#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/40/1514023.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_1514023
loop_
_publ_author_name
'Ya-Jiun Shiao'
'Pei-Chen Chiang'
'Annamalai Senthilvelan'
'Ming-Tsung Tsai'
'Gene-Hsiang Lee'
'Wen-Sheng Chung'
_publ_section_title
;
 Capping the upper and lower rims of calix[4]arenes by aryl dinitrile
 oxide reactions
;
_journal_issue                   47
_journal_name_full               'Tetrahedron Letters'
_journal_page_first              8383
_journal_page_last               8386
_journal_paper_doi               10.1016/j.tetlet.2006.09.070
_journal_volume                  47
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_sum            'C42.25 H37 N2 O6.25'
_chemical_formula_weight         672.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6377(2)
_cell_length_b                   9.6377(2)
_cell_length_c                   35.9818(7)
_cell_measurement_reflns_used    5169
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      21.42
_cell_measurement_theta_min      2.19
_cell_volume                     3342.18(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART ApexCCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            27298
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1418
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0515
_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)+(0.0816P)²+0.8782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                3507
_reflns_number_total             3849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            2006-8383.cif
_cod_data_source_block           ic9676
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P4(1)2(1)2
_cod_database_code               1514023
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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
O1 O 0.01500(15) 0.30175(16) 0.00804(4) 0.0350(3) Uani 1 1 d .
H1A H 0.054(3) 0.250(3) 0.0244(8) 0.052 Uiso 1 1 d .
O2 O 0.18959(15) 0.14809(15) 0.04886(4) 0.0328(3) Uani 1 1 d .
H2A H 0.230(3) 0.103(3) 0.0325(8) 0.049 Uiso 1 1 d .
O3 O 0.75791(18) 0.4316(2) 0.12359(5) 0.0499(5) Uani 1 1 d .
N1 N 0.7521(2) 0.4455(2) 0.08456(6) 0.0458(5) Uani 1 1 d .
C1 C 0.7012(3) 0.5043(4) 0.00835(8) 0.0664(9) Uani 1 1 d .
H1B H 0.7683 0.4350 0.0138 0.080 Uiso 1 1 calc R
C2 C 0.6351(2) 0.5738(3) 0.03714(7) 0.0410(5) Uani 1 1 d .
C3 C 0.5350(4) 0.6704(3) 0.02811(8) 0.0649(9) Uani 1 1 d .
H3A H 0.4862 0.7165 0.0474 0.078 Uiso 1 1 calc R
C4 C 0.6637(2) 0.5388(3) 0.07612(7) 0.0403(5) Uani 1 1 d .
C5 C 0.5961(3) 0.6052(3) 0.10914(7) 0.0439(6) Uani 1 1 d .
H5A H 0.4938 0.6057 0.1068 0.053 Uiso 1 1 calc R
H5B H 0.6295 0.7013 0.1129 0.053 Uiso 1 1 calc R
C6 C 0.6440(2) 0.5096(3) 0.14013(7) 0.0451(6) Uani 1 1 d .
H6A H 0.6808 0.5670 0.1611 0.054 Uiso 1 1 calc R
C7 C 0.5363(2) 0.4099(3) 0.15515(6) 0.0401(5) Uani 1 1 d .
H7A H 0.5843 0.3371 0.1697 0.048 Uiso 1 1 calc R
H7B H 0.4749 0.4611 0.1724 0.048 Uiso 1 1 calc R
C8 C 0.4473(2) 0.3405(2) 0.12594(5) 0.0314(4) Uani 1 1 d .
C9 C 0.4937(2) 0.2265(2) 0.10593(5) 0.0316(4) Uani 1 1 d .
H9A H 0.5845 0.1921 0.1104 0.038 Uiso 1 1 calc R
C10 C 0.4113(2) 0.1612(2) 0.07949(5) 0.0295(4) Uani 1 1 d .
C11 C 0.2784(2) 0.2132(2) 0.07337(5) 0.0271(4) Uani 1 1 d .
C12 C 0.22866(19) 0.3291(2) 0.09214(5) 0.0272(4) Uani 1 1 d .
C13 C 0.3147(2) 0.3906(2) 0.11840(5) 0.0300(4) Uani 1 1 d .
H13A H 0.2821 0.4695 0.1316 0.036 Uiso 1 1 calc R
C14 C 0.0892(2) 0.3920(2) 0.08253(5) 0.0298(4) Uani 1 1 d .
H14A H 0.0560 0.4484 0.1037 0.036 Uiso 1 1 calc R
H14B H 0.0211 0.3168 0.0782 0.036 Uiso 1 1 calc R
C15 C 0.0983(2) 0.4825(2) 0.04815(6) 0.0310(4) Uani 1 1 d .
C16 C 0.1458(3) 0.6171(2) 0.05147(6) 0.0444(6) Uani 1 1 d .
H16A H 0.1709 0.6517 0.0753 0.053 Uiso 1 1 calc R
C17 C 0.1574(4) 0.7016(3) 0.02102(7) 0.0615(8) Uani 1 1 d .
H17A H 0.1891 0.7943 0.0239 0.074 Uiso 1 1 calc R
C18 C 0.1231(3) 0.6520(3) -0.01402(7) 0.0536(7) Uani 1 1 d .
H18A H 0.1318 0.7115 -0.0349 0.064 Uiso 1 1 calc R
C19 C 0.0767(2) 0.5186(2) -0.01899(6) 0.0351(5) Uani 1 1 d .
C20 C 0.0638(2) 0.4353(2) 0.01261(6) 0.0298(4) Uani 1 1 d .
C21 C 0.4661(2) 0.0381(2) 0.05751(5) 0.0342(5) Uani 1 1 d .
H21A H 0.3912 -0.0315 0.0550 0.041 Uiso 1 1 calc R
H21B H 0.5427 -0.0055 0.0716 0.041 Uiso 1 1 calc R
O4 O -0.0423(12) 0.9577(12) 0.0000 0.085(4) Uiso 0.25 2 d SP
H4A H 0.0346 0.8931 0.0029 0.127 Uiso 0.13 1 d P
C22 C -0.1444(17) 0.8556(17) 0.0000 0.075(5) Uiso 0.25 2 d SP
H22A H -0.1718 0.8759 -0.0251 0.113 Uiso 0.13 1 d P
H22B H -0.1939 0.8971 0.0062 0.113 Uiso 0.25 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'
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
N1 O3 C6 109.09(17) . .
C4 N1 O3 109.3(2) . .
C3 C1 C2 120.5(3) 7 .
C3 C2 C1 118.1(3) . .
C3 C2 C4 120.8(2) . .
C1 C2 C4 121.0(2) . .
C1 C3 C2 121.4(3) 7 .
N1 C4 C2 121.0(2) . .
N1 C4 C5 113.7(2) . .
C2 C4 C5 125.3(2) . .
C4 C5 C6 101.0(2) . .
O3 C6 C7 109.6(2) . .
O3 C6 C5 104.01(19) . .
C7 C6 C5 116.05(19) . .
C8 C7 C6 114.92(18) . .
C9 C8 C13 118.04(18) . .
C9 C8 C7 121.84(19) . .
C13 C8 C7 120.12(19) . .
C8 C9 C10 121.92(18) . .
C9 C10 C11 118.12(18) . .
C9 C10 C21 120.67(18) . .
C11 C10 C21 121.20(18) . .
O2 C11 C12 117.54(16) . .
O2 C11 C10 120.52(17) . .
C12 C11 C10 121.93(18) . .
C13 C12 C11 117.86(17) . .
C13 C12 C14 120.93(18) . .
C11 C12 C14 121.09(17) . .
C12 C13 C8 122.10(18) . .
C12 C14 C15 111.42(16) . .
C16 C15 C20 117.63(19) . .
C16 C15 C14 119.26(19) . .
C20 C15 C14 123.08(19) . .
C17 C16 C15 121.1(2) . .
C16 C17 C18 120.2(2) . .
C19 C18 C17 121.2(2) . .
C18 C19 C20 117.4(2) . .
C18 C19 C21 120.6(2) . 7
C20 C19 C21 121.9(2) . 7
O1 C20 C19 117.97(18) . .
O1 C20 C15 119.56(18) . .
C19 C20 C15 122.5(2) . .
C10 C21 C19 113.46(17) . 7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C20 1.381(3) .
O2 C11 1.380(2) .
O3 N1 1.412(3) .
O3 C6 1.458(3) .
N1 C4 1.275(3) .
C1 C3 1.377(4) 7
C1 C2 1.389(4) .
C2 C3 1.379(4) .
C2 C4 1.469(3) .
C3 C1 1.377(4) 7
C4 C5 1.499(3) .
C5 C6 1.518(4) .
C6 C7 1.514(4) .
C7 C8 1.513(3) .
C8 C9 1.388(3) .
C8 C13 1.392(3) .
C9 C10 1.390(3) .
C10 C11 1.393(3) .
C10 C21 1.521(3) .
C11 C12 1.390(3) .
C12 C13 1.390(3) .
C12 C14 1.515(3) .
C14 C15 1.516(3) .
C15 C16 1.381(3) .
C15 C20 1.397(3) .
C16 C17 1.369(3) .
C17 C18 1.388(4) .
C18 C19 1.373(4) .
C19 C20 1.397(3) .
C19 C21 1.521(3) 7
C21 C19 1.521(3) 7
O4 C22 1.39(3) .
