#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/45/4504516.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_4504516
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            'C21 H18 N O3'
_chemical_formula_weight         332.36
_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                90.401(3)
_cell_angle_beta                 102.338(3)
_cell_angle_gamma                96.760(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2627(13)
_cell_length_b                   10.0415(16)
_cell_length_c                   10.3726(17)
_cell_measurement_reflns_used    724
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.54
_cell_volume                     834.4(2)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5840
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_type   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0433
_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)+(0.0695P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                2843
_reflns_number_total             3770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050251psi20050603_044455.cif
_cod_data_source_block           4100
_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_database_code               4504516
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 0.05734(14) 0.08822(10) 0.67910(11) 0.0446(3) Uani 1 1 d .
H1A H 0.131(2) 0.042(2) 0.7223(18) 0.065(6) Uiso 1 1 d .
O2 O 0.28112(15) 0.92306(10) 0.80676(11) 0.0480(3) Uani 1 1 d .
H2A H 0.340(3) 0.907(2) 0.748(2) 0.080(6) Uiso 1 1 d .
O3 O 0.42110(13) 0.63166(11) 0.51464(10) 0.0434(3) Uani 1 1 d .
H3A H 0.469(2) 0.624(2) 0.453(2) 0.080(7) Uiso 1 1 d .
N1 N 0.43565(15) 0.95878(12) 0.60778(11) 0.0408(3) Uani 1 1 d .
C1 C 0.31103(15) 0.64184(12) 0.74875(12) 0.0273(3) Uani 1 1 d .
H1 H 0.2477 0.6901 0.6756 0.033 Uiso 1 1 calc R
C2 C 0.25103(15) 0.49218(12) 0.72208(11) 0.0273(3) Uani 1 1 d .
C3 C 0.35293(16) 0.39442(13) 0.76720(13) 0.0324(3) Uani 1 1 d .
H3 H 0.4654 0.4203 0.8080 0.039 Uiso 1 1 calc R
C4 C 0.29197(17) 0.25902(13) 0.75317(13) 0.0345(3) Uani 1 1 d .
H4 H 0.3628 0.1943 0.7849 0.041 Uiso 1 1 calc R
C5 C 0.12720(16) 0.21946(13) 0.69261(13) 0.0320(3) Uani 1 1 d .
C6 C 0.02517(16) 0.31578(13) 0.64289(13) 0.0324(3) Uani 1 1 d .
H6 H -0.0859 0.2896 0.5986 0.039 Uiso 1 1 calc R
C7 C 0.08701(15) 0.45014(13) 0.65857(12) 0.0297(3) Uani 1 1 d .
H7 H 0.0165 0.5146 0.6255 0.036 Uiso 1 1 calc R
C8 C 0.27065(15) 0.69211(12) 0.87627(12) 0.0279(3) Uani 1 1 d .
C9 C 0.23848(17) 0.60562(14) 0.97432(13) 0.0351(3) Uani 1 1 d .
H9 H 0.2426 0.5133 0.9620 0.042 Uiso 1 1 calc R
C10 C 0.20067(18) 0.65070(15) 1.08932(13) 0.0405(3) Uani 1 1 d .
H10 H 0.1788 0.5896 1.1535 0.049 Uiso 1 1 calc R
C11 C 0.19515(18) 0.78533(15) 1.10936(14) 0.0429(4) Uani 1 1 d .
H11 H 0.1704 0.8167 1.1877 0.051 Uiso 1 1 calc R
C12 C 0.22603(18) 0.87422(15) 1.01428(14) 0.0421(4) Uani 1 1 d .
H12 H 0.2225 0.9664 1.0279 0.051 Uiso 1 1 calc R
C13 C 0.26231(16) 0.82806(13) 0.89835(13) 0.0331(3) Uani 1 1 d .
C14 C 0.49508(15) 0.67319(12) 0.74545(12) 0.0283(3) Uani 1 1 d .
C15 C 0.54510(16) 0.66150(13) 0.62601(13) 0.0329(3) Uani 1 1 d .
C16 C 0.71157(19) 0.68230(14) 0.61973(16) 0.0430(4) Uani 1 1 d .
H16 H 0.7431 0.6721 0.5387 0.052 Uiso 1 1 calc R
C17 C 0.83097(18) 0.71803(15) 0.73296(17) 0.0476(4) Uani 1 1 d .
H17 H 0.9442 0.7329 0.7288 0.057 Uiso 1 1 calc R
C18 C 0.78597(18) 0.73206(15) 0.85207(16) 0.0454(4) Uani 1 1 d .
H18 H 0.8677 0.7570 0.9291 0.055 Uiso 1 1 calc R
C19 C 0.61854(17) 0.70900(14) 0.85740(14) 0.0363(3) Uani 1 1 d .
H19 H 0.5882 0.7179 0.9391 0.044 Uiso 1 1 calc R
C20 C 0.33706(18) 0.97850(14) 0.49245(15) 0.0409(3) Uani 1 1 d .
H20 H 0.2207 0.9643 0.4837 0.049 Uiso 1 1 calc R
C21 C 0.59879(19) 0.98070(14) 0.61461(14) 0.0407(3) Uani 1 1 d .
H21 H 0.6725 0.9680 0.6949 0.049 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_3
C20 N1 C21 116.72(12) .
C14 C1 C8 112.92(10) .
C14 C1 C2 111.21(9) .
C8 C1 C2 111.41(10) .
C3 C2 C7 117.81(12) .
C3 C2 C1 121.93(11) .
C7 C2 C1 120.13(10) .
C2 C3 C4 121.25(12) .
C5 C4 C3 120.00(12) .
O1 C5 C4 123.17(12) .
O1 C5 C6 117.38(12) .
C4 C5 C6 119.45(12) .
C7 C6 C5 119.90(12) .
C6 C7 C2 121.53(12) .
C9 C8 C13 116.96(12) .
C9 C8 C1 122.11(11) .
C13 C8 C1 120.92(11) .
C10 C9 C8 122.23(13) .
C11 C10 C9 119.67(13) .
C10 C11 C12 119.80(13) .
C11 C12 C13 120.23(13) .
O2 C13 C12 115.76(12) .
O2 C13 C8 123.07(12) .
C12 C13 C8 121.11(12) .
C19 C14 C15 117.44(12) .
C19 C14 C1 123.00(11) .
C15 C14 C1 119.52(11) .
O3 C15 C16 121.60(13) .
O3 C15 C14 116.98(11) .
C16 C15 C14 121.40(13) .
C17 C16 C15 119.59(14) .
C18 C17 C16 120.55(13) .
C17 C18 C19 119.30(14) .
C14 C19 C18 121.70(14) .
N1 C20 C21 121.49(14) 2_676
N1 C21 C20 121.80(13) 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.3688(16) .
O2 C13 1.3702(16) .
O3 C15 1.3752(17) .
N1 C20 1.3261(19) .
N1 C21 1.3266(19) .
C1 C14 1.5240(17) .
C1 C8 1.5280(16) .
C1 C2 1.5299(17) .
C2 C3 1.3871(17) .
C2 C7 1.3888(18) .
C3 C4 1.3886(18) .
C4 C5 1.3819(19) .
C5 C6 1.3875(19) .
C6 C7 1.3809(18) .
C8 C9 1.3903(18) .
C8 C13 1.3947(18) .
C9 C10 1.3822(18) .
C10 C11 1.374(2) .
C11 C12 1.379(2) .
C12 C13 1.3891(18) .
C14 C19 1.3856(18) .
C14 C15 1.3955(18) .
C15 C16 1.382(2) .
C16 C17 1.377(2) .
C17 C18 1.375(2) .
C18 C19 1.389(2) .
C20 C21 1.374(2) 2_676
C21 C20 1.374(2) 2_676
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
O2 H2A N1 0.89(2) 1.85(2) 2.6548(16) 151(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86069944
