#------------------------------------------------------------------------------
#$Date: 2017-11-07 03:16:45 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/71/1547170.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_1547170
loop_
_publ_author_name
'Barker, Joshua E.'
'Frederickson, Conerd K.'
'Jones, Michael H.'
'Zakharov, Lev N.'
'Haley, Michael M.'
_publ_section_title
;
 Synthesis and Properties of Quinoidal Fluorenofluorenes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5312
_journal_page_last               5315
_journal_paper_doi               10.1021/acs.orglett.7b02605
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C42 H34'
_chemical_formula_weight         538.69
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                87.837(4)
_cell_angle_beta                 88.161(4)
_cell_angle_gamma                75.494(4)
_cell_formula_units_Z            1
_cell_length_a                   7.1561(6)
_cell_length_b                   8.0619(6)
_cell_length_c                   12.8650(10)
_cell_measurement_reflns_used    4672
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.46
_cell_measurement_theta_min      5.67
_cell_volume                     717.84(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8275
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.500
_diffrn_reflns_theta_min         3.439
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            dark-blue
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0621
_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)+(0.0876P)²+0.7347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2183
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02605_si_002.cif
_cod_data_source_block           cu_mhrr148_0m
_cod_depositor_comments          'Adding full bibliography for 1547170.cif.'
_cod_database_code               1547170
_shelx_shelxl_version_number     2014/7
_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   0.954
_shelx_estimated_absorpt_t_max   0.969
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C -0.0985(3) 0.0560(3) 0.50454(17) 0.0225(5) Uani 1 1 d . .
C2 C -0.1546(3) 0.2022(3) 0.43402(18) 0.0264(5) Uani 1 1 d . .
H2A H -0.2802 0.2761 0.4412 0.032 Uiso 1 1 calc R U
C3 C -0.0344(3) 0.2373(3) 0.35834(18) 0.0262(5) Uani 1 1 d . .
H3A H -0.0766 0.3331 0.3120 0.031 Uiso 1 1 calc R U
C4 C 0.1569(3) 0.1298(3) 0.34814(17) 0.0226(5) Uani 1 1 d . .
C5 C 0.2218(3) -0.0152(3) 0.41951(17) 0.0217(5) Uani 1 1 d . .
C6 C 0.4254(3) -0.0945(3) 0.38919(17) 0.0224(5) Uani 1 1 d . .
C7 C 0.4708(3) 0.0016(3) 0.30164(17) 0.0235(5) Uani 1 1 d . .
C8 C 0.3015(3) 0.1403(3) 0.27646(17) 0.0236(5) Uani 1 1 d . .
C9 C 0.6534(3) -0.0383(3) 0.25474(19) 0.0302(6) Uani 1 1 d . .
H9A H 0.6822 0.0274 0.1963 0.036 Uiso 1 1 calc R U
C10 C 0.7937(3) -0.1764(3) 0.2948(2) 0.0328(6) Uani 1 1 d . .
H10A H 0.9188 -0.2061 0.2631 0.039 Uiso 1 1 calc R U
C11 C 0.7514(3) -0.2707(3) 0.38091(19) 0.0305(6) Uani 1 1 d . .
H11A H 0.8484 -0.3642 0.4077 0.037 Uiso 1 1 calc R U
C12 C 0.5685(3) -0.2302(3) 0.42873(18) 0.0263(5) Uani 1 1 d . .
H12A H 0.5418 -0.2951 0.4880 0.032 Uiso 1 1 calc R U
C13 C 0.2875(3) 0.2622(3) 0.18609(18) 0.0237(5) Uani 1 1 d . .
C14 C 0.2730(3) 0.2039(3) 0.08564(18) 0.0278(5) Uani 1 1 d . .
C15 C 0.2581(3) 0.3180(3) 0.00103(19) 0.0323(6) Uani 1 1 d . .
H15A H 0.2507 0.2774 -0.0667 0.039 Uiso 1 1 calc R U
C16 C 0.2538(3) 0.4895(3) 0.0123(2) 0.0324(6) Uani 1 1 d . .
C17 C 0.2652(3) 0.5455(3) 0.1119(2) 0.0319(6) Uani 1 1 d . .
H17A H 0.2603 0.6629 0.1210 0.038 Uiso 1 1 calc R U
C18 C 0.2836(3) 0.4354(3) 0.19895(19) 0.0266(5) Uani 1 1 d . .
C19 C 0.2636(4) 0.0219(3) 0.0701(2) 0.0381(6) Uani 1 1 d . .
H19A H 0.2763 -0.0408 0.1373 0.057 Uiso 1 1 calc R U
H19B H 0.1394 0.0219 0.0401 0.057 Uiso 1 1 calc R U
H19C H 0.3689 -0.0336 0.0229 0.057 Uiso 1 1 calc R U
C20 C 0.2364(4) 0.6108(4) -0.0813(2) 0.0458(8) Uani 1 1 d . .
H20A H 0.2302 0.5483 -0.1444 0.069 Uiso 1 1 calc R U
H20B H 0.1187 0.7033 -0.0740 0.069 Uiso 1 1 calc R U
H20C H 0.3490 0.6595 -0.0862 0.069 Uiso 1 1 calc R U
C21 C 0.3071(4) 0.5014(3) 0.3046(2) 0.0372(6) Uani 1 1 d . .
H21A H 0.3180 0.4084 0.3571 0.056 Uiso 1 1 calc R U
H21B H 0.4240 0.5439 0.3040 0.056 Uiso 1 1 calc R U
H21C H 0.1945 0.5949 0.3213 0.056 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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
C5 C1 C2 122.8(2) 2_556 .
C5 C1 C1 118.2(2) 2_556 2_556
C2 C1 C1 119.0(2) . 2_556
C3 C2 C1 122.1(2) . .
C3 C2 H2A 119.0 . .
C1 C2 H2A 119.0 . .
C2 C3 C4 119.7(2) . .
C2 C3 H3A 120.2 . .
C4 C3 H3A 120.2 . .
C8 C4 C3 129.4(2) . .
C8 C4 C5 110.45(19) . .
C3 C4 C5 120.1(2) . .
C1 C5 C4 120.9(2) 2_556 .
C1 C5 C6 133.0(2) 2_556 .
C4 C5 C6 106.11(18) . .
C12 C6 C7 118.8(2) . .
C12 C6 C5 134.4(2) . .
C7 C6 C5 106.78(18) . .
C9 C7 C6 121.4(2) . .
C9 C7 C8 129.6(2) . .
C6 C7 C8 109.03(19) . .
C4 C8 C7 107.61(19) . .
C4 C8 C13 127.0(2) . .
C7 C8 C13 125.4(2) . .
C7 C9 C10 118.9(2) . .
C7 C9 H9A 120.6 . .
C10 C9 H9A 120.6 . .
C11 C10 C9 120.3(2) . .
C11 C10 H10A 119.8 . .
C9 C10 H10A 119.8 . .
C10 C11 C12 121.0(2) . .
C10 C11 H11A 119.5 . .
C12 C11 H11A 119.5 . .
C6 C12 C11 119.7(2) . .
C6 C12 H12A 120.1 . .
C11 C12 H12A 120.1 . .
C18 C13 C14 119.4(2) . .
C18 C13 C8 121.4(2) . .
C14 C13 C8 119.2(2) . .
C15 C14 C13 119.3(2) . .
C15 C14 C19 120.0(2) . .
C13 C14 C19 120.6(2) . .
C14 C15 C16 122.1(2) . .
C14 C15 H15A 119.0 . .
C16 C15 H15A 119.0 . .
C17 C16 C15 117.9(2) . .
C17 C16 C20 121.3(2) . .
C15 C16 C20 120.8(2) . .
C16 C17 C18 122.1(2) . .
C16 C17 H17A 118.9 . .
C18 C17 H17A 118.9 . .
C17 C18 C13 119.2(2) . .
C17 C18 C21 119.7(2) . .
C13 C18 C21 121.1(2) . .
C14 C19 H19A 109.5 . .
C14 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C14 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C16 C20 H20A 109.5 . .
C16 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C16 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.381(3) 2_556
C1 C2 1.442(3) .
C1 C1 1.474(4) 2_556
C2 C3 1.347(3) .
C2 H2A 0.9500 .
C3 C4 1.431(3) .
C3 H3A 0.9500 .
C4 C8 1.380(3) .
C4 C5 1.449(3) .
C5 C1 1.381(3) 2_556
C5 C6 1.484(3) .
C6 C12 1.390(3) .
C6 C7 1.418(3) .
C7 C9 1.389(3) .
C7 C8 1.464(3) .
C8 C13 1.483(3) .
C9 C10 1.394(3) .
C9 H9A 0.9500 .
C10 C11 1.388(4) .
C10 H10A 0.9500 .
C11 C12 1.396(3) .
C11 H11A 0.9500 .
C12 H12A 0.9500 .
C13 C18 1.405(3) .
C13 C14 1.407(3) .
C14 C15 1.387(3) .
C14 C19 1.506(3) .
C15 C16 1.388(4) .
C15 H15A 0.9500 .
C16 C17 1.387(4) .
C16 C20 1.510(3) .
C17 C18 1.391(3) .
C17 H17A 0.9500 .
C18 C21 1.507(3) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 C1 C2 C3 -178.0(2) 2_556 .
C1 C1 C2 C3 1.8(4) 2_556 .
C1 C2 C3 C4 -1.5(4) . .
C2 C3 C4 C8 179.1(2) . .
C2 C3 C4 C5 -0.6(3) . .
C8 C4 C5 C1 -177.1(2) . 2_556
C3 C4 C5 C1 2.6(3) . 2_556
C8 C4 C5 C6 1.9(2) . .
C3 C4 C5 C6 -178.40(19) . .
C1 C5 C6 C12 -4.5(4) 2_556 .
C4 C5 C6 C12 176.7(2) . .
C1 C5 C6 C7 177.4(2) 2_556 .
C4 C5 C6 C7 -1.4(2) . .
C12 C6 C7 C9 0.6(3) . .
C5 C6 C7 C9 179.0(2) . .
C12 C6 C7 C8 -178.00(19) . .
C5 C6 C7 C8 0.4(2) . .
C3 C4 C8 C7 178.7(2) . .
C5 C4 C8 C7 -1.6(2) . .
C3 C4 C8 C13 -4.7(4) . .
C5 C4 C8 C13 175.1(2) . .
C9 C7 C8 C4 -177.7(2) . .
C6 C7 C8 C4 0.7(2) . .
C9 C7 C8 C13 5.6(4) . .
C6 C7 C8 C13 -176.0(2) . .
C6 C7 C9 C10 0.3(3) . .
C8 C7 C9 C10 178.6(2) . .
C7 C9 C10 C11 -0.8(4) . .
C9 C10 C11 C12 0.3(4) . .
C7 C6 C12 C11 -1.0(3) . .
C5 C6 C12 C11 -178.9(2) . .
C10 C11 C12 C6 0.6(3) . .
C4 C8 C13 C18 74.6(3) . .
C7 C8 C13 C18 -109.3(3) . .
C4 C8 C13 C14 -103.8(3) . .
C7 C8 C13 C14 72.3(3) . .
C18 C13 C14 C15 1.0(3) . .
C8 C13 C14 C15 179.4(2) . .
C18 C13 C14 C19 -176.0(2) . .
C8 C13 C14 C19 2.5(3) . .
C13 C14 C15 C16 -1.1(4) . .
C19 C14 C15 C16 175.9(2) . .
C14 C15 C16 C17 0.1(4) . .
C14 C15 C16 C20 -179.6(2) . .
C15 C16 C17 C18 1.0(4) . .
C20 C16 C17 C18 -179.2(2) . .
C16 C17 C18 C13 -1.1(4) . .
C16 C17 C18 C21 176.4(2) . .
C14 C13 C18 C17 0.1(3) . .
C8 C13 C18 C17 -178.3(2) . .
C14 C13 C18 C21 -177.4(2) . .
C8 C13 C18 C21 4.2(3) . .
