#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:34:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180227 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/13/7111347.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111347
loop_
_publ_author_name
'Wilson, James N.'
'Smith, Mark D.'
'Enkelmann, Volker'
'Bunz, Uwe H. F.'
_publ_section_title
;
 Cruciform ?-systems: effect of aggregation on emissionElectronic
 supplementary information (ESI) available: X-ray data of 1?4 and electron
 diffraction (experimental and simulated) of 3. See
 http://www.rsc.org/suppdata/cc/b4/b406495j/
;
_journal_issue                   15
_journal_name_full               'Chemical Communications'
_journal_page_first              1700
_journal_page_last               1701
_journal_paper_doi               10.1039/b406495j
_journal_year                    2004
_chemical_formula_sum            'C58 H56 F12 N2'
_chemical_formula_weight         1009.05
_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                 128.2140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   42.3302(15)
_cell_length_b                   5.1937(2)
_cell_length_c                   28.8208(11)
_cell_measurement_reflns_used    9712
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.259
_cell_volume                     4978.4(3)
_computing_cell_refinement       'SAINT+ NT V6.02a (Bruker, 1998)'
_computing_data_collection       'SMART NT V5.625 (Bruker, 2000)'
_computing_data_reduction        'SAINT+ NT V6.02a'
_computing_molecular_graphics    'SHELXTL V5.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL V5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16856
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0541
_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)+(0.0791P)²+1.6060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                3383
_reflns_number_total             4406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b406495jsup1.cif
_cod_data_source_block           jw06s
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7111347
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
C1 C 0.28244(6) 0.6204(4) 0.55218(9) 0.0282(5) Uani 1 1 d .
C2 C 0.28929(6) 0.8240(4) 0.52823(9) 0.0292(5) Uani 1 1 d .
H2 H 0.3162 0.8782 0.5474 0.033(6) Uiso 1 1 calc R
C3 C 0.25822(6) 0.9520(4) 0.47717(9) 0.0267(5) Uani 1 1 d .
C4 C 0.26724(6) 1.1575(4) 0.45389(9) 0.0297(5) Uani 1 1 d .
C5 C 0.27251(7) 1.3297(4) 0.43175(10) 0.0310(5) Uani 1 1 d .
C6 C 0.27547(7) 1.5322(4) 0.40090(9) 0.0297(5) Uani 1 1 d .
C7 C 0.31251(7) 1.6143(4) 0.41760(10) 0.0311(5) Uani 1 1 d .
H7 H 0.3367 1.5405 0.4511 0.029(6) Uiso 1 1 calc R
C8 C 0.31408(7) 1.8048(4) 0.38511(10) 0.0317(5) Uani 1 1 d .
C9 C 0.27908(7) 1.9130(4) 0.33612(10) 0.0329(5) Uani 1 1 d .
H9 H 0.2803 2.0410 0.3137 0.034(6) Uiso 1 1 calc R
C10 C 0.24238(7) 1.8337(4) 0.32005(10) 0.0312(5) Uani 1 1 d .
C11 C 0.24051(7) 1.6457(4) 0.35227(9) 0.0307(5) Uani 1 1 d .
H11 H 0.2151 1.5936 0.3411 0.032(6) Uiso 1 1 calc R
C12 C 0.35341(7) 1.8902(5) 0.40149(11) 0.0390(6) Uani 1 1 d .
C13 C 0.20467(7) 1.9485(4) 0.26637(10) 0.0364(5) Uani 1 1 d .
C14 C 0.31475(6) 0.4764(4) 0.60410(10) 0.0316(5) Uani 1 1 d .
H14 H 0.3063 0.3421 0.6166 0.050(7) Uiso 1 1 calc R
C15 C 0.35420(7) 0.5073(4) 0.63612(10) 0.0329(5) Uani 1 1 d .
H15 H 0.3634 0.6469 0.6260 0.056(8) Uiso 1 1 calc R
C16 C 0.38470(6) 0.3448(4) 0.68565(10) 0.0318(5) Uani 1 1 d .
C17 C 0.37540(7) 0.1651(4) 0.71171(11) 0.0402(6) Uani 1 1 d .
H17 H 0.3485 0.1555 0.6982 0.041(7) Uiso 1 1 calc R
C18 C 0.40348(7) 0.0025(4) 0.75589(11) 0.0408(6) Uani 1 1 d .
H18 H 0.3956 -0.1136 0.7726 0.062(8) Uiso 1 1 calc R
C19 C 0.44362(7) 0.0031(4) 0.77716(10) 0.0335(5) Uani 1 1 d .
C20 C 0.45355(7) 0.1896(4) 0.75298(10) 0.0340(5) Uani 1 1 d .
H20 H 0.4806 0.2030 0.7672 0.034(6) Uiso 1 1 calc R
C21 C 0.42488(7) 0.3547(4) 0.70895(10) 0.0347(5) Uani 1 1 d .
H21 H 0.4329 0.4796 0.6941 0.040(7) Uiso 1 1 calc R
C22 C 0.46046(7) -0.3446(4) 0.84725(10) 0.0392(6) Uani 1 1 d .
H22A H 0.4791 -0.4932 0.8639 0.031(6) Uiso 1 1 calc R
H22B H 0.4330 -0.4116 0.8167 0.046(7) Uiso 1 1 calc R
C23 C 0.46163(7) -0.2218(5) 0.89619(11) 0.0425(6) Uani 1 1 d .
H23A H 0.4900 -0.1870 0.9304 0.043(7) Uiso 1 1 calc R
H23B H 0.4473 -0.0547 0.8821 0.052(7) Uiso 1 1 calc R
C24 C 0.44277(8) -0.3878(5) 0.91623(12) 0.0484(7) Uani 1 1 d .
H24A H 0.4532 -0.5656 0.9226 0.042(7) Uiso 1 1 calc R
H24B H 0.4133 -0.3934 0.8845 0.057(8) Uiso 1 1 calc R
C25 C 0.45113(9) -0.2914(6) 0.97266(13) 0.0601(8) Uani 1 1 d .
H25A H 0.4801 -0.2956 1.0049 0.056(8) Uiso 1 1 calc R
H25B H 0.4373 -0.4021 0.9826 0.083(11) Uiso 1 1 calc R
H25C H 0.4413 -0.1144 0.9669 0.085(11) Uiso 1 1 calc R
C26 C 0.51196(7) -0.1811(4) 0.83820(11) 0.0390(6) Uani 1 1 d .
H26A H 0.5109 -0.1543 0.8033 0.048(7) Uiso 1 1 calc R
H26B H 0.5228 -0.3561 0.8535 0.038(6) Uiso 1 1 calc R
C27 C 0.54118(7) 0.0132(4) 0.88533(10) 0.0381(6) Uani 1 1 d .
H27A H 0.5317 0.1892 0.8693 0.049(7) Uiso 1 1 calc R
H27B H 0.5412 -0.0051 0.9195 0.062(8) Uiso 1 1 calc R
C28 C 0.58376(7) -0.0187(5) 0.90628(11) 0.0421(6) Uani 1 1 d .
H28A H 0.5833 -0.0266 0.8715 0.053(8) Uiso 1 1 calc R
H28B H 0.5947 -0.1839 0.9278 0.059(8) Uiso 1 1 calc R
C29 C 0.61127(8) 0.1985(5) 0.94633(12) 0.0492(7) Uani 1 1 d .
H29A H 0.6019 0.3606 0.9242 0.065(9) Uiso 1 1 calc R
H29B H 0.6387 0.1628 0.9607 0.078(10) Uiso 1 1 calc R
H29C H 0.6110 0.2123 0.9800 0.074(10) Uiso 1 1 calc R
F1 F 0.38480(4) 1.7995(3) 0.45363(7) 0.0586(5) Uani 1 1 d .
F2 F 0.35698(4) 2.1460(3) 0.40498(7) 0.0540(4) Uani 1 1 d .
F3 F 0.35869(5) 1.8189(4) 0.36252(8) 0.0684(5) Uani 1 1 d .
F4 F 0.20295(6) 2.1978(3) 0.26925(8) 0.0851(7) Uani 1 1 d .
F5 F 0.17179(5) 1.8608(5) 0.25560(10) 0.1174(10) Uani 1 1 d .
F6 F 0.20086(6) 1.9052(4) 0.21832(7) 0.0834(6) Uani 1 1 d .
N1 N 0.47120(6) -0.1714(3) 0.81908(8) 0.0373(5) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 117.03(19) . 7_566
C2 C1 C14 123.22(19) . .
C3 C1 C14 119.72(19) 7_566 .
C1 C2 C3 122.5(2) . .
C2 C3 C1 120.44(19) . 7_566
C2 C3 C4 119.94(19) . .
C1 C3 C4 119.62(19) 7_566 .
C5 C4 C3 176.3(2) . .
C4 C5 C6 175.2(2) . .
C11 C6 C7 119.13(19) . .
C11 C6 C5 119.3(2) . .
C7 C6 C5 121.5(2) . .
C8 C7 C6 119.8(2) . .
C9 C8 C7 120.6(2) . .
C9 C8 C12 118.9(2) . .
C7 C8 C12 120.5(2) . .
C10 C9 C8 119.5(2) . .
C9 C10 C11 120.3(2) . .
C9 C10 C13 119.14(19) . .
C11 C10 C13 120.5(2) . .
C10 C11 C6 120.6(2) . .
F3 C12 F1 106.5(2) . .
F3 C12 F2 105.74(19) . .
F1 C12 F2 106.24(19) . .
F3 C12 C8 112.89(19) . .
F1 C12 C8 113.05(19) . .
F2 C12 C8 111.90(19) . .
F4 C13 F5 105.6(2) . .
F4 C13 F6 105.2(2) . .
F5 C13 F6 105.8(2) . .
F4 C13 C10 113.3(2) . .
F5 C13 C10 113.88(19) . .
F6 C13 C10 112.25(19) . .
C15 C14 C1 128.9(2) . .
C14 C15 C16 125.5(2) . .
C21 C16 C17 115.6(2) . .
C21 C16 C15 121.8(2) . .
C17 C16 C15 122.5(2) . .
C18 C17 C16 122.7(2) . .
C17 C18 C19 121.6(2) . .
N1 C19 C20 122.6(2) . .
N1 C19 C18 121.4(2) . .
C20 C19 C18 116.0(2) . .
C21 C20 C19 121.5(2) . .
C20 C21 C16 122.5(2) . .
N1 C22 C23 114.49(19) . .
C24 C23 C22 113.2(2) . .
C23 C24 C25 113.1(2) . .
N1 C26 C27 115.76(19) . .
C28 C27 C26 113.13(19) . .
C27 C28 C29 112.7(2) . .
C19 N1 C26 121.26(19) . .
C19 N1 C22 120.43(19) . .
C26 N1 C22 118.25(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.388(3) .
C1 C3 1.421(3) 7_566
C1 C14 1.462(3) .
C2 C3 1.394(3) .
C3 C1 1.421(3) 7_566
C3 C4 1.433(3) .
C4 C5 1.197(3) .
C5 C6 1.431(3) .
C6 C11 1.391(3) .
C6 C7 1.392(3) .
C7 C8 1.392(3) .
C8 C9 1.385(3) .
C8 C12 1.490(3) .
C9 C10 1.381(3) .
C10 C11 1.383(3) .
C10 C13 1.497(3) .
C12 F3 1.326(3) .
C12 F1 1.332(3) .
C12 F2 1.334(3) .
C13 F4 1.302(3) .
C13 F5 1.306(3) .
C13 F6 1.311(3) .
C14 C15 1.326(3) .
C15 C16 1.462(3) .
C16 C21 1.390(3) .
C16 C17 1.398(3) .
C17 C18 1.369(3) .
C18 C19 1.405(3) .
C19 N1 1.378(3) .
C19 C20 1.401(3) .
C20 C21 1.383(3) .
C22 N1 1.460(3) .
C22 C23 1.521(3) .
C23 C24 1.511(4) .
C24 C25 1.519(4) .
C26 N1 1.452(3) .
C26 C27 1.522(3) .
C27 C28 1.515(3) .
C28 C29 1.516(3) .
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
C3 C1 C2 C3 -1.0(3) 7_566 .
C14 C1 C2 C3 177.07(19) . .
C1 C2 C3 C1 1.1(3) . 7_566
C1 C2 C3 C4 -178.74(19) . .
C2 C3 C4 C5 174(100) . .
C1 C3 C4 C5 -6(4) 7_566 .
C3 C4 C5 C6 -11(6) . .
C4 C5 C6 C11 22(3) . .
C4 C5 C6 C7 -157(3) . .
C11 C6 C7 C8 -1.0(3) . .
C5 C6 C7 C8 177.5(2) . .
C6 C7 C8 C9 -0.2(3) . .
C6 C7 C8 C12 -178.48(19) . .
C7 C8 C9 C10 1.0(3) . .
C12 C8 C9 C10 179.3(2) . .
C8 C9 C10 C11 -0.6(3) . .
C8 C9 C10 C13 -178.92(19) . .
C9 C10 C11 C6 -0.6(3) . .
C13 C10 C11 C6 177.67(19) . .
C7 C6 C11 C10 1.4(3) . .
C5 C6 C11 C10 -177.11(19) . .
C9 C8 C12 F3 -67.9(3) . .
C7 C8 C12 F3 110.4(2) . .
C9 C8 C12 F1 171.2(2) . .
C7 C8 C12 F1 -10.5(3) . .
C9 C8 C12 F2 51.3(3) . .
C7 C8 C12 F2 -130.4(2) . .
C9 C10 C13 F4 -58.8(3) . .
C11 C10 C13 F4 122.9(2) . .
C9 C10 C13 F5 -179.5(2) . .
C11 C10 C13 F5 2.1(3) . .
C9 C10 C13 F6 60.3(3) . .
C11 C10 C13 F6 -118.1(2) . .
C2 C1 C14 C15 -0.6(4) . .
C3 C1 C14 C15 177.5(2) 7_566 .
C1 C14 C15 C16 -176.3(2) . .
C14 C15 C16 C21 166.2(2) . .
C14 C15 C16 C17 -12.2(4) . .
C21 C16 C17 C18 -2.2(4) . .
C15 C16 C17 C18 176.2(2) . .
C16 C17 C18 C19 -1.3(4) . .
C17 C18 C19 N1 -176.0(2) . .
C17 C18 C19 C20 3.7(4) . .
N1 C19 C20 C21 176.9(2) . .
C18 C19 C20 C21 -2.8(3) . .
C19 C20 C21 C16 -0.6(4) . .
C17 C16 C21 C20 3.1(3) . .
C15 C16 C21 C20 -175.3(2) . .
N1 C22 C23 C24 168.7(2) . .
C22 C23 C24 C25 168.6(2) . .
N1 C26 C27 C28 176.1(2) . .
C26 C27 C28 C29 171.5(2) . .
C20 C19 N1 C26 -3.7(3) . .
C18 C19 N1 C26 176.0(2) . .
C20 C19 N1 C22 173.7(2) . .
C18 C19 N1 C22 -6.6(3) . .
C27 C26 N1 C19 82.6(3) . .
C27 C26 N1 C22 -94.9(2) . .
C23 C22 N1 C19 -79.1(3) . .
C23 C22 N1 C26 98.4(2) . .
