#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104069.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_4104069
loop_
_publ_author_name
'Manfred T. Reetz'
'Hongchao Guo'
'Jun-An Ma'
'Richard Goddard'
'Richard J. Mynott'
_publ_section_title
;
 Helical Triskelion Monophosphites as Ligands in Asymmetric Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4136
_journal_page_last               4142
_journal_paper_doi               10.1021/ja809297a
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_compound_source        dichloromethane/pentane
_chemical_formula_moiety         'C93 H81 O9 P'
_chemical_formula_sum            'C93 H81 O9 P'
_chemical_formula_weight         1373.55
_chemical_name_systematic
; 
 anti-tris[(R)-2'-(1-adamantylcarbonyl)oxy-1,1'-binaphthyl-2-yl]phosphite
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      146
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GUO-GB-273-01
_audit_creation_date             2006-10-19
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                120.0
_cell_formula_units_Z            3
_cell_length_a                   23.9458(3)
_cell_length_b                   23.9458(3)
_cell_length_c                   10.7465(2)
_cell_measurement_reflns_used    6172
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.20
_cell_measurement_theta_min      3.69
_cell_volume                     5336.50(14)
_computing_cell_refinement       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13728
_diffrn_reflns_theta_full        63.20
_diffrn_reflns_theta_max         63.20
_diffrn_reflns_theta_min         3.69
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.78165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             2178
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0302
_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)+(0.0520P)²+3.9511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                3562
_reflns_number_total             3582
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja809297a_si_003.cif
_cod_data_source_block           (R,R,R)-3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 
;
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4104069
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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 1.07127(9) 1.17773(9) 1.01566(16) 0.0172(4) Uani 1 1 d .
C2 C 1.01877(9) 1.11687(8) 1.03309(16) 0.0164(4) Uani 1 1 d .
C3 C 0.95485(9) 1.10352(9) 1.01569(18) 0.0220(4) Uani 1 1 d .
H3 H 0.9204 1.0624 1.0310 0.026 Uiso 1 1 calc R
C4 C 0.94385(9) 1.15147(9) 0.97616(18) 0.0228(4) Uani 1 1 d .
H4 H 0.9017 1.1425 0.9645 0.027 Uiso 1 1 calc R
C5 C 0.99533(9) 1.21418(9) 0.95285(17) 0.0200(4) Uani 1 1 d .
C6 C 0.98446(10) 1.26384(10) 0.90859(17) 0.0235(4) Uani 1 1 d .
H6 H 0.9424 1.2555 0.8990 0.028 Uiso 1 1 calc R
C7 C 1.03456(10) 1.32341(9) 0.87994(17) 0.0260(4) Uani 1 1 d .
H7 H 1.0267 1.3552 0.8498 0.031 Uiso 1 1 calc R
C8 C 1.09821(11) 1.33641(9) 0.89623(18) 0.0264(4) Uani 1 1 d .
H8 H 1.1323 1.3767 0.8744 0.032 Uiso 1 1 calc R
C9 C 1.11074(9) 1.29094(9) 0.94357(17) 0.0221(4) Uani 1 1 d .
H9 H 1.1532 1.3013 0.9574 0.027 Uiso 1 1 calc R
C10 C 1.05977(9) 1.22792(9) 0.97199(16) 0.0186(4) Uani 1 1 d .
C11 C 1.13813(9) 1.19243(8) 1.04627(17) 0.0177(4) Uani 1 1 d .
C12 C 1.15527(9) 1.19255(9) 1.16853(17) 0.0201(4) Uani 1 1 d .
C13 C 1.21807(9) 1.20849(9) 1.20432(19) 0.0239(4) Uani 1 1 d .
H13 H 1.2281 1.2085 1.2879 0.029 Uiso 1 1 calc R
C14 C 1.26423(9) 1.22396(9) 1.11473(19) 0.0245(4) Uani 1 1 d .
H14 H 1.3059 1.2351 1.1382 0.029 Uiso 1 1 calc R
C15 C 1.24951(9) 1.22329(9) 0.98666(18) 0.0215(4) Uani 1 1 d .
C16 C 1.29563(9) 1.23593(9) 0.8926(2) 0.0259(4) Uani 1 1 d .
H16 H 1.3373 1.2464 0.9148 0.031 Uiso 1 1 calc R
C17 C 1.27985(9) 1.23301(9) 0.76908(19) 0.0255(4) Uani 1 1 d .
H17 H 1.3108 1.2419 0.7082 0.031 Uiso 1 1 calc R
C18 C 1.21695(9) 1.21656(9) 0.73500(18) 0.0226(4) Uani 1 1 d .
H18 H 1.2063 1.2143 0.6512 0.027 Uiso 1 1 calc R
C19 C 1.17088(9) 1.20379(8) 0.82368(18) 0.0189(4) Uani 1 1 d .
H19 H 1.1294 1.1931 0.7993 0.023 Uiso 1 1 calc R
C20 C 1.18570(9) 1.20676(8) 0.95191(18) 0.0189(4) Uani 1 1 d .
C21 C 1.11068(10) 1.20158(10) 1.3628(2) 0.0308(5) Uani 1 1 d .
C22 C 1.04811(10) 1.17181(9) 1.43562(19) 0.0249(4) Uani 1 1 d .
C23 C 0.99948(10) 1.10177(10) 1.39665(18) 0.0262(4) Uani 1 1 d .
H23A H 0.9892 1.1005 1.3090 0.031 Uiso 1 1 calc R
H23B H 1.0183 1.0745 1.4097 0.031 Uiso 1 1 calc R
C24 C 1.01683(10) 1.21375(10) 1.4121(2) 0.0282(4) Uani 1 1 d .
H24A H 1.0469 1.2582 1.4343 0.034 Uiso 1 1 calc R
H24B H 1.0064 1.2124 1.3246 0.034 Uiso 1 1 calc R
C25 C 1.06342(10) 1.17356(10) 1.57483(19) 0.0274(5) Uani 1 1 d .
H25A H 1.0831 1.1473 1.5903 0.033 Uiso 1 1 calc R
H25B H 1.0938 1.2175 1.5996 0.033 Uiso 1 1 calc R
C26 C 0.93775(9) 1.07681(9) 1.47467(19) 0.0252(4) Uani 1 1 d .
H26 H 0.9070 1.0323 1.4505 0.030 Uiso 1 1 calc R
C27 C 0.95531(10) 1.18870(10) 1.49010(19) 0.0285(5) Uani 1 1 d .
H27 H 0.9359 1.2157 1.4754 0.034 Uiso 1 1 calc R
C28 C 1.00169(10) 1.14819(10) 1.65148(19) 0.0285(5) Uani 1 1 d .
H28 H 1.0119 1.1494 1.7401 0.034 Uiso 1 1 calc R
C29 C 0.95450(10) 1.07866(10) 1.6126(2) 0.0282(5) Uani 1 1 d .
H29A H 0.9156 1.0617 1.6623 0.034 Uiso 1 1 calc R
H29B H 0.9738 1.0520 1.6269 0.034 Uiso 1 1 calc R
C30 C 0.90764(10) 1.11899(10) 1.4520(2) 0.0284(5) Uani 1 1 d .
H30A H 0.8683 1.1028 1.5002 0.034 Uiso 1 1 calc R
H30B H 0.8968 1.1175 1.3647 0.034 Uiso 1 1 calc R
C31 C 0.97126(10) 1.19038(10) 1.6276(2) 0.0294(5) Uani 1 1 d .
H31A H 0.9322 1.1747 1.6767 0.035 Uiso 1 1 calc R
H31B H 1.0010 1.2344 1.6527 0.035 Uiso 1 1 calc R
O1 O 1.02951(6) 1.06808(6) 1.07616(11) 0.0188(3) Uani 1 1 d .
O2 O 1.10524(6) 1.17102(6) 1.25506(12) 0.0231(3) Uani 1 1 d .
O3 O 1.16033(9) 1.24724(9) 1.39682(19) 0.0676(7) Uani 1 1 d .
P P 1.0000 1.0000 0.99967(7) 0.01701(18) Uani 0.99 3 d SP
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C2 C1 C10 118.18(16) . . y
C2 C1 C11 121.44(16) . . y
C10 C1 C11 120.33(16) . . y
C1 C2 O1 118.51(15) . . y
C1 C2 C3 122.21(16) . . y
O1 C2 C3 119.18(15) . . y
C4 C3 C2 119.56(18) . . y
C3 C4 C5 121.11(18) . . y
C4 C5 C6 121.51(17) . . y
C4 C5 C10 119.38(17) . . y
C6 C5 C10 119.10(17) . . y
C7 C6 C5 121.20(18) . . y
C6 C7 C8 119.54(19) . . y
C9 C8 C7 121.10(19) . . y
C8 C9 C10 120.86(18) . . y
C9 C10 C5 118.10(17) . . y
C9 C10 C1 122.38(17) . . y
C5 C10 C1 119.49(16) . . y
C12 C11 C20 118.34(16) . . y
C12 C11 C1 119.61(16) . . y
C20 C11 C1 122.05(16) . . y
C11 C12 O2 115.80(16) . . y
C11 C12 C13 122.59(18) . . y
O2 C12 C13 121.43(17) . . y
C14 C13 C12 119.30(18) . . y
C13 C14 C15 121.10(17) . . y
C16 C15 C14 121.86(17) . . y
C16 C15 C20 119.15(18) . . y
C14 C15 C20 118.93(17) . . y
C17 C16 C15 120.98(18) . . y
C16 C17 C18 119.80(18) . . y
C19 C18 C17 120.84(19) . . y
C18 C19 C20 120.76(18) . . y
C19 C20 C15 118.47(17) . . y
C19 C20 C11 121.83(16) . . y
C15 C20 C11 119.69(17) . . y
O3 C21 O2 122.8(2) . . y
O3 C21 C22 124.5(2) . . y
O2 C21 C22 112.69(17) . . y
C21 C22 C25 108.88(17) . . y
C21 C22 C24 107.25(17) . . y
C25 C22 C24 109.16(16) . . y
C21 C22 C23 113.68(16) . . y
C25 C22 C23 109.48(16) . . y
C24 C22 C23 108.30(16) . . y
C26 C23 C22 109.29(16) . . y
C27 C24 C22 109.88(17) . . y
C28 C25 C22 110.12(16) . . y
C30 C26 C29 109.82(17) . . y
C30 C26 C23 109.67(16) . . y
C29 C26 C23 109.27(16) . . y
C31 C27 C24 109.94(17) . . y
C31 C27 C30 109.17(17) . . y
C24 C27 C30 109.08(17) . . y
C25 C28 C29 109.07(16) . . y
C25 C28 C31 109.38(17) . . y
C29 C28 C31 109.60(16) . . y
C28 C29 C26 109.62(17) . . y
C26 C30 C27 109.70(17) . . y
C27 C31 C28 109.89(17) . . y
C2 O1 P 119.92(11) . . y
C21 O2 C12 122.86(16) . . y
O1 P O1 97.00(6) 3_675 . y
O1 P O1 97.00(6) 3_675 2_765 y
O1 P O1 97.00(6) . 2_765 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 C2 1.381(3) . y
C1 C10 1.439(3) . y
C1 C11 1.494(3) . y
C2 O1 1.395(2) . y
C2 C3 1.411(3) . y
C3 C4 1.368(3) . y
C4 C5 1.409(3) . y
C5 C6 1.420(3) . y
C5 C10 1.422(3) . y
C6 C7 1.363(3) . y
C7 C8 1.406(3) . y
C8 C9 1.364(3) . y
C9 C10 1.421(3) . y
C11 C12 1.376(3) . y
C11 C20 1.433(3) . y
C12 O2 1.396(2) . y
C12 C13 1.408(3) . y
C13 C14 1.370(3) . y
C14 C15 1.419(3) . y
C15 C16 1.414(3) . y
C15 C20 1.423(3) . y
C16 C17 1.373(3) . y
C17 C18 1.402(3) . y
C18 C19 1.372(3) . y
C19 C20 1.416(3) . y
C21 O3 1.201(3) . y
C21 O2 1.341(2) . y
C21 C22 1.516(3) . y
C22 C25 1.536(3) . y
C22 C24 1.545(3) . y
C22 C23 1.546(3) . y
C23 C26 1.537(3) . y
C24 C27 1.532(3) . y
C25 C28 1.528(3) . y
C26 C30 1.526(3) . y
C26 C29 1.531(3) . y
C27 C31 1.522(3) . y
C27 C30 1.533(3) . y
C28 C29 1.530(3) . y
C28 C31 1.534(3) . y
O1 P 1.6372(13) . y
P O1 1.6371(13) 3_675 y
P O1 1.6372(13) 2_765 y
