#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:59:05 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301833 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/43/4114385.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_4114385
loop_
_publ_author_name
'Venu R. Vangala'
'Balakrishna R. Bhogala'
'Archan Dey'
'Gautam R. Desiraju'
'Charlotte K. Broder'
'Philip S. Smith'
'Raju Mondal'
'Judith A. K. Howard'
'Chick C. Wilson'
_publ_contact_author_address
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_email       desiraju@uohyd.ernet.in
_publ_contact_author_fax         '91 40 3010567'
_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_phone       '91 40 3010567'
_publ_section_title
;
 Correspondence between Molecular Functionality and Crystal Structures.
 Supramolecular Chemistry of a Family of Homologated Aminophenols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14495
_journal_page_last               14509
_journal_paper_doi               10.1021/ja037227p
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22
_chemical_melting_point          455(3)
_chemical_name_systematic
; 
 4-(3-aminophenyl)phenol  
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.2352(8)
_cell_length_b                   6.0039(3)
_cell_length_c                   8.1627(4)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.112
_cell_measurement_theta_min      3.273
_cell_volume                     942.68(8)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL-98 (Bruker, 1998)'
_computing_publication_material  'SHELXTL-98 (Bruker, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  /w
_diffrn_measurement_method       'Bruker SMART-6000'
_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  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9004
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       Plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(17)
_refine_ls_extinction_coef       'not refined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0378
_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)+(0.0513P)²+0.0193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                1688
_reflns_number_total             2083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037227psi20030927_031934_01.cif
_cod_data_source_block           6a
_cod_database_code               4114385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
O1 O 0.31922(6) 1.0099(2) 0.19993(18) 0.0300(3) Uani 1 1 d .
H1 H 0.3066(9) 0.917(3) 0.284(3) 0.035(6) Uiso 1 1 d .
N1 N 0.76189(8) 1.2374(3) 0.4411(2) 0.0301(4) Uani 1 1 d .
H1A H 0.7459(14) 1.143(3) 0.515(3) 0.057(8) Uiso 1 1 d .
H1B H 0.7946(11) 1.334(4) 0.489(3) 0.040(6) Uiso 1 1 d .
C1 C 0.38487(8) 1.0934(3) 0.2158(2) 0.0249(4) Uani 1 1 d .
C2 C 0.40384(10) 1.2713(3) 0.1190(2) 0.0315(4) Uani 1 1 d .
H2 H 0.3711 1.3343 0.0452 0.038 Uiso 1 1 calc R
C3 C 0.47037(9) 1.3589(3) 0.1286(2) 0.0314(4) Uani 1 1 d .
H3 H 0.4825 1.4805 0.0598 0.038 Uiso 1 1 calc R
C4 C 0.52001(9) 1.2740(3) 0.2364(2) 0.0248(4) Uani 1 1 d .
C5 C 0.49886(9) 1.0969(3) 0.3349(3) 0.0347(5) Uani 1 1 d .
H5 H 0.5309 1.0370 0.4116 0.042 Uiso 1 1 calc R
C6 C 0.43293(8) 1.0049(3) 0.3253(3) 0.0328(4) Uani 1 1 d .
H6 H 0.4206 0.8824 0.3930 0.039 Uiso 1 1 calc R
C7 C 0.59105(9) 1.3718(3) 0.2485(2) 0.0263(4) Uani 1 1 d .
C8 C 0.64353(9) 1.2624(3) 0.3363(2) 0.0255(4) Uani 1 1 d .
H8 H 0.6341 1.1211 0.3838 0.031 Uiso 1 1 calc R
C9 C 0.70919(9) 1.3567(3) 0.3554(2) 0.0272(4) Uani 1 1 d .
C10 C 0.72411(10) 1.5617(3) 0.2838(2) 0.0316(4) Uani 1 1 d .
H10 H 0.7688 1.6270 0.2965 0.038 Uiso 1 1 calc R
C11 C 0.67326(9) 1.6689(3) 0.1943(3) 0.0328(4) Uani 1 1 d .
H11 H 0.6835 1.8077 0.1439 0.039 Uiso 1 1 calc R
C12 C 0.60728(10) 1.5769(3) 0.1766(2) 0.0315(4) Uani 1 1 d .
H12 H 0.5729 1.6541 0.1151 0.038 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0219(6) 0.0376(7) 0.0303(7) 0.0038(7) -0.0030(6) -0.0036(5)
N1 0.0219(8) 0.0381(9) 0.0303(8) -0.0008(8) -0.0011(7) -0.0025(7)
C1 0.0205(8) 0.0289(9) 0.0252(9) -0.0048(7) 0.0005(7) 0.0009(7)
C2 0.0257(9) 0.0372(10) 0.0317(10) 0.0078(9) -0.0047(7) 0.0013(8)
C3 0.0302(10) 0.0319(10) 0.0321(9) 0.0063(8) 0.0004(8) -0.0006(8)
C4 0.0215(8) 0.0265(9) 0.0262(9) -0.0022(7) 0.0016(6) 0.0030(7)
C5 0.0264(10) 0.0379(11) 0.0398(11) 0.0101(10) -0.0079(8) -0.0020(8)
C6 0.0264(9) 0.0340(10) 0.0378(11) 0.0089(9) -0.0024(9) -0.0022(8)
C7 0.0243(8) 0.0280(10) 0.0266(9) -0.0051(7) 0.0010(7) 0.0014(7)
C8 0.0244(8) 0.0290(8) 0.0232(8) -0.0027(7) 0.0029(7) -0.0007(7)
C9 0.0247(9) 0.0324(10) 0.0246(9) -0.0066(8) 0.0022(8) 0.0033(7)
C10 0.0249(9) 0.0346(10) 0.0352(10) -0.0055(9) 0.0067(7) -0.0075(8)
C11 0.0316(10) 0.0290(9) 0.0379(10) 0.0009(10) 0.0050(8) -0.0037(8)
C12 0.0276(9) 0.0314(9) 0.0353(11) 0.0027(9) 0.0006(8) 0.0003(8)
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
C1 O1 H1 113.5(12)
C9 N1 H1A 114.2(17)
C9 N1 H1B 111.7(13)
H1A N1 H1B 110(2)
O1 C1 C2 118.36(16)
O1 C1 C6 122.41(16)
C2 C1 C6 119.23(16)
C1 C2 C3 120.41(17)
C1 C2 H2 119.8
C3 C2 H2 119.8
C2 C3 C4 121.94(18)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 116.30(17)
C5 C4 C7 122.00(15)
C3 C4 C7 121.68(16)
C6 C5 C4 122.60(17)
C6 C5 H5 118.7
C4 C5 H5 118.7
C5 C6 C1 119.50(17)
C5 C6 H6 120.2
C1 C6 H6 120.2
C12 C7 C8 117.78(16)
C12 C7 C4 121.57(16)
C8 C7 C4 120.64(15)
C9 C8 C7 121.34(17)
C9 C8 H8 119.3
C7 C8 H8 119.3
C10 C9 C8 119.95(17)
C10 C9 N1 120.25(16)
C8 C9 N1 119.72(17)
C11 C10 C9 119.23(17)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C12 121.08(17)
C10 C11 H11 119.5
C12 C11 H11 119.5
C11 C12 C7 120.60(17)
C11 C12 H12 119.7
C7 C12 H12 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3647(19)
O1 H1 0.91(2)
N1 C9 1.425(2)
N1 H1A 0.88(2)
N1 H1B 0.94(2)
C1 C2 1.378(2)
C1 C6 1.391(2)
C2 C3 1.386(3)
C2 H2 0.9500
C3 C4 1.395(2)
C3 H3 0.9500
C4 C5 1.393(2)
C4 C7 1.491(2)
C5 C6 1.385(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C12 1.400(2)
C7 C8 1.402(2)
C8 C9 1.393(2)
C8 H8 0.9500
C9 C10 1.392(2)
C10 C11 1.381(3)
C10 H10 0.9500
C11 C12 1.391(2)
C11 H11 0.9500
C12 H12 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -178.76(17)
C6 C1 C2 C3 1.0(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 -0.5(3)
C2 C3 C4 C7 -178.79(17)
C3 C4 C5 C6 1.5(3)
C7 C4 C5 C6 179.79(17)
C4 C5 C6 C1 -1.2(3)
O1 C1 C6 C5 179.72(17)
C2 C1 C6 C5 -0.1(3)
C5 C4 C7 C12 -165.93(18)
C3 C4 C7 C12 12.3(3)
C5 C4 C7 C8 12.5(3)
C3 C4 C7 C8 -169.27(17)
C12 C7 C8 C9 1.6(3)
C4 C7 C8 C9 -176.86(15)
C7 C8 C9 C10 -1.2(2)
C7 C8 C9 N1 -178.00(17)
C8 C9 C10 C11 -0.1(3)
N1 C9 C10 C11 176.68(17)
C9 C10 C11 C12 0.9(3)
C10 C11 C12 C7 -0.5(3)
C8 C7 C12 C11 -0.8(3)
C4 C7 C12 C11 177.71(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2037126
2 PubChem 2756362
