#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025471.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_4025471
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            'C58 H64 N12'
_chemical_formula_weight         929.21
_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                115.77(3)
_cell_angle_beta                 98.47(3)
_cell_angle_gamma                103.57(3)
_cell_formula_units_Z            1
_cell_length_a                   10.748(2)
_cell_length_b                   11.622(2)
_cell_length_c                   12.647(3)
_cell_measurement_reflns_used    11138
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.03
_cell_volume                     1325.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11138
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         6061
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.277
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.0991
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2518
_reflns_number_gt                3521
_reflns_number_total             6061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100571c_si_001_09.cif
_cod_data_source_block           22NNB22NNB
_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        1325.7(5)
_cod_database_code               4025471
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
N1 N -0.0779(2) 0.2633(2) 0.8063(2) 0.0537(6) Uani 1 1 d U . .
N2 N 0.0105(2) 0.2449(2) 0.9816(2) 0.0622(7) Uani 1 1 d U . .
N3 N 0.1576(2) 0.3443(2) 0.8959(2) 0.0605(7) Uani 1 1 d U . .
N4 N 0.0692(2) 0.3581(2) 0.7281(2) 0.0549(6) Uani 1 1 d U . .
N5 N -0.2153(2) 0.1668(2) 0.8898(2) 0.0589(7) Uani 1 1 d U . .
N11 N 0.2398(3) 0.3206(3) 1.0610(3) 0.0817(9) Uani 1 1 d U . .
C1 C -0.0892(3) 0.2278(3) 0.8928(3) 0.0544(7) Uani 1 1 d U . .
C2 C 0.1314(3) 0.3031(3) 0.9768(3) 0.0616(8) Uani 1 1 d U . .
C3 C 0.0487(3) 0.3209(3) 0.8134(2) 0.0518(7) Uani 1 1 d U . .
C4 C -0.0398(3) 0.3489(3) 0.6386(3) 0.0599(8) Uani 1 1 d U . .
H4A H -0.0205 0.4346 0.6385 0.072 Uiso 1 1 calc R . .
H4B H -0.1208 0.3341 0.6633 0.072 Uiso 1 1 calc R . .
C5 C -0.0641(3) 0.2360(3) 0.5096(3) 0.0579(8) Uani 1 1 d U . .
C6 C -0.1069(4) 0.1024(4) 0.4820(3) 0.0912(12) Uani 1 1 d U . .
H6B H -0.1225 0.0807 0.5425 0.109 Uiso 1 1 calc R . .
C7 C -0.1265(5) 0.0013(4) 0.3660(4) 0.1143(16) Uani 1 1 d U . .
H7B H -0.1556 -0.0886 0.3486 0.137 Uiso 1 1 calc R . .
C8 C -0.1045(4) 0.0298(5) 0.2764(4) 0.1082(15) Uani 1 1 d U . .
H8B H -0.1164 -0.0398 0.1984 0.130 Uiso 1 1 calc R . .
C9 C -0.0652(4) 0.1594(6) 0.3009(4) 0.1028(13) Uani 1 1 d U . .
H9A H -0.0527 0.1795 0.2387 0.123 Uiso 1 1 calc R . .
C10 C -0.0431(4) 0.2640(4) 0.4185(3) 0.0816(10) Uani 1 1 d U . .
H10A H -0.0138 0.3536 0.4349 0.098 Uiso 1 1 calc R . .
C11 C 0.2019(3) 0.4090(3) 0.7191(3) 0.0647(8) Uani 1 1 d U . .
H11A H 0.2008 0.3638 0.6338 0.078 Uiso 1 1 calc R . .
H11B H 0.2634 0.3854 0.7637 0.078 Uiso 1 1 calc R . .
C12 C 0.2245(3) 0.6491(3) 0.8691(2) 0.0545(7) Uani 1 1 d U . .
H12A H 0.1691 0.6142 0.9058 0.065 Uiso 1 1 calc R . .
C13 C 0.2533(3) 0.5607(3) 0.7682(2) 0.0539(7) Uani 1 1 d U . .
C14 C 0.3350(3) 0.6151(4) 0.7141(3) 0.0704(9) Uani 1 1 d U . .
H14A H 0.3543 0.5574 0.6450 0.084 Uiso 1 1 calc R . .
C15 C 0.3875(3) 0.7521(4) 0.7613(3) 0.0817(11) Uani 1 1 d U . .
H15A H 0.4434 0.7871 0.7251 0.098 Uiso 1 1 calc R . .
C16 C 0.3581(3) 0.8381(3) 0.8615(3) 0.0704(9) Uani 1 1 d U . .
H16A H 0.3939 0.9313 0.8926 0.084 Uiso 1 1 calc R . .
C17 C 0.2757(3) 0.7878(3) 0.9170(2) 0.0545(7) Uani 1 1 d U . .
C18 C -0.2389(3) 0.1170(3) 0.9747(3) 0.0656(8) Uani 1 1 d U . .
H18A H -0.1591 0.1023 1.0050 0.079 Uiso 1 1 calc R . .
H18B H -0.3104 0.0302 0.9310 0.079 Uiso 1 1 calc R . .
C19 C -0.3302(3) 0.1429(3) 0.7982(3) 0.0639(8) Uani 1 1 d U . .
H19A H -0.3084 0.2108 0.7725 0.077 Uiso 1 1 calc R . .
H19B H -0.4027 0.1543 0.8348 0.077 Uiso 1 1 calc R . .
C20 C -0.3773(3) 0.0041(3) 0.6868(3) 0.0578(8) Uani 1 1 d U . .
C21 C -0.5060(3) -0.0505(4) 0.6124(3) 0.0843(11) Uani 1 1 d U . .
H21A H -0.5656 -0.0035 0.6327 0.101 Uiso 1 1 calc R . .
C22 C -0.5477(5) -0.1767(5) 0.5064(4) 0.1149(17) Uani 1 1 d U . .
H22A H -0.6344 -0.2125 0.4554 0.138 Uiso 1 1 calc R . .
C23 C -0.4621(7) -0.2475(5) 0.4775(4) 0.135(2) Uani 1 1 d U . .
H23A H -0.4906 -0.3318 0.4072 0.162 Uiso 1 1 calc R . .
C24 C -0.3359(5) -0.1956(5) 0.5505(4) 0.1244(17) Uani 1 1 d U . .
H24A H -0.2776 -0.2443 0.5304 0.149 Uiso 1 1 calc R . .
C25 C -0.2927(4) -0.0701(4) 0.6554(3) 0.0856(11) Uani 1 1 d U . .
H25A H -0.2056 -0.0355 0.7053 0.103 Uiso 1 1 calc R . .
C51 C 0.2240(4) 0.2755(4) 1.1524(3) 0.0901(11) Uani 1 1 d U . .
H51A H 0.1423 0.1988 1.1192 0.108 Uiso 1 1 calc R . .
H51B H 0.2981 0.2464 1.1702 0.108 Uiso 1 1 calc R . .
C52 C 0.2194(6) 0.3851(5) 1.2653(4) 0.142(2) Uani 1 1 d U . .
H52A H 0.2162 0.3561 1.3256 0.213 Uiso 1 1 calc R . .
H52B H 0.1412 0.4081 1.2491 0.213 Uiso 1 1 calc R . .
H52C H 0.2976 0.4630 1.2954 0.213 Uiso 1 1 calc R . .
C53 C 0.3754(3) 0.3889(5) 1.0653(4) 0.0958(13) Uani 1 1 d U . .
H53A H 0.3741 0.4606 1.0456 0.115 Uiso 1 1 calc R . .
H53B H 0.4334 0.4304 1.1479 0.115 Uiso 1 1 calc R . .
C54 C 0.4293(5) 0.2962(6) 0.9803(6) 0.148(2) Uani 1 1 d U . .
H54A H 0.5201 0.3437 0.9904 0.221 Uiso 1 1 calc R . .
H54B H 0.3769 0.2612 0.8979 0.221 Uiso 1 1 calc R . .
H54C H 0.4266 0.2225 0.9968 0.221 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
C3 N1 C1 113.4(2) . . ?
C1 N2 C2 112.9(3) . . ?
C3 N3 C2 113.7(2) . . ?
C3 N4 C11 122.2(3) . . ?
C3 N4 C4 122.4(2) . . ?
C11 N4 C4 115.4(3) . . ?
C1 N5 C19 121.4(3) . . ?
C1 N5 C18 121.1(3) . . ?
C19 N5 C18 117.4(2) . . ?
C2 N11 C53 120.5(3) . . ?
C2 N11 C51 121.3(3) . . ?
C53 N11 C51 118.2(3) . . ?
N1 C1 N2 127.0(3) . . ?
N1 C1 N5 116.4(3) . . ?
N2 C1 N5 116.6(3) . . ?
N3 C2 N2 126.6(3) . . ?
N3 C2 N11 116.2(3) . . ?
N2 C2 N11 117.3(3) . . ?
N3 C3 N1 126.4(3) . . ?
N3 C3 N4 116.3(2) . . ?
N1 C3 N4 117.2(3) . . ?
N4 C4 C5 113.5(2) . . ?
N4 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N4 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C10 C5 C6 118.2(3) . . ?
C10 C5 C4 121.1(3) . . ?
C6 C5 C4 120.6(3) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6B 119.8 . . ?
C5 C6 H6B 119.8 . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7B 119.4 . . ?
C6 C7 H7B 119.4 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8B 120.3 . . ?
C7 C8 H8B 120.3 . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C9 120.4(4) . . ?
C5 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
N4 C11 C13 114.2(2) . . ?
N4 C11 H11A 108.7 . . ?
C13 C11 H11A 108.7 . . ?
N4 C11 H11B 108.7 . . ?
C13 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C13 121.7(3) . . ?
C17 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C12 C13 C14 118.1(3) . . ?
C12 C13 C11 121.6(2) . . ?
C14 C13 C11 120.2(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C12 C17 C16 118.5(3) . . ?
C12 C17 C18 120.9(2) . 2_567 ?
C16 C17 C18 120.6(3) . 2_567 ?
N5 C18 C17 113.7(3) . 2_567 ?
N5 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 2_567 . ?
N5 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 2_567 . ?
H18A C18 H18B 107.7 . . ?
N5 C19 C20 113.8(3) . . ?
N5 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N5 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C25 118.3(3) . . ?
C21 C20 C19 120.3(3) . . ?
C25 C20 C19 121.4(3) . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23A 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C23 C24 C25 120.3(5) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C20 C25 C24 120.9(4) . . ?
C20 C25 H25A 119.6 . . ?
C24 C25 H25A 119.6 . . ?
C52 C51 N11 110.8(4) . . ?
C52 C51 H51A 109.5 . . ?
N11 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
N11 C51 H51B 109.5 . . ?
H51A C51 H51B 108.1 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C53 N11 112.4(4) . . ?
C54 C53 H53A 109.1 . . ?
N11 C53 H53A 109.1 . . ?
C54 C53 H53B 109.1 . . ?
N11 C53 H53B 109.1 . . ?
H53A C53 H53B 107.9 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 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 C3 1.339(3) . ?
N1 C1 1.339(4) . ?
N2 C1 1.341(4) . ?
N2 C2 1.340(4) . ?
N3 C3 1.333(4) . ?
N3 C2 1.343(4) . ?
N4 C3 1.353(4) . ?
N4 C11 1.451(3) . ?
N4 C4 1.452(4) . ?
N5 C1 1.360(3) . ?
N5 C19 1.442(4) . ?
N5 C18 1.451(4) . ?
N11 C2 1.366(4) . ?
N11 C53 1.468(4) . ?
N11 C51 1.477(5) . ?
C4 C5 1.518(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.361(4) . ?
C5 C6 1.375(5) . ?
C6 C7 1.368(5) . ?
C6 H6B 0.9300 . ?
C7 C8 1.348(7) . ?
C7 H7B 0.9300 . ?
C8 C9 1.343(6) . ?
C8 H8B 0.9300 . ?
C9 C10 1.391(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C13 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.380(4) . ?
C12 C13 1.380(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(4) . ?
C14 C15 1.365(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.367(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.518(4) 2_567 ?
C18 C17 1.518(4) 2_567 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.509(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.374(4) . ?
C20 C25 1.379(5) . ?
C21 C22 1.398(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.360(7) . ?
C22 H22A 0.9300 . ?
C23 C24 1.349(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.386(5) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C51 C52 1.460(6) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.457(7) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
