# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_TRYA1_a
_database_code_depnum_ccdc_archive 'CCDC 1444012'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.41800(10)
_cell_length_b                   7.55290(10)
_cell_length_c                   10.9647(2)
_cell_angle_alpha                80.8360(10)
_cell_angle_beta                 86.5030(10)
_cell_angle_gamma                84.0740(10)
_cell_volume                     602.621(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .11
_exptl_crystal_size_min          .09
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12824
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         30.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3589
_reflns_number_gt                3102
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3589
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.88538(9) -0.00470(9) 0.12169(6) 0.02282(19) Uani 1 1 d . . . . .
O002 O 0.72268(11) 0.31621(10) 0.04258(6) 0.0283(2) Uani 1 1 d . . . . .
N003 N 0.74830(15) 0.38521(14) 0.46508(9) 0.0357(3) Uani 1 1 d . . . . .
C004 C 0.35605(12) 1.03658(12) 0.22394(9) 0.0176(2) Uani 1 1 d . . . . .
C005 C 0.68125(12) 0.42062(12) 0.23397(8) 0.0177(2) Uani 1 1 d . . . . .
C006 C 0.82800(12) 0.10465(12) 0.20754(8) 0.0170(2) Uani 1 1 d . . . . .
C007 C 0.87025(13) 0.01887(13) 0.32263(9) 0.0204(2) Uani 1 1 d . . . . .
H007 H 0.8459 0.0639 0.3967 0.024 Uiso 1 1 calc R U . . .
C008 C 0.74299(12) 0.28092(12) 0.15410(8) 0.0179(2) Uani 1 1 d . . . . .
C009 C 0.58491(12) 0.57456(12) 0.18200(9) 0.0188(2) Uani 1 1 d . . . . .
H009 H 0.5608 0.5835 0.0989 0.023 Uiso 1 1 calc R U . . .
C00A C 0.42799(13) 0.87169(13) 0.17839(9) 0.0195(2) Uani 1 1 d . . . . .
H00A H 0.4107 0.8673 0.0957 0.023 Uiso 1 1 calc R U . . .
C00B C 0.51720(13) 0.72377(12) 0.24243(9) 0.0195(2) Uani 1 1 d . . . . .
H00B H 0.5345 0.7193 0.3262 0.023 Uiso 1 1 calc R U . . .
C00C C 0.71945(13) 0.39829(13) 0.36185(9) 0.0223(2) Uani 1 1 d . . . . .
C00D C 0.36394(13) 1.06214(13) 0.34723(9) 0.0212(2) Uani 1 1 d . . . . .
H00D H 0.4167 0.9702 0.4045 0.025 Uiso 1 1 calc R U . . .
C00E C 0.27444(13) 1.17707(13) 0.14026(9) 0.0205(2) Uani 1 1 d . . . . .
H00E H 0.2669 1.1618 0.0583 0.025 Uiso 1 1 calc R U . . .
C00F C 0.20453(13) 1.33873(13) 0.17740(10) 0.0245(2) Uani 1 1 d . . . . .
H00F H 0.1513 1.4310 0.1205 0.029 Uiso 1 1 calc R U . . .
C00G C 0.95862(13) -0.15242(13) 0.30752(10) 0.0242(2) Uani 1 1 d . . . . .
H00G H 1.0032 -0.2420 0.3696 0.029 Uiso 1 1 calc R U . . .
C00H C 0.21438(14) 1.36214(13) 0.29970(10) 0.0248(2) Uani 1 1 d . . . . .
H00H H 0.1681 1.4703 0.3250 0.030 Uiso 1 1 calc R U . . .
C00I C 0.96508(14) -0.15938(13) 0.18505(10) 0.0254(2) Uani 1 1 d . . . . .
H00I H 1.0171 -0.2570 0.1489 0.030 Uiso 1 1 calc R U . . .
C00J C 0.29377(14) 1.22319(13) 0.38439(10) 0.0242(2) Uani 1 1 d . . . . .
H00J H 0.2997 1.2386 0.4665 0.029 Uiso 1 1 calc R U . . .


_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
O001 C00I 1.3586(11) . ?
O001 C006 1.3695(10) . ?
O002 C008 1.2245(11) . ?
N003 C00C 1.1517(13) . ?
C004 C00E 1.3997(12) . ?
C004 C00D 1.4011(13) . ?
C004 C00A 1.4538(12) . ?
C005 C009 1.3618(12) . ?
C005 C00C 1.4276(13) . ?
C005 C008 1.4951(12) . ?
C006 C007 1.3624(13) . ?
C006 C008 1.4618(12) . ?
C007 C00G 1.4180(12) . ?
C007 H007 0.9300 . ?
C009 C00B 1.4289(12) . ?
C009 H009 0.9300 . ?
C00A C00B 1.3540(12) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00D C00J 1.3848(12) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.3883(13) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.3874(15) . ?
C00F H00F 0.9300 . ?
C00G C00I 1.3499(15) . ?
C00G H00G 0.9300 . ?
C00H C00J 1.3926(14) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00J 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
C00I O001 C006 106.51(7) . . ?
C00E C004 C00D 118.29(8) . . ?
C00E C004 C00A 118.27(8) . . ?
C00D C004 C00A 123.44(8) . . ?
C009 C005 C00C 119.16(8) . . ?
C009 C005 C008 118.34(8) . . ?
C00C C005 C008 122.51(8) . . ?
C007 C006 O001 109.69(8) . . ?
C007 C006 C008 136.56(9) . . ?
O001 C006 C008 113.74(8) . . ?
C006 C007 C00G 106.64(8) . . ?
C006 C007 H007 126.7 . . ?
C00G C007 H007 126.7 . . ?
O002 C008 C006 120.06(8) . . ?
O002 C008 C005 119.15(8) . . ?
C006 C008 C005 120.79(8) . . ?
C005 C009 C00B 126.49(9) . . ?
C005 C009 H009 116.8 . . ?
C00B C009 H009 116.8 . . ?
C00B C00A C004 127.54(9) . . ?
C00B C00A H00A 116.2 . . ?
C004 C00A H00A 116.2 . . ?
C00A C00B C009 120.36(8) . . ?
C00A C00B H00B 119.8 . . ?
C009 C00B H00B 119.8 . . ?
N003 C00C C005 178.07(10) . . ?
C00J C00D C004 120.51(9) . . ?
C00J C00D H00D 119.7 . . ?
C004 C00D H00D 119.7 . . ?
C00F C00E C004 121.22(9) . . ?
C00F C00E H00E 119.4 . . ?
C004 C00E H00E 119.4 . . ?
C00H C00F C00E 119.74(9) . . ?
C00H C00F H00F 120.1 . . ?
C00E C00F H00F 120.1 . . ?
C00I C00G C007 106.25(8) . . ?
C00I C00G H00G 126.9 . . ?
C007 C00G H00G 126.9 . . ?
C00F C00H C00J 119.79(9) . . ?
C00F C00H H00H 120.1 . . ?
C00J C00H H00H 120.1 . . ?
C00G C00I O001 110.91(8) . . ?
C00G C00I H00I 124.5 . . ?
O001 C00I H00I 124.5 . . ?
C00D C00J C00H 120.46(9) . . ?
C00D C00J H00J 119.8 . . ?
C00H C00J H00J 119.8 . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

