#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025042.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_4025042
loop_
_publ_author_name
'En-Xuan Zhang'
'De-Xian Wang'
'Zhi-Tang Huang'
'Mei-Xiang Wang'
_publ_section_title
;
Synthesis of (NH)m(NMe)4-m-Bridged Calix[4]pyridines and the Effect of NH
Bridge on Structure and Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8595
_journal_page_last               8603
_journal_paper_doi               10.1021/jo901609u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H20 N8'
_chemical_formula_sum            'C22 H20 N8'
_chemical_formula_weight         396.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 112.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.734(5)
_cell_length_b                   10.295(2)
_cell_length_c                   17.953(4)
_cell_measurement_reflns_used    876
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     3871.7(13)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6546
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+8.1101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1569
_reflns_number_gt                2952
_reflns_number_total             3412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901609u_si_002.cif
_cod_data_source_block           sx2577
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4025042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.48959(11) 0.6103(2) 0.11327(14) 0.0178(5) Uani 1 1 d . . .
N2 N 0.52995(11) 0.4135(2) 0.17596(14) 0.0189(5) Uani 1 1 d . . .
H2A H 0.5620 0.3675 0.2093 0.023 Uiso 1 1 calc R . .
N3 N 0.43644(11) 0.3009(2) 0.15623(13) 0.0171(5) Uani 1 1 d . . .
N4 N 0.34007(11) 0.1995(2) 0.14409(14) 0.0195(5) Uani 1 1 d . . .
N5 N 0.29656(11) 0.4038(2) 0.11132(14) 0.0191(5) Uani 1 1 d . . .
N6 N 0.26109(12) 0.6128(2) 0.07580(16) 0.0253(6) Uani 1 1 d . . .
H6A H 0.2395 0.6809 0.0806 0.030 Uiso 1 1 calc R . .
N7 N 0.34836(11) 0.7025(2) 0.05653(14) 0.0206(6) Uani 1 1 d . . .
N8 N 0.43985(12) 0.7945(2) 0.04611(15) 0.0220(6) Uani 1 1 d . . .
C1 C 0.48916(14) 0.7406(3) 0.11280(16) 0.0182(6) Uani 1 1 d . . .
C2 C 0.53392(15) 0.8145(3) 0.17318(18) 0.0238(7) Uani 1 1 d . . .
H2B H 0.5338 0.9067 0.1705 0.029 Uiso 1 1 calc R . .
C3 C 0.57860(15) 0.7482(3) 0.23737(18) 0.0249(7) Uani 1 1 d . . .
H3B H 0.6090 0.7958 0.2806 0.030 Uiso 1 1 calc R . .
C4 C 0.57982(15) 0.6144(3) 0.23977(18) 0.0243(7) Uani 1 1 d . . .
H4A H 0.6108 0.5685 0.2833 0.029 Uiso 1 1 calc R . .
C5 C 0.53356(13) 0.5492(3) 0.17543(16) 0.0172(6) Uani 1 1 d . . .
C6 C 0.47436(13) 0.3517(3) 0.12242(17) 0.0173(6) Uani 1 1 d . . .
C7 C 0.38218(14) 0.2448(3) 0.10705(17) 0.0178(6) Uani 1 1 d . . .
C8 C 0.36396(14) 0.2346(3) 0.02427(17) 0.0204(6) Uani 1 1 d . . .
H8A H 0.3251 0.1933 -0.0085 0.024 Uiso 1 1 calc R . .
C9 C 0.40433(14) 0.2867(3) -0.00917(17) 0.0210(6) Uani 1 1 d . . .
H9A H 0.3935 0.2812 -0.0658 0.025 Uiso 1 1 calc R . .
C10 C 0.46003(14) 0.3463(3) 0.03982(17) 0.0191(6) Uani 1 1 d . . .
H10A H 0.4881 0.3829 0.0178 0.023 Uiso 1 1 calc R . .
C11 C 0.36764(16) 0.1081(3) 0.2110(2) 0.0312(8) Uani 1 1 d . . .
H11A H 0.3352 0.0835 0.2318 0.047 Uiso 1 1 calc R . .
H11B H 0.4038 0.1492 0.2542 0.047 Uiso 1 1 calc R . .
H11C H 0.3824 0.0304 0.1919 0.047 Uiso 1 1 calc R . .
C12 C 0.29708(13) 0.2916(3) 0.14934(16) 0.0178(6) Uani 1 1 d . . .
C13 C 0.25773(15) 0.2695(3) 0.19171(18) 0.0247(7) Uani 1 1 d . . .
H13A H 0.2589 0.1895 0.2186 0.030 Uiso 1 1 calc R . .
C14 C 0.21699(15) 0.3687(3) 0.19284(18) 0.0257(7) Uani 1 1 d . . .
H14A H 0.1893 0.3564 0.2205 0.031 Uiso 1 1 calc R . .
C15 C 0.21602(14) 0.4851(3) 0.15458(17) 0.0225(7) Uani 1 1 d . . .
H15A H 0.1883 0.5536 0.1554 0.027 Uiso 1 1 calc R . .
C16 C 0.25761(13) 0.4983(3) 0.11437(17) 0.0186(6) Uani 1 1 d . . .
C17 C 0.29865(14) 0.6233(3) 0.02868(18) 0.0205(6) Uani 1 1 d . . .
C18 C 0.28152(14) 0.5544(3) -0.04332(18) 0.0239(7) Uani 1 1 d . . .
H18A H 0.2462 0.4966 -0.0603 0.029 Uiso 1 1 calc R . .
C19 C 0.31736(15) 0.5724(3) -0.08930(18) 0.0256(7) Uani 1 1 d . . .
H19A H 0.3063 0.5287 -0.1395 0.031 Uiso 1 1 calc R . .
C20 C 0.36966(14) 0.6549(3) -0.06154(17) 0.0227(7) Uani 1 1 d . . .
H20A H 0.3950 0.6693 -0.0922 0.027 Uiso 1 1 calc R . .
C21 C 0.38387(14) 0.7154(3) 0.01203(17) 0.0202(6) Uani 1 1 d . . .
C22 C 0.42817(18) 0.9338(3) 0.0455(2) 0.0386(9) Uani 1 1 d . . .
H22A H 0.4690 0.9799 0.0693 0.058 Uiso 1 1 calc R . .
H22B H 0.4023 0.9522 0.0771 0.058 Uiso 1 1 calc R . .
H22C H 0.4053 0.9632 -0.0103 0.058 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'
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
_geom_angle_publ_flag
C5 N1 C1 118.6(3) . . ?
C5 N2 C6 119.1(2) . . ?
C5 N2 H2A 120.5 . . ?
C6 N2 H2A 120.5 . . ?
C7 N3 C6 117.4(2) . . ?
C12 N4 C7 114.9(2) . . ?
C12 N4 C11 118.1(2) . . ?
C7 N4 C11 116.0(2) . . ?
C16 N5 C12 118.9(2) . . ?
C16 N6 C17 121.8(2) . . ?
C16 N6 H6A 119.1 . . ?
C17 N6 H6A 119.1 . . ?
C17 N7 C21 117.3(3) . . ?
C1 N8 C21 115.1(2) . . ?
C1 N8 C22 118.7(3) . . ?
C21 N8 C22 115.2(3) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 N8 113.8(3) . . ?
C2 C1 N8 123.5(3) . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2B 121.4 . . ?
C1 C2 H2B 121.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3B 119.4 . . ?
C2 C3 H3B 119.4 . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 H4A 121.5 . . ?
C5 C4 H4A 121.5 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 N2 116.7(3) . . ?
C4 C5 N2 120.1(3) . . ?
N3 C6 C10 122.9(3) . . ?
N3 C6 N2 115.6(2) . . ?
C10 C6 N2 121.5(3) . . ?
N3 C7 C8 123.8(3) . . ?
N3 C7 N4 116.3(2) . . ?
C8 C7 N4 119.8(3) . . ?
C7 C8 C9 117.6(3) . . ?
C7 C8 H8A 121.2 . . ?
C9 C8 H8A 121.2 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C6 118.5(3) . . ?
C9 C10 H10A 120.8 . . ?
C6 C10 H10A 120.8 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 N4 114.9(2) . . ?
N5 C12 C13 122.4(3) . . ?
N4 C12 C13 122.7(3) . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13A 121.3 . . ?
C12 C13 H13A 121.3 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 117.3(3) . . ?
C14 C15 H15A 121.4 . . ?
C16 C15 H15A 121.4 . . ?
N5 C16 N6 115.7(2) . . ?
N5 C16 C15 122.9(3) . . ?
N6 C16 C15 121.4(3) . . ?
N7 C17 C18 123.7(3) . . ?
N7 C17 N6 116.4(3) . . ?
C18 C17 N6 119.9(3) . . ?
C19 C18 C17 118.1(3) . . ?
C19 C18 H18A 121.0 . . ?
C17 C18 H18A 121.0 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C21 C20 C19 118.0(3) . . ?
C21 C20 H20A 121.0 . . ?
C19 C20 H20A 121.0 . . ?
N7 C21 C20 123.5(3) . . ?
N7 C21 N8 116.2(3) . . ?
C20 C21 N8 120.3(3) . . ?
N8 C22 H22A 109.5 . . ?
N8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.332(4) . ?
N1 C1 1.342(4) . ?
N2 C5 1.399(4) . ?
N2 C6 1.408(4) . ?
N2 H2A 0.8800 . ?
N3 C7 1.337(4) . ?
N3 C6 1.339(4) . ?
N4 C12 1.391(4) . ?
N4 C7 1.439(4) . ?
N4 C11 1.461(4) . ?
N5 C16 1.330(4) . ?
N5 C12 1.340(4) . ?
N6 C16 1.385(4) . ?
N6 C17 1.420(4) . ?
N6 H6A 0.8800 . ?
N7 C17 1.324(4) . ?
N7 C21 1.345(4) . ?
N8 C1 1.398(4) . ?
N8 C21 1.432(4) . ?
N8 C22 1.459(4) . ?
C1 C2 1.390(4) . ?
C2 C3 1.384(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.378(4) . ?
C3 H3B 0.9500 . ?
C4 C5 1.395(4) . ?
C4 H4A 0.9500 . ?
C6 C10 1.390(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.385(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.374(4) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.400(4) . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.376(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.401(4) . ?
C15 H15A 0.9500 . ?
C17 C18 1.391(4) . ?
C18 C19 1.379(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.381(4) . ?
C20 H20A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
_geom_hbond_site_symmetry_A
N2 H2A N3 0.88 2.50 3.036(3) 120.2 2_655
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 2.1(4) . . . . ?
C5 N1 C1 N8 -178.1(2) . . . . ?
C21 N8 C1 N1 27.7(3) . . . . ?
C22 N8 C1 N1 170.2(3) . . . . ?
C21 N8 C1 C2 -152.5(3) . . . . ?
C22 N8 C1 C2 -10.0(4) . . . . ?
N1 C1 C2 C3 -2.7(4) . . . . ?
N8 C1 C2 C3 177.5(3) . . . . ?
C1 C2 C3 C4 2.1(4) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C1 N1 C5 C4 -0.8(4) . . . . ?
C1 N1 C5 N2 176.3(2) . . . . ?
C3 C4 C5 N1 0.3(4) . . . . ?
C3 C4 C5 N2 -176.7(3) . . . . ?
C6 N2 C5 N1 -13.2(4) . . . . ?
C6 N2 C5 C4 164.0(3) . . . . ?
C7 N3 C6 C10 -1.1(4) . . . . ?
C7 N3 C6 N2 178.0(2) . . . . ?
C5 N2 C6 N3 -107.2(3) . . . . ?
C5 N2 C6 C10 71.9(4) . . . . ?
C6 N3 C7 C8 1.2(4) . . . . ?
C6 N3 C7 N4 -175.6(2) . . . . ?
C12 N4 C7 N3 87.6(3) . . . . ?
C11 N4 C7 N3 -56.0(3) . . . . ?
C12 N4 C7 C8 -89.3(3) . . . . ?
C11 N4 C7 C8 127.1(3) . . . . ?
N3 C7 C8 C9 -0.5(4) . . . . ?
N4 C7 C8 C9 176.1(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C6 0.4(4) . . . . ?
N3 C6 C10 C9 0.3(4) . . . . ?
N2 C6 C10 C9 -178.7(3) . . . . ?
C16 N5 C12 N4 -178.9(2) . . . . ?
C16 N5 C12 C13 0.5(4) . . . . ?
C7 N4 C12 N5 7.0(3) . . . . ?
C11 N4 C12 N5 149.8(3) . . . . ?
C7 N4 C12 C13 -172.4(3) . . . . ?
C11 N4 C12 C13 -29.6(4) . . . . ?
N5 C12 C13 C14 0.4(4) . . . . ?
N4 C12 C13 C14 179.8(3) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C12 N5 C16 N6 178.1(2) . . . . ?
C12 N5 C16 C15 -1.1(4) . . . . ?
C17 N6 C16 N5 6.7(4) . . . . ?
C17 N6 C16 C15 -174.1(3) . . . . ?
C14 C15 C16 N5 0.7(4) . . . . ?
C14 C15 C16 N6 -178.4(3) . . . . ?
C21 N7 C17 C18 -0.3(4) . . . . ?
C21 N7 C17 N6 -178.9(2) . . . . ?
C16 N6 C17 N7 -113.8(3) . . . . ?
C16 N6 C17 C18 67.5(4) . . . . ?
N7 C17 C18 C19 -1.8(4) . . . . ?
N6 C17 C18 C19 176.7(3) . . . . ?
C17 C18 C19 C20 1.7(4) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C17 N7 C21 C20 2.5(4) . . . . ?
C17 N7 C21 N8 -175.8(2) . . . . ?
C19 C20 C21 N7 -2.6(4) . . . . ?
C19 C20 C21 N8 175.7(3) . . . . ?
C1 N8 C21 N7 70.7(3) . . . . ?
C22 N8 C21 N7 -73.1(3) . . . . ?
C1 N8 C21 C20 -107.7(3) . . . . ?
C22 N8 C21 C20 108.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659086
