#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:49:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178825 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/79/4107905.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_4107905
loop_
_publ_author_name
'Edward L. Clennan'
'Chen Liao'
'Erambo Ayokosok'
_publ_section_title
;
 Pyrylogens: Synthesis, Structural, Electrochemical, and Photophysical
 Characterization of a New Class of Electron Transfer Sensitizers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7552
_journal_page_last               7553
_journal_paper_doi               10.1021/ja802343v
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C23 H19 N O, 2(C24 B F20)'
_chemical_formula_sum            'C71 H19 B2 F40 N O'
_chemical_formula_weight         1683.49
_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'
_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                 108.852(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.306(3)
_cell_length_b                   16.092(3)
_cell_length_c                   21.832(4)
_cell_measurement_reflns_used    9413
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.45
_cell_volume                     6419(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL V. 6.14'
_computing_publication_material  'Bruker SHELXTL V. 6.14'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            108152
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9511
_exptl_absorpt_correction_T_min  0.9426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       Rectangular_prism
_exptl_crystal_F_000             3320
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         11151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+2.2857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                5489
_reflns_number_total             11151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802343v-file002.cif
_cod_data_source_block           cl01
_cod_original_cell_volume        6418.7(18)
_cod_database_code               4107905
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5000 0.99328(9) 0.2500 0.0525(4) Uani 1 2 d S . .
C1 C 0.48685(8) 0.95328(10) 0.19297(7) 0.0498(3) Uani 1 1 d . . .
C2 C 0.48954(9) 0.86824(10) 0.19293(8) 0.0530(4) Uani 1 1 d . . .
H2 H 0.4819(9) 0.8396(11) 0.1538(9) 0.060(5) Uiso 1 1 d . . .
C3 C 0.5000 0.82475(13) 0.2500 0.0505(5) Uani 1 2 d S . .
C4 C 0.5000 0.73284(13) 0.2500 0.0492(5) Uani 1 2 d S . .
C5 C 0.54548(10) 0.68871(10) 0.22358(8) 0.0545(4) Uani 1 1 d . . .
H5 H 0.5774(9) 0.7170(10) 0.2055(8) 0.052(4) Uiso 1 1 d . . .
C6 C 0.54477(10) 0.60354(11) 0.22468(8) 0.0574(4) Uani 1 1 d . . .
H6 H 0.5749(10) 0.5717(12) 0.2075(9) 0.072(6) Uiso 1 1 d . . .
N1 N 0.5000 0.56230(11) 0.2500 0.0551(5) Uani 1 2 d S . .
C7 C 0.5000 0.47006(15) 0.2500 0.0766(8) Uani 1 2 d S . .
H7A H 0.4652 0.4502 0.2696 0.115 Uiso 0.50 1 calc PR A -1
H7B H 0.5479 0.4502 0.2741 0.115 Uiso 0.50 1 calc PR A -1
H7C H 0.4868 0.4502 0.2063 0.115 Uiso 0.50 1 calc PR A -1
C8 C 0.47037(9) 1.00829(10) 0.13736(7) 0.0526(4) Uani 1 1 d . . .
C9 C 0.44296(11) 0.97488(13) 0.07532(9) 0.0661(5) Uani 1 1 d . . .
H9 H 0.4358(10) 0.9165(13) 0.0675(9) 0.074(6) Uiso 1 1 d . . .
C10 C 0.42560(12) 1.02664(15) 0.02239(10) 0.0743(5) Uani 1 1 d . . .
H10 H 0.4081(11) 1.0011(12) -0.0182(11) 0.077(6) Uiso 1 1 d . . .
C11 C 0.43494(13) 1.11091(15) 0.03046(10) 0.0794(6) Uani 1 1 d . . .
H11 H 0.4206(12) 1.1464(14) -0.0051(12) 0.091(7) Uiso 1 1 d . . .
C12 C 0.46203(13) 1.14481(14) 0.09092(10) 0.0791(6) Uani 1 1 d . . .
H12 H 0.4707(14) 1.2053(18) 0.0952(12) 0.110(8) Uiso 1 1 d . . .
C13 C 0.47996(11) 1.09389(12) 0.14481(10) 0.0676(5) Uani 1 1 d . . .
H13 H 0.5004(11) 1.1143(13) 0.1880(10) 0.075(6) Uiso 1 1 d . . .
B1 B 0.18837(10) 0.82990(11) 0.13960(9) 0.0503(4) Uani 1 1 d . . .
C14 C 0.10449(9) 0.83306(9) 0.08712(8) 0.0500(4) Uani 1 1 d . . .
C15 C 0.07759(9) 0.78584(10) 0.03102(8) 0.0536(4) Uani 1 1 d . . .
F15 F 0.11679(6) 0.72354(7) 0.01762(5) 0.0689(3) Uani 1 1 d . . .
C16 C 0.01043(10) 0.79898(12) -0.01548(8) 0.0645(5) Uani 1 1 d . . .
F16 F -0.01121(6) 0.75038(8) -0.06892(5) 0.0866(4) Uani 1 1 d . . .
C17 C -0.03420(11) 0.86056(16) -0.00817(11) 0.0790(6) Uani 1 1 d . . .
F17 F -0.09919(7) 0.87417(12) -0.05373(8) 0.1271(6) Uani 1 1 d . . .
C18 C -0.01140(11) 0.90955(13) 0.04571(11) 0.0782(6) Uani 1 1 d . . .
F18 F -0.05344(8) 0.97219(10) 0.05486(8) 0.1190(5) Uani 1 1 d . . .
C19 C 0.05633(10) 0.89556(11) 0.09070(8) 0.0603(4) Uani 1 1 d . . .
F19 F 0.07719(7) 0.94864(7) 0.14166(5) 0.0780(3) Uani 1 1 d . . .
C20 C 0.22283(9) 0.91790(10) 0.12301(8) 0.0541(4) Uani 1 1 d . . .
C21 C 0.23184(9) 0.93002(11) 0.06315(8) 0.0559(4) Uani 1 1 d . . .
F21 F 0.21849(6) 0.86554(6) 0.02099(5) 0.0685(3) Uani 1 1 d . . .
C22 C 0.25194(10) 1.00350(12) 0.04179(9) 0.0640(4) Uani 1 1 d . . .
F22 F 0.25874(7) 1.00932(8) -0.01719(6) 0.0892(4) Uani 1 1 d . . .
C23 C 0.26464(11) 1.07185(12) 0.08099(10) 0.0722(5) Uani 1 1 d . . .
F23 F 0.28254(9) 1.14488(8) 0.06114(7) 0.1047(4) Uani 1 1 d . . .
C24 C 0.25587(12) 1.06477(12) 0.14036(10) 0.0749(5) Uani 1 1 d . . .
F24 F 0.26510(10) 1.13167(8) 0.17922(7) 0.1160(5) Uani 1 1 d . . .
C25 C 0.23469(12) 0.99006(11) 0.15975(9) 0.0657(5) Uani 1 1 d . . .
F25 F 0.22300(9) 0.99247(7) 0.21756(5) 0.0935(4) Uani 1 1 d . . .
C26 C 0.19469(10) 0.82538(9) 0.21688(8) 0.0548(4) Uani 1 1 d . . .
C27 C 0.13983(11) 0.81180(11) 0.24299(8) 0.0630(5) Uani 1 1 d . . .
F27 F 0.06961(6) 0.79920(7) 0.20435(5) 0.0779(3) Uani 1 1 d . . .
C28 C 0.15045(15) 0.81008(12) 0.30873(10) 0.0794(6) Uani 1 1 d . . .
F28 F 0.09269(10) 0.79871(10) 0.32984(7) 0.1135(5) Uani 1 1 d . . .
C29 C 0.21939(18) 0.82048(12) 0.35187(9) 0.0872(8) Uani 1 1 d . . .
F29 F 0.22982(12) 0.81947(9) 0.41574(6) 0.1289(7) Uani 1 1 d . . .
C30 C 0.27650(15) 0.83046(12) 0.32872(10) 0.0798(6) Uani 1 1 d . . .
F30 F 0.34500(9) 0.83933(9) 0.36992(6) 0.1159(5) Uani 1 1 d . . .
C31 C 0.26349(12) 0.83282(11) 0.26332(9) 0.0661(5) Uani 1 1 d . . .
F31 F 0.32306(6) 0.84499(8) 0.24439(6) 0.0815(3) Uani 1 1 d . . .
C32 C 0.23280(9) 0.74452(10) 0.13210(7) 0.0504(4) Uani 1 1 d . . .
C33 C 0.30054(9) 0.73738(11) 0.12410(8) 0.0582(4) Uani 1 1 d . . .
F33 F 0.33833(6) 0.80532(7) 0.11704(6) 0.0769(3) Uani 1 1 d . . .
C34 C 0.33563(10) 0.66225(13) 0.12487(9) 0.0678(5) Uani 1 1 d . . .
F34 F 0.40193(6) 0.66055(9) 0.11654(6) 0.0951(4) Uani 1 1 d . . .
C35 C 0.30463(11) 0.59013(13) 0.13469(9) 0.0727(6) Uani 1 1 d . . .
F35 F 0.34022(8) 0.51749(8) 0.13816(7) 0.1073(5) Uani 1 1 d . . .
C36 C 0.23685(11) 0.59221(11) 0.14186(8) 0.0659(5) Uani 1 1 d . . .
F36 F 0.20328(8) 0.52177(7) 0.14888(6) 0.0922(4) Uani 1 1 d . . .
C37 C 0.20305(9) 0.66840(10) 0.14075(8) 0.0563(4) Uani 1 1 d . . .
F37 F 0.13701(6) 0.66633(6) 0.14897(6) 0.0714(3) Uani 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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1 O1 C1 123.09(17) . 2_655
O1 C1 C2 118.74(14) . .
O1 C1 C8 113.92(14) . .
C2 C1 C8 127.34(15) . .
C1 C2 C3 119.91(16) . .
C1 C2 H2 119.7(11) . .
C3 C2 H2 120.3(11) . .
C2 C3 C2 119.3(2) 2_655 .
C2 C3 C4 120.34(11) 2_655 .
C2 C3 C4 120.34(11) . .
C5 C4 C5 118.6(2) 2_655 .
C5 C4 C3 120.70(11) 2_655 .
C5 C4 C3 120.70(11) . .
C6 C5 C4 119.46(17) . .
C6 C5 H5 119.9(10) . .
C4 C5 H5 120.6(10) . .
N1 C6 C5 120.86(17) . .
N1 C6 H6 117.3(12) . .
C5 C6 H6 121.8(12) . .
C6 N1 C6 120.7(2) . 2_655
C6 N1 C7 119.63(10) . .
C6 N1 C7 119.63(10) 2_655 .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 119.32(16) . .
C13 C8 C1 121.35(15) . .
C9 C8 C1 119.31(16) . .
C10 C9 C8 119.7(2) . .
C10 C9 H9 117.6(12) . .
C8 C9 H9 122.7(12) . .
C11 C10 C9 120.3(2) . .
C11 C10 H10 123.3(13) . .
C9 C10 H10 116.4(13) . .
C12 C11 C10 120.8(2) . .
C12 C11 H11 118.6(14) . .
C10 C11 H11 120.5(14) . .
C11 C12 C13 119.9(2) . .
C11 C12 H12 119.0(15) . .
C13 C12 H12 121.1(15) . .
C12 C13 C8 119.97(19) . .
C12 C13 H13 123.1(13) . .
C8 C13 H13 116.9(13) . .
C26 B1 C20 111.03(13) . .
C26 B1 C14 116.16(14) . .
C20 B1 C14 101.25(12) . .
C26 B1 C32 101.23(12) . .
C20 B1 C32 115.53(14) . .
C14 B1 C32 112.29(12) . .
C19 C14 C15 112.25(15) . .
C19 C14 B1 120.42(14) . .
C15 C14 B1 126.59(13) . .
F15 C15 C16 114.54(15) . .
F15 C15 C14 121.51(14) . .
C16 C15 C14 123.95(16) . .
F16 C16 C17 119.53(17) . .
F16 C16 C15 120.01(17) . .
C17 C16 C15 120.45(18) . .
F17 C17 C16 120.6(2) . .
F17 C17 C18 120.5(2) . .
C16 C17 C18 118.90(17) . .
F18 C18 C17 121.15(19) . .
F18 C18 C19 119.6(2) . .
C17 C18 C19 119.19(17) . .
F19 C19 C18 116.37(16) . .
F19 C19 C14 118.38(15) . .
C18 C19 C14 125.24(18) . .
C21 C20 C25 112.30(16) . .
C21 C20 B1 120.58(14) . .
C25 C20 B1 126.36(15) . .
F21 C21 C22 116.20(15) . .
F21 C21 C20 118.55(15) . .
C22 C21 C20 125.23(16) . .
F22 C22 C23 119.51(17) . .
F22 C22 C21 120.89(16) . .
C23 C22 C21 119.60(17) . .
F23 C23 C24 120.39(18) . .
F23 C23 C22 121.18(19) . .
C24 C23 C22 118.39(17) . .
F24 C24 C23 119.99(18) . .
F24 C24 C25 119.70(19) . .
C23 C24 C25 120.27(17) . .
F25 C25 C24 114.63(15) . .
F25 C25 C20 121.15(16) . .
C24 C25 C20 124.17(18) . .
C27 C26 C31 113.20(17) . .
C27 C26 B1 128.19(16) . .
C31 C26 B1 118.56(16) . .
F27 C27 C26 120.93(15) . .
F27 C27 C28 115.11(19) . .
C26 C27 C28 124.0(2) . .
F28 C28 C29 120.6(2) . .
F28 C28 C27 119.7(2) . .
C29 C28 C27 119.7(2) . .
F29 C29 C30 121.2(3) . .
F29 C29 C28 119.9(3) . .
C30 C29 C28 118.84(19) . .
F30 C30 C29 120.2(2) . .
F30 C30 C31 120.3(3) . .
C29 C30 C31 119.5(2) . .
F31 C31 C30 115.74(19) . .
F31 C31 C26 119.61(16) . .
C30 C31 C26 124.6(2) . .
C33 C32 C37 113.19(15) . .
C33 C32 B1 128.65(15) . .
C37 C32 B1 117.86(15) . .
F33 C33 C32 121.08(15) . .
F33 C33 C34 115.37(16) . .
C32 C33 C34 123.51(18) . .
F34 C34 C35 119.39(17) . .
F34 C34 C33 119.9(2) . .
C35 C34 C33 120.74(18) . .
F35 C35 C34 120.6(2) . .
F35 C35 C36 120.3(2) . .
C34 C35 C36 119.03(16) . .
F36 C36 C35 120.59(17) . .
F36 C36 C37 120.56(19) . .
C35 C36 C37 118.85(18) . .
F37 C37 C36 115.95(16) . .
F37 C37 C32 119.41(14) . .
C36 C37 C32 124.65(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3507(17) .
O1 C1 1.3507(17) 2_655
C1 C2 1.370(2) .
C1 C8 1.452(2) .
C2 C3 1.386(2) .
C2 H2 0.940(18) .
C3 C2 1.386(2) 2_655
C3 C4 1.479(3) .
C4 C5 1.391(2) 2_655
C4 C5 1.391(2) .
C5 C6 1.371(2) .
C5 H5 0.949(17) .
C6 N1 1.342(2) .
C6 H6 0.94(2) .
N1 C6 1.342(2) 2_655
N1 C7 1.484(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C13 1.393(3) .
C8 C9 1.393(2) .
C9 C10 1.375(3) .
C9 H9 0.96(2) .
C10 C11 1.372(3) .
C10 H10 0.93(2) .
C11 C12 1.366(3) .
C11 H11 0.93(2) .
C12 C13 1.383(3) .
C12 H12 0.99(3) .
C13 H13 0.96(2) .
B1 C26 1.653(2) .
B1 C20 1.654(3) .
B1 C14 1.655(2) .
B1 C32 1.656(2) .
C14 C19 1.389(2) .
C14 C15 1.391(2) .
C15 F15 1.3441(19) .
C15 C16 1.380(2) .
C16 F16 1.354(2) .
C16 C17 1.356(3) .
C17 F17 1.344(2) .
C17 C18 1.365(3) .
C18 F18 1.349(2) .
C18 C19 1.377(3) .
C19 F19 1.356(2) .
C20 C21 1.387(2) .
C20 C25 1.388(2) .
C21 F21 1.3554(18) .
C21 C22 1.372(3) .
C22 F22 1.339(2) .
C22 C23 1.366(3) .
C23 F23 1.336(2) .
C23 C24 1.365(3) .
C24 F24 1.346(2) .
C24 C25 1.380(3) .
C25 F25 1.353(2) .
C26 C27 1.373(3) .
C26 C31 1.391(3) .
C27 F27 1.361(2) .
C27 C28 1.383(3) .
C28 F28 1.349(3) .
C28 C29 1.370(4) .
C29 F29 1.343(2) .
C29 C30 1.363(4) .
C30 F30 1.345(3) .
C30 C31 1.368(3) .
C31 F31 1.356(2) .
C32 C33 1.379(2) .
C32 C37 1.392(2) .
C33 F33 1.351(2) .
C33 C34 1.383(2) .
C34 F34 1.350(2) .
C34 C35 1.354(3) .
C35 F35 1.346(2) .
C35 C36 1.367(3) .
C36 F36 1.339(2) .
C36 C37 1.385(2) .
C37 F37 1.344(2) .
