# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_tpak-y
_audit_block_doi                 10.5517/ccdc.csd.cc2dl6z6
_database_code_depnum_ccdc_archive 'CCDC 2222048'
loop_
_audit_author_name
_audit_author_address
'Miao Yu'
;Capital Normal University
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_audit_creation_date             2022-01-25
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.2349(6)
_cell_length_b                   9.6558(8)
_cell_length_c                   17.2969(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.280(7)
_cell_angle_gamma                90
_cell_volume                     1542.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2710
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      27.7120
_cell_measurement_theta_min      2.4370
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.355
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  81.00   1.00    4.00    --   11.90  37.00 -90.00   42
  2  ω      6.00  81.00   1.00    4.00    --   11.90  37.00-180.00   75
  3  ω     -5.00  26.00   1.00    4.00    --  -11.35 -99.00-150.00   31
  4  ω     41.00  98.00   1.00    4.00    --   11.90-178.00 120.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0181789000
_diffrn_orient_matrix_UB_12      0.0159513000
_diffrn_orient_matrix_UB_13      -0.0388927000
_diffrn_orient_matrix_UB_21      0.0167731000
_diffrn_orient_matrix_UB_22      0.0706300000
_diffrn_orient_matrix_UB_23      0.0068313000
_diffrn_orient_matrix_UB_31      0.0727173000
_diffrn_orient_matrix_UB_32      -0.0123372000
_diffrn_orient_matrix_UB_33      -0.0110707000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             2708
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.3028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59065(12) 0.14633(13) 0.53631(7) 0.0442(3) Uani 1 1 d D . . . .
H1 H 0.606(3) 0.0627(17) 0.5193(19) 0.158(14) Uiso 1 1 d D . . . .
O2 O 0.35585(12) 0.10472(12) 0.51524(7) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.31915(13) 0.71280(13) 0.65768(8) 0.0350(3) Uani 1 1 d . . . . .
C1 C 0.17809(16) 0.77111(16) 0.64629(9) 0.0310(4) Uani 1 1 d . . . . .
C2 C 0.09631(17) 0.81085(17) 0.70887(9) 0.0371(4) Uani 1 1 d . . . . .
H2 H 0.133976 0.802665 0.758620 0.045 Uiso 1 1 calc R U . . .
C3 C -0.04177(17) 0.86292(19) 0.69780(10) 0.0445(5) Uani 1 1 d . . . . .
H3 H -0.096925 0.888460 0.740323 0.053 Uiso 1 1 calc R U . . .
C4 C -0.09807(18) 0.87724(19) 0.62487(11) 0.0473(5) Uani 1 1 d . . . . .
H4 H -0.191555 0.910932 0.617847 0.057 Uiso 1 1 calc R U . . .
C5 C -0.01527(18) 0.8414(2) 0.56202(11) 0.0479(5) Uani 1 1 d . . . . .
H5 H -0.052227 0.852983 0.512330 0.057 Uiso 1 1 calc R U . . .
C6 C 0.12254(17) 0.78821(19) 0.57230(9) 0.0419(4) Uani 1 1 d . . . . .
H6 H 0.177889 0.763944 0.529619 0.050 Uiso 1 1 calc R U . . .
C7 C 0.41903(15) 0.78673(17) 0.70563(9) 0.0320(4) Uani 1 1 d . . . . .
C8 C 0.45205(18) 0.92247(18) 0.68853(10) 0.0426(4) Uani 1 1 d . . . . .
H8 H 0.408953 0.965224 0.646089 0.051 Uiso 1 1 calc R U . . .
C9 C 0.54873(19) 0.9953(2) 0.73405(12) 0.0532(5) Uani 1 1 d . . . . .
H9 H 0.571278 1.086572 0.721830 0.064 Uiso 1 1 calc R U . . .
C10 C 0.61153(19) 0.9338(2) 0.79708(12) 0.0571(6) Uani 1 1 d . . . . .
H10 H 0.675995 0.983227 0.827979 0.068 Uiso 1 1 calc R U . . .
C11 C 0.5789(2) 0.7984(2) 0.81453(11) 0.0566(6) Uani 1 1 d . . . . .
H11 H 0.622402 0.756145 0.856996 0.068 Uiso 1 1 calc R U . . .
C12 C 0.48147(18) 0.72442(19) 0.76928(10) 0.0437(4) Uani 1 1 d . . . . .
H12 H 0.458481 0.633394 0.781798 0.052 Uiso 1 1 calc R U . . .
C13 C 0.35400(16) 0.58337(16) 0.62738(8) 0.0301(4) Uani 1 1 d . . . . .
C14 C 0.49822(16) 0.54424(16) 0.61630(8) 0.0313(4) Uani 1 1 d . . . . .
H14 H 0.572319 0.605803 0.628521 0.038 Uiso 1 1 calc R U . . .
C15 C 0.53130(16) 0.41531(17) 0.58744(8) 0.0324(4) Uani 1 1 d . . . . .
H15 H 0.627773 0.390572 0.580815 0.039 Uiso 1 1 calc R U . . .
C16 C 0.42297(16) 0.32144(16) 0.56802(8) 0.0303(4) Uani 1 1 d . . . . .
C17 C 0.27962(17) 0.36145(17) 0.57781(9) 0.0363(4) Uani 1 1 d . . . . .
H17 H 0.205764 0.300438 0.564334 0.044 Uiso 1 1 calc R U . . .
C18 C 0.24506(16) 0.48963(17) 0.60706(9) 0.0375(4) Uani 1 1 d . . . . .
H18 H 0.148437 0.514097 0.613356 0.045 Uiso 1 1 calc R U . . .
C19 C 0.45716(17) 0.18345(17) 0.53768(8) 0.0324(4) 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
O1 H1 0.871(10) . ?
O1 C19 1.2841(18) . ?
O2 C19 1.2651(19) . ?
N1 C1 1.4319(19) . ?
N1 C7 1.4287(19) . ?
N1 C13 1.3935(19) . ?
C1 C2 1.377(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 C12 1.378(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(2) . ?
C13 C18 1.397(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C16 C17 1.390(2) . ?
C16 C19 1.467(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(2) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 H1 115(2) . . ?
C7 N1 C1 117.89(12) . . ?
C13 N1 C1 120.83(12) . . ?
C13 N1 C7 121.12(12) . . ?
C2 C1 N1 120.22(14) . . ?
C2 C1 C6 119.37(14) . . ?
C6 C1 N1 120.41(14) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.08(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.66(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.50(16) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.42(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.94(16) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 N1 119.57(14) . . ?
C8 C7 C12 119.63(15) . . ?
C12 C7 N1 120.79(15) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.36(18) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.25(19) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.67(18) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(19) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.55(18) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N1 C13 C14 121.04(14) . . ?
N1 C13 C18 120.56(13) . . ?
C18 C13 C14 118.40(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.49(14) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.12(14) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.30(14) . . ?
C15 C16 C19 121.52(14) . . ?
C17 C16 C19 120.18(14) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.18(15) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.50(14) . . ?
C17 C18 H18 119.7 . . ?
O1 C19 C16 117.93(14) . . ?
O2 C19 O1 122.37(14) . . ?
O2 C19 C16 119.69(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -177.88(15) . . . . ?
N1 C1 C6 C5 178.37(16) . . . . ?
N1 C7 C8 C9 -179.75(15) . . . . ?
N1 C7 C12 C11 179.57(15) . . . . ?
N1 C13 C14 C15 179.00(14) . . . . ?
N1 C13 C18 C17 -179.41(15) . . . . ?
C1 N1 C7 C8 -55.8(2) . . . . ?
C1 N1 C7 C12 123.48(16) . . . . ?
C1 N1 C13 C14 159.58(14) . . . . ?
C1 N1 C13 C18 -20.2(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C7 N1 C1 C2 -51.4(2) . . . . ?
C7 N1 C1 C6 128.52(16) . . . . ?
C7 N1 C13 C14 -25.0(2) . . . . ?
C7 N1 C13 C18 155.20(15) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C7 1.1(3) . . . . ?
C12 C7 C8 C9 1.0(2) . . . . ?
C13 N1 C1 C2 124.10(16) . . . . ?
C13 N1 C1 C6 -55.9(2) . . . . ?
C13 N1 C7 C8 128.69(16) . . . . ?
C13 N1 C7 C12 -52.0(2) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C19 -179.61(14) . . . . ?
C15 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C19 O1 6.5(2) . . . . ?
C15 C16 C19 O2 -174.74(14) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C17 C16 C19 O1 -173.71(14) . . . . ?
C17 C16 C19 O2 5.1(2) . . . . ?
C18 C13 C14 C15 -1.2(2) . . . . ?
C19 C16 C17 C18 179.18(15) . . . . ?

_olex2_date_sample_data_collection 2022-01-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.967
_oxdiff_exptl_absorpt_empirical_full_min 0.521
####################################################################### 
# 
# 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_b-3
_database_code_depnum_ccdc_archive 'CCDC 2222049'
loop_
_audit_author_name
_audit_author_address
'Miao Yu'
;cnu
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-12-29 downloaded from the CCDC.
;
_audit_creation_date             2022-06-18
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.3100(10)
_cell_length_b                   9.7399(8)
_cell_length_c                   17.6380(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.742(9)
_cell_angle_gamma                90.00
_cell_volume                     1599.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2543
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      24.5840
_cell_measurement_theta_min      5.1840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1202
_diffrn_reflns_av_unetI/netI     0.1430
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28777
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.133
_diffrn_reflns_theta_min         4.855
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00   7.00   0.50    1.00    --   -0.80  57.00-150.00   60
  2  ω     28.00  81.00   0.50    1.00    --   -0.80  57.00-150.00  106
  3  ω      2.00  28.00   0.50    1.00    --   -0.80  57.00 120.00   52
  4  ω     32.00  79.00   0.50    1.00    --   -0.80  57.00 120.00   94
  5  ω     61.00  89.00   0.50    1.00    --   -0.80  57.00 150.00   56
  6  ω    -19.00  63.00   0.50    1.00    --   -0.80  19.00 -60.00  164
  7  ω    -22.00  41.00   0.50    1.00    --   -0.80  57.00 -60.00  126
  8  ω      8.00  34.00   0.50    1.00    --   -0.80  57.00 -30.00   52
  9  ω      2.00  86.00   0.50    1.00    --   -0.80  57.00  30.00  168
 10  ω     19.00  89.00   0.50    1.00    --   -0.80  37.00 -30.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0604727000
_diffrn_orient_matrix_UB_12      -0.0005780000
_diffrn_orient_matrix_UB_13      -0.0240492000
_diffrn_orient_matrix_UB_21      0.0460727000
_diffrn_orient_matrix_UB_22      0.0086529000
_diffrn_orient_matrix_UB_23      0.0319881000
_diffrn_orient_matrix_UB_31      0.0050755000
_diffrn_orient_matrix_UB_32      -0.0723063000
_diffrn_orient_matrix_UB_33      0.0039827000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1661
_reflns_number_total             4223
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      0.862
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C006(H006), C007(H007), C00C(H00C), C00F(H00F), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T), C011(H011),
 C01A(H01A), C01D(H01D)
2.b Tetrahedral OH refined with riding coordinates:
 O00D(H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.41049(17) -0.35545(18) 0.46411(10) 0.0787(5) Uani 1 1 d . . . . .
O00D O 0.64444(18) -0.39514(17) 0.48443(10) 0.0808(5) Uani 1 1 d . . . . .
H00D H 0.638157 -0.469793 0.463112 0.121 Uiso 1 1 calc R U . . .
N00B N 0.67976(18) 0.20761(19) 0.34227(11) 0.0636(5) Uani 1 1 d . . . . .
C1 C 1.0949(3) 0.3703(3) 0.37389(19) 0.0903(9) Uani 1 1 d . . . . .
H1 H 1.187858 0.403567 0.380442 0.108 Uiso 1 1 calc R U . . .
C002 C 0.8204(2) 0.2649(2) 0.35383(12) 0.0583(5) Uani 1 1 d . . . . .
C003 C 0.5426(2) -0.3178(2) 0.46192(12) 0.0593(5) Uani 1 1 d . . . . .
C006 C 0.5181(3) 0.2191(3) 0.23197(14) 0.0796(7) Uani 1 1 d . . . . .
H006 H 0.541578 0.129067 0.219497 0.096 Uiso 1 1 calc R U . . .
C007 C 0.5023(2) 0.0405(2) 0.38418(12) 0.0587(5) Uani 1 1 d . . . . .
H007 H 0.428930 0.102088 0.372561 0.070 Uiso 1 1 calc R U . . .
C00C C 0.9018(2) 0.3024(3) 0.29206(14) 0.0689(6) Uani 1 1 d . . . . .
H00C H 0.864375 0.292852 0.243190 0.083 Uiso 1 1 calc R U . . .
C00F C 0.4503(3) 0.4865(3) 0.2668(2) 0.0991(10) Uani 1 1 d . . . . .
H00F H 0.428161 0.577140 0.278497 0.119 Uiso 1 1 calc R U . . .
C00G C 0.5801(2) 0.2800(2) 0.29475(12) 0.0601(6) Uani 1 1 d . . . . .
C00H C 0.6454(2) 0.0779(2) 0.37247(11) 0.0572(5) Uani 1 1 d . . . . .
C00L C 0.4204(3) 0.2918(4) 0.18709(18) 0.1017(10) Uani 1 1 d . . . . .
H00L H 0.377264 0.250158 0.145136 0.122 Uiso 1 1 calc R U . . .
C00M C 1.0384(3) 0.3541(3) 0.30315(17) 0.0852(8) Uani 1 1 d . . . . .
H00M H 1.092776 0.378160 0.261359 0.102 Uiso 1 1 calc R U . . .
C00N C 0.3878(3) 0.4260(4) 0.2052(2) 0.1069(12) Uani 1 1 d . . . . .
H00N H 0.322977 0.475175 0.175245 0.128 Uiso 1 1 calc R U . . .
C00O C 0.7531(2) -0.0152(2) 0.39171(14) 0.0693(7) Uani 1 1 d . . . . .
H00O H 0.848852 0.008489 0.384826 0.083 Uiso 1 1 calc R U . . .
C00Q C 0.4691(2) -0.0880(2) 0.41302(11) 0.0587(6) Uani 1 1 d . . . . .
H00Q H 0.373581 -0.112191 0.419895 0.070 Uiso 1 1 calc R U . . .
C00T C 0.7192(2) -0.1428(3) 0.42106(14) 0.0683(6) Uani 1 1 d . . . . .
H00T H 0.792458 -0.203775 0.433786 0.082 Uiso 1 1 calc R U . . .
C011 C 0.5461(3) 0.4152(3) 0.31189(16) 0.0784(7) Uani 1 1 d . . . . .
H011 H 0.588135 0.457556 0.353916 0.094 Uiso 1 1 calc R U . . .
C018 C 0.5771(2) -0.1809(2) 0.43173(11) 0.0570(5) Uani 1 1 d . . . . .
C01A C 1.0137(3) 0.3372(3) 0.43581(17) 0.0913(9) Uani 1 1 d . . . . .
H01A H 1.051288 0.349701 0.484426 0.110 Uiso 1 1 calc R U . . .
C01D C 0.8752(3) 0.2850(3) 0.42609(14) 0.0804(7) Uani 1 1 d . . . . .
H01D H 0.820011 0.263871 0.468076 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C003 1.285(3) . ?
O00D H00D 0.8200 . ?
O00D C003 1.270(3) . ?
N00B C002 1.436(2) . ?
N00B C00G 1.429(2) . ?
N00B C00H 1.410(3) . ?
C1 H1 0.9300 . ?
C1 C00M 1.357(4) . ?
C1 C01A 1.375(4) . ?
C002 C00C 1.385(3) . ?
C002 C01D 1.380(3) . ?
C003 C018 1.474(3) . ?
C006 H006 0.9300 . ?
C006 C00G 1.376(3) . ?
C006 C00L 1.392(4) . ?
C007 H007 0.9300 . ?
C007 C00H 1.400(3) . ?
C007 C00Q 1.388(3) . ?
C00C H00C 0.9300 . ?
C00C C00M 1.380(3) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.359(5) . ?
C00F C011 1.376(4) . ?
C00G C011 1.388(3) . ?
C00H C00O 1.390(3) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.380(5) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00T 1.385(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C018 1.389(3) . ?
C00T H00T 0.9300 . ?
C00T C018 1.389(3) . ?
C011 H011 0.9300 . ?
C01A H01A 0.9300 . ?
C01A C01D 1.395(4) . ?
C01D H01D 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C003 O00D H00D 109.5 . . ?
C00G N00B C002 118.38(17) . . ?
C00H N00B C002 120.40(16) . . ?
C00H N00B C00G 121.05(16) . . ?
C00M C1 H1 120.3 . . ?
C00M C1 C01A 119.5(2) . . ?
C01A C1 H1 120.3 . . ?
C00C C002 N00B 119.90(19) . . ?
C01D C002 N00B 120.8(2) . . ?
C01D C002 C00C 119.3(2) . . ?
O001 C003 C018 118.9(2) . . ?
O00D C003 O001 122.2(2) . . ?
O00D C003 C018 118.94(19) . . ?
C00G C006 H006 119.9 . . ?
C00G C006 C00L 120.2(3) . . ?
C00L C006 H006 119.9 . . ?
C00H C007 H007 119.8 . . ?
C00Q C007 H007 119.8 . . ?
C00Q C007 C00H 120.4(2) . . ?
C002 C00C H00C 120.1 . . ?
C00M C00C C002 119.9(2) . . ?
C00M C00C H00C 120.1 . . ?
C00N C00F H00F 119.6 . . ?
C00N C00F C011 120.7(3) . . ?
C011 C00F H00F 119.6 . . ?
C006 C00G N00B 121.4(2) . . ?
C006 C00G C011 119.3(2) . . ?
C011 C00G N00B 119.3(2) . . ?
C007 C00H N00B 120.70(19) . . ?
C00O C00H N00B 120.68(18) . . ?
C00O C00H C007 118.6(2) . . ?
C006 C00L H00L 120.2 . . ?
C00N C00L C006 119.6(3) . . ?
C00N C00L H00L 120.2 . . ?
C1 C00M C00C 121.2(3) . . ?
C1 C00M H00M 119.4 . . ?
C00C C00M H00M 119.4 . . ?
C00F C00N C00L 120.1(3) . . ?
C00F C00N H00N 119.9 . . ?
C00L C00N H00N 119.9 . . ?
C00H C00O H00O 119.7 . . ?
C00T C00O C00H 120.58(19) . . ?
C00T C00O H00O 119.7 . . ?
C007 C00Q H00Q 119.6 . . ?
C007 C00Q C018 120.72(19) . . ?
C018 C00Q H00Q 119.6 . . ?
C00O C00T H00T 119.5 . . ?
C00O C00T C018 120.9(2) . . ?
C018 C00T H00T 119.5 . . ?
C00F C011 C00G 120.1(3) . . ?
C00F C011 H011 120.0 . . ?
C00G C011 H011 120.0 . . ?
C00Q C018 C003 120.97(19) . . ?
C00T C018 C003 120.3(2) . . ?
C00T C018 C00Q 118.7(2) . . ?
C1 C01A H01A 119.8 . . ?
C1 C01A C01D 120.4(3) . . ?
C01D C01A H01A 119.8 . . ?
C002 C01D C01A 119.7(2) . . ?
C002 C01D H01D 120.2 . . ?
C01A C01D H01D 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C003 C018 C00Q 6.5(3) . . . . ?
O001 C003 C018 C00T -173.1(2) . . . . ?
O00D C003 C018 C00Q -174.0(2) . . . . ?
O00D C003 C018 C00T 6.4(3) . . . . ?
N00B C002 C00C C00M -178.3(2) . . . . ?
N00B C002 C01D C01A 178.2(3) . . . . ?
N00B C00G C011 C00F 180.0(2) . . . . ?
N00B C00H C00O C00T -179.7(2) . . . . ?
C1 C01A C01D C002 0.8(5) . . . . ?
C002 N00B C00G C006 122.8(2) . . . . ?
C002 N00B C00G C011 -56.6(3) . . . . ?
C002 N00B C00H C007 158.6(2) . . . . ?
C002 N00B C00H C00O -21.0(3) . . . . ?
C002 C00C C00M C1 -0.6(4) . . . . ?
C006 C00G C011 C00F 0.6(4) . . . . ?
C006 C00L C00N C00F -0.3(5) . . . . ?
C007 C00H C00O C00T 0.7(4) . . . . ?
C007 C00Q C018 C003 -179.60(19) . . . . ?
C007 C00Q C018 C00T 0.0(3) . . . . ?
C00C C002 C01D C01A -2.7(4) . . . . ?
C00G N00B C002 C00C -51.8(3) . . . . ?
C00G N00B C002 C01D 127.3(3) . . . . ?
C00G N00B C00H C007 -26.3(3) . . . . ?
C00G N00B C00H C00O 154.1(2) . . . . ?
C00G C006 C00L C00N 1.1(4) . . . . ?
C00H N00B C002 C00C 123.4(2) . . . . ?
C00H N00B C002 C01D -57.5(3) . . . . ?
C00H N00B C00G C006 -52.4(3) . . . . ?
C00H N00B C00G C011 128.2(2) . . . . ?
C00H C007 C00Q C018 0.9(3) . . . . ?
C00H C00O C00T C018 0.2(4) . . . . ?
C00L C006 C00G N00B 179.4(2) . . . . ?
C00L C006 C00G C011 -1.2(4) . . . . ?
C00M C1 C01A C01D 1.1(5) . . . . ?
C00N C00F C011 C00G 0.1(4) . . . . ?
C00O C00T C018 C003 179.1(2) . . . . ?
C00O C00T C018 C00Q -0.6(4) . . . . ?
C00Q C007 C00H N00B 179.18(19) . . . . ?
C00Q C007 C00H C00O -1.3(3) . . . . ?
C011 C00F C00N C00L -0.2(5) . . . . ?
C01A C1 C00M C00C -1.2(5) . . . . ?
C01D C002 C00C C00M 2.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.423
_oxdiff_exptl_absorpt_empirical_full_min 0.478
