#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/47/2204762.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_2204762
loop_
_publ_author_name
'Jian-Ming Gu'
'Mao-Sheng Xu'
'Xiu-Rong Hu'
_publ_section_title
;
 1-(Diphenylphosphinoyl)-3,3-dimethylbut-1-yne
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2177
_journal_page_last               o2178
_journal_paper_doi               10.1107/S1600536804027217
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C18 H19 O P'
_chemical_formula_moiety         'C18 H19 O P'
_chemical_formula_sum            'C18 H19 O P'
_chemical_formula_weight         282.32
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4742(7)
_cell_length_b                   9.5767(7)
_cell_length_c                   11.2075(6)
_cell_measurement_reflns_used    8920
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_cell_volume                     1553.53(16)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'CRYSTALS (Watkin et al., 1996)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7260
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             600.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details '(Flack, 1983), 632 Friedel pairs'
_refine_ls_abs_structure_Flack   0.010(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1309
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.001Fo² + 1.1σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1309
_reflns_number_total             1688
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6424.cif
_cod_data_source_block           I
_cod_original_cell_volume        1553.5(2)
_cod_database_code               2204762
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,+Z
3 +X,-Y,1/2+Z
4 -X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,+Z
7 1/2+X,1/2-Y,1/2+Z
8 1/2-X,1/2-Y,1/2+Z
loop_
_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
_atom_site_type_symbol
P1 0.5000 0.58355(8) 0.35768(9) 0.0410(2) Uani d S 1.00 P
O1 0.5000 0.6571(3) 0.4734(2) 0.0557(7) Uani d S 1.00 O
C1 0.5000 0.2789(3) 0.3852(3) 0.0480(10) Uani d S 1.00 C
C2 0.5000 0.4020(3) 0.3694(4) 0.0483(8) Uani d S 1.00 C
C3 0.39870(10) 0.6231(2) 0.2707(2) 0.0399(5) Uani d .. 1.00 C
C4 0.3396(2) 0.7249(3) 0.3147(2) 0.0548(7) Uani d .. 1.00 C
C5 0.2606(2) 0.7590(3) 0.2540(3) 0.0697(9) Uani d .. 1.00 C
C6 0.2402(2) 0.6943(3) 0.1485(3) 0.0655(9) Uani d .. 1.00 C
C7 0.2978(2) 0.5947(3) 0.1034(3) 0.0625(8) Uani d .. 1.00 C
C8 0.3773(2) 0.5582(2) 0.1647(2) 0.0525(7) Uani d .. 1.00 C
C9 0.5000 0.1272(4) 0.4057(3) 0.0455(9) Uani d S 1.00 C
C10 0.500000(10) 0.0535(4) 0.2855(4) 0.0700(10) Uani d S 1.00 C
C11 0.4137(2) 0.0888(3) 0.4755(3) 0.0711(9) Uani d .. 1.00 C
H4 0.3550 0.7721 0.3887 0.066 Uiso c R 1.00 H
H5 0.2191 0.8298 0.2849 0.084 Uiso c R 1.00 H
H6 0.1842 0.7185 0.1058 0.079 Uiso c R 1.00 H
H7 0.2829 0.5490 0.0286 0.075 Uiso c R 1.00 H
H8 0.4189 0.4874 0.1337 0.063 Uiso c R 1.00 H
H102 0.4455 0.0813 0.2412 0.084 Uiso c R 1.00 H
H101 0.5000 -0.0470 0.2965 0.084 Uiso c R 1.00 H
H111 0.4270 0.0939 0.5603 0.086 Uiso c R 1.00 H
H112 0.3641 0.1532 0.4563 0.086 Uiso c R 1.00 H
H113 0.3950 -0.0055 0.4551 0.086 Uiso c R 1.00 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
C2 P1 O1 . . . 114.2(2)
C3 P1 O1 . . . 112.04(9)
C3 P1 O1 2_655 . . 112.04(9)
P1 C2 C1 . . . 175.8(4)
C3 P1 C2 . . . 104.50(10)
C3 P1 C2 2_655 . . 104.50(10)
C3 P1 C3 2_655 . . 109.00(10)
P1 C3 C4 . . . 117.2(2)
P1 C3 C8 . . . 123.7(2)
P1 C3 C4 . 2_655 2_655 117.2(2)
P1 C3 C8 . 2_655 2_655 123.7(2)
C9 C1 C2 . . . 179.5(4)
C1 C9 C10 . . . 108.6(3)
C1 C9 C11 . . . 108.6(2)
C1 C9 C11 . . 2_655 108.6(2)
C8 C3 C4 . . . 119.1(2)
C3 C4 C5 . . . 120.4(2)
C3 C8 C7 . . . 120.0(2)
C4 C5 C6 . . . 120.1(3)
C5 C6 C7 . . . 120.4(3)
C6 C7 C8 . . . 120.0(3)
C11 C9 C10 . . . 110.1(2)
C11 C9 C10 2_655 . . 110.1(2)
C11 C9 C11 2_655 . . 110.6(3)
C3 C4 H4 . . . 119.4125
C3 C8 H8 . . . 119.0518
H4 C4 C5 . . . 120.2290
C4 C5 H5 . . . 120.4393
H5 C5 C6 . . . 119.4669
C5 C6 H6 . . . 119.9531
C6 C7 H7 . . . 120.0094
H6 C6 C7 . . . 119.6636
C7 C8 H8 . . . 120.9117
H7 C7 C8 . . . 119.9652
C9 C10 H102 . . . 109.0384
C9 C10 H102 . . 2_655 109.0384
C9 C10 H101 . . . 110.3236
C9 C11 H111 . . . 109.1616
C9 C11 H112 . . . 109.8444
C9 C11 H113 . . . 109.4044
C9 C11 H111 . 2_655 2_655 109.1616
C9 C11 H112 . 2_655 2_655 109.8444
C9 C11 H113 . 2_655 2_655 109.4044
H102 C10 H102 2_655 . . 108.8849
H101 C10 H102 . . . 109.7640
H101 C10 H102 . . 2_655 109.7640
H112 C11 H111 . . . 109.4717
H113 C11 H111 . . . 109.4678
H113 C11 H112 . . . 109.4765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 O1 . 1.476(2)
P1 C2 . 1.744(3)
P1 C3 . 1.801(2)
P1 C3 2_655 1.801(2)
C1 C2 . 1.192(4)
C1 C9 . 1.472(5)
C3 C4 . 1.387(3)
C3 C8 . 1.376(3)
C4 C5 . 1.370(4)
C5 C6 . 1.367(4)
C6 C7 . 1.364(4)
C7 C8 . 1.385(4)
C9 C10 . 1.521(5)
C9 C10 2_655 1.521(5)
C9 C11 . 1.519(4)
C9 C11 2_655 1.519(4)
C4 H4 . 0.9700
C5 H5 . 0.9700
C6 H6 . 0.9699
C7 H7 . 0.9700
C8 H8 . 0.9700
C10 H102 . 0.9700
C10 H102 2_655 0.9700
C10 H101 . 0.9700
C10 H101 2_655 0.9700
C11 H111 . 0.9700
C11 H112 . 0.9700
C11 H113 . 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8 O1 3_564 0.97 2.55 3.464(3) 156 yes
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
O(1) P(1) C(3) C(4) 6.4(2)
O(1) P(1) C(3) C(8) -173.5(3)
C(2) P(1) C(3) C(4) 130.5(3)
C(2) P(1) C(3) C(8) -49.4(4)
P(1) C(3) C(4) C(5) -179.1(2)
C(8) C(3) C(4) C(5) 0.7(4)
P(1) C(3) C(8) C(7) 179.9(2)
C(4) C(3) C(8) C(7) 0.0(3)
C(3) C(4) C(5) C(6) -1.0(4)
C(4) C(5) C(6) C(7) 0.5(5)
C(5) C(6) C(7) C(8) 0.2(4)
C(6) C(7) C(8) C(3) -0.5(4)
