# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

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

data_dm-anm-3-br-ome_mo
_database_code_depnum_ccdc_archive 'CCDC 1496537'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H18 Br N O5 S'
_chemical_formula_sum            'C20 H18 Br N O5 S'
_chemical_formula_weight         464.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 Br1 N1 O5 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'
Br Br -0.2901 2.4595 '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                   7.88851(18)
_cell_length_b                   8.9545(2)
_cell_length_c                   14.9033(3)
_cell_angle_alpha                92.1745(19)
_cell_angle_beta                 99.8465(19)
_cell_angle_gamma                107.839(2)
_cell_volume                     982.76(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7103
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1930
_cell_measurement_theta_min      2.3910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.198
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.880
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7447
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00  36.00  360
  2  ω    -78.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  194
  3  ω    -71.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  180
  4  ω    -33.50  17.50   0.50    8.00    --  -20.00 -72.00 -36.00  102
  5  ω     -2.00   8.50   0.50    8.00    --  -20.00  72.00-180.00   21
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338098000
_diffrn_orient_matrix_UB_12      0.0610916000
_diffrn_orient_matrix_UB_13      -0.0157336000
_diffrn_orient_matrix_UB_21      -0.0338774000
_diffrn_orient_matrix_UB_22      -0.0424693000
_diffrn_orient_matrix_UB_23      -0.0438982000
_diffrn_orient_matrix_UB_31      -0.0835032000
_diffrn_orient_matrix_UB_32      -0.0381227000
_diffrn_orient_matrix_UB_33      0.0134403000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3208
_reflns_number_total             3392
_reflns_odcompleteness_completeness 88.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.04
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0322P)²+0.5771P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0675
_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 Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00D), C00K(H00E,H00G), C00L(H00I,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00J),
 C00P(H00P), C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00N(H00L,H00M,H00N)
;
_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
Br01 Br 0.81147(3) 0.25093(3) 0.59089(2) 0.03475(10) Uani 1 1 d . . . . .
S002 S 0.78755(7) 0.71212(6) 0.17574(3) 0.02683(13) Uani 1 1 d . . . . .
O003 O -0.28851(18) 0.12858(16) 0.27938(9) 0.0278(3) Uani 1 1 d . . . . .
O004 O -0.21076(19) -0.01256(17) 0.39051(10) 0.0333(3) Uani 1 1 d . . . . .
O005 O 0.9551(2) 0.82202(17) 0.22038(10) 0.0348(4) Uani 1 1 d . . . . .
O006 O 0.8248(2) 0.61266(17) 0.09331(10) 0.0347(4) Uani 1 1 d . . . . .
O007 O 0.6441(2) 0.7704(2) 0.14065(12) 0.0437(4) Uani 1 1 d . . . . .
C008 C 0.5967(3) 0.4738(2) 0.38362(13) 0.0236(4) Uani 1 1 d . . . . .
C009 C 0.1529(3) 0.1766(2) 0.40652(13) 0.0240(4) Uani 1 1 d . . . . .
H009 H 0.1198 0.0944 0.4449 0.029 Uiso 1 1 calc R . . . .
C00A C 0.6502(3) 0.3052(2) 0.49774(13) 0.0242(4) Uani 1 1 d . . . . .
C00B C 0.4678(3) 0.2222(2) 0.48442(13) 0.0231(4) Uani 1 1 d . . . . .
H00B H 0.4253 0.1364 0.5191 0.028 Uiso 1 1 calc R . . . .
C00C C 0.4128(3) 0.3924(2) 0.36980(13) 0.0245(4) Uani 1 1 d . . . . .
H00C H 0.3307 0.4233 0.3259 0.029 Uiso 1 1 calc R . . . .
C00D C 0.3466(3) 0.2652(2) 0.41976(13) 0.0228(4) Uani 1 1 d . . . . .
C00E C -0.1677(3) 0.0936(2) 0.34320(13) 0.0249(4) Uani 1 1 d . . . . .
C00F C 0.7175(3) 0.4297(2) 0.44808(13) 0.0249(4) Uani 1 1 d . . . . .
H00F H 0.8440 0.4842 0.4578 0.030 Uiso 1 1 calc R . . . .
C00G C -0.4756(3) 0.0282(3) 0.27271(15) 0.0305(5) Uani 1 1 d . . . . .
H00A H -0.5143 0.0362 0.3320 0.037 Uiso 1 1 calc R . . . .
H00D H -0.4860 -0.0831 0.2571 0.037 Uiso 1 1 calc R . . . .
C00H C 0.0184(3) 0.1975(2) 0.34727(14) 0.0264(4) Uani 1 1 d . . . . .
H00H H 0.0423 0.2791 0.3077 0.032 Uiso 1 1 calc R . . . .
N00I N 1.2181(4) 0.5357(3) 0.18840(17) 0.0620(7) Uani 1 1 d . . . . .
C00J C 0.8898(3) 0.7762(3) -0.02924(15) 0.0359(5) Uani 1 1 d . . . . .
H00J H 0.7686 0.7790 -0.0410 0.043 Uiso 1 1 calc R . . . .
C00K C 0.7134(3) 0.5541(2) 0.24191(15) 0.0307(5) Uani 1 1 d . . . . .
H00E H 0.6059 0.4725 0.2055 0.037 Uiso 1 1 calc R . . . .
H00G H 0.8106 0.5059 0.2584 0.037 Uiso 1 1 calc R . . . .
C00L C 0.6647(3) 0.6108(2) 0.32869(14) 0.0271(4) Uani 1 1 d . . . . .
H00I H 0.7730 0.6902 0.3660 0.033 Uiso 1 1 calc R . . . .
H00K H 0.5697 0.6614 0.3124 0.033 Uiso 1 1 calc R . . . .
C00M C 0.9470(3) 0.6976(2) 0.04049(14) 0.0276(4) Uani 1 1 d . . . . .
C00N C -0.5929(3) 0.0815(3) 0.19987(16) 0.0379(5) Uani 1 1 d . . . . .
H00L H -0.5562 0.0699 0.1411 0.057 Uiso 1 1 calc GR . . . .
H00M H -0.5796 0.1924 0.2152 0.057 Uiso 1 1 calc GR . . . .
H00N H -0.7199 0.0173 0.1955 0.057 Uiso 1 1 calc GR . . . .
C00O C 1.1767(3) 0.6061(3) 0.13139(16) 0.0396(5) Uani 1 1 d . . . . .
C00P C 1.2441(3) 0.7677(3) 0.00412(16) 0.0375(5) Uani 1 1 d . . . . .
H00P H 1.3652 0.7647 0.0152 0.045 Uiso 1 1 calc R . . . .
C00Q C 1.1227(3) 0.6914(2) 0.05864(14) 0.0300(5) Uani 1 1 d . . . . .
C00R C 1.1866(3) 0.8470(3) -0.06569(16) 0.0393(5) Uani 1 1 d . . . . .
H00R H 1.2688 0.8993 -0.1028 0.047 Uiso 1 1 calc R . . . .
C00S C 1.0123(3) 0.8516(3) -0.08233(16) 0.0412(6) Uani 1 1 d . . . . .
H00S H 0.9749 0.9072 -0.1309 0.049 Uiso 1 1 calc R . . . .


_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
Br01 C00A 1.899(2) . ?
S002 O005 1.4179(16) . ?
S002 O006 1.6089(15) . ?
S002 O007 1.4165(17) . ?
S002 C00K 1.7643(19) . ?
O003 C00E 1.344(2) . ?
O003 C00G 1.458(2) . ?
O004 C00E 1.205(2) . ?
O006 C00M 1.409(2) . ?
C008 C00C 1.384(3) . ?
C008 C00F 1.391(3) . ?
C008 C00L 1.512(3) . ?
C009 H009 0.9500 . ?
C009 C00D 1.465(3) . ?
C009 C00H 1.324(3) . ?
C00A C00B 1.378(3) . ?
C00A C00F 1.380(3) . ?
C00B H00B 0.9500 . ?
C00B C00D 1.389(3) . ?
C00C H00C 0.9500 . ?
C00C C00D 1.399(3) . ?
C00E C00H 1.467(3) . ?
C00F H00F 0.9500 . ?
C00G H00A 0.9900 . ?
C00G H00D 0.9900 . ?
C00G C00N 1.493(3) . ?
C00H H00H 0.9500 . ?
N00I C00O 1.139(3) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.367(3) . ?
C00J C00S 1.385(3) . ?
C00K H00E 0.9900 . ?
C00K H00G 0.9900 . ?
C00K C00L 1.522(3) . ?
C00L H00I 0.9900 . ?
C00L H00K 0.9900 . ?
C00M C00Q 1.385(3) . ?
C00N H00L 0.9800 . ?
C00N H00M 0.9800 . ?
C00N H00N 0.9800 . ?
C00O C00Q 1.430(3) . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.397(3) . ?
C00P C00R 1.373(3) . ?
C00R H00R 0.9500 . ?
C00R C00S 1.369(3) . ?
C00S H00S 0.9500 . ?

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
O005 S002 O006 108.43(9) . . ?
O005 S002 C00K 111.52(10) . . ?
O006 S002 C00K 97.30(9) . . ?
O007 S002 O005 118.14(11) . . ?
O007 S002 O006 108.28(10) . . ?
O007 S002 C00K 111.04(10) . . ?
C00E O003 C00G 114.47(15) . . ?
C00M O006 S002 116.70(13) . . ?
C00C C008 C00F 119.90(17) . . ?
C00C C008 C00L 119.69(18) . . ?
C00F C008 C00L 120.41(17) . . ?
C00D C009 H009 116.2 . . ?
C00H C009 H009 116.2 . . ?
C00H C009 C00D 127.61(17) . . ?
C00B C00A Br01 118.50(14) . . ?
C00B C00A C00F 122.04(18) . . ?
C00F C00A Br01 119.41(15) . . ?
C00A C00B H00B 120.3 . . ?
C00A C00B C00D 119.40(17) . . ?
C00D C00B H00B 120.3 . . ?
C008 C00C H00C 119.6 . . ?
C008 C00C C00D 120.75(18) . . ?
C00D C00C H00C 119.6 . . ?
C00B C00D C009 118.89(16) . . ?
C00B C00D C00C 119.09(17) . . ?
C00C C00D C009 122.02(18) . . ?
O003 C00E C00H 112.47(16) . . ?
O004 C00E O003 122.60(18) . . ?
O004 C00E C00H 124.93(19) . . ?
C008 C00F H00F 120.6 . . ?
C00A C00F C008 118.82(17) . . ?
C00A C00F H00F 120.6 . . ?
O003 C00G H00A 110.1 . . ?
O003 C00G H00D 110.1 . . ?
O003 C00G C00N 108.23(17) . . ?
H00A C00G H00D 108.4 . . ?
C00N C00G H00A 110.1 . . ?
C00N C00G H00D 110.1 . . ?
C009 C00H C00E 119.44(18) . . ?
C009 C00H H00H 120.3 . . ?
C00E C00H H00H 120.3 . . ?
C00M C00J H00J 120.7 . . ?
C00M C00J C00S 118.5(2) . . ?
C00S C00J H00J 120.7 . . ?
S002 C00K H00E 109.5 . . ?
S002 C00K H00G 109.5 . . ?
H00E C00K H00G 108.1 . . ?
C00L C00K S002 110.74(14) . . ?
C00L C00K H00E 109.5 . . ?
C00L C00K H00G 109.5 . . ?
C008 C00L C00K 110.30(16) . . ?
C008 C00L H00I 109.6 . . ?
C008 C00L H00K 109.6 . . ?
C00K C00L H00I 109.6 . . ?
C00K C00L H00K 109.6 . . ?
H00I C00L H00K 108.1 . . ?
C00J C00M O006 120.5(2) . . ?
C00J C00M C00Q 121.73(19) . . ?
C00Q C00M O006 117.71(18) . . ?
C00G C00N H00L 109.5 . . ?
C00G C00N H00M 109.5 . . ?
C00G C00N H00N 109.5 . . ?
H00L C00N H00M 109.5 . . ?
H00L C00N H00N 109.5 . . ?
H00M C00N H00N 109.5 . . ?
N00I C00O C00Q 178.8(3) . . ?
C00Q C00P H00P 120.3 . . ?
C00R C00P H00P 120.3 . . ?
C00R C00P C00Q 119.3(2) . . ?
C00M C00Q C00O 120.0(2) . . ?
C00M C00Q C00P 118.9(2) . . ?
C00P C00Q C00O 121.1(2) . . ?
C00P C00R H00R 119.6 . . ?
C00S C00R C00P 120.7(2) . . ?
C00S C00R H00R 119.6 . . ?
C00J C00S H00S 119.6 . . ?
C00R C00S C00J 120.8(2) . . ?
C00R C00S H00S 119.6 . . ?

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
Br01 C00A C00B C00D 176.82(14) . . . . ?
Br01 C00A C00F C008 -176.45(14) . . . . ?
S002 O006 C00M C00J -82.7(2) . . . . ?
S002 O006 C00M C00Q 100.66(19) . . . . ?
S002 C00K C00L C008 178.50(14) . . . . ?
O003 C00E C00H C009 -179.46(18) . . . . ?
O004 C00E C00H C009 0.0(3) . . . . ?
O005 S002 O006 C00M -41.76(17) . . . . ?
O005 S002 C00K C00L 66.99(18) . . . . ?
O006 S002 C00K C00L -179.86(15) . . . . ?
O006 C00M C00Q C00O -2.5(3) . . . . ?
O006 C00M C00Q C00P 176.66(18) . . . . ?
O007 S002 O006 C00M 87.56(16) . . . . ?
O007 S002 C00K C00L -67.02(18) . . . . ?
C008 C00C C00D C009 -179.83(18) . . . . ?
C008 C00C C00D C00B 0.7(3) . . . . ?
C00A C00B C00D C009 -179.72(18) . . . . ?
C00A C00B C00D C00C -0.2(3) . . . . ?
C00B C00A C00F C008 1.0(3) . . . . ?
C00C C008 C00F C00A -0.5(3) . . . . ?
C00C C008 C00L C00K -91.5(2) . . . . ?
C00D C009 C00H C00E 178.78(18) . . . . ?
C00E O003 C00G C00N 179.71(17) . . . . ?
C00F C008 C00C C00D -0.3(3) . . . . ?
C00F C008 C00L C00K 88.8(2) . . . . ?
C00F C00A C00B C00D -0.6(3) . . . . ?
C00G O003 C00E O004 0.4(3) . . . . ?
C00G O003 C00E C00H 179.92(16) . . . . ?
C00H C009 C00D C00B -178.37(19) . . . . ?
C00H C009 C00D C00C 2.1(3) . . . . ?
C00J C00M C00Q C00O -179.1(2) . . . . ?
C00J C00M C00Q C00P 0.1(3) . . . . ?
C00K S002 O006 C00M -157.39(16) . . . . ?
C00L C008 C00C C00D 179.97(17) . . . . ?
C00L C008 C00F C00A 179.23(18) . . . . ?
C00M C00J C00S C00R 0.3(4) . . . . ?
C00P C00R C00S C00J -0.1(4) . . . . ?
C00Q C00P C00R C00S -0.2(4) . . . . ?
C00R C00P C00Q C00M 0.2(3) . . . . ?
C00R C00P C00Q C00O 179.3(2) . . . . ?
C00S C00J C00M O006 -176.8(2) . . . . ?
C00S C00J C00M C00Q -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.858
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_dm-am-10-cha-863_mo
_database_code_depnum_ccdc_archive 'CCDC 1498305'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H26 N2 O6 S'
_chemical_formula_sum            'C25 H26 N2 O6 S'
_chemical_formula_weight         482.54
_chemical_melting_point          ?
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                   8.3702(10)
_cell_length_b                   12.3731(11)
_cell_length_c                   13.2427(8)
_cell_angle_alpha                108.688(7)
_cell_angle_beta                 105.715(8)
_cell_angle_gamma                98.948(9)
_cell_volume                     1205.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0570
_cell_measurement_theta_min      1.9840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.033
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16935
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  25.00   0.50    8.00    --  -20.00   0.00 108.00  270
  2  ω   -110.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  258
  3  ω    -74.50  19.00   0.50    8.00    --  -20.00 -72.00-108.00  187
  4  ω    -71.00 -11.00   0.50    8.00    --  -20.00 -72.00  36.00  120
  5  ω    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00-180.00   60
  6  ω    -59.00  70.00   0.50    8.00    --  -20.00  72.00-108.00  258
  7  ω    -59.00  60.50   0.50    8.00    --  -20.00  72.00-180.00  239
  8  ω    -78.00 -21.00   0.50    8.00    --  -20.00 -72.00 -36.00  114
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134625000
_diffrn_orient_matrix_UB_12      0.0121871000
_diffrn_orient_matrix_UB_13      0.0582252000
_diffrn_orient_matrix_UB_21      0.0208674000
_diffrn_orient_matrix_UB_22      0.0615732000
_diffrn_orient_matrix_UB_23      0.0117361000
_diffrn_orient_matrix_UB_31      -0.0878730000
_diffrn_orient_matrix_UB_32      -0.0008455000
_diffrn_orient_matrix_UB_33      -0.0097270000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3104
_reflns_number_total             4231
_reflns_odcompleteness_completeness 91.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.024
_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)+(0.0908P)²+0.4343P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1798
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C18(H18A,H18B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C5(H5), C4(H4), C11(H11), C9(H9), C21(H21), C13(H13),
 C22(H22), C20(H20), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_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 1.08257(10) 0.69391(7) 1.00292(6) 0.0321(3) Uani 1 1 d . . . . .
O6 O 1.2130(3) 0.76645(18) 0.96272(17) 0.0333(5) Uani 1 1 d . . . . .
O1 O 0.7338(3) 0.59925(19) 0.23675(18) 0.0378(6) Uani 1 1 d . . . . .
O2 O 0.4942(3) 0.4462(2) 0.15877(18) 0.0388(6) Uani 1 1 d . . . . .
O5 O 1.0349(3) 0.7770(2) 1.08483(18) 0.0409(6) Uani 1 1 d . . . . .
O4 O 1.1644(3) 0.6112(2) 1.03392(19) 0.0425(6) Uani 1 1 d . . . . .
O3 O 0.3323(3) -0.0039(2) 0.64985(19) 0.0489(7) Uani 1 1 d . . . . .
N1 N 0.1437(4) -0.0943(2) 0.4715(2) 0.0375(7) Uani 1 1 d . . . . .
C6 C 0.6318(4) 0.4026(3) 0.4820(2) 0.0296(7) Uani 1 1 d . . . . .
C7 C 0.7692(4) 0.4825(3) 0.5784(3) 0.0326(7) Uani 1 1 d . . . . .
H7 H 0.8321 0.5495 0.5751 0.039 Uiso 1 1 calc R . . . .
C12 C 0.4852(4) 0.1776(3) 0.5996(3) 0.0338(8) Uani 1 1 d . . . . .
H12 H 0.5249 0.1722 0.6700 0.041 Uiso 1 1 calc R . . . .
C5 C 0.5878(4) 0.4204(3) 0.3736(3) 0.0324(7) Uani 1 1 d . . . . .
H5 H 0.4883 0.3686 0.3157 0.039 Uiso 1 1 calc R . . . .
C19 C 1.2572(4) 0.8908(3) 1.0064(3) 0.0305(7) Uani 1 1 d . . . . .
C10 C 0.5773(4) 0.2821(3) 0.5882(3) 0.0299(7) Uani 1 1 d . . . . .
C4 C 0.6749(4) 0.5021(3) 0.3505(3) 0.0345(8) Uani 1 1 d . . . . .
H4 H 0.7743 0.5561 0.4067 0.041 Uiso 1 1 calc R . . . .
C11 C 0.5370(4) 0.3037(3) 0.4881(3) 0.0323(7) Uani 1 1 d . . . . .
H11 H 0.4454 0.2509 0.4246 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6197(4) 0.5105(3) 0.2383(3) 0.0315(7) Uani 1 1 d . . . . .
C24 C 1.1796(4) 0.9475(3) 0.9391(3) 0.0357(8) Uani 1 1 d . . . . .
C8 C 0.8117(4) 0.4626(3) 0.6779(3) 0.0316(7) Uani 1 1 d . . . . .
N2 N 0.9377(5) 0.8269(3) 0.7460(3) 0.0647(10) Uani 1 1 d . . . . .
C9 C 0.7154(4) 0.3624(3) 0.6815(3) 0.0335(8) Uani 1 1 d . . . . .
H9 H 0.7442 0.3489 0.7485 0.040 Uiso 1 1 calc R . . . .
C21 C 1.4362(5) 1.0752(3) 1.1475(3) 0.0407(8) Uani 1 1 d . . . . .
H21 H 1.5214 1.1187 1.2178 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3534(4) 0.0910(3) 0.5222(3) 0.0364(8) Uani 1 1 d . . . . .
H13 H 0.3087 0.0903 0.4496 0.044 Uiso 1 1 calc R . . . .
C2 C 0.7001(5) 0.6172(3) 0.1296(3) 0.0380(8) Uani 1 1 d . . . . .
H2A H 0.6396 0.5422 0.0667 0.046 Uiso 1 1 calc R . . . .
H2B H 0.8084 0.6466 0.1215 0.046 Uiso 1 1 calc R . . . .
C14 C 0.2767(4) -0.0062(3) 0.5525(3) 0.0363(8) Uani 1 1 d . . . . .
C22 C 1.3619(5) 1.1328(3) 1.0806(3) 0.0451(9) Uani 1 1 d . . . . .
H22 H 1.3998 1.2147 1.1059 0.054 Uiso 1 1 calc R . . . .
C18 C 0.9075(4) 0.6189(3) 0.8755(3) 0.0314(7) Uani 1 1 d . . . . .
H18A H 0.8215 0.5672 0.8879 0.038 Uiso 1 1 calc R . . . .
H18B H 0.8555 0.6760 0.8528 0.038 Uiso 1 1 calc R . . . .
C17 C 0.9624(4) 0.5458(3) 0.7809(3) 0.0353(8) Uani 1 1 d . . . . .
H17A H 1.0309 0.5988 0.7588 0.042 Uiso 1 1 calc R . . . .
H17B H 1.0344 0.5003 0.8093 0.042 Uiso 1 1 calc R . . . .
C20 C 1.3840(4) 0.9535(3) 1.1099(3) 0.0367(8) Uani 1 1 d . . . . .
H20 H 1.4341 0.9145 1.1542 0.044 Uiso 1 1 calc R . . . .
C1 C 0.5949(5) 0.7031(3) 0.1269(3) 0.0424(9) Uani 1 1 d . . . . .
H1A H 0.5765 0.7156 0.0571 0.064 Uiso 1 1 calc GR . . . .
H1B H 0.6543 0.7769 0.1898 0.064 Uiso 1 1 calc GR . . . .
H1C H 0.4859 0.6724 0.1319 0.064 Uiso 1 1 calc GR . . . .
C23 C 1.2341(5) 1.0710(3) 0.9784(3) 0.0440(9) Uani 1 1 d . . . . .
H23 H 1.1835 1.1106 0.9350 0.053 Uiso 1 1 calc R . . . .
C25 C 1.0459(5) 0.8800(3) 0.8304(3) 0.0457(9) Uani 1 1 d . . . . .
C16 C 0.0611(5) -0.1879(3) 0.4995(3) 0.0463(9) Uani 1 1 d . . . . .
H16A H 0.0942 -0.2587 0.4679 0.070 Uiso 1 1 calc GR . . . .
H16B H -0.0617 -0.2030 0.4685 0.070 Uiso 1 1 calc GR . . . .
H16C H 0.0963 -0.1638 0.5804 0.070 Uiso 1 1 calc GR . . . .
C15 C 0.0754(5) -0.1064(3) 0.3536(3) 0.0509(10) Uani 1 1 d . . . . .
H15A H -0.0083 -0.0620 0.3460 0.076 Uiso 1 1 calc GR . . . .
H15B H 0.0221 -0.1884 0.3061 0.076 Uiso 1 1 calc GR . . . .
H15C H 0.1675 -0.0770 0.3312 0.076 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 O6 1.612(2) . ?
S1 O5 1.428(2) . ?
S1 O4 1.421(2) . ?
S1 C18 1.757(3) . ?
O6 C19 1.405(4) . ?
O1 C3 1.347(4) . ?
O1 C2 1.464(3) . ?
O2 C3 1.204(4) . ?
O3 C14 1.235(4) . ?
N1 C14 1.343(4) . ?
N1 C16 1.457(4) . ?
N1 C15 1.458(4) . ?
C6 C7 1.404(4) . ?
C6 C5 1.480(4) . ?
C6 C11 1.389(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C10 1.471(4) . ?
C12 C13 1.316(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.317(4) . ?
C19 C24 1.391(4) . ?
C19 C20 1.372(4) . ?
C10 C11 1.399(4) . ?
C10 C9 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.475(4) . ?
C11 H11 0.9300 . ?
C24 C23 1.399(5) . ?
C24 C25 1.445(5) . ?
C8 C9 1.392(4) . ?
C8 C17 1.509(4) . ?
N2 C25 1.139(5) . ?
C9 H9 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.386(5) . ?
C21 C20 1.379(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.492(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.486(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.364(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.521(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C20 H20 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C23 H23 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O6 S1 C18 101.38(13) . . ?
O5 S1 O6 108.31(12) . . ?
O5 S1 C18 110.93(15) . . ?
O4 S1 O6 105.89(13) . . ?
O4 S1 O5 119.18(14) . . ?
O4 S1 C18 109.52(15) . . ?
C19 O6 S1 120.32(18) . . ?
C3 O1 C2 116.6(3) . . ?
C14 N1 C16 119.3(3) . . ?
C14 N1 C15 124.8(3) . . ?
C16 N1 C15 115.8(3) . . ?
C7 C6 C5 121.4(3) . . ?
C11 C6 C7 119.3(3) . . ?
C11 C6 C5 119.3(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C10 C12 H12 116.0 . . ?
C13 C12 H12 116.0 . . ?
C13 C12 C10 128.0(3) . . ?
C6 C5 H5 116.6 . . ?
C4 C5 C6 126.7(3) . . ?
C4 C5 H5 116.6 . . ?
C24 C19 O6 118.7(3) . . ?
C20 C19 O6 119.8(3) . . ?
C20 C19 C24 121.3(3) . . ?
C11 C10 C12 123.8(3) . . ?
C9 C10 C12 118.1(3) . . ?
C9 C10 C11 118.0(3) . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C6 C11 C10 121.0(3) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
O1 C3 C4 109.8(3) . . ?
O2 C3 O1 124.8(3) . . ?
O2 C3 C4 125.4(3) . . ?
C19 C24 C23 118.8(3) . . ?
C19 C24 C25 120.6(3) . . ?
C23 C24 C25 120.6(3) . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 C17 121.1(3) . . ?
C9 C8 C17 119.9(3) . . ?
C10 C9 C8 122.1(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.1(3) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
O1 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
O1 C2 C1 110.4(3) . . ?
H2A C2 H2B 108.1 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
O3 C14 N1 121.4(3) . . ?
O3 C14 C13 120.7(3) . . ?
N1 C14 C13 117.9(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
S1 C18 H18A 109.3 . . ?
S1 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C17 C18 S1 111.8(2) . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C8 C17 C18 112.9(3) . . ?
C8 C17 H17A 109.0 . . ?
C8 C17 H17B 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
N2 C25 C24 178.3(4) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 O6 C19 C24 -102.5(3) . . . . ?
S1 O6 C19 C20 82.2(3) . . . . ?
S1 C18 C17 C8 168.9(2) . . . . ?
O6 S1 C18 C17 55.3(2) . . . . ?
O6 C19 C24 C23 -174.6(3) . . . . ?
O6 C19 C24 C25 5.0(4) . . . . ?
O6 C19 C20 C21 174.6(3) . . . . ?
O5 S1 O6 C19 -1.5(3) . . . . ?
O5 S1 C18 C17 170.2(2) . . . . ?
O4 S1 O6 C19 -130.4(2) . . . . ?
O4 S1 C18 C17 -56.2(3) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C8 C17 178.2(3) . . . . ?
C6 C5 C4 C3 179.2(3) . . . . ?
C7 C6 C5 C4 6.4(5) . . . . ?
C7 C6 C11 C10 -0.5(5) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C7 C8 C17 C18 108.9(3) . . . . ?
C12 C10 C11 C6 -178.4(3) . . . . ?
C12 C10 C9 C8 178.9(3) . . . . ?
C12 C13 C14 O3 2.2(5) . . . . ?
C12 C13 C14 N1 -179.2(3) . . . . ?
C5 C6 C7 C8 -178.0(3) . . . . ?
C5 C6 C11 C10 178.4(3) . . . . ?
C5 C4 C3 O1 -178.3(3) . . . . ?
C5 C4 C3 O2 -0.1(5) . . . . ?
C19 C24 C23 C22 0.4(5) . . . . ?
C10 C12 C13 C14 -178.9(3) . . . . ?
C11 C6 C7 C8 0.9(5) . . . . ?
C11 C6 C5 C4 -172.5(3) . . . . ?
C11 C10 C9 C8 0.5(5) . . . . ?
C3 O1 C2 C1 91.1(3) . . . . ?
C24 C19 C20 C21 -0.5(5) . . . . ?
C9 C10 C11 C6 -0.2(5) . . . . ?
C9 C8 C17 C18 -72.4(4) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C13 C12 C10 C11 -1.1(5) . . . . ?
C13 C12 C10 C9 -179.3(3) . . . . ?
C2 O1 C3 O2 0.0(5) . . . . ?
C2 O1 C3 C4 178.2(3) . . . . ?
C22 C21 C20 C19 -0.5(5) . . . . ?
C18 S1 O6 C19 115.3(2) . . . . ?
C17 C8 C9 C10 -178.9(3) . . . . ?
C20 C19 C24 C23 0.6(5) . . . . ?
C20 C19 C24 C25 -179.8(3) . . . . ?
C20 C21 C22 C23 1.5(5) . . . . ?
C25 C24 C23 C22 -179.2(3) . . . . ?
C16 N1 C14 O3 1.2(5) . . . . ?
C16 N1 C14 C13 -177.4(3) . . . . ?
C15 N1 C14 O3 -177.1(3) . . . . ?
C15 N1 C14 C13 4.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.824
_oxdiff_exptl_absorpt_empirical_full_min 0.331
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
