# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_hh
_database_code_depnum_ccdc_archive 'CCDC 1501144'
_audit_update_record             
;
2016-08-26 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.33

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   7.2650(3)
_cell_length_b                   8.2770(5)
_cell_length_c                   24.8418(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1493.80(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2144
_cell_measurement_theta_min      3.4750
_cell_measurement_theta_max      25.3940

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.7500
_exptl_crystal_size_mid          0.6500
_exptl_crystal_size_min          0.3000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5363
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2503
_reflns_number_gt                2098
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;

_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)+(0.0477P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(14)
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O2 O 0.60627(18) -0.06410(17) 0.13658(5) 0.0553(4) Uani 1 1 d . . .
N1 N 0.1916(2) 0.31542(18) 0.08517(6) 0.0457(4) Uani 1 1 d . . .
C7 C 0.3066(2) 0.0629(2) 0.07614(7) 0.0401(4) Uani 1 1 d . . .
C2 C 0.4054(2) 0.1477(2) 0.11781(7) 0.0413(4) Uani 1 1 d . . .
C12 C 0.1723(2) 0.1712(2) 0.05711(7) 0.0430(4) Uani 1 1 d . . .
C3 C 0.3300(2) 0.3002(2) 0.12189(7) 0.0433(4) Uani 1 1 d . . .
O1 O 0.61796(19) 0.15250(18) 0.19046(6) 0.0683(5) Uani 1 1 d . . .
C1 C 0.5513(2) 0.0867(2) 0.15221(8) 0.0440(5) Uani 1 1 d . . .
C8 C 0.3151(3) -0.0915(2) 0.05295(8) 0.0488(5) Uani 1 1 d . . .
H8 H 0.4028 -0.1659 0.0644 0.059 Uiso 1 1 calc R . .
C13 C 0.7452(3) -0.1368(2) 0.16798(8) 0.0463(5) Uani 1 1 d . . .
C5 C 0.0635(3) 0.4505(3) 0.08028(10) 0.0592(6) Uani 1 1 d . . .
H5A H 0.0289 0.4632 0.0428 0.071 Uiso 1 1 calc R . .
H5B H 0.1245 0.5490 0.0917 0.071 Uiso 1 1 calc R . .
C11 C 0.0482(3) 0.1313(3) 0.01713(9) 0.0570(5) Uani 1 1 d . . .
H11 H -0.0401 0.2046 0.0053 0.068 Uiso 1 1 calc R . .
C14 C 0.6964(3) -0.2328(3) 0.21011(9) 0.0589(6) Uani 1 1 d . . .
H14 H 0.5730 -0.2475 0.2188 0.071 Uiso 1 1 calc R . .
C9 C 0.1918(3) -0.1312(3) 0.01306(8) 0.0600(6) Uani 1 1 d . . .
H9 H 0.1966 -0.2334 -0.0024 0.072 Uiso 1 1 calc R . .
C4 C 0.3828(3) 0.4376(3) 0.15733(9) 0.0586(5) Uani 1 1 d . . .
H4A H 0.4079 0.5311 0.1357 0.088 Uiso 1 1 calc R . .
H4B H 0.4909 0.4093 0.1775 0.088 Uiso 1 1 calc R . .
H4C H 0.2837 0.4610 0.1817 0.088 Uiso 1 1 calc R . .
C10 C 0.0604(3) -0.0216(3) -0.00461(9) 0.0643(6) Uani 1 1 d . . .
H10 H -0.0210 -0.0519 -0.0317 0.077 Uiso 1 1 calc R . .
C18 C 0.9256(3) -0.1149(3) 0.15382(9) 0.0588(6) Uani 1 1 d . . .
H18 H 0.9564 -0.0506 0.1245 0.071 Uiso 1 1 calc R . .
C15 C 0.8314(3) -0.3075(3) 0.23970(9) 0.0729(7) Uani 1 1 d . . .
H15 H 0.7996 -0.3737 0.2685 0.087 Uiso 1 1 calc R . .
C16 C 1.0148(3) -0.2843(3) 0.22668(9) 0.0679(7) Uani 1 1 d . . .
H16 H 1.1067 -0.3331 0.2471 0.081 Uiso 1 1 calc R . .
C6 C -0.1079(3) 0.4261(3) 0.11372(11) 0.0799(7) Uani 1 1 d . . .
H6A H -0.1714 0.3311 0.1016 0.120 Uiso 1 1 calc R . .
H6B H -0.1869 0.5184 0.1100 0.120 Uiso 1 1 calc R . .
H6C H -0.0742 0.4132 0.1509 0.120 Uiso 1 1 calc R . .
C17 C 1.0602(3) -0.1890(3) 0.18355(10) 0.0678(6) Uani 1 1 d . . .
H17 H 1.1833 -0.1746 0.1744 0.081 Uiso 1 1 calc R . .

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
O2 0.0577(7) 0.0526(8) 0.0557(8) -0.0092(7) -0.0170(7) 0.0189(7)
N1 0.0423(8) 0.0414(9) 0.0533(9) 0.0062(8) -0.0016(8) 0.0036(7)
C7 0.0376(8) 0.0423(10) 0.0404(10) 0.0056(8) 0.0027(8) -0.0002(8)
C2 0.0388(9) 0.0412(10) 0.0441(10) 0.0007(8) 0.0013(8) 0.0017(9)
C12 0.0391(9) 0.0440(11) 0.0461(10) 0.0079(9) 0.0000(9) -0.0011(9)
C3 0.0386(9) 0.0426(11) 0.0487(10) 0.0023(9) 0.0029(9) 0.0008(9)
O1 0.0693(9) 0.0624(9) 0.0733(10) -0.0212(8) -0.0276(8) 0.0171(8)
C1 0.0387(9) 0.0461(11) 0.0470(11) -0.0040(9) -0.0019(9) 0.0030(9)
C8 0.0521(10) 0.0460(11) 0.0482(10) 0.0011(9) -0.0033(10) 0.0031(9)
C13 0.0475(10) 0.0448(11) 0.0465(11) -0.0053(9) -0.0072(8) 0.0106(10)
C5 0.0589(12) 0.0459(11) 0.0728(14) 0.0088(11) -0.0050(11) 0.0128(10)
C11 0.0556(11) 0.0595(13) 0.0559(12) 0.0108(11) -0.0137(10) 0.0021(11)
C14 0.0533(11) 0.0657(14) 0.0577(13) 0.0037(11) 0.0035(11) 0.0086(11)
C9 0.0716(13) 0.0519(12) 0.0563(12) -0.0033(11) -0.0118(12) -0.0021(12)
C4 0.0643(12) 0.0469(12) 0.0645(13) -0.0052(10) -0.0017(11) 0.0058(11)
C10 0.0721(14) 0.0668(15) 0.0541(13) 0.0029(11) -0.0187(11) -0.0092(13)
C18 0.0520(12) 0.0562(13) 0.0682(14) 0.0059(11) -0.0006(10) 0.0064(10)
C15 0.0930(16) 0.0744(16) 0.0513(13) 0.0110(12) 0.0000(13) 0.0265(15)
C16 0.0701(15) 0.0714(16) 0.0621(15) -0.0097(12) -0.0215(12) 0.0313(13)
C6 0.0560(12) 0.0863(18) 0.0975(18) -0.0080(15) 0.0085(13) 0.0161(14)
C17 0.0479(11) 0.0672(15) 0.0884(17) -0.0092(14) -0.0103(12) 0.0095(12)

_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
O2 C1 1.367(2) . ?
O2 C13 1.410(2) . ?
N1 C3 1.363(2) . ?
N1 C12 1.390(3) . ?
N1 C5 1.460(2) . ?
C7 C8 1.404(3) . ?
C7 C12 1.407(2) . ?
C7 C2 1.442(2) . ?
C2 C3 1.380(3) . ?
C2 C1 1.453(3) . ?
C12 C11 1.381(3) . ?
C3 C4 1.488(3) . ?
O1 C1 1.197(2) . ?
C8 C9 1.375(3) . ?
C13 C14 1.361(3) . ?
C13 C18 1.369(3) . ?
C5 C6 1.510(3) . ?
C11 C10 1.378(3) . ?
C14 C15 1.373(3) . ?
C9 C10 1.388(3) . ?
C18 C17 1.371(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.371(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
C1 O2 C13 116.18(14) . . ?
C3 N1 C12 109.34(14) . . ?
C3 N1 C5 126.62(17) . . ?
C12 N1 C5 123.48(16) . . ?
C8 C7 C12 118.19(17) . . ?
C8 C7 C2 135.74(17) . . ?
C12 C7 C2 106.06(16) . . ?
C3 C2 C7 107.51(16) . . ?
C3 C2 C1 124.37(17) . . ?
C7 C2 C1 128.05(17) . . ?
C11 C12 N1 129.21(18) . . ?
C11 C12 C7 122.84(18) . . ?
N1 C12 C7 107.95(15) . . ?
N1 C3 C2 109.12(16) . . ?
N1 C3 C4 121.03(17) . . ?
C2 C3 C4 129.82(17) . . ?
O1 C1 O2 121.54(17) . . ?
O1 C1 C2 127.13(18) . . ?
O2 C1 C2 111.31(16) . . ?
C9 C8 C7 118.98(19) . . ?
C14 C13 C18 121.62(19) . . ?
C14 C13 O2 119.20(17) . . ?
C18 C13 O2 119.12(18) . . ?
N1 C5 C6 112.18(17) . . ?
C10 C11 C12 117.32(19) . . ?
C13 C14 C15 119.28(19) . . ?
C8 C9 C10 121.3(2) . . ?
C11 C10 C9 121.3(2) . . ?
C13 C18 C17 119.0(2) . . ?
C14 C15 C16 120.0(2) . . ?
C17 C16 C15 119.6(2) . . ?
C16 C17 C18 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
