#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/23/7102339.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_7102339
loop_
_publ_author_name
'Vogel, Ulf'
'Nixon, John F'
'Scheer, Manfred'
_publ_section_title
;
 Copper(I) mediated oligomerisation of a phosphaalkyne.
;
_journal_issue                   47
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5055
_journal_page_last               5057
_journal_paper_doi               10.1039/b712161j
_journal_year                    2007
_chemical_formula_moiety         'C20 H37 P5, 0.5(C7 H8)'
_chemical_formula_structural     '(P5 H C4)(C4 H9)4 * 0.5(C7 H8)'
_chemical_formula_sum            'C23.5 H41 P5'
_chemical_formula_weight         478.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.7888(3)
_cell_length_b                   11.2636(2)
_cell_length_c                   10.38680(10)
_cell_measurement_reflns_used    16404
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      65.3244
_cell_measurement_theta_min      1.9472
_cell_volume                     2643.85(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
;
_computing_molecular_graphics    Siemens-XP
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5431
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Gemini R-Ultra'
_diffrn_measurement_method       'combined 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  0.1366
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25696
_diffrn_reflns_theta_full        65.50
_diffrn_reflns_theta_max         65.50
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    3.259
_exptl_absorpt_correction_T_max  0.613
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.973
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0810
_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)+(0.1503P)²+10.0028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2302
_refine_ls_wR_factor_ref         0.2363
_reflns_number_gt                2156
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b712161j.txt
_cod_data_source_block           u512_2
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_original_formula_sum        'C23.50 H41 P5'
_cod_database_code               7102339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.82551(4) 0.37921(8) 0.16827(9) 0.0276(4) Uani 1 1 d .
P3 P 0.80058(6) 0.5000 0.37558(13) 0.0306(4) Uani 1 2 d S
P4 P 0.91659(6) 0.5000 0.42535(14) 0.0346(5) Uani 1 2 d S
P5 P 0.94957(7) 0.5000 0.25403(16) 0.0497(6) Uani 1 2 d S
H1 H 0.9586 0.6095 0.2447 0.050 Uiso 0.50 1 d PR
C1 C 0.85654(16) 0.3850(3) 0.3599(4) 0.0287(9) Uani 1 1 d .
C2 C 0.7731(2) 0.5000 0.1860(5) 0.0236(10) Uani 1 2 d S
C3 C 0.8729(2) 0.5000 0.1280(5) 0.0266(11) Uani 1 2 d S
C4 C 0.86377(18) 0.2653(4) 0.4348(4) 0.0356(9) Uani 1 1 d .
C5 C 0.8054(2) 0.1972(4) 0.3913(5) 0.0459(11) Uani 1 1 d .
H5A H 0.7925 0.1859 0.2928 0.069 Uiso 1 1 calc R
H5B H 0.7753 0.2423 0.4169 0.069 Uiso 1 1 calc R
H5C H 0.8109 0.1196 0.4362 0.069 Uiso 1 1 calc R
C6 C 0.8809(2) 0.2853(5) 0.5882(4) 0.0492(12) Uani 1 1 d .
H6A H 0.8885 0.2086 0.6350 0.074 Uiso 1 1 calc R
H6B H 0.8485 0.3258 0.6098 0.074 Uiso 1 1 calc R
H6C H 0.9167 0.3343 0.6180 0.074 Uiso 1 1 calc R
C7 C 0.9122(2) 0.1934(5) 0.4013(6) 0.0589(14) Uani 1 1 d .
H7A H 0.9003 0.1778 0.3037 0.088 Uiso 1 1 calc R
H7B H 0.9181 0.1179 0.4506 0.088 Uiso 1 1 calc R
H7C H 0.9493 0.2386 0.4283 0.088 Uiso 1 1 calc R
C8 C 0.7058(2) 0.5000 0.1169(6) 0.0299(12) Uani 1 2 d S
C9 C 0.6888(3) 0.5000 -0.0368(6) 0.0473(16) Uani 1 2 d S
H9A H 0.7056 0.5714 -0.0597 0.050 Uiso 1 1 d R
H9B H 0.6457 0.5000 -0.0697 0.050 Uiso 1 2 d SR
C10 C 0.68004(19) 0.6110(4) 0.1615(5) 0.0480(12) Uani 1 1 d .
H10A H 0.6378 0.6169 0.1108 0.072 Uiso 1 1 calc R
H10B H 0.7007 0.6814 0.1437 0.072 Uiso 1 1 calc R
H10C H 0.6851 0.6060 0.2587 0.072 Uiso 1 1 calc R
C11 C 0.8788(2) 0.5000 -0.0176(5) 0.0328(12) Uani 1 2 d S
C12 C 0.9122(2) 0.3885(5) -0.0373(5) 0.0469(12) Uani 1 1 d .
H12A H 0.9528 0.3913 0.0245 0.070 Uiso 1 1 calc R
H12B H 0.9128 0.3852 -0.1311 0.070 Uiso 1 1 calc R
H12C H 0.8922 0.3179 -0.0178 0.070 Uiso 1 1 calc R
C13 C 0.8176(3) 0.5000 -0.1249(6) 0.0437(15) Uani 1 2 d S
H13A H 0.8220 0.5000 -0.2135 0.052 Uiso 1 2 d SR
H13B H 0.7962 0.4305 -0.1142 0.052 Uiso 1 1 d R
C1S C 0.4954(5) 0.5000 -0.0764(16) 0.048(3) Uani 0.50 2 d SP
C2S C 0.4979(4) 0.3943(10) 0.1258(13) 0.061(3) Uani 0.50 1 d P
H2SA H 0.4924 0.3195 0.1648 0.074 Uiso 0.50 1 d PR
C3S C 0.4970(4) 0.5000 -0.2070(10) 0.074(2) Uani 1 2 d S
H3SA H 0.4933 0.5799 -0.2407 0.111 Uiso 0.25 1 d PR
H3SB H 0.5339 0.4671 -0.2094 0.111 Uiso 0.25 1 d PR
H3SC H 0.4649 0.4529 -0.2626 0.111 Uiso 0.25 1 d PR
H3SD H 0.4908 0.5000 -0.3029 0.089 Uiso 0.50 2 d SPR
C4S C 0.5000 0.3953(6) 0.0000 0.0519(18) Uani 1 2 d S
H4SA H 0.5050 0.3212 -0.0408 0.062 Uiso 0.50 1 d PR
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'
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
C2 P1 C3 87.74(16) . .
C2 P1 C1 85.74(19) . .
C3 P1 C1 98.26(19) . .
C2 P3 C1 86.21(16) . .
C2 P3 C1 86.21(16) . 6_565
C1 P3 C1 85.9(2) . 6_565
C2 P3 P4 101.90(16) . .
C1 P3 P4 45.62(12) . .
C1 P3 P4 45.62(12) 6_565 .
C1 P4 C1 86.5(2) . 6_565
C1 P4 P5 97.59(13) . .
C1 P4 P5 97.59(13) 6_565 .
C1 P4 P3 45.93(12) . .
C1 P4 P3 45.93(12) 6_565 .
P5 P4 P3 117.71(8) . .
C3 P5 P4 92.88(16) . .
C3 P5 H1 95.6 . .
P4 P5 H1 100.2 . .
C4 C1 P4 117.8(3) . .
C4 C1 P1 116.5(3) . .
P4 C1 P1 113.80(19) . .
C4 C1 P3 121.6(3) . .
P4 C1 P3 88.45(17) . .
P1 C1 P3 93.42(17) . .
C8 C2 P3 117.5(4) . .
C8 C2 P1 125.2(2) . .
P3 C2 P1 94.47(19) . .
C8 C2 P1 125.2(2) . 6_565
P3 C2 P1 94.47(19) . 6_565
P1 C2 P1 91.9(2) . 6_565
C11 C3 P5 108.2(3) . .
C11 C3 P1 117.0(2) . .
P5 C3 P1 111.1(2) . .
C11 C3 P1 117.0(2) . 6_565
P5 C3 P1 111.1(2) . 6_565
P1 C3 P1 91.8(2) . 6_565
C5 C4 C6 107.7(3) . .
C5 C4 C7 110.2(4) . .
C6 C4 C7 109.8(4) . .
C5 C4 C1 110.0(3) . .
C6 C4 C1 110.4(4) . .
C7 C4 C1 108.7(3) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C10 108.6(3) . 6_565
C9 C8 C10 108.6(3) . .
C10 C8 C10 110.0(5) 6_565 .
C9 C8 C2 112.8(4) . .
C10 C8 C2 108.5(3) 6_565 .
C10 C8 C2 108.5(3) . .
C8 C9 H9A 105.4 . .
C8 C9 H9B 105.9 . .
H9A C9 H9B 112.7 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C13 C11 C12 108.5(3) . 6_565
C13 C11 C12 108.5(3) . .
C12 C11 C12 110.0(5) 6_565 .
C13 C11 C3 110.6(4) . .
C12 C11 C3 109.7(3) 6_565 .
C12 C11 C3 109.7(3) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.4 . .
C2S C1S C2S 127.8(17) 2_655 5_665
C2S C1S C3S 64.7(9) 2_655 .
C2S C1S C3S 64.7(9) 5_665 .
C2S C1S C4S 57.9(6) 2_655 .
C2S C1S C4S 166.9(13) 5_665 .
C3S C1S C4S 122.5(5) . .
C2S C1S C4S 166.9(13) 2_655 5_665
C2S C1S C4S 57.9(6) 5_665 5_665
C3S C1S C4S 122.5(5) . 5_665
C4S C1S C4S 114.0(11) . 5_665
C2S C1S C1S 113.9(9) 2_655 5_665
C2S C1S C1S 113.9(9) 5_665 5_665
C3S C1S C1S 170.8(14) . 5_665
C4S C1S C1S 57.0(5) . 5_665
C4S C1S C1S 57.0(5) 5_665 5_665
C4S C2S C1S 64.1(9) . 5_665
C4S C2S C3S 123.2(9) . 5_665
C1S C2S C3S 59.1(8) 5_665 5_665
C4S C2S H2SA 118.4 . .
C1S C2S H2SA 177.4 5_665 .
C3S C2S H2SA 118.4 5_665 .
C1S C3S C2S 56.2(6) . 2_655
C1S C3S C2S 56.2(6) . 5_665
C2S C3S C2S 111.3(11) 2_655 5_665
C1S C3S H3SA 109.5 . .
C2S C3S H3SA 165.7 2_655 .
C2S C3S H3SA 54.5 5_665 .
C1S C3S H3SB 109.4 . .
C2S C3S H3SB 77.6 2_655 .
C2S C3S H3SB 115.0 5_665 .
H3SA C3S H3SB 109.5 . .
C1S C3S H3SC 109.5 . .
C2S C3S H3SC 78.6 2_655 .
C2S C3S H3SC 135.6 5_665 .
H3SA C3S H3SC 109.5 . .
H3SB C3S H3SC 109.5 . .
C1S C3S H3SD 170.2 . .
C2S C3S H3SD 124.3 2_655 .
C2S C3S H3SD 124.3 5_665 .
H3SA C3S H3SD 69.8 . .
H3SB C3S H3SD 79.5 . .
H3SC C3S H3SD 62.7 . .
C2S C4S C2S 179.0(11) . 2_655
C2S C4S C1S 123.0(8) . .
C2S C4S C1S 58.0(7) 2_655 .
C2S C4S C1S 58.0(7) . 5_665
C2S C4S C1S 123.0(8) 2_655 5_665
C1S C4S C1S 66.0(11) . 5_665
C2S C4S H4SA 118.4 . .
C2S C4S H4SA 60.6 2_655 .
C1S C4S H4SA 118.6 . .
C1S C4S H4SA 168.4 5_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C2 1.893(3) .
P1 C3 1.895(3) .
P1 C1 1.896(4) .
P3 C2 1.871(5) .
P3 C1 1.901(4) .
P3 C1 1.901(4) 6_565
P3 P4 2.644(2) .
P4 C1 1.891(4) .
P4 C1 1.891(4) 6_565
P4 P5 2.157(2) .
P5 C3 1.884(5) .
P5 H1 1.2609 .
C1 C4 1.539(5) .
C2 C8 1.536(7) .
C2 P1 1.893(3) 6_565
C3 C11 1.562(7) .
C3 P1 1.895(3) 6_565
C4 C5 1.527(6) .
C4 C6 1.533(6) .
C4 C7 1.535(6) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.519(8) .
C8 C10 1.527(5) 6_565
C8 C10 1.527(5) .
C9 H9A 0.9600 .
C9 H9B 0.9751 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C13 1.533(8) .
C11 C12 1.533(5) 6_565
C11 C12 1.533(5) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9586 .
C13 H13B 0.9587 .
C1S C2S 1.326(12) 2_655
C1S C2S 1.326(12) 5_665
C1S C3S 1.369(17) .
C1S C4S 1.406(10) .
C1S C4S 1.406(10) 5_665
C1S C1S 1.53(3) 5_665
C2S C4S 1.324(13) .
C2S C1S 1.326(12) 5_665
C2S C3S 1.442(14) 5_665
C2S H2SA 0.9601 .
C3S C2S 1.442(14) 2_655
C3S C2S 1.442(14) 5_665
C3S H3SA 0.9600 .
C3S H3SB 0.9600 .
C3S H3SC 0.9601 .
C3S H3SD 0.9600 .
C4S C2S 1.324(13) 2_655
C4S C1S 1.406(10) 5_665
C4S H4SA 0.9600 .
