#------------------------------------------------------------------------------
#$Date: 2019-10-10 12:36:40 +0300 (Thu, 10 Oct 2019) $
#$Revision: 219247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/38/4023869.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_4023869
loop_
_publ_author_name
'Ellis, J. Michael'
'Overman, Larry E.'
'Tanner, Huw R.'
'Wang, Jocelyn'
_publ_section_title
;
 A Versatile Synthesis of Unsymmetrical 3,3'-Bioxindoles: Stereoselective
 Mukaiyama Aldol Reactions of 2-Siloxyindoles with Isatins
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   22
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              9151
_journal_page_last               9154
_journal_paper_doi               10.1021/jo801867w
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.45
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                111.929(2)
_cell_angle_beta                 108.080(2)
_cell_angle_gamma                93.745(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1562(12)
_cell_length_b                   10.6764(14)
_cell_length_c                   12.1295(16)
_cell_measurement_temperature    155(2)
_cell_volume                     1023.3(2)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      155(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10666
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0369
_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)+(0.0479P)²+0.3914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                3903
_reflns_number_total             4498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801867w_si_001.cif
_cod_data_source_block           leo212
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-10
;
_cod_database_code               4023869
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
O1 O 0.23848(11) 0.54735(9) 0.05841(8) 0.0283(2) Uani 1 1 d . . .
O2 O -0.01291(11) 0.59347(9) 0.17300(9) 0.0257(2) Uani 1 1 d . . .
O3 O 0.31564(10) 0.88355(9) 0.13911(8) 0.0232(2) Uani 1 1 d . . .
O4 O -0.08546(10) 1.20442(9) 0.16629(9) 0.0254(2) Uani 1 1 d . . .
N1 N 0.37792(12) 0.69212(10) 0.26781(10) 0.0209(2) Uani 1 1 d . . .
N2 N 0.12294(11) 1.00965(10) 0.15468(9) 0.0194(2) Uani 1 1 d . . .
C1 C 0.24671(14) 0.63466(12) 0.16156(12) 0.0221(3) Uani 1 1 d . . .
C2 C 0.10758(13) 0.69669(12) 0.19175(11) 0.0198(2) Uani 1 1 d . . .
C3 C 0.18464(14) 0.78854(12) 0.33213(11) 0.0195(2) Uani 1 1 d . . .
C4 C 0.12112(15) 0.86327(13) 0.41904(12) 0.0232(3) Uani 1 1 d . . .
C5 C 0.21907(16) 0.93314(13) 0.54704(12) 0.0250(3) Uani 1 1 d . . .
C6 C 0.37767(15) 0.92915(13) 0.58493(12) 0.0235(3) Uani 1 1 d . . .
C7 C 0.44298(14) 0.85406(12) 0.49741(12) 0.0215(2) Uani 1 1 d . . .
C8 C 0.34372(14) 0.78307(12) 0.37195(11) 0.0192(2) Uani 1 1 d . . .
C9 C 0.18119(13) 0.89186(12) 0.13386(11) 0.0190(2) Uani 1 1 d . . .
C10 C 0.05096(13) 0.77414(12) 0.10563(11) 0.0186(2) Uani 1 1 d . . .
C11 C -0.08354(13) 0.84557(12) 0.11778(11) 0.0185(2) Uani 1 1 d . . .
C12 C -0.23750(14) 0.79318(13) 0.09684(11) 0.0214(2) Uani 1 1 d . . .
C13 C -0.34191(14) 0.88251(14) 0.10215(12) 0.0233(3) Uani 1 1 d . . .
C14 C -0.29524(14) 1.01934(13) 0.12571(11) 0.0227(3) Uani 1 1 d . . .
C15 C -0.14116(14) 1.07271(12) 0.14622(11) 0.0201(2) Uani 1 1 d . . .
C16 C -0.03596(13) 0.98329(12) 0.14307(10) 0.0184(2) Uani 1 1 d . . .
C17 C 0.22211(15) 1.14216(13) 0.19221(13) 0.0238(3) Uani 1 1 d . . .
C18 C -0.19027(17) 1.29911(14) 0.17802(14) 0.0288(3) Uani 1 1 d . . .
C19 C 0.53487(14) 0.67489(13) 0.26835(12) 0.0226(3) Uani 1 1 d . . .
C20 C 0.61220(14) 0.60235(12) 0.34956(11) 0.0211(2) Uani 1 1 d . . .
C21 C 0.53321(18) 0.47849(15) 0.33457(16) 0.0357(3) Uani 1 1 d . . .
C22 C 0.6039(2) 0.4111(2) 0.4081(2) 0.0498(4) Uani 1 1 d . . .
C23 C 0.7534(2) 0.46562(19) 0.49631(16) 0.0440(4) Uani 1 1 d . . .
C24 C 0.8335(2) 0.58773(19) 0.51210(15) 0.0426(4) Uani 1 1 d . . .
C25 C 0.76296(17) 0.65736(16) 0.43877(14) 0.0335(3) Uani 1 1 d . . .
H2 H -0.071(2) 0.5481(18) 0.0900(19) 0.040(5) Uiso 1 1 d . . .
H4A H 0.0087(19) 0.8627(15) 0.3901(14) 0.027(4) Uiso 1 1 d . . .
H5A H 0.1757(18) 0.9843(16) 0.6093(15) 0.029(4) Uiso 1 1 d . . .
H6A H 0.4452(18) 0.9815(16) 0.6729(15) 0.028(4) Uiso 1 1 d . . .
H7A H 0.5524(19) 0.8501(15) 0.5240(14) 0.025(4) Uiso 1 1 d . . .
H10A H 0.0244(17) 0.7072(15) 0.0167(14) 0.023(4) Uiso 1 1 d . . .
H12A H -0.2701(17) 0.6968(15) 0.0773(13) 0.021(3) Uiso 1 1 d . . .
H13A H -0.448(2) 0.8490(16) 0.0887(15) 0.031(4) Uiso 1 1 d . . .
H14A H -0.3696(18) 1.0790(15) 0.1259(14) 0.027(4) Uiso 1 1 d . . .
H17A H 0.322(2) 1.1250(18) 0.1930(17) 0.043(5) Uiso 1 1 d . . .
H17B H 0.233(2) 1.2058(18) 0.2762(18) 0.041(5) Uiso 1 1 d . . .
H17C H 0.178(2) 1.1819(17) 0.1327(17) 0.036(4) Uiso 1 1 d . . .
H18A H -0.2796(19) 1.2691(16) 0.0974(16) 0.031(4) Uiso 1 1 d . . .
H18B H -0.1261(19) 1.3887(17) 0.1996(15) 0.031(4) Uiso 1 1 d . . .
H18C H -0.2304(19) 1.3028(17) 0.2465(16) 0.035(4) Uiso 1 1 d . . .
H19A H 0.6023(18) 0.7678(16) 0.3001(14) 0.026(4) Uiso 1 1 d . . .
H19B H 0.5191(17) 0.6197(15) 0.1768(15) 0.025(4) Uiso 1 1 d . . .
H21A H 0.423(2) 0.440(2) 0.2692(19) 0.051(5) Uiso 1 1 d . . .
H22A H 0.544(3) 0.323(2) 0.402(2) 0.071(7) Uiso 1 1 d . . .
H23A H 0.799(2) 0.415(2) 0.544(2) 0.061(6) Uiso 1 1 d . . .
H24A H 0.933(3) 0.629(2) 0.569(2) 0.055(6) Uiso 1 1 d . . .
H25A H 0.816(2) 0.7427(19) 0.4506(18) 0.043(5) Uiso 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'
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
C15 O4 C18 117.39(10) . . ?
C1 N1 C8 110.81(10) . . ?
C1 N1 C19 123.45(10) . . ?
C8 N1 C19 125.28(10) . . ?
C9 N2 C16 110.58(10) . . ?
C9 N2 C17 121.53(10) . . ?
C16 N2 C17 127.75(10) . . ?
O1 C1 N1 125.65(11) . . ?
O1 C1 C2 125.41(11) . . ?
N1 C1 C2 108.94(10) . . ?
O2 C2 C3 109.47(10) . . ?
O2 C2 C10 112.42(9) . . ?
C3 C2 C10 114.72(10) . . ?
O2 C2 C1 111.19(10) . . ?
C3 C2 C1 101.39(9) . . ?
C10 C2 C1 107.07(9) . . ?
C4 C3 C8 120.34(11) . . ?
C4 C3 C2 130.52(11) . . ?
C8 C3 C2 109.01(10) . . ?
C3 C4 C5 118.60(12) . . ?
C6 C5 C4 120.47(12) . . ?
C5 C6 C7 121.26(12) . . ?
C8 C7 C6 117.45(11) . . ?
C7 C8 C3 121.84(11) . . ?
C7 C8 N1 128.37(11) . . ?
C3 C8 N1 109.72(10) . . ?
O3 C9 N2 125.23(11) . . ?
O3 C9 C10 126.35(11) . . ?
N2 C9 C10 108.41(10) . . ?
C11 C10 C9 102.71(9) . . ?
C11 C10 C2 117.61(10) . . ?
C9 C10 C2 111.40(9) . . ?
C12 C11 C16 120.76(11) . . ?
C12 C11 C10 130.75(11) . . ?
C16 C11 C10 108.18(10) . . ?
C11 C12 C13 117.95(11) . . ?
C14 C13 C12 121.38(11) . . ?
C13 C14 C15 121.09(11) . . ?
O4 C15 C14 125.35(11) . . ?
O4 C15 C16 117.29(11) . . ?
C14 C15 C16 117.35(11) . . ?
C11 C16 C15 121.46(11) . . ?
C11 C16 N2 110.03(10) . . ?
C15 C16 N2 128.38(11) . . ?
N1 C19 C20 113.44(10) . . ?
C25 C20 C21 119.03(12) . . ?
C25 C20 C19 120.76(12) . . ?
C21 C20 C19 120.21(12) . . ?
C22 C21 C20 120.44(15) . . ?
C23 C22 C21 120.48(16) . . ?
C24 C23 C22 119.88(14) . . ?
C23 C24 C25 120.20(15) . . ?
C20 C25 C24 119.96(15) . . ?
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
O1 C1 1.2252(15) . ?
O2 C2 1.4077(14) . ?
O3 C9 1.2236(14) . ?
O4 C15 1.3676(15) . ?
O4 C18 1.4378(15) . ?
N1 C1 1.3538(16) . ?
N1 C8 1.4162(15) . ?
N1 C19 1.4590(16) . ?
N2 C9 1.3652(15) . ?
N2 C16 1.4161(15) . ?
N2 C17 1.4588(15) . ?
C1 C2 1.5537(17) . ?
C2 C3 1.5085(16) . ?
C2 C10 1.5520(16) . ?
C3 C4 1.3781(18) . ?
C3 C8 1.3978(16) . ?
C4 C5 1.3980(18) . ?
C5 C6 1.3894(19) . ?
C6 C7 1.3957(18) . ?
C7 C8 1.3807(17) . ?
C9 C10 1.5323(16) . ?
C10 C11 1.5071(16) . ?
C11 C12 1.3904(16) . ?
C11 C16 1.3937(17) . ?
C12 C13 1.3925(17) . ?
C13 C14 1.3890(19) . ?
C14 C15 1.3958(17) . ?
C15 C16 1.3988(16) . ?
C19 C20 1.5100(16) . ?
C20 C25 1.3833(19) . ?
C20 C21 1.3851(19) . ?
C21 C22 1.383(2) . ?
C22 C23 1.371(3) . ?
C23 C24 1.370(3) . ?
C24 C25 1.400(2) . ?
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 O1 -176.48(12) . . . . ?
C19 N1 C1 O1 10.85(19) . . . . ?
C8 N1 C1 C2 3.15(13) . . . . ?
C19 N1 C1 C2 -169.52(10) . . . . ?
O1 C1 C2 O2 59.97(16) . . . . ?
N1 C1 C2 O2 -119.66(11) . . . . ?
O1 C1 C2 C3 176.26(12) . . . . ?
N1 C1 C2 C3 -3.37(12) . . . . ?
O1 C1 C2 C10 -63.19(15) . . . . ?
N1 C1 C2 C10 117.17(10) . . . . ?
O2 C2 C3 C4 -55.88(16) . . . . ?
C10 C2 C3 C4 71.58(16) . . . . ?
C1 C2 C3 C4 -173.42(12) . . . . ?
O2 C2 C3 C8 119.97(10) . . . . ?
C10 C2 C3 C8 -112.57(11) . . . . ?
C1 C2 C3 C8 2.43(12) . . . . ?
C8 C3 C4 C5 0.09(18) . . . . ?
C2 C3 C4 C5 175.55(11) . . . . ?
C3 C4 C5 C6 1.23(18) . . . . ?
C4 C5 C6 C7 -1.05(19) . . . . ?
C5 C6 C7 C8 -0.47(18) . . . . ?
C6 C7 C8 C3 1.82(17) . . . . ?
C6 C7 C8 N1 -174.85(11) . . . . ?
C4 C3 C8 C7 -1.66(18) . . . . ?
C2 C3 C8 C7 -178.01(10) . . . . ?
C4 C3 C8 N1 175.57(10) . . . . ?
C2 C3 C8 N1 -0.78(13) . . . . ?
C1 N1 C8 C7 175.44(11) . . . . ?
C19 N1 C8 C7 -12.05(19) . . . . ?
C1 N1 C8 C3 -1.56(13) . . . . ?
C19 N1 C8 C3 170.95(10) . . . . ?
C16 N2 C9 O3 -179.06(11) . . . . ?
C17 N2 C9 O3 -2.98(18) . . . . ?
C16 N2 C9 C10 -0.09(12) . . . . ?
C17 N2 C9 C10 175.98(10) . . . . ?
O3 C9 C10 C11 177.42(11) . . . . ?
N2 C9 C10 C11 -1.53(12) . . . . ?
O3 C9 C10 C2 50.64(15) . . . . ?
N2 C9 C10 C2 -128.30(10) . . . . ?
O2 C2 C10 C11 58.23(14) . . . . ?
C3 C2 C10 C11 -67.72(13) . . . . ?
C1 C2 C10 C11 -179.37(10) . . . . ?
O2 C2 C10 C9 176.37(9) . . . . ?
C3 C2 C10 C9 50.43(13) . . . . ?
C1 C2 C10 C9 -61.23(12) . . . . ?
C9 C10 C11 C12 176.18(12) . . . . ?
C2 C10 C11 C12 -61.13(16) . . . . ?
C9 C10 C11 C16 2.62(12) . . . . ?
C2 C10 C11 C16 125.31(11) . . . . ?
C16 C11 C12 C13 -0.10(17) . . . . ?
C10 C11 C12 C13 -172.98(11) . . . . ?
C11 C12 C13 C14 0.93(18) . . . . ?
C12 C13 C14 C15 -0.64(19) . . . . ?
C18 O4 C15 C14 5.60(17) . . . . ?
C18 O4 C15 C16 -175.97(10) . . . . ?
C13 C14 C15 O4 177.93(11) . . . . ?
C13 C14 C15 C16 -0.50(17) . . . . ?
C12 C11 C16 C15 -1.06(17) . . . . ?
C10 C11 C16 C15 173.27(10) . . . . ?
C12 C11 C16 N2 -177.17(10) . . . . ?
C10 C11 C16 N2 -2.84(12) . . . . ?
O4 C15 C16 C11 -177.22(10) . . . . ?
C14 C15 C16 C11 1.34(17) . . . . ?
O4 C15 C16 N2 -1.88(17) . . . . ?
C14 C15 C16 N2 176.68(11) . . . . ?
C9 N2 C16 C11 1.88(13) . . . . ?
C17 N2 C16 C11 -173.89(11) . . . . ?
C9 N2 C16 C15 -173.89(11) . . . . ?
C17 N2 C16 C15 10.34(19) . . . . ?
C1 N1 C19 C20 -117.63(13) . . . . ?
C8 N1 C19 C20 70.77(15) . . . . ?
N1 C19 C20 C25 -129.92(13) . . . . ?
N1 C19 C20 C21 50.78(16) . . . . ?
C25 C20 C21 C22 0.2(2) . . . . ?
C19 C20 C21 C22 179.53(15) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C21 C20 C25 C24 0.1(2) . . . . ?
C19 C20 C25 C24 -179.18(13) . . . . ?
C23 C24 C25 C20 -0.4(2) . . . . ?
