#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023996.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_4023996
loop_
_publ_author_name
'Bao-Yong Hou'
'De-Xian Wang'
'Hai-Bo Yang'
'Qi-Yu Zheng'
'Mei-Xiang Wang'
_publ_section_title
;
 Synthesis and Structure of Upper-Rim
 1,3-Alternate Tetraoxacalix[2]arene[2]triazine Azacrowns
 and Change of Cavity in Response to Fluoride Anion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5218
_journal_page_last               5226
_journal_paper_doi               10.1021/jo0706168
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C48 H50 N8 O14'
_chemical_formula_weight         962.96
_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                 119.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.154(5)
_cell_length_b                   13.507(3)
_cell_length_c                   18.307(4)
_cell_measurement_reflns_used    5958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.79
_cell_volume                     5206.0(18)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1402
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5958
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.417
_refine_diff_density_min         -1.878
_refine_diff_density_rms         0.382
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.471
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5958
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.487
_refine_ls_R_factor_all          0.4487
_refine_ls_R_factor_gt           0.2236
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2750P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5351
_refine_ls_wR_factor_ref         0.6645
_reflns_number_gt                1548
_reflns_number_total             5958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0706168si20070324_094451.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4023996
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
O1 O 0.1116(3) 0.4247(8) 0.1902(5) 0.107(3) Uani 1 1 d . . .
O1W O 0.0000 0.149(6) 0.2500 0.52(4) Uiso 1 2 d S . .
O2 O 0.1156(3) 0.3947(8) 0.4421(5) 0.104(3) Uani 1 1 d . . .
O3 O 0.0268(5) 0.7393(8) 0.0309(8) 0.141(4) Uani 1 1 d D . .
O4 O -0.0778(6) 0.7208(10) -0.0238(9) 0.169(5) Uani 1 1 d D . .
O5 O 0.2373(17) -0.004(2) 0.318(2) 0.89(6) Uani 0.50 1 d PD A 1
O6 O 0.176(3) -0.145(9) 0.380(4) 1.6(4) Uiso 1 1 d D . .
O7 O 0.080(2) -0.283(4) 0.287(4) 0.62(4) Uiso 1 1 d D . .
N1 N 0.1065(4) 0.4122(8) 0.3125(6) 0.080(3) Uani 1 1 d . . .
N2 N 0.1843(4) 0.3316(8) 0.2907(6) 0.090(3) Uani 1 1 d . . .
N3 N 0.1874(4) 0.3203(7) 0.4217(5) 0.081(3) Uani 1 1 d . . .
N4 N 0.2599(4) 0.2402(9) 0.3983(6) 0.097(3) Uani 1 1 d . . .
H4A H 0.2794 0.2297 0.4515 0.117 Uiso 1 1 calc R . .
C1 C 0.1353(5) 0.3875(11) 0.2701(8) 0.089(4) Uani 1 1 d . . .
C2 C 0.2089(5) 0.2980(9) 0.3679(8) 0.080(3) Uani 1 1 d . . .
C3 C 0.1375(5) 0.3755(9) 0.3887(7) 0.077(3) Uani 1 1 d . . .
C4 C 0.0598(4) 0.4509(10) 0.4162(6) 0.075(3) Uani 1 1 d . . .
C5 C 0.0020(5) 0.4126(9) 0.3652(7) 0.078(3) Uani 1 1 d . . .
H5A H -0.0024 0.3509 0.3404 0.093 Uiso 1 1 calc R . .
C6 C 0.0506(4) 0.4676(11) 0.1492(6) 0.079(3) Uani 1 1 d . . .
C7 C 0.0451(5) 0.5568(10) 0.1137(7) 0.080(3) Uani 1 1 d . . .
H7A H 0.0813 0.5920 0.1240 0.097 Uiso 1 1 calc R . .
C8 C -0.0140(5) 0.5964(9) 0.0621(6) 0.076(3) Uani 1 1 d . . .
C9 C -0.0686(5) 0.5416(12) 0.0468(7) 0.091(4) Uani 1 1 d . . .
H9A H -0.1091 0.5667 0.0127 0.109 Uiso 1 1 calc R . .
C10 C -0.0196(8) 0.6938(11) 0.0210(9) 0.105(4) Uani 1 1 d D . .
C11 C -0.0889(10) 0.8077(19) -0.0767(16) 0.274(15) Uiso 1 1 d D . .
H11A H -0.1010 0.7876 -0.1335 0.329 Uiso 1 1 calc R . .
H11B H -0.0507 0.8476 -0.0552 0.329 Uiso 1 1 calc R . .
C12 C -0.1409(16) 0.865(3) -0.076(2) 0.56(6) Uiso 1 1 d D . .
C13 C -0.201(2) 0.863(10) -0.143(4) 2.0(7) Uiso 1 1 d D . .
H13A H -0.2075 0.8357 -0.1937 2.400 Uiso 1 1 calc R . .
C14 C -0.2497(19) 0.902(12) -0.136(5) 2.0(8) Uiso 1 1 d D . .
H14A H -0.2906 0.9006 -0.1819 2.400 Uiso 1 1 calc R . .
C15 C -0.239(2) 0.944(4) -0.063(4) 0.38(3) Uiso 1 1 d D . .
H15A H -0.2719 0.9533 -0.0508 0.458 Uiso 1 1 calc R . .
C16 C -0.177(3) 0.970(4) -0.006(4) 0.41(3) Uiso 1 1 d D . .
H16A H -0.1690 1.0201 0.0332 0.487 Uiso 1 1 calc R . .
C17 C -0.129(2) 0.923(9) -0.009(5) 1.03(19) Uiso 1 1 d D . .
H17A H -0.0876 0.9303 0.0347 1.242 Uiso 1 1 calc R . .
C18 C 0.2870(6) 0.1913(15) 0.3482(11) 0.168(9) Uani 1 1 d D A .
H18A H 0.2726 0.2275 0.2962 0.201 Uiso 1 1 calc R . .
H18B H 0.3329 0.1962 0.3795 0.201 Uiso 1 1 calc R . .
C19 C 0.2690(10) 0.0846(16) 0.3278(16) 0.29(2) Uani 1 1 d D . .
H19A H 0.2635 0.0866 0.2717 0.347 Uiso 1 1 calc R A 1
H19B H 0.3115 0.0581 0.3612 0.347 Uiso 1 1 calc R A 1
C20 C 0.2173(8) -0.0948(11) 0.2803(11) 1.65(3) Uani 1 1 d D A 1
H20A H 0.2529 -0.1266 0.2790 1.985 Uiso 1 1 calc R A 1
H20B H 0.1847 -0.0841 0.2226 1.985 Uiso 1 1 calc R A 1
C21 C 0.1926(19) -0.163(2) 0.319(3) 0.39(3) Uiso 1 1 d D . .
H21A H 0.1546 -0.1904 0.2723 0.473 Uiso 1 1 calc R A 1
H21B H 0.2232 -0.2162 0.3404 0.473 Uiso 1 1 calc R A 1
C22 C 0.111(3) -0.153(5) 0.339(5) 2.0(6) Uiso 1 1 d D . .
H22A H 0.0963 -0.0876 0.3420 2.400 Uiso 1 1 calc R A .
H22B H 0.1022 -0.1946 0.3751 2.400 Uiso 1 1 calc R . .
C23 C 0.067(3) -0.187(6) 0.255(4) 0.58(6) Uiso 1 1 d D A .
H23A H 0.0236 -0.1666 0.2349 0.694 Uiso 1 1 calc R . .
H23B H 0.0806 -0.1728 0.2140 0.694 Uiso 1 1 calc R . .
C24 C 0.023(3) -0.312(4) 0.277(4) 0.51(5) Uiso 1 1 d D . .
H24A H 0.0297 -0.3800 0.2966 0.607 Uiso 1 1 calc R . .
H24B H 0.0182 -0.2742 0.3184 0.607 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
C1 O1 C6 119.7(8) . . ?
C3 O2 C4 120.7(9) . . ?
C10 O4 C11 116.1(14) . . ?
C20 O5 C19 150(2) . . ?
C21 O6 C22 104.2(19) . . ?
C24 O7 C23 101.7(19) . . ?
C1 N1 C3 109.9(9) . . ?
C1 N2 C2 112.4(10) . . ?
C3 N3 C2 113.1(10) . . ?
C2 N4 C18 126.1(11) . . ?
N2 C1 N1 130.5(12) . . ?
N2 C1 O1 111.4(10) . . ?
N1 C1 O1 118.1(10) . . ?
N2 C2 N4 119.3(10) . . ?
N2 C2 N3 124.9(10) . . ?
N4 C2 N3 115.8(11) . . ?
N3 C3 N1 129.2(10) . . ?
N3 C3 O2 112.4(10) . . ?
N1 C3 O2 118.5(10) . . ?
C5 C4 C9 123.0(11) . 2 ?
C5 C4 O2 121.5(12) . . ?
C9 C4 O2 115.2(10) 2 . ?
C4 C5 C6 118.1(12) . 2 ?
C7 C6 C5 121.7(10) . 2 ?
C7 C6 O1 117.2(10) . . ?
C5 C6 O1 120.3(12) 2 . ?
C6 C7 C8 120.3(10) . . ?
C7 C8 C9 119.0(11) . . ?
C7 C8 C10 119.8(11) . . ?
C9 C8 C10 121.2(11) . . ?
C4 C9 C8 117.9(10) 2 . ?
O3 C10 O4 126.4(14) . . ?
O3 C10 C8 121.6(12) . . ?
O4 C10 C8 111.9(14) . . ?
O4 C11 C12 106.8(16) . . ?
C17 C12 C13 119.3(14) . . ?
C17 C12 C11 120.4(16) . . ?
C13 C12 C11 120.1(15) . . ?
C14 C13 C12 119.3(16) . . ?
C13 C14 C15 120.0(14) . . ?
C14 C15 C16 117(2) . . ?
C17 C16 C15 119(2) . . ?
C16 C17 C12 120.1(9) . . ?
C19 C18 N4 114.4(13) . . ?
O5 C19 C18 159.4(19) . . ?
O5 C20 C21 116.2(18) . . ?
O6 C21 C20 130(5) . . ?
O6 C22 C23 131(3) . . ?
O7 C23 C22 87.3(13) . . ?
C24 C24 O7 131(9) 2 . ?
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 C1 1.378(14) . ?
O1 C6 1.409(12) . ?
O2 C3 1.346(12) . ?
O2 C4 1.412(12) . ?
O3 C10 1.211(16) . ?
O4 C10 1.285(16) . ?
O4 C11 1.460(16) . ?
O5 C20 1.381(17) . ?
O5 C19 1.381(18) . ?
O6 C21 1.38(2) . ?
O6 C22 1.378(19) . ?
O7 C24 1.37(2) . ?
O7 C23 1.39(2) . ?
N1 C1 1.314(14) . ?
N1 C3 1.315(13) . ?
N2 C1 1.294(14) . ?
N2 C2 1.318(14) . ?
N3 C3 1.287(13) . ?
N3 C2 1.352(13) . ?
N4 C2 1.328(13) . ?
N4 C18 1.515(18) . ?
C4 C5 1.345(15) . ?
C4 C9 1.366(18) 2 ?
C5 C6 1.381(15) 2 ?
C6 C7 1.345(16) . ?
C6 C5 1.381(15) 2 ?
C7 C8 1.375(14) . ?
C8 C9 1.415(16) . ?
C8 C10 1.488(18) . ?
C9 C4 1.366(17) 2 ?
C11 C12 1.484(12) . ?
C12 C17 1.358(16) . ?
C12 C13 1.365(17) . ?
C13 C14 1.360(16) . ?
C14 C15 1.364(19) . ?
C15 C16 1.385(19) . ?
C16 C17 1.352(17) . ?
C18 C19 1.498(17) . ?
C20 C21 1.451(18) . ?
C22 C23 1.45(2) . ?
C24 C24 1.06(12) 2 ?
