#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/86/4118613.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_4118613
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        dichloromethane/heptane
_chemical_formula_moiety         'C27 H23 Br O2'
_chemical_formula_sum            'C27 H23 Br O2'
_chemical_formula_weight         459.36
_chemical_name_systematic
;
 23p
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                TLL-TB-274-01
_audit_creation_date             2012-04-13
_cell_angle_alpha                90.00
_cell_angle_beta                 101.470(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2326(2)
_cell_length_b                   9.9596(3)
_cell_length_c                   12.9633(4)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.0969
_cell_measurement_theta_min      3.4789
_cell_volume                     1041.68(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29097
_diffrn_reflns_theta_full        66.73
_diffrn_reflns_theta_max         66.73
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    2.851
_exptl_absorpt_correction_T_max  0.90912
_exptl_absorpt_correction_T_min  0.53854
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.030(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.0379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0701
_reflns_number_gt                3267
_reflns_number_total             3391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303641p_si_005.cif
_cod_data_source_block           7061
_cod_original_sg_symbol_Hall     'Pp 2yb'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4118613
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C 0.0695(3) 0.9752(3) 0.3884(2) 0.0154(5) Uani 1 1 d .
C2 C 0.2020(3) 0.9884(3) 0.3224(2) 0.0137(5) Uani 1 1 d .
C3 C 0.1008(3) 1.1095(3) 0.3362(2) 0.0141(5) Uani 1 1 d .
H3 H 0.0147 1.1319 0.2726 0.017 Uiso 1 1 calc R
C4 C 0.1832(3) 1.2315(3) 0.3936(2) 0.0183(5) Uani 1 1 d .
H4A H 0.1147 1.2640 0.4432 0.022 Uiso 1 1 calc R
H4B H 0.1876 1.3038 0.3419 0.022 Uiso 1 1 calc R
C5 C 0.3604(3) 1.2037(3) 0.4554(2) 0.0191(5) Uani 1 1 d .
H5A H 0.4218 1.2893 0.4703 0.023 Uiso 1 1 calc R
H5B H 0.3557 1.1599 0.5233 0.023 Uiso 1 1 calc R
C6 C 0.4477(3) 1.1133(3) 0.3902(2) 0.0187(5) Uani 1 1 d .
H6A H 0.4454 1.1550 0.3206 0.022 Uiso 1 1 calc R
H6B H 0.5650 1.1023 0.4257 0.022 Uiso 1 1 calc R
C7 C -0.0809(3) 0.9021(3) 0.33251(19) 0.0153(5) Uani 1 1 d .
H7 H -0.1590 0.8695 0.3714 0.018 Uiso 1 1 calc R
C8 C -0.1069(2) 0.8821(4) 0.22980(17) 0.0171(4) Uani 1 1 d .
H8 H -0.2043 0.8352 0.1977 0.021 Uiso 1 1 calc R
C9 C 0.1751(3) 0.9194(3) 0.2146(2) 0.0137(5) Uani 1 1 d .
C10 C 0.1094(3) 0.9598(3) 0.5053(2) 0.0135(5) Uani 1 1 d .
C11 C 0.0368(3) 1.0439(3) 0.5694(2) 0.0169(5) Uani 1 1 d .
H11 H -0.0308 1.1163 0.5383 0.020 Uiso 1 1 calc R
C12 C 0.0611(3) 1.0243(3) 0.6774(2) 0.0177(5) Uani 1 1 d .
H12 H 0.0110 1.0824 0.7201 0.021 Uiso 1 1 calc R
C13 C 0.1598(3) 0.9183(3) 0.7215(2) 0.0159(6) Uani 1 1 d .
C14 C 0.2364(3) 0.8343(3) 0.6614(2) 0.0168(5) Uani 1 1 d .
H14 H 0.3056 0.7633 0.6932 0.020 Uiso 1 1 calc R
C15 C 0.2106(3) 0.8556(2) 0.5532(2) 0.0151(6) Uani 1 1 d .
H15 H 0.2628 0.7981 0.5112 0.018 Uiso 1 1 calc R
C16 C 0.2628(3) 1.0038(3) 0.1443(2) 0.0149(5) Uani 1 1 d .
C17 C 0.4291(3) 0.9775(3) 0.1401(2) 0.0194(6) Uani 1 1 d .
H17 H 0.4838 0.9019 0.1759 0.023 Uiso 1 1 calc R
C18 C 0.5132(3) 1.0617(3) 0.0838(2) 0.0234(6) Uani 1 1 d .
H18 H 0.6258 1.0436 0.0818 0.028 Uiso 1 1 calc R
C19 C 0.4356(4) 1.1717(3) 0.0305(2) 0.0231(6) Uani 1 1 d .
H19 H 0.4939 1.2285 -0.0084 0.028 Uiso 1 1 calc R
C20 C 0.2717(3) 1.1980(3) 0.0345(2) 0.0207(6) Uani 1 1 d .
H20 H 0.2172 1.2732 -0.0022 0.025 Uiso 1 1 calc R
C21 C 0.1861(3) 1.1150(3) 0.0921(2) 0.0176(6) Uani 1 1 d .
H21 H 0.0744 1.1350 0.0955 0.021 Uiso 1 1 calc R
C22 C 0.2265(3) 0.7714(3) 0.2151(2) 0.0141(5) Uani 1 1 d .
C23 C 0.1697(3) 0.6975(3) 0.1242(2) 0.0173(6) Uani 1 1 d .
H23 H 0.0986 0.7392 0.0664 0.021 Uiso 1 1 calc R
C24 C 0.2146(3) 0.5638(3) 0.1160(2) 0.0207(6) Uani 1 1 d .
H24 H 0.1724 0.5145 0.0537 0.025 Uiso 1 1 calc R
C25 C 0.3208(4) 0.5029(3) 0.1989(2) 0.0242(6) Uani 1 1 d .
H25 H 0.3536 0.4122 0.1933 0.029 Uiso 1 1 calc R
C26 C 0.3787(3) 0.5751(3) 0.2897(2) 0.0240(6) Uani 1 1 d .
H26 H 0.4507 0.5331 0.3470 0.029 Uiso 1 1 calc R
C27 C 0.3330(3) 0.7083(3) 0.2984(2) 0.0195(6) Uani 1 1 d .
H27 H 0.3745 0.7567 0.3613 0.023 Uiso 1 1 calc R
Br1 Br 0.18879(3) 0.88639(3) 0.868674(17) 0.02347(9) Uani 1 1 d .
O1 O 0.3693(2) 0.98434(18) 0.37605(14) 0.0151(4) Uani 1 1 d .
O2 O -0.0010(2) 0.92518(17) 0.16622(14) 0.0161(4) 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 0.0181 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'
Br Br -0.6763 1.2805 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 1.00 0.0250
-1.00 0.00 -1.00 0.0250
0.00 -1.00 0.00 0.2100
0.00 1.00 0.00 0.2000
0.00 0.00 -1.00 0.0200
0.00 0.00 1.00 0.0200
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C10 C1 C7 115.9(2) y
C10 C1 C2 122.8(2) y
C7 C1 C2 112.8(2) y
C10 C1 C3 120.7(2) y
C7 C1 C3 113.9(2) y
C2 C1 C3 58.51(16) y
O1 C2 C3 118.3(2) y
O1 C2 C1 117.3(2) y
C3 C2 C1 61.55(16) y
O1 C2 C9 112.66(19) y
C3 C2 C9 119.2(2) y
C1 C2 C9 119.0(2) y
C2 C3 C4 120.0(2) y
C2 C3 C1 59.95(16) y
C4 C3 C1 125.3(2) y
C3 C4 C5 113.4(2) y
C6 C5 C4 108.8(2) y
O1 C6 C5 110.7(2) y
C8 C7 C1 121.0(2) y
C7 C8 O2 124.0(2) y
O2 C9 C16 105.61(19) y
O2 C9 C22 106.82(19) y
C16 C9 C22 111.7(2) y
O2 C9 C2 108.93(19) y
C16 C9 C2 107.4(2) y
C22 C9 C2 115.9(2) y
C11 C10 C15 118.0(2) y
C11 C10 C1 120.6(2) y
C15 C10 C1 121.3(2) y
C12 C11 C10 121.6(2) y
C13 C12 C11 118.6(2) y
C14 C13 C12 121.7(2) y
C14 C13 Br1 119.03(19) y
C12 C13 Br1 119.24(19) y
C13 C14 C15 118.8(2) y
C14 C15 C10 121.3(2) y
C21 C16 C17 118.9(3) y
C21 C16 C9 120.6(2) y
C17 C16 C9 120.1(2) y
C18 C17 C16 120.1(3) y
C19 C18 C17 120.9(3) y
C18 C19 C20 119.2(3) y
C19 C20 C21 120.4(3) y
C16 C21 C20 120.4(3) y
C23 C22 C27 118.1(3) y
C23 C22 C9 117.4(2) y
C27 C22 C9 124.5(2) y
C22 C23 C24 121.5(3) y
C25 C24 C23 119.8(3) y
C26 C25 C24 119.4(3) y
C25 C26 C27 120.9(3) y
C26 C27 C22 120.3(3) y
C2 O1 C6 114.04(19) y
C8 O2 C9 114.92(18) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C10 1.493(4) y
C1 C7 1.493(4) y
C1 C2 1.520(3) y
C1 C3 1.544(4) y
C2 O1 1.414(3) y
C2 C3 1.497(4) y
C2 C9 1.534(4) y
C3 C4 1.513(4) y
C4 C5 1.543(4) y
C5 C6 1.512(4) y
C6 O1 1.432(3) y
C7 C8 1.321(3) y
C8 O2 1.382(3) y
C9 O2 1.461(3) y
C9 C16 1.523(4) y
C9 C22 1.533(4) y
C10 C11 1.395(4) y
C10 C15 1.397(3) y
C11 C12 1.389(4) y
C12 C13 1.384(4) y
C13 C14 1.379(4) y
C13 Br1 1.902(2) y
C14 C15 1.392(4) y
C16 C21 1.383(4) y
C16 C17 1.405(4) y
C17 C18 1.383(4) y
C18 C19 1.382(4) y
C19 C20 1.385(4) y
C20 C21 1.395(4) y
C22 C23 1.389(4) y
C22 C27 1.398(4) y
C23 C24 1.392(4) y
C24 C25 1.383(4) y
C25 C26 1.381(4) y
C26 C27 1.390(4) y
