#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:10:25 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179955 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/50/7025076.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_7025076
loop_
_publ_author_name
'Edwards, Peter G.'
'Knight, James C.'
'Newman, Paul D.'
_publ_section_title
;
 Synthesis of (1R,4S,6R)-5,5,6-trimethyl-2-phosphabicyclo[2.2.2]octane and
 derivatives.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3851
_journal_page_last               3860
_journal_paper_doi               10.1039/b924983d
_journal_volume                  39
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C12 H24 P, I'
_chemical_formula_sum            'C12 H24 I P'
_chemical_formula_weight         326.18
_chemical_name_common            pge0506
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1710(2)
_cell_length_b                   10.4460(3)
_cell_length_c                   18.5870(5)
_cell_measurement_reflns_used    6068
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_volume                     1392.32(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 (A. Altomare et al., 1992)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7691
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_T_max  0.5551
_exptl_absorpt_correction_T_min  0.4136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+1.1036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                2955
_reflns_number_total             3068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b924983d.txt
_cod_data_source_block           compound9
_cod_database_code               7025076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
C9 C 0.7758(7) 1.0552(4) 0.2703(2) 0.0223(9) Uani 1 1 d .
H1A H 0.6658 1.0535 0.3016 0.033 Uiso 1 1 calc R
H1B H 0.7718 1.1318 0.2399 0.033 Uiso 1 1 calc R
H1C H 0.8889 1.0571 0.2999 0.033 Uiso 1 1 calc R
C2 C 0.7749(8) 0.7779(4) 0.2722(2) 0.0235(9) Uani 1 1 d .
H2A H 0.8836 0.7800 0.3041 0.035 Uiso 1 1 calc R
H2B H 0.7787 0.7000 0.2428 0.035 Uiso 1 1 calc R
H2C H 0.6606 0.7783 0.3011 0.035 Uiso 1 1 calc R
C3 C 0.9743(6) 0.9149(5) 0.15296(18) 0.0216(8) Uani 1 1 d .
H3A H 1.0369 0.9993 0.1535 0.026 Uiso 1 1 calc R
H3B H 1.0660 0.8490 0.1676 0.026 Uiso 1 1 calc R
C4 C 0.8995(6) 0.8851(4) 0.0762(2) 0.0186(8) Uani 1 1 d .
H4 H 1.0088 0.8715 0.0437 0.022 Uiso 1 1 calc R
C8 C 0.7863(7) 0.7604(4) 0.0787(2) 0.0227(9) Uani 1 1 d .
H5A H 0.8542 0.6960 0.1078 0.027 Uiso 1 1 calc R
H5B H 0.7721 0.7261 0.0294 0.027 Uiso 1 1 calc R
C7 C 0.5907(7) 0.7839(4) 0.1121(2) 0.0208(9) Uani 1 1 d .
H6A H 0.4954 0.7836 0.0735 0.025 Uiso 1 1 calc R
H6B H 0.5608 0.7140 0.1461 0.025 Uiso 1 1 calc R
C1 C 0.5851(5) 0.9123(4) 0.15170(18) 0.0161(7) Uani 1 1 d .
H7 H 0.4639 0.9223 0.1777 0.019 Uiso 1 1 calc R
C5 C 0.7801(7) 0.9965(4) 0.0450(2) 0.0210(8) Uani 1 1 d .
C6 C 0.6154(6) 1.0263(4) 0.0988(2) 0.0181(8) Uani 1 1 d .
H9 H 0.6544 1.1017 0.1284 0.022 Uiso 1 1 calc R
C10 C 0.4299(7) 1.0611(5) 0.0629(2) 0.0287(10) Uani 1 1 d .
H10A H 0.3774 0.9850 0.0396 0.043 Uiso 1 1 calc R
H10B H 0.4510 1.1279 0.0268 0.043 Uiso 1 1 calc R
H10C H 0.3426 1.0927 0.0994 0.043 Uiso 1 1 calc R
C11 C 0.7136(7) 0.9570(4) -0.0305(2) 0.0274(10) Uani 1 1 d .
H11A H 0.8219 0.9385 -0.0609 0.041 Uiso 1 1 calc R
H11B H 0.6411 1.0269 -0.0518 0.041 Uiso 1 1 calc R
H11C H 0.6354 0.8803 -0.0268 0.041 Uiso 1 1 calc R
C12 C 0.8956(8) 1.1187(4) 0.0351(3) 0.0311(11) Uani 1 1 d .
H12A H 0.9986 1.1018 0.0017 0.047 Uiso 1 1 calc R
H12B H 0.9459 1.1458 0.0817 0.047 Uiso 1 1 calc R
H12C H 0.8161 1.1866 0.0155 0.047 Uiso 1 1 calc R
P1 P 0.77785(13) 0.91534(9) 0.21484(4) 0.01518(19) Uani 1 1 d .
I1 I 0.72753(4) 1.41530(2) 0.169366(13) 0.02099(9) 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 0.0033 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
P1 C9 H1A 109.5
P1 C9 H1B 109.5
H1A C9 H1B 109.5
P1 C9 H1C 109.5
H1A C9 H1C 109.5
H1B C9 H1C 109.5
P1 C2 H2A 109.5
P1 C2 H2B 109.5
H2A C2 H2B 109.5
P1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C4 C3 P1 108.3(3)
C4 C3 H3A 110.0
P1 C3 H3A 110.0
C4 C3 H3B 110.0
P1 C3 H3B 110.0
H3A C3 H3B 108.4
C8 C4 C3 108.8(3)
C8 C4 C5 110.8(4)
C3 C4 C5 112.5(3)
C8 C4 H4 108.2
C3 C4 H4 108.2
C5 C4 H4 108.2
C4 C8 C7 110.8(3)
C4 C8 H5A 109.5
C7 C8 H5A 109.5
C4 C8 H5B 109.5
C7 C8 H5B 109.5
H5A C8 H5B 108.1
C1 C7 C8 110.8(3)
C1 C7 H6A 109.5
C8 C7 H6A 109.5
C1 C7 H6B 109.5
C8 C7 H6B 109.5
H6A C7 H6B 108.1
C7 C1 C6 111.2(3)
C7 C1 P1 107.9(3)
C6 C1 P1 106.7(3)
C7 C1 H7 110.3
C6 C1 H7 110.3
P1 C1 H7 110.3
C12 C5 C11 106.3(3)
C12 C5 C4 111.7(4)
C11 C5 C4 108.1(3)
C12 C5 C6 108.4(3)
C11 C5 C6 113.5(4)
C4 C5 C6 108.8(3)
C10 C6 C1 109.5(4)
C10 C6 C5 114.9(3)
C1 C6 C5 110.7(3)
C10 C6 H9 107.1
C1 C6 H9 107.1
C5 C6 H9 107.1
C6 C10 H10A 109.5
C6 C10 H10B 109.5
H10A C10 H10B 109.5
C6 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C5 C11 H11A 109.5
C5 C11 H11B 109.5
H11A C11 H11B 109.5
C5 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C5 C12 H12A 109.5
C5 C12 H12B 109.5
H12A C12 H12B 109.5
C5 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C2 P1 C9 108.19(18)
C2 P1 C1 111.3(2)
C9 P1 C1 112.4(2)
C2 P1 C3 112.6(2)
C9 P1 C3 111.9(2)
C1 P1 C3 100.43(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 P1 1.789(4)
C9 H1A 0.9800
C9 H1B 0.9800
C9 H1C 0.9800
C2 P1 1.789(4)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C4 1.556(5)
C3 P1 1.819(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C8 1.536(6)
C4 C5 1.556(6)
C4 H4 1.0000
C8 C7 1.553(6)
C8 H5A 0.9900
C8 H5B 0.9900
C7 C1 1.530(6)
C7 H6A 0.9900
C7 H6B 0.9900
C1 C6 1.559(5)
C1 P1 1.814(4)
C1 H7 1.0000
C5 C12 1.533(6)
C5 C11 1.538(5)
C5 C6 1.579(6)
C6 C10 1.532(6)
C6 H9 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
P1 C3 C4 C8 -54.0(4)
P1 C3 C4 C5 69.1(4)
C3 C4 C8 C7 76.9(4)
C5 C4 C8 C7 -47.3(4)
C4 C8 C7 C1 -15.9(5)
C8 C7 C1 C6 63.8(4)
C8 C7 C1 P1 -53.0(4)
C8 C4 C5 C12 -174.5(3)
C3 C4 C5 C12 63.5(4)
C8 C4 C5 C11 -57.8(4)
C3 C4 C5 C11 -179.9(4)
C8 C4 C5 C6 65.8(4)
C3 C4 C5 C6 -56.2(5)
C7 C1 C6 C10 83.5(4)
P1 C1 C6 C10 -159.1(3)
C7 C1 C6 C5 -44.2(4)
P1 C1 C6 C5 73.2(4)
C12 C5 C6 C10 95.7(5)
C11 C5 C6 C10 -22.2(5)
C4 C5 C6 C10 -142.6(4)
C12 C5 C6 C1 -139.6(4)
C11 C5 C6 C1 102.5(4)
C4 C5 C6 C1 -17.9(5)
C7 C1 P1 C2 -53.5(3)
C6 C1 P1 C2 -173.1(3)
C7 C1 P1 C9 -175.0(3)
C6 C1 P1 C9 65.4(3)
C7 C1 P1 C3 65.9(3)
C6 C1 P1 C3 -53.7(3)
C4 C3 P1 C2 107.4(3)
C4 C3 P1 C9 -130.5(3)
C4 C3 P1 C1 -11.0(3)
