# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_20160425lmf_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1476581'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34

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                   8.805(3)
_cell_length_b                   9.007(4)
_cell_length_c                   10.923(4)
_cell_angle_alpha                67.435(9)
_cell_angle_beta                 78.145(9)
_cell_angle_gamma                73.817(10)
_cell_volume                     763.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3200
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            3752
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0855
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2598
_reflns_number_gt                2324
_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-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)+(0.1653P)²+0.3552P] 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         2598
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2368
_refine_ls_wR_factor_gt          0.2292
_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
C1 C 0.1487(4) 1.2487(3) -0.0703(3) 0.0363(7) Uani 1 1 d . . .
H1A H 0.2615 1.2121 -0.0886 0.054 Uiso 1 1 calc R . .
H1B H 0.1179 1.3653 -0.1163 0.054 Uiso 1 1 calc R . .
H1C H 0.0942 1.1924 -0.1003 0.054 Uiso 1 1 calc R . .
C2 C 0.1421(3) 1.0484(3) 0.1515(2) 0.0194(6) Uani 1 1 d . . .
C3 C 0.2166(3) 0.9199(3) 0.1069(2) 0.0232(6) Uani 1 1 d . . .
H3 H 0.2482 0.9409 0.0163 0.028 Uiso 1 1 calc R . .
C4 C 0.2454(3) 0.7574(3) 0.1966(2) 0.0218(6) Uani 1 1 d . . .
H4 H 0.2951 0.6717 0.1647 0.026 Uiso 1 1 calc R . .
C5 C 0.2007(3) 0.7222(3) 0.3330(2) 0.0176(5) Uani 1 1 d . . .
C6 C 0.1281(3) 0.8549(3) 0.3767(2) 0.0194(6) Uani 1 1 d . . .
H6 H 0.0999 0.8350 0.4675 0.023 Uiso 1 1 calc R . .
C7 C 0.0972(3) 1.0151(3) 0.2881(2) 0.0209(6) Uani 1 1 d . . .
H7 H 0.0463 1.1010 0.3195 0.025 Uiso 1 1 calc R . .
C8 C 0.2656(3) 0.4153(3) 0.3945(2) 0.0158(5) Uani 1 1 d . . .
C9 C 0.1506(3) 0.4116(3) 0.3062(2) 0.0167(5) Uani 1 1 d . . .
C10 C 0.4019(3) 0.3494(3) 0.2048(2) 0.0180(6) Uani 1 1 d . . .
C11 C 0.5259(3) 0.3100(3) 0.1148(2) 0.0224(6) Uani 1 1 d . . .
H11 H 0.5088 0.2865 0.0436 0.027 Uiso 1 1 calc R . .
C12 C 0.6776(3) 0.3068(3) 0.1349(2) 0.0247(6) Uani 1 1 d . . .
H12 H 0.7640 0.2809 0.0758 0.030 Uiso 1 1 calc R . .
C13 C 0.7028(3) 0.3417(3) 0.2418(2) 0.0247(6) Uani 1 1 d . . .
H13 H 0.8055 0.3395 0.2528 0.030 Uiso 1 1 calc R . .
C14 C 0.5766(3) 0.3798(3) 0.3322(2) 0.0201(6) Uani 1 1 d . . .
H14 H 0.5937 0.4020 0.4041 0.024 Uiso 1 1 calc R . .
C15 C 0.4244(3) 0.3839(3) 0.3132(2) 0.0174(6) Uani 1 1 d . . .
C16 C 0.2512(3) 0.2651(3) 0.5252(2) 0.0190(6) Uani 1 1 d . . .
H16A H 0.1447 0.2849 0.5705 0.023 Uiso 1 1 calc R . .
H16B H 0.2652 0.1681 0.5019 0.023 Uiso 1 1 calc R . .
C17 C 0.3688(3) 0.2300(3) 0.6197(2) 0.0249(6) Uani 1 1 d . . .
H17 H 0.3717 0.3144 0.6478 0.030 Uiso 1 1 calc R . .
C18 C 0.4675(3) 0.0878(4) 0.6651(3) 0.0347(7) Uani 1 1 d . . .
H18A H 0.4673 0.0011 0.6388 0.042 Uiso 1 1 calc R . .
H18B H 0.5379 0.0734 0.7237 0.042 Uiso 1 1 calc R . .
N1 N 0.2282(2) 0.5623(2) 0.42887(18) 0.0174(5) Uani 1 1 d . . .
H1D H 0.1606 0.5515 0.4992 0.021 Uiso 1 1 d R . .
N2 N 0.2376(2) 0.3667(2) 0.20386(18) 0.0184(5) Uani 1 1 d . . .
H2A H 0.1932 0.3447 0.1462 0.022 Uiso 1 1 d R . .
O1 O 0.00504(18) 0.4373(2) 0.32896(15) 0.0224(5) Uani 1 1 d . . .
O2 O 0.1073(2) 1.2130(2) 0.07071(16) 0.0239(5) Uani 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
C1 O2 1.437(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.374(4) . ?
C2 O2 1.388(3) . ?
C2 C7 1.398(3) . ?
C3 C4 1.400(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 N1 1.408(3) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.446(3) . ?
C8 C15 1.512(3) . ?
C8 C9 1.551(3) . ?
C8 C16 1.557(3) . ?
C9 O1 1.227(3) . ?
C9 N2 1.350(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.396(3) . ?
C10 N2 1.413(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C16 C17 1.497(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.309(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9300 . ?
C18 H18B 0.9300 . ?
N1 H1D 0.8613 . ?
N2 H2A 0.9095 . ?

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
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O2 124.9(2) . . ?
C3 C2 C7 119.1(2) . . ?
O2 C2 C7 116.0(2) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 N1 124.0(2) . . ?
C6 C5 N1 118.5(2) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 C8 C15 115.78(17) . . ?
N1 C8 C9 115.12(18) . . ?
C15 C8 C9 101.27(17) . . ?
N1 C8 C16 108.48(18) . . ?
C15 C8 C16 110.92(18) . . ?
C9 C8 C16 104.63(17) . . ?
O1 C9 N2 125.6(2) . . ?
O1 C9 C8 125.7(2) . . ?
N2 C9 C8 108.62(18) . . ?
C11 C10 C15 122.6(2) . . ?
C11 C10 N2 128.1(2) . . ?
C15 C10 N2 109.25(19) . . ?
C10 C11 C12 117.1(2) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 C8 131.3(2) . . ?
C10 C15 C8 109.01(19) . . ?
C17 C16 C8 114.25(18) . . ?
C17 C16 H16A 108.7 . . ?
C8 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C8 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 123.9(2) . . ?
C18 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C5 N1 C8 122.73(18) . . ?
C5 N1 H1D 113.3 . . ?
C8 N1 H1D 109.8 . . ?
C9 N2 C10 111.45(18) . . ?
C9 N2 H2A 122.5 . . ?
C10 N2 H2A 126.0 . . ?
C2 O2 C1 116.60(19) . . ?

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
O2 C2 C3 C4 -179.5(2) . . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 N1 -178.9(2) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
N1 C5 C6 C7 -179.88(19) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C3 C2 C7 C6 0.2(3) . . . . ?
O2 C2 C7 C6 -179.47(18) . . . . ?
N1 C8 C9 O1 -51.6(3) . . . . ?
C15 C8 C9 O1 -177.2(2) . . . . ?
C16 C8 C9 O1 67.4(3) . . . . ?
N1 C8 C9 N2 131.72(19) . . . . ?
C15 C8 C9 N2 6.0(2) . . . . ?
C16 C8 C9 N2 -109.3(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
N2 C10 C11 C12 177.5(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C13 C14 C15 C8 177.8(2) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
N2 C10 C15 C14 -178.04(19) . . . . ?
C11 C10 C15 C8 -177.7(2) . . . . ?
N2 C10 C15 C8 3.9(2) . . . . ?
N1 C8 C15 C14 51.1(3) . . . . ?
C9 C8 C15 C14 176.4(2) . . . . ?
C16 C8 C15 C14 -73.0(3) . . . . ?
N1 C8 C15 C10 -131.1(2) . . . . ?
C9 C8 C15 C10 -5.9(2) . . . . ?
C16 C8 C15 C10 104.7(2) . . . . ?
N1 C8 C16 C17 -64.4(3) . . . . ?
C15 C8 C16 C17 63.9(3) . . . . ?
C9 C8 C16 C17 172.28(19) . . . . ?
C8 C16 C17 C18 -124.1(3) . . . . ?
C4 C5 N1 C8 -17.3(3) . . . . ?
C6 C5 N1 C8 164.5(2) . . . . ?
C15 C8 N1 C5 67.0(3) . . . . ?
C9 C8 N1 C5 -50.8(3) . . . . ?
C16 C8 N1 C5 -167.61(18) . . . . ?
O1 C9 N2 C10 179.1(2) . . . . ?
C8 C9 N2 C10 -4.2(2) . . . . ?
C11 C10 N2 C9 -178.0(2) . . . . ?
C15 C10 N2 C9 0.2(3) . . . . ?
C3 C2 O2 C1 2.0(3) . . . . ?
C7 C2 O2 C1 -178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.097
