#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206905.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_2206905
loop_
_publ_author_name
'Liu, Jian-Chao'
'Chen, He-Lian'
'Chen, Ting'
'He, Hong-Wu'
'Ding, Ming-Wu'
_publ_section_title
3-(4-Chlorophenyl)-5-methyl-2-propylamino-8,9,10,11-tetrahydro-2-benzothieno[2',3';2,3]pyrido[4,5-d]pyrimidin-4(3H)-one
_journal_coeditor_code           CI6618
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3187
_journal_page_last               o3189
_journal_paper_doi               10.1107/S1600536805027595
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C23 H23 Cl N4 O S'
_chemical_formula_moiety         'C23 H23 Cl N4 O S'
_chemical_formula_sum            'C23 H23 Cl N4 O S'
_chemical_formula_weight         438.96
_chemical_name_systematic
;
3-(4-Chlorophenyl)-5-methyl-2-propylamino-8,9,10,11-tetrahydro-
2-benzothieno[2'3';2,3]pyrido[4,5-d]pyrimidin-4(3H)-one
;
_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                114.0540(10)
_cell_angle_beta                 98.9260(10)
_cell_angle_gamma                101.3350(10)
_cell_formula_units_Z            4
_cell_length_a                   11.8884(6)
_cell_length_b                   13.3784(7)
_cell_length_c                   15.7892(8)
_cell_measurement_reflns_used    3870
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.34
_cell_volume                     2169.42(19)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25134
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9167
_exptl_absorpt_correction_T_min  0.8911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         9849
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0525
_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)+(0.0778P)²+0.1323P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1562
_reflns_number_gt                6468
_reflns_number_total             9849
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6618.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206905
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
S1 0.83965(7) 0.78315(6) 0.38004(4) 0.0676(2) Uani d . 1 . . S
Cl1 0.69608(9) -0.01047(6) -0.43385(5) 0.0987(3) Uani d . 1 . . Cl
O1 0.75577(16) 0.26620(13) 0.01717(11) 0.0590(4) Uani d . 1 . . O
N1 0.77021(15) 0.38157(14) -0.05490(12) 0.0424(4) Uani d . 1 . . N
N2 0.81663(15) 0.58305(14) 0.03154(12) 0.0431(4) Uani d . 1 . . N
N3 0.79331(16) 0.49906(15) -0.13039(12) 0.0482(4) Uani d . 1 . . N
H3 0.7750 0.4378 -0.1838 0.058 Uiso calc R 1 . . H
N4 0.79378(17) 0.55450(16) 0.28406(13) 0.0506(5) Uani d . 1 . . N
C1 0.79393(17) 0.49006(17) -0.04908(14) 0.0404(5) Uani d . 1 . . C
C2 0.76997(18) 0.36276(18) 0.02714(15) 0.0427(5) Uani d . 1 . . C
C3 0.78741(17) 0.46588(17) 0.11601(14) 0.0411(5) Uani d . 1 . . C
C4 0.81125(17) 0.57168(17) 0.11311(14) 0.0396(5) Uani d . 1 . . C
C5 0.78045(18) 0.46055(18) 0.20347(15) 0.0448(5) Uani d . 1 . . C
C6 0.7560(2) 0.3517(2) 0.21206(17) 0.0582(6) Uani d . 1 . . C
H6A 0.7439 0.3665 0.2743 0.087 Uiso calc R 1 . . H
H6B 0.8225 0.3212 0.2043 0.087 Uiso calc R 1 . . H
H6C 0.6860 0.2976 0.1632 0.087 Uiso calc R 1 . . H
C7 0.81831(19) 0.65471(19) 0.27952(15) 0.0486(5) Uani d . 1 . . C
C8 0.82894(18) 0.67145(18) 0.19942(14) 0.0432(5) Uani d . 1 . . C
C9 0.85478(18) 0.79069(18) 0.22070(15) 0.0461(5) Uani d . 1 . . C
C10 0.8729(2) 0.84047(19) 0.15200(17) 0.0527(6) Uani d . 1 . . C
H10A 0.8099 0.7967 0.0929 0.063 Uiso calc R 1 . . H
H10B 0.9479 0.8345 0.1364 0.063 Uiso calc R 1 . . H
C11 0.8735(3) 0.9652(2) 0.1946(2) 0.0797(8) Uani d . 1 . . C
H11A 0.9088 1.0000 0.1581 0.096 Uiso calc R 1 . . H
H11B 0.7920 0.9685 0.1876 0.096 Uiso calc R 1 . . H
C12 0.9395(3) 1.0330(2) 0.2976(2) 0.0866(9) Uani d . 1 . . C
H12A 0.9361 1.1112 0.3193 0.104 Uiso calc R 1 . . H
H12B 1.0223 1.0343 0.3042 0.104 Uiso calc R 1 . . H
C13 0.8916(3) 0.9870(2) 0.3606(2) 0.0767(8) Uani d . 1 . . C
H13A 0.8201 1.0088 0.3720 0.092 Uiso calc R 1 . . H
H13B 0.9497 1.0193 0.4222 0.092 Uiso calc R 1 . . H
C14 0.8632(2) 0.8585(2) 0.31397(17) 0.0581(6) Uani d . 1 . . C
C15 0.75202(19) 0.28309(17) -0.14585(14) 0.0442(5) Uani d . 1 . . C
C16 0.6392(2) 0.21056(19) -0.19575(16) 0.0525(6) Uani d . 1 . . C
H16 0.5751 0.2229 -0.1700 0.063 Uiso calc R 1 . . H
C17 0.6219(2) 0.1191(2) -0.28468(17) 0.0616(7) Uani d . 1 . . C
H17 0.5462 0.0697 -0.3192 0.074 Uiso calc R 1 . . H
C18 0.7177(3) 0.10216(19) -0.32121(16) 0.0588(6) Uani d . 1 . . C
C19 0.8304(2) 0.1727(2) -0.27115(17) 0.0584(6) Uani d . 1 . . C
H19 0.8946 0.1596 -0.2966 0.070 Uiso calc R 1 . . H
C20 0.8474(2) 0.2634(2) -0.18246(16) 0.0520(6) Uani d . 1 . . C
H20 0.9237 0.3112 -0.1474 0.062 Uiso calc R 1 . . H
C21 0.82263(19) 0.60916(19) -0.13101(16) 0.0483(5) Uani d . 1 . . C
H21A 0.7896 0.6604 -0.0850 0.058 Uiso calc R 1 . . H
H21B 0.7861 0.5997 -0.1942 0.058 Uiso calc R 1 . . H
C22 0.9532(2) 0.6620(2) -0.1070(2) 0.0648(7) Uani d . 1 . . C
H22A 0.9859 0.6122 -0.1544 0.078 Uiso calc R 1 . . H
H22B 0.9903 0.6691 -0.0448 0.078 Uiso calc R 1 . . H
C23 0.9826(3) 0.7784(3) -0.1044(3) 0.1018(11) Uani d . 1 . . C
H23A 1.0673 0.8114 -0.0844 0.153 Uiso calc R 1 . . H
H23B 0.9472 0.8270 -0.0598 0.153 Uiso calc R 1 . . H
H23C 0.9521 0.7710 -0.1673 0.153 Uiso calc R 1 . . H
S1' 0.59009(6) 0.06546(6) 0.18901(4) 0.06011(19) Uani d . 1 . . S
Cl1' 0.53506(6) 0.69778(7) 1.00401(4) 0.0787(2) Uani d . 1 . . Cl
O1' 0.68877(14) 0.37945(15) 0.66260(10) 0.0613(4) Uani d . 1 . . O
N1' 0.50461(15) 0.38250(15) 0.60285(11) 0.0429(4) Uani d . 1 . . N
N2' 0.40559(15) 0.28553(15) 0.43701(12) 0.0452(4) Uani d . 1 . . N
N3' 0.31617(16) 0.39209(18) 0.54449(13) 0.0595(5) Uani d D 1 . . N
H3'A 0.3276 0.4486 0.5999 0.071 Uiso calc PR 0.515(8) A 1 H
H3'B 0.3138 0.4340 0.6052 0.071 Uiso d PR 0.485(8) A 2 H
N4' 0.70662(17) 0.17901(16) 0.37671(13) 0.0516(5) Uani d . 1 . . N
C1' 0.40820(19) 0.35119(18) 0.52575(14) 0.0435(5) Uani d . 1 A . C
C2' 0.60838(19) 0.34809(18) 0.59099(14) 0.0445(5) Uani d . 1 . . C
C3' 0.60749(18) 0.27802(17) 0.49249(14) 0.0409(5) Uani d . 1 . . C
C4' 0.50282(18) 0.24763(17) 0.42087(14) 0.0406(5) Uani d . 1 . . C
C5' 0.70776(19) 0.24138(19) 0.46733(15) 0.0468(5) Uani d . 1 . . C
C6' 0.8233(2) 0.2721(2) 0.53933(17) 0.0619(6) Uani d . 1 . . C
H6'A 0.8788 0.2404 0.5065 0.093 Uiso calc R 1 . . H
H6'B 0.8098 0.2418 0.5837 0.093 Uiso calc R 1 . . H
H6'C 0.8550 0.3538 0.5738 0.093 Uiso calc R 1 . . H
C7' 0.6044(2) 0.14785(18) 0.31009(15) 0.0471(5) Uani d . 1 . . C
C8' 0.49967(19) 0.17450(17) 0.32520(14) 0.0431(5) Uani d . 1 . . C
C9' 0.4048(2) 0.12283(17) 0.23743(14) 0.0448(5) Uani d . 1 . . C
C10' 0.2773(2) 0.1222(2) 0.22841(16) 0.0548(6) Uani d . 1 . . C
H10C 0.2695 0.1955 0.2345 0.066 Uiso calc R 1 . . H
H10D 0.2510 0.1102 0.2796 0.066 Uiso calc R 1 . . H
C11' 0.1996(2) 0.0268(2) 0.13060(17) 0.0656(7) Uani d . 1 . . C
H11C 0.1944 -0.0469 0.1297 0.079 Uiso calc R 1 . . H
H11D 0.1199 0.0348 0.1208 0.079 Uiso calc R 1 . . H
C12' 0.2512(3) 0.0324(2) 0.05077(17) 0.0712(8) Uani d . 1 . . C
H12C 0.2613 0.1080 0.0545 0.085 Uiso calc R 1 . . H
H12D 0.1966 -0.0226 -0.0108 0.085 Uiso calc R 1 . . H
C13' 0.3702(3) 0.0071(2) 0.05733(16) 0.0660(7) Uani d . 1 . . C
H13C 0.3576 -0.0747 0.0317 0.079 Uiso calc R 1 . . H
H13D 0.4126 0.0335 0.0191 0.079 Uiso calc R 1 . . H
C14' 0.4433(2) 0.06570(18) 0.16013(15) 0.0519(6) Uani d . 1 . . C
C15' 0.50559(18) 0.45880(18) 0.69984(14) 0.0411(5) Uani d . 1 . . C
C16' 0.4849(2) 0.4146(2) 0.76316(15) 0.0491(5) Uani d . 1 . . C
H16A 0.4655 0.3361 0.7426 0.059 Uiso calc R 1 . . H
C17' 0.4934(2) 0.4883(2) 0.85735(16) 0.0537(6) Uani d . 1 . . C
H17A 0.4809 0.4602 0.9012 0.064 Uiso calc R 1 . . H
C18' 0.52042(19) 0.6032(2) 0.88507(15) 0.0490(5) Uani d . 1 . . C
C19' 0.53746(19) 0.64733(19) 0.82174(16) 0.0505(5) Uani d . 1 . . C
H19A 0.5532 0.7255 0.8417 0.061 Uiso calc R 1 . . H
C20' 0.53092(19) 0.57393(19) 0.72802(15) 0.0468(5) Uani d . 1 . . C
H20A 0.5436 0.6024 0.6844 0.056 Uiso calc R 1 . . H
C21' 0.1968(5) 0.3482(7) 0.4780(5) 0.053(2) Uani d PD 0.515(8) A 1 C
H21C 0.1361 0.3497 0.5126 0.063 Uiso calc PR 0.515(8) A 1 H
H21D 0.1836 0.2703 0.4300 0.063 Uiso calc PR 0.515(8) A 1 H
C22' 0.1936(6) 0.4259(5) 0.4315(5) 0.075(2) Uani d PD 0.515(8) A 1 C
H22C 0.2507 0.4193 0.3932 0.090 Uiso calc PR 0.515(8) A 1 H
H22D 0.2153 0.5045 0.4807 0.090 Uiso calc PR 0.515(8) A 1 H
C23' 0.0679(8) 0.3939(10) 0.3669(6) 0.093(3) Uani d PD 0.515(8) A 1 C
H23D 0.0721 0.4232 0.3209 0.140 Uiso calc PR 0.515(8) A 1 H
H23E 0.0176 0.4263 0.4059 0.140 Uiso calc PR 0.515(8) A 1 H
H23F 0.0357 0.3122 0.3339 0.140 Uiso calc PR 0.515(8) A 1 H
C21A 0.2202(6) 0.3681(10) 0.4607(5) 0.066(3) Uani d PD 0.485(8) A 2 C
H21E 0.1756 0.2879 0.4307 0.079 Uiso calc PR 0.485(8) A 2 H
H21F 0.2557 0.3825 0.4139 0.079 Uiso calc PR 0.485(8) A 2 H
C22A 0.1364(6) 0.4392(6) 0.4871(5) 0.082(3) Uani d PD 0.485(8) A 2 C
H22E 0.1784 0.5187 0.5082 0.098 Uiso calc PR 0.485(8) A 2 H
H22F 0.1096 0.4335 0.5404 0.098 Uiso calc PR 0.485(8) A 2 H
C23A 0.0286(8) 0.4018(11) 0.4032(6) 0.093(3) Uani d PD 0.485(8) A 2 C
H23G 0.0117 0.4680 0.4009 0.139 Uiso calc PR 0.485(8) A 2 H
H23H -0.0388 0.3577 0.4118 0.139 Uiso calc PR 0.485(8) A 2 H
H23I 0.0452 0.3560 0.3442 0.139 Uiso calc PR 0.485(8) A 2 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C7 S1 C14 91.00(11) y
C1 N1 C2 122.21(17) ?
C1 N1 C15 120.14(16) ?
C2 N1 C15 117.55(16) ?
C1 N2 C4 118.07(18) y
C1 N3 C21 121.83(17) ?
C1 N3 H3 119.1 ?
C21 N3 H3 119.1 ?
C5 N4 C7 116.82(18) y
N2 C1 N3 118.99(19) ?
N2 C1 N1 123.28(18) ?
N3 C1 N1 117.74(17) ?
O1 C2 N1 118.30(18) ?
O1 C2 C3 127.29(19) ?
N1 C2 C3 114.41(18) ?
C4 C3 C5 120.52(18) ?
C4 C3 C2 118.07(18) ?
C5 C3 C2 121.41(19) ?
N2 C4 C3 123.73(18) ?
N2 C4 C8 118.32(18) ?
C3 C4 C8 117.95(18) ?
N4 C5 C3 121.34(19) ?
N4 C5 C6 115.15(19) ?
C3 C5 C6 123.50(19) ?
C5 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C5 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
N4 C7 C8 127.34(19) ?
N4 C7 S1 121.17(17) ?
C8 C7 S1 111.49(17) ?
C7 C8 C4 115.99(19) ?
C7 C8 C9 112.30(19) ?
C4 C8 C9 131.7(2) ?
C14 C9 C8 111.9(2) ?
C14 C9 C10 121.1(2) ?
C8 C9 C10 126.98(19) ?
C9 C10 C11 111.6(2) ?
C9 C10 H10A 109.3 ?
C11 C10 H10A 109.3 ?
C9 C10 H10B 109.3 ?
C11 C10 H10B 109.3 ?
H10A C10 H10B 108.0 ?
C12 C11 C10 113.9(2) ?
C12 C11 H11A 108.8 ?
C10 C11 H11A 108.8 ?
C12 C11 H11B 108.8 ?
C10 C11 H11B 108.8 ?
H11A C11 H11B 107.7 ?
C11 C12 C13 113.2(3) ?
C11 C12 H12A 108.9 ?
C13 C12 H12A 108.9 ?
C11 C12 H12B 108.9 ?
C13 C12 H12B 108.9 ?
H12A C12 H12B 107.8 ?
C12 C13 C14 110.4(2) ?
C12 C13 H13A 109.6 ?
C14 C13 H13A 109.6 ?
C12 C13 H13B 109.6 ?
C14 C13 H13B 109.6 ?
H13A C13 H13B 108.1 ?
C9 C14 C13 125.7(2) ?
C9 C14 S1 113.33(18) ?
C13 C14 S1 120.97(19) ?
C20 C15 C16 120.4(2) ?
C20 C15 N1 119.65(19) ?
C16 C15 N1 119.94(19) ?
C15 C16 C17 119.6(2) ?
C15 C16 H16 120.2 ?
C17 C16 H16 120.2 ?
C18 C17 C16 119.3(2) ?
C18 C17 H17 120.4 ?
C16 C17 H17 120.4 ?
C19 C18 C17 121.4(2) ?
C19 C18 Cl1 119.1(2) ?
C17 C18 Cl1 119.5(2) ?
C18 C19 C20 119.1(2) ?
C18 C19 H19 120.4 ?
C20 C19 H19 120.4 ?
C15 C20 C19 120.1(2) ?
C15 C20 H20 119.9 ?
C19 C20 H20 119.9 ?
N3 C21 C22 112.82(19) ?
N3 C21 H21A 109.0 ?
C22 C21 H21A 109.0 ?
N3 C21 H21B 109.0 ?
C22 C21 H21B 109.0 ?
H21A C21 H21B 107.8 ?
C21 C22 C23 112.3(2) ?
C21 C22 H22A 109.1 ?
C23 C22 H22A 109.1 ?
C21 C22 H22B 109.1 ?
C23 C22 H22B 109.1 ?
H22A C22 H22B 107.9 ?
C22 C23 H23A 109.5 ?
C22 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C22 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
C7' S1' C14' 91.06(10) y
C1' N1' C2' 122.54(17) ?
C1' N1' C15' 120.77(17) ?
C2' N1' C15' 116.59(16) ?
C1' N2' C4' 117.71(17) y
C1' N3' C21' 125.3(4) ?
C1' N3' C21A 116.9(3) ?
C1' N3' H3'A 117.3 ?
C21' N3' H3'A 117.3 ?
C21A N3' H3'A 121.9 ?
C1' N3' H3'B 121.4 ?
C21' N3' H3'B 110.6 ?
C21A N3' H3'B 121.7 ?
C5' N4' C7' 116.56(18) y
N2' C1' N3' 119.66(18) ?
N2' C1' N1' 122.58(19) ?
N3' C1' N1' 117.75(18) ?
O1' C2' N1' 118.21(18) ?
O1' C2' C3' 126.62(19) ?
N1' C2' C3' 115.17(17) ?
C4' C3' C5' 120.47(18) ?
C4' C3' C2' 117.15(18) ?
C5' C3' C2' 122.38(18) ?
N2' C4' C3' 124.73(18) ?
N2' C4' C8' 118.07(18) ?
C3' C4' C8' 117.19(19) ?
N4' C5' C3' 121.82(19) ?
N4' C5' C6' 114.54(19) ?
C3' C5' C6' 123.62(19) ?
C5' C6' H6'A 109.5 ?
C5' C6' H6'B 109.5 ?
H6'A C6' H6'B 109.5 ?
C5' C6' H6'C 109.5 ?
H6'A C6' H6'C 109.5 ?
H6'B C6' H6'C 109.5 ?
N4' C7' C8' 127.31(19) ?
N4' C7' S1' 121.46(16) ?
C8' C7' S1' 111.23(16) ?
C7' C8' C4' 116.41(19) ?
C7' C8' C9' 112.77(18) ?
C4' C8' C9' 130.8(2) ?
C14' C9' C8' 111.1(2) ?
C14' C9' C10' 121.7(2) ?
C8' C9' C10' 127.08(18) ?
C9' C10' C11' 110.02(19) ?
C9' C10' H10C 109.7 ?
C11' C10' H10C 109.7 ?
C9' C10' H10D 109.7 ?
C11' C10' H10D 109.7 ?
H10C C10' H10D 108.2 ?
C12' C11' C10' 110.5(2) ?
C12' C11' H11C 109.6 ?
C10' C11' H11C 109.6 ?
C12' C11' H11D 109.6 ?
C10' C11' H11D 109.6 ?
H11C C11' H11D 108.1 ?
C11' C12' C13' 111.1(2) ?
C11' C12' H12C 109.4 ?
C13' C12' H12C 109.4 ?
C11' C12' H12D 109.4 ?
C13' C12' H12D 109.4 ?
H12C C12' H12D 108.0 ?
C14' C13' C12' 110.3(2) ?
C14' C13' H13C 109.6 ?
C12' C13' H13C 109.6 ?
C14' C13' H13D 109.6 ?
C12' C13' H13D 109.6 ?
H13C C13' H13D 108.1 ?
C9' C14' C13' 125.4(2) ?
C9' C14' S1' 113.70(17) ?
C13' C14' S1' 120.92(18) ?
C20' C15' C16' 121.16(19) ?
C20' C15' N1' 119.35(18) ?
C16' C15' N1' 119.45(18) ?
C15' C16' C17' 119.3(2) ?
C15' C16' H16A 120.3 ?
C17' C16' H16A 120.3 ?
C18' C17' C16' 119.0(2) ?
C18' C17' H17A 120.5 ?
C16' C17' H17A 120.5 ?
C17' C18' C19' 121.9(2) ?
C17' C18' Cl1' 119.74(18) ?
C19' C18' Cl1' 118.33(18) ?
C18' C19' C20' 119.1(2) ?
C18' C19' H19A 120.5 ?
C20' C19' H19A 120.5 ?
C15' C20' C19' 119.4(2) ?
C15' C20' H20A 120.3 ?
C19' C20' H20A 120.3 ?
N3' C21' C22' 105.8(5) ?
N3' C21' H21C 110.6 ?
C22' C21' H21C 110.6 ?
N3' C21' H21D 110.6 ?
C22' C21' H21D 110.6 ?
H21C C21' H21D 108.7 ?
C21' C22' C23' 110.0(5) ?
C21' C22' H22C 109.7 ?
C23' C22' H22C 109.7 ?
C21' C22' H22D 109.7 ?
C23' C22' H22D 109.7 ?
H22C C22' H22D 108.2 ?
N3' C21A C22A 112.9(6) ?
N3' C21A H21E 109.0 ?
C22A C21A H21E 109.0 ?
N3' C21A H21F 109.0 ?
C22A C21A H21F 109.0 ?
H21E C21A H21F 107.8 ?
C21A C22A C23A 112.2(6) ?
C21A C22A H22E 109.2 ?
C23A C22A H22E 109.2 ?
C21A C22A H22F 109.2 ?
C23A C22A H22F 109.2 ?
H22E C22A H22F 107.9 ?
C22A C23A H23G 109.5 ?
C22A C23A H23H 109.5 ?
H23G C23A H23H 109.5 ?
C22A C23A H23I 109.5 ?
H23G C23A H23I 109.5 ?
H23H C23A H23I 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.737(2) y
S1 C14 1.738(3) y
Cl1 C18 1.738(2) ?
O1 C2 1.209(2) y
N1 C1 1.384(3) ?
N1 C2 1.417(3) ?
N1 C15 1.447(2) ?
N2 C1 1.308(2) y
N2 C4 1.367(3) y
N3 C1 1.337(3) ?
N3 C21 1.450(3) ?
N3 H3 0.86 ?
N4 C5 1.334(3) y
N4 C7 1.349(3) y
C2 C3 1.461(3) ?
C3 C4 1.409(3) ?
C3 C5 1.426(3) ?
C4 C8 1.414(3) ?
C5 C6 1.493(3) ?
C6 H6A 0.96 ?
C6 H6B 0.96 ?
C6 H6C 0.96 ?
C7 C8 1.391(3) ?
C8 C9 1.446(3) ?
C9 C14 1.353(3) ?
C9 C10 1.507(3) ?
C10 C11 1.522(3) ?
C10 H10A 0.97 ?
C10 H10B 0.97 ?
C11 C12 1.486(4) ?
C11 H11A 0.97 ?
C11 H11B 0.97 ?
C12 C13 1.494(4) ?
C12 H12A 0.97 ?
C12 H12B 0.97 ?
C13 C14 1.508(3) ?
C13 H13A 0.97 ?
C13 H13B 0.97 ?
C15 C20 1.374(3) ?
C15 C16 1.378(3) ?
C16 C17 1.387(3) ?
C16 H16 0.93 ?
C17 C18 1.371(4) ?
C17 H17 0.93 ?
C18 C19 1.370(4) ?
C19 C20 1.380(3) ?
C19 H19 0.93 ?
C20 H20 0.93 ?
C21 C22 1.490(3) ?
C21 H21A 0.97 ?
C21 H21B 0.97 ?
C22 C23 1.510(4) ?
C22 H22A 0.97 ?
C22 H22B 0.97 ?
C23 H23A 0.96 ?
C23 H23B 0.96 ?
C23 H23C 0.96 ?
S1' C7' 1.734(2) y
S1' C14' 1.735(3) y
Cl1' C18' 1.741(2) ?
O1' C2' 1.220(2) y
N1' C1' 1.391(3) ?
N1' C2' 1.412(3) ?
N1' C15' 1.450(2) ?
N2' C1' 1.307(2) y
N2' C4' 1.369(3) y
N3' C1' 1.337(3) ?
N3' C21' 1.473(6) ?
N3' C21A 1.483(6) ?
N3' H3'A 0.86 ?
N3' H3'B 0.90 ?
N4' C5' 1.327(3) y
N4' C7' 1.343(3) y
C2' C3' 1.449(3) ?
C3' C4' 1.408(3) ?
C3' C5' 1.427(3) ?
C4' C8' 1.415(3) ?
C5' C6' 1.503(3) ?
C6' H6'A 0.96 ?
C6' H6'B 0.96 ?
C6' H6'C 0.96 ?
C7' C8' 1.390(3) ?
C8' C9' 1.448(3) ?
C9' C14' 1.353(3) ?
C9' C10' 1.498(3) ?
C10' C11' 1.535(3) ?
C10' H10C 0.97 ?
C10' H10D 0.97 ?
C11' C12' 1.507(4) ?
C11' H11C 0.97 ?
C11' H11D 0.97 ?
C12' C13' 1.515(4) ?
C12' H12C 0.97 ?
C12' H12D 0.97 ?
C13' C14' 1.504(3) ?
C13' H13C 0.97 ?
C13' H13D 0.97 ?
C15' C20' 1.371(3) ?
C15' C16' 1.382(3) ?
C16' C17' 1.383(3) ?
C16' H16A 0.93 ?
C17' C18' 1.368(3) ?
C17' H17A 0.93 ?
C18' C19' 1.373(3) ?
C19' C20' 1.382(3) ?
C19' H19A 0.93 ?
C20' H20A 0.93 ?
C21' C22' 1.499(7) ?
C21' H21C 0.97 ?
C21' H21D 0.97 ?
C22' C23' 1.541(7) ?
C22' H22C 0.97 ?
C22' H22D 0.97 ?
C23' H23D 0.96 ?
C23' H23E 0.96 ?
C23' H23F 0.96 ?
C21A C22A 1.500(8) ?
C21A H21E 0.97 ?
C21A H21F 0.97 ?
C22A C23A 1.525(7) ?
C22A H22E 0.97 ?
C22A H22F 0.97 ?
C23A H23G 0.96 ?
C23A H23H 0.96 ?
C23A H23I 0.96 ?
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
N3' H3'B N4 2_666 0.90 2.30 3.072(3) 144
N3 H3 O1' 1_554 0.86 2.22 2.912(2) 138
C13' H13C O1 2_655 0.97 2.38 3.285(3) 154
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
C4 N2 C1 N3 176.93(18)
C4 N2 C1 N1 -3.1(3)
C21 N3 C1 N2 3.0(3)
C21 N3 C1 N1 -177.02(17)
C2 N1 C1 N2 -0.7(3)
C15 N1 C1 N2 -176.76(18)
C2 N1 C1 N3 179.31(18)
C15 N1 C1 N3 3.3(3)
C1 N1 C2 O1 -175.47(18)
C15 N1 C2 O1 0.7(3)
C1 N1 C2 C3 4.6(3)
C15 N1 C2 C3 -179.30(16)
O1 C2 C3 C4 175.3(2)
N1 C2 C3 C4 -4.7(3)
O1 C2 C3 C5 -4.8(3)
N1 C2 C3 C5 175.16(18)
C1 N2 C4 C3 2.7(3)
C1 N2 C4 C8 -176.41(17)
C5 C3 C4 N2 -178.51(18)
C2 C3 C4 N2 1.4(3)
C5 C3 C4 C8 0.6(3)
C2 C3 C4 C8 -179.56(17)
C7 N4 C5 C3 -2.3(3)
C7 N4 C5 C6 178.72(19)
C4 C3 C5 N4 1.4(3)
C2 C3 C5 N4 -178.49(19)
C4 C3 C5 C6 -179.8(2)
C2 C3 C5 C6 0.4(3)
C5 N4 C7 C8 1.5(3)
C5 N4 C7 S1 -179.10(16)
C14 S1 C7 N4 -179.7(2)
C14 S1 C7 C8 -0.19(18)
N4 C7 C8 C4 0.4(3)
S1 C7 C8 C4 -179.06(14)
N4 C7 C8 C9 179.4(2)
S1 C7 C8 C9 0.0(2)
N2 C4 C8 C7 177.77(18)
C3 C4 C8 C7 -1.4(3)
N2 C4 C8 C9 -1.0(3)
C3 C4 C8 C9 179.8(2)
C7 C8 C9 C14 0.3(3)
C4 C8 C9 C14 179.1(2)
C7 C8 C9 C10 179.5(2)
C4 C8 C9 C10 -1.6(4)
C14 C9 C10 C11 -12.4(3)
C8 C9 C10 C11 168.5(2)
C9 C10 C11 C12 41.3(3)
C10 C11 C12 C13 -58.9(4)
C11 C12 C13 C14 42.8(4)
C8 C9 C14 C13 178.7(2)
C10 C9 C14 C13 -0.6(4)
C8 C9 C14 S1 -0.4(3)
C10 C9 C14 S1 -179.73(17)
C12 C13 C14 C9 -14.4(4)
C12 C13 C14 S1 164.7(2)
C7 S1 C14 C9 0.4(2)
C7 S1 C14 C13 -178.8(2)
C1 N1 C15 C20 73.4(3)
C2 N1 C15 C20 -102.8(2)
C1 N1 C15 C16 -105.8(2)
C2 N1 C15 C16 78.0(3)
C20 C15 C16 C17 -1.8(3)
N1 C15 C16 C17 177.4(2)
C15 C16 C17 C18 0.3(4)
C16 C17 C18 C19 1.0(4)
C16 C17 C18 Cl1 -178.53(18)
C17 C18 C19 C20 -0.7(4)
Cl1 C18 C19 C20 178.84(18)
C16 C15 C20 C19 2.1(3)
N1 C15 C20 C19 -177.1(2)
C18 C19 C20 C15 -0.9(4)
C1 N3 C21 C22 82.8(3)
N3 C21 C22 C23 -178.0(2)
C4' N2' C1' N3' 178.58(19)
C4' N2' C1' N1' -0.4(3)
C21' N3' C1' N2' 16.4(5)
C21A N3' C1' N2' -5.5(6)
C21' N3' C1' N1' -164.6(4)
C21A N3' C1' N1' 173.6(6)
C2' N1' C1' N2' 1.6(3)
C15' N1' C1' N2' 177.81(19)
C2' N1' C1' N3' -177.4(2)
C15' N1' C1' N3' -1.2(3)
C1' N1' C2' O1' -180.0(2)
C15' N1' C2' O1' 3.7(3)
C1' N1' C2' C3' 0.2(3)
C15' N1' C2' C3' -176.12(17)
O1' C2' C3' C4' 177.3(2)
N1' C2' C3' C4' -3.0(3)
O1' C2' C3' C5' -3.4(4)
N1' C2' C3' C5' 176.36(19)
C1' N2' C4' C3' -2.7(3)
C1' N2' C4' C8' 178.67(19)
C5' C3' C4' N2' -174.88(19)
C2' C3' C4' N2' 4.5(3)
C5' C3' C4' C8' 3.7(3)
C2' C3' C4' C8' -176.92(18)
C7' N4' C5' C3' -2.8(3)
C7' N4' C5' C6' 178.8(2)
C4' C3' C5' N4' 0.6(3)
C2' C3' C5' N4' -178.7(2)
C4' C3' C5' C6' 178.8(2)
C2' C3' C5' C6' -0.5(3)
C5' N4' C7' C8' 0.7(3)
C5' N4' C7' S1' -179.56(17)
C14' S1' C7' N4' 179.32(19)
C14' S1' C7' C8' -0.88(18)
N4' C7' C8' C4' 3.6(3)
S1' C7' C8' C4' -176.18(15)
N4' C7' C8' C9' -177.6(2)
S1' C7' C8' C9' 2.6(2)
N2' C4' C8' C7' 173.20(18)
C3' C4' C8' C7' -5.5(3)
N2' C4' C8' C9' -5.4(3)
C3' C4' C8' C9' 176.0(2)
C7' C8' C9' C14' -3.5(3)
C4' C8' C9' C14' 175.1(2)
C7' C8' C9' C10' 172.5(2)
C4' C8' C9' C10' -8.9(4)
C14' C9' C10' C11' 14.9(3)
C8' C9' C10' C11' -160.7(2)
C9' C10' C11' C12' -49.8(3)
C10' C11' C12' C13' 65.6(3)
C11' C12' C13' C14' -41.8(3)
C8' C9' C14' C13' -176.7(2)
C10' C9' C14' C13' 7.0(4)
C8' C9' C14' S1' 2.8(2)
C10' C9' C14' S1' -173.43(17)
C12' C13' C14' C9' 6.6(3)
C12' C13' C14' S1' -172.92(18)
C7' S1' C14' C9' -1.19(19)
C7' S1' C14' C13' 178.4(2)
C1' N1' C15' C20' -78.1(3)
C2' N1' C15' C20' 98.3(2)
C1' N1' C15' C16' 104.0(2)
C2' N1' C15' C16' -79.5(2)
C20' C15' C16' C17' -1.9(3)
N1' C15' C16' C17' 175.91(19)
C15' C16' C17' C18' 0.9(3)
C16' C17' C18' C19' 1.1(3)
C16' C17' C18' Cl1' -178.44(17)
C17' C18' C19' C20' -2.1(3)
Cl1' C18' C19' C20' 177.41(16)
C16' C15' C20' C19' 0.9(3)
N1' C15' C20' C19' -176.94(18)
C18' C19' C20' C15' 1.1(3)
C1' N3' C21' C22' -98.1(7)
C21A N3' C21' C22' -26.3(15)
N3' C21' C22' C23' -174.9(6)
C1' N3' C21A C22A -166.4(7)
C21' N3' C21A C22A 73.9(16)
N3' C21A C22A C23A -171.7(8)
