#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:52:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178409 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/30/4023051.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_4023051
loop_
_publ_author_name
'Hanns Martin Kaiser'
'Ivo Zenz'
'Wei Fun Lo'
'Anke Spannenberg'
'Kristin Schröder'
'Haijun Jiao'
'Dirk Gördes'
'Matthias Beller'
'Man Kin Tse'
_publ_section_title
;
 Preparation of Novel Unsymmetrical Bisindoles under Solvent-Free
 Conditions: Synthesis, Crystal Structures, and Mechanistic Aspects
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8847
_journal_page_last               8858
_journal_paper_doi               10.1021/jo7016026
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C28 H31 N3 O7 S'
_chemical_formula_weight         553.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.041(3)
_cell_angle_beta                 71.034(3)
_cell_angle_gamma                68.628(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3736(4)
_cell_length_b                   11.4650(5)
_cell_length_c                   13.1802(5)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    200(2)
_cell_volume                     1374.19(10)
_computing_data_collection       STOE-X-AREA
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'STOE-IPDS II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19916
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9094
_exptl_absorpt_correction_T_min  0.7267
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0197(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0379
_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)+(0.0564P)²+0.0791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                4087
_reflns_number_total             5403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7016026-File004.cif
_cod_data_source_block           ks649t
_cod_database_code               4023051
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.63125(17) 0.27370(15) 0.59091(14) 0.0260(3) Uani 1 1 d . . .
C2 C 0.55628(17) 0.23936(15) 0.69700(14) 0.0275(4) Uani 1 1 d . . .
C3 C 0.46623(19) 0.12312(15) 0.59851(14) 0.0286(4) Uani 1 1 d . . .
H3A H 0.4216 0.0587 0.6159 0.034 Uiso 1 1 calc R . .
H3B H 0.5711 0.0804 0.5545 0.034 Uiso 1 1 calc R . .
C4 C 0.38898(17) 0.21841(15) 0.53547(13) 0.0271(4) Uani 1 1 d . . .
H4 H 0.2799 0.2443 0.5572 0.033 Uiso 1 1 calc R . .
C5 C 0.45171(16) 0.31243(15) 0.48872(13) 0.0249(3) Uani 1 1 d . . .
H5 H 0.3803 0.3957 0.4806 0.030 Uiso 1 1 calc R . .
C6 C 0.58548(16) 0.31386(14) 0.50490(13) 0.0243(3) Uani 1 1 d . . .
C7 C 0.68398(17) 0.36803(14) 0.43718(14) 0.0260(3) Uani 1 1 d . . .
C8 C 0.69229(19) 0.42306(16) 0.34003(14) 0.0314(4) Uani 1 1 d . . .
H8 H 0.6231 0.4294 0.3053 0.038 Uiso 1 1 calc R . .
C9 C 0.8030(2) 0.46776(17) 0.29591(16) 0.0375(4) Uani 1 1 d . . .
H9 H 0.8100 0.5055 0.2300 0.045 Uiso 1 1 calc R . .
C10 C 0.90554(19) 0.45859(17) 0.34634(16) 0.0371(4) Uani 1 1 d . . .
H10 H 0.9807 0.4903 0.3138 0.044 Uiso 1 1 calc R . .
C11 C 0.90034(18) 0.40494(16) 0.44179(16) 0.0325(4) Uani 1 1 d . . .
H11 H 0.9706 0.3984 0.4755 0.039 Uiso 1 1 calc R . .
C12 C 0.78765(17) 0.36066(14) 0.48675(14) 0.0269(4) Uani 1 1 d . . .
C13 C 0.86313(18) 0.24119(16) 0.62990(15) 0.0315(4) Uani 1 1 d . . .
C14 C 0.97753(18) 0.03703(16) 0.68985(14) 0.0310(4) Uani 1 1 d . . .
C15 C 0.9471(2) -0.08175(18) 0.68609(18) 0.0448(5) Uani 1 1 d . . .
H15A H 0.8454 -0.0663 0.7311 0.067 Uiso 1 1 calc R . .
H15B H 1.0143 -0.1491 0.7131 0.067 Uiso 1 1 calc R . .
H15C H 0.9618 -0.1068 0.6116 0.067 Uiso 1 1 calc R . .
C16 C 0.9373(2) 0.0900(2) 0.80409(16) 0.0479(5) Uani 1 1 d . . .
H16A H 0.8353 0.1010 0.8445 0.072 Uiso 1 1 calc R . .
H16B H 0.9479 0.1716 0.8034 0.072 Uiso 1 1 calc R . .
H16C H 1.0026 0.0319 0.8386 0.072 Uiso 1 1 calc R . .
C17 C 1.1335(2) 0.0168(2) 0.62080(18) 0.0464(5) Uani 1 1 d . . .
H17A H 1.1526 -0.0174 0.5480 0.070 Uiso 1 1 calc R . .
H17B H 1.2020 -0.0425 0.6523 0.070 Uiso 1 1 calc R . .
H17C H 1.1471 0.0973 0.6174 0.070 Uiso 1 1 calc R . .
C18 C 0.34511(18) 0.17785(15) 0.79246(14) 0.0289(4) Uani 1 1 d . . .
C19 C 0.23417(19) 0.24656(16) 0.98388(15) 0.0422(5) Uani 1 1 d D . .
C20A C 0.0788(3) 0.2576(5) 1.0015(4) 0.0576(12) Uiso 0.629(7) 1 d PD A 1
H20A H 0.0250 0.3385 0.9799 0.086 Uiso 0.629(7) 1 calc PR A 1
H20B H 0.0298 0.2525 1.0779 0.086 Uiso 0.629(7) 1 calc PR A 1
H20C H 0.0806 0.1889 0.9581 0.086 Uiso 0.629(7) 1 calc PR A 1
C21A C 0.3249(5) 0.1238(3) 1.0161(3) 0.0627(13) Uiso 0.629(7) 1 d PD A 1
H21A H 0.4247 0.1211 1.0023 0.094 Uiso 0.629(7) 1 calc PR A 1
H21B H 0.3289 0.0531 0.9739 0.094 Uiso 0.629(7) 1 calc PR A 1
H21C H 0.2796 0.1180 1.0930 0.094 Uiso 0.629(7) 1 calc PR A 1
C22A C 0.2319(5) 0.3581(4) 1.0445(3) 0.0463(10) Uiso 0.629(7) 1 d PD A 1
H22A H 0.3330 0.3509 1.0325 0.069 Uiso 0.629(7) 1 calc PR A 1
H22B H 0.1814 0.3591 1.1217 0.069 Uiso 0.629(7) 1 calc PR A 1
H22C H 0.1800 0.4363 1.0183 0.069 Uiso 0.629(7) 1 calc PR A 1
C20B C 0.0807(4) 0.3109(7) 0.9778(6) 0.0530(18) Uiso 0.371(7) 1 d PD A 2
H20D H 0.0641 0.2580 0.9303 0.080 Uiso 0.371(7) 1 calc PR A 2
H20E H 0.0710 0.3925 0.9492 0.080 Uiso 0.371(7) 1 calc PR A 2
H20F H 0.0079 0.3236 1.0501 0.080 Uiso 0.371(7) 1 calc PR A 2
C21B C 0.2458(12) 0.1144(4) 1.0111(8) 0.087(3) Uiso 0.371(7) 1 d PD A 2
H21D H 0.2204 0.0756 0.9591 0.131 Uiso 0.371(7) 1 calc PR A 2
H21E H 0.1780 0.1179 1.0838 0.131 Uiso 0.371(7) 1 calc PR A 2
H21F H 0.3466 0.0643 1.0079 0.131 Uiso 0.371(7) 1 calc PR A 2
C22B C 0.2755(8) 0.3132(8) 1.0580(5) 0.0539(19) Uiso 0.371(7) 1 d PD A 2
H22D H 0.2608 0.3993 1.0387 0.081 Uiso 0.371(7) 1 calc PR A 2
H22E H 0.3789 0.2679 1.0507 0.081 Uiso 0.371(7) 1 calc PR A 2
H22F H 0.2136 0.3157 1.1327 0.081 Uiso 0.371(7) 1 calc PR A 2
C23 C 0.48537(19) 0.28476(16) 0.22820(14) 0.0310(4) Uani 1 1 d . . .
C24 C 0.6199(2) 0.19724(18) 0.16674(15) 0.0398(4) Uani 1 1 d . . .
H24 H 0.6500 0.1120 0.1827 0.048 Uiso 1 1 calc R . .
C25 C 0.7094(3) 0.2357(2) 0.08201(18) 0.0521(5) Uani 1 1 d . . .
H25 H 0.8021 0.1766 0.0389 0.063 Uiso 1 1 calc R . .
C26 C 0.6654(3) 0.3595(2) 0.05932(18) 0.0537(6) Uani 1 1 d . . .
H26 H 0.7276 0.3850 0.0003 0.064 Uiso 1 1 calc R . .
C27 C 0.5321(3) 0.4465(2) 0.12142(18) 0.0483(5) Uani 1 1 d . . .
H27 H 0.5031 0.5317 0.1055 0.058 Uiso 1 1 calc R . .
C28 C 0.4396(2) 0.41006(18) 0.20740(16) 0.0389(4) Uani 1 1 d . . .
H28 H 0.3473 0.4694 0.2508 0.047 Uiso 1 1 calc R . .
N1 N 0.75497(14) 0.30239(13) 0.58106(12) 0.0285(3) Uani 1 1 d . . .
N2 N 0.45447(15) 0.18523(13) 0.69877(11) 0.0284(3) Uani 1 1 d . . .
N3 N 0.47303(14) 0.20226(13) 0.41808(11) 0.0261(3) Uani 1 1 d . . .
O1 O 0.58248(13) 0.26036(13) 0.77601(10) 0.0384(3) Uani 1 1 d . . .
O2 O 0.27852(15) 0.11172(14) 0.79319(11) 0.0480(4) Uani 1 1 d . . .
O3 O 0.32268(15) 0.25506(13) 0.87341(10) 0.0432(3) Uani 1 1 d . A .
O4 O 0.93325(16) 0.29358(13) 0.65096(14) 0.0521(4) Uani 1 1 d . . .
O5 O 0.87536(12) 0.12328(10) 0.63857(9) 0.0278(3) Uani 1 1 d . . .
O6 O 0.23645(13) 0.33852(14) 0.38262(11) 0.0461(4) Uani 1 1 d . . .
O7 O 0.37164(15) 0.11794(13) 0.30520(11) 0.0445(3) Uani 1 1 d . . .
S1 S 0.37262(5) 0.23522(4) 0.33664(4) 0.03166(13) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 N1 108.81(14)
C6 C1 C2 131.76(14)
N1 C1 C2 117.30(14)
O1 C2 N2 123.82(16)
O1 C2 C1 120.15(15)
N2 C2 C1 116.01(14)
N2 C3 C4 110.13(13)
C5 C4 N3 60.93(10)
C5 C4 C3 118.12(14)
N3 C4 C3 113.75(13)
C4 C5 C6 120.77(14)
C4 C5 N3 60.01(10)
C6 C5 N3 115.78(12)
C1 C6 C7 107.77(14)
C1 C6 C5 126.53(15)
C7 C6 C5 125.50(15)
C8 C7 C12 119.34(15)
C8 C7 C6 133.45(15)
C12 C7 C6 107.21(15)
C9 C8 C7 118.46(17)
C8 C9 C10 121.17(18)
C11 C10 C9 121.74(16)
C10 C11 C12 117.04(16)
C11 C12 N1 130.01(15)
C11 C12 C7 122.25(16)
N1 C12 C7 107.73(14)
O4 C13 O5 129.06(16)
O4 C13 N1 121.63(16)
O5 C13 N1 109.15(13)
O5 C14 C16 109.50(14)
O5 C14 C17 108.77(15)
C16 C14 C17 113.45(16)
O5 C14 C15 101.54(13)
C16 C14 C15 111.91(17)
C17 C14 C15 110.95(16)
O2 C18 O3 126.11(16)
O2 C18 N2 121.68(16)
O3 C18 N2 112.13(14)
O3 C19 C20A 116.6(2)
O3 C19 C22B 106.5(3)
C20A C19 C22B 123.7(3)
O3 C19 C21B 114.8(4)
C20A C19 C21B 79.9(4)
C22B C19 C21B 113.5(5)
O3 C19 C21A 105.0(2)
C20A C19 C21A 112.8(3)
C22B C19 C21A 87.3(4)
C21B C19 C21A 34.1(4)
O3 C19 C20B 100.1(3)
C20A C19 C20B 25.9(3)
C22B C19 C20B 116.4(4)
C21B C19 C20B 105.2(5)
C21A C19 C20B 138.7(4)
O3 C19 C22A 101.48(19)
C20A C19 C22A 109.7(2)
C22B C19 C22A 23.4(3)
C21B C19 C22A 133.4(4)
C21A C19 C22A 110.6(3)
C20B C19 C22A 95.7(3)
C24 C23 C28 121.70(18)
C24 C23 S1 118.55(14)
C28 C23 S1 119.74(14)
C25 C24 C23 118.85(19)
C24 C25 C26 120.4(2)
C27 C26 C25 120.5(2)
C26 C27 C28 120.23(19)
C23 C28 C27 118.31(19)
C12 N1 C1 108.48(13)
C12 N1 C13 121.59(13)
C1 N1 C13 125.58(14)
C2 N2 C18 124.35(14)
C2 N2 C3 119.37(14)
C18 N2 C3 116.13(13)
C4 N3 C5 59.06(10)
C4 N3 S1 115.73(10)
C5 N3 S1 115.34(10)
C18 O3 C19 121.33(13)
C13 O5 C14 121.16(13)
O7 S1 O6 119.37(9)
O7 S1 N3 105.69(8)
O6 S1 N3 111.55(8)
O7 S1 C23 109.97(8)
O6 S1 C23 108.46(9)
N3 S1 C23 100.07(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.370(2)
C1 N1 1.403(2)
C1 C2 1.481(2)
C2 O1 1.210(2)
C2 N2 1.401(2)
C3 N2 1.471(2)
C3 C4 1.503(2)
C4 C5 1.473(2)
C4 N3 1.488(2)
C5 C6 1.477(2)
C5 N3 1.501(2)
C6 C7 1.435(2)
C7 C8 1.399(3)
C7 C12 1.406(2)
C8 C9 1.376(2)
C9 C10 1.399(3)
C10 C11 1.375(3)
C11 C12 1.392(2)
C12 N1 1.393(2)
C13 O4 1.195(2)
C13 O5 1.316(2)
C13 N1 1.425(2)
C14 O5 1.488(2)
C14 C16 1.510(3)
C14 C17 1.511(3)
C14 C15 1.512(3)
C18 O2 1.195(2)
C18 O3 1.315(2)
C18 N2 1.404(2)
C19 O3 1.469(2)
C19 C20A 1.510(2)
C19 C22B 1.512(2)
C19 C21B 1.515(2)
C19 C21A 1.516(2)
C19 C20B 1.519(2)
C19 C22A 1.520(2)
C23 C24 1.382(3)
C23 C28 1.387(3)
C23 S1 1.7537(19)
C24 C25 1.377(3)
C25 C26 1.379(3)
C26 C27 1.375(3)
C27 C28 1.390(3)
N3 S1 1.6708(14)
O6 S1 1.4278(14)
O7 S1 1.4251(14)
