#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/45/4504518.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_4504518
loop_
_publ_author_name
'Jayaraman, Akhila'
'Balasubramaniam, Venkataramanan'
'Valiyaveettil, Suresh'
_publ_section_title
;
 Formation of Interesting Organic Supramolecular Structures in the
 Solid-State Self-Assembly of Triphenol Adducts
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              150
_journal_paper_doi               10.1021/cg050251p
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C25 H22 N O3.5'
_chemical_formula_weight         392.44
_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                106.0180(10)
_cell_angle_beta                 105.7870(10)
_cell_angle_gamma                97.4340(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1353(5)
_cell_length_b                   10.4475(6)
_cell_length_c                   12.0967(7)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.38
_cell_volume                     1041.42(10)
_computing_cell_refinement       'Bruker SMART'
_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      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10922
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            GOLD
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0605
_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)+(0.0771P)²+0.7272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1645
_reflns_number_gt                3038
_reflns_number_total             3671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050251psi20050603_045628.cif
_cod_data_source_block           4177
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C25 H22 N O3.50'
_cod_database_code               4504518
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
O1 O 0.3213(2) 0.8045(2) 0.05079(14) 0.0539(5) Uani 1 1 d .
H1A H 0.3687 0.7853 0.0010 0.081 Uiso 1 1 calc R
O2 O 0.0766(3) 0.52955(17) 0.19228(18) 0.0646(6) Uani 1 1 d .
H2A H 0.0381 0.4498 0.1844 0.097 Uiso 1 1 calc R
O3 O -0.0449(2) 1.25885(15) 0.12633(15) 0.0460(4) Uani 1 1 d .
H3A H -0.1238 1.2317 0.0651 0.069 Uiso 1 1 calc R
C1 C 0.1722(2) 0.8024(2) 0.22418(19) 0.0316(5) Uani 1 1 d .
H1 H 0.1250 0.7279 0.1454 0.038 Uiso 1 1 calc R
C2 C 0.3478(2) 0.8165(2) 0.25438(19) 0.0322(5) Uani 1 1 d .
C3 C 0.4150(3) 0.8141(2) 0.1630(2) 0.0381(5) Uani 1 1 d .
C4 C 0.5736(3) 0.8208(3) 0.1861(2) 0.0491(6) Uani 1 1 d .
H4 H 0.6172 0.8197 0.1239 0.059 Uiso 1 1 calc R
C5 C 0.6676(3) 0.8290(3) 0.2990(2) 0.0536(7) Uani 1 1 d .
H5 H 0.7746 0.8318 0.3136 0.064 Uiso 1 1 calc R
C6 C 0.6041(3) 0.8331(3) 0.3906(2) 0.0506(6) Uani 1 1 d .
H6 H 0.6676 0.8388 0.4681 0.061 Uiso 1 1 calc R
C7 C 0.4464(3) 0.8288(2) 0.3680(2) 0.0407(5) Uani 1 1 d .
H7 H 0.4050 0.8344 0.4318 0.049 Uiso 1 1 calc R
C8 C 0.1077(2) 0.7561(2) 0.31379(19) 0.0338(5) Uani 1 1 d .
C9 C 0.0550(3) 0.6172(2) 0.2910(2) 0.0438(6) Uani 1 1 d .
C10 C -0.0170(3) 0.5723(3) 0.3649(3) 0.0562(7) Uani 1 1 d .
H10 H -0.0568 0.4785 0.3462 0.067 Uiso 1 1 calc R
C11 C -0.0301(3) 0.6648(3) 0.4654(3) 0.0571(7) Uani 1 1 d .
H11 H -0.0796 0.6340 0.5150 0.068 Uiso 1 1 calc R
C12 C 0.0288(3) 0.8019(3) 0.4939(2) 0.0508(6) Uani 1 1 d .
H12 H 0.0243 0.8648 0.5648 0.061 Uiso 1 1 calc R
C13 C 0.0949(3) 0.8462(2) 0.4168(2) 0.0402(5) Uani 1 1 d .
H13 H 0.1322 0.9403 0.4350 0.048 Uiso 1 1 calc R
C14 C 0.1160(2) 0.9278(2) 0.20316(18) 0.0304(5) Uani 1 1 d .
C15 C -0.0359(2) 0.9108(2) 0.12976(19) 0.0331(5) Uani 1 1 d .
H15 H -0.1018 0.8233 0.0965 0.040 Uiso 1 1 calc R
C16 C -0.0929(3) 1.0195(2) 0.1043(2) 0.0353(5) Uani 1 1 d .
H16 H -0.1962 1.0059 0.0544 0.042 Uiso 1 1 calc R
C17 C 0.0038(3) 1.1483(2) 0.15309(19) 0.0338(5) Uani 1 1 d .
C18 C 0.1536(3) 1.1682(2) 0.2286(2) 0.0390(5) Uani 1 1 d .
H18 H 0.2180 1.2564 0.2638 0.047 Uiso 1 1 calc R
C19 C 0.2098(3) 1.0585(2) 0.25290(19) 0.0359(5) Uani 1 1 d .
H19 H 0.3128 1.0728 0.3038 0.043 Uiso 1 1 calc R
O1S O 0.2297(11) 0.4626(12) -0.0024(8) 0.176(4) Uani 0.50 1 d PD
H1SA H 0.223(7) 0.481(7) 0.074(2) 0.080 Uiso 0.50 1 d PD
H1SB H 0.144(5) 0.474(7) -0.055(4) 0.080 Uiso 0.50 1 d PD
N1 N 0.4254(3) 0.7259(3) -0.1344(2) 0.0647(7) Uani 1 1 d .
C20 C 0.4600(4) 0.5412(4) -0.4856(3) 0.0778(10) Uani 1 1 d .
H20A H 0.4004 0.5692 -0.5476 0.093 Uiso 1 1 calc R
C21 C 0.4884(4) 0.6179(4) -0.1530(3) 0.0735(9) Uani 1 1 d .
H21 H 0.5248 0.5847 -0.0882 0.088 Uiso 1 1 calc R
C22 C 0.5025(4) 0.5519(3) -0.2655(3) 0.0754(9) Uani 1 1 d .
H22 H 0.5477 0.4753 -0.2759 0.091 Uiso 1 1 calc R
C23 C 0.4495(3) 0.5998(3) -0.3617(2) 0.0636(8) Uani 1 1 d .
C24 C 0.3837(4) 0.7106(4) -0.3407(3) 0.0683(9) Uani 1 1 d .
H24 H 0.3450 0.7460 -0.4036 0.082 Uiso 1 1 calc R
C25 C 0.3746(4) 0.7692(4) -0.2285(3) 0.0673(8) Uani 1 1 d .
H25 H 0.3293 0.8455 -0.2164 0.081 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
C2 C1 C8 113.34(17) .
C2 C1 C14 113.97(17) .
C8 C1 C14 111.58(16) .
C7 C2 C3 117.2(2) .
C7 C2 C1 123.53(19) .
C3 C2 C1 119.21(18) .
O1 C3 C4 120.8(2) .
O1 C3 C2 118.57(19) .
C4 C3 C2 120.7(2) .
C5 C4 C3 120.7(2) .
C4 C5 C6 119.6(2) .
C5 C6 C7 119.7(2) .
C6 C7 C2 122.1(2) .
C13 C8 C9 117.6(2) .
C13 C8 C1 122.99(19) .
C9 C8 C1 119.38(19) .
O2 C9 C10 122.6(2) .
O2 C9 C8 116.6(2) .
C10 C9 C8 120.8(2) .
C11 C10 C9 120.0(2) .
C12 C11 C10 120.4(2) .
C11 C12 C13 119.1(2) .
C8 C13 C12 122.0(2) .
C19 C14 C15 117.97(19) .
C19 C14 C1 123.33(19) .
C15 C14 C1 118.69(18) .
C16 C15 C14 121.65(19) .
C17 C16 C15 119.2(2) .
C18 C17 O3 118.28(19) .
C18 C17 C16 120.13(19) .
O3 C17 C16 121.6(2) .
C17 C18 C19 120.1(2) .
C18 C19 C14 120.9(2) .
C21 N1 C25 117.0(3) .
C20 C20 C23 125.8(5) 2_664
N1 C21 C22 122.2(3) .
C23 C22 C21 119.5(3) .
C24 C23 C22 117.3(3) .
C24 C23 C20 117.5(3) .
C22 C23 C20 125.2(3) .
C25 C24 C23 119.5(3) .
N1 C25 C24 124.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.362(3) .
O2 C9 1.369(3) .
O3 C17 1.378(3) .
C1 C2 1.523(3) .
C1 C8 1.523(3) .
C1 C14 1.527(3) .
C2 C7 1.384(3) .
C2 C3 1.399(3) .
C3 C4 1.387(3) .
C4 C5 1.373(4) .
C5 C6 1.377(4) .
C6 C7 1.384(3) .
C8 C13 1.383(3) .
C8 C9 1.393(3) .
C9 C10 1.387(4) .
C10 C11 1.374(4) .
C11 C12 1.374(4) .
C12 C13 1.387(3) .
C14 C19 1.387(3) .
C14 C15 1.388(3) .
C15 C16 1.383(3) .
C16 C17 1.382(3) .
C17 C18 1.376(3) .
C18 C19 1.385(3) .
N1 C21 1.323(4) .
N1 C25 1.329(4) .
C20 C20 1.238(7) 2_664
C20 C23 1.490(4) .
C21 C22 1.395(4) .
C22 C23 1.385(5) .
C23 C24 1.366(5) .
C24 C25 1.357(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.83 1.82 2.635(3) 166.1 .
O2 H2A O3 0.83 1.90 2.707(2) 165.3 1_545
O3 H3A O1 0.83 1.88 2.692(2) 167.3 2_575
O1S H1SA O2 0.907(10) 2.22(3) 3.021(9) 147(4) .
O1S H1SB O2 0.907(10) 2.226(16) 3.127(9) 172(7) 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145534
