#------------------------------------------------------------------------------
#$Date: 2020-09-11 02:54:57 +0300 (Fri, 11 Sep 2020) $
#$Revision: 256316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038747.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_4038747
loop_
_publ_author_name
'Yuan, Wei-Cheng'
'Quan, Bao-Xue'
'Zhao, Jian-Qiang'
'You, Yong'
'Wang, Zhen-Hua'
'Zhou, Ming-Qiang'
_publ_section_title
;
 [4 + 2] Annulation Reaction of In Situ Generated Azoalkenes with
 Azlactones: Access to 4,5-Dihydropyridazin-3(2H)-Ones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01592
_journal_year                    2020
_chemical_formula_moiety         'C30 H25 N3 O4 S'
_chemical_formula_sum            'C30 H25 N3 O4 S'
_chemical_formula_weight         523.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.6255(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.4299(4)
_cell_length_b                   8.50556(7)
_cell_length_c                   22.1713(3)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8940
_cell_measurement_theta_min      4.2410
_cell_volume                     5296.81(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -73.00 -20.00   0.50    0.50    --  -33.50 -57.00 -90.00  106
  2  ω    -47.00  31.00   0.50    0.50    --  -33.50  37.00 -90.00  156
  3  ω    -68.00 -32.00   0.50    0.50    --  -33.50 178.00  30.00   72
  4  ω    -70.00 -24.00   0.50    0.50    --  -33.50 -57.00-120.00   92
  5  ω     59.00 109.00   0.50    0.50    --   36.47 178.00 -60.00  100
  6  ω     17.00  45.00   0.50    0.50    --   36.47 -57.00 -60.00   56
  7  ω    -32.00  34.00   0.50    0.50    --   36.47 -57.00  60.00  132
  8  ω     22.00 105.00   0.50    0.50    --   36.47  37.00 -60.00  166
  9  ω     73.00 104.00   0.50    0.50    --   36.47 178.00-120.00   62
 10  ω     50.00  75.00   0.50    0.50    --   36.47 -99.00-180.00   50
 11  ω      6.00  33.00   0.50    0.50    --   36.47 -99.00-180.00   54
 12  ω     76.00 103.00   0.50    0.50    --   36.47 178.00 -30.00   54
 13  ω     88.00 178.00   0.50    2.50    --  108.00  45.00-120.00  180
 14  ω     42.00 109.00   0.50    2.50    --  108.00 -94.00 -30.00  134
 15  ω     92.00 132.00   0.50    2.50    --  108.00 -30.00  60.00   80
 16  ω     41.00  69.00   0.50    2.50    --  108.00 -30.00  60.00   56
 17  ω     46.00 116.00   0.50    2.50    --  108.00 -45.00 -60.00  140
 18  ω     82.00 110.00   0.50    2.50    --  108.00 -94.00 150.00   56
 19  ω     71.00 105.00   0.50    2.50    --  108.00 -94.00  30.00   68
 20  ω     62.00  99.00   0.50    2.50    --  108.00-111.00 150.00   74
 21  ω     83.00 162.00   0.50    2.50    --  108.00  30.00-180.00  158
 22  ω    107.00 160.00   0.50    2.50    --  108.00 111.00  60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0093913300
_diffrn_orient_matrix_UB_12      -0.0696520677
_diffrn_orient_matrix_UB_13      0.0679940877
_diffrn_orient_matrix_UB_21      -0.0492896574
_diffrn_orient_matrix_UB_22      0.0573207736
_diffrn_orient_matrix_UB_23      -0.0049143706
_diffrn_orient_matrix_UB_31      -0.0221531891
_diffrn_orient_matrix_UB_32      -0.1570346586
_diffrn_orient_matrix_UB_33      -0.0319457309
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11203
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.256
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0802P)²+3.4767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4002
_reflns_number_total             4716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01592_si_002.cif
_cod_data_source_block           201908201a
_cod_original_cell_volume        5296.82(13)
_cod_database_code               4038747
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c20h20n4o4s1
_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_max   0.848
_shelx_estimated_absorpt_t_min   0.774
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4A-C17A
 1.2 with sigma of 0.02
 C17-C18
 1.5 with sigma of 0.02
 C17A-C18A
 1.5 with sigma of 0.02
 C17A-N3
 1.4 with sigma of 0.02
 C17-N3
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C7) = Uanis(C7A)
Uanis(C6) = Uanis(C6A)
Uanis(C8) = Uanis(C8A)
Uanis(C18) = Uanis(C18A)
Uanis(C23) = Uanis(C23A)
Uanis(C22) = Uanis(C22A)
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C19) = Uanis(C19A)
Uanis(C17) = Uanis(C17A)
Uanis(O4) = Uanis(O4A)
Uanis(C5) = Uanis(C5A)
4. Others
 Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=
 Sof(H9A)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(C5)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(H7)=
 Sof(C6)=Sof(H6)=FVAR(1)
 Sof(C17A)=Sof(C18A)=Sof(C23A)=Sof(H23A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=
 Sof(H21A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(H19A)=Sof(H3BB)=Sof(O4A)=1-FVAR(2)
 Sof(C17)=Sof(C18)=Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=Sof(H3AA)=Sof(O4)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C7(H7), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C23(H23), C22(H22), C21(H21), C20(H20), C19(H19),
 C23A(H23A), C22A(H22A), C21A(H21A), C20A(H20A), C19A(H19A), C25(H25), C26(H26),
  C28(H28), C29(H29), N3(H3AA), N3(H3BB), C6A(H6A), C7A(H7A), C8A(H8A),
 C9A(H9A), C10A(H10A)
5.c Fitted hexagon refined as free rotating group:
 C5(C10,C9,C8,C7,C6), C18(C23,C22,C21,C20,C19), C18A(C23A,C22A,C21A,C20A,C19A),
  C5A(C6A,C7A,C8A,C9A,C10A)
5.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.870
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.36888(7) 0.1527(2) 0.14250(10) 0.0426(4) Uani 1 1 d . . . . .
C2 C 0.38634(7) 0.2741(2) 0.19792(10) 0.0415(4) Uani 1 1 d . . . . .
C3 C 0.41913(8) 0.1903(3) 0.26014(11) 0.0537(5) Uani 1 1 d . . . . .
H3A H 0.4474 0.1521 0.2546 0.064 Uiso 1 1 calc R . . . .
H3B H 0.4290 0.2627 0.2968 0.064 Uiso 1 1 calc R . . . .
C4 C 0.39233(8) 0.0560(2) 0.27288(10) 0.0483(5) Uani 1 1 d . . . . .
C5 C 0.38919(12) 0.0146(3) 0.33798(11) 0.0446(9) Uani 0.655(4) 1 d . . P A 1
C10 C 0.40938(15) 0.1161(3) 0.39059(14) 0.0746(13) Uani 0.655(4) 1 d G . P A 1
H10 H 0.4222 0.2115 0.3848 0.090 Uiso 0.655(4) 1 calc R . P A 1
C9 C 0.41039(17) 0.0751(3) 0.45179(12) 0.0920(17) Uani 0.655(4) 1 d G . P A 1
H9 H 0.4239 0.1430 0.4870 0.110 Uiso 0.655(4) 1 calc R . P A 1
C8 C 0.39119(14) -0.0674(4) 0.46038(13) 0.0794(16) Uani 0.655(4) 1 d G . P A 1
H8 H 0.3919 -0.0948 0.5013 0.095 Uiso 0.655(4) 1 calc R . P A 1
C7 C 0.37099(13) -0.1689(4) 0.40776(16) 0.0775(13) Uani 0.655(4) 1 d G . P A 1
H7 H 0.3582 -0.2642 0.4135 0.093 Uiso 0.655(4) 1 calc R . P A 1
C6 C 0.36999(12) -0.1279(4) 0.34656(13) 0.0645(12) Uani 0.655(4) 1 d G . P A 1
H6 H 0.3565 -0.1958 0.3114 0.077 Uiso 0.655(4) 1 calc R . P A 1
C11 C 0.34336(7) 0.3439(2) 0.20828(10) 0.0448(4) Uani 1 1 d . . . . .
C12 C 0.29733(9) 0.3039(3) 0.16962(15) 0.0694(7) Uani 1 1 d . . . . .
H12 H 0.2915 0.2343 0.1350 0.083 Uiso 1 1 calc R . . . .
C13 C 0.25939(11) 0.3667(5) 0.1818(2) 0.0976(11) Uani 1 1 d . . . . .
H13 H 0.2285 0.3385 0.1551 0.117 Uiso 1 1 calc R . . . .
C14 C 0.26652(15) 0.4674(4) 0.2314(2) 0.0987(12) Uani 1 1 d . . . . .
H14 H 0.2408 0.5086 0.2391 0.118 Uiso 1 1 calc R . . . .
C15 C 0.31174(15) 0.5079(4) 0.27004(18) 0.0927(11) Uani 1 1 d . . . . .
H15 H 0.3170 0.5774 0.3045 0.111 Uiso 1 1 calc R . . . .
C16 C 0.35033(11) 0.4474(3) 0.25900(14) 0.0691(7) Uani 1 1 d . . . . .
H16 H 0.3811 0.4768 0.2860 0.083 Uiso 1 1 calc R . . . .
C17 C 0.4488(6) 0.3881(11) 0.1625(11) 0.0469(18) Uani 0.522(4) 1 d D . P B 1
C17A C 0.4467(7) 0.3444(12) 0.1595(13) 0.0469(18) Uani 0.478(4) 1 d D . P B 2
C18 C 0.4689(2) 0.5304(5) 0.1443(3) 0.0481(13) Uani 0.522(4) 1 d D . P B 1
C23 C 0.4935(2) 0.5091(5) 0.1035(3) 0.0727(15) Uani 0.522(4) 1 d G . P B 1
H23 H 0.4970 0.4086 0.0894 0.087 Uiso 0.522(4) 1 calc R . P B 1
C22 C 0.5127(2) 0.6378(6) 0.0837(3) 0.092(2) Uani 0.522(4) 1 d G . P B 1
H22 H 0.5291 0.6235 0.0564 0.111 Uiso 0.522(4) 1 calc R . P B 1
C21 C 0.5074(2) 0.7879(6) 0.1048(3) 0.098(2) Uani 0.522(4) 1 d G . P B 1
H21 H 0.5203 0.8740 0.0916 0.118 Uiso 0.522(4) 1 calc R . P B 1
C20 C 0.4829(2) 0.8093(5) 0.1456(3) 0.0876(17) Uani 0.522(4) 1 d G . P B 1
H20 H 0.4793 0.9097 0.1597 0.105 Uiso 0.522(4) 1 calc R . P B 1
C19 C 0.4636(2) 0.6805(5) 0.1654(3) 0.0634(15) Uani 0.522(4) 1 d G . P B 1
H19 H 0.4472 0.6948 0.1927 0.076 Uiso 0.522(4) 1 calc R . P B 1
C18A C 0.4721(2) 0.4732(5) 0.1404(4) 0.0481(13) Uani 0.478(4) 1 d D . P B 2
C23A C 0.4957(2) 0.4323(5) 0.1000(4) 0.0727(15) Uani 0.478(4) 1 d G . P B 2
H23A H 0.4945 0.3294 0.0854 0.087 Uiso 0.478(4) 1 calc R . P B 2
C22A C 0.5211(2) 0.5454(7) 0.0816(3) 0.092(2) Uani 0.478(4) 1 d G . P B 2
H22A H 0.5369 0.5181 0.0545 0.111 Uiso 0.478(4) 1 calc R . P B 2
C21A C 0.5229(2) 0.6993(7) 0.1035(3) 0.098(2) Uani 0.478(4) 1 d G . P B 2
H21A H 0.5399 0.7749 0.0911 0.118 Uiso 0.478(4) 1 calc R . P B 2
C20A C 0.4993(2) 0.7401(6) 0.1439(3) 0.0876(17) Uani 0.478(4) 1 d G . P B 2
H20A H 0.5005 0.8431 0.1585 0.105 Uiso 0.478(4) 1 calc R . P B 2
C19A C 0.4739(2) 0.6271(6) 0.1624(3) 0.0634(15) Uani 0.478(4) 1 d G . P B 2
H19A H 0.4582 0.6544 0.1894 0.076 Uiso 0.478(4) 1 calc R . P B 2
C24 C 0.28235(9) -0.1197(2) 0.08156(10) 0.0556(5) Uani 1 1 d . . . . .
C25 C 0.26029(11) -0.0256(3) 0.02722(13) 0.0729(7) Uani 1 1 d . . . . .
H25 H 0.2778 0.0181 0.0051 0.088 Uiso 1 1 calc R . . . .
C26 C 0.21261(12) 0.0022(4) 0.00645(14) 0.0828(9) Uani 1 1 d . . . . .
H26 H 0.1979 0.0664 -0.0297 0.099 Uiso 1 1 calc R . . . .
C27 C 0.18582(11) -0.0629(4) 0.03804(14) 0.0790(8) Uani 1 1 d . . . . .
C28 C 0.20850(11) -0.1588(4) 0.09194(15) 0.0813(8) Uani 1 1 d . . . . .
H28 H 0.1908 -0.2041 0.1135 0.098 Uiso 1 1 calc R . . . .
C29 C 0.25676(10) -0.1878(3) 0.11399(12) 0.0688(7) Uani 1 1 d . . . . .
H29 H 0.2717 -0.2520 0.1501 0.083 Uiso 1 1 calc R . . . .
C30 C 0.13288(13) -0.0359(5) 0.0133(2) 0.1117(13) Uani 1 1 d . . . . .
H30A H 0.1261 0.0727 0.0015 0.168 Uiso 1 1 calc GR . . . .
H30B H 0.1216 -0.0625 0.0469 0.168 Uiso 1 1 calc GR . . . .
H30C H 0.1172 -0.1007 -0.0244 0.168 Uiso 1 1 calc GR . . . .
N1 N 0.36791(7) -0.00168(18) 0.16459(8) 0.0478(4) Uani 1 1 d . . . . .
N2 N 0.36746(7) -0.03542(19) 0.22678(8) 0.0506(4) Uani 1 1 d . . . . .
N3 N 0.41114(6) 0.3995(2) 0.17943(9) 0.0487(4) Uani 1 1 d D . . . .
H3AA H 0.4003 0.4929 0.1793 0.058 Uiso 0.522(4) 1 calc R . P B 1
H3BB H 0.4046 0.4976 0.1807 0.058 Uiso 0.478(4) 1 calc R . P B 2
O1 O 0.35561(6) 0.18588(18) 0.08563(7) 0.0551(4) Uani 1 1 d . . . . .
O2 O 0.36075(8) -0.1313(2) 0.05968(9) 0.0734(5) Uani 1 1 d . . . . .
O3 O 0.35513(7) -0.29074(17) 0.14899(9) 0.0645(4) Uani 1 1 d . . . . .
O4 O 0.4649(5) 0.2549(10) 0.1618(8) 0.0660(15) Uani 0.522(4) 1 d . . P B 1
O4A O 0.4580(5) 0.2077(10) 0.1579(9) 0.0660(15) Uani 0.478(4) 1 d D . P B 2
S1 S 0.34366(2) -0.15180(6) 0.11020(3) 0.05372(19) Uani 1 1 d . . . . .
C5A C 0.4018(3) 0.0354(8) 0.3418(2) 0.0446(9) Uani 0.345(4) 1 d . . P A 2
C6A C 0.3679(2) -0.0560(8) 0.3532(3) 0.0645(12) Uani 0.345(4) 1 d G . P A 2
H6A H 0.3424 -0.0976 0.3182 0.077 Uiso 0.345(4) 1 calc R . P A 2
C7A C 0.3721(2) -0.0853(9) 0.4169(4) 0.0775(13) Uani 0.345(4) 1 d G . P A 2
H7A H 0.3494 -0.1465 0.4245 0.093 Uiso 0.345(4) 1 calc R . P A 2
C8A C 0.4102(3) -0.0232(9) 0.4691(3) 0.0794(16) Uani 0.345(4) 1 d G . P A 2
H8A H 0.4130 -0.0428 0.5117 0.095 Uiso 0.345(4) 1 calc R . P A 2
C9A C 0.4441(3) 0.0683(8) 0.4577(2) 0.0920(17) Uani 0.345(4) 1 d G . P A 2
H9A H 0.4696 0.1098 0.4927 0.110 Uiso 0.345(4) 1 calc R . P A 2
C10A C 0.4399(3) 0.0976(7) 0.3941(3) 0.0746(13) Uani 0.345(4) 1 d G . P A 2
H10A H 0.4625 0.1588 0.3864 0.090 Uiso 0.345(4) 1 calc R . P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.36(16) . . ?
O1 C1 C2 123.76(17) . . ?
O1 C1 N1 122.83(18) . . ?
C3 C2 C1 108.24(16) . . ?
C3 C2 C11 110.08(17) . . ?
C11 C2 C1 109.17(16) . . ?
N3 C2 C1 108.98(16) . . ?
N3 C2 C3 111.48(16) . . ?
N3 C2 C11 108.87(15) . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.20(17) . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C3 C4 C5 126.4(2) . . ?
N2 C4 C3 120.92(19) . . ?
N2 C4 C5 112.6(2) . . ?
N2 C4 C5A 125.9(3) . . ?
C5A C4 C3 112.9(3) . . ?
C10 C5 C4 118.89(18) . . ?
C10 C5 C6 120.0 . . ?
C6 C5 C4 120.91(18) . . ?
C5 C10 H10 120.0 . . ?
C5 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C12 C11 C2 122.3(2) . . ?
C12 C11 C16 117.8(2) . . ?
C16 C11 C2 119.8(2) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 120.4(3) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
N3 C17 C18 120.3(8) . . ?
O4 C17 C18 122.6(10) . . ?
O4 C17 N3 117.1(10) . . ?
N3 C17A C18A 113.1(7) . . ?
O4A C17A C18A 120.6(11) . . ?
O4A C17A N3 126.2(12) . . ?
C23 C18 C17 116.9(6) . . ?
C23 C18 C19 120.0 . . ?
C19 C18 C17 123.1(6) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C22 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C23A C18A C17A 116.8(7) . . ?
C23A C18A C19A 120.0 . . ?
C19A C18A C17A 123.2(7) . . ?
C18A C23A H23A 120.0 . . ?
C22A C23A C18A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C23A C22A C21A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C21A C20A C19A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C25 C24 S1 119.9(2) . . ?
C29 C24 C25 121.0(3) . . ?
C29 C24 S1 119.03(19) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 120.3 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.3(3) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 118.5(3) . . ?
C26 C27 C30 120.8(3) . . ?
C28 C27 C30 120.7(3) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.2(3) . . ?
C29 C28 H28 119.4 . . ?
C24 C29 C28 118.6(3) . . ?
C24 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 N1 N2 122.61(16) . . ?
C1 N1 S1 120.74(14) . . ?
N2 N1 S1 111.82(12) . . ?
C4 N2 N1 115.64(17) . . ?
C2 N3 H3AA 115.9 . . ?
C2 N3 H3BB 123.5 . . ?
C17 N3 C2 128.2(4) . . ?
C17 N3 H3AA 115.9 . . ?
C17A N3 C2 113.1(4) . . ?
C17A N3 H3BB 123.5 . . ?
N1 S1 C24 104.46(9) . . ?
O2 S1 C24 111.08(12) . . ?
O2 S1 N1 105.96(10) . . ?
O2 S1 O3 120.07(11) . . ?
O3 S1 C24 109.19(11) . . ?
O3 S1 N1 104.70(10) . . ?
C6A C5A C4 113.5(4) . . ?
C6A C5A C10A 120.0 . . ?
C10A C5A C4 126.5(4) . . ?
C5A C6A H6A 120.0 . . ?
C5A C6A C7A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C5A C10A H10A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
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
C1 C2 1.535(3) . ?
C1 N1 1.406(2) . ?
C1 O1 1.200(2) . ?
C2 C3 1.532(3) . ?
C2 C11 1.532(3) . ?
C2 N3 1.454(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.493(3) . ?
C4 C5 1.524(3) . ?
C4 N2 1.275(3) . ?
C4 C5A 1.452(5) . ?
C5 C10 1.3900 . ?
C5 C6 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 H6 0.9300 . ?
C11 C12 1.374(3) . ?
C11 C16 1.379(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.344(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.356(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.481(9) . ?
C17 N3 1.339(11) . ?
C17 O4 1.236(13) . ?
C17A C18A 1.493(11) . ?
C17A N3 1.398(13) . ?
C17A O4A 1.217(13) . ?
C18 C23 1.3900 . ?
C18 C19 1.3900 . ?
C23 H23 0.9300 . ?
C23 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C18A C23A 1.3900 . ?
C18A C19A 1.3900 . ?
C23A H23A 0.9300 . ?
C23A C22A 1.3900 . ?
C22A H22A 0.9300 . ?
C22A C21A 1.3900 . ?
C21A H21A 0.9300 . ?
C21A C20A 1.3900 . ?
C20A H20A 0.9300 . ?
C20A C19A 1.3900 . ?
C19A H19A 0.9300 . ?
C24 C25 1.386(3) . ?
C24 C29 1.374(4) . ?
C24 S1 1.746(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(5) . ?
C27 C28 1.391(4) . ?
C27 C30 1.506(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N1 N2 1.414(2) . ?
N1 S1 1.7160(17) . ?
N3 H3AA 0.8600 . ?
N3 H3BB 0.8600 . ?
O2 S1 1.4153(18) . ?
O3 S1 1.4238(16) . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.3900 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.3900 . ?
C8A H8A 0.9300 . ?
C8A C9A 1.3900 . ?
C9A H9A 0.9300 . ?
C9A C10A 1.3900 . ?
C10A H10A 0.9300 . ?
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
N3 H3AA O3 0.86 2.24 3.069(2) 161.9 1_565
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
C1 C2 C3 C4 -55.8(2) . . . . ?
C1 C2 C11 C12 -3.1(3) . . . . ?
C1 C2 C11 C16 175.09(19) . . . . ?
C1 C2 N3 C17 -57.0(13) . . . . ?
C1 C2 N3 C17A -52.0(12) . . . . ?
C1 N1 N2 C4 -36.7(3) . . . . ?
C1 N1 S1 C24 -73.43(18) . . . . ?
C1 N1 S1 O2 43.96(19) . . . . ?
C1 N1 S1 O3 171.82(16) . . . . ?
C2 C1 N1 N2 19.7(3) . . . . ?
C2 C1 N1 S1 173.09(13) . . . . ?
C2 C3 C4 C5 -132.7(2) . . . . ?
C2 C3 C4 N2 44.7(3) . . . . ?
C2 C3 C4 C5A -140.8(3) . . . . ?
C2 C11 C12 C13 178.2(3) . . . . ?
C2 C11 C16 C15 -178.1(2) . . . . ?
C3 C2 C11 C12 -121.7(2) . . . . ?
C3 C2 C11 C16 56.4(2) . . . . ?
C3 C2 N3 C17 62.4(13) . . . . ?
C3 C2 N3 C17A 67.4(12) . . . . ?
C3 C4 C5 C10 5.9(3) . . . . ?
C3 C4 C5 C6 -168.9(2) . . . . ?
C3 C4 N2 N1 0.9(3) . . . . ?
C3 C4 C5A C6A 162.4(3) . . . . ?
C3 C4 C5A C10A -17.3(6) . . . . ?
C4 C5 C10 C9 -174.8(3) . . . . ?
C4 C5 C6 C7 174.7(3) . . . . ?
C4 C5A C6A C7A -179.7(6) . . . . ?
C4 C5A C10A C9A 179.7(6) . . . . ?
C5 C4 N2 N1 178.68(19) . . . . ?
C5 C10 C9 C8 0.0 . . . . ?
C10 C5 C6 C7 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C8 C7 C6 C5 0.0 . . . . ?
C6 C5 C10 C9 0.0 . . . . ?
C11 C2 C3 C4 63.4(2) . . . . ?
C11 C2 N3 C17 -176.0(13) . . . . ?
C11 C2 N3 C17A -171.0(12) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C16 C11 C12 C13 0.0(4) . . . . ?
C17 C18 C23 C22 179.1(11) . . . . ?
C17 C18 C19 C20 -179.1(12) . . . . ?
C17A C18A C23A C22A -178.5(12) . . . . ?
C17A C18A C19A C20A 178.4(13) . . . . ?
C18 C17 N3 C2 179.3(9) . . . . ?
C18 C23 C22 C21 0.0 . . . . ?
C23 C18 C19 C20 0.0 . . . . ?
C23 C22 C21 C20 0.0 . . . . ?
C22 C21 C20 C19 0.0 . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C19 C18 C23 C22 0.0 . . . . ?
C18A C17A N3 C2 180.0(12) . . . . ?
C18A C23A C22A C21A 0.0 . . . . ?
C23A C18A C19A C20A 0.0 . . . . ?
C23A C22A C21A C20A 0.0 . . . . ?
C22A C21A C20A C19A 0.0 . . . . ?
C21A C20A C19A C18A 0.0 . . . . ?
C19A C18A C23A C22A 0.0 . . . . ?
C24 C25 C26 C27 -0.8(4) . . . . ?
C25 C24 C29 C28 -0.9(4) . . . . ?
C25 C24 S1 N1 89.3(2) . . . . ?
C25 C24 S1 O2 -24.5(2) . . . . ?
C25 C24 S1 O3 -159.11(19) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C25 C26 C27 C30 -177.8(3) . . . . ?
C26 C27 C28 C29 0.5(5) . . . . ?
C27 C28 C29 C24 0.0(4) . . . . ?
C29 C24 C25 C26 1.3(4) . . . . ?
C29 C24 S1 N1 -90.1(2) . . . . ?
C29 C24 S1 O2 156.10(19) . . . . ?
C29 C24 S1 O3 21.5(2) . . . . ?
C30 C27 C28 C29 178.2(3) . . . . ?
N1 C1 C2 C3 26.8(2) . . . . ?
N1 C1 C2 C11 -93.04(19) . . . . ?
N1 C1 C2 N3 148.18(17) . . . . ?
N2 C4 C5 C10 -171.7(2) . . . . ?
N2 C4 C5 C6 13.5(3) . . . . ?
N2 C4 C5A C6A -23.5(6) . . . . ?
N2 C4 C5A C10A 156.8(4) . . . . ?
N2 N1 S1 C24 82.57(15) . . . . ?
N2 N1 S1 O2 -160.04(15) . . . . ?
N2 N1 S1 O3 -32.18(17) . . . . ?
N3 C2 C3 C4 -175.64(18) . . . . ?
N3 C2 C11 C12 115.8(2) . . . . ?
N3 C2 C11 C16 -66.1(2) . . . . ?
N3 C17 C18 C23 -154.7(13) . . . . ?
N3 C17 C18 C19 24(2) . . . . ?
N3 C17A C18A C23A -158.7(12) . . . . ?
N3 C17A C18A C19A 23(2) . . . . ?
O1 C1 C2 C3 -155.9(2) . . . . ?
O1 C1 C2 C11 84.3(2) . . . . ?
O1 C1 C2 N3 -34.5(3) . . . . ?
O1 C1 N1 N2 -157.6(2) . . . . ?
O1 C1 N1 S1 -4.3(3) . . . . ?
O4 C17 C18 C23 24(3) . . . . ?
O4 C17 C18 C19 -156.9(17) . . . . ?
O4 C17 N3 C2 1(3) . . . . ?
O4A C17A C18A C23A 23(3) . . . . ?
O4A C17A C18A C19A -155.9(19) . . . . ?
O4A C17A N3 C2 -1(3) . . . . ?
S1 C24 C25 C26 -178.1(2) . . . . ?
S1 C24 C29 C28 178.5(2) . . . . ?
S1 N1 N2 C4 167.81(15) . . . . ?
C5A C4 N2 N1 -172.8(4) . . . . ?
C5A C6A C7A C8A 0.0 . . . . ?
C6A C5A C10A C9A 0.0 . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C8A C9A C10A C5A 0.0 . . . . ?
C10A C5A C6A C7A 0.0 . . . . ?
