#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:59:21 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180054 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/00/7050006.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_7050006
loop_
_publ_author_name
'Rostron, James P.'
'Ulrich, Gilles'
'Retailleau, Pascal'
'Harriman, Anthony'
'Ziessel, Raymond'
_publ_section_title
;
 Engineering of an electronically decoupled difluoroindacene-pyrene
 dyad possessing high affinity for DNA
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1241
_journal_paper_doi               10.1039/b507585h
_journal_volume                  29
_journal_year                    2005
_chemical_formula_moiety         'C33 H31 B F2 N2, C1 H3 N1 O2'
_chemical_formula_sum            'C34 H34 B F2 N3 O2'
_chemical_formula_weight         565.45
_chemical_name_common
;
4,4-difluoro-8-(-1-pyrenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-
bora-3a,4a-diaza-s-indacene
;
_chemical_name_systematic
;
4,4-difluoro-8-(-1-pyrenyl)-1,3,5,7-tetramethyl-2,4-diethyl-4-bora-
3a,4a-diaza-s-indacene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.33
_cell_angle_beta                 90.79(2)
_cell_angle_gamma                104.64
_cell_formula_units_Z            2
_cell_length_a                   7.266(4)
_cell_length_b                   12.168(3)
_cell_length_c                   17.628(4)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.257
_cell_measurement_theta_min      0.998
_cell_volume                     1480.6(10)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6784
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1192P)²+1.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2070
_refine_ls_wR_factor_ref         0.2367
_reflns_number_gt                2784
_reflns_number_total             4181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507585h.txt
_cod_data_source_block           GU65
_cod_database_code               7050006
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B B 0.0546(8) 0.0234(4) 0.3376(3) 0.0600(13) Uani 1 1 d . . .
F1 F -0.0791(4) -0.0826(2) 0.31429(15) 0.0828(8) Uani 1 1 d . . .
F2 F 0.1340(4) 0.0267(2) 0.41046(12) 0.0834(8) Uani 1 1 d . . .
N1A N -0.0403(5) 0.1234(3) 0.34004(17) 0.0546(8) Uani 1 1 d . . .
N1B N 0.2126(5) 0.0395(3) 0.28009(17) 0.0538(8) Uani 1 1 d . . .
C2A C -0.1139(6) 0.2853(3) 0.3148(2) 0.0595(10) Uani 1 1 d . . .
C2B C 0.4157(6) 0.1154(3) 0.1944(2) 0.0535(10) Uani 1 1 d . . .
C3A C -0.2361(6) 0.2404(4) 0.3681(2) 0.0659(11) Uani 1 1 d . . .
C3B C 0.4597(6) 0.0159(3) 0.2084(2) 0.0588(11) Uani 1 1 d . . .
C4A C -0.1876(6) 0.1412(4) 0.3824(2) 0.0611(11) Uani 1 1 d . . .
C4B C 0.3326(6) -0.0287(3) 0.2617(2) 0.0564(10) Uani 1 1 d . . .
C5A C 0.0091(6) 0.2116(3) 0.2970(2) 0.0527(10) Uani 1 1 d . . .
C5B C 0.2592(6) 0.1298(3) 0.2391(2) 0.0508(10) Uani 1 1 d . . .
C6A C -0.1206(7) 0.3908(4) 0.2830(3) 0.0772(13) Uani 1 1 d . . .
H6A H -0.0229 0.4560 0.3093 0.093 Uiso 1 1 calc R . .
H6B H -0.2430 0.4062 0.2905 0.093 Uiso 1 1 calc R . .
H6C H -0.1001 0.3778 0.2288 0.093 Uiso 1 1 calc R . .
C6B C 0.5211(6) 0.1907(4) 0.1420(3) 0.0695(12) Uani 1 1 d . . .
H6D H 0.6452 0.1777 0.1353 0.083 Uiso 1 1 calc R . .
H6E H 0.5338 0.2705 0.1643 0.083 Uiso 1 1 calc R . .
H6F H 0.4516 0.1723 0.0926 0.083 Uiso 1 1 calc R . .
C7A C -0.3865(7) 0.2915(5) 0.4071(3) 0.0889(15) Uani 1 1 d . . .
H7A H -0.4820 0.2308 0.4240 0.102 Uiso 1 1 calc R . .
H7B H -0.4488 0.3226 0.3702 0.102 Uiso 1 1 calc R . .
C8A C -0.3049(10) 0.3868(6) 0.4763(4) 0.135(3) Uani 1 1 d . . .
H8A H -0.2522 0.3550 0.5149 0.162 Uiso 1 1 calc R . .
H8B H -0.4042 0.4198 0.4973 0.162 Uiso 1 1 calc R . .
H8C H -0.2066 0.4456 0.4603 0.162 Uiso 1 1 calc R . .
C7B C 0.6097(6) -0.0376(4) 0.1717(3) 0.0733(13) Uani 1 1 d . . .
H7C H 0.6262 -0.0971 0.1991 0.084 Uiso 1 1 calc R . .
H7D H 0.7299 0.0211 0.1769 0.084 Uiso 1 1 calc R . .
C8B C 0.5616(7) -0.0903(4) 0.0872(3) 0.0810(14) Uani 1 1 d . . .
H8D H 0.4384 -0.1445 0.0812 0.097 Uiso 1 1 calc R . .
H8E H 0.6556 -0.1296 0.0682 0.097 Uiso 1 1 calc R . .
H8F H 0.5603 -0.0304 0.0586 0.097 Uiso 1 1 calc R . .
C9A C -0.2821(7) 0.0623(4) 0.4346(3) 0.0815(14) Uani 1 1 d . . .
H9A H -0.2018 0.0754 0.4808 0.098 Uiso 1 1 calc R . .
H9B H -0.3031 -0.0166 0.4086 0.098 Uiso 1 1 calc R . .
H9C H -0.4021 0.0777 0.4479 0.098 Uiso 1 1 calc R . .
C9B C 0.3231(7) -0.1345(4) 0.2947(3) 0.0774(13) Uani 1 1 d . . .
H9D H 0.2635 -0.1280 0.3430 0.093 Uiso 1 1 calc R . .
H9E H 0.4497 -0.1422 0.3031 0.093 Uiso 1 1 calc R . .
H9F H 0.2501 -0.2013 0.2594 0.093 Uiso 1 1 calc R . .
C10 C 0.1578(5) 0.2140(3) 0.2473(2) 0.0500(10) Uani 1 1 d . . .
C19 C 0.2091(5) 0.3099(3) 0.2027(2) 0.0488(9) Uani 1 1 d . . .
C20 C 0.3141(6) 0.4182(3) 0.2397(2) 0.0582(10) Uani 1 1 d . . .
H20 H 0.3524 0.4296 0.2917 0.067 Uiso 1 1 calc R . .
C21 C 0.3629(6) 0.5092(3) 0.2015(2) 0.0616(11) Uani 1 1 d . . .
H21 H 0.4328 0.5812 0.2280 0.071 Uiso 1 1 calc R . .
C22 C 0.3090(5) 0.4951(3) 0.1233(2) 0.0530(10) Uani 1 1 d . . .
C23 C 0.3566(6) 0.5874(4) 0.0811(3) 0.0672(12) Uani 1 1 d . . .
H23 H 0.4226 0.6607 0.1070 0.077 Uiso 1 1 calc R . .
C24 C 0.3099(6) 0.5723(4) 0.0065(3) 0.0716(13) Uani 1 1 d . . .
H24 H 0.3432 0.6351 -0.0185 0.082 Uiso 1 1 calc R . .
C25 C 0.2086(6) 0.4610(4) -0.0370(2) 0.0620(11) Uani 1 1 d . . .
C26 C 0.1663(7) 0.4395(5) -0.1162(3) 0.0788(14) Uani 1 1 d . . .
H26 H 0.1999 0.5000 -0.1431 0.091 Uiso 1 1 calc R . .
C27 C 0.0773(7) 0.3321(6) -0.1552(3) 0.0881(16) Uani 1 1 d . . .
H27 H 0.0550 0.3198 -0.2085 0.101 Uiso 1 1 calc R . .
C28 C 0.0187(6) 0.2401(5) -0.1171(2) 0.0742(13) Uani 1 1 d . . .
H28 H -0.0440 0.1673 -0.1448 0.085 Uiso 1 1 calc R . .
C29 C 0.0538(5) 0.2564(4) -0.0370(2) 0.0552(10) Uani 1 1 d . . .
C30 C -0.0018(5) 0.1652(3) 0.0051(2) 0.0549(10) Uani 1 1 d . . .
H30 H -0.0708 0.0926 -0.0208 0.063 Uiso 1 1 calc R . .
C31 C 0.0430(5) 0.1813(3) 0.0815(2) 0.0511(9) Uani 1 1 d . . .
H31 H 0.0031 0.1198 0.1073 0.059 Uiso 1 1 calc R . .
C32 C 0.1531(5) 0.3672(3) 0.0032(2) 0.0500(9) Uani 1 1 d . . .
C33 C 0.2039(5) 0.3850(3) 0.0839(2) 0.0462(9) Uani 1 1 d . . .
C34 C 0.1510(5) 0.2913(3) 0.1240(2) 0.0442(9) Uani 1 1 d . . .
C1' C 0.1562(10) 0.2414(6) 0.5441(4) 0.134(2) Uani 1 1 d . . .
H1'1 H 0.0280 0.2139 0.5583 0.200 Uiso 1 1 calc R . .
H1'2 H 0.2060 0.1767 0.5243 0.200 Uiso 1 1 calc R . .
H1'3 H 0.1568 0.2873 0.5051 0.200 Uiso 1 1 calc R . .
N1' N 0.2713(13) 0.3098(8) 0.6100(5) 0.166(3) Uiso 1 1 d D . .
O1A O 0.202(2) 0.3630(8) 0.6484(5) 0.427(12) Uani 1 1 d D . .
O1B O 0.4210(12) 0.2771(8) 0.6090(6) 0.291(5) Uani 1 1 d 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
F2 B F1 108.7(3) . . ?
F2 B N1A 110.0(3) . . ?
F1 B N1A 110.4(4) . . ?
F2 B N1B 109.7(4) . . ?
F1 B N1B 110.6(3) . . ?
N1A B N1B 107.4(3) . . ?
C4A N1A C5A 107.7(3) . . ?
C4A N1A B 126.7(3) . . ?
C5A N1A B 125.5(3) . . ?
C4B N1B C5B 108.1(3) . . ?
C4B N1B B 126.6(3) . . ?
C5B N1B B 125.3(3) . . ?
C3A C2A C5A 106.8(3) . . ?
C3A C2A C6A 124.5(4) . . ?
C5A C2A C6A 128.7(4) . . ?
C3B C2B C5B 107.1(3) . . ?
C3B C2B C6B 124.3(4) . . ?
C5B C2B C6B 128.6(3) . . ?
C2A C3A C4A 107.5(4) . . ?
C2A C3A C7A 126.7(4) . . ?
C4A C3A C7A 125.7(4) . . ?
C2B C3B C4B 107.4(4) . . ?
C2B C3B C7B 126.8(4) . . ?
C4B C3B C7B 125.8(4) . . ?
N1A C4A C3A 109.9(3) . . ?
N1A C4A C9A 123.1(4) . . ?
C3A C4A C9A 127.0(4) . . ?
N1B C4B C3B 109.6(3) . . ?
N1B C4B C9B 122.7(4) . . ?
C3B C4B C9B 127.6(4) . . ?
C10 C5A N1A 119.9(3) . . ?
C10 C5A C2A 132.0(3) . . ?
N1A C5A C2A 108.1(3) . . ?
C10 C5B N1B 120.4(3) . . ?
C10 C5B C2B 131.8(3) . . ?
N1B C5B C2B 107.8(3) . . ?
C3A C7A C8A 112.4(4) . . ?
C3B C7B C8B 113.1(3) . . ?
C5B C10 C5A 121.5(3) . . ?
C5B C10 C19 119.7(3) . . ?
C5A C10 C19 118.8(3) . . ?
C20 C19 C34 119.9(3) . . ?
C20 C19 C10 119.4(3) . . ?
C34 C19 C10 120.8(3) . . ?
C21 C20 C19 121.5(4) . . ?
C20 C21 C22 120.8(4) . . ?
C21 C22 C33 118.7(3) . . ?
C21 C22 C23 122.8(4) . . ?
C33 C22 C23 118.5(4) . . ?
C24 C23 C22 122.3(4) . . ?
C23 C24 C25 121.5(4) . . ?
C26 C25 C32 118.3(4) . . ?
C26 C25 C24 123.5(4) . . ?
C32 C25 C24 118.1(4) . . ?
C27 C26 C25 121.4(4) . . ?
C26 C27 C28 121.2(4) . . ?
C27 C28 C29 120.2(5) . . ?
C28 C29 C32 118.6(4) . . ?
C28 C29 C30 122.7(4) . . ?
C32 C29 C30 118.7(3) . . ?
C31 C30 C29 121.7(4) . . ?
C30 C31 C34 121.4(3) . . ?
C29 C32 C25 120.1(4) . . ?
C29 C32 C33 120.1(3) . . ?
C25 C32 C33 119.7(4) . . ?
C22 C33 C34 120.3(3) . . ?
C22 C33 C32 119.9(3) . . ?
C34 C33 C32 119.8(3) . . ?
C19 C34 C33 118.7(3) . . ?
C19 C34 C31 123.1(3) . . ?
C33 C34 C31 118.2(3) . . ?
O1A N1' O1B 138.7(13) . . ?
O1A N1' C1' 114.9(11) . . ?
O1B N1' C1' 105.7(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B F2 1.391(5) . ?
B F1 1.393(5) . ?
B N1A 1.538(6) . ?
B N1B 1.540(6) . ?
N1A C4A 1.353(5) . ?
N1A C5A 1.400(4) . ?
N1B C4B 1.354(5) . ?
N1B C5B 1.397(4) . ?
C2A C3A 1.390(6) . ?
C2A C5A 1.419(5) . ?
C2A C6A 1.502(6) . ?
C2B C3B 1.389(5) . ?
C2B C5B 1.422(5) . ?
C2B C6B 1.500(5) . ?
C3A C4A 1.402(6) . ?
C3A C7A 1.504(6) . ?
C3B C4B 1.408(6) . ?
C3B C7B 1.503(6) . ?
C4A C9A 1.497(6) . ?
C4B C9B 1.492(5) . ?
C5A C10 1.399(5) . ?
C5B C10 1.394(5) . ?
C7A C8A 1.519(8) . ?
C7B C8B 1.510(6) . ?
C10 C19 1.496(5) . ?
C19 C20 1.384(5) . ?
C19 C34 1.406(5) . ?
C20 C21 1.371(5) . ?
C21 C22 1.397(5) . ?
C22 C33 1.412(5) . ?
C22 C23 1.430(5) . ?
C23 C24 1.322(6) . ?
C24 C25 1.439(6) . ?
C25 C26 1.389(6) . ?
C25 C32 1.426(5) . ?
C26 C27 1.355(7) . ?
C27 C28 1.386(7) . ?
C28 C29 1.401(6) . ?
C29 C32 1.411(5) . ?
C29 C30 1.422(5) . ?
C30 C31 1.350(5) . ?
C31 C34 1.435(5) . ?
C32 C33 1.429(5) . ?
C33 C34 1.422(5) . ?
C1' N1' 1.420(9) . ?
N1' O1A 1.069(9) . ?
N1' O1B 1.248(5) . ?
