#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203271.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_2203271
loop_
_publ_author_name
'Jones, Peter G.'
'Berger, Harald'
'Bubenitschek, Peter'
'Hopf, Henning'
_publ_section_title
;
 1,3-Di-tert-butyl-6-phenylethynyl-fulvene
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o444
_journal_page_last             o445
_journal_volume                60
_journal_year                  2004
_chemical_formula_moiety       ?
_chemical_formula_sum          'C22 H26'
_chemical_formula_weight       290.43
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
 1,3-Di-tert-butyl-6-phenylethynyl-fulvene
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_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               106.19(3)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 6.518(2)
_cell_length_b                 28.543(6)
_cell_length_c                 10.194(2)
_cell_measurement_reflns_used  56
_cell_measurement_temperature  143(2)
_cell_measurement_theta_max    11.5
_cell_measurement_theta_min    10
_cell_volume                   1821.3(8)
_computing_cell_refinement     DIF4
_computing_data_collection     'DIF4 (Stoe & Cie, 1992)'
_computing_data_reduction      'REDU4 (Stoe & Cie, 1992)'
_computing_molecular_graphics  'XP (Siemens, 1994)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature    143(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'Stoe STADI-4'
_diffrn_measurement_method     omega-scan
_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 0.0298
_diffrn_reflns_av_sigmaI/netI  0.0404
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_number          6153
_diffrn_reflns_theta_full      25.04
_diffrn_reflns_theta_max       25.04
_diffrn_reflns_theta_min       3.33
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 60
_diffrn_standards_number       3
_exptl_absorpt_coefficient_mu  0.059
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          red
_exptl_crystal_density_diffrn  1.059
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           632
_exptl_crystal_size_max        0.70
_exptl_crystal_size_mid        0.25
_exptl_crystal_size_min        0.25
_refine_diff_density_max       0.191
_refine_diff_density_min       -0.252
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.028
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   205
_refine_ls_number_reflns       3200
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.028
_refine_ls_R_factor_all        0.0732
_refine_ls_R_factor_gt         0.0525
_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/[\s^2^(Fo^2^)+(0.0665P)^2^+0.4622P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1249
_refine_ls_wR_factor_ref       0.1409
_reflns_number_gt              2436
_reflns_number_total           3200
_reflns_threshold_expression   I>2\s(I)
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 1.0910(3) 0.11045(6) 0.37829(17) 0.0307(4) Uani d . 1 . . C
C2 1.2319(3) 0.08072(6) 0.45808(17) 0.0321(4) Uani d . 1 . . C
H2 1.3424 0.0651 0.4311 0.039 Uiso calc R 1 . . H
C3 1.1925(3) 0.07550(6) 0.59238(17) 0.0324(4) Uani d . 1 . . C
C4 1.0260(3) 0.10306(6) 0.59402(18) 0.0323(4) Uani d . 1 . . C
H4 0.9670 0.1068 0.6687 0.039 Uiso calc R 1 . . H
C5 0.9508(3) 0.12642(6) 0.46142(17) 0.0310(4) Uani d . 1 . . C
C6 0.7851(3) 0.15678(6) 0.42770(19) 0.0351(4) Uani d . 1 . . C
H6 0.7466 0.1696 0.3382 0.042 Uiso calc R 1 . . H
C7 0.6660(3) 0.17048(6) 0.51747(19) 0.0366(4) Uani d . 1 . . C
C8 0.5617(3) 0.18297(6) 0.59189(19) 0.0364(5) Uani d . 1 . . C
C9 0.4385(3) 0.19612(6) 0.68187(18) 0.0342(4) Uani d . 1 . . C
C10 0.5122(4) 0.18667(7) 0.8213(2) 0.0439(5) Uani d . 1 . . C
H10 0.6478 0.1724 0.8574 0.053 Uiso calc R 1 . . H
C11 0.3898(4) 0.19790(7) 0.9070(2) 0.0509(6) Uani d . 1 . . C
H11 0.4416 0.1912 1.0018 0.061 Uiso calc R 1 . . H
C12 0.1929(4) 0.21876(7) 0.8567(2) 0.0484(5) Uani d . 1 . . C
H12 0.1086 0.2262 0.9163 0.058 Uiso calc R 1 . . H
C13 0.1192(3) 0.22878(7) 0.7194(2) 0.0431(5) Uani d . 1 . . C
H13 -0.0159 0.2434 0.6845 0.052 Uiso calc R 1 . . H
C14 0.2400(3) 0.21767(6) 0.63213(19) 0.0368(4) Uani d . 1 . . C
H14 0.1876 0.2247 0.5376 0.044 Uiso calc R 1 . . H
C15 1.0815(3) 0.12577(7) 0.23423(18) 0.0370(5) Uani d . 1 . . C
C16 0.8652(4) 0.11254(8) 0.1341(2) 0.0526(6) Uani d . 1 . . C
H16A 0.8643 0.1216 0.0413 0.063 Uiso calc R 1 . . H
H16B 0.7501 0.1289 0.1599 0.063 Uiso calc R 1 . . H
H16C 0.8436 0.0786 0.1375 0.063 Uiso calc R 1 . . H
C17 1.1180(4) 0.17881(7) 0.2294(2) 0.0480(5) Uani d . 1 . . C
H17A 1.1158 0.1880 0.1363 0.058 Uiso calc R 1 . . H
H17B 1.2568 0.1869 0.2924 0.058 Uiso calc R 1 . . H
H17C 1.0046 0.1955 0.2562 0.058 Uiso calc R 1 . . H
C18 1.2573(4) 0.10123(8) 0.1870(2) 0.0474(5) Uani d . 1 . . C
H18A 1.2529 0.1120 0.0949 0.057 Uiso calc R 1 . . H
H18B 1.2347 0.0673 0.1858 0.057 Uiso calc R 1 . . H
H18C 1.3969 0.1087 0.2500 0.057 Uiso calc R 1 . . H
C19 1.3198(3) 0.04312(6) 0.70285(18) 0.0365(4) Uani d . 1 . . C
C20 1.2510(4) 0.04804(9) 0.8322(2) 0.0645(7) Uani d . 1 . . C
H20A 1.3391 0.0276 0.9031 0.077 Uiso calc R 1 . . H
H20B 1.1006 0.0390 0.8139 0.077 Uiso calc R 1 . . H
H20C 1.2688 0.0807 0.8633 0.077 Uiso calc R 1 . . H
C21 1.2849(3) -0.00721(7) 0.6498(2) 0.0489(5) Uani d . 1 . . C
H21A 1.3716 -0.0286 0.7184 0.059 Uiso calc R 1 . . H
H21B 1.3270 -0.0099 0.5650 0.059 Uiso calc R 1 . . H
H21C 1.1336 -0.0154 0.6320 0.059 Uiso calc R 1 . . H
C22 1.5590(3) 0.05460(8) 0.7337(2) 0.0511(6) Uani d . 1 . . C
H22A 1.6412 0.0332 0.8041 0.061 Uiso calc R 1 . . H
H22B 1.5840 0.0870 0.7664 0.061 Uiso calc R 1 . . H
H22C 1.6043 0.0510 0.6503 0.061 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0274(9) 0.0322(9) 0.0334(9) 0.0000(7) 0.0099(8) 0.0003(7)
C2 0.0296(10) 0.0334(9) 0.0343(9) 0.0027(7) 0.0106(8) -0.0004(7)
C3 0.0313(10) 0.0310(9) 0.0339(9) -0.0015(7) 0.0076(8) -0.0018(7)
C4 0.0329(10) 0.0340(9) 0.0318(9) 0.0008(7) 0.0120(8) 0.0007(7)
C5 0.0283(9) 0.0293(9) 0.0351(9) -0.0003(7) 0.0083(8) 0.0008(7)
C6 0.0315(10) 0.0358(10) 0.0375(9) 0.0018(8) 0.0087(8) 0.0038(8)
C7 0.0321(10) 0.0342(10) 0.0416(10) 0.0048(8) 0.0073(9) 0.0034(8)
C8 0.0308(10) 0.0333(10) 0.0432(10) 0.0022(8) 0.0071(9) 0.0016(8)
C9 0.0363(11) 0.0279(9) 0.0385(10) -0.0028(7) 0.0107(9) -0.0025(7)
C10 0.0457(12) 0.0395(11) 0.0431(11) 0.0035(9) 0.0067(10) -0.0001(8)
C11 0.0703(16) 0.0465(12) 0.0364(10) -0.0019(11) 0.0158(11) -0.0019(9)
C12 0.0610(15) 0.0425(12) 0.0502(12) -0.0042(10) 0.0296(11) -0.0096(9)
C13 0.0384(11) 0.0411(11) 0.0523(12) 0.0007(8) 0.0168(10) -0.0051(9)
C14 0.0347(11) 0.0380(10) 0.0379(10) -0.0002(8) 0.0103(9) -0.0017(8)
C15 0.0331(10) 0.0463(11) 0.0324(9) 0.0052(8) 0.0106(8) 0.0047(8)
C16 0.0459(13) 0.0729(15) 0.0352(11) 0.0021(11) 0.0050(10) 0.0046(10)
C17 0.0529(13) 0.0491(12) 0.0480(11) 0.0065(10) 0.0239(10) 0.0157(9)
C18 0.0525(13) 0.0580(13) 0.0365(10) 0.0103(10) 0.0203(10) 0.0057(9)
C19 0.0364(11) 0.0374(10) 0.0338(9) 0.0040(8) 0.0066(8) 0.0044(8)
C20 0.0790(18) 0.0784(17) 0.0391(11) 0.0317(14) 0.0215(12) 0.0217(11)
C21 0.0464(13) 0.0373(11) 0.0571(12) 0.0030(9) 0.0047(10) 0.0088(9)
C22 0.0401(12) 0.0508(13) 0.0516(12) 0.0007(9) -0.0048(10) 0.0071(10)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C5 . . 105.92(15) ?
C2 C1 C15 . . 127.18(17) ?
C5 C1 C15 . . 126.87(15) ?
C1 C2 C3 . . 111.14(16) ?
C1 C2 H2 . . 124.4 ?
C3 C2 H2 . . 124.4 ?
C4 C3 C2 . . 107.67(15) ?
C4 C3 C19 . . 128.69(17) ?
C2 C3 C19 . . 123.62(16) ?
C3 C4 C5 . . 108.59(16) ?
C3 C4 H4 . . 125.7 ?
C5 C4 H4 . . 125.7 ?
C6 C5 C4 . . 124.38(17) y
C6 C5 C1 . . 128.93(16) ?
C4 C5 C1 . . 106.68(15) ?
C5 C6 C7 . . 123.90(17) y
C5 C6 H6 . . 118.0 ?
C7 C6 H6 . . 118.0 ?
C8 C7 C6 . . 178.4(2) y
C7 C8 C9 . . 177.97(19) y
C10 C9 C14 . . 118.48(18) ?
C10 C9 C8 . . 120.60(17) ?
C14 C9 C8 . . 120.90(16) ?
C11 C10 C9 . . 120.5(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.65(19) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C13 . . 119.5(2) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 120.38(18) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C1 C15 C18 . . 109.90(15) ?
C1 C15 C17 . . 110.53(15) ?
C18 C15 C17 . . 107.73(17) ?
C1 C15 C16 . . 110.74(16) ?
C18 C15 C16 . . 107.85(17) ?
C17 C15 C16 . . 110.00(16) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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 C3 . . 110.96(16) ?
C20 C19 C21 . . 110.14(18) ?
C3 C19 C21 . . 108.30(15) ?
C20 C19 C22 . . 109.39(18) ?
C3 C19 C22 . . 109.65(16) ?
C21 C19 C22 . . 108.35(17) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C19 C21 H21A . . 109.5 ?
C19 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C19 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.345(2) ?
C1 C5 . 1.481(3) ?
C1 C15 . 1.517(2) ?
C2 C3 . 1.469(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.344(2) ?
C3 C19 . 1.513(2) ?
C4 C5 . 1.464(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.352(2) ?
C6 C7 . 1.410(3) y
C6 H6 . 0.9500 ?
C7 C8 . 1.205(3) y
C8 C9 . 1.427(3) y
C9 C10 . 1.394(3) ?
C9 C14 . 1.395(3) ?
C10 C11 . 1.375(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.377(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C18 . 1.531(3) ?
C15 C17 . 1.535(3) ?
C15 C16 . 1.539(3) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 C20 . 1.513(3) ?
C19 C21 . 1.530(3) ?
C19 C22 . 1.538(3) ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C3 . . . . 0.38(19) ?
C15 C1 C2 C3 . . . . 178.63(16) ?
C1 C2 C3 C4 . . . . -0.7(2) ?
C1 C2 C3 C19 . . . . 177.82(16) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C19 C3 C4 C5 . . . . -177.73(17) ?
C3 C4 C5 C6 . . . . -179.96(17) ?
C3 C4 C5 C1 . . . . -0.5(2) ?
C2 C1 C5 C6 . . . . 179.50(18) ?
C15 C1 C5 C6 . . . . 1.2(3) ?
C2 C1 C5 C4 . . . . 0.04(19) ?
C15 C1 C5 C4 . . . . -178.22(16) ?
C4 C5 C6 C7 . . . . 1.3(3) ?
C1 C5 C6 C7 . . . . -178.09(17) ?
C14 C9 C10 C11 . . . . 0.8(3) ?
C8 C9 C10 C11 . . . . -177.72(18) ?
C9 C10 C11 C12 . . . . -0.2(3) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
C11 C12 C13 C14 . . . . 0.6(3) ?
C12 C13 C14 C9 . . . . 0.0(3) ?
C10 C9 C14 C13 . . . . -0.7(3) ?
C8 C9 C14 C13 . . . . 177.80(17) ?
C2 C1 C15 C18 . . . . 1.3(3) ?
C5 C1 C15 C18 . . . . 179.23(17) ?
C2 C1 C15 C17 . . . . -117.5(2) ?
C5 C1 C15 C17 . . . . 60.4(2) ?
C2 C1 C15 C16 . . . . 120.4(2) ?
C5 C1 C15 C16 . . . . -61.7(2) ?
C4 C3 C19 C20 . . . . -5.7(3) ?
C2 C3 C19 C20 . . . . 176.12(18) ?
C4 C3 C19 C21 . . . . 115.3(2) ?
C2 C3 C19 C21 . . . . -62.9(2) ?
C4 C3 C19 C22 . . . . -126.6(2) ?
C2 C3 C19 C22 . . . . 55.2(2) ?