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

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

data_exp_5503
_database_code_depnum_ccdc_archive 'CCDC 1855184'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br Mn N2 O3 S'
_chemical_formula_weight         477.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   16.5242(15)
_cell_length_b                   9.5030(8)
_cell_length_c                   26.035(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4088.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2262
_cell_measurement_theta_min      3.6090
_cell_measurement_theta_max      25.6300

_exptl_crystal_description       dumble
_exptl_crystal_colour            reddish
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    2.721
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9731
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3597
_reflns_number_gt                2444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0813P)²+0.0000P] 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         3597
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_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 0.38130(4) 0.11211(5) 0.30784(3) 0.0541(2) Uani 1 1 d . . .
Mn1 Mn 0.45897(5) 0.51252(8) 0.38604(3) 0.0379(3) Uani 1 1 d . . .
S1 S 0.43326(8) 0.73432(13) 0.34852(5) 0.0399(4) Uani 1 1 d . . .
N1 N 0.3602(3) 0.5707(4) 0.42925(17) 0.0407(11) Uani 1 1 d . . .
N2 N 0.3671(3) 0.4434(4) 0.33756(17) 0.0403(10) Uani 1 1 d . . .
H13 H 0.3816 0.3561 0.3265 0.048 Uiso 1 1 calc R . .
O3 O 0.5838(3) 0.4134(5) 0.31378(19) 0.0731(14) Uani 1 1 d . . .
O2 O 0.5879(3) 0.6235(5) 0.4534(2) 0.0798(15) Uani 1 1 d . . .
O1 O 0.4794(3) 0.2400(4) 0.43919(17) 0.0707(13) Uani 1 1 d . . .
C4 C 0.2169(4) 0.5550(6) 0.4367(2) 0.0547(15) Uani 1 1 d . . .
H16 H 0.1682 0.5191 0.4244 0.066 Uiso 1 1 calc R . .
C8 C 0.3519(3) 0.6849(5) 0.3055(2) 0.0444(13) Uani 1 1 d . . .
H11A H 0.3003 0.7019 0.3221 0.053 Uiso 1 1 calc R . .
H11B H 0.3543 0.7425 0.2747 0.053 Uiso 1 1 calc R . .
C5 C 0.2887(3) 0.5217(5) 0.4125(2) 0.0403(13) Uani 1 1 d . . .
C6 C 0.2913(3) 0.4263(5) 0.3667(2) 0.0444(14) Uani 1 1 d . . .
H14A H 0.2864 0.3294 0.3780 0.053 Uiso 1 1 calc R . .
H14B H 0.2457 0.4469 0.3445 0.053 Uiso 1 1 calc R . .
C10 C 0.5837(3) 0.8434(6) 0.3314(2) 0.0478(14) Uani 1 1 d . . .
C9 C 0.5105(3) 0.7905(6) 0.3035(2) 0.0469(14) Uani 1 1 d . . .
H9A H 0.5256 0.7121 0.2817 0.056 Uiso 1 1 calc R . .
H9B H 0.4890 0.8646 0.2818 0.056 Uiso 1 1 calc R . .
C17 C 0.5368(4) 0.5827(6) 0.4275(2) 0.0490(14) Uani 1 1 d . . .
C7 C 0.3579(3) 0.5325(5) 0.2908(2) 0.0451(14) Uani 1 1 d . . .
H12A H 0.3097 0.5046 0.2723 0.054 Uiso 1 1 calc R . .
H12B H 0.4042 0.5188 0.2684 0.054 Uiso 1 1 calc R . .
C1 C 0.3606(4) 0.6570(6) 0.4704(2) 0.0537(15) Uani 1 1 d . . .
H19 H 0.4097 0.6935 0.4817 0.064 Uiso 1 1 calc R . .
C18 C 0.5359(3) 0.4571(6) 0.3411(2) 0.0457(14) Uani 1 1 d . . .
C16 C 0.4681(4) 0.3440(6) 0.4180(2) 0.0507(15) Uani 1 1 d . . .
C11 C 0.6578(4) 0.7795(7) 0.3251(3) 0.0651(18) Uani 1 1 d . . .
H4 H 0.6622 0.7002 0.3043 0.078 Uiso 1 1 calc R . .
C3 C 0.2177(4) 0.6421(7) 0.4792(3) 0.0693(19) Uani 1 1 d . . .
H17 H 0.1698 0.6657 0.4959 0.083 Uiso 1 1 calc R . .
C2 C 0.2908(4) 0.6929(7) 0.4961(2) 0.0671(18) Uani 1 1 d . . .
H18 H 0.2931 0.7511 0.5248 0.081 Uiso 1 1 calc R . .
C15 C 0.5782(4) 0.9607(7) 0.3632(3) 0.072(2) Uani 1 1 d . . .
H8 H 0.5286 1.0049 0.3680 0.087 Uiso 1 1 calc R . .
C13 C 0.7192(5) 0.9476(10) 0.3806(4) 0.097(3) Uani 1 1 d . . .
H6 H 0.7650 0.9823 0.3971 0.117 Uiso 1 1 calc R . .
C14 C 0.6462(6) 1.0114(8) 0.3874(3) 0.100(3) Uani 1 1 d . . .
H7 H 0.6422 1.0899 0.4087 0.120 Uiso 1 1 calc R . .
C12 C 0.7251(4) 0.8320(9) 0.3493(3) 0.087(2) Uani 1 1 d . . .
H5 H 0.7751 0.7889 0.3444 0.104 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
Mn1 C17 1.806(6) . ?
Mn1 C18 1.807(6) . ?
Mn1 C16 1.811(6) . ?
Mn1 N1 2.058(4) . ?
Mn1 N2 2.081(4) . ?
Mn1 S1 2.3617(15) . ?
S1 C9 1.813(5) . ?
S1 C8 1.813(5) . ?
N1 C5 1.343(6) . ?
N1 C1 1.349(7) . ?
N2 C6 1.473(6) . ?
N2 C7 1.490(7) . ?
N2 H13 0.9100 . ?
O3 C18 1.141(6) . ?
O2 C17 1.148(6) . ?
O1 C16 1.147(6) . ?
C4 C5 1.380(7) . ?
C4 C3 1.382(9) . ?
C4 H16 0.9300 . ?
C8 C7 1.500(7) . ?
C8 H11A 0.9700 . ?
C8 H11B 0.9700 . ?
C5 C6 1.498(7) . ?
C6 H14A 0.9700 . ?
C6 H14B 0.9700 . ?
C10 C11 1.376(8) . ?
C10 C15 1.391(9) . ?
C10 C9 1.498(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H12A 0.9700 . ?
C7 H12B 0.9700 . ?
C1 C2 1.377(8) . ?
C1 H19 0.9300 . ?
C11 C12 1.373(9) . ?
C11 H4 0.9300 . ?
C3 C2 1.374(9) . ?
C3 H17 0.9300 . ?
C2 H18 0.9300 . ?
C15 C14 1.376(10) . ?
C15 H8 0.9300 . ?
C13 C14 1.363(11) . ?
C13 C12 1.371(11) . ?
C13 H6 0.9300 . ?
C14 H7 0.9300 . ?
C12 H5 0.9300 . ?

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
C17 Mn1 C18 89.6(3) . . ?
C17 Mn1 C16 89.6(3) . . ?
C18 Mn1 C16 89.0(3) . . ?
C17 Mn1 N1 98.0(2) . . ?
C18 Mn1 N1 172.1(2) . . ?
C16 Mn1 N1 93.0(2) . . ?
C17 Mn1 N2 176.7(2) . . ?
C18 Mn1 N2 91.6(2) . . ?
C16 Mn1 N2 93.5(2) . . ?
N1 Mn1 N2 80.65(18) . . ?
C17 Mn1 S1 92.61(19) . . ?
C18 Mn1 S1 96.81(18) . . ?
C16 Mn1 S1 173.8(2) . . ?
N1 Mn1 S1 81.01(12) . . ?
N2 Mn1 S1 84.23(12) . . ?
C9 S1 C8 101.5(3) . . ?
C9 S1 Mn1 113.81(18) . . ?
C8 S1 Mn1 99.08(17) . . ?
C5 N1 C1 118.3(5) . . ?
C5 N1 Mn1 115.3(3) . . ?
C1 N1 Mn1 126.4(4) . . ?
C6 N2 C7 113.4(4) . . ?
C6 N2 Mn1 110.1(3) . . ?
C7 N2 Mn1 112.9(3) . . ?
C6 N2 H13 106.7 . . ?
C7 N2 H13 106.7 . . ?
Mn1 N2 H13 106.7 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H16 120.2 . . ?
C3 C4 H16 120.2 . . ?
C7 C8 S1 110.9(3) . . ?
C7 C8 H11A 109.5 . . ?
S1 C8 H11A 109.5 . . ?
C7 C8 H11B 109.5 . . ?
S1 C8 H11B 109.5 . . ?
H11A C8 H11B 108.0 . . ?
N1 C5 C4 121.9(5) . . ?
N1 C5 C6 116.3(5) . . ?
C4 C5 C6 121.7(5) . . ?
N2 C6 C5 111.5(4) . . ?
N2 C6 H14A 109.3 . . ?
C5 C6 H14A 109.3 . . ?
N2 C6 H14B 109.3 . . ?
C5 C6 H14B 109.3 . . ?
H14A C6 H14B 108.0 . . ?
C11 C10 C15 118.8(6) . . ?
C11 C10 C9 120.8(6) . . ?
C15 C10 C9 120.3(6) . . ?
C10 C9 S1 110.7(4) . . ?
C10 C9 H9A 109.5 . . ?
S1 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C17 Mn1 177.7(6) . . ?
N2 C7 C8 110.4(4) . . ?
N2 C7 H12A 109.6 . . ?
C8 C7 H12A 109.6 . . ?
N2 C7 H12B 109.6 . . ?
C8 C7 H12B 109.6 . . ?
H12A C7 H12B 108.1 . . ?
N1 C1 C2 122.2(6) . . ?
N1 C1 H19 118.9 . . ?
C2 C1 H19 118.9 . . ?
O3 C18 Mn1 175.5(6) . . ?
O1 C16 Mn1 175.1(6) . . ?
C12 C11 C10 120.4(7) . . ?
C12 C11 H4 119.8 . . ?
C10 C11 H4 119.8 . . ?
C2 C3 C4 118.4(6) . . ?
C2 C3 H17 120.8 . . ?
C4 C3 H17 120.8 . . ?
C3 C2 C1 119.6(6) . . ?
C3 C2 H18 120.2 . . ?
C1 C2 H18 120.2 . . ?
C14 C15 C10 120.0(7) . . ?
C14 C15 H8 120.0 . . ?
C10 C15 H8 120.0 . . ?
C14 C13 C12 119.9(8) . . ?
C14 C13 H6 120.1 . . ?
C12 C13 H6 120.1 . . ?
C13 C14 C15 120.4(8) . . ?
C13 C14 H7 119.8 . . ?
C15 C14 H7 119.8 . . ?
C13 C12 C11 120.4(7) . . ?
C13 C12 H5 119.8 . . ?
C11 C12 H5 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.106
