# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_bs_sb2_0m
_database_code_depnum_ccdc_archive 'CCDC 1476263'
_audit_update_record             
;
2016-04-22 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35

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'

_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                   8.0877(4)
_cell_length_b                   8.9461(4)
_cell_length_c                   10.5339(5)
_cell_angle_alpha                93.626(2)
_cell_angle_beta                 92.834(2)
_cell_angle_gamma                94.652(2)
_cell_volume                     756.99(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7433
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            12347
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.63
_reflns_number_total             3439
_reflns_number_gt                3143
_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-2014 (Sheldrick, 2014)'
_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)+(0.0646P)²+0.1892P] 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         3439
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O 0.28817(9) 0.30708(9) 0.35478(7) 0.02082(19) Uani 1 1 d . . .
O3 O 0.27131(10) 0.53301(11) 0.94378(7) 0.0307(2) Uani 1 1 d . . .
N1 N 0.21969(11) 0.44662(10) 0.73468(8) 0.0193(2) Uani 1 1 d . . .
C14 C 0.26620(18) 0.05922(17) -0.00325(12) 0.0360(3) Uani 1 1 d . . .
H14A H 0.2070 0.1413 -0.0306 0.054 Uiso 1 1 calc R . .
H14B H 0.1984 -0.0334 -0.0220 0.054 Uiso 1 1 calc R . .
H14C H 0.3672 0.0559 -0.0472 0.054 Uiso 1 1 calc R . .
C13 C 0.30744(16) 0.08122(14) 0.13979(11) 0.0282(3) Uani 1 1 d . . .
H13A H 0.3602 -0.0054 0.1680 0.034 Uiso 1 1 calc R . .
H13B H 0.2052 0.0874 0.1836 0.034 Uiso 1 1 calc R . .
C12 C 0.42248(13) 0.22322(12) 0.17609(10) 0.0211(2) Uani 1 1 d . . .
H12A H 0.5316 0.2097 0.1451 0.025 Uiso 1 1 calc R . .
H12B H 0.3794 0.3072 0.1351 0.025 Uiso 1 1 calc R . .
C8 C 0.43836(13) 0.25907(12) 0.31724(10) 0.0187(2) Uani 1 1 d . . .
C7 C 0.25748(13) 0.34800(12) 0.47732(10) 0.0188(2) Uani 1 1 d . . .
C6 C 0.39137(13) 0.34238(11) 0.57400(9) 0.0171(2) Uani 1 1 d . . .
C1 C 0.36918(13) 0.38693(11) 0.70428(10) 0.0178(2) Uani 1 1 d . . .
C10 C 0.18097(13) 0.51917(12) 0.84684(10) 0.0204(2) Uani 1 1 d . . .
C11 C 0.01412(14) 0.58260(14) 0.84048(10) 0.0244(2) Uani 1 1 d . . .
H11A H -0.0619 0.5243 0.8888 0.037 Uiso 1 1 calc R . .
H11B H -0.0277 0.5790 0.7533 0.037 Uiso 1 1 calc R . .
H11C H 0.0255 0.6850 0.8752 0.037 Uiso 1 1 calc R . .
C2 C 0.49650(14) 0.37147(12) 0.79533(10) 0.0206(2) Uani 1 1 d . . .
H2 H 0.4830 0.3974 0.8808 0.025 Uiso 1 1 calc R . .
C3 C 0.64398(14) 0.31695(12) 0.75756(10) 0.0222(2) Uani 1 1 d . . .
H3 H 0.7280 0.3066 0.8191 0.027 Uiso 1 1 calc R . .
C4 C 0.66977(13) 0.27762(12) 0.63112(10) 0.0206(2) Uani 1 1 d . . .
H4 H 0.7708 0.2438 0.6088 0.025 Uiso 1 1 calc R . .
C5 C 0.54353(13) 0.28884(11) 0.53697(10) 0.0177(2) Uani 1 1 d . . .
C9 C 0.56491(13) 0.24729(11) 0.40247(10) 0.0179(2) Uani 1 1 d . . .
C15 C 0.72706(13) 0.19116(12) 0.36175(10) 0.0196(2) Uani 1 1 d . . .
H15A H 0.8182 0.2505 0.4091 0.024 Uiso 1 1 calc R . .
H15B H 0.7377 0.2067 0.2721 0.024 Uiso 1 1 calc R . .
C16 C 0.74238(13) 0.02435(12) 0.38242(10) 0.0207(2) Uani 1 1 d . . .
H16A H 0.7326 0.0078 0.4720 0.025 Uiso 1 1 calc R . .
H16B H 0.6525 -0.0361 0.3345 0.025 Uiso 1 1 calc R . .
C17 C 0.90861(14) -0.02494(13) 0.33991(11) 0.0240(2) Uani 1 1 d . . .
H17A H 0.9150 -0.0154 0.2500 0.036 Uiso 1 1 calc R . .
H17B H 0.9177 -0.1278 0.3582 0.036 Uiso 1 1 calc R . .
H17C H 0.9977 0.0375 0.3848 0.036 Uiso 1 1 calc R . .
O2 O 0.11685(10) 0.38347(10) 0.49395(7) 0.0254(2) Uani 1 1 d . . .
H1A H 0.1449(19) 0.4458(17) 0.6664(15) 0.032(4) Uiso 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
O1 C7 1.3596(12) . ?
O1 C8 1.3881(12) . ?
O3 C10 1.2196(14) . ?
N1 C10 1.3740(13) . ?
N1 C1 1.4038(13) . ?
N1 H1A 0.916(16) . ?
C14 C13 1.5239(16) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C12 1.5288(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C8 1.4981(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 C9 1.3429(15) . ?
C7 O2 1.2232(13) . ?
C7 C6 1.4555(14) . ?
C6 C5 1.4197(14) . ?
C6 C1 1.4287(14) . ?
C1 C2 1.3933(14) . ?
C10 C11 1.5059(15) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C2 C3 1.3912(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.3862(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.4019(14) . ?
C4 H4 0.9300 . ?
C5 C9 1.4640(14) . ?
C9 C15 1.5136(14) . ?
C15 C16 1.5356(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.5275(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C7 O1 C8 123.88(8) . . ?
C10 N1 C1 128.60(9) . . ?
C10 N1 H1A 117.4(9) . . ?
C1 N1 H1A 113.6(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C14 C13 C12 112.35(10) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C8 C12 C13 112.05(9) . . ?
C8 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C8 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C9 C8 O1 121.26(9) . . ?
C9 C8 C12 130.93(10) . . ?
O1 C8 C12 107.78(8) . . ?
O2 C7 O1 115.26(9) . . ?
O2 C7 C6 127.09(9) . . ?
O1 C7 C6 117.64(9) . . ?
C5 C6 C1 120.50(9) . . ?
C5 C6 C7 118.78(9) . . ?
C1 C6 C7 120.71(9) . . ?
C2 C1 N1 122.76(9) . . ?
C2 C1 C6 119.08(10) . . ?
N1 C1 C6 118.16(9) . . ?
O3 C10 N1 124.32(10) . . ?
O3 C10 C11 121.87(10) . . ?
N1 C10 C11 113.81(9) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C2 C1 119.62(10) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 122.12(10) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.98(10) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 118.65(9) . . ?
C4 C5 C9 121.81(9) . . ?
C6 C5 C9 119.54(9) . . ?
C8 C9 C5 118.82(9) . . ?
C8 C9 C15 121.17(9) . . ?
C5 C9 C15 120.00(9) . . ?
C9 C15 C16 113.78(8) . . ?
C9 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C9 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 111.15(9) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.094
