#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/32/2203271.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_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_paper_doi               10.1107/S1600536804003964
_journal_volume                  60
_journal_year                    2004
_chemical_formula_sum            'C22 H26'
_chemical_formula_weight         290.43
_chemical_name_systematic
;
 1,3-Di-tert-butyl-6-phenylethynyl-fulvene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 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_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_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.059
_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_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/[σ²(Fo²)+(0.0665P)²+0.4622P] where P = (Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            bt6413.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2203271
_cod_database_fobs_code          2203271
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_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_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_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_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
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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174455
