# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_mo_20141120a_0m
_database_code_depnum_ccdc_archive 'CCDC 1414495'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl N O2'
_chemical_formula_weight         389.86

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.7898(8)
_cell_length_b                   21.266(2)
_cell_length_c                   10.9725(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.651(2)
_cell_angle_gamma                90.00
_cell_volume                     1965.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3595
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11034
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3494
_reflns_number_gt                2710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0785P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3494
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30648(7) 0.25015(2) 0.15025(6) 0.0535(2) Uani 1 1 d . . .
C14 C 0.1607(2) 0.13763(8) 0.12932(17) 0.0296(4) Uani 1 1 d . . .
C7 C 0.0724(2) 0.08153(8) 0.16659(17) 0.0305(4) Uani 1 1 d . . .
H7 H 0.0052 0.0651 0.0856 0.037 Uiso 1 1 calc R . .
C21 C 0.1953(2) 0.19037(8) 0.19597(18) 0.0321(4) Uani 1 1 d . . .
C8 C -0.0422(2) 0.09560(9) 0.24465(18) 0.0344(4) Uani 1 1 d . . .
C15 C 0.2021(2) 0.12916(8) 0.00707(18) 0.0334(4) Uani 1 1 d . . .
C1 C 0.1868(2) 0.02802(8) 0.22261(17) 0.0310(4) Uani 1 1 d . . .
C20 C 0.1357(2) 0.16899(10) -0.09436(19) 0.0400(5) Uani 1 1 d . . .
H20 H 0.0709 0.2020 -0.0842 0.048 Uiso 1 1 calc R . .
C2 C 0.3411(2) 0.03826(10) 0.29558(19) 0.0395(5) Uani 1 1 d . . .
H2 H 0.3790 0.0791 0.3120 0.047 Uiso 1 1 calc R . .
C22 C 0.2500(3) 0.20559(10) 0.4220(2) 0.0458(5) Uani 1 1 d . . .
C6 C 0.1329(2) -0.03331(9) 0.2003(2) 0.0412(5) Uani 1 1 d . . .
H6 H 0.0294 -0.0409 0.1511 0.049 Uiso 1 1 calc R . .
C16 C 0.2995(3) 0.08087(10) -0.0117(2) 0.0469(5) Uani 1 1 d . . .
H16 H 0.3468 0.0539 0.0551 0.056 Uiso 1 1 calc R . .
C19 C 0.1647(2) 0.16016(12) -0.2100(2) 0.0499(6) Uani 1 1 d . . .
H19 H 0.1189 0.1872 -0.2771 0.060 Uiso 1 1 calc R . .
C4 C 0.3848(3) -0.07261(10) 0.3227(2) 0.0504(6) Uani 1 1 d . . .
H4 H 0.4508 -0.1063 0.3566 0.060 Uiso 1 1 calc R . .
C9 C -0.0075(3) 0.08099(11) 0.3733(2) 0.0472(5) Uani 1 1 d . . .
H9 H 0.0894 0.0626 0.4150 0.057 Uiso 1 1 calc R . .
C17 C 0.3266(3) 0.07254(12) -0.1284(2) 0.0602(7) Uani 1 1 d . . .
H17 H 0.3909 0.0396 -0.1398 0.072 Uiso 1 1 calc R . .
C3 C 0.4402(3) -0.01222(10) 0.3446(2) 0.0453(5) Uani 1 1 d . . .
H3 H 0.5446 -0.0050 0.3925 0.054 Uiso 1 1 calc R . .
C18 C 0.2600(3) 0.11221(12) -0.2276(2) 0.0553(6) Uani 1 1 d . . .
H18 H 0.2792 0.1066 -0.3060 0.066 Uiso 1 1 calc R . .
C5 C 0.2309(3) -0.08312(10) 0.2502(2) 0.0527(6) Uani 1 1 d . . .
H5 H 0.1930 -0.1241 0.2348 0.063 Uiso 1 1 calc R . .
C13 C -0.1886(2) 0.12145(11) 0.1856(2) 0.0512(6) Uani 1 1 d . . .
H13 H -0.2153 0.1305 0.0991 0.061 Uiso 1 1 calc R . .
C10 C -0.1162(3) 0.09365(13) 0.4396(2) 0.0604(7) Uani 1 1 d . . .
H10 H -0.0915 0.0839 0.5257 0.072 Uiso 1 1 calc R . .
C23 C 0.0355(3) 0.26283(14) 0.4316(2) 0.0632(7) Uani 1 1 d . . .
H23A H 0.0239 0.3066 0.4522 0.076 Uiso 1 1 calc R . .
H23B H -0.0480 0.2386 0.4512 0.076 Uiso 1 1 calc R . .
C12 C -0.2963(3) 0.13413(13) 0.2527(3) 0.0654(7) Uani 1 1 d . . .
H12 H -0.3939 0.1520 0.2110 0.078 Uiso 1 1 calc R . .
C11 C -0.2616(3) 0.12075(12) 0.3792(3) 0.0639(7) Uani 1 1 d . . .
H11 H -0.3341 0.1297 0.4241 0.077 Uiso 1 1 calc R . .
N1 N 0.14852(17) 0.20752(7) 0.30296(14) 0.0327(4) Uani 1 1 d . . .
O1 O 0.3764(2) 0.17896(9) 0.45708(16) 0.0744(6) Uani 1 1 d . . .
O2 O 0.1883(2) 0.23958(8) 0.50101(15) 0.0631(5) Uani 1 1 d . . .
C24 C 0.0281(3) 0.25586(10) 0.2944(2) 0.0437(5) Uani 1 1 d . . .
H24A H -0.0759 0.2419 0.2437 0.052 Uiso 1 1 calc R . .
H24B H 0.0554 0.2947 0.2594 0.052 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
Cl1 C21 1.7616(18) . ?
C14 C21 1.326(3) . ?
C14 C15 1.498(2) . ?
C14 C7 1.541(2) . ?
C7 C1 1.526(2) . ?
C7 C8 1.527(2) . ?
C21 N1 1.399(2) . ?
C8 C13 1.378(3) . ?
C8 C9 1.391(3) . ?
C15 C20 1.387(3) . ?
C15 C16 1.389(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.385(3) . ?
C20 C19 1.377(3) . ?
C2 C3 1.390(3) . ?
C22 O1 1.208(3) . ?
C22 N1 1.355(3) . ?
C22 O2 1.356(3) . ?
C6 C5 1.375(3) . ?
C16 C17 1.380(3) . ?
C19 C18 1.368(3) . ?
C4 C3 1.370(3) . ?
C4 C5 1.377(3) . ?
C9 C10 1.384(3) . ?
C17 C18 1.369(3) . ?
C13 C12 1.383(3) . ?
C10 C11 1.385(3) . ?
C23 O2 1.429(3) . ?
C23 C24 1.496(3) . ?
C12 C11 1.363(4) . ?
N1 C24 1.459(2) . ?

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
C21 C14 C15 121.28(16) . . ?
C21 C14 C7 124.21(16) . . ?
C15 C14 C7 114.49(15) . . ?
C1 C7 C8 112.61(15) . . ?
C1 C7 C14 111.12(14) . . ?
C8 C7 C14 117.42(14) . . ?
C14 C21 N1 127.37(16) . . ?
C14 C21 Cl1 120.79(14) . . ?
N1 C21 Cl1 111.80(13) . . ?
C13 C8 C9 118.04(19) . . ?
C13 C8 C7 119.43(18) . . ?
C9 C8 C7 122.48(17) . . ?
C20 C15 C16 117.91(18) . . ?
C20 C15 C14 119.36(16) . . ?
C16 C15 C14 122.66(17) . . ?
C2 C1 C6 118.70(17) . . ?
C2 C1 C7 122.72(16) . . ?
C6 C1 C7 118.58(16) . . ?
C19 C20 C15 120.62(19) . . ?
C1 C2 C3 120.36(19) . . ?
O1 C22 N1 127.8(2) . . ?
O1 C22 O2 123.1(2) . . ?
N1 C22 O2 109.07(17) . . ?
C5 C6 C1 120.77(19) . . ?
C17 C16 C15 120.7(2) . . ?
C18 C19 C20 121.0(2) . . ?
C3 C4 C5 119.63(19) . . ?
C10 C9 C8 120.4(2) . . ?
C18 C17 C16 120.7(2) . . ?
C4 C3 C2 120.3(2) . . ?
C19 C18 C17 119.1(2) . . ?
C6 C5 C4 120.3(2) . . ?
C8 C13 C12 121.1(2) . . ?
C9 C10 C11 120.7(2) . . ?
O2 C23 C24 105.38(19) . . ?
C11 C12 C13 120.9(2) . . ?
C12 C11 C10 118.8(2) . . ?
C22 N1 C21 122.04(16) . . ?
C22 N1 C24 110.40(16) . . ?
C21 N1 C24 120.78(15) . . ?
C22 O2 C23 109.33(17) . . ?
N1 C24 C23 100.56(17) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_mo_20150507b_0m
_database_code_depnum_ccdc_archive 'CCDC 1414496'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Br N O2'
_chemical_formula_weight         434.32

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.3958(19)
_cell_length_b                   9.1841(11)
_cell_length_c                   16.013(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.983(2)
_cell_angle_gamma                90.00
_cell_volume                     2017.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5329
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.18
_reflns_number_total             2941
_reflns_number_gt                2720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0143P)²+0.0671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.036(8)
_refine_ls_number_reflns         2941
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.20952(2) 0.61419(3) 0.27576(2) 0.06139(13) Uani 1 1 d . . .
C2 C 0.0533(3) 1.1008(3) 0.2233(3) 0.0463(8) Uani 1 1 d . . .
H2 H 0.1088 1.0428 0.2497 0.056 Uiso 1 1 calc R . .
C6 C -0.1188(3) 1.1272(4) 0.1537(3) 0.0562(9) Uani 1 1 d . . .
H6 H -0.1808 1.0872 0.1317 0.067 Uiso 1 1 calc R . .
C1 C -0.0371(2) 1.0374(3) 0.1922(2) 0.0373(6) Uani 1 1 d . . .
C4 C -0.0166(3) 1.3373(4) 0.1786(3) 0.0594(10) Uani 1 1 d . . .
H4 H -0.0098 1.4371 0.1733 0.071 Uiso 1 1 calc R . .
C3 C 0.0632(3) 1.2501(4) 0.2160(3) 0.0551(10) Uani 1 1 d . . .
H3 H 0.1250 1.2905 0.2369 0.066 Uiso 1 1 calc R . .
C5 C -0.1079(3) 1.2766(4) 0.1483(3) 0.0675(11) Uani 1 1 d . . .
H5 H -0.1626 1.3362 0.1241 0.081 Uiso 1 1 calc R . .
C7 C -0.0516(2) 0.8731(3) 0.1966(2) 0.0368(6) Uani 1 1 d . . .
H7 H -0.1052 0.8490 0.1352 0.044 Uiso 1 1 calc R . .
C8 C -0.0884(2) 0.8282(3) 0.2663(2) 0.0394(7) Uani 1 1 d . . .
C9 C -0.1418(2) 0.7004(4) 0.2505(3) 0.0519(8) Uani 1 1 d . . .
H9 H -0.1556 0.6458 0.1970 0.062 Uiso 1 1 calc R . .
C13 C -0.0707(3) 0.9081(4) 0.3464(3) 0.0497(9) Uani 1 1 d . . .
H13 H -0.0353 0.9943 0.3589 0.060 Uiso 1 1 calc R . .
C12 C -0.1054(4) 0.8599(5) 0.4074(3) 0.0679(11) Uani 1 1 d . . .
H12 H -0.0937 0.9146 0.4603 0.082 Uiso 1 1 calc R . .
C11 C -0.1570(3) 0.7323(5) 0.3907(3) 0.0706(12) Uani 1 1 d . . .
H11 H -0.1796 0.7001 0.4323 0.085 Uiso 1 1 calc R . .
C10 C -0.1746(3) 0.6535(5) 0.3129(3) 0.0630(11) Uani 1 1 d . . .
H10 H -0.2093 0.5668 0.3016 0.076 Uiso 1 1 calc R . .
C15 C 0.0357(2) 0.7701(3) 0.1078(2) 0.0399(7) Uani 1 1 d . . .
C14 C 0.0358(2) 0.7871(3) 0.2007(2) 0.0361(6) Uani 1 1 d . . .
C20 C -0.0401(3) 0.6957(3) 0.0360(2) 0.0480(8) Uani 1 1 d . . .
H20 H -0.0906 0.6571 0.0458 0.058 Uiso 1 1 calc R . .
C16 C 0.1095(3) 0.8309(4) 0.0915(3) 0.0550(8) Uani 1 1 d . . .
H16 H 0.1600 0.8827 0.1384 0.066 Uiso 1 1 calc R . .
C18 C 0.0324(4) 0.7375(4) -0.0651(3) 0.0686(11) Uani 1 1 d . . .
H18 H 0.0314 0.7256 -0.1232 0.082 Uiso 1 1 calc R . .
C17 C 0.1065(3) 0.8128(5) 0.0038(3) 0.0664(11) Uani 1 1 d . . .
H17 H 0.1556 0.8526 -0.0078 0.080 Uiso 1 1 calc R . .
C19 C -0.0406(3) 0.6792(4) -0.0491(3) 0.0666(11) Uani 1 1 d . . .
H19 H -0.0910 0.6279 -0.0965 0.080 Uiso 1 1 calc R . .
C21 C 0.1061(2) 0.7317(3) 0.2783(2) 0.0405(7) Uani 1 1 d . . .
C24 C 0.1833(3) 0.8375(4) 0.4325(2) 0.0527(8) Uani 1 1 d . . .
C22 C 0.1017(4) 0.6183(5) 0.4180(3) 0.0706(12) Uani 1 1 d . . .
H22A H 0.1410 0.5356 0.4183 0.085 Uiso 1 1 calc R . .
H22B H 0.0337 0.5897 0.3910 0.085 Uiso 1 1 calc R . .
O2 O 0.1998(2) 0.8010(4) 0.5197(2) 0.0786(8) Uani 1 1 d . . .
C23 C 0.1367(4) 0.6833(6) 0.5154(3) 0.0878(15) Uani 1 1 d . . .
H23A H 0.0821 0.7186 0.5243 0.105 Uiso 1 1 calc R . .
H23B H 0.1719 0.6113 0.5633 0.105 Uiso 1 1 calc R . .
N1 N 0.11642(19) 0.7435(3) 0.36953(19) 0.0448(6) Uani 1 1 d . . .
O1 O 0.2244(2) 0.9372(3) 0.4170(2) 0.0659(7) 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
Br1 C21 1.939(3) . ?
C2 C1 1.376(5) . ?
C2 C3 1.390(4) . ?
C6 C5 1.389(5) . ?
C6 C1 1.394(5) . ?
C1 C7 1.532(4) . ?
C4 C3 1.358(5) . ?
C4 C5 1.380(6) . ?
C7 C8 1.521(4) . ?
C7 C14 1.536(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.393(5) . ?
C9 C10 1.378(5) . ?
C13 C12 1.382(6) . ?
C12 C11 1.372(7) . ?
C11 C10 1.357(7) . ?
C15 C20 1.390(5) . ?
C15 C16 1.394(4) . ?
C15 C14 1.495(4) . ?
C14 C21 1.324(4) . ?
C20 C19 1.367(5) . ?
C16 C17 1.393(5) . ?
C18 C17 1.362(7) . ?
C18 C19 1.371(6) . ?
C21 N1 1.401(4) . ?
C24 O1 1.201(5) . ?
C24 O2 1.343(4) . ?
C24 N1 1.372(5) . ?
C22 N1 1.461(4) . ?
C22 C23 1.522(8) . ?
O2 C23 1.434(6) . ?

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
C1 C2 C3 121.2(3) . . ?
C5 C6 C1 120.0(4) . . ?
C2 C1 C6 118.1(3) . . ?
C2 C1 C7 123.0(3) . . ?
C6 C1 C7 118.8(3) . . ?
C3 C4 C5 119.4(3) . . ?
C4 C3 C2 120.4(4) . . ?
C4 C5 C6 120.7(4) . . ?
C8 C7 C1 114.3(2) . . ?
C8 C7 C14 116.2(2) . . ?
C1 C7 C14 111.4(2) . . ?
C9 C8 C13 117.8(3) . . ?
C9 C8 C7 118.8(3) . . ?
C13 C8 C7 123.4(3) . . ?
C10 C9 C8 120.9(4) . . ?
C12 C13 C8 120.3(4) . . ?
C11 C12 C13 120.7(4) . . ?
C10 C11 C12 119.4(3) . . ?
C11 C10 C9 120.8(4) . . ?
C20 C15 C16 119.5(3) . . ?
C20 C15 C14 119.8(3) . . ?
C16 C15 C14 120.7(3) . . ?
C21 C14 C15 121.7(3) . . ?
C21 C14 C7 124.4(3) . . ?
C15 C14 C7 113.9(3) . . ?
C19 C20 C15 120.1(3) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C18 C19 120.3(4) . . ?
C18 C17 C16 120.6(4) . . ?
C20 C19 C18 120.6(4) . . ?
C14 C21 N1 127.3(3) . . ?
C14 C21 Br1 121.6(2) . . ?
N1 C21 Br1 111.1(2) . . ?
O1 C24 O2 122.5(4) . . ?
O1 C24 N1 128.2(3) . . ?
O2 C24 N1 109.4(3) . . ?
N1 C22 C23 99.6(3) . . ?
C24 O2 C23 109.5(3) . . ?
O2 C23 C22 105.2(3) . . ?
C24 N1 C21 120.5(3) . . ?
C24 N1 C22 110.5(3) . . ?
C21 N1 C22 121.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.18
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_mo_20150525a_0m
_database_code_depnum_ccdc_archive 'CCDC 1414497'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Cl N O2 S'
_chemical_formula_weight         411.93

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3660(6)
_cell_length_b                   11.2874(8)
_cell_length_c                   12.1577(9)
_cell_angle_alpha                86.279(2)
_cell_angle_beta                 71.4270(10)
_cell_angle_gamma                82.812(2)
_cell_volume                     1079.33(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5395
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11062
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3807
_reflns_number_gt                3219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0767P)²+0.3691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6828(2) 0.83329(18) 0.99518(15) 0.0754(5) Uani 1 1 d . . .
Cl1 Cl 0.63785(8) 0.92503(7) 0.71861(6) 0.0922(3) Uani 1 1 d . . .
S1 S 0.56887(7) 0.75971(5) 0.97682(5) 0.0531(2) Uani 1 1 d . . .
C1 C 1.1032(2) 0.94268(16) 0.67381(17) 0.0432(4) Uani 1 1 d . . .
C21 C 0.7494(2) 0.79641(18) 0.75952(17) 0.0460(5) Uani 1 1 d . . .
C14 C 0.9159(2) 0.77283(17) 0.71395(16) 0.0398(4) Uani 1 1 d . . .
C6 C 1.2377(3) 0.99985(19) 0.6019(2) 0.0533(5) Uani 1 1 d . . .
H6 H 1.2826 0.9801 0.5242 0.064 Uiso 1 1 calc R . .
C15 C 0.9987(2) 0.66024(17) 0.75421(17) 0.0429(4) Uani 1 1 d . . .
C20 C 1.0584(3) 0.6588(2) 0.84829(19) 0.0523(5) Uani 1 1 d . . .
H20 H 1.0454 0.7285 0.8884 0.063 Uiso 1 1 calc R . .
C8 C 1.1577(3) 0.78031(18) 0.52650(17) 0.0463(5) Uani 1 1 d . . .
N1 N 0.6464(2) 0.72108(16) 0.84115(15) 0.0470(4) Uani 1 1 d . . .
C7 C 1.0255(2) 0.85287(17) 0.62209(16) 0.0429(4) Uani 1 1 d . . .
H7 H 0.9493 0.9002 0.5851 0.052 Uiso 1 1 calc R . .
C2 C 1.0386(3) 0.97517(19) 0.78888(19) 0.0544(5) Uani 1 1 d . . .
H2 H 0.9470 0.9397 0.8387 0.065 Uiso 1 1 calc R . .
C3 C 1.1095(4) 1.0603(2) 0.8306(2) 0.0661(6) Uani 1 1 d . . .
H3 H 1.0657 1.0805 0.9082 0.079 Uiso 1 1 calc R . .
C13 C 1.1290(3) 0.7683(2) 0.4221(2) 0.0610(6) Uani 1 1 d . . .
H13 H 1.0293 0.8047 0.4105 0.073 Uiso 1 1 calc R . .
C9 C 1.3075(3) 0.7252(2) 0.5413(2) 0.0582(6) Uani 1 1 d . . .
H9 H 1.3289 0.7325 0.6109 0.070 Uiso 1 1 calc R . .
C16 C 1.0196(3) 0.5554(2) 0.6960(2) 0.0640(6) Uani 1 1 d . . .
H16 H 0.9813 0.5546 0.6322 0.077 Uiso 1 1 calc R . .
C12 C 1.2487(4) 0.7021(3) 0.3340(2) 0.0820(9) Uani 1 1 d . . .
H12 H 1.2282 0.6943 0.2642 0.098 Uiso 1 1 calc R . .
C17 C 1.0984(4) 0.4502(2) 0.7328(3) 0.0783(8) Uani 1 1 d . . .
H17 H 1.1116 0.3798 0.6935 0.094 Uiso 1 1 calc R . .
C10 C 1.4257(3) 0.6591(2) 0.4530(3) 0.0711(7) Uani 1 1 d . . .
H10 H 1.5253 0.6218 0.4640 0.085 Uiso 1 1 calc R . .
C19 C 1.1373(3) 0.5545(3) 0.8834(2) 0.0688(7) Uani 1 1 d . . .
H19 H 1.1779 0.5550 0.9462 0.083 Uiso 1 1 calc R . .
C5 C 1.3063(3) 1.0856(2) 0.6437(2) 0.0622(6) Uani 1 1 d . . .
H5 H 1.3954 1.1236 0.5938 0.075 Uiso 1 1 calc R . .
C4 C 1.2434(3) 1.1150(2) 0.7585(2) 0.0643(6) Uani 1 1 d . . .
H4 H 1.2911 1.1713 0.7871 0.077 Uiso 1 1 calc R . .
C11 C 1.3954(4) 0.6489(3) 0.3494(3) 0.0813(9) Uani 1 1 d . . .
H11 H 1.4752 0.6055 0.2899 0.098 Uiso 1 1 calc R . .
C18 C 1.1557(3) 0.4508(3) 0.8256(3) 0.0792(9) Uani 1 1 d . . .
H18 H 1.2074 0.3807 0.8500 0.095 Uiso 1 1 calc R . .
O2 O 0.5346(3) 0.65272(17) 1.04455(16) 0.0805(6) Uani 1 1 d . . .
C23 C 0.3730(3) 0.8472(3) 0.9933(3) 0.0843(9) Uani 1 1 d . . .
H23A H 0.3221 0.8690 1.0730 0.126 Uiso 1 1 calc R . .
H23B H 0.2989 0.8021 0.9709 0.126 Uiso 1 1 calc R . .
H23C H 0.3914 0.9181 0.9450 0.126 Uiso 1 1 calc R . .
C22 C 0.5615(4) 0.6355(3) 0.7994(3) 0.0862(9) Uani 1 1 d . . .
H22A H 0.4752 0.6781 0.7710 0.129 Uiso 1 1 calc R . .
H22B H 0.5106 0.5823 0.8621 0.129 Uiso 1 1 calc R . .
H22C H 0.6431 0.5904 0.7380 0.129 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
O1 S1 1.4165(18) . ?
Cl1 C21 1.757(2) . ?
S1 O2 1.4233(19) . ?
S1 N1 1.6348(18) . ?
S1 C23 1.764(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.534(3) . ?
C21 C14 1.325(3) . ?
C21 N1 1.407(3) . ?
C14 C15 1.500(3) . ?
C14 C7 1.526(3) . ?
C6 C5 1.383(3) . ?
C6 H6 0.9300 . ?
C15 C16 1.382(3) . ?
C15 C20 1.385(3) . ?
C20 C19 1.386(3) . ?
C20 H20 0.9300 . ?
C8 C13 1.383(3) . ?
C8 C9 1.387(3) . ?
C8 C7 1.524(3) . ?
N1 C22 1.469(3) . ?
C7 H7 0.9800 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C13 C12 1.393(4) . ?
C13 H13 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C16 C17 1.403(4) . ?
C16 H16 0.9300 . ?
C12 C11 1.360(5) . ?
C12 H12 0.9300 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C19 C18 1.372(4) . ?
C19 H19 0.9300 . ?
C5 C4 1.372(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.07(13) . . ?
O1 S1 N1 106.21(10) . . ?
O2 S1 N1 106.81(11) . . ?
O1 S1 C23 108.21(14) . . ?
O2 S1 C23 107.52(14) . . ?
N1 S1 C23 107.42(13) . . ?
C2 C1 C6 117.77(19) . . ?
C2 C1 C7 122.75(18) . . ?
C6 C1 C7 119.37(18) . . ?
C14 C21 N1 123.84(18) . . ?
C14 C21 Cl1 121.79(16) . . ?
N1 C21 Cl1 114.35(14) . . ?
C21 C14 C15 117.58(18) . . ?
C21 C14 C7 123.39(18) . . ?
C15 C14 C7 119.03(15) . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C16 C15 C20 118.5(2) . . ?
C16 C15 C14 120.14(19) . . ?
C20 C15 C14 121.38(18) . . ?
C15 C20 C19 120.8(2) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C13 C8 C9 118.6(2) . . ?
C13 C8 C7 119.78(19) . . ?
C9 C8 C7 121.64(19) . . ?
C21 N1 C22 118.60(19) . . ?
C21 N1 S1 119.32(14) . . ?
C22 N1 S1 118.43(16) . . ?
C8 C7 C14 111.74(15) . . ?
C8 C7 C1 112.58(16) . . ?
C14 C7 C1 113.01(15) . . ?
C8 C7 H7 106.3 . . ?
C14 C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C8 C13 C12 120.4(3) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C15 C16 C17 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.042
