#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/54/7205419.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_7205419
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            'C27 H38 Br N O5'
_chemical_formula_weight         536.48
_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                 105.385(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   43.2178(12)
_cell_length_b                   7.6050(2)
_cell_length_c                   17.6312(4)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.66
_cell_measurement_theta_min      2.34
_cell_volume                     5587.2(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0938
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43040
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  0.696
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6964
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0655P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                6598
_reflns_number_total             6964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00518E.TXT
_cod_data_source_block           p-cresolBr
_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      C2/c
_cod_database_code               7205419
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.244667(9) 0.97096(5) 0.143684(19) 0.07386(17) Uani 1 1 d . . .
N1 N 0.19356(6) 0.9399(3) 0.39091(14) 0.0495(6) Uani 1 1 d . . .
C2 C 0.17668(7) 1.2474(4) 0.37228(19) 0.0645(8) Uani 1 1 d . . .
H2A H 0.1804 1.3668 0.3918 0.077 Uiso 1 1 calc R . .
H2B H 0.1788 1.2434 0.3189 0.077 Uiso 1 1 calc R . .
C1 C 0.19968(7) 1.1224(4) 0.42428(18) 0.0608(8) Uani 1 1 d . . .
H1A H 0.1968 1.1250 0.4770 0.073 Uiso 1 1 calc R . .
H1B H 0.2216 1.1570 0.4273 0.073 Uiso 1 1 calc R . .
O1 O 0.14575(4) 1.1875(3) 0.37517(11) 0.0595(5) Uani 1 1 d . . .
C3 C 0.11893(7) 1.2371(4) 0.31754(16) 0.0501(7) Uani 1 1 d . . .
C4 C 0.09029(7) 1.1812(4) 0.32953(17) 0.0560(8) Uani 1 1 d . . .
H4 H 0.0902 1.1185 0.3747 0.067 Uiso 1 1 calc R . .
C8 C 0.11913(7) 1.3301(4) 0.25082(17) 0.0594(8) Uani 1 1 d . . .
H8 H 0.1383 1.3693 0.2423 0.071 Uiso 1 1 calc R . .
C5 C 0.06186(7) 1.2181(4) 0.27473(18) 0.0640(9) Uani 1 1 d . . .
H5 H 0.0427 1.1799 0.2835 0.077 Uiso 1 1 calc R . .
C7 C 0.09017(9) 1.3643(4) 0.19659(18) 0.0692(9) Uani 1 1 d . . .
H7 H 0.0903 1.4262 0.1512 0.083 Uiso 1 1 calc R . .
C6 C 0.06123(8) 1.3107(4) 0.20687(17) 0.0646(9) Uani 1 1 d . . .
C9 C 0.02982(8) 1.3483(6) 0.1466(2) 0.1039(14) Uani 1 1 d . . .
H9A H 0.0151 1.4008 0.1721 0.156 Uiso 1 1 calc R . .
H9B H 0.0210 1.2404 0.1219 0.156 Uiso 1 1 calc R . .
H9C H 0.0335 1.4276 0.1075 0.156 Uiso 1 1 calc R . .
C12 C 0.11459(7) 0.7442(4) 0.42241(17) 0.0527(7) Uani 1 1 d . . .
C17 C 0.09216(7) 0.7038(4) 0.35341(17) 0.0602(8) Uani 1 1 d . . .
H17 H 0.0986 0.6599 0.3109 0.072 Uiso 1 1 calc R . .
C11 C 0.17133(7) 0.7811(4) 0.48557(17) 0.0657(9) Uani 1 1 d . . .
H11A H 0.1754 0.6962 0.5281 0.079 Uiso 1 1 calc R . .
H11B H 0.1658 0.8930 0.5049 0.079 Uiso 1 1 calc R . .
C13 C 0.10502(8) 0.8027(4) 0.48651(18) 0.0654(9) Uani 1 1 d . . .
H13 H 0.1199 0.8263 0.5341 0.078 Uiso 1 1 calc R . .
C10 C 0.20008(7) 0.7997(4) 0.45357(18) 0.0642(9) Uani 1 1 d . . .
H10A H 0.2045 0.6887 0.4314 0.077 Uiso 1 1 calc R . .
H10B H 0.2187 0.8316 0.4956 0.077 Uiso 1 1 calc R . .
C14 C 0.07248(9) 0.8255(4) 0.4779(2) 0.0759(10) Uani 1 1 d . . .
H14 H 0.0659 0.8654 0.5210 0.091 Uiso 1 1 calc R . .
C15 C 0.04970(8) 0.7924(4) 0.4096(2) 0.0745(10) Uani 1 1 d . . .
C16 C 0.05997(8) 0.7287(4) 0.3475(2) 0.0693(9) Uani 1 1 d . . .
H16 H 0.0449 0.7017 0.3005 0.083 Uiso 1 1 calc R . .
C18 C 0.01425(8) 0.8225(5) 0.4027(3) 0.1151(15) Uani 1 1 d . . .
H18A H 0.0034 0.7113 0.3977 0.173 Uiso 1 1 calc R . .
H18B H 0.0051 0.8931 0.3571 0.173 Uiso 1 1 calc R . .
H18C H 0.0119 0.8820 0.4489 0.173 Uiso 1 1 calc R . .
O2 O 0.14611(5) 0.7216(3) 0.42052(11) 0.0641(6) Uani 1 1 d . . .
C24 C 0.08372(7) 0.7251(4) 0.05047(16) 0.0516(7) Uani 1 1 d . . .
C22 C 0.10420(7) 0.8757(4) 0.17424(16) 0.0519(7) Uani 1 1 d . . .
H22 H 0.1003 0.9428 0.2148 0.062 Uiso 1 1 calc R . .
C21 C 0.13507(7) 0.8279(4) 0.17549(16) 0.0506(7) Uani 1 1 d . . .
C23 C 0.07914(7) 0.8232(4) 0.11240(16) 0.0539(7) Uani 1 1 d . . .
H23 H 0.0584 0.8551 0.1124 0.065 Uiso 1 1 calc R . .
C25 C 0.11484(7) 0.6804(4) 0.05288(17) 0.0630(8) Uani 1 1 d . . .
H25 H 0.1187 0.6152 0.0117 0.076 Uiso 1 1 calc R . .
C26 C 0.14051(7) 0.7294(4) 0.11472(18) 0.0628(8) Uani 1 1 d . . .
H26 H 0.1613 0.6961 0.1152 0.075 Uiso 1 1 calc R . .
C20 C 0.18852(6) 0.7959(4) 0.26239(17) 0.0613(8) Uani 1 1 d . . .
H20A H 0.1979 0.7832 0.2185 0.074 Uiso 1 1 calc R . .
H20B H 0.1854 0.6800 0.2820 0.074 Uiso 1 1 calc R . .
C27 C 0.05583(7) 0.6695(4) -0.01648(17) 0.0725(9) Uani 1 1 d . . .
H27A H 0.0449 0.7719 -0.0421 0.109 Uiso 1 1 calc R . .
H27B H 0.0413 0.5997 0.0036 0.109 Uiso 1 1 calc R . .
H27C H 0.0636 0.6016 -0.0535 0.109 Uiso 1 1 calc R . .
C19 C 0.20968(7) 0.9058(5) 0.32624(18) 0.0628(8) Uani 1 1 d . . .
H19A H 0.2143 1.0169 0.3044 0.075 Uiso 1 1 calc R . .
H19B H 0.2299 0.8454 0.3477 0.075 Uiso 1 1 calc R . .
O3 O 0.15884(4) 0.8889(3) 0.23901(11) 0.0638(6) Uani 1 1 d . . .
O4 O 0.21581(6) 0.4274(4) 0.57076(16) 0.0853(7) Uani 1 1 d D . .
O5 O 0.20636(7) 0.6673(4) 0.68827(16) 0.0903(7) Uani 1 1 d D . .
H1N H 0.1720(6) 0.936(3) 0.3699(13) 0.035(7) Uiso 1 1 d . . .
H1O H 0.2134(9) 0.499(4) 0.6097(15) 0.096(14) Uiso 1 1 d D . .
H2O H 0.2258(8) 0.329(3) 0.593(2) 0.126(17) Uiso 1 1 d D . .
H3O H 0.2210(7) 0.641(5) 0.7337(12) 0.115(15) Uiso 1 1 d D . .
H4O H 0.2147(9) 0.771(3) 0.678(2) 0.125(18) Uiso 1 1 d 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'
Br Br -0.2901 2.4595 '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
C1 N1 C10 112.8(2) . . ?
C1 N1 C19 112.7(2) . . ?
C10 N1 C19 113.5(2) . . ?
O1 C2 C1 104.6(2) . . ?
C2 C1 N1 109.1(2) . . ?
C3 O1 C2 120.0(2) . . ?
C8 C3 O1 125.3(3) . . ?
C8 C3 C4 120.0(3) . . ?
O1 C3 C4 114.7(2) . . ?
C5 C4 C3 120.1(3) . . ?
C3 C8 C7 118.6(3) . . ?
C4 C5 C6 121.4(3) . . ?
C6 C7 C8 122.8(3) . . ?
C7 C6 C5 117.1(3) . . ?
C7 C6 C9 122.1(3) . . ?
C5 C6 C9 120.8(3) . . ?
C17 C12 C13 120.3(3) . . ?
C17 C12 O2 114.8(3) . . ?
C13 C12 O2 124.9(3) . . ?
C12 C17 C16 119.8(3) . . ?
O2 C11 C10 105.0(2) . . ?
C12 C13 C14 117.9(3) . . ?
C11 C10 N1 109.3(2) . . ?
C15 C14 C13 123.3(3) . . ?
C14 C15 C16 117.3(3) . . ?
C14 C15 C18 121.3(4) . . ?
C16 C15 C18 121.4(4) . . ?
C15 C16 C17 121.3(3) . . ?
C12 O2 C11 119.2(2) . . ?
C25 C24 C23 117.0(3) . . ?
C25 C24 C27 121.8(3) . . ?
C23 C24 C27 121.2(3) . . ?
C23 C22 C21 119.4(3) . . ?
C22 C21 C26 119.7(3) . . ?
C22 C21 O3 115.6(2) . . ?
C26 C21 O3 124.7(3) . . ?
C22 C23 C24 122.4(3) . . ?
C24 C25 C26 122.0(3) . . ?
C21 C26 C25 119.5(3) . . ?
O3 C20 C19 105.2(2) . . ?
C20 C19 N1 110.5(2) . . ?
C21 O3 C20 119.0(2) . . ?
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 C1 1.503(4) . ?
N1 C10 1.507(4) . ?
N1 C19 1.508(4) . ?
C2 O1 1.426(3) . ?
C2 C1 1.499(4) . ?
O1 C3 1.376(3) . ?
C3 C8 1.375(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.375(4) . ?
C8 C7 1.383(4) . ?
C5 C6 1.383(4) . ?
C7 C6 1.372(4) . ?
C6 C9 1.513(4) . ?
C12 C17 1.374(4) . ?
C12 C13 1.376(4) . ?
C12 O2 1.382(3) . ?
C17 C16 1.380(4) . ?
C11 O2 1.430(3) . ?
C11 C10 1.501(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.362(4) . ?
C15 C16 1.375(5) . ?
C15 C18 1.521(4) . ?
C24 C25 1.377(4) . ?
C24 C23 1.379(4) . ?
C24 C27 1.507(4) . ?
C22 C23 1.376(4) . ?
C22 C21 1.377(4) . ?
C21 C26 1.378(4) . ?
C21 O3 1.384(3) . ?
C25 C26 1.384(4) . ?
C20 O3 1.426(3) . ?
C20 C19 1.502(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653731
2 PubChem 139195664
