#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/54/7205422.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_7205422
loop_
_publ_author_name
'Dey, Sandeep Kumar'
'Pramanik, Avijit'
'Das, Gopal'
_publ_section_title
;
 Anion specificity induced conformational changes in cresol-based
 tripodal podands controlled by weak interactions: structural and
 Hirshfeld surface analysis
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1664
_journal_paper_doi               10.1039/c0ce00518e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C37 H39 N O11'
_chemical_formula_weight         673.69
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 104.935(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4682(13)
_cell_length_b                   13.6433(13)
_cell_length_c                   20.291(2)
_cell_measurement_temperature    298(2)
_cell_volume                     3602.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.1090
_diffrn_reflns_av_sigmaI/netI    0.1040
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16599
_diffrn_reflns_theta_full        26.80
_diffrn_reflns_theta_max         26.80
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADAS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                7498
_reflns_number_total             7600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00518E.TXT
_cod_data_source_block           p-CresolPMA
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7205422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.70825(19) 0.93142(19) 0.33714(15) 0.0550(8) Uani 1 1 d . . .
C1 C 0.8158(2) 0.9539(2) 0.33407(18) 0.0626(10) Uani 1 1 d . . .
H1A H 0.8411 1.0076 0.3651 0.075 Uiso 1 1 calc R . .
H1B H 0.8133 0.9768 0.2884 0.075 Uiso 1 1 calc R . .
C2 C 0.8926(2) 0.8716(2) 0.35092(19) 0.0656(10) Uani 1 1 d . . .
H2A H 0.8599 0.8100 0.3342 0.079 Uiso 1 1 calc R . .
H2B H 0.9482 0.8831 0.3295 0.079 Uiso 1 1 calc R . .
C3 C 1.0233(3) 0.8180(3) 0.4484(2) 0.0663(10) Uani 1 1 d . . .
C5 C 1.1659(3) 0.7955(3) 0.5447(2) 0.0859(12) Uani 1 1 d . . .
H5 H 1.1990 0.8107 0.5897 0.103 Uiso 1 1 calc R . .
C4 C 1.0735(3) 0.8398(3) 0.5143(2) 0.0823(12) Uani 1 1 d . . .
H4 H 1.0452 0.8848 0.5387 0.099 Uiso 1 1 calc R . .
C8 C 1.0637(3) 0.7500(3) 0.4131(2) 0.0768(11) Uani 1 1 d . . .
H8 H 1.0291 0.7334 0.3686 0.092 Uiso 1 1 calc R . .
C6 C 1.2097(3) 0.7297(3) 0.5100(2) 0.0802(12) Uani 1 1 d . . .
C7 C 1.1574(3) 0.7058(3) 0.4444(2) 0.0857(12) Uani 1 1 d . . .
H7 H 1.1850 0.6595 0.4205 0.103 Uiso 1 1 calc R . .
C9 C 1.3150(3) 0.6846(3) 0.5420(2) 0.1262(17) Uani 1 1 d . . .
H9A H 1.3468 0.6660 0.5067 0.189 Uiso 1 1 calc R . .
H9B H 1.3068 0.6277 0.5680 0.189 Uiso 1 1 calc R . .
H9C H 1.3574 0.7317 0.5715 0.189 Uiso 1 1 calc R . .
O1 O 0.93153(17) 0.86777(17) 0.42255(13) 0.0797(8) Uani 1 1 d . . .
C11 C 0.5976(3) 0.8906(3) 0.4158(2) 0.0771(11) Uani 1 1 d . . .
H11A H 0.5607 0.8378 0.3878 0.093 Uiso 1 1 calc R . .
H11B H 0.5991 0.8778 0.4630 0.093 Uiso 1 1 calc R . .
C12 C 0.4516(3) 0.9975(3) 0.40100(18) 0.0675(10) Uani 1 1 d . . .
C10 C 0.7059(2) 0.8990(2) 0.4071(2) 0.0734(11) Uani 1 1 d . . .
H10A H 0.7442 0.9455 0.4402 0.088 Uiso 1 1 calc R . .
H10B H 0.7396 0.8359 0.4165 0.088 Uiso 1 1 calc R . .
C16 C 0.3151(3) 1.1127(3) 0.3883(2) 0.0871(13) Uani 1 1 d . . .
H16 H 0.2899 1.1756 0.3772 0.104 Uiso 1 1 calc R . .
C17 C 0.4137(3) 1.0905(3) 0.3840(2) 0.0816(12) Uani 1 1 d . . .
H17 H 0.4536 1.1377 0.3698 0.098 Uiso 1 1 calc R . .
C13 C 0.3912(3) 0.9276(3) 0.42072(19) 0.0808(12) Uani 1 1 d . . .
H13 H 0.4161 0.8645 0.4318 0.097 Uiso 1 1 calc R . .
C15 C 0.2530(3) 1.0445(3) 0.4086(2) 0.0799(12) Uani 1 1 d . . .
C14 C 0.2930(3) 0.9527(3) 0.4239(2) 0.0850(12) Uani 1 1 d . . .
H14 H 0.2525 0.9051 0.4370 0.102 Uiso 1 1 calc R . .
C18 C 0.1452(3) 1.0707(3) 0.4128(2) 0.1115(15) Uani 1 1 d . . .
H18A H 0.0992 1.0691 0.3680 0.167 Uiso 1 1 calc R . .
H18B H 0.1455 1.1353 0.4316 0.167 Uiso 1 1 calc R . .
H18C H 0.1229 1.0244 0.4416 0.167 Uiso 1 1 calc R . .
O2 O 0.55010(19) 0.98154(16) 0.39465(13) 0.0795(8) Uani 1 1 d . . .
C20 C 0.6532(3) 0.8881(3) 0.2118(2) 0.0755(11) Uani 1 1 d . . .
H20A H 0.5963 0.8572 0.1792 0.091 Uiso 1 1 calc R . .
H20B H 0.6473 0.9585 0.2055 0.091 Uiso 1 1 calc R . .
C19 C 0.6513(2) 0.8614(2) 0.2832(2) 0.0711(11) Uani 1 1 d . . .
H19A H 0.6807 0.7966 0.2935 0.085 Uiso 1 1 calc R . .
H19B H 0.5803 0.8582 0.2855 0.085 Uiso 1 1 calc R . .
C21 C 0.7678(3) 0.8730(3) 0.1401(3) 0.0781(12) Uani 1 1 d . . .
C22 C 0.8661(4) 0.8511(3) 0.1374(3) 0.1022(15) Uani 1 1 d . . .
H22 H 0.9136 0.8264 0.1754 0.123 Uiso 1 1 calc R . .
C26 C 0.6986(4) 0.9067(3) 0.0835(3) 0.1073(15) Uani 1 1 d . . .
H25 H 0.6318 0.9213 0.0849 0.129 Uiso 1 1 calc R . .
C24 C 0.8273(5) 0.9013(4) 0.0193(3) 0.1200(17) Uani 1 1 d . . .
C23 C 0.8933(4) 0.8664(4) 0.0771(3) 0.1195(18) Uani 1 1 d . . .
H23 H 0.9603 0.8521 0.0759 0.143 Uiso 1 1 calc R . .
C27 C 0.8610(5) 0.9210(4) -0.0464(3) 0.185(3) Uani 1 1 d . . .
H26A H 0.9321 0.9038 -0.0394 0.277 Uiso 1 1 calc R . .
H26B H 0.8519 0.9892 -0.0580 0.277 Uiso 1 1 calc R . .
H26C H 0.8200 0.8823 -0.0830 0.277 Uiso 1 1 calc R . .
O3 O 0.74719(19) 0.85512(17) 0.20185(15) 0.0776(8) Uani 1 1 d . . .
C32 C 0.3072(2) 0.77790(19) 0.24249(15) 0.0413(8) Uani 1 1 d . . .
C31 C 0.2076(2) 0.77400(19) 0.24900(15) 0.0438(8) Uani 1 1 d . . .
C28 C 0.2934(2) 0.95530(19) 0.22681(16) 0.0447(8) Uani 1 1 d . . .
C33 C 0.3475(2) 0.8678(2) 0.23142(16) 0.0499(9) Uani 1 1 d . . .
H28 H 0.4144 0.8698 0.2268 0.060 Uiso 1 1 calc R . .
C29 C 0.1920(2) 0.9513(2) 0.23433(16) 0.0460(8) Uani 1 1 d . . .
C30 C 0.1522(2) 0.8600(2) 0.24477(16) 0.0522(9) Uani 1 1 d . . .
H31 H 0.0852 0.8569 0.2491 0.063 Uiso 1 1 calc R . .
C34 C 0.3528(3) 1.0445(2) 0.21552(18) 0.0582(10) Uani 1 1 d . . .
C35 C 0.1166(3) 1.0348(2) 0.23327(18) 0.0585(10) Uani 1 1 d . . .
C37 C 0.3707(2) 0.6875(2) 0.24188(19) 0.0512(9) Uani 1 1 d . . .
C36 C 0.1621(2) 0.6789(2) 0.26347(18) 0.0528(9) Uani 1 1 d . . .
O7 O 0.34426(16) 0.62490(15) 0.19938(12) 0.0666(7) Uani 1 1 d . . .
O4 O 0.31267(17) 1.12869(16) 0.20919(14) 0.0836(8) Uani 1 1 d . . .
O11 O 0.14124(16) 1.12349(15) 0.22236(15) 0.0812(8) Uani 1 1 d . . .
H11 H 0.1989 1.1241 0.2159 0.122 Uiso 1 1 calc R . .
O5 O 0.44260(17) 1.03179(14) 0.21200(14) 0.0803(8) Uani 1 1 d . . .
O10 O 0.03300(17) 1.01695(14) 0.24330(14) 0.0798(8) Uani 1 1 d . . .
O9 O 0.06195(15) 0.67545(18) 0.24061(14) 0.0848(9) Uani 1 1 d . . .
H9 H 0.0465 0.6677 0.1991 0.127 Uiso 1 1 calc R . .
O6 O 0.45621(16) 0.68760(14) 0.28948(14) 0.0843(9) Uani 1 1 d . . .
H6 H 0.4877 0.6367 0.2875 0.127 Uiso 1 1 calc R . .
O8 O 0.21280(16) 0.61301(15) 0.29418(12) 0.0691(7) Uani 1 1 d . . .
C25 C 0.7287(5) 0.9192(4) 0.0235(3) 0.1318(19) Uani 1 1 d . . .
H37 H 0.6802 0.9404 -0.0153 0.158 Uiso 1 1 calc R . .
H1N H 0.672(2) 0.997(2) 0.3342(15) 0.082(11) Uiso 1 1 d . . .
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
C10 N1 C1 110.9(2) . . ?
C10 N1 C19 111.8(3) . . ?
C1 N1 C19 114.7(3) . . ?
N1 C1 C2 117.0(3) . . ?
O1 C2 C1 108.2(3) . . ?
C4 C3 C8 119.8(3) . . ?
C4 C3 O1 115.5(4) . . ?
C8 C3 O1 124.7(4) . . ?
C6 C5 C4 121.2(4) . . ?
C3 C4 C5 120.3(4) . . ?
C3 C8 C7 119.3(4) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 C9 121.5(4) . . ?
C7 C6 C9 120.2(4) . . ?
C6 C7 C8 121.1(4) . . ?
C3 O1 C2 117.7(3) . . ?
O2 C11 C10 105.8(3) . . ?
C13 C12 C17 120.2(4) . . ?
C13 C12 O2 124.8(3) . . ?
C17 C12 O2 115.0(4) . . ?
N1 C10 C11 112.9(3) . . ?
C15 C16 C17 122.4(4) . . ?
C12 C17 C16 118.9(4) . . ?
C12 C13 C14 119.0(4) . . ?
C14 C15 C16 116.7(4) . . ?
C14 C15 C18 122.0(4) . . ?
C16 C15 C18 121.3(4) . . ?
C15 C14 C13 122.8(4) . . ?
C12 O2 C11 118.7(3) . . ?
O3 C20 C19 107.6(3) . . ?
C20 C19 N1 114.5(3) . . ?
C26 C21 C22 119.8(5) . . ?
C26 C21 O3 125.1(5) . . ?
C22 C21 O3 115.0(4) . . ?
C21 C22 C23 118.8(5) . . ?
C21 C26 C25 119.4(5) . . ?
C23 C24 C25 115.8(5) . . ?
C23 C24 C27 122.4(6) . . ?
C25 C24 C27 121.8(6) . . ?
C24 C23 C22 123.6(5) . . ?
C21 O3 C20 118.4(3) . . ?
C31 C32 C33 118.7(2) . . ?
C31 C32 C37 122.5(2) . . ?
C33 C32 C37 118.6(2) . . ?
C30 C31 C32 118.9(2) . . ?
C30 C31 C36 120.5(3) . . ?
C32 C31 C36 120.6(3) . . ?
C33 C28 C29 117.6(2) . . ?
C33 C28 C34 114.5(3) . . ?
C29 C28 C34 127.9(3) . . ?
C32 C33 C28 123.5(3) . . ?
C30 C29 C28 118.1(2) . . ?
C30 C29 C35 112.9(3) . . ?
C28 C29 C35 128.9(3) . . ?
C31 C30 C29 123.1(3) . . ?
O5 C34 O4 121.3(3) . . ?
O5 C34 C28 117.4(3) . . ?
O4 C34 C28 121.3(3) . . ?
O10 C35 O11 120.4(3) . . ?
O10 C35 C29 119.3(3) . . ?
O11 C35 C29 120.3(3) . . ?
O7 C37 O6 125.2(3) . . ?
O7 C37 C32 121.7(3) . . ?
O6 C37 C32 113.0(3) . . ?
O8 C36 O9 123.5(3) . . ?
O8 C36 C31 123.0(3) . . ?
O9 C36 C31 113.5(3) . . ?
C24 C25 C26 122.5(5) . . ?
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
N1 C10 1.495(4) . ?
N1 C1 1.497(4) . ?
N1 C19 1.505(4) . ?
C1 C2 1.505(4) . ?
C2 O1 1.413(4) . ?
C3 C4 1.366(4) . ?
C3 C8 1.368(4) . ?
C3 O1 1.389(4) . ?
C5 C6 1.364(5) . ?
C5 C4 1.378(5) . ?
C8 C7 1.395(4) . ?
C6 C7 1.376(5) . ?
C6 C9 1.529(5) . ?
C11 O2 1.411(3) . ?
C11 C10 1.518(4) . ?
C12 C13 1.377(5) . ?
C12 C17 1.379(4) . ?
C12 O2 1.383(4) . ?
C16 C15 1.382(5) . ?
C16 C17 1.387(5) . ?
C13 C14 1.383(4) . ?
C15 C14 1.368(5) . ?
C15 C18 1.519(5) . ?
C20 O3 1.406(4) . ?
C20 C19 1.501(4) . ?
C21 C26 1.360(5) . ?
C21 C22 1.372(5) . ?
C21 O3 1.373(5) . ?
C22 C23 1.378(6) . ?
C26 C25 1.388(6) . ?
C24 C23 1.362(6) . ?
C24 C25 1.374(7) . ?
C24 C27 1.540(7) . ?
C32 C31 1.382(4) . ?
C32 C33 1.383(3) . ?
C32 C37 1.502(4) . ?
C31 C30 1.381(4) . ?
C31 C36 1.496(4) . ?
C28 C33 1.389(4) . ?
C28 C29 1.414(4) . ?
C28 C34 1.506(4) . ?
C29 C30 1.393(4) . ?
C29 C35 1.523(4) . ?
C34 O5 1.241(3) . ?
C34 O4 1.262(3) . ?
C35 O10 1.220(3) . ?
C35 O11 1.288(3) . ?
C37 O7 1.201(3) . ?
C37 O6 1.299(3) . ?
C36 O8 1.201(3) . ?
C36 O9 1.310(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653732
2 PubChem 139195666
