#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/37/2213716.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2213716
loop_
_publ_author_name
'Kirsten, Leo'
'Steyl, Gideon'
'Roodt, Andreas'
_publ_section_title
;
 Tris(1-naphthyl) phosphite
;
_journal_coeditor_code           CF2097
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2828
_journal_page_last               o2830
_journal_paper_doi               10.1107/S1600536807019629
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C30 H21 O3 P'
_chemical_formula_moiety         'C30 H21 O3 P'
_chemical_formula_sum            'C30 H21 O3 P'
_chemical_formula_weight         460.44
_chemical_name_systematic
;
Tris(1-naphthyl) phosphite
;
_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                106.782(2)
_cell_angle_beta                 97.780(2)
_cell_angle_gamma                92.8900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5057(2)
_cell_length_b                   10.8272(4)
_cell_length_c                   14.6167(5)
_cell_measurement_reflns_used    5337
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.25
_cell_volume                     1121.75(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker X8 APEXII
;
_diffrn_measurement_method       'φ and ω'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19931
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.040
_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)+(0.0485P)²+0.4566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                4452
_reflns_number_total             5403
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2097.cif
_cod_data_source_block           I
_cod_original_cell_volume        1121.75(6)
_cod_database_code               2213716
_cod_database_fobs_code          2213716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
P P 0.20126(5) 0.62334(4) 0.18790(3) 0.01547(10) Uani d . 1
O O1 0.38719(14) 0.55003(10) 0.17832(7) 0.0170(2) Uani d . 1
O O2 0.22280(14) 0.65535(10) 0.30562(7) 0.0171(2) Uani d . 1
O O3 0.27689(13) 0.75907(10) 0.17675(7) 0.0161(2) Uani d . 1
C C11 0.3803(2) 0.41869(14) 0.17032(10) 0.0156(3) Uani d . 1
C C12 0.52499(19) 0.35270(14) 0.13158(10) 0.0152(3) Uani d . 1
C C13 0.6688(2) 0.41668(15) 0.10347(10) 0.0173(3) Uani d . 1
H H13 0.6704 0.5067 0.1102 0.021 Uiso calc R 1
C C14 0.8051(2) 0.34810(16) 0.06664(11) 0.0207(3) Uani d . 1
H H14 0.9009 0.3910 0.0478 0.025 Uiso calc R 1
C C15 0.8043(2) 0.21501(16) 0.05652(11) 0.0230(3) Uani d . 1
H H15 0.8998 0.1690 0.0310 0.028 Uiso calc R 1
C C16 0.6676(2) 0.15085(16) 0.08287(11) 0.0207(3) Uani d . 1
H H16 0.6687 0.0608 0.0753 0.025 Uiso calc R 1
C C17 0.5241(2) 0.21812(15) 0.12147(10) 0.0171(3) Uani d . 1
C C18 0.3808(2) 0.15365(15) 0.14905(11) 0.0203(3) Uani d . 1
H H18 0.3794 0.0635 0.1418 0.024 Uiso calc R 1
C C19 0.2450(2) 0.22087(15) 0.18594(11) 0.0216(3) Uani d . 1
H H19 0.1494 0.1769 0.2041 0.026 Uiso calc R 1
C C110 0.2441(2) 0.35488(15) 0.19756(11) 0.0196(3) Uani d . 1
H H110 0.1494 0.4007 0.2242 0.024 Uiso calc R 1
C C21 0.0805(2) 0.67074(14) 0.35833(10) 0.0149(3) Uani d . 1
C C22 0.12295(19) 0.65795(14) 0.45288(10) 0.0147(3) Uani d . 1
C C23 0.2957(2) 0.62959(14) 0.48984(11) 0.0182(3) Uani d . 1
H H23 0.3886 0.6175 0.4508 0.022 Uiso calc R 1
C C24 0.3286(2) 0.61969(16) 0.58180(12) 0.0230(3) Uani d . 1
H H24 0.4449 0.6015 0.6064 0.028 Uiso calc R 1
C C25 0.1922(2) 0.63610(15) 0.64034(11) 0.0232(3) Uani d . 1
H H25 0.2166 0.6287 0.7039 0.028 Uiso calc R 1
C C26 0.0248(2) 0.66264(15) 0.60574(11) 0.0205(3) Uani d . 1
H H26 -0.0666 0.6729 0.6457 0.025 Uiso calc R 1
C C27 -0.0151(2) 0.67516(14) 0.51161(10) 0.0160(3) Uani d . 1
C C28 -0.1879(2) 0.70372(15) 0.47510(11) 0.0200(3) Uani d . 1
H H28 -0.2802 0.7156 0.5146 0.024 Uiso calc R 1
C C29 -0.2228(2) 0.71431(16) 0.38363(12) 0.0215(3) Uani d . 1
H H29 -0.3395 0.7324 0.3597 0.026 Uiso calc R 1
C C210 -0.0868(2) 0.69869(15) 0.32426(11) 0.0183(3) Uani d . 1
H H210 -0.1114 0.7075 0.2611 0.022 Uiso calc R 1
C C31 0.40992(19) 0.85082(14) 0.24061(10) 0.0149(3) Uani d . 1
C C32 0.57929(19) 0.86504(14) 0.20994(10) 0.0139(3) Uani d . 1
C C33 0.6219(2) 0.78828(14) 0.12072(10) 0.0156(3) Uani d . 1
H H33 0.5351 0.7228 0.0783 0.019 Uiso calc R 1
C C34 0.7873(2) 0.80794(15) 0.09528(11) 0.0179(3) Uani d . 1
H H34 0.8143 0.7561 0.0352 0.021 Uiso calc R 1
C C35 0.9184(2) 0.90466(15) 0.15754(11) 0.0189(3) Uani d . 1
H H35 1.0330 0.9174 0.1392 0.023 Uiso calc R 1
C C36 0.8808(2) 0.98001(15) 0.24417(11) 0.0184(3) Uani d . 1
H H36 0.9700 1.0445 0.2856 0.022 Uiso calc R 1
C C37 0.7105(2) 0.96315(14) 0.27295(10) 0.0156(3) Uani d . 1
C C38 0.6678(2) 1.04133(15) 0.36173(11) 0.0206(3) Uani d . 1
H H38 0.7560 1.1056 0.4044 0.025 Uiso calc R 1
C C39 0.5014(2) 1.02521(15) 0.38660(11) 0.0215(3) Uani d . 1
H H39 0.4740 1.0796 0.4457 0.026 Uiso calc R 1
C C310 0.3697(2) 0.92871(15) 0.32542(11) 0.0189(3) Uani d . 1
H H310 0.2540 0.9180 0.3431 0.023 Uiso calc R 1
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'
O O 0.0106 0.0060 '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_publ_flag
O2 P O1 94.73(5) y
O3 P O1 98.02(5) y
O3 P O2 101.91(6) y
C11 O1 P 119.03(9) ?
C21 O2 P 124.86(9) ?
C31 O3 P 127.49(9) ?
C110 C11 O1 123.07(13) ?
C110 C11 C12 121.17(14) ?
O1 C11 C12 115.75(13) ?
C17 C12 C11 118.04(13) ?
C17 C12 C13 119.60(14) ?
C11 C12 C13 122.36(14) ?
C14 C13 C12 119.83(15) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C15 120.61(15) ?
C13 C14 H14 119.7 ?
C15 C14 H14 119.7 ?
C16 C15 C14 120.85(15) ?
C16 C15 H15 119.6 ?
C14 C15 H15 119.6 ?
C15 C16 C17 120.39(15) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C18 C17 C16 121.40(14) ?
C18 C17 C12 119.88(14) ?
C16 C17 C12 118.72(14) ?
C19 C18 C17 120.05(14) ?
C19 C18 H18 120.0 ?
C17 C18 H18 120.0 ?
C18 C19 C110 121.03(15) ?
C18 C19 H19 119.5 ?
C110 C19 H19 119.5 ?
C11 C110 C19 119.83(14) ?
C11 C110 H110 120.1 ?
C19 C110 H110 120.1 ?
C210 C21 O2 123.56(13) ?
C210 C21 C22 121.87(13) ?
O2 C21 C22 114.56(13) ?
C27 C22 C23 119.57(13) ?
C27 C22 C21 117.62(13) ?
C23 C22 C21 122.81(13) ?
C24 C23 C22 120.00(14) ?
C24 C23 H23 120.0 ?
C22 C23 H23 120.0 ?
C23 C24 C25 120.78(15) ?
C23 C24 H24 119.6 ?
C25 C24 H24 119.6 ?
C26 C25 C24 120.00(14) ?
C26 C25 H25 120.0 ?
C24 C25 H25 120.0 ?
C25 C26 C27 121.32(15) ?
C25 C26 H26 119.3 ?
C27 C26 H26 119.3 ?
C26 C27 C28 121.88(14) ?
C26 C27 C22 118.32(14) ?
C28 C27 C22 119.80(13) ?
C29 C28 C27 120.50(14) ?
C29 C28 H28 119.8 ?
C27 C28 H28 119.8 ?
C28 C29 C210 120.64(14) ?
C28 C29 H29 119.7 ?
C210 C29 H29 119.7 ?
C21 C210 C29 119.57(14) ?
C21 C210 H210 120.2 ?
C29 C210 H210 120.2 ?
C310 C31 O3 119.90(13) ?
C310 C31 C32 122.43(14) ?
O3 C31 C32 117.50(12) ?
C33 C32 C31 123.44(13) ?
C33 C32 C37 119.35(13) ?
C31 C32 C37 117.21(13) ?
C34 C33 C32 120.40(14) ?
C34 C33 H33 119.8 ?
C32 C33 H33 119.8 ?
C33 C34 C35 120.60(14) ?
C33 C34 H34 119.7 ?
C35 C34 H34 119.7 ?
C36 C35 C34 120.18(14) ?
C36 C35 H35 119.9 ?
C34 C35 H35 119.9 ?
C35 C36 C37 120.94(14) ?
C35 C36 H36 119.5 ?
C37 C36 H36 119.5 ?
C36 C37 C38 121.89(14) ?
C36 C37 C32 118.53(13) ?
C38 C37 C32 119.58(14) ?
C39 C38 C37 120.70(14) ?
C39 C38 H38 119.6 ?
C37 C38 H38 119.6 ?
C38 C39 C310 120.62(14) ?
C38 C39 H39 119.7 ?
C310 C39 H39 119.7 ?
C31 C310 C39 119.43(14) ?
C31 C310 H310 120.3 ?
C39 C310 H310 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O1 1.6425(11) y
P O2 1.6376(11) y
P O3 1.6086(11) y
O1 C11 1.3906(18) y
O2 C21 1.3889(17) y
O3 C31 1.4026(17) y
C11 C110 1.371(2) ?
C11 C12 1.422(2) ?
C12 C17 1.421(2) ?
C12 C13 1.422(2) ?
C13 C14 1.372(2) ?
C13 H13 0.950 ?
C14 C15 1.405(2) ?
C14 H14 0.950 ?
C15 C16 1.369(2) ?
C15 H15 0.950 ?
C16 C17 1.419(2) ?
C16 H16 0.950 ?
C17 C18 1.418(2) ?
C18 C19 1.362(2) ?
C18 H18 0.950 ?
C19 C110 1.412(2) ?
C19 H19 0.950 ?
C110 H110 0.950 ?
C21 C210 1.368(2) ?
C21 C22 1.424(2) ?
C22 C27 1.419(2) ?
C22 C23 1.419(2) ?
C23 C24 1.369(2) ?
C23 H23 0.950 ?
C24 C25 1.407(2) ?
C24 H24 0.950 ?
C25 C26 1.366(2) ?
C25 H25 0.950 ?
C26 C27 1.415(2) ?
C26 H26 0.950 ?
C27 C28 1.418(2) ?
C28 C29 1.366(2) ?
C28 H28 0.950 ?
C29 C210 1.412(2) ?
C29 H29 0.950 ?
C210 H210 0.950 ?
C31 C310 1.365(2) ?
C31 C32 1.420(2) ?
C32 C33 1.417(2) ?
C32 C37 1.425(2) ?
C33 C34 1.367(2) ?
C33 H33 0.950 ?
C34 C35 1.413(2) ?
C34 H34 0.950 ?
C35 C36 1.368(2) ?
C35 H35 0.950 ?
C36 C37 1.417(2) ?
C36 H36 0.950 ?
C37 C38 1.417(2) ?
C38 C39 1.364(2) ?
C38 H38 0.950 ?
C39 C310 1.409(2) ?
C39 H39 0.950 ?
C310 H310 0.950 ?
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_publ_flag
O3 P O1 C11 -171.12(10) ?
O2 P O1 C11 86.13(10) y
O3 P O2 C21 107.89(11) y
O1 P O2 C21 -152.88(11) ?
O2 P O3 C31 30.61(12) ?
O1 P O3 C31 -65.99(12) y
P O1 C11 C110 -19.62(18) ?
P O1 C11 C12 160.36(10) y
C110 C11 C12 C17 0.2(2) ?
O1 C11 C12 C17 -179.74(12) ?
C110 C11 C12 C13 -179.48(14) ?
O1 C11 C12 C13 0.5(2) ?
C17 C12 C13 C14 0.2(2) ?
C11 C12 C13 C14 179.88(14) ?
C12 C13 C14 C15 -0.1(2) ?
C13 C14 C15 C16 0.2(2) ?
C14 C15 C16 C17 -0.3(2) ?
C15 C16 C17 C18 179.83(14) ?
C15 C16 C17 C12 0.4(2) ?
C11 C12 C17 C18 0.5(2) ?
C13 C12 C17 C18 -179.77(13) ?
C11 C12 C17 C16 179.98(13) ?
C13 C12 C17 C16 -0.3(2) ?
C16 C17 C18 C19 179.97(14) ?
C12 C17 C18 C19 -0.6(2) ?
C17 C18 C19 C110 -0.1(2) ?
O1 C11 C110 C19 179.07(13) ?
C12 C11 C110 C19 -0.9(2) ?
C18 C19 C110 C11 0.8(2) ?
P O2 C21 C210 -19.9(2) ?
P O2 C21 C22 161.44(10) y
C210 C21 C22 C27 0.0(2) ?
O2 C21 C22 C27 178.73(12) ?
C210 C21 C22 C23 -179.70(14) ?
O2 C21 C22 C23 -1.0(2) ?
C27 C22 C23 C24 -0.4(2) ?
C21 C22 C23 C24 179.40(14) ?
C22 C23 C24 C25 0.6(2) ?
C23 C24 C25 C26 -0.2(2) ?
C24 C25 C26 C27 -0.5(2) ?
C25 C26 C27 C28 -179.49(15) ?
C25 C26 C27 C22 0.7(2) ?
C23 C22 C27 C26 -0.3(2) ?
C21 C22 C27 C26 179.94(13) ?
C23 C22 C27 C28 179.89(13) ?
C21 C22 C27 C28 0.1(2) ?
C26 C27 C28 C29 -179.54(15) ?
C22 C27 C28 C29 0.3(2) ?
C27 C28 C29 C210 -0.8(2) ?
O2 C21 C210 C29 -179.16(14) ?
C22 C21 C210 C29 -0.6(2) ?
C28 C29 C210 C21 1.0(2) ?
P O3 C31 C310 -75.04(17) ?
P O3 C31 C32 109.66(13) y
C310 C31 C32 C33 -177.79(14) ?
O3 C31 C32 C33 -2.6(2) ?
C310 C31 C32 C37 1.6(2) ?
O3 C31 C32 C37 176.76(12) ?
C31 C32 C33 C34 179.40(14) ?
C37 C32 C33 C34 0.1(2) ?
C32 C33 C34 C35 0.2(2) ?
C33 C34 C35 C36 -0.1(2) ?
C34 C35 C36 C37 -0.2(2) ?
C35 C36 C37 C38 -179.09(14) ?
C35 C36 C37 C32 0.5(2) ?
C33 C32 C37 C36 -0.4(2) ?
C31 C32 C37 C36 -179.79(13) ?
C33 C32 C37 C38 179.20(13) ?
C31 C32 C37 C38 -0.2(2) ?
C36 C37 C38 C39 178.37(15) ?
C32 C37 C38 C39 -1.2(2) ?
C37 C38 C39 C310 1.3(2) ?
O3 C31 C310 C39 -176.61(13) ?
C32 C31 C310 C39 -1.5(2) ?
C38 C39 C310 C31 0.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9628801
