#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025464.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_4025464
loop_
_publ_author_name
'Yin Chen'
'De-Xian Wang'
'Zhi-Tang Huang'
'Mei-Xiang Wang'
_publ_section_title
;
 Synthesis, Structure, and Functionalization of Homo
 Heterocalix[2]arene[2]triazines: Versatile Conformation and Cavity
 Structures Regulated by the Bridging Elements
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3786
_journal_page_last               3796
_journal_paper_doi               10.1021/jo100571c
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C34 H44 N8 O4'
_chemical_formula_weight         628.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                117.05(3)
_cell_angle_beta                 94.98(3)
_cell_angle_gamma                99.20(3)
_cell_formula_units_Z            1
_cell_length_a                   8.0502(16)
_cell_length_b                   10.501(2)
_cell_length_c                   11.409(2)
_cell_measurement_reflns_used    5131
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.04
_cell_volume                     833.8(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5131
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0856
_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)+(0.1262P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2196
_refine_ls_wR_factor_ref         0.2388
_reflns_number_gt                2357
_reflns_number_total             2938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100571c_si_001_02.cif
_cod_data_source_block           22O22O
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        833.8(3)
_cod_database_code               4025464
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9368(2) 0.4361(2) 1.3197(2) 0.0375(6) Uani 1 1 d . . .
O2 O 0.4682(2) 0.2193(2) 0.99206(19) 0.0299(5) Uani 1 1 d . . .
N1 N 0.7227(3) 0.5499(2) 1.3442(2) 0.0298(6) Uani 1 1 d . . .
N2 N 0.4718(3) 0.4386(2) 1.1738(2) 0.0276(6) Uani 1 1 d . . .
N3 N 0.7054(3) 0.3224(2) 1.1479(2) 0.0301(6) Uani 1 1 d . . .
N4 N 0.4911(3) 0.6571(2) 1.3648(2) 0.0289(6) Uani 1 1 d . . .
C1 C 1.0041(4) 0.3080(3) 1.2476(4) 0.0394(8) Uani 1 1 d . . .
H1B H 1.1295 0.3331 1.2783 0.047 Uiso 1 1 calc R . .
H1C H 0.9829 0.2788 1.1510 0.047 Uiso 1 1 calc R . .
C2 C 0.7818(3) 0.4350(3) 1.2674(3) 0.0288(7) Uani 1 1 d . . .
C3 C 0.5655(3) 0.5467(3) 1.2931(3) 0.0260(6) Uani 1 1 d . . .
C4 C 0.5776(4) 0.7779(3) 1.4963(3) 0.0299(7) Uani 1 1 d . . .
H4A H 0.5404 0.8681 1.5093 0.036 Uiso 1 1 calc R . .
H4B H 0.7025 0.7956 1.4979 0.036 Uiso 1 1 calc R . .
C5 C 0.5423(4) 0.7493(3) 1.6114(3) 0.0359(7) Uani 1 1 d . . .
H5A H 0.5896 0.6651 1.6041 0.043 Uiso 1 1 calc R . .
H5B H 0.4171 0.7234 1.6062 0.043 Uiso 1 1 calc R . .
C6 C 0.6221(4) 0.8838(3) 1.7459(3) 0.0406(8) Uani 1 1 d . . .
H6A H 0.5960 0.8628 1.8185 0.061 Uiso 1 1 calc R . .
H6B H 0.5751 0.9671 1.7532 0.061 Uiso 1 1 calc R . .
H6C H 0.7464 0.9078 1.7522 0.061 Uiso 1 1 calc R . .
C7 C 0.3157(4) 0.6526(3) 1.3160(3) 0.0325(7) Uani 1 1 d . . .
H7A H 0.2616 0.7058 1.3936 0.039 Uiso 1 1 calc R . .
H7B H 0.2507 0.5492 1.2678 0.039 Uiso 1 1 calc R . .
C8 C 0.3034(5) 0.7188(4) 1.2244(4) 0.0541(10) Uani 1 1 d . . .
H8A H 0.3597 0.6672 1.1478 0.065 Uiso 1 1 calc R . .
H8B H 0.3655 0.8230 1.2732 0.065 Uiso 1 1 calc R . .
C9 C 0.1213(5) 0.7097(5) 1.1725(4) 0.0655(12) Uani 1 1 d . . .
H9A H 0.1197 0.7525 1.1120 0.098 Uiso 1 1 calc R . .
H9B H 0.0662 0.7640 1.2478 0.098 Uiso 1 1 calc R . .
H9C H 0.0592 0.6067 1.1239 0.098 Uiso 1 1 calc R . .
C10 C 0.5506(3) 0.3337(3) 1.1100(3) 0.0258(6) Uani 1 1 d . . .
C11 C 0.2976(4) 0.2230(3) 0.9455(3) 0.0325(7) Uani 1 1 d . . .
H11A H 0.3020 0.3020 0.9204 0.039 Uiso 1 1 calc R . .
H11B H 0.2288 0.2425 1.0172 0.039 Uiso 1 1 calc R . .
C12 C 0.2181(4) 0.0766(3) 0.8261(3) 0.0284(7) Uani 1 1 d . . .
C13 C 0.1545(3) -0.0448(3) 0.8424(3) 0.0289(7) Uani 1 1 d . . .
H13A H 0.1658 -0.0352 0.9299 0.035 Uiso 1 1 calc R . .
C14 C 0.0749(3) -0.1796(3) 0.7334(3) 0.0306(7) Uani 1 1 d . . .
C15 C 0.0611(4) -0.1928(3) 0.6050(3) 0.0373(8) Uani 1 1 d . . .
H15A H 0.0073 -0.2842 0.5292 0.045 Uiso 1 1 calc R . .
C16 C 0.1261(4) -0.0724(3) 0.5880(3) 0.0375(8) Uani 1 1 d . . .
H16A H 0.1171 -0.0822 0.5005 0.045 Uiso 1 1 calc R . .
C17 C 0.2035(4) 0.0611(3) 0.6975(3) 0.0330(7) Uani 1 1 d . . .
H17A H 0.2469 0.1428 0.6850 0.040 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
_geom_angle_publ_flag
C2 O1 C1 116.8(2) . . ?
C10 O2 C11 116.4(2) . . ?
C2 N1 C3 113.4(2) . . ?
C10 N2 C3 113.6(2) . . ?
C10 N3 C2 111.9(2) . . ?
C3 N4 C7 119.8(2) . . ?
C3 N4 C4 121.7(2) . . ?
C7 N4 C4 118.4(2) . . ?
O1 C1 C14 112.7(3) . 2_657 ?
O1 C1 H1B 109.0 . . ?
C14 C1 H1B 109.0 2_657 . ?
O1 C1 H1C 109.0 . . ?
C14 C1 H1C 109.0 2_657 . ?
H1B C1 H1C 107.8 . . ?
N1 C2 O1 113.5(3) . . ?
N1 C2 N3 128.1(3) . . ?
O1 C2 N3 118.5(3) . . ?
N1 C3 N4 118.3(3) . . ?
N1 C3 N2 125.0(3) . . ?
N4 C3 N2 116.7(3) . . ?
N4 C4 C5 113.6(2) . . ?
N4 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N4 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C5 C6 111.2(2) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 113.3(3) . . ?
N4 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
N4 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 112.5(3) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 N3 128.1(3) . . ?
N2 C10 O2 118.7(2) . . ?
N3 C10 O2 113.3(2) . . ?
O2 C11 C12 108.0(2) . . ?
O2 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O2 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 C11 120.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 C1 121.0(3) . 2_657 ?
C15 C14 C1 120.1(3) . 2_657 ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C12 C17 H17A 119.8 . . ?
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
O1 C2 1.331(3) . ?
O1 C1 1.444(4) . ?
O2 C10 1.347(3) . ?
O2 C11 1.441(3) . ?
N1 C2 1.320(4) . ?
N1 C3 1.335(4) . ?
N2 C10 1.311(4) . ?
N2 C3 1.361(4) . ?
N3 C10 1.324(4) . ?
N3 C2 1.339(4) . ?
N4 C3 1.347(4) . ?
N4 C7 1.457(4) . ?
N4 C4 1.466(4) . ?
C1 C14 1.511(4) 2_657 ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.501(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.504(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.503(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.392(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.390(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.400(4) . ?
C14 C1 1.511(4) 2_657 ?
C15 C16 1.393(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.381(4) . ?
C16 H16A 0.9500 . ?
C17 H17A 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 O1 C1 C14 -76.5(3) . . . 2_657 ?
C3 N1 C2 O1 -178.4(2) . . . . ?
C3 N1 C2 N3 1.5(4) . . . . ?
C1 O1 C2 N1 174.6(2) . . . . ?
C1 O1 C2 N3 -5.3(4) . . . . ?
C10 N3 C2 N1 -1.6(4) . . . . ?
C10 N3 C2 O1 178.3(2) . . . . ?
C2 N1 C3 N4 178.5(2) . . . . ?
C2 N1 C3 N2 -0.6(4) . . . . ?
C7 N4 C3 N1 -176.2(2) . . . . ?
C4 N4 C3 N1 -0.7(4) . . . . ?
C7 N4 C3 N2 3.0(4) . . . . ?
C4 N4 C3 N2 178.5(2) . . . . ?
C10 N2 C3 N1 0.0(4) . . . . ?
C10 N2 C3 N4 -179.2(2) . . . . ?
C3 N4 C4 C5 -89.9(3) . . . . ?
C7 N4 C4 C5 85.6(3) . . . . ?
N4 C4 C5 C6 -174.8(2) . . . . ?
C3 N4 C7 C8 -88.0(3) . . . . ?
C4 N4 C7 C8 96.3(3) . . . . ?
N4 C7 C8 C9 178.6(3) . . . . ?
C3 N2 C10 N3 -0.1(4) . . . . ?
C3 N2 C10 O2 178.5(2) . . . . ?
C2 N3 C10 N2 0.8(4) . . . . ?
C2 N3 C10 O2 -177.9(2) . . . . ?
C11 O2 C10 N2 0.2(4) . . . . ?
C11 O2 C10 N3 179.0(2) . . . . ?
C10 O2 C11 C12 -170.9(2) . . . . ?
O2 C11 C12 C17 -103.8(3) . . . . ?
O2 C11 C12 C13 77.7(3) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
C11 C12 C13 C14 177.6(3) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C12 C13 C14 C1 -175.9(3) . . . 2_657 ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C1 C14 C15 C16 176.6(3) 2_657 . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C16 C17 C12 0.3(4) . . . . ?
C13 C12 C17 C16 0.4(4) . . . . ?
C11 C12 C17 C16 -178.2(3) . . . . ?
