# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ic19115
_database_code_depnum_ccdc_archive 'CCDC 2005723'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17.19 N3 O1.10'
_chemical_formula_weight         365.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.5627(3)
_cell_length_b                   8.8564(3)
_cell_length_c                   19.8868(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.7088(9)
_cell_angle_gamma                90
_cell_volume                     1838.91(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      4.48
_cell_measurement_theta_max      75.06

_exptl_crystal_description       plate
_exptl_crystal_colour            light-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.657
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12050
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.484
_diffrn_reflns_theta_max         74.982
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3770
_reflns_number_gt                3459
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0454P)²+0.6822P] 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         3770
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 -0.03541(7) 0.56666(9) 0.15854(4) 0.02656(18) Uani 1 1 d . . . . .
N1 N -0.04608(10) 0.95604(12) 0.11869(5) 0.0300(2) Uani 1 1 d . . . . .
H1 H -0.0237(17) 1.050(2) 0.1248(9) 0.052(5) Uiso 1 1 d . . . . .
N2 N 0.31920(10) 0.89896(13) 0.26218(5) 0.0343(2) Uani 1 1 d . . . . .
H2 H 0.3757(18) 0.946(2) 0.2930(9) 0.053(5) Uiso 1 1 d . . . . .
N3 N -0.24512(10) 0.95183(13) 0.28314(6) 0.0366(2) Uani 1 1 d . . . . .
H3 H -0.3133(18) 1.004(2) 0.2922(9) 0.055(5) Uiso 1 1 d . . . . .
C1 C -0.00968(10) 0.84217(12) 0.17204(5) 0.0240(2) Uani 1 1 d . . . . .
C2 C -0.05118(10) 0.69331(12) 0.13337(5) 0.0234(2) Uani 1 1 d . . . . .
C3 C -0.10944(11) 0.73445(14) 0.06549(6) 0.0303(3) Uani 1 1 d . . . . .
C4 C -0.15999(16) 0.64515(17) 0.00979(7) 0.0468(4) Uani 1 1 d . . . . .
H4 H -0.1632 0.5384 0.0138 0.056 Uiso 1 1 calc R U . . .
C5 C -0.20500(18) 0.7152(2) -0.05089(8) 0.0589(5) Uani 1 1 d . . . . .
H5 H -0.2395 0.6568 -0.0894 0.071 Uiso 1 1 calc R U . . .
C6 C -0.19985(14) 0.87319(19) -0.05584(7) 0.0485(4) Uani 1 1 d . . . . .
H6 H -0.2323 0.9196 -0.0980 0.058 Uiso 1 1 calc R U . . .
C7 C -0.14971(11) 0.96340(16) -0.00201(6) 0.0357(3) Uani 1 1 d . . . . .
H7 H -0.1471 1.0701 -0.0065 0.043 Uiso 1 1 calc R U . . .
C8 C -0.10260(10) 0.89212(14) 0.05976(6) 0.0282(2) Uani 1 1 d . . . . .
C9 C 0.18931(11) 0.91630(14) 0.25490(6) 0.0302(2) Uani 1 1 d . . . . .
H9 H 0.1451 0.9709 0.2853 0.036 Uiso 1 1 calc R U . . .
C10 C 0.13228(10) 0.84375(12) 0.19762(5) 0.0242(2) Uani 1 1 d . . . . .
C11 C 0.23386(10) 0.77851(12) 0.16614(5) 0.0237(2) Uani 1 1 d . . . . .
C12 C 0.24067(11) 0.69429(13) 0.10702(6) 0.0275(2) Uani 1 1 d . . . . .
H12 H 0.1648 0.6678 0.0774 0.033 Uiso 1 1 calc R U . . .
C13 C 0.35930(12) 0.65023(14) 0.09239(6) 0.0334(3) Uani 1 1 d . . . . .
H13 H 0.3642 0.5942 0.0521 0.040 Uiso 1 1 calc R U . . .
C14 C 0.47245(12) 0.68676(15) 0.13591(7) 0.0363(3) Uani 1 1 d . . . . .
H14 H 0.5525 0.6541 0.1249 0.044 Uiso 1 1 calc R U . . .
C15 C 0.46907(12) 0.76920(15) 0.19427(7) 0.0353(3) Uani 1 1 d . . . . .
H15 H 0.5455 0.7938 0.2239 0.042 Uiso 1 1 calc R U . . .
C16 C 0.34991(11) 0.81536(13) 0.20856(6) 0.0285(2) Uani 1 1 d . . . . .
C17 C -0.19112(11) 0.96207(14) 0.22508(6) 0.0320(3) Uani 1 1 d . . . . .
H17 H -0.2188 1.0283 0.1882 0.038 Uiso 1 1 calc R U . . .
C18 C -0.09133(10) 0.86286(13) 0.22791(6) 0.0256(2) Uani 1 1 d . . . . .
C19 C -0.08362(11) 0.78394(13) 0.29171(6) 0.0268(2) Uani 1 1 d . . . . .
C20 C -0.00512(12) 0.67001(14) 0.32449(6) 0.0323(3) Uani 1 1 d . . . . .
H20 H 0.0617 0.6274 0.3036 0.039 Uiso 1 1 calc R U . . .
C21 C -0.02689(14) 0.62076(17) 0.38788(7) 0.0420(3) Uani 1 1 d . . . . .
H21 H 0.0252 0.5427 0.4102 0.050 Uiso 1 1 calc R U . . .
C22 C -0.12394(16) 0.68347(18) 0.41979(7) 0.0469(4) Uani 1 1 d . . . . .
H22 H -0.1355 0.6483 0.4636 0.056 Uiso 1 1 calc R U . . .
C23 C -0.20285(14) 0.79484(17) 0.38901(7) 0.0430(3) Uani 1 1 d . . . . .
H23 H -0.2691 0.8368 0.4106 0.052 Uiso 1 1 calc R U . . .
C24 C -0.18203(12) 0.84414(14) 0.32489(6) 0.0327(3) Uani 1 1 d . . . . .
O2 O -0.0240(14) 1.2884(13) 0.0876(8) 0.067(5) Uani 0.098(4) 1 d . . P . .
H2A H -0.0252 1.3794 0.1011 0.101 Uiso 0.098(4) 1 d R U P . .
H2B H 0.0531 1.2597 0.0988 0.101 Uiso 0.098(4) 1 d R U 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
O1 C2 1.2292(13) . ?
N1 C8 1.3558(15) . ?
N1 C1 1.4722(14) . ?
N2 C9 1.3663(16) . ?
N2 C16 1.3768(16) . ?
N3 C17 1.3660(17) . ?
N3 C24 1.3695(18) . ?
C1 C10 1.5088(15) . ?
C1 C18 1.5172(15) . ?
C1 C2 1.5555(15) . ?
C2 C3 1.4431(15) . ?
C3 C4 1.3994(18) . ?
C3 C8 1.4038(17) . ?
C4 C5 1.376(2) . ?
C5 C6 1.404(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.4037(16) . ?
C9 C10 1.3658(16) . ?
C10 C11 1.4423(15) . ?
C11 C12 1.4034(16) . ?
C11 C16 1.4169(15) . ?
C12 C13 1.3847(17) . ?
C13 C14 1.4031(19) . ?
C14 C15 1.3761(19) . ?
C15 C16 1.3929(17) . ?
C17 C18 1.3668(16) . ?
C18 C19 1.4400(16) . ?
C19 C20 1.4025(17) . ?
C19 C24 1.4170(16) . ?
C20 C21 1.3857(18) . ?
C21 C22 1.400(2) . ?
C22 C23 1.374(2) . ?
C23 C24 1.3963(18) . ?

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
C8 N1 C1 111.70(9) . . ?
C9 N2 C16 109.20(10) . . ?
C17 N3 C24 109.36(10) . . ?
N1 C1 C10 111.99(9) . . ?
N1 C1 C18 109.25(9) . . ?
C10 C1 C18 113.46(9) . . ?
N1 C1 C2 101.59(8) . . ?
C10 C1 C2 111.46(9) . . ?
C18 C1 C2 108.39(9) . . ?
O1 C2 C3 128.58(10) . . ?
O1 C2 C1 124.15(9) . . ?
C3 C2 C1 107.27(9) . . ?
C4 C3 C8 121.07(11) . . ?
C4 C3 C2 130.95(12) . . ?
C8 C3 C2 107.89(10) . . ?
C5 C4 C3 118.62(14) . . ?
C4 C5 C6 119.92(14) . . ?
C7 C6 C5 122.58(12) . . ?
C6 C7 C8 117.61(12) . . ?
N1 C8 C7 128.31(12) . . ?
N1 C8 C3 111.51(10) . . ?
C7 C8 C3 120.17(11) . . ?
C10 C9 N2 110.15(10) . . ?
C9 C10 C11 106.70(10) . . ?
C9 C10 C1 125.16(10) . . ?
C11 C10 C1 128.07(10) . . ?
C12 C11 C16 118.15(10) . . ?
C12 C11 C10 135.43(10) . . ?
C16 C11 C10 106.42(10) . . ?
C13 C12 C11 119.25(11) . . ?
C12 C13 C14 121.25(11) . . ?
C15 C14 C13 120.94(11) . . ?
C14 C15 C16 117.86(11) . . ?
N2 C16 C15 129.94(11) . . ?
N2 C16 C11 107.51(10) . . ?
C15 C16 C11 122.54(11) . . ?
N3 C17 C18 109.92(11) . . ?
C17 C18 C19 106.78(10) . . ?
C17 C18 C1 124.60(11) . . ?
C19 C18 C1 128.61(10) . . ?
C20 C19 C24 118.55(11) . . ?
C20 C19 C18 135.18(11) . . ?
C24 C19 C18 106.27(10) . . ?
C21 C20 C19 118.79(12) . . ?
C20 C21 C22 121.43(14) . . ?
C23 C22 C21 121.29(13) . . ?
C22 C23 C24 117.55(13) . . ?
N3 C24 C23 129.94(12) . . ?
N3 C24 C19 107.67(11) . . ?
C23 C24 C19 122.39(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.87(2) 2.24(2) 3.024(12) 150.6(16) .
N2 H2 O1 0.890(19) 2.105(19) 2.9693(13) 163.5(16) 2
N3 H3 O1 0.89(2) 2.07(2) 2.9271(13) 159.2(16) 2_455

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_ic19495
_database_code_depnum_ccdc_archive 'CCDC 2005726'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   19.1254(4)
_cell_length_b                   5.49360(10)
_cell_length_c                   11.5714(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.8783(9)
_cell_angle_gamma                90
_cell_volume                     1201.21(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      75.07

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.770
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6179
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8444
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.338
_diffrn_reflns_theta_max         74.885
_diffrn_reflns_theta_full        67.679
_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             2456
_reflns_number_gt                2262
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0446P)²+0.7661P] 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         2456
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.31155(6) 0.2015(2) 0.88007(8) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.19943(5) 0.34222(18) 0.70253(8) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.30411(7) 0.2347(2) 0.63779(10) 0.0297(3) Uani 1 1 d . . . . .
H1 H 0.2962(10) 0.280(4) 0.5637(18) 0.040(5) Uiso 1 1 d . . . . .
N2 N 0.21436(7) -0.0540(2) 0.85678(11) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.2173(13) -0.183(5) 0.901(2) 0.069(7) Uiso 1 1 d . . . . .
C1 C 0.24556(8) 0.1388(3) 0.68387(11) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.27214(8) 0.0228(3) 0.80336(12) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.3032 -0.1195 0.7932 0.032 Uiso 1 1 calc R U . . .
C3 C 0.35391(8) 0.3638(3) 0.83175(12) 0.0272(3) Uani 1 1 d . . . . .
C4 C 0.39905(8) 0.5099(3) 0.90656(13) 0.0330(4) Uani 1 1 d . . . . .
H4 H 0.4012 0.4936 0.9888 0.040 Uiso 1 1 calc R U . . .
C5 C 0.44123(9) 0.6802(3) 0.86193(15) 0.0388(4) Uani 1 1 d . . . . .
H5 H 0.4723 0.7808 0.9134 0.047 Uiso 1 1 calc R U . . .
C6 C 0.43794(9) 0.7033(3) 0.74154(16) 0.0399(4) Uani 1 1 d . . . . .
H6 H 0.4668 0.8196 0.7106 0.048 Uiso 1 1 calc R U . . .
C7 C 0.39267(8) 0.5571(3) 0.66676(13) 0.0338(4) Uani 1 1 d . . . . .
H7 H 0.3909 0.5736 0.5846 0.041 Uiso 1 1 calc R U . . .
C8 C 0.34975(8) 0.3863(3) 0.71015(12) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.15022(8) 0.2993(3) 0.77543(11) 0.0259(3) Uani 1 1 d . . . . .
C10 C 0.09483(8) 0.4617(3) 0.77236(13) 0.0319(3) Uani 1 1 d . . . . .
H10 H 0.0912 0.5957 0.7199 0.038 Uiso 1 1 calc R U . . .
C11 C 0.04445(9) 0.4307(3) 0.84521(15) 0.0371(4) Uani 1 1 d . . . . .
H11 H 0.0064 0.5426 0.8427 0.044 Uiso 1 1 calc R U . . .
C12 C 0.05000(9) 0.2347(3) 0.92190(14) 0.0372(4) Uani 1 1 d . . . . .
H12 H 0.0156 0.2124 0.9720 0.045 Uiso 1 1 calc R U . . .
C13 C 0.10542(8) 0.0722(3) 0.92567(13) 0.0320(3) Uani 1 1 d . . . . .
H13 H 0.1086 -0.0617 0.9782 0.038 Uiso 1 1 calc R U . . .
C14 C 0.15676(8) 0.1021(3) 0.85349(12) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.20590(9) -0.0448(3) 0.60101(13) 0.0348(4) Uani 1 1 d . . . . .
H15A H 0.1974 0.0232 0.5218 0.052 Uiso 1 1 calc R U . . .
H15B H 0.1605 -0.0828 0.6263 0.052 Uiso 1 1 calc R U . . .
H15C H 0.2341 -0.1939 0.6013 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 1.3799(18) . ?
O1 C2 1.4538(17) . ?
O2 C9 1.3775(17) . ?
O2 C1 1.4602(17) . ?
N1 C8 1.3898(19) . ?
N1 C1 1.4141(19) . ?
N2 C14 1.392(2) . ?
N2 C2 1.4114(19) . ?
C1 C15 1.513(2) . ?
C1 C2 1.5362(18) . ?
C3 C4 1.381(2) . ?
C3 C8 1.4024(19) . ?
C4 C5 1.386(2) . ?
C5 C6 1.391(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.391(2) . ?
C9 C10 1.381(2) . ?
C9 C14 1.404(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.381(2) . ?
C13 C14 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
C3 O1 C2 118.07(10) . . ?
C9 O2 C1 116.43(11) . . ?
C8 N1 C1 117.15(11) . . ?
C14 N2 C2 118.29(12) . . ?
N1 C1 O2 107.62(11) . . ?
N1 C1 C15 110.98(12) . . ?
O2 C1 C15 110.42(12) . . ?
N1 C1 C2 108.82(12) . . ?
O2 C1 C2 107.94(11) . . ?
C15 C1 C2 110.95(12) . . ?
N2 C2 O1 107.56(11) . . ?
N2 C2 C1 110.21(12) . . ?
O1 C2 C1 109.73(11) . . ?
O1 C3 C4 118.08(12) . . ?
O1 C3 C8 121.17(13) . . ?
C4 C3 C8 120.72(14) . . ?
C3 C4 C5 120.13(14) . . ?
C4 C5 C6 119.71(15) . . ?
C7 C6 C5 120.09(15) . . ?
C6 C7 C8 120.89(14) . . ?
N1 C8 C7 122.54(13) . . ?
N1 C8 C3 119.00(13) . . ?
C7 C8 C3 118.46(14) . . ?
O2 C9 C10 117.88(13) . . ?
O2 C9 C14 121.64(13) . . ?
C10 C9 C14 120.45(14) . . ?
C9 C10 C11 120.51(15) . . ?
C10 C11 C12 119.51(15) . . ?
C13 C12 C11 120.25(15) . . ?
C12 C13 C14 120.86(14) . . ?
N2 C14 C13 122.60(13) . . ?
N2 C14 C9 118.99(13) . . ?
C13 C14 C9 118.41(14) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_ic19379
_database_code_depnum_ccdc_archive 'CCDC 2005724'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24.25 H14.50 Br3 Cl0.50 N3 O'
_chemical_formula_weight         621.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   26.7209(6)
_cell_length_b                   15.6427(3)
_cell_length_c                   11.8698(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.3612(4)
_cell_angle_gamma                90
_cell_volume                     4806.38(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    19784
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      75.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             2420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    6.913
_shelx_estimated_absorpt_T_min   0.386
_shelx_estimated_absorpt_T_max   0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17387
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         74.999
_diffrn_reflns_theta_full        67.679
_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             4951
_reflns_number_gt                4667
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0849P)²+32.6636P] 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         4951
_refine_ls_number_parameters     304
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1673
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.57143(3) 0.27360(4) 0.21693(6) 0.0700(2) Uani 1 1 d . . . . .
Br2 Br 0.53460(2) 0.89172(4) -0.08143(8) 0.0779(3) Uani 1 1 d . . . . .
Br3 Br 0.92465(3) 0.67142(6) 0.71067(6) 0.0900(3) Uani 1 1 d . . . . .
O1 O 0.73065(12) 0.53817(18) -0.0151(2) 0.0365(6) Uani 1 1 d . . . . .
N1 N 0.69546(13) 0.5430(2) 0.2550(3) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.709(2) 0.536(4) 0.325(5) 0.045(14) Uiso 1 1 d . . . . .
N2 N 0.73035(14) 0.8091(2) 0.1112(3) 0.0357(7) Uani 1 1 d D . . . .
H2 H 0.7457(17) 0.850(2) 0.090(4) 0.035(12) Uiso 1 1 d D . . . .
N3 N 0.86834(16) 0.5272(3) 0.2909(4) 0.0503(10) Uani 1 1 d D . . . .
H3 H 0.8945(14) 0.501(3) 0.284(5) 0.057(17) Uiso 1 1 d D . . . .
C1 C 0.72951(14) 0.5795(2) 0.1845(3) 0.0278(7) Uani 1 1 d . . . . .
C2 C 0.71387(15) 0.5258(2) 0.0710(3) 0.0286(7) Uani 1 1 d . . . . .
C3 C 0.67705(15) 0.4628(2) 0.0870(3) 0.0314(8) Uani 1 1 d . . . . .
C4 C 0.65062(18) 0.3990(3) 0.0118(4) 0.0398(9) Uani 1 1 d . . . . .
H4 H 0.6548 0.3939 -0.0651 0.048 Uiso 1 1 calc R U . . .
C5 C 0.61878(19) 0.3445(3) 0.0512(4) 0.0449(10) Uani 1 1 d . . . . .
H5 H 0.6000 0.3016 0.0018 0.054 Uiso 1 1 calc R U . . .
C6 C 0.61438(18) 0.3531(3) 0.1660(4) 0.0421(10) Uani 1 1 d . . . . .
C7 C 0.63887(16) 0.4154(3) 0.2420(4) 0.0355(8) Uani 1 1 d . . . . .
H7 H 0.6348 0.4193 0.3191 0.043 Uiso 1 1 calc R U . . .
C8 C 0.67011(14) 0.4728(2) 0.1993(3) 0.0288(7) Uani 1 1 d . . . . .
C9 C 0.82204(18) 0.5229(3) 0.2080(4) 0.0422(9) Uani 1 1 d . . . . .
H9 H 0.8167 0.4943 0.1354 0.051 Uiso 1 1 calc R U . . .
C10 C 0.78516(15) 0.5657(2) 0.2459(3) 0.0309(7) Uani 1 1 d . . . . .
C11 C 0.80973(15) 0.5989(2) 0.3601(3) 0.0325(8) Uani 1 1 d . . . . .
C12 C 0.86174(17) 0.5730(3) 0.3842(4) 0.0407(9) Uani 1 1 d . . . . .
C13 C 0.89717(18) 0.5947(3) 0.4894(5) 0.0530(13) Uani 1 1 d . . . . .
H13 H 0.9324 0.5782 0.5051 0.064 Uiso 1 1 calc R U . . .
C14 C 0.8784(2) 0.6404(4) 0.5671(4) 0.0529(13) Uani 1 1 d . . . . .
C15 C 0.8274(2) 0.6670(3) 0.5473(4) 0.0492(11) Uani 1 1 d . . . . .
H15 H 0.8162 0.6987 0.6048 0.059 Uiso 1 1 calc R U . . .
C16 C 0.79274(17) 0.6467(3) 0.4424(3) 0.0383(9) Uani 1 1 d . . . . .
H16 H 0.7579 0.6653 0.4271 0.046 Uiso 1 1 calc R U . . .
C17 C 0.75409(16) 0.7344(2) 0.1553(3) 0.0335(8) Uani 1 1 d . . . . .
H17 H 0.7904 0.7269 0.1824 0.040 Uiso 1 1 calc R U . . .
C18 C 0.71818(14) 0.6723(2) 0.1548(3) 0.0281(7) Uani 1 1 d . . . . .
C19 C 0.66843(15) 0.7100(2) 0.1038(3) 0.0309(7) Uani 1 1 d . . . . .
C20 C 0.67825(15) 0.7959(2) 0.0771(3) 0.0317(8) Uani 1 1 d . . . . .
C21 C 0.63889(17) 0.8519(3) 0.0238(4) 0.0381(9) Uani 1 1 d . . . . .
H21 H 0.6458 0.9094 0.0067 0.046 Uiso 1 1 calc R U . . .
C22 C 0.58962(18) 0.8197(3) -0.0026(4) 0.0452(10) Uani 1 1 d . . . . .
C23 C 0.57787(19) 0.7358(3) 0.0220(5) 0.0527(12) Uani 1 1 d . . . . .
H23 H 0.5431 0.7166 0.0022 0.063 Uiso 1 1 calc R U . . .
C24 C 0.61735(17) 0.6807(3) 0.0757(4) 0.0424(9) Uani 1 1 d . . . . .
H24 H 0.6098 0.6236 0.0933 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4787(19) 0.477(3) 0.085(3) 0.144(18) Uiso 0.25 1 d D . P A -1
H25A H 0.4405 0.4785 0.0676 0.173 Uiso 0.25 1 calc R U P A -1
H25B H 0.4903 0.4209 0.1196 0.173 Uiso 0.25 1 calc R U P A -1
Cl1 Cl 0.4972(10) 0.4869(15) -0.0462(14) 0.201(8) Uiso 0.25 1 d D . P A -1
Cl2 Cl 0.5034(12) 0.5565(18) 0.1844(17) 0.263(12) Uiso 0.25 1 d D . P A -1


_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
Br1 C6 1.890(4) . ?
Br2 C22 1.904(5) . ?
Br3 C14 1.903(4) . ?
O1 C2 1.228(4) . ?
N1 C8 1.371(5) . ?
N1 C1 1.494(4) . ?
N2 C20 1.366(5) . ?
N2 C17 1.371(5) . ?
N3 C12 1.368(7) . ?
N3 C9 1.378(6) . ?
C1 C10 1.501(5) . ?
C1 C18 1.506(5) . ?
C1 C2 1.555(5) . ?
C2 C3 1.438(5) . ?
C3 C8 1.399(5) . ?
C3 C4 1.407(5) . ?
C4 C5 1.366(6) . ?
C5 C6 1.402(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.403(5) . ?
C9 C10 1.357(6) . ?
C10 C11 1.447(5) . ?
C11 C16 1.394(6) . ?
C11 C12 1.407(6) . ?
C12 C13 1.408(7) . ?
C13 C14 1.357(9) . ?
C14 C15 1.389(8) . ?
C15 C16 1.391(6) . ?
C17 C18 1.364(5) . ?
C18 C19 1.443(6) . ?
C19 C24 1.399(6) . ?
C19 C20 1.420(5) . ?
C20 C21 1.394(6) . ?
C21 C22 1.372(6) . ?
C22 C23 1.397(7) . ?
C23 C24 1.389(7) . ?
C25 Cl2 1.729(10) . ?
C25 Cl1 1.748(10) . ?

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
C8 N1 C1 109.5(3) . . ?
C20 N2 C17 109.0(3) . . ?
C12 N3 C9 109.3(4) . . ?
N1 C1 C10 109.9(3) . . ?
N1 C1 C18 112.6(3) . . ?
C10 C1 C18 111.7(3) . . ?
N1 C1 C2 102.0(3) . . ?
C10 C1 C2 111.4(3) . . ?
C18 C1 C2 108.8(3) . . ?
O1 C2 C3 128.4(3) . . ?
O1 C2 C1 124.1(3) . . ?
C3 C2 C1 107.5(3) . . ?
C8 C3 C4 121.3(3) . . ?
C8 C3 C2 107.8(3) . . ?
C4 C3 C2 130.9(3) . . ?
C5 C4 C3 118.8(4) . . ?
C4 C5 C6 118.8(4) . . ?
C7 C6 C5 124.2(4) . . ?
C7 C6 Br1 118.9(3) . . ?
C5 C6 Br1 116.9(3) . . ?
C6 C7 C8 116.4(4) . . ?
N1 C8 C3 112.5(3) . . ?
N1 C8 C7 127.2(3) . . ?
C3 C8 C7 120.3(3) . . ?
C10 C9 N3 109.7(4) . . ?
C9 C10 C11 106.8(4) . . ?
C9 C10 C1 128.6(4) . . ?
C11 C10 C1 124.6(3) . . ?
C16 C11 C12 119.2(4) . . ?
C16 C11 C10 134.3(4) . . ?
C12 C11 C10 106.5(4) . . ?
N3 C12 C11 107.8(4) . . ?
N3 C12 C13 130.6(5) . . ?
C11 C12 C13 121.6(5) . . ?
C14 C13 C12 116.7(5) . . ?
C13 C14 C15 123.7(4) . . ?
C13 C14 Br3 118.4(4) . . ?
C15 C14 Br3 117.9(4) . . ?
C14 C15 C16 119.4(5) . . ?
C15 C16 C11 119.3(4) . . ?
C18 C17 N2 110.3(4) . . ?
C17 C18 C19 106.6(3) . . ?
C17 C18 C1 125.8(4) . . ?
C19 C18 C1 127.1(3) . . ?
C24 C19 C20 118.7(4) . . ?
C24 C19 C18 135.1(4) . . ?
C20 C19 C18 106.2(3) . . ?
N2 C20 C21 129.7(4) . . ?
N2 C20 C19 107.9(3) . . ?
C21 C20 C19 122.4(4) . . ?
C22 C21 C20 116.5(4) . . ?
C21 C22 C23 123.4(4) . . ?
C21 C22 Br2 118.4(3) . . ?
C23 C22 Br2 118.2(4) . . ?
C24 C23 C22 119.6(4) . . ?
C23 C24 C19 119.4(4) . . ?
Cl2 C25 Cl1 113.7(9) . . ?

_refine_diff_density_max         2.114
_refine_diff_density_min         -2.347
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_ic19387
_database_code_depnum_ccdc_archive 'CCDC 2005725'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 N3 O'
_chemical_formula_weight         405.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.4157(2)
_cell_length_b                   10.5063(2)
_cell_length_c                   11.3815(2)
_cell_angle_alpha                112.5285(8)
_cell_angle_beta                 108.7529(8)
_cell_angle_gamma                99.9684(8)
_cell_volume                     1024.96(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9145
_cell_measurement_theta_min      4.65
_cell_measurement_theta_max      75.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8034
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_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         4.650
_diffrn_reflns_theta_max         74.991
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4193
_reflns_number_gt                3732
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0443P)²+0.4156P] 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         4193
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.69395(11) 0.69550(10) 0.24841(10) 0.0352(2) Uani 1 1 d . . . . .
N1 N 0.83977(11) 0.50698(11) 0.42836(11) 0.0261(2) Uani 1 1 d . . . . .
H1 H 0.869(2) 0.490(2) 0.498(2) 0.058(6) Uiso 1 1 d . . . . .
N2 N 1.12655(11) 0.99015(11) 0.62282(11) 0.0259(2) Uani 1 1 d . . . . .
H2 H 1.1658(17) 1.0868(19) 0.6765(17) 0.036(4) Uiso 1 1 d . . . . .
N3 N 0.53395(13) 0.70181(16) 0.56987(15) 0.0445(3) Uani 1 1 d . . . . .
H3 H 0.448(2) 0.702(2) 0.557(2) 0.061(6) Uiso 1 1 d . . . . .
C1 C 0.81563(12) 0.64657(13) 0.44290(12) 0.0237(2) Uani 1 1 d . . . . .
C2 C 0.72603(13) 0.60681(13) 0.28657(13) 0.0250(3) Uani 1 1 d . . . . .
C3 C 0.69374(12) 0.45173(13) 0.20219(12) 0.0230(2) Uani 1 1 d . . . . .
C4 C 0.61576(13) 0.36145(13) 0.05702(13) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.5709 0.3999 -0.0019 0.030 Uiso 1 1 calc R U . . .
C5 C 0.60488(13) 0.21573(13) 0.00044(13) 0.0258(3) Uani 1 1 d . . . . .
C6 C 0.67253(13) 0.16335(13) 0.09201(13) 0.0270(3) Uani 1 1 d . . . . .
H6 H 0.6652 0.0632 0.0529 0.032 Uiso 1 1 calc R U . . .
C7 C 0.74904(13) 0.25024(13) 0.23581(13) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.7918 0.2109 0.2947 0.030 Uiso 1 1 calc R U . . .
C8 C 0.76134(12) 0.39828(13) 0.29159(12) 0.0216(2) Uani 1 1 d . . . . .
C9 C 0.52367(16) 0.11399(15) -0.15515(14) 0.0352(3) Uani 1 1 d . . . . .
H9A H 0.4371 0.0413 -0.1731 0.053 Uiso 1 1 calc R U . . .
H9B H 0.5854 0.0640 -0.1892 0.053 Uiso 1 1 calc R U . . .
H9C H 0.4957 0.1705 -0.2043 0.053 Uiso 1 1 calc R U . . .
C10 C 0.99865(13) 0.90769(13) 0.60703(12) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.9479 0.9425 0.6615 0.029 Uiso 1 1 calc R U . . .
C11 C 0.95501(12) 0.76801(13) 0.50136(12) 0.0228(2) Uani 1 1 d . . . . .
C12 C 1.06043(12) 0.76375(13) 0.44445(12) 0.0231(2) Uani 1 1 d . . . . .
C13 C 1.07525(13) 0.65667(13) 0.33361(13) 0.0264(3) Uani 1 1 d . . . . .
H13 H 1.0066 0.5604 0.2804 0.032 Uiso 1 1 calc R U . . .
C14 C 1.19004(14) 0.69182(14) 0.30219(14) 0.0294(3) Uani 1 1 d . . . . .
C15 C 1.29149(14) 0.83499(15) 0.38262(14) 0.0320(3) Uani 1 1 d . . . . .
H15 H 1.3702 0.8580 0.3606 0.038 Uiso 1 1 calc R U . . .
C16 C 1.28058(14) 0.94272(14) 0.49194(13) 0.0294(3) Uani 1 1 d . . . . .
H16 H 1.3495 1.0388 0.5445 0.035 Uiso 1 1 calc R U . . .
C17 C 1.16474(13) 0.90554(13) 0.52255(12) 0.0244(2) Uani 1 1 d . . . . .
C18 C 1.20569(17) 0.58044(17) 0.18079(16) 0.0399(3) Uani 1 1 d . . . . .
H18A H 1.2639 0.5270 0.2141 0.060 Uiso 1 1 calc R U . . .
H18B H 1.2532 0.6306 0.1411 0.060 Uiso 1 1 calc R U . . .
H18C H 1.1102 0.5115 0.1083 0.060 Uiso 1 1 calc R U . . .
C19 C 0.58364(15) 0.67068(17) 0.46804(16) 0.0380(3) Uani 1 1 d . . . . .
H19 H 0.5279 0.6451 0.3728 0.046 Uiso 1 1 calc R U . . .
C20 C 0.72497(13) 0.68179(13) 0.52330(13) 0.0269(3) Uani 1 1 d . . . . .
C21 C 0.76620(13) 0.72224(13) 0.67000(13) 0.0262(3) Uani 1 1 d . . . . .
C22 C 0.89397(14) 0.75097(14) 0.78298(13) 0.0274(3) Uani 1 1 d . . . . .
H22 H 0.9777 0.7430 0.7684 0.033 Uiso 1 1 calc R U . . .
C23 C 0.89804(15) 0.79082(14) 0.91542(14) 0.0320(3) Uani 1 1 d . . . . .
C24 C 0.77246(17) 0.79979(16) 0.93500(16) 0.0384(3) Uani 1 1 d . . . . .
H24 H 0.7756 0.8260 1.0258 0.046 Uiso 1 1 calc R U . . .
C25 C 0.64522(16) 0.77186(17) 0.82678(17) 0.0401(3) Uani 1 1 d . . . . .
H25 H 0.5614 0.7782 0.8418 0.048 Uiso 1 1 calc R U . . .
C26 C 0.64338(15) 0.73405(15) 0.69487(16) 0.0345(3) Uani 1 1 d . . . . .
C27 C 1.03482(18) 0.82399(18) 1.03817(15) 0.0421(3) Uani 1 1 d . . . . .
H27A H 1.0974 0.7764 1.0032 0.063 Uiso 1 1 calc R U . . .
H27B H 1.0110 0.7870 1.0983 0.063 Uiso 1 1 calc R U . . .
H27C H 1.0848 0.9301 1.0927 0.063 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 C2 1.2220(15) . ?
N1 C8 1.3754(15) . ?
N1 C1 1.4865(15) . ?
N2 C10 1.3729(16) . ?
N2 C17 1.3739(16) . ?
N3 C19 1.368(2) . ?
N3 C26 1.376(2) . ?
C1 C11 1.5051(16) . ?
C1 C20 1.5109(17) . ?
C1 C2 1.5617(16) . ?
C2 C3 1.4469(17) . ?
C3 C4 1.3996(16) . ?
C3 C8 1.4003(16) . ?
C4 C5 1.3817(17) . ?
C5 C6 1.4097(18) . ?
C5 C9 1.5057(17) . ?
C6 C7 1.3826(17) . ?
C7 C8 1.4002(17) . ?
C10 C11 1.3681(17) . ?
C11 C12 1.4420(17) . ?
C12 C13 1.4066(17) . ?
C12 C17 1.4120(16) . ?
C13 C14 1.3845(18) . ?
C14 C15 1.4106(19) . ?
C14 C18 1.5090(19) . ?
C15 C16 1.3778(19) . ?
C16 C17 1.3933(18) . ?
C19 C20 1.3657(18) . ?
C20 C21 1.4439(18) . ?
C21 C22 1.4068(18) . ?
C21 C26 1.4117(18) . ?
C22 C23 1.3850(18) . ?
C23 C24 1.408(2) . ?
C23 C27 1.509(2) . ?
C24 C25 1.378(2) . ?
C25 C26 1.391(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
C8 N1 C1 110.16(10) . . ?
C10 N2 C17 108.73(10) . . ?
C19 N3 C26 109.20(12) . . ?
N1 C1 C11 111.64(10) . . ?
N1 C1 C20 110.16(10) . . ?
C11 C1 C20 114.44(10) . . ?
N1 C1 C2 101.89(9) . . ?
C11 C1 C2 108.72(9) . . ?
C20 C1 C2 109.22(10) . . ?
O1 C2 C3 128.76(11) . . ?
O1 C2 C1 123.96(11) . . ?
C3 C2 C1 107.27(10) . . ?
C4 C3 C8 121.70(11) . . ?
C4 C3 C2 130.35(11) . . ?
C8 C3 C2 107.90(10) . . ?
C5 C4 C3 119.18(11) . . ?
C4 C5 C6 118.42(11) . . ?
C4 C5 C9 121.45(11) . . ?
C6 C5 C9 120.13(12) . . ?
C7 C6 C5 123.38(11) . . ?
C6 C7 C8 117.66(11) . . ?
N1 C8 C7 128.08(11) . . ?
N1 C8 C3 112.21(10) . . ?
C7 C8 C3 119.64(11) . . ?
C11 C10 N2 110.08(11) . . ?
C10 C11 C12 106.68(11) . . ?
C10 C11 C1 127.12(11) . . ?
C12 C11 C1 125.82(11) . . ?
C13 C12 C17 118.84(11) . . ?
C13 C12 C11 134.78(11) . . ?
C17 C12 C11 106.35(11) . . ?
C14 C13 C12 119.88(12) . . ?
C13 C14 C15 119.40(12) . . ?
C13 C14 C18 120.92(12) . . ?
C15 C14 C18 119.65(12) . . ?
C16 C15 C14 122.38(12) . . ?
C15 C16 C17 117.54(12) . . ?
N2 C17 C16 129.92(11) . . ?
N2 C17 C12 108.11(11) . . ?
C16 C17 C12 121.95(12) . . ?
C20 C19 N3 110.10(13) . . ?
C19 C20 C21 106.52(12) . . ?
C19 C20 C1 126.20(12) . . ?
C21 C20 C1 127.11(11) . . ?
C22 C21 C26 118.54(12) . . ?
C22 C21 C20 134.83(12) . . ?
C26 C21 C20 106.62(11) . . ?
C23 C22 C21 120.17(12) . . ?
C22 C23 C24 119.31(13) . . ?
C22 C23 C27 120.83(13) . . ?
C24 C23 C27 119.86(13) . . ?
C25 C24 C23 122.16(13) . . ?
C24 C25 C26 117.86(13) . . ?
N3 C26 C25 130.51(13) . . ?
N3 C26 C21 107.55(12) . . ?
C25 C26 C21 121.94(13) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_ic19457
_database_code_depnum_ccdc_archive 'CCDC 2005727'
loop_
_audit_author_name
_audit_author_address
'Gene-Hsiang Lee'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   14.1319(5)
_cell_length_b                   3.86820(10)
_cell_length_c                   15.5153(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.9456(10)
_cell_angle_gamma                90
_cell_volume                     792.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9527
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      75.04

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    0.806
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5152
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.635
_diffrn_reflns_theta_max         74.974
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             2954
_reflns_number_gt                2868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_max     0.824
_reflns_Friedel_fraction_full    0.859

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0345P)²+0.0739P] 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_abs_structure_details 
; 
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.22(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.59435(11) 0.6670(4) 0.31297(10) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.92153(11) 0.2253(5) 0.31021(11) 0.0474(4) Uani 1 1 d . . . . .
N1 N 0.76323(11) 0.4267(4) 0.29598(10) 0.0290(3) Uani 1 1 d . . . . .
H1 H 0.732(2) 0.540(7) 0.329(2) 0.043(7) Uiso 1 1 d . . . . .
C1 C 0.70069(13) 0.3149(4) 0.20810(11) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.74031(14) 0.1426(4) 0.14935(13) 0.0299(4) Uani 1 1 d . . . . .
H2A H 0.8108 0.0941 0.1695 0.036 Uiso 1 1 calc R U . . .
C3 C 0.67758(16) 0.0420(5) 0.06203(13) 0.0331(4) Uani 1 1 d . . . . .
H3 H 0.7058 -0.0745 0.0229 0.040 Uiso 1 1 calc R U . . .
C4 C 0.57494(15) 0.1077(5) 0.03068(13) 0.0339(4) Uani 1 1 d . . . . .
H4 H 0.5327 0.0410 -0.0298 0.041 Uiso 1 1 calc R U . . .
C5 C 0.53466(14) 0.2724(5) 0.08879(13) 0.0312(4) Uani 1 1 d . . . . .
H5 H 0.4638 0.3147 0.0677 0.037 Uiso 1 1 calc R U . . .
C6 C 0.59493(13) 0.3786(4) 0.17764(12) 0.0263(3) Uani 1 1 d . . . . .
C7 C 0.54553(13) 0.5531(5) 0.23605(13) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.43201(15) 0.5905(6) 0.20084(16) 0.0407(5) Uani 1 1 d . . . . .
H8A H 0.4117 0.7112 0.2470 0.061 Uiso 1 1 calc R U . . .
H8B H 0.4006 0.3610 0.1893 0.061 Uiso 1 1 calc R U . . .
H8C H 0.4098 0.7237 0.1433 0.061 Uiso 1 1 calc R U . . .
C9 C 0.86426(15) 0.3783(6) 0.33940(13) 0.0347(4) Uani 1 1 d . . . . .
H9 H 0.889(2) 0.501(7) 0.402(2) 0.047(7) Uiso 1 1 d . . . . .
O3 O 0.72707(12) 0.9402(5) 0.73181(11) 0.0510(4) Uani 1 1 d . . . . .
O4 O 0.79528(11) 0.8701(5) 0.48532(11) 0.0472(4) Uani 1 1 d . . . . .
N2 N 0.67894(12) 0.9768(4) 0.55091(11) 0.0322(3) Uani 1 1 d . . . . .
H2 H 0.718(2) 0.882(7) 0.604(2) 0.041(6) Uiso 1 1 d . . . . .
C10 C 0.58767(14) 1.1212(4) 0.54996(13) 0.0290(4) Uani 1 1 d . . . . .
C11 C 0.50984(15) 1.1854(5) 0.46593(14) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.5185 1.1260 0.4098 0.041 Uiso 1 1 calc R U . . .
C12 C 0.42013(16) 1.3349(5) 0.46385(17) 0.0406(5) Uani 1 1 d . . . . .
H12 H 0.3681 1.3825 0.4063 0.049 Uiso 1 1 calc R U . . .
C13 C 0.40567(16) 1.4158(5) 0.54545(18) 0.0426(5) Uani 1 1 d . . . . .
H13 H 0.3442 1.5205 0.5438 0.051 Uiso 1 1 calc R U . . .
C14 C 0.48094(17) 1.3435(5) 0.62891(16) 0.0395(5) Uani 1 1 d . . . . .
H14 H 0.4701 1.3967 0.6845 0.047 Uiso 1 1 calc R U . . .
C15 C 0.57325(15) 1.1931(5) 0.63384(14) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.65112(17) 1.1073(5) 0.72462(15) 0.0377(4) Uani 1 1 d . . . . .
C17 C 0.6349(2) 1.2193(7) 0.81179(16) 0.0511(6) Uani 1 1 d . . . . .
H17A H 0.6968 1.1775 0.8652 0.077 Uiso 1 1 calc R U . . .
H17B H 0.5789 1.0867 0.8186 0.077 Uiso 1 1 calc R U . . .
H17C H 0.6184 1.4663 0.8080 0.077 Uiso 1 1 calc R U . . .
C18 C 0.71741(15) 1.0087(5) 0.48312(14) 0.0333(4) Uani 1 1 d . . . . .
H18 H 0.6783(19) 1.159(6) 0.4306(18) 0.036(6) Uiso 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
O1 C7 1.227(2) . ?
O2 C9 1.213(3) . ?
N1 C9 1.356(2) . ?
N1 C1 1.402(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.419(2) . ?
C2 C3 1.384(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.489(2) . ?
C7 C8 1.505(3) . ?
O3 C16 1.223(3) . ?
O4 C18 1.214(2) . ?
N2 C18 1.351(2) . ?
N2 C10 1.401(2) . ?
C10 C11 1.395(3) . ?
C10 C15 1.415(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.379(4) . ?
C14 C15 1.405(3) . ?
C15 C16 1.482(3) . ?
C16 C17 1.514(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C1 128.77(16) . . ?
C2 C1 N1 121.41(16) . . ?
C2 C1 C6 119.04(16) . . ?
N1 C1 C6 119.55(15) . . ?
C3 C2 C1 120.45(17) . . ?
C4 C3 C2 121.25(17) . . ?
C3 C4 C5 118.79(17) . . ?
C4 C5 C6 122.06(17) . . ?
C5 C6 C1 118.38(15) . . ?
C5 C6 C7 118.71(16) . . ?
C1 C6 C7 122.91(15) . . ?
O1 C7 C6 122.13(16) . . ?
O1 C7 C8 118.30(17) . . ?
C6 C7 C8 119.56(17) . . ?
O2 C9 N1 127.30(19) . . ?
C18 N2 C10 125.50(16) . . ?
C11 C10 N2 119.75(17) . . ?
C11 C10 C15 120.00(17) . . ?
N2 C10 C15 120.23(17) . . ?
C12 C11 C10 120.40(19) . . ?
C11 C12 C13 120.4(2) . . ?
C14 C13 C12 119.68(19) . . ?
C13 C14 C15 121.63(19) . . ?
C14 C15 C10 117.87(19) . . ?
C14 C15 C16 120.26(18) . . ?
C10 C15 C16 121.86(18) . . ?
O3 C16 C15 122.28(18) . . ?
O3 C16 C17 118.6(2) . . ?
C15 C16 C17 119.1(2) . . ?
O4 C18 N2 123.43(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.90(3) 1.94(3) 2.661(2) 136(3) .
N1 H1 O4 0.90(3) 2.60(3) 3.290(2) 134(2) .
C2 H2A O2 0.95 2.24 2.884(2) 124.1 .
C9 H9 O4 1.03(3) 2.58(3) 3.357(3) 132(2) .
N2 H2 O3 0.89(3) 1.96(3) 2.645(2) 133(2) .
C17 H17B O2 0.98 2.49 3.464(3) 170.9 2_465

_refine_diff_density_max         0.132
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026

