#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/12/7211258.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_7211258
loop_
_publ_author_name
'Sekiya, Ryo'
'Yamasaki, Yutaro'
'Katayama, Susumu'
'Shio, Hidemi'
'Haino, Takeharu'
_publ_section_title
;
 Head-to-tail polymeric columnar structure of calix[4]arene possessing
 catechol arms in the solid state
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              8404
_journal_paper_doi               10.1039/c3ce41660g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C54 H58 N2 O10, 2(C4 H10 O2)'
_chemical_formula_sum            'C62 H78 N2 O14'
_chemical_formula_weight         1075.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2013-08-16T15:39:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.125(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   36.162(12)
_cell_length_b                   9.347(3)
_cell_length_c                   17.877(6)
_cell_measurement_reflns_used    1558
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      17.86
_cell_measurement_theta_min      2.26
_cell_volume                     5598(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.381
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bluker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5842
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         17.863
_diffrn_reflns_theta_min         2.262
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.059
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0572P)²+12.6348P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1507
_reflns_number_total             1881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c3ce41660g.txt
_cod_data_source_block           1BuOH2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        5597(3)
_cod_database_code               7211258
loop_
_space_group_symop_operation_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.61638(16) 0.1106(5) 1.0112(3) 0.0259(12) Uani 1 d . .
C2 C 0.62430(14) 0.1567(5) 0.9453(3) 0.0295(13) Uani 1 d . .
H2 H 0.6485 0.1292 0.9399 0.035 Uiso 1 calc . .
C3 C 0.59737(16) 0.2424(5) 0.8874(3) 0.0253(12) Uani 1 d . .
C4 C 0.56307(16) 0.2841(5) 0.8980(3) 0.0273(12) Uani 1 d . .
C5 C 0.55297(14) 0.2328(5) 0.9606(3) 0.0268(12) Uani 1 d . .
C6 C 0.58029(18) 0.1456(5) 1.0174(3) 0.0286(12) Uani 1 d . .
H6A H 0.5743 0.1092 1.0611 0.034 Uiso 1 calc . .
C7 C 0.51187(14) 0.2565(5) 0.9625(3) 0.0317(13) Uani 1 d . .
H7A H 0.5061 0.3602 0.9602 0.038 Uiso 1 calc . .
H7B H 0.511 0.2181 1.0134 0.038 Uiso 1 calc . .
C8 C 0.48064(14) 0.1818(6) 0.8910(3) 0.0253(12) Uani 1 d . .
C9 C 0.48375(14) 0.0378(7) 0.8800(3) 0.0346(13) Uani 1 d . .
H9 H 0.5041 -0.0151 0.9201 0.042 Uiso 1 calc . .
C10 C 0.45829(18) -0.0326(6) 0.8126(4) 0.0435(14) Uani 1 d . .
H10 H 0.4601 -0.1333 0.8076 0.052 Uiso 1 calc . .
C11 C 0.43028(16) 0.0453(7) 0.7527(3) 0.0378(13) Uani 1 d . .
H11 H 0.4135 -0.0021 0.705 0.045 Uiso 1 calc . .
C12 C 0.57416(13) 0.1902(6) 0.7400(3) 0.0274(13) Uani 1 d . .
C13 C 0.45029(15) 0.2562(6) 0.8319(3) 0.0250(12) Uani 1 d . .
C14 C 0.60305(13) 0.2758(5) 0.8099(3) 0.0327(13) Uani 1 d . .
H14A H 0.6308 0.2529 0.8163 0.039 Uiso 1 calc . .
H14B H 0.5987 0.3793 0.7981 0.039 Uiso 1 calc . .
C15 C 0.67652(19) -0.0395(5) 1.0795(3) 0.0330(14) Uani 1 d . .
C16 C 0.69910(15) -0.1209(5) 1.1552(3) 0.0294(13) Uani 1 d . .
C17 C 0.73111(18) -0.2042(6) 1.1553(3) 0.0465(15) Uani 1 d . .
H17 H 0.7374 -0.2074 1.1083 0.056 Uiso 1 calc . .
C18 C 0.75393(17) -0.2823(6) 1.2226(4) 0.0605(17) Uani 1 d . .
H18 H 0.7754 -0.3392 1.2212 0.073 Uiso 1 calc . .
C19 C 0.74569(17) -0.2778(6) 1.2915(4) 0.0488(15) Uani 1 d . .
H19 H 0.7614 -0.3315 1.3377 0.059 Uiso 1 calc . .
C20 C 0.71468(17) -0.1957(6) 1.2936(3) 0.0362(14) Uani 1 d . .
C21 C 0.69168(15) -0.1164(5) 1.2260(4) 0.0288(13) Uani 1 d . .
C28 C 0.65098(17) 0.7618(6) 0.8477(3) 0.0658(17) Uani 1 d . .
H28A H 0.6357 0.7566 0.7887 0.079 Uiso 1 calc . .
H28B H 0.6316 0.7751 0.8741 0.079 Uiso 1 calc . .
C29 C 0.67221(16) 0.6220(6) 0.8753(3) 0.0629(17) Uani 1 d . .
H29A H 0.6522 0.5442 0.8605 0.075 Uiso 1 calc . .
H29B H 0.6902 0.6052 0.8459 0.075 Uiso 1 calc . .
C30 C 0.69595(16) 0.6140(6) 0.9630(3) 0.0568(16) Uani 1 d . .
H30A H 0.6792 0.6492 0.9921 0.068 Uiso 1 calc . .
H30B H 0.719 0.6798 0.9758 0.068 Uiso 1 calc . .
C31 C 0.71165(16) 0.4667(6) 0.9956(3) 0.0514(15) Uani 1 d . .
H31A H 0.728 0.4742 1.054 0.062 Uiso 1 calc . .
H31B H 0.6888 0.4026 0.9891 0.062 Uiso 1 calc . .
N1 N 0.64262(14) 0.0257(4) 1.0742(2) 0.0333(11) Uani 1 d . .
H1 H 0.6357 0.0138 1.116 0.04 Uiso 1 calc . .
O1 O 0.53570(9) 0.3706(3) 0.83907(18) 0.0377(8) Uani 1 d . .
O2 O 0.44520(9) 0.4010(4) 0.84104(17) 0.0427(8) Uani 1 d . .
O3 O 0.69032(9) -0.0341(3) 1.0246(2) 0.0422(10) Uani 1 d . .
O4 O 0.66128(10) -0.0337(4) 1.22966(17) 0.0399(9) Uani 1 d . .
H4 H 0.6661 -0.0112 1.2779 0.06 Uiso 1 calc . .
O5 O 0.70511(9) -0.1819(3) 1.3601(2) 0.0454(10) Uani 1 d . .
H5 H 0.7152 -0.2498 1.3921 0.068 Uiso 1 calc . .
O6 O 0.67593(11) 0.8817(4) 0.86383(18) 0.0525(10) Uani 1 d . .
H6 H 0.6802 0.9115 0.9107 0.079 Uiso 1 calc . .
O7 O 0.73510(10) 0.4059(4) 0.9554(2) 0.0576(10) Uani 1 d . .
H7 H 0.7564 0.4524 0.9671 0.086 Uiso 1 calc . .
C22A C 0.5297(3) 0.5155(8) 0.8623(5) 0.0377(8) Uani 0.664(5) d A 1
H22A H 0.5277 0.5134 0.916 0.045 Uiso 0.664(5) calc A 1
H22B H 0.5042 0.5535 0.823 0.045 Uiso 0.664(5) calc A 1
C23A C 0.5635(2) 0.6133(8) 0.8651(4) 0.0377(8) Uani 0.664(5) d A 1
H23A H 0.589 0.5778 0.9055 0.045 Uiso 0.664(5) calc A 1
H23B H 0.5659 0.6153 0.8117 0.045 Uiso 0.664(5) calc A 1
C24A C 0.5550(2) 0.7607(8) 0.8876(5) 0.0377(8) Uani 0.664(5) d A 1
H24A H 0.5331 0.8031 0.8421 0.057 Uiso 0.664(5) calc A 1
H24B H 0.5789 0.8202 0.9006 0.057 Uiso 0.664(5) calc A 1
H24C H 0.5475 0.7551 0.9347 0.057 Uiso 0.664(5) calc A 1
C22B C 0.5505(5) 0.5157(17) 0.8426(9) 0.0377(8) Uani 0.336(5) d A 2
H22C H 0.5371 0.5631 0.7897 0.045 Uiso 0.336(5) calc A 2
H22D H 0.5796 0.5137 0.8545 0.045 Uiso 0.336(5) calc A 2
C23B C 0.5429(4) 0.5958(16) 0.9052(9) 0.0377(8) Uani 0.336(5) d A 2
H23C H 0.5512 0.5362 0.9546 0.045 Uiso 0.336(5) calc A 2
H23D H 0.5137 0.6111 0.8874 0.045 Uiso 0.336(5) calc A 2
C24B C 0.5649(5) 0.7500(17) 0.9288(9) 0.0377(8) Uani 0.336(5) d A 2
H24D H 0.5895 0.7491 0.9178 0.057 Uiso 0.336(5) calc A 2
H24E H 0.5714 0.769 0.9862 0.057 Uiso 0.336(5) calc A 2
H24F H 0.5471 0.825 0.8965 0.057 Uiso 0.336(5) calc A 2
C25A C 0.4062(4) 0.3989(14) 0.8626(8) 0.0427(8) Uani 0.451(5) d B 3
H25A H 0.3853 0.3368 0.8248 0.051 Uiso 0.451(5) calc B 3
H25B H 0.4125 0.3646 0.9185 0.051 Uiso 0.451(5) calc B 3
C26A C 0.3930(3) 0.5528(13) 0.8538(6) 0.0427(8) Uani 0.451(5) d B 3
H26A H 0.3885 0.5852 0.7983 0.051 Uiso 0.451(5) calc B 3
H26B H 0.4147 0.612 0.8917 0.051 Uiso 0.451(5) calc B 3
C27A C 0.3551(3) 0.5767(14) 0.8702(7) 0.0427(8) Uani 0.451(5) d B 3
H27A H 0.335 0.5056 0.8405 0.064 Uiso 0.451(5) calc B 3
H27B H 0.3447 0.673 0.8524 0.064 Uiso 0.451(5) calc B 3
H27C H 0.3611 0.567 0.9282 0.064 Uiso 0.451(5) calc B 3
C25B C 0.4256(3) 0.4533(11) 0.8877(6) 0.0427(8) Uani 0.549(5) d B 4
H25C H 0.4321 0.5558 0.8992 0.051 Uiso 0.549(5) calc B 4
H25D H 0.4346 0.4013 0.9398 0.051 Uiso 0.549(5) calc B 4
C26B C 0.3823(3) 0.4367(12) 0.8466(5) 0.0427(8) Uani 0.549(5) d B 4
H26C H 0.3761 0.3354 0.8307 0.051 Uiso 0.549(5) calc B 4
H26D H 0.3731 0.4952 0.7967 0.051 Uiso 0.549(5) calc B 4
C27B C 0.3599(3) 0.4828(11) 0.9006(6) 0.0427(8) Uani 0.549(5) d B 4
H27D H 0.3664 0.417 0.9465 0.064 Uiso 0.549(5) calc B 4
H27E H 0.3311 0.4806 0.8692 0.064 Uiso 0.549(5) calc B 4
H27F H 0.3679 0.5801 0.9205 0.064 Uiso 0.549(5) calc B 4
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 0 '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 0.006 '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
C2 C1 C6 119.8(4) . .
C2 C1 N1 124.2(5) . .
C6 C1 N1 116.0(5) . .
C3 C2 C1 120.4(4) . .
C2 C3 C4 118.6(4) . .
C2 C3 C14 120.5(5) . .
C4 C3 C14 120.5(5) . .
C3 C4 C5 122.4(4) . .
C3 C4 O1 118.5(5) . .
C5 C4 O1 118.7(5) . .
C6 C5 C4 117.6(4) . .
C6 C5 C7 120.3(5) . .
C4 C5 C7 121.7(5) . .
C5 C6 C1 120.8(4) . .
C5 C7 C8 109.8(4) . .
C9 C8 C13 117.8(4) . .
C9 C8 C7 119.8(5) . .
C13 C8 C7 122.2(5) . .
C8 C9 C10 122.0(5) . .
C11 C10 C9 118.9(5) . .
C10 C11 C12 121.7(5) . 2_656
C11 C12 C13 117.8(4) 2_656 2_656
C11 C12 C14 120.6(5) 2_656 .
C13 C12 C14 121.6(5) 2_656 .
O2 C13 C8 120.1(5) . .
O2 C13 C12 118.3(5) . 2_656
C8 C13 C12 121.5(4) . 2_656
C3 C14 C12 110.9(4) . .
O3 C15 N1 123.2(5) . .
O3 C15 C16 118.9(6) . .
N1 C15 C16 117.9(5) . .
C21 C16 C17 117.4(5) . .
C21 C16 C15 125.5(5) . .
C17 C16 C15 117.1(6) . .
C18 C17 C16 121.3(5) . .
C19 C18 C17 120.3(5) . .
C20 C19 C18 119.8(5) . .
O5 C20 C19 123.7(5) . .
O5 C20 C21 116.2(5) . .
C19 C20 C21 120.1(5) . .
O4 C21 C16 119.7(5) . .
O4 C21 C20 119.2(5) . .
C16 C21 C20 121.1(5) . .
O6 C28 C29 114.8(4) . .
C30 C29 C28 114.4(5) . .
C29 C30 C31 115.9(5) . .
O7 C31 C30 112.2(4) . .
C15 N1 C1 129.4(4) . .
C4 O1 C22B 111.2(7) . .
C4 O1 C22A 117.5(4) . .
C25B O2 C13 122.8(5) . .
C13 O2 C25A 100.7(5) . .
O1 C22A C23A 111.4(6) . .
C24A C23A C22A 108.6(6) . .
O1 C22B C23B 109.9(13) . .
C22B C23B C24B 116.1(13) . .
C26A C25A O2 103.6(9) . .
C25A C26A C27A 113.1(11) . .
O2 C25B C26B 110.9(8) . .
C25B C26B C27B 111.8(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.381(6) .
C1 C6 1.389(6) .
C1 N1 1.412(6) .
C2 C3 1.379(6) .
C3 C4 1.380(6) .
C3 C14 1.507(6) .
C4 C5 1.387(6) .
C4 O1 1.399(5) .
C5 C6 1.384(6) .
C5 C7 1.515(6) .
C7 C8 1.519(6) .
C8 C9 1.371(6) .
C8 C13 1.390(6) .
C9 C10 1.377(6) .
C10 C11 1.373(6) .
C11 C12 1.375(6) 2_656
C12 C11 1.376(6) 2_656
C12 C13 1.399(6) 2_656
C12 C14 1.521(6) .
C13 O2 1.384(5) .
C13 C12 1.399(6) 2_656
C15 O3 1.259(5) .
C15 N1 1.340(6) .
C15 C16 1.498(6) .
C16 C21 1.390(6) .
C16 C17 1.394(6) .
C17 C18 1.384(7) .
C18 C19 1.373(6) .
C19 C20 1.371(7) .
C20 O5 1.364(5) .
C20 C21 1.395(6) .
C21 O4 1.365(5) .
C28 O6 1.399(6) .
C28 C29 1.502(7) .
C29 C30 1.479(7) .
C30 C31 1.519(7) .
C31 O7 1.420(5) .
O1 C22B 1.450(16) .
O1 C22A 1.456(8) .
O2 C25B 1.372(8) .
O2 C25A 1.597(13) .
C22A C23A 1.513(12) .
C23A C24A 1.499(10) .
C22B C23B 1.46(2) .
C23B C24B 1.62(2) .
C25A C26A 1.505(17) .
C26A C27A 1.525(13) .
C25B C26B 1.464(14) .
C26B C27B 1.539(11) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197275
