# Electronic Supplementary Material (ESI) for ChemComm.
# 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_z063m
_database_code_depnum_ccdc_archive 'CCDC 1404860'
_audit_update_record             
;
2015-06-04 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        lcy-Q-103
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H36 Br N3 O3 S'
_chemical_formula_sum            'C35 H36 Br N3 O3 S'
_chemical_formula_weight         658.64

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'
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   P2(1)

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

_cell_length_a                   9.4805(11)
_cell_length_b                   15.3417(19)
_cell_length_c                   11.8162(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.930(2)
_cell_angle_gamma                90.00
_cell_volume                     1594.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            coloress
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7679
_exptl_absorpt_correction_T_max  0.8181
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10385
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.05
_reflns_number_total             6126
_reflns_number_gt                5145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0710P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6126
_refine_ls_number_parameters     393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.010
_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 0.37522(5) 0.71143(4) -0.31710(4) 0.04606(16) Uani 1 1 d . . .
S2 S 0.11775(14) 0.63514(8) 0.34704(11) 0.0385(3) Uani 1 1 d . . .
C1 C 0.1129(5) 0.6290(3) -0.0686(4) 0.0298(9) Uani 1 1 d . . .
C2 C 0.2709(5) 0.6759(3) -0.2167(4) 0.0338(10) Uani 1 1 d . . .
N3 N 0.0976(4) 0.6258(2) 0.1263(3) 0.0319(8) Uani 1 1 d . . .
C3 C 0.1281(5) 0.6396(3) -0.2680(4) 0.0334(10) Uani 1 1 d . . .
H3 H 0.0850 0.6300 -0.3517 0.040 Uiso 1 1 calc R . .
O1 O -0.7444(3) 0.3399(2) -0.2924(3) 0.0388(8) Uani 1 1 d . . .
C4 C 0.0273(5) 0.6083(3) 0.0107(4) 0.0315(10) Uani 1 1 d . . .
N1 N 0.0749(4) 0.3867(2) 0.0861(3) 0.0297(8) Uani 1 1 d . . .
C5 C -0.6059(5) 0.3784(3) -0.2406(4) 0.0349(11) Uani 1 1 d . . .
N2 N 0.0216(5) 0.6061(3) 0.2032(4) 0.0389(10) Uani 1 1 d . . .
H2 H -0.0662 0.5815 0.1789 0.047 Uiso 1 1 calc R . .
O3 O 0.0338(4) 0.5983(3) 0.4122(3) 0.0510(10) Uani 1 1 d . . .
C6 C 0.1771(5) 0.3920(3) 0.0180(4) 0.0350(11) Uani 1 1 d . . .
H6 H 0.1276 0.4297 -0.0527 0.042 Uiso 1 1 calc R . .
C7 C 0.0499(5) 0.6175(3) -0.1954(4) 0.0300(10) Uani 1 1 d . . .
H7 H -0.0474 0.5944 -0.2311 0.036 Uiso 1 1 calc R . .
O2 O 0.1423(4) 0.7267(2) 0.3467(3) 0.0546(10) Uani 1 1 d . . .
C8 C 0.2589(5) 0.6616(3) -0.0179(4) 0.0356(11) Uani 1 1 d . . .
H8 H 0.3050 0.6667 0.0665 0.043 Uiso 1 1 calc R . .
C9 C -0.0672(5) 0.4263(3) 0.0552(4) 0.0297(10) Uani 1 1 d . . .
C10 C -0.0086(5) 0.3637(3) 0.2405(4) 0.0295(9) Uani 1 1 d . . .
C11 C -0.1428(5) 0.4746(3) -0.0644(4) 0.0286(9) Uani 1 1 d . . .
H11 H -0.0876 0.4598 -0.1174 0.034 Uiso 1 1 calc R . .
C12 C -0.3373(5) 0.3554(3) -0.1548(5) 0.0351(10) Uani 1 1 d . . .
H12 H -0.2552 0.3173 -0.1352 0.042 Uiso 1 1 calc R . .
C13 C -0.1197(5) 0.4137(3) 0.1476(4) 0.0287(9) Uani 1 1 d . . .
C14 C 0.0047(6) 0.3314(3) 0.3541(4) 0.0352(11) Uani 1 1 d . . .
H14 H -0.0710 0.3433 0.3842 0.042 Uiso 1 1 calc R . .
C15 C -0.5829(6) 0.4665(3) -0.2183(5) 0.0444(13) Uani 1 1 d . . .
H15 H -0.6650 0.5046 -0.2389 0.053 Uiso 1 1 calc R . .
C16 C 0.1104(5) 0.3474(3) 0.1993(4) 0.0301(10) Uani 1 1 d . . .
C17 C -0.3102(5) 0.4434(3) -0.1294(4) 0.0260(9) Uani 1 1 d . . .
C18 C 0.5544(6) 0.5866(4) 0.4159(6) 0.0512(14) Uani 1 1 d . . .
H18 H 0.6350 0.6151 0.4051 0.061 Uiso 1 1 calc R . .
C19 C 0.5791(6) 0.5053(4) 0.4691(5) 0.0466(13) Uani 1 1 d . . .
C20 C 0.3383(5) 0.6868(3) -0.0900(4) 0.0358(11) Uani 1 1 d . . .
H20 H 0.4352 0.7107 -0.0547 0.043 Uiso 1 1 calc R . .
C21 C 0.2978(5) 0.5841(3) 0.3930(4) 0.0362(11) Uani 1 1 d . . .
C22 C -0.1308(5) 0.5735(3) -0.0442(4) 0.0306(10) Uani 1 1 d . . .
H22A H -0.1820 0.6021 -0.1221 0.037 Uiso 1 1 calc R . .
H22B H -0.1846 0.5891 0.0084 0.037 Uiso 1 1 calc R . .
C23 C 0.7357(7) 0.4618(5) 0.5160(7) 0.075(2) Uani 1 1 d . . .
H23A H 0.7242 0.4005 0.4993 0.113 Uiso 1 1 calc R . .
H23B H 0.7838 0.4709 0.6024 0.113 Uiso 1 1 calc R . .
H23C H 0.7972 0.4868 0.4757 0.113 Uiso 1 1 calc R . .
C24 C -0.4333(5) 0.4976(3) -0.1638(5) 0.0399(12) Uani 1 1 d . . .
H24 H -0.4175 0.5572 -0.1508 0.048 Uiso 1 1 calc R . .
C25 C 0.2372(5) 0.2969(3) 0.2674(5) 0.0391(11) Uani 1 1 d . . .
H25 H 0.3142 0.2850 0.2388 0.047 Uiso 1 1 calc R . .
C26 C -0.4825(5) 0.3228(3) -0.2083(5) 0.0362(11) Uani 1 1 d . . .
H26 H -0.4976 0.2633 -0.2228 0.043 Uiso 1 1 calc R . .
C27 C -0.8759(5) 0.3953(3) -0.3247(5) 0.0427(12) Uani 1 1 d . . .
H27A H -0.8762 0.4351 -0.3875 0.064 Uiso 1 1 calc R . .
H27B H -0.8729 0.4276 -0.2543 0.064 Uiso 1 1 calc R . .
H27C H -0.9663 0.3603 -0.3539 0.064 Uiso 1 1 calc R . .
C28 C 0.1268(6) 0.2828(3) 0.4217(5) 0.0424(12) Uani 1 1 d . . .
H28 H 0.1334 0.2608 0.4969 0.051 Uiso 1 1 calc R . .
C29 C 0.4172(6) 0.6268(3) 0.3785(5) 0.0481(13) Uani 1 1 d . . .
H29 H 0.4043 0.6821 0.3438 0.058 Uiso 1 1 calc R . .
C30 C -0.2680(5) 0.4414(4) 0.1550(5) 0.0417(12) Uani 1 1 d . . .
H30A H -0.3240 0.4758 0.0846 0.063 Uiso 1 1 calc R . .
H30B H -0.2485 0.4755 0.2274 0.063 Uiso 1 1 calc R . .
H30C H -0.3261 0.3908 0.1575 0.063 Uiso 1 1 calc R . .
C31 C 0.4576(6) 0.4635(4) 0.4827(6) 0.0543(15) Uani 1 1 d . . .
H31 H 0.4718 0.4090 0.5196 0.065 Uiso 1 1 calc R . .
C32 C 0.3168(6) 0.5010(3) 0.4429(5) 0.0448(12) Uani 1 1 d . . .
H32 H 0.2346 0.4712 0.4492 0.054 Uiso 1 1 calc R . .
C33 C 0.3274(6) 0.4355(4) 0.0954(6) 0.0503(14) Uani 1 1 d . . .
H33A H 0.3834 0.3977 0.1618 0.075 Uiso 1 1 calc R . .
H33B H 0.3073 0.4897 0.1271 0.075 Uiso 1 1 calc R . .
H33C H 0.3861 0.4462 0.0459 0.075 Uiso 1 1 calc R . .
C34 C 0.2428(6) 0.2658(3) 0.3782(5) 0.0464(13) Uani 1 1 d . . .
H34 H 0.3259 0.2326 0.4256 0.056 Uiso 1 1 calc R . .
C35 C 0.1977(6) 0.3031(3) -0.0306(5) 0.0453(13) Uani 1 1 d . . .
H35A H 0.1007 0.2812 -0.0836 0.068 Uiso 1 1 calc R . .
H35B H 0.2419 0.2636 0.0364 0.068 Uiso 1 1 calc R . .
H35C H 0.2637 0.3084 -0.0752 0.068 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
Br1 C2 1.887(5) . ?
S2 O3 1.416(4) . ?
S2 O2 1.424(4) . ?
S2 N2 1.662(4) . ?
S2 C21 1.769(5) . ?
C1 C8 1.381(6) . ?
C1 C7 1.401(6) . ?
C1 C4 1.485(7) . ?
C2 C3 1.378(6) . ?
C2 C20 1.401(6) . ?
N3 C4 1.305(6) . ?
N3 N2 1.388(6) . ?
C3 C7 1.369(6) . ?
O1 C5 1.359(5) . ?
O1 C27 1.438(6) . ?
C4 C22 1.491(6) . ?
N1 C16 1.389(6) . ?
N1 C9 1.397(5) . ?
N1 C6 1.475(6) . ?
C5 C15 1.378(7) . ?
C5 C26 1.382(6) . ?
C6 C35 1.522(7) . ?
C6 C33 1.529(7) . ?
C8 C20 1.386(7) . ?
C9 C13 1.372(6) . ?
C9 C11 1.518(6) . ?
C10 C14 1.393(6) . ?
C10 C16 1.408(6) . ?
C10 C13 1.427(6) . ?
C11 C22 1.535(6) . ?
C11 C17 1.558(6) . ?
C12 C26 1.376(6) . ?
C12 C17 1.387(6) . ?
C13 C30 1.502(6) . ?
C14 C28 1.357(7) . ?
C15 C24 1.404(7) . ?
C16 C25 1.403(6) . ?
C17 C24 1.364(6) . ?
C18 C29 1.356(8) . ?
C18 C19 1.376(8) . ?
C19 C31 1.380(8) . ?
C19 C23 1.530(8) . ?
C21 C29 1.372(7) . ?
C21 C32 1.388(7) . ?
C25 C34 1.376(7) . ?
C28 C34 1.402(8) . ?
C31 C32 1.365(8) . ?

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
O3 S2 O2 121.4(2) . . ?
O3 S2 N2 104.1(2) . . ?
O2 S2 N2 106.8(2) . . ?
O3 S2 C21 109.3(2) . . ?
O2 S2 C21 107.3(2) . . ?
N2 S2 C21 107.0(2) . . ?
C8 C1 C7 117.9(4) . . ?
C8 C1 C4 120.0(4) . . ?
C7 C1 C4 122.2(4) . . ?
C3 C2 C20 120.0(4) . . ?
C3 C2 Br1 120.0(4) . . ?
C20 C2 Br1 120.0(3) . . ?
C4 N3 N2 116.9(4) . . ?
C7 C3 C2 119.8(4) . . ?
C5 O1 C27 117.3(4) . . ?
N3 C4 C1 115.5(4) . . ?
N3 C4 C22 124.5(4) . . ?
C1 C4 C22 120.0(4) . . ?
C16 N1 C9 107.7(4) . . ?
C16 N1 C6 125.2(3) . . ?
C9 N1 C6 126.8(4) . . ?
O1 C5 C15 124.7(4) . . ?
O1 C5 C26 115.6(4) . . ?
C15 C5 C26 119.7(4) . . ?
N3 N2 S2 113.0(3) . . ?
N1 C6 C35 111.0(4) . . ?
N1 C6 C33 110.7(4) . . ?
C35 C6 C33 113.2(4) . . ?
C3 C7 C1 121.6(4) . . ?
C1 C8 C20 121.4(4) . . ?
C13 C9 N1 109.4(4) . . ?
C13 C9 C11 128.7(4) . . ?
N1 C9 C11 122.0(4) . . ?
C14 C10 C16 118.3(4) . . ?
C14 C10 C13 135.0(4) . . ?
C16 C10 C13 106.7(4) . . ?
C9 C11 C22 110.8(4) . . ?
C9 C11 C17 110.5(3) . . ?
C22 C11 C17 112.5(3) . . ?
C26 C12 C17 121.7(4) . . ?
C9 C13 C10 107.7(4) . . ?
C9 C13 C30 129.1(4) . . ?
C10 C13 C30 123.1(4) . . ?
C28 C14 C10 120.9(5) . . ?
C5 C15 C24 118.7(4) . . ?
N1 C16 C25 129.7(4) . . ?
N1 C16 C10 108.5(4) . . ?
C25 C16 C10 121.7(4) . . ?
C24 C17 C12 117.4(4) . . ?
C24 C17 C11 124.1(4) . . ?
C12 C17 C11 118.5(4) . . ?
C29 C18 C19 122.7(5) . . ?
C18 C19 C31 117.8(5) . . ?
C18 C19 C23 122.5(6) . . ?
C31 C19 C23 119.6(6) . . ?
C8 C20 C2 119.2(4) . . ?
C29 C21 C32 120.6(5) . . ?
C29 C21 S2 119.8(4) . . ?
C32 C21 S2 119.6(4) . . ?
C4 C22 C11 115.2(4) . . ?
C17 C24 C15 122.4(4) . . ?
C34 C25 C16 117.2(5) . . ?
C12 C26 C5 120.0(4) . . ?
C14 C28 C34 120.0(5) . . ?
C18 C29 C21 118.5(5) . . ?
C32 C31 C19 121.0(6) . . ?
C31 C32 C21 119.2(5) . . ?
C25 C34 C28 121.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.103
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Trichloromethane and petroleum ether'
