#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:45:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178914 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/43/4114331.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_4114331
loop_
_publ_author_name
'Olivier Siri'
'Pierre Braunstein'
'Marie-Madeleine Rohmer'
'Marc Bénard'
'Richard Welter'
_publ_contact_author_address
;
Institut Le Bel, rue Blaise Pascal, 67000 STRASBOURG, FRANCE
;
_publ_contact_author_email       braunst@chimie.u-strasbg.fr
_publ_contact_author_fax         0390241322
_publ_contact_author_name
;
Pierre Braunstein 
;
_publ_contact_author_phone       0390241308
_publ_section_title
;
 Novel "Potentially Antiaromatic", Acidichromic Quinonediimines with
 Tunable Delocalization of Their 6π-Electron Subunits
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13793
_journal_page_last               13803
_journal_paper_doi               10.1021/ja035463u
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C26 H49 N4, B F4'
_chemical_formula_sum            'C26 H49 B F4 N4'
_chemical_formula_weight         504.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                90.000(5)
_cell_angle_beta                 96.949(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   10.944(5)
_cell_length_b                   22.920(5)
_cell_length_c                   12.172(5)
_cell_measurement_reflns_used    29000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      1.4
_cell_volume                     3031(2)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.3132
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8067
_diffrn_reflns_theta_full        29.06
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         8066
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.3093
_refine_ls_R_factor_gt           0.0941
_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)+(0.0751P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.2358
_reflns_number_gt                5096
_reflns_number_total             8066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035463usi20030704_044358.cif
_cod_data_source_block           5.HBF4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4114331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.2312(3) 0.15091(14) 0.1800(3) 0.0441(9) Uani 1 1 d .
H1 H 0.2538 0.1326 0.1242 0.053 Uiso 1 1 calc .
N2 N 0.1693(3) 0.03901(15) 0.1154(3) 0.0616(11) Uani 1 1 d .
H2 H 0.2165 0.0610 0.0819 0.074 Uiso 1 1 calc .
N3 N -0.0197(3) 0.13409(14) 0.4736(3) 0.0481(9) Uani 1 1 d .
H3 H -0.0702 0.1105 0.4995 0.058 Uiso 1 1 calc .
N4 N -0.1068(3) 0.03662(13) 0.3962(3) 0.0465(9) Uani 1 1 d .
C12 C 0.0037(4) 0.18822(17) 0.5346(3) 0.0478(11) Uani 1 1 d .
H12A H 0.0391 0.2165 0.4882 0.057 Uiso 1 1 calc .
H12B H 0.0630 0.1811 0.5992 0.057 Uiso 1 1 calc .
C6 C -0.0228(3) 0.05778(16) 0.3422(3) 0.0372(10) Uani 1 1 d .
C1 C 0.0287(4) 0.03362(16) 0.2500(3) 0.0411(10) Uani 1 1 d .
H1A H 0.0037 -0.0033 0.2249 0.049 Uiso 1 1 calc .
C5 C 0.0256(3) 0.11625(16) 0.3847(3) 0.0364(10) Uani 1 1 d .
C7 C 0.2836(4) 0.20846(17) 0.2006(3) 0.0449(11) Uani 1 1 d .
H7A H 0.2356 0.2292 0.2501 0.054 Uiso 1 1 calc .
H7B H 0.2769 0.2298 0.1313 0.054 Uiso 1 1 calc .
C4 C 0.1108(3) 0.14598(16) 0.3299(3) 0.0388(10) Uani 1 1 d .
H4 H 0.1404 0.1820 0.3565 0.047 Uiso 1 1 calc .
C3 C 0.1522(3) 0.12267(16) 0.2364(3) 0.0370(10) Uani 1 1 d .
C8 C 0.4183(4) 0.20828(18) 0.2512(4) 0.0507(12) Uani 1 1 d .
C2 C 0.1129(4) 0.06265(17) 0.1975(3) 0.0400(10) Uani 1 1 d .
C19 C -0.3726(4) 0.0312(2) 0.3417(4) 0.0664(14) Uani 1 1 d .
H19A H -0.4542 0.0313 0.3632 0.100 Uiso 1 1 calc .
H19B H -0.3771 0.0260 0.2631 0.100 Uiso 1 1 calc .
H19C H -0.3331 0.0677 0.3621 0.100 Uiso 1 1 calc .
C18 C -0.2985(4) -0.01853(17) 0.4003(3) 0.0432(11) Uani 1 1 d .
C21 C -0.3582(4) -0.0771(2) 0.3681(4) 0.0673(15) Uani 1 1 d .
H21A H -0.4395 -0.0781 0.3901 0.101 Uiso 1 1 calc .
H21B H -0.3097 -0.1079 0.4046 0.101 Uiso 1 1 calc .
H21C H -0.3632 -0.0822 0.2894 0.101 Uiso 1 1 calc .
C17 C -0.1693(4) -0.01820(17) 0.3654(3) 0.0489(12) Uani 1 1 d .
H17A H -0.1221 -0.0504 0.4008 0.059 Uiso 1 1 calc .
H17B H -0.1744 -0.0235 0.2859 0.059 Uiso 1 1 calc .
C13 C -0.1137(4) 0.21328(18) 0.5714(4) 0.0491(11) Uani 1 1 d .
C14 C -0.0765(4) 0.26755(19) 0.6402(4) 0.0622(13) Uani 1 1 d .
H14A H -0.0204 0.2567 0.7037 0.093 Uiso 1 1 calc .
H14B H -0.1484 0.2851 0.6640 0.093 Uiso 1 1 calc .
H14C H -0.0373 0.2949 0.5961 0.093 Uiso 1 1 calc .
C20 C -0.2930(4) -0.0099(2) 0.5253(4) 0.0635(14) Uani 1 1 d .
H20A H -0.3751 -0.0092 0.5456 0.095 Uiso 1 1 calc .
H20B H -0.2527 0.0263 0.5459 0.095 Uiso 1 1 calc .
H20C H -0.2479 -0.0415 0.5629 0.095 Uiso 1 1 calc .
C22 C 0.1548(5) -0.0211(2) 0.0808(6) 0.105(2) Uani 1 1 d .
H22A H 0.0986 -0.0225 0.0129 0.126 Uiso 1 1 calc .
H22B H 0.1171 -0.0424 0.1367 0.126 Uiso 1 1 calc .
C15 C -0.1712(5) 0.1695(2) 0.6440(5) 0.095(2) Uani 1 1 d .
H15A H -0.1133 0.1602 0.7073 0.142 Uiso 1 1 calc .
H15B H -0.1926 0.1347 0.6024 0.142 Uiso 1 1 calc .
H15C H -0.2440 0.1861 0.6682 0.142 Uiso 1 1 calc .
C11 C 0.4287(4) 0.1807(2) 0.3662(4) 0.0743(15) Uani 1 1 d .
H11A H 0.5135 0.1801 0.3977 0.112 Uiso 1 1 calc .
H11B H 0.3976 0.1415 0.3604 0.112 Uiso 1 1 calc .
H11C H 0.3816 0.2031 0.4127 0.112 Uiso 1 1 calc .
C16 C -0.2029(5) 0.2296(2) 0.4701(5) 0.103(2) Uani 1 1 d .
H16A H -0.2767 0.2456 0.4934 0.154 Uiso 1 1 calc .
H16B H -0.2229 0.1955 0.4260 0.154 Uiso 1 1 calc .
H16C H -0.1653 0.2581 0.4271 0.154 Uiso 1 1 calc .
C10 C 0.4972(4) 0.1736(2) 0.1784(5) 0.0806(16) Uani 1 1 d .
H10A H 0.4895 0.1904 0.1057 0.121 Uiso 1 1 calc .
H10B H 0.4697 0.1338 0.1736 0.121 Uiso 1 1 calc .
H10C H 0.5818 0.1749 0.2103 0.121 Uiso 1 1 calc .
C9 C 0.4632(4) 0.2714(2) 0.2598(4) 0.0716(15) Uani 1 1 d .
H9A H 0.4554 0.2886 0.1873 0.107 Uiso 1 1 calc .
H9B H 0.5480 0.2723 0.2912 0.107 Uiso 1 1 calc .
H9C H 0.4146 0.2931 0.3061 0.107 Uiso 1 1 calc .
C23 C 0.2697(4) -0.05112(15) 0.0620(3) 0.0474(11) Uani 1 1 d D
C25 C 0.3893(6) -0.0436(4) 0.1429(7) 0.069(3) Uiso 0.50 1 d PD
H25A H 0.4541 -0.0660 0.1170 0.104 Uiso 0.50 1 calc P
H25B H 0.3756 -0.0570 0.2151 0.104 Uiso 0.50 1 calc P
H25C H 0.4122 -0.0031 0.1466 0.104 Uiso 0.50 1 calc P
C24 C 0.3015(15) -0.0628(7) 0.1877(5) 0.143(5) Uiso 0.50 1 d PD
H24A H 0.3796 -0.0822 0.2008 0.215 Uiso 0.50 1 calc P
H24B H 0.2390 -0.0870 0.2130 0.215 Uiso 0.50 1 calc P
H24C H 0.3055 -0.0264 0.2270 0.215 Uiso 0.50 1 calc P
C29 C 0.2590(8) -0.11833(19) 0.0504(8) 0.053(3) Uiso 0.50 1 d PD
H29A H 0.3363 -0.1341 0.0347 0.079 Uiso 0.50 1 calc P
H29B H 0.1962 -0.1278 -0.0090 0.079 Uiso 0.50 1 calc P
H29C H 0.2378 -0.1347 0.1182 0.079 Uiso 0.50 1 calc P
C28 C 0.2308(10) -0.1070(3) -0.0046(9) 0.081(4) Uiso 0.50 1 d PD
H28A H 0.3028 -0.1285 -0.0179 0.122 Uiso 0.50 1 calc P
H28B H 0.1850 -0.0964 -0.0740 0.122 Uiso 0.50 1 calc P
H28C H 0.1804 -0.1307 0.0368 0.122 Uiso 0.50 1 calc P
C27 C 0.2981(9) -0.0268(4) -0.0508(5) 0.059(3) Uiso 0.50 1 d PD
H27A H 0.3762 -0.0414 -0.0669 0.089 Uiso 0.50 1 calc P
H27B H 0.3009 0.0151 -0.0477 0.089 Uiso 0.50 1 calc P
H27C H 0.2349 -0.0388 -0.1079 0.089 Uiso 0.50 1 calc P
C26 C 0.3695(9) -0.0150(5) 0.0135(11) 0.108(4) Uiso 0.50 1 d PD
H26A H 0.4408 -0.0389 0.0089 0.162 Uiso 0.50 1 calc P
H26B H 0.3918 0.0179 0.0604 0.162 Uiso 0.50 1 calc P
H26C H 0.3381 -0.0015 -0.0592 0.162 Uiso 0.50 1 calc P
B1 B 0.1608(6) 0.1511(3) -0.1089(5) 0.0630(16) Uani 1 1 d .
F1 F 0.1706(4) 0.14804(17) -0.2186(3) 0.1384(15) Uani 1 1 d .
F2 F 0.1635(4) 0.20799(15) -0.0872(3) 0.1355(15) Uani 1 1 d .
F3 F 0.0636(3) 0.1276(2) -0.0791(5) 0.215(3) Uani 1 1 d .
F4 F 0.2637(3) 0.12546(12) -0.0507(2) 0.0779(9) 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'
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
C3 N1 C7 128.3(3)
C2 N2 C22 123.7(4)
C5 N3 C12 128.9(3)
C6 N4 C17 122.3(4)
N3 C12 C13 111.7(3)
N4 C6 C1 129.0(4)
N4 C6 C5 113.7(4)
C1 C6 C5 117.3(3)
C2 C1 C6 122.3(4)
N3 C5 C4 125.9(4)
N3 C5 C6 114.1(4)
C4 C5 C6 119.9(4)
N1 C7 C8 114.2(3)
C3 C4 C5 120.8(4)
N1 C3 C4 122.2(4)
N1 C3 C2 117.5(4)
C4 C3 C2 120.3(4)
C11 C8 C7 109.4(4)
C11 C8 C9 110.0(4)
C7 C8 C9 108.2(3)
C11 C8 C10 109.3(4)
C7 C8 C10 110.6(4)
C9 C8 C10 109.3(4)
N2 C2 C1 123.3(4)
N2 C2 C3 117.5(4)
C1 C2 C3 119.1(4)
C21 C18 C17 108.4(3)
C21 C18 C19 110.6(4)
C17 C18 C19 108.9(3)
C21 C18 C20 109.5(4)
C17 C18 C20 110.6(4)
C19 C18 C20 108.9(4)
N4 C17 C18 110.7(3)
C15 C13 C16 111.3(4)
C15 C13 C12 110.2(4)
C16 C13 C12 109.6(4)
C15 C13 C14 108.7(4)
C16 C13 C14 110.2(4)
C12 C13 C14 106.8(3)
N2 C22 C23 115.2(4)
C22 C23 C26 117.7(6)
C22 C23 C28 106.3(5)
C26 C23 C28 113.9(7)
C22 C23 C25 121.3(5)
C26 C23 C25 66.5(6)
C28 C23 C25 125.7(6)
C22 C23 C27 103.6(5)
C26 C23 C27 40.5(5)
C28 C23 C27 84.6(6)
C25 C23 C27 106.2(6)
C22 C23 C24 91.2(7)
C26 C23 C24 112.7(8)
C28 C23 C24 112.9(8)
C25 C23 C24 47.2(6)
C27 C23 C24 153.1(8)
C22 C23 C29 114.9(5)
C26 C23 C29 123.2(7)
C28 C23 C29 28.0(5)
C25 C23 C29 102.6(6)
C27 C23 C29 107.3(5)
C24 C23 C29 85.7(7)
F3 B1 F2 110.7(6)
F3 B1 F1 115.1(6)
F2 B1 F1 104.1(5)
F3 B1 F4 109.2(5)
F2 B1 F4 108.5(5)
F1 B1 F4 109.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.334(4)
N1 C7 1.448(5)
N2 C2 1.350(5)
N2 C22 1.443(6)
N3 C5 1.309(5)
N3 C12 1.453(5)
N4 C6 1.289(5)
N4 C17 1.457(5)
C12 C13 1.524(5)
C6 C1 1.427(5)
C6 C5 1.509(5)
C1 C2 1.357(5)
C5 C4 1.389(5)
C7 C8 1.527(6)
C4 C3 1.383(5)
C3 C2 1.501(5)
C8 C11 1.527(6)
C8 C9 1.528(6)
C8 C10 1.532(6)
C19 C18 1.525(6)
C18 C21 1.524(6)
C18 C17 1.525(5)
C18 C20 1.528(6)
C13 C15 1.522(6)
C13 C16 1.524(6)
C13 C14 1.527(5)
C22 C23 1.475(6)
C23 C26 1.545(3)
C23 C28 1.547(3)
C23 C25 1.549(3)
C23 C27 1.549(3)
C23 C24 1.550(3)
C23 C29 1.550(3)
B1 F3 1.282(6)
B1 F2 1.330(6)
B1 F1 1.355(6)
B1 F4 1.387(6)
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
C5 N3 C12 C13 139.0(4)
C17 N4 C6 C1 -2.6(6)
C17 N4 C6 C5 177.3(3)
N4 C6 C1 C2 176.4(4)
C5 C6 C1 C2 -3.6(5)
C12 N3 C5 C4 1.7(7)
C12 N3 C5 C6 -178.4(4)
N4 C6 C5 N3 4.3(5)
C1 C6 C5 N3 -175.8(3)
N4 C6 C5 C4 -175.8(3)
C1 C6 C5 C4 4.1(5)
C3 N1 C7 C8 105.4(5)
N3 C5 C4 C3 179.9(4)
C6 C5 C4 C3 0.1(6)
C7 N1 C3 C4 -2.1(6)
C7 N1 C3 C2 -179.5(3)
C5 C4 C3 N1 177.9(4)
C5 C4 C3 C2 -4.7(6)
N1 C7 C8 C11 -64.5(5)
N1 C7 C8 C9 175.7(4)
N1 C7 C8 C10 56.0(5)
C22 N2 C2 C1 -5.6(7)
C22 N2 C2 C3 170.4(4)
C6 C1 C2 N2 175.0(4)
C6 C1 C2 C3 -0.9(6)
N1 C3 C2 N2 6.6(5)
C4 C3 C2 N2 -170.9(4)
N1 C3 C2 C1 -177.3(3)
C4 C3 C2 C1 5.3(6)
C6 N4 C17 C18 -152.0(4)
C21 C18 C17 N4 -178.9(3)
C19 C18 C17 N4 60.7(5)
C20 C18 C17 N4 -58.9(4)
N3 C12 C13 C15 58.7(5)
N3 C12 C13 C16 -64.0(5)
N3 C12 C13 C14 176.6(3)
C2 N2 C22 C23 -135.9(5)
N2 C22 C23 C26 -35.2(9)
N2 C22 C23 C28 -164.3(6)
N2 C22 C23 C25 42.8(8)
N2 C22 C23 C27 -76.1(6)
N2 C22 C23 C24 81.3(8)
N2 C22 C23 C29 167.1(6)
