#------------------------------------------------------------------------------
#$Date: 2019-10-02 18:09:26 +0300 (Wed, 02 Oct 2019) $
#$Revision: 219040 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/89/4028963.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4028963
loop_
_publ_author_name
'Öberg, Elisabet'
'Schäfer, Bernhard'
'Geng, Xue-Li'
'Pettersson, Jenny'
'Hu, Qi'
'Kritikos, Mikael'
'Rasmussen, Torben'
'Ott, Sascha'
_publ_section_title
;
 C,C-Diacetylenic Phosphaalkenes as Heavy Diethynylethene Analogues
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   24
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              9265
_journal_page_last               9273
_journal_paper_doi               10.1021/jo901942u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C35 H38.5 N O2 P'
_chemical_formula_weight         536.14
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.142(15)
_cell_angle_beta                 93.977(15)
_cell_angle_gamma                92.936(15)
_cell_formula_units_Z            2
_cell_length_a                   8.7338(10)
_cell_length_b                   13.3618(17)
_cell_length_c                   14.4726(19)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3
_cell_measurement_theta_min      2.6
_cell_volume                     1566.2(4)
_computing_cell_refinement       'IPDS Software, Stoe & Cie (1997)'
_computing_data_collection       'IPDS Software, by Stoe & Cie (1997)'
_computing_data_reduction        'IPDS Software,  Stoe & Cie (1997)'
_computing_molecular_graphics
'PLATON99 (Spek, 2000), DIAMOND (Brandenburg, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_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    0.1158
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12404
_diffrn_reflns_theta_full        26.18
_diffrn_reflns_theta_max         26.18
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             573
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0523
_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)+(0.0705P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                2571
_reflns_number_total             5809
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901942usup2.cif
_cod_data_source_block           cmpd1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-10-01
;
_cod_original_cell_volume        1566.2(3)
_cod_original_formula_sum        'C35 H38.50 N O2 P'
_cod_database_code               4028963
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.90743(11) 0.83951(7) 0.69149(6) 0.0587(3) Uani 1 1 d .
N1 N 1.6384(5) 0.0891(3) 0.5888(4) 0.1143(13) Uani 1 1 d .
O1 O 1.6527(5) 0.0649(3) 0.6615(4) 0.1743(19) Uani 1 1 d .
O2 O 1.6835(4) 0.0381(3) 0.5088(3) 0.1480(15) Uani 1 1 d .
C1 C 1.0066(3) 0.7625(2) 0.59956(18) 0.0469(7) Uani 1 1 d .
C2 C 1.1063(3) 0.6865(2) 0.61163(19) 0.0508(7) Uani 1 1 d .
C3 C 1.1831(3) 0.6173(2) 0.6177(2) 0.0530(7) Uani 1 1 d .
C4 C 1.2669(4) 0.5348(2) 0.6203(2) 0.0563(8) Uani 1 1 d .
C5 C 1.3359(4) 0.4591(2) 0.6178(2) 0.0606(8) Uani 1 1 d .
C6 C 1.4134(3) 0.3657(2) 0.6113(2) 0.0564(8) Uani 1 1 d .
C7 C 1.4795(4) 0.3093(3) 0.5255(2) 0.0776(11) Uani 1 1 d .
H7 H 1.4745 0.3331 0.4725 0.093 Uiso 1 1 calc .
C8 C 1.5519(5) 0.2189(3) 0.5179(3) 0.0861(12) Uani 1 1 d .
H8 H 1.5952 0.1805 0.4598 0.103 Uiso 1 1 calc .
C9 C 1.5598(4) 0.1859(2) 0.5964(3) 0.0768(11) Uani 1 1 d .
C10 C 1.4981(5) 0.2403(3) 0.6822(3) 0.0889(12) Uani 1 1 d .
H10 H 1.5055 0.2164 0.7352 0.107 Uiso 1 1 calc .
C11 C 1.4251(5) 0.3305(3) 0.6898(3) 0.0793(11) Uani 1 1 d .
H11 H 1.3830 0.3684 0.7484 0.095 Uiso 1 1 calc .
C12 C 0.9898(3) 0.7686(2) 0.49878(18) 0.0492(7) Uani 1 1 d .
C13 C 0.9239(4) 0.8526(2) 0.4824(2) 0.0651(9) Uani 1 1 d .
H13 H 0.8890 0.9073 0.5353 0.078 Uiso 1 1 calc .
C14 C 0.9090(5) 0.8568(3) 0.3885(2) 0.0839(12) Uani 1 1 d .
H14 H 0.8641 0.9142 0.3786 0.101 Uiso 1 1 calc .
C15 C 0.9592(5) 0.7778(3) 0.3105(2) 0.0911(13) Uani 1 1 d .
H15 H 0.9496 0.7816 0.2475 0.109 Uiso 1 1 calc .
C16 C 1.0231(5) 0.6937(3) 0.3241(2) 0.0917(13) Uani 1 1 d .
H16 H 1.0568 0.6394 0.2703 0.110 Uiso 1 1 calc .
C17 C 1.0385(4) 0.6881(3) 0.4174(2) 0.0657(8) Uiso 1 1 d .
H17 H 1.0821 0.6296 0.4260 0.079 Uiso 1 1 calc .
C18 C 0.9850(3) 0.8052(2) 0.79631(18) 0.0478(7) Uani 1 1 d .
C19 C 0.8785(4) 0.1399(2) 0.14664(19) 0.0498(7) Uani 1 1 d .
C20 C 0.8013(4) 0.1857(2) 0.0859(2) 0.0540(7) Uani 1 1 d .
H20 H 0.7080 0.1517 0.0510 0.065 Uiso 1 1 calc .
C21 C 1.1429(4) 0.7213(2) 0.92446(19) 0.0507(7) Uani 1 1 d .
C22 C 1.0000(4) 0.6773(2) 0.8777(2) 0.0545(8) Uani 1 1 d .
H22 H 0.9573 0.6177 0.8885 0.065 Uiso 1 1 calc .
C23 C 0.9155(3) 0.7163(2) 0.81519(19) 0.0491(7) Uani 1 1 d .
C24 C 0.7539(4) 0.6613(2) 0.7699(2) 0.0603(8) Uani 1 1 d .
C25 C 0.7562(4) 0.5863(3) 0.6608(2) 0.0800(10) Uani 1 1 d .
H25A H 0.6544 0.5533 0.6346 0.120 Uiso 1 1 calc R
H25B H 0.8251 0.5315 0.6570 0.120 Uiso 1 1 calc R
H25C H 0.7905 0.6273 0.6225 0.120 Uiso 1 1 calc R
C26 C 0.6348(4) 0.7437(3) 0.7772(3) 0.0840(11) Uani 1 1 d .
H26A H 0.5359 0.7065 0.7484 0.126 Uiso 1 1 calc R
H26B H 0.6653 0.7889 0.7420 0.126 Uiso 1 1 calc R
H26C H 0.6285 0.7871 0.8459 0.126 Uiso 1 1 calc R
C27 C 0.6934(5) 0.5909(3) 0.8259(3) 0.0907(12) Uani 1 1 d .
H27A H 0.5929 0.5578 0.7962 0.136 Uiso 1 1 calc R
H27B H 0.6874 0.6350 0.8944 0.136 Uiso 1 1 calc R
H27C H 0.7623 0.5361 0.8220 0.136 Uiso 1 1 calc R
C28 C 0.7686(4) 0.3317(3) 0.0128(2) 0.0611(8) Uani 1 1 d .
C29 C 0.8588(6) 0.3338(4) -0.0715(3) 0.1143(16) Uani 1 1 d .
H29A H 0.8020 0.3668 -0.1105 0.172 Uiso 1 1 calc R
H29B H 0.8757 0.2616 -0.1127 0.172 Uiso 1 1 calc R
H29C H 0.9561 0.3745 -0.0451 0.172 Uiso 1 1 calc R
C30 C 0.6100(5) 0.2733(4) -0.0303(3) 0.1021(14) Uani 1 1 d .
H30A H 0.5513 0.2716 0.0229 0.153 Uiso 1 1 calc R
H30B H 0.6218 0.2010 -0.0739 0.153 Uiso 1 1 calc R
H30C H 0.5572 0.3106 -0.0669 0.153 Uiso 1 1 calc R
C31 C 1.2589(5) 0.5533(3) 0.9199(3) 0.1034(14) Uani 1 1 d .
H31A H 1.3133 0.5556 0.8652 0.155 Uiso 1 1 calc R
H31B H 1.1617 0.5120 0.8949 0.155 Uiso 1 1 calc R
H31C H 1.3189 0.5204 0.9575 0.155 Uiso 1 1 calc R
C32 C 0.8083(4) 0.0307(2) 0.1453(2) 0.0672(9) Uani 1 1 d .
C33 C 0.9327(6) -0.0469(3) 0.1416(4) 0.1149(16) Uani 1 1 d .
H33A H 0.8859 -0.1137 0.1411 0.172 Uiso 1 1 calc R
H33B H 1.0059 -0.0158 0.1991 0.172 Uiso 1 1 calc R
H33C H 0.9843 -0.0597 0.0825 0.172 Uiso 1 1 calc R
C34 C 0.7177(5) 0.0440(3) 0.2349(3) 0.1059(14) Uani 1 1 d .
H34A H 0.6764 -0.0254 0.2314 0.159 Uiso 1 1 calc R
H34B H 0.6350 0.0885 0.2345 0.159 Uiso 1 1 calc R
H34C H 0.7848 0.0771 0.2950 0.159 Uiso 1 1 calc R
C35 C 1.3001(7) 1.0265(3) 0.9483(4) 0.140(2) Uani 1 1 d .
H35A H 1.3258 1.0993 0.9540 0.211 Uiso 1 1 calc R
H35B H 1.3922 0.9896 0.9445 0.211 Uiso 1 1 calc R
H35C H 1.2504 1.0266 1.0055 0.211 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
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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
C1 P1 C18 101.00(12) . .
O1 N1 O2 124.5(4) . .
O1 N1 C9 118.2(5) . .
O2 N1 C9 117.3(4) . .
C2 C1 C12 116.0(2) . .
C2 C1 P1 123.01(19) . .
C12 C1 P1 120.99(18) . .
C3 C2 C1 175.6(3) . .
C2 C3 C4 177.1(3) . .
C5 C4 C3 176.5(3) . .
C4 C5 C6 177.4(3) . .
C11 C6 C7 118.8(3) . .
C11 C6 C5 121.1(3) . .
C7 C6 C5 120.1(3) . .
C8 C7 C6 120.6(3) . .
C9 C8 C7 118.9(3) . .
C10 C9 C8 122.0(3) . .
C10 C9 N1 118.8(4) . .
C8 C9 N1 119.2(4) . .
C9 C10 C11 119.1(3) . .
C10 C11 C6 120.5(3) . .
C13 C12 C17 117.6(2) . .
C13 C12 C1 121.6(2) . .
C17 C12 C1 120.8(2) . .
C12 C13 C14 120.8(3) . .
C15 C14 C13 120.4(3) . .
C16 C15 C14 120.2(3) . .
C15 C16 C17 120.1(3) . .
C16 C17 C12 120.9(3) . .
C19 C18 C23 119.2(2) 2_766 .
C19 C18 P1 120.2(2) 2_766 .
C23 C18 P1 120.3(2) . .
C20 C19 C18 118.3(3) . 2_766
C20 C19 C32 117.3(3) . .
C18 C19 C32 124.4(2) 2_766 .
C21 C20 C19 122.9(3) 2_766 .
C22 C21 C20 117.2(3) . 2_766
C22 C21 C28 120.0(3) . 2_766
C20 C21 C28 122.8(3) 2_766 2_766
C21 C22 C23 123.8(3) . .
C22 C23 C18 117.4(3) . .
C22 C23 C24 118.5(3) . .
C18 C23 C24 124.0(2) . .
C26 C24 C25 109.7(3) . .
C26 C24 C27 105.8(3) . .
C25 C24 C27 106.6(3) . .
C26 C24 C23 111.9(3) . .
C25 C24 C23 111.3(2) . .
C27 C24 C23 111.3(3) . .
C29 C28 C30 108.8(3) . .
C29 C28 C21 110.2(3) . 2_766
C30 C28 C21 112.2(3) . 2_766
C29 C28 C31 110.3(3) . 2_766
C30 C28 C31 106.6(3) . 2_766
C21 C28 C31 108.6(3) 2_766 2_766
C35 C32 C34 107.8(4) 2_766 .
C35 C32 C33 104.8(3) 2_766 .
C34 C32 C33 109.4(3) . .
C35 C32 C19 111.1(3) 2_766 .
C34 C32 C19 112.1(3) . .
C33 C32 C19 111.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.686(3) .
P1 C18 1.833(3) .
N1 O1 1.207(5) .
N1 O2 1.218(5) .
N1 C9 1.469(4) .
C1 C2 1.420(3) .
C1 C12 1.488(3) .
C2 C3 1.195(3) .
C3 C4 1.364(4) .
C4 C5 1.194(4) .
C5 C6 1.427(4) .
C6 C11 1.378(4) .
C6 C7 1.382(4) .
C7 C8 1.365(4) .
C8 C9 1.358(5) .
C9 C10 1.357(5) .
C10 C11 1.365(4) .
C12 C13 1.374(4) .
C12 C17 1.388(4) .
C13 C14 1.377(4) .
C14 C15 1.356(4) .
C15 C16 1.350(5) .
C16 C17 1.377(4) .
C18 C19 1.407(4) 2_766
C18 C23 1.427(4) .
C19 C20 1.396(4) .
C19 C18 1.407(4) 2_766
C19 C32 1.546(4) .
C20 C21 1.373(4) 2_766
C21 C22 1.372(4) .
C21 C20 1.373(4) 2_766
C21 C28 1.532(4) 2_766
C22 C23 1.386(4) .
C23 C24 1.543(4) .
C24 C26 1.534(4) .
C24 C25 1.537(4) .
C24 C27 1.542(5) .
C28 C29 1.505(5) .
C28 C30 1.528(5) .
C28 C21 1.532(4) 2_766
C28 C31 1.536(5) 2_766
C31 C28 1.536(5) 2_766
C32 C35 1.523(5) 2_766
C32 C34 1.526(5) .
C32 C33 1.530(5) .
C35 C32 1.523(5) 2_766
