# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BA55M
_database_code_depnum_ccdc_archive 'CCDC 1446305'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-4-(4-methoxyphenyl)-1-(methylsulfonyl)-2-(tosylmethylene)-2,3-dihydro-1H-benzo[b]azepine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N O5 S2'
_chemical_formula_sum            'C26 H25 N O5 S2'
_chemical_formula_weight         495.59

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9256(9)
_cell_length_b                   10.3322(7)
_cell_length_c                   17.0868(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.6470(10)
_cell_angle_gamma                90
_cell_volume                     2450.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9568
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22843
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.467
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4319
_reflns_number_gt                3814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+0.8219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4319
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20248(15) 1.1335(2) 0.81255(12) 0.0492(5) Uani 1 1 d . . . . .
C2 C 0.16289(17) 1.2563(2) 0.80558(14) 0.0593(6) Uani 1 1 d . . . . .
H2 H 0.1183 1.2831 0.8399 0.071 Uiso 1 1 calc R U . . .
C3 C 0.18968(19) 1.3392(2) 0.74755(15) 0.0670(7) Uani 1 1 d . . . . .
H3 H 0.1640 1.4222 0.7433 0.080 Uiso 1 1 calc R U . . .
C4 C 0.25412(19) 1.2984(3) 0.69652(16) 0.0720(7) Uani 1 1 d . . . . .
H4 H 0.2709 1.3533 0.6567 0.086 Uiso 1 1 calc R U . . .
C5 C 0.29415(18) 1.1772(3) 0.70365(14) 0.0663(6) Uani 1 1 d . . . . .
H5 H 0.3380 1.1511 0.6685 0.080 Uiso 1 1 calc R U . . .
C6 C 0.27048(16) 1.0922(2) 0.76256(12) 0.0528(5) Uani 1 1 d . . . . .
C7 C 0.31919(16) 0.9674(2) 0.77284(13) 0.0552(5) Uani 1 1 d . . . . .
H7 H 0.3308 0.9197 0.7284 0.066 Uiso 1 1 calc R U . . .
C8 C 0.34786(15) 0.9189(2) 0.84353(12) 0.0498(5) Uani 1 1 d . . . . .
C9 C 0.33145(15) 0.9975(2) 0.91637(12) 0.0506(5) Uani 1 1 d . . . . .
H9A H 0.3707 0.9631 0.9611 0.061 Uiso 1 1 calc R U . . .
H9B H 0.3505 1.0866 0.9087 0.061 Uiso 1 1 calc R U . . .
C10 C 0.22699(15) 0.99259(18) 0.93239(11) 0.0449(5) Uani 1 1 d . . . . .
C11 C 0.19011(16) 0.9441(2) 0.99598(11) 0.0491(5) Uani 1 1 d . . . . .
H11 H 0.1246 0.9579 0.9995 0.059 Uiso 1 1 calc R U . . .
C12 C 0.0898(2) 0.8160(3) 0.82013(18) 0.0832(8) Uani 1 1 d . . . . .
H12A H 0.0326 0.7686 0.8032 0.125 Uiso 1 1 calc R U . . .
H12B H 0.1210 0.7757 0.8660 0.125 Uiso 1 1 calc R U . . .
H12C H 0.1328 0.8163 0.7790 0.125 Uiso 1 1 calc R U . . .
C13 C 0.39162(14) 0.7889(2) 0.85359(12) 0.0487(5) Uani 1 1 d . . . . .
C14 C 0.36013(16) 0.6881(2) 0.80479(13) 0.0559(5) Uani 1 1 d . . . . .
H14 H 0.3111 0.7035 0.7656 0.067 Uiso 1 1 calc R U . . .
C15 C 0.39894(17) 0.5653(2) 0.81221(13) 0.0579(6) Uani 1 1 d . . . . .
H15 H 0.3766 0.4996 0.7782 0.069 Uiso 1 1 calc R U . . .
C16 C 0.47149(16) 0.5408(2) 0.87074(13) 0.0560(6) Uani 1 1 d . . . . .
C17 C 0.50408(16) 0.6393(2) 0.91988(13) 0.0597(6) Uani 1 1 d . . . . .
H17 H 0.5530 0.6231 0.9590 0.072 Uiso 1 1 calc R U . . .
C18 C 0.46532(16) 0.7617(2) 0.91204(13) 0.0564(5) Uani 1 1 d . . . . .
H18 H 0.4883 0.8271 0.9460 0.068 Uiso 1 1 calc R U . . .
C19 C 0.4742(2) 0.3157(3) 0.83924(19) 0.0839(8) Uani 1 1 d . . . . .
H19A H 0.4072 0.3072 0.8476 0.126 Uiso 1 1 calc R U . . .
H19B H 0.5077 0.2380 0.8559 0.126 Uiso 1 1 calc R U . . .
H19C H 0.4810 0.3299 0.7844 0.126 Uiso 1 1 calc R U . . .
C20 C 0.20931(17) 0.6978(2) 1.05774(11) 0.0521(5) Uani 1 1 d . . . . .
C21 C 0.2546(2) 0.6158(2) 1.00883(15) 0.0688(7) Uani 1 1 d . . . . .
H21 H 0.3067 0.6448 0.9829 0.083 Uiso 1 1 calc R U . . .
C22 C 0.2221(2) 0.4910(3) 0.99877(17) 0.0772(8) Uani 1 1 d . . . . .
H22 H 0.2528 0.4364 0.9655 0.093 Uiso 1 1 calc R U . . .
C23 C 0.1464(2) 0.4444(3) 1.03586(15) 0.0739(7) Uani 1 1 d . . . . .
C24 C 0.1016(3) 0.5275(3) 1.08427(18) 0.0901(9) Uani 1 1 d . . . . .
H24 H 0.0498 0.4977 1.1103 0.108 Uiso 1 1 calc R U . . .
C25 C 0.1320(2) 0.6543(3) 1.09519(15) 0.0756(7) Uani 1 1 d . . . . .
H25 H 0.1003 0.7094 1.1276 0.091 Uiso 1 1 calc R U . . .
C26 C 0.1124(3) 0.3060(3) 1.0258(2) 0.1099(12) Uani 1 1 d . . . . .
H26A H 0.0596 0.3022 0.9861 0.165 Uiso 1 1 calc R U . . .
H26B H 0.0917 0.2747 1.0746 0.165 Uiso 1 1 calc R U . . .
H26C H 0.1644 0.2532 1.0103 0.165 Uiso 1 1 calc R U . . .
N1 N 0.16560(12) 1.04619(17) 0.86980(10) 0.0489(4) Uani 1 1 d . . . . .
O1 O 0.02340(13) 1.0387(2) 0.77216(10) 0.0788(6) Uani 1 1 d . . . . .
O2 O 0.00220(12) 0.9727(2) 0.90732(10) 0.0769(5) Uani 1 1 d . . . . .
O3 O 0.21181(15) 0.90179(18) 1.14396(9) 0.0766(5) Uani 1 1 d . . . . .
O4 O 0.35221(13) 0.86033(16) 1.06883(10) 0.0694(5) Uani 1 1 d . . . . .
O5 O 0.51408(13) 0.42262(18) 0.88343(11) 0.0738(5) Uani 1 1 d . . . . .
S1 S 0.05904(4) 0.97567(6) 0.84236(3) 0.05638(19) Uani 1 1 d . . . . .
S2 S 0.25003(4) 0.85812(5) 1.07329(3) 0.05484(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(3) . ?
C1 C6 1.393(3) . ?
C1 N1 1.454(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(3) . ?
C7 C8 1.339(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.478(3) . ?
C8 C9 1.519(3) . ?
C9 C10 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.336(3) . ?
C10 N1 1.426(3) . ?
C11 S2 1.747(2) . ?
C11 H11 0.9300 . ?
C12 S1 1.754(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.384(3) . ?
C13 C18 1.401(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 O5 1.367(3) . ?
C16 C17 1.373(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O5 1.425(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.372(3) . ?
C20 C21 1.378(3) . ?
C20 S2 1.764(2) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(4) . ?
C23 C26 1.512(4) . ?
C24 C25 1.385(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 S1 1.6852(18) . ?
O1 S1 1.4190(17) . ?
O2 S1 1.4149(18) . ?
O3 S2 1.4315(17) . ?
O4 S2 1.4312(19) . ?

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
C2 C1 C6 120.9(2) . . ?
C2 C1 N1 117.8(2) . . ?
C6 C1 N1 121.15(19) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.5(2) . . ?
C1 C6 C7 121.92(19) . . ?
C5 C6 C7 120.5(2) . . ?
C8 C7 C6 122.7(2) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C13 122.4(2) . . ?
C7 C8 C9 119.0(2) . . ?
C13 C8 C9 118.58(18) . . ?
C10 C9 C8 110.07(17) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 N1 120.59(19) . . ?
C11 C10 C9 127.04(19) . . ?
N1 C10 C9 112.37(17) . . ?
C10 C11 S2 127.87(17) . . ?
C10 C11 H11 116.1 . . ?
S2 C11 H11 116.1 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.2(2) . . ?
C14 C13 C8 120.42(18) . . ?
C18 C13 C8 122.4(2) . . ?
C15 C14 C13 122.3(2) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
O5 C16 C17 116.6(2) . . ?
O5 C16 C15 124.0(2) . . ?
C17 C16 C15 119.5(2) . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.8(2) . . ?
C25 C20 S2 119.49(18) . . ?
C21 C20 S2 120.72(19) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 122.3(3) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 117.7(3) . . ?
C22 C23 C26 121.9(3) . . ?
C24 C23 C26 120.4(3) . . ?
C23 C24 C25 121.5(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C20 C25 C24 119.3(3) . . ?
C20 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C10 N1 C1 121.49(17) . . ?
C10 N1 S1 120.11(14) . . ?
C1 N1 S1 115.59(13) . . ?
C16 O5 C19 117.6(2) . . ?
O2 S1 O1 119.57(12) . . ?
O2 S1 N1 109.09(10) . . ?
O1 S1 N1 106.05(10) . . ?
O2 S1 C12 108.15(14) . . ?
O1 S1 C12 108.90(14) . . ?
N1 S1 C12 103.99(12) . . ?
O3 S2 O4 118.62(11) . . ?
O3 S2 C11 106.86(10) . . ?
O4 S2 C11 111.57(11) . . ?
O3 S2 C20 106.62(11) . . ?
O4 S2 C20 108.41(10) . . ?
C11 S2 C20 103.64(10) . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and dichloromethane'
####################################################################### 
# 
# 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_BB24M
_database_code_depnum_ccdc_archive 'CCDC 1446306'
_audit_update_record             
;
2016-01-09 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
7-chloro-4-(4-methoxyphenyl)-1-(methylsulfonyl)-2-(tosylmethyl)-1H-benzo[b]azepine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 Cl N O5 S2'
_chemical_formula_sum            'C26 H24 Cl N O5 S2'
_chemical_formula_weight         530.03

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7246(6)
_cell_length_b                   11.0418(6)
_cell_length_c                   12.8181(7)
_cell_angle_alpha                70.8320(10)
_cell_angle_beta                 71.9300(10)
_cell_angle_gamma                88.3310(10)
_cell_volume                     1231.88(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7113
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.363
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14559
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5780
_reflns_number_gt                5049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.4442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5780
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24341(16) 1.08659(14) 0.15072(12) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.23480(17) 1.21069(15) 0.08078(13) 0.0360(3) Uani 1 1 d . . . . .
H2 H 0.1802 1.2249 0.0304 0.043 Uiso 1 1 calc R U . . .
C3 C 0.30744(19) 1.31328(16) 0.08595(14) 0.0409(4) Uani 1 1 d . . . . .
H3 H 0.3038 1.3968 0.0385 0.049 Uiso 1 1 calc R U . . .
C4 C 0.38559(19) 1.28894(16) 0.16311(15) 0.0421(4) Uani 1 1 d . . . . .
C5 C 0.39610(18) 1.16712(16) 0.23270(15) 0.0405(4) Uani 1 1 d . . . . .
H5 H 0.4510 1.1544 0.2827 0.049 Uiso 1 1 calc R U . . .
C6 C 0.32368(16) 1.06131(15) 0.22832(13) 0.0333(3) Uani 1 1 d . . . . .
C7 C 0.33774(17) 0.93281(15) 0.30304(14) 0.0353(3) Uani 1 1 d . . . . .
H7 H 0.4253 0.9199 0.3186 0.042 Uiso 1 1 calc R U . . .
C8 C 0.23874(16) 0.83052(15) 0.35228(13) 0.0320(3) Uani 1 1 d . . . . .
C9 C 0.09421(16) 0.83577(14) 0.33958(13) 0.0332(3) Uani 1 1 d . . . . .
H9 H 0.0197 0.7842 0.4030 0.040 Uiso 1 1 calc R U . . .
C10 C 0.05722(16) 0.90623(14) 0.24720(13) 0.0305(3) Uani 1 1 d . . . . .
C11 C -0.09777(16) 0.91612(15) 0.24839(14) 0.0354(3) Uani 1 1 d . . . . .
H11A H -0.1412 0.8306 0.2667 0.042 Uiso 1 1 calc R U . . .
H11B H -0.0989 0.9670 0.1710 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3592(2) 0.8139(2) 0.07658(18) 0.0538(5) Uani 1 1 d . . . . .
H12A H 0.3100 0.7467 0.1481 0.081 Uiso 1 1 calc R U . . .
H12B H 0.4353 0.8574 0.0871 0.081 Uiso 1 1 calc R U . . .
H12C H 0.4000 0.7774 0.0163 0.081 Uiso 1 1 calc R U . . .
C13 C 0.26504(16) 0.70706(14) 0.43235(13) 0.0321(3) Uani 1 1 d . . . . .
C14 C 0.34982(17) 0.70084(15) 0.50348(13) 0.0343(3) Uani 1 1 d . . . . .
H14 H 0.3949 0.7762 0.4992 0.041 Uiso 1 1 calc R U . . .
C15 C 0.36836(17) 0.58469(15) 0.58049(14) 0.0367(3) Uani 1 1 d . . . . .
H15 H 0.4249 0.5826 0.6277 0.044 Uiso 1 1 calc R U . . .
C16 C 0.30254(18) 0.47174(15) 0.58711(14) 0.0379(3) Uani 1 1 d . . . . .
C17 C 0.2210(2) 0.47554(16) 0.51456(16) 0.0444(4) Uani 1 1 d . . . . .
H17 H 0.1796 0.3996 0.5165 0.053 Uiso 1 1 calc R U . . .
C18 C 0.20143(19) 0.59171(16) 0.43969(15) 0.0410(4) Uani 1 1 d . . . . .
H18 H 0.1445 0.5933 0.3929 0.049 Uiso 1 1 calc R U . . .
C19 C 0.3823(2) 0.34315(19) 0.74437(18) 0.0541(5) Uani 1 1 d . . . . .
H19A H 0.4816 0.3766 0.7041 0.081 Uiso 1 1 calc R U . . .
H19B H 0.3788 0.2547 0.7914 0.081 Uiso 1 1 calc R U . . .
H19C H 0.3356 0.3920 0.7933 0.081 Uiso 1 1 calc R U . . .
C20 C -0.12894(18) 1.14619(18) 0.30169(15) 0.0418(4) Uani 1 1 d . . . . .
C21 C -0.1649(2) 1.23849(19) 0.21297(18) 0.0517(4) Uani 1 1 d . . . . .
H21 H -0.2268 1.2164 0.1783 0.062 Uiso 1 1 calc R U . . .
C22 C -0.1073(3) 1.3637(2) 0.1768(2) 0.0591(5) Uani 1 1 d . . . . .
H22 H -0.1313 1.4261 0.1174 0.071 Uiso 1 1 calc R U . . .
C23 C -0.0146(2) 1.3987(2) 0.22701(19) 0.0582(5) Uani 1 1 d . . . . .
C24 C 0.0205(2) 1.3044(2) 0.31438(18) 0.0562(5) Uani 1 1 d . . . . .
H24 H 0.0832 1.3265 0.3484 0.067 Uiso 1 1 calc R U . . .
C25 C -0.0351(2) 1.1784(2) 0.35252(16) 0.0485(4) Uani 1 1 d . . . . .
H25 H -0.0101 1.1161 0.4113 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 0.47207(8) 1.41909(5) 0.17288(6) 0.07392(19) Uani 1 1 d . . . . .
N1 N 0.16627(14) 0.98287(12) 0.14261(11) 0.0317(3) Uani 1 1 d . . . . .
O1 O 0.31552(17) 1.02876(13) -0.06301(11) 0.0562(4) Uani 1 1 d . . . . .
O2 O 0.11691(16) 0.85530(14) 0.03132(12) 0.0563(4) Uani 1 1 d . . . . .
O3 O -0.34833(14) 0.99142(15) 0.33808(14) 0.0617(4) Uani 1 1 d . . . . .
O4 O -0.19157(15) 0.92048(15) 0.46316(11) 0.0580(4) Uani 1 1 d . . . . .
O5 O 0.30962(15) 0.35237(11) 0.66215(12) 0.0521(3) Uani 1 1 d . . . . .
S1 S 0.23475(5) 0.92438(4) 0.03666(3) 0.03882(11) Uani 1 1 d . . . . .
S2 S -0.20644(4) 0.98697(4) 0.35058(4) 0.04215(12) Uani 1 1 d . . . . .
C26 C 0.0460(3) 1.5364(3) 0.1868(3) 0.0850(8) Uani 1 1 d . . . . .
H26A H -0.0046 1.5759 0.2428 0.127 Uiso 1 1 calc R U . . .
H26B H 0.0339 1.5825 0.1128 0.127 Uiso 1 1 calc R U . . .
H26C H 0.1474 1.5385 0.1791 0.127 Uiso 1 1 calc R U . . .


_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
C1 C2 1.386(2) . ?
C1 C6 1.401(2) . ?
C1 N1 1.4359(18) . ?
C2 C3 1.383(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.370(2) . ?
C4 Cl1 1.7442(16) . ?
C5 C6 1.407(2) . ?
C6 C7 1.458(2) . ?
C7 C8 1.349(2) . ?
C8 C9 1.462(2) . ?
C8 C13 1.484(2) . ?
C9 C10 1.334(2) . ?
C10 N1 1.4365(19) . ?
C10 C11 1.504(2) . ?
C11 S2 1.7917(17) . ?
C12 S1 1.761(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.395(2) . ?
C14 C15 1.385(2) . ?
C15 C16 1.384(2) . ?
C16 O5 1.3677(19) . ?
C16 C17 1.388(2) . ?
C17 C18 1.376(2) . ?
C19 O5 1.417(2) . ?
C20 C21 1.385(3) . ?
C20 C25 1.387(2) . ?
C20 S2 1.7641(19) . ?
C21 C22 1.380(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.380(3) . ?
C23 C26 1.508(3) . ?
C24 C25 1.378(3) . ?
N1 S1 1.6415(13) . ?
O1 S1 1.4286(13) . ?
O2 S1 1.4261(14) . ?
O3 S2 1.4353(13) . ?
O4 S2 1.4387(14) . ?

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
C2 C1 C6 121.71(14) . . ?
C2 C1 N1 118.14(13) . . ?
C6 C1 N1 120.15(13) . . ?
C3 C2 C1 119.97(15) . . ?
C4 C3 C2 118.52(15) . . ?
C5 C4 C3 122.52(15) . . ?
C5 C4 Cl1 119.10(13) . . ?
C3 C4 Cl1 118.38(13) . . ?
C4 C5 C6 119.86(15) . . ?
C1 C6 C5 117.42(14) . . ?
C1 C6 C7 124.08(13) . . ?
C5 C6 C7 118.50(14) . . ?
C8 C7 C6 127.68(14) . . ?
C7 C8 C9 123.06(14) . . ?
C7 C8 C13 121.70(13) . . ?
C9 C8 C13 115.03(13) . . ?
C10 C9 C8 127.29(14) . . ?
C9 C10 N1 120.35(13) . . ?
C9 C10 C11 122.81(14) . . ?
N1 C10 C11 116.75(12) . . ?
C10 C11 S2 113.96(10) . . ?
C14 C13 C18 117.63(14) . . ?
C14 C13 C8 122.54(14) . . ?
C18 C13 C8 119.82(13) . . ?
C15 C14 C13 121.36(14) . . ?
C16 C15 C14 119.85(14) . . ?
O5 C16 C15 124.92(15) . . ?
O5 C16 C17 115.42(14) . . ?
C15 C16 C17 119.65(14) . . ?
C18 C17 C16 119.95(15) . . ?
C17 C18 C13 121.51(14) . . ?
C21 C20 C25 120.70(18) . . ?
C21 C20 S2 118.92(14) . . ?
C25 C20 S2 120.38(15) . . ?
C22 C21 C20 118.93(19) . . ?
C21 C22 C23 121.5(2) . . ?
C24 C23 C22 118.27(19) . . ?
C24 C23 C26 121.1(2) . . ?
C22 C23 C26 120.6(2) . . ?
C25 C24 C23 121.69(19) . . ?
C24 C25 C20 118.89(19) . . ?
C1 N1 C10 116.68(12) . . ?
C1 N1 S1 120.62(10) . . ?
C10 N1 S1 119.47(10) . . ?
C16 O5 C19 118.16(14) . . ?
O2 S1 O1 119.92(9) . . ?
O2 S1 N1 106.18(8) . . ?
O1 S1 N1 106.95(7) . . ?
O2 S1 C12 108.21(10) . . ?
O1 S1 C12 107.25(10) . . ?
N1 S1 C12 107.81(8) . . ?
O3 S2 O4 118.96(9) . . ?
O3 S2 C20 108.29(9) . . ?
O4 S2 C20 108.41(9) . . ?
O3 S2 C11 106.39(8) . . ?
O4 S2 C11 108.77(8) . . ?
C20 S2 C11 105.18(8) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and dichloromethane'
