# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_140928_dhl499105_2r
_database_code_depnum_ccdc_archive 'CCDC 1403019'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_audit_creation_date             2014-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H22 N4 O3 S'
_chemical_formula_sum            'C26 H22 N4 O3 S'
_chemical_formula_weight         470.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.2558(6)
_cell_length_b                   10.1328(7)
_cell_length_c                   13.9082(11)
_cell_angle_alpha                77.492(6)
_cell_angle_beta                 79.130(6)
_cell_angle_gamma                85.572(6)
_cell_volume                     1114.69(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5122
_cell_measurement_theta_min      3.1557
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7209
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0448165000
_diffrn_orient_matrix_UB_12      0.0530650000
_diffrn_orient_matrix_UB_13      -0.0338585000
_diffrn_orient_matrix_UB_21      0.0195445000
_diffrn_orient_matrix_UB_22      0.0233089000
_diffrn_orient_matrix_UB_23      0.0408449000
_diffrn_orient_matrix_UB_31      0.0726229000
_diffrn_orient_matrix_UB_32      -0.0423014000
_diffrn_orient_matrix_UB_33      -0.0013939000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2928
_reflns_number_total             4054
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1446
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C23(H23), C15(H15), C19(H19), C5(H5), C1(H1A), C20(H20), C24(H24),
 C26(H26), C12(H12), C25(H25), C13(H13), C4(H4), C2(H2), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.19896(8) 0.86256(6) 0.27986(5) 0.0501(2) Uani 1 d . . .
N3 N 0.3059(2) 0.46294(19) 0.48731(14) 0.0398(5) Uani 1 d . . .
O3 O 0.4710(2) 0.24073(18) 0.54357(13) 0.0547(5) Uani 1 d . . .
H3 H 0.3975 0.2987 0.5513 0.082 Uiso 1 calc . . GR
C17 C 0.4968(3) 0.3633(2) 0.37150(17) 0.0384(6) Uani 1 d . . .
C22 C 0.5732(3) 0.3699(2) 0.26970(18) 0.0401(6) Uani 1 d . . .
N1 N 0.2102(3) 0.71421(19) 0.35156(15) 0.0437(5) Uani 1 d . . .
H1 H 0.2665 0.6521 0.3251 0.052 Uiso 1 calc . . R
C8 C 0.1421(3) 0.6799(2) 0.44553(18) 0.0387(6) Uani 1 d . . .
N2 N 0.0195(2) 0.7395(2) 0.50402(16) 0.0456(5) Uani 1 d . . .
C10 C 0.1016(3) 0.5505(2) 0.60953(18) 0.0419(6) Uani 1 d . . .
C6 C 0.3827(3) 0.8580(2) 0.19341(19) 0.0467(6) Uani 1 d . . .
O1 O 0.2103(3) 0.96575(18) 0.33421(16) 0.0684(6) Uani 1 d . . .
C21 C 0.6823(3) 0.2607(3) 0.2455(2) 0.0476(6) Uani 1 d . . .
C23 C 0.5482(3) 0.4790(3) 0.19101(19) 0.0501(7) Uani 1 d . . .
H23 H 0.4772 0.5511 0.2047 0.060 Uiso 1 calc . . R
C18 C 0.5330(3) 0.2531(2) 0.44450(18) 0.0414(6) Uani 1 d . . .
O2 O 0.0633(2) 0.8730(2) 0.22759(16) 0.0715(6) Uani 1 d . . .
C15 C 0.1010(4) 0.4599(3) 0.6995(2) 0.0539(7) Uani 1 d . . .
H15 H 0.1717 0.3837 0.7041 0.065 Uiso 1 calc . . R
C11 C -0.0052(3) 0.6643(3) 0.6034(2) 0.0455(6) Uani 1 d . . .
C19 C 0.6401(3) 0.1480(3) 0.4187(2) 0.0525(7) Uani 1 d . . .
H19 H 0.6616 0.0746 0.4682 0.063 Uiso 1 calc . . R
C3 C 0.6773(4) 0.8485(3) 0.0588(2) 0.0597(8) Uani 1 d . . .
C5 C 0.3817(4) 0.8322(3) 0.0998(2) 0.0560(7) Uani 1 d . . .
H5 H 0.2831 0.8173 0.0816 0.067 Uiso 1 calc . . R
C1 C 0.5307(4) 0.8813(3) 0.2194(2) 0.0556(7) Uani 1 d . . .
H1A H 0.5317 0.9009 0.2816 0.067 Uiso 1 calc . . R
C20 C 0.7132(3) 0.1513(3) 0.3224(2) 0.0561(7) Uani 1 d . . .
H20 H 0.7847 0.0804 0.3069 0.067 Uiso 1 calc . . R
C24 C 0.6262(4) 0.4807(3) 0.0955(2) 0.0619(8) Uani 1 d . . .
H24 H 0.6087 0.5543 0.0450 0.074 Uiso 1 calc . . R
C26 C 0.7588(4) 0.2665(3) 0.1453(2) 0.0625(8) Uani 1 d . . .
H26 H 0.8292 0.1953 0.1291 0.075 Uiso 1 calc . . R
C12 C -0.1131(3) 0.6913(3) 0.6864(2) 0.0578(7) Uani 1 d . . .
H12 H -0.1833 0.7678 0.6821 0.069 Uiso 1 calc . . R
C25 C 0.7320(4) 0.3737(3) 0.0720(2) 0.0654(8) Uani 1 d . . .
H25 H 0.7840 0.3760 0.0063 0.078 Uiso 1 calc . . R
C16 C -0.0956(3) 0.8497(3) 0.4703(2) 0.0617(8) Uani 1 d . . .
H16A H -0.0496 0.9350 0.4673 0.093 Uiso 1 calc . . GR
H16B H -0.1985 0.8415 0.5164 0.093 Uiso 1 calc . . GR
H16C H -0.1142 0.8450 0.4050 0.093 Uiso 1 calc . . GR
C13 C -0.1125(4) 0.6003(3) 0.7758(2) 0.0666(8) Uani 1 d . . .
H13 H -0.1840 0.6160 0.8327 0.080 Uiso 1 calc . . R
C4 C 0.5292(4) 0.8289(3) 0.0337(2) 0.0636(8) Uani 1 d . . .
H4 H 0.5279 0.8129 -0.0295 0.076 Uiso 1 calc . . R
C2 C 0.6755(4) 0.8752(3) 0.1530(2) 0.0609(8) Uani 1 d . . .
H2 H 0.7744 0.8893 0.1714 0.073 Uiso 1 calc . . R
C14 C -0.0082(4) 0.4860(3) 0.7831(2) 0.0652(8) Uani 1 d . . .
H14 H -0.0113 0.4262 0.8444 0.078 Uiso 1 calc . . R
C7 C 0.8377(4) 0.8407(4) -0.0127(3) 0.0865(11) Uani 1 d . . .
H7A H 0.8657 0.7480 -0.0165 0.130 Uiso 1 calc . . GR
H7B H 0.9234 0.8771 0.0107 0.130 Uiso 1 calc . . GR
H7C H 0.8261 0.8921 -0.0778 0.130 Uiso 1 calc . . GR
N4 N 0.3885(2) 0.47087(19) 0.39432(14) 0.0413(5) Uani 1 d . . .
C9 C 0.1956(3) 0.5553(2) 0.50986(18) 0.0390(5) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
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 N1 1.621(2) . ?
S1 C6 1.753(3) . ?
S1 O1 1.434(2) . ?
S1 O2 1.432(2) . ?
N3 N4 1.332(3) . ?
N3 C9 1.301(3) . ?
O3 H3 0.8200 . ?
O3 C18 1.358(3) . ?
C17 C22 1.427(3) . ?
C17 C18 1.392(3) . ?
C17 N4 1.408(3) . ?
C22 C21 1.429(3) . ?
C22 C23 1.410(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.304(3) . ?
C8 N2 1.364(3) . ?
C8 C9 1.470(3) . ?
N2 C11 1.412(3) . ?
N2 C16 1.466(3) . ?
C10 C15 1.382(4) . ?
C10 C11 1.394(3) . ?
C10 C9 1.448(3) . ?
C6 C5 1.383(4) . ?
C6 C1 1.388(4) . ?
C21 C20 1.408(4) . ?
C21 C26 1.408(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.360(4) . ?
C18 C19 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.390(4) . ?
C11 C12 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.355(4) . ?
C3 C4 1.374(4) . ?
C3 C2 1.391(4) . ?
C3 C7 1.506(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.372(4) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.394(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.356(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(4) . ?
C25 H25 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.386(4) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C14 H14 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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 S1 C6 100.53(11) . . ?
O1 S1 N1 110.19(12) . . ?
O1 S1 C6 108.02(13) . . ?
O2 S1 N1 110.72(12) . . ?
O2 S1 C6 108.29(13) . . ?
O2 S1 O1 117.65(13) . . ?
C9 N3 N4 121.37(19) . . ?
C18 O3 H3 109.5 . . ?
C18 C17 C22 119.5(2) . . ?
C18 C17 N4 122.4(2) . . ?
N4 C17 C22 118.1(2) . . ?
C17 C22 C21 118.5(2) . . ?
C23 C22 C17 123.7(2) . . ?
C23 C22 C21 117.7(2) . . ?
S1 N1 H1 116.8 . . ?
C8 N1 S1 126.36(17) . . ?
C8 N1 H1 116.8 . . ?
N1 C8 N2 132.3(2) . . ?
N1 C8 C9 121.2(2) . . ?
N2 C8 C9 106.5(2) . . ?
C8 N2 C11 110.42(19) . . ?
C8 N2 C16 127.0(2) . . ?
C11 N2 C16 121.6(2) . . ?
C15 C10 C11 120.5(2) . . ?
C15 C10 C9 133.0(2) . . ?
C11 C10 C9 106.5(2) . . ?
C5 C6 S1 120.9(2) . . ?
C5 C6 C1 119.8(3) . . ?
C1 C6 S1 119.3(2) . . ?
C20 C21 C22 119.4(2) . . ?
C20 C21 C26 121.6(2) . . ?
C26 C21 C22 119.0(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
O3 C18 C17 123.6(2) . . ?
O3 C18 C19 115.8(2) . . ?
C17 C18 C19 120.6(2) . . ?
C10 C15 H15 120.9 . . ?
C10 C15 C14 118.2(3) . . ?
C14 C15 H15 120.9 . . ?
C10 C11 N2 109.3(2) . . ?
C12 C11 N2 129.1(2) . . ?
C12 C11 C10 121.6(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 C7 121.4(3) . . ?
C2 C3 C7 120.6(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C1 H1A 120.1 . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 H1A 120.1 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.9(2) . . ?
C19 C20 H20 119.6 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H26 119.4 . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.4(3) . . ?
C13 C12 H12 121.3 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C3 C2 H2 119.3 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.3 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 N4 C17 119.44(19) . . ?
N3 C9 C8 129.4(2) . . ?
N3 C9 C10 123.4(2) . . ?
C10 C9 C8 107.20(19) . . ?

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 N1 C8 N2 16.6(4) . . . . ?
S1 N1 C8 C9 -163.40(18) . . . . ?
S1 C6 C5 C4 -179.8(2) . . . . ?
S1 C6 C1 C2 178.7(2) . . . . ?
O3 C18 C19 C20 -178.1(3) . . . . ?
C17 C22 C21 C20 -0.9(4) . . . . ?
C17 C22 C21 C26 -179.8(2) . . . . ?
C17 C22 C23 C24 179.1(3) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C22 C17 C18 O3 177.5(2) . . . . ?
C22 C17 C18 C19 -1.5(4) . . . . ?
C22 C17 N4 N3 175.0(2) . . . . ?
C22 C21 C20 C19 0.4(4) . . . . ?
C22 C21 C26 C25 0.6(4) . . . . ?
C22 C23 C24 C25 0.7(5) . . . . ?
N1 S1 C6 C5 100.8(2) . . . . ?
N1 S1 C6 C1 -79.6(2) . . . . ?
N1 C8 N2 C11 -177.6(3) . . . . ?
N1 C8 N2 C16 13.5(4) . . . . ?
N1 C8 C9 N3 -2.1(4) . . . . ?
N1 C8 C9 C10 177.5(2) . . . . ?
C8 N2 C11 C10 -1.5(3) . . . . ?
C8 N2 C11 C12 177.9(3) . . . . ?
N2 C8 C9 N3 177.9(2) . . . . ?
N2 C8 C9 C10 -2.6(3) . . . . ?
N2 C11 C12 C13 -180.0(3) . . . . ?
C10 C15 C14 C13 -0.4(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C6 S1 N1 C8 153.5(2) . . . . ?
C6 C5 C4 C3 1.0(4) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
O1 S1 N1 C8 39.7(2) . . . . ?
O1 S1 C6 C5 -143.8(2) . . . . ?
O1 S1 C6 C1 35.9(2) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C21 C26 C25 C24 -0.3(5) . . . . ?
C23 C22 C21 C20 178.6(2) . . . . ?
C23 C22 C21 C26 -0.2(4) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C18 C17 C22 C21 1.5(4) . . . . ?
C18 C17 C22 C23 -178.1(2) . . . . ?
C18 C17 N4 N3 -5.9(3) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
O2 S1 N1 C8 -92.2(2) . . . . ?
O2 S1 C6 C5 -15.4(2) . . . . ?
O2 S1 C6 C1 164.3(2) . . . . ?
C15 C10 C11 N2 -179.8(2) . . . . ?
C15 C10 C11 C12 0.8(4) . . . . ?
C15 C10 C9 N3 0.8(4) . . . . ?
C15 C10 C9 C8 -178.8(3) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
C11 C10 C9 N3 -178.7(2) . . . . ?
C11 C10 C9 C8 1.7(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C5 C6 C1 C2 -1.6(4) . . . . ?
C1 C6 C5 C4 0.6(4) . . . . ?
C20 C21 C26 C25 -178.2(3) . . . . ?
C26 C21 C20 C19 179.2(3) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C16 N2 C11 C10 168.2(2) . . . . ?
C16 N2 C11 C12 -12.5(4) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C7 C3 C4 C5 178.2(3) . . . . ?
C7 C3 C2 C1 -179.3(3) . . . . ?
N4 N3 C9 C8 -1.1(4) . . . . ?
N4 N3 C9 C10 179.4(2) . . . . ?
N4 C17 C22 C21 -179.5(2) . . . . ?
N4 C17 C22 C23 1.0(4) . . . . ?
N4 C17 C18 O3 -1.6(4) . . . . ?
N4 C17 C18 C19 179.5(2) . . . . ?
C9 N3 N4 C17 -174.8(2) . . . . ?
C9 C8 N2 C11 2.5(3) . . . . ?
C9 C8 N2 C16 -166.5(2) . . . . ?
C9 C10 C15 C14 -179.7(3) . . . . ?
C9 C10 C11 N2 -0.2(3) . . . . ?
C9 C10 C11 C12 -179.6(2) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150420_dhl507168
_database_code_depnum_ccdc_archive 'CCDC 1403020'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H20 B F N4 O3 S'
_chemical_formula_sum            'C26 H20 B F N4 O3 S'
_chemical_formula_weight         498.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 B1'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8786(8)
_cell_length_b                   14.6539(7)
_cell_length_c                   14.7921(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.989(8)
_cell_angle_gamma                90.00
_cell_volume                     2370.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4006
_cell_measurement_theta_min      3.1509
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9863
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0042323000
_diffrn_orient_matrix_UB_12      -0.0480242000
_diffrn_orient_matrix_UB_13      0.0065365000
_diffrn_orient_matrix_UB_21      -0.0600959000
_diffrn_orient_matrix_UB_22      -0.0009726000
_diffrn_orient_matrix_UB_23      -0.0008558000
_diffrn_orient_matrix_UB_31      -0.0240003000
_diffrn_orient_matrix_UB_32      -0.0060862000
_diffrn_orient_matrix_UB_33      -0.0516648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3352
_reflns_number_total             4317
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.017
_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)+(0.0465P)²+0.7038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.12515(4) 0.81877(3) 0.02193(4) 0.04017(15) Uani 1 d . . .
F1 F 0.23591(11) 0.99487(8) -0.11912(8) 0.0504(3) Uani 1 d . . .
O1 O 0.09371(14) 0.83942(10) 0.10322(11) 0.0555(4) Uani 1 d . . .
O2 O 0.03144(12) 0.79619(10) -0.07014(10) 0.0501(4) Uani 1 d . . .
O3 O 0.20846(12) 0.83697(9) -0.15041(9) 0.0436(3) Uani 1 d . . .
N1 N 0.25848(15) 0.99739(11) 0.15632(12) 0.0434(4) Uani 1 d . . .
N2 N 0.19870(14) 0.91013(10) 0.00321(11) 0.0368(4) Uani 1 d . . .
N3 N 0.39196(14) 0.88554(10) -0.02713(10) 0.0351(4) Uani 1 d . . .
N4 N 0.46733(14) 0.91023(11) 0.05980(11) 0.0365(4) Uani 1 d . . .
C1 C 0.3881(2) 1.07266(17) 0.31535(17) 0.0631(7) Uani 1 d . . .
H1 H 0.3231 1.0893 0.3320 0.076 Uiso 1 calc . . R
C2 C 0.5064(3) 1.09351(19) 0.37465(18) 0.0710(7) Uani 1 d . . .
H2 H 0.5219 1.1252 0.4328 0.085 Uiso 1 calc . . R
C3 C 0.6035(2) 1.06867(17) 0.35034(17) 0.0632(7) Uani 1 d . . .
H3 H 0.6826 1.0841 0.3924 0.076 Uiso 1 calc . . R
C4 C 0.5854(2) 1.02150(15) 0.26498(15) 0.0488(5) Uani 1 d . . .
H4 H 0.6510 1.0049 0.2490 0.059 Uiso 1 calc . . R
C5 C 0.46621(19) 0.99966(13) 0.20376(14) 0.0393(5) Uani 1 d . . .
C6 C 0.36952(19) 1.02572(14) 0.22960(14) 0.0445(5) Uani 1 d . . .
C7 C 0.28325(17) 0.95378(12) 0.08580(13) 0.0365(4) Uani 1 d . . .
C8 C 0.41004(17) 0.95448(13) 0.10996(13) 0.0360(4) Uani 1 d . . .
C9 C 0.1399(2) 1.02892(17) 0.15145(18) 0.0572(6) Uani 1 d . . .
H9A H 0.0789 1.0170 0.0872 0.086 Uiso 1 calc . . GR
H9B H 0.1436 1.0933 0.1643 0.086 Uiso 1 calc . . GR
H9C H 0.1192 0.9972 0.1996 0.086 Uiso 1 calc . . GR
C10 C 0.41893(18) 0.82388(13) -0.08758(13) 0.0369(4) Uani 1 d . . .
C11 C 0.30788(18) 0.79779(14) -0.15881(13) 0.0402(5) Uani 1 d . . .
C12 C 0.3011(2) 0.73462(16) -0.23155(15) 0.0518(6) Uani 1 d . . .
H12 H 0.2261 0.7158 -0.2781 0.062 Uiso 1 calc . . R
C13 C 0.4077(2) 0.70162(16) -0.23203(16) 0.0559(6) Uani 1 d . . .
H13 H 0.4046 0.6601 -0.2805 0.067 Uiso 1 calc . . R
C14 C 0.5238(2) 0.72806(15) -0.16140(15) 0.0490(5) Uani 1 d . . .
C15 C 0.53195(18) 0.79069(13) -0.08532(14) 0.0387(4) Uani 1 d . . .
C16 C 0.64784(18) 0.81723(15) -0.01710(14) 0.0453(5) Uani 1 d . . .
H16 H 0.6539 0.8577 0.0330 0.054 Uiso 1 calc . . R
C17 C 0.7511(2) 0.78395(18) -0.02419(17) 0.0583(6) Uani 1 d . . .
H17 H 0.8272 0.8023 0.0211 0.070 Uiso 1 calc . . R
C18 C 0.7445(2) 0.7228(2) -0.09825(18) 0.0672(7) Uani 1 d . . .
H18 H 0.8159 0.7005 -0.1019 0.081 Uiso 1 calc . . R
C19 C 0.6342(2) 0.69586(18) -0.16496(17) 0.0634(7) Uani 1 d . . .
H19 H 0.6311 0.6553 -0.2142 0.076 Uiso 1 calc . . R
C20 C 0.23722(16) 0.73349(13) 0.05691(13) 0.0361(4) Uani 1 d . . .
C21 C 0.33141(18) 0.73822(13) 0.14902(14) 0.0408(5) Uani 1 d . . .
H21 H 0.3313 0.7831 0.1934 0.049 Uiso 1 calc . . R
C22 C 0.42508(19) 0.67575(14) 0.17400(15) 0.0464(5) Uani 1 d . . .
H22 H 0.4891 0.6793 0.2353 0.056 Uiso 1 calc . . R
C23 C 0.4257(2) 0.60760(16) 0.10935(17) 0.0536(6) Uani 1 d . . .
C24 C 0.3285(2) 0.60355(16) 0.01832(17) 0.0575(6) Uani 1 d . . .
H24 H 0.3267 0.5574 -0.0253 0.069 Uiso 1 calc . . R
C25 C 0.23496(19) 0.66622(14) -0.00861(15) 0.0467(5) Uani 1 d . . .
H25 H 0.1712 0.6632 -0.0701 0.056 Uiso 1 calc . . R
C26 C 0.5294(3) 0.5407(2) 0.1364(2) 0.0938(10) Uani 1 d . . .
H26A H 0.5933 0.5655 0.1195 0.141 Uiso 1 calc . . GR
H26B H 0.5007 0.4846 0.1014 0.141 Uiso 1 calc . . GR
H26C H 0.5605 0.5291 0.2058 0.141 Uiso 1 calc . . GR
B1 B 0.2506(2) 0.90895(15) -0.07776(16) 0.0390(5) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
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 O1 1.4240(15) . ?
S1 O2 1.4209(15) . ?
S1 N2 1.6796(16) . ?
S1 C20 1.7504(19) . ?
F1 B1 1.381(2) . ?
O3 C11 1.362(2) . ?
O3 B1 1.448(3) . ?
N1 C6 1.404(3) . ?
N1 C7 1.350(2) . ?
N1 C9 1.457(2) . ?
N2 C7 1.397(2) . ?
N2 B1 1.546(3) . ?
N3 N4 1.299(2) . ?
N3 C10 1.394(2) . ?
N3 B1 1.587(3) . ?
N4 C8 1.352(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(3) . ?
C1 C6 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(3) . ?
C5 C6 1.398(3) . ?
C5 C8 1.444(3) . ?
C7 C8 1.406(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.382(3) . ?
C10 C15 1.416(3) . ?
C11 C12 1.398(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.420(3) . ?
C14 C15 1.426(3) . ?
C14 C19 1.414(3) . ?
C15 C16 1.407(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.362(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.355(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(3) . ?
C20 C25 1.375(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(3) . ?
C23 C24 1.391(3) . ?
C23 C26 1.502(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(3) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
O1 S1 N2 107.14(9) . . ?
O1 S1 C20 108.79(9) . . ?
O2 S1 O1 119.55(9) . . ?
O2 S1 N2 106.91(8) . . ?
O2 S1 C20 109.74(9) . . ?
N2 S1 C20 103.49(8) . . ?
C11 O3 B1 108.32(15) . . ?
C6 N1 C9 122.89(16) . . ?
C7 N1 C6 108.30(16) . . ?
C7 N1 C9 127.60(17) . . ?
C7 N2 S1 117.61(12) . . ?
C7 N2 B1 108.34(15) . . ?
B1 N2 S1 120.60(13) . . ?
N4 N3 C10 125.00(16) . . ?
N4 N3 B1 126.90(15) . . ?
C10 N3 B1 107.67(15) . . ?
N3 N4 C8 112.14(15) . . ?
C2 C1 H1 121.5 . . ?
C2 C1 C6 117.1(2) . . ?
C6 C1 H1 121.5 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.7(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.9(2) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 119.76(18) . . ?
C4 C5 C8 134.71(19) . . ?
C6 C5 C8 105.50(17) . . ?
C1 C6 N1 128.4(2) . . ?
C1 C6 C5 122.2(2) . . ?
C5 C6 N1 109.43(16) . . ?
N1 C7 N2 126.38(17) . . ?
N1 C7 C8 109.60(17) . . ?
N2 C7 C8 123.96(16) . . ?
N4 C8 C5 127.18(17) . . ?
N4 C8 C7 125.16(17) . . ?
C7 C8 C5 107.14(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C15 131.37(17) . . ?
C11 C10 N3 106.16(16) . . ?
C11 C10 C15 122.46(17) . . ?
O3 C11 C10 114.66(16) . . ?
O3 C11 C12 123.92(18) . . ?
C10 C11 C12 121.40(19) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.8(2) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 118.7 . . ?
C12 C13 C14 122.6(2) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 120.20(19) . . ?
C19 C14 C13 122.0(2) . . ?
C19 C14 C15 117.8(2) . . ?
C10 C15 C14 115.54(18) . . ?
C16 C15 C10 125.11(17) . . ?
C16 C15 C14 119.31(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.30(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
C21 C20 S1 118.91(15) . . ?
C25 C20 S1 120.01(15) . . ?
C25 C20 C21 120.97(18) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.23(19) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.09(19) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C24 118.2(2) . . ?
C22 C23 C26 120.8(2) . . ?
C24 C23 C26 121.0(2) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 H24 119.2 . . ?
C20 C25 H25 120.5 . . ?
C24 C25 C20 118.90(19) . . ?
C24 C25 H25 120.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
F1 B1 O3 112.84(16) . . ?
F1 B1 N2 108.28(16) . . ?
F1 B1 N3 109.47(17) . . ?
O3 B1 N2 117.15(17) . . ?
O3 B1 N3 100.82(15) . . ?
N2 B1 N3 107.77(15) . . ?

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 N2 C7 N1 -64.3(2) . . . . ?
S1 N2 C7 C8 112.36(18) . . . . ?
S1 N2 B1 F1 143.44(14) . . . . ?
S1 N2 B1 O3 14.5(2) . . . . ?
S1 N2 B1 N3 -98.23(16) . . . . ?
S1 C20 C21 C22 -174.76(15) . . . . ?
S1 C20 C25 C24 175.70(17) . . . . ?
O1 S1 N2 C7 41.30(16) . . . . ?
O1 S1 N2 B1 177.50(14) . . . . ?
O1 S1 C20 C21 -41.66(18) . . . . ?
O1 S1 C20 C25 142.10(16) . . . . ?
O2 S1 N2 C7 170.59(13) . . . . ?
O2 S1 N2 B1 -53.22(16) . . . . ?
O2 S1 C20 C21 -174.16(14) . . . . ?
O2 S1 C20 C25 9.61(18) . . . . ?
O3 C11 C12 C13 179.3(2) . . . . ?
N1 C7 C8 N4 174.05(17) . . . . ?
N1 C7 C8 C5 1.8(2) . . . . ?
N2 S1 C20 C21 72.02(16) . . . . ?
N2 S1 C20 C25 -104.22(16) . . . . ?
N2 C7 C8 N4 -3.1(3) . . . . ?
N2 C7 C8 C5 -175.36(16) . . . . ?
N3 N4 C8 C5 -172.96(17) . . . . ?
N3 N4 C8 C7 16.4(3) . . . . ?
N3 C10 C11 O3 -0.3(2) . . . . ?
N3 C10 C11 C12 -179.05(18) . . . . ?
N3 C10 C15 C14 -179.08(19) . . . . ?
N3 C10 C15 C16 -1.4(3) . . . . ?
N4 N3 C10 C11 163.85(16) . . . . ?
N4 N3 C10 C15 -17.2(3) . . . . ?
N4 N3 B1 F1 82.6(2) . . . . ?
N4 N3 B1 O3 -158.24(16) . . . . ?
N4 N3 B1 N2 -34.9(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C1 C6 N1 -179.1(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C8 178.2(2) . . . . ?
C4 C5 C6 N1 179.21(18) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C8 N4 8.2(4) . . . . ?
C4 C5 C8 C7 -179.7(2) . . . . ?
C6 N1 C7 N2 175.67(17) . . . . ?
C6 N1 C7 C8 -1.4(2) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C5 C8 N4 -173.51(18) . . . . ?
C6 C5 C8 C7 -1.5(2) . . . . ?
C7 N1 C6 C1 -180.0(2) . . . . ?
C7 N1 C6 C5 0.5(2) . . . . ?
C7 N2 B1 F1 -76.81(19) . . . . ?
C7 N2 B1 O3 154.22(16) . . . . ?
C7 N2 B1 N3 41.52(19) . . . . ?
C8 C5 C6 N1 0.6(2) . . . . ?
C8 C5 C6 C1 -179.0(2) . . . . ?
C9 N1 C6 C1 11.8(3) . . . . ?
C9 N1 C6 C5 -167.81(19) . . . . ?
C9 N1 C7 N2 -16.8(3) . . . . ?
C9 N1 C7 C8 166.13(19) . . . . ?
C10 N3 N4 C8 -166.52(16) . . . . ?
C10 N3 B1 F1 -104.60(17) . . . . ?
C10 N3 B1 O3 14.53(18) . . . . ?
C10 N3 B1 N2 137.84(15) . . . . ?
C10 C11 C12 C13 -2.1(3) . . . . ?
C10 C15 C16 C17 -177.1(2) . . . . ?
C11 O3 B1 F1 102.25(19) . . . . ?
C11 O3 B1 N2 -130.99(17) . . . . ?
C11 O3 B1 N3 -14.42(18) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C10 C15 C16 177.47(19) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C12 C13 C14 C19 -177.5(2) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C13 C14 C15 C16 -178.9(2) . . . . ?
C13 C14 C19 C18 178.8(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C10 C11 O3 -179.41(17) . . . . ?
C15 C10 C11 C12 1.8(3) . . . . ?
C15 C14 C19 C18 0.4(4) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
C19 C14 C15 C10 177.4(2) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C20 S1 N2 C7 -73.57(15) . . . . ?
C20 S1 N2 B1 62.63(15) . . . . ?
C20 C21 C22 C23 -1.0(3) . . . . ?
C21 C20 C25 C24 -0.5(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C21 C22 C23 C26 178.9(2) . . . . ?
C22 C23 C24 C25 1.4(4) . . . . ?
C23 C24 C25 C20 -1.0(3) . . . . ?
C25 C20 C21 C22 1.4(3) . . . . ?
C26 C23 C24 C25 -177.9(3) . . . . ?
B1 O3 C11 C10 10.5(2) . . . . ?
B1 O3 C11 C12 -170.79(19) . . . . ?
B1 N2 C7 N1 154.57(18) . . . . ?
B1 N2 C7 C8 -28.8(2) . . . . ?
B1 N3 N4 C8 5.1(2) . . . . ?
B1 N3 C10 C11 -9.09(19) . . . . ?
B1 N3 C10 C15 169.91(19) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_141127_dhl507052_2_cj
_database_code_depnum_ccdc_archive 'CCDC 1446777'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_audit_creation_date             2014-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H26 N4 O4 S'
_chemical_formula_sum            'C26 H26 N4 O4 S'
_chemical_formula_weight         490.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.094(3)
_cell_length_b                   9.7382(7)
_cell_length_c                   15.8855(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.540(7)
_cell_angle_gamma                90.00
_cell_volume                     5086.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2166
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5006
_cell_measurement_theta_min      3.3191
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10123
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0197537000
_diffrn_orient_matrix_UB_12      -0.0098772000
_diffrn_orient_matrix_UB_13      0.0215519000
_diffrn_orient_matrix_UB_21      -0.0086128000
_diffrn_orient_matrix_UB_22      -0.0146213000
_diffrn_orient_matrix_UB_23      0.0379039000
_diffrn_orient_matrix_UB_31      -0.0010008000
_diffrn_orient_matrix_UB_32      -0.0706845000
_diffrn_orient_matrix_UB_33      -0.0108535000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2775
_reflns_number_total             4653
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0667P)²+1.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C3(H3), C4(H4A), C5(H5), C11(H11), C12(H12), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.15411(3) 0.36351(7) 0.39927(5) 0.0811(3) Uani 1 d . . .
O1 O 0.13331(10) 0.2703(2) 0.44848(15) 0.1270(10) Uani 1 d . . .
O2 O 0.19332(8) 0.3217(3) 0.37664(15) 0.1121(9) Uani 1 d . . .
O3 O 0.04607(7) 0.7457(3) 0.39358(18) 0.1088(8) Uani 1 d . . .
O4 O 0.03792(7) 0.9703(2) 0.37362(15) 0.0926(7) Uani 1 d . . .
N1 N 0.21232(7) 0.5119(2) 0.55172(13) 0.0694(6) Uani 1 d . . .
N2 N 0.15535(7) 0.5155(2) 0.43989(14) 0.0664(6) Uani 1 d . . .
N3 N 0.15973(6) 0.8136(2) 0.47655(12) 0.0557(5) Uani 1 d . . .
N4 N 0.12927(7) 0.7799(2) 0.42072(13) 0.0622(6) Uani 1 d . . .
H4 H 0.1241 0.6950 0.4090 0.075 Uiso 1 calc . . R
C1 C 0.21732(8) 0.7432(3) 0.57637(16) 0.0600(7) Uani 1 d . . .
C2 C 0.23402(8) 0.8608(4) 0.61456(18) 0.0754(8) Uani 1 d . . .
H2 H 0.2235 0.9470 0.5995 0.090 Uiso 1 calc . . R
C3 C 0.26722(10) 0.8460(5) 0.6766(2) 0.0948(11) Uani 1 d . . .
H3 H 0.2791 0.9235 0.7030 0.114 Uiso 1 calc . . R
C4 C 0.28250(10) 0.7178(6) 0.6990(2) 0.1051(13) Uani 1 d . . .
H4A H 0.3044 0.7108 0.7411 0.126 Uiso 1 calc . . R
C5 C 0.26646(10) 0.6004(5) 0.6612(2) 0.0918(11) Uani 1 d . . .
H5 H 0.2771 0.5144 0.6763 0.110 Uiso 1 calc . . R
C6 C 0.23366(8) 0.6152(3) 0.59931(16) 0.0669(8) Uani 1 d . . .
C7 C 0.18259(8) 0.5691(3) 0.49651(15) 0.0571(7) Uani 1 d . . .
C8 C 0.18378(7) 0.7173(3) 0.51161(15) 0.0520(6) Uani 1 d . . .
C9 C 0.22026(13) 0.3658(4) 0.5683(2) 0.1121(14) Uani 1 d . . .
H9A H 0.1977 0.3126 0.5428 0.168 Uiso 1 calc . . GR
H9B H 0.2238 0.3500 0.6283 0.168 Uiso 1 calc . . GR
H9C H 0.2445 0.3391 0.5446 0.168 Uiso 1 calc . . GR
C10 C 0.12228(10) 0.3967(2) 0.30537(17) 0.0627(7) Uani 1 d . . .
C11 C 0.08158(12) 0.4178(4) 0.3057(2) 0.1029(12) Uani 1 d . . .
H11 H 0.0701 0.4143 0.3564 0.124 Uiso 1 calc . . R
C12 C 0.05755(11) 0.4443(5) 0.2317(3) 0.1192(15) Uani 1 d . . .
H12 H 0.0299 0.4588 0.2336 0.143 Uiso 1 calc . . R
C13 C 0.07215(11) 0.4501(3) 0.1561(2) 0.0811(9) Uani 1 d . . .
C14 C 0.11264(11) 0.4287(3) 0.15619(19) 0.0786(9) Uani 1 d . . .
H14 H 0.1237 0.4316 0.1050 0.094 Uiso 1 calc . . R
C15 C 0.13783(10) 0.4029(3) 0.2293(2) 0.0738(8) Uani 1 d . . .
H15 H 0.1655 0.3896 0.2271 0.089 Uiso 1 calc . . R
C16 C 0.04475(13) 0.4820(5) 0.0758(2) 0.1321(16) Uani 1 d . . .
H16A H 0.0605 0.5227 0.0352 0.198 Uiso 1 calc . . GR
H16B H 0.0239 0.5448 0.0883 0.198 Uiso 1 calc . . GR
H16C H 0.0325 0.3987 0.0530 0.198 Uiso 1 calc . . GR
C17 C 0.10446(8) 0.8877(3) 0.37884(16) 0.0608(7) Uani 1 d . . .
H17 H 0.1114 0.9743 0.4085 0.073 Uiso 1 calc . . R
C18 C 0.11260(7) 0.9039(2) 0.28740(16) 0.0545(6) Uani 1 d . . .
C19 C 0.12953(9) 1.0224(3) 0.2597(2) 0.0737(8) Uani 1 d . . .
H19 H 0.1353 1.0950 0.2971 0.088 Uiso 1 calc . . R
C20 C 0.13797(10) 1.0346(3) 0.1777(2) 0.0884(10) Uani 1 d . . .
H20 H 0.1492 1.1158 0.1600 0.106 Uiso 1 calc . . R
C21 C 0.13018(11) 0.9299(3) 0.1219(2) 0.0848(9) Uani 1 d . . .
H21 H 0.1365 0.9384 0.0666 0.102 Uiso 1 calc . . R
C22 C 0.11304(10) 0.8121(3) 0.14766(19) 0.0810(9) Uani 1 d . . .
H22 H 0.1071 0.7407 0.1094 0.097 Uiso 1 calc . . R
C23 C 0.10440(9) 0.7982(3) 0.23025(17) 0.0684(8) Uani 1 d . . .
H23 H 0.0930 0.7171 0.2474 0.082 Uiso 1 calc . . R
C24 C 0.05985(9) 0.8578(3) 0.38413(18) 0.0691(8) Uani 1 d . . .
C25 C -0.00613(10) 0.9579(5) 0.3717(3) 0.1103(13) Uani 1 d . . .
H25A H -0.0130 0.9106 0.4219 0.132 Uiso 1 calc . . R
H25B H -0.0173 0.9063 0.3222 0.132 Uiso 1 calc . . R
C26 C -0.02277(14) 1.0990(6) 0.3685(4) 0.164(2) Uani 1 d . . .
H26A H -0.0202 1.1387 0.3141 0.246 Uiso 1 calc . . GR
H26B H -0.0080 1.1537 0.4119 0.246 Uiso 1 calc . . GR
H26C H -0.0510 1.0963 0.3776 0.246 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
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 O1 1.425(2) . ?
S1 O2 1.444(3) . ?
S1 N2 1.613(2) . ?
S1 C10 1.755(3) . ?
O3 C24 1.199(3) . ?
O4 C24 1.314(3) . ?
O4 C25 1.460(4) . ?
N1 C6 1.401(4) . ?
N1 C7 1.361(3) . ?
N1 C9 1.465(4) . ?
N2 C7 1.308(3) . ?
N3 N4 1.306(3) . ?
N3 C8 1.313(3) . ?
N4 H4 0.8600 . ?
N4 C17 1.447(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.391(4) . ?
C1 C8 1.447(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(5) . ?
C4 H4A 0.9300 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C7 C8 1.462(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.363(4) . ?
C10 C15 1.367(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.345(5) . ?
C13 C14 1.356(4) . ?
C13 C16 1.510(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.515(4) . ?
C17 C24 1.516(4) . ?
C18 C19 1.376(4) . ?
C18 C23 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.368(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.357(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.363(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.479(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
O1 S1 O2 117.44(17) . . ?
O1 S1 N2 110.89(14) . . ?
O1 S1 C10 107.63(16) . . ?
O2 S1 N2 112.07(15) . . ?
O2 S1 C10 108.04(14) . . ?
N2 S1 C10 99.00(12) . . ?
C24 O4 C25 118.0(3) . . ?
C6 N1 C9 122.1(2) . . ?
C7 N1 C6 109.7(2) . . ?
C7 N1 C9 128.0(3) . . ?
C7 N2 S1 128.73(19) . . ?
N4 N3 C8 119.5(2) . . ?
N3 N4 H4 120.6 . . ?
N3 N4 C17 118.9(2) . . ?
C17 N4 H4 120.6 . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 C8 133.9(3) . . ?
C6 C1 C8 105.9(2) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.9(3) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(4) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 N1 110.2(2) . . ?
C5 C6 N1 127.9(3) . . ?
C5 C6 C1 121.9(3) . . ?
N1 C7 C8 107.1(2) . . ?
N2 C7 N1 132.2(2) . . ?
N2 C7 C8 120.7(2) . . ?
N3 C8 C1 123.8(2) . . ?
N3 C8 C7 129.2(2) . . ?
C1 C8 C7 107.0(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 121.5(2) . . ?
C11 C10 C15 117.9(3) . . ?
C15 C10 S1 120.6(2) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 118.6 . . ?
C13 C12 C11 122.8(3) . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 116.6(3) . . ?
C12 C13 C16 121.3(4) . . ?
C14 C13 C16 122.1(3) . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 120.1(3) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17 108.3 . . ?
N4 C17 C18 111.3(2) . . ?
N4 C17 C24 109.9(2) . . ?
C18 C17 H17 108.3 . . ?
C18 C17 C24 110.7(2) . . ?
C24 C17 H17 108.3 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 C23 118.2(3) . . ?
C23 C18 C17 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.4(3) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
O3 C24 O4 124.2(3) . . ?
O3 C24 C17 124.6(3) . . ?
O4 C24 C17 111.1(3) . . ?
O4 C25 H25A 110.3 . . ?
O4 C25 H25B 110.3 . . ?
O4 C25 C26 106.9(4) . . ?
H25A C25 H25B 108.6 . . ?
C26 C25 H25A 110.3 . . ?
C26 C25 H25B 110.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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 N2 C7 N1 -16.6(5) . . . . ?
S1 N2 C7 C8 165.82(19) . . . . ?
S1 C10 C11 C12 179.6(3) . . . . ?
S1 C10 C15 C14 179.9(2) . . . . ?
O1 S1 N2 C7 89.4(3) . . . . ?
O1 S1 C10 C11 42.1(3) . . . . ?
O1 S1 C10 C15 -138.3(2) . . . . ?
O2 S1 N2 C7 -44.0(3) . . . . ?
O2 S1 C10 C11 169.8(3) . . . . ?
O2 S1 C10 C15 -10.6(3) . . . . ?
N1 C7 C8 N3 -176.4(2) . . . . ?
N1 C7 C8 C1 2.6(3) . . . . ?
N2 S1 C10 C11 -73.3(3) . . . . ?
N2 S1 C10 C15 106.3(2) . . . . ?
N2 C7 C8 N3 1.7(4) . . . . ?
N2 C7 C8 C1 -179.2(2) . . . . ?
N3 N4 C17 C18 107.2(2) . . . . ?
N3 N4 C17 C24 -129.8(2) . . . . ?
N4 N3 C8 C1 -177.5(2) . . . . ?
N4 N3 C8 C7 1.4(4) . . . . ?
N4 C17 C18 C19 -115.0(3) . . . . ?
N4 C17 C18 C23 62.9(3) . . . . ?
N4 C17 C24 O3 -23.9(4) . . . . ?
N4 C17 C24 O4 158.6(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 N1 -179.1(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C8 N3 -3.2(4) . . . . ?
C2 C1 C8 C7 177.7(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 N1 179.7(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C6 N1 C7 N2 179.9(3) . . . . ?
C6 N1 C7 C8 -2.3(3) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
C6 C1 C8 N3 177.2(2) . . . . ?
C6 C1 C8 C7 -1.9(3) . . . . ?
C7 N1 C6 C1 1.1(3) . . . . ?
C7 N1 C6 C5 -178.9(3) . . . . ?
C8 N3 N4 C17 -176.3(2) . . . . ?
C8 C1 C2 C3 179.9(3) . . . . ?
C8 C1 C6 N1 0.6(3) . . . . ?
C8 C1 C6 C5 -179.4(3) . . . . ?
C9 N1 C6 C1 -173.8(3) . . . . ?
C9 N1 C6 C5 6.2(5) . . . . ?
C9 N1 C7 N2 -5.6(5) . . . . ?
C9 N1 C7 C8 172.2(3) . . . . ?
C10 S1 N2 C7 -157.8(3) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C10 C15 C14 -0.5(4) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C11 C12 C13 C16 -178.9(4) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C15 C10 C11 C12 0.0(5) . . . . ?
C16 C13 C14 C15 178.4(3) . . . . ?
C17 C18 C19 C20 177.9(3) . . . . ?
C17 C18 C23 C22 -178.0(3) . . . . ?
C18 C17 C24 O3 99.4(3) . . . . ?
C18 C17 C24 O4 -78.1(3) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 C18 C23 C22 -0.1(4) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C23 -1.3(5) . . . . ?
C21 C22 C23 C18 0.7(5) . . . . ?
C23 C18 C19 C20 0.0(4) . . . . ?
C24 O4 C25 C26 174.1(3) . . . . ?
C24 C17 C18 C19 122.5(3) . . . . ?
C24 C17 C18 C23 -59.6(3) . . . . ?
C25 O4 C24 O3 -1.2(5) . . . . ?
C25 O4 C24 C17 176.3(3) . . . . ?

