# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lkm5046

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O'
_chemical_formula_weight         342.43

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 0.0016 '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)/c

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

_cell_length_a                   22.0227(5)
_cell_length_b                   5.5302(2)
_cell_length_c                   15.8613(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.984(2)
_cell_angle_gamma                90.00
_cell_volume                     1882.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1008
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      22.93

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_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 area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17282
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_sigmaI/netI    0.0999
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4323
_reflns_number_gt                2108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2010)'

_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)+(0.0685P)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_number_reflns         4323
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.98530(9) 0.6945(4) 0.90544(16) 0.0582(7) Uani 1 1 d . . .
N1 N 0.65099(10) 0.5326(4) 0.88485(14) 0.0308(6) Uani 1 1 d . . .
N2 N 0.70201(10) 0.5738(4) 0.95224(15) 0.0361(6) Uani 1 1 d . . .
C1 C 0.80273(12) 0.7521(5) 0.93534(18) 0.0315(7) Uani 1 1 d . . .
C2 C 0.84817(13) 0.9228(5) 0.9677(2) 0.0442(8) Uani 1 1 d . . .
H2 H 0.8379 1.0566 0.9972 0.053 Uiso 1 1 calc R . .
C3 C 0.90827(14) 0.8979(6) 0.9569(2) 0.0507(9) Uani 1 1 d . . .
H3 H 0.9381 1.0142 0.9792 0.061 Uiso 1 1 calc R . .
C4 C 0.92431(13) 0.7012(6) 0.9133(2) 0.0433(8) Uani 1 1 d . . .
C5 C 0.88031(13) 0.5249(6) 0.88258(19) 0.0419(8) Uani 1 1 d . . .
H5 H 0.8910 0.3890 0.8546 0.050 Uiso 1 1 calc R . .
C6 C 0.81990(13) 0.5525(5) 0.89398(18) 0.0365(7) Uani 1 1 d . . .
H6 H 0.7904 0.4338 0.8733 0.044 Uiso 1 1 calc R . .
C7 C 1.00364(14) 0.4999(8) 0.8580(2) 0.0630(11) Uani 1 1 d . . .
H7A H 0.9782 0.4973 0.7995 0.076 Uiso 1 1 calc R . .
H7B H 0.9985 0.3470 0.8856 0.076 Uiso 1 1 calc R . .
C8 C 1.07126(15) 0.5383(8) 0.8564(3) 0.0762(13) Uani 1 1 d . . .
H8A H 1.0760 0.6928 0.8310 0.114 Uiso 1 1 calc R . .
H8B H 1.0845 0.4130 0.8227 0.114 Uiso 1 1 calc R . .
H8C H 1.0962 0.5335 0.9144 0.114 Uiso 1 1 calc R . .
C9 C 0.73619(12) 0.7960(5) 0.94105(18) 0.0329(7) Uani 1 1 d . . .
H9 H 0.7354 0.9077 0.9888 0.039 Uiso 1 1 calc R . .
C10 C 0.69560(12) 0.8983(5) 0.85630(17) 0.0325(7) Uani 1 1 d . . .
H10A H 0.6770 1.0515 0.8662 0.039 Uiso 1 1 calc R . .
H10B H 0.7198 0.9200 0.8128 0.039 Uiso 1 1 calc R . .
C11 C 0.64673(11) 0.7057(5) 0.82978(17) 0.0264(6) Uani 1 1 d . . .
C12 C 0.59898(11) 0.7033(5) 0.74927(16) 0.0261(6) Uani 1 1 d . . .
C13 C 0.55555(12) 0.5148(5) 0.72941(17) 0.0305(7) Uani 1 1 d . . .
H13 H 0.5561 0.3904 0.7690 0.037 Uiso 1 1 calc R . .
C14 C 0.51223(12) 0.5117(5) 0.65219(17) 0.0334(7) Uani 1 1 d . . .
H14 H 0.4836 0.3857 0.6401 0.040 Uiso 1 1 calc R . .
C15 C 0.51079(13) 0.6953(5) 0.59204(18) 0.0373(7) Uani 1 1 d . . .
H15 H 0.4818 0.6917 0.5394 0.045 Uiso 1 1 calc R . .
C16 C 0.55298(13) 0.8837(5) 0.61130(18) 0.0381(7) Uani 1 1 d . . .
H16 H 0.5517 1.0088 0.5718 0.046 Uiso 1 1 calc R . .
C17 C 0.59702(12) 0.8881(5) 0.68848(17) 0.0320(7) Uani 1 1 d . . .
H17 H 0.6255 1.0146 0.7001 0.038 Uiso 1 1 calc R . .
C18 C 0.70899(12) 0.4369(5) 1.02748(17) 0.0315(7) Uani 1 1 d . . .
C19 C 0.66681(12) 0.2537(5) 1.03320(18) 0.0330(7) Uani 1 1 d . . .
H19 H 0.6324 0.2283 0.9880 0.040 Uiso 1 1 calc R . .
C20 C 0.67611(14) 0.1099(6) 1.10597(18) 0.0422(8) Uani 1 1 d . . .
H20 H 0.6482 -0.0142 1.1089 0.051 Uiso 1 1 calc R . .
C21 C 0.72609(14) 0.1470(6) 1.1743(2) 0.0464(8) Uani 1 1 d . . .
H21 H 0.7321 0.0483 1.2230 0.056 Uiso 1 1 calc R . .
C22 C 0.76709(14) 0.3317(6) 1.16993(19) 0.0455(8) Uani 1 1 d . . .
H22 H 0.8007 0.3585 1.2162 0.055 Uiso 1 1 calc R . .
C23 C 0.75890(13) 0.4788(6) 1.09714(18) 0.0401(8) Uani 1 1 d . . .
H23 H 0.7866 0.6044 1.0950 0.048 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
O1 C4 1.377(3) . ?
O1 C7 1.422(4) . ?
N1 C11 1.285(3) . ?
N1 N2 1.385(3) . ?
N2 C18 1.392(3) . ?
N2 C9 1.473(3) . ?
C1 C6 1.380(4) . ?
C1 C2 1.387(4) . ?
C1 C9 1.508(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.510(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.545(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.505(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.461(3) . ?
C12 C17 1.399(4) . ?
C12 C13 1.402(4) . ?
C13 C14 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.391(4) . ?
C18 C23 1.392(4) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C4 O1 C7 117.8(3) . . ?
C11 N1 N2 109.0(2) . . ?
N1 N2 C18 119.1(2) . . ?
N1 N2 C9 113.1(2) . . ?
C18 N2 C9 126.6(2) . . ?
C6 C1 C2 117.9(3) . . ?
C6 C1 C9 122.1(3) . . ?
C2 C1 C9 119.9(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O1 C4 C3 115.6(3) . . ?
O1 C4 C5 124.7(3) . . ?
C3 C4 C5 119.7(3) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 121.5(3) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O1 C7 C8 107.5(3) . . ?
O1 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C1 113.8(2) . . ?
N2 C9 C10 101.5(2) . . ?
C1 C9 C10 112.8(2) . . ?
N2 C9 H9 109.5 . . ?
C1 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C11 C10 C9 102.8(2) . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
N1 C11 C12 121.1(2) . . ?
N1 C11 C10 113.5(2) . . ?
C12 C11 C10 125.4(2) . . ?
C17 C12 C13 118.3(2) . . ?
C17 C12 C11 120.0(2) . . ?
C13 C12 C11 121.6(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 119.3(3) . . ?
C19 C18 N2 120.3(2) . . ?
C23 C18 N2 120.4(3) . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 119.6(3) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 983902'
