# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_n0216b-8
_database_code_depnum_ccdc_archive 'CCDC 1053232'
_audit_update_record             
;
2015-03-11 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N2 O2'
_chemical_formula_sum            'C15 H20 N2 O2'
_chemical_formula_weight         260.33

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   P2(1)
_chemical_absolute_configuration syn

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

_cell_length_a                   9.4882(18)
_cell_length_b                   10.3774(19)
_cell_length_c                   15.575(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.509(6)
_cell_angle_gamma                90.00
_cell_volume                     1462.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15954
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      28.28

_exptl_crystal_description       rod
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15954
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         28.28
_reflns_number_total             5733
_reflns_number_gt                4455
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1711P)²+7.0050P] 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         5733
_refine_ls_number_parameters     343
_refine_ls_number_restraints     337
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.1445
_refine_ls_wR_factor_ref         0.3965
_refine_ls_wR_factor_gt          0.3846
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.117
_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
N1 N 0.8856(7) 0.7925(6) 0.6454(4) 0.0172(11) Uani 1 1 d U . .
H1B H 0.7895 0.8009 0.6347 0.021 Uiso 1 1 calc R . .
N2 N 0.9637(8) 0.4727(7) 0.6147(5) 0.0276(15) Uani 1 1 d U . .
H2B H 0.9247 0.4036 0.5839 0.033 Uiso 1 1 calc R . .
H2C H 1.0602 0.4831 0.6327 0.033 Uiso 1 1 calc R . .
O1 O 1.0970(6) 0.8865(5) 0.6388(4) 0.0267(12) Uani 1 1 d U . .
O2 O 0.7425(6) 0.5525(6) 0.6112(4) 0.0264(12) Uani 1 1 d U . .
C1 C 0.8591(11) 1.1152(10) 0.7885(6) 0.0362(19) Uani 1 1 d U . .
H1A H 0.7549 1.1077 0.7636 0.043 Uiso 1 1 calc R . .
C2 C 0.9195(14) 1.1173(10) 0.8797(7) 0.043(2) Uani 1 1 d U . .
H2A H 0.8575 1.1096 0.9172 0.052 Uiso 1 1 calc R . .
C3 C 1.0705(15) 1.1305(10) 0.9180(6) 0.048(2) Uani 1 1 d U . .
H3A H 1.1133 1.1326 0.9815 0.057 Uiso 1 1 calc R . .
C4 C 1.1581(13) 1.1407(10) 0.8606(7) 0.042(2) Uani 1 1 d U . .
H4A H 1.2620 1.1511 0.8852 0.050 Uiso 1 1 calc R . .
C5 C 1.0946(12) 1.1357(11) 0.7675(7) 0.041(2) Uani 1 1 d U . .
H5A H 1.1552 1.1407 0.7289 0.049 Uiso 1 1 calc R . .
C6 C 0.9442(10) 1.1236(8) 0.7318(5) 0.0272(15) Uani 1 1 d U . .
C7 C 0.8659(10) 1.1194(8) 0.6310(5) 0.0259(15) Uani 1 1 d U . .
H7A H 0.7683 1.1647 0.6126 0.031 Uiso 1 1 calc R . .
C8 C 0.9415(10) 1.1183(8) 0.5605(6) 0.0287(16) Uani 1 1 d U . .
H8A H 0.8941 1.1656 0.5039 0.034 Uiso 1 1 calc R . .
H8B H 1.0508 1.1205 0.5803 0.034 Uiso 1 1 calc R . .
C9 C 0.8699(10) 1.0003(8) 0.5772(5) 0.0247(15) Uani 1 1 d U . .
H9A H 0.7750 0.9781 0.5305 0.030 Uiso 1 1 calc R . .
C10 C 0.9604(8) 0.8896(7) 0.6208(5) 0.0190(13) Uani 1 1 d U . .
C11 C 0.9551(8) 0.6757(7) 0.6882(5) 0.0203(13) Uani 1 1 d U . .
H11A H 1.0605 0.6756 0.6883 0.024 Uiso 1 1 calc R . .
C12 C 0.8774(8) 0.5607(7) 0.6340(5) 0.0160(12) Uani 1 1 d U . .
C13 C 0.9515(9) 0.6611(8) 0.7872(5) 0.0259(16) Uani 1 1 d U . .
H13A H 0.8462 0.6558 0.7871 0.031 Uiso 1 1 calc R . .
C14 C 1.0240(17) 0.7772(11) 0.8428(7) 0.054(3) Uani 1 1 d U . .
H14A H 1.0209 0.7670 0.9048 0.081 Uiso 1 1 calc R . .
H14B H 0.9707 0.8557 0.8168 0.081 Uiso 1 1 calc R . .
H14C H 1.1270 0.7836 0.8428 0.081 Uiso 1 1 calc R . .
C15 C 1.0319(12) 0.5370(10) 0.8285(6) 0.037(2) Uani 1 1 d U . .
H15A H 1.0282 0.5279 0.8905 0.055 Uiso 1 1 calc R . .
H15B H 1.1351 0.5412 0.8287 0.055 Uiso 1 1 calc R . .
H15C H 0.9836 0.4627 0.7929 0.055 Uiso 1 1 calc R . .
N3 N 0.4762(7) 0.6404(6) 0.6615(4) 0.0186(12) Uani 1 1 d U . .
H3B H 0.5617 0.6259 0.6521 0.022 Uiso 1 1 calc R . .
N4 N 0.3331(7) 0.9247(7) 0.5646(4) 0.0222(13) Uani 1 1 d U . .
H4B H 0.3324 0.9730 0.5180 0.027 Uiso 1 1 calc R . .
H4C H 0.2538 0.9199 0.5826 0.027 Uiso 1 1 calc R . .
O3 O 0.2655(6) 0.5516(6) 0.6712(4) 0.0251(12) Uani 1 1 d U . .
O4 O 0.5687(6) 0.8627(7) 0.5846(4) 0.0296(14) Uani 1 1 d U . .
C16 C 0.4140(11) 0.3602(10) 0.8300(6) 0.0350(19) Uani 1 1 d U . .
H16A H 0.3133 0.3487 0.7960 0.042 Uiso 1 1 calc R . .
C17 C 0.4541(15) 0.3926(10) 0.9225(7) 0.047(2) Uani 1 1 d U . .
H17A H 0.3778 0.4048 0.9496 0.057 Uiso 1 1 calc R . .
C18 C 0.6004(16) 0.4072(11) 0.9755(7) 0.052(2) Uani 1 1 d U . .
H18A H 0.6243 0.4263 1.0379 0.063 Uiso 1 1 calc R . .
C19 C 0.7066(14) 0.3934(10) 0.9353(7) 0.046(2) Uani 1 1 d U . .
H19A H 0.8067 0.4042 0.9706 0.055 Uiso 1 1 calc R . .
C20 C 0.6760(10) 0.3632(8) 0.8422(7) 0.0347(18) Uani 1 1 d U . .
H20A H 0.7536 0.3550 0.8156 0.042 Uiso 1 1 calc R . .
C21 C 0.5262(10) 0.3456(7) 0.7903(5) 0.0255(15) Uani 1 1 d U . .
C22 C 0.4979(10) 0.3205(9) 0.6931(6) 0.0316(17) Uani 1 1 d U . .
H22A H 0.5780 0.2687 0.6801 0.038 Uiso 1 1 calc R . .
C23 C 0.3539(9) 0.2983(8) 0.6282(6) 0.0275(15) Uani 1 1 d U . .
H23A H 0.2662 0.3041 0.6500 0.033 Uiso 1 1 calc R . .
H23B H 0.3469 0.2322 0.5813 0.033 Uiso 1 1 calc R . .
C24 C 0.4336(9) 0.4204(8) 0.6221(5) 0.0227(14) Uani 1 1 d U . .
H24A H 0.4779 0.4281 0.5717 0.027 Uiso 1 1 calc R . .
C25 C 0.3810(9) 0.5404(8) 0.6537(5) 0.0220(14) Uani 1 1 d U . .
C26 C 0.4432(8) 0.7712(7) 0.6848(5) 0.0182(13) Uani 1 1 d U . .
H26A H 0.3388 0.7734 0.6868 0.022 Uiso 1 1 calc R . .
C27 C 0.4551(7) 0.8583(7) 0.6081(4) 0.0152(12) Uani 1 1 d U . .
C28 C 0.5437(9) 0.8209(7) 0.7744(5) 0.0231(14) Uani 1 1 d U . .
H28A H 0.6457 0.8278 0.7688 0.028 Uiso 1 1 calc R . .
C29 C 0.5499(13) 0.7257(10) 0.8504(7) 0.041(2) Uani 1 1 d U . .
H29A H 0.5798 0.6407 0.8347 0.062 Uiso 1 1 calc R . .
H29B H 0.4521 0.7194 0.8592 0.062 Uiso 1 1 calc R . .
H29C H 0.6217 0.7559 0.9062 0.062 Uiso 1 1 calc R . .
C30 C 0.4960(11) 0.9558(8) 0.7930(6) 0.0304(17) Uani 1 1 d U . .
H30A H 0.4922 1.0122 0.7419 0.046 Uiso 1 1 calc R . .
H30B H 0.5672 0.9903 0.8475 0.046 Uiso 1 1 calc R . .
H30C H 0.3979 0.9516 0.8016 0.046 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 C10 1.353(9) . ?
N1 C11 1.444(9) . ?
N2 C12 1.320(10) . ?
O1 C10 1.241(9) . ?
O2 C12 1.225(9) . ?
C1 C2 1.362(14) . ?
C1 C6 1.367(13) . ?
C2 C3 1.383(18) . ?
C3 C4 1.396(17) . ?
C4 C5 1.393(14) . ?
C5 C6 1.372(14) . ?
C6 C7 1.523(11) . ?
C7 C8 1.482(11) . ?
C7 C9 1.500(11) . ?
C8 C9 1.461(11) . ?
C9 C10 1.472(11) . ?
C11 C12 1.518(10) . ?
C11 C13 1.559(10) . ?
C13 C14 1.522(13) . ?
C13 C15 1.536(12) . ?
N3 C25 1.357(11) . ?
N3 C26 1.463(9) . ?
N4 C27 1.342(9) . ?
O3 C25 1.212(9) . ?
O4 C27 1.239(8) . ?
C16 C21 1.392(12) . ?
C16 C17 1.415(14) . ?
C17 C18 1.394(19) . ?
C18 C19 1.345(18) . ?
C19 C20 1.426(14) . ?
C20 C21 1.419(12) . ?
C21 C22 1.478(11) . ?
C22 C23 1.453(13) . ?
C22 C24 1.505(12) . ?
C23 C24 1.494(11) . ?
C24 C25 1.479(10) . ?
C26 C28 1.523(10) . ?
C26 C27 1.529(10) . ?
C28 C30 1.526(10) . ?
C28 C29 1.530(12) . ?

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
C10 N1 C11 123.4(6) . . ?
C2 C1 C6 121.8(10) . . ?
C1 C2 C3 120.5(9) . . ?
C2 C3 C4 118.1(9) . . ?
C5 C4 C3 120.6(10) . . ?
C6 C5 C4 119.8(9) . . ?
C1 C6 C5 119.3(8) . . ?
C1 C6 C7 117.6(8) . . ?
C5 C6 C7 123.1(8) . . ?
C8 C7 C9 58.7(5) . . ?
C8 C7 C6 124.7(8) . . ?
C9 C7 C6 120.9(7) . . ?
C9 C8 C7 61.3(5) . . ?
C8 C9 C10 119.9(8) . . ?
C8 C9 C7 60.0(5) . . ?
C10 C9 C7 119.7(7) . . ?
O1 C10 N1 121.2(7) . . ?
O1 C10 C9 123.3(7) . . ?
N1 C10 C9 115.4(7) . . ?
N1 C11 C12 109.0(6) . . ?
N1 C11 C13 113.3(6) . . ?
C12 C11 C13 108.8(6) . . ?
O2 C12 N2 123.5(7) . . ?
O2 C12 C11 120.4(6) . . ?
N2 C12 C11 116.1(6) . . ?
C14 C13 C15 110.0(8) . . ?
C14 C13 C11 110.2(8) . . ?
C15 C13 C11 109.9(6) . . ?
C25 N3 C26 123.0(6) . . ?
C21 C16 C17 118.1(9) . . ?
C18 C17 C16 122.9(10) . . ?
C19 C18 C17 117.7(9) . . ?
C18 C19 C20 123.1(10) . . ?
C21 C20 C19 118.0(10) . . ?
C16 C21 C20 120.1(8) . . ?
C16 C21 C22 123.1(8) . . ?
C20 C21 C22 116.6(8) . . ?
C23 C22 C21 125.7(8) . . ?
C23 C22 C24 60.6(5) . . ?
C21 C22 C24 122.6(7) . . ?
C22 C23 C24 61.4(6) . . ?
C25 C24 C23 117.7(6) . . ?
C25 C24 C22 116.0(6) . . ?
C23 C24 C22 58.0(6) . . ?
O3 C25 N3 121.9(7) . . ?
O3 C25 C24 125.0(8) . . ?
N3 C25 C24 113.1(6) . . ?
N3 C26 C28 114.8(6) . . ?
N3 C26 C27 106.4(5) . . ?
C28 C26 C27 110.0(6) . . ?
O4 C27 N4 121.8(6) . . ?
O4 C27 C26 121.9(6) . . ?
N4 C27 C26 116.3(6) . . ?
C26 C28 C30 110.2(7) . . ?
C26 C28 C29 111.0(7) . . ?
C30 C28 C29 112.9(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O4 0.88 2.10 2.959(8) 163.6 .
N3 H3B O2 0.88 2.14 3.003(8) 166.3 .
N2 H2C O3 0.88 1.99 2.851(9) 166.1 1_655
N4 H4B O2 0.88 2.09 2.931(8) 159.0 2_656

_diffrn_measured_fraction_theta_max 0.815
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.767
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.122
