#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/19/7051965.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_7051965
loop_
_publ_author_name
'Olivier, Jean-Hubert'
'Camerel, Franck'
'Ziessel, Raymond'
'Retailleau, Pascal'
'Amadou, Julien'
'Pham-Huu, Cuong'
_publ_section_title
;
 Microwave-promoted hydrogenation and alkynylation reactions with
 palladium-loaded multi-walled carbon nanotubes
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              920
_journal_paper_doi               10.1039/b802014k
_journal_volume                  32
_journal_year                    2008
_chemical_formula_moiety         'C27 H24 O2'
_chemical_formula_sum            'C27 H24 O2'
_chemical_formula_weight         380.46
_chemical_name_systematic
;
?
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.02(5)
_cell_angle_beta                 82.48(5)
_cell_angle_gamma                81.90(4)
_cell_formula_units_Z            2
_cell_length_a                   5.644(1)
_cell_length_b                   12.047(2)
_cell_length_c                   16.159(2)
_cell_measurement_reflns_used    11120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.257
_cell_measurement_theta_min      0.407
_cell_volume                     1070.2(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .992
_diffrn_measured_fraction_theta_max .992
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22116
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Gaussian integration (Coppens, 1970)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.18
_refine_diff_density_max         .162
_refine_diff_density_min         -.121
_refine_diff_density_rms         .027
_refine_ls_extinction_coef       0.094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0475
_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)+(0.0820P)²+0.0851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2158
_reflns_number_total             3081
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802014k.txt
_cod_data_source_block           jho204_ccdc_661999
_cod_database_code               7051965
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3314(3) 0.27326(11) 0.02914(9) 0.0779(5) Uani 1 1 d . . .
O2 O 0.4340(3) 0.37680(14) 0.11883(12) 0.1144(7) Uani 1 1 d . . .
C1 C 1.3142(3) -0.10998(16) 0.23877(12) 0.0635(5) Uani 1 1 d . . .
C2 C 1.1489(3) -0.08999(16) 0.18312(12) 0.0675(5) Uani 1 1 d . . .
H2 H 1.1440 -0.1501 0.1533 0.081 Uiso 1 1 calc R . .
C3 C 0.9774(3) 0.00888(16) 0.16158(12) 0.0632(5) Uani 1 1 d . . .
C4 C 0.9582(4) 0.11224(18) 0.19392(14) 0.0779(6) Uani 1 1 d . . .
H4 H 1.0621 0.1213 0.2320 0.093 Uiso 1 1 calc R . .
C5 C 0.7886(4) 0.20037(17) 0.17030(13) 0.0764(6) Uani 1 1 d . . .
H5 H 0.7784 0.2678 0.1931 0.092 Uiso 1 1 calc R . .
C6 C 0.6329(3) 0.19071(16) 0.11335(11) 0.0639(5) Uani 1 1 d . . .
C7 C 0.6496(4) 0.08930(17) 0.08038(13) 0.0707(6) Uani 1 1 d . . .
H7 H 0.5461 0.0809 0.0420 0.085 Uiso 1 1 calc R . .
C8 C 0.8193(4) 0.00091(17) 0.10444(13) 0.0716(6) Uani 1 1 d . . .
H8 H 0.8282 -0.0665 0.0816 0.086 Uiso 1 1 calc R . .
C9 C 0.4591(4) 0.28981(17) 0.08910(13) 0.0719(6) Uani 1 1 d . . .
C10 C 0.1593(4) 0.36755(18) 0.00123(15) 0.0838(7) Uani 1 1 d . . .
H10A H 0.2429 0.4300 -0.0265 0.101 Uiso 1 1 calc R . .
H10B H 0.0531 0.3929 0.0490 0.101 Uiso 1 1 calc R . .
C12 C 1.4684(3) -0.22104(16) 0.25178(11) 0.0620(5) Uani 1 1 d . . .
C13 C 1.4185(3) -0.31829(17) 0.22266(13) 0.0724(6) Uani 1 1 d . . .
H13 H 1.2839 -0.3144 0.1942 0.087 Uiso 1 1 calc R . .
C14 C 1.5632(4) -0.41953(17) 0.23495(13) 0.0732(6) Uani 1 1 d . . .
H14 H 1.5244 -0.4823 0.2145 0.088 Uiso 1 1 calc R . .
C15 C 1.7638(3) -0.43035(17) 0.27667(12) 0.0661(5) Uani 1 1 d . . .
C16 C 1.8127(4) -0.33463(19) 0.30685(13) 0.0755(6) Uani 1 1 d . . .
H16 H 1.9463 -0.3394 0.3359 0.091 Uiso 1 1 calc R . .
C17 C 1.6690(3) -0.23297(18) 0.29504(13) 0.0729(6) Uani 1 1 d . . .
H17 H 1.7072 -0.1708 0.3165 0.087 Uiso 1 1 calc R . .
C18 C 1.9294(4) -0.53931(19) 0.28697(15) 0.0892(7) Uani 1 1 d . . .
H18A H 1.8359 -0.6008 0.3050 0.134 Uiso 1 1 calc R . .
H18B H 2.0349 -0.5357 0.3283 0.134 Uiso 1 1 calc R . .
H18C H 2.0232 -0.5510 0.2342 0.134 Uiso 1 1 calc R . .
C19 C 1.3578(3) -0.02665(16) 0.28825(12) 0.0671(5) Uani 1 1 d . . .
C20 C 1.4154(3) 0.03721(17) 0.33053(13) 0.0690(6) Uani 1 1 d . . .
C21 C 1.4914(3) 0.11424(17) 0.37893(12) 0.0661(5) Uani 1 1 d . . .
C22 C 1.3810(4) 0.2225(2) 0.38003(17) 0.0961(8) Uani 1 1 d . . .
H22 H 1.2497 0.2467 0.3499 0.115 Uiso 1 1 calc R . .
C23 C 1.4601(5) 0.2965(2) 0.42488(19) 0.1076(9) Uani 1 1 d . . .
H23 H 1.3828 0.3701 0.4233 0.129 Uiso 1 1 calc R . .
C11 C 0.0179(4) 0.32905(18) -0.05814(13) 0.0823(7) Uani 1 1 d . . .
H11A H 0.1244 0.3046 -0.1053 0.124 Uiso 1 1 calc R . .
H11B H -0.0978 0.3903 -0.0774 0.124 Uiso 1 1 calc R . .
H11C H -0.0643 0.2674 -0.0301 0.124 Uiso 1 1 calc R . .
C24 C 1.6473(5) 0.2652(2) 0.47120(14) 0.0889(7) Uani 1 1 d . . .
C25 C 1.7583(5) 0.1572(3) 0.47001(16) 0.1128(10) Uani 1 1 d . . .
H25 H 1.8889 0.1334 0.5005 0.135 Uiso 1 1 calc R . .
C26 C 1.6819(5) 0.0818(2) 0.42464(17) 0.1033(9) Uani 1 1 d . . .
H26 H 1.7611 0.0087 0.4254 0.124 Uiso 1 1 calc R . .
C27 C 1.7360(6) 0.3463(3) 0.52026(17) 0.1370(13) Uani 1 1 d . . .
H27A H 1.8786 0.3106 0.5443 0.205 Uiso 1 1 calc R . .
H27B H 1.6133 0.3672 0.5643 0.205 Uiso 1 1 calc R . .
H27C H 1.7725 0.4127 0.4832 0.205 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
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.250000
-1 0 0 0.350000
0 1 0 0.140000
0 -1 0 0.140000
0 0 1 0.240000
0 0 -1 0.360000
4 -6 -5 0.267000
-1 2 10 0.291000
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
_geom_angle_publ_flag
C9 O1 C10 116.06(15) . . ?
C2 C1 C19 122.98(18) . . ?
C2 C1 C12 121.98(18) . . ?
C19 C1 C12 115.02(16) . . ?
C1 C2 C3 131.57(18) . . ?
C1 C2 H2 114.2 . . ?
C3 C2 H2 114.2 . . ?
C8 C3 C4 116.78(18) . . ?
C8 C3 C2 117.83(17) . . ?
C4 C3 C2 125.39(17) . . ?
C5 C4 C3 121.06(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.26(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 118.56(19) . . ?
C5 C6 C9 118.39(18) . . ?
C7 C6 C9 123.03(18) . . ?
C8 C7 C6 120.04(18) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 122.30(18) . . ?
C7 C8 H8 118.9 . . ?
C3 C8 H8 118.9 . . ?
O2 C9 O1 122.5(2) . . ?
O2 C9 C6 124.54(19) . . ?
O1 C9 C6 112.92(17) . . ?
O1 C10 C11 107.99(17) . . ?
O1 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O1 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C17 C12 C13 116.34(19) . . ?
C17 C12 C1 121.08(17) . . ?
C13 C12 C1 122.58(16) . . ?
C14 C13 C12 121.67(17) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 121.69(19) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 117.01(19) . . ?
C14 C15 C18 122.08(19) . . ?
C16 C15 C18 120.88(18) . . ?
C17 C16 C15 121.81(18) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C12 121.46(19) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C1 173.7(2) . . ?
C19 C20 C21 178.0(2) . . ?
C26 C21 C22 117.5(2) . . ?
C26 C21 C20 120.7(2) . . ?
C22 C21 C20 121.89(18) . . ?
C21 C22 C23 121.3(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C23 C24 C25 116.9(2) . . ?
C23 C24 C27 122.1(3) . . ?
C25 C24 C27 120.9(3) . . ?
C24 C25 C26 121.9(2) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C25 120.5(2) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.332(2) . ?
O1 C10 1.449(3) . ?
O2 C9 1.195(2) . ?
C1 C2 1.354(3) . ?
C1 C19 1.432(3) . ?
C1 C12 1.494(3) . ?
C2 C3 1.458(3) . ?
C2 H2 0.9300 . ?
C3 C8 1.386(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(3) . ?
C6 C9 1.477(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.483(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C17 1.388(3) . ?
C12 C13 1.398(3) . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(3) . ?
C15 C18 1.503(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.199(3) . ?
C20 C21 1.435(3) . ?
C21 C26 1.365(3) . ?
C21 C22 1.365(3) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(3) . ?
C23 H23 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C24 C25 1.363(4) . ?
C24 C27 1.514(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C1 C2 C3 -2.8(3) . . . . ?
C12 C1 C2 C3 178.33(19) . . . . ?
C1 C2 C3 C8 -176.2(2) . . . . ?
C1 C2 C3 C4 3.8(4) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C4 C5 C6 C9 -178.4(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C9 C6 C7 C8 178.64(19) . . . . ?
C6 C7 C8 C3 0.2(3) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
C2 C3 C8 C7 179.60(19) . . . . ?
C10 O1 C9 O2 0.3(3) . . . . ?
C10 O1 C9 C6 -179.16(18) . . . . ?
C5 C6 C9 O2 -4.3(3) . . . . ?
C7 C6 C9 O2 176.9(2) . . . . ?
C5 C6 C9 O1 175.14(18) . . . . ?
C7 C6 C9 O1 -3.7(3) . . . . ?
C9 O1 C10 C11 -173.93(17) . . . . ?
C2 C1 C12 C17 166.32(19) . . . . ?
C19 C1 C12 C17 -12.6(3) . . . . ?
C2 C1 C12 C13 -14.6(3) . . . . ?
C19 C1 C12 C13 166.46(18) . . . . ?
C17 C12 C13 C14 -1.2(3) . . . . ?
C1 C12 C13 C14 179.70(18) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C13 C14 C15 C18 -177.1(2) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C18 C15 C16 C17 177.3(2) . . . . ?
C15 C16 C17 C12 -0.4(3) . . . . ?
C13 C12 C17 C16 1.3(3) . . . . ?
C1 C12 C17 C16 -179.59(19) . . . . ?
C26 C21 C22 C23 0.6(4) . . . . ?
C20 C21 C22 C23 -178.1(2) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C22 C23 C24 C25 1.4(4) . . . . ?
C22 C23 C24 C27 179.7(2) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C27 C24 C25 C26 -179.2(2) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
C20 C21 C26 C25 178.6(2) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652915
