#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224702.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_2224702
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Hakim Al-arique, Q. N. M.'
'Yathirajan, H. S.'
'Ramesha, A.R.'
_publ_section_title
11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,e]thiepin-11-ol
_journal_coeditor_code           LH2968
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o161
_journal_page_last               o162
_journal_paper_doi               10.1107/S1600536809053434
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H23 N O S'
_chemical_formula_moiety         'C19 H23 N O S'
_chemical_formula_sum            'C19 H23 N O S'
_chemical_formula_weight         313.44
_chemical_name_systematic
;
11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,e]thiepin-
11-ol
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.401(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7215(4)
_cell_length_b                   15.3729(10)
_cell_length_c                   27.9274(16)
_cell_measurement_reflns_used    6805
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.9681
_cell_measurement_theta_min      4.2752
_cell_volume                     3300.3(3)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14666
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.18
_diffrn_reflns_theta_min         4.29
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.557
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1079P)²+0.6589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                5490
_reflns_number_total             6565
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2968.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224702
_cod_database_fobs_code          2224702
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_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 S1A 0.69626(7) 0.25999(3) 0.288172(19) 0.02978(15) Uani d . 1 . .
O O1A 0.91923(17) 0.54941(9) 0.28401(5) 0.0240(3) Uani d . 1 . .
H H1A 1.0075 0.5603 0.2696 0.029 Uiso calc R 1 . .
N N1A 1.2061(2) 0.56334(11) 0.23664(6) 0.0242(4) Uani d . 1 . .
C C1A 0.7385(2) 0.44069(13) 0.31337(6) 0.0189(4) Uani d . 1 . .
C C2A 0.6889(2) 0.50798(13) 0.34289(6) 0.0230(4) Uani d . 1 . .
H H2AA 0.7418 0.5635 0.3408 0.028 Uiso calc R 1 . .
C C3A 0.5643(3) 0.49613(15) 0.37524(7) 0.0276(4) Uani d . 1 . .
H H3AA 0.5350 0.5429 0.3952 0.033 Uiso calc R 1 . .
C C4A 0.4833(3) 0.41658(15) 0.37828(7) 0.0284(4) Uani d . 1 . .
H H4AA 0.3984 0.4079 0.4003 0.034 Uiso calc R 1 . .
C C5A 0.5275(3) 0.34982(14) 0.34876(7) 0.0264(4) Uani d . 1 . .
H H5AA 0.4697 0.2955 0.3502 0.032 Uiso calc R 1 . .
C C6A 0.6554(2) 0.35985(13) 0.31669(6) 0.0202(4) Uani d . 1 . .
C C7A 0.7862(3) 0.28132(13) 0.23129(7) 0.0238(4) Uani d . 1 . .
H H7AA 0.9147 0.2814 0.2370 0.029 Uiso calc R 1 . .
H H7AB 0.7527 0.2330 0.2089 0.029 Uiso calc R 1 . .
C C8A 0.7295(2) 0.36527(13) 0.20746(6) 0.0202(4) Uani d . 1 . .
C C9A 0.6275(3) 0.36079(15) 0.16343(7) 0.0280(4) Uani d . 1 . .
H H9AA 0.5927 0.3055 0.1508 0.034 Uiso calc R 1 . .
C C10A 0.5764(3) 0.43455(17) 0.13802(7) 0.0331(5) Uani d . 1 . .
H H10A 0.5075 0.4301 0.1081 0.040 Uiso calc R 1 . .
C C11A 0.6263(3) 0.51514(16) 0.15646(7) 0.0306(5) Uani d . 1 . .
H H11A 0.5926 0.5665 0.1391 0.037 Uiso calc R 1 . .
C C12A 0.7258(2) 0.52091(13) 0.20050(7) 0.0232(4) Uani d . 1 . .
H H12A 0.7588 0.5766 0.2129 0.028 Uiso calc R 1 . .
C C13A 0.7782(2) 0.44720(12) 0.22683(6) 0.0170(4) Uani d . 1 . .
C C14A 0.8737(2) 0.46053(12) 0.27754(6) 0.0181(4) Uani d . 1 . .
C C15A 1.0403(2) 0.40533(13) 0.28923(6) 0.0207(4) Uani d . 1 . .
H H15A 1.1021 0.4278 0.3194 0.025 Uiso calc R 1 . .
H H15B 1.0046 0.3448 0.2955 0.025 Uiso calc R 1 . .
C C16A 1.1698(2) 0.40312(13) 0.25052(7) 0.0218(4) Uani d . 1 . .
H H16A 1.2402 0.3494 0.2550 0.026 Uiso calc R 1 . .
H H16B 1.1027 0.3994 0.2186 0.026 Uiso calc R 1 . .
C C17A 1.2933(2) 0.48049(13) 0.25020(7) 0.0241(4) Uani d . 1 . .
H H17A 1.3558 0.4868 0.2826 0.029 Uiso calc R 1 . .
H H17B 1.3810 0.4683 0.2274 0.029 Uiso calc R 1 . .
C C18A 1.1570(3) 0.56816(15) 0.18463(7) 0.0296(5) Uani d . 1 . .
H H18A 1.0974 0.6234 0.1769 0.044 Uiso calc R 1 . .
H H18B 1.0791 0.5197 0.1748 0.044 Uiso calc R 1 . .
H H18C 1.2618 0.5646 0.1675 0.044 Uiso calc R 1 . .
C C19A 1.3169(3) 0.63736(16) 0.25201(10) 0.0396(6) Uani d . 1 . .
H H19A 1.2540 0.6917 0.2442 0.059 Uiso calc R 1 . .
H H19B 1.4230 0.6358 0.2353 0.059 Uiso calc R 1 . .
H H19C 1.3477 0.6342 0.2868 0.059 Uiso calc R 1 . .
S S1B 0.66729(7) 0.22246(4) 0.627252(18) 0.03356(16) Uani d . 1 . .
O O1B 0.39362(17) 0.32974(9) 0.47928(5) 0.0224(3) Uani d . 1 . .
H H1B 0.2941 0.3119 0.4691 0.027 Uiso calc R 1 . .
N N1B 0.0713(2) 0.27183(13) 0.45327(6) 0.0272(4) Uani d . 1 . .
C C1B 0.6076(2) 0.33566(12) 0.54588(6) 0.0194(4) Uani d . 1 . .
C C2B 0.6575(2) 0.41167(13) 0.52343(7) 0.0225(4) Uani d . 1 . .
H H2BA 0.5966 0.4284 0.4937 0.027 Uiso calc R 1 . .
C C3B 0.7936(3) 0.46361(14) 0.54324(8) 0.0269(4) Uani d . 1 . .
H H3BA 0.8237 0.5154 0.5274 0.032 Uiso calc R 1 . .
C C4B 0.8849(3) 0.43913(14) 0.58631(8) 0.0296(5) Uani d . 1 . .
H H4BA 0.9773 0.4743 0.6003 0.036 Uiso calc R 1 . .
C C5B 0.8406(3) 0.36365(14) 0.60857(7) 0.0279(4) Uani d . 1 . .
H H5BA 0.9048 0.3467 0.6378 0.033 Uiso calc R 1 . .
C C6B 0.7032(2) 0.31114(13) 0.58920(7) 0.0227(4) Uani d . 1 . .
C C7B 0.5684(3) 0.13299(14) 0.59244(7) 0.0292(4) Uani d . 1 . .
H H7BA 0.6145 0.0780 0.6070 0.035 Uiso calc R 1 . .
H H7BB 0.4418 0.1340 0.5955 0.035 Uiso calc R 1 . .
C C8B 0.5951(2) 0.13126(13) 0.53919(7) 0.0249(4) Uani d . 1 . .
C C9B 0.6839(3) 0.05921(14) 0.52276(9) 0.0340(5) Uani d . 1 . .
H H9BA 0.7316 0.0173 0.5453 0.041 Uiso calc R 1 . .
C C10B 0.7035(3) 0.04778(15) 0.47439(10) 0.0382(6) Uani d . 1 . .
H H10B 0.7637 -0.0015 0.4638 0.046 Uiso calc R 1 . .
C C11B 0.6349(3) 0.10843(16) 0.44183(8) 0.0341(5) Uani d . 1 . .
H H11B 0.6440 0.1002 0.4084 0.041 Uiso calc R 1 . .
C C12B 0.5524(2) 0.18169(14) 0.45762(7) 0.0257(4) Uani d . 1 . .
H H12B 0.5087 0.2240 0.4348 0.031 Uiso calc R 1 . .
C C13B 0.5316(2) 0.19501(13) 0.50640(7) 0.0199(4) Uani d . 1 . .
C C14B 0.4538(2) 0.28306(12) 0.52111(6) 0.0187(4) Uani d . 1 . .
C C15B 0.3036(2) 0.27781(14) 0.55385(7) 0.0231(4) Uani d . 1 . .
H H15C 0.3525 0.2592 0.5863 0.028 Uiso calc R 1 . .
H H15D 0.2554 0.3370 0.5570 0.028 Uiso calc R 1 . .
C C16B 0.1534(2) 0.21639(14) 0.53708(7) 0.0258(4) Uani d . 1 . .
H H16C 0.2030 0.1642 0.5227 0.031 Uiso calc R 1 . .
H H16D 0.0976 0.1970 0.5657 0.031 Uiso calc R 1 . .
C C17B 0.0125(2) 0.25346(13) 0.50080(7) 0.0220(4) Uani d . 1 . .
H H17C -0.0853 0.2116 0.4968 0.026 Uiso calc R 1 . .
H H17D -0.0321 0.3080 0.5140 0.026 Uiso calc R 1 . .
C C18B 0.0944(3) 0.1914(2) 0.42672(9) 0.0515(8) Uani d . 1 . .
H H18D 0.1890 0.1573 0.4433 0.077 Uiso calc R 1 . .
H H18E 0.1232 0.2054 0.3942 0.077 Uiso calc R 1 . .
H H18F -0.0136 0.1575 0.4248 0.077 Uiso calc R 1 . .
C C19B -0.0530(3) 0.3298(2) 0.42629(9) 0.0479(7) Uani d . 1 . .
H H19D -0.0118 0.3430 0.3950 0.072 Uiso calc R 1 . .
H H19E -0.0635 0.3839 0.4444 0.072 Uiso calc R 1 . .
H H19F -0.1668 0.3012 0.4215 0.072 Uiso calc R 1 . .
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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6A S1A C7A . . 109.55(9) ?
C14A O1A H1A . . 109.5 ?
C19A N1A C18A . . 109.89(18) ?
C19A N1A C17A . . 110.88(17) ?
C18A N1A C17A . . 111.53(16) ?
C2A C1A C6A . . 117.58(17) ?
C2A C1A C14A . . 118.41(17) ?
C6A C1A C14A . . 123.95(16) ?
C3A C2A C1A . . 122.01(19) ?
C3A C2A H2AA . . 119.0 ?
C1A C2A H2AA . . 119.0 ?
C4A C3A C2A . . 120.05(19) ?
C4A C3A H3AA . . 120.0 ?
C2A C3A H3AA . . 120.0 ?
C5A C4A C3A . . 118.91(18) ?
C5A C4A H4AA . . 120.5 ?
C3A C4A H4AA . . 120.5 ?
C4A C5A C6A . . 121.9(2) ?
C4A C5A H5AA . . 119.0 ?
C6A C5A H5AA . . 119.0 ?
C5A C6A C1A . . 119.50(18) ?
C5A C6A S1A . . 110.96(15) ?
C1A C6A S1A . . 129.40(14) ?
C8A C7A S1A . . 115.01(13) ?
C8A C7A H7AA . . 108.5 ?
S1A C7A H7AA . . 108.5 ?
C8A C7A H7AB . . 108.5 ?
S1A C7A H7AB . . 108.5 ?
H7AA C7A H7AB . . 107.5 ?
C9A C8A C13A . . 119.34(18) ?
C9A C8A C7A . . 117.71(18) ?
C13A C8A C7A . . 122.93(16) ?
C10A C9A C8A . . 121.6(2) ?
C10A C9A H9AA . . 119.2 ?
C8A C9A H9AA . . 119.2 ?
C9A C10A C11A . . 119.35(18) ?
C9A C10A H10A . . 120.3 ?
C11A C10A H10A . . 120.3 ?
C10A C11A C12A . . 119.9(2) ?
C10A C11A H11A . . 120.1 ?
C12A C11A H11A . . 120.1 ?
C13A C12A C11A . . 121.7(2) ?
C13A C12A H12A . . 119.2 ?
C11A C12A H12A . . 119.2 ?
C12A C13A C8A . . 118.18(17) ?
C12A C13A C14A . . 117.78(17) ?
C8A C13A C14A . . 123.85(16) ?
O1A C14A C1A . . 106.40(14) ?
O1A C14A C13A . . 109.58(15) ?
C1A C14A C13A . . 105.90(14) ?
O1A C14A C15A . . 108.06(14) ?
C1A C14A C15A . . 110.73(14) ?
C13A C14A C15A . . 115.78(14) ?
C16A C15A C14A . . 116.41(15) ?
C16A C15A H15A . . 108.2 ?
C14A C15A H15A . . 108.2 ?
C16A C15A H15B . . 108.2 ?
C14A C15A H15B . . 108.2 ?
H15A C15A H15B . . 107.3 ?
C17A C16A C15A . . 115.75(16) ?
C17A C16A H16A . . 108.3 ?
C15A C16A H16A . . 108.3 ?
C17A C16A H16B . . 108.3 ?
C15A C16A H16B . . 108.3 ?
H16A C16A H16B . . 107.4 ?
N1A C17A C16A . . 113.87(15) ?
N1A C17A H17A . . 108.8 ?
C16A C17A H17A . . 108.8 ?
N1A C17A H17B . . 108.8 ?
C16A C17A H17B . . 108.8 ?
H17A C17A H17B . . 107.7 ?
N1A C18A H18A . . 109.5 ?
N1A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
N1A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
N1A C19A H19A . . 109.5 ?
N1A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
N1A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C6B S1B C7B . . 110.20(9) ?
C14B O1B H1B . . 109.5 ?
C18B N1B C19B . . 111.0(2) ?
C18B N1B C17B . . 111.00(19) ?
C19B N1B C17B . . 109.77(18) ?
C2B C1B C6B . . 117.73(17) ?
C2B C1B C14B . . 118.00(15) ?
C6B C1B C14B . . 124.27(17) ?
C3B C2B C1B . . 122.07(18) ?
C3B C2B H2BA . . 119.0 ?
C1B C2B H2BA . . 119.0 ?
C4B C3B C2B . . 119.4(2) ?
C4B C3B H3BA . . 120.3 ?
C2B C3B H3BA . . 120.3 ?
C5B C4B C3B . . 119.56(19) ?
C5B C4B H4BA . . 120.2 ?
C3B C4B H4BA . . 120.2 ?
C4B C5B C6B . . 121.55(18) ?
C4B C5B H5BA . . 119.2 ?
C6B C5B H5BA . . 119.2 ?
C5B C6B C1B . . 119.62(19) ?
C5B C6B S1B . . 111.62(14) ?
C1B C6B S1B . . 128.64(16) ?
C8B C7B S1B . . 116.69(14) ?
C8B C7B H7BA . . 108.1 ?
S1B C7B H7BA . . 108.1 ?
C8B C7B H7BB . . 108.1 ?
S1B C7B H7BB . . 108.1 ?
H7BA C7B H7BB . . 107.3 ?
C13B C8B C9B . . 119.4(2) ?
C13B C8B C7B . . 123.82(18) ?
C9B C8B C7B . . 116.7(2) ?
C10B C9B C8B . . 121.4(2) ?
C10B C9B H9BA . . 119.3 ?
C8B C9B H9BA . . 119.3 ?
C11B C10B C9B . . 119.3(2) ?
C11B C10B H10B . . 120.3 ?
C9B C10B H10B . . 120.3 ?
C10B C11B C12B . . 120.1(2) ?
C10B C11B H11B . . 120.0 ?
C12B C11B H11B . . 120.0 ?
C11B C12B C13B . . 121.7(2) ?
C11B C12B H12B . . 119.1 ?
C13B C12B H12B . . 119.1 ?
C8B C13B C12B . . 117.96(18) ?
C8B C13B C14B . . 123.96(16) ?
C12B C13B C14B . . 117.86(17) ?
O1B C14B C1B . . 106.49(15) ?
O1B C14B C15B . . 108.00(14) ?
C1B C14B C15B . . 110.53(14) ?
O1B C14B C13B . . 109.25(14) ?
C1B C14B C13B . . 105.96(14) ?
C15B C14B C13B . . 116.21(16) ?
C16B C15B C14B . . 116.08(16) ?
C16B C15B H15C . . 108.3 ?
C14B C15B H15C . . 108.3 ?
C16B C15B H15D . . 108.3 ?
C14B C15B H15D . . 108.3 ?
H15C C15B H15D . . 107.4 ?
C17B C16B C15B . . 116.37(17) ?
C17B C16B H16C . . 108.2 ?
C15B C16B H16C . . 108.2 ?
C17B C16B H16D . . 108.2 ?
C15B C16B H16D . . 108.2 ?
H16C C16B H16D . . 107.3 ?
N1B C17B C16B . . 114.20(16) ?
N1B C17B H17C . . 108.7 ?
C16B C17B H17C . . 108.7 ?
N1B C17B H17D . . 108.7 ?
C16B C17B H17D . . 108.7 ?
H17C C17B H17D . . 107.6 ?
N1B C18B H18D . . 109.5 ?
N1B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
N1B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
N1B C19B H19D . . 109.5 ?
N1B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
N1B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
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
S1A C6A . 1.7713(19) ?
S1A C7A . 1.822(2) ?
O1A C14A . 1.418(2) ?
O1A H1A . 0.8400 ?
N1A C19A . 1.463(3) ?
N1A C18A . 1.468(3) ?
N1A C17A . 1.473(3) ?
C1A C2A . 1.398(3) ?
C1A C6A . 1.406(3) ?
C1A C14A . 1.543(2) ?
C2A C3A . 1.393(3) ?
C2A H2AA . 0.9500 ?
C3A C4A . 1.380(3) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.380(3) ?
C4A H4AA . 0.9500 ?
C5A C6A . 1.402(3) ?
C5A H5AA . 0.9500 ?
C7A C8A . 1.498(3) ?
C7A H7AA . 0.9900 ?
C7A H7AB . 0.9900 ?
C8A C9A . 1.398(3) ?
C8A C13A . 1.408(3) ?
C9A C10A . 1.376(3) ?
C9A H9AA . 0.9500 ?
C10A C11A . 1.382(3) ?
C10A H10A . 0.9500 ?
C11A C12A . 1.390(3) ?
C11A H11A . 0.9500 ?
C12A C13A . 1.390(3) ?
C12A H12A . 0.9500 ?
C13A C14A . 1.548(2) ?
C14A C15A . 1.550(2) ?
C15A C16A . 1.540(2) ?
C15A H15A . 0.9900 ?
C15A H15B . 0.9900 ?
C16A C17A . 1.525(3) ?
C16A H16A . 0.9900 ?
C16A H16B . 0.9900 ?
C17A H17A . 0.9900 ?
C17A H17B . 0.9900 ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
C19A H19A . 0.9800 ?
C19A H19B . 0.9800 ?
C19A H19C . 0.9800 ?
S1B C6B . 1.766(2) ?
S1B C7B . 1.811(2) ?
O1B C14B . 1.412(2) ?
O1B H1B . 0.8400 ?
N1B C18B . 1.461(3) ?
N1B C19B . 1.465(3) ?
N1B C17B . 1.470(2) ?
C1B C2B . 1.397(3) ?
C1B C6B . 1.408(2) ?
C1B C14B . 1.545(2) ?
C2B C3B . 1.393(3) ?
C2B H2BA . 0.9500 ?
C3B C4B . 1.388(3) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.375(3) ?
C4B H4BA . 0.9500 ?
C5B C6B . 1.401(3) ?
C5B H5BA . 0.9500 ?
C7B C8B . 1.521(3) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C13B . 1.398(3) ?
C8B C9B . 1.402(3) ?
C9B C10B . 1.384(4) ?
C9B H9BA . 0.9500 ?
C10B C11B . 1.373(4) ?
C10B H10B . 0.9500 ?
C11B C12B . 1.386(3) ?
C11B H11B . 0.9500 ?
C12B C13B . 1.402(3) ?
C12B H12B . 0.9500 ?
C13B C14B . 1.552(3) ?
C14B C15B . 1.545(2) ?
C15B C16B . 1.534(3) ?
C15B H15C . 0.9900 ?
C15B H15D . 0.9900 ?
C16B C17B . 1.525(3) ?
C16B H16C . 0.9900 ?
C16B H16D . 0.9900 ?
C17B H17C . 0.9900 ?
C17B H17D . 0.9900 ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
C19B H19D . 0.9800 ?
C19B H19E . 0.9800 ?
C19B H19F . 0.9800 ?
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
O1A H1A N1A . 0.84 1.86 2.693(2) 169.9
O1B H1B N1B . 0.84 1.84 2.679(2) 174.1
C4A H4AA O1B . 0.95 2.51 3.253(2) 134.7
C3A H3AA Cg7 3_666 0.95 2.74 3.526(6) 140
C17A H17A Cg1 1_655 0.99 2.67 3.537(7) 147
C17A H17B Cg2 1_655 0.99 2.75 3.720(3) 167
C17B H17C Cg8 1_455 0.99 2.68 3.663(6) 170
C17B 17D Cg7 1_455 0.99 2.64 3.5380(10) 149
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
C6A C1A C2A C3A . . . . 1.2(3) ?
C14A C1A C2A C3A . . . . 178.23(17) ?
C1A C2A C3A C4A . . . . -1.2(3) ?
C2A C3A C4A C5A . . . . -0.2(3) ?
C3A C4A C5A C6A . . . . 1.6(3) ?
C4A C5A C6A C1A . . . . -1.6(3) ?
C4A C5A C6A S1A . . . . 174.51(16) ?
C2A C1A C6A C5A . . . . 0.2(3) ?
C14A C1A C6A C5A . . . . -176.66(16) ?
C2A C1A C6A S1A . . . . -175.12(14) ?
C14A C1A C6A S1A . . . . 8.0(3) ?
C7A S1A C6A C5A . . . . 156.28(14) ?
C7A S1A C6A C1A . . . . -28.0(2) ?
C6A S1A C7A C8A . . . . -29.24(17) ?
S1A C7A C8A C9A . . . . -114.43(17) ?
S1A C7A C8A C13A . . . . 67.3(2) ?
C13A C8A C9A C10A . . . . 1.4(3) ?
C7A C8A C9A C10A . . . . -176.99(18) ?
C8A C9A C10A C11A . . . . -0.3(3) ?
C9A C10A C11A C12A . . . . -0.6(3) ?
C10A C11A C12A C13A . . . . 0.3(3) ?
C11A C12A C13A C8A . . . . 0.7(3) ?
C11A C12A C13A C14A . . . . -174.38(16) ?
C9A C8A C13A C12A . . . . -1.6(3) ?
C7A C8A C13A C12A . . . . 176.71(17) ?
C9A C8A C13A C14A . . . . 173.24(17) ?
C7A C8A C13A C14A . . . . -8.5(3) ?
C2A C1A C14A O1A . . . . 0.3(2) ?
C6A C1A C14A O1A . . . . 177.21(16) ?
C2A C1A C14A C13A . . . . -116.21(17) ?
C6A C1A C14A C13A . . . . 60.7(2) ?
C2A C1A C14A C15A . . . . 117.54(18) ?
C6A C1A C14A C15A . . . . -65.6(2) ?
C12A C13A C14A O1A . . . . -11.1(2) ?
C8A C13A C14A O1A . . . . 174.06(15) ?
C12A C13A C14A C1A . . . . 103.27(18) ?
C8A C13A C14A C1A . . . . -71.5(2) ?
C12A C13A C14A C15A . . . . -133.61(17) ?
C8A C13A C14A C15A . . . . 51.6(2) ?
O1A C14A C15A C16A . . . . -76.66(19) ?
C1A C14A C15A C16A . . . . 167.18(15) ?
C13A C14A C15A C16A . . . . 46.6(2) ?
C14A C15A C16A C17A . . . . 81.9(2) ?
C19A N1A C17A C16A . . . . 161.24(17) ?
C18A N1A C17A C16A . . . . -75.9(2) ?
C15A C16A C17A N1A . . . . -66.7(2) ?
C6B C1B C2B C3B . . . . -1.7(3) ?
C14B C1B C2B C3B . . . . 179.50(17) ?
C1B C2B C3B C4B . . . . 0.8(3) ?
C2B C3B C4B C5B . . . . 0.6(3) ?
C3B C4B C5B C6B . . . . -1.0(3) ?
C4B C5B C6B C1B . . . . 0.1(3) ?
C4B C5B C6B S1B . . . . -176.25(16) ?
C2B C1B C6B C5B . . . . 1.2(3) ?
C14B C1B C6B C5B . . . . 179.94(17) ?
C2B C1B C6B S1B . . . . 176.89(15) ?
C14B C1B C6B S1B . . . . -4.4(3) ?
C7B S1B C6B C5B . . . . -153.88(15) ?
C7B S1B C6B C1B . . . . 30.1(2) ?
C6B S1B C7B C8B . . . . 22.7(2) ?
S1B C7B C8B C13B . . . . -63.9(2) ?
S1B C7B C8B C9B . . . . 118.40(19) ?
C13B C8B C9B C10B . . . . -2.9(3) ?
C7B C8B C9B C10B . . . . 174.94(19) ?
C8B C9B C10B C11B . . . . 0.2(3) ?
C9B C10B C11B C12B . . . . 2.2(3) ?
C10B C11B C12B C13B . . . . -1.9(3) ?
C9B C8B C13B C12B . . . . 3.1(3) ?
C7B C8B C13B C12B . . . . -174.58(17) ?
C9B C8B C13B C14B . . . . -171.44(17) ?
C7B C8B C13B C14B . . . . 10.9(3) ?
C11B C12B C13B C8B . . . . -0.7(3) ?
C11B C12B C13B C14B . . . . 174.11(17) ?
C2B C1B C14B O1B . . . . -1.8(2) ?
C6B C1B C14B O1B . . . . 179.50(16) ?
C2B C1B C14B C15B . . . . -118.81(18) ?
C6B C1B C14B C15B . . . . 62.4(2) ?
C2B C1B C14B C13B . . . . 114.50(18) ?
C6B C1B C14B C13B . . . . -64.2(2) ?
C8B C13B C14B O1B . . . . -176.78(16) ?
C12B C13B C14B O1B . . . . 8.7(2) ?
C8B C13B C14B C1B . . . . 68.8(2) ?
C12B C13B C14B C1B . . . . -105.66(18) ?
C8B C13B C14B C15B . . . . -54.3(2) ?
C12B C13B C14B C15B . . . . 131.16(17) ?
O1B C14B C15B C16B . . . . 72.5(2) ?
C1B C14B C15B C16B . . . . -171.34(16) ?
C13B C14B C15B C16B . . . . -50.6(2) ?
C14B C15B C16B C17B . . . . -84.3(2) ?
C18B N1B C17B C16B . . . . 73.7(2) ?
C19B N1B C17B C16B . . . . -163.21(19) ?
C15B C16B C17B N1B . . . . 67.5(2) ?
