#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023538.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_4023538
loop_
_publ_author_name
'Kohei Ogawa'
'Shinya Minegishi'
'Koichi Komatsu'
'Toshikazu Kitagawa'
_publ_contact_author_address
;
    Department of Chemistry for Materials, Graduate School of Engineering, 
    Mie University, Tsu, Mie 514-8507, Japan. 
;
_publ_contact_author_email       ' kitagawa@chem.mie-u.ac.jp'
_publ_contact_author_fax         ' +81-59-231-9416 '
_publ_contact_author_name        ' Toshikazu Kitagawa '
_publ_contact_author_phone       ' +81-59-231-9416 '
_publ_section_title
;
 Generation and Reaction of a Phenyl-Substituted Cyclopentadienyl
 Cation Annelated with Two Homoadamantene Frameworks
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5248
_journal_page_last               5254
_journal_paper_doi               10.1021/jo800340g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C29 H34'
_chemical_formula_sum            'C29 H34'
_chemical_formula_weight         382.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.512(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3533(12)
_cell_length_b                   17.527(3)
_cell_length_c                   18.820(4)
_cell_measurement_temperature    100(2)
_cell_volume                     2082.2(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10646
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9932
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                2366
_reflns_number_total             3672
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800340g-File001.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023538
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.4885(3) 0.24075(12) 0.28276(11) 0.0233(5) Uani 1 1 d . . .
C24 C 0.5383(3) 0.31332(12) 0.31993(10) 0.0233(5) Uani 1 1 d . . .
C3 C 0.3900(3) 0.11822(12) 0.25057(11) 0.0234(5) Uani 1 1 d . . .
C16 C 0.1990(3) 0.13380(12) 0.08573(11) 0.0261(6) Uani 1 1 d . . .
H16A H 0.1591 0.1007 0.0438 0.031 Uiso 1 1 calc R . .
H16B H 0.1030 0.1219 0.1221 0.031 Uiso 1 1 calc R . .
C4 C 0.4607(3) 0.14736(12) 0.19145(11) 0.0230(5) Uani 1 1 d . . .
C19 C 0.5408(4) 0.22544(12) 0.03475(11) 0.0268(6) Uani 1 1 d . . .
H19 H 0.6302 0.2329 -0.0052 0.032 Uiso 1 1 calc R . .
C29 C 0.3953(4) 0.34870(12) 0.36088(11) 0.0260(5) Uani 1 1 d . . .
H29 H 0.2619 0.3256 0.3647 0.031 Uiso 1 1 calc R . .
C5 C 0.5407(4) 0.22709(12) 0.20704(10) 0.0250(5) Uani 1 1 d . . .
H5 H 0.6985 0.2260 0.2085 0.030 Uiso 1 1 calc R . .
C21 C 0.4560(3) 0.28726(12) 0.15141(10) 0.0228(5) Uani 1 1 d . . .
H21 H 0.4689 0.3381 0.1757 0.027 Uiso 1 1 calc R . .
C22 C 0.5856(4) 0.14524(12) 0.06612(11) 0.0275(5) Uani 1 1 d . . .
H22A H 0.7294 0.1452 0.0927 0.033 Uiso 1 1 calc R . .
H22B H 0.5866 0.1088 0.0260 0.033 Uiso 1 1 calc R . .
C6 C 0.3472(3) 0.15967(13) 0.38084(11) 0.0259(5) Uani 1 1 d . . .
H6 H 0.3792 0.2066 0.4104 0.031 Uiso 1 1 calc R . .
C25 C 0.7294(4) 0.35050(13) 0.31414(11) 0.0269(5) Uani 1 1 d . . .
H25 H 0.8276 0.3285 0.2856 0.032 Uiso 1 1 calc R . .
C12 C 0.2955(4) 0.04059(12) 0.25982(11) 0.0283(6) Uani 1 1 d . . .
H12 H 0.2931 0.0134 0.2130 0.034 Uiso 1 1 calc R . .
C15 C 0.4282(3) 0.11591(12) 0.11656(10) 0.0238(5) Uani 1 1 d . . .
H15 H 0.4431 0.0592 0.1198 0.029 Uiso 1 1 calc R . .
C17 C 0.1697(3) 0.21717(12) 0.06320(11) 0.0254(5) Uani 1 1 d . . .
H17 H 0.0188 0.2244 0.0427 0.030 Uiso 1 1 calc R . .
C2 C 0.4071(3) 0.17576(12) 0.30761(11) 0.0241(5) Uani 1 1 d . . .
C7 C 0.4797(4) 0.09417(13) 0.41726(12) 0.0386(7) Uani 1 1 d . . .
H7A H 0.6288 0.1011 0.4080 0.046 Uiso 1 1 calc R . .
H7B H 0.4754 0.0980 0.4696 0.046 Uiso 1 1 calc R . .
C28 C 0.4459(4) 0.41711(13) 0.39601(11) 0.0283(6) Uani 1 1 d . . .
H28 H 0.3479 0.4400 0.4241 0.034 Uiso 1 1 calc R . .
C26 C 0.7792(4) 0.41862(13) 0.34900(11) 0.0317(6) Uani 1 1 d . . .
H26 H 0.9111 0.4427 0.3446 0.038 Uiso 1 1 calc R . .
C18 C 0.3096(4) 0.23284(13) 0.00427(11) 0.0283(6) Uani 1 1 d . . .
H18A H 0.2768 0.1959 -0.0353 0.034 Uiso 1 1 calc R . .
H18B H 0.2821 0.2849 -0.0150 0.034 Uiso 1 1 calc R . .
C20 C 0.5904(4) 0.29033(12) 0.08913(11) 0.0282(6) Uani 1 1 d . . .
H20A H 0.7420 0.2877 0.1083 0.034 Uiso 1 1 calc R . .
H20B H 0.5664 0.3399 0.0642 0.034 Uiso 1 1 calc R . .
C14 C 0.4349(4) -0.00688(13) 0.31588(11) 0.0394(7) Uani 1 1 d . . .
H14A H 0.3999 -0.0615 0.3083 0.047 Uiso 1 1 calc R . .
H14B H 0.5852 0.0001 0.3082 0.047 Uiso 1 1 calc R . .
C23 C 0.2192(3) 0.27532(13) 0.12466(11) 0.0281(6) Uani 1 1 d . . .
H23A H 0.1582 0.3252 0.1085 0.034 Uiso 1 1 calc R . .
H23B H 0.1459 0.2585 0.1657 0.034 Uiso 1 1 calc R . .
C27 C 0.6378(4) 0.45177(13) 0.39025(11) 0.0305(6) Uani 1 1 d . . .
H27 H 0.6728 0.4983 0.4146 0.037 Uiso 1 1 calc R . .
C13 C 0.1100(4) 0.14295(16) 0.38014(14) 0.0478(8) Uani 1 1 d . . .
H13A H 0.0293 0.1789 0.3469 0.057 Uiso 1 1 calc R . .
H13B H 0.0688 0.1524 0.4286 0.057 Uiso 1 1 calc R . .
C11 C 0.0678(4) 0.04407(16) 0.27792(13) 0.0479(8) Uani 1 1 d . . .
H11A H -0.0023 -0.0052 0.2647 0.057 Uiso 1 1 calc R . .
H11B H -0.0086 0.0843 0.2484 0.057 Uiso 1 1 calc R . .
C8 C 0.4087(5) 0.01391(15) 0.39325(13) 0.0516(8) Uani 1 1 d . . .
H8 H 0.4935 -0.0233 0.4250 0.062 Uiso 1 1 calc R . .
C9 C 0.1807(6) 0.00438(17) 0.40503(15) 0.0700(11) Uani 1 1 d . . .
H9A H 0.1632 0.0140 0.4559 0.084 Uiso 1 1 calc R . .
H9B H 0.1341 -0.0485 0.3931 0.084 Uiso 1 1 calc R . .
C10 C 0.0470(5) 0.06057(18) 0.35763(16) 0.0612(10) Uani 1 1 d . . .
H10 H -0.1045 0.0529 0.3655 0.073 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 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'
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
C2 C1 C24 129.28(19) . . ?
C2 C1 C5 108.89(18) . . ?
C24 C1 C5 121.70(19) . . ?
C25 C24 C29 117.5(2) . . ?
C25 C24 C1 120.7(2) . . ?
C29 C24 C1 121.8(2) . . ?
C4 C3 C2 109.85(19) . . ?
C4 C3 C12 127.81(19) . . ?
C2 C3 C12 122.28(19) . . ?
C17 C16 C15 112.37(18) . . ?
C3 C4 C5 109.16(18) . . ?
C3 C4 C15 127.7(2) . . ?
C5 C4 C15 122.00(18) . . ?
C18 C19 C20 107.70(18) . . ?
C18 C19 C22 110.57(18) . . ?
C20 C19 C22 113.90(17) . . ?
C28 C29 C24 121.0(2) . . ?
C4 C5 C1 102.97(17) . . ?
C4 C5 C21 114.80(17) . . ?
C1 C5 C21 115.69(18) . . ?
C20 C21 C5 111.31(18) . . ?
C20 C21 C23 111.29(17) . . ?
C5 C21 C23 112.39(18) . . ?
C19 C22 C15 115.83(18) . . ?
C2 C6 C13 112.34(18) . . ?
C2 C6 C7 111.55(18) . . ?
C13 C6 C7 110.4(2) . . ?
C26 C25 C24 121.5(2) . . ?
C3 C12 C11 113.0(2) . . ?
C3 C12 C14 111.18(19) . . ?
C11 C12 C14 110.8(2) . . ?
C4 C15 C16 107.60(17) . . ?
C4 C15 C22 115.10(18) . . ?
C16 C15 C22 110.61(17) . . ?
C18 C17 C16 108.16(18) . . ?
C18 C17 C23 109.86(18) . . ?
C16 C17 C23 114.51(17) . . ?
C1 C2 C3 108.93(18) . . ?
C1 C2 C6 128.5(2) . . ?
C3 C2 C6 122.55(19) . . ?
C8 C7 C6 115.3(2) . . ?
C27 C28 C29 120.1(2) . . ?
C27 C26 C25 120.1(2) . . ?
C19 C18 C17 109.19(17) . . ?
C21 C20 C19 113.22(18) . . ?
C8 C14 C12 114.0(2) . . ?
C21 C23 C17 116.14(18) . . ?
C28 C27 C26 119.8(2) . . ?
C6 C13 C10 113.9(2) . . ?
C12 C11 C10 114.3(2) . . ?
C9 C8 C14 109.0(2) . . ?
C9 C8 C7 108.4(2) . . ?
C14 C8 C7 116.1(2) . . ?
C8 C9 C10 109.0(2) . . ?
C9 C10 C13 109.5(2) . . ?
C9 C10 C11 110.1(2) . . ?
C13 C10 C11 113.1(2) . . ?
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
C1 C2 1.356(3) . ?
C1 C24 1.469(3) . ?
C1 C5 1.518(3) . ?
C24 C25 1.393(3) . ?
C24 C29 1.401(3) . ?
C3 C4 1.347(3) . ?
C3 C2 1.468(3) . ?
C3 C12 1.505(3) . ?
C16 C17 1.527(3) . ?
C16 C15 1.537(3) . ?
C4 C5 1.504(3) . ?
C4 C15 1.506(3) . ?
C19 C18 1.521(3) . ?
C19 C20 1.539(3) . ?
C19 C22 1.539(3) . ?
C29 C28 1.389(3) . ?
C5 C21 1.539(3) . ?
C21 C20 1.527(3) . ?
C21 C23 1.546(3) . ?
C22 C15 1.543(3) . ?
C6 C2 1.498(3) . ?
C6 C13 1.533(3) . ?
C6 C7 1.538(3) . ?
C25 C26 1.382(3) . ?
C12 C11 1.525(3) . ?
C12 C14 1.542(3) . ?
C17 C18 1.523(3) . ?
C17 C23 1.547(3) . ?
C7 C8 1.530(3) . ?
C28 C27 1.378(3) . ?
C26 C27 1.380(3) . ?
C14 C8 1.528(3) . ?
C13 C10 1.545(4) . ?
C11 C10 1.548(3) . ?
C8 C9 1.499(4) . ?
C9 C10 1.522(4) . ?
