# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_osj58m
_database_code_depnum_ccdc_archive 'CCDC 1517809'
_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N3 O2'
_chemical_formula_sum            'C22 H23 N3 O2'
_chemical_formula_weight         361.43

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.496(6)
_cell_length_b                   11.107(8)
_cell_length_c                   9.921(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.155(12)
_cell_angle_gamma                90.00
_cell_volume                     932.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1240
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.75

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 100
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10681
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2233
_reflns_number_gt                1673
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0411P)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    constr
_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   ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2233
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
N1 N 0.6164(2) 0.88808(19) 0.1891(2) 0.0242(5) Uani 1 1 d . . .
N2 N 0.4591(3) 1.1293(2) 0.2531(2) 0.0251(5) Uani 1 1 d . . .
N3 N 0.4327(3) 1.0429(2) 0.4517(2) 0.0261(6) Uani 1 1 d . . .
O1 O 0.4479(2) 0.69908(16) 0.01843(17) 0.0262(4) Uani 1 1 d . . .
H1 H 0.4682 0.6956 -0.0628 0.039 Uiso 1 1 calc R . .
O2 O 0.7134(2) 0.91082(19) 0.40719(18) 0.0345(5) Uani 1 1 d . . .
C1 C 0.5100(3) 0.9103(3) 0.0657(2) 0.0234(6) Uani 1 1 d . . .
H1A H 0.4619 0.9923 0.0697 0.028 Uiso 1 1 calc R . .
C2 C 0.6264(3) 0.9069(3) -0.0442(3) 0.0286(6) Uani 1 1 d . . .
H2A H 0.6680 0.9884 -0.0600 0.034 Uiso 1 1 calc R . .
H2B H 0.5737 0.8759 -0.1303 0.034 Uiso 1 1 calc R . .
C3 C 0.7613(3) 0.8215(3) 0.0102(3) 0.0326(7) Uani 1 1 d . . .
H3A H 0.7527 0.7432 -0.0376 0.039 Uiso 1 1 calc R . .
H3B H 0.8655 0.8574 -0.0029 0.039 Uiso 1 1 calc R . .
C4 C 0.7424(3) 0.8049(3) 0.1599(3) 0.0286(7) Uani 1 1 d . . .
H4A H 0.7126 0.7209 0.1791 0.034 Uiso 1 1 calc R . .
H4B H 0.8419 0.8247 0.2151 0.034 Uiso 1 1 calc R . .
C5 C 0.6166(3) 0.9401(3) 0.3117(3) 0.0258(6) Uani 1 1 d . . .
C6 C 0.5009(3) 1.0367(2) 0.3330(2) 0.0227(6) Uani 1 1 d . . .
C7 C 0.3416(3) 1.1445(3) 0.4459(3) 0.0301(7) Uani 1 1 d . . .
H7 H 0.2787 1.1731 0.5136 0.036 Uiso 1 1 calc R . .
C8 C 0.3585(3) 1.1964(3) 0.3243(3) 0.0274(6) Uani 1 1 d . . .
H8 H 0.3081 1.2687 0.2929 0.033 Uiso 1 1 calc R . .
C9 C 0.3781(3) 0.8136(2) 0.0438(2) 0.0238(6) Uani 1 1 d . . .
C10 C 0.2546(3) 0.8459(2) -0.0731(3) 0.0238(6) Uani 1 1 d . . .
C11 C 0.2168(4) 0.9633(3) -0.1112(3) 0.0320(7) Uani 1 1 d . . .
H11 H 0.2748 1.0282 -0.0687 0.038 Uiso 1 1 calc R . .
C12 C 0.0946(4) 0.9871(3) -0.2111(3) 0.0374(8) Uani 1 1 d . . .
H12 H 0.0683 1.0680 -0.2345 0.045 Uiso 1 1 calc R . .
C13 C 0.0116(3) 0.8938(3) -0.2763(3) 0.0345(7) Uani 1 1 d . . .
H13 H -0.0705 0.9100 -0.3454 0.041 Uiso 1 1 calc R . .
C14 C 0.0492(3) 0.7765(3) -0.2399(3) 0.0332(7) Uani 1 1 d . . .
H14 H -0.0078 0.7118 -0.2839 0.040 Uiso 1 1 calc R . .
C15 C 0.1691(3) 0.7524(3) -0.1399(3) 0.0289(7) Uani 1 1 d . . .
H15 H 0.1938 0.6713 -0.1162 0.035 Uiso 1 1 calc R . .
C16 C 0.2940(3) 0.7994(2) 0.1729(2) 0.0236(6) Uani 1 1 d . . .
C17 C 0.3153(3) 0.6976(3) 0.2531(3) 0.0307(7) Uani 1 1 d . . .
H17 H 0.3848 0.6359 0.2286 0.037 Uiso 1 1 calc R . .
C18 C 0.2359(4) 0.6846(3) 0.3695(3) 0.0379(8) Uani 1 1 d . . .
H18 H 0.2507 0.6140 0.4233 0.046 Uiso 1 1 calc R . .
C19 C 0.1360(4) 0.7742(3) 0.4063(3) 0.0416(9) Uani 1 1 d . . .
H19 H 0.0801 0.7647 0.4844 0.050 Uiso 1 1 calc R . .
C20 C 0.1171(3) 0.8781(3) 0.3297(3) 0.0373(8) Uani 1 1 d . . .
H20 H 0.0510 0.9410 0.3568 0.045 Uiso 1 1 calc R . .
C21 C 0.1947(3) 0.8903(3) 0.2131(3) 0.0311(7) Uani 1 1 d . . .
H21 H 0.1802 0.9613 0.1601 0.037 Uiso 1 1 calc R . .
C22 C 0.4428(4) 0.9560(3) 0.5622(3) 0.0348(7) Uani 1 1 d . . .
H22A H 0.4447 0.8742 0.5252 0.052 Uiso 1 1 calc R . .
H22B H 0.3508 0.9650 0.6143 0.052 Uiso 1 1 calc R . .
H22C H 0.5396 0.9703 0.6215 0.052 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
N1 C5 1.346(3) . ?
N1 C4 1.462(3) . ?
N1 C1 1.476(3) . ?
N2 C6 1.327(3) . ?
N2 C8 1.376(3) . ?
N3 C6 1.360(3) . ?
N3 C7 1.367(4) . ?
N3 C22 1.457(3) . ?
O1 C9 1.435(3) . ?
O1 H1 0.8400 . ?
O2 C5 1.240(3) . ?
C1 C2 1.537(4) . ?
C1 C9 1.554(4) . ?
C1 H1A 1.0000 . ?
C2 C3 1.547(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.520(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.483(4) . ?
C7 C8 1.356(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C16 1.530(4) . ?
C9 C10 1.535(4) . ?
C10 C11 1.386(4) . ?
C10 C15 1.400(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 C21 1.397(4) . ?
C17 C18 1.397(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C5 N1 C4 120.6(2) . . ?
C5 N1 C1 128.9(2) . . ?
C4 N1 C1 110.23(19) . . ?
C6 N2 C8 104.9(2) . . ?
C6 N3 C7 106.8(2) . . ?
C6 N3 C22 128.1(2) . . ?
C7 N3 C22 125.0(2) . . ?
C9 O1 H1 109.5 . . ?
N1 C1 C2 101.5(2) . . ?
N1 C1 C9 112.4(2) . . ?
C2 C1 C9 112.6(2) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
C9 C1 H1A 110.0 . . ?
C1 C2 C3 105.8(2) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 105.9(2) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C3 105.1(2) . . ?
N1 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
N1 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
O2 C5 N1 121.6(3) . . ?
O2 C5 C6 118.9(2) . . ?
N1 C5 C6 119.5(2) . . ?
N2 C6 N3 111.5(2) . . ?
N2 C6 C5 128.4(2) . . ?
N3 C6 C5 119.9(2) . . ?
C8 C7 N3 106.5(2) . . ?
C8 C7 H7 126.8 . . ?
N3 C7 H7 126.8 . . ?
C7 C8 N2 110.3(2) . . ?
C7 C8 H8 124.8 . . ?
N2 C8 H8 124.8 . . ?
O1 C9 C16 106.7(2) . . ?
O1 C9 C10 109.9(2) . . ?
C16 C9 C10 108.5(2) . . ?
O1 C9 C1 109.5(2) . . ?
C16 C9 C1 109.8(2) . . ?
C10 C9 C1 112.3(2) . . ?
C11 C10 C15 118.1(3) . . ?
C11 C10 C9 123.5(2) . . ?
C15 C10 C9 118.3(2) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C9 121.2(2) . . ?
C21 C16 C9 120.3(2) . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 119.9(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
