#------------------------------------------------------------------------------
#$Date: 2022-04-07 00:54:10 +0300 (Thu, 07 Apr 2022) $
#$Revision: 274402 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/99/7129932.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7129932
loop_
_publ_author_name
'Tanaka, Katsumasa'
'Hattori, Hiroshi'
'Yabe, Ryota'
'Nishimura, Takahiro'
_publ_section_title
;
 Ir-catalyzed cyclization of α,ω-dienes with an N-methyl group via two
 C--H activation steps
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01275H
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H29 N3 O S'
_chemical_formula_sum            'C25 H29 N3 O S'
_chemical_formula_weight         419.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_audit_creation_date             2021-6-10
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-04 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.764(3)
_cell_length_b                   15.357(5)
_cell_length_c                   18.436(6)
_cell_measurement_reflns_used    6270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.4662
_cell_measurement_theta_min      2.5771
_cell_volume                     2198.2(13)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 55.0061
	          2theta: -25.3157
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 55.0061
	          2theta: -25.3157
scan:
	Number of images: 360
	           Slice: -115.0000 - 65.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 55.0061
	          2theta: -25.3157

;
_diffrn_measurement_device       'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_device_details 'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku AFC11 with Saturn 724+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22594
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         2.577
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             896
_exptl_crystal_preparation
'mounted on the CryoLoop with Palaton oil and placed in N2 stream at 100(2) K'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4440
_reflns_number_total             4988
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc01275h2.cif
_cod_data_source_block           tk2083
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2198.1(13)
_cod_database_code               7129932
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82487(8) 0.88206(4) 0.08002(3) 0.02362(15) Uani 1 1 d . . . . .
C1 C 0.7810(3) 0.77080(14) 0.08749(12) 0.0197(5) Uani 1 1 d . . . . .
C2 C 0.6130(3) 0.73400(17) 0.06220(13) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.518(4) 0.7736(18) 0.0744(15) 0.031(7) Uiso 1 1 d . . . . .
H2B H 0.614(3) 0.7244(18) 0.0108(14) 0.027(7) Uiso 1 1 d . . . . .
C3 C 0.5821(3) 0.64771(16) 0.10136(13) 0.0239(5) Uani 1 1 d . . . . .
H3A H 0.554(3) 0.6593(16) 0.1562(14) 0.024(7) Uiso 1 1 d . . . . .
H3B H 0.483(3) 0.6203(17) 0.0825(14) 0.023(6) Uiso 1 1 d . . . . .
C4 C 0.7389(3) 0.58827(15) 0.09392(12) 0.0198(5) Uani 1 1 d . . . . .
H4A H 0.767(3) 0.5833(13) 0.0409(11) 0.005(5) Uiso 1 1 d . . . . .
C5 C 0.9027(3) 0.62619(14) 0.13161(12) 0.0180(4) Uani 1 1 d . . . . .
C6 C 0.9098(3) 0.72479(14) 0.11993(11) 0.0172(5) Uani 1 1 d . . . . .
C7 C 1.0504(3) 0.78103(14) 0.14307(12) 0.0181(5) Uani 1 1 d . . . . .
C8 C 1.2022(3) 0.76193(16) 0.18145(12) 0.0208(5) Uani 1 1 d . . . . .
H8A H 1.234(3) 0.7036(18) 0.1945(12) 0.023(6) Uiso 1 1 d . . . . .
C9 C 1.3142(3) 0.82779(15) 0.20084(12) 0.0235(5) Uani 1 1 d . . . . .
H9A H 1.422(3) 0.8114(16) 0.2280(13) 0.024(7) Uiso 1 1 d . . . . .
C10 C 1.2799(3) 0.91454(17) 0.18232(13) 0.0268(6) Uani 1 1 d . . . . .
H10A H 1.366(4) 0.9592(18) 0.1991(13) 0.032(7) Uiso 1 1 d . . . . .
C11 C 1.1341(3) 0.93578(15) 0.14362(13) 0.0258(5) Uani 1 1 d . . . . .
H11A H 1.111(3) 0.9928(18) 0.1286(15) 0.036(8) Uiso 1 1 d . . . . .
C12 C 1.0204(3) 0.86941(15) 0.12477(12) 0.0207(5) Uani 1 1 d . . . . .
C13 C 0.9001(3) 0.60728(17) 0.21369(13) 0.0228(5) Uani 1 1 d . . . . .
H13A H 0.791(3) 0.6279(16) 0.2375(13) 0.021(6) Uiso 1 1 d . . . . .
H13B H 0.991(4) 0.6367(19) 0.2390(15) 0.036(8) Uiso 1 1 d . . . . .
H13C H 0.918(3) 0.5444(17) 0.2235(12) 0.019(6) Uiso 1 1 d . . . . .
C14 C 1.0615(3) 0.58343(17) 0.09666(15) 0.0241(5) Uani 1 1 d . . . . .
H14A H 1.168(4) 0.6022(16) 0.1193(14) 0.030(7) Uiso 1 1 d . . . . .
H14B H 1.055(3) 0.5218(19) 0.1013(14) 0.028(7) Uiso 1 1 d . . . . .
H14C H 1.064(3) 0.5977(18) 0.0432(16) 0.034(8) Uiso 1 1 d . . . . .
C15 C 0.6982(3) 0.49647(16) 0.12138(15) 0.0261(5) Uani 1 1 d . . . . .
H15A H 0.659(3) 0.4988(15) 0.1703(13) 0.018(6) Uiso 1 1 d . . . . .
H15B H 0.800(4) 0.4595(16) 0.1220(14) 0.025(7) Uiso 1 1 d . . . . .
N1 N 0.5620(3) 0.45447(14) 0.07989(13) 0.0268(5) Uani 1 1 d . . . . .
H1N H 0.588(4) 0.436(2) 0.0405(17) 0.036(9) Uiso 1 1 d . . . . .
N2 N 0.3922(3) 0.43489(13) 0.18146(11) 0.0240(5) Uani 1 1 d . . . . .
C16 C 0.4202(3) 0.41865(15) 0.11060(12) 0.0197(5) Uani 1 1 d . . . . .
C17 C 0.3042(3) 0.36645(13) 0.06890(12) 0.0188(5) Uani 1 1 d . . . . .
C18 C 0.1738(3) 0.32373(15) 0.10569(13) 0.0242(5) Uani 1 1 d . . . . .
H18A H 0.100(3) 0.2777(17) 0.0788(13) 0.025(6) Uiso 1 1 d . . . . .
C19 C 0.1490(3) 0.33786(18) 0.17929(14) 0.0304(6) Uani 1 1 d . . . . .
H19A H 0.063(4) 0.310(2) 0.2043(16) 0.047(9) Uiso 1 1 d . . . . .
C20 C 0.2583(3) 0.39563(18) 0.21329(14) 0.0294(6) Uani 1 1 d . . . . .
H20A H 0.244(3) 0.4097(16) 0.2632(14) 0.027(7) Uiso 1 1 d . . . . .
C21 C 0.3308(3) 0.35565(14) -0.01073(12) 0.0207(5) Uani 1 1 d . . . . .
O1 O 0.4782(2) 0.35725(11) -0.03803(9) 0.0275(4) Uani 1 1 d . . . . .
N3 N 0.1929(3) 0.34387(12) -0.05381(10) 0.0225(4) Uani 1 1 d . . . . .
C22 C 0.0095(3) 0.36016(17) -0.03686(14) 0.0237(5) Uani 1 1 d . . . . .
H22A H -0.003(4) 0.4050(19) 0.0020(14) 0.032(8) Uiso 1 1 d . . . . .
H22B H -0.042(4) 0.3068(19) -0.0187(14) 0.031(7) Uiso 1 1 d . . . . .
C23 C -0.0641(4) 0.3892(2) -0.10922(15) 0.0359(7) Uani 1 1 d . . . . .
H23A H -0.188(4) 0.3804(18) -0.1107(15) 0.041(8) Uiso 1 1 d . . . . .
H23B H -0.044(4) 0.451(2) -0.1161(17) 0.055(10) Uiso 1 1 d . . . . .
C24 C 0.0371(4) 0.3348(3) -0.16360(15) 0.0414(7) Uani 1 1 d . . . . .
H24A H 0.033(4) 0.3672(19) -0.2124(16) 0.040(8) Uiso 1 1 d . . . . .
H24B H -0.014(5) 0.274(2) -0.1665(18) 0.062(11) Uiso 1 1 d . . . . .
C25 C 0.2190(4) 0.3351(2) -0.13263(14) 0.0359(7) Uani 1 1 d . . . . .
H25A H 0.294(4) 0.3857(19) -0.1473(15) 0.046(9) Uiso 1 1 d . . . . .
H25B H 0.283(4) 0.283(2) -0.1402(15) 0.041(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C1 91.36(11) . . ?
C6 C1 C2 125.5(2) . . ?
C6 C1 S1 113.47(17) . . ?
C2 C1 S1 120.99(17) . . ?
C1 C2 C3 108.5(2) . . ?
C1 C2 H2A 110.6(16) . . ?
C3 C2 H2A 108.0(16) . . ?
C1 C2 H2B 110.9(17) . . ?
C3 C2 H2B 109.6(16) . . ?
H2A C2 H2B 109(2) . . ?
C4 C3 C2 110.5(2) . . ?
C4 C3 H3A 110.7(14) . . ?
C2 C3 H3A 109.9(14) . . ?
C4 C3 H3B 110.4(15) . . ?
C2 C3 H3B 109.9(16) . . ?
H3A C3 H3B 105(2) . . ?
C3 C4 C15 110.87(19) . . ?
C3 C4 C5 112.69(18) . . ?
C15 C4 C5 111.36(19) . . ?
C3 C4 H4A 107.9(12) . . ?
C15 C4 H4A 107.3(12) . . ?
C5 C4 H4A 106.4(12) . . ?
C6 C5 C14 109.52(18) . . ?
C6 C5 C13 108.97(18) . . ?
C14 C5 C13 109.9(2) . . ?
C6 C5 C4 109.63(18) . . ?
C14 C5 C4 107.88(17) . . ?
C13 C5 C4 110.88(18) . . ?
C1 C6 C7 111.8(2) . . ?
C1 C6 C5 123.2(2) . . ?
C7 C6 C5 125.0(2) . . ?
C8 C7 C12 117.2(2) . . ?
C8 C7 C6 130.7(2) . . ?
C12 C7 C6 112.0(2) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8A 117.0(15) . . ?
C7 C8 H8A 122.6(15) . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9A 117.9(14) . . ?
C10 C9 H9A 121.1(15) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10A 123.0(16) . . ?
C9 C10 H10A 116.5(16) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 H11A 122.3(17) . . ?
C12 C11 H11A 119.1(17) . . ?
C11 C12 C7 122.5(2) . . ?
C11 C12 S1 126.18(18) . . ?
C7 C12 S1 111.29(17) . . ?
C5 C13 H13A 112.4(13) . . ?
C5 C13 H13B 112.3(17) . . ?
H13A C13 H13B 105(2) . . ?
C5 C13 H13C 111.2(14) . . ?
H13A C13 H13C 110(2) . . ?
H13B C13 H13C 105(2) . . ?
C5 C14 H14A 112.1(16) . . ?
C5 C14 H14B 110.1(16) . . ?
H14A C14 H14B 108(2) . . ?
C5 C14 H14C 109.4(16) . . ?
H14A C14 H14C 110(2) . . ?
H14B C14 H14C 108(2) . . ?
N1 C15 C4 112.6(2) . . ?
N1 C15 H15A 106.3(15) . . ?
C4 C15 H15A 110.2(14) . . ?
N1 C15 H15B 109.6(15) . . ?
C4 C15 H15B 112.1(15) . . ?
H15A C15 H15B 106(2) . . ?
C16 N1 C15 123.4(2) . . ?
C16 N1 H1N 116(2) . . ?
C15 N1 H1N 116(2) . . ?
C20 N2 C16 117.9(2) . . ?
N2 C16 N1 117.5(2) . . ?
N2 C16 C17 121.5(2) . . ?
N1 C16 C17 121.0(2) . . ?
C18 C17 C16 117.6(2) . . ?
C18 C17 C21 122.1(2) . . ?
C16 C17 C21 120.3(2) . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18A 119.5(14) . . ?
C19 C18 H18A 120.0(14) . . ?
C20 C19 C18 117.4(2) . . ?
C20 C19 H19A 121(2) . . ?
C18 C19 H19A 121(2) . . ?
N2 C20 C19 124.7(2) . . ?
N2 C20 H20A 114.2(16) . . ?
C19 C20 H20A 121.1(16) . . ?
O1 C21 N3 119.6(2) . . ?
O1 C21 C17 121.4(2) . . ?
N3 C21 C17 119.1(2) . . ?
C21 N3 C25 119.0(2) . . ?
C21 N3 C22 128.22(19) . . ?
C25 N3 C22 110.88(19) . . ?
N3 C22 C23 103.1(2) . . ?
N3 C22 H22A 111.1(16) . . ?
C23 C22 H22A 113.1(15) . . ?
N3 C22 H22B 109.2(16) . . ?
C23 C22 H22B 113.2(16) . . ?
H22A C22 H22B 107(2) . . ?
C22 C23 C24 102.9(2) . . ?
C22 C23 H23A 110.9(17) . . ?
C24 C23 H23A 114.6(17) . . ?
C22 C23 H23B 110(2) . . ?
C24 C23 H23B 112(2) . . ?
H23A C23 H23B 107(3) . . ?
C23 C24 C25 103.3(2) . . ?
C23 C24 H24A 107.2(16) . . ?
C25 C24 H24A 110.6(16) . . ?
C23 C24 H24B 110(2) . . ?
C25 C24 H24B 113(2) . . ?
H24A C24 H24B 113(2) . . ?
N3 C25 C24 104.0(2) . . ?
N3 C25 H25A 105.9(16) . . ?
C24 C25 H25A 115.9(17) . . ?
N3 C25 H25B 107.0(17) . . ?
C24 C25 H25B 115.2(18) . . ?
H25A C25 H25B 108(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.739(2) . ?
S1 C1 1.748(2) . ?
C1 C6 1.363(3) . ?
C1 C2 1.495(3) . ?
C2 C3 1.528(4) . ?
C2 H2A 0.98(3) . ?
C2 H2B 0.96(3) . ?
C3 C4 1.528(3) . ?
C3 H3A 1.05(2) . ?
C3 H3B 0.94(3) . ?
C4 C15 1.531(3) . ?
C4 C5 1.562(3) . ?
C4 H4A 1.00(2) . ?
C5 C6 1.530(3) . ?
C5 C14 1.539(3) . ?
C5 C13 1.541(3) . ?
C6 C7 1.456(3) . ?
C7 C8 1.405(3) . ?
C7 C12 1.418(3) . ?
C8 C9 1.381(3) . ?
C8 H8A 0.96(3) . ?
C9 C10 1.401(4) . ?
C9 H9A 1.00(3) . ?
C10 C11 1.377(4) . ?
C10 H10A 1.01(3) . ?
C11 C12 1.392(3) . ?
C11 H11A 0.94(3) . ?
C13 H13A 1.01(3) . ?
C13 H13B 0.96(3) . ?
C13 H13C 0.99(3) . ?
C14 H14A 0.97(3) . ?
C14 H14B 0.95(3) . ?
C14 H14C 1.01(3) . ?
C15 N1 1.456(3) . ?
C15 H15A 0.95(2) . ?
C15 H15B 0.97(3) . ?
N1 C16 1.354(3) . ?
N1 H1N 0.81(3) . ?
N2 C20 1.337(3) . ?
N2 C16 1.348(3) . ?
C16 C17 1.430(3) . ?
C17 C18 1.384(3) . ?
C17 C21 1.492(3) . ?
C18 C19 1.387(3) . ?
C18 H18A 1.04(3) . ?
C19 C20 1.378(4) . ?
C19 H19A 0.92(3) . ?
C20 H20A 0.95(3) . ?
C21 O1 1.251(3) . ?
C21 N3 1.345(3) . ?
N3 C25 1.473(3) . ?
N3 C22 1.479(3) . ?
C22 C23 1.518(4) . ?
C22 H22A 1.00(3) . ?
C22 H22B 0.97(3) . ?
C23 C24 1.523(4) . ?
C23 H23A 0.97(3) . ?
C23 H23B 0.97(3) . ?
C24 C25 1.524(4) . ?
C24 H24A 1.03(3) . ?
C24 H24B 1.02(4) . ?
C25 H25A 1.01(3) . ?
C25 H25B 0.96(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15A N2 0.95(2) 2.30(3) 2.786(3) 110.9(18) . yes
N1 H1N O1 0.81(3) 2.07(3) 2.716(3) 137(3) . yes
C20 H20A S1 0.95(3) 2.97(3) 3.871(3) 158.3(19) 4_645 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C6 -2.10(18) . . . . ?
C12 S1 C1 C2 175.8(2) . . . . ?
C6 C1 C2 C3 19.9(3) . . . . ?
S1 C1 C2 C3 -157.73(17) . . . . ?
C1 C2 C3 C4 -51.6(3) . . . . ?
C2 C3 C4 C15 -170.2(2) . . . . ?
C2 C3 C4 C5 64.2(3) . . . . ?
C3 C4 C5 C6 -38.6(2) . . . . ?
C15 C4 C5 C6 -163.90(19) . . . . ?
C3 C4 C5 C14 -157.8(2) . . . . ?
C15 C4 C5 C14 76.9(2) . . . . ?
C3 C4 C5 C13 81.8(2) . . . . ?
C15 C4 C5 C13 -43.5(3) . . . . ?
C2 C1 C6 C7 -175.5(2) . . . . ?
S1 C1 C6 C7 2.3(2) . . . . ?
C2 C1 C6 C5 3.2(3) . . . . ?
S1 C1 C6 C5 -179.05(16) . . . . ?
C14 C5 C6 C1 124.2(2) . . . . ?
C13 C5 C6 C1 -115.5(2) . . . . ?
C4 C5 C6 C1 6.0(3) . . . . ?
C14 C5 C6 C7 -57.4(3) . . . . ?
C13 C5 C6 C7 62.9(3) . . . . ?
C4 C5 C6 C7 -175.55(19) . . . . ?
C1 C6 C7 C8 176.3(2) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C1 C6 C7 C12 -1.3(3) . . . . ?
C5 C6 C7 C12 -179.92(19) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 -176.6(2) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C10 C11 C12 S1 176.78(19) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C6 C7 C12 C11 177.7(2) . . . . ?
C8 C7 C12 S1 -178.20(16) . . . . ?
C6 C7 C12 S1 -0.3(2) . . . . ?
C1 S1 C12 C11 -176.6(2) . . . . ?
C1 S1 C12 C7 1.28(17) . . . . ?
C3 C4 C15 N1 62.1(3) . . . . ?
C5 C4 C15 N1 -171.5(2) . . . . ?
C4 C15 N1 C16 -127.4(2) . . . . ?
C20 N2 C16 N1 -176.1(2) . . . . ?
C20 N2 C16 C17 4.6(3) . . . . ?
C15 N1 C16 N2 10.6(3) . . . . ?
C15 N1 C16 C17 -170.1(2) . . . . ?
N2 C16 C17 C18 -8.2(3) . . . . ?
N1 C16 C17 C18 172.5(2) . . . . ?
N2 C16 C17 C21 174.9(2) . . . . ?
N1 C16 C17 C21 -4.4(3) . . . . ?
C16 C17 C18 C19 5.6(3) . . . . ?
C21 C17 C18 C19 -177.6(2) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C16 N2 C20 C19 1.7(4) . . . . ?
C18 C19 C20 N2 -4.1(4) . . . . ?
C18 C17 C21 O1 -146.0(2) . . . . ?
C16 C17 C21 O1 30.8(3) . . . . ?
C18 C17 C21 N3 33.9(3) . . . . ?
C16 C17 C21 N3 -149.3(2) . . . . ?
O1 C21 N3 C25 -1.4(3) . . . . ?
C17 C21 N3 C25 178.7(2) . . . . ?
O1 C21 N3 C22 -164.2(2) . . . . ?
C17 C21 N3 C22 15.9(3) . . . . ?
C21 N3 C22 C23 146.6(2) . . . . ?
C25 N3 C22 C23 -17.3(3) . . . . ?
N3 C22 C23 C24 34.9(3) . . . . ?
C22 C23 C24 C25 -39.8(3) . . . . ?
C21 N3 C25 C24 -172.9(2) . . . . ?
C22 N3 C25 C24 -7.3(3) . . . . ?
C23 C24 C25 N3 29.0(3) . . . . ?
