# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_tht160623-1
_database_code_depnum_ccdc_archive 'CCDC 1539434'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.0348(7)
_cell_length_b                   21.2718(12)
_cell_length_c                   7.2221(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1695.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1090
_cell_measurement_temperature    184.3(3)
_cell_measurement_theta_max      28.5310
_cell_measurement_theta_min      3.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6362
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.415
_diffrn_ambient_temperature      184.3(3)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   57.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   38.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   77.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   52.0000   48.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0368903000
_diffrn_orient_matrix_UB_12      -0.0272179000
_diffrn_orient_matrix_UB_13      0.0063556000
_diffrn_orient_matrix_UB_21      -0.0162701000
_diffrn_orient_matrix_UB_22      0.0034709000
_diffrn_orient_matrix_UB_23      -0.0944466000
_diffrn_orient_matrix_UB_31      0.0500242000
_diffrn_orient_matrix_UB_32      -0.0189791000
_diffrn_orient_matrix_UB_33      -0.0261397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                2472
_reflns_number_total             2770
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.2789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00E,H00F,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.7395(3) 0.11525(13) 0.3817(5) 0.0407(8) Uani 1 1 d . . . . .
N002 N 0.7641(3) 0.31054(14) 0.5078(6) 0.0279(8) Uani 1 1 d . . . . .
O003 O 0.6773(3) 0.47476(13) 0.5189(7) 0.0568(11) Uani 1 1 d . . . . .
N004 N 0.8875(3) 0.31309(15) 0.4972(6) 0.0325(9) Uani 1 1 d . . . . .
C005 C 0.8211(3) 0.21150(18) 0.4886(6) 0.0262(9) Uani 1 1 d . . . . .
C006 C 0.9435(3) 0.10901(17) 0.4771(6) 0.0259(10) Uani 1 1 d . . . . .
C007 C 1.0259(4) 0.1253(2) 0.6130(6) 0.0305(10) Uani 1 1 d . . . . .
H007 H 1.0105 0.1596 0.6891 0.037 Uiso 1 1 calc R . . . .
C008 C 0.7183(3) 0.25042(17) 0.5055(6) 0.0256(9) Uani 1 1 d . . . . .
C009 C 0.8264(4) 0.14311(19) 0.4474(6) 0.0272(10) Uani 1 1 d . . . . .
C00A C 0.5319(4) 0.18467(19) 0.5490(6) 0.0305(10) Uani 1 1 d . . . . .
H00A H 0.5776 0.1480 0.5451 0.037 Uiso 1 1 calc R . . . .
C00B C 0.6944(3) 0.36513(18) 0.5164(7) 0.0306(10) Uani 1 1 d . . . . .
C00C C 0.5886(4) 0.24328(17) 0.5256(6) 0.0262(9) Uani 1 1 d . . . . .
C00D C 0.9184(4) 0.25330(18) 0.4853(6) 0.0300(10) Uani 1 1 d . . . . .
H00D H 0.9985 0.2401 0.4755 0.036 Uiso 1 1 calc R . . . .
O00E O 0.8232(3) 0.54518(16) 0.5297(11) 0.095(2) Uani 1 1 d . . . . .
C00F C 0.5170(4) 0.29855(19) 0.5325(7) 0.0334(11) Uani 1 1 d . . . . .
C00G C 0.9680(4) 0.0573(2) 0.3637(7) 0.0343(11) Uani 1 1 d . . . . .
H00G H 0.9123 0.0453 0.2738 0.041 Uiso 1 1 calc R . . . .
C00H C 1.0743(4) 0.0240(2) 0.3846(7) 0.0405(12) Uani 1 1 d . . . . .
H00H H 1.0905 -0.0099 0.3070 0.049 Uiso 1 1 calc R . . . .
C00I C 0.5742(4) 0.35918(19) 0.5240(7) 0.0368(11) Uani 1 1 d . . . . .
H00I H 0.5263 0.3951 0.5239 0.044 Uiso 1 1 calc R . . . .
C00J C 0.7660(4) 0.42526(17) 0.5144(8) 0.0362(11) Uani 1 1 d . . . . .
H00B H 0.8189 0.4276 0.6215 0.043 Uiso 1 1 calc R . . . .
H00C H 0.8150 0.4281 0.4031 0.043 Uiso 1 1 calc R . . . .
C00K C 1.1564(4) 0.0404(2) 0.5186(8) 0.0393(12) Uani 1 1 d . . . . .
H00K H 1.2283 0.0180 0.5308 0.047 Uiso 1 1 calc R . . . .
C00L C 1.1318(4) 0.0907(2) 0.6369(7) 0.0361(11) Uani 1 1 d . . . . .
H00L H 1.1859 0.1011 0.7309 0.043 Uiso 1 1 calc R . . . .
C00M C 0.4095(4) 0.1816(2) 0.5774(7) 0.0401(12) Uani 1 1 d . . . . .
H00M H 0.3732 0.1427 0.5962 0.048 Uiso 1 1 calc R . . . .
C00N C 0.3910(4) 0.2927(2) 0.5572(8) 0.0473(15) Uani 1 1 d . . . . .
H00N H 0.3429 0.3286 0.5588 0.057 Uiso 1 1 calc R . . . .
C00O C 0.3386(4) 0.2353(2) 0.5786(8) 0.0476(14) Uani 1 1 d . . . . .
H00O H 0.2551 0.2322 0.5942 0.057 Uiso 1 1 calc R . . . .
C00P C 0.7189(5) 0.5337(2) 0.5271(12) 0.0581(16) Uani 1 1 d . . . . .
C00Q C 0.6169(5) 0.5798(2) 0.5311(14) 0.086(3) Uani 1 1 d . . . . .
H00E H 0.5489 0.5629 0.4650 0.128 Uiso 1 1 calc GR . . . .
H00F H 0.6422 0.6183 0.4737 0.128 Uiso 1 1 calc GR . . . .
H00J H 0.5941 0.5879 0.6571 0.128 Uiso 1 1 calc GR . . . .


_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 C009 1.223(5) . ?
N002 N004 1.365(4) . ?
N002 C008 1.375(5) . ?
N002 C00B 1.394(5) . ?
O003 C00J 1.438(5) . ?
O003 C00P 1.337(5) . ?
N004 C00D 1.319(5) . ?
C005 C008 1.410(5) . ?
C005 C009 1.486(5) . ?
C005 C00D 1.394(5) . ?
C006 C007 1.382(6) . ?
C006 C009 1.498(6) . ?
C006 C00G 1.397(6) . ?
C007 H007 0.9300 . ?
C007 C00L 1.391(6) . ?
C008 C00C 1.447(6) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.405(5) . ?
C00A C00M 1.367(6) . ?
C00B C00I 1.333(5) . ?
C00B C00J 1.504(5) . ?
C00C C00F 1.417(6) . ?
C00D H00D 0.9300 . ?
O00E C00P 1.177(5) . ?
C00F C00I 1.438(6) . ?
C00F C00N 1.407(6) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.380(6) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.370(7) . ?
C00I H00I 0.9300 . ?
C00J H00B 0.9700 . ?
C00J H00C 0.9700 . ?
C00K H00K 0.9300 . ?
C00K C00L 1.396(7) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.385(7) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.360(6) . ?
C00O H00O 0.9300 . ?
C00P C00Q 1.492(7) . ?
C00Q H00E 0.9600 . ?
C00Q H00F 0.9600 . ?
C00Q H00J 0.9600 . ?

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
N004 N002 C008 113.8(3) . . ?
N004 N002 C00B 121.3(3) . . ?
C008 N002 C00B 124.9(3) . . ?
C00P O003 C00J 117.0(3) . . ?
C00D N004 N002 102.9(3) . . ?
C008 C005 C009 128.6(4) . . ?
C00D C005 C008 104.3(3) . . ?
C00D C005 C009 126.2(4) . . ?
C007 C006 C009 123.2(4) . . ?
C007 C006 C00G 119.1(4) . . ?
C00G C006 C009 117.7(4) . . ?
C006 C007 H007 119.7 . . ?
C006 C007 C00L 120.6(4) . . ?
C00L C007 H007 119.7 . . ?
N002 C008 C005 104.6(3) . . ?
N002 C008 C00C 117.4(3) . . ?
C005 C008 C00C 138.0(3) . . ?
O001 C009 C005 121.4(4) . . ?
O001 C009 C006 119.8(4) . . ?
C005 C009 C006 118.7(3) . . ?
C00C C00A H00A 120.0 . . ?
C00M C00A H00A 120.0 . . ?
C00M C00A C00C 120.0(4) . . ?
N002 C00B C00J 114.7(3) . . ?
C00I C00B N002 118.1(4) . . ?
C00I C00B C00J 127.2(4) . . ?
C00A C00C C008 123.1(4) . . ?
C00A C00C C00F 118.9(4) . . ?
C00F C00C C008 117.9(3) . . ?
N004 C00D C005 114.5(3) . . ?
N004 C00D H00D 122.7 . . ?
C005 C00D H00D 122.7 . . ?
C00C C00F C00I 119.9(4) . . ?
C00N C00F C00C 118.8(4) . . ?
C00N C00F C00I 121.2(4) . . ?
C006 C00G H00G 119.8 . . ?
C00H C00G C006 120.3(4) . . ?
C00H C00G H00G 119.8 . . ?
C00G C00H H00H 119.7 . . ?
C00K C00H C00G 120.6(5) . . ?
C00K C00H H00H 119.7 . . ?
C00B C00I C00F 121.6(4) . . ?
C00B C00I H00I 119.2 . . ?
C00F C00I H00I 119.2 . . ?
O003 C00J C00B 105.4(3) . . ?
O003 C00J H00B 110.7 . . ?
O003 C00J H00C 110.7 . . ?
C00B C00J H00B 110.7 . . ?
C00B C00J H00C 110.7 . . ?
H00B C00J H00C 108.8 . . ?
C00H C00K H00K 120.0 . . ?
C00H C00K C00L 119.9(4) . . ?
C00L C00K H00K 120.0 . . ?
C007 C00L C00K 119.5(4) . . ?
C007 C00L H00L 120.3 . . ?
C00K C00L H00L 120.3 . . ?
C00A C00M H00M 119.3 . . ?
C00A C00M C00O 121.3(4) . . ?
C00O C00M H00M 119.3 . . ?
C00F C00N H00N 119.6 . . ?
C00O C00N C00F 120.9(4) . . ?
C00O C00N H00N 119.6 . . ?
C00M C00O H00O 120.0 . . ?
C00N C00O C00M 120.0(4) . . ?
C00N C00O H00O 120.0 . . ?
O003 C00P C00Q 111.0(4) . . ?
O00E C00P O003 122.0(4) . . ?
O00E C00P C00Q 126.9(4) . . ?
C00P C00Q H00E 109.5 . . ?
C00P C00Q H00F 109.5 . . ?
C00P C00Q H00J 109.5 . . ?
H00E C00Q H00F 109.5 . . ?
H00E C00Q H00J 109.5 . . ?
H00F C00Q H00J 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
