# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_160616_sgr4_079a
_database_code_depnum_ccdc_archive 'CCDC 1574179'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-06-17
_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 H27 N3 O4 S'
_chemical_formula_sum            'C26 H27 N3 O4 S'
_chemical_formula_weight         477.57
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o2 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.6582(4)
_cell_length_b                   10.5543(6)
_cell_length_c                   25.8744(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2364.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1983
_cell_measurement_theta_min      3.1371
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97991
_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    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15997
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.14
_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      0.0208946000
_diffrn_orient_matrix_UB_12      0.0604440000
_diffrn_orient_matrix_UB_13      0.0097456000
_diffrn_orient_matrix_UB_21      0.0108766000
_diffrn_orient_matrix_UB_22      0.0222965000
_diffrn_orient_matrix_UB_23      -0.0256010000
_diffrn_orient_matrix_UB_31      -0.0784698000
_diffrn_orient_matrix_UB_32      0.0191415000
_diffrn_orient_matrix_UB_33      -0.0009473000
_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                3477
_reflns_number_total             4337
_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         0.191
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack (1983), 1848 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.023
_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)+(0.0550P)²+0.1466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1056
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4A), C13(H13), C14(H14), C16(H16), C17(H17),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.99893(8) 1.06023(7) 0.11490(3) 0.0529(2) Uani 1 d . . .
O1 O 0.8717(2) 1.14776(18) 0.11682(10) 0.0724(7) Uani 1 d . . .
O2 O 1.1281(3) 1.0994(2) 0.08457(9) 0.0781(7) Uani 1 d . . .
O3 O 0.6492(2) 0.99062(16) 0.04036(7) 0.0442(4) Uani 1 d . . .
O4 O 0.5046(6) 1.1454(2) -0.03793(11) 0.1323(14) Uani 1 d . . .
H4 H 0.5283 1.2012 -0.0585 0.198 Uiso 1 calc . . GR
N1 N 0.8297(2) 0.74132(19) 0.07419(8) 0.0393(5) Uani 1 d . . .
N2 N 0.5894(2) 0.98534(19) 0.12569(8) 0.0422(5) Uani 1 d . . .
N3 N 0.9577(2) 0.9198(2) 0.09543(8) 0.0475(6) Uani 1 d . . .
C1 C 0.4174(3) 0.7592(3) 0.06618(10) 0.0426(6) Uani 1 d . . .
H1 H 0.3426 0.8198 0.0736 0.051 Uiso 1 calc . . R
C1A C 1.1625(3) 0.9726(3) 0.27745(11) 0.0549(7) Uani 1 d . . .
C2 C 0.3756(3) 0.6401(3) 0.04832(11) 0.0470(7) Uani 1 d . . .
H2 H 0.2719 0.6208 0.0432 0.056 Uiso 1 calc . . R
C3 C 0.4866(3) 0.5505(2) 0.03810(10) 0.0488(6) Uani 1 d . . .
H3 H 0.4563 0.4718 0.0255 0.059 Uiso 1 calc . . R
C4 C 0.6416(3) 0.5738(3) 0.04594(10) 0.0453(6) Uani 1 d . . .
H4A H 0.7160 0.5121 0.0397 0.054 Uiso 1 calc . . R
C5 C 0.6810(3) 0.6936(2) 0.06357(9) 0.0351(6) Uani 1 d . . .
C6 C 0.5720(3) 0.7859(2) 0.07270(9) 0.0342(5) Uani 1 d . . .
C7 C 0.6538(3) 0.9105(2) 0.08422(9) 0.0373(6) Uani 1 d . . .
C8 C 0.8266(3) 0.8645(2) 0.08778(9) 0.0387(6) Uani 1 d . . .
C9 C 0.5277(3) 1.1038(2) 0.10520(11) 0.0473(7) Uani 1 d . . .
H9A H 0.5961 1.1744 0.1123 0.057 Uiso 1 calc . . R
H9B H 0.4261 1.1220 0.1192 0.057 Uiso 1 calc . . R
C10 C 0.5201(3) 1.0754(2) 0.04827(10) 0.0491(6) Uani 1 d . . .
H10 H 0.4237 1.0305 0.0406 0.059 Uiso 1 calc . . R
C11 C 0.5349(5) 1.1874(3) 0.01298(14) 0.0787(10) Uani 1 d . . .
H11A H 0.4615 1.2526 0.0228 0.094 Uiso 1 calc . . R
H11B H 0.6382 1.2225 0.0152 0.094 Uiso 1 calc . . R
C12 C 0.6152(3) 0.9640(2) 0.17816(9) 0.0380(6) Uani 1 d . . .
C13 C 0.5826(3) 1.0573(3) 0.21459(11) 0.0487(7) Uani 1 d . . .
H13 H 0.5429 1.1348 0.2038 0.058 Uiso 1 calc . . R
C14 C 0.6084(3) 1.0363(3) 0.26620(11) 0.0554(8) Uani 1 d . . .
H14 H 0.5859 1.1007 0.2896 0.066 Uiso 1 calc . . R
C15 C 0.6664(3) 0.9232(3) 0.28480(10) 0.0535(7) Uani 1 d . . .
C16 C 0.6963(3) 0.8293(3) 0.24853(11) 0.0522(7) Uani 1 d . . .
H16 H 0.7348 0.7516 0.2596 0.063 Uiso 1 calc . . R
C17 C 0.6701(3) 0.8486(2) 0.19638(10) 0.0438(6) Uani 1 d . . .
H17 H 0.6896 0.7834 0.1731 0.053 Uiso 1 calc . . R
C18 C 0.7009(5) 0.9024(4) 0.34163(12) 0.0821(11) Uani 1 d . . .
H18A H 0.7683 0.9681 0.3538 0.123 Uiso 1 calc . . GR
H18B H 0.7500 0.8216 0.3461 0.123 Uiso 1 calc . . GR
H18C H 0.6062 0.9042 0.3609 0.123 Uiso 1 calc . . GR
C19 C 1.0626(3) 1.0277(2) 0.17811(11) 0.0456(7) Uani 1 d . . .
C20 C 0.9917(3) 1.0854(3) 0.21962(12) 0.0573(7) Uani 1 d . . .
H20 H 0.9111 1.1424 0.2147 0.069 Uiso 1 calc . . R
C21 C 1.0436(3) 1.0565(3) 0.26883(12) 0.0637(8) Uani 1 d . . .
H21 H 0.9965 1.0951 0.2970 0.076 Uiso 1 calc . . R
C22 C 0.9729(3) 0.6711(3) 0.06774(12) 0.0547(7) Uani 1 d . . .
H22A H 0.9500 0.5832 0.0623 0.082 Uiso 1 calc . . GR
H22B H 1.0351 0.6802 0.0982 0.082 Uiso 1 calc . . GR
H22C H 1.0282 0.7037 0.0385 0.082 Uiso 1 calc . . GR
C23 C 1.2309(3) 0.9165(3) 0.23542(12) 0.0597(8) Uani 1 d . . .
H23 H 1.3114 0.8593 0.2403 0.072 Uiso 1 calc . . R
C24 C 1.1820(3) 0.9437(3) 0.18621(11) 0.0604(8) Uani 1 d . . .
H24 H 1.2298 0.9052 0.1581 0.072 Uiso 1 calc . . R
C25 C 1.2178(4) 0.9425(4) 0.33160(12) 0.0829(11) Uani 1 d . . .
H25A H 1.2785 1.0118 0.3444 0.124 Uiso 1 calc . . GR
H25B H 1.2796 0.8670 0.3309 0.124 Uiso 1 calc . . GR
H25C H 1.1303 0.9297 0.3538 0.124 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 1.438(2) . ?
S1 O2 1.427(2) . ?
S1 N3 1.605(2) . ?
S1 C19 1.760(3) . ?
O3 C7 1.416(3) . ?
O3 C10 1.446(3) . ?
O4 H4 0.8200 . ?
O4 C11 1.414(4) . ?
N1 C5 1.410(3) . ?
N1 C8 1.347(3) . ?
N1 C22 1.454(3) . ?
N2 C7 1.444(3) . ?
N2 C9 1.459(3) . ?
N2 C12 1.395(3) . ?
N3 C8 1.292(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(4) . ?
C1 C6 1.379(3) . ?
C1A C21 1.376(4) . ?
C1A C23 1.373(4) . ?
C1A C25 1.514(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4A 0.9300 . ?
C4 C5 1.387(4) . ?
C5 C6 1.377(3) . ?
C6 C7 1.523(3) . ?
C7 C8 1.576(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.499(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.392(3) . ?
C12 C17 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(4) . ?
C15 C16 1.390(4) . ?
C15 C18 1.517(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.379(4) . ?
C19 C24 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(4) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.372(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 N3 115.70(11) . . ?
O1 S1 C19 109.46(14) . . ?
O2 S1 O1 115.67(14) . . ?
O2 S1 N3 105.59(14) . . ?
O2 S1 C19 108.79(13) . . ?
N3 S1 C19 100.42(12) . . ?
C7 O3 C10 106.12(18) . . ?
C11 O4 H4 109.5 . . ?
C5 N1 C22 125.1(2) . . ?
C8 N1 C5 112.19(19) . . ?
C8 N1 C22 122.6(2) . . ?
C7 N2 C9 109.9(2) . . ?
C12 N2 C7 124.96(19) . . ?
C12 N2 C9 123.4(2) . . ?
C8 N3 S1 131.33(18) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.6(2) . . ?
C21 C1A C25 121.4(3) . . ?
C23 C1A C21 118.2(3) . . ?
C23 C1A C25 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4A 121.6 . . ?
C3 C4 C5 116.8(2) . . ?
C5 C4 H4A 121.6 . . ?
C4 C5 N1 127.9(2) . . ?
C6 C5 N1 109.8(2) . . ?
C6 C5 C4 122.2(2) . . ?
C1 C6 C7 130.7(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 109.06(19) . . ?
O3 C7 N2 104.96(18) . . ?
O3 C7 C6 110.22(19) . . ?
O3 C7 C8 104.92(18) . . ?
N2 C7 C6 116.0(2) . . ?
N2 C7 C8 119.5(2) . . ?
C6 C7 C8 100.74(18) . . ?
N1 C8 C7 107.5(2) . . ?
N3 C8 N1 117.3(2) . . ?
N3 C8 C7 134.8(2) . . ?
N2 C9 H9A 111.4 . . ?
N2 C9 H9B 111.4 . . ?
N2 C9 C10 101.6(2) . . ?
H9A C9 H9B 109.3 . . ?
C10 C9 H9A 111.4 . . ?
C10 C9 H9B 111.4 . . ?
O3 C10 C9 103.19(19) . . ?
O3 C10 H10 109.3 . . ?
O3 C10 C11 109.6(2) . . ?
C9 C10 H10 109.3 . . ?
C11 C10 C9 115.8(2) . . ?
C11 C10 H10 109.3 . . ?
O4 C11 C10 107.7(3) . . ?
O4 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 N2 120.8(2) . . ?
C17 C12 N2 121.8(2) . . ?
C17 C12 C13 117.4(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.5(3) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C16 116.7(3) . . ?
C14 C15 C18 122.3(3) . . ?
C16 C15 C18 121.0(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 S1 119.9(2) . . ?
C24 C19 S1 120.1(2) . . ?
C24 C19 C20 120.0(3) . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.3(3) . . ?
C21 C20 H20 120.8 . . ?
C1A C21 C20 122.3(3) . . ?
C1A C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1A C23 H23 119.6 . . ?
C24 C23 C1A 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.5(3) . . ?
C23 C24 H24 119.7 . . ?
C1A C25 H25A 109.5 . . ?
C1A C25 H25B 109.5 . . ?
C1A C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 N3 C8 N1 -175.9(2) . . . . ?
S1 N3 C8 C7 12.6(4) . . . . ?
S1 C19 C20 C21 179.3(2) . . . . ?
S1 C19 C24 C23 -179.1(2) . . . . ?
O1 S1 N3 C8 -11.1(3) . . . . ?
O1 S1 C19 C20 -0.7(3) . . . . ?
O1 S1 C19 C24 178.6(2) . . . . ?
O2 S1 N3 C8 -140.4(2) . . . . ?
O2 S1 C19 C20 126.5(2) . . . . ?
O2 S1 C19 C24 -54.1(3) . . . . ?
O3 C7 C8 N1 -108.3(2) . . . . ?
O3 C7 C8 N3 63.7(3) . . . . ?
O3 C10 C11 O4 71.5(4) . . . . ?
N1 C5 C6 C1 -178.3(2) . . . . ?
N1 C5 C6 C7 7.2(3) . . . . ?
N2 C7 C8 N1 134.4(2) . . . . ?
N2 C7 C8 N3 -53.5(4) . . . . ?
N2 C9 C10 O3 -32.2(3) . . . . ?
N2 C9 C10 C11 -151.9(3) . . . . ?
N2 C12 C13 C14 -179.8(2) . . . . ?
N2 C12 C17 C16 179.5(2) . . . . ?
N3 S1 C19 C20 -122.9(2) . . . . ?
N3 S1 C19 C24 56.4(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C6 C7 O3 -71.3(3) . . . . ?
C1 C6 C7 N2 47.8(4) . . . . ?
C1 C6 C7 C8 178.3(3) . . . . ?
C1A C23 C24 C19 -0.3(5) . . . . ?
C2 C1 C6 C5 -2.7(4) . . . . ?
C2 C1 C6 C7 170.5(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 N1 -179.5(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 2.4(4) . . . . ?
C4 C5 C6 C7 -172.1(2) . . . . ?
C5 N1 C8 N3 -176.1(2) . . . . ?
C5 N1 C8 C7 -2.4(3) . . . . ?
C5 C6 C7 O3 102.5(2) . . . . ?
C5 C6 C7 N2 -138.5(2) . . . . ?
C5 C6 C7 C8 -8.0(2) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C6 C7 C8 N1 6.2(2) . . . . ?
C6 C7 C8 N3 178.2(3) . . . . ?
C7 O3 C10 C9 38.6(2) . . . . ?
C7 O3 C10 C11 162.6(2) . . . . ?
C7 N2 C9 C10 15.5(3) . . . . ?
C7 N2 C12 C13 163.4(2) . . . . ?
C7 N2 C12 C17 -18.3(4) . . . . ?
C8 N1 C5 C4 176.2(2) . . . . ?
C8 N1 C5 C6 -3.0(3) . . . . ?
C9 N2 C7 O3 7.5(2) . . . . ?
C9 N2 C7 C6 -114.4(2) . . . . ?
C9 N2 C7 C8 124.7(2) . . . . ?
C9 N2 C12 C13 -0.1(4) . . . . ?
C9 N2 C12 C17 178.2(2) . . . . ?
C9 C10 C11 O4 -172.3(3) . . . . ?
C10 O3 C7 N2 -28.8(2) . . . . ?
C10 O3 C7 C6 96.8(2) . . . . ?
C10 O3 C7 C8 -155.50(19) . . . . ?
C12 N2 C7 O3 -157.9(2) . . . . ?
C12 N2 C7 C6 80.2(3) . . . . ?
C12 N2 C7 C8 -40.7(3) . . . . ?
C12 N2 C9 C10 -178.8(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C12 C17 C16 -2.2(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C13 C14 C15 C18 177.4(3) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C12 1.1(4) . . . . ?
C17 C12 C13 C14 1.8(4) . . . . ?
C18 C15 C16 C17 -177.8(3) . . . . ?
C19 S1 N3 C8 106.5(3) . . . . ?
C19 C20 C21 C1A -0.1(4) . . . . ?
C20 C19 C24 C23 0.3(4) . . . . ?
C21 C1A C23 C24 0.1(5) . . . . ?
C22 N1 C5 C4 0.7(4) . . . . ?
C22 N1 C5 C6 -178.5(2) . . . . ?
C22 N1 C8 N3 -0.4(4) . . . . ?
C22 N1 C8 C7 173.3(2) . . . . ?
C23 C1A C21 C20 0.1(4) . . . . ?
C24 C19 C20 C21 -0.1(4) . . . . ?
C25 C1A C21 C20 179.8(3) . . . . ?
C25 C1A C23 C24 -179.7(3) . . . . ?

####################################################################### 
# 
# 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_161101_sgr4_100b
_database_code_depnum_ccdc_archive 'CCDC 1574180'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-11-01
_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 H27 N3 O4 S'
_chemical_formula_sum            'C26 H27 N3 O4 S'
_chemical_formula_weight         477.57
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.6243(6)
_cell_length_b                   10.5297(7)
_cell_length_c                   25.811(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2344.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4828
_cell_measurement_theta_min      2.8349
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85554
_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    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16008
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_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      0.0359862000
_diffrn_orient_matrix_UB_12      -0.0396638000
_diffrn_orient_matrix_UB_13      0.0186735000
_diffrn_orient_matrix_UB_21      0.0027150000
_diffrn_orient_matrix_UB_22      0.0515983000
_diffrn_orient_matrix_UB_23      0.0176455000
_diffrn_orient_matrix_UB_31      -0.0738758000
_diffrn_orient_matrix_UB_32      -0.0174572000
_diffrn_orient_matrix_UB_33      0.0097480000
_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                3643
_reflns_number_total             4297
_reflns_odcompleteness_completeness 99.60
_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         0.177
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack (1983), 1831 Friedel pairs'
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0187(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.030
_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)+(0.0478P)²+0.4055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0982
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-O1
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), 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 0.00147(8) 0.43964(6) 0.88503(3) 0.0521(2) Uani 1 d . . .
O0 O 0.35148(19) 0.50969(14) 0.95963(6) 0.0437(4) Uani 1 d . . .
O1 O 0.4965(6) 0.3545(2) 1.03759(10) 0.1304(13) Uani 1 d . . D
H1 H 0.459(6) 0.292(4) 1.055(2) 0.19(3) Uiso 1 d . . D
O2 O -0.1279(2) 0.4000(2) 0.91539(8) 0.0746(6) Uani 1 d . . .
O3 O 0.1288(2) 0.35205(17) 0.88304(9) 0.0717(6) Uani 1 d . . .
N1 N 0.1703(2) 0.75888(17) 0.92568(7) 0.0392(4) Uani 1 d . . .
N2 N 0.4108(2) 0.51506(17) 0.87410(8) 0.0411(5) Uani 1 d . . .
N3 N 0.0423(2) 0.5804(2) 0.90448(8) 0.0473(5) Uani 1 d . . .
C1 C 0.5832(3) 0.7406(2) 0.93368(9) 0.0414(6) Uani 1 d . . .
H1A H 0.6584 0.6800 0.9261 0.050 Uiso 1 calc . . R
C2 C 0.6247(3) 0.8602(2) 0.95169(10) 0.0468(6) Uani 1 d . . .
H2 H 0.7287 0.8798 0.9567 0.056 Uiso 1 calc . . R
C3 C 0.5134(3) 0.9496(2) 0.96216(9) 0.0483(6) Uani 1 d . . .
H3 H 0.5437 1.0283 0.9750 0.058 Uiso 1 calc . . R
C4 C 0.3578(3) 0.9262(2) 0.95419(9) 0.0432(6) Uani 1 d . . .
H4 H 0.2828 0.9878 0.9604 0.052 Uiso 1 calc . . R
C5 C 0.3196(2) 0.8066(2) 0.93651(8) 0.0353(5) Uani 1 d . . .
C6 C 0.4283(3) 0.7141(2) 0.92727(8) 0.0339(5) Uani 1 d . . .
C7 C 0.3469(2) 0.5897(2) 0.91555(8) 0.0360(5) Uani 1 d . . .
C8 C 0.1738(3) 0.6356(2) 0.91216(9) 0.0373(5) Uani 1 d . . .
C9 C 0.0271(3) 0.8286(3) 0.93230(11) 0.0525(7) Uani 1 d . . .
H9A H -0.0274 0.7965 0.9620 0.079 Uiso 1 calc . . GR
H9B H -0.0361 0.8186 0.9020 0.079 Uiso 1 calc . . GR
H9C H 0.0499 0.9170 0.9374 0.079 Uiso 1 calc . . GR
C10 C 0.4731(3) 0.3966(2) 0.89467(9) 0.0457(6) Uani 1 d . . .
H10A H 0.5749 0.3784 0.8805 0.055 Uiso 1 calc . . R
H10B H 0.4045 0.3257 0.8877 0.055 Uiso 1 calc . . R
C11 C 0.4812(3) 0.4253(2) 0.95156(9) 0.0478(6) Uani 1 d . . .
H11 H 0.5782 0.4700 0.9593 0.057 Uiso 1 calc . . R
C12 C 0.4648(5) 0.3129(2) 0.98687(12) 0.0758(10) Uani 1 d . . .
H12A H 0.3604 0.2790 0.9848 0.091 Uiso 1 calc . . R
H12B H 0.5370 0.2467 0.9769 0.091 Uiso 1 calc . . R
C13 C -0.0628(3) 0.4717(2) 0.82177(10) 0.0440(6) Uani 1 d . . .
C14 C -0.1819(3) 0.5560(3) 0.81389(10) 0.0591(7) Uani 1 d . . .
H14 H -0.2296 0.5947 0.8421 0.071 Uiso 1 calc . . R
C15 C -0.2311(3) 0.5835(3) 0.76453(11) 0.0592(7) Uani 1 d . . .
H15 H -0.3119 0.6407 0.7596 0.071 Uiso 1 calc . . R
C16 C -0.1621(3) 0.5273(2) 0.72226(10) 0.0538(7) Uani 1 d . . .
C17 C -0.0437(3) 0.4429(3) 0.73108(11) 0.0625(7) Uani 1 d . . .
H17 H 0.0031 0.4034 0.7029 0.075 Uiso 1 calc . . R
C18 C 0.0082(3) 0.4147(2) 0.78012(11) 0.0554(6) Uani 1 d . . .
H18 H 0.0897 0.3581 0.7850 0.067 Uiso 1 calc . . R
C19 C -0.2175(4) 0.5575(4) 0.66813(11) 0.0818(10) Uani 1 d . . .
H19A H -0.1300 0.5769 0.6465 0.123 Uiso 1 calc . . GR
H19B H -0.2861 0.6293 0.6692 0.123 Uiso 1 calc . . GR
H19C H -0.2716 0.4855 0.6542 0.123 Uiso 1 calc . . GR
C20 C 0.3846(3) 0.5363(2) 0.82186(9) 0.0375(5) Uani 1 d . . .
C21 C 0.3301(3) 0.6514(2) 0.80342(9) 0.0437(6) Uani 1 d . . .
H21 H 0.3108 0.7169 0.8267 0.052 Uiso 1 calc . . R
C22 C 0.3038(3) 0.6710(2) 0.75146(10) 0.0501(6) Uani 1 d . . .
H22 H 0.2657 0.7491 0.7404 0.060 Uiso 1 calc . . R
C23 C 0.3330(3) 0.5767(3) 0.71515(9) 0.0529(6) Uani 1 d . . .
C24 C 0.3915(3) 0.4635(3) 0.73365(10) 0.0532(7) Uani 1 d . . .
H24 H 0.4142 0.3991 0.7102 0.064 Uiso 1 calc . . R
C25 C 0.4173(3) 0.4426(2) 0.78541(10) 0.0472(6) Uani 1 d . . .
H25 H 0.4572 0.3650 0.7963 0.057 Uiso 1 calc . . R
C26 C 0.2998(4) 0.5974(4) 0.65820(11) 0.0799(10) Uani 1 d . . .
H26A H 0.3957 0.6006 0.6394 0.120 Uiso 1 calc . . GR
H26B H 0.2450 0.6760 0.6538 0.120 Uiso 1 calc . . GR
H26C H 0.2376 0.5287 0.6453 0.120 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 O2 1.426(2) . ?
S1 O3 1.435(2) . ?
S1 N3 1.604(2) . ?
S1 C13 1.757(3) . ?
O0 C7 1.416(3) . ?
O0 C11 1.444(3) . ?
O1 H1 0.86(2) . ?
O1 C12 1.407(4) . ?
N1 C5 1.410(3) . ?
N1 C8 1.345(3) . ?
N1 C9 1.447(3) . ?
N2 C7 1.438(3) . ?
N2 C10 1.458(3) . ?
N2 C20 1.385(3) . ?
N3 C8 1.290(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.375(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.571(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.501(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.500(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.373(4) . ?
C13 C18 1.376(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(4) . ?
C16 C17 1.373(4) . ?
C16 C19 1.511(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.385(3) . ?
C20 C25 1.392(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(3) . ?
C23 C24 1.379(4) . ?
C23 C26 1.513(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(4) . ?
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
O2 S1 O3 115.48(13) . . ?
O2 S1 N3 105.68(13) . . ?
O2 S1 C13 108.67(12) . . ?
O3 S1 N3 115.93(11) . . ?
O3 S1 C13 109.38(13) . . ?
N3 S1 C13 100.51(11) . . ?
C7 O0 C11 105.80(16) . . ?
C12 O1 H1 101(4) . . ?
C5 N1 C9 125.10(19) . . ?
C8 N1 C5 112.03(18) . . ?
C8 N1 C9 122.7(2) . . ?
C7 N2 C10 109.76(18) . . ?
C20 N2 C7 125.01(18) . . ?
C20 N2 C10 123.53(18) . . ?
C8 N3 S1 131.11(17) . . ?
C2 C1 H1A 120.8 . . ?
C6 C1 H1A 120.8 . . ?
C6 C1 C2 118.3(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.8 . . ?
C3 C4 C5 116.4(2) . . ?
C5 C4 H4 121.8 . . ?
C4 C5 N1 127.5(2) . . ?
C6 C5 N1 109.66(19) . . ?
C6 C5 C4 122.8(2) . . ?
C1 C6 C7 130.5(2) . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 109.32(18) . . ?
O0 C7 N2 105.17(17) . . ?
O0 C7 C6 109.91(17) . . ?
O0 C7 C8 104.73(17) . . ?
N2 C7 C6 116.30(18) . . ?
N2 C7 C8 119.41(18) . . ?
C6 C7 C8 100.70(17) . . ?
N1 C8 C7 107.68(19) . . ?
N3 C8 N1 117.1(2) . . ?
N3 C8 C7 134.9(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 . . ?
N2 C10 H10A 111.4 . . ?
N2 C10 H10B 111.4 . . ?
N2 C10 C11 101.62(17) . . ?
H10A C10 H10B 109.3 . . ?
C11 C10 H10A 111.4 . . ?
C11 C10 H10B 111.4 . . ?
O0 C11 C10 103.22(18) . . ?
O0 C11 H11 109.6 . . ?
O0 C11 C12 108.9(2) . . ?
C10 C11 H11 109.6 . . ?
C12 C11 C10 115.6(2) . . ?
C12 C11 H11 109.6 . . ?
O1 C12 C11 107.6(2) . . ?
O1 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C14 C13 S1 119.9(2) . . ?
C14 C13 C18 120.0(2) . . ?
C18 C13 S1 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C19 120.4(3) . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 C19 121.7(3) . . ?
C16 C17 H17 118.8 . . ?
C16 C17 C18 122.3(3) . . ?
C18 C17 H17 118.8 . . ?
C13 C18 H18 120.7 . . ?
C17 C18 C13 118.7(3) . . ?
C17 C18 H18 120.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C25 120.7(2) . . ?
C21 C20 N2 122.1(2) . . ?
C21 C20 C25 117.2(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.3(2) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C26 121.2(3) . . ?
C24 C23 C22 116.8(2) . . ?
C24 C23 C26 122.0(3) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 C23 122.3(2) . . ?
C25 C24 H24 118.8 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.8(2) . . ?
C24 C25 H25 119.6 . . ?
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 . . ?

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 N3 C8 N1 175.90(18) . . . . ?
S1 N3 C8 C7 -12.2(4) . . . . ?
S1 C13 C14 C15 178.8(2) . . . . ?
S1 C13 C18 C17 -179.3(2) . . . . ?
O0 C7 C8 N1 108.31(19) . . . . ?
O0 C7 C8 N3 -64.1(3) . . . . ?
O0 C11 C12 O1 -72.4(4) . . . . ?
O2 S1 N3 C8 140.3(2) . . . . ?
O2 S1 C13 C14 54.8(2) . . . . ?
O2 S1 C13 C18 -126.7(2) . . . . ?
O3 S1 N3 C8 11.0(3) . . . . ?
O3 S1 C13 C14 -178.4(2) . . . . ?
O3 S1 C13 C18 0.2(2) . . . . ?
N1 C5 C6 C1 178.0(2) . . . . ?
N1 C5 C6 C7 -7.3(2) . . . . ?
N2 C7 C8 N1 -134.4(2) . . . . ?
N2 C7 C8 N3 53.2(4) . . . . ?
N2 C10 C11 O0 32.3(2) . . . . ?
N2 C10 C11 C12 151.1(3) . . . . ?
N2 C20 C21 C22 -179.7(2) . . . . ?
N2 C20 C25 C24 -180.0(2) . . . . ?
N3 S1 C13 C14 -55.9(2) . . . . ?
N3 S1 C13 C18 122.7(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C1 C6 C7 O0 71.7(3) . . . . ?
C1 C6 C7 N2 -47.6(3) . . . . ?
C1 C6 C7 C8 -178.2(3) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
C2 C1 C6 C7 -170.7(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 N1 179.6(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -2.6(4) . . . . ?
C4 C5 C6 C7 172.2(2) . . . . ?
C5 N1 C8 N3 175.9(2) . . . . ?
C5 N1 C8 C7 1.9(2) . . . . ?
C5 C6 C7 O0 -102.3(2) . . . . ?
C5 C6 C7 N2 138.4(2) . . . . ?
C5 C6 C7 C8 7.8(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C7 C8 N1 -5.8(2) . . . . ?
C6 C7 C8 N3 -178.2(3) . . . . ?
C7 O0 C11 C10 -38.8(2) . . . . ?
C7 O0 C11 C12 -162.1(2) . . . . ?
C7 N2 C10 C11 -15.5(2) . . . . ?
C7 N2 C20 C21 18.5(4) . . . . ?
C7 N2 C20 C25 -163.5(2) . . . . ?
C8 N1 C5 C4 -176.1(2) . . . . ?
C8 N1 C5 C6 3.3(3) . . . . ?
C9 N1 C5 C4 -1.2(3) . . . . ?
C9 N1 C5 C6 178.3(2) . . . . ?
C9 N1 C8 N3 0.8(3) . . . . ?
C9 N1 C8 C7 -173.1(2) . . . . ?
C10 N2 C7 O0 -7.7(2) . . . . ?
C10 N2 C7 C6 114.2(2) . . . . ?
C10 N2 C7 C8 -124.8(2) . . . . ?
C10 N2 C20 C21 -177.8(2) . . . . ?
C10 N2 C20 C25 0.1(4) . . . . ?
C10 C11 C12 O1 172.0(3) . . . . ?
C11 O0 C7 N2 29.0(2) . . . . ?
C11 O0 C7 C6 -96.9(2) . . . . ?
C11 O0 C7 C8 155.68(17) . . . . ?
C13 S1 N3 C8 -106.8(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C19 179.6(3) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C13 1.0(4) . . . . ?
C18 C13 C14 C15 0.2(4) . . . . ?
C19 C16 C17 C18 179.9(3) . . . . ?
C20 N2 C7 O0 157.9(2) . . . . ?
C20 N2 C7 C6 -80.3(3) . . . . ?
C20 N2 C7 C8 40.8(3) . . . . ?
C20 N2 C10 C11 178.7(2) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C20 C25 C24 -2.0(4) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C21 C22 C23 C26 178.3(3) . . . . ?
C22 C23 C24 C25 1.3(4) . . . . ?
C23 C24 C25 C20 0.2(4) . . . . ?
C25 C20 C21 C22 2.3(4) . . . . ?
C26 C23 C24 C25 -177.9(3) . . . . ?

####################################################################### 
# 
# 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_170601_sgr4_189a
_database_code_depnum_ccdc_archive 'CCDC 1574183'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2017-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N3 O3 S'
_chemical_formula_sum            'C27 H29 N3 O3 S'
_chemical_formula_weight         475.59
_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'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0863(10)
_cell_length_b                   11.6603(10)
_cell_length_c                   11.8746(10)
_cell_angle_alpha                109.645(8)
_cell_angle_beta                 100.679(7)
_cell_angle_gamma                113.710(8)
_cell_volume                     1228.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2216
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.2930
_cell_measurement_theta_min      3.0200
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89966
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7663
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.026
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -12.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -62.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000 -150.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0597918000
_diffrn_orient_matrix_UB_12      0.0610253000
_diffrn_orient_matrix_UB_13      0.0085641000
_diffrn_orient_matrix_UB_21      -0.0426316000
_diffrn_orient_matrix_UB_22      0.0027874000
_diffrn_orient_matrix_UB_23      -0.0503916000
_diffrn_orient_matrix_UB_31      -0.0165247000
_diffrn_orient_matrix_UB_32      0.0429421000
_diffrn_orient_matrix_UB_33      0.0453295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3417
_reflns_number_total             4479
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.034
_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)+(0.0564P)²+0.1419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.38094(6) 0.36017(6) 0.15521(5) 0.02105(18) Uani 1 1 d . . . . .
O1 O 0.62545(15) 0.24951(15) 0.27245(14) 0.0227(4) Uani 1 1 d . . . . .
O2 O 0.51009(16) 0.45394(17) 0.15018(16) 0.0299(4) Uani 1 1 d . . . . .
O3 O 0.36794(16) 0.39419(16) 0.27868(14) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.34204(19) -0.00633(19) 0.03434(17) 0.0212(4) Uani 1 1 d . . . . .
N2 N 0.46338(18) 0.22586(19) 0.36739(17) 0.0211(4) Uani 1 1 d . . . . .
N3 N 0.34644(19) 0.20056(19) 0.07842(17) 0.0224(4) Uani 1 1 d . . . . .
C1 C 0.5294(2) -0.0280(2) 0.3001(2) 0.0261(5) Uani 1 1 d . . . . .
H1 H 0.579567 0.032075 0.389930 0.031 Uiso 1 1 calc R . . . .
C2 C 0.5157(2) -0.1610(2) 0.2444(2) 0.0288(6) Uani 1 1 d . . . . .
H2 H 0.556832 -0.192402 0.296285 0.035 Uiso 1 1 calc R . . . .
C3 C 0.4422(2) -0.2468(2) 0.1135(2) 0.0286(6) Uani 1 1 d . . . . .
H3 H 0.435118 -0.336335 0.076598 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3785(2) -0.2064(2) 0.0343(2) 0.0268(6) Uani 1 1 d . . . . .
H4 H 0.327416 -0.266481 -0.055490 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3926(2) -0.0750(2) 0.0918(2) 0.0226(5) Uani 1 1 d . . . . .
C6 C 0.4690(2) 0.0139(2) 0.2227(2) 0.0226(5) Uani 1 1 d . . . . .
C7 C 0.4839(2) 0.1574(2) 0.2531(2) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.3840(2) 0.1265(2) 0.1204(2) 0.0201(5) Uani 1 1 d . . . . .
C9 C 0.6724(2) 0.3886(2) 0.3720(2) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.641176 0.440313 0.332539 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5931(2) 0.3586(2) 0.4594(2) 0.0217(5) Uani 1 1 d . . . . .
H10 H 0.568751 0.433541 0.495012 0.026 Uiso 1 1 calc R . . . .
C11 C 0.8322(2) 0.4646(3) 0.4284(2) 0.0329(6) Uani 1 1 d . . . . .
H11A H 0.867709 0.555780 0.501988 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.869596 0.479406 0.362871 0.049 Uiso 1 1 calc GR . . . .
H11C H 0.863097 0.407898 0.457093 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.6711(3) 0.3446(3) 0.5692(2) 0.0313(6) Uani 1 1 d . . . . .
H12A H 0.606015 0.306848 0.609608 0.047 Uiso 1 1 calc GR . . . .
H12B H 0.751194 0.437346 0.633200 0.047 Uiso 1 1 calc GR . . . .
H12C H 0.706370 0.280695 0.535475 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.3324(2) 0.1843(2) 0.3807(2) 0.0208(5) Uani 1 1 d . . . . .
C14 C 0.2071(2) 0.0668(2) 0.2826(2) 0.0244(5) Uani 1 1 d . . . . .
H14 H 0.211210 0.008466 0.206874 0.029 Uiso 1 1 calc R . . . .
C15 C 0.0773(2) 0.0347(3) 0.2951(2) 0.0283(6) Uani 1 1 d . . . . .
H15 H -0.006209 -0.044528 0.226238 0.034 Uiso 1 1 calc R . . . .
C16 C 0.0647(2) 0.1140(3) 0.4042(2) 0.0287(6) Uani 1 1 d . . . . .
C17 C 0.1914(3) 0.2255(3) 0.5042(2) 0.0294(6) Uani 1 1 d . . . . .
H17 H 0.187565 0.278674 0.582668 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3219(2) 0.2614(2) 0.4935(2) 0.0239(5) Uani 1 1 d . . . . .
H18 H 0.405274 0.339217 0.563515 0.029 Uiso 1 1 calc R . . . .
C19 C -0.0770(3) 0.0813(3) 0.4160(3) 0.0408(7) Uani 1 1 d . . . . .
H19A H -0.070366 0.091327 0.502596 0.061 Uiso 1 1 calc GR . . . .
H19B H -0.148662 -0.015481 0.351970 0.061 Uiso 1 1 calc GR . . . .
H19C H -0.104303 0.146662 0.401082 0.061 Uiso 1 1 calc GR . . . .
C20 C 0.2382(2) 0.3507(2) 0.0498(2) 0.0201(5) Uani 1 1 d . . . . .
C21 C 0.2517(2) 0.3729(2) -0.0549(2) 0.0248(5) Uani 1 1 d . . . . .
H21 H 0.337359 0.394102 -0.070346 0.030 Uiso 1 1 calc R . . . .
C22 C 0.1384(3) 0.3638(2) -0.1377(2) 0.0305(6) Uani 1 1 d . . . . .
H22 H 0.147437 0.379919 -0.209735 0.037 Uiso 1 1 calc R . . . .
C23 C 0.0122(3) 0.3319(2) -0.1175(2) 0.0300(6) Uani 1 1 d . . . . .
C24 C 0.0020(2) 0.3102(3) -0.0111(2) 0.0330(6) Uani 1 1 d . . . . .
H24 H -0.083891 0.288337 0.004028 0.040 Uiso 1 1 calc R . . . .
C25 C 0.1136(2) 0.3195(2) 0.0738(2) 0.0279(6) Uani 1 1 d . . . . .
H25 H 0.105242 0.304907 0.146724 0.033 Uiso 1 1 calc R . . . .
C26 C -0.1126(3) 0.3164(3) -0.2113(3) 0.0468(8) Uani 1 1 d . . . . .
H26A H -0.079239 0.364074 -0.262453 0.070 Uiso 1 1 calc GR . . . .
H26B H -0.159441 0.358664 -0.163689 0.070 Uiso 1 1 calc GR . . . .
H26C H -0.180040 0.216238 -0.268633 0.070 Uiso 1 1 calc GR . . . .
C27 C 0.2512(2) -0.0693(2) -0.0999(2) 0.0276(6) Uani 1 1 d . . . . .
H27A H 0.154422 -0.091343 -0.105828 0.041 Uiso 1 1 calc GR . . . .
H27B H 0.250659 -0.155907 -0.149368 0.041 Uiso 1 1 calc GR . . . .
H27C H 0.287403 -0.002924 -0.134895 0.041 Uiso 1 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 O2 1.4373(17) . ?
S1 O3 1.4356(16) . ?
S1 N3 1.6121(18) . ?
S1 C20 1.765(2) . ?
O1 C7 1.419(3) . ?
O1 C9 1.450(3) . ?
N1 C5 1.418(3) . ?
N1 C8 1.357(3) . ?
N1 C27 1.455(3) . ?
N2 C7 1.436(3) . ?
N2 C10 1.465(3) . ?
N2 C13 1.392(3) . ?
N3 C8 1.292(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(3) . ?
C1 C6 1.368(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.519(3) . ?
C7 C8 1.578(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(3) . ?
C9 C11 1.506(3) . ?
C10 H10 1.0000 . ?
C10 C12 1.521(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.400(3) . ?
C13 C18 1.396(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 C17 1.395(3) . ?
C16 C19 1.506(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.375(3) . ?
C20 C25 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 C24 1.385(4) . ?
C23 C26 1.510(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
O2 S1 N3 108.96(10) . . ?
O2 S1 C20 107.90(10) . . ?
O3 S1 O2 117.31(10) . . ?
O3 S1 N3 114.19(10) . . ?
O3 S1 C20 108.11(10) . . ?
N3 S1 C20 98.52(9) . . ?
C7 O1 C9 108.83(15) . . ?
C5 N1 C27 125.29(18) . . ?
C8 N1 C5 112.21(18) . . ?
C8 N1 C27 122.47(18) . . ?
C7 N2 C10 111.01(17) . . ?
C13 N2 C7 124.43(18) . . ?
C13 N2 C10 123.78(17) . . ?
C8 N3 S1 129.50(16) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.6(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.9(2) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 N1 128.8(2) . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 N1 109.43(18) . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 C7 129.6(2) . . ?
C5 C6 C7 109.22(19) . . ?
O1 C7 N2 105.10(16) . . ?
O1 C7 C6 107.27(16) . . ?
O1 C7 C8 107.64(17) . . ?
N2 C7 C6 117.35(19) . . ?
N2 C7 C8 117.68(16) . . ?
C6 C7 C8 101.20(16) . . ?
N1 C8 C7 107.32(17) . . ?
N3 C8 N1 117.77(19) . . ?
N3 C8 C7 134.66(19) . . ?
O1 C9 H9 109.4 . . ?
O1 C9 C10 103.45(17) . . ?
O1 C9 C11 107.05(17) . . ?
C10 C9 H9 109.4 . . ?
C11 C9 H9 109.4 . . ?
C11 C9 C10 117.89(19) . . ?
N2 C10 C9 101.24(17) . . ?
N2 C10 H10 109.5 . . ?
N2 C10 C12 111.89(19) . . ?
C9 C10 H10 109.5 . . ?
C9 C10 C12 114.86(19) . . ?
C12 C10 H10 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 122.1(2) . . ?
N2 C13 C18 120.4(2) . . ?
C18 C13 C14 117.5(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 118.8 . . ?
C14 C15 C16 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 116.2(2) . . ?
C15 C16 C19 122.3(2) . . ?
C17 C16 C19 121.6(2) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.6(2) . . ?
C18 C17 H17 118.7 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 S1 119.54(17) . . ?
C21 C20 C25 121.3(2) . . ?
C25 C20 S1 119.19(18) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.0(2) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C24 118.2(2) . . ?
C22 C23 C26 120.9(3) . . ?
C24 C23 C26 120.8(2) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.7(2) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 H25 120.8 . . ?
C24 C25 C20 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
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 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_161124_sgr4_110b
_database_code_depnum_ccdc_archive 'CCDC 1574181'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2016-11-24
_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 H29 N3 O3 S'
_chemical_formula_sum            'C26 H29 N3 O3 S'
_chemical_formula_weight         463.58
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.1615(7)
_cell_length_b                   11.8908(7)
_cell_length_c                   16.8761(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.719(7)
_cell_angle_gamma                90.00
_cell_volume                     2412.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2877
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2900
_cell_measurement_theta_min      3.1704
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88214
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10119
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_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      -0.0558246000
_diffrn_orient_matrix_UB_12      0.0021021000
_diffrn_orient_matrix_UB_13      0.0074355000
_diffrn_orient_matrix_UB_21      -0.0041766000
_diffrn_orient_matrix_UB_22      -0.0592553000
_diffrn_orient_matrix_UB_23      -0.0046324000
_diffrn_orient_matrix_UB_31      0.0186337000
_diffrn_orient_matrix_UB_32      -0.0070121000
_diffrn_orient_matrix_UB_33      0.0415699000
_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                3088
_reflns_number_total             4406
_reflns_odcompleteness_completeness 99.40
_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         0.175
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.039
_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)+(0.0627P)²+0.4146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1422
_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. Restrained distances
 H3-O3
 0.85 with sigma of 0.02
3.a Riding coordinates:
 N2(H2)
3.b Ternary CH refined with riding coordinates:
 C17(H17)
3.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C20(H20), C21(H21), C23(H23), C24(H24)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), 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 0.42435(5) 0.42517(6) 0.22197(4) 0.0695(2) Uani 1 d . . .
O1 O 0.43264(16) 0.54433(15) 0.21569(12) 0.0841(6) Uani 1 d . . .
O2 O 0.50264(15) 0.35590(18) 0.19092(13) 0.0962(7) Uani 1 d . . .
O3 O 0.42877(14) 0.17062(15) 0.36963(13) 0.0754(5) Uani 1 d . . D
H3 H 0.461(2) 0.123(2) 0.3427(17) 0.111(12) Uiso 1 d . . D
N1 N 0.41091(16) 0.54771(16) 0.40463(13) 0.0616(5) Uani 1 d . . .
N2 N 0.43652(14) 0.39369(17) 0.31654(13) 0.0630(5) Uani 1 d . . .
H2 H 0.4314 0.3221 0.3221 0.076 Uiso 1 d . . R
N3 N 0.22901(13) 0.30736(14) 0.37924(10) 0.0463(4) Uani 1 d . . .
C1 C 0.1790(2) 0.5004(2) 0.50558(15) 0.0691(7) Uani 1 d . . .
H1 H 0.1227 0.4470 0.5037 0.083 Uiso 1 calc . . R
C2 C 0.1850(3) 0.5878(3) 0.55809(17) 0.0914(9) Uani 1 d . . .
H2A H 0.1331 0.5930 0.5932 0.110 Uiso 1 calc . . R
C3 C 0.2659(4) 0.6684(3) 0.56031(19) 0.1025(12) Uani 1 d . . .
H3A H 0.2674 0.7267 0.5972 0.123 Uiso 1 calc . . R
C4 C 0.3442(3) 0.6663(2) 0.51049(18) 0.0830(9) Uani 1 d . . .
H4 H 0.3978 0.7224 0.5118 0.100 Uiso 1 calc . . R
C5 C 0.3402(2) 0.5761(2) 0.45755(14) 0.0615(6) Uani 1 d . . .
C6 C 0.25849(19) 0.49229(18) 0.45487(13) 0.0529(6) Uani 1 d . . .
C7 C 0.28154(16) 0.41213(17) 0.39691(13) 0.0472(5) Uani 1 d . . .
C8 C 0.37386(17) 0.44866(18) 0.36808(14) 0.0530(6) Uani 1 d . . .
C9 C 0.11867(15) 0.30449(17) 0.34034(12) 0.0447(5) Uani 1 d . . .
C10 C 0.05831(17) 0.20539(19) 0.33229(14) 0.0555(6) Uani 1 d . . .
H10 H 0.0906 0.1392 0.3541 0.067 Uiso 1 calc . . R
C11 C -0.05017(19) 0.2038(2) 0.29183(15) 0.0634(6) Uani 1 d . . .
H11 H -0.0890 0.1362 0.2874 0.076 Uiso 1 calc . . R
C12 C -0.10136(18) 0.2981(3) 0.25853(14) 0.0650(7) Uani 1 d . . .
C13 C -0.04060(19) 0.3969(2) 0.26641(14) 0.0640(6) Uani 1 d . . .
H13 H -0.0733 0.4627 0.2443 0.077 Uiso 1 calc . . R
C14 C 0.06731(17) 0.4004(2) 0.30616(13) 0.0520(5) Uani 1 d . . .
H14 H 0.1060 0.4681 0.3100 0.062 Uiso 1 calc . . R
C15 C -0.2205(2) 0.2943(3) 0.21558(19) 0.1019(11) Uani 1 d . . .
H15A H -0.2648 0.3472 0.2399 0.153 Uiso 1 calc . . GR
H15B H -0.2501 0.2200 0.2196 0.153 Uiso 1 calc . . GR
H15C H -0.2220 0.3133 0.1601 0.153 Uiso 1 calc . . GR
C16 C 0.27145(17) 0.21333(18) 0.43029(13) 0.0506(5) Uani 1 d . . .
H16A H 0.2098 0.1796 0.4521 0.061 Uiso 1 calc . . R
H16B H 0.3232 0.2424 0.4750 0.061 Uiso 1 calc . . R
C17 C 0.32915(17) 0.12254(19) 0.38971(14) 0.0545(6) Uani 1 d . . .
H17 H 0.2812 0.0995 0.3404 0.065 Uiso 1 calc . . R
C18 C 0.3542(2) 0.0219(2) 0.44317(17) 0.0769(8) Uani 1 d . . .
H18A H 0.3954 -0.0322 0.4173 0.115 Uiso 1 calc . . GR
H18B H 0.2857 -0.0113 0.4534 0.115 Uiso 1 calc . . GR
H18C H 0.3974 0.0448 0.4929 0.115 Uiso 1 calc . . GR
C19 C 0.2914(2) 0.3873(2) 0.17602(15) 0.0639(6) Uani 1 d . . .
C20 C 0.2595(2) 0.2759(2) 0.17663(16) 0.0739(7) Uani 1 d . . .
H20 H 0.3075 0.2220 0.2025 0.089 Uiso 1 calc . . R
C21 C 0.1551(3) 0.2458(3) 0.13824(17) 0.0858(9) Uani 1 d . . .
H21 H 0.1329 0.1711 0.1395 0.103 Uiso 1 calc . . R
C22 C 0.0840(3) 0.3222(4) 0.09869(18) 0.0916(10) Uani 1 d . . .
C23 C 0.1169(3) 0.4327(4) 0.09872(18) 0.0965(10) Uani 1 d . . .
H23 H 0.0685 0.4860 0.0726 0.116 Uiso 1 calc . . R
C24 C 0.2200(3) 0.4662(3) 0.13664(17) 0.0802(8) Uani 1 d . . .
H24 H 0.2412 0.5413 0.1357 0.096 Uiso 1 calc . . R
C25 C -0.0290(3) 0.2881(4) 0.0561(2) 0.1402(17) Uani 1 d . . .
H25A H -0.0242 0.2713 0.0011 0.210 Uiso 1 calc . . GR
H25B H -0.0806 0.3486 0.0585 0.210 Uiso 1 calc . . GR
H25C H -0.0541 0.2227 0.0815 0.210 Uiso 1 calc . . GR
C26 C 0.5130(2) 0.6063(2) 0.39584(19) 0.0832(9) Uani 1 d . . .
H26A H 0.5561 0.5611 0.3647 0.125 Uiso 1 calc . . GR
H26B H 0.5552 0.6198 0.4478 0.125 Uiso 1 calc . . GR
H26C H 0.4954 0.6768 0.3692 0.125 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 1.4256(19) . ?
S1 O2 1.4179(18) . ?
S1 N2 1.624(2) . ?
S1 C19 1.743(3) . ?
O3 H3 0.854(18) . ?
O3 C17 1.426(3) . ?
N1 C5 1.373(3) . ?
N1 C8 1.373(3) . ?
N1 C26 1.451(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.402(3) . ?
N3 C7 1.411(3) . ?
N3 C9 1.402(2) . ?
N3 C16 1.457(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(4) . ?
C1 C6 1.388(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3A 0.9300 . ?
C3 C4 1.363(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(4) . ?
C5 C6 1.403(3) . ?
C6 C7 1.424(3) . ?
C7 C8 1.361(3) . ?
C9 C10 1.384(3) . ?
C9 C14 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(4) . ?
C12 C13 1.384(4) . ?
C12 C15 1.520(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.507(3) . ?
C17 H17 0.9800 . ?
C17 C18 1.502(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.380(4) . ?
C19 C24 1.379(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.358(5) . ?
C22 C23 1.373(5) . ?
C22 C25 1.506(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
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 107.77(12) . . ?
O1 S1 C19 107.16(13) . . ?
O2 S1 O1 119.40(12) . . ?
O2 S1 N2 105.25(12) . . ?
O2 S1 C19 108.35(12) . . ?
N2 S1 C19 108.53(10) . . ?
C17 O3 H3 109(2) . . ?
C5 N1 C8 107.92(19) . . ?
C5 N1 C26 125.4(2) . . ?
C8 N1 C26 126.4(2) . . ?
S1 N2 H2 109.8 . . ?
C8 N2 S1 121.68(16) . . ?
C8 N2 H2 109.8 . . ?
C7 N3 C16 116.36(16) . . ?
C9 N3 C7 119.40(17) . . ?
C9 N3 C16 119.09(16) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.7(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2A 119.3 . . ?
C1 C2 C3 121.3(3) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3A 118.8 . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 H3A 118.8 . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.7(3) . . ?
C5 C4 H4 121.6 . . ?
N1 C5 C4 129.9(3) . . ?
N1 C5 C6 108.4(2) . . ?
C4 C5 C6 121.6(3) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 134.3(2) . . ?
C5 C6 C7 106.6(2) . . ?
N3 C7 C6 127.32(19) . . ?
C8 C7 N3 125.30(19) . . ?
C8 C7 C6 106.92(19) . . ?
N1 C8 N2 120.42(19) . . ?
C7 C8 N1 110.2(2) . . ?
C7 C8 N2 128.9(2) . . ?
C10 C9 N3 121.49(19) . . ?
C14 C9 N3 120.99(18) . . ?
C14 C9 C10 117.49(18) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.1(2) . . ?
C11 C12 C15 121.1(3) . . ?
C13 C12 C15 121.8(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 108.4 . . ?
N3 C16 H16B 108.4 . . ?
N3 C16 C17 115.37(17) . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
O3 C17 C16 106.95(18) . . ?
O3 C17 H17 109.1 . . ?
O3 C17 C18 111.11(19) . . ?
C16 C17 H17 109.1 . . ?
C18 C17 C16 111.3(2) . . ?
C18 C17 H17 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 S1 119.2(2) . . ?
C24 C19 S1 120.8(2) . . ?
C24 C19 C20 119.9(3) . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.0(3) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.9(3) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 C23 118.4(3) . . ?
C21 C22 C25 121.4(4) . . ?
C23 C22 C25 120.1(4) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.5(3) . . ?
C24 C23 H23 119.3 . . ?
C19 C24 H24 120.4 . . ?
C23 C24 C19 119.3(3) . . ?
C23 C24 H24 120.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 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 C8 N1 -86.3(2) . . . . ?
S1 N2 C8 C7 102.0(3) . . . . ?
S1 C19 C20 C21 -178.26(18) . . . . ?
S1 C19 C24 C23 177.9(2) . . . . ?
O1 S1 N2 C8 49.50(19) . . . . ?
O1 S1 C19 C20 -177.27(19) . . . . ?
O1 S1 C19 C24 5.3(2) . . . . ?
O2 S1 N2 C8 177.94(17) . . . . ?
O2 S1 C19 C20 52.7(2) . . . . ?
O2 S1 C19 C24 -124.8(2) . . . . ?
N1 C5 C6 C1 177.8(2) . . . . ?
N1 C5 C6 C7 -0.9(2) . . . . ?
N2 S1 C19 C20 -61.1(2) . . . . ?
N2 S1 C19 C24 121.4(2) . . . . ?
N3 C7 C8 N1 -172.61(19) . . . . ?
N3 C7 C8 N2 -0.3(4) . . . . ?
N3 C9 C10 C11 -178.47(19) . . . . ?
N3 C9 C14 C13 178.63(19) . . . . ?
N3 C16 C17 O3 67.2(2) . . . . ?
N3 C16 C17 C18 -171.30(19) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C6 C7 N3 -5.4(4) . . . . ?
C1 C6 C7 C8 -177.9(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C1 C6 C7 176.3(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 N1 -175.4(3) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -177.9(2) . . . . ?
C5 N1 C8 N2 -173.7(2) . . . . ?
C5 N1 C8 C7 -0.6(3) . . . . ?
C5 C6 C7 N3 172.99(19) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C6 C7 C8 N1 0.1(2) . . . . ?
C6 C7 C8 N2 172.4(2) . . . . ?
C7 N3 C9 C10 -170.31(19) . . . . ?
C7 N3 C9 C14 11.9(3) . . . . ?
C7 N3 C16 C17 -112.6(2) . . . . ?
C8 N1 C5 C4 177.6(2) . . . . ?
C8 N1 C5 C6 0.9(2) . . . . ?
C9 N3 C7 C6 70.3(3) . . . . ?
C9 N3 C7 C8 -118.5(2) . . . . ?
C9 N3 C16 C17 92.9(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 C15 -179.2(2) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C15 C12 C13 C14 179.3(2) . . . . ?
C16 N3 C7 C6 -84.1(2) . . . . ?
C16 N3 C7 C8 87.0(3) . . . . ?
C16 N3 C9 C10 -16.6(3) . . . . ?
C16 N3 C9 C14 165.59(18) . . . . ?
C19 S1 N2 C8 -66.2(2) . . . . ?
C19 C20 C21 C22 1.3(4) . . . . ?
C20 C19 C24 C23 0.4(4) . . . . ?
C20 C21 C22 C23 -1.4(4) . . . . ?
C20 C21 C22 C25 179.1(3) . . . . ?
C21 C22 C23 C24 1.0(5) . . . . ?
C22 C23 C24 C19 -0.5(4) . . . . ?
C24 C19 C20 C21 -0.8(4) . . . . ?
C25 C22 C23 C24 -179.5(3) . . . . ?
C26 N1 C5 C4 3.6(4) . . . . ?
C26 N1 C5 C6 -173.1(2) . . . . ?
C26 N1 C8 N2 0.2(3) . . . . ?
C26 N1 C8 C7 173.3(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_170118_sgr4_145a
_database_code_depnum_ccdc_archive 'CCDC 1574182'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2017-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.5082(14)
_cell_length_b                   9.5276(15)
_cell_length_c                   18.393(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1666.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4801
_cell_measurement_theta_min      3.2167
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76193
_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_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3614
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.223
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00   21.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965  -77.0000   30.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0085617000
_diffrn_orient_matrix_UB_12      -0.0739435000
_diffrn_orient_matrix_UB_13      -0.0013361000
_diffrn_orient_matrix_UB_21      0.0170170000
_diffrn_orient_matrix_UB_22      -0.0006858000
_diffrn_orient_matrix_UB_23      0.0375342000
_diffrn_orient_matrix_UB_31      -0.0721307000
_diffrn_orient_matrix_UB_32      -0.0087593000
_diffrn_orient_matrix_UB_33      0.0087039000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.686
_reflns_Friedel_fraction_max     0.685
_reflns_number_gt                1919
_reflns_number_total             2607
_reflns_odcompleteness_completeness 97.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.097
_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)+(0.0508P)²+0.0351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1409
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.5336(4) 0.6576(4) 0.1636(2) 0.0944(12) Uani 1 1 d . . . . .
O2 O 0.4375(3) 0.7836(4) 0.02299(16) 0.0784(10) Uani 1 1 d . . . . .
N1 N 0.5890(4) 0.8904(5) 0.1711(2) 0.0691(10) Uani 1 1 d . . . . .
N2 N 0.2615(3) 0.7829(4) 0.10700(17) 0.0546(9) Uani 1 1 d . . . . .
C1 C 0.3527(6) 1.0949(6) 0.0648(3) 0.0735(13) Uani 1 1 d . . . . .
H1 H 0.274471 1.077213 0.035817 0.088 Uiso 1 1 calc R . . . .
C2 C 0.3996(7) 1.2330(6) 0.0772(3) 0.0898(16) Uani 1 1 d . . . . .
H2 H 0.353444 1.308144 0.055475 0.108 Uiso 1 1 calc R . . . .
C3 C 0.5133(7) 1.2567(6) 0.1214(3) 0.0904(18) Uani 1 1 d . . . . .
H3 H 0.543411 1.348435 0.128700 0.108 Uiso 1 1 calc R . . . .
C4 C 0.5841(6) 1.1496(6) 0.1550(3) 0.0822(15) Uani 1 1 d . . . . .
H4 H 0.659920 1.167300 0.185578 0.099 Uiso 1 1 calc R . . . .
C5 C 0.5388(5) 1.0154(5) 0.1419(2) 0.0605(11) Uani 1 1 d . . . . .
C6 C 0.4245(5) 0.9894(5) 0.0961(2) 0.0571(11) Uani 1 1 d . . . . .
C7 C 0.4026(4) 0.8353(4) 0.0932(2) 0.0540(10) Uani 1 1 d . . . . .
C8 C 0.5151(5) 0.7793(6) 0.1472(3) 0.0674(12) Uani 1 1 d . . . . .
C9 C 0.3293(5) 0.6935(5) -0.0039(2) 0.0662(12) Uani 1 1 d . . . . .
H9 H 0.270618 0.745670 -0.038380 0.079 Uiso 1 1 calc R . . . .
C10 C 0.2435(5) 0.6582(5) 0.0625(2) 0.0586(11) Uani 1 1 d . . . . .
H10A H 0.145436 0.643420 0.050179 0.070 Uiso 1 1 calc R . . . .
H10B H 0.279598 0.575382 0.086803 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7024(6) 0.8805(7) 0.2239(3) 0.0979(19) Uani 1 1 d . . . . .
H11A H 0.787864 0.914976 0.202660 0.147 Uiso 1 1 calc GR . . . .
H11B H 0.714720 0.784234 0.237990 0.147 Uiso 1 1 calc GR . . . .
H11C H 0.679323 0.935622 0.265921 0.147 Uiso 1 1 calc GR . . . .
C12 C 0.3957(7) 0.5709(5) -0.0423(3) 0.0898(17) Uani 1 1 d . . . . .
H12A H 0.450135 0.604152 -0.082708 0.135 Uiso 1 1 calc GR . . . .
H12B H 0.323559 0.508748 -0.059456 0.135 Uiso 1 1 calc GR . . . .
H12C H 0.455943 0.521468 -0.009080 0.135 Uiso 1 1 calc GR . . . .
C13 C 0.2016(4) 0.7914(5) 0.1762(2) 0.0505(9) Uani 1 1 d . . . . .
C14 C 0.0978(4) 0.6959(5) 0.1974(2) 0.0601(11) Uani 1 1 d . . . . .
H14 H 0.071694 0.624039 0.165932 0.072 Uiso 1 1 calc R . . . .
C15 C 0.0341(5) 0.7068(5) 0.2638(3) 0.0671(12) Uani 1 1 d . . . . .
H15 H -0.034272 0.641257 0.276292 0.080 Uiso 1 1 calc R . . . .
C16 C 0.0668(5) 0.8104(5) 0.3128(2) 0.0607(12) Uani 1 1 d . . . . .
C17 C 0.1686(5) 0.9034(5) 0.2923(2) 0.0597(11) Uani 1 1 d . . . . .
H17 H 0.193793 0.974448 0.324464 0.072 Uiso 1 1 calc R . . . .
C18 C 0.2363(4) 0.8961(4) 0.2253(2) 0.0557(11) Uani 1 1 d . . . . .
H18 H 0.304978 0.961707 0.213511 0.067 Uiso 1 1 calc R . . . .
C19 C -0.0050(7) 0.8195(6) 0.3856(3) 0.0954(18) Uani 1 1 d . . . . .
H19A H 0.001639 0.730619 0.409925 0.143 Uiso 1 1 calc GR . . . .
H19B H -0.102169 0.843411 0.378762 0.143 Uiso 1 1 calc GR . . . .
H19C H 0.039818 0.890433 0.414592 0.143 Uiso 1 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
O1 C8 1.211(5) . ?
O2 C7 1.421(5) . ?
O2 C9 1.428(5) . ?
N1 C5 1.390(6) . ?
N1 C8 1.344(6) . ?
N1 C11 1.454(6) . ?
N2 C7 1.453(5) . ?
N2 C10 1.453(5) . ?
N2 C13 1.396(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.408(7) . ?
C1 C6 1.345(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(6) . ?
C5 C6 1.397(6) . ?
C6 C7 1.484(6) . ?
C7 C8 1.554(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.506(6) . ?
C9 C12 1.504(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.398(6) . ?
C13 C18 1.386(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(6) . ?
C16 C17 1.365(6) . ?
C16 C19 1.506(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(6) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C7 O2 C9 110.8(3) . . ?
C5 N1 C11 124.6(4) . . ?
C8 N1 C5 111.6(4) . . ?
C8 N1 C11 123.7(5) . . ?
C7 N2 C10 106.9(3) . . ?
C13 N2 C7 121.1(3) . . ?
C13 N2 C10 120.8(3) . . ?
C2 C1 H1 121.1 . . ?
C6 C1 H1 121.1 . . ?
C6 C1 C2 117.9(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.5(5) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C6 110.4(4) . . ?
C4 C5 N1 128.6(5) . . ?
C4 C5 C6 121.0(5) . . ?
C1 C6 C5 121.4(4) . . ?
C1 C6 C7 130.7(4) . . ?
C5 C6 C7 107.8(4) . . ?
O2 C7 N2 104.8(3) . . ?
O2 C7 C6 110.0(3) . . ?
O2 C7 C8 107.5(3) . . ?
N2 C7 C6 117.6(4) . . ?
N2 C7 C8 114.0(3) . . ?
C6 C7 C8 102.7(4) . . ?
O1 C8 N1 126.6(5) . . ?
O1 C8 C7 126.0(5) . . ?
N1 C8 C7 107.4(4) . . ?
O2 C9 H9 109.2 . . ?
O2 C9 C10 104.1(3) . . ?
O2 C9 C12 109.1(4) . . ?
C10 C9 H9 109.2 . . ?
C12 C9 H9 109.2 . . ?
C12 C9 C10 115.7(4) . . ?
N2 C10 C9 102.1(3) . . ?
N2 C10 H10A 111.3 . . ?
N2 C10 H10B 111.3 . . ?
C9 C10 H10A 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 120.3(4) . . ?
C18 C13 N2 122.6(4) . . ?
C18 C13 C14 117.0(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 118.6 . . ?
C14 C15 C16 122.7(4) . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C19 121.5(4) . . ?
C17 C16 C15 116.5(4) . . ?
C17 C16 C19 121.9(5) . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.6(4) . . ?
C18 C17 H17 118.7 . . ?
C13 C18 C17 120.2(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
