#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/63/1506308.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_1506308
loop_
_publ_author_name
'Wang, Qi-Qiang'
'Wang, De-Xian'
'Ma, Hong-Wei'
'Wang, Mei-Xiang'
_publ_section_title
;
 Synthesis of tetraazacalix[2]arene[2]triazines: tuning the cavity by the
 substituents on the bridging nitrogen atoms.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              5967
_journal_page_last               5970
_journal_paper_doi               10.1021/ol062441e
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C51 H50 Cl2 N12 O4'
_chemical_formula_weight         965.93
_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                 110.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.598(5)
_cell_length_b                   9.4281(19)
_cell_length_c                   20.033(4)
_cell_measurement_reflns_used    10211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      1.63
_cell_volume                     4714.4(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10211
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9302
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.0085(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0588
_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)+(0.0857P)²+4.2112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1714
_reflns_number_gt                4163
_reflns_number_total             5352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062441esi20061004_092749.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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        4714.4(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506308
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
Cl1 Cl -0.00108(4) 0.04073(9) -0.17827(4) 0.0865(3) Uani 1 1 d .
O1 O -0.16359(7) 0.2829(2) -0.20898(9) 0.0661(6) Uani 1 1 d .
O2 O -0.26699(10) -0.1132(2) 0.04823(11) 0.0843(7) Uani 1 1 d .
N1 N 0.13079(7) 0.1176(2) 0.05757(9) 0.0462(5) Uani 1 1 d .
N2 N 0.05414(7) 0.2269(2) 0.05920(8) 0.0372(4) Uani 1 1 d .
N3 N 0.12969(7) 0.1923(2) 0.16649(9) 0.0392(4) Uani 1 1 d .
N4 N 0.05080(7) 0.3051(2) 0.17069(9) 0.0369(4) Uani 1 1 d .
N5 N -0.02076(6) 0.34105(19) 0.06896(8) 0.0358(4) Uani 1 1 d .
N6 N -0.12343(7) 0.2728(2) 0.22656(9) 0.0396(4) Uani 1 1 d .
C1 C 0.10656(11) 0.1011(3) -0.01921(12) 0.0553(6) Uani 1 1 d .
H1A H 0.0717 0.1444 -0.0353 0.083 Uiso 1 1 calc R
H1B H 0.1032 0.0020 -0.0310 0.083 Uiso 1 1 calc R
H1C H 0.1288 0.1461 -0.0419 0.083 Uiso 1 1 calc R
C2 C 0.18388(10) 0.0584(4) 0.09154(15) 0.0624(8) Uani 1 1 d .
H2B H 0.1954 0.0758 0.1418 0.094 Uiso 1 1 calc R
H2C H 0.2085 0.1023 0.0723 0.094 Uiso 1 1 calc R
H2D H 0.1829 -0.0419 0.0830 0.094 Uiso 1 1 calc R
C3 C 0.10403(8) 0.1805(2) 0.09556(11) 0.0365(4) Uani 1 1 d .
C4 C 0.10034(8) 0.2556(2) 0.19989(10) 0.0349(4) Uani 1 1 d .
C5 C 0.03021(8) 0.2887(2) 0.09984(10) 0.0333(4) Uani 1 1 d .
C6 C -0.05330(8) 0.3286(2) -0.00469(10) 0.0337(4) Uani 1 1 d .
C7 C -0.08619(9) 0.4407(2) -0.03630(11) 0.0433(5) Uani 1 1 d .
H7A H -0.0833 0.5253 -0.0113 0.052 Uiso 1 1 calc R
C8 C -0.12352(10) 0.4303(3) -0.10441(12) 0.0479(5) Uani 1 1 d .
H8A H -0.1457 0.5068 -0.1246 0.057 Uiso 1 1 calc R
C9 C -0.12757(9) 0.3061(3) -0.14195(11) 0.0452(5) Uani 1 1 d .
C10 C -0.09333(10) 0.1950(3) -0.11169(12) 0.0506(6) Uani 1 1 d .
H10A H -0.0950 0.1123 -0.1377 0.061 Uiso 1 1 calc R
C11 C -0.05667(9) 0.2050(2) -0.04354(12) 0.0452(5) Uani 1 1 d .
H11A H -0.0342 0.1290 -0.0237 0.054 Uiso 1 1 calc R
C12 C -0.20763(11) 0.3780(5) -0.23482(15) 0.0877(12) Uani 1 1 d .
H12A H -0.2297 0.3502 -0.2819 0.132 Uiso 1 1 calc R
H12B H -0.1945 0.4725 -0.2360 0.132 Uiso 1 1 calc R
H12C H -0.2283 0.3755 -0.2040 0.132 Uiso 1 1 calc R
C13 C -0.07595(7) 0.3142(2) 0.14269(10) 0.0329(4) Uani 1 1 d .
H13A H -0.0819 0.2204 0.1278 0.040 Uiso 1 1 calc R
C14 C -0.04610(7) 0.4023(2) 0.11563(10) 0.0330(4) Uani 1 1 d .
C15 C -0.03900(9) 0.5437(2) 0.13439(11) 0.0407(5) Uani 1 1 d .
H15A H -0.0188 0.6023 0.1160 0.049 Uiso 1 1 calc R
C16 C -0.06253(10) 0.5965(2) 0.18105(12) 0.0451(5) Uani 1 1 d .
H16A H -0.0591 0.6923 0.1929 0.054 Uiso 1 1 calc R
C17 C -0.09109(9) 0.5089(2) 0.21021(12) 0.0416(5) Uani 1 1 d .
H17A H -0.1063 0.5455 0.2419 0.050 Uiso 1 1 calc R
C18 C -0.09705(8) 0.3665(2) 0.19222(10) 0.0346(4) Uani 1 1 d .
C19 C -0.16236(8) 0.1756(2) 0.18338(10) 0.0376(5) Uani 1 1 d .
C20 C -0.20393(9) 0.2247(3) 0.12532(13) 0.0492(6) Uani 1 1 d .
H20A H -0.2081 0.3218 0.1171 0.059 Uiso 1 1 calc R
C21 C -0.23977(10) 0.1315(3) 0.07874(13) 0.0553(6) Uani 1 1 d .
H21A H -0.2675 0.1664 0.0397 0.066 Uiso 1 1 calc R
C22 C -0.23416(11) -0.0119(3) 0.09062(13) 0.0545(6) Uani 1 1 d .
C23 C -0.19340(12) -0.0615(3) 0.14937(13) 0.0604(7) Uani 1 1 d .
H23A H -0.1898 -0.1585 0.1582 0.073 Uiso 1 1 calc R
C24 C -0.15793(11) 0.0310(3) 0.19512(12) 0.0516(6) Uani 1 1 d .
H24A H -0.1306 -0.0043 0.2345 0.062 Uiso 1 1 calc R
C25 C -0.30360(12) -0.0721(4) -0.01825(16) 0.0749(9) Uani 1 1 d .
H25A H -0.3238 -0.1532 -0.0419 0.112 Uiso 1 1 calc R
H25B H -0.2845 -0.0331 -0.0468 0.112 Uiso 1 1 calc R
H25C H -0.3275 -0.0018 -0.0115 0.112 Uiso 1 1 calc R
C26 C 0.0000 -0.0538(6) -0.2500 0.0865(18) Uani 1 2 d S
H26A H -0.011(3) -0.138(6) -0.254(5) 0.07(2) Uiso 0.50 1 d P
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'
Cl Cl 0.1484 0.1585 '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
C9 O1 C12 117.7(2) . .
C22 O2 C25 118.6(2) . .
C3 N1 C2 121.55(18) . .
C3 N1 C1 121.11(19) . .
C2 N1 C1 117.30(19) . .
C5 N2 C3 113.70(17) . .
C4 N3 C3 113.22(17) . .
C4 N4 C5 113.93(17) . .
C5 N5 C6 125.80(17) . .
C5 N5 C14 117.38(15) . .
C6 N5 C14 116.53(15) . .
C4 N6 C19 121.80(17) 2 .
C4 N6 C18 117.75(16) 2 .
C19 N6 C18 118.31(16) . .
N1 C3 N2 116.86(18) . .
N1 C3 N3 117.20(18) . .
N2 C3 N3 125.94(19) . .
N4 C4 N3 126.92(18) . .
N4 C4 N6 115.58(17) . 2
N3 C4 N6 117.50(17) . 2
N2 C5 N4 126.28(18) . .
N2 C5 N5 119.28(17) . .
N4 C5 N5 114.43(17) . .
C7 C6 C11 118.61(19) . .
C7 C6 N5 118.11(19) . .
C11 C6 N5 123.04(19) . .
C6 C7 C8 121.5(2) . .
C9 C8 C7 119.5(2) . .
O1 C9 C8 124.6(2) . .
O1 C9 C10 116.1(2) . .
C8 C9 C10 119.3(2) . .
C11 C10 C9 121.0(2) . .
C10 C11 C6 120.0(2) . .
C14 C13 C18 119.73(19) . .
C15 C14 C13 121.11(18) . .
C15 C14 N5 120.70(18) . .
C13 C14 N5 118.15(19) . .
C14 C15 C16 118.7(2) . .
C17 C16 C15 120.9(2) . .
C16 C17 C18 120.0(2) . .
C17 C18 C13 119.45(19) . .
C17 C18 N6 120.03(18) . .
C13 C18 N6 120.49(19) . .
C20 C19 C24 118.1(2) . .
C20 C19 N6 119.8(2) . .
C24 C19 N6 121.90(19) . .
C19 C20 C21 121.2(2) . .
C22 C21 C20 119.8(2) . .
O2 C22 C21 124.8(2) . .
O2 C22 C23 115.9(3) . .
C21 C22 C23 119.3(2) . .
C24 C23 C22 120.7(3) . .
C23 C24 C19 120.9(2) . .
Cl1 C26 Cl1 116.7(3) 2_554 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C26 1.700(3) .
O1 C9 1.371(3) .
O1 C12 1.423(4) .
O2 C22 1.372(3) .
O2 C25 1.406(4) .
N1 C3 1.346(3) .
N1 C2 1.451(3) .
N1 C1 1.456(3) .
N2 C5 1.329(2) .
N2 C3 1.347(3) .
N3 C4 1.332(3) .
N3 C3 1.352(3) .
N4 C4 1.328(3) .
N4 C5 1.342(2) .
N5 C5 1.373(3) .
N5 C6 1.434(2) .
N5 C14 1.448(2) .
N6 C4 1.396(2) 2
N6 C19 1.429(3) .
N6 C18 1.442(3) .
C4 N6 1.396(2) 2
C6 C7 1.379(3) .
C6 C11 1.386(3) .
C7 C8 1.386(3) .
C8 C9 1.376(3) .
C9 C10 1.383(3) .
C10 C11 1.380(3) .
C13 C14 1.382(3) .
C13 C18 1.388(3) .
C14 C15 1.380(3) .
C15 C16 1.385(3) .
C16 C17 1.381(3) .
C17 C18 1.385(3) .
C19 C20 1.379(3) .
C19 C24 1.381(3) .
C20 C21 1.392(3) .
C21 C22 1.372(4) .
C22 C23 1.378(4) .
C23 C24 1.376(4) .
C26 Cl1 1.700(3) 2_554
