# 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_th4036
_database_code_depnum_ccdc_archive 'CCDC 1894788'
loop_
_audit_author_name
_audit_author_address
'Ganesh kumar Dhandabani'
;Kaohsiung medical university
Taiwan
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H19 N, 0.45(H2 O)'
_chemical_formula_sum            'C24 H19.90 N O0.45'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         329.51

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                   9.2367(4)
_cell_length_b                   10.2565(5)
_cell_length_c                   11.0747(6)
_cell_angle_alpha                104.8513(17)
_cell_angle_beta                 109.5128(15)
_cell_angle_gamma                108.1988(15)
_cell_volume                     859.89(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      3.203
_cell_measurement_theta_max      26.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             349
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28959
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3517
_reflns_number_gt                2774
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0572P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3517
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.010
_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
N N 0.42505(14) 0.73656(12) 0.02202(11) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.54751(16) 1.00332(15) 0.17094(13) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.69904(18) 1.13665(16) 0.26598(14) 0.0254(3) Uani 1 1 d . . . . .
H2A H 0.6913 1.2274 0.3023 0.031 Uiso 1 1 calc R U . . .
C3 C 0.85588(18) 1.13636(18) 0.30592(15) 0.0301(3) Uani 1 1 d . . . . .
H3A H 0.9558 1.2269 0.3688 0.036 Uiso 1 1 calc R U . . .
C4 C 0.87035(18) 1.00310(18) 0.25463(15) 0.0297(3) Uani 1 1 d . . . . .
H4A H 0.9797 1.0037 0.2848 0.036 Uiso 1 1 calc R U . . .
C5 C 0.72754(18) 0.87221(17) 0.16119(14) 0.0257(3) Uani 1 1 d . . . . .
H5A H 0.7387 0.7831 0.1258 0.031 Uiso 1 1 calc R U . . .
C6 C 0.56324(16) 0.86945(15) 0.11714(13) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.27107(16) 0.73249(14) -0.01574(13) 0.0180(3) Uani 1 1 d . . . . .
C8 C 0.12231(17) 0.59109(14) -0.12502(13) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.14142(19) 0.48500(16) -0.21897(15) 0.0265(3) Uani 1 1 d . . . . .
H9A H 0.2517 0.5022 -0.2118 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0005(2) 0.35518(17) -0.32227(16) 0.0328(4) Uani 1 1 d . . . . .
H10A H 0.0145 0.2835 -0.3855 0.039 Uiso 1 1 calc R U . . .
C11 C -0.1609(2) 0.32980(17) -0.33354(16) 0.0331(4) Uani 1 1 d . . . . .
H11A H -0.2577 0.2413 -0.4051 0.040 Uiso 1 1 calc R U . . .
C12 C -0.18096(18) 0.43347(16) -0.24044(15) 0.0280(3) Uani 1 1 d . . . . .
H12A H -0.2917 0.4150 -0.2481 0.034 Uiso 1 1 calc R U . . .
C13 C -0.04060(17) 0.56465(15) -0.13565(14) 0.0212(3) Uani 1 1 d . . . . .
C14 C -0.05719(17) 0.67941(15) -0.03231(15) 0.0229(3) Uani 1 1 d . . . . .
H14A H -0.0271 0.6656 0.0566 0.027 Uiso 1 1 calc R U . . .
H14B H -0.1770 0.6653 -0.0694 0.027 Uiso 1 1 calc R U . . .
C15 C 0.06012(17) 0.83780(15) -0.00472(15) 0.0216(3) Uani 1 1 d . . . . .
H15A H 0.0200 0.8562 -0.0907 0.026 Uiso 1 1 calc R U . . .
H15B H 0.0552 0.9115 0.0697 0.026 Uiso 1 1 calc R U . . .
C16 C 0.24249(16) 0.85932(15) 0.03967(13) 0.0184(3) Uani 1 1 d . . . . .
C17 C 0.38062(17) 0.99593(15) 0.12811(13) 0.0189(3) Uani 1 1 d . . . . .
C18 C 0.35693(17) 1.13581(15) 0.17880(14) 0.0221(3) Uani 1 1 d . . . . .
H18A H 0.2502 1.1247 0.1067 0.027 Uiso 1 1 calc R U . . .
H18B H 0.4525 1.2220 0.1877 0.027 Uiso 1 1 calc R U . . .
C19 C 0.34865(16) 1.17203(15) 0.31745(14) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.33538(18) 1.30306(15) 0.37471(15) 0.0253(3) Uani 1 1 d . . . . .
H20A H 0.3332 1.3679 0.3271 0.030 Uiso 1 1 calc R U . . .
C21 C 0.32534(19) 1.34008(17) 0.50005(16) 0.0299(3) Uani 1 1 d . . . . .
H21A H 0.3166 1.4300 0.5376 0.036 Uiso 1 1 calc R U . . .
C22 C 0.32794(19) 1.24692(17) 0.57093(15) 0.0299(3) Uani 1 1 d . . . . .
H22A H 0.3215 1.2726 0.6571 0.036 Uiso 1 1 calc R U . . .
C23 C 0.33999(19) 1.11596(18) 0.51492(16) 0.0300(3) Uani 1 1 d . . . . .
H23A H 0.3410 1.0510 0.5625 0.036 Uiso 1 1 calc R U . . .
C24 C 0.35066(17) 1.07875(16) 0.38903(15) 0.0236(3) Uani 1 1 d . . . . .
H24A H 0.3594 0.9888 0.3517 0.028 Uiso 1 1 calc R U . . .
O O 0.4682(3) 0.4860(3) 0.0941(3) 0.0338(6) Uiso 0.45 1 d . . P . .
H0A H 0.464(6) 0.531(5) 0.053(5) 0.050(13) Uiso 0.45 1 d . . P . .
H0B H 0.508(8) 0.412(7) 0.032(7) 0.11(2) Uiso 0.45 1 d . . P . .


_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
N C7 1.3251(17) . ?
N C6 1.3695(17) . ?
C1 C6 1.4228(19) . ?
C1 C2 1.4211(19) . ?
C1 C17 1.4238(18) . ?
C2 C3 1.367(2) . ?
C3 C4 1.405(2) . ?
C4 C5 1.372(2) . ?
C5 C6 1.4189(19) . ?
C7 C16 1.4325(18) . ?
C7 C8 1.4834(18) . ?
C8 C9 1.4001(19) . ?
C8 C13 1.4007(19) . ?
C9 C10 1.385(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.385(2) . ?
C12 C13 1.3938(19) . ?
C13 C14 1.5027(19) . ?
C14 C15 1.5269(18) . ?
C15 C16 1.5122(18) . ?
C16 C17 1.3767(19) . ?
C17 C18 1.5122(18) . ?
C18 C19 1.5184(18) . ?
C19 C24 1.3907(19) . ?
C19 C20 1.3933(18) . ?
C20 C21 1.385(2) . ?
C21 C22 1.384(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.393(2) . ?

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
C7 N C6 118.10(11) . . ?
C6 C1 C2 118.24(12) . . ?
C6 C1 C17 118.19(12) . . ?
C2 C1 C17 123.56(13) . . ?
C3 C2 C1 121.02(14) . . ?
C2 C3 C4 120.47(14) . . ?
C5 C4 C3 120.45(13) . . ?
C4 C5 C6 120.28(14) . . ?
N C6 C1 122.48(12) . . ?
N C6 C5 118.00(12) . . ?
C1 C6 C5 119.52(12) . . ?
N C7 C16 123.21(12) . . ?
N C7 C8 118.02(11) . . ?
C16 C7 C8 118.72(11) . . ?
C9 C8 C13 119.50(12) . . ?
C9 C8 C7 121.24(12) . . ?
C13 C8 C7 119.25(12) . . ?
C8 C9 C10 120.43(14) . . ?
C9 C10 C11 120.02(14) . . ?
C12 C11 C10 119.99(14) . . ?
C11 C12 C13 120.79(14) . . ?
C12 C13 C8 119.27(13) . . ?
C12 C13 C14 122.33(12) . . ?
C8 C13 C14 118.40(12) . . ?
C13 C14 C15 110.62(11) . . ?
C16 C15 C14 111.14(11) . . ?
C17 C16 C7 119.19(12) . . ?
C17 C16 C15 122.62(12) . . ?
C7 C16 C15 118.17(11) . . ?
C16 C17 C1 118.56(12) . . ?
C16 C17 C18 121.10(12) . . ?
C1 C17 C18 120.34(12) . . ?
C17 C18 C19 115.26(11) . . ?
C24 C19 C20 118.31(12) . . ?
C24 C19 C18 122.91(12) . . ?
C20 C19 C18 118.77(12) . . ?
C21 C20 C19 120.94(13) . . ?
C22 C21 C20 120.43(14) . . ?
C21 C22 C23 119.29(13) . . ?
C22 C23 C24 120.37(14) . . ?
C19 C24 C23 120.67(13) . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_th6194
_database_code_depnum_ccdc_archive 'CCDC 1902433'
loop_
_audit_author_name
_audit_author_address
'Ganesh kumar Dhandabani'
;Kaohsiung medical university
Taiwan
;
_audit_update_record             
;
2019-03-10 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Debenzolyation
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H11 N'
_chemical_formula_sum            'C17 H11 N'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         229.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.5356(4)
_cell_length_b                   17.1340(14)
_cell_length_c                   17.5416(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1363.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6644
_cell_measurement_theta_min      3.323
_cell_measurement_theta_max      26.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18945
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.324
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2789
_reflns_number_gt                2045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0744P)²+0.4970P] 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_abs_structure_details 
;
 Flack x determined using 713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1496
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N N -0.2234(6) 0.45038(17) 0.75608(15) 0.0351(7) Uani 1 1 d . . . . .
C1 C -0.3442(7) 0.5223(2) 0.76358(18) 0.0334(8) Uani 1 1 d . . . . .
C2 C -0.5527(8) 0.5492(2) 0.70924(19) 0.0415(9) Uani 1 1 d . . . . .
H2A H -0.6086 0.5164 0.6681 0.050 Uiso 1 1 calc R U . . .
C3 C -0.6713(8) 0.6207(3) 0.7155(2) 0.0503(10) Uani 1 1 d . . . . .
H3A H -0.8097 0.6377 0.6784 0.060 Uiso 1 1 calc R U . . .
C4 C -0.5946(9) 0.6711(2) 0.7761(2) 0.0502(10) Uani 1 1 d . . . . .
H4A H -0.6800 0.7216 0.7796 0.060 Uiso 1 1 calc R U . . .
C5 C -0.3958(8) 0.6465(2) 0.8300(2) 0.0428(9) Uani 1 1 d . . . . .
H5A H -0.3439 0.6804 0.8707 0.051 Uiso 1 1 calc R U . . .
C6 C -0.2676(7) 0.57181(19) 0.82575(18) 0.0323(7) Uani 1 1 d . . . . .
C7 C -0.0652(7) 0.54400(19) 0.87957(18) 0.0313(7) Uani 1 1 d . . . . .
H7A H -0.0112 0.5762 0.9214 0.038 Uiso 1 1 calc R U . . .
C8 C 0.0565(7) 0.47094(19) 0.87278(17) 0.0277(7) Uani 1 1 d . . . . .
C9 C 0.2666(7) 0.43922(19) 0.92698(17) 0.0285(7) Uani 1 1 d . . . . .
C10 C 0.3627(7) 0.4806(2) 0.99145(19) 0.0360(8) Uani 1 1 d . . . . .
H10A H 0.2886 0.5317 1.0005 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5622(8) 0.4488(2) 1.0418(2) 0.0417(9) Uani 1 1 d . . . . .
H11A H 0.6238 0.4780 1.0850 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6743(8) 0.3742(2) 1.0300(2) 0.0428(9) Uani 1 1 d . . . . .
H12A H 0.8117 0.3525 1.0649 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5847(8) 0.3326(2) 0.9677(2) 0.0399(9) Uani 1 1 d . . . . .
H13A H 0.6619 0.2817 0.9596 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3817(7) 0.36321(19) 0.91549(19) 0.0330(8) Uani 1 1 d . . . . .
C15 C 0.2876(8) 0.3201(2) 0.8497(2) 0.0404(9) Uani 1 1 d . . . . .
H15A H 0.3645 0.2692 0.8417 0.048 Uiso 1 1 calc R U . . .
C16 C 0.0942(8) 0.3493(2) 0.7990(2) 0.0397(9) Uani 1 1 d . . . . .
H16A H 0.0396 0.3188 0.7561 0.048 Uiso 1 1 calc R U . . .
C17 C -0.0305(7) 0.42510(19) 0.80846(18) 0.0316(7) 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
N C17 1.341(4) . ?
N C1 1.355(4) . ?
C1 C6 1.425(5) . ?
C1 C2 1.420(5) . ?
C2 C3 1.341(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.414(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.372(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.408(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.400(4) . ?
C7 C8 1.373(4) . ?
C7 H7A 0.9500 . ?
C8 C17 1.430(4) . ?
C8 C9 1.451(4) . ?
C9 C14 1.417(5) . ?
C9 C10 1.405(5) . ?
C10 C11 1.378(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.367(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.401(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.434(5) . ?
C15 C16 1.346(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.426(5) . ?
C16 H16A 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
C17 N C1 119.4(3) . . ?
N C1 C6 121.1(3) . . ?
N C1 C2 120.0(3) . . ?
C6 C1 C2 118.9(3) . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2A 119.7 . . ?
C1 C2 H2A 119.7 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C7 C6 C1 118.3(3) . . ?
C7 C6 C5 123.0(3) . . ?
C1 C6 C5 118.8(3) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C7 C8 C17 117.3(3) . . ?
C7 C8 C9 123.3(3) . . ?
C17 C8 C9 119.5(3) . . ?
C14 C9 C10 117.7(3) . . ?
C14 C9 C8 119.5(3) . . ?
C10 C9 C8 122.8(3) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C13 C14 C9 119.5(3) . . ?
C13 C14 C15 121.9(3) . . ?
C9 C14 C15 118.5(3) . . ?
C16 C15 C14 122.3(3) . . ?
C16 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16A 119.3 . . ?
C17 C16 H16A 119.3 . . ?
N C17 C16 118.3(3) . . ?
N C17 C8 122.9(3) . . ?
C16 C17 C8 118.8(3) . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_th3175
_database_code_depnum_ccdc_archive 'CCDC 1894798'
loop_
_audit_author_name
_audit_author_address
'Ganesh kumar Dhandabani'
;Kaohsiung medical university
Taiwan
;
_audit_update_record             
;
2019-01-31 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C34 H26 N2'
_chemical_formula_sum            'C34 H26 N2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         462.57

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'

_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                   20.9893(8)
_cell_length_b                   11.0183(4)
_cell_length_c                   11.5218(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.8192(16)
_cell_angle_gamma                90
_cell_volume                     2639.83(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7666
_cell_measurement_theta_min      3.472
_cell_measurement_theta_max      26.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8284
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23416
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.570
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2696
_reflns_number_gt                2147
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0763P)²+4.6009P] 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         2696
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N N 0.04741(7) 1.14829(14) 0.18224(13) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.00794(9) 0.81469(16) 0.18738(15) 0.0184(4) Uani 1 1 d . . . . .
H1A H 0.0370 0.7458 0.1778 0.022 Uiso 1 1 calc R U . . .
H1B H -0.0322 0.8018 0.1329 0.022 Uiso 1 1 calc R U . . .
C2 C 0.03934(8) 0.93060(16) 0.15393(15) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.02326(8) 1.04158(16) 0.20640(14) 0.0138(4) Uani 1 1 d . . . . .
C4 C 0.08826(9) 1.15247(17) 0.09996(15) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.11349(10) 1.2673(2) 0.07367(18) 0.0275(5) Uani 1 1 d . . . . .
H5A H 0.1019 1.3375 0.1139 0.033 Uiso 1 1 calc R U . . .
C6 C 0.15419(11) 1.2781(2) -0.00869(19) 0.0350(5) Uani 1 1 d . . . . .
H6A H 0.1709 1.3554 -0.0250 0.042 Uiso 1 1 calc R U . . .
C7 C 0.17140(10) 1.1753(2) -0.06934(19) 0.0349(5) Uani 1 1 d . . . . .
H7A H 0.1994 1.1835 -0.1271 0.042 Uiso 1 1 calc R U . . .
C8 C 0.14810(9) 1.0634(2) -0.04573(18) 0.0280(5) Uani 1 1 d . . . . .
H8A H 0.1602 0.9949 -0.0877 0.034 Uiso 1 1 calc R U . . .
C9 C 0.10607(8) 1.04717(18) 0.04022(15) 0.0194(4) Uani 1 1 d . . . . .
C10 C 0.08066(8) 0.93323(17) 0.07000(15) 0.0170(4) Uani 1 1 d . . . . .
C11 C 0.09892(9) 0.81687(18) 0.01165(16) 0.0213(4) Uani 1 1 d . . . . .
H11A H 0.1105 0.8363 -0.0667 0.026 Uiso 1 1 calc R U . . .
H11B H 0.0613 0.7618 0.0007 0.026 Uiso 1 1 calc R U . . .
C12 C 0.15524(9) 0.75213(18) 0.08365(16) 0.0221(4) Uani 1 1 d . . . . .
C13 C 0.21450(9) 0.8083(2) 0.11396(17) 0.0255(4) Uani 1 1 d . . . . .
H13A H 0.2203 0.8894 0.0895 0.031 Uiso 1 1 calc R U . . .
C14 C 0.26531(10) 0.7481(2) 0.17939(17) 0.0289(5) Uani 1 1 d . . . . .
H14A H 0.3056 0.7876 0.1983 0.035 Uiso 1 1 calc R U . . .
C15 C 0.25737(11) 0.6305(2) 0.21699(19) 0.0337(5) Uani 1 1 d . . . . .
H15A H 0.2917 0.5897 0.2634 0.040 Uiso 1 1 calc R U . . .
C16 C 0.19951(12) 0.5736(2) 0.1866(2) 0.0433(6) Uani 1 1 d . . . . .
H16A H 0.1940 0.4924 0.2111 0.052 Uiso 1 1 calc R U . . .
C17 C 0.14859(11) 0.6336(2) 0.1199(2) 0.0352(5) Uani 1 1 d . . . . .
H17A H 0.1089 0.5926 0.0992 0.042 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
N C3 1.325(2) . ?
N C4 1.363(2) . ?
C1 C2 1.511(2) . ?
C1 C1 1.525(3) 2 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C10 1.384(2) . ?
C2 C3 1.425(2) . ?
C3 C3 1.493(3) 2 ?
C4 C5 1.420(3) . ?
C4 C9 1.425(3) . ?
C5 C6 1.366(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.404(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.367(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.424(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.424(3) . ?
C10 C11 1.521(3) . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.384(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.370(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 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
C3 N C4 118.11(15) . . ?
C2 C1 C1 113.61(11) . 2 ?
C2 C1 H1A 108.8 . . ?
C1 C1 H1A 108.8 2 . ?
C2 C1 H1B 108.8 . . ?
C1 C1 H1B 108.8 2 . ?
H1A C1 H1B 107.7 . . ?
C10 C2 C3 119.05(16) . . ?
C10 C2 C1 122.16(16) . . ?
C3 C2 C1 118.71(15) . . ?
N C3 C2 123.56(16) . . ?
N C3 C3 116.44(10) . 2 ?
C2 C3 C3 119.99(10) . 2 ?
N C4 C5 117.82(17) . . ?
N C4 C9 122.68(17) . . ?
C5 C4 C9 119.51(17) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C8 C7 C6 120.34(19) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
C10 C9 C8 124.47(18) . . ?
C10 C9 C4 118.04(16) . . ?
C8 C9 C4 117.49(18) . . ?
C2 C10 C9 118.52(16) . . ?
C2 C10 C11 120.71(16) . . ?
C9 C10 C11 120.77(16) . . ?
C10 C11 C12 112.15(15) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C17 C12 C13 117.88(18) . . ?
C17 C12 C11 120.20(18) . . ?
C13 C12 C11 121.92(18) . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 119.3(2) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C17 120.7(2) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.054


_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_th5094
_database_code_depnum_ccdc_archive 'CCDC 1902337'
loop_
_audit_author_name
_audit_author_address
'Ganesh kumar Dhandabani'
;Kaohsiung medical university
Taiwan
;
_audit_update_record             
;
2019-03-10 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H16 F N O2'
_chemical_formula_sum            'C23 H16 F N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         357.37

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   29.6855(15)
_cell_length_b                   29.6855(15)
_cell_length_c                   11.124(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8489.4(18)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8811
_cell_measurement_theta_min      2.783
_cell_measurement_theta_max      26.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             3348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8247
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41148
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.745
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3846
_reflns_number_gt                2711
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00066(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3846
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_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
F F 0.38129(11) -0.21264(11) 1.0085(2) 0.0775(9) Uani 1 1 d . . . . .
O1 O 0.51609(12) 0.01380(11) 0.7728(2) 0.0499(8) Uani 1 1 d . . . . .
O2 O 0.64258(11) 0.10059(13) 0.8132(2) 0.0613(9) Uani 1 1 d . . . . .
N N 0.54831(12) 0.05803(13) 1.0412(2) 0.0368(8) Uani 1 1 d . . . . .
H0A H 0.5385(15) 0.0484(14) 1.109(4) 0.038(10) Uiso 1 1 d . . . . .
C1 C 0.51795(17) -0.01471(16) 0.8494(3) 0.0401(10) Uani 1 1 d . . . . .
C2 C 0.47646(16) -0.06694(16) 0.8825(3) 0.0387(10) Uani 1 1 d . . . . .
C3 C 0.42703(18) -0.09702(19) 0.8330(3) 0.0510(12) Uani 1 1 d . . . . .
H3A H 0.4157 -0.0837 0.7696 0.061 Uiso 1 1 calc R U . . .
C4 C 0.39516(19) -0.1459(2) 0.8767(4) 0.0579(12) Uani 1 1 d . . . . .
H4A H 0.3615 -0.1673 0.8436 0.069 Uiso 1 1 calc R U . . .
C5 C 0.41293(19) -0.16336(18) 0.9696(4) 0.0514(11) Uani 1 1 d . . . . .
C6 C 0.46045(18) -0.13488(16) 1.0220(3) 0.0475(11) Uani 1 1 d . . . . .
H6A H 0.4709 -0.1483 1.0870 0.057 Uiso 1 1 calc R U . . .
C7 C 0.49293(17) -0.08553(15) 0.9770(3) 0.0431(10) Uani 1 1 d . . . . .
C8 C 0.5472(2) -0.04686(17) 1.0155(4) 0.0698(15) Uani 1 1 d . . . . .
H8A H 0.5699 -0.0625 1.0128 0.084 Uiso 1 1 calc R U . . .
H8B H 0.5474 -0.0346 1.0984 0.084 Uiso 1 1 calc R U . . .
C9 C 0.56601(17) -0.00176(16) 0.9253(3) 0.0435(10) Uani 1 1 d . . . . .
H9A H 0.5929 -0.0021 0.8720 0.052 Uiso 1 1 calc R U . . .
C10 C 0.58929(14) 0.05171(14) 0.9850(3) 0.0313(8) Uani 1 1 d . . . . .
C11 C 0.54855(14) 0.10120(15) 0.9983(3) 0.0337(8) Uani 1 1 d . . . . .
C12 C 0.51761(18) 0.1224(2) 1.0337(4) 0.0581(14) Uani 1 1 d . . . . .
H12A H 0.4934 0.1078 1.0980 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5237(3) 0.1652(3) 0.9716(5) 0.0810(19) Uani 1 1 d . . . . .
H13A H 0.5028 0.1797 0.9937 0.097 Uiso 1 1 calc R U . . .
C14 C 0.5588(3) 0.1879(2) 0.8790(5) 0.0764(17) Uani 1 1 d . . . . .
H14A H 0.5616 0.2175 0.8390 0.092 Uiso 1 1 calc R U . . .
C15 C 0.58968(18) 0.16796(16) 0.8441(4) 0.0518(11) Uani 1 1 d . . . . .
H15A H 0.6142 0.1834 0.7808 0.062 Uiso 1 1 calc R U . . .
C16 C 0.58372(15) 0.12409(14) 0.9053(3) 0.0336(9) Uani 1 1 d . . . . .
C17 C 0.60962(15) 0.09481(15) 0.8872(3) 0.0355(9) Uani 1 1 d . . . . .
C18 C 0.63467(15) 0.06321(14) 1.0691(3) 0.0321(9) Uani 1 1 d . . . . .
C19 C 0.64081(16) 0.08823(14) 1.1783(3) 0.0393(9) Uani 1 1 d . . . . .
H19A H 0.6156 0.0969 1.2040 0.047 Uiso 1 1 calc R U . . .
C20 C 0.68392(17) 0.10066(17) 1.2507(3) 0.0487(11) Uani 1 1 d . . . . .
H20A H 0.6879 0.1180 1.3251 0.058 Uiso 1 1 calc R U . . .
C21 C 0.72044(17) 0.08803(17) 1.2156(4) 0.0528(11) Uani 1 1 d . . . . .
H21A H 0.7497 0.0967 1.2653 0.063 Uiso 1 1 calc R U . . .
C22 C 0.71465(18) 0.06247(18) 1.1072(3) 0.0515(11) Uani 1 1 d . . . . .
H22A H 0.7396 0.0531 1.0832 0.062 Uiso 1 1 calc R U . . .
C23 C 0.67191(15) 0.05064(15) 1.0336(3) 0.0418(10) Uani 1 1 d . . . . .
H23A H 0.6683 0.0338 0.9586 0.050 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
F C5 1.355(5) . ?
O1 C1 1.222(4) . ?
O2 C17 1.223(4) . ?
N C11 1.364(5) . ?
N C10 1.461(5) . ?
N H0A 0.81(4) . ?
C1 C2 1.465(6) . ?
C1 C9 1.532(5) . ?
C2 C7 1.385(5) . ?
C2 C3 1.394(6) . ?
C3 C4 1.365(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.361(6) . ?
C6 C7 1.384(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.500(6) . ?
C8 C9 1.538(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.530(5) . ?
C9 H9A 1.0000 . ?
C10 C18 1.532(5) . ?
C10 C17 1.553(5) . ?
C11 C16 1.382(5) . ?
C11 C12 1.405(5) . ?
C12 C13 1.375(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(8) . ?
C13 H13A 0.9500 . ?
C14 C15 1.372(7) . ?
C14 H14A 0.9500 . ?
C15 C16 1.400(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.434(5) . ?
C18 C19 1.388(5) . ?
C18 C23 1.389(5) . ?
C19 C20 1.397(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.369(6) . ?
C20 H20A 0.9500 . ?
C21 C22 1.389(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.399(6) . ?
C22 H22A 0.9500 . ?
C23 H23A 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
C11 N C10 110.9(3) . . ?
C11 N H0A 119(3) . . ?
C10 N H0A 122(3) . . ?
O1 C1 C2 127.1(4) . . ?
O1 C1 C9 124.7(4) . . ?
C2 C1 C9 108.1(3) . . ?
C7 C2 C3 120.8(4) . . ?
C7 C2 C1 109.6(3) . . ?
C3 C2 C1 129.6(3) . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
C6 C5 F 118.5(4) . . ?
C6 C5 C4 124.2(4) . . ?
F C5 C4 117.2(5) . . ?
C5 C6 C7 117.4(4) . . ?
C5 C6 H6A 121.3 . . ?
C7 C6 H6A 121.3 . . ?
C6 C7 C2 119.9(4) . . ?
C6 C7 C8 128.3(4) . . ?
C2 C7 C8 111.8(4) . . ?
C7 C8 C9 105.2(3) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C9 C1 112.4(3) . . ?
C10 C9 C8 113.5(3) . . ?
C1 C9 C8 104.8(3) . . ?
C10 C9 H9A 108.7 . . ?
C1 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
N C10 C9 110.2(3) . . ?
N C10 C18 114.0(3) . . ?
C9 C10 C18 112.8(3) . . ?
N C10 C17 101.5(3) . . ?
C9 C10 C17 109.8(3) . . ?
C18 C10 C17 107.9(3) . . ?
N C11 C16 111.8(3) . . ?
N C11 C12 128.7(4) . . ?
C16 C11 C12 119.5(4) . . ?
C13 C12 C11 117.2(4) . . ?
C13 C12 H12A 121.4 . . ?
C11 C12 H12A 121.4 . . ?
C12 C13 C14 123.2(4) . . ?
C12 C13 H13A 118.4 . . ?
C14 C13 H13A 118.4 . . ?
C15 C14 C13 120.3(5) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C14 C15 C16 117.6(4) . . ?
C14 C15 H15A 121.2 . . ?
C16 C15 H15A 121.2 . . ?
C11 C16 C15 122.3(4) . . ?
C11 C16 C17 108.0(3) . . ?
C15 C16 C17 129.7(4) . . ?
O2 C17 C16 130.0(3) . . ?
O2 C17 C10 122.8(3) . . ?
C16 C17 C10 107.2(3) . . ?
C19 C18 C23 118.9(4) . . ?
C19 C18 C10 121.3(3) . . ?
C23 C18 C10 119.7(3) . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21A 120.0 . . ?
C22 C21 H21A 120.0 . . ?
C21 C22 C23 119.6(4) . . ?
C21 C22 H22A 120.2 . . ?
C23 C22 H22A 120.2 . . ?
C18 C23 C22 120.7(4) . . ?
C18 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.038



