#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:17:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178893 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112299.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_4112299
loop_
_publ_author_name
'J. Chris Slootweg'
'Marius Schakel'
'Frans J. J. de Kanter'
'Andreas W. Ehlers'
'Sergei I. Kozhushkov'
'Armin de Meijere'
'Martin Lutz'
'Anthony L. Spek'
'Koop Lammertsma'
_publ_contact_author_address
; Bijvoet Center for Biomolecular Research
  Dep. Crystal and Structural Chemistry
  Utrecht University
  Padualaan 8
  3584 CH Utrecht
  The Netherlands
;
_publ_contact_author_email       m.lutz@chem.uu.nl
_publ_contact_author_fax         '[+31] 30 2533940'
_publ_contact_author_name        'Martin Lutz'
_publ_contact_author_phone       '[+31] 30 2533902'
_publ_section_title
;
 Branched Phospha[7]triangulanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3050
_journal_page_last               3051
_journal_paper_doi               10.1021/ja031648p
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C20 H21 P'
_chemical_formula_sum            'C20 H21 P'
_chemical_formula_weight         292.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.6968(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8462(1)
_cell_length_b                   12.9734(2)
_cell_length_c                   8.7058(1)
_cell_measurement_reflns_used    25677
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     798.538(19)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15383
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0307
_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)+(0.0360P)²+0.3154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                1738
_reflns_number_total             1913
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja031648psi20031211_113904_2.cif
_cod_data_source_block           s2644a
_cod_original_cell_volume        798.537(18)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4112299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
P1 P 0.56283(5) 0.2500 0.45078(5) 0.01887(12) Uani 1 2 d S
C1 C 0.67813(14) 0.19333(8) 0.66589(13) 0.0169(2) Uani 1 1 d .
C2 C 0.82087(15) 0.11021(8) 0.74333(13) 0.0188(2) Uani 1 1 d .
C3 C 1.02861(16) 0.10029(9) 0.84602(15) 0.0242(3) Uani 1 1 d .
H3A H 1.0747(19) 0.0656(12) 0.9579(19) 0.032(4) Uiso 1 1 d .
H3B H 1.1090(19) 0.1574(11) 0.8383(17) 0.028(4) Uiso 1 1 d .
C4 C 0.92396(18) 0.03629(10) 0.68435(17) 0.0264(3) Uani 1 1 d .
H4A H 0.905(2) -0.0368(13) 0.697(2) 0.038(4) Uiso 1 1 d .
H4B H 0.9449(19) 0.0557(12) 0.5860(19) 0.032(4) Uiso 1 1 d .
C5 C 0.64557(15) 0.10895(8) 0.76586(14) 0.0197(2) Uani 1 1 d .
C6 C 0.49745(19) 0.03190(10) 0.74551(18) 0.0303(3) Uani 1 1 d .
H6A H 0.536(2) -0.0403(13) 0.754(2) 0.039(4) Uiso 1 1 d .
H6B H 0.368(2) 0.0471(12) 0.665(2) 0.037(4) Uiso 1 1 d .
C7 C 0.58773(17) 0.09744(10) 0.90656(16) 0.0260(3) Uani 1 1 d .
H7A H 0.511(2) 0.1508(12) 0.9191(17) 0.028(4) Uiso 1 1 d .
H7B H 0.673(2) 0.0650(13) 1.009(2) 0.037(4) Uiso 1 1 d .
C8 C 0.3110(2) 0.2500 0.39938(19) 0.0180(3) Uani 1 2 d S
C9 C 0.1898(2) 0.2500 0.22569(19) 0.0204(3) Uani 1 2 d S
H9 H 0.2417 0.2500 0.1453 0.024 Uiso 1 2 calc SR
C10 C -0.0059(2) 0.2500 0.1675(2) 0.0234(3) Uani 1 2 d S
H10 H -0.0866 0.2500 0.0488 0.028 Uiso 1 2 calc SR
C11 C -0.0818(2) 0.2500 0.2847(2) 0.0234(3) Uani 1 2 d S
H11 H -0.2151 0.2500 0.2463 0.028 Uiso 1 2 calc SR
C12 C 0.0372(2) 0.2500 0.4587(2) 0.0221(3) Uani 1 2 d S
H12 H -0.0153 0.2500 0.5386 0.026 Uiso 1 2 calc SR
C13 C 0.2324(2) 0.2500 0.51598(19) 0.0206(3) Uani 1 2 d S
H13 H 0.3127 0.2500 0.6349 0.025 Uiso 1 2 calc SR
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'
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
C8 P1 C1 104.55(6) . 4_565
C8 P1 C1 104.55(6) . .
C1 P1 C1 47.02(6) 4_565 .
C1 C1 C5 137.37(6) 4_565 .
C1 C1 C2 136.40(6) 4_565 .
C5 C1 C2 59.24(7) . .
C1 C1 P1 66.49(3) 4_565 .
C5 C1 P1 139.00(8) . .
C2 C1 P1 133.67(8) . .
C5 C2 C4 136.14(10) . .
C5 C2 C3 139.79(10) . .
C4 C2 C3 62.07(8) . .
C5 C2 C1 60.35(7) . .
C4 C2 C1 136.71(10) . .
C3 C2 C1 138.46(10) . .
C2 C3 C4 58.85(7) . .
C2 C3 H3A 118.0(8) . .
C4 C3 H3A 118.7(9) . .
C2 C3 H3B 117.2(8) . .
C4 C3 H3B 116.5(8) . .
H3A C3 H3B 115.7(11) . .
C2 C4 C3 59.09(7) . .
C2 C4 H4A 117.0(9) . .
C3 C4 H4A 118.0(9) . .
C2 C4 H4B 117.6(9) . .
C3 C4 H4B 116.2(9) . .
H4A C4 H4B 116.6(13) . .
C2 C5 C6 136.10(10) . .
C2 C5 C7 138.41(10) . .
C6 C5 C7 61.82(8) . .
C2 C5 C1 60.41(7) . .
C6 C5 C1 138.58(10) . .
C7 C5 C1 138.33(10) . .
C5 C6 C7 59.18(8) . .
C5 C6 H6A 116.1(9) . .
C7 C6 H6A 117.3(9) . .
C5 C6 H6B 118.1(9) . .
C7 C6 H6B 118.2(9) . .
H6A C6 H6B 116.1(13) . .
C5 C7 C6 59.00(8) . .
C5 C7 H7A 117.1(8) . .
C6 C7 H7A 116.4(8) . .
C5 C7 H7B 118.3(9) . .
C6 C7 H7B 118.3(10) . .
H7A C7 H7B 115.9(12) . .
C9 C8 C13 118.61(14) . .
C9 C8 P1 115.00(11) . .
C13 C8 P1 126.38(12) . .
C10 C9 C8 121.37(14) . .
C10 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C11 C10 C9 119.34(15) . .
C11 C10 H10 120.3 . .
C9 C10 H10 120.3 . .
C10 C11 C12 120.09(15) . .
C10 C11 H11 120.0 . .
C12 C11 H11 120.0 . .
C13 C12 C11 120.32(15) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C8 120.27(14) . .
C12 C13 H13 119.9 . .
C8 C13 H13 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C8 1.8265(15) .
P1 C1 1.8430(11) 4_565
P1 C1 1.8430(11) .
C1 C1 1.470(2) 4_565
C1 C5 1.4879(14) .
C1 C2 1.4889(14) .
C2 C5 1.4712(15) .
C2 C4 1.4825(15) .
C2 C3 1.4862(15) .
C3 C4 1.5305(17) .
C3 H3A 0.988(15) .
C3 H3B 0.994(15) .
C4 H4A 0.974(16) .
C4 H4B 0.972(15) .
C5 C6 1.4841(15) .
C5 C7 1.4869(16) .
C6 C7 1.5262(18) .
C6 H6A 0.976(17) .
C6 H6B 0.974(16) .
C7 H7A 0.956(15) .
C7 H7B 0.952(16) .
C8 C9 1.394(2) .
C8 C13 1.398(2) .
C9 C10 1.393(2) .
C9 H9 0.9500 .
C10 C11 1.386(2) .
C10 H10 0.9500 .
C11 C12 1.393(2) .
C11 H11 0.9500 .
C12 C13 1.390(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
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_4
C8 P1 C1 C1 -96.48(3) . 4_565
C8 P1 C1 C5 39.77(12) . .
C1 P1 C1 C5 136.26(11) 4_565 .
C8 P1 C1 C2 130.94(10) . .
C1 P1 C1 C2 -132.58(10) 4_565 .
C1 C1 C2 C5 128.06(8) 4_565 .
P1 C1 C2 C5 -130.24(11) . .
C1 C1 C2 C4 -104.67(13) 4_565 .
C5 C1 C2 C4 127.27(15) . .
P1 C1 C2 C4 -3.0(2) . .
C1 C1 C2 C3 -4.99(19) 4_565 .
C5 C1 C2 C3 -133.05(16) . .
P1 C1 C2 C3 96.71(16) . .
C5 C2 C3 C4 129.56(16) . .
C1 C2 C3 C4 -130.09(16) . .
C5 C2 C4 C3 -134.09(15) . .
C1 C2 C4 C3 132.28(15) . .
C4 C2 C5 C6 2.8(2) . .
C3 C2 C5 C6 -97.84(19) . .
C1 C2 C5 C6 130.81(16) . .
C4 C2 C5 C7 101.08(19) . .
C3 C2 C5 C7 0.5(2) . .
C1 C2 C5 C7 -130.86(16) . .
C4 C2 C5 C1 -128.05(15) . .
C3 C2 C5 C1 131.36(16) . .
C1 C1 C5 C2 -126.71(8) 4_565 .
P1 C1 C5 C2 122.69(12) . .
C1 C1 C5 C6 105.78(14) 4_565 .
C2 C1 C5 C6 -127.51(16) . .
P1 C1 C5 C6 -4.8(2) . .
C1 C1 C5 C7 4.26(19) 4_565 .
C2 C1 C5 C7 130.97(16) . .
P1 C1 C5 C7 -106.34(16) . .
C2 C5 C6 C7 131.83(15) . .
C1 C5 C6 C7 -132.35(16) . .
C2 C5 C7 C6 -128.89(16) . .
C1 C5 C7 C6 132.65(16) . .
C1 P1 C8 C9 155.66(3) 4_565 .
C1 P1 C8 C9 -155.66(3) . .
C1 P1 C8 C13 -24.34(3) 4_565 .
C1 P1 C8 C13 24.34(3) . .
C13 C8 C9 C10 0.0 . .
P1 C8 C9 C10 180.0 . .
C8 C9 C10 C11 0.0 . .
C9 C10 C11 C12 0.0 . .
C10 C11 C12 C13 0.0 . .
C11 C12 C13 C8 0.0 . .
C9 C8 C13 C12 0.0 . .
P1 C8 C13 C12 180.0 . .
