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#$Date: 2016-03-22 11:51:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178920 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/49/4114964.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_4114964
loop_
_publ_author_name
'Christopher J. Woods'
'Salvatore Camiolo'
'Mark E. Light'
'Simon J. Coles'
'Michael B. Hursthouse'
'Michael A. King'
'Philip A. Gale'
'Jonathan W. Essex'
_publ_section_title
;
 Fluoride-Selective Binding in a New Deep Cavity Calix[4]pyrrole:
 Experiment and Theory
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8644
_journal_page_last               8652
_journal_paper_doi               10.1021/ja025572t
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C62 H61 N7 O8'
_chemical_formula_weight         1032.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           85
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4a'
_symmetry_space_group_name_H-M   'P 4/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3723(16)
_cell_length_b                   11.3723(16)
_cell_length_c                   21.020(4)
_cell_measurement_temperature    150(2)
_cell_volume                     2718.5(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23657
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9916
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0043(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.441
_refine_ls_shift/su_mean         0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0823P)²+0.1320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1918
_reflns_number_total             3120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja025572t_s1_2.cif
_cod_data_source_block           s93
_cod_original_cell_volume        2718.4(8)
_cod_original_sg_symbol_H-M      'P 4/n'
_cod_database_code               4114964
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -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 0.92080(14) 0.53748(14) 0.38168(7) 0.0268(4) Uani 1 1 d .
C2 C 0.90788(15) 0.45269(14) 0.42733(8) 0.0320(4) Uani 1 1 d .
H2 H 0.9679 0.4235 0.4545 0.038 Uiso 1 1 calc R
C3 C 0.78920(15) 0.41644(15) 0.42681(8) 0.0322(4) Uani 1 1 d .
H3 H 0.7555 0.3587 0.4539 0.039 Uiso 1 1 calc R
C4 C 0.73085(14) 0.47786(14) 0.38094(7) 0.0263(4) Uani 1 1 d .
C5 C 1.02799(14) 0.60463(14) 0.35902(7) 0.0274(4) Uani 1 1 d .
C6 C 1.13897(15) 0.54704(16) 0.38708(9) 0.0351(4) Uani 1 1 d .
H6A H 1.2087 0.5903 0.3729 0.053 Uiso 1 1 calc R
H6B H 1.1441 0.4653 0.3726 0.053 Uiso 1 1 calc R
H6C H 1.1347 0.5489 0.4336 0.053 Uiso 1 1 calc R
C7 C 1.03869(14) 0.59552(15) 0.28610(8) 0.0285(4) Uani 1 1 d .
C8 C 1.00642(16) 0.49145(16) 0.25573(8) 0.0347(4) Uani 1 1 d .
H8 H 0.9735 0.4292 0.2801 0.042 Uiso 1 1 calc R
C9 C 1.02137(16) 0.47693(17) 0.19083(8) 0.0387(5) Uani 1 1 d .
H9 H 0.9993 0.4054 0.1707 0.046 Uiso 1 1 calc R
C10 C 1.06866(15) 0.56777(17) 0.15595(8) 0.0360(5) Uani 1 1 d .
C11 C 1.10245(16) 0.67205(17) 0.18419(8) 0.0374(5) Uani 1 1 d .
H11 H 1.1350 0.7340 0.1595 0.045 Uiso 1 1 calc R
C12 C 1.08780(16) 0.68430(16) 0.24950(8) 0.0348(4) Uani 1 1 d .
H12 H 1.1120 0.7552 0.2695 0.042 Uiso 1 1 calc R
C13 C 1.18519(17) 0.54646(18) 0.06313(9) 0.0419(5) Uani 1 1 d .
C14 C 1.17922(19) 0.5038(2) -0.00370(9) 0.0509(6) Uani 1 1 d .
H14A H 1.2563 0.5133 -0.0240 0.076 Uiso 1 1 calc R
H14B H 1.1204 0.5494 -0.0272 0.076 Uiso 1 1 calc R
H14C H 1.1571 0.4205 -0.0040 0.076 Uiso 1 1 calc R
C15 C 0.2500 0.2500 0.5130(2) 0.0587(12) Uani 1 4 d S
H15A H 0.2138 0.1773 0.5286 0.088 Uiso 0.25 1 calc PR
H15B H 0.2051 0.3177 0.5286 0.088 Uiso 0.25 1 calc PR
H15C H 0.3311 0.2550 0.5286 0.088 Uiso 0.25 1 calc PR
C16 C 0.2500 0.2500 0.4445(2) 0.0374(9) Uani 1 4 d S
C17 C 0.2500 0.2500 0.2223(3) 0.0863(17) Uani 1 4 d S
H17A H 0.3207 0.2900 0.2379 0.129 Uiso 0.25 1 calc PR
H17B H 0.2493 0.1688 0.2379 0.129 Uiso 0.25 1 calc PR
H17C H 0.1800 0.2912 0.2379 0.129 Uiso 0.25 1 calc PR
C18 C 0.2500 0.2500 0.1550(3) 0.0717(15) Uani 1 4 d S
C19 C 0.7500 0.7500 0.1276(3) 0.162(4) Uani 1 4 d SU
H19A H 0.6786 0.7111 0.1121 0.242 Uiso 0.25 1 calc PR
H19B H 0.8193 0.7076 0.1121 0.242 Uiso 0.25 1 calc PR
H19C H 0.7520 0.8312 0.1121 0.242 Uiso 0.25 1 calc PR
C20 C 0.7500 0.7500 0.19587(19) 0.0517(11) Uani 1 4 d S
N1 N 0.81170(11) 0.55376(11) 0.35467(6) 0.0265(3) Uani 1 1 d .
H1 H 0.7959 0.6055 0.3248 0.032 Uiso 1 1 calc R
N2 N 0.2500 0.2500 0.39022(18) 0.0513(9) Uani 1 4 d S
N3 N 0.2500 0.2500 0.1007(3) 0.1005(17) Uani 1 4 d S
N4 N 0.7500 0.7500 0.24928(15) 0.0415(8) Uani 1 4 d S
O1 O 1.07729(11) 0.55003(12) 0.08974(5) 0.0445(4) Uani 1 1 d .
O2 O 1.27221(13) 0.57576(17) 0.09083(7) 0.0672(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'
O O 0.0106 0.0060 '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 N1 106.68(14) . .
C2 C1 C5 131.46(15) . .
N1 C1 C5 121.84(14) . .
C1 C2 C3 107.65(15) . .
C4 C3 C2 108.74(15) . .
C3 C4 N1 106.26(14) . .
C3 C4 C5 131.03(15) . 4_565
N1 C4 C5 122.71(14) . 4_565
C4 C5 C1 110.36(13) 3_655 .
C4 C5 C6 108.90(13) 3_655 .
C1 C5 C6 108.95(13) . .
C4 C5 C7 111.79(13) 3_655 .
C1 C5 C7 110.01(13) . .
C6 C5 C7 106.73(13) . .
C12 C7 C8 118.05(16) . .
C12 C7 C5 122.31(15) . .
C8 C7 C5 119.46(15) . .
C9 C8 C7 121.34(17) . .
C10 C9 C8 118.90(17) . .
C9 C10 C11 121.64(16) . .
C9 C10 O1 116.46(16) . .
C11 C10 O1 121.86(16) . .
C10 C11 C12 118.51(17) . .
C7 C12 C11 121.55(17) . .
O2 C13 O1 122.85(18) . .
O2 C13 C14 126.06(19) . .
O1 C13 C14 111.09(17) . .
N2 C16 C15 180.000(1) . .
N3 C18 C17 180.000(1) . .
N4 C20 C19 180.000(1) . .
C4 N1 C1 110.62(13) . .
C13 O1 C10 118.49(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.368(2) .
C1 N1 1.377(2) .
C1 C5 1.515(2) .
C2 C3 1.411(2) .
C3 C4 1.363(2) .
C4 N1 1.377(2) .
C4 C5 1.509(2) 4_565
C5 C4 1.509(2) 3_655
C5 C6 1.539(2) .
C5 C7 1.541(2) .
C7 C12 1.387(2) .
C7 C8 1.394(2) .
C8 C9 1.385(2) .
C9 C10 1.376(3) .
C10 C11 1.381(3) .
C10 O1 1.410(2) .
C11 C12 1.390(2) .
C13 O2 1.196(2) .
C13 O1 1.349(2) .
C13 C14 1.488(3) .
C15 C16 1.440(6) .
C16 N2 1.142(5) .
C17 C18 1.414(8) .
C18 N3 1.141(7) .
C19 C20 1.434(7) .
C20 N4 1.123(5) .
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
N1 H1 N4 0.88 2.34 3.222(3) 177.0
