#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:07:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180288 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/02/7150248.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_7150248
loop_
_publ_author_name
'Danila, Crenguta'
'Böhmer, Volker'
'Bolte, Michael'
_publ_section_title
;
 Conformational properties of cyanomethoxy calix[4]arenes.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3508
_journal_page_last               3513
_journal_paper_doi               10.1039/b507780j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C46 H48 N4 O8'
_chemical_formula_weight         784.88
_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                92.126(11)
_cell_angle_beta                 109.791(10)
_cell_angle_gamma                101.734(11)
_cell_formula_units_Z            1
_cell_length_a                   9.7073(14)
_cell_length_b                   10.5690(14)
_cell_length_c                   10.9986(15)
_cell_measurement_reflns_used    10490
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      3.6
_cell_volume                     1032.7(3)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            11250
_diffrn_reflns_theta_full        25.65
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         3.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9862
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0434
_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)+(0.0630P)²+0.0000P] where

P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2611
_reflns_number_total             3800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b507780j.txt
_cod_data_source_block           boeh13
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        1032.7(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150248
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
C1 C -0.06546(19) 0.79661(15) 0.50162(18) 0.0286(4) Uani 1 1 d . . .
H1A H -0.0457 0.7809 0.5935 0.034 Uiso 1 1 calc R . .
H1B H -0.0894 0.8832 0.4915 0.034 Uiso 1 1 calc R . .
C11 C 0.07516(18) 0.79697(15) 0.46982(18) 0.0271(4) Uani 1 1 d . . .
C12 C 0.18681(19) 0.73701(15) 0.54286(18) 0.0274(4) Uani 1 1 d . . .
C13 C 0.30764(18) 0.72606(15) 0.50505(18) 0.0289(4) Uani 1 1 d . . .
C14 C 0.3221(2) 0.78615(17) 0.3984(2) 0.0330(4) Uani 1 1 d . . .
H14 H 0.4054 0.7808 0.3732 0.040 Uiso 1 1 calc R . .
C15 C 0.2183(2) 0.85410(16) 0.3270(2) 0.0334(4) Uani 1 1 d . . .
C16 C 0.09454(19) 0.85544(16) 0.36311(18) 0.0299(4) Uani 1 1 d . . .
H16 H 0.0202 0.8978 0.3133 0.036 Uiso 1 1 calc R . .
C151 C 0.2334(2) 0.9223(2) 0.2097(2) 0.0428(5) Uani 1 1 d . . .
C152 C 0.1024(4) 0.8564(3) 0.0861(3) 0.0685(7) Uani 1 1 d . . .
H15A H 0.1060 0.7654 0.0708 0.103 Uiso 1 1 calc R . .
H15B H 0.1104 0.9017 0.0118 0.103 Uiso 1 1 calc R . .
H15C H 0.0069 0.8600 0.0967 0.103 Uiso 1 1 calc R . .
C153 C 0.2239(3) 1.0645(2) 0.2299(3) 0.0605(7) Uani 1 1 d . . .
H15D H 0.3070 1.1091 0.3082 0.091 Uiso 1 1 calc R . .
H15E H 0.1279 1.0670 0.2399 0.091 Uiso 1 1 calc R . .
H15F H 0.2307 1.1081 0.1543 0.091 Uiso 1 1 calc R . .
C154 C 0.3834(4) 0.9223(4) 0.1925(4) 0.0969(13) Uani 1 1 d . . .
H15G H 0.4664 0.9669 0.2709 0.145 Uiso 1 1 calc R . .
H15H H 0.3885 0.9675 0.1174 0.145 Uiso 1 1 calc R . .
H15I H 0.3913 0.8324 0.1781 0.145 Uiso 1 1 calc R . .
O12 O 0.17128(13) 0.68050(11) 0.65177(12) 0.0299(3) Uani 1 1 d . . .
C17 C 0.2683(2) 0.75270(17) 0.77164(19) 0.0351(4) Uani 1 1 d . . .
H17A H 0.3735 0.7676 0.7749 0.042 Uiso 1 1 calc R . .
H17B H 0.2599 0.7021 0.8438 0.042 Uiso 1 1 calc R . .
C18 C 0.2310(2) 0.87902(18) 0.78900(19) 0.0346(4) Uani 1 1 d . . .
N19 N 0.1995(2) 0.97622(17) 0.7995(2) 0.0500(5) Uani 1 1 d . . .
C2 C 0.42374(19) 0.65221(16) 0.5774(2) 0.0313(4) Uani 1 1 d . . .
H2A H 0.4964 0.7102 0.6550 0.038 Uiso 1 1 calc R . .
H2B H 0.4798 0.6356 0.5205 0.038 Uiso 1 1 calc R . .
C21 C 0.36925(18) 0.52333(16) 0.62231(18) 0.0280(4) Uani 1 1 d . . .
C22 C 0.24501(18) 0.42681(15) 0.54298(17) 0.0262(4) Uani 1 1 d . . .
C23 C 0.20007(18) 0.30662(15) 0.58530(18) 0.0267(4) Uani 1 1 d . . .
C24 C 0.28180(19) 0.28444(16) 0.71065(19) 0.0300(4) Uani 1 1 d . . .
H24 H 0.2540 0.2044 0.7424 0.036 Uiso 1 1 calc R . .
C25 C 0.40285(19) 0.37925(17) 0.78788(18) 0.0307(4) Uani 1 1 d . . .
C26 C 0.44810(19) 0.49800(17) 0.74581(19) 0.0302(4) Uani 1 1 d . . .
H26 H 0.5327 0.5612 0.8017 0.036 Uiso 1 1 calc R . .
N25 N 0.48781(18) 0.35563(15) 0.91994(17) 0.0390(4) Uani 1 1 d . . .
O251 O 0.43021(19) 0.26686(15) 0.96829(16) 0.0576(5) Uani 1 1 d . . .
O252 O 0.61366(16) 0.42572(14) 0.97640(15) 0.0485(4) Uani 1 1 d . . .
O22 O 0.15663(13) 0.45232(11) 0.42353(12) 0.0297(3) Uani 1 1 d . . .
C27 C 0.2101(2) 0.4375(2) 0.3195(2) 0.0407(5) Uani 1 1 d . . .
H27A H 0.2156 0.3460 0.3046 0.049 Uiso 1 1 calc R . .
H27B H 0.3122 0.4935 0.3417 0.049 Uiso 1 1 calc R . .
C28 C 0.1051(3) 0.4750(3) 0.1994(2) 0.0560(6) Uani 1 1 d . . .
H28 H 0.1264 0.4657 0.1219 0.067 Uiso 1 1 calc R . .
C29 C -0.0135(2) 0.5194(2) 0.1915(2) 0.0547(6) Uani 1 1 d . . .
H29A H -0.0392 0.5303 0.2666 0.066 Uiso 1 1 calc R . .
H29B H -0.0740 0.5408 0.1106 0.066 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
C23 C1 C11 112.33(15) 2_566 . ?
C23 C1 H1A 109.1 2_566 . ?
C11 C1 H1A 109.1 . . ?
C23 C1 H1B 109.1 2_566 . ?
C11 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C16 C11 C12 117.78(15) . . ?
C16 C11 C1 120.32(14) . . ?
C12 C11 C1 121.88(15) . . ?
C13 C12 C11 121.41(15) . . ?
C13 C12 O12 119.78(14) . . ?
C11 C12 O12 118.70(15) . . ?
C14 C13 C12 118.41(15) . . ?
C14 C13 C2 119.40(16) . . ?
C12 C13 C2 122.18(15) . . ?
C13 C14 C15 122.15(17) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C16 C15 C14 117.43(16) . . ?
C16 C15 C151 119.65(15) . . ?
C14 C15 C151 122.89(16) . . ?
C15 C16 C11 122.55(15) . . ?
C15 C16 H16 118.7 . . ?
C11 C16 H16 118.7 . . ?
C154 C151 C152 110.1(2) . . ?
C154 C151 C153 108.0(2) . . ?
C152 C151 C153 107.83(19) . . ?
C154 C151 C15 112.32(17) . . ?
C152 C151 C15 109.55(17) . . ?
C153 C151 C15 108.97(19) . . ?
C151 C152 H15A 109.5 . . ?
C151 C152 H15B 109.5 . . ?
H15A C152 H15B 109.5 . . ?
C151 C152 H15C 109.5 . . ?
H15A C152 H15C 109.5 . . ?
H15B C152 H15C 109.5 . . ?
C151 C153 H15D 109.5 . . ?
C151 C153 H15E 109.5 . . ?
H15D C153 H15E 109.5 . . ?
C151 C153 H15F 109.5 . . ?
H15D C153 H15F 109.5 . . ?
H15E C153 H15F 109.5 . . ?
C151 C154 H15G 109.5 . . ?
C151 C154 H15H 109.5 . . ?
H15G C154 H15H 109.5 . . ?
C151 C154 H15I 109.5 . . ?
H15G C154 H15I 109.5 . . ?
H15H C154 H15I 109.5 . . ?
C12 O12 C17 113.88(13) . . ?
O12 C17 C18 111.39(14) . . ?
O12 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O12 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N19 C18 C17 178.3(2) . . ?
C13 C2 C21 118.33(14) . . ?
C13 C2 H2A 107.7 . . ?
C21 C2 H2A 107.7 . . ?
C13 C2 H2B 107.7 . . ?
C21 C2 H2B 107.7 . . ?
H2A C2 H2B 107.1 . . ?
C26 C21 C22 118.21(15) . . ?
C26 C21 C2 118.52(16) . . ?
C22 C21 C2 123.24(16) . . ?
O22 C22 C23 117.84(15) . . ?
O22 C22 C21 119.86(14) . . ?
C23 C22 C21 122.13(15) . . ?
C24 C23 C22 118.17(16) . . ?
C24 C23 C1 120.37(14) . 2_566 ?
C22 C23 C1 121.46(15) . 2_566 ?
C25 C24 C23 119.45(15) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 122.45(16) . . ?
C24 C25 N25 119.19(15) . . ?
C26 C25 N25 118.36(16) . . ?
C21 C26 C25 119.58(17) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
O251 N25 O252 123.27(16) . . ?
O251 N25 C25 118.46(16) . . ?
O252 N25 C25 118.27(15) . . ?
C22 O22 C27 116.13(13) . . ?
O22 C27 C28 108.99(16) . . ?
O22 C27 H27A 109.9 . . ?
C28 C27 H27A 109.9 . . ?
O22 C27 H27B 109.9 . . ?
C28 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C29 C28 C27 125.9(2) . . ?
C29 C28 H28 117.1 . . ?
C27 C28 H28 117.1 . . ?
C28 C29 H29A 120.0 . . ?
C28 C29 H29B 120.0 . . ?
H29A C29 H29B 120.0 . . ?
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
C1 C23 1.519(2) 2_566 ?
C1 C11 1.519(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C11 C16 1.397(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.394(2) . ?
C12 O12 1.398(2) . ?
C13 C14 1.390(3) . ?
C13 C2 1.519(2) . ?
C14 C15 1.396(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 C151 1.536(3) . ?
C16 H16 0.9500 . ?
C151 C154 1.531(3) . ?
C151 C152 1.532(4) . ?
C151 C153 1.537(3) . ?
C152 H15A 0.9800 . ?
C152 H15B 0.9800 . ?
C152 H15C 0.9800 . ?
C153 H15D 0.9800 . ?
C153 H15E 0.9800 . ?
C153 H15F 0.9800 . ?
C154 H15G 0.9800 . ?
C154 H15H 0.9800 . ?
C154 H15I 0.9800 . ?
O12 C17 1.414(2) . ?
C17 C18 1.474(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N19 1.143(2) . ?
C2 C21 1.521(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C21 C26 1.382(3) . ?
C21 C22 1.406(3) . ?
C22 O22 1.375(2) . ?
C22 C23 1.406(2) . ?
C23 C24 1.394(3) . ?
C23 C1 1.519(2) 2_566 ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(2) . ?
C25 N25 1.467(2) . ?
C26 H26 0.9500 . ?
N25 O251 1.225(2) . ?
N25 O252 1.229(2) . ?
O22 C27 1.423(2) . ?
C27 C28 1.494(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.306(3) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9500 . ?
C29 H29B 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
C23 C1 C11 C16 78.73(19) 2_566 . . . ?
C23 C1 C11 C12 -99.63(19) 2_566 . . . ?
C16 C11 C12 C13 -5.2(3) . . . . ?
C1 C11 C12 C13 173.23(16) . . . . ?
C16 C11 C12 O12 178.57(16) . . . . ?
C1 C11 C12 O12 -3.0(2) . . . . ?
C11 C12 C13 C14 5.4(3) . . . . ?
O12 C12 C13 C14 -178.36(17) . . . . ?
C11 C12 C13 C2 -175.24(17) . . . . ?
O12 C12 C13 C2 1.0(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C2 C13 C14 C15 179.23(18) . . . . ?
C13 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C151 179.4(2) . . . . ?
C14 C15 C16 C11 2.9(3) . . . . ?
C151 C15 C16 C11 -179.05(18) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C1 C11 C16 C15 -177.50(17) . . . . ?
C16 C15 C151 C154 174.4(2) . . . . ?
C14 C15 C151 C154 -7.6(3) . . . . ?
C16 C15 C151 C152 -62.9(3) . . . . ?
C14 C15 C151 C152 115.1(2) . . . . ?
C16 C15 C151 C153 54.8(3) . . . . ?
C14 C15 C151 C153 -127.2(2) . . . . ?
C13 C12 O12 C17 77.79(19) . . . . ?
C11 C12 O12 C17 -105.90(17) . . . . ?
C12 O12 C17 C18 65.76(19) . . . . ?
O12 C17 C18 N19 -2(8) . . . . ?
C14 C13 C2 C21 -139.07(19) . . . . ?
C12 C13 C2 C21 41.6(3) . . . . ?
C13 C2 C21 C26 -136.72(18) . . . . ?
C13 C2 C21 C22 45.2(3) . . . . ?
C26 C21 C22 O22 174.84(16) . . . . ?
C2 C21 C22 O22 -7.1(2) . . . . ?
C26 C21 C22 C23 -0.3(2) . . . . ?
C2 C21 C22 C23 177.74(16) . . . . ?
O22 C22 C23 C24 -174.70(15) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
O22 C22 C23 C1 4.7(2) . . . 2_566 ?
C21 C22 C23 C1 179.95(15) . . . 2_566 ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C1 C23 C24 C25 -179.76(16) 2_566 . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C23 C24 C25 N25 179.63(16) . . . . ?
C22 C21 C26 C25 -0.1(2) . . . . ?
C2 C21 C26 C25 -178.27(16) . . . . ?
C24 C25 C26 C21 0.3(3) . . . . ?
N25 C25 C26 C21 -179.39(16) . . . . ?
C24 C25 N25 O251 -16.4(3) . . . . ?
C26 C25 N25 O251 163.34(18) . . . . ?
C24 C25 N25 O252 163.34(18) . . . . ?
C26 C25 N25 O252 -16.9(3) . . . . ?
C23 C22 O22 C27 -102.00(18) . . . . ?
C21 C22 O22 C27 82.6(2) . . . . ?
C22 O22 C27 C28 -177.31(16) . . . . ?
O22 C27 C28 C29 2.6(3) . . . . ?
