#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180197 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/93/7109394.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_7109394
loop_
_publ_author_name
P.S.Salini
K.S.Anju
M.L.P.Reddy
'A. Srinivasan'
_publ_section_title
;
 Syntheses of normal, expanded, strapped and N-confused calixbenzophyrins
 from a single starting material
;
_journal_name_full               Chem.Commun.
_journal_page_first              5769
_journal_paper_doi               10.1039/c3cc41601a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C54 H42 F10 N4'
_chemical_formula_weight         936.92
_chemical_name_systematic
;
?
;
_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                103.975(2)
_cell_angle_beta                 94.023(2)
_cell_angle_gamma                103.426(2)
_cell_formula_units_Z            1
_cell_length_a                   10.7122(4)
_cell_length_b                   10.8416(5)
_cell_length_c                   11.2497(5)
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2
_cell_measurement_theta_min      2.7
_cell_volume                     1222.11(9)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14183
_diffrn_reflns_theta_full        21.88
_diffrn_reflns_theta_max         21.88
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0087(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0398
_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)+(0.0556P)²+0.4283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                2187
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41601a.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7109394
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
C1 C 0.0437(3) 0.0081(3) 0.1824(3) 0.0638(8) Uani 1 1 d .
C2 C -0.0613(3) -0.0917(3) 0.1835(4) 0.0824(10) Uani 1 1 d .
C3 C -0.1292(3) -0.0803(3) 0.2813(4) 0.0775(10) Uani 1 1 d .
C4 C -0.0927(3) 0.0287(3) 0.3772(3) 0.0644(8) Uani 1 1 d .
C5 C 0.0122(3) 0.1276(3) 0.3740(3) 0.0537(7) Uani 1 1 d .
C6 C 0.0828(2) 0.1212(3) 0.2767(2) 0.0462(7) Uani 1 1 d .
C7 C 0.1942(2) 0.2315(2) 0.2729(2) 0.0423(6) Uani 1 1 d .
C8 C 0.1691(2) 0.3331(3) 0.2318(2) 0.0436(7) Uani 1 1 d .
C9 C 0.0469(3) 0.3510(3) 0.1884(2) 0.0559(8) Uani 1 1 d .
H9 H -0.0342 0.2935 0.1813 0.067 Uiso 1 1 calc R
C10 C 0.0725(3) 0.4661(3) 0.1603(3) 0.0611(8) Uani 1 1 d .
H10 H 0.0125 0.5040 0.1293 0.073 Uiso 1 1 calc R
C11 C 0.2110(3) 0.5207(3) 0.1869(2) 0.0473(7) Uani 1 1 d .
C12 C 0.2851(3) 0.6514(3) 0.1714(2) 0.0557(8) Uani 1 1 d .
C13 C 0.2150(4) 0.7552(3) 0.2308(3) 0.1004(14) Uani 1 1 d .
H13A H 0.1313 0.7374 0.1840 0.151 Uiso 1 1 calc R
H13B H 0.2652 0.8411 0.2312 0.151 Uiso 1 1 calc R
H13C H 0.2048 0.7517 0.3141 0.151 Uiso 1 1 calc R
C14 C 0.4245(3) 0.6876(3) 0.2351(3) 0.0907(12) Uani 1 1 d .
H14A H 0.4241 0.6925 0.3215 0.136 Uiso 1 1 calc R
H14B H 0.4701 0.7713 0.2256 0.136 Uiso 1 1 calc R
H14C H 0.4669 0.6217 0.1983 0.136 Uiso 1 1 calc R
C15 C 0.2893(2) 0.6439(2) 0.0349(2) 0.0430(6) Uani 1 1 d .
C16 C 0.2768(3) 0.5270(3) -0.0518(2) 0.0540(7) Uani 1 1 d .
H16 H 0.2600 0.4494 -0.0273 0.065 Uiso 1 1 calc R
C17 C 0.2884(3) 0.5212(3) -0.1743(2) 0.0550(7) Uani 1 1 d .
H17 H 0.2782 0.4398 -0.2303 0.066 Uiso 1 1 calc R
C18 C 0.3146(2) 0.6323(3) -0.2155(2) 0.0443(7) Uani 1 1 d .
C19 C 0.3278(3) 0.7497(3) -0.1283(3) 0.0590(8) Uani 1 1 d .
H19 H 0.3465 0.8275 -0.1525 0.071 Uiso 1 1 calc R
C20 C 0.3142(3) 0.7553(3) -0.0068(2) 0.0585(8) Uani 1 1 d .
H20 H 0.3221 0.8365 0.0487 0.070 Uiso 1 1 calc R
C21 C 0.3313(2) 0.6314(3) -0.3499(2) 0.0520(7) Uani 1 1 d .
C22 C 0.3225(3) 0.4938(3) -0.4315(3) 0.0762(10) Uani 1 1 d .
H22A H 0.3369 0.4989 -0.5136 0.114 Uiso 1 1 calc R
H22B H 0.2381 0.4377 -0.4340 0.114 Uiso 1 1 calc R
H22C H 0.3870 0.4585 -0.3980 0.114 Uiso 1 1 calc R
C23 C 0.2269(3) 0.6859(4) -0.4033(3) 0.0872(12) Uani 1 1 d .
H23A H 0.2345 0.7740 -0.3549 0.131 Uiso 1 1 calc R
H23B H 0.1428 0.6315 -0.4013 0.131 Uiso 1 1 calc R
H23C H 0.2378 0.6863 -0.4872 0.131 Uiso 1 1 calc R
C24 C 0.4638(2) 0.7178(3) -0.3499(2) 0.0468(7) Uani 1 1 d .
C25 C 0.5061(3) 0.8298(3) -0.3882(2) 0.0577(8) Uani 1 1 d .
H25 H 0.4539 0.8727 -0.4235 0.069 Uiso 1 1 calc R
C26 C 0.6403(3) 0.8676(3) -0.3651(2) 0.0556(7) Uani 1 1 d .
H26 H 0.6938 0.9404 -0.3821 0.067 Uiso 1 1 calc R
C27 C 0.6807(2) 0.7783(2) -0.3124(2) 0.0422(6) Uani 1 1 d .
N1 N 0.26804(19) 0.4427(2) 0.22869(18) 0.0446(6) Uani 1 1 d .
N2 N 0.56980(19) 0.6885(2) -0.30481(19) 0.0439(6) Uani 1 1 d .
F1 F 0.10971(19) -0.00620(18) 0.08556(18) 0.0954(7) Uani 1 1 d .
F2 F -0.0961(2) -0.2001(2) 0.0892(2) 0.1396(10) Uani 1 1 d .
F3 F -0.2319(2) -0.17691(19) 0.2835(2) 0.1261(9) Uani 1 1 d .
F4 F -0.15859(18) 0.0404(2) 0.47474(19) 0.1001(7) Uani 1 1 d .
F5 F 0.04537(17) 0.23361(18) 0.47139(15) 0.0814(6) Uani 1 1 d .
H2 H 0.572(2) 0.624(2) -0.277(2) 0.037(7) 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'
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
F1 C1 C6 119.2(2) . .
F1 C1 C2 118.5(3) . .
C6 C1 C2 122.3(3) . .
F2 C2 C3 120.1(3) . .
F2 C2 C1 120.2(3) . .
C3 C2 C1 119.7(3) . .
F3 C3 C4 119.7(3) . .
F3 C3 C2 120.3(3) . .
C4 C3 C2 120.0(3) . .
F4 C4 C3 120.4(3) . .
F4 C4 C5 120.2(3) . .
C3 C4 C5 119.4(3) . .
F5 C5 C4 117.4(3) . .
F5 C5 C6 119.9(2) . .
C4 C5 C6 122.7(3) . .
C1 C6 C5 115.9(2) . .
C1 C6 C7 122.0(2) . .
C5 C6 C7 122.1(2) . .
C8 C7 C27 125.0(2) . 2_665
C8 C7 C6 118.4(2) . .
C27 C7 C6 116.6(2) 2_665 .
C7 C8 N1 122.0(2) . .
C7 C8 C9 129.1(2) . .
N1 C8 C9 108.8(2) . .
C10 C9 C8 106.6(2) . .
C10 C9 H9 126.7 . .
C8 C9 H9 126.7 . .
C9 C10 C11 107.1(2) . .
C9 C10 H10 126.4 . .
C11 C10 H10 126.4 . .
N1 C11 C10 111.3(2) . .
N1 C11 C12 122.3(2) . .
C10 C11 C12 126.3(2) . .
C11 C12 C15 110.3(2) . .
C11 C12 C14 110.3(2) . .
C15 C12 C14 108.1(2) . .
C11 C12 C13 107.3(2) . .
C15 C12 C13 110.7(2) . .
C14 C12 C13 110.2(3) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 116.4(2) . .
C16 C15 C12 121.9(2) . .
C20 C15 C12 121.5(2) . .
C15 C16 C17 121.9(2) . .
C15 C16 H16 119.1 . .
C17 C16 H16 119.1 . .
C18 C17 C16 121.7(3) . .
C18 C17 H17 119.2 . .
C16 C17 H17 119.2 . .
C17 C18 C19 116.4(2) . .
C17 C18 C21 123.6(2) . .
C19 C18 C21 119.9(2) . .
C20 C19 C18 121.9(2) . .
C20 C19 H19 119.0 . .
C18 C19 H19 119.0 . .
C19 C20 C15 121.7(3) . .
C19 C20 H20 119.2 . .
C15 C20 H20 119.2 . .
C24 C21 C22 108.2(2) . .
C24 C21 C23 110.0(2) . .
C22 C21 C23 108.9(2) . .
C24 C21 C18 107.7(2) . .
C22 C21 C18 112.7(2) . .
C23 C21 C18 109.4(2) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
N2 C24 C25 107.0(2) . .
N2 C24 C21 119.7(2) . .
C25 C24 C21 133.3(2) . .
C24 C25 C26 108.0(2) . .
C24 C25 H25 126.0 . .
C26 C25 H25 126.0 . .
C27 C26 C25 108.1(2) . .
C27 C26 H26 126.0 . .
C25 C26 H26 126.0 . .
N2 C27 C26 105.8(2) . .
N2 C27 C7 122.4(2) . 2_665
C26 C27 C7 131.8(2) . 2_665
C11 N1 C8 106.1(2) . .
C24 N2 C27 111.1(2) . .
C24 N2 H2 126.8(16) . .
C27 N2 H2 122.1(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F1 1.337(3) .
C1 C6 1.369(4) .
C1 C2 1.371(4) .
C2 F2 1.335(4) .
C2 C3 1.358(5) .
C3 F3 1.338(3) .
C3 C4 1.350(4) .
C4 F4 1.343(3) .
C4 C5 1.370(4) .
C5 F5 1.340(3) .
C5 C6 1.371(4) .
C6 C7 1.491(3) .
C7 C8 1.365(3) .
C7 C27 1.418(3) 2_665
C8 N1 1.406(3) .
C8 C9 1.436(3) .
C9 C10 1.332(4) .
C9 H9 0.9300 .
C10 C11 1.444(4) .
C10 H10 0.9300 .
C11 N1 1.305(3) .
C11 C12 1.511(4) .
C12 C15 1.523(3) .
C12 C14 1.530(4) .
C12 C13 1.542(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.371(3) .
C15 C20 1.376(3) .
C16 C17 1.381(3) .
C16 H16 0.9300 .
C17 C18 1.369(3) .
C17 H17 0.9300 .
C18 C19 1.377(4) .
C18 C21 1.533(3) .
C19 C20 1.373(4) .
C19 H19 0.9300 .
C20 H20 0.9300 .
C21 C24 1.509(4) .
C21 C22 1.529(4) .
C21 C23 1.532(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 N2 1.346(3) .
C24 C25 1.375(3) .
C25 C26 1.387(4) .
C25 H25 0.9300 .
C26 C27 1.384(3) .
C26 H26 0.9300 .
C27 N2 1.372(3) .
C27 C7 1.418(3) 2_665
N2 H2 0.84(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.84(2) 2.10(2) 2.702(3) 129(2) 2_665
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
F1 C1 C2 F2 -0.2(5) . .
C6 C1 C2 F2 179.7(3) . .
F1 C1 C2 C3 179.3(3) . .
C6 C1 C2 C3 -0.7(5) . .
F2 C2 C3 F3 -0.5(5) . .
C1 C2 C3 F3 180.0(3) . .
F2 C2 C3 C4 179.2(3) . .
C1 C2 C3 C4 -0.4(5) . .
F3 C3 C4 F4 0.2(5) . .
C2 C3 C4 F4 -179.5(3) . .
F3 C3 C4 C5 -179.7(3) . .
C2 C3 C4 C5 0.7(5) . .
F4 C4 C5 F5 0.5(4) . .
C3 C4 C5 F5 -179.7(3) . .
F4 C4 C5 C6 -179.8(2) . .
C3 C4 C5 C6 0.1(4) . .
F1 C1 C6 C5 -178.6(3) . .
C2 C1 C6 C5 1.4(4) . .
F1 C1 C6 C7 2.3(4) . .
C2 C1 C6 C7 -177.7(3) . .
F5 C5 C6 C1 178.7(2) . .
C4 C5 C6 C1 -1.1(4) . .
F5 C5 C6 C7 -2.2(4) . .
C4 C5 C6 C7 178.0(3) . .
C1 C6 C7 C8 95.5(3) . .
C5 C6 C7 C8 -83.6(3) . .
C1 C6 C7 C27 -84.2(3) . 2_665
C5 C6 C7 C27 96.7(3) . 2_665
C27 C7 C8 N1 -2.2(4) 2_665 .
C6 C7 C8 N1 178.1(2) . .
C27 C7 C8 C9 179.0(2) 2_665 .
C6 C7 C8 C9 -0.7(4) . .
C7 C8 C9 C10 179.2(3) . .
N1 C8 C9 C10 0.2(3) . .
C8 C9 C10 C11 -0.4(3) . .
C9 C10 C11 N1 0.4(3) . .
C9 C10 C11 C12 -179.1(2) . .
N1 C11 C12 C15 107.6(3) . .
C10 C11 C12 C15 -73.0(3) . .
N1 C11 C12 C14 -11.7(4) . .
C10 C11 C12 C14 167.7(3) . .
N1 C11 C12 C13 -131.8(3) . .
C10 C11 C12 C13 47.7(3) . .
C11 C12 C15 C16 -24.6(3) . .
C14 C12 C15 C16 96.1(3) . .
C13 C12 C15 C16 -143.2(3) . .
C11 C12 C15 C20 159.7(2) . .
C14 C12 C15 C20 -79.7(3) . .
C13 C12 C15 C20 41.1(4) . .
C20 C15 C16 C17 -0.1(4) . .
C12 C15 C16 C17 -176.0(3) . .
C15 C16 C17 C18 0.8(4) . .
C16 C17 C18 C19 -0.4(4) . .
C16 C17 C18 C21 178.6(2) . .
C17 C18 C19 C20 -0.6(4) . .
C21 C18 C19 C20 -179.7(2) . .
C18 C19 C20 C15 1.4(4) . .
C16 C15 C20 C19 -1.0(4) . .
C12 C15 C20 C19 175.0(3) . .
C17 C18 C21 C24 -122.2(3) . .
C19 C18 C21 C24 56.8(3) . .
C17 C18 C21 C22 -2.9(3) . .
C19 C18 C21 C22 176.0(2) . .
C17 C18 C21 C23 118.4(3) . .
C19 C18 C21 C23 -62.7(3) . .
C22 C21 C24 N2 -62.1(3) . .
C23 C21 C24 N2 179.0(2) . .
C18 C21 C24 N2 59.9(3) . .
C22 C21 C24 C25 118.1(3) . .
C23 C21 C24 C25 -0.8(4) . .
C18 C21 C24 C25 -119.8(3) . .
N2 C24 C25 C26 0.0(3) . .
C21 C24 C25 C26 179.7(3) . .
C24 C25 C26 C27 0.1(3) . .
C25 C26 C27 N2 0.0(3) . .
C25 C26 C27 C7 178.7(3) . 2_665
C10 C11 N1 C8 -0.3(3) . .
C12 C11 N1 C8 179.2(2) . .
C7 C8 N1 C11 -179.0(2) . .
C9 C8 N1 C11 0.0(3) . .
C25 C24 N2 C27 0.0(3) . .
C21 C24 N2 C27 -179.8(2) . .
C26 C27 N2 C24 0.0(3) . .
C7 C27 N2 C24 -178.9(2) 2_665 .
