# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_I
_chemical_name_systematic        ?
_chemical_name_common            LWJ-161C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         277.32

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9957(12)
_cell_length_b                   7.6225(6)
_cell_length_c                   11.9828(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.022(3)
_cell_angle_gamma                90
_cell_volume                     1369.47(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    153
_cell_measurement_theta_min      2.9882
_cell_measurement_theta_max      25.6211
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              'Sealed Microfocusing Source'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  n/a

_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            49120
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          '? '

_reflns_number_total             3141
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0941
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.7934P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2013.6-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.70965(6) 0.55048(13) 0.13882(7) 0.0241(2) Uani d . . . 1 . .
N N1 0.95891(6) 0.61702(13) 0.28447(8) 0.0168(2) Uani d . . . 1 . .
N N2 0.92889(7) 0.66656(15) 0.38759(8) 0.0212(2) Uani d . . . 1 . .
N N3 0.84202(7) 0.66684(14) 0.38133(8) 0.0202(2) Uani d . . . 1 . .
C C1 1.05338(8) 0.61113(15) 0.26704(10) 0.0174(2) Uani d . . . 1 . .
C C2 1.10771(8) 0.53615(16) 0.34915(10) 0.0214(3) Uani d . . . 1 . .
H H2 1.0826 0.4847 0.4136 0.026 Uiso calc U . R 1 . .
C C3 1.19958(9) 0.53787(18) 0.33512(12) 0.0263(3) Uani d . . . 1 . .
H H3 1.2378 0.4879 0.3906 0.032 Uiso calc U . R 1 . .
C C4 1.23556(8) 0.61229(18) 0.24045(12) 0.0278(3) Uani d . . . 1 . .
H H4 1.2984 0.6135 0.2316 0.033 Uiso calc U . R 1 . .
C C5 1.18040(8) 0.68498(18) 0.15860(11) 0.0250(3) Uani d . . . 1 . .
H H5 1.2055 0.7343 0.0935 0.03 Uiso calc U . R 1 . .
C C6 1.08840(8) 0.68581(16) 0.17169(10) 0.0202(3) Uani d . . . 1 . .
H H6 1.0503 0.7366 0.1164 0.024 Uiso calc U . R 1 . .
C C7 0.89018(8) 0.58499(15) 0.21294(9) 0.0153(2) Uani d . . . 1 . .
C C8 0.81529(8) 0.61966(15) 0.27570(9) 0.0163(2) Uani d . . . 1 . .
C C9 0.90019(8) 0.51549(16) 0.09798(9) 0.0192(2) Uani d . . . 1 . .
H H9A 0.892 0.611 0.044 0.029 Uiso calc U . R 1 . .
H H9B 0.8552 0.4245 0.0837 0.029 Uiso calc U . R 1 . .
H H9C 0.9599 0.4651 0.0904 0.029 Uiso calc U . R 1 . .
C C10 0.72205(8) 0.60154(15) 0.23506(9) 0.0170(2) Uani d . . . 1 . .
C C11 0.64428(8) 0.63897(15) 0.30708(9) 0.0172(2) Uani d . . . 1 . .
C C12 0.64663(8) 0.74877(16) 0.40061(10) 0.0186(2) Uani d . . . 1 . .
H H12 0.7009 0.8034 0.4232 0.022 Uiso calc U . R 1 . .
C C13 0.56932(8) 0.77794(16) 0.46058(10) 0.0193(2) Uani d . . . 1 . .
H H13 0.5714 0.8549 0.5229 0.023 Uiso calc U . R 1 . .
C C14 0.48883(8) 0.69666(16) 0.43114(10) 0.0187(2) Uani d . . . 1 . .
C C15 0.48762(8) 0.58510(16) 0.33858(10) 0.0205(3) Uani d . . . 1 . .
H H15 0.4338 0.5268 0.3178 0.025 Uiso calc U . R 1 . .
C C16 0.56344(8) 0.55817(16) 0.27668(10) 0.0194(2) Uani d . . . 1 . .
H H16 0.5607 0.4842 0.2129 0.023 Uiso calc U . R 1 . .
C C17 0.40572(8) 0.72792(17) 0.49722(11) 0.0232(3) Uani d . . . 1 . .
H H17A 0.3646 0.8026 0.4541 0.035 Uiso calc U . R 1 . .
H H17B 0.4217 0.7861 0.5677 0.035 Uiso calc U . R 1 . .
H H17C 0.3769 0.6154 0.5128 0.035 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.2281(14) ?
N1 C7 . 1.3509(15) ?
N1 N2 . 1.3755(14) ?
N1 C1 . 1.4363(15) ?
N2 N3 . 1.3034(14) ?
N3 C8 . 1.3689(15) ?
C1 C6 . 1.3881(17) ?
C1 C2 . 1.3893(17) ?
C2 C3 . 1.3909(18) ?
C3 C4 . 1.386(2) ?
C4 C5 . 1.387(2) ?
C5 C6 . 1.3913(17) ?
C7 C8 . 1.3880(16) ?
C7 C9 . 1.4861(16) ?
C8 C10 . 1.4788(16) ?
C10 C11 . 1.4907(16) ?
C11 C12 . 1.3987(17) ?
C11 C16 . 1.4021(16) ?
C12 C13 . 1.3928(17) ?
C13 C14 . 1.3964(17) ?
C14 C15 . 1.3974(18) ?
C14 C17 . 1.5073(16) ?
C15 C16 . 1.3839(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 N2 . . 111.18(9) ?
C7 N1 C1 . . 130.20(10) ?
N2 N1 C1 . . 118.60(9) ?
N3 N2 N1 . . 106.95(9) ?
N2 N3 C8 . . 109.19(10) ?
C6 C1 C2 . . 121.73(11) ?
C6 C1 N1 . . 119.70(11) ?
C2 C1 N1 . . 118.51(11) ?
C1 C2 C3 . . 118.69(12) ?
C4 C3 C2 . . 120.24(12) ?
C3 C4 C5 . . 120.41(12) ?
C4 C5 C6 . . 120.14(12) ?
C1 C6 C5 . . 118.78(12) ?
N1 C7 C8 . . 103.73(10) ?
N1 C7 C9 . . 124.33(10) ?
C8 C7 C9 . . 131.78(11) ?
N3 C8 C7 . . 108.94(10) ?
N3 C8 C10 . . 126.06(10) ?
C7 C8 C10 . . 124.97(10) ?
O1 C10 C8 . . 117.73(11) ?
O1 C10 C11 . . 119.83(10) ?
C8 C10 C11 . . 122.43(10) ?
C12 C11 C16 . . 118.70(11) ?
C12 C11 C10 . . 124.72(10) ?
C16 C11 C10 . . 116.57(10) ?
C13 C12 C11 . . 119.98(11) ?
C12 C13 C14 . . 121.50(11) ?
C13 C14 C15 . . 118.00(11) ?
C13 C14 C17 . . 121.07(11) ?
C15 C14 C17 . . 120.93(11) ?
C16 C15 C14 . . 121.09(11) ?
C15 C16 C11 . . 120.69(11) ?



_database_code_depnum_ccdc_archive 'CCDC 983786'
