# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1941999'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;INEOS RAS 
Russia
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl N3 O2'
_chemical_formula_sum            'C20 H16 Cl N3 O2'
_chemical_formula_weight         365.81

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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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                   12.174(2)
_cell_length_b                   12.709(3)
_cell_length_c                   12.335(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.06(3)
_cell_angle_gamma                90
_cell_volume                     1699.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2425
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   0.930
_exptl_transmission_factor_max   0.955
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14513
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4465
_reflns_number_gt                3927
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0452P)²+0.7490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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 0.61557(11) 0.14344(10) 0.99056(11) 0.0215(2) Uani 1 1 d . . . . .
H1A H 0.660885 0.107708 1.065586 0.026 Uiso 1 1 calc R U . . .
C2 C 0.52073(11) 0.09262(9) 0.89453(10) 0.0188(2) Uani 1 1 d . . . . .
H2A H 0.503446 0.021215 0.903762 0.023 Uiso 1 1 calc R U . . .
C3 C 0.44979(10) 0.14361(9) 0.78443(10) 0.0158(2) Uani 1 1 d . . . . .
C4 C 0.47665(10) 0.24933(9) 0.77569(10) 0.0165(2) Uani 1 1 d . . . . .
C5 C 0.57499(11) 0.29941(9) 0.86964(11) 0.0202(2) Uani 1 1 d . . . . .
H5A H 0.594684 0.370027 0.860098 0.024 Uiso 1 1 calc R U . . .
C6 C 0.64449(11) 0.24630(10) 0.97743(11) 0.0222(2) Uani 1 1 d . . . . .
H6A H 0.711850 0.280422 1.042181 0.027 Uiso 1 1 calc R U . . .
C7 C 0.34891(10) 0.08606(8) 0.68421(10) 0.0156(2) Uani 1 1 d . . . . .
C8 C 0.26141(11) 0.03313(9) 0.70764(11) 0.0190(2) Uani 1 1 d . . . . .
H8A H 0.266156 0.037066 0.786564 0.023 Uiso 1 1 calc R U . . .
C9 C 0.16798(12) -0.02491(10) 0.61818(12) 0.0229(2) Uani 1 1 d . . . . .
H9A H 0.108951 -0.060294 0.635392 0.027 Uiso 1 1 calc R U . . .
C10 C 0.16141(12) -0.03088(10) 0.50335(11) 0.0234(2) Uani 1 1 d . . . . .
H10A H 0.097109 -0.070152 0.441297 0.028 Uiso 1 1 calc R U . . .
C11 C 0.24747(11) 0.01972(9) 0.47833(11) 0.0203(2) Uani 1 1 d . . . . .
H11A H 0.242255 0.014393 0.399301 0.024 Uiso 1 1 calc R U . . .
C12 C 0.34216(11) 0.07869(9) 0.56761(10) 0.0171(2) Uani 1 1 d . . . . .
N13 N 0.42536(11) 0.13266(8) 0.53910(10) 0.0217(2) Uani 1 1 d . . . . .
H13B H 0.4193(15) 0.1160(13) 0.4673(15) 0.025(4) Uiso 1 1 d . . . . .
H13A H 0.5039(17) 0.1286(14) 0.5988(16) 0.033(4) Uiso 1 1 d . . . . .
C14 C 0.34085(11) 0.39502(9) 0.68079(10) 0.0167(2) Uani 1 1 d . . . . .
N15 N 0.39741(9) 0.30856(7) 0.67138(9) 0.01721(19) Uani 1 1 d . . . . .
H15 H 0.3780(16) 0.2823(14) 0.5997(16) 0.029(4) Uiso 1 1 d . . . . .
C16 C 0.24710(10) 0.43877(9) 0.55713(10) 0.0164(2) Uani 1 1 d . . . . .
O17 O 0.35638(9) 0.43868(7) 0.77547(8) 0.02310(19) Uani 1 1 d . . . . .
N18 N 0.18744(9) 0.52098(8) 0.57456(9) 0.0176(2) Uani 1 1 d . . . . .
H18 H 0.2102(15) 0.5362(12) 0.6485(16) 0.023(4) Uiso 1 1 d . . . . .
C19 C 0.09769(10) 0.58615(9) 0.48930(10) 0.0169(2) Uani 1 1 d . . . . .
C20 C 0.05359(12) 0.66963(9) 0.53204(11) 0.0209(2) Uani 1 1 d . . . . .
C21 C -0.03571(12) 0.73739(10) 0.45355(12) 0.0247(3) Uani 1 1 d . . . . .
H21A H -0.065415 0.793033 0.484513 0.030 Uiso 1 1 calc R U . . .
C22 C -0.08148(12) 0.72352(10) 0.32945(12) 0.0246(3) Uani 1 1 d . . . . .
H22A H -0.142432 0.770019 0.274401 0.030 Uiso 1 1 calc R U . . .
C23 C -0.03814(11) 0.64166(10) 0.28584(11) 0.0223(2) Uani 1 1 d . . . . .
H23A H -0.069449 0.632679 0.200451 0.027 Uiso 1 1 calc R U . . .
C24 C 0.04996(11) 0.57252(9) 0.36413(11) 0.0193(2) Uani 1 1 d . . . . .
H24A H 0.077772 0.515979 0.332567 0.023 Uiso 1 1 calc R U . . .
O25 O 0.23328(8) 0.40072(7) 0.46133(8) 0.02170(18) Uani 1 1 d . . . . .
Cl26 Cl 0.11255(4) 0.68855(3) 0.68770(3) 0.03354(10) 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 1.3817(18) . ?
C1 C6 1.3823(18) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3939(16) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3985(16) . ?
C3 C7 1.4799(16) . ?
C4 C5 1.3852(17) . ?
C4 N15 1.4226(15) . ?
C5 C6 1.3842(17) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3967(16) . ?
C7 C12 1.4059(15) . ?
C8 C9 1.3833(18) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3840(18) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3788(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3958(17) . ?
C11 H11A 0.9500 . ?
C12 N13 1.3944(15) . ?
N13 H13B 0.881(17) . ?
N13 H13A 0.905(18) . ?
C14 O17 1.2275(14) . ?
C14 N15 1.3296(15) . ?
C14 C16 1.5344(16) . ?
N15 H15 0.871(18) . ?
C16 O25 1.2157(14) . ?
C16 N18 1.3444(15) . ?
N18 C19 1.3930(15) . ?
N18 H18 0.846(17) . ?
C19 C24 1.3912(16) . ?
C19 C20 1.3961(16) . ?
C20 C21 1.3796(18) . ?
C20 Cl26 1.7337(14) . ?
C21 C22 1.3815(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3814(19) . ?
C22 H22A 0.9500 . ?
C23 C24 1.3829(17) . ?
C23 H23A 0.9500 . ?
C24 H24A 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
C2 C1 C6 119.98(11) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.58(11) . . ?
C1 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C2 C3 C4 117.31(10) . . ?
C2 C3 C7 119.67(10) . . ?
C4 C3 C7 123.00(10) . . ?
C5 C4 C3 121.35(10) . . ?
C5 C4 N15 119.07(10) . . ?
C3 C4 N15 119.47(10) . . ?
C6 C5 C4 119.84(11) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 119.78(11) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C12 118.97(11) . . ?
C8 C7 C3 119.10(10) . . ?
C12 C7 C3 121.84(10) . . ?
C9 C8 C7 121.30(11) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C10 119.30(11) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C11 C10 C9 120.50(12) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.85(11) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
N13 C12 C11 119.94(10) . . ?
N13 C12 C7 120.94(11) . . ?
C11 C12 C7 119.07(11) . . ?
C12 N13 H13B 113.4(11) . . ?
C12 N13 H13A 112.8(11) . . ?
H13B N13 H13A 112.3(15) . . ?
O17 C14 N15 126.51(11) . . ?
O17 C14 C16 120.33(10) . . ?
N15 C14 C16 113.16(10) . . ?
C14 N15 C4 121.56(10) . . ?
C14 N15 H15 119.5(11) . . ?
C4 N15 H15 118.3(11) . . ?
O25 C16 N18 128.22(11) . . ?
O25 C16 C14 122.24(10) . . ?
N18 C16 C14 109.53(10) . . ?
C16 N18 C19 129.54(10) . . ?
C16 N18 H18 114.5(11) . . ?
C19 N18 H18 115.9(11) . . ?
C24 C19 N18 123.51(11) . . ?
C24 C19 C20 118.39(11) . . ?
N18 C19 C20 118.10(10) . . ?
C21 C20 C19 121.66(12) . . ?
C21 C20 Cl26 119.19(10) . . ?
C19 C20 Cl26 119.14(9) . . ?
C20 C21 C22 119.33(12) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C23 C22 C21 119.64(12) . . ?
C23 C22 H22A 120.2 . . ?
C21 C22 H22A 120.2 . . ?
C22 C23 C24 121.26(12) . . ?
C22 C23 H23A 119.4 . . ?
C24 C23 H23A 119.4 . . ?
C23 C24 C19 119.71(11) . . ?
C23 C24 H24A 120.1 . . ?
C19 C24 H24A 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A O17 0.95 2.56 3.3641(16) 142.6 4_565
N13 H13B O17 0.881(17) 2.240(17) 3.1012(15) 165.7(14) 4_565
N15 H15 N13 0.871(18) 2.214(18) 2.8776(15) 132.8(15) .
N18 H18 O17 0.846(17) 2.150(16) 2.6131(16) 114.2(13) .
N18 H18 Cl26 0.846(17) 2.433(16) 2.9106(11) 116.5(13) .

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_a_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1942001'
loop_
_audit_author_name
_audit_author_address
'Konstantin Lyssenko'
;INEOS RAS 
Russia
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl N3 O2 , S O C2 H6'
_chemical_formula_sum            'C22 H19 Cl N3 O3 S'
_chemical_formula_weight         440.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.957(3)
_cell_length_b                   6.1171(5)
_cell_length_c                   19.5083(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.604(2)
_cell_angle_gamma                90
_cell_volume                     4262.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2360
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1832
_exptl_transmission_factor_min   0.880
_exptl_transmission_factor_max   0.958
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.306
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24783
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5675
_reflns_number_gt                4770
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1140P)²+7.3396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5675
_refine_ls_number_parameters     229
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.2045
_refine_ls_wR_factor_gt          0.1951
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_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 0.3427(2) -0.6204(18) 0.6653(7) 0.0357(14) Uani 0.479(3) 1 d G U P A 1
H1A H 0.343769 -0.748407 0.693056 0.043 Uiso 0.479(3) 1 calc R U P A 1
C2 C 0.37489(18) -0.4988(19) 0.6603(5) 0.0359(13) Uani 0.479(3) 1 d G U P A 1
H2A H 0.398038 -0.543725 0.684677 0.043 Uiso 0.479(3) 1 calc R U P A 1
C3 C 0.3733(3) -0.3116(19) 0.6198(6) 0.0258(13) Uani 0.479(3) 1 d G U P A 1
C4 C 0.3394(4) -0.246(3) 0.5841(8) 0.0222(10) Uani 0.479(3) 1 d G U P A 1
C5 C 0.3072(3) -0.367(3) 0.5891(9) 0.0257(7) Uani 0.479(3) 1 d G U P A 1
H5A H 0.284026 -0.322542 0.564779 0.031 Uiso 0.479(3) 1 calc R U P A 1
C6 C 0.3088(2) -0.555(3) 0.6297(9) 0.0298(9) Uani 0.479(3) 1 d G . P A 1
H6A H 0.286762 -0.637813 0.633106 0.036 Uiso 0.479(3) 1 calc R U P A 1
C7 C 0.40840(14) -0.1796(9) 0.6168(3) 0.0420(11) Uani 0.479(3) 1 d G U P A 1
C8 C 0.42651(16) -0.1950(10) 0.5578(3) 0.0545(12) Uani 0.479(3) 1 d G U P A 1
H8A H 0.417635 -0.294187 0.522121 0.065 Uiso 0.479(3) 1 calc R U P A 1
C9 C 0.45760(14) -0.0653(10) 0.5509(2) 0.0740(15) Uani 0.479(3) 1 d G U P A 1
H9A H 0.469977 -0.075806 0.510534 0.089 Uiso 0.479(3) 1 calc R U P A 1
C10 C 0.47059(11) 0.0798(9) 0.6031(3) 0.0685(16) Uani 0.479(3) 1 d G U P A 1
H10A H 0.491837 0.168461 0.598349 0.082 Uiso 0.479(3) 1 calc R U P A 1
C11 C 0.45248(11) 0.0952(7) 0.6621(3) 0.0642(13) Uani 0.479(3) 1 d G U P A 1
H11A H 0.461356 0.194349 0.697751 0.077 Uiso 0.479(3) 1 calc R U P A 1
C12 C 0.42139(11) -0.0345(8) 0.6690(2) 0.0448(10) Uani 0.479(3) 1 d G U P A 1
N13 N 0.40821(17) -0.0337(13) 0.7282(3) 0.0720(13) Uani 0.479(3) 1 d . . P A 1
H13D H 0.418931 0.047075 0.762243 0.086 Uiso 0.479(3) 1 calc R U P A 1
H13E H 0.388548 -0.113979 0.734367 0.086 Uiso 0.479(3) 1 calc R U P A 1
C14 C 0.32673(5) 0.2515(3) 0.47383(10) 0.0241(4) Uani 1 1 d . . . . .
N15 N 0.29991(4) 0.3735(3) 0.43902(8) 0.0235(3) Uani 1 1 d . . . . .
H15A H 0.276617 0.334159 0.442075 0.028 Uiso 1 1 calc R U . . .
C16 C 0.31070(5) 0.0623(3) 0.51402(9) 0.0216(3) Uani 1 1 d . . . . .
O17 O 0.27703(4) 0.0356(2) 0.51417(8) 0.0290(3) Uani 1 1 d . . . . .
N18 N 0.33866(4) -0.0576(3) 0.54635(9) 0.0251(3) Uani 1 1 d . . . . .
H18N H 0.358661 -0.008814 0.540282 0.035(7) Uiso 1 1 d R . . A .
C19 C 0.30515(5) 0.5588(3) 0.39795(9) 0.0224(4) Uani 1 1 d . . . . .
C20 C 0.33954(6) 0.6602(4) 0.39705(13) 0.0367(5) Uani 1 1 d . . . . .
H20A H 0.360984 0.603168 0.424181 0.044 Uiso 1 1 calc R U . . .
C21 C 0.34288(6) 0.8450(4) 0.35666(13) 0.0366(5) Uani 1 1 d . . . . .
H21A H 0.366473 0.914784 0.356525 0.044 Uiso 1 1 calc R U . . .
C22 C 0.31190(6) 0.9264(3) 0.31693(10) 0.0267(4) Uani 1 1 d . . . . .
C23 C 0.27729(6) 0.8262(4) 0.31646(11) 0.0300(4) Uani 1 1 d . . . . .
H23A H 0.256022 0.882823 0.288731 0.036 Uiso 1 1 calc R U . . .
C24 C 0.27405(5) 0.6419(3) 0.35700(10) 0.0266(4) Uani 1 1 d . . . . .
H24A H 0.250449 0.571978 0.356784 0.032 Uiso 1 1 calc R U . . .
Cl25 Cl 0.31642(2) 1.15875(9) 0.26696(3) 0.03571(16) Uani 1 1 d . . . . .
O26 O 0.36063(4) 0.2761(3) 0.47596(9) 0.0381(4) Uani 1 1 d . . . . .
C1' C 0.3323(2) -0.6259(16) 0.6679(6) 0.0357(14) Uani 0.521(3) 1 d G U P A 2
H1'A H 0.331423 -0.754578 0.694930 0.043 Uiso 0.521(3) 1 calc R U P A 2
C2' C 0.36527(17) -0.5056(17) 0.6708(4) 0.0359(13) Uani 0.521(3) 1 d G U P A 2
H2'A H 0.386870 -0.552053 0.699734 0.043 Uiso 0.521(3) 1 calc R U P A 2
C3' C 0.3666(2) -0.3173(17) 0.6312(5) 0.0258(13) Uani 0.521(3) 1 d G U P A 2
C4' C 0.3350(3) -0.249(2) 0.5888(7) 0.0222(10) Uani 0.521(3) 1 d G U P A 2
C5' C 0.3021(3) -0.370(3) 0.5860(8) 0.0257(7) Uani 0.521(3) 1 d G U P A 2
H5'A H 0.280461 -0.323224 0.556995 0.031 Uiso 0.521(3) 1 calc R U P A 2
C6' C 0.3007(2) -0.558(2) 0.6255(8) 0.0298(9) Uani 0.521(3) 1 d G U P A 2
H6'A H 0.278218 -0.640162 0.623559 0.036 Uiso 0.521(3) 1 calc R U P A 2
C7' C 0.40279(12) -0.1853(9) 0.6349(2) 0.0420(11) Uani 0.521(3) 1 d G U P A 2
C8' C 0.41241(12) -0.0708(9) 0.6960(2) 0.0545(12) Uani 0.521(3) 1 d G U P A 2
H8'A H 0.396935 -0.079393 0.732181 0.065 Uiso 0.521(3) 1 calc R U P A 2
C9' C 0.44468(13) 0.0561(9) 0.7040(2) 0.0740(15) Uani 0.521(3) 1 d G U P A 2
H9'A H 0.451256 0.134335 0.745661 0.089 Uiso 0.521(3) 1 calc R U P A 2
C10' C 0.46733(10) 0.0686(8) 0.6509(3) 0.0685(16) Uani 0.521(3) 1 d G U P A 2
H10B H 0.489380 0.155390 0.656419 0.082 Uiso 0.521(3) 1 calc R U P A 2
C11' C 0.45770(10) -0.0458(8) 0.5899(2) 0.0642(13) Uani 0.521(3) 1 d G U P A 2
H11B H 0.473181 -0.037280 0.553697 0.077 Uiso 0.521(3) 1 calc R U P A 2
C12' C 0.42544(12) -0.1728(8) 0.5819(2) 0.0448(10) Uani 0.521(3) 1 d G U P A 2
N13' N 0.41522(15) -0.3009(12) 0.5202(3) 0.0720(13) Uani 0.521(3) 1 d . . P A 2
H13A H 0.429585 -0.299675 0.486634 0.086 Uiso 0.521(3) 1 calc R U P A 2
H13C H 0.394650 -0.380063 0.516343 0.086 Uiso 0.521(3) 1 calc R U P A 2


_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 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1A 0.9500 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9500 . ?
C3 C4 1.3900 . ?
C3 C7 1.506(9) . ?
C4 N18 1.366(11) . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8A 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9A 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11A 0.9500 . ?
C12 N13 1.299(7) . ?
N13 H13D 0.8800 . ?
N13 H13E 0.8800 . ?
C14 O26 1.224(2) . ?
C14 N15 1.341(2) . ?
C14 C16 1.546(3) . ?
N15 C19 1.413(2) . ?
N15 H15A 0.8800 . ?
C16 O17 1.222(2) . ?
C16 N18 1.342(2) . ?
N18 C4' 1.451(10) . ?
N18 H18N 0.8000 . ?
C19 C20 1.386(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.391(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.375(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.387(3) . ?
C22 Cl25 1.741(2) . ?
C23 C24 1.389(3) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C1' H1'A 0.9500 . ?
C2' C3' 1.3900 . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.3900 . ?
C3' C7' 1.526(8) . ?
C4' C5' 1.3900 . ?
C5' C6' 1.3900 . ?
C5' H5'A 0.9500 . ?
C6' H6'A 0.9500 . ?
C7' C8' 1.3900 . ?
C7' C12' 1.3900 . ?
C8' C9' 1.3900 . ?
C8' H8'A 0.9500 . ?
C9' C10' 1.3900 . ?
C9' H9'A 0.9500 . ?
C10' C11' 1.3900 . ?
C10' H10B 0.9500 . ?
C11' C12' 1.3900 . ?
C11' H11B 0.9500 . ?
C12' N13' 1.448(7) . ?
N13' H13A 0.8800 . ?
N13' H13C 0.8800 . ?

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 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C7 121.1(8) . . ?
C2 C3 C7 118.9(8) . . ?
N18 C4 C5 121.6(9) . . ?
N18 C4 C3 118.4(9) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C1 C6 H6A 120.0 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C3 118.0(5) . . ?
C12 C7 C3 121.8(5) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
N13 C12 C11 117.6(4) . . ?
N13 C12 C7 121.9(4) . . ?
C11 C12 C7 120.0 . . ?
C12 N13 H13D 120.0 . . ?
C12 N13 H13E 120.0 . . ?
H13D N13 H13E 120.0 . . ?
O26 C14 N15 127.18(18) . . ?
O26 C14 C16 120.15(17) . . ?
N15 C14 C16 112.67(16) . . ?
C14 N15 C19 126.77(16) . . ?
C14 N15 H15A 116.6 . . ?
C19 N15 H15A 116.6 . . ?
O17 C16 N18 127.94(18) . . ?
O17 C16 C14 121.88(17) . . ?
N18 C16 C14 110.18(15) . . ?
C4 N18 C16 133.0(6) . . ?
C16 N18 C4' 126.7(5) . . ?
C4 N18 H18N 115.6 . . ?
C16 N18 H18N 111.3 . . ?
C4' N18 H18N 121.9 . . ?
C20 C19 C24 119.20(18) . . ?
C20 C19 N15 122.94(17) . . ?
C24 C19 N15 117.85(17) . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C21 C22 C23 120.79(19) . . ?
C21 C22 Cl25 119.29(16) . . ?
C23 C22 Cl25 119.92(16) . . ?
C22 C23 C24 119.27(19) . . ?
C22 C23 H23A 120.4 . . ?
C24 C23 H23A 120.4 . . ?
C23 C24 C19 120.54(18) . . ?
C23 C24 H24A 119.7 . . ?
C19 C24 H24A 119.7 . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' H1'A 120.0 . . ?
C6' C1' H1'A 120.0 . . ?
C1' C2' C3' 120.0 . . ?
C1' C2' H2'A 120.0 . . ?
C3' C2' H2'A 120.0 . . ?
C4' C3' C2' 120.0 . . ?
C4' C3' C7' 120.3(7) . . ?
C2' C3' C7' 119.7(7) . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' N18 122.6(8) . . ?
C3' C4' N18 117.4(8) . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5'A 120.0 . . ?
C6' C5' H5'A 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' H6'A 120.0 . . ?
C1' C6' H6'A 120.0 . . ?
C8' C7' C12' 120.0 . . ?
C8' C7' C3' 115.7(5) . . ?
C12' C7' C3' 124.3(5) . . ?
C9' C8' C7' 120.0 . . ?
C9' C8' H8'A 120.0 . . ?
C7' C8' H8'A 120.0 . . ?
C10' C9' C8' 120.0 . . ?
C10' C9' H9'A 120.0 . . ?
C8' C9' H9'A 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C9' C10' H10B 120.0 . . ?
C11' C10' H10B 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C12' C11' H11B 120.0 . . ?
C10' C11' H11B 120.0 . . ?
C11' C12' C7' 120.0 . . ?
C11' C12' N13' 121.6(3) . . ?
C7' C12' N13' 118.3(3) . . ?
C12' N13' H13A 120.0 . . ?
C12' N13' H13C 120.0 . . ?
H13A N13' H13C 120.0 . . ?

_refine_diff_density_max         1.034
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.076




