINT Software
Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA
Siemens(1996), SMART Software Reference Manual, Siemens Energy &
Automation Inc., Madison, Wisconsin, USA Siemens(1994), SHELXTL^TM^
Version 5 Reference Manual, Siemens Energy & Automation Inc., Madison,
Wisconsin, USA
;