#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/60/2016034.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_2016034
loop_
_publ_author_name
'McAdam, C. John'
'Robinson, Brian H.'
'Simpson, Jim'
_publ_section_title
;(η⁵-Cyclopentadienyl)(3-hydroxy-3-methylbut-1-ynyl-κC¹)(triphenylphosphine-κP)nickel(II):
 novel O---H···π bonding in an organometallic molecule
;
_journal_coeditor_code           GA3055
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m338
_journal_page_last               m340
_journal_paper_doi               10.1107/S0108270107026522
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Ni (C5 H5) (C5 H7 O) (C18 H15 P)]'
_chemical_formula_moiety         'C28 H27 Ni O P'
_chemical_formula_sum            'C28 H27 Ni O P'
_chemical_formula_weight         469.18
_chemical_name_systematic
;
(η⁵-Cyclopentadienyl)(3-hydroxy-3-methylbut-1-ynyl-
\kC¹)(triphenylphosphine-\kP)nickel(II)
;
_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
_cell_angle_alpha                100.643(5)
_cell_angle_beta                 109.694(4)
_cell_angle_gamma                94.490(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9097(8)
_cell_length_b                   11.0904(8)
_cell_length_c                   12.7489(14)
_cell_measurement_reflns_used    6347
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      32.36
_cell_measurement_theta_min      2.26
_cell_volume                     1152.13(19)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al.,  2002)'
_computing_publication_material
;
SHELXL97, enCIFer (Allen et al.,  2004), PLATON (Spek,
2003) and
PARST (Nardelli, 1995)
;
_computing_structure_refinement
'SHELXL97 (Sheldrick, 1997) and TITAN2000 (Hunter & Simpson, 1999)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.796
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_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  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28022
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         34.40
_diffrn_reflns_theta_min         1.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.450
_refine_diff_density_min         -1.733
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         7726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1339P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                6277
_reflns_number_total             7726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3055.cif
_cod_data_source_block           I
_cod_original_cell_volume        1152.13(18)
_cod_database_code               2016034
_cod_database_fobs_code          2016034
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
Ni Ni1 0.00183(3) 0.45924(2) 0.28343(2) 0.01420(10) Uani d . 1
C C1 0.1783(3) 0.41027(19) 0.38395(18) 0.0171(4) Uani d . 1
C C2 0.2950(3) 0.3709(2) 0.43907(18) 0.0179(4) Uani d . 1
C C3 0.4289(3) 0.3062(2) 0.49585(18) 0.0189(4) Uani d . 1
O O1 0.5384(2) 0.38328(16) 0.60236(14) 0.0209(3) Uani d . 1
H H1 0.584(5) 0.438(4) 0.590(3) 0.043(10) Uiso d . 1
C C4 0.3608(3) 0.1937(2) 0.5288(2) 0.0249(5) Uani d . 1
H H4A 0.4473 0.1458 0.5584 0.037 Uiso calc R 1
H H4B 0.2758 0.1412 0.4612 0.037 Uiso calc R 1
H H4C 0.3159 0.2221 0.5878 0.037 Uiso calc R 1
C C5 0.5204(3) 0.2676(3) 0.4158(2) 0.0275(5) Uani d . 1
H H5A 0.5653 0.3415 0.3982 0.041 Uiso calc R 1
H H5B 0.4464 0.2121 0.3449 0.041 Uiso calc R 1
H H5C 0.6082 0.2243 0.4531 0.041 Uiso calc R 1
C C11 -0.0306(3) 0.6143(2) 0.38877(19) 0.0221(4) Uani d . 1
H H11 0.0093 0.6269 0.4697 0.027 Uiso calc R 1
C C12 -0.1853(3) 0.5531(2) 0.31481(19) 0.0214(4) Uani d . 1
H H12 -0.2707 0.5225 0.3362 0.026 Uiso calc R 1
C C13 -0.1877(3) 0.5463(2) 0.20206(19) 0.0188(4) Uani d . 1
H H13 -0.2726 0.5030 0.1340 0.023 Uiso calc R 1
C C14 -0.0408(3) 0.6157(2) 0.2073(2) 0.0204(4) Uani d . 1
H H14 -0.0153 0.6320 0.1442 0.024 Uiso calc R 1
C C15 0.0568(3) 0.6543(2) 0.3222(2) 0.0221(4) Uani d . 1
H H15 0.1629 0.6995 0.3514 0.027 Uiso calc R 1
P P1 -0.01647(6) 0.28870(5) 0.16853(4) 0.01307(12) Uani d . 1
C C21 -0.1898(2) 0.23487(19) 0.03469(17) 0.0148(4) Uani d . 1
C C22 -0.2246(2) 0.3098(2) -0.04507(18) 0.0173(4) Uani d . 1
H H22 -0.1646 0.3904 -0.0262 0.021 Uiso calc R 1
C C23 -0.3464(3) 0.2671(2) -0.15174(18) 0.0205(4) Uani d . 1
H H23 -0.3679 0.3178 -0.2060 0.025 Uiso calc R 1
C C24 -0.4365(3) 0.1499(2) -0.17882(19) 0.0220(4) Uani d . 1
H H24 -0.5196 0.1209 -0.2516 0.026 Uiso calc R 1
C C25 -0.4059(3) 0.0753(2) -0.10029(19) 0.0215(4) Uani d . 1
H H25 -0.4683 -0.0044 -0.1188 0.026 Uiso calc R 1
C C26 -0.2827(3) 0.1178(2) 0.00634(18) 0.0177(4) Uani d . 1
H H26 -0.2617 0.0667 0.0602 0.021 Uiso calc R 1
C C31 0.1473(2) 0.29096(18) 0.11290(17) 0.0146(4) Uani d . 1
C C32 0.1464(3) 0.1984(2) 0.02203(18) 0.0175(4) Uani d . 1
H H32 0.0616 0.1299 -0.0100 0.021 Uiso calc R 1
C C33 0.2701(3) 0.2064(2) -0.02186(19) 0.0195(4) Uani d . 1
H H33 0.2691 0.1432 -0.0837 0.023 Uiso calc R 1
C C34 0.3938(3) 0.3058(2) 0.02441(19) 0.0210(4) Uani d . 1
H H34 0.4787 0.3104 -0.0046 0.025 Uiso calc R 1
C C35 0.3933(3) 0.3990(2) 0.1138(2) 0.0224(4) Uani d . 1
H H35 0.4776 0.4679 0.1450 0.027 Uiso calc R 1
C C36 0.2706(3) 0.3921(2) 0.15750(18) 0.0186(4) Uani d . 1
H H36 0.2707 0.4565 0.2181 0.022 Uiso calc R 1
C C41 -0.0134(2) 0.15683(18) 0.23507(17) 0.0147(4) Uani d . 1
C C42 0.0757(3) 0.06126(19) 0.22151(18) 0.0176(4) Uani d . 1
H H42 0.1440 0.0650 0.1785 0.021 Uiso calc R 1
C C43 0.0651(3) -0.0395(2) 0.27061(19) 0.0217(4) Uani d . 1
H H43 0.1258 -0.1045 0.2607 0.026 Uiso calc R 1
C C44 -0.0343(3) -0.0456(2) 0.3343(2) 0.0231(4) Uani d . 1
H H44 -0.0422 -0.1150 0.3671 0.028 Uiso calc R 1
C C45 -0.1218(3) 0.0503(2) 0.34955(19) 0.0222(4) Uani d . 1
H H45 -0.1887 0.0469 0.3936 0.027 Uiso calc R 1
C C46 -0.1117(3) 0.1509(2) 0.30057(19) 0.0194(4) Uani d . 1
H H46 -0.1716 0.2162 0.3114 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'
Ni Ni 0.3393 1.1124 '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
C1 Ni1 C13 167.17(9) ?
C1 Ni1 C11 101.20(9) ?
C13 Ni1 C11 65.98(9) ?
C1 Ni1 C15 104.11(9) ?
C13 Ni1 C15 66.01(9) ?
C11 Ni1 C15 40.02(9) ?
C1 Ni1 P1 86.12(6) y
C13 Ni1 P1 106.62(6) ?
C11 Ni1 P1 168.12(8) ?
C15 Ni1 P1 147.29(7) ?
C1 Ni1 C14 135.76(9) ?
C13 Ni1 C14 39.94(9) ?
C11 Ni1 C14 65.63(9) ?
C15 Ni1 C14 38.24(9) ?
P1 Ni1 C14 115.31(6) ?
C1 Ni1 C12 130.30(9) ?
C13 Ni1 C12 39.26(8) ?
C11 Ni1 C12 39.01(9) ?
C15 Ni1 C12 66.06(9) ?
P1 Ni1 C12 129.49(7) ?
C14 Ni1 C12 65.88(9) ?
C2 C1 Ni1 172.94(18) y
C1 C2 C3 172.3(2) y
O1 C3 C2 111.68(18) ?
O1 C3 C5 109.83(19) ?
C2 C3 C5 109.55(18) ?
O1 C3 C4 104.86(18) ?
C2 C3 C4 109.50(19) ?
C5 C3 C4 111.4(2) ?
C3 O1 H1 109(3) ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
C3 C5 H5A 109.5 ?
C3 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C3 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C12 C11 C15 109.1(2) ?
C12 C11 Ni1 72.86(12) ?
C15 C11 Ni1 71.00(12) ?
C12 C11 H11 125.5 ?
C15 C11 H11 125.5 ?
Ni1 C11 H11 122.3 ?
C11 C12 C13 106.2(2) ?
C11 C12 Ni1 68.13(12) ?
C13 C12 Ni1 67.79(12) ?
C11 C12 H12 126.9 ?
C13 C12 H12 126.9 ?
Ni1 C12 H12 128.7 ?
C12 C13 C14 109.0(2) ?
C12 C13 Ni1 72.95(13) ?
C14 C13 Ni1 72.41(12) ?
C12 C13 H13 125.5 ?
C14 C13 H13 125.5 ?
Ni1 C13 H13 120.9 ?
C15 C14 C13 107.2(2) ?
C15 C14 Ni1 69.69(13) ?
C13 C14 Ni1 67.66(12) ?
C15 C14 H14 126.4 ?
C13 C14 H14 126.4 ?
Ni1 C14 H14 127.8 ?
C14 C15 C11 108.1(2) ?
C14 C15 Ni1 72.07(13) ?
C11 C15 Ni1 68.98(12) ?
C14 C15 H15 125.9 ?
C11 C15 H15 125.9 ?
Ni1 C15 H15 124.6 ?
C41 P1 C31 108.21(9) ?
C41 P1 C21 102.17(9) ?
C31 P1 C21 100.12(9) ?
C41 P1 Ni1 112.27(7) ?
C31 P1 Ni1 111.33(7) ?
C21 P1 Ni1 121.43(7) ?
C26 C21 C22 118.75(19) ?
C26 C21 P1 122.07(16) ?
C22 C21 P1 119.05(15) ?
C23 C22 C21 120.5(2) ?
C23 C22 H22 119.7 ?
C21 C22 H22 119.7 ?
C24 C23 C22 119.9(2) ?
C24 C23 H23 120.1 ?
C22 C23 H23 120.1 ?
C25 C24 C23 120.4(2) ?
C25 C24 H24 119.8 ?
C23 C24 H24 119.8 ?
C24 C25 C26 119.6(2) ?
C24 C25 H25 120.2 ?
C26 C25 H25 120.2 ?
C25 C26 C21 120.8(2) ?
C25 C26 H26 119.6 ?
C21 C26 H26 119.6 ?
C36 C31 C32 119.29(19) ?
C36 C31 P1 118.81(14) ?
C32 C31 P1 121.76(16) ?
C31 C32 C33 120.1(2) ?
C31 C32 H32 119.9 ?
C33 C32 H32 119.9 ?
C34 C33 C32 120.22(19) ?
C34 C33 H33 119.9 ?
C32 C33 H33 119.9 ?
C33 C34 C35 119.7(2) ?
C33 C34 H34 120.2 ?
C35 C34 H34 120.2 ?
C36 C35 C34 120.4(2) ?
C36 C35 H35 119.8 ?
C34 C35 H35 119.8 ?
C35 C36 C31 120.22(19) ?
C35 C36 H36 119.9 ?
C31 C36 H36 119.9 ?
C42 C41 C46 119.09(19) ?
C42 C41 P1 123.89(16) ?
C46 C41 P1 116.99(16) ?
C43 C42 C41 120.3(2) ?
C43 C42 H42 119.9 ?
C41 C42 H42 119.9 ?
C42 C43 C44 120.3(2) ?
C42 C43 H43 119.8 ?
C44 C43 H43 119.8 ?
C45 C44 C43 119.7(2) ?
C45 C44 H44 120.2 ?
C43 C44 H44 120.2 ?
C46 C45 C44 120.1(2) ?
C46 C45 H45 119.9 ?
C44 C45 H45 119.9 ?
C45 C46 C41 120.4(2) ?
C45 C46 H46 119.8 ?
C41 C46 H46 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 C1 1.855(2) y
Ni1 C13 2.075(2) ?
Ni1 C11 2.081(2) ?
Ni1 C15 2.108(2) ?
Ni1 P1 2.1253(6) y
Ni1 C14 2.138(2) ?
Ni1 C12 2.143(2) ?
C1 C2 1.208(3) y
C2 C3 1.485(3) y
C3 O1 1.440(3) y
C3 C4 1.533(3) y
C3 C5 1.531(3) y
O1 H1 0.77(4) y
C4 H4A 0.9800 ?
C4 H4B 0.9800 ?
C4 H4C 0.9800 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C11 C12 1.411(3) ?
C11 C15 1.433(3) ?
C11 H11 0.9500 ?
C12 C13 1.418(3) ?
C12 H12 0.9500 ?
C13 C14 1.440(3) ?
C13 H13 0.9500 ?
C14 C15 1.391(3) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
P1 C41 1.819(2) ?
P1 C31 1.825(2) ?
P1 C21 1.832(2) ?
C21 C26 1.399(3) ?
C21 C22 1.400(3) ?
C22 C23 1.392(3) ?
C22 H22 0.9500 ?
C23 C24 1.391(3) ?
C23 H23 0.9500 ?
C24 C25 1.386(3) ?
C24 H24 0.9500 ?
C25 C26 1.397(3) ?
C25 H25 0.9500 ?
C26 H26 0.9500 ?
C31 C36 1.392(3) ?
C31 C32 1.396(3) ?
C32 C33 1.397(3) ?
C32 H32 0.9500 ?
C33 C34 1.382(3) ?
C33 H33 0.9500 ?
C34 C35 1.391(3) ?
C34 H34 0.9500 ?
C35 C36 1.388(3) ?
C35 H35 0.9500 ?
C36 H36 0.9500 ?
C41 C42 1.393(3) ?
C41 C46 1.405(3) ?
C42 C43 1.389(3) ?
C42 H42 0.9500 ?
C43 C44 1.394(3) ?
C43 H43 0.9500 ?
C44 C45 1.390(3) ?
C44 H44 0.9500 ?
C45 C46 1.386(3) ?
C45 H45 0.9500 ?
C46 H46 0.9500 ?
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
C36 H36 O1 2_666 0.95 2.59 3.389(3) 142.3
C23 H23 O1 1_454 0.95 2.56 3.475(3) 160.8
C34 H34 Cg1 1_655 0.95 2.63 3.460(3) 147
