#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/34/7203433.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_7203433
loop_
_publ_author_name
'Dey, Archan'
'Desiraju, Gautam R.'
_publ_section_title
;
 Dimorphs of 4′-amino-4-hydroxy-2′-methylbiphenyl:
 Assessment of likelihood of polymorphism in flexible molecules
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              477
_journal_paper_doi               10.1039/b605751a
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_name_systematic
;
4-amino-2-methyl-4'-hydroxydiphenyl
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.3320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1587(2)
_cell_length_b                   9.5748(2)
_cell_length_c                   19.9175(4)
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.239
_cell_measurement_theta_min      2.201
_cell_volume                     2115.05(7)
_computing_cell_refinement       'Bruker SAINT'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       /w
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16432
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0406
_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)+(0.0578P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2929
_reflns_number_total             4855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b605751a.txt
_cod_data_source_block           FORM-II
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7203433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.38007(10) 0.56281(12) 0.23858(5) 0.0308(3) Uani 1 1 d . . .
H1A H 0.3930(18) 0.484(2) 0.2171(9) 0.055(6) Uiso 1 1 d . . .
C1 C 0.46399(14) 0.57071(15) 0.29460(7) 0.0242(3) Uani 1 1 d . . .
C2 C 0.46924(15) 0.69317(15) 0.33181(7) 0.0277(4) Uani 1 1 d . . .
H2 H 0.4182 0.7671 0.3183 0.033 Uiso 1 1 calc R . .
C3 C 0.55045(15) 0.70520(15) 0.38902(7) 0.0272(4) Uani 1 1 d . . .
H3 H 0.5525 0.7874 0.4140 0.033 Uiso 1 1 calc R . .
C4 C 0.62980(14) 0.59697(15) 0.41043(7) 0.0239(3) Uani 1 1 d . . .
C5 C 0.62377(15) 0.47541(15) 0.37129(7) 0.0267(4) Uani 1 1 d . . .
H5 H 0.6760 0.4020 0.3840 0.032 Uiso 1 1 calc R . .
C6 C 0.54237(15) 0.46160(15) 0.31442(7) 0.0260(4) Uani 1 1 d . . .
H6 H 0.5398 0.3795 0.2893 0.031 Uiso 1 1 calc R . .
C7 C 0.71551(15) 0.61313(14) 0.47243(7) 0.0240(3) Uani 1 1 d . . .
C8 C 0.67237(15) 0.62062(15) 0.53559(7) 0.0261(3) Uani 1 1 d . . .
H8 H 0.5901 0.6109 0.5383 0.031 Uiso 1 1 calc R . .
C9 C 0.74887(15) 0.64203(15) 0.59417(7) 0.0281(4) Uani 1 1 d . . .
H9 H 0.7180 0.6445 0.6357 0.034 Uiso 1 1 calc R . .
C10 C 0.87136(15) 0.65986(14) 0.59113(7) 0.0257(3) Uani 1 1 d . . .
C11 C 0.91638(15) 0.65032(15) 0.52864(7) 0.0271(4) Uani 1 1 d . . .
H11 H 0.9988 0.6596 0.5264 0.033 Uiso 1 1 calc R . .
C12 C 0.83999(15) 0.62713(15) 0.46943(7) 0.0254(3) Uani 1 1 d . . .
C13 C 0.89237(16) 0.62358(18) 0.40285(8) 0.0357(4) Uani 1 1 d . . .
H13A H 0.9783 0.6344 0.4106 0.054 Uiso 1 1 calc R . .
H13B H 0.8587 0.6983 0.3746 0.054 Uiso 1 1 calc R . .
H13C H 0.8734 0.5358 0.3809 0.054 Uiso 1 1 calc R . .
N1 N 0.94991(15) 0.68057(15) 0.65134(7) 0.0315(3) Uani 1 1 d . . .
H1B H 0.9210(17) 0.7433(19) 0.6778(9) 0.044(6) Uiso 1 1 d . . .
H1C H 1.0266(19) 0.7054(19) 0.6425(9) 0.048(6) Uiso 1 1 d . . .
O2 O 0.40997(11) 0.33229(11) 0.16526(5) 0.0292(3) Uani 1 1 d . . .
H2A H 0.4006(18) 0.248(2) 0.1848(10) 0.055(6) Uiso 1 1 d . . .
C21 C 0.34412(14) 0.34548(15) 0.10287(7) 0.0240(3) Uani 1 1 d . . .
C22 C 0.35801(15) 0.46713(15) 0.06624(7) 0.0282(4) Uani 1 1 d . . .
H22 H 0.4130 0.5347 0.0832 0.034 Uiso 1 1 calc R . .
C23 C 0.29020(15) 0.48768(15) 0.00466(7) 0.0266(4) Uani 1 1 d . . .
H23 H 0.3000 0.5696 -0.0192 0.032 Uiso 1 1 calc R . .
C24 C 0.20728(14) 0.38785(15) -0.02245(7) 0.0234(3) Uani 1 1 d . . .
C26 C 0.26461(15) 0.24378(15) 0.07623(7) 0.0262(4) Uani 1 1 d . . .
H26 H 0.2568 0.1608 0.0996 0.031 Uiso 1 1 calc R . .
C25 C 0.19685(14) 0.26571(15) 0.01493(7) 0.0257(3) Uani 1 1 d . . .
H25 H 0.1426 0.1972 -0.0020 0.031 Uiso 1 1 calc R . .
C27 C 0.12861(14) 0.40782(14) -0.08726(7) 0.0224(3) Uani 1 1 d . . .
C28 C 0.00362(14) 0.40034(14) -0.08690(7) 0.0243(3) Uani 1 1 d . . .
H28 H -0.0277 0.3890 -0.0459 0.029 Uiso 1 1 calc R . .
C29 C -0.07521(15) 0.40919(14) -0.14548(7) 0.0242(3) Uani 1 1 d . . .
H29 H -0.1580 0.4060 -0.1434 0.029 Uiso 1 1 calc R . .
C30 C -0.02978(15) 0.42296(14) -0.20761(7) 0.0235(3) Uani 1 1 d . . .
C31 C 0.09407(14) 0.43328(15) -0.20849(7) 0.0257(3) Uani 1 1 d . . .
H31 H 0.1247 0.4444 -0.2497 0.031 Uiso 1 1 calc R . .
C32 C 0.17411(14) 0.42752(15) -0.14968(7) 0.0253(3) Uani 1 1 d . . .
C33 C 0.30759(16) 0.43897(19) -0.15484(8) 0.0394(4) Uani 1 1 d . . .
H33A H 0.3250 0.4037 -0.1978 0.059 Uiso 1 1 calc R . .
H33B H 0.3510 0.3854 -0.1194 0.059 Uiso 1 1 calc R . .
H33C H 0.3317 0.5351 -0.1506 0.059 Uiso 1 1 calc R . .
N2 N -0.10796(14) 0.42001(14) -0.26925(7) 0.0278(3) Uani 1 1 d . . .
H2C H -0.1857(19) 0.4331(19) -0.2616(9) 0.048(6) Uiso 1 1 d . . .
H2B H -0.0865(16) 0.4891(19) -0.2989(9) 0.042(5) 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
C1 O1 H1A 107.8(13) . . ?
O1 C1 C2 117.70(13) . . ?
O1 C1 C6 122.58(13) . . ?
C2 C1 C6 119.72(14) . . ?
C3 C2 C1 119.84(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.72(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.18(14) . . ?
C5 C4 C7 122.52(13) . . ?
C3 C4 C7 120.30(13) . . ?
C6 C5 C4 121.67(14) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.86(13) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C12 118.32(14) . . ?
C8 C7 C4 119.99(15) . . ?
C12 C7 C4 121.63(13) . . ?
C9 C8 C7 121.68(16) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 120.11(14) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.00(14) . . ?
C9 C10 N1 120.04(14) . . ?
C11 C10 N1 120.88(16) . . ?
C12 C11 C10 121.19(15) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 119.65(14) . . ?
C11 C12 C13 119.16(15) . . ?
C7 C12 C13 121.13(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 N1 H1B 111.5(12) . . ?
C10 N1 H1C 111.9(11) . . ?
H1B N1 H1C 110.3(16) . . ?
C21 O2 H2A 113.2(12) . . ?
O2 C21 C26 122.49(13) . . ?
O2 C21 C22 118.05(13) . . ?
C26 C21 C22 119.45(14) . . ?
C23 C22 C21 120.17(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 121.33(14) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 117.19(14) . . ?
C23 C24 C27 123.27(13) . . ?
C25 C24 C27 119.51(13) . . ?
C25 C26 C21 119.88(14) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C26 C25 C24 121.94(14) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C28 C27 C32 117.98(14) . . ?
C28 C27 C24 118.79(13) . . ?
C32 C27 C24 123.16(14) . . ?
C29 C28 C27 122.30(14) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C28 C29 C30 119.64(15) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 118.56(14) . . ?
C31 C30 N2 120.41(14) . . ?
C29 C30 N2 120.97(15) . . ?
C30 C31 C32 122.24(14) . . ?
C30 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
C31 C32 C27 119.21(15) . . ?
C31 C32 C33 119.08(14) . . ?
C27 C32 C33 121.69(14) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 N2 H2C 111.0(12) . . ?
C30 N2 H2B 110.8(11) . . ?
H2C N2 H2B 109.0(15) . . ?
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
O1 C1 1.3774(18) . ?
O1 H1A 0.89(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(2) . ?
C4 C7 1.484(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.397(2) . ?
C7 C12 1.403(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(2) . ?
C10 N1 1.419(2) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.507(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 H1B 0.883(19) . ?
N1 H1C 0.92(2) . ?
O2 C21 1.3778(17) . ?
O2 H2A 0.91(2) . ?
C21 C26 1.383(2) . ?
C21 C22 1.392(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(2) . ?
C24 C27 1.491(2) . ?
C26 C25 1.379(2) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C27 C28 1.397(2) . ?
C27 C32 1.407(2) . ?
C28 C29 1.384(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.394(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.388(2) . ?
C30 N2 1.4258(19) . ?
C31 C32 1.393(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.508(2) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N2 H2C 0.91(2) . ?
N2 H2B 0.936(18) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.90(14) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C7 -179.65(15) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C7 C4 C5 C6 179.05(14) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
O1 C1 C6 C5 -179.50(14) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C5 C4 C7 C8 -112.17(17) . . . . ?
C3 C4 C7 C8 67.59(19) . . . . ?
C5 C4 C7 C12 70.5(2) . . . . ?
C3 C4 C7 C12 -109.71(17) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C4 C7 C8 C9 -177.01(13) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C9 C10 C11 -2.5(2) . . . . ?
C8 C9 C10 N1 -179.43(13) . . . . ?
C9 C10 C11 C12 1.8(2) . . . . ?
N1 C10 C11 C12 178.68(13) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C10 C11 C12 C13 177.49(14) . . . . ?
C8 C7 C12 C11 -1.1(2) . . . . ?
C4 C7 C12 C11 176.23(13) . . . . ?
C8 C7 C12 C13 -178.51(13) . . . . ?
C4 C7 C12 C13 -1.2(2) . . . . ?
O2 C21 C22 C23 -177.32(14) . . . . ?
C26 C21 C22 C23 1.9(2) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
C22 C23 C24 C25 -0.7(2) . . . . ?
C22 C23 C24 C27 177.44(14) . . . . ?
O2 C21 C26 C25 176.90(14) . . . . ?
C22 C21 C26 C25 -2.3(2) . . . . ?
C21 C26 C25 C24 1.2(2) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C27 C24 C25 C26 -177.91(14) . . . . ?
C23 C24 C27 C28 -121.96(16) . . . . ?
C25 C24 C27 C28 56.17(19) . . . . ?
C23 C24 C27 C32 61.1(2) . . . . ?
C25 C24 C27 C32 -120.78(16) . . . . ?
C32 C27 C28 C29 1.1(2) . . . . ?
C24 C27 C28 C29 -175.96(12) . . . . ?
C27 C28 C29 C30 1.5(2) . . . . ?
C28 C29 C30 C31 -2.7(2) . . . . ?
C28 C29 C30 N2 174.44(13) . . . . ?
C29 C30 C31 C32 1.3(2) . . . . ?
N2 C30 C31 C32 -175.81(13) . . . . ?
C30 C31 C32 C27 1.3(2) . . . . ?
C30 C31 C32 C33 179.77(14) . . . . ?
C28 C27 C32 C31 -2.5(2) . . . . ?
C24 C27 C32 C31 174.49(13) . . . . ?
C28 C27 C32 C33 179.09(14) . . . . ?
C24 C27 C32 C33 -3.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195124
