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#$Date: 2016-03-22 13:53:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178981 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/04/4120489.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_4120489
loop_
_publ_author_name
'Chang, Kai-Chi'
'Minami, Tsuyoshi'
'Koutnik, Petr'
'Savechenkov, Pavel Y.'
'Liu, Yuanli'
'Anzenbacher, Jr, Pavel'
_publ_section_title
;
 Anion Binding Modes in meso-Substituted Hexapyrrolic Calix[4]pyrrole
 Isomers.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1520
_journal_page_last               1525
_journal_paper_doi               10.1021/ja411391c
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C26 H18 N2 O2'
_chemical_formula_weight         390.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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                111.592(5)
_cell_angle_beta                 92.851(4)
_cell_angle_gamma                113.076(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2870(13)
_cell_length_b                   11.1500(10)
_cell_length_c                   13.0400(17)
_cell_measurement_temperature    153(2)
_cell_volume                     1246.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1514
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3762
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.067
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.484
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.502
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1123
_refine_ls_shift/su_max          0.449
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2212
_reflns_number_gt                2232
_reflns_number_total             3762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja411391c_si_003.cif
_cod_data_source_block           spa-24-1
_cod_database_code               4120489
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
N1 N 0.4922(4) 0.2809(3) 0.4862(3) 0.0356(10) Uani 1 1 d U
H1 H 0.4351 0.3019 0.4507 0.043 Uiso 1 1 calc R
N2 N 0.3584(4) 0.4826(3) 0.6319(3) 0.0355(10) Uani 1 1 d U
H2 H 0.4536 0.5274 0.6531 0.043 Uiso 1 1 calc R
C3 C 0.2741(5) 0.5475(4) 0.6205(4) 0.0335(11) Uani 1 1 d U
O4 O 0.3318(4) 0.3454(3) 0.3396(3) 0.0484(9) Uani 1 1 d U
N5 N 0.4265(4) 0.0858(4) 0.2392(3) 0.0355(10) Uani 1 1 d U
H5 H 0.4102 0.0564 0.2934 0.043 Uiso 1 1 calc R
C7 C 0.5312(5) 0.2124(4) 0.1438(4) 0.0332(11) Uani 1 1 d U
C8 C 0.6147(5) 0.2684(4) 0.4549(4) 0.0339(12) Uani 1 1 d U
O9 O 0.1766(4) -0.1438(3) 0.1915(3) 0.0586(11) Uani 1 1 d U
C10 C 0.2782(5) 0.3393(5) 0.6067(4) 0.0371(12) Uani 1 1 d U
C11 C 0.6668(5) 0.2958(4) 0.3537(4) 0.0339(12) Uani 1 1 d U
C12 C 0.4734(5) 0.2555(5) 0.5807(4) 0.0379(12) Uani 1 1 d U
C13 C 0.1958(6) -0.1063(5) 0.1043(5) 0.0436(13) Uani 1 1 d U
C14 C 0.3345(5) 0.0661(5) -0.0443(4) 0.0449(13) Uani 1 1 d U
H14A H 0.2749 -0.0387 -0.0882 0.054 Uiso 1 1 calc R
H14B H 0.4141 0.0977 -0.0822 0.054 Uiso 1 1 calc R
C15 C 0.5458(5) 0.2061(4) 0.2475(4) 0.0339(12) Uani 1 1 d U
C16 C 0.3974(5) 0.0954(5) 0.0725(4) 0.0351(12) Uani 1 1 d U
C17 C 0.2080(5) 0.2989(5) 0.2881(4) 0.0387(12) Uani 1 1 d U
C18 C 0.6715(5) 0.2332(5) 0.5290(4) 0.0426(13) Uani 1 1 d U
H18 H 0.7563 0.2183 0.5288 0.051 Uiso 1 1 calc R
C19 C 0.1360(5) 0.3132(5) 0.5775(4) 0.0432(13) Uani 1 1 d U
H19 H 0.0538 0.2232 0.5551 0.052 Uiso 1 1 calc R
C20 C 0.7892(5) 0.2474(5) 0.3312(4) 0.0438(13) Uani 1 1 d U
H20A H 0.7511 0.1450 0.3142 0.066 Uiso 1 1 calc R
H20B H 0.8694 0.3034 0.3984 0.066 Uiso 1 1 calc R
H20C H 0.8244 0.2632 0.2666 0.066 Uiso 1 1 calc R
C21 C 0.3420(5) 0.2489(5) 0.6297(4) 0.0422(13) Uani 1 1 d U
C22 C 0.2405(6) 0.1438(5) -0.0440(4) 0.0546(15) Uani 1 1 d U
H22A H 0.1596 0.1102 -0.0089 0.082 Uiso 1 1 calc R
H22B H 0.2023 0.1233 -0.1220 0.082 Uiso 1 1 calc R
H22C H 0.2992 0.2476 -0.0008 0.082 Uiso 1 1 calc R
C23 C 0.1321(5) 0.4424(5) 0.5862(4) 0.0415(13) Uani 1 1 d U
H23 H 0.0478 0.4544 0.5712 0.050 Uiso 1 1 calc R
C24 C 0.3369(5) 0.0191(5) 0.1332(4) 0.0371(12) Uani 1 1 d U
C25 C 0.0928(5) 0.1560(5) 0.2730(5) 0.0521(14) Uani 1 1 d U
H25A H 0.1369 0.1070 0.3008 0.078 Uiso 1 1 calc R
H25B H 0.0457 0.0971 0.1925 0.078 Uiso 1 1 calc R
H25C H 0.0204 0.1704 0.3158 0.078 Uiso 1 1 calc R
C26 C 0.5807(6) 0.2226(5) 0.6075(4) 0.0453(13) Uani 1 1 d U
H26 H 0.5929 0.1970 0.6679 0.054 Uiso 1 1 calc R
C27 C 0.1619(6) 0.3820(5) 0.2409(5) 0.0568(15) Uani 1 1 d U
H27A H 0.1066 0.4231 0.2893 0.085 Uiso 1 1 calc R
H27B H 0.1009 0.3182 0.1644 0.085 Uiso 1 1 calc R
H27C H 0.2477 0.4596 0.2377 0.085 Uiso 1 1 calc R
C28 C 0.6394(5) 0.3184(5) 0.1076(4) 0.0492(14) Uani 1 1 d U
H28A H 0.7152 0.3966 0.1739 0.074 Uiso 1 1 calc R
H28B H 0.5896 0.3579 0.0730 0.074 Uiso 1 1 calc R
H28C H 0.6835 0.2693 0.0524 0.074 Uiso 1 1 calc R
C29 C 0.3879(7) 0.3030(6) 0.7580(5) 0.0633(17) Uani 1 1 d U
H29A H 0.4609 0.4037 0.7906 0.095 Uiso 1 1 calc R
H29B H 0.4290 0.2446 0.7745 0.095 Uiso 1 1 calc R
H29C H 0.3031 0.2955 0.7911 0.095 Uiso 1 1 calc R
C30 C 0.2255(6) 0.0915(5) 0.5789(5) 0.0714(18) Uani 1 1 d U
H30A H 0.1451 0.0841 0.6173 0.107 Uiso 1 1 calc R
H30B H 0.2679 0.0307 0.5891 0.107 Uiso 1 1 calc R
H30C H 0.1893 0.0595 0.4979 0.107 Uiso 1 1 calc R
C31 C 0.0375(6) -0.2711(6) 0.1711(5) 0.0719(18) Uani 1 1 d U
H31A H -0.0298 -0.2957 0.1017 0.086 Uiso 1 1 calc R
H31B H -0.0092 -0.2497 0.2357 0.086 Uiso 1 1 calc R
O32 O 0.1116(4) -0.1687(4) 0.0137(3) 0.0580(10) Uani 1 1 d U
C33 C 0.0706(8) -0.3894(7) 0.1584(7) 0.107(3) Uani 1 1 d U
H33A H 0.1295 -0.4004 0.1019 0.161 Uiso 1 1 calc R
H33B H -0.0198 -0.4780 0.1335 0.161 Uiso 1 1 calc R
H33C H 0.1247 -0.3702 0.2312 0.161 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'
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
C8 N1 C12 109.7(4) . .
C8 N1 H1 125.2 . .
C12 N1 H1 125.2 . .
C3 N2 C10 112.6(4) . .
C3 N2 H2 123.7 . .
C10 N2 H2 123.7 . .
N2 C3 C23 106.2(4) . .
N2 C3 C11 123.7(4) . 2_666
C23 C3 C11 130.1(4) . 2_666
C24 N5 C15 109.5(3) . .
C24 N5 H5 125.3 . .
C15 N5 H5 125.3 . .
C15 C7 C16 108.0(4) . .
C15 C7 C28 127.2(4) . .
C16 C7 C28 124.7(4) . .
C18 C8 N1 107.5(4) . .
C18 C8 C11 130.7(5) . .
N1 C8 C11 121.8(4) . .
C13 O9 C31 115.3(4) . .
C19 C10 N2 104.9(4) . .
C19 C10 C21 131.0(4) . .
N2 C10 C21 123.2(4) . .
C15 C11 C3 110.7(4) . 2_666
C15 C11 C8 111.1(4) . .
C3 C11 C8 110.8(4) 2_666 .
C15 C11 C20 107.4(3) . .
C3 C11 C20 109.2(4) 2_666 .
C8 C11 C20 107.6(4) . .
C26 C12 N1 107.3(4) . .
C26 C12 C21 130.0(4) . .
N1 C12 C21 122.2(4) . .
O32 C13 O9 125.0(5) . .
O32 C13 C24 124.2(5) . .
O9 C13 C24 110.7(4) . .
C16 C14 C22 111.8(4) . .
C16 C14 H14A 109.3 . .
C22 C14 H14A 109.3 . .
C16 C14 H14B 109.3 . .
C22 C14 H14B 109.3 . .
H14A C14 H14B 107.9 . .
C7 C15 N5 106.9(4) . .
C7 C15 C11 132.2(4) . .
N5 C15 C11 120.7(4) . .
C24 C16 C7 106.9(4) . .
C24 C16 C14 127.0(4) . .
C7 C16 C14 126.1(4) . .
O4 C17 C27 122.2(4) . .
O4 C17 C25 121.3(4) . .
C27 C17 C25 116.6(4) . .
C8 C18 C26 107.4(5) . .
C8 C18 H18 126.3 . .
C26 C18 H18 126.3 . .
C10 C19 C23 109.1(4) . .
C10 C19 H19 125.5 . .
C23 C19 H19 125.5 . .
C11 C20 H20A 109.5 . .
C11 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C11 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C10 C21 C12 113.2(4) . .
C10 C21 C29 108.4(4) . .
C12 C21 C29 108.2(4) . .
C10 C21 C30 108.9(4) . .
C12 C21 C30 108.8(4) . .
C29 C21 C30 109.4(4) . .
C14 C22 H22A 109.5 . .
C14 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C14 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C3 C23 C19 107.2(4) . .
C3 C23 H23 126.4 . .
C19 C23 H23 126.4 . .
C16 C24 N5 108.6(4) . .
C16 C24 C13 130.4(5) . .
N5 C24 C13 120.8(4) . .
C17 C25 H25A 109.5 . .
C17 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C17 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C12 C26 C18 108.1(4) . .
C12 C26 H26 126.0 . .
C18 C26 H26 126.0 . .
C17 C27 H27A 109.5 . .
C17 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C17 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C7 C28 H28A 109.5 . .
C7 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C7 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C21 C29 H29A 109.5 . .
C21 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C21 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C21 C30 H30A 109.5 . .
C21 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C21 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
O9 C31 C33 107.7(5) . .
O9 C31 H31A 110.2 . .
C33 C31 H31A 110.2 . .
O9 C31 H31B 110.2 . .
C33 C31 H31B 110.2 . .
H31A C31 H31B 108.5 . .
C31 C33 H33A 109.5 . .
C31 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
C31 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C8 1.386(6) .
N1 C12 1.368(5) .
N1 H1 0.8800 .
N2 C3 1.362(5) .
N2 C10 1.376(5) .
N2 H2 0.8800 .
C3 C23 1.383(6) .
C3 C11 1.500(6) 2_666
O4 C17 1.218(5) .
N5 C24 1.376(5) .
N5 C15 1.381(5) .
N5 H5 0.8800 .
C7 C15 1.383(6) .
C7 C16 1.426(6) .
C7 C28 1.514(6) .
C8 C18 1.354(6) .
C8 C11 1.537(6) .
O9 C13 1.347(6) .
O9 C31 1.492(6) .
C10 C19 1.377(6) .
C10 C21 1.503(6) .
C11 C15 1.517(6) .
C11 C3 1.500(6) 2_666
C11 C20 1.554(6) .
C12 C26 1.359(6) .
C12 C21 1.511(7) .
C13 O32 1.204(5) .
C13 C24 1.474(6) .
C14 C16 1.488(6) .
C14 C22 1.530(7) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C16 C24 1.367(6) .
C17 C27 1.482(6) .
C17 C25 1.500(6) .
C18 C26 1.425(7) .
C18 H18 0.9500 .
C19 C23 1.420(6) .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C29 1.531(7) .
C21 C30 1.540(6) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23 0.9500 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26 0.9500 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 C33 1.443(8) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
