# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_170725lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1841164'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
Taiwan
;
_audit_update_record             
;
2018-05-03 deposited with the CCDC.	2019-04-03 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            'C15 H10 O2'
_chemical_formula_weight         222.23

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.4742(8)
_cell_length_b                   5.9923(2)
_cell_length_c                   19.2732(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.981(2)
_cell_angle_gamma                90
_cell_volume                     2107.44(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      2.8411
_cell_measurement_theta_max      26.2097

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8877
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8563
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2159
_reflns_number_gt                1765
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0431P)²+1.5385P] 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         2159
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
O1 O 0.42927(5) 0.20893(16) 0.50254(5) 0.0185(2) Uani 1 1 d . . . . .
O2 O 0.36190(5) 0.06093(16) 0.40991(5) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.52499(7) 0.5158(3) 0.65072(7) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.5663 0.4981 0.6863 0.027 Uiso 1 1 calc R U . . .
C2 C 0.50717(7) 0.3484(2) 0.60153(7) 0.0199(3) Uani 1 1 d . . . . .
H10 H 0.5357 0.2161 0.6028 0.024 Uiso 1 1 calc R U . . .
C3 C 0.44649(7) 0.3797(2) 0.55026(7) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.37072(7) 0.2196(2) 0.44906(7) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.32526(7) 0.4220(2) 0.44370(7) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.26345(7) 0.4352(2) 0.38417(7) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.25502(7) 0.6247(2) 0.34156(7) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.2878 0.7468 0.3516 0.021 Uiso 1 1 calc R U . . .
C8 C 0.19875(7) 0.6357(2) 0.28442(7) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.1940 0.7636 0.2549 0.024 Uiso 1 1 calc R U . . .
C9 C 0.14966(7) 0.4598(2) 0.27048(7) 0.0202(3) Uani 1 1 d . . . . .
H2 H 0.1114 0.4671 0.2314 0.024 Uiso 1 1 calc R U . . .
C10 C 0.34291(7) 0.5892(2) 0.49011(7) 0.0153(3) Uani 1 1 d . . . . .
H5 H 0.3141 0.7213 0.4857 0.018 Uiso 1 1 calc R U . . .
C11 C 0.40414(7) 0.5732(2) 0.54608(7) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.42338(7) 0.7390(2) 0.59673(7) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.3952 0.8721 0.5953 0.022 Uiso 1 1 calc R U . . .
C13 C 0.48312(8) 0.7100(3) 0.64876(7) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.4957 0.8225 0.6833 0.026 Uiso 1 1 calc R U . . .
C14 C 0.21375(7) 0.2598(2) 0.36970(7) 0.0176(3) Uani 1 1 d . . . . .
H6 H 0.2190 0.1300 0.3983 0.021 Uiso 1 1 calc R U . . .
C15 C 0.15672(7) 0.2736(2) 0.31373(7) 0.0197(3) Uani 1 1 d . . . . .
H9 H 0.1224 0.1550 0.3050 0.024 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
O1 C4 1.3741(16) . ?
O1 C3 1.3795(16) . ?
O2 C4 1.2089(16) . ?
C1 C2 1.384(2) . ?
C1 C13 1.394(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3865(18) . ?
C2 H10 0.9500 . ?
C3 C11 1.3942(19) . ?
C4 C5 1.4695(19) . ?
C5 C10 1.3490(19) . ?
C5 C6 1.4892(18) . ?
C6 C14 1.3951(19) . ?
C6 C7 1.3957(19) . ?
C7 C8 1.3929(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C15 1.387(2) . ?
C9 H2 0.9500 . ?
C10 C11 1.4392(18) . ?
C10 H5 0.9500 . ?
C11 C12 1.3993(19) . ?
C12 C13 1.3815(19) . ?
C12 H3 0.9500 . ?
C13 H4 0.9500 . ?
C14 C15 1.3876(18) . ?
C14 H6 0.9500 . ?
C15 H9 0.9500 . ?

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
C4 O1 C3 122.56(10) . . ?
C2 C1 C13 120.96(13) . . ?
C2 C1 H1 119.5 . . ?
C13 C1 H1 119.5 . . ?
C1 C2 C3 118.01(13) . . ?
C1 C2 H10 121.0 . . ?
C3 C2 H10 121.0 . . ?
O1 C3 C2 116.84(12) . . ?
O1 C3 C11 120.63(12) . . ?
C2 C3 C11 122.53(13) . . ?
O2 C4 O1 116.44(12) . . ?
O2 C4 C5 125.82(12) . . ?
O1 C4 C5 117.74(11) . . ?
C10 C5 C4 119.35(12) . . ?
C10 C5 C6 123.24(12) . . ?
C4 C5 C6 117.34(12) . . ?
C14 C6 C7 119.07(12) . . ?
C14 C6 C5 121.03(12) . . ?
C7 C6 C5 119.90(12) . . ?
C8 C7 C6 120.30(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.09(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C15 C9 C8 119.80(13) . . ?
C15 C9 H2 120.1 . . ?
C8 C9 H2 120.1 . . ?
C5 C10 C11 121.85(12) . . ?
C5 C10 H5 119.1 . . ?
C11 C10 H5 119.1 . . ?
C3 C11 C12 118.10(12) . . ?
C3 C11 C10 117.85(12) . . ?
C12 C11 C10 124.05(12) . . ?
C13 C12 C11 120.27(13) . . ?
C13 C12 H3 119.9 . . ?
C11 C12 H3 119.9 . . ?
C12 C13 C1 120.12(13) . . ?
C12 C13 H4 119.9 . . ?
C1 C13 H4 119.9 . . ?
C15 C14 C6 120.44(13) . . ?
C15 C14 H6 119.8 . . ?
C6 C14 H6 119.8 . . ?
C9 C15 C14 120.27(13) . . ?
C9 C15 H9 119.9 . . ?
C14 C15 H9 119.9 . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_170811LT_a
_database_code_depnum_ccdc_archive 'CCDC 1841165'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
Taiwan
;
_audit_update_record             
;
2018-05-03 deposited with the CCDC.	2019-04-03 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 H9 N O2'
_chemical_formula_weight         247.24

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.795(7)
_cell_length_b                   7.246(4)
_cell_length_c                   12.168(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.255(11)
_cell_angle_gamma                90
_cell_volume                     1173.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1598
_cell_measurement_theta_min      3.0612
_cell_measurement_theta_max      25.9207

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7321
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10299
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.530
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2329
_reflns_number_gt                1431
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1451P)²+1.6899P] 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     SHELXL
_refine_ls_extinction_coef       0.028(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2329
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0912
_refine_ls_wR_factor_ref         0.2722
_refine_ls_wR_factor_gt          0.2398
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.4468(3) 0.6715(5) 0.8646(4) 0.0200(9) Uani 1 1 d . . . . .
C2 C 0.4936(3) 0.6214(5) 0.7729(3) 0.0181(9) Uani 1 1 d . . . . .
C3 C 0.4328(3) 0.5868(5) 0.6682(3) 0.0195(9) Uani 1 1 d . . . . .
H3 H 0.4625 0.5562 0.6084 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3259(3) 0.5944(5) 0.6438(4) 0.0209(9) Uani 1 1 d . . . . .
C5 C 0.2608(3) 0.5645(5) 0.5351(4) 0.0265(10) Uani 1 1 d . . . . .
H5 H 0.2877 0.5367 0.4727 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1587(3) 0.5754(5) 0.5188(4) 0.0308(11) Uani 1 1 d . . . . .
H6 H 0.1151 0.5552 0.4452 0.037 Uiso 1 1 calc R U . . .
C7 C 0.1190(3) 0.6159(6) 0.6099(4) 0.0332(11) Uani 1 1 d . . . . .
H7 H 0.0482 0.6238 0.5978 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1810(3) 0.6449(5) 0.7176(4) 0.0269(10) Uani 1 1 d . . . . .
H8 H 0.1536 0.6707 0.7799 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2829(3) 0.6356(5) 0.7328(4) 0.0205(9) Uani 1 1 d . . . . .
C10 C 0.6044(3) 0.6185(5) 0.7983(3) 0.0184(9) Uani 1 1 d . . . . .
C11 C 0.6655(3) 0.5554(5) 0.9017(4) 0.0212(9) Uani 1 1 d . . . . .
H11 H 0.6355 0.5137 0.9591 0.025 Uiso 1 1 calc R U . . .
C12 C 0.7684(3) 0.5523(5) 0.9224(4) 0.0236(9) Uani 1 1 d . . . . .
H12 H 0.8090 0.5099 0.9936 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8130(3) 0.6126(5) 0.8372(4) 0.0229(9) Uani 1 1 d . . . . .
C14 C 0.7531(3) 0.6766(5) 0.7338(4) 0.0227(9) Uani 1 1 d . . . . .
H14 H 0.7835 0.7195 0.6770 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6504(3) 0.6783(5) 0.7133(4) 0.0212(9) Uani 1 1 d . . . . .
H15 H 0.6100 0.7197 0.6417 0.025 Uiso 1 1 calc R U . . .
C16 C 0.9196(3) 0.6053(5) 0.8557(4) 0.0299(10) Uani 1 1 d . . . . .
N1 N 1.0054(3) 0.5978(6) 0.8678(4) 0.0457(12) Uani 1 1 d . . . . .
O1 O 0.34391(19) 0.6691(4) 0.8403(2) 0.0233(7) Uani 1 1 d . . . . .
O2 O 0.4916(2) 0.7163(4) 0.9604(2) 0.0268(8) Uani 1 1 d . . . . .


_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 O2 1.212(5) . ?
C1 O1 1.372(5) . ?
C1 C2 1.474(5) . ?
C2 C3 1.352(6) . ?
C2 C10 1.477(5) . ?
C3 C4 1.427(5) . ?
C3 H3 0.9500 . ?
C4 C9 1.396(6) . ?
C4 C5 1.406(6) . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9500 . ?
C9 O1 1.378(5) . ?
C10 C11 1.395(6) . ?
C10 C15 1.416(5) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(6) . ?
C13 C16 1.429(6) . ?
C14 C15 1.372(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N1 1.154(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
O2 C1 O1 116.6(3) . . ?
O2 C1 C2 125.5(3) . . ?
O1 C1 C2 118.0(4) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C10 123.1(3) . . ?
C1 C2 C10 118.7(3) . . ?
C2 C3 C4 122.7(4) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C9 C4 C5 117.8(4) . . ?
C9 C4 C3 118.3(4) . . ?
C5 C4 C3 124.0(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 118.6(4) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 O1 117.9(3) . . ?
C8 C9 C4 122.4(4) . . ?
O1 C9 C4 119.7(3) . . ?
C11 C10 C15 118.6(4) . . ?
C11 C10 C2 122.7(3) . . ?
C15 C10 C2 118.7(4) . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 C16 119.8(4) . . ?
C12 C13 C16 120.3(4) . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N1 C16 C13 178.2(5) . . ?
C1 O1 C9 123.0(3) . . ?

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_170926lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1841166'
loop_
_audit_author_name
_audit_author_address
'Vaibhav Charpe'
;NTHU
Taiwan
;
_audit_update_record             
;
2018-05-03 deposited with the CCDC.	2019-04-03 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            'C17 H14 O2'
_chemical_formula_weight         250.28

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.4167(12)
_cell_length_b                   7.2031(8)
_cell_length_c                   13.9328(15)
_cell_angle_alpha                90
_cell_angle_beta                 106.425(5)
_cell_angle_gamma                90
_cell_volume                     1291.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7027
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.861
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             2464
_reflns_number_gt                1973
_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)+(0.0576P)²+0.4253P] 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         2464
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.42651(7) 0.91436(15) 0.09188(7) 0.0209(3) Uani 1 1 d . . . . .
O2 O 0.25848(7) 0.95608(16) 0.03055(7) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.69714(11) 0.8446(2) 0.22544(12) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.7637 0.8663 0.2162 0.035 Uiso 1 1 calc R U . . .
C2 C 0.60901(11) 0.8944(2) 0.15078(11) 0.0239(3) Uani 1 1 d . . . . .
H14 H 0.6140 0.9485 0.0901 0.029 Uiso 1 1 calc R U . . .
C3 C 0.51323(10) 0.8632(2) 0.16712(10) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.32702(10) 0.9015(2) 0.10130(10) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.31490(10) 0.8212(2) 0.19421(10) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.20940(10) 0.8085(2) 0.20813(11) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.12184(10) 0.7618(2) 0.12979(11) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.1291 0.7390 0.0650 0.027 Uiso 1 1 calc R U . . .
C8 C 0.02419(11) 0.7482(2) 0.14570(12) 0.0252(4) Uani 1 1 d . . . . .
C9 C -0.07046(11) 0.6999(3) 0.06059(13) 0.0340(4) Uani 1 1 d . . . . .
H2 H -0.1139 0.6115 0.0842 0.051 Uiso 1 1 calc R U . . .
H11 H -0.0484 0.6439 0.0058 0.051 Uiso 1 1 calc R U . . .
H12 H -0.1104 0.8128 0.0366 0.051 Uiso 1 1 calc R U . . .
C10 C 0.40000(10) 0.7618(2) 0.26499(10) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.3915 0.7040 0.3235 0.024 Uiso 1 1 calc R U . . .
C11 C 0.50289(10) 0.7832(2) 0.25478(10) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.59382(11) 0.7308(2) 0.32823(11) 0.0228(3) Uani 1 1 d . . . . .
H4 H 0.5891 0.6730 0.3881 0.027 Uiso 1 1 calc R U . . .
C13 C 0.68999(11) 0.7631(2) 0.31378(11) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.7514 0.7296 0.3642 0.032 Uiso 1 1 calc R U . . .
C14 C 0.01505(11) 0.7827(2) 0.24083(12) 0.0273(4) Uani 1 1 d . . . . .
H10 H -0.0514 0.7736 0.2521 0.033 Uiso 1 1 calc R U . . .
C15 C 0.10030(11) 0.8300(2) 0.32014(11) 0.0245(4) Uani 1 1 d . . . . .
C16 C 0.19746(11) 0.8414(2) 0.30271(11) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.2566 0.8721 0.3564 0.026 Uiso 1 1 calc R U . . .
C17 C 0.08825(13) 0.8754(3) 0.42204(12) 0.0348(4) Uani 1 1 d . . . . .
H7 H 0.0804 1.0098 0.4278 0.052 Uiso 1 1 calc R U . . .
H9 H 0.1499 0.8333 0.4739 0.052 Uiso 1 1 calc R U . . .
H8 H 0.0266 0.8124 0.4306 0.052 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
O1 C3 1.3780(16) . ?
O1 C4 1.3808(16) . ?
O2 C4 1.2081(16) . ?
C1 C2 1.383(2) . ?
C1 C13 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3855(19) . ?
C2 H14 0.9500 . ?
C3 C11 1.392(2) . ?
C4 C5 1.4680(19) . ?
C5 C10 1.3500(19) . ?
C5 C6 1.4849(18) . ?
C6 C16 1.392(2) . ?
C6 C7 1.3999(19) . ?
C7 C8 1.3926(19) . ?
C7 H13 0.9500 . ?
C8 C14 1.387(2) . ?
C8 C9 1.513(2) . ?
C9 H2 0.9800 . ?
C9 H11 0.9800 . ?
C9 H12 0.9800 . ?
C10 C11 1.4355(18) . ?
C10 H5 0.9500 . ?
C11 C12 1.4043(19) . ?
C12 C13 1.381(2) . ?
C12 H4 0.9500 . ?
C13 H3 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H10 0.9500 . ?
C15 C16 1.3943(19) . ?
C15 C17 1.509(2) . ?
C16 H6 0.9500 . ?
C17 H7 0.9800 . ?
C17 H9 0.9800 . ?
C17 H8 0.9800 . ?

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
C3 O1 C4 122.73(11) . . ?
C2 C1 C13 121.12(13) . . ?
C2 C1 H1 119.4 . . ?
C13 C1 H1 119.4 . . ?
C1 C2 C3 118.00(14) . . ?
C1 C2 H14 121.0 . . ?
C3 C2 H14 121.0 . . ?
O1 C3 C2 117.03(13) . . ?
O1 C3 C11 120.39(12) . . ?
C2 C3 C11 122.58(13) . . ?
O2 C4 O1 115.70(12) . . ?
O2 C4 C5 126.81(12) . . ?
O1 C4 C5 117.48(11) . . ?
C10 C5 C4 119.16(12) . . ?
C10 C5 C6 121.71(13) . . ?
C4 C5 C6 119.13(12) . . ?
C16 C6 C7 118.90(13) . . ?
C16 C6 C5 118.84(12) . . ?
C7 C6 C5 122.26(13) . . ?
C8 C7 C6 120.83(14) . . ?
C8 C7 H13 119.6 . . ?
C6 C7 H13 119.6 . . ?
C14 C8 C7 118.73(14) . . ?
C14 C8 C9 120.58(13) . . ?
C7 C8 C9 120.68(14) . . ?
C8 C9 H2 109.5 . . ?
C8 C9 H11 109.5 . . ?
H2 C9 H11 109.5 . . ?
C8 C9 H12 109.5 . . ?
H2 C9 H12 109.5 . . ?
H11 C9 H12 109.5 . . ?
C5 C10 C11 122.14(13) . . ?
C5 C10 H5 118.9 . . ?
C11 C10 H5 118.9 . . ?
C3 C11 C12 117.97(12) . . ?
C3 C11 C10 117.94(12) . . ?
C12 C11 C10 124.09(13) . . ?
C13 C12 C11 120.24(14) . . ?
C13 C12 H4 119.9 . . ?
C11 C12 H4 119.9 . . ?
C12 C13 C1 120.07(14) . . ?
C12 C13 H3 120.0 . . ?
C1 C13 H3 120.0 . . ?
C8 C14 C15 121.89(13) . . ?
C8 C14 H10 119.1 . . ?
C15 C14 H10 119.1 . . ?
C14 C15 C16 118.41(14) . . ?
C14 C15 C17 121.20(13) . . ?
C16 C15 C17 120.35(14) . . ?
C6 C16 C15 121.23(14) . . ?
C6 C16 H6 119.4 . . ?
C15 C16 H6 119.4 . . ?
C15 C17 H7 109.5 . . ?
C15 C17 H9 109.5 . . ?
H7 C17 H9 109.5 . . ?
C15 C17 H8 109.5 . . ?
H7 C17 H8 109.5 . . ?
H9 C17 H8 109.5 . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.042

_shelxl_version_number           2014/6

