#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:29:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178901 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/30/4113098.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_4113098
loop_
_publ_author_name
'Bohumil Dolenský'
'Jiří Kroulík'
'Vladimír Král'
'Jonathan L. Sessler'
'Hana Dvořáková'
'Petr Bouř'
'Markéta Bernátková'
'Christophe Bucher'
'Vincent Lynch'
_publ_section_title
;
 Calix[4]phyrins. Effect of Peripheral Substituents on Conformational
 Mobility and Structure within a Series of Related Systems
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13714
_journal_page_last               13722
_journal_paper_doi               10.1021/ja048075g
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C46 H26 F10 N4'
_chemical_formula_weight         824.71
_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                90.00
_cell_angle_beta                 111.306(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.2116(3)
_cell_length_b                   11.8259(3)
_cell_length_c                   11.5544(2)
_cell_measurement_temperature    153(2)
_cell_volume                     1809.17(7)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;
SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω-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  0.0811
_diffrn_reflns_av_sigmaI/netI    0.1714
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7324
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'olive green'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       plates
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0069(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.255
_refine_ls_R_factor_all          0.2066
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1781
_reflns_number_gt                1725
_reflns_number_total             4084
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja048075gsi20040403_012451.cif
_cod_data_source_block           1e
_cod_database_code               4113098
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
F1 F 0.15089(18) 0.5245(2) 0.6013(2) 0.0523(7) Uani 1 1 d .
F2 F -0.01799(19) 0.6197(2) 0.6075(2) 0.0657(8) Uani 1 1 d .
F3 F -0.08134(19) 0.8225(2) 0.4941(3) 0.0704(9) Uani 1 1 d .
F4 F 0.02515(19) 0.9265(2) 0.3732(2) 0.0590(8) Uani 1 1 d .
F5 F 0.19463(17) 0.83123(18) 0.3651(2) 0.0474(7) Uani 1 1 d .
N1 N 0.4492(2) 0.5719(2) 0.6289(3) 0.0305(8) Uani 1 1 d .
N2 N 0.3610(3) 0.5400(3) 0.3519(3) 0.0293(8) Uani 1 1 d .
C1 C 0.4956(3) 0.5875(3) 0.7485(3) 0.0287(9) Uani 1 1 d .
C2 C 0.4371(3) 0.6542(3) 0.8033(4) 0.0334(10) Uani 1 1 d .
H2 H 0.4577 0.6766 0.8888 0.040 Uiso 1 1 d R
C3 C 0.3496(3) 0.6774(3) 0.7123(3) 0.0332(10) Uani 1 1 d .
H3A H 0.2940 0.7196 0.7187 0.040 Uiso 1 1 d R
C4 C 0.3539(3) 0.6269(3) 0.6002(3) 0.0294(9) Uani 1 1 d .
C5 C 0.2767(3) 0.6248(3) 0.4873(3) 0.0297(9) Uani 1 1 d .
C6 C 0.2771(3) 0.5808(3) 0.3732(3) 0.0285(9) Uani 1 1 d .
C7 C 0.1951(3) 0.5661(3) 0.2617(3) 0.0318(9) Uani 1 1 d .
H7 H 0.1262 0.5843 0.2487 0.038 Uiso 1 1 d R
C8 C 0.2301(3) 0.5194(3) 0.1749(3) 0.0323(10) Uani 1 1 d .
H8 H 0.1907 0.5017 0.0900 0.039 Uiso 1 1 d R
C9 C 0.3348(3) 0.5043(3) 0.2328(3) 0.0283(9) Uani 1 1 d .
C10 C 0.4061(3) 0.4690(3) 0.1703(3) 0.0299(9) Uani 1 1 d .
C11 C 0.1787(3) 0.6749(3) 0.4831(3) 0.0293(9) Uani 1 1 d .
C12 C 0.1211(3) 0.6237(3) 0.5425(4) 0.0395(11) Uani 1 1 d .
C13 C 0.0340(3) 0.6721(4) 0.5460(4) 0.0425(11) Uani 1 1 d .
C14 C 0.0017(3) 0.7729(4) 0.4884(4) 0.0450(11) Uani 1 1 d .
C15 C 0.0561(3) 0.8259(3) 0.4270(4) 0.0410(11) Uani 1 1 d .
C16 C 0.1417(3) 0.7764(3) 0.4242(3) 0.0336(10) Uani 1 1 d .
C17 C 0.4404(3) 0.5781(3) 0.1228(4) 0.0364(10) Uani 1 1 d .
H17A H 0.4757 0.6265 0.1916 0.055 Uiso 1 1 d R
H17B H 0.4845 0.5582 0.0797 0.055 Uiso 1 1 d R
H17C H 0.3823 0.6168 0.0671 0.055 Uiso 1 1 d R
C18 C 0.3487(3) 0.3873(3) 0.0650(3) 0.0300(10) Uani 1 1 d .
C19 C 0.3122(3) 0.4171(3) -0.0591(4) 0.0400(11) Uani 1 1 d .
H19 H 0.3231 0.4927 -0.0818 0.048 Uiso 1 1 d R
C20 C 0.2609(3) 0.3395(4) -0.1507(4) 0.0469(12) Uani 1 1 d .
H20 H 0.2341 0.3620 -0.2364 0.056 Uiso 1 1 d R
C21 C 0.2472(3) 0.2301(4) -0.1187(4) 0.0502(12) Uani 1 1 d .
H21 H 0.2139 0.1754 -0.1817 0.060 Uiso 1 1 d R
C22 C 0.2829(3) 0.1998(4) 0.0048(4) 0.0463(12) Uani 1 1 d .
H22 H 0.2719 0.1243 0.0277 0.056 Uiso 1 1 d R
C23 C 0.3331(3) 0.2768(3) 0.0954(4) 0.0367(10) Uani 1 1 d .
H23 H 0.3575 0.2545 0.1811 0.044 Uiso 1 1 d R
H2N H 0.423(3) 0.538(3) 0.406(3) 0.024(10) 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
C1 N1 C4 104.6(3) . .
C9 N2 C6 110.5(3) . .
C9 N2 H2N 124(2) . .
C6 N2 H2N 126(2) . .
N1 C1 C2 112.9(3) . .
N1 C1 C10 125.7(3) . 3_666
C2 C1 C10 120.8(3) . 3_666
C3 C2 C1 106.7(3) . .
C3 C2 H2 127.0 . .
C1 C2 H2 126.3 . .
C2 C3 C4 106.8(3) . .
C2 C3 H3A 127.2 . .
C4 C3 H3A 126.0 . .
C5 C4 N1 125.3(3) . .
C5 C4 C3 125.5(3) . .
N1 C4 C3 109.0(3) . .
C4 C5 C6 128.4(3) . .
C4 C5 C11 116.0(3) . .
C6 C5 C11 115.6(3) . .
N2 C6 C7 106.0(3) . .
N2 C6 C5 125.8(3) . .
C7 C6 C5 128.2(3) . .
C8 C7 C6 108.6(3) . .
C8 C7 H7 126.1 . .
C6 C7 H7 125.3 . .
C7 C8 C9 107.6(3) . .
C7 C8 H8 126.7 . .
C9 C8 H8 125.7 . .
N2 C9 C8 107.3(3) . .
N2 C9 C10 126.2(3) . .
C8 C9 C10 126.2(3) . .
C9 C10 C1 117.0(3) . 3_666
C9 C10 C18 107.4(3) . .
C1 C10 C18 108.4(3) 3_666 .
C9 C10 C17 107.1(3) . .
C1 C10 C17 104.3(3) 3_666 .
C18 C10 C17 112.9(3) . .
C16 C11 C12 115.7(3) . .
C16 C11 C5 122.8(3) . .
C12 C11 C5 121.5(3) . .
F1 C12 C13 118.0(4) . .
F1 C12 C11 119.8(3) . .
C13 C12 C11 122.2(4) . .
F2 C13 C14 120.5(4) . .
F2 C13 C12 119.7(4) . .
C14 C13 C12 119.8(4) . .
F3 C14 C13 120.4(4) . .
F3 C14 C15 119.7(4) . .
C13 C14 C15 119.9(4) . .
F4 C15 C14 119.5(4) . .
F4 C15 C16 121.1(4) . .
C14 C15 C16 119.4(4) . .
F5 C16 C15 118.1(3) . .
F5 C16 C11 118.8(3) . .
C15 C16 C11 123.0(4) . .
C10 C17 H17A 109.9 . .
C10 C17 H17B 109.2 . .
H17A C17 H17B 109.5 . .
C10 C17 H17C 109.3 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 C23 117.9(3) . .
C19 C18 C10 123.5(3) . .
C23 C18 C10 118.6(3) . .
C18 C19 C20 121.2(4) . .
C18 C19 H19 119.0 . .
C20 C19 H19 119.9 . .
C21 C20 C19 120.0(4) . .
C21 C20 H20 119.7 . .
C19 C20 H20 120.3 . .
C20 C21 C22 119.2(4) . .
C20 C21 H21 120.5 . .
C22 C21 H21 120.3 . .
C23 C22 C21 120.6(4) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.5 . .
C22 C23 C18 121.1(4) . .
C22 C23 H23 119.7 . .
C18 C23 H23 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C12 1.345(4) .
F2 C13 1.349(4) .
F3 C14 1.341(4) .
F4 C15 1.340(4) .
F5 C16 1.352(4) .
N1 C1 1.310(4) .
N1 C4 1.429(5) .
N2 C9 1.356(5) .
N2 C6 1.389(5) .
N2 H2N 0.88(4) .
C1 C2 1.447(5) .
C1 C10 1.525(5) 3_666
C2 C3 1.334(5) .
C2 H2 0.9600 .
C3 C4 1.448(5) .
C3 H3A 0.9600 .
C4 C5 1.366(5) .
C5 C6 1.419(5) .
C5 C11 1.497(5) .
C6 C7 1.399(5) .
C7 C8 1.386(5) .
C7 H7 0.9601 .
C8 C9 1.404(5) .
C8 H8 0.9600 .
C9 C10 1.502(5) .
C10 C1 1.525(5) 3_666
C10 C18 1.536(5) .
C10 C17 1.548(5) .
C11 C16 1.386(5) .
C11 C12 1.385(5) .
C12 C13 1.376(5) .
C13 C14 1.362(6) .
C14 C15 1.375(6) .
C15 C16 1.362(5) .
C17 H17A 0.9599 .
C17 H17B 0.9601 .
C17 H17C 0.9600 .
C18 C19 1.381(5) .
C18 C23 1.391(5) .
C19 C20 1.391(5) .
C19 H19 0.9600 .
C20 C21 1.379(6) .
C20 H20 0.9600 .
C21 C22 1.377(6) .
C21 H21 0.9601 .
C22 C23 1.375(5) .
C22 H22 0.9600 .
C23 H23 0.9600 .
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
C4 N1 C1 C2 -1.7(4) . .
C4 N1 C1 C10 170.4(3) . 3_666
N1 C1 C2 C3 1.7(4) . .
C10 C1 C2 C3 -170.8(3) 3_666 .
C1 C2 C3 C4 -0.9(4) . .
C1 N1 C4 C5 -174.5(4) . .
C1 N1 C4 C3 1.1(4) . .
C2 C3 C4 C5 175.5(4) . .
C2 C3 C4 N1 -0.1(4) . .
N1 C4 C5 C6 -7.7(6) . .
C3 C4 C5 C6 177.3(4) . .
N1 C4 C5 C11 171.9(3) . .
C3 C4 C5 C11 -3.1(6) . .
C9 N2 C6 C7 1.6(4) . .
C9 N2 C6 C5 180.0(3) . .
C4 C5 C6 N2 -6.7(6) . .
C11 C5 C6 N2 173.7(3) . .
C4 C5 C6 C7 171.3(4) . .
C11 C5 C6 C7 -8.3(6) . .
N2 C6 C7 C8 -1.1(4) . .
C5 C6 C7 C8 -179.4(4) . .
C6 C7 C8 C9 0.2(4) . .
C6 N2 C9 C8 -1.5(4) . .
C6 N2 C9 C10 171.5(3) . .
C7 C8 C9 N2 0.7(4) . .
C7 C8 C9 C10 -172.3(3) . .
N2 C9 C10 C1 32.4(5) . 3_666
C8 C9 C10 C1 -155.9(4) . 3_666
N2 C9 C10 C18 154.4(3) . .
C8 C9 C10 C18 -33.9(5) . .
N2 C9 C10 C17 -84.1(4) . .
C8 C9 C10 C17 87.6(4) . .
C4 C5 C11 C16 109.0(4) . .
C6 C5 C11 C16 -71.3(5) . .
C4 C5 C11 C12 -68.5(5) . .
C6 C5 C11 C12 111.2(4) . .
C16 C11 C12 F1 179.5(3) . .
C5 C11 C12 F1 -2.8(6) . .
C16 C11 C12 C13 -1.7(6) . .
C5 C11 C12 C13 176.0(4) . .
F1 C12 C13 F2 0.2(6) . .
C11 C12 C13 F2 -178.6(4) . .
F1 C12 C13 C14 179.5(4) . .
C11 C12 C13 C14 0.7(7) . .
F2 C13 C14 F3 1.3(6) . .
C12 C13 C14 F3 -178.0(4) . .
F2 C13 C14 C15 179.4(4) . .
C12 C13 C14 C15 0.1(7) . .
F3 C14 C15 F4 -0.2(6) . .
C13 C14 C15 F4 -178.3(4) . .
F3 C14 C15 C16 178.3(4) . .
C13 C14 C15 C16 0.2(6) . .
F4 C15 C16 F5 -0.3(6) . .
C14 C15 C16 F5 -178.9(4) . .
F4 C15 C16 C11 177.2(3) . .
C14 C15 C16 C11 -1.4(6) . .
C12 C11 C16 F5 179.5(3) . .
C5 C11 C16 F5 1.9(5) . .
C12 C11 C16 C15 2.0(6) . .
C5 C11 C16 C15 -175.6(4) . .
C9 C10 C18 C19 104.4(4) . .
C1 C10 C18 C19 -128.4(4) 3_666 .
C17 C10 C18 C19 -13.4(5) . .
C9 C10 C18 C23 -76.1(4) . .
C1 C10 C18 C23 51.1(4) 3_666 .
C17 C10 C18 C23 166.1(3) . .
C23 C18 C19 C20 0.3(6) . .
C10 C18 C19 C20 179.8(4) . .
C18 C19 C20 C21 -0.9(6) . .
C19 C20 C21 C22 1.3(6) . .
C20 C21 C22 C23 -1.0(6) . .
C21 C22 C23 C18 0.3(6) . .
C19 C18 C23 C22 0.1(6) . .
C10 C18 C23 C22 -179.5(3) . .
