#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024597.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024597
loop_
_publ_author_name
'Liang Cheng'
'Li Liu'
'Han Jia'
'Dong Wang'
'Yong-Jun Chen'
_publ_section_title
;
Enantioselective Organocatalytic anti-Mannich-Type Reaction of N-Unprotected
3-Substituted 2-Oxindoles with Aromatic N-Ts-aldimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4650
_journal_page_last               4653
_journal_paper_doi               10.1021/jo9006688
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H25 Br N2 O3 S'
_chemical_formula_sum            'C29 H25 Br N2 O3 S'
_chemical_formula_weight         561.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4440(19)
_cell_length_b                   13.4440(19)
_cell_length_c                   32.156(6)
_cell_measurement_reflns_used    879
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     5811.9(16)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.2584
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            7514
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    1.517
_exptl_absorpt_correction_T_max  0.5752
_exptl_absorpt_correction_T_min  0.5236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.512(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6601
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.545
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0150P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0855
_reflns_number_gt                2391
_reflns_number_total             6601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9006688_si_001.cif
_cod_data_source_block           sx2619
_cod_original_sg_symbol_H-M      P4(3)2(1)2
_cod_database_code               4024597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'
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 0.37592(5) 0.76814(4) 0.022171(14) 0.0742(2) Uani 1 1 d . . .
S1 S 0.70020(8) 0.11196(9) 0.05277(3) 0.0404(3) Uani 1 1 d . . .
O1 O 0.80092(19) 0.1121(2) 0.03800(7) 0.0451(8) Uani 1 1 d . . .
O2 O 0.62031(19) 0.1271(2) 0.02360(7) 0.0491(7) Uani 1 1 d . . .
O3 O 0.39154(19) 0.29052(19) 0.12166(7) 0.0406(7) Uani 1 1 d . . .
N1 N 0.6943(2) 0.1975(2) 0.08834(8) 0.0351(8) Uani 1 1 d . . .
H1B H 0.7464 0.2345 0.0941 0.042 Uiso 1 1 calc R . .
N2 N 0.4812(2) 0.3905(2) 0.16609(8) 0.0379(8) Uani 1 1 d . . .
H2B H 0.4343 0.4039 0.1843 0.046 Uiso 1 1 calc R . .
C1 C 0.5839(3) -0.0462(3) 0.07617(12) 0.0455(12) Uani 1 1 d . . .
H1C H 0.5341 -0.0179 0.0589 0.055 Uiso 1 1 calc R . .
C2 C 0.5643(4) -0.1313(4) 0.09838(13) 0.0575(14) Uani 1 1 d . . .
H2C H 0.5005 -0.1614 0.0965 0.069 Uiso 1 1 calc R . .
C3 C 0.6357(5) -0.1733(3) 0.12318(14) 0.0623(16) Uani 1 1 d . . .
C4 C 0.7288(4) -0.1284(4) 0.12500(13) 0.0634(14) Uani 1 1 d . . .
H4A H 0.7789 -0.1579 0.1418 0.076 Uiso 1 1 calc R . .
C5 C 0.7509(4) -0.0438(3) 0.10362(13) 0.0655(16) Uani 1 1 d . . .
H5A H 0.8150 -0.0142 0.1054 0.079 Uiso 1 1 calc R . .
C6 C 0.6764(4) -0.0021(3) 0.07908(12) 0.0430(12) Uani 1 1 d . . .
C7 C 0.6154(4) -0.2691(3) 0.14824(12) 0.0802(17) Uani 1 1 d . . .
H7A H 0.5463 -0.2900 0.1440 0.120 Uiso 1 1 calc R . .
H7B H 0.6267 -0.2563 0.1779 0.120 Uiso 1 1 calc R . .
H7C H 0.6604 -0.3219 0.1388 0.120 Uiso 1 1 calc R . .
C8 C 0.59983(11) 0.21180(10) 0.11079(4) 0.0293(9) Uani 1 1 d . . .
H8A H 0.5481 0.1746 0.0948 0.035 Uiso 1 1 calc R . .
C9 C 0.59882(11) 0.16883(10) 0.15454(4) 0.0393(11) Uani 1 1 d RD . .
C10 C 0.51946(11) 0.10840(10) 0.16593(4) 0.0640(14) Uani 1 1 d RD . .
H10 H 0.4683 0.0941 0.1464 0.077 Uiso 1 1 calc R . .
C11 C 0.51495(11) 0.06888(10) 0.20583(4) 0.0743(17) Uani 1 1 d RD . .
H11 H 0.4607 0.0276 0.2136 0.089 Uiso 1 1 calc R . .
C12 C 0.58979(11) 0.08978(10) 0.23434(4) 0.0642(15) Uani 1 1 d RD . .
H12 H 0.5867 0.0628 0.2616 0.077 Uiso 1 1 calc R . .
C13 C 0.66915(11) 0.15020(10) 0.22296(4) 0.0590(14) Uani 1 1 d RD . .
H13 H 0.7203 0.1645 0.2425 0.071 Uiso 1 1 calc R . .
C14 C 0.67366(11) 0.18973(10) 0.18306(4) 0.0488(12) Uani 1 1 d RD . .
H14 H 0.7279 0.2310 0.1753 0.059 Uiso 1 1 calc R . .
C15 C 0.56841(11) 0.32712(10) 0.10899(4) 0.0321(10) Uani 1 1 d R . .
C16 C 0.63181(11) 0.39171(10) 0.13493(4) 0.0289(9) Uani 1 1 d R . .
C17 C 0.73212(11) 0.42057(10) 0.13180(4) 0.0437(11) Uani 1 1 d R . .
H17A H 0.7717 0.3977 0.1093 0.052 Uiso 1 1 calc R . .
C18 C 0.7728(3) 0.4822(3) 0.16160(13) 0.0537(13) Uani 1 1 d . . .
H18A H 0.8402 0.5027 0.1593 0.064 Uiso 1 1 calc R . .
C19 C 0.7171(4) 0.5134(3) 0.19402(14) 0.0516(13) Uani 1 1 d . . .
H19A H 0.7476 0.5546 0.2144 0.062 Uiso 1 1 calc R . .
C20 C 0.6196(3) 0.4891(3) 0.19905(12) 0.0480(12) Uani 1 1 d . . .
H20A H 0.5813 0.5128 0.2218 0.058 Uiso 1 1 calc R . .
C21 C 0.5798(3) 0.4273(3) 0.16871(12) 0.0404(11) Uani 1 1 d . . .
C22 C 0.4679(3) 0.3319(3) 0.13204(11) 0.0322(10) Uani 1 1 d . . .
C23 C 0.5561(3) 0.3582(3) 0.06363(11) 0.0355(11) Uani 1 1 d . . .
H23A H 0.6220 0.3558 0.0499 0.043 Uiso 1 1 calc R . .
H23B H 0.5127 0.3092 0.0495 0.043 Uiso 1 1 calc R . .
C24 C 0.5128(3) 0.4599(3) 0.05766(11) 0.0360(11) Uani 1 1 d . . .
C25 C 0.5716(3) 0.5459(3) 0.05545(12) 0.0470(12) Uani 1 1 d . . .
H25A H 0.6414 0.5406 0.0597 0.056 Uiso 1 1 calc R . .
C26 C 0.5307(4) 0.6383(3) 0.04725(12) 0.0492(12) Uani 1 1 d . . .
H26A H 0.5712 0.6962 0.0472 0.059 Uiso 1 1 calc R . .
C27 C 0.4327(4) 0.6451(3) 0.03932(12) 0.0489(13) Uani 1 1 d . . .
C28 C 0.3703(4) 0.5647(3) 0.04128(12) 0.0486(13) Uani 1 1 d . . .
H28A H 0.3011 0.5718 0.0361 0.058 Uiso 1 1 calc R . .
C29 C 0.4107(3) 0.4727(3) 0.05098(11) 0.0445(12) Uani 1 1 d . . .
H29A H 0.3679 0.4168 0.0531 0.053 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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'
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
O1 S1 O2 119.19(15) . . ?
O1 S1 N1 106.19(17) . . ?
O2 S1 N1 108.77(17) . . ?
O1 S1 C6 109.1(2) . . ?
O2 S1 C6 107.3(2) . . ?
N1 S1 C6 105.44(16) . . ?
C8 N1 S1 118.7(2) . . ?
C8 N1 H1B 120.6 . . ?
S1 N1 H1B 120.6 . . ?
C22 N2 C21 111.9(3) . . ?
C22 N2 H2B 124.1 . . ?
C21 N2 H2B 124.1 . . ?
C2 C1 C6 119.7(4) . . ?
C2 C1 H1C 120.2 . . ?
C6 C1 H1C 120.2 . . ?
C3 C2 C1 120.8(5) . . ?
C3 C2 H2C 119.6 . . ?
C1 C2 H2C 119.6 . . ?
C2 C3 C4 118.5(4) . . ?
C2 C3 C7 121.6(5) . . ?
C4 C3 C7 119.9(5) . . ?
C5 C4 C3 122.5(5) . . ?
C5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.7 . . ?
C4 C5 C6 117.7(5) . . ?
C4 C5 H5A 121.1 . . ?
C6 C5 H5A 121.1 . . ?
C1 C6 C5 120.9(4) . . ?
C1 C6 S1 120.0(4) . . ?
C5 C6 S1 119.1(4) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 114.29(12) . . ?
N1 C8 C15 109.57(14) . . ?
C9 C8 C15 113.4 . . ?
N1 C8 H8A 106.3 . . ?
C9 C8 H8A 106.3 . . ?
C15 C8 H8A 106.3 . . ?
C14 C9 C10 120.0 . . ?
C14 C9 C8 121.8 . . ?
C10 C9 C8 118.2 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C16 C15 C23 116.23(16) . . ?
C16 C15 C22 102.11(17) . . ?
C23 C15 C22 110.7(2) . . ?
C16 C15 C8 113.3 . . ?
C23 C15 C8 109.06(15) . . ?
C22 C15 C8 104.65(15) . . ?
C21 C16 C17 116.6(2) . . ?
C21 C16 C15 110.9(2) . . ?
C17 C16 C15 132.5 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C20 123.4(5) . . ?
C18 C19 H19A 118.3 . . ?
C20 C19 H19A 118.3 . . ?
C19 C20 C21 115.6(4) . . ?
C19 C20 H20A 122.2 . . ?
C21 C20 H20A 122.2 . . ?
C16 C21 C20 124.5(4) . . ?
C16 C21 N2 107.9(3) . . ?
C20 C21 N2 127.6(4) . . ?
O3 C22 N2 126.7(4) . . ?
O3 C22 C15 126.1(3) . . ?
N2 C22 C15 107.2(3) . . ?
C24 C23 C15 114.4(3) . . ?
C24 C23 H23A 108.6 . . ?
C15 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C15 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C29 C24 C25 116.3(4) . . ?
C29 C24 C23 120.8(4) . . ?
C25 C24 C23 122.7(4) . . ?
C26 C25 C24 121.7(4) . . ?
C26 C25 H25A 119.2 . . ?
C24 C25 H25A 119.2 . . ?
C27 C26 C25 119.2(5) . . ?
C27 C26 H26A 120.4 . . ?
C25 C26 H26A 120.4 . . ?
C26 C27 C28 122.5(5) . . ?
C26 C27 Br1 120.5(4) . . ?
C28 C27 Br1 117.0(4) . . ?
C27 C28 C29 118.4(4) . . ?
C27 C28 H28A 120.8 . . ?
C29 C28 H28A 120.8 . . ?
C28 C29 C24 121.9(5) . . ?
C28 C29 H29A 119.1 . . ?
C24 C29 H29A 119.1 . . ?
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 C27 1.903(4) . ?
S1 O1 1.435(3) . ?
S1 O2 1.440(2) . ?
S1 N1 1.623(3) . ?
S1 C6 1.780(4) . ?
O3 C22 1.215(4) . ?
N1 C8 1.473(3) . ?
N1 H1B 0.8800 . ?
N2 C22 1.361(4) . ?
N2 C21 1.417(5) . ?
N2 H2B 0.8800 . ?
C1 C2 1.374(6) . ?
C1 C6 1.381(6) . ?
C1 H1C 0.9500 . ?
C2 C3 1.369(6) . ?
C2 H2C 0.9500 . ?
C3 C4 1.391(6) . ?
C3 C7 1.544(6) . ?
C4 C5 1.362(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(5) . ?
C5 H5A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5209 . ?
C8 C15 1.6079 . ?
C8 H8A 1.0000 . ?
C9 C14 1.3901 . ?
C9 C10 1.3901 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3899 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3901 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.4752 . ?
C15 C23 1.526(4) . ?
C15 C22 1.542(4) . ?
C16 C21 1.377(4) . ?
C16 C17 1.4069 . ?
C17 C18 1.379(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.351(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.361(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.389(5) . ?
C20 H20A 0.9500 . ?
C23 C24 1.499(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C29 1.400(5) . ?
C24 C25 1.403(6) . ?
C25 C26 1.384(6) . ?
C25 H25A 0.9500 . ?
C26 C27 1.345(6) . ?
C26 H26A 0.9500 . ?
C27 C28 1.369(6) . ?
C28 C29 1.387(5) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?
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
N1 H1B O3 0.88 2.27 2.952(4) 134.8 6
N2 H2B O1 0.88 2.01 2.839(4) 155.7 6_455
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
O1 S1 N1 C8 -177.3(2) . . . . ?
O2 S1 N1 C8 53.3(3) . . . . ?
C6 S1 N1 C8 -61.5(3) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C1 C2 C3 C7 -179.7(4) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C7 C3 C4 C5 -179.9(4) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C2 C1 C6 C5 1.3(7) . . . . ?
C2 C1 C6 S1 -176.4(3) . . . . ?
C4 C5 C6 C1 -0.9(7) . . . . ?
C4 C5 C6 S1 176.8(3) . . . . ?
O1 S1 C6 C1 -144.2(4) . . . . ?
O2 S1 C6 C1 -13.8(4) . . . . ?
N1 S1 C6 C1 102.1(4) . . . . ?
O1 S1 C6 C5 38.0(4) . . . . ?
O2 S1 C6 C5 168.5(3) . . . . ?
N1 S1 C6 C5 -75.7(4) . . . . ?
S1 N1 C8 C9 103.42(17) . . . . ?
S1 N1 C8 C15 -128.05(17) . . . . ?
N1 C8 C9 C14 50.69(15) . . . . ?
C15 C8 C9 C14 -75.9 . . . . ?
N1 C8 C9 C10 -130.31(15) . . . . ?
C15 C8 C9 C10 103.1 . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 C11 -179.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
C8 C9 C14 C13 179.0 . . . . ?
N1 C8 C15 C16 -71.39(13) . . . . ?
C9 C8 C15 C16 57.6 . . . . ?
N1 C8 C15 C23 59.7(2) . . . . ?
C9 C8 C15 C23 -171.24(17) . . . . ?
N1 C8 C15 C22 178.2(2) . . . . ?
C9 C8 C15 C22 -52.78(16) . . . . ?
C23 C15 C16 C21 122.2(3) . . . . ?
C22 C15 C16 C21 1.6(2) . . . . ?
C8 C15 C16 C21 -110.36(18) . . . . ?
C23 C15 C16 C17 -59.19(17) . . . . ?
C22 C15 C16 C17 -179.75(14) . . . . ?
C8 C15 C16 C17 68.3 . . . . ?
C21 C16 C17 C18 -0.6(3) . . . . ?
C15 C16 C17 C18 -179.1(2) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C18 C19 C20 C21 1.2(7) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
C15 C16 C21 C20 179.3(3) . . . . ?
C17 C16 C21 N2 179.75(19) . . . . ?
C15 C16 C21 N2 -1.4(3) . . . . ?
C19 C20 C21 C16 -0.7(6) . . . . ?
C19 C20 C21 N2 -179.9(4) . . . . ?
C22 N2 C21 C16 0.5(4) . . . . ?
C22 N2 C21 C20 179.8(4) . . . . ?
C21 N2 C22 O3 -179.7(4) . . . . ?
C21 N2 C22 C15 0.6(4) . . . . ?
C16 C15 C22 O3 179.0(3) . . . . ?
C23 C15 C22 O3 54.7(4) . . . . ?
C8 C15 C22 O3 -62.7(4) . . . . ?
C16 C15 C22 N2 -1.3(3) . . . . ?
C23 C15 C22 N2 -125.6(3) . . . . ?
C8 C15 C22 N2 117.0(2) . . . . ?
C16 C15 C23 C24 -58.8(3) . . . . ?
C22 C15 C23 C24 57.1(4) . . . . ?
C8 C15 C23 C24 171.7(3) . . . . ?
C15 C23 C24 C29 -95.5(4) . . . . ?
C15 C23 C24 C25 89.2(5) . . . . ?
C29 C24 C25 C26 0.2(7) . . . . ?
C23 C24 C25 C26 175.7(4) . . . . ?
C24 C25 C26 C27 -3.1(7) . . . . ?
C25 C26 C27 C28 3.7(7) . . . . ?
C25 C26 C27 Br1 -173.3(3) . . . . ?
C26 C27 C28 C29 -1.4(7) . . . . ?
Br1 C27 C28 C29 175.8(3) . . . . ?
C27 C28 C29 C24 -1.7(7) . . . . ?
C25 C24 C29 C28 2.2(7) . . . . ?
C23 C24 C29 C28 -173.5(4) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.210 0.210 0.500 215 74 ' '
2 0.290 0.710 0.250 215 74 ' '
3 0.710 0.290 0.750 216 74 ' '
4 0.790 0.790 1.000 215 74 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658968
