# Electronic Supplementary Material (ESI) for Green 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_20151203b_0m
_database_code_depnum_ccdc_archive 'CCDC 1449407'
_audit_update_record             
;
2016-01-24 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.2486(15)
_cell_length_b                   7.0891(9)
_cell_length_c                   13.5496(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.155(4)
_cell_angle_gamma                90.00
_cell_volume                     1161.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4947
_cell_measurement_theta_min      3.2957
_cell_measurement_theta_max      27.4773

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9921
_exptl_absorpt_correction_T_max  0.9984
_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 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10466
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1937
_reflns_number_gt                1519
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_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)+(0.0671P)²+0.5934P] 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     SHELXL
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1937
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
C2 C 0.84422(17) 0.2328(3) 0.85536(17) 0.0355(6) Uani 1 1 d . . .
C3 C 0.75694(18) 0.1963(3) 0.89081(17) 0.0358(6) Uani 1 1 d . . .
C1 C 0.79243(19) 0.2654(3) 0.74540(18) 0.0382(6) Uani 1 1 d . . .
H1 H 0.8284 0.2933 0.7009 0.046 Uiso 1 1 calc R . .
C8 C 0.65676(18) 0.2071(3) 0.79847(18) 0.0373(6) Uani 1 1 d . . .
C7 C 0.5546(2) 0.1751(4) 0.8009(2) 0.0524(7) Uani 1 1 d . . .
H7 H 0.4894 0.1820 0.7385 0.063 Uiso 1 1 calc R . .
C4 C 0.7528(2) 0.1512(4) 0.9894(2) 0.0506(7) Uani 1 1 d . . .
H4 H 0.8174 0.1424 1.0523 0.061 Uiso 1 1 calc R . .
C5 C 0.6517(2) 0.1204(5) 0.9915(2) 0.0648(8) Uani 1 1 d . . .
H5 H 0.6484 0.0902 1.0568 0.078 Uiso 1 1 calc R . .
C6 C 0.5542(2) 0.1329(5) 0.8991(3) 0.0641(8) Uani 1 1 d . . .
H6 H 0.4871 0.1121 0.9040 0.077 Uiso 1 1 calc R . .
N1 N 0.68202(15) 0.2508(3) 0.71230(15) 0.0423(5) Uani 1 1 d . . .
H1A H 0.6343 0.2666 0.6469 0.051 Uiso 1 1 calc R . .
C9 C 0.96071(19) 0.2418(3) 0.92360(18) 0.0389(6) Uani 1 1 d . . .
C11 C 1.1388(2) 0.3584(4) 0.9260(2) 0.0528(7) Uani 1 1 d . . .
H11 H 1.1490 0.4258 0.9882 0.063 Uiso 1 1 calc R . .
C15 C 1.0311(2) 0.1490(4) 0.7841(2) 0.0502(7) Uani 1 1 d . . .
H15 H 0.9683 0.0753 0.7496 0.060 Uiso 1 1 calc R . .
C10 C 1.04381(18) 0.2513(3) 0.87546(18) 0.0400(6) Uani 1 1 d . . .
C14 C 1.1124(3) 0.1565(5) 0.7440(3) 0.0663(9) Uani 1 1 d . . .
H14 H 1.1036 0.0883 0.6824 0.080 Uiso 1 1 calc R . .
C12 C 1.2184(2) 0.3662(5) 0.8852(3) 0.0680(9) Uani 1 1 d . . .
H12 H 1.2810 0.4406 0.9188 0.082 Uiso 1 1 calc R . .
C13 C 1.2048(3) 0.2636(5) 0.7948(3) 0.0734(10) Uani 1 1 d . . .
H13 H 1.2591 0.2672 0.7679 0.088 Uiso 1 1 calc R . .
O1 O 0.99364(13) 0.2422(3) 1.02266(13) 0.0570(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0329(12) 0.0348(13) 0.0312(11) 0.0009(9) 0.0054(10) -0.0014(10)
C3 0.0329(12) 0.0312(12) 0.0357(12) -0.0006(9) 0.0064(10) -0.0010(9)
C1 0.0351(12) 0.0387(13) 0.0347(12) 0.0002(10) 0.0081(10) 0.0001(10)
C8 0.0348(12) 0.0306(12) 0.0391(12) -0.0001(10) 0.0076(10) -0.0012(10)
C7 0.0310(13) 0.0512(17) 0.0632(17) 0.0002(13) 0.0073(12) -0.0023(12)
C4 0.0465(15) 0.0622(18) 0.0383(13) 0.0058(12) 0.0125(11) -0.0051(13)
C5 0.0581(18) 0.083(2) 0.0625(18) 0.0073(16) 0.0341(15) -0.0095(16)
C6 0.0450(16) 0.071(2) 0.080(2) 0.0047(16) 0.0294(15) -0.0092(14)
N1 0.0328(11) 0.0475(12) 0.0323(10) 0.0036(9) -0.0014(8) 0.0015(9)
C9 0.0330(13) 0.0425(14) 0.0336(12) -0.0019(10) 0.0059(10) -0.0023(10)
C11 0.0427(14) 0.0554(17) 0.0552(16) -0.0024(13) 0.0149(12) -0.0071(13)
C15 0.0453(14) 0.0485(16) 0.0540(15) -0.0034(12) 0.0175(12) 0.0014(12)
C10 0.0334(13) 0.0407(14) 0.0410(13) 0.0032(10) 0.0103(10) 0.0011(10)
C14 0.0648(19) 0.076(2) 0.0681(19) -0.0051(16) 0.0375(16) 0.0080(17)
C12 0.0484(17) 0.075(2) 0.083(2) 0.0024(18) 0.0296(16) -0.0140(15)
C13 0.062(2) 0.088(3) 0.086(2) 0.0085(19) 0.0460(18) 0.0020(18)
O1 0.0329(9) 0.0970(16) 0.0310(9) -0.0042(9) 0.0028(7) -0.0055(9)

_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
C2 C1 1.381(3) . ?
C2 C9 1.440(3) . ?
C2 C3 1.446(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.405(3) . ?
C1 N1 1.347(3) . ?
C8 N1 1.375(3) . ?
C8 C7 1.386(3) . ?
C7 C6 1.366(4) . ?
C4 C5 1.369(4) . ?
C5 C6 1.386(4) . ?
C9 O1 1.230(3) . ?
C9 C10 1.493(3) . ?
C11 C12 1.377(4) . ?
C11 C10 1.387(3) . ?
C15 C10 1.384(3) . ?
C15 C14 1.393(4) . ?
C14 C13 1.364(5) . ?
C12 C13 1.372(5) . ?

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
C1 C2 C9 127.9(2) . . ?
C1 C2 C3 106.06(19) . . ?
C9 C2 C3 126.0(2) . . ?
C4 C3 C8 118.2(2) . . ?
C4 C3 C2 135.1(2) . . ?
C8 C3 C2 106.7(2) . . ?
N1 C1 C2 109.8(2) . . ?
N1 C8 C7 129.5(2) . . ?
N1 C8 C3 107.4(2) . . ?
C7 C8 C3 123.1(2) . . ?
C6 C7 C8 116.9(2) . . ?
C5 C4 C3 118.6(2) . . ?
C4 C5 C6 122.0(3) . . ?
C7 C6 C5 121.3(3) . . ?
C1 N1 C8 110.06(19) . . ?
O1 C9 C2 120.6(2) . . ?
O1 C9 C10 118.7(2) . . ?
C2 C9 C10 120.6(2) . . ?
C12 C11 C10 120.8(3) . . ?
C10 C15 C14 119.9(3) . . ?
C15 C10 C11 118.8(2) . . ?
C15 C10 C9 121.6(2) . . ?
C11 C10 C9 119.4(2) . . ?
C13 C14 C15 120.2(3) . . ?
C11 C12 C13 119.7(3) . . ?
C14 C13 C12 120.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.046
