#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:38:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178957 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/86/4118614.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_4118614
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_compound_source        dichloromethane,hexane
_chemical_formula_moiety         'C27 H23 Br O2 '
_chemical_formula_sum            'C27 H23 Br O2'
_chemical_formula_weight         459.36
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_block_code                TLL-TL-053-01
_audit_creation_date             2012-04-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                105.241(3)
_cell_angle_beta                 101.586(3)
_cell_angle_gamma                98.300(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0137(13)
_cell_length_b                   11.1334(16)
_cell_length_c                   11.4146(16)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.5040
_cell_measurement_theta_min      4.9406
_cell_volume                     1058.9(3)
_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_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2011)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2011)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45630
_diffrn_reflns_theta_full        66.94
_diffrn_reflns_theta_max         66.94
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             1.6
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.805
_exptl_absorpt_correction_T_max  0.66985
_exptl_absorpt_correction_T_min  0.41176
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0260
_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)+(0.0299P)²+0.8519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                3646
_reflns_number_total             3651
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303641p_si_006.cif
_cod_data_source_block           7336neu
_cod_database_code               4118614
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
Br1 Br 0.70896(2) 0.294810(18) -0.195312(18) 0.02658(8) Uani 1 1 d .
O1 O 0.09748(13) 0.35463(11) 0.35945(10) 0.0164(2) Uani 1 1 d .
O2 O 0.17477(13) 0.05539(10) 0.32001(11) 0.0163(2) Uani 1 1 d .
C1 C 0.24117(18) 0.19017(15) 0.37048(15) 0.0143(3) Uani 1 1 d .
C2 C 0.16440(18) 0.26761(15) 0.29057(15) 0.0141(3) Uani 1 1 d .
C3 C 0.0535(2) 0.45145(17) 0.30488(16) 0.0209(4) Uani 1 1 d .
H3A H 0.1452 0.5144 0.3147 0.025 Uiso 1 1 calc R
H3B H -0.0150 0.4941 0.3487 0.025 Uiso 1 1 calc R
C4 C -0.0272(2) 0.39438(18) 0.16723(17) 0.0223(4) Uani 1 1 d .
H4A H -0.0600 0.4601 0.1331 0.027 Uiso 1 1 calc R
H4B H -0.1182 0.3304 0.1566 0.027 Uiso 1 1 calc R
C5 C 0.0847(2) 0.33403(16) 0.09831(16) 0.0197(3) Uani 1 1 d .
H5A H 0.0280 0.2791 0.0155 0.024 Uiso 1 1 calc R
H5B H 0.1596 0.4001 0.0884 0.024 Uiso 1 1 calc R
C6 C 0.16858(18) 0.25691(15) 0.17097(15) 0.0157(3) Uani 1 1 d .
C7 C 0.24218(18) 0.15926(16) 0.10282(15) 0.0163(3) Uani 1 1 d .
C8 C 0.2133(2) 0.04061(16) 0.11149(16) 0.0186(3) Uani 1 1 d .
H8 H 0.2601 -0.0207 0.0696 0.022 Uiso 1 1 calc R
C9 C 0.1069(2) 0.00608(16) 0.18773(16) 0.0193(3) Uani 1 1 d .
H9A H 0.0137 0.0384 0.1678 0.023 Uiso 1 1 calc R
H9B H 0.0772 -0.0859 0.1648 0.023 Uiso 1 1 calc R
C10 C 0.34891(19) 0.19426(16) 0.02762(16) 0.0172(3) Uani 1 1 d .
C11 C 0.4440(2) 0.31589(16) 0.06465(16) 0.0184(3) Uani 1 1 d .
H11 H 0.4347 0.3777 0.1341 0.022 Uiso 1 1 calc R
C12 C 0.5514(2) 0.34601(16) -0.00009(17) 0.0201(3) Uani 1 1 d .
H12 H 0.6143 0.4269 0.0259 0.024 Uiso 1 1 calc R
C13 C 0.5638(2) 0.25428(17) -0.10364(17) 0.0201(3) Uani 1 1 d .
C14 C 0.4700(2) 0.13356(17) -0.14480(17) 0.0235(4) Uani 1 1 d .
H14 H 0.4783 0.0729 -0.2155 0.028 Uiso 1 1 calc R
C15 C 0.3636(2) 0.10508(16) -0.07876(17) 0.0210(4) Uani 1 1 d .
H15 H 0.3002 0.0243 -0.1060 0.025 Uiso 1 1 calc R
C16 C 0.41683(18) 0.21348(15) 0.38284(15) 0.0149(3) Uani 1 1 d .
C17 C 0.49943(19) 0.32950(16) 0.38372(16) 0.0180(3) Uani 1 1 d .
H17 H 0.4470 0.3929 0.3710 0.022 Uiso 1 1 calc R
C18 C 0.6598(2) 0.35177(17) 0.40344(17) 0.0221(4) Uani 1 1 d .
H18 H 0.7136 0.4296 0.4034 0.027 Uiso 1 1 calc R
C19 C 0.7396(2) 0.25835(18) 0.42320(17) 0.0233(4) Uani 1 1 d .
H19 H 0.8465 0.2724 0.4348 0.028 Uiso 1 1 calc R
C20 C 0.6579(2) 0.14339(17) 0.42547(17) 0.0216(4) Uani 1 1 d .
H20 H 0.7108 0.0809 0.4403 0.026 Uiso 1 1 calc R
C21 C 0.49776(19) 0.12109(16) 0.40570(15) 0.0176(3) Uani 1 1 d .
H21 H 0.4443 0.0440 0.4077 0.021 Uiso 1 1 calc R
C22 C 0.21163(18) 0.22617(15) 0.50221(15) 0.0150(3) Uani 1 1 d .
C23 C 0.3150(2) 0.31989(16) 0.60314(16) 0.0195(3) Uani 1 1 d .
H23 H 0.4054 0.3620 0.5919 0.023 Uiso 1 1 calc R
C24 C 0.2839(2) 0.35084(17) 0.72035(17) 0.0230(4) Uani 1 1 d .
H24 H 0.3534 0.4141 0.7868 0.028 Uiso 1 1 calc R
C25 C 0.1501(2) 0.28849(17) 0.73950(17) 0.0224(4) Uani 1 1 d .
H25 H 0.1299 0.3094 0.8183 0.027 Uiso 1 1 calc R
C26 C 0.0470(2) 0.19465(17) 0.63960(17) 0.0213(4) Uani 1 1 d .
H26 H -0.0431 0.1524 0.6512 0.026 Uiso 1 1 calc R
C27 C 0.07808(19) 0.16367(16) 0.52214(16) 0.0181(3) Uani 1 1 d .
H27 H 0.0086 0.1002 0.4559 0.022 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 0.0181 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 0.00 0.0900
-1.00 0.00 0.00 0.0900
0.00 -1.00 1.00 0.1700
0.00 1.00 -1.00 0.1100
0.00 1.00 1.00 0.1300
0.00 -2.00 -3.00 0.2800
-3.00 -1.00 -3.00 0.1300
1.00 -3.00 2.00 0.1780
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
C2 O1 C3 115.94(12) y
C9 O2 C1 117.27(12) y
O2 C1 C2 112.33(13) y
O2 C1 C16 109.93(12) y
O2 C1 C22 103.72(12) y
C16 C1 C2 110.49(13) y
C16 C1 C22 109.12(13) y
C22 C1 C2 111.03(13) y
O1 C2 C1 111.04(13) y
C6 C2 O1 123.75(14) y
C6 C2 C1 125.13(14) y
O1 C3 H3A 109.4 y
O1 C3 H3B 109.4 y
O1 C3 C4 111.06(14) y
H3A C3 H3B 108.0 y
C4 C3 H3A 109.4 y
C4 C3 H3B 109.4 y
C3 C4 H4A 109.9 y
C3 C4 H4B 109.9 y
C3 C4 C5 108.87(14) y
H4A C4 H4B 108.3 y
C5 C4 H4A 109.9 y
C5 C4 H4B 109.9 y
C4 C5 H5A 109.6 y
C4 C5 H5B 109.6 y
H5A C5 H5B 108.1 y
C6 C5 C4 110.36(14) y
C6 C5 H5A 109.6 y
C6 C5 H5B 109.6 y
C2 C6 C5 121.36(15) y
C2 C6 C7 120.27(14) y
C7 C6 C5 118.07(14) y
C6 C7 C10 119.77(14) y
C8 C7 C6 119.39(15) y
C8 C7 C10 120.84(15) y
C7 C8 H8 119.7 y
C7 C8 C9 120.68(15) y
C9 C8 H8 119.7 y
O2 C9 C8 113.05(13) y
O2 C9 H9A 109.0 y
O2 C9 H9B 109.0 y
C8 C9 H9A 109.0 y
C8 C9 H9B 109.0 y
H9A C9 H9B 107.8 y
C11 C10 C7 121.22(15) y
C15 C10 C7 121.07(15) y
C15 C10 C11 117.63(16) y
C10 C11 H11 119.3 y
C12 C11 C10 121.37(16) y
C12 C11 H11 119.3 y
C11 C12 H12 120.5 y
C13 C12 C11 119.07(16) y
C13 C12 H12 120.5 y
C12 C13 Br1 119.64(13) y
C12 C13 C14 121.37(16) y
C14 C13 Br1 118.97(13) y
C13 C14 H14 120.6 y
C15 C14 C13 118.75(17) y
C15 C14 H14 120.6 y
C10 C15 H15 119.1 y
C14 C15 C10 121.79(16) y
C14 C15 H15 119.1 y
C17 C16 C1 121.54(14) y
C17 C16 C21 118.85(15) y
C21 C16 C1 119.32(14) y
C16 C17 H17 119.6 y
C16 C17 C18 120.71(15) y
C18 C17 H17 119.6 y
C17 C18 H18 119.9 y
C19 C18 C17 120.25(16) y
C19 C18 H18 119.9 y
C18 C19 H19 120.4 y
C18 C19 C20 119.24(16) y
C20 C19 H19 120.4 y
C19 C20 H20 119.7 y
C21 C20 C19 120.51(16) y
C21 C20 H20 119.7 y
C16 C21 H21 119.8 y
C20 C21 C16 120.41(16) y
C20 C21 H21 119.8 y
C23 C22 C1 121.99(14) y
C27 C22 C1 119.47(14) y
C27 C22 C23 118.54(15) y
C22 C23 H23 119.8 y
C24 C23 C22 120.45(16) y
C24 C23 H23 119.8 y
C23 C24 H24 119.6 y
C23 C24 C25 120.73(17) y
C25 C24 H24 119.6 y
C24 C25 H25 120.4 y
C26 C25 C24 119.17(16) y
C26 C25 H25 120.4 y
C25 C26 H26 119.9 y
C25 C26 C27 120.11(16) y
C27 C26 H26 119.9 y
C22 C27 H27 119.5 y
C26 C27 C22 121.00(16) y
C26 C27 H27 119.5 y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 1.9071(17) y
O1 C2 1.3708(19) y
O1 C3 1.444(2) y
O2 C1 1.4455(19) y
O2 C9 1.432(2) y
C1 C2 1.545(2) y
C1 C16 1.538(2) y
C1 C22 1.539(2) y
C2 C6 1.348(2) y
C3 H3A 0.9700 y
C3 H3B 0.9700 y
C3 C4 1.511(3) y
C4 H4A 0.9700 y
C4 H4B 0.9700 y
C4 C5 1.525(2) y
C5 H5A 0.9700 y
C5 H5B 0.9700 y
C5 C6 1.519(2) y
C6 C7 1.482(2) y
C7 C8 1.342(2) y
C7 C10 1.488(2) y
C8 H8 0.9300 y
C8 C9 1.493(2) y
C9 H9A 0.9700 y
C9 H9B 0.9700 y
C10 C11 1.402(2) y
C10 C15 1.395(3) y
C11 H11 0.9300 y
C11 C12 1.386(2) y
C12 H12 0.9300 y
C12 C13 1.380(3) y
C13 C14 1.387(3) y
C14 H14 0.9300 y
C14 C15 1.384(3) y
C15 H15 0.9300 y
C16 C17 1.391(2) y
C16 C21 1.393(2) y
C17 H17 0.9300 y
C17 C18 1.392(2) y
C18 H18 0.9300 y
C18 C19 1.387(3) y
C19 H19 0.9300 y
C19 C20 1.391(3) y
C20 H20 0.9300 y
C20 C21 1.390(2) y
C21 H21 0.9300 y
C22 C23 1.393(2) y
C22 C27 1.392(2) y
C23 H23 0.9300 y
C23 C24 1.387(3) y
C24 H24 0.9300 y
C24 C25 1.388(3) y
C25 H25 0.9300 y
C25 C26 1.387(3) y
C26 H26 0.9300 y
C26 C27 1.389(3) y
C27 H27 0.9300 y
