#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029283.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_4029283
loop_
_publ_author_name
'Fa, Shi-Xin'
'Wang, Li-Xia'
'Wang, De-Xian'
'Zhao, Liang'
'Wang, Mei-Xiang'
_publ_section_title
;
 Synthesis, Structure, and Fullerene-Complexing Property of
 Azacalix[6]aromatics.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3559
_journal_page_last               3571
_journal_paper_doi               10.1021/jo5003714
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C42 H42 N6'
_chemical_formula_sum            'C42 H42 N6'
_chemical_formula_weight         630.82
_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                 110.578(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.366(2)
_cell_length_b                   15.991(3)
_cell_length_c                   9.6640(19)
_cell_measurement_reflns_used    435
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1644.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7271
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0595
_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)+(0.0328P)²+0.7797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                3180
_reflns_number_total             3717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5003714_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029283.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4029283
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
_atom_site_refinement_flags
N1 N 0.35960(13) 0.18371(8) 0.57400(17) 0.0311(3) Uani 1 1 d .
N2 N 0.80361(13) 0.25935(9) 0.76805(16) 0.0310(3) Uani 1 1 d .
N3 N 0.67830(13) 0.51549(8) 0.48559(16) 0.0273(3) Uani 1 1 d .
C1 C 0.19423(16) 0.40941(11) 0.6339(2) 0.0317(4) Uani 1 1 d .
H1A H 0.1555 0.4603 0.6456 0.038 Uiso 1 1 calc R
C2 C 0.16316(17) 0.33481(12) 0.6846(2) 0.0337(4) Uani 1 1 d .
H2A H 0.1023 0.3347 0.7314 0.040 Uiso 1 1 calc R
C3 C 0.21862(16) 0.26051(11) 0.66872(19) 0.0298(4) Uani 1 1 d .
H3A H 0.1960 0.2102 0.7052 0.036 Uiso 1 1 calc R
C4 C 0.30792(15) 0.25854(10) 0.59931(18) 0.0247(4) Uani 1 1 d .
C5 C 0.29947(18) 0.10576(11) 0.5865(2) 0.0390(5) Uani 1 1 d .
H5A H 0.2088 0.1102 0.5329 0.059 Uiso 1 1 calc R
H5B H 0.3150 0.0939 0.6909 0.059 Uiso 1 1 calc R
H5C H 0.3339 0.0604 0.5440 0.059 Uiso 1 1 calc R
C6 C 0.48185(16) 0.17974(10) 0.56648(18) 0.0259(4) Uani 1 1 d .
C7 C 0.50433(17) 0.12754(11) 0.46312(19) 0.0307(4) Uani 1 1 d .
H7A H 0.4368 0.0980 0.3933 0.037 Uiso 1 1 calc R
C8 C 0.62479(18) 0.11877(11) 0.4622(2) 0.0333(4) Uani 1 1 d .
H8A H 0.6398 0.0825 0.3924 0.040 Uiso 1 1 calc R
C9 C 0.72397(17) 0.16213(11) 0.5616(2) 0.0314(4) Uani 1 1 d .
H9A H 0.8066 0.1555 0.5603 0.038 Uiso 1 1 calc R
C10 C 0.70193(15) 0.21529(10) 0.66291(18) 0.0258(4) Uani 1 1 d .
C11 C 0.58119(15) 0.22370(10) 0.66616(18) 0.0257(4) Uani 1 1 d .
H11A H 0.5665 0.2596 0.7367 0.031 Uiso 1 1 calc R
C12 C 0.90248(17) 0.20913(12) 0.8716(2) 0.0397(5) Uani 1 1 d .
H12A H 0.9210 0.2306 0.9720 0.060 Uiso 1 1 calc R
H12B H 0.9783 0.2122 0.8457 0.060 Uiso 1 1 calc R
H12C H 0.8746 0.1509 0.8667 0.060 Uiso 1 1 calc R
C13 C 0.82542(14) 0.34305(10) 0.74654(18) 0.0241(3) Uani 1 1 d .
C14 C 0.92993(15) 0.38451(11) 0.84409(18) 0.0274(4) Uani 1 1 d .
H14A H 0.9857 0.3564 0.9282 0.033 Uiso 1 1 calc R
C15 C 0.95124(16) 0.46709(11) 0.81662(18) 0.0289(4) Uani 1 1 d .
H15A H 1.0235 0.4946 0.8821 0.035 Uiso 1 1 calc R
C16 C 0.87163(15) 0.51082(11) 0.69797(18) 0.0275(4) Uani 1 1 d .
H16A H 0.8890 0.5674 0.6821 0.033 Uiso 1 1 calc R
C17 C 0.76461(14) 0.47092(10) 0.60065(17) 0.0232(3) Uani 1 1 d .
C18 C 0.74384(15) 0.38708(10) 0.62549(18) 0.0247(4) Uani 1 1 d .
H18A H 0.6727 0.3592 0.5587 0.030 Uiso 1 1 calc R
C19 C 0.57584(17) 0.47207(11) 0.3748(2) 0.0381(5) Uani 1 1 d .
H19A H 0.5286 0.4394 0.4236 0.057 Uiso 1 1 calc R
H19B H 0.6099 0.4345 0.3181 0.057 Uiso 1 1 calc R
H19C H 0.5199 0.5130 0.3080 0.057 Uiso 1 1 calc R
C20 C 0.71662(15) 0.59151(10) 0.43454(18) 0.0251(4) Uani 1 1 d .
C21 C 0.66121(15) 0.66544(10) 0.45243(18) 0.0247(3) Uani 1 1 d .
H21A H 0.6012 0.6650 0.5005 0.030 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
C4 N1 C6 121.95(13) . .
C4 N1 C5 119.02(14) . .
C6 N1 C5 117.75(14) . .
C13 N2 C10 120.73(13) . .
C13 N2 C12 119.93(14) . .
C10 N2 C12 116.94(14) . .
C17 N3 C20 119.59(13) . .
C17 N3 C19 120.09(13) . .
C20 N3 C19 114.40(13) . .
C2 C1 C20 118.61(16) . 3_666
C2 C1 H1A 120.7 . .
C20 C1 H1A 120.7 3_666 .
C3 C2 C1 121.38(16) . .
C3 C2 H2A 119.3 . .
C1 C2 H2A 119.3 . .
C2 C3 C4 120.64(16) . .
C2 C3 H3A 119.7 . .
C4 C3 H3A 119.7 . .
N1 C4 C3 121.69(15) . .
N1 C4 C21 120.50(14) . 3_666
C3 C4 C21 117.71(15) . 3_666
N1 C5 H5A 109.5 . .
N1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C11 C6 C7 119.40(16) . .
C11 C6 N1 120.91(15) . .
C7 C6 N1 119.59(15) . .
C8 C7 C6 119.88(16) . .
C8 C7 H7A 120.1 . .
C6 C7 H7A 120.1 . .
C7 C8 C9 120.89(16) . .
C7 C8 H8A 119.6 . .
C9 C8 H8A 119.6 . .
C8 C9 C10 119.53(16) . .
C8 C9 H9A 120.2 . .
C10 C9 H9A 120.2 . .
C9 C10 C11 120.05(16) . .
C9 C10 N2 120.25(15) . .
C11 C10 N2 119.65(15) . .
C6 C11 C10 120.22(15) . .
C6 C11 H11A 119.9 . .
C10 C11 H11A 119.9 . .
N2 C12 H12A 109.5 . .
N2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 C14 120.66(15) . .
N2 C13 C18 120.55(14) . .
C14 C13 C18 118.78(15) . .
C15 C14 C13 119.18(15) . .
C15 C14 H14A 120.4 . .
C13 C14 H14A 120.4 . .
C16 C15 C14 122.42(16) . .
C16 C15 H15A 118.8 . .
C14 C15 H15A 118.8 . .
C15 C16 C17 119.28(15) . .
C15 C16 H16A 120.4 . .
C17 C16 H16A 120.4 . .
N3 C17 C18 120.94(14) . .
N3 C17 C16 120.28(14) . .
C18 C17 C16 118.72(15) . .
C17 C18 C13 121.59(15) . .
C17 C18 H18A 119.2 . .
C13 C18 H18A 119.2 . .
N3 C19 H19A 109.5 . .
N3 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N3 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 C1 120.66(15) . 3_666
C21 C20 N3 118.41(14) . .
C1 C20 N3 120.92(15) 3_666 .
C20 C21 C4 121.00(15) . 3_666
C20 C21 H21A 119.5 . .
C4 C21 H21A 119.5 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.392(2) .
N1 C6 1.418(2) .
N1 C5 1.447(2) .
N2 C13 1.390(2) .
N2 C10 1.428(2) .
N2 C12 1.455(2) .
N3 C17 1.393(2) .
N3 C20 1.436(2) .
N3 C19 1.452(2) .
C1 C2 1.382(3) .
C1 C20 1.392(2) 3_666
C1 H1A 0.9500 .
C2 C3 1.379(3) .
C2 H2A 0.9500 .
C3 C4 1.400(2) .
C3 H3A 0.9500 .
C4 C21 1.405(2) 3_666
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C11 1.390(2) .
C6 C7 1.393(2) .
C7 C8 1.379(3) .
C7 H7A 0.9500 .
C8 C9 1.383(3) .
C8 H8A 0.9500 .
C9 C10 1.384(2) .
C9 H9A 0.9500 .
C10 C11 1.390(2) .
C11 H11A 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.397(2) .
C13 C18 1.401(2) .
C14 C15 1.385(2) .
C14 H14A 0.9500 .
C15 C16 1.376(2) .
C15 H15A 0.9500 .
C16 C17 1.403(2) .
C16 H16A 0.9500 .
C17 C18 1.397(2) .
C18 H18A 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 C21 1.379(2) .
C20 C1 1.392(2) 3_666
C21 C4 1.405(2) 3_666
C21 H21A 0.9500 .
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
C20 C1 C2 C3 0.1(3) 3_666 .
C1 C2 C3 C4 -0.5(3) . .
C6 N1 C4 C3 -151.77(16) . .
C5 N1 C4 C3 15.0(2) . .
C6 N1 C4 C21 32.0(2) . 3_666
C5 N1 C4 C21 -161.18(17) . 3_666
C2 C3 C4 N1 -176.06(16) . .
C2 C3 C4 C21 0.2(2) . 3_666
C4 N1 C6 C11 42.3(2) . .
C5 N1 C6 C11 -124.60(18) . .
C4 N1 C6 C7 -141.21(16) . .
C5 N1 C6 C7 51.8(2) . .
C11 C6 C7 C8 1.2(2) . .
N1 C6 C7 C8 -175.34(15) . .
C6 C7 C8 C9 -0.9(3) . .
C7 C8 C9 C10 -0.3(3) . .
C8 C9 C10 C11 1.2(2) . .
C8 C9 C10 N2 178.85(15) . .
C13 N2 C10 C9 101.02(19) . .
C12 N2 C10 C9 -61.4(2) . .
C13 N2 C10 C11 -81.3(2) . .
C12 N2 C10 C11 116.32(18) . .
C7 C6 C11 C10 -0.3(2) . .
N1 C6 C11 C10 176.20(15) . .
C9 C10 C11 C6 -0.9(2) . .
N2 C10 C11 C6 -178.60(14) . .
C10 N2 C13 C14 -175.56(15) . .
C12 N2 C13 C14 -13.7(2) . .
C10 N2 C13 C18 3.6(2) . .
C12 N2 C13 C18 165.47(16) . .
N2 C13 C14 C15 177.80(15) . .
C18 C13 C14 C15 -1.4(2) . .
C13 C14 C15 C16 1.4(2) . .
C14 C15 C16 C17 0.1(2) . .
C20 N3 C17 C18 -161.63(15) . .
C19 N3 C17 C18 -10.2(2) . .
C20 N3 C17 C16 21.2(2) . .
C19 N3 C17 C16 172.65(16) . .
C15 C16 C17 N3 175.69(15) . .
C15 C16 C17 C18 -1.5(2) . .
N3 C17 C18 C13 -175.66(14) . .
C16 C17 C18 C13 1.5(2) . .
N2 C13 C18 C17 -179.26(15) . .
C14 C13 C18 C17 -0.1(2) . .
C17 N3 C20 C21 -115.42(17) . .
C19 N3 C20 C21 91.61(19) . .
C17 N3 C20 C1 65.8(2) . 3_666
C19 N3 C20 C1 -87.2(2) . 3_666
C1 C20 C21 C4 0.7(2) 3_666 3_666
N3 C20 C21 C4 -178.06(14) . 3_666
