#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:11:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179779 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/75/7007577.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_7007577
loop_
_publ_author_name
'Doherty, Ruth'
'Haddow, Mairi F.'
'Harrison, Zoë A'
'Orpen, A. Guy'
'Pringle, Paul G.'
'Turner, Alex'
'Wingad, Richard L.'
_publ_section_title
;
 Bulky 4-phosphacyclohexanones: diastereoselective complexations,
 orthometallations and unprecedented [3.1.1]metallabicycles.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4310
_journal_page_last               4320
_journal_paper_doi               10.1039/b607490a
_journal_year                    2006
_chemical_formula_moiety         'C23 H27 O2 P'
_chemical_formula_sum            'C23 H27 O2 P'
_chemical_formula_weight         366.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2849(13)
_cell_length_b                   22.074(4)
_cell_length_c                   14.046(3)
_cell_measurement_reflns_used    1102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.017
_cell_measurement_theta_min      4.006
_cell_volume                     1900.8(7)
_computing_cell_refinement       'Bruker SMART V5.625 (Bruker AXS, 2001)'
_computing_data_collection       'Bruker SMART V5.625 (Bruker AXS, 2001)'
_computing_data_reduction        'Bruker SAINT V7.06 (Bruker AXS, 2003)'
_computing_molecular_graphics    'Bruker SHELXTL V6.14 (Bruker AXS, 2003)'
_computing_publication_material  'Bruker SHELXTL V6.14 (Bruker AXS, 2003)'
_computing_structure_refinement  'SHELXL V6.12 (Bruker 2001)'
_computing_structure_solution    'SHELXS V6.12 (Bruker 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.849
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1763
_diffrn_reflns_av_sigmaI/netI    0.1547
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10169
_diffrn_reflns_theta_full        70.01
_diffrn_reflns_theta_max         70.01
_diffrn_reflns_theta_min         3.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.383
_exptl_absorpt_correction_T_max  0.990000
_exptl_absorpt_correction_T_min  0.525841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0828
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1356P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2561
_reflns_number_gt                1974
_reflns_number_total             3068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607490a.txt
_cod_data_source_block           rac-CyLb(O)_zahlhsad
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               7007577
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.1330(3) 0.34511(5) 0.27363(8) 0.0192(4) Uani 1 1 d . . .
O1 O -0.1086(7) 0.34969(15) 0.2477(3) 0.0283(10) Uani 1 1 d . . .
O2 O 0.5374(7) 0.17706(15) 0.2858(3) 0.0296(10) Uani 1 1 d . . .
C1 C 0.2359(10) 0.29298(19) 0.3758(3) 0.0205(12) Uani 1 1 d . . .
H1 H 0.3884 0.3057 0.4062 0.025 Uiso 1 1 calc R . .
C2 C 0.2474(10) 0.22761(19) 0.3376(3) 0.0242(13) Uani 1 1 d . . .
H2A H 0.2800 0.1993 0.3936 0.029 Uiso 1 1 calc R . .
H2B H 0.1038 0.2164 0.2965 0.029 Uiso 1 1 calc R . .
C3 C 0.4178(11) 0.2214(2) 0.2793(3) 0.0267(13) Uani 1 1 d . . .
C4 C 0.4476(10) 0.2727(2) 0.2108(4) 0.0278(14) Uani 1 1 d . . .
H4A H 0.4946 0.2555 0.1537 0.033 Uiso 1 1 calc R . .
H4B H 0.5644 0.3001 0.2451 0.033 Uiso 1 1 calc R . .
C5 C 0.2368(10) 0.30939(19) 0.1754(3) 0.0216(13) Uani 1 1 d . . .
H5 H 0.1235 0.2790 0.1456 0.026 Uiso 1 1 calc R . .
C6 C 0.1023(9) 0.30032(19) 0.4526(3) 0.0201(12) Uani 1 1 d . . .
C7 C 0.1643(11) 0.3415(2) 0.5280(4) 0.0286(14) Uani 1 1 d . . .
H7 H 0.2955 0.3637 0.5322 0.034 Uiso 1 1 calc R . .
C8 C 0.0434(11) 0.3515(2) 0.5974(4) 0.0292(14) Uani 1 1 d . . .
H8 H 0.0915 0.3797 0.6487 0.035 Uiso 1 1 calc R . .
C9 C -0.1510(10) 0.3195(2) 0.5910(3) 0.0264(13) Uani 1 1 d . . .
H9 H -0.2403 0.3272 0.6361 0.032 Uiso 1 1 calc R . .
C10 C -0.2125(10) 0.2765(2) 0.5186(3) 0.0266(13) Uani 1 1 d . . .
H10 H -0.3390 0.2527 0.5172 0.032 Uiso 1 1 calc R . .
C11 C -0.0913(10) 0.2677(2) 0.4477(3) 0.0225(12) Uani 1 1 d . . .
H11 H -0.1398 0.2397 0.3962 0.027 Uiso 1 1 calc R . .
C12 C 0.2465(10) 0.35447(19) 0.0937(3) 0.0198(12) Uani 1 1 d . . .
C13 C 0.4396(10) 0.3762(2) 0.0748(3) 0.0251(13) Uani 1 1 d . . .
H13 H 0.5747 0.3624 0.1133 0.030 Uiso 1 1 calc R . .
C14 C 0.4390(11) 0.4181(2) -0.0001(4) 0.0284(14) Uani 1 1 d . . .
H14 H 0.5728 0.4326 -0.0122 0.034 Uiso 1 1 calc R . .
C15 C 0.2429(11) 0.4382(2) -0.0564(4) 0.0315(15) Uani 1 1 d . . .
H15 H 0.2420 0.4667 -0.1070 0.038 Uiso 1 1 calc R . .
C16 C 0.0457(12) 0.4166(2) -0.0389(4) 0.0315(15) Uani 1 1 d . . .
H16 H -0.0894 0.4305 -0.0773 0.038 Uiso 1 1 calc R . .
C17 C 0.0497(10) 0.3744(2) 0.0357(3) 0.0227(12) Uani 1 1 d . . .
H17 H -0.0838 0.3591 0.0470 0.027 Uiso 1 1 calc R . .
C18 C 0.2644(10) 0.41697(19) 0.3128(3) 0.0204(12) Uani 1 1 d . . .
H18 H 0.2341 0.4247 0.3787 0.025 Uiso 1 1 calc R . .
C19 C 0.5155(10) 0.4183(2) 0.3284(4) 0.0270(14) Uani 1 1 d . . .
H19A H 0.5793 0.3859 0.3745 0.032 Uiso 1 1 calc R . .
H19B H 0.5571 0.4105 0.2655 0.032 Uiso 1 1 calc R . .
C20 C 0.6079(12) 0.4800(2) 0.3688(4) 0.0361(16) Uani 1 1 d . . .
H20A H 0.5881 0.4847 0.4364 0.043 Uiso 1 1 calc R . .
H20B H 0.7662 0.4813 0.3707 0.043 Uiso 1 1 calc R . .
C21 C 0.4945(12) 0.5324(2) 0.3061(4) 0.0388(18) Uani 1 1 d . . .
H21A H 0.5499 0.5712 0.3371 0.047 Uiso 1 1 calc R . .
H21B H 0.5311 0.5307 0.2412 0.047 Uiso 1 1 calc R . .
C22 C 0.2504(12) 0.5303(2) 0.2935(4) 0.0327(16) Uani 1 1 d . . .
H22A H 0.1840 0.5641 0.2509 0.039 Uiso 1 1 calc R . .
H22B H 0.2128 0.5357 0.3579 0.039 Uiso 1 1 calc R . .
C23 C 0.1557(11) 0.4699(2) 0.2485(4) 0.0279(14) Uani 1 1 d . . .
H23A H 0.1823 0.4658 0.1819 0.034 Uiso 1 1 calc R . .
H23B H -0.0038 0.4691 0.2437 0.034 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'
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
O1 P1 C18 112.8(2) . . yes
O1 P1 C5 111.0(2) . . yes
C18 P1 C5 113.0(2) . . yes
O1 P1 C1 113.5(2) . . yes
C18 P1 C1 104.6(2) . . yes
C5 P1 C1 101.3(2) . . yes
C6 C1 C2 115.0(4) . . ?
C6 C1 P1 109.5(3) . . ?
C2 C1 P1 110.3(3) . . ?
C6 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
P1 C1 H1 107.2 . . ?
C3 C2 C1 111.7(4) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O2 C3 C2 122.4(4) . . ?
O2 C3 C4 118.8(5) . . ?
C2 C3 C4 118.8(4) . . ?
C3 C4 C5 112.2(5) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C12 C5 C4 114.3(4) . . ?
C12 C5 P1 111.4(3) . . ?
C4 C5 P1 114.0(3) . . ?
C12 C5 H5 105.4 . . ?
C4 C5 H5 105.4 . . ?
P1 C5 H5 105.4 . . ?
C7 C6 C11 118.0(5) . . ?
C7 C6 C1 120.6(5) . . ?
C11 C6 C1 121.4(4) . . ?
C8 C7 C6 122.7(6) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 118.9(5) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.9(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C13 C12 C17 118.8(4) . . ?
C13 C12 C5 123.4(5) . . ?
C17 C12 C5 117.8(5) . . ?
C12 C13 C14 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.8(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C12 C17 C16 121.0(5) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C23 C18 C19 112.0(4) . . ?
C23 C18 P1 111.8(4) . . ?
C19 C18 P1 116.2(3) . . ?
C23 C18 H18 105.2 . . ?
C19 C18 H18 105.2 . . ?
P1 C18 H18 105.2 . . ?
C20 C19 C18 111.1(5) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C19 111.4(5) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 112.2(5) . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 111.5(4) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C18 109.6(4) . . ?
C22 C23 H23A 109.8 . . ?
C18 C23 H23A 109.8 . . ?
C22 C23 H23B 109.8 . . ?
C18 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
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
P1 O1 1.485(5) . yes
P1 C18 1.817(5) . yes
P1 C5 1.830(4) . yes
P1 C1 1.842(5) . yes
O2 C3 1.226(7) . ?
C1 C6 1.515(6) . ?
C1 C2 1.547(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.490(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(6) . ?
C4 C5 1.540(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.530(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.384(7) . ?
C6 C11 1.402(7) . ?
C7 C8 1.379(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.383(8) . ?
C12 C17 1.394(8) . ?
C13 C14 1.400(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.398(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.541(7) . ?
C18 C19 1.545(9) . ?
C18 H18 1.0000 . ?
C19 C20 1.538(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.531(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.506(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.538(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C6 -40.0(4) . . . . ?
C18 P1 C1 C6 83.3(4) . . . . ?
C5 P1 C1 C6 -159.1(4) . . . . ?
O1 P1 C1 C2 87.6(4) . . . . ?
C18 P1 C1 C2 -149.2(4) . . . . ?
C5 P1 C1 C2 -31.5(5) . . . . ?
C6 C1 C2 C3 -167.7(5) . . . . ?
P1 C1 C2 C3 67.9(6) . . . . ?
C1 C2 C3 O2 139.5(5) . . . . ?
C1 C2 C3 C4 -39.3(7) . . . . ?
O2 C3 C4 C5 154.5(5) . . . . ?
C2 C3 C4 C5 -26.7(7) . . . . ?
C3 C4 C5 C12 -170.4(4) . . . . ?
C3 C4 C5 P1 59.8(5) . . . . ?
O1 P1 C5 C12 79.9(4) . . . . ?
C18 P1 C5 C12 -47.9(5) . . . . ?
C1 P1 C5 C12 -159.3(4) . . . . ?
O1 P1 C5 C4 -148.9(3) . . . . ?
C18 P1 C5 C4 83.3(4) . . . . ?
C1 P1 C5 C4 -28.1(4) . . . . ?
C2 C1 C6 C7 144.5(5) . . . . ?
P1 C1 C6 C7 -90.6(5) . . . . ?
C2 C1 C6 C11 -38.0(7) . . . . ?
P1 C1 C6 C11 86.9(5) . . . . ?
C11 C6 C7 C8 -0.2(8) . . . . ?
C1 C6 C7 C8 177.3(5) . . . . ?
C6 C7 C8 C9 -0.8(8) . . . . ?
C7 C8 C9 C10 3.2(8) . . . . ?
C8 C9 C10 C11 -4.6(8) . . . . ?
C9 C10 C11 C6 3.6(7) . . . . ?
C7 C6 C11 C10 -1.1(7) . . . . ?
C1 C6 C11 C10 -178.7(4) . . . . ?
C4 C5 C12 C13 -20.9(6) . . . . ?
P1 C5 C12 C13 110.1(5) . . . . ?
C4 C5 C12 C17 159.1(4) . . . . ?
P1 C5 C12 C17 -69.9(5) . . . . ?
C17 C12 C13 C14 0.9(7) . . . . ?
C5 C12 C13 C14 -179.1(4) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C17 -0.3(8) . . . . ?
C13 C12 C17 C16 -1.5(7) . . . . ?
C5 C12 C17 C16 178.5(4) . . . . ?
C15 C16 C17 C12 1.2(7) . . . . ?
O1 P1 C18 C23 -41.9(4) . . . . ?
C5 P1 C18 C23 85.0(4) . . . . ?
C1 P1 C18 C23 -165.7(4) . . . . ?
O1 P1 C18 C19 -172.3(3) . . . . ?
C5 P1 C18 C19 -45.4(4) . . . . ?
C1 P1 C18 C19 63.9(4) . . . . ?
C23 C18 C19 C20 54.1(5) . . . . ?
P1 C18 C19 C20 -175.6(3) . . . . ?
C18 C19 C20 C21 -52.4(6) . . . . ?
C19 C20 C21 C22 54.5(6) . . . . ?
C20 C21 C22 C23 -57.1(5) . . . . ?
C21 C22 C23 C18 57.0(5) . . . . ?
C19 C18 C23 C22 -55.7(5) . . . . ?
P1 C18 C23 C22 171.7(4) . . . . ?
