#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/86/4118616.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_4118616
loop_
_publ_author_name
'Henrik Teller'
'Matthieu Corbet'
'Luca Mantilli'
'Gopinadhanpillai Gopakumar'
'Richard Goddard'
'Walter Thiel'
'Alois Fürstner'
_publ_section_title
;
 One-Point Binding Ligands for Asymmetric Gold Catalysis: Phosphoramidites
 with a TADDOL-Related but Acyclic Backbone
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15331
_journal_page_last               15342
_journal_paper_doi               10.1021/ja303641p
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        pentane/dichloromethane/acetonitrile
_chemical_formula_moiety         '4(C21 H21 N3 O7), C H2 Cl2, C2 H3 N'
_chemical_formula_sum            'C87 H89 Cl2 N13 O28'
_chemical_formula_weight         1835.61
_chemical_name_systematic
;
(3,5-dinitro)-(3-(2,2-dimethylvinyl)-4,6-dimethoxy-2,3-dihydroindolyl)methanone
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                COB-CB-069-01
_audit_creation_date             2012-04-13
_cell_angle_alpha                90.00
_cell_angle_beta                 122.791(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   24.4670(11)
_cell_length_b                   7.0733(3)
_cell_length_c                   15.2093(7)
_cell_measurement_reflns_used    9084
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.8578
_cell_measurement_theta_min      3.4568
_cell_volume                     2212.73(18)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30030
_diffrn_reflns_theta_full        66.47
_diffrn_reflns_theta_max         66.47
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3332
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0614
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1175P)²+2.8766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1712
_reflns_number_gt                3234
_reflns_number_total             3332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303641p_si_008.cif
_cod_data_source_block           7290
_cod_original_cell_volume        2212.73(17)
_cod_original_sg_symbol_Hall     'c 2y'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4118616
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'
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 0.73521(14) 0.6128(5) 1.0227(2) 0.0203(7) Uani 1 1 d . . .
C2 C 0.79298(14) 0.6037(5) 1.1341(2) 0.0191(7) Uani 1 1 d . . .
C3 C 0.78054(16) 0.6639(5) 1.2093(2) 0.0204(7) Uani 1 1 d . . .
H3 H 0.7390 0.7124 1.1886 0.024 Uiso 1 1 calc R . .
C4 C 0.82922(17) 0.6520(5) 1.3136(3) 0.0228(7) Uani 1 1 d . . .
C5 C 0.89062(16) 0.5833(6) 1.3484(2) 0.0250(8) Uani 1 1 d . . .
H5 H 0.9240 0.5796 1.4206 0.030 Uiso 1 1 calc R . .
C6 C 0.90062(16) 0.5208(5) 1.2727(3) 0.0227(7) Uani 1 1 d . . .
C7 C 0.85330(15) 0.5244(5) 1.1668(3) 0.0213(7) Uani 1 1 d . . .
H7 H 0.8617 0.4739 1.1174 0.026 Uiso 1 1 calc R . .
C8 C 0.80711(15) 0.6345(6) 0.9477(2) 0.0235(7) Uani 1 1 d . . .
H8A H 0.8312 0.5137 0.9646 0.028 Uiso 1 1 calc R . .
H8B H 0.8348 0.7284 1.0023 0.028 Uiso 1 1 calc R . .
C9 C 0.78825(15) 0.7059(6) 0.8390(2) 0.0213(7) Uani 1 1 d . . .
H9 H 0.7940 0.8460 0.8404 0.026 Uiso 1 1 calc R . .
C10 C 0.71663(15) 0.6559(5) 0.7736(2) 0.0198(7) Uani 1 1 d . . .
C11 C 0.67376(15) 0.6620(5) 0.6649(2) 0.0210(7) Uani 1 1 d . . .
C12 C 0.61005(15) 0.6010(6) 0.6199(2) 0.0222(7) Uani 1 1 d . . .
H12 H 0.5809 0.6007 0.5461 0.027 Uiso 1 1 calc R . .
C13 C 0.58937(15) 0.5400(5) 0.6849(3) 0.0211(7) Uani 1 1 d . . .
C14 C 0.62925(16) 0.5416(5) 0.7931(2) 0.0206(7) Uani 1 1 d . . .
H14 H 0.6141 0.5052 0.8364 0.025 Uiso 1 1 calc R . .
C15 C 0.69332(14) 0.6004(5) 0.8345(2) 0.0198(7) Uani 1 1 d . . .
C16 C 0.82826(15) 0.6092(6) 0.8042(2) 0.0261(8) Uani 1 1 d . . .
H16 H 0.8344 0.4770 0.8166 0.031 Uiso 1 1 calc R . .
C17 C 0.85588(17) 0.6865(7) 0.7583(3) 0.0332(9) Uani 1 1 d . . .
C18 C 0.8528(3) 0.8916(9) 0.7323(5) 0.0557(14) Uani 1 1 d . . .
H18A H 0.8278 0.9075 0.6561 0.083 Uiso 1 1 calc R . .
H18B H 0.8970 0.9402 0.7620 0.083 Uiso 1 1 calc R . .
H18C H 0.8317 0.9617 0.7616 0.083 Uiso 1 1 calc R . .
C19 C 0.8918(2) 0.5661(8) 0.7244(4) 0.0481(12) Uani 1 1 d . . .
H19A H 0.8917 0.4343 0.7442 0.072 Uiso 1 1 calc R . .
H19B H 0.9368 0.6107 0.7586 0.072 Uiso 1 1 calc R . .
H19C H 0.8705 0.5746 0.6484 0.072 Uiso 1 1 calc R . .
C20 C 0.66127(18) 0.7135(7) 0.4987(2) 0.0317(9) Uani 1 1 d . . .
H20A H 0.6492 0.5804 0.4807 0.048 Uiso 1 1 calc R . .
H20B H 0.6874 0.7545 0.4712 0.048 Uiso 1 1 calc R . .
H20C H 0.6218 0.7909 0.4680 0.048 Uiso 1 1 calc R . .
C21 C 0.49959(16) 0.4255(6) 0.6925(3) 0.0260(8) Uani 1 1 d . . .
H21A H 0.5267 0.3258 0.7418 0.039 Uiso 1 1 calc R . .
H21B H 0.4552 0.3782 0.6459 0.039 Uiso 1 1 calc R . .
H21C H 0.4990 0.5351 0.7314 0.039 Uiso 1 1 calc R . .
N1 N 0.74502(12) 0.6074(5) 0.94176(19) 0.0194(6) Uani 1 1 d . . .
N2 N 0.81499(14) 0.7115(5) 1.3923(2) 0.0263(7) Uani 1 1 d . . .
N3 N 0.96470(13) 0.4434(5) 1.3054(2) 0.0264(7) Uani 1 1 d . . .
O1 O 0.68071(11) 0.6244(5) 1.00709(17) 0.0285(6) Uani 1 1 d . . .
O2 O 0.69867(11) 0.7350(4) 0.61129(16) 0.0256(6) Uani 1 1 d . . .
O3 O 0.52568(11) 0.4800(4) 0.63186(17) 0.0264(6) Uani 1 1 d . . .
O4 O 0.75933(13) 0.7606(4) 1.36141(19) 0.0334(6) Uani 1 1 d . . .
O5 O 0.85989(13) 0.7093(5) 1.48394(17) 0.0360(7) Uani 1 1 d . . .
O6 O 1.00658(12) 0.4392(5) 1.4000(2) 0.0397(7) Uani 1 1 d . . .
O7 O 0.97326(11) 0.3869(4) 1.2381(2) 0.0315(6) Uani 1 1 d . . .
Cl1 Cl 0.95127(13) 0.9579(6) 1.0268(2) 0.0712(9) Uani 0.50 1 d P A 1
C22 C 1.0000 0.843(3) 1.0000 0.070(4) Uani 0.50 2 d SPU . 1
H22A H 0.9720 0.7594 0.9396 0.084 Uiso 0.25 1 calc PR . 1
H22B H 1.0280 0.7594 1.0604 0.084 Uiso 0.25 1 calc PR . 1
N4 N 0.9584(8) 0.788(3) 1.0670(13) 0.060(4) Uani 0.25 1 d PDU B -2
C23 C 0.9746(12) 0.650(3) 1.0418(19) 0.077(7) Uani 0.25 1 d PDU B -2
C24 C 0.9831(15) 0.458(4) 1.013(2) 0.090(8) Uani 0.25 1 d PDU B -2
H24A H 1.0052 0.3722 1.0760 0.135 Uiso 0.25 1 d P C -2
H24B H 1.0091 0.4563 0.9819 0.135 Uiso 0.25 1 d P D -2
H24C H 0.9403 0.3977 0.9627 0.135 Uiso 0.25 1 d P E -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0190
0.00 1.00 0.00 0.0190
0.00 1.00 2.00 0.1260
0.00 -1.00 -2.00 0.1600
-2.00 -1.00 -1.00 0.4000
2.00 1.00 1.00 0.4000
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_3
_geom_angle_publ_flag
O1 C1 N1 121.9(3) . y
O1 C1 C2 118.7(3) . y
N1 C1 C2 119.5(3) . y
C7 C2 C3 119.2(3) . y
C7 C2 C1 125.8(3) . y
C3 C2 C1 114.7(3) . y
C4 C3 C2 119.2(3) . y
C3 C4 C5 123.0(3) . y
C3 C4 N2 118.7(3) . y
C5 C4 N2 118.3(3) . y
C6 C5 C4 116.3(3) . y
C5 C6 C7 123.6(3) . y
C5 C6 N3 118.6(3) . y
C7 C6 N3 117.8(3) . y
C6 C7 C2 118.6(3) . y
N1 C8 C9 105.9(2) . y
C16 C9 C10 113.8(3) . y
C16 C9 C8 110.8(3) . y
C10 C9 C8 101.3(3) . y
C15 C10 C11 118.9(3) . y
C15 C10 C9 112.1(3) . y
C11 C10 C9 129.0(3) . y
O2 C11 C12 124.9(3) . y
O2 C11 C10 115.4(3) . y
C12 C11 C10 119.7(3) . y
C11 C12 C13 119.1(3) . y
O3 C13 C14 123.0(3) . y
O3 C13 C12 114.1(3) . y
C14 C13 C12 123.0(3) . y
C13 C14 C15 115.7(3) . y
C10 C15 C14 123.4(3) . y
C10 C15 N1 109.0(3) . y
C14 C15 N1 127.6(3) . y
C17 C16 C9 127.8(4) . y
C16 C17 C18 125.0(4) . y
C16 C17 C19 120.5(4) . y
C18 C17 C19 114.5(4) . y
C1 N1 C15 123.2(3) . y
C1 N1 C8 127.6(2) . y
C15 N1 C8 108.6(2) . y
O5 N2 O4 124.5(3) . y
O5 N2 C4 117.4(3) . y
O4 N2 C4 118.1(3) . y
O7 N3 O6 124.0(3) . y
O7 N3 C6 118.4(3) . y
O6 N3 C6 117.5(3) . y
C11 O2 C20 118.0(3) . y
C13 O3 C21 117.6(2) . y
Cl1 C22 Cl1 121.6(14) 2_757 y
N4 C23 C24 167(3) . y
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
C1 O1 1.224(4) . y
C1 N1 1.376(4) . y
C1 C2 1.510(4) . y
C2 C7 1.394(5) . y
C2 C3 1.400(4) . y
C3 C4 1.378(5) . y
C4 C5 1.383(5) . y
C4 N2 1.476(4) . y
C5 C6 1.373(5) . y
C6 C7 1.385(4) . y
C6 N3 1.471(4) . y
C8 N1 1.484(4) . y
C8 C9 1.541(4) . y
C9 C16 1.506(5) . y
C9 C10 1.516(4) . y
C10 C15 1.382(5) . y
C10 C11 1.399(4) . y
C11 O2 1.357(4) . y
C11 C12 1.389(5) . y
C12 C13 1.400(5) . y
C13 O3 1.377(4) . y
C13 C14 1.386(4) . y
C14 C15 1.399(4) . y
C15 N1 1.424(4) . y
C16 C17 1.324(5) . y
C17 C18 1.495(8) . y
C17 C19 1.502(6) . y
C20 O2 1.447(4) . y
C21 O3 1.430(4) . y
N2 O5 1.222(4) . y
N2 O4 1.226(4) . y
N3 O7 1.218(4) . y
N3 O6 1.234(4) . y
Cl1 C22 1.666(11) . y
C22 Cl1 1.666(11) 2_757 y
N4 C23 1.193(18) . y
C23 C24 1.472(19) . y
