#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552281.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_1552281
loop_
_publ_author_name
'Detert, Heiner'
'Schollmeyer, Dieter'
_publ_section_title
;
 5,10-Dihydroindeno[2,1-a]indene
;
_journal_coeditor_code           BT4085
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x191179
_journal_paper_doi               10.1107/S2414314619011799
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C16 H12'
_chemical_formula_moiety         'C16 H12'
_chemical_formula_sum            'C16 H12'
_chemical_formula_weight         204.26
_chemical_name_systematic
;
5,10-Dihydroindeno[2,1-a]indene
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                99.733(11)
_cell_angle_beta                 100.641(11)
_cell_angle_gamma                90.523(9)
_cell_formula_units_Z            4
_cell_length_a                   7.5009(9)
_cell_length_b                   7.6819(9)
_cell_length_c                   19.387(3)
_cell_measurement_reflns_used    2411
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.76
_cell_volume                     1081.1(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 1996)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 1996)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 1996)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14443
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_min         2.693
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         14443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0513P)²+0.1143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                7500
_reflns_number_total             14443
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4085sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1081.2(2)
_cod_database_code               1552281
_cod_database_fobs_code          1552281
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
C C1A 0.6265(4) 0.1349(3) 0.58366(16) 0.0420(7) Uani d 1
H H1A 0.570270 0.239199 0.607100 0.050 Uiso calc 1
H H1B 0.758394 0.160278 0.588948 0.050 Uiso calc 1
C C2A 0.5377(3) 0.0821(3) 0.50682(15) 0.0379(7) Uani d 1
C C3A 0.5094(3) 0.1575(3) 0.44194(16) 0.0371(7) Uani d 1
C C4A 0.5622(3) 0.3197(3) 0.42737(17) 0.0424(7) Uani d 1
H H4A 0.627703 0.406985 0.464147 0.051 Uiso calc 1
C C5A 0.5171(4) 0.3509(4) 0.35798(18) 0.0463(8) Uani d 1
H H5A 0.553328 0.460341 0.347082 0.056 Uiso calc 1
C C6A 0.4206(4) 0.2254(4) 0.30472(18) 0.0475(8) Uani d 1
H H6A 0.390593 0.250000 0.257642 0.057 Uiso calc 1
C C7A 0.3663(4) 0.0633(4) 0.31857(17) 0.0461(8) Uani d 1
H H7A 0.299603 -0.022537 0.281531 0.055 Uiso calc 1
C C8A 0.4111(3) 0.0299(3) 0.38696(16) 0.0396(7) Uani d 1
C C1B 0.9607(4) 0.6291(3) 0.58564(17) 0.0485(8) Uani d 1
H H1C 0.834972 0.652170 0.592501 0.058 Uiso calc 1
H H1D 1.040849 0.733646 0.609137 0.058 Uiso calc 1
C C2B 0.9702(4) 0.5806(3) 0.50825(17) 0.0428(7) Uani d 1
C C3B 0.9306(3) 0.6610(3) 0.44363(17) 0.0416(7) Uani d 1
C C4B 0.8648(4) 0.8222(3) 0.43136(18) 0.0472(8) Uani d 1
H H4B 0.837765 0.907055 0.469307 0.057 Uiso calc 1
C C5B 0.8391(4) 0.8579(4) 0.36300(19) 0.0512(8) Uani d 1
H H5B 0.792298 0.967956 0.353938 0.061 Uiso calc 1
C C6B 0.8799(4) 0.7372(4) 0.30744(19) 0.0523(8) Uani d 1
H H6B 0.862114 0.765677 0.260901 0.063 Uiso calc 1
C C7B 0.9472(4) 0.5735(4) 0.3191(2) 0.0537(9) Uani d 1
H H7B 0.974921 0.489898 0.280873 0.064 Uiso calc 1
C C8B 0.9724(3) 0.5359(3) 0.38743(18) 0.0439(7) Uani d 1
C C1C 0.6484(4) 0.4528(4) 0.08155(17) 0.0491(8) Uani d 1
H H1E 0.760177 0.527069 0.102405 0.059 Uiso calc 1
H H1F 0.670975 0.328768 0.087230 0.059 Uiso calc 1
C C2C 0.5827(3) 0.4677(3) 0.00581(17) 0.0422(7) Uani d 1
C C3C 0.6498(4) 0.4309(3) -0.06130(17) 0.0422(7) Uani d 1
C C4C 0.8104(4) 0.3624(3) -0.07899(18) 0.0506(8) Uani d 1
H H4C 0.903217 0.330126 -0.043541 0.061 Uiso calc 1
C C5C 0.8316(4) 0.3425(3) -0.14959(19) 0.0530(8) Uani d 1
H H5C 0.939557 0.295384 -0.162728 0.064 Uiso calc 1
C C6C 0.6969(4) 0.3906(4) -0.20061(19) 0.0537(8) Uani d 1
H H6C 0.713696 0.377195 -0.248581 0.064 Uiso calc 1
C C7C 0.5370(4) 0.4585(4) -0.18306(19) 0.0512(8) Uani d 1
H H7C 0.445029 0.491165 -0.218706 0.061 Uiso calc 1
C C8C 0.5134(4) 0.4776(3) -0.11433(17) 0.0429(7) Uani d 1
C C1D 0.1447(4) 0.1273(4) 0.08064(18) 0.0545(8) Uani d 1
H H1G 0.168542 0.255730 0.083898 0.065 Uiso calc 1
H H1H 0.255170 0.074407 0.103547 0.065 Uiso calc 1
C C2D 0.0818(4) 0.0383(3) 0.00570(18) 0.0461(8) Uani d 1
C C3D 0.1529(4) 0.0084(3) -0.06117(18) 0.0451(7) Uani d 1
C C4D 0.3153(4) 0.0594(3) -0.07869(19) 0.0525(8) Uani d 1
H H4D 0.406367 0.127811 -0.043834 0.063 Uiso calc 1
C C5D 0.3409(4) 0.0080(4) -0.1484(2) 0.0555(8) Uani d 1
H H5D 0.450338 0.041999 -0.161536 0.067 Uiso calc 1
C C6D 0.2082(5) -0.0922(4) -0.1985(2) 0.0569(9) Uani d 1
H H6D 0.227975 -0.128483 -0.245749 0.068 Uiso calc 1
C C7D 0.0464(4) -0.1404(4) -0.18077(19) 0.0538(8) Uani d 1
H H7D -0.044961 -0.208078 -0.215738 0.065 Uiso calc 1
C C8D 0.0193(4) -0.0903(3) -0.11304(19) 0.0467(8) Uani d 1
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
C2A C1A C8A . 2_656 101.2(2)
C2A C1A H1A . . 111.5
C8A C1A H1A 2_656 . 111.5
C2A C1A H1B . . 111.5
C8A C1A H1B 2_656 . 111.5
H1A C1A H1B . . 109.3
C2A C2A C3A 2_656 . 109.8(3)
C2A C2A C1A 2_656 . 111.8(3)
C3A C2A C1A . . 138.4(2)
C4A C3A C8A . . 120.1(3)
C4A C3A C2A . . 132.5(3)
C8A C3A C2A . . 107.5(2)
C5A C4A C3A . . 118.5(3)
C5A C4A H4A . . 120.7
C3A C4A H4A . . 120.7
C6A C5A C4A . . 120.9(3)
C6A C5A H5A . . 119.6
C4A C5A H5A . . 119.6
C5A C6A C7A . . 121.2(3)
C5A C6A H6A . . 119.4
C7A C6A H6A . . 119.4
C8A C7A C6A . . 118.6(3)
C8A C7A H7A . . 120.7
C6A C7A H7A . . 120.7
C7A C8A C3A . . 120.7(3)
C7A C8A C1A . 2_656 129.7(3)
C3A C8A C1A . 2_656 109.6(3)
C2B C1B C8B . 2_766 101.0(2)
C2B C1B H1C . . 111.6
C8B C1B H1C 2_766 . 111.6
C2B C1B H1D . . 111.6
C8B C1B H1D 2_766 . 111.6
H1C C1B H1D . . 109.4
C2B C2B C3B 2_766 . 109.3(4)
C2B C2B C1B 2_766 . 112.7(4)
C3B C2B C1B . . 138.0(2)
C4B C3B C8B . . 120.6(3)
C4B C3B C2B . . 132.7(3)
C8B C3B C2B . . 106.7(2)
C5B C4B C3B . . 118.7(3)
C5B C4B H4B . . 120.7
C3B C4B H4B . . 120.7
C4B C5B C6B . . 121.5(3)
C4B C5B H5B . . 119.3
C6B C5B H5B . . 119.3
C5B C6B C7B . . 120.5(3)
C5B C6B H6B . . 119.7
C7B C6B H6B . . 119.7
C8B C7B C6B . . 118.5(3)
C8B C7B H7B . . 120.7
C6B C7B H7B . . 120.7
C7B C8B C3B . . 120.2(3)
C7B C8B C1B . 2_766 129.5(3)
C3B C8B C1B . 2_766 110.3(3)
C2C C1C C8C . 2_665 100.7(2)
C2C C1C H1E . . 111.6
C8C C1C H1E 2_665 . 111.6
C2C C1C H1F . . 111.6
C8C C1C H1F 2_665 . 111.6
H1E C1C H1F . . 109.4
C2C C2C C3C 2_665 . 109.6(3)
C2C C2C C1C 2_665 . 113.0(4)
C3C C2C C1C . . 137.4(2)
C4C C3C C8C . . 120.1(3)
C4C C3C C2C . . 133.1(3)
C8C C3C C2C . . 106.8(2)
C5C C4C C3C . . 118.6(3)
C5C C4C H4C . . 120.7
C3C C4C H4C . . 120.7
C6C C5C C4C . . 120.4(3)
C6C C5C H5C . . 119.8
C4C C5C H5C . . 119.8
C5C C6C C7C . . 121.1(3)
C5C C6C H6C . . 119.5
C7C C6C H6C . . 119.5
C8C C7C C6C . . 119.3(3)
C8C C7C H7C . . 120.3
C6C C7C H7C . . 120.3
C7C C8C C3C . . 120.5(3)
C7C C8C C1C . 2_665 129.5(3)
C3C C8C C1C . 2_665 109.9(3)
C2D C1D C8D . 2 100.7(2)
C2D C1D H1G . . 111.6
C8D C1D H1G 2 . 111.6
C2D C1D H1H . . 111.6
C8D C1D H1H 2 . 111.6
H1G C1D H1H . . 109.4
C2D C2D C3D 2 . 109.2(4)
C2D C2D C1D 2 . 113.2(4)
C3D C2D C1D . . 137.5(2)
C4D C3D C8D . . 120.2(3)
C4D C3D C2D . . 132.9(3)
C8D C3D C2D . . 106.9(3)
C5D C4D C3D . . 118.5(3)
C5D C4D H4D . . 120.8
C3D C4D H4D . . 120.8
C6D C5D C4D . . 120.3(3)
C6D C5D H5D . . 119.8
C4D C5D H5D . . 119.8
C5D C6D C7D . . 120.7(3)
C5D C6D H6D . . 119.6
C7D C6D H6D . . 119.6
C8D C7D C6D . . 119.6(3)
C8D C7D H7D . . 120.2
C6D C7D H7D . . 120.2
C7D C8D C3D . . 120.7(3)
C7D C8D C1D . 2 129.4(3)
C3D C8D C1D . 2 109.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1A C2A . 1.500(4)
C1A C8A 2_656 1.518(4)
C1A H1A . 0.9900
C1A H1B . 0.9900
C2A C2A 2_656 1.341(4)
C2A C3A . 1.453(4)
C3A C4A . 1.393(3)
C3A C8A . 1.408(4)
C4A C5A . 1.387(4)
C4A H4A . 0.9500
C5A C6A . 1.376(4)
C5A H5A . 0.9500
C6A C7A . 1.390(4)
C6A H6A . 0.9500
C7A C8A . 1.374(4)
C7A H7A . 0.9500
C1B C2B . 1.499(4)
C1B C8B 2_766 1.506(4)
C1B H1C . 0.9900
C1B H1D . 0.9900
C2B C2B 2_766 1.329(5)
C2B C3B . 1.472(4)
C3B C4B . 1.379(4)
C3B C8B . 1.410(4)
C4B C5B . 1.378(4)
C4B H4B . 0.9500
C5B C6B . 1.379(4)
C5B H5B . 0.9500
C6B C7B . 1.397(4)
C6B H6B . 0.9500
C7B C8B . 1.384(4)
C7B H7B . 0.9500
C1C C2C . 1.484(4)
C1C C8C 2_665 1.531(4)
C1C H1E . 0.9900
C1C H1F . 0.9900
C2C C2C 2_665 1.335(5)
C2C C3C . 1.465(4)
C3C C4C . 1.396(4)
C3C C8C . 1.406(4)
C4C C5C . 1.390(4)
C4C H4C . 0.9500
C5C C6C . 1.377(4)
C5C H5C . 0.9500
C6C C7C . 1.388(4)
C6C H6C . 0.9500
C7C C8C . 1.360(4)
C7C H7C . 0.9500
C1D C2D . 1.485(4)
C1D C8D 2 1.526(4)
C1D H1G . 0.9900
C1D H1H . 0.9900
C2D C2D 2 1.321(5)
C2D C3D . 1.475(4)
C3D C4D . 1.393(4)
C3D C8D . 1.395(4)
C4D C5D . 1.392(4)
C4D H4D . 0.9500
C5D C6D . 1.380(4)
C5D H5D . 0.9500
C6D C7D . 1.385(4)
C6D H6D . 0.9500
C7D C8D . 1.357(4)
C7D H7D . 0.9500
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_4
_geom_torsion
C8A C1A C2A C2A 2_656 2_656 -0.1(3)
C8A C1A C2A C3A 2_656 . -179.9(3)
C2A C2A C3A C4A 2_656 . -178.8(3)
C1A C2A C3A C4A . . 1.0(5)
C2A C2A C3A C8A 2_656 . 0.1(3)
C1A C2A C3A C8A . . 179.9(3)
C8A C3A C4A C5A . . -0.5(4)
C2A C3A C4A C5A . . 178.3(3)
C3A C4A C5A C6A . . 0.7(4)
C4A C5A C6A C7A . . -0.4(4)
C5A C6A C7A C8A . . -0.1(4)
C6A C7A C8A C3A . . 0.3(4)
C6A C7A C8A C1A . 2_656 -178.5(2)
C4A C3A C8A C7A . . 0.0(4)
C2A C3A C8A C7A . . -179.1(2)
C4A C3A C8A C1A . 2_656 179.0(2)
C2A C3A C8A C1A . 2_656 -0.1(3)
C8B C1B C2B C2B 2_766 2_766 0.2(4)
C8B C1B C2B C3B 2_766 . 179.7(3)
C2B C2B C3B C4B 2_766 . 179.1(3)
C1B C2B C3B C4B . . -0.4(5)
C2B C2B C3B C8B 2_766 . -0.4(4)
C1B C2B C3B C8B . . -179.9(3)
C8B C3B C4B C5B . . 0.6(4)
C2B C3B C4B C5B . . -178.9(3)
C3B C4B C5B C6B . . -0.9(4)
C4B C5B C6B C7B . . 0.7(4)
C5B C6B C7B C8B . . -0.3(4)
C6B C7B C8B C3B . . 0.0(4)
C6B C7B C8B C1B . 2_766 178.9(3)
C4B C3B C8B C7B . . -0.2(4)
C2B C3B C8B C7B . . 179.4(2)
C4B C3B C8B C1B . 2_766 -179.3(2)
C2B C3B C8B C1B . 2_766 0.3(3)
C8C C1C C2C C2C 2_665 2_665 0.0(4)
C8C C1C C2C C3C 2_665 . -180.0(3)
C2C C2C C3C C4C 2_665 . -179.4(3)
C1C C2C C3C C4C . . 0.6(5)
C2C C2C C3C C8C 2_665 . 0.0(3)
C1C C2C C3C C8C . . -180.0(3)
C8C C3C C4C C5C . . 0.2(4)
C2C C3C C4C C5C . . 179.5(3)
C3C C4C C5C C6C . . 0.4(4)
C4C C5C C6C C7C . . -0.5(4)
C5C C6C C7C C8C . . 0.0(4)
C6C C7C C8C C3C . . 0.6(4)
C6C C7C C8C C1C . 2_665 -179.6(2)
C4C C3C C8C C7C . . -0.7(4)
C2C C3C C8C C7C . . 179.8(2)
C4C C3C C8C C1C . 2_665 179.5(2)
C2C C3C C8C C1C . 2_665 0.0(3)
C8D C1D C2D C2D 2 2 -0.7(4)
C8D C1D C2D C3D 2 . -179.7(3)
C2D C2D C3D C4D 2 . 179.8(3)
C1D C2D C3D C4D . . -1.2(5)
C2D C2D C3D C8D 2 . 0.4(4)
C1D C2D C3D C8D . . 179.4(3)
C8D C3D C4D C5D . . -0.8(4)
C2D C3D C4D C5D . . 179.9(3)
C3D C4D C5D C6D . . -0.4(4)
C4D C5D C6D C7D . . 1.2(4)
C5D C6D C7D C8D . . -0.8(4)
C6D C7D C8D C3D . . -0.3(4)
C6D C7D C8D C1D . 2 -179.6(3)
C4D C3D C8D C7D . . 1.1(4)
C2D C3D C8D C7D . . -179.4(2)
C4D C3D C8D C1D . 2 -179.5(2)
C2D C3D C8D C1D . 2 0.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303205
