# 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_130409lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1057272'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-04-28 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 H17 N O2'
_chemical_formula_weight         267.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_hall  '-P 2yn'

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                   7.8554(7)
_cell_length_b                   19.1071(17)
_cell_length_c                   9.8166(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.458(2)
_cell_angle_gamma                90.00
_cell_volume                     1361.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3691
_cell_measurement_theta_min      2.4852
_cell_measurement_theta_max      26.4505

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8490
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_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 8.3333
_diffrn_reflns_number            10878
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2802
_reflns_number_gt                2300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0438P)²+0.5884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2802
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.34798(13) 1.05785(5) 0.89596(10) 0.0195(2) Uani 1 1 d . . .
O2 O 0.26898(12) 0.99196(5) 0.69311(10) 0.0170(2) Uani 1 1 d . . .
N1 N 0.02923(14) 0.86754(6) 0.40774(12) 0.0152(2) Uani 1 1 d . . .
C1 C 0.45655(19) 1.12976(7) 1.10988(15) 0.0219(3) Uani 1 1 d . . .
H1A H 0.5817 1.1138 1.1273 0.033 Uiso 1 1 calc R . .
H1B H 0.4467 1.1399 1.2045 0.033 Uiso 1 1 calc R . .
H1C H 0.4296 1.1723 1.0494 0.033 Uiso 1 1 calc R . .
C2 C 0.32121(19) 1.07359(7) 1.03097(15) 0.0205(3) Uani 1 1 d . . .
H2A H 0.3426 1.0312 1.0934 0.025 Uiso 1 1 calc R . .
H2B H 0.1937 1.0900 1.0081 0.025 Uiso 1 1 calc R . .
C3 C 0.23173(18) 1.00987(7) 0.81209(14) 0.0169(3) Uani 1 1 d . . .
C4 C 0.13788(17) 0.94154(7) 0.61743(14) 0.0162(3) Uani 1 1 d . . .
C5 C 0.15617(17) 0.91289(7) 0.48675(14) 0.0160(3) Uani 1 1 d . . .
C6 C -0.09189(18) 0.79014(7) 0.20183(14) 0.0166(3) Uani 1 1 d . . .
C7 C -0.07884(19) 0.76088(7) 0.07808(15) 0.0195(3) Uani 1 1 d . . .
H7 H -0.1682 0.7275 0.0231 0.023 Uiso 1 1 calc R . .
C8 C 0.06365(19) 0.77915(8) 0.03079(15) 0.0223(3) Uani 1 1 d . . .
H8 H 0.0680 0.7585 -0.0558 0.027 Uiso 1 1 calc R . .
C9 C -0.24633(19) 0.77152(7) 0.25014(16) 0.0207(3) Uani 1 1 d . . .
H9A H -0.3220 0.7346 0.1862 0.031 Uiso 1 1 calc R . .
H9B H -0.3226 0.8130 0.2434 0.031 Uiso 1 1 calc R . .
H9C H -0.1950 0.7549 0.3523 0.031 Uiso 1 1 calc R . .
C10 C 0.19567(19) 0.82646(8) 0.10884(15) 0.0216(3) Uani 1 1 d . . .
H10 H 0.2912 0.8386 0.0762 0.026 Uiso 1 1 calc R . .
C11 C 0.19012(18) 0.85738(7) 0.23814(15) 0.0177(3) Uani 1 1 d . . .
C12 C 0.32393(18) 0.90530(7) 0.32701(15) 0.0203(3) Uani 1 1 d . . .
H12 H 0.4243 0.9184 0.3010 0.024 Uiso 1 1 calc R . .
C13 C 0.30854(19) 0.93264(7) 0.44985(15) 0.0202(3) Uani 1 1 d . . .
H13 H 0.3983 0.9645 0.5104 0.024 Uiso 1 1 calc R . .
C14 C 0.02304(18) 0.92979(7) 0.68987(14) 0.0176(3) Uani 1 1 d . . .
C15 C 0.08545(18) 0.97405(7) 0.81720(15) 0.0187(3) Uani 1 1 d . . .
H15 H 0.0345 0.9776 0.8905 0.022 Uiso 1 1 calc R . .
C16 C -0.13838(16) 0.88134(7) 0.64820(12) 0.0237(3) Uani 1 1 d . . .
H16A H -0.2524 0.9087 0.6167 0.035 Uiso 1 1 calc R . .
H16B H -0.1287 0.8525 0.7334 0.035 Uiso 1 1 calc R . .
H16C H -0.1398 0.8510 0.5672 0.035 Uiso 1 1 calc R . .
C17 C 0.04410(14) 0.83952(6) 0.28467(11) 0.0151(3) Uani 1 1 d 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 C3 1.3334(16) . ?
O1 C2 1.4505(16) . ?
O2 C3 1.3521(15) . ?
O2 C4 1.3985(15) . ?
N1 C5 1.3252(17) . ?
N1 C17 1.3665(14) . ?
C1 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C15 1.3548(19) . ?
C4 C14 1.3638(18) . ?
C4 C5 1.4514(18) . ?
C5 C13 1.4273(18) . ?
C6 C7 1.3762(19) . ?
C6 C17 1.4244(16) . ?
C6 C9 1.5043(18) . ?
C7 C8 1.4097(19) . ?
C7 H7 0.9500 . ?
C8 C10 1.368(2) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4157(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4155(19) . ?
C11 C17 1.4287(15) . ?
C12 C13 1.3613(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.4316(19) . ?
C14 C16 1.4953(16) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C3 O1 C2 113.74(10) . . ?
C3 O2 C4 105.95(10) . . ?
C5 N1 C17 118.31(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.37(11) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O1 C3 O2 112.60(11) . . ?
O1 C3 C15 135.64(12) . . ?
O2 C3 C15 111.75(12) . . ?
C14 C4 O2 109.63(11) . . ?
C14 C4 C5 135.02(12) . . ?
O2 C4 C5 115.33(11) . . ?
N1 C5 C13 122.74(12) . . ?
N1 C5 C4 117.23(11) . . ?
C13 C5 C4 120.02(12) . . ?
C7 C6 C17 118.72(11) . . ?
C7 C6 C9 121.55(12) . . ?
C17 C6 C9 119.73(11) . . ?
C6 C7 C8 121.76(13) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C10 C8 C7 120.43(13) . . ?
C10 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 120.09(12) . . ?
C8 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 123.54(12) . . ?
C12 C11 C17 117.09(11) . . ?
C10 C11 C17 119.37(12) . . ?
C13 C12 C11 119.86(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C5 119.36(13) . . ?
C12 C13 H13 120.3 . . ?
C5 C13 H13 120.3 . . ?
C4 C14 C15 106.50(12) . . ?
C4 C14 C16 128.31(12) . . ?
C15 C14 C16 125.19(11) . . ?
C3 C15 C14 106.17(11) . . ?
C3 C15 H15 126.9 . . ?
C14 C15 H15 126.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C6 117.74(9) . . ?
N1 C17 C11 122.63(10) . . ?
C6 C17 C11 119.62(10) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.042
