#------------------------------------------------------------------------------
#$Date: 2021-09-18 01:10:36 +0300 (Sat, 18 Sep 2021) $
#$Revision: 269186 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564669.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_1564669
loop_
_publ_author_name
'Tian, Jingye'
'Shi, Donglei'
'Zhang, Yanhui'
'Li, Xiaokang'
'Xinming, Li'
'Teng, Hao'
'James, Tony D.'
'Li, Jian'
'Guo, Yuan'
_publ_section_title
;
   Stress response decay with aging visualized using a dual-channel
 logic-based fluorescent probe 
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04162B
_journal_year                    2021
_chemical_formula_moiety         'C33 H26 N4 O3 S'
_chemical_formula_sum            'C33 H26 N4 O3 S'
_chemical_formula_weight         558.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-24 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                101.301(3)
_cell_angle_beta                 96.718(3)
_cell_angle_gamma                105.176(3)
_cell_formula_units_Z            2
_cell_length_a                   10.077(2)
_cell_length_b                   10.691(2)
_cell_length_c                   13.476(3)
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.198
_cell_measurement_theta_min      2.408
_cell_volume                     1352.1(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7038
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.031
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0535 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8971. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0567
_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)+(0.0870P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3197
_reflns_number_total             4942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04162b2.cif
_cod_data_source_block           xb2319_0m
_cod_original_cell_volume        1352.1(4)
_cod_database_code               1564669
_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_max   0.984
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C29-C28 \\sim C29A-C28
 with sigma of 0.02
 C30-C29 \\sim C30-C29A
 with sigma of 0.02
 C32-C31 \\sim C32A-C31
 with sigma of 0.02
 C33-C32 \\sim C33-C32A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C29A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H28C)=Sof(H28D)=Sof(H30C)=Sof(H30D)=Sof(H31C)=Sof(H31D)=Sof(H33C)=
 Sof(H33D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C29A)=Sof(H29C)=Sof(H29D)=1-FVAR(1)
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H30A)=Sof(H30B)=
 Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(H33A)=Sof(H33B)=FVAR(1)
5.a Rotating group:
 N3(H3A,H3B)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C28(H28C,H28D), C29(H29A,H29B), C30(H30A,H30B), C30(H30C,
 H30D), C31(H31A,H31B), C31(H31C,H31D), C32(H32A,H32B), C33(H33A,H33B),
 C33(H33C,H33D), C32A(H32C,H32D), C29A(H29C,H29D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3C), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C19(H19), C24(H24),
 C25(H25), C26(H26), C27(H27)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.30444(8) 0.08646(8) 0.94943(7) 0.0561(3) Uani 1 1 d . . . . .
O1 O 0.7059(2) 0.5598(2) 0.92246(16) 0.0616(6) Uani 1 1 d . . . . .
O2 O 0.0920(2) 0.48697(19) 0.67650(15) 0.0511(5) Uani 1 1 d . . . . .
O3 O -0.1089(2) 0.0859(2) 0.76031(19) 0.0607(6) Uani 1 1 d . . . . .
H3 H -0.091853 0.032453 0.792302 0.091 Uiso 1 1 calc GR . . . .
N1 N 0.0452(3) -0.0217(2) 0.86574(19) 0.0499(6) Uani 1 1 d . . . . .
N2 N 0.4781(2) 0.5463(2) 0.86067(15) 0.0371(5) Uani 1 1 d . . . . .
N3 N 0.4446(3) 0.6078(2) 0.95188(16) 0.0481(6) Uani 1 1 d . . . . .
H3A H 0.383871 0.549167 0.971948 0.058 Uiso 1 1 d GR . . . .
H3B H 0.520002 0.637526 0.997559 0.058 Uiso 1 1 d GR . . . .
N4 N 0.2315(3) 0.9286(3) 0.6278(2) 0.0635(8) Uani 1 1 d . . . . .
C1 C 0.6057(3) 0.5306(3) 0.8530(2) 0.0418(7) Uani 1 1 d . . . . .
C2 C 0.5967(3) 0.4687(3) 0.7432(2) 0.0443(7) Uani 1 1 d . . . . .
C3 C 0.6995(4) 0.4371(3) 0.6940(3) 0.0640(9) Uani 1 1 d . . . . .
H3C H 0.789603 0.454409 0.729676 0.077 Uiso 1 1 calc R . . . .
C4 C 0.6657(5) 0.3799(4) 0.5916(3) 0.0762(11) Uani 1 1 d . . . . .
H4 H 0.733562 0.356801 0.556962 0.091 Uiso 1 1 calc R . . . .
C5 C 0.5328(5) 0.3555(3) 0.5381(3) 0.0695(11) Uani 1 1 d . . . . .
H5 H 0.512623 0.315975 0.468082 0.083 Uiso 1 1 calc R . . . .
C6 C 0.4271(4) 0.3890(3) 0.5873(2) 0.0528(8) Uani 1 1 d . . . . .
H6 H 0.337409 0.373095 0.551448 0.063 Uiso 1 1 calc R . . . .
C7 C 0.4629(3) 0.4464(2) 0.6909(2) 0.0394(6) Uani 1 1 d . . . . .
C8 C 0.3752(3) 0.4999(2) 0.76384(18) 0.0354(6) Uani 1 1 d . . . . .
C9 C 0.2464(3) 0.3939(2) 0.77195(19) 0.0346(6) Uani 1 1 d . . . . .
C10 C 0.2547(3) 0.2936(3) 0.8214(2) 0.0389(6) Uani 1 1 d . . . . .
H10 H 0.341370 0.296307 0.855723 0.047 Uiso 1 1 calc R . . . .
C11 C 0.1393(3) 0.1890(3) 0.8221(2) 0.0412(7) Uani 1 1 d . . . . .
C12 C 0.0087(3) 0.1851(3) 0.7680(2) 0.0454(7) Uani 1 1 d . . . . .
C13 C -0.0022(3) 0.2872(3) 0.7213(2) 0.0461(7) Uani 1 1 d . . . . .
H13 H -0.088712 0.286234 0.687813 0.055 Uiso 1 1 calc R . . . .
C14 C 0.1146(3) 0.3901(3) 0.7245(2) 0.0405(7) Uani 1 1 d . . . . .
C15 C 0.2007(3) 0.6041(3) 0.6899(2) 0.0400(7) Uani 1 1 d . . . . .
C16 C 0.1622(3) 0.7052(3) 0.6526(2) 0.0481(7) Uani 1 1 d . . . . .
C17 C 0.2658(4) 0.8243(3) 0.6607(2) 0.0477(8) Uani 1 1 d . . . . .
C18 C 0.4056(3) 0.8397(3) 0.7032(2) 0.0493(8) Uani 1 1 d . . . . .
C19 C 0.4359(3) 0.7364(3) 0.7391(2) 0.0446(7) Uani 1 1 d . . . . .
H19 H 0.527605 0.747168 0.768557 0.053 Uiso 1 1 calc R . . . .
C20 C 0.3345(3) 0.6159(2) 0.73306(19) 0.0383(6) Uani 1 1 d . . . . .
C21 C 0.1503(3) 0.0835(3) 0.8737(2) 0.0440(7) Uani 1 1 d . . . . .
C22 C 0.2210(3) -0.0693(3) 0.9678(2) 0.0491(7) Uani 1 1 d . . . . .
C23 C 0.0829(3) -0.1102(3) 0.9185(2) 0.0494(7) Uani 1 1 d . . . . .
C24 C -0.0051(4) -0.2310(3) 0.9239(3) 0.0665(10) Uani 1 1 d . . . . .
H24 H -0.098027 -0.259021 0.891374 0.080 Uiso 1 1 calc R . . . .
C25 C 0.0473(4) -0.3089(3) 0.9783(3) 0.0719(10) Uani 1 1 d . . . . .
H25 H -0.010709 -0.390783 0.981724 0.086 Uiso 1 1 calc R . . . .
C26 C 0.1832(4) -0.2679(3) 1.0274(3) 0.0688(10) Uani 1 1 d . . . . .
H26 H 0.215381 -0.321878 1.064761 0.083 Uiso 1 1 calc R . . . .
C27 C 0.2746(4) -0.1477(3) 1.0228(2) 0.0611(9) Uani 1 1 d . . . . .
H27 H 0.367615 -0.120815 1.055095 0.073 Uiso 1 1 calc R . . . .
C28 C 0.0126(4) 0.6836(3) 0.6045(3) 0.0671(10) Uani 1 1 d D . . . .
H28A H -0.005431 0.630233 0.534594 0.081 Uiso 0.861(8) 1 calc R . P A 1
H28B H -0.049394 0.634617 0.642854 0.081 Uiso 0.861(8) 1 calc R . P A 1
H28C H -0.022889 0.593976 0.560939 0.081 Uiso 0.139(8) 1 calc R . P A 2
H28D H -0.042288 0.688639 0.658916 0.081 Uiso 0.139(8) 1 calc R . P A 2
C29 C -0.0181(5) 0.8138(4) 0.6034(4) 0.0796(17) Uani 0.861(8) 1 d D . P A 1
H29A H -0.027453 0.855338 0.671963 0.096 Uiso 0.861(8) 1 calc R . P A 1
H29B H -0.105819 0.797211 0.557677 0.096 Uiso 0.861(8) 1 calc R . P A 1
C30 C 0.0972(5) 0.9067(4) 0.5681(3) 0.0911(14) Uani 1 1 d D . . . .
H30A H 0.098492 0.869550 0.496643 0.109 Uiso 0.861(8) 1 calc R . P A 1
H30B H 0.077830 0.991657 0.572314 0.109 Uiso 0.861(8) 1 calc R . P A 1
H30C H 0.113065 0.929292 0.503305 0.109 Uiso 0.139(8) 1 calc R . P A 2
H30D H 0.056475 0.971666 0.603267 0.109 Uiso 0.139(8) 1 calc R . P A 2
C31 C 0.3431(5) 1.0414(4) 0.6153(3) 0.0836(13) Uani 1 1 d D . . . .
H31A H 0.307777 1.117684 0.616290 0.100 Uiso 0.861(8) 1 calc R . P A 1
H31B H 0.369992 1.017938 0.548883 0.100 Uiso 0.861(8) 1 calc R . P A 1
H31C H 0.316279 1.062760 0.550560 0.100 Uiso 0.139(8) 1 calc R . P A 2
H31D H 0.352147 1.118664 0.670016 0.100 Uiso 0.139(8) 1 calc R . P A 2
C32 C 0.4706(5) 1.0796(4) 0.6989(4) 0.0758(17) Uani 0.861(8) 1 d D . P A 1
H32A H 0.544263 1.149137 0.684633 0.091 Uiso 0.861(8) 1 calc R . P A 1
H32B H 0.447329 1.114086 0.764583 0.091 Uiso 0.861(8) 1 calc R . P A 1
C33 C 0.5201(4) 0.9617(3) 0.7039(3) 0.0713(10) Uani 1 1 d D . . . .
H33A H 0.588905 0.982956 0.766047 0.086 Uiso 0.861(8) 1 calc R . P A 1
H33B H 0.565978 0.942650 0.645725 0.086 Uiso 0.861(8) 1 calc R . P A 1
H33C H 0.535615 1.027427 0.768193 0.086 Uiso 0.139(8) 1 calc R . P A 2
H33D H 0.606289 0.939158 0.696934 0.086 Uiso 0.139(8) 1 calc R . P A 2
C32A C 0.478(2) 1.016(2) 0.6167(17) 0.067(10) Uani 0.139(8) 1 d D . P A 2
H32C H 0.547950 1.099172 0.619368 0.080 Uiso 0.139(8) 1 calc R . P A 2
H32D H 0.474778 0.954132 0.552977 0.080 Uiso 0.139(8) 1 calc R . P A 2
C29A C -0.010(3) 0.778(2) 0.543(2) 0.071(9) Uani 0.139(8) 1 d D U P A 2
H29C H -0.016427 0.735913 0.471245 0.086 Uiso 0.139(8) 1 calc R . P A 2
H29D H -0.099111 0.792968 0.551171 0.086 Uiso 0.139(8) 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 0.0033 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
C22 S1 C21 89.34(14) . . ?
C14 O2 C15 118.5(2) . . ?
C12 O3 H3 109.5 . . ?
C21 N1 C23 111.5(3) . . ?
N3 N2 C8 120.9(2) . . ?
C1 N2 N3 123.5(2) . . ?
C1 N2 C8 115.6(2) . . ?
N2 N3 H3A 108.9 . . ?
N2 N3 H3B 107.6 . . ?
H3A N3 H3B 109.0 . . ?
C17 N4 C30 120.0(3) . . ?
C17 N4 C31 119.6(3) . . ?
C30 N4 C31 115.7(3) . . ?
O1 C1 N2 127.1(3) . . ?
O1 C1 C2 127.7(3) . . ?
N2 C1 C2 105.2(2) . . ?
C3 C2 C1 128.7(3) . . ?
C3 C2 C7 121.8(3) . . ?
C7 C2 C1 109.5(2) . . ?
C2 C3 H3C 121.0 . . ?
C4 C3 C2 118.0(4) . . ?
C4 C3 H3C 121.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 121.6 . . ?
C7 C6 C5 116.7(3) . . ?
C7 C6 H6 121.6 . . ?
C2 C7 C8 109.9(2) . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 C8 129.2(3) . . ?
N2 C8 C7 99.8(2) . . ?
N2 C8 C9 111.64(19) . . ?
N2 C8 C20 110.8(2) . . ?
C9 C8 C7 113.1(2) . . ?
C9 C8 C20 110.2(2) . . ?
C20 C8 C7 110.9(2) . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 C14 117.3(2) . . ?
C14 C9 C8 120.6(2) . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 122.9(3) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C12 117.8(2) . . ?
C10 C11 C21 122.2(3) . . ?
C12 C11 C21 120.0(2) . . ?
O3 C12 C11 122.8(3) . . ?
O3 C12 C13 117.2(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
O2 C14 C9 122.8(2) . . ?
C13 C14 O2 115.4(2) . . ?
C13 C14 C9 121.8(2) . . ?
O2 C15 C16 114.6(2) . . ?
C20 C15 O2 122.0(2) . . ?
C20 C15 C16 123.4(3) . . ?
C15 C16 C28 120.1(3) . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 C28 121.8(3) . . ?
N4 C17 C16 120.0(3) . . ?
N4 C17 C18 119.7(3) . . ?
C16 C17 C18 120.3(2) . . ?
C17 C18 C33 121.1(3) . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 C33 120.4(3) . . ?
C18 C19 H19 118.6 . . ?
C18 C19 C20 122.8(3) . . ?
C20 C19 H19 118.6 . . ?
C15 C20 C8 121.9(2) . . ?
C15 C20 C19 117.0(2) . . ?
C19 C20 C8 120.8(2) . . ?
N1 C21 S1 114.8(2) . . ?
N1 C21 C11 122.2(3) . . ?
C11 C21 S1 123.0(2) . . ?
C23 C22 S1 109.7(2) . . ?
C23 C22 C27 121.5(3) . . ?
C27 C22 S1 128.9(3) . . ?
C22 C23 N1 114.7(3) . . ?
C24 C23 N1 125.3(3) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 C23 118.8(3) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.2 . . ?
C25 C26 C27 121.6(3) . . ?
C27 C26 H26 119.2 . . ?
C22 C27 H27 121.5 . . ?
C26 C27 C22 117.1(3) . . ?
C26 C27 H27 121.5 . . ?
C16 C28 H28A 109.3 . . ?
C16 C28 H28B 109.3 . . ?
C16 C28 H28C 108.4 . . ?
C16 C28 H28D 108.4 . . ?
H28A C28 H28B 108.0 . . ?
H28C C28 H28D 107.4 . . ?
C29 C28 C16 111.5(3) . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C29A C28 C16 115.6(10) . . ?
C29A C28 H28C 108.4 . . ?
C29A C28 H28D 108.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 C30 110.8(4) . . ?
H29A C29 H29B 108.1 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
N4 C30 C29 112.7(3) . . ?
N4 C30 H30A 109.1 . . ?
N4 C30 H30B 109.1 . . ?
N4 C30 H30C 106.8 . . ?
N4 C30 H30D 106.8 . . ?
N4 C30 C29A 122.1(8) . . ?
C29 C30 H30A 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
H30C C30 H30D 106.6 . . ?
C29A C30 H30C 106.8 . . ?
C29A C30 H30D 106.8 . . ?
N4 C31 H31A 109.1 . . ?
N4 C31 H31B 109.1 . . ?
N4 C31 H31C 108.8 . . ?
N4 C31 H31D 108.8 . . ?
N4 C31 C32 112.3(3) . . ?
H31A C31 H31B 107.9 . . ?
H31C C31 H31D 107.7 . . ?
C32 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
C32A C31 N4 113.8(8) . . ?
C32A C31 H31C 108.8 . . ?
C32A C31 H31D 108.8 . . ?
C31 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.2 . . ?
C33 C32 C31 110.1(4) . . ?
C33 C32 H32A 109.6 . . ?
C33 C32 H32B 109.6 . . ?
C18 C33 H33A 108.9 . . ?
C18 C33 H33B 108.9 . . ?
C18 C33 H33C 110.1 . . ?
C18 C33 H33D 110.1 . . ?
C32 C33 C18 113.4(3) . . ?
C32 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
H33C C33 H33D 108.4 . . ?
C32A C33 C18 108.0(10) . . ?
C32A C33 H33C 110.1 . . ?
C32A C33 H33D 110.1 . . ?
C31 C32A C33 114.1(11) . . ?
C31 C32A H32C 108.7 . . ?
C31 C32A H32D 108.7 . . ?
C33 C32A H32C 108.7 . . ?
C33 C32A H32D 108.7 . . ?
H32C C32A H32D 107.6 . . ?
C28 C29A H29C 108.3 . . ?
C28 C29A H29D 108.3 . . ?
C30 C29A C28 115.8(13) . . ?
C30 C29A H29C 108.3 . . ?
C30 C29A H29D 108.3 . . ?
H29C C29A H29D 107.4 . . ?
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 C21 1.745(3) . ?
S1 C22 1.738(3) . ?
O1 C1 1.222(3) . ?
O2 C14 1.376(3) . ?
O2 C15 1.396(3) . ?
O3 H3 0.8200 . ?
O3 C12 1.346(3) . ?
N1 C21 1.304(3) . ?
N1 C23 1.391(4) . ?
N2 N3 1.398(3) . ?
N2 C1 1.353(3) . ?
N2 C8 1.478(3) . ?
N3 H3A 0.8632 . ?
N3 H3B 0.8632 . ?
N4 C17 1.385(3) . ?
N4 C30 1.428(5) . ?
N4 C31 1.470(5) . ?
C1 C2 1.479(4) . ?
C2 C3 1.373(4) . ?
C2 C7 1.384(4) . ?
C3 H3C 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.374(4) . ?
C7 C8 1.523(4) . ?
C8 C9 1.514(4) . ?
C8 C20 1.519(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.392(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(4) . ?
C11 C12 1.414(4) . ?
C11 C21 1.458(4) . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C15 C16 1.399(4) . ?
C15 C20 1.368(4) . ?
C16 C17 1.395(4) . ?
C16 C28 1.509(4) . ?
C17 C18 1.412(4) . ?
C18 C19 1.378(4) . ?
C18 C33 1.496(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.400(4) . ?
C22 C23 1.386(4) . ?
C22 C27 1.389(4) . ?
C23 C24 1.383(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.366(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(4) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C28 H28D 0.9700 . ?
C28 C29 1.505(5) . ?
C28 C29A 1.465(16) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.508(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
C30 H30D 0.9700 . ?
C30 C29A 1.462(17) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C31 H31D 0.9700 . ?
C31 C32 1.514(6) . ?
C31 C32A 1.447(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.482(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 H33C 0.9700 . ?
C33 H33D 0.9700 . ?
C33 C32A 1.479(15) . ?
C32A H32C 0.9700 . ?
C32A H32D 0.9700 . ?
C29A H29C 0.9700 . ?
C29A H29D 0.9700 . ?
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
O3 H3 N1 0.82 1.88 2.610(3) 147.2 . yes
N3 H3A O1 0.86 2.14 2.957(3) 156.8 2_667 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
S1 C22 C23 N1 1.2(3) . . . . ?
S1 C22 C23 C24 -178.9(2) . . . . ?
S1 C22 C27 C26 178.4(3) . . . . ?
O1 C1 C2 C3 -3.9(5) . . . . ?
O1 C1 C2 C7 177.2(3) . . . . ?
O2 C15 C16 C17 -178.4(2) . . . . ?
O2 C15 C16 C28 1.2(4) . . . . ?
O2 C15 C20 C8 3.5(4) . . . . ?
O2 C15 C20 C19 177.7(2) . . . . ?
O3 C12 C13 C14 -178.6(3) . . . . ?
N1 C23 C24 C25 179.4(3) . . . . ?
N2 C1 C2 C3 177.0(3) . . . . ?
N2 C1 C2 C7 -1.9(3) . . . . ?
N2 C8 C9 C10 -40.8(3) . . . . ?
N2 C8 C9 C14 142.7(2) . . . . ?
N2 C8 C20 C15 -142.1(2) . . . . ?
N2 C8 C20 C19 43.9(3) . . . . ?
N3 N2 C1 O1 4.0(4) . . . . ?
N3 N2 C1 C2 -176.9(2) . . . . ?
N3 N2 C8 C7 178.5(2) . . . . ?
N3 N2 C8 C9 -61.7(3) . . . . ?
N3 N2 C8 C20 61.7(3) . . . . ?
N4 C17 C18 C19 177.5(2) . . . . ?
N4 C17 C18 C33 -6.1(4) . . . . ?
N4 C30 C29A C28 16(3) . . . . ?
N4 C31 C32 C33 54.6(5) . . . . ?
N4 C31 C32A C33 -49(2) . . . . ?
C1 N2 C8 C7 1.4(3) . . . . ?
C1 N2 C8 C9 121.2(2) . . . . ?
C1 N2 C8 C20 -115.5(2) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C1 C2 C7 C6 -179.7(2) . . . . ?
C1 C2 C7 C8 2.9(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C7 C8 N2 -2.6(2) . . . . ?
C2 C7 C8 C9 -121.3(2) . . . . ?
C2 C7 C8 C20 114.3(2) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
C3 C2 C7 C8 -176.1(2) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C2 -0.4(4) . . . . ?
C5 C6 C7 C8 176.5(2) . . . . ?
C6 C7 C8 N2 -179.7(3) . . . . ?
C6 C7 C8 C9 61.6(3) . . . . ?
C6 C7 C8 C20 -62.8(3) . . . . ?
C7 C2 C3 C4 -1.4(4) . . . . ?
C7 C8 C9 C10 70.8(3) . . . . ?
C7 C8 C9 C14 -105.7(3) . . . . ?
C7 C8 C20 C15 108.0(3) . . . . ?
C7 C8 C20 C19 -66.0(3) . . . . ?
C8 N2 C1 O1 -179.0(3) . . . . ?
C8 N2 C1 C2 0.2(3) . . . . ?
C8 C9 C10 C11 -174.3(2) . . . . ?
C8 C9 C14 O2 -6.1(4) . . . . ?
C8 C9 C14 C13 173.0(2) . . . . ?
C9 C8 C20 C15 -18.0(3) . . . . ?
C9 C8 C20 C19 168.0(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C9 C10 C11 C21 179.4(2) . . . . ?
C10 C9 C14 O2 177.3(2) . . . . ?
C10 C9 C14 C13 -3.6(4) . . . . ?
C10 C11 C12 O3 177.5(3) . . . . ?
C10 C11 C12 C13 -3.4(4) . . . . ?
C10 C11 C21 S1 6.3(4) . . . . ?
C10 C11 C21 N1 -172.9(3) . . . . ?
C11 C12 C13 C14 2.3(4) . . . . ?
C12 C11 C21 S1 -175.4(2) . . . . ?
C12 C11 C21 N1 5.4(4) . . . . ?
C12 C13 C14 O2 -179.5(2) . . . . ?
C12 C13 C14 C9 1.4(4) . . . . ?
C14 O2 C15 C16 -170.2(2) . . . . ?
C14 O2 C15 C20 11.9(4) . . . . ?
C14 C9 C10 C11 2.3(4) . . . . ?
C15 O2 C14 C9 -10.5(4) . . . . ?
C15 O2 C14 C13 170.3(2) . . . . ?
C15 C16 C17 N4 -177.9(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C15 C16 C28 C29 160.1(4) . . . . ?
C15 C16 C28 C29A -163.7(16) . . . . ?
C16 C15 C20 C8 -174.3(2) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C16 C17 C18 C19 -2.0(4) . . . . ?
C16 C17 C18 C33 174.4(3) . . . . ?
C16 C28 C29 C30 45.0(5) . . . . ?
C16 C28 C29A C30 -24(3) . . . . ?
C17 N4 C30 C29 38.7(5) . . . . ?
C17 N4 C30 C29A 2.5(19) . . . . ?
C17 N4 C31 C32 -38.7(5) . . . . ?
C17 N4 C31 C32A 13.5(11) . . . . ?
C17 C16 C28 C29 -20.3(5) . . . . ?
C17 C16 C28 C29A 15.9(17) . . . . ?
C17 C18 C19 C20 1.5(4) . . . . ?
C17 C18 C33 C32 24.1(5) . . . . ?
C17 C18 C33 C32A -27.0(9) . . . . ?
C18 C19 C20 C8 173.9(2) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C18 C33 C32A C31 54.3(18) . . . . ?
C19 C18 C33 C32 -159.6(3) . . . . ?
C19 C18 C33 C32A 149.4(9) . . . . ?
C20 C8 C9 C10 -164.5(2) . . . . ?
C20 C8 C9 C14 19.1(3) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?
C20 C15 C16 C28 179.1(3) . . . . ?
C21 S1 C22 C23 -1.7(2) . . . . ?
C21 S1 C22 C27 178.9(3) . . . . ?
C21 N1 C23 C22 0.2(4) . . . . ?
C21 N1 C23 C24 -179.6(3) . . . . ?
C21 C11 C12 O3 -0.8(4) . . . . ?
C21 C11 C12 C13 178.3(3) . . . . ?
C22 S1 C21 N1 2.0(2) . . . . ?
C22 S1 C21 C11 -177.3(2) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?
C23 N1 C21 S1 -1.7(3) . . . . ?
C23 N1 C21 C11 177.6(2) . . . . ?
C23 C22 C27 C26 -0.9(5) . . . . ?
C23 C24 C25 C26 0.8(5) . . . . ?
C24 C25 C26 C27 -1.3(6) . . . . ?
C25 C26 C27 C22 1.3(5) . . . . ?
C27 C22 C23 N1 -179.3(3) . . . . ?
C27 C22 C23 C24 0.5(5) . . . . ?
C28 C16 C17 N4 2.5(4) . . . . ?
C28 C16 C17 C18 -178.0(3) . . . . ?
C28 C29 C30 N4 -55.2(5) . . . . ?
C30 N4 C17 C16 -11.9(5) . . . . ?
C30 N4 C17 C18 168.6(3) . . . . ?
C30 N4 C31 C32 165.6(3) . . . . ?
C30 N4 C31 C32A -142.3(10) . . . . ?
C31 N4 C17 C16 -166.6(3) . . . . ?
C31 N4 C17 C18 13.9(4) . . . . ?
C31 N4 C30 C29 -165.7(4) . . . . ?
C31 N4 C30 C29A 158.1(18) . . . . ?
C31 C32 C33 C18 -47.1(5) . . . . ?
C33 C18 C19 C20 -175.0(3) . . . . ?
