#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/06/2200600.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_2200600
loop_
_publ_author_name
'Jovanovic, Jovan'
'Schürmann, Markus'
'Preut, Hans'
'Spiteller, Michael'
_publ_section_title
;
 Second modification of
 (E)-2,3,2',3'-tetrahydro-[1,1']biindenylidene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1100
_journal_page_last               o1101
_journal_paper_doi               10.1107/S1600536801017767
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C18 H16'
_chemical_formula_moiety         'C18 H16'
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.860(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   43.717(5)
_cell_length_b                   8.0751(10)
_cell_length_c                   7.2651(12)
_cell_measurement_reflns_used    7904
_cell_measurement_temperature    291.0(10)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.45
_cell_volume                     2546.4(6)
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO and SCALEPACK
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material
;
SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291.0(10)
_diffrn_detector_area_resol_mean '19 vertical, 18 horizontal'
_diffrn_measured_fraction_theta_full .964
_diffrn_measured_fraction_theta_max .964
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
588 frames via ω-rotation (Δω=0.5%) and two times
20 s perframe (three sets at different κ-angles)
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .024
_diffrn_reflns_av_sigmaI/netI    .2294
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2826
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .08
_refine_diff_density_max         .149
_refine_diff_density_min         -.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .832
_refine_ls_R_factor_all          .2648
_refine_ls_R_factor_gt           .0500
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0150P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0968
_reflns_number_gt                780
_reflns_number_total             2826
_reflns_threshold_expression     I>σ(I)
_cod_data_source_file            bt6089.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2200600
_cod_database_fobs_code          2200600
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C11 .01521(4) 1.0118(3) .0133(3) .0502(8) Uani d . 1 . . C
C12 .03039(5) 1.1832(3) .0262(3) .0583(7) Uani d . 1 . . C
H12A .0241 1.2451 .1297 .070 Uiso calc R 1 . . H
H12B .0247 1.2455 -.0869 .070 Uiso calc R 1 . . H
C13 .06565(5) 1.1502(3) .0552(3) .0652(8) Uani d . 1 . . C
H13A .0755 1.1982 -.0450 .078 Uiso calc R 1 . . H
H13B .0749 1.1972 .1716 .078 Uiso calc R 1 . . H
C14 .06890(7) .9662(4) .0569(3) .0543(7) Uani d . 1 . . C
C15 .09603(6) .8768(4) .0803(3) .0659(8) Uani d . 1 . . C
H15 .1149 .9315 .0975 .079 Uiso calc R 1 . . H
C16 .09508(7) .7075(4) .0783(3) .0729(9) Uani d . 1 . . C
H16 .1133 .6469 .0920 .087 Uiso calc R 1 . . H
C17 .06692(8) .6265(3) .0558(3) .0747(9) Uani d . 1 . . C
H17 .0663 .5114 .0562 .090 Uiso calc R 1 . . H
C18 .03965(6) .7159(4) .0327(3) .0647(8) Uani d . 1 . . C
H18 .0209 .6602 .0170 .078 Uiso calc R 1 . . H
C19 .04016(6) .8894(4) .0329(3) .0523(7) Uani d . 1 . . C
C21 .23499(4) .7659(3) .4731(3) .0479(7) Uani d . 1 . . C
C22 .22266(5) .8502(3) .2909(3) .0660(8) Uani d . 1 . . C
H22A .2276 .7850 .1862 .079 Uiso calc R 1 . . H
H22B .2317 .9594 .2835 .079 Uiso calc R 1 . . H
C23 .18768(5) .8634(3) .2900(3) .0747(9) Uani d . 1 . . C
H23A .1812 .9784 .2867 .090 Uiso calc R 1 . . H
H23B .1770 .8065 .1834 .090 Uiso calc R 1 . . H
C24 .18113(6) .7826(3) .4661(3) .0554(7) Uani d . 1 . . C
C25 .15281(6) .7589(3) .5273(4) .0646(8) Uani d . 1 . . C
H25 .1350 .7944 .4554 .077 Uiso calc R 1 . . H
C26 .15098(6) .6829(3) .6943(4) .0696(9) Uani d . 1 . . C
H26 .1319 .6672 .7363 .084 Uiso calc R 1 . . H
C27 .17765(7) .6294(3) .8006(4) .0693(8) Uani d . 1 . . C
H27 .1763 .5782 .9140 .083 Uiso calc R 1 . . H
C28 .20603(6) .6511(3) .7400(4) .0654(8) Uani d . 1 . . C
H28 .2237 .6147 .8123 .078 Uiso calc R 1 . . H
C29 .20818(5) .7280(3) .5700(4) .0503(7) Uani d . 1 . . C
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'
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
C11 C11 C19 5_575 129.3(3)
C11 C11 C12 5_575 123.7(3)
C19 C11 C12 . 106.94(19)
C11 C12 C13 . 105.60(19)
C11 C12 H12A . 110.6
C13 C12 H12A . 110.6
C11 C12 H12B . 110.6
C13 C12 H12B . 110.6
H12A C12 H12B . 108.8
C14 C13 C12 . 105.3(2)
C14 C13 H13A . 110.7
C12 C13 H13A . 110.7
C14 C13 H13B . 110.7
C12 C13 H13B . 110.7
H13A C13 H13B . 108.8
C15 C14 C19 . 122.0(3)
C15 C14 C13 . 126.9(3)
C19 C14 C13 . 111.0(3)
C16 C15 C14 . 119.8(3)
C16 C15 H15 . 120.1
C14 C15 H15 . 120.1
C15 C16 C17 . 119.9(3)
C15 C16 H16 . 120.0
C17 C16 H16 . 120.0
C16 C17 C18 . 120.5(3)
C16 C17 H17 . 119.8
C18 C17 H17 . 119.8
C17 C18 C19 . 120.5(2)
C17 C18 H18 . 119.8
C19 C18 H18 . 119.8
C14 C19 C18 . 117.3(2)
C14 C19 C11 . 111.1(3)
C18 C19 C11 . 131.5(3)
C21 C21 C29 7_566 128.7(3)
C21 C21 C22 7_566 124.5(3)
C29 C21 C22 . 106.78(18)
C21 C22 C23 . 106.46(17)
C21 C22 H22A . 110.4
C23 C22 H22A . 110.4
C21 C22 H22B . 110.4
C23 C22 H22B . 110.4
H22A C22 H22B . 108.6
C24 C23 C22 . 105.02(18)
C24 C23 H23A . 110.7
C22 C23 H23A . 110.7
C24 C23 H23B . 110.7
C22 C23 H23B . 110.7
H23A C23 H23B . 108.8
C25 C24 C29 . 121.2(2)
C25 C24 C23 . 127.5(2)
C29 C24 C23 . 111.4(2)
C26 C25 C24 . 119.8(2)
C26 C25 H25 . 120.1
C24 C25 H25 . 120.1
C25 C26 C27 . 119.8(2)
C25 C26 H26 . 120.1
C27 C26 H26 . 120.1
C28 C27 C26 . 120.8(2)
C28 C27 H27 . 119.6
C26 C27 H27 . 119.6
C27 C28 C29 . 119.9(2)
C27 C28 H28 . 120.1
C29 C28 H28 . 120.1
C28 C29 C24 . 118.5(2)
C28 C29 C21 . 131.2(2)
C24 C29 C21 . 110.3(2)
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
C11 C11 5_575 1.335(4) ?
C11 C19 . 1.466(3) ?
C11 C12 . 1.532(3) ?
C12 C13 . 1.553(3) ?
C12 H12A . .9700 ?
C12 H12B . .9700 ?
C13 C14 . 1.492(3) ?
C13 H13A . .9700 ?
C13 H13B . .9700 ?
C14 C15 . 1.382(3) ?
C14 C19 . 1.394(3) ?
C15 C16 . 1.368(3) ?
C15 H15 . .9300 ?
C16 C17 . 1.386(3) ?
C16 H16 . .9300 ?
C17 C18 . 1.386(3) ?
C17 H17 . .9300 ?
C18 C19 . 1.401(3) ?
C18 H18 . .9300 ?
C21 C21 7_566 1.349(4) ?
C21 C29 . 1.470(3) ?
C21 C22 . 1.528(3) ?
C22 C23 . 1.532(2) ?
C22 H22A . .9700 ?
C22 H22B . .9700 ?
C23 C24 . 1.494(3) ?
C23 H23A . .9700 ?
C23 H23B . .9700 ?
C24 C25 . 1.378(3) ?
C24 C29 . 1.396(3) ?
C25 C26 . 1.371(3) ?
C25 H25 . .9300 ?
C26 C27 . 1.389(3) ?
C26 H26 . .9300 ?
C27 C28 . 1.376(3) ?
C27 H27 . .9300 ?
C28 C29 . 1.396(3) ?
C28 H28 . .9300 ?
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
C11 C11 C12 C13 5_575 -179.5(3)
C19 C11 C12 C13 . -.2(2)
C11 C12 C13 C14 . .1(2)
C12 C13 C14 C15 . -179.4(2)
C12 C13 C14 C19 . -.1(3)
C19 C14 C15 C16 . .7(4)
C13 C14 C15 C16 . -179.9(2)
C14 C15 C16 C17 . -1.1(4)
C15 C16 C17 C18 . .9(4)
C16 C17 C18 C19 . -.4(4)
C15 C14 C19 C18 . -.2(4)
C13 C14 C19 C18 . -179.6(2)
C15 C14 C19 C11 . 179.3(2)
C13 C14 C19 C11 . -.1(3)
C17 C18 C19 C14 . .0(4)
C17 C18 C19 C11 . -179.4(2)
C11 C11 C19 C14 5_575 179.4(3)
C12 C11 C19 C14 . .2(3)
C11 C11 C19 C18 5_575 -1.1(5)
C12 C11 C19 C18 . 179.6(2)
C21 C21 C22 C23 7_566 -179.0(3)
C29 C21 C22 C23 . 1.6(2)
C21 C22 C23 C24 . -1.7(2)
C22 C23 C24 C25 . -178.1(2)
C22 C23 C24 C29 . 1.3(3)
C29 C24 C25 C26 . 1.1(4)
C23 C24 C25 C26 . -179.5(3)
C24 C25 C26 C27 . -.4(4)
C25 C26 C27 C28 . -.2(4)
C26 C27 C28 C29 . .1(4)
C27 C28 C29 C24 . .7(3)
C27 C28 C29 C21 . -179.8(2)
C25 C24 C29 C28 . -1.3(3)
C23 C24 C29 C28 . 179.3(2)
C25 C24 C29 C21 . 179.1(2)
C23 C24 C29 C21 . -.4(3)
C21 C21 C29 C28 7_566 .2(5)
C22 C21 C29 C28 . 179.6(2)
C21 C21 C29 C24 7_566 179.8(3)
C22 C21 C29 C24 . -.8(2)
