#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202481.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202481
loop_
_publ_author_name
'Sundari Bhaskaran'
'S. Selvanayagam'
'D. Velmurugan'
'K. Ravikumar'
'M. Anniyappan'
'D. Muralidharan'
'P. T. Perumal'
_publ_section_title
N-(4a-Morpholino-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)phenylamine
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1301
_journal_page_last               o1303
_journal_paper_doi               10.1107/S1600536803017173
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C23 H28 N2 O2'
_chemical_formula_moiety         'C23 H28 N2 O2'
_chemical_formula_sum            'C23 H28 N2 O2'
_chemical_formula_weight         364.47
_chemical_name_systematic
;
N-(4a-Morpholino-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)phenylamine
;
_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                81.3590(10)
_cell_angle_beta                 80.1650(10)
_cell_angle_gamma                64.9200(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6452(7)
_cell_length_b                   10.1247(8)
_cell_length_c                   11.1168(9)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.214
_cell_measurement_theta_min      2.348
_cell_volume                     965.11(13)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990)'
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6035
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.088P)²+0.492P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                3415
_reflns_number_total             4223
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6248.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        965.11(18)
_cod_database_code               2202481
_cod_database_fobs_code          2202481
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
O1 0.63667(15) 0.25375(14) 0.17134(11) 0.0347(3) Uani d . 1 . . O
C2 0.7884(2) 0.1737(2) 0.20895(16) 0.0308(4) Uani d . 1 . . C
C3 0.8958(2) 0.1738(2) 0.09030(18) 0.0385(5) Uani d . 1 . . C
H3A 1.0016 0.1146 0.1057 0.046 Uiso calc R 1 . . H
H3B 0.8726 0.1295 0.0291 0.046 Uiso calc R 1 . . H
C4 0.8796(3) 0.3276(3) 0.0403(2) 0.0505(6) Uani d . 1 . . C
H4A 0.9529 0.3224 -0.0324 0.061 Uiso calc R 1 . . H
H4B 0.7767 0.3847 0.0173 0.061 Uiso calc R 1 . . H
C5 0.9088(3) 0.4018(3) 0.1363(2) 0.0556(6) Uani d . 1 . . C
H5A 0.8952 0.5006 0.1044 0.067 Uiso calc R 1 . . H
H5B 1.0143 0.3485 0.1548 0.067 Uiso calc R 1 . . H
C6 0.7984(3) 0.4073(2) 0.2534(2) 0.0437(5) Uani d . 1 . . C
H6A 0.6937 0.4683 0.2360 0.052 Uiso calc R 1 . . H
H6B 0.8218 0.4520 0.3141 0.052 Uiso calc R 1 . . H
C7 0.8086(2) 0.2550(2) 0.30666(17) 0.0333(4) Uani d . 1 . . C
H7 0.9114 0.1984 0.3326 0.040 Uiso calc R 1 . . H
C8 0.6889(2) 0.2674(2) 0.41974(17) 0.0374(4) Uani d . 1 . . C
H8 0.6817 0.3485 0.4624 0.045 Uiso calc R 1 . . H
C9 0.5305(2) 0.3101(2) 0.38125(17) 0.0330(4) Uani d . 1 . . C
C10 0.3968(2) 0.3610(2) 0.46364(18) 0.0371(4) Uani d . 1 . . C
H10 0.4052 0.3641 0.5452 0.045 Uiso calc R 1 . . H
C11 0.2532(2) 0.4067(2) 0.4277(2) 0.0437(5) Uani d . 1 . . C
H11 0.1659 0.4380 0.4849 0.052 Uiso calc R 1 . . H
C12 0.2387(2) 0.4061(2) 0.3068(2) 0.0468(5) Uani d . 1 . . C
H12 0.1414 0.4411 0.2816 0.056 Uiso calc R 1 . . H
C13 0.3687(2) 0.3536(2) 0.2228(2) 0.0409(5) Uani d . 1 . . C
H13 0.3589 0.3519 0.1414 0.049 Uiso calc R 1 . . H
C14 0.5143(2) 0.30333(19) 0.26049(17) 0.0320(4) Uani d . 1 . . C
N15 0.79895(17) 0.02740(17) 0.26236(14) 0.0315(4) Uani d . 1 . . N
C16 0.9542(2) -0.0761(2) 0.2889(2) 0.0413(5) Uani d . 1 . . C
H16A 0.9949 -0.0319 0.3376 0.050 Uiso calc R 1 . . H
H16B 1.0223 -0.0999 0.2130 0.050 Uiso calc R 1 . . H
C17 0.9471(3) -0.2134(2) 0.3580(2) 0.0487(5) Uani d . 1 . . C
H17A 1.0500 -0.2811 0.3756 0.058 Uiso calc R 1 . . H
H17B 0.8828 -0.1892 0.4356 0.058 Uiso calc R 1 . . H
O18 0.88758(19) -0.28253(16) 0.29196(16) 0.0530(4) Uani d . 1 . . O
C19 0.7387(3) -0.1820(3) 0.2638(2) 0.0519(6) Uani d . 1 . . C
H19A 0.6702 -0.1563 0.3394 0.062 Uiso calc R 1 . . H
H19B 0.6983 -0.2286 0.2172 0.062 Uiso calc R 1 . . H
C20 0.7407(3) -0.0447(2) 0.1912(2) 0.0421(5) Uani d . 1 . . C
H20A 0.8063 -0.0688 0.1141 0.050 Uiso calc R 1 . . H
H20B 0.6373 0.0208 0.1732 0.050 Uiso calc R 1 . . H
N21 0.7352(2) 0.1391(2) 0.50510(16) 0.0445(4) Uani d . 1 . . N
H21 0.7949 0.0562 0.4772 0.053 Uiso calc R 1 . . H
C22 0.6874(2) 0.1424(3) 0.63196(18) 0.0419(5) Uani d . 1 . . C
C23 0.6910(3) 0.0140(3) 0.6964(2) 0.0498(5) Uani d . 1 . . C
H23 0.7175 -0.0681 0.6548 0.060 Uiso calc R 1 . . H
C24 0.6557(3) 0.0060(3) 0.8213(2) 0.0578(7) Uani d . 1 . . C
H24 0.6600 -0.0822 0.8631 0.069 Uiso calc R 1 . . H
C25 0.6145(3) 0.1239(3) 0.8861(2) 0.0600(7) Uani d . 1 . . C
H25 0.5907 0.1168 0.9708 0.072 Uiso calc R 1 . . H
C26 0.6090(3) 0.2535(3) 0.8234(2) 0.0556(6) Uani d . 1 . . C
H26 0.5805 0.3353 0.8658 0.067 Uiso calc R 1 . . H
C27 0.6459(3) 0.2627(3) 0.6965(2) 0.0476(5) Uani d . 1 . . C
H27 0.6425 0.3506 0.6549 0.057 Uiso calc R 1 . . H
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_publ_flag
C14 O1 C2 118.10(10) ?
O1 C2 N15 107.33(14) ?
O1 C2 C3 103.46(15) ?
N15 C2 C3 114.86(15) ?
O1 C2 C7 108.99(14) ?
N15 C2 C7 109.78(14) ?
C3 C2 C7 112.01(15) ?
C4 C3 C2 112.25(16) ?
C4 C3 H3A 109.2 ?
C2 C3 H3A 109.2 ?
C4 C3 H3B 109.2 ?
C2 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
C5 C4 C3 110.25(19) ?
C5 C4 H4A 109.6 ?
C3 C4 H4A 109.6 ?
C5 C4 H4B 109.6 ?
C3 C4 H4B 109.6 ?
H4A C4 H4B 108.1 ?
C4 C5 C6 110.77(19) ?
C4 C5 H5A 109.5 ?
C6 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
C6 C5 H5B 109.5 ?
H5A C5 H5B 108.1 ?
C5 C6 C7 112.50(18) ?
C5 C6 H6A 109.1 ?
C7 C6 H6A 109.1 ?
C5 C6 H6B 109.1 ?
C7 C6 H6B 109.1 ?
H6A C6 H6B 107.8 ?
C6 C7 C8 110.36(16) ?
C6 C7 C2 110.82(15) ?
C8 C7 C2 111.22(15) ?
C6 C7 H7 108.1 ?
C8 C7 H7 108.1 ?
C2 C7 H7 108.1 ?
N21 C8 C9 113.15(17) ?
N21 C8 C7 112.77(17) ?
C9 C8 C7 110.48(15) ?
N21 C8 H8 106.7 ?
C9 C8 H8 106.7 ?
C7 C8 H8 106.7 ?
C14 C9 C10 117.68(18) ?
C14 C9 C8 120.62(16) ?
C10 C9 C8 121.67(17) ?
C11 C10 C9 121.80(19) ?
C11 C10 H10 119.1 ?
C9 C10 H10 119.1 ?
C10 C11 C12 119.79(19) ?
C10 C11 H11 120.1 ?
C12 C11 H11 120.1 ?
C11 C12 C13 120.1(2) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C12 C13 C14 119.8(2) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
O1 C14 C13 116.00(17) ?
O1 C14 C9 123.27(17) ?
C13 C14 C9 120.68(18) ?
C20 N15 C16 107.9(2) y
C20 N15 C2 115.0(2) y
C16 N15 C2 114.30(10) y
N15 C16 C17 109.55(17) ?
N15 C16 H16A 109.8 ?
C17 C16 H16A 109.8 ?
N15 C16 H16B 109.8 ?
C17 C16 H16B 109.8 ?
H16A C16 H16B 108.2 ?
O18 C17 C16 112.42(19) ?
O18 C17 H17A 109.1 ?
C16 C17 H17A 109.1 ?
O18 C17 H17B 109.1 ?
C16 C17 H17B 109.1 ?
H17A C17 H17B 107.9 ?
C17 O18 C19 108.99(17) ?
O18 C19 C20 112.28(18) ?
O18 C19 H19A 109.1 ?
C20 C19 H19A 109.1 ?
O18 C19 H19B 109.1 ?
C20 C19 H19B 109.1 ?
H19A C19 H19B 107.9 ?
N15 C20 C19 109.22(18) ?
N15 C20 H20A 109.8 ?
C19 C20 H20A 109.8 ?
N15 C20 H20B 109.8 ?
C19 C20 H20B 109.8 ?
H20A C20 H20B 108.3 ?
C22 N21 C8 123.27(18) ?
C22 N21 H21 118.4 ?
C8 N21 H21 118.4 ?
C23 C22 C27 118.2(2) ?
C23 C22 N21 117.2(2) ?
C27 C22 N21 124.6(2) ?
C24 C23 C22 120.6(2) ?
C24 C23 H23 119.7 ?
C22 C23 H23 119.7 ?
C25 C24 C23 121.8(2) ?
C25 C24 H24 119.1 ?
C23 C24 H24 119.1 ?
C24 C25 C26 118.6(2) ?
C24 C25 H25 120.7 ?
C26 C25 H25 120.7 ?
C25 C26 C27 120.2(2) ?
C25 C26 H26 119.9 ?
C27 C26 H26 119.9 ?
C22 C27 C26 120.6(2) ?
C22 C27 H27 119.7 ?
C26 C27 H27 119.7 ?
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 C14 . 1.369(2) y
O1 C2 . 1.440(2) y
C2 N15 . 1.479(2) y
C2 C3 . 1.532(2) ?
C2 C7 . 1.540(3) y
C3 C4 . 1.524(3) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.519(3) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 C6 . 1.527(3) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C7 . 1.534(3) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.535(3) y
C7 H7 . 0.98 ?
C8 N21 . 1.439(3) y
C8 C9 . 1.521(3) y
C8 H8 . 0.98 ?
C9 C14 . 1.393(3) y
C9 C10 . 1.394(3) ?
C10 C11 . 1.372(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.376(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.392(3) ?
C13 H13 . 0.93 ?
N15 C20 . 1.465(3) y
N15 C16 . 1.468(2) y
C16 C17 . 1.506(3) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 O18 . 1.414(3) y
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
O18 C19 . 1.420(3) y
C19 C20 . 1.505(3) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
N21 C22 . 1.408(3) ?
N21 H21 . 0.86 ?
C22 C23 . 1.378(3) ?
C22 C27 . 1.381(3) ?
C23 C24 . 1.371(4) ?
C23 H23 . 0.93 ?
C24 C25 . 1.364(4) ?
C24 H24 . 0.93 ?
C25 C26 . 1.374(4) ?
C25 H25 . 0.93 ?
C26 C27 . 1.394(3) ?
C26 H26 . 0.93 ?
C27 H27 . 0.93 ?
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
N21 H21 N15 . 0.86 2.44 2.949(3) 118
C20 H20B O1 . 0.97 2.35 2.737(2) 103
C11 H11 O18 2_656 0.93 2.82 3.458(3) 126
C12 H12 O18 1_465 0.93 2.83 3.524(3) 132
C27 H27 CgC 2_666 0.93 2.87 3.704(3) 150
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_publ_flag
C14 O1 C2 N15 73.21(18) ?
C14 O1 C2 C3 -164.95(15) ?
C14 O1 C2 C7 -45.6(2) ?
O1 C2 C3 C4 63.5(2) ?
N15 C2 C3 C4 -179.82(17) ?
C7 C2 C3 C4 -53.7(2) ?
C2 C3 C4 C5 56.5(3) ?
C3 C4 C5 C6 -57.4(3) ?
C4 C5 C6 C7 56.8(3) ?
C5 C6 C7 C8 -176.72(19) ?
C5 C6 C7 C2 -53.1(2) ?
O1 C2 C7 C6 -62.82(19) ?
N15 C2 C7 C6 179.89(15) ?
C3 C2 C7 C6 51.0(2) ?
O1 C2 C7 C8 60.34(19) ?
N15 C2 C7 C8 -56.9(2) ?
C3 C2 C7 C8 174.20(16) ?
C6 C7 C8 N21 -152.43(18) ?
C2 C7 C8 N21 84.2(2) ?
C6 C7 C8 C9 79.8(2) ?
C2 C7 C8 C9 -43.6(2) ?
N21 C8 C9 C14 -114.40(19) ?
C7 C8 C9 C14 13.1(3) ?
N21 C8 C9 C10 67.5(2) ?
C7 C8 C9 C10 -165.00(17) ?
C14 C9 C10 C11 -1.6(3) ?
C8 C9 C10 C11 176.58(18) ?
C9 C10 C11 C12 -1.6(3) ?
C10 C11 C12 C13 2.8(3) ?
C11 C12 C13 C14 -0.9(3) ?
C2 O1 C14 C13 -167.60(16) ?
C2 O1 C14 C9 15.0(3) ?
C12 C13 C14 O1 -179.76(18) ?
C12 C13 C14 C9 -2.3(3) ?
C10 C9 C14 O1 -179.21(17) ?
C8 C9 C14 O1 2.6(3) ?
C10 C9 C14 C13 3.5(3) ?
C8 C9 C14 C13 -174.70(18) ?
O1 C2 N15 C20 45.73(19) ?
C3 C2 N15 C20 -68.7(2) ?
C7 C2 N15 C20 164.05(16) ?
O1 C2 N15 C16 171.42(15) y
C3 C2 N15 C16 57.0(2) y
C7 C2 N15 C16 -70.27(19) ?
C20 N15 C16 C17 -58.2(2) ?
C2 N15 C16 C17 172.44(17) ?
N15 C16 C17 O18 59.0(2) ?
C16 C17 O18 C19 -57.4(2) ?
C17 O18 C19 C20 57.9(3) ?
C16 N15 C20 C19 58.6(2) ?
C2 N15 C20 C19 -172.46(17) ?
O18 C19 C20 N15 -59.9(3) ?
C9 C8 N21 C22 -82.1(2) ?
C7 C8 N21 C22 151.6(2) y
C8 N21 C22 C23 157.2(2) ?
C8 N21 C22 C27 -26.6(3) y
C27 C22 C23 C24 -0.7(3) ?
N21 C22 C23 C24 175.8(2) ?
C22 C23 C24 C25 0.7(4) ?
C23 C24 C25 C26 -0.2(4) ?
C24 C25 C26 C27 -0.4(4) ?
C23 C22 C27 C26 0.1(3) ?
N21 C22 C27 C26 -176.1(2) ?
C25 C26 C27 C22 0.4(4) ?
