#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:00:33 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178983 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/06/4120656.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_4120656
loop_
_publ_author_name
'Adriaenssens, Louis'
'Gil-Ramírez, Guzmán'
'Frontera, Antonio'
'Quiñonero, David'
'Escudero-Adán, Eduardo C'
'Ballester, Pablo'
_publ_section_title
;
 Thermodynamic Characterization of Halide-π Interactions in Solution
 Using "Two-Wall" Aryl Extended Calix[4]pyrroles as Model
 System.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3208
_journal_paper_doi               10.1021/ja412098v
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C42 H36 F10 N6'
_chemical_formula_weight         814.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.366(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8894(9)
_cell_length_b                   11.8311(10)
_cell_length_c                   14.1611(12)
_cell_measurement_reflns_used    7799
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.13
_cell_measurement_theta_min      3.52
_cell_volume                     1938.0(3)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37093
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         39.29
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         11053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0648P)²+0.3032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                9342
_reflns_number_total             11053
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412098v_si_010.cif
_cod_data_source_block           gg131a1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4120656
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 1.02095(4) 0.81715(4) 0.06691(3) 0.01343(7) Uani 1 1 d .
H1 H 0.9556 0.8367 0.0269 0.016 Uiso 1 1 calc R
C1 C 1.11490(4) 0.77141(4) 0.03919(4) 0.01340(8) Uani 1 1 d .
F1 F 0.89628(4) 0.65225(3) 0.15021(4) 0.02418(9) Uani 1 1 d .
N2 N 0.92435(4) 1.06548(4) 0.12485(3) 0.01346(7) Uani 1 1 d .
H2 H 0.8855 1.0342 0.0707 0.016 Uiso 1 1 calc R
C2 C 1.19992(5) 0.75463(5) 0.12226(4) 0.01702(9) Uani 1 1 d .
H2A H 1.2749 0.7248 0.1255 0.020 Uiso 1 1 calc R
F2 F 0.68515(5) 0.58644(4) 0.06212(4) 0.03055(10) Uani 1 1 d .
C3 C 1.15520(5) 0.79012(5) 0.20263(4) 0.01709(9) Uani 1 1 d .
H3 H 1.1948 0.7881 0.2691 0.021 Uiso 1 1 calc R
F3 F 0.50233(4) 0.73102(5) 0.04410(4) 0.03022(11) Uani 1 1 d .
C4 C 1.04426(5) 0.82772(4) 0.16629(4) 0.01359(8) Uani 1 1 d .
F4 F 0.53686(4) 0.94073(5) 0.12389(4) 0.03209(11) Uani 1 1 d .
C5 C 0.95954(5) 0.88093(5) 0.21864(4) 0.01412(8) Uani 1 1 d .
F5 F 0.74547(4) 1.00987(4) 0.21313(4) 0.02469(9) Uani 1 1 d .
C6 C 0.83517(5) 0.83953(5) 0.17618(4) 0.01500(8) Uani 1 1 d .
C7 C 0.81159(5) 0.72926(5) 0.14126(5) 0.01770(9) Uani 1 1 d .
C8 C 0.70154(6) 0.69194(6) 0.09664(5) 0.02113(11) Uani 1 1 d .
C9 C 0.60879(6) 0.76434(6) 0.08797(5) 0.02211(11) Uani 1 1 d .
C10 C 0.62692(5) 0.87156(6) 0.12741(5) 0.02141(11) Uani 1 1 d .
C11 C 0.73752(5) 0.90691(5) 0.17210(4) 0.01766(9) Uani 1 1 d .
C12 C 0.99195(6) 0.84739(6) 0.32688(4) 0.01958(10) Uani 1 1 d .
H12A H 1.0720 0.8697 0.3552 0.029 Uiso 1 1 calc R
H12B H 0.9842 0.7654 0.3328 0.029 Uiso 1 1 calc R
H12C H 0.9402 0.8858 0.3613 0.029 Uiso 1 1 calc R
C13 C 0.97006(5) 1.00802(5) 0.20952(4) 0.01379(8) Uani 1 1 d .
C14 C 1.02693(5) 1.08540(5) 0.27625(4) 0.01712(9) Uani 1 1 d .
H14 H 1.0677 1.0697 0.3409 0.021 Uiso 1 1 calc R
C15 C 1.01332(5) 1.19359(5) 0.23036(4) 0.01704(9) Uani 1 1 d .
H15 H 1.0437 1.2630 0.2590 0.020 Uiso 1 1 calc R
C16 C 0.94829(4) 1.17932(4) 0.13721(4) 0.01346(8) Uani 1 1 d .
C17 C 0.89071(5) 1.26621(4) 0.06356(4) 0.01468(8) Uani 1 1 d .
C18 C 0.95728(7) 1.37875(5) 0.08227(5) 0.02337(12) Uani 1 1 d .
H18A H 1.0375 1.3668 0.0781 0.035 Uiso 1 1 calc R
H18B H 0.9559 1.4067 0.1471 0.035 Uiso 1 1 calc R
H18C H 0.9208 1.4344 0.0335 0.035 Uiso 1 1 calc R
C19 C 0.76725(6) 1.28584(6) 0.07665(5) 0.02336(12) Uani 1 1 d .
H19A H 0.7289 1.3433 0.0304 0.035 Uiso 1 1 calc R
H19B H 0.7707 1.3118 0.1430 0.035 Uiso 1 1 calc R
H19C H 0.7236 1.2150 0.0649 0.035 Uiso 1 1 calc R
C1S C 0.74251(5) 0.94616(6) -0.13134(5) 0.02050(10) Uani 1 1 d .
N1S N 0.79867(6) 0.91911(6) -0.05757(5) 0.02827(12) Uani 1 1 d .
C2S C 0.67031(6) 0.98057(6) -0.22426(5) 0.02386(12) Uani 1 1 d .
H2SA H 0.6475 1.0598 -0.2207 0.036 Uiso 1 1 calc R
H2SB H 0.6010 0.9330 -0.2399 0.036 Uiso 1 1 calc R
H2SC H 0.7137 0.9722 -0.2749 0.036 Uiso 1 1 calc R
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
C4 N1 C1 110.02(4) . .
C2 C1 N1 107.26(5) . .
C2 C1 C17 129.93(5) . 3_775
N1 C1 C17 122.20(5) . 3_775
C13 N2 C16 110.08(4) . .
C1 C2 C3 107.69(5) . .
C4 C3 C2 107.40(5) . .
C3 C4 N1 107.62(5) . .
C3 C4 C5 129.71(5) . .
N1 C4 C5 122.52(5) . .
C13 C5 C4 107.00(4) . .
C13 C5 C6 111.85(4) . .
C4 C5 C6 111.26(4) . .
C13 C5 C12 109.44(5) . .
C4 C5 C12 109.68(5) . .
C6 C5 C12 107.60(4) . .
C11 C6 C7 114.83(5) . .
C11 C6 C5 123.18(5) . .
C7 C6 C5 121.96(5) . .
F1 C7 C8 115.79(5) . .
F1 C7 C6 120.97(5) . .
C8 C7 C6 123.24(6) . .
F2 C8 C9 120.05(6) . .
F2 C8 C7 120.38(6) . .
C9 C8 C7 119.57(6) . .
F3 C9 C8 120.73(7) . .
F3 C9 C10 120.11(7) . .
C8 C9 C10 119.14(6) . .
F4 C10 C9 119.79(6) . .
F4 C10 C11 119.91(6) . .
C9 C10 C11 120.28(6) . .
F5 C11 C10 115.83(5) . .
F5 C11 C6 121.61(5) . .
C10 C11 C6 122.55(6) . .
C14 C13 N2 107.59(5) . .
C14 C13 C5 129.66(5) . .
N2 C13 C5 122.69(5) . .
C13 C14 C15 107.33(5) . .
C16 C15 C14 107.80(5) . .
C15 C16 N2 107.16(5) . .
C15 C16 C17 129.98(5) . .
N2 C16 C17 121.97(5) . .
C1 C17 C16 112.16(4) 3_775 .
C1 C17 C19 109.27(5) 3_775 .
C16 C17 C19 108.18(5) . .
C1 C17 C18 109.11(5) 3_775 .
C16 C17 C18 109.67(5) . .
C19 C17 C18 108.37(5) . .
N1S C1S C2S 179.37(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.3757(7) .
N1 C1 1.3775(7) .
C1 C2 1.3767(8) .
C1 C17 1.5082(8) 3_775
F1 C7 1.3419(8) .
N2 C13 1.3762(7) .
N2 C16 1.3793(7) .
C2 C3 1.4263(9) .
F2 C8 1.3382(8) .
C3 C4 1.3743(8) .
F3 C9 1.3341(8) .
C4 C5 1.5185(8) .
F4 C10 1.3394(8) .
C5 C13 1.5168(8) .
C5 C6 1.5418(8) .
C5 C12 1.5434(8) .
F5 C11 1.3436(8) .
C6 C11 1.3984(8) .
C6 C7 1.4005(8) .
C7 C8 1.3870(9) .
C8 C9 1.3792(10) .
C9 C10 1.3827(10) .
C10 C11 1.3856(9) .
C13 C14 1.3758(8) .
C14 C15 1.4277(9) .
C15 C16 1.3765(8) .
C16 C17 1.5110(8) .
C17 C1 1.5083(8) 3_775
C17 C19 1.5391(8) .
C17 C18 1.5403(8) .
C1S N1S 1.1475(9) .
C1S C2S 1.4533(9) .
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 -1.09(6) . .
C4 N1 C1 C17 170.79(5) . 3_775
N1 C1 C2 C3 0.72(6) . .
C17 C1 C2 C3 -170.31(5) 3_775 .
C1 C2 C3 C4 -0.10(7) . .
C2 C3 C4 N1 -0.56(6) . .
C2 C3 C4 C5 -176.05(5) . .
C1 N1 C4 C3 1.03(6) . .
C1 N1 C4 C5 176.92(5) . .
C3 C4 C5 C13 95.85(7) . .
N1 C4 C5 C13 -79.05(6) . .
C3 C4 C5 C6 -141.69(6) . .
N1 C4 C5 C6 43.40(7) . .
C3 C4 C5 C12 -22.77(8) . .
N1 C4 C5 C12 162.33(5) . .
C13 C5 C6 C11 -27.61(7) . .
C4 C5 C6 C11 -147.22(5) . .
C12 C5 C6 C11 92.62(6) . .
C13 C5 C6 C7 154.39(5) . .
C4 C5 C6 C7 34.78(7) . .
C12 C5 C6 C7 -85.38(6) . .
C11 C6 C7 F1 -173.01(5) . .
C5 C6 C7 F1 5.14(9) . .
C11 C6 C7 C8 6.43(9) . .
C5 C6 C7 C8 -175.42(6) . .
F1 C7 C8 F2 -2.59(9) . .
C6 C7 C8 F2 177.94(6) . .
F1 C7 C8 C9 177.43(6) . .
C6 C7 C8 C9 -2.03(10) . .
F2 C8 C9 F3 -0.96(10) . .
C7 C8 C9 F3 179.01(6) . .
F2 C8 C9 C10 177.54(6) . .
C7 C8 C9 C10 -2.49(10) . .
F3 C9 C10 F4 1.90(10) . .
C8 C9 C10 F4 -176.60(6) . .
F3 C9 C10 C11 -179.30(6) . .
C8 C9 C10 C11 2.19(10) . .
F4 C10 C11 F5 2.54(9) . .
C9 C10 C11 F5 -176.25(6) . .
F4 C10 C11 C6 -178.55(6) . .
C9 C10 C11 C6 2.66(10) . .
C7 C6 C11 F5 172.14(5) . .
C5 C6 C11 F5 -5.99(9) . .
C7 C6 C11 C10 -6.70(9) . .
C5 C6 C11 C10 175.17(5) . .
C16 N2 C13 C14 -1.73(6) . .
C16 N2 C13 C5 -179.17(5) . .
C4 C5 C13 C14 -101.63(7) . .
C6 C5 C13 C14 136.29(6) . .
C12 C5 C13 C14 17.14(8) . .
C4 C5 C13 N2 75.20(6) . .
C6 C5 C13 N2 -46.88(7) . .
C12 C5 C13 N2 -166.02(5) . .
N2 C13 C14 C15 0.90(7) . .
C5 C13 C14 C15 178.11(5) . .
C13 C14 C15 C16 0.22(7) . .
C14 C15 C16 N2 -1.26(6) . .
C14 C15 C16 C17 167.89(5) . .
C13 N2 C16 C15 1.86(6) . .
C13 N2 C16 C17 -168.34(5) . .
C15 C16 C17 C1 148.97(6) . 3_775
N2 C16 C17 C1 -43.28(7) . 3_775
C15 C16 C17 C19 -90.45(7) . .
N2 C16 C17 C19 77.31(6) . .
C15 C16 C17 C18 27.57(8) . .
N2 C16 C17 C18 -164.67(5) . .
