##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-(4-hydroxyphenyl)-2,2,4-trimethylchroman
;
_chemical_name_common
;
racemic guest-free Dianin's compound
;
_chemical_formula_moiety     'C18 H20 O2'
_chemical_formula_sum     'C18 H20 O2'
_chemical_formula_iupac     'C18 H20 O2'
_chemical_formula_weight     268.34
_chemical_melting_point     ?
_symmetry_cell_setting     hexagonal
_space_group_name_H-M_alt     'R -3'
_space_group_name_Hall     '-R 3'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-y, x-y, z'
    '-x+y, -x, z'
    'x+2/3, y+1/3, z+1/3'
    '-y+2/3, x-y+1/3, z+1/3'
    '-x+y+2/3, -x+1/3, z+1/3'
    'x+1/3, y+2/3, z+2/3'
    '-y+1/3, x-y+2/3, z+2/3'
    '-x+y+1/3, -x+2/3, z+2/3'
    '-x, -y, -z'
    'y, -x+y, -z'
    'x-y, x, -z'
    '-x+2/3, -y+1/3, -z+1/3'
    'y+2/3, -x+y+1/3, -z+1/3'
    'x-y+2/3, x+1/3, -z+1/3'
    '-x+1/3, -y+2/3, -z+2/3'
    'y+1/3, -x+y+2/3, -z+2/3'
    'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a     26.7321(5)
_cell_length_b     26.7321(5)
_cell_length_c     10.8700(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     120.00
_cell_volume     6727.1(3)
_cell_formula_units_Z     18
_cell_measurement_reflns_used     6337
_cell_measurement_theta_min     3.3038
_cell_measurement_theta_max     76.0230
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.192
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2592
_exptl_absorpt_coefficient_mu     0.599
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlisPro; Agilent Technologies, 2010)'
_exptl_absorpt_correction_T_min     0.83552
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type
                       'Agilent SuperNova Dual (Cu at zero) with Atlas detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.5598
_diffrn_reflns_number     11837
_diffrn_reflns_av_R_equivalents     0.0183
_diffrn_reflns_av_sigmaI/netI     0.0150
_diffrn_reflns_theta_min     9.02
_diffrn_reflns_theta_max     74.49
_diffrn_reflns_theta_full     74.49
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -31
_diffrn_reflns_limit_h_max     33
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_k_max     33
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     3047
_reflns_number_gt     2871
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0390
_refine_ls_R_factor_gt     0.0371
_refine_ls_wR_factor_gt     0.1227
_refine_ls_wR_factor_ref     0.1261
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     3047
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.1000P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.257
_refine_diff_density_min     -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_cell_refinement     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.07179(3) 0.57876(3) 0.03764(6) 0.0167(2) Uani d . 1 . .
    O O2 0.21522(3) 0.60269(4) 0.64902(7) 0.0232(2) Uani d . 1 . .
    H H2A 0.2306(8) 0.5849(8) 0.6528(18) 0.044(5) Uiso d . 1 . .
    C C2 0.10884(4) 0.55538(4) 0.07176(9) 0.0149(2) Uani d . 1 . .
    C C3 0.07361(4) 0.50052(4) 0.14702(8) 0.0144(2) Uani d . 1 . .
    H H3A 0.0991 0.4851 0.1703 0.017 Uiso calc R 1 . .
    H H3B 0.0426 0.4714 0.0940 0.017 Uiso calc R 1 . .
    C C4 0.04576(4) 0.50773(4) 0.26490(9) 0.0137(2) Uani d . 1 . .
    C C5 0.02017(4) 0.54590(4) 0.23359(9) 0.0142(2) Uani d . 1 . .
    C C6 -0.02024(4) 0.54841(4) 0.31163(9) 0.0162(2) Uani d . 1 . .
    H H6A -0.0313 0.5261 0.3850 0.019 Uiso calc R 1 . .
    C C7 -0.04456(4) 0.58248(4) 0.28507(9) 0.0182(2) Uani d . 1 . .
    H H7A -0.0716 0.5836 0.3399 0.022 Uiso calc R 1 . .
    C C8 -0.02891(4) 0.61496(4) 0.17747(10) 0.0182(2) Uani d . 1 . .
    H H8A -0.0451 0.6387 0.1588 0.022 Uiso calc R 1 . .
    C C9 0.01026(4) 0.61267(4) 0.09758(9) 0.0167(2) Uani d . 1 . .
    H H9A 0.0204 0.6343 0.0234 0.020 Uiso calc R 1 . .
    C C10 0.03508(4) 0.57864(4) 0.12539(9) 0.0144(2) Uani d . 1 . .
    C C11 0.08958(4) 0.53276(4) 0.37129(8) 0.0139(2) Uani d . 1 . .
    C C12 0.11769(4) 0.50340(4) 0.41207(9) 0.0161(2) Uani d . 1 . .
    H H12A 0.1083 0.4675 0.3754 0.019 Uiso calc R 1 . .
    C C13 0.15895(4) 0.52555(5) 0.50485(9) 0.0173(2) Uani d . 1 . .
    H H13A 0.1773 0.5048 0.5311 0.021 Uiso calc R 1 . .
    C C14 0.17331(4) 0.57812(4) 0.55921(9) 0.0158(2) Uani d . 1 . .
    C C15 0.14512(4) 0.60733(4) 0.52297(9) 0.0164(2) Uani d . 1 . .
    H H15A 0.1539 0.6427 0.5615 0.020 Uiso calc R 1 . .
    C C16 0.10388(4) 0.58463(4) 0.42984(9) 0.0154(2) Uani d . 1 . .
    H H16A 0.0849 0.6051 0.4055 0.018 Uiso calc R 1 . .
    C C17 -0.00316(4) 0.44682(4) 0.30097(9) 0.0174(2) Uani d . 1 . .
    H H17A -0.0201 0.4489 0.3794 0.026 Uiso calc R 1 . .
    H H17B 0.0126 0.4208 0.3093 0.026 Uiso calc R 1 . .
    H H17C -0.0330 0.4321 0.2370 0.026 Uiso calc R 1 . .
    C C18 0.12616(5) 0.54015(5) -0.04963(9) 0.0195(2) Uani d . 1 . .
    H H18A 0.1458 0.5748 -0.1011 0.029 Uiso calc R 1 . .
    H H18B 0.0916 0.5107 -0.0922 0.029 Uiso calc R 1 . .
    H H18C 0.1523 0.5251 -0.0339 0.029 Uiso calc R 1 . .
    C C19 0.16176(4) 0.60295(4) 0.13728(9) 0.0183(2) Uani d . 1 . .
    H H19A 0.1841 0.6347 0.0798 0.028 Uiso calc R 1 . .
    H H19B 0.1859 0.5874 0.1670 0.028 Uiso calc R 1 . .
    H H19C 0.1493 0.6173 0.2071 0.028 Uiso calc R 1 . .
_geom_special_details
;
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C10 . 1.3674(12) ?
    O1 C2 . 1.4587(11) ?
    O2 C14 . 1.3798(12) ?
    O2 H2A . 0.77(2) ?
    C2 C18 . 1.5199(13) ?
    C2 C3 . 1.5251(13) ?
    C2 C19 . 1.5252(13) ?
    C3 C4 . 1.5418(12) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.5241(13) ?
    C4 C11 . 1.5406(13) ?
    C4 C17 . 1.5446(13) ?
    C5 C10 . 1.3998(13) ?
    C5 C6 . 1.4012(13) ?
    C6 C7 . 1.3884(14) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.3905(15) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.3852(14) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.4009(14) ?
    C9 H9A . 0.9500 ?
    C11 C16 . 1.3943(14) ?
    C11 C12 . 1.4025(13) ?
    C12 C13 . 1.3897(14) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.3899(14) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.3863(14) ?
    C15 C16 . 1.3926(14) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 O1 C2 . . 117.51(7) ?
    C14 O2 H2A . . 107.5(14) ?
    O1 C2 C18 . . 104.90(7) ?
    O1 C2 C3 . . 108.86(8) ?
    C18 C2 C3 . . 109.41(8) ?
    O1 C2 C19 . . 107.88(8) ?
    C18 C2 C19 . . 110.42(8) ?
    C3 C2 C19 . . 114.87(8) ?
    C2 C3 C4 . . 115.48(8) ?
    C2 C3 H3A . . 108.4 ?
    C4 C3 H3A . . 108.4 ?
    C2 C3 H3B . . 108.4 ?
    C4 C3 H3B . . 108.4 ?
    H3A C3 H3B . . 107.5 ?
    C5 C4 C11 . . 112.04(8) ?
    C5 C4 C3 . . 107.74(8) ?
    C11 C4 C3 . . 111.60(8) ?
    C5 C4 C17 . . 109.61(8) ?
    C11 C4 C17 . . 109.06(8) ?
    C3 C4 C17 . . 106.64(7) ?
    C10 C5 C6 . . 117.66(9) ?
    C10 C5 C4 . . 121.56(9) ?
    C6 C5 C4 . . 120.77(9) ?
    C7 C6 C5 . . 122.04(9) ?
    C7 C6 H6A . . 119.0 ?
    C5 C6 H6A . . 119.0 ?
    C6 C7 C8 . . 119.42(9) ?
    C6 C7 H7A . . 120.3 ?
    C8 C7 H7A . . 120.3 ?
    C9 C8 C7 . . 119.86(9) ?
    C9 C8 H8A . . 120.1 ?
    C7 C8 H8A . . 120.1 ?
    C8 C9 C10 . . 120.49(9) ?
    C8 C9 H9A . . 119.8 ?
    C10 C9 H9A . . 119.8 ?
    O1 C10 C5 . . 124.56(9) ?
    O1 C10 C9 . . 114.86(8) ?
    C5 C10 C9 . . 120.53(9) ?
    C16 C11 C12 . . 117.08(9) ?
    C16 C11 C4 . . 123.05(8) ?
    C12 C11 C4 . . 119.87(8) ?
    C13 C12 C11 . . 121.60(9) ?
    C13 C12 H12A . . 119.2 ?
    C11 C12 H12A . . 119.2 ?
    C12 C13 C14 . . 119.91(9) ?
    C12 C13 H13A . . 120.0 ?
    C14 C13 H13A . . 120.0 ?
    O2 C14 C15 . . 118.27(9) ?
    O2 C14 C13 . . 122.02(9) ?
    C15 C14 C13 . . 119.71(9) ?
    C14 C15 C16 . . 119.74(9) ?
    C14 C15 H15A . . 120.1 ?
    C16 C15 H15A . . 120.1 ?
    C15 C16 C11 . . 121.92(9) ?
    C15 C16 H16A . . 119.0 ?
    C11 C16 H16A . . 119.0 ?
    C4 C17 H17A . . 109.5 ?
    C4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C2 C18 H18A . . 109.5 ?
    C2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C2 C19 H19A . . 109.5 ?
    C2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 O1 C2 C18 . . . . 159.09(8) ?
    C10 O1 C2 C3 . . . . 42.07(11) ?
    C10 O1 C2 C19 . . . . -83.19(10) ?
    O1 C2 C3 C4 . . . . -57.81(10) ?
    C18 C2 C3 C4 . . . . -171.92(8) ?
    C19 C2 C3 C4 . . . . 63.25(11) ?
    C2 C3 C4 C5 . . . . 43.21(10) ?
    C2 C3 C4 C11 . . . . -80.17(10) ?
    C2 C3 C4 C17 . . . . 160.82(8) ?
    C11 C4 C5 C10 . . . . 108.14(10) ?
    C3 C4 C5 C10 . . . . -14.99(12) ?
    C17 C4 C5 C10 . . . . -130.66(9) ?
    C11 C4 C5 C6 . . . . -73.21(11) ?
    C3 C4 C5 C6 . . . . 163.66(8) ?
    C17 C4 C5 C6 . . . . 48.00(11) ?
    C10 C5 C6 C7 . . . . -0.86(14) ?
    C4 C5 C6 C7 . . . . -179.56(9) ?
    C5 C6 C7 C8 . . . . 0.48(15) ?
    C6 C7 C8 C9 . . . . 0.54(15) ?
    C7 C8 C9 C10 . . . . -1.15(15) ?
    C2 O1 C10 C5 . . . . -16.20(13) ?
    C2 O1 C10 C9 . . . . 166.42(8) ?
    C6 C5 C10 O1 . . . . -177.00(9) ?
    C4 C5 C10 O1 . . . . 1.70(14) ?
    C6 C5 C10 C9 . . . . 0.24(14) ?
    C4 C5 C10 C9 . . . . 178.93(8) ?
    C8 C9 C10 O1 . . . . 178.24(9) ?
    C8 C9 C10 C5 . . . . 0.75(14) ?
    C5 C4 C11 C16 . . . . -0.58(13) ?
    C3 C4 C11 C16 . . . . 120.33(10) ?
    C17 C4 C11 C16 . . . . -122.10(10) ?
    C5 C4 C11 C12 . . . . -179.68(8) ?
    C3 C4 C11 C12 . . . . -58.76(11) ?
    C17 C4 C11 C12 . . . . 58.80(11) ?
    C16 C11 C12 C13 . . . . -1.41(14) ?
    C4 C11 C12 C13 . . . . 177.74(8) ?
    C11 C12 C13 C14 . . . . -0.20(15) ?
    C12 C13 C14 O2 . . . . -178.01(9) ?
    C12 C13 C14 C15 . . . . 1.89(15) ?
    O2 C14 C15 C16 . . . . 177.99(9) ?
    C13 C14 C15 C16 . . . . -1.91(14) ?
    C14 C15 C16 C11 . . . . 0.25(15) ?
    C12 C11 C16 C15 . . . . 1.39(14) ?
    C4 C11 C16 C15 . . . . -177.74(9) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O2 H2A O2 15_556 0.77(2) 2.00(2) 2.7642(8) 170(2) y
data_III
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(R)-4-(4-Aminophenyl)-2,2,4-trimethylchroman
;
_chemical_name_common
;
Dianin's amine
;
_chemical_formula_moiety     'C18 H21 N O'
_chemical_formula_sum     'C18 H21 N O'
_chemical_formula_iupac     'C18 H21 N O'
_chemical_formula_weight     267.36
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     10.23394(11)
_cell_length_b     10.25106(10)
_cell_length_c     13.47563(13)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1413.71(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     19066
_cell_measurement_theta_min     3.2769
_cell_measurement_theta_max     76.1074
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.256
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.597
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlisPro; Agilent Technologies, 2010)'
_exptl_absorpt_correction_T_min     0.69678
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type
                       'Agilent SuperNova Dual (Cu at zero) with Atlas detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.5598
_diffrn_reflns_number     25124
_diffrn_reflns_av_R_equivalents     0.0239
_diffrn_reflns_av_sigmaI/netI     0.0092
_diffrn_reflns_theta_min     8.99
_diffrn_reflns_theta_max     74.47
_diffrn_reflns_theta_full     74.47
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     2876
_reflns_number_gt     2864
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0265
_refine_ls_R_factor_gt     0.0264
_refine_ls_wR_factor_gt     0.0713
_refine_ls_wR_factor_ref     0.0715
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     1.003
_refine_ls_number_reflns     2876
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0475P)²+0.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.207
_refine_diff_density_min     -0.140
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0082(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
Flack (1983), with 1221 Friedel pairs;
Hooft et al. (2008)
;
_refine_ls_abs_structure_Flack     -0.07(18)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_cell_refinement     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.88215(7) 0.94223(7) 0.65565(5) 0.01961(17) Uani d . 1 . .
    N N1 0.13938(10) 0.86523(11) 0.52978(9) 0.0337(2) Uani d . 1 . .
    H H1A 0.0613(18) 0.8628(18) 0.5687(13) 0.046(5) Uiso d . 1 . .
    H H1B 0.1449(17) 0.8104(17) 0.4768(13) 0.045(4) Uiso d . 1 . .
    C C2 0.83851(9) 0.89108(10) 0.75111(7) 0.0175(2) Uani d . 1 . .
    C C3 0.68941(9) 0.88319(10) 0.74965(7) 0.0171(2) Uani d . 1 . .
    H H3A 0.6596 0.8502 0.8149 0.021 Uiso calc R 1 . .
    H H3B 0.6632 0.8184 0.6990 0.021 Uiso calc R 1 . .
    C C4 0.61698(10) 1.01271(9) 0.72775(7) 0.0162(2) Uani d . 1 . .
    C C5 0.69978(9) 1.09576(9) 0.65762(7) 0.0158(2) Uani d . 1 . .
    C C6 0.65302(10) 1.21559(10) 0.62335(8) 0.0190(2) Uani d . 1 . .
    H H6A 0.5697 1.2449 0.6450 0.023 Uiso calc R 1 . .
    C C7 0.72424(11) 1.29314(10) 0.55870(8) 0.0211(2) Uani d . 1 . .
    H H7A 0.6904 1.3747 0.5372 0.025 Uiso calc R 1 . .
    C C8 0.84560(10) 1.25052(10) 0.52562(7) 0.0208(2) Uani d . 1 . .
    H H8A 0.8946 1.3022 0.4805 0.025 Uiso calc R 1 . .
    C C9 0.89490(10) 1.13243(10) 0.55870(7) 0.0189(2) Uani d . 1 . .
    H H9A 0.9776 1.1029 0.5358 0.023 Uiso calc R 1 . .
    C C10 0.82369(10) 1.05686(9) 0.62538(7) 0.0164(2) Uani d . 1 . .
    C C11 0.48717(9) 0.97822(9) 0.67655(7) 0.0159(2) Uani d . 1 . .
    C C12 0.36565(10) 0.98970(10) 0.72178(8) 0.0200(2) Uani d . 1 . .
    H H12A 0.3605 1.0251 0.7868 0.024 Uiso calc R 1 . .
    C C13 0.25137(10) 0.95068(10) 0.67439(9) 0.0233(2) Uani d . 1 . .
    H H13A 0.1700 0.9596 0.7077 0.028 Uiso calc R 1 . .
    C C14 0.25438(10) 0.89886(10) 0.57923(8) 0.0218(2) Uani d . 1 . .
    C C15 0.37561(10) 0.88785(10) 0.53240(7) 0.0207(2) Uani d . 1 . .
    H H15A 0.3804 0.8533 0.4671 0.025 Uiso calc R 1 . .
    C C16 0.48875(10) 0.92670(9) 0.58016(7) 0.0182(2) Uani d . 1 . .
    H H16A 0.5700 0.9182 0.5466 0.022 Uiso calc R 1 . .
    C C17 0.59236(10) 1.08932(10) 0.82441(7) 0.0205(2) Uani d . 1 . .
    H H17A 0.6762 1.1129 0.8546 0.031 Uiso calc R 1 . .
    H H17B 0.5424 1.0350 0.8707 0.031 Uiso calc R 1 . .
    H H17C 0.5429 1.1687 0.8094 0.031 Uiso calc R 1 . .
    C C18 0.89498(10) 0.97503(10) 0.83433(8) 0.0218(2) Uani d . 1 . .
    H H18A 0.9902 0.9648 0.8360 0.033 Uiso calc R 1 . .
    H H18B 0.8579 0.9474 0.8980 0.033 Uiso calc R 1 . .
    H H18C 0.8731 1.0668 0.8224 0.033 Uiso calc R 1 . .
    C C19 0.89637(10) 0.75535(10) 0.75672(8) 0.0222(2) Uani d . 1 . .
    H H19A 0.9917 0.7607 0.7508 0.033 Uiso calc R 1 . .
    H H19B 0.8614 0.7020 0.7025 0.033 Uiso calc R 1 . .
    H H19C 0.8735 0.7155 0.8205 0.033 Uiso calc R 1 . .
_geom_special_details
;
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C10 . 1.3803(12) ?
    O1 C2 . 1.4592(11) ?
    N1 C14 . 1.3957(14) ?
    N1 H1A . 0.956(19) ?
    N1 H1B . 0.911(18) ?
    C2 C19 . 1.5140(14) ?
    C2 C18 . 1.5272(14) ?
    C2 C3 . 1.5281(13) ?
    C3 C4 . 1.5490(13) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.5283(13) ?
    C4 C11 . 1.5382(13) ?
    C4 C17 . 1.5417(13) ?
    C5 C6 . 1.3969(14) ?
    C5 C10 . 1.3985(14) ?
    C6 C7 . 1.3864(15) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.3900(15) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.3851(15) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.3924(14) ?
    C9 H9A . 0.9500 ?
    C11 C12 . 1.3899(14) ?
    C11 C16 . 1.4024(13) ?
    C12 C13 . 1.3913(15) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.3883(16) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.3966(15) ?
    C15 C16 . 1.3833(15) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 O1 C2 . . 115.71(8) ?
    C14 N1 H1A . . 116.7(10) ?
    C14 N1 H1B . . 118.3(11) ?
    H1A N1 H1B . . 117.8(15) ?
    O1 C2 C19 . . 104.74(8) ?
    O1 C2 C18 . . 109.21(8) ?
    C19 C2 C18 . . 109.47(8) ?
    O1 C2 C3 . . 108.25(8) ?
    C19 C2 C3 . . 110.03(8) ?
    C18 C2 C3 . . 114.66(8) ?
    C2 C3 C4 . . 115.78(8) ?
    C2 C3 H3A . . 108.3 ?
    C4 C3 H3A . . 108.3 ?
    C2 C3 H3B . . 108.3 ?
    C4 C3 H3B . . 108.3 ?
    H3A C3 H3B . . 107.4 ?
    C5 C4 C11 . . 109.24(7) ?
    C5 C4 C17 . . 109.22(8) ?
    C11 C4 C17 . . 110.79(8) ?
    C5 C4 C3 . . 109.27(8) ?
    C11 C4 C3 . . 107.56(8) ?
    C17 C4 C3 . . 110.73(8) ?
    C6 C5 C10 . . 117.30(9) ?
    C6 C5 C4 . . 120.29(9) ?
    C10 C5 C4 . . 122.41(9) ?
    C7 C6 C5 . . 122.14(10) ?
    C7 C6 H6A . . 118.9 ?
    C5 C6 H6A . . 118.9 ?
    C6 C7 C8 . . 119.41(10) ?
    C6 C7 H7A . . 120.3 ?
    C8 C7 H7A . . 120.3 ?
    C9 C8 C7 . . 119.80(10) ?
    C9 C8 H8A . . 120.1 ?
    C7 C8 H8A . . 120.1 ?
    C8 C9 C10 . . 120.21(10) ?
    C8 C9 H9A . . 119.9 ?
    C10 C9 H9A . . 119.9 ?
    O1 C10 C9 . . 115.94(9) ?
    O1 C10 C5 . . 122.95(9) ?
    C9 C10 C5 . . 121.10(9) ?
    C12 C11 C16 . . 116.64(9) ?
    C12 C11 C4 . . 123.82(8) ?
    C16 C11 C4 . . 119.48(8) ?
    C11 C12 C13 . . 121.77(9) ?
    C11 C12 H12A . . 119.1 ?
    C13 C12 H12A . . 119.1 ?
    C14 C13 C12 . . 121.02(10) ?
    C14 C13 H13A . . 119.5 ?
    C12 C13 H13A . . 119.5 ?
    C13 C14 N1 . . 121.12(10) ?
    C13 C14 C15 . . 117.91(9) ?
    N1 C14 C15 . . 120.89(10) ?
    C16 C15 C14 . . 120.67(9) ?
    C16 C15 H15A . . 119.7 ?
    C14 C15 H15A . . 119.7 ?
    C15 C16 C11 . . 121.99(9) ?
    C15 C16 H16A . . 119.0 ?
    C11 C16 H16A . . 119.0 ?
    C4 C17 H17A . . 109.5 ?
    C4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C2 C18 H18A . . 109.5 ?
    C2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C2 C19 H19A . . 109.5 ?
    C2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 O1 C2 C19 . . . . 169.32(8) ?
    C10 O1 C2 C18 . . . . -73.51(10) ?
    C10 O1 C2 C3 . . . . 51.95(11) ?
    O1 C2 C3 C4 . . . . -57.00(10) ?
    C19 C2 C3 C4 . . . . -170.92(8) ?
    C18 C2 C3 C4 . . . . 65.18(11) ?
    C2 C3 C4 C5 . . . . 32.29(11) ?
    C2 C3 C4 C11 . . . . 150.77(8) ?
    C2 C3 C4 C17 . . . . -88.05(10) ?
    C11 C4 C5 C6 . . . . 59.95(11) ?
    C17 C4 C5 C6 . . . . -61.37(12) ?
    C3 C4 C5 C6 . . . . 177.37(8) ?
    C11 C4 C5 C10 . . . . -120.26(10) ?
    C17 C4 C5 C10 . . . . 118.42(10) ?
    C3 C4 C5 C10 . . . . -2.84(12) ?
    C10 C5 C6 C7 . . . . 1.03(15) ?
    C4 C5 C6 C7 . . . . -179.17(9) ?
    C5 C6 C7 C8 . . . . 0.72(16) ?
    C6 C7 C8 C9 . . . . -1.03(15) ?
    C7 C8 C9 C10 . . . . -0.42(15) ?
    C2 O1 C10 C9 . . . . 155.85(8) ?
    C2 O1 C10 C5 . . . . -25.06(13) ?
    C8 C9 C10 O1 . . . . -178.64(8) ?
    C8 C9 C10 C5 . . . . 2.24(14) ?
    C6 C5 C10 O1 . . . . 178.45(9) ?
    C4 C5 C10 O1 . . . . -1.35(14) ?
    C6 C5 C10 C9 . . . . -2.50(13) ?
    C4 C5 C10 C9 . . . . 177.70(9) ?
    C5 C4 C11 C12 . . . . -133.17(9) ?
    C17 C4 C11 C12 . . . . -12.80(13) ?
    C3 C4 C11 C12 . . . . 108.34(10) ?
    C5 C4 C11 C16 . . . . 49.71(11) ?
    C17 C4 C11 C16 . . . . 170.07(8) ?
    C3 C4 C11 C16 . . . . -68.79(10) ?
    C16 C11 C12 C13 . . . . 0.73(14) ?
    C4 C11 C12 C13 . . . . -176.47(9) ?
    C11 C12 C13 C14 . . . . -0.25(16) ?
    C12 C13 C14 N1 . . . . -177.03(10) ?
    C12 C13 C14 C15 . . . . -0.36(16) ?
    C13 C14 C15 C16 . . . . 0.46(15) ?
    N1 C14 C15 C16 . . . . 177.14(10) ?
    C14 C15 C16 C11 . . . . 0.03(15) ?
    C12 C11 C16 C15 . . . . -0.62(14) ?
    C4 C11 C16 C15 . . . . 176.71(9) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1A O1 1_455 0.956(19) 2.323(19) 3.2295(14) 157.9(15) y
data_IV
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(S)-4-(4-Aminophenyl)-2,2,4-trimethylthiachroman
;
_chemical_name_common
;
Thiadianin's amine
;
_chemical_formula_moiety     'C18 H21 N S'
_chemical_formula_sum     'C18 H21 N S'
_chemical_formula_iupac     'C18 H21 N S'
_chemical_formula_weight     283.42
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     10.6043(6)
_cell_length_b     10.4104(5)
_cell_length_c     13.4126(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1480.68(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5377
_cell_measurement_theta_min     3.2923
_cell_measurement_theta_max     75.7604
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.271
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     1.830
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlisPro; Agilent Technologies, 2010)'
_exptl_absorpt_correction_T_min     0.65435
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.0(10)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type
                       'Agilent SuperNova Dual (Cu at zero) with Atlas detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.5598
_diffrn_reflns_number     6825
_diffrn_reflns_av_R_equivalents     0.0188
_diffrn_reflns_av_sigmaI/netI     0.0220
_diffrn_reflns_theta_min     8.91
_diffrn_reflns_theta_max     74.48
_diffrn_reflns_theta_full     74.48
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     3015
_reflns_number_gt     2976
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0276
_refine_ls_R_factor_gt     0.0272
_refine_ls_wR_factor_gt     0.0693
_refine_ls_wR_factor_ref     0.0697
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     3015
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0510P)²+0.1850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.226
_refine_diff_density_min     -0.262
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), with 1281 Friedel pairs'
_refine_ls_abs_structure_Flack     0.016(11)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_cell_refinement     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_data_reduction     'CrysAlisPro (Agilent Technologies, 2010)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and Mercury (Version 2.4; Macrae et
al., 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.38897(3) 0.91546(3) 0.36886(2) 0.01926(9) Uani d . 1 . .
    N N1 -0.31310(12) 0.85585(12) 0.49801(10) 0.0248(3) Uani d . 1 . .
    H H1A -0.3838(19) 0.8461(18) 0.4644(13) 0.025(4) Uiso d . 1 . .
    H H1B -0.2944(19) 0.788(2) 0.5429(15) 0.035(5) Uiso d . 1 . .
    C C2 0.33254(12) 0.87819(12) 0.24344(9) 0.0169(2) Uani d . 1 . .
    C C3 0.18820(11) 0.88597(12) 0.24655(9) 0.0153(2) Uani d . 1 . .
    H H3A 0.1582 0.8205 0.2945 0.018 Uiso calc R 1 . .
    H H3B 0.1563 0.8607 0.1800 0.018 Uiso calc R 1 . .
    C C4 0.12454(11) 1.01631(11) 0.27477(8) 0.0141(2) Uani d . 1 . .
    C C5 0.20406(11) 1.10235(12) 0.34388(9) 0.0144(2) Uani d . 1 . .
    C C6 0.15741(12) 1.22434(12) 0.36787(10) 0.0189(2) Uani d . 1 . .
    H H6A 0.0794 1.2508 0.3397 0.023 Uiso calc R 1 . .
    C C7 0.22048(13) 1.30817(13) 0.43106(10) 0.0208(3) Uani d . 1 . .
    H H7A 0.1861 1.3904 0.4452 0.025 Uiso calc R 1 . .
    C C8 0.33499(13) 1.27065(13) 0.47374(9) 0.0196(2) Uani d . 1 . .
    H H8A 0.3790 1.3267 0.5175 0.024 Uiso calc R 1 . .
    C C9 0.38292(12) 1.15119(13) 0.45126(9) 0.0181(2) Uani d . 1 . .
    H H9A 0.4609 1.1253 0.4797 0.022 Uiso calc R 1 . .
    C C10 0.31913(11) 1.06723(12) 0.38749(8) 0.0150(2) Uani d . 1 . .
    C C11 0.00344(12) 0.98106(11) 0.33143(9) 0.0140(2) Uani d . 1 . .
    C C12 -0.11773(12) 0.99061(11) 0.29291(9) 0.0171(2) Uani d . 1 . .
    H H12A -0.1297 1.0272 0.2287 0.021 Uiso calc R 1 . .
    C C13 -0.22232(12) 0.94758(13) 0.34639(10) 0.0192(3) Uani d . 1 . .
    H H13A -0.3040 0.9547 0.3178 0.023 Uiso calc R 1 . .
    C C14 -0.20898(11) 0.89450(12) 0.44087(10) 0.0175(2) Uani d . 1 . .
    C C15 -0.08745(12) 0.88703(12) 0.48142(9) 0.0173(2) Uani d . 1 . .
    H H15A -0.0758 0.8530 0.5465 0.021 Uiso calc R 1 . .
    C C16 0.01529(11) 0.92868(12) 0.42750(9) 0.0151(2) Uani d . 1 . .
    H H16A 0.0969 0.9217 0.4562 0.018 Uiso calc R 1 . .
    C C17 0.09506(12) 1.09065(13) 0.17800(9) 0.0191(2) Uani d . 1 . .
    H H17A 0.0498 1.1700 0.1944 0.029 Uiso calc R 1 . .
    H H17B 0.0426 1.0373 0.1344 0.029 Uiso calc R 1 . .
    H H17C 0.1740 1.1118 0.1438 0.029 Uiso calc R 1 . .
    C C18 0.39319(13) 0.96648(10) 0.16643(8) 0.0248(3) Uani d . 1 . .
    H H18A 0.3593 0.9468 0.1002 0.037 Uiso calc R 1 . .
    H H18B 0.4847 0.9533 0.1664 0.037 Uiso calc R 1 . .
    H H18C 0.3745 1.0561 0.1832 0.037 Uiso calc R 1 . .
    C C19 0.37274(13) 0.73983(13) 0.22426(10) 0.0216(3) Uani d . 1 . .
    H H19A 0.3445 0.7134 0.1578 0.032 Uiso calc R 1 . .
    H H19B 0.3348 0.6836 0.2746 0.032 Uiso calc R 1 . .
    H H19C 0.4648 0.7335 0.2281 0.032 Uiso calc R 1 . .
_geom_special_details
;
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C10 . 1.7627(13) ?
    S1 C2 . 1.8271(13) ?
    N1 C14 . 1.4030(16) ?
    N1 H1A . 0.88(2) ?
    N1 H1B . 0.95(2) ?
    C2 C19 . 1.5240(17) ?
    C2 C18 . 1.5249(17) ?
    C2 C3 . 1.5334(17) ?
    C3 C4 . 1.5622(16) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C11 . 1.5367(16) ?
    C4 C5 . 1.5403(16) ?
    C4 C17 . 1.5432(15) ?
    C5 C6 . 1.4004(17) ?
    C5 C10 . 1.4017(17) ?
    C6 C7 . 1.3883(19) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.398(2) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.3770(19) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.3975(17) ?
    C9 H9A . 0.9500 ?
    C11 C12 . 1.3885(17) ?
    C11 C16 . 1.4047(17) ?
    C12 C13 . 1.3947(18) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.3897(19) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.4010(17) ?
    C15 C16 . 1.3777(18) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 S1 C2 . . 100.56(6) ?
    C14 N1 H1A . . 115.1(12) ?
    C14 N1 H1B . . 113.3(12) ?
    H1A N1 H1B . . 114.7(17) ?
    C19 C2 C18 . . 109.71(10) ?
    C19 C2 C3 . . 109.49(10) ?
    C18 C2 C3 . . 114.05(11) ?
    C19 C2 S1 . . 105.34(9) ?
    C18 C2 S1 . . 110.95(9) ?
    C3 C2 S1 . . 106.90(8) ?
    C2 C3 C4 . . 118.93(10) ?
    C2 C3 H3A . . 107.6 ?
    C4 C3 H3A . . 107.6 ?
    C2 C3 H3B . . 107.6 ?
    C4 C3 H3B . . 107.6 ?
    H3A C3 H3B . . 107.0 ?
    C11 C4 C5 . . 107.38(9) ?
    C11 C4 C17 . . 111.50(10) ?
    C5 C4 C17 . . 109.00(10) ?
    C11 C4 C3 . . 105.87(9) ?
    C5 C4 C3 . . 114.48(10) ?
    C17 C4 C3 . . 108.62(10) ?
    C6 C5 C10 . . 116.63(11) ?
    C6 C5 C4 . . 118.18(10) ?
    C10 C5 C4 . . 125.17(11) ?
    C7 C6 C5 . . 122.70(12) ?
    C7 C6 H6A . . 118.7 ?
    C5 C6 H6A . . 118.7 ?
    C6 C7 C8 . . 119.52(13) ?
    C6 C7 H7A . . 120.2 ?
    C8 C7 H7A . . 120.2 ?
    C9 C8 C7 . . 118.90(12) ?
    C9 C8 H8A . . 120.5 ?
    C7 C8 H8A . . 120.5 ?
    C8 C9 C10 . . 121.34(12) ?
    C8 C9 H9A . . 119.3 ?
    C10 C9 H9A . . 119.3 ?
    C9 C10 C5 . . 120.91(12) ?
    C9 C10 S1 . . 116.35(10) ?
    C5 C10 S1 . . 122.71(10) ?
    C12 C11 C16 . . 116.87(11) ?
    C12 C11 C4 . . 124.90(11) ?
    C16 C11 C4 . . 118.14(10) ?
    C11 C12 C13 . . 121.43(11) ?
    C11 C12 H12A . . 119.3 ?
    C13 C12 H12A . . 119.3 ?
    C14 C13 C12 . . 121.05(11) ?
    C14 C13 H13A . . 119.5 ?
    C12 C13 H13A . . 119.5 ?
    C13 C14 C15 . . 118.01(11) ?
    C13 C14 N1 . . 122.15(12) ?
    C15 C14 N1 . . 119.73(12) ?
    C16 C15 C14 . . 120.41(11) ?
    C16 C15 H15A . . 119.8 ?
    C14 C15 H15A . . 119.8 ?
    C15 C16 C11 . . 122.20(11) ?
    C15 C16 H16A . . 118.9 ?
    C11 C16 H16A . . 118.9 ?
    C4 C17 H17A . . 109.5 ?
    C4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C2 C18 H18A . . 109.5 ?
    C2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C2 C19 H19A . . 109.5 ?
    C2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 S1 C2 C19 . . . . -172.58(8) ?
    C10 S1 C2 C18 . . . . 68.76(10) ?
    C10 S1 C2 C3 . . . . -56.16(9) ?
    C19 C2 C3 C4 . . . . 174.57(10) ?
    C18 C2 C3 C4 . . . . -62.07(14) ?
    S1 C2 C3 C4 . . . . 60.94(12) ?
    C2 C3 C4 C11 . . . . -146.59(11) ?
    C2 C3 C4 C5 . . . . -28.51(15) ?
    C2 C3 C4 C17 . . . . 93.55(12) ?
    C11 C4 C5 C6 . . . . -66.66(13) ?
    C17 C4 C5 C6 . . . . 54.26(14) ?
    C3 C4 C5 C6 . . . . 176.12(10) ?
    C11 C4 C5 C10 . . . . 111.56(13) ?
    C17 C4 C5 C10 . . . . -127.51(12) ?
    C3 C4 C5 C10 . . . . -5.66(16) ?
    C10 C5 C6 C7 . . . . 0.29(18) ?
    C4 C5 C6 C7 . . . . 178.67(12) ?
    C5 C6 C7 C8 . . . . -0.4(2) ?
    C6 C7 C8 C9 . . . . 0.46(19) ?
    C7 C8 C9 C10 . . . . -0.38(19) ?
    C8 C9 C10 C5 . . . . 0.26(18) ?
    C8 C9 C10 S1 . . . . -177.90(9) ?
    C6 C5 C10 C9 . . . . -0.20(16) ?
    C4 C5 C10 C9 . . . . -178.45(11) ?
    C6 C5 C10 S1 . . . . 177.84(9) ?
    C4 C5 C10 S1 . . . . -0.41(16) ?
    C2 S1 C10 C9 . . . . -151.41(9) ?
    C2 S1 C10 C5 . . . . 30.47(11) ?
    C5 C4 C11 C12 . . . . 131.44(12) ?
    C17 C4 C11 C12 . . . . 12.11(17) ?
    C3 C4 C11 C12 . . . . -105.85(13) ?
    C5 C4 C11 C16 . . . . -52.17(14) ?
    C17 C4 C11 C16 . . . . -171.50(10) ?
    C3 C4 C11 C16 . . . . 70.54(13) ?
    C16 C11 C12 C13 . . . . -1.34(18) ?
    C4 C11 C12 C13 . . . . 175.09(12) ?
    C11 C12 C13 C14 . . . . 0.6(2) ?
    C12 C13 C14 C15 . . . . 0.84(19) ?
    C12 C13 C14 N1 . . . . 177.07(12) ?
    C13 C14 C15 C16 . . . . -1.47(19) ?
    N1 C14 C15 C16 . . . . -177.79(12) ?
    C14 C15 C16 C11 . . . . 0.72(18) ?
    C12 C11 C16 C15 . . . . 0.69(18) ?
    C4 C11 C16 C15 . . . . -175.99(12) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1A S1 1_455 0.88(2) 2.82(2) 3.6562(14) 158.3(16) y
data_global
_journal_date_recd_electronic     2011-03-22
_journal_date_accepted     2011-03-31
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2011
_journal_volume     67
_journal_issue      5
_journal_page_first     o188
_journal_page_last     o191
_journal_paper_category     FO
_journal_coeditor_code     BM3104
_publ_contact_author_name     'Professor C. S. Frampton'
_publ_contact_author_address
;
Pharmorphix Solid State Services
A Sigma--Aldrich Company
250 Cambridge Science Park
Milton Road
Cambridge CB4 0WE
England
;
_publ_contact_author_email     chris.frampton@sial.com
_publ_contact_author_fax     '01223 424930'
_publ_contact_author_phone     '01223 425105'
_publ_section_title
;
(R)-4-(4-Aminophenyl)-2,2,4-trimethylchroman and
(S)-4-(4-Aminophenyl)-2,2,4-trimethylthiachroman,
and a redetermination of rac-4-(4-hydroxyphenyl)-2,2,4-trimethylchroman
at 100 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Frampton, Christopher S.'
;
Pharmorphix Solid State Services
A Sigma--Aldrich Company
250 Cambridge Science Park
Milton Road
Cambridge CB4 0WE
England
;
    'MacNicol, David D.'
;
Department of Chemistry
University of Glasgow
Glasgow G12 8QQ
Scotland
;
    'Wilson, Derek R.'
;
Department of Chemistry
University of Glasgow
Glasgow G12 8QQ
Scotland
;
