#------------------------------------------------------------------------------
#$Date: 2019-11-24 03:11:17 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/40/1554008.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_1554008
loop_
_publ_author_name
'Kobin, Björn'
'Behren, Sandra'
'Braun-Cula, Beatrice'
'Hecht, Stefan'
_publ_section_title
;
 Photochemical Degradation of Various Bridge-Substituted Fluorene-Based
 Materials.
;
_journal_issue                   28
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              5474
_journal_page_last               5480
_journal_paper_doi               10.1021/acs.jpca.6b02127
_journal_volume                  120
_journal_year                    2016
_chemical_formula_moiety         'C25 H16 F2'
_chemical_formula_sum            'C25 H16 F2'
_chemical_formula_weight         354.38
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 110.275(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6134(4)
_cell_length_b                   19.6360(10)
_cell_length_c                   9.8168(4)
_cell_measurement_reflns_used    12646
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      4.63
_cell_volume                     1738.29(14)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'PLATON, 1990'
_computing_publication_material  'PLATON, 1990'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      ' 354 frames, detector distance = 90 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27855
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         4.70
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0383
_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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2791
_reflns_number_total             4091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp6b02127_si_005.cif
_cod_data_source_block           kbjka
_cod_original_cell_volume        1738.29(13)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1554008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.47536(12) 0.2500 0.17263(13) 0.0212(3) Uani 1 2 d S
F2 F 0.56944(12) 0.2500 0.00166(12) 0.0209(3) Uani 1 2 d S
C1 C 0.6092(2) 0.2500 0.1508(2) 0.0164(4) Uani 1 2 d S
C2 C 0.70414(15) 0.18925(7) 0.21894(15) 0.0170(3) Uani 1 1 d .
C3 C 0.84043(15) 0.21251(7) 0.31335(14) 0.0178(3) Uani 1 1 d .
C4 C 0.94825(16) 0.16589(8) 0.38843(16) 0.0214(3) Uani 1 1 d .
C5 C 0.91777(16) 0.09697(7) 0.36522(16) 0.0204(3) Uani 1 1 d .
C6 C 0.78224(15) 0.07307(7) 0.26940(15) 0.0170(3) Uani 1 1 d .
C7 C 0.67264(16) 0.12087(7) 0.19589(15) 0.0174(3) Uani 1 1 d .
C8 C 0.75622(14) -0.00112(7) 0.24321(14) 0.0161(3) Uani 1 1 d .
C9 C 0.87522(16) -0.04556(7) 0.26184(15) 0.0188(3) Uani 1 1 d .
C10 C 0.85189(16) -0.11487(8) 0.23618(16) 0.0225(3) Uani 1 1 d .
C11 C 0.70988(17) -0.14135(8) 0.19106(16) 0.0221(3) Uani 1 1 d .
C12 C 0.59009(17) -0.09798(7) 0.17121(16) 0.0206(3) Uani 1 1 d .
C13 C 0.61299(16) -0.02871(7) 0.19776(15) 0.0193(3) Uani 1 1 d .
F3 F 0.48872(12) 0.2500 0.60355(13) 0.0245(3) Uani 1 2 d S
F4 F 0.64846(14) 0.2500 0.49262(12) 0.0265(3) Uani 1 2 d S
C14 C 0.6396(2) 0.2500 0.6283(2) 0.0193(4) Uani 1 2 d S
C15 C 0.71368(15) 0.18952(7) 0.71857(15) 0.0173(3) Uani 1 1 d .
C16 C 0.80866(14) 0.21220(7) 0.85369(15) 0.0174(3) Uani 1 1 d .
C17 C 0.88315(15) 0.16463(7) 0.95779(16) 0.0188(3) Uani 1 1 d .
C18 C 0.86198(15) 0.09557(7) 0.92256(15) 0.0189(3) Uani 1 1 d .
C19 C 0.76929(15) 0.07295(7) 0.78658(15) 0.0175(3) Uani 1 1 d .
C20 C 0.69392(15) 0.12179(7) 0.68269(16) 0.0179(3) Uani 1 1 d .
C21 C 0.74743(14) -0.00072(7) 0.75068(14) 0.0171(3) Uani 1 1 d .
C22 C 0.71458(15) -0.02333(7) 0.60791(16) 0.0195(3) Uani 1 1 d .
C23 C 0.68931(16) -0.09172(8) 0.57334(16) 0.0221(3) Uani 1 1 d .
C24 C 0.69566(16) -0.13887(8) 0.68021(17) 0.0232(3) Uani 1 1 d .
C25 C 0.72989(16) -0.11756(8) 0.82253(17) 0.0217(3) Uani 1 1 d .
C26 C 0.75566(15) -0.04906(7) 0.85791(16) 0.0193(3) Uani 1 1 d .
H501 H 0.9771(16) -0.0266(7) 0.2914(15) 0.015(4) Uiso 1 1 d .
H502 H 0.7778(16) -0.0351(8) 0.9583(17) 0.020(4) Uiso 1 1 d .
H503 H 0.7349(17) -0.1496(8) 0.8997(18) 0.026(4) Uiso 1 1 d .
H504 H 0.9927(17) 0.0642(8) 0.4153(17) 0.023(4) Uiso 1 1 d .
H505 H 0.6650(17) -0.1057(8) 0.4709(18) 0.024(4) Uiso 1 1 d .
H506 H 0.9402(19) -0.1456(9) 0.2515(18) 0.035(5) Uiso 1 1 d .
H507 H 0.5761(17) 0.1056(7) 0.1276(16) 0.017(4) Uiso 1 1 d .
H508 H 0.6253(16) 0.1091(7) 0.5881(16) 0.015(4) Uiso 1 1 d .
H509 H 0.6938(17) -0.1925(9) 0.1778(17) 0.028(4) Uiso 1 1 d .
H510 H 0.4894(18) -0.1175(8) 0.1381(17) 0.023(4) Uiso 1 1 d .
H511 H 0.5293(18) 0.0006(9) 0.1870(17) 0.027(4) Uiso 1 1 d .
H512 H 0.9167(16) 0.0634(8) 0.9957(17) 0.020(4) Uiso 1 1 d .
H513 H 0.6765(17) -0.1870(9) 0.6581(18) 0.026(4) Uiso 1 1 d .
H514 H 0.9503(17) 0.1783(8) 1.0530(18) 0.024(4) Uiso 1 1 d .
H515 H 1.0419(17) 0.1814(8) 0.4559(17) 0.019(4) Uiso 1 1 d .
H516 H 0.7113(16) 0.0096(8) 0.5316(16) 0.021(4) Uiso 1 1 d .
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'
F F 0.0171 0.0103 '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
F1 C1 F2 103.61(15) . .
F1 C1 C2 112.64(10) . .
F2 C1 C2 111.92(10) . .
F1 C1 C2 112.64(10) . 4_565
F2 C1 C2 111.92(10) . 4_565
C2 C1 C2 104.36(16) . 4_565
C7 C2 C3 122.08(13) . .
C7 C2 C1 129.22(13) . .
C3 C2 C1 108.68(12) . .
C4 C3 C2 119.60(13) . .
C4 C3 C3 131.27(8) . 4_565
C2 C3 C3 109.13(8) . 4_565
C5 C4 C3 118.69(14) . .
C5 C4 H515 121.0(9) . .
C3 C4 H515 120.3(9) . .
C4 C5 C6 122.20(13) . .
C4 C5 H504 119.3(9) . .
C6 C5 H504 118.5(9) . .
C5 C6 C7 118.57(13) . .
C5 C6 C8 120.50(12) . .
C7 C6 C8 120.91(13) . .
C2 C7 C6 118.84(13) . .
C2 C7 H507 120.7(9) . .
C6 C7 H507 120.5(9) . .
C9 C8 C13 117.98(13) . .
C9 C8 C6 120.52(12) . .
C13 C8 C6 121.49(12) . .
C10 C9 C8 120.95(13) . .
C10 C9 H501 120.1(8) . .
C8 C9 H501 118.9(8) . .
C11 C10 C9 120.42(14) . .
C11 C10 H506 120.6(10) . .
C9 C10 H506 119.0(10) . .
C10 C11 C12 119.50(14) . .
C10 C11 H509 120.1(9) . .
C12 C11 H509 120.3(9) . .
C13 C12 C11 120.27(14) . .
C13 C12 H510 121.1(9) . .
C11 C12 H510 118.6(9) . .
C12 C13 C8 120.88(13) . .
C12 C13 H511 119.5(10) . .
C8 C13 H511 119.6(10) . .
F4 C14 F3 104.14(16) . .
F4 C14 C15 113.45(10) . 4_565
F3 C14 C15 110.89(10) . 4_565
F4 C14 C15 113.45(10) . .
F3 C14 C15 110.89(10) . .
C15 C14 C15 104.21(16) 4_565 .
C20 C15 C16 122.65(13) . .
C20 C15 C14 128.22(13) . .
C16 C15 C14 109.12(13) . .
C17 C16 C15 119.05(13) . .
C17 C16 C16 132.35(8) . 4_565
C15 C16 C16 108.59(8) . 4_565
C16 C17 C18 118.54(13) . .
C16 C17 H514 121.6(10) . .
C18 C17 H514 119.8(9) . .
C19 C18 C17 122.38(13) . .
C19 C18 H512 120.4(9) . .
C17 C18 H512 117.1(9) . .
C18 C19 C20 118.36(13) . .
C18 C19 C21 121.82(13) . .
C20 C19 C21 119.82(13) . .
C15 C20 C19 118.99(13) . .
C15 C20 H508 119.0(9) . .
C19 C20 H508 122.0(9) . .
C22 C21 C26 118.23(13) . .
C22 C21 C19 120.73(12) . .
C26 C21 C19 121.02(12) . .
C23 C22 C21 120.85(14) . .
C23 C22 H516 119.7(9) . .
C21 C22 H516 119.5(9) . .
C24 C23 C22 120.30(14) . .
C24 C23 H505 121.2(9) . .
C22 C23 H505 118.5(9) . .
C25 C24 C23 119.68(14) . .
C25 C24 H513 118.6(10) . .
C23 C24 H513 121.7(10) . .
C24 C25 C26 120.28(14) . .
C24 C25 H503 121.4(10) . .
C26 C25 H503 118.3(10) . .
C25 C26 C21 120.65(13) . .
C25 C26 H502 118.9(9) . .
C21 C26 H502 120.5(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.376(2) .
F2 C1 1.379(2) .
C1 C2 1.5101(18) .
C1 C2 1.5101(18) 4_565
C2 C7 1.378(2) .
C2 C3 1.3938(19) .
C3 C4 1.388(2) .
C3 C3 1.472(3) 4_565
C4 C5 1.387(2) .
C4 H515 0.963(16) .
C5 C6 1.398(2) .
C5 H504 0.964(16) .
C6 C7 1.409(2) .
C6 C8 1.4854(19) .
C7 H507 0.984(15) .
C8 C9 1.3995(19) .
C8 C13 1.4010(19) .
C9 C10 1.388(2) .
C9 H501 0.993(14) .
C10 C11 1.383(2) .
C10 H506 1.009(17) .
C11 C12 1.391(2) .
C11 H509 1.017(16) .
C12 C13 1.388(2) .
C12 H510 0.985(16) .
C13 H511 0.965(17) .
F3 C14 1.385(2) .
F4 C14 1.364(2) .
C14 C15 1.5048(19) 4_565
C14 C15 1.5049(19) .
C15 C20 1.372(2) .
C15 C16 1.3972(19) .
C16 C17 1.387(2) .
C16 C16 1.484(3) 4_565
C17 C18 1.397(2) .
C17 H514 0.972(17) .
C18 C19 1.396(2) .
C18 H512 0.964(16) .
C19 C20 1.404(2) .
C19 C21 1.487(2) .
C20 H508 0.967(15) .
C21 C22 1.3981(19) .
C21 C26 1.3991(19) .
C22 C23 1.386(2) .
C22 H516 0.982(15) .
C23 C24 1.385(2) .
C23 H505 0.990(16) .
C24 C25 1.384(2) .
C24 H513 0.973(17) .
C25 C26 1.390(2) .
C25 H503 0.973(17) .
C26 H502 0.973(15) .
