# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1056763'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31

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'

_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                   12.175(2)
_cell_length_b                   10.945(2)
_cell_length_c                   20.162(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.26(3)
_cell_angle_gamma                90
_cell_volume                     2686.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3451
_cell_measurement_theta_min      2.6853
_cell_measurement_theta_max      28.7645

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8535
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            7633
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2551
_reflns_number_gt                2235
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0501P)²+1.0632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2551
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
O1 O -0.12807(7) 0.71885(8) 0.47462(5) 0.0268(2) Uani 1 1 d . . . . .
O2 O 0.01739(8) 0.64519(8) 0.42079(5) 0.0298(3) Uani 1 1 d . . . . .
N1 N -0.09117(8) 0.94536(10) 0.43373(5) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.25793(10) 1.10761(12) 0.31827(7) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.2540 1.1552 0.3563 0.029 Uiso 1 1 calc R U . . .
C2 C 0.34551(11) 1.12152(12) 0.27625(7) 0.0282(3) Uani 1 1 d . . . . .
H2 H 0.4007 1.1774 0.2868 0.034 Uiso 1 1 calc R U . . .
C3 C 0.35173(11) 1.05286(13) 0.21863(7) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.4104 1.0630 0.1904 0.035 Uiso 1 1 calc R U . . .
C4 C 0.26977(11) 0.96919(13) 0.20362(7) 0.0277(3) Uani 1 1 d . . . . .
H4 H 0.2731 0.9231 0.1650 0.033 Uiso 1 1 calc R U . . .
C5 C 0.18254(11) 0.95377(12) 0.24599(6) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.1281 0.8968 0.2356 0.029 Uiso 1 1 calc R U . . .
C6 C 0.17548(10) 1.02253(12) 0.30380(6) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.08272(10) 1.00029(12) 0.34962(6) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.06418(10) 0.88101(12) 0.37122(6) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.1092 0.8176 0.3576 0.026 Uiso 1 1 calc R U . . .
C9 C -0.02224(10) 0.85827(11) 0.41320(6) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.01148(10) 1.09268(12) 0.37049(6) 0.0202(3) Uani 1 1 d . . . . .
C11 C -0.07486(10) 1.05983(12) 0.41253(6) 0.0203(3) Uani 1 1 d . . . . .
C12 C -0.15991(10) 1.15079(12) 0.43485(7) 0.0243(3) Uani 1 1 d . . . . .
H12A H -0.1651 1.1458 0.4827 0.029 Uiso 1 1 calc R U . . .
H12B H -0.2308 1.1276 0.4158 0.029 Uiso 1 1 calc R U . . .
C13 C -0.13640(11) 1.28275(12) 0.41591(6) 0.0249(3) Uani 1 1 d . . . . .
H13A H -0.2039 1.3297 0.4169 0.030 Uiso 1 1 calc R U . . .
H13B H -0.0849 1.3181 0.4479 0.030 Uiso 1 1 calc R U . . .
C14 C -0.08867(11) 1.28978(13) 0.34687(7) 0.0278(3) Uani 1 1 d . . . . .
H14A H -0.0784 1.3746 0.3344 0.033 Uiso 1 1 calc R U . . .
H14B H -0.1390 1.2525 0.3149 0.033 Uiso 1 1 calc R U . . .
C15 C 0.02137(11) 1.22306(12) 0.34665(7) 0.0254(3) Uani 1 1 d . . . . .
H15A H 0.0494 1.2232 0.3020 0.030 Uiso 1 1 calc R U . . .
H15B H 0.0736 1.2663 0.3751 0.030 Uiso 1 1 calc R U . . .
C16 C -0.04069(10) 0.72973(12) 0.43617(6) 0.0217(3) Uani 1 1 d . . . . .
C17 C -0.15246(12) 0.59552(13) 0.49651(7) 0.0301(3) Uani 1 1 d . . . . .
H17A H -0.1570 0.5421 0.4588 0.045 Uiso 1 1 calc R U . . .
H17B H -0.2213 0.5951 0.5188 0.045 Uiso 1 1 calc R U . . .
H17C H -0.0952 0.5678 0.5264 0.045 Uiso 1 1 calc R U . . .


_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 C16 1.3353(16) . ?
O1 C17 1.4528(16) . ?
O2 C16 1.2091(15) . ?
N1 C11 1.3400(17) . ?
N1 C9 1.3415(17) . ?
C1 C2 1.3848(19) . ?
C1 C6 1.3954(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3878(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3916(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4948(18) . ?
C7 C8 1.3961(18) . ?
C7 C10 1.4028(18) . ?
C8 C9 1.3872(18) . ?
C8 H8 0.9300 . ?
C9 C16 1.4997(18) . ?
C10 C11 1.4113(18) . ?
C10 C15 1.5114(18) . ?
C11 C12 1.5120(18) . ?
C12 C13 1.5227(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.5221(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5259(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 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
C16 O1 C17 115.47(10) . . ?
C11 N1 C9 117.89(11) . . ?
C2 C1 C6 120.36(13) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.65(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.32(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.27(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.79(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.60(12) . . ?
C5 C6 C7 119.41(11) . . ?
C1 C6 C7 121.95(12) . . ?
C8 C7 C10 118.38(12) . . ?
C8 C7 C6 118.33(11) . . ?
C10 C7 C6 123.27(11) . . ?
C9 C8 C7 119.21(12) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N1 C9 C8 123.29(12) . . ?
N1 C9 C16 118.18(11) . . ?
C8 C9 C16 118.53(11) . . ?
C7 C10 C11 118.04(12) . . ?
C7 C10 C15 122.08(11) . . ?
C11 C10 C15 119.81(11) . . ?
N1 C11 C10 123.18(11) . . ?
N1 C11 C12 114.42(11) . . ?
C10 C11 C12 122.35(12) . . ?
C11 C12 C13 114.59(11) . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 110.78(11) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 109.35(11) . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C10 C15 C14 112.01(11) . . ?
C10 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C10 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O2 C16 O1 123.96(12) . . ?
O2 C16 C9 123.11(12) . . ?
O1 C16 C9 112.93(11) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.12(19) . . . . ?
C4 C5 C6 C7 -177.69(11) . . . . ?
C2 C1 C6 C5 -0.95(19) . . . . ?
C2 C1 C6 C7 176.81(11) . . . . ?
C5 C6 C7 C8 52.76(16) . . . . ?
C1 C6 C7 C8 -124.98(13) . . . . ?
C5 C6 C7 C10 -125.37(13) . . . . ?
C1 C6 C7 C10 56.90(17) . . . . ?
C10 C7 C8 C9 -1.09(17) . . . . ?
C6 C7 C8 C9 -179.31(11) . . . . ?
C11 N1 C9 C8 -0.22(17) . . . . ?
C11 N1 C9 C16 -179.39(10) . . . . ?
C7 C8 C9 N1 1.09(18) . . . . ?
C7 C8 C9 C16 -179.73(11) . . . . ?
C8 C7 C10 C11 0.30(17) . . . . ?
C6 C7 C10 C11 178.42(11) . . . . ?
C8 C7 C10 C15 -176.60(11) . . . . ?
C6 C7 C10 C15 1.53(19) . . . . ?
C9 N1 C11 C10 -0.65(17) . . . . ?
C9 N1 C11 C12 176.72(10) . . . . ?
C7 C10 C11 N1 0.60(17) . . . . ?
C15 C10 C11 N1 177.56(11) . . . . ?
C7 C10 C11 C12 -176.56(11) . . . . ?
C15 C10 C11 C12 0.40(17) . . . . ?
N1 C11 C12 C13 175.01(11) . . . . ?
C10 C11 C12 C13 -7.60(17) . . . . ?
C11 C12 C13 C14 38.60(15) . . . . ?
C12 C13 C14 C15 -62.97(14) . . . . ?
C7 C10 C15 C14 152.29(12) . . . . ?
C11 C10 C15 C14 -24.55(16) . . . . ?
C13 C14 C15 C10 55.35(15) . . . . ?
C17 O1 C16 O2 -1.52(18) . . . . ?
C17 O1 C16 C9 177.90(11) . . . . ?
N1 C9 C16 O2 -179.44(12) . . . . ?
C8 C9 C16 O2 1.35(18) . . . . ?
N1 C9 C16 O1 1.14(16) . . . . ?
C8 C9 C16 O1 -178.08(10) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035

