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#$Date: 2016-03-22 11:45:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178914 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/43/4114344.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_4114344
loop_
_publ_author_name
'Jonathan L. Sessler'
'Deqiang An'
'Won-Seob Cho'
'Vincent Lynch'
_publ_section_title
;
 Calix[2]bipyrrole[2]furan and Calix[2]bipyrrole[2]thiophene: New Pyrrolic
 Receptors Exhibiting a Preference for Carboxylate Anions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13646
_journal_page_last               13647
_journal_paper_doi               10.1021/ja038264j
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C36 H40 N4 O2'
_chemical_formula_weight         560.72
_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                 107.2090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.60460(10)
_cell_length_b                   18.4424(4)
_cell_length_c                   7.9205(2)
_cell_measurement_temperature    153(2)
_cell_volume                     1479.70(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6179
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            grey
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       lathes
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0079(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.1372
_refine_ls_R_factor_gt           0.0946
_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)+(0.0190P)²+1.5031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                2554
_reflns_number_total             3392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja038264jsi20030901_071441.cif
_cod_data_source_block           furan
_cod_database_code               4114344
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
O1 O 0.23989(15) 0.53112(9) 0.8239(2) 0.0196(4) Uani 1 1 d
N1 N 0.5137(2) 0.34237(11) 0.3960(3) 0.0186(5) Uani 1 1 d
N2 N 0.3235(2) 0.40218(12) 0.6953(3) 0.0192(5) Uani 1 1 d
C1 C 0.6275(2) 0.37161(13) 0.3755(3) 0.0176(5) Uani 1 1 d
C2 C 0.6712(3) 0.42279(14) 0.5049(3) 0.0225(6) Uani 1 1 d
C3 C 0.5820(3) 0.42458(14) 0.6066(3) 0.0228(6) Uani 1 1 d
C4 C 0.4850(2) 0.37528(13) 0.5379(3) 0.0179(6) Uani 1 1 d
C5 C 0.3696(2) 0.35557(13) 0.5912(3) 0.0183(5) Uani 1 1 d
C6 C 0.2904(3) 0.29569(14) 0.5628(3) 0.0227(6) Uani 1 1 d
C7 C 0.1931(3) 0.30655(14) 0.6510(3) 0.0233(6) Uani 1 1 d
C8 C 0.2152(2) 0.37272(13) 0.7321(3) 0.0191(6) Uani 1 1 d
C9 C 0.1460(2) 0.41220(14) 0.8490(3) 0.0216(6) Uani 1 1 d
C10 C 0.1250(2) 0.49070(13) 0.7947(3) 0.0196(6) Uani 1 1 d
C11 C 0.0212(2) 0.53341(15) 0.7236(3) 0.0242(6) Uani 1 1 d
C12 C 0.0704(3) 0.60442(15) 0.7051(3) 0.0245(6) Uani 1 1 d
C13 C 0.2028(2) 0.60095(13) 0.7656(3) 0.0194(6) Uani 1 1 d
C14 C 0.3147(2) 0.65166(13) 0.7709(3) 0.0200(6) Uani 1 1 d
C15 C 0.2301(3) 0.40891(16) 1.0456(3) 0.0229(6) Uani 1 1 d
C16 C 0.0118(3) 0.37698(18) 0.8289(4) 0.0295(7) Uani 1 1 d
C17 C 0.4200(3) 0.64659(16) 0.9518(3) 0.0234(6) Uani 1 1 d
C18 C 0.2615(3) 0.72930(15) 0.7406(4) 0.0285(7) Uani 1 1 d
H2N H 0.356(3) 0.4473(16) 0.724(4) 0.031(8) Uiso 1 1 d
H2 H 0.745(3) 0.4535(15) 0.521(3) 0.028(7) Uiso 1 1 d
H3 H 0.589(2) 0.4551(14) 0.706(3) 0.021(7) Uiso 1 1 d
H6 H 0.300(2) 0.2569(15) 0.493(3) 0.023(7) Uiso 1 1 d
H7 H 0.121(3) 0.2736(15) 0.657(4) 0.036(8) Uiso 1 1 d
H11 H -0.070(3) 0.5185(14) 0.688(3) 0.029(7) Uiso 1 1 d
H12 H 0.024(3) 0.6471(16) 0.658(4) 0.038(8) Uiso 1 1 d
H15A H 0.315(3) 0.4275(14) 1.061(3) 0.023(7) Uiso 1 1 d
H15B H 0.191(3) 0.4350(16) 1.117(4) 0.036(8) Uiso 1 1 d
H15C H 0.240(3) 0.3613(17) 1.083(4) 0.034(8) Uiso 1 1 d
H16A H -0.045(3) 0.3762(14) 0.708(4) 0.026(7) Uiso 1 1 d
H16B H 0.027(2) 0.3276(16) 0.851(3) 0.025(7) Uiso 1 1 d
H16C H -0.031(3) 0.4001(16) 0.904(4) 0.037(8) Uiso 1 1 d
H17A H 0.491(3) 0.6802(15) 0.960(3) 0.030(7) Uiso 1 1 d
H17B H 0.378(2) 0.6573(14) 1.042(3) 0.025(7) Uiso 1 1 d
H17C H 0.455(3) 0.5967(16) 0.972(3) 0.028(7) Uiso 1 1 d
H18A H 0.220(3) 0.7404(15) 0.826(4) 0.029(7) Uiso 1 1 d
H18B H 0.196(3) 0.7341(15) 0.627(4) 0.029(8) Uiso 1 1 d
H18C H 0.337(3) 0.7629(16) 0.748(4) 0.039(8) Uiso 1 1 d
H1N H 0.462(3) 0.3080(16) 0.325(4) 0.038(9) 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'
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
C13 O1 C10 107.18(18) . .
C1 N1 C4 109.5(2) . .
C1 N1 H1N 126.0(18) . .
C4 N1 H1N 124.4(18) . .
C5 N2 C8 110.3(2) . .
C5 N2 H2N 123.1(17) . .
C8 N2 H2N 126.4(17) . .
C2 C1 N1 107.3(2) . .
C2 C1 C14 129.8(2) . 3_666
N1 C1 C14 122.9(2) . 3_666
C1 C2 C3 107.9(2) . .
C1 C2 H2 126.7(16) . .
C3 C2 H2 125.3(16) . .
C4 C3 C2 108.1(2) . .
C4 C3 H3 126.1(15) . .
C2 C3 H3 125.8(15) . .
C3 C4 N1 107.2(2) . .
C3 C4 C5 130.7(2) . .
N1 C4 C5 122.1(2) . .
C6 C5 N2 107.1(2) . .
C6 C5 C4 133.1(2) . .
N2 C5 C4 119.7(2) . .
C5 C6 C7 107.8(2) . .
C5 C6 H6 123.6(16) . .
C7 C6 H6 128.6(16) . .
C8 C7 C6 108.0(2) . .
C8 C7 H7 123.9(16) . .
C6 C7 H7 128.2(16) . .
C7 C8 N2 106.9(2) . .
C7 C8 C9 131.7(2) . .
N2 C8 C9 121.4(2) . .
C10 C9 C8 109.99(19) . .
C10 C9 C16 108.9(2) . .
C8 C9 C16 109.5(2) . .
C10 C9 C15 108.5(2) . .
C8 C9 C15 110.7(2) . .
C16 C9 C15 109.2(2) . .
C11 C10 O1 109.1(2) . .
C11 C10 C9 136.1(2) . .
O1 C10 C9 114.8(2) . .
C10 C11 C12 107.6(2) . .
C10 C11 H11 125.9(16) . .
C12 C11 H11 126.5(16) . .
C13 C12 C11 107.1(2) . .
C13 C12 H12 123.3(17) . .
C11 C12 H12 129.6(17) . .
C12 C13 O1 109.0(2) . .
C12 C13 C14 135.5(2) . .
O1 C13 C14 115.2(2) . .
C13 C14 C1 107.2(2) . 3_666
C13 C14 C18 109.1(2) . .
C1 C14 C18 110.9(2) 3_666 .
C13 C14 C17 109.8(2) . .
C1 C14 C17 110.3(2) 3_666 .
C18 C14 C17 109.6(2) . .
C9 C15 H15A 111.4(16) . .
C9 C15 H15B 111.3(18) . .
H15A C15 H15B 109(2) . .
C9 C15 H15C 109.6(18) . .
H15A C15 H15C 107(2) . .
H15B C15 H15C 109(2) . .
C9 C16 H16A 113.4(16) . .
C9 C16 H16B 106.9(16) . .
H16A C16 H16B 101(2) . .
C9 C16 H16C 110.3(17) . .
H16A C16 H16C 111(2) . .
H16B C16 H16C 114(2) . .
C14 C17 H17A 111.2(16) . .
C14 C17 H17B 108.1(15) . .
H17A C17 H17B 110(2) . .
C14 C17 H17C 109.9(15) . .
H17A C17 H17C 110(2) . .
H17B C17 H17C 108(2) . .
C14 C18 H18A 108.9(17) . .
C14 C18 H18B 111.3(17) . .
H18A C18 H18B 107(2) . .
C14 C18 H18C 108.7(17) . .
H18A C18 H18C 111(2) . .
H18B C18 H18C 110(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.385(3) .
O1 C10 1.388(3) .
N1 C1 1.375(3) .
N1 C4 1.388(3) .
N1 H1N 0.91(3) .
N2 C5 1.377(3) .
N2 C8 1.378(3) .
N2 H2N 0.90(3) .
C1 C2 1.369(4) .
C1 C14 1.525(3) 3_666
C2 C3 1.413(3) .
C2 H2 0.94(3) .
C3 C4 1.360(3) .
C3 H3 0.95(3) .
C4 C5 1.454(3) .
C5 C6 1.365(3) .
C6 C7 1.421(4) .
C6 H6 0.93(3) .
C7 C8 1.367(4) .
C7 H7 0.99(3) .
C8 C9 1.526(3) .
C9 C10 1.508(4) .
C9 C16 1.529(4) .
C9 C15 1.550(4) .
C10 C11 1.335(4) .
C11 C12 1.433(4) .
C11 H11 0.96(3) .
C12 C13 1.345(3) .
C12 H12 0.95(3) .
C13 C14 1.501(3) .
C14 C1 1.525(3) 3_666
C14 C18 1.532(4) .
C14 C17 1.537(4) .
C15 H15A 0.94(3) .
C15 H15B 0.93(3) .
C15 H15C 0.92(3) .
C16 H16A 0.97(3) .
C16 H16B 0.93(3) .
C16 H16C 0.95(3) .
C17 H17A 0.96(3) .
C17 H17B 0.97(3) .
C17 H17C 0.99(3) .
C18 H18A 0.93(3) .
C18 H18B 0.96(3) .
C18 H18C 1.00(3) .
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
N2 H2N O1 0.90(3) 2.26(3) 2.831(3) 120(2)
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 0.2(3) . .
C4 N1 C1 C14 -178.9(2) . 3_666
N1 C1 C2 C3 0.2(3) . .
C14 C1 C2 C3 179.2(2) 3_666 .
C1 C2 C3 C4 -0.5(3) . .
C2 C3 C4 N1 0.6(3) . .
C2 C3 C4 C5 -179.8(2) . .
C1 N1 C4 C3 -0.6(3) . .
C1 N1 C4 C5 179.8(2) . .
C8 N2 C5 C6 -0.5(3) . .
C8 N2 C5 C4 -179.2(2) . .
C3 C4 C5 C6 -159.0(3) . .
N1 C4 C5 C6 20.6(4) . .
C3 C4 C5 N2 19.3(4) . .
N1 C4 C5 N2 -161.1(2) . .
N2 C5 C6 C7 0.4(3) . .
C4 C5 C6 C7 178.9(3) . .
C5 C6 C7 C8 -0.3(3) . .
C6 C7 C8 N2 0.0(3) . .
C6 C7 C8 C9 -178.0(3) . .
C5 N2 C8 C7 0.3(3) . .
C5 N2 C8 C9 178.5(2) . .
C7 C8 C9 C10 -136.1(3) . .
N2 C8 C9 C10 46.2(3) . .
C7 C8 C9 C16 -16.4(4) . .
N2 C8 C9 C16 165.8(2) . .
C7 C8 C9 C15 104.1(3) . .
N2 C8 C9 C15 -73.7(3) . .
C13 O1 C10 C11 -0.7(3) . .
C13 O1 C10 C9 179.49(19) . .
C8 C9 C10 C11 113.9(3) . .
C16 C9 C10 C11 -6.1(4) . .
C15 C9 C10 C11 -124.9(3) . .
C8 C9 C10 O1 -66.4(3) . .
C16 C9 C10 O1 173.6(2) . .
C15 C9 C10 O1 54.9(3) . .
O1 C10 C11 C12 0.2(3) . .
C9 C10 C11 C12 180.0(3) . .
C10 C11 C12 C13 0.4(3) . .
C11 C12 C13 O1 -0.8(3) . .
C11 C12 C13 C14 173.5(3) . .
C10 O1 C13 C12 0.9(3) . .
C10 O1 C13 C14 -174.64(19) . .
C12 C13 C14 C1 -102.4(3) . 3_666
O1 C13 C14 C1 71.6(2) . 3_666
C12 C13 C14 C18 17.7(4) . .
O1 C13 C14 C18 -168.3(2) . .
C12 C13 C14 C17 137.8(3) . .
O1 C13 C14 C17 -48.2(3) . .
