# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_datam
_database_code_depnum_ccdc_archive 'CCDC 1050424'
_audit_update_record             
;
2015-02-19 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28

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'

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                   8.804(7)
_cell_length_b                   7.685(5)
_cell_length_c                   21.631(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.287(12)
_cell_angle_gamma                90.00
_cell_volume                     1439.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    1792
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1997'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      301(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  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11239
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2973
_reflns_number_gt                1887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0598P)²+0.2847P] 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         2973
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_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 0.1121(3) -0.8317(4) -0.07354(13) 0.0572(8) Uani 1 1 d . . .
C2 C 0.1098(4) -0.6693(4) -0.10023(14) 0.0718(9) Uani 1 1 d . . .
H2 H 0.0727 -0.6544 -0.1429 0.086 Uiso 1 1 calc R . .
C3 C 0.1630(4) -0.5285(4) -0.06305(13) 0.0710(9) Uani 1 1 d . . .
H3 H 0.1609 -0.4183 -0.0809 0.085 Uiso 1 1 calc R . .
C4 C 0.2199(3) -0.5491(4) 0.00108(12) 0.0592(8) Uani 1 1 d . . .
C5 C 0.2160(4) -0.7135(5) 0.02673(14) 0.0725(9) Uani 1 1 d . . .
H5 H 0.2503 -0.7288 0.0696 0.087 Uiso 1 1 calc R . .
C6 C 0.1627(4) -0.8550(4) -0.00975(14) 0.0719(9) Uani 1 1 d . . .
H6 H 0.1608 -0.9647 0.0082 0.086 Uiso 1 1 calc R . .
C7 C 0.0594(4) -0.9800(5) -0.11261(15) 0.0689(9) Uani 1 1 d . . .
C8 C 0.2798(4) -0.4036(5) 0.03918(14) 0.0689(9) Uani 1 1 d . . .
C9 C 0.3351(4) -0.2864(5) 0.07267(14) 0.0694(9) Uani 1 1 d . . .
C10 C 0.3978(3) -0.1451(4) 0.11195(12) 0.0587(8) Uani 1 1 d . . .
C11 C 0.5029(4) -0.0315(5) 0.09388(14) 0.0714(9) Uani 1 1 d . . .
H11 H 0.5335 -0.0467 0.0553 0.086 Uiso 1 1 calc R . .
C12 C 0.5638(3) 0.1053(4) 0.13243(14) 0.0672(9) Uani 1 1 d . . .
H12 H 0.6333 0.1816 0.1191 0.081 Uiso 1 1 calc R . .
C13 C 0.5220(3) 0.1288(4) 0.19003(13) 0.0570(8) Uani 1 1 d . . .
C14 C 0.4164(3) 0.0130(4) 0.20934(11) 0.0494(7) Uani 1 1 d . . .
C15 C 0.3572(3) -0.1214(4) 0.17168(12) 0.0558(8) Uani 1 1 d . . .
H15 H 0.2891 -0.1987 0.1854 0.067 Uiso 1 1 calc R . .
C16 C 0.6722(5) 0.3886(6) 0.21242(19) 0.1074(14) Uani 1 1 d . . .
H16B H 0.7040 0.4689 0.2463 0.161 Uiso 1 1 calc R . .
H16C H 0.6149 0.4498 0.1771 0.161 Uiso 1 1 calc R . .
H16A H 0.7617 0.3360 0.2006 0.161 Uiso 1 1 calc R . .
C17 C 0.2754(4) -0.0675(4) 0.28964(14) 0.0776(10) Uani 1 1 d . . .
H17A H 0.2624 -0.0327 0.3310 0.116 Uiso 1 1 calc R . .
H17B H 0.3131 -0.1849 0.2909 0.116 Uiso 1 1 calc R . .
H17C H 0.1779 -0.0609 0.2615 0.116 Uiso 1 1 calc R . .
N7 N 0.0239(4) -1.1002(5) -0.14254(15) 0.0983(10) Uani 1 1 d . . .
O13 O 0.5768(2) 0.2562(3) 0.23231(10) 0.0736(7) Uani 1 1 d . . .
O14 O 0.3837(2) 0.0457(3) 0.26798(8) 0.0643(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
C1 0.0554(18) 0.065(2) 0.0514(17) -0.0023(15) 0.0097(13) 0.0050(15)
C2 0.096(3) 0.070(2) 0.0479(17) 0.0012(16) 0.0085(16) -0.0036(19)
C3 0.094(2) 0.065(2) 0.0509(18) 0.0058(16) 0.0041(16) -0.0050(18)
C4 0.0655(19) 0.063(2) 0.0495(17) -0.0089(15) 0.0115(13) 0.0022(15)
C5 0.092(2) 0.079(2) 0.0435(17) -0.0013(17) 0.0050(15) 0.0103(19)
C6 0.097(3) 0.060(2) 0.060(2) 0.0083(17) 0.0169(17) 0.0083(18)
C7 0.063(2) 0.073(2) 0.068(2) -0.0074(19) 0.0050(15) 0.0029(17)
C8 0.077(2) 0.078(2) 0.0527(18) -0.0079(17) 0.0162(15) 0.0035(18)
C9 0.084(2) 0.073(2) 0.0543(18) -0.0098(17) 0.0194(16) 0.0082(18)
C10 0.0615(19) 0.066(2) 0.0473(16) -0.0052(14) 0.0066(13) 0.0047(15)
C11 0.070(2) 0.093(3) 0.0545(18) -0.0053(18) 0.0206(15) -0.0010(19)
C12 0.0544(18) 0.084(2) 0.065(2) 0.0005(18) 0.0154(14) -0.0093(17)
C13 0.0471(16) 0.0632(19) 0.0588(18) -0.0038(15) 0.0042(13) 0.0011(14)
C14 0.0545(17) 0.0482(17) 0.0457(15) -0.0015(13) 0.0095(12) 0.0034(13)
C15 0.0653(19) 0.0494(17) 0.0545(17) -0.0006(14) 0.0155(13) 0.0001(14)
C16 0.102(3) 0.099(3) 0.126(3) -0.024(3) 0.032(2) -0.052(3)
C17 0.119(3) 0.057(2) 0.0669(19) -0.0004(16) 0.0432(19) -0.0147(19)
N7 0.106(3) 0.081(2) 0.105(2) -0.0248(19) 0.0114(19) -0.0105(19)
O13 0.0715(15) 0.0690(15) 0.0817(14) -0.0149(12) 0.0176(11) -0.0221(12)
O14 0.0879(15) 0.0575(13) 0.0506(11) -0.0077(10) 0.0211(10) -0.0114(11)

_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 C2 1.374(4) . ?
C1 C6 1.384(4) . ?
C1 C7 1.445(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.383(4) . ?
C4 C8 1.433(4) . ?
C5 C6 1.375(4) . ?
C7 N7 1.139(4) . ?
C8 C9 1.203(4) . ?
C9 C10 1.427(4) . ?
C10 C11 1.378(4) . ?
C10 C15 1.412(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.373(4) . ?
C13 O13 1.367(3) . ?
C13 C14 1.404(4) . ?
C14 C15 1.360(4) . ?
C14 O14 1.373(3) . ?
C16 O13 1.434(4) . ?
C17 O14 1.430(3) . ?

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
C2 C1 C6 121.0(3) . . ?
C2 C1 C7 119.5(3) . . ?
C6 C1 C7 119.6(3) . . ?
C1 C2 C3 119.3(3) . . ?
C2 C3 C4 120.9(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C8 121.0(3) . . ?
C3 C4 C8 120.8(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 C1 119.1(3) . . ?
N7 C7 C1 177.0(4) . . ?
C9 C8 C4 177.0(4) . . ?
C8 C9 C10 178.8(4) . . ?
C11 C10 C15 118.0(3) . . ?
C11 C10 C9 121.4(3) . . ?
C15 C10 C9 120.6(3) . . ?
C10 C11 C12 121.1(3) . . ?
C13 C12 C11 120.5(3) . . ?
O13 C13 C12 125.6(3) . . ?
O13 C13 C14 115.4(2) . . ?
C12 C13 C14 119.1(3) . . ?
C15 C14 O14 124.9(2) . . ?
C15 C14 C13 120.4(2) . . ?
O14 C14 C13 114.7(2) . . ?
C14 C15 C10 120.9(3) . . ?
C13 O13 C16 117.6(3) . . ?
C14 O14 C17 116.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034
