# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_taoyang_11
_database_code_depnum_ccdc_archive 'CCDC 2193454'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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 0.0181 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   3.9181(6)
_cell_length_b                   24.592(3)
_cell_length_c                   13.0589(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.386(11)
_cell_angle_gamma                90.00
_cell_volume                     1250.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0120
_cell_measurement_theta_min      6.3560
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96584
_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_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        70.16
_diffrn_reflns_theta_max         70.16
_diffrn_reflns_theta_min         3.59
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  77.00   1.50    3.00    --   54.00  57.00  60.00   22
  2  ω     86.00 122.00   1.50    3.00    --   54.00  57.00  60.00   24
  3  ω    101.00 131.00   1.50    4.00    --  108.00  63.00  60.00   20
  4  ω    118.00 176.50   1.50    4.00    --  108.00 111.00   0.00   39
  5  ω    121.00 161.50   1.50    4.00    --  108.00  50.00   0.00   27
  6  ω    104.00 129.50   1.50    4.00    --  108.00 -50.00 120.00   17
  7  ω     88.00 115.00   1.50    4.00    --  108.00-111.00  30.00   18
  8  ω     44.00  71.00   1.50    4.00    --  108.00-111.00  30.00   18
  9  ω     24.00  90.00   1.50    3.00    --   54.00-125.00  30.00   44
 10  ω     39.00  91.50   1.50    4.00    --  108.00-111.00 150.00   35
 11  ω     90.00 174.00   1.50    4.00    --  108.00  63.00 150.00   56
 12  ω     60.00 150.00   1.50    4.00    --  108.00 178.00  60.00   60
 13  ω     50.00 122.00   1.50    3.00    --   54.00  57.00-180.00   48
 14  ω    104.00 170.00   1.50    4.00    --  108.00 111.00-180.00   44
 15  ω     17.00  62.00   1.50    3.00    --   54.00 -57.00-180.00   30
 16  ω    -42.00 -16.50   1.50    1.50    --    0.00 -57.00 120.00   17
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0915045000
_diffrn_orient_matrix_UB_12      0.0601025000
_diffrn_orient_matrix_UB_13      0.0154633000
_diffrn_orient_matrix_UB_21      -0.3224565000
_diffrn_orient_matrix_UB_22      -0.0175097000
_diffrn_orient_matrix_UB_23      0.0491490000
_diffrn_orient_matrix_UB_31      0.2107825000
_diffrn_orient_matrix_UB_32      -0.0006180000
_diffrn_orient_matrix_UB_33      0.1069397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1663
_reflns_number_total             2317
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0574P)²+0.1351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.0033(5) 0.80747(7) 0.04162(12) 0.0581(5) Uani 1 d . . .
N1 N 0.4899(5) 0.74452(7) 0.32118(13) 0.0362(4) Uani 1 d . . .
H1 H 0.5898 0.7647 0.3693 0.043 Uiso 1 calc . . R
N2 N 0.3214(5) 0.82240(7) 0.22450(13) 0.0419(5) Uani 1 d . . .
H2 H 0.2229 0.8335 0.1661 0.050 Uiso 1 calc . . R
C1 C 0.1705(5) 0.73446(9) 0.15621(15) 0.0344(5) Uani 1 d . . .
C2 C 0.3298(5) 0.76862(9) 0.23594(15) 0.0325(5) Uani 1 d . . .
C3 C 0.4992(6) 0.69017(10) 0.33382(17) 0.0453(6) Uani 1 d . . .
H3 H 0.6135 0.6756 0.3938 0.054 Uiso 1 calc . . R
C4 C 0.3457(7) 0.65647(10) 0.26116(19) 0.0519(7) Uani 1 d . . .
H4 H 0.3494 0.6190 0.2707 0.062 Uiso 1 calc . . R
C5 C 0.1815(6) 0.67960(10) 0.17130(17) 0.0427(6) Uani 1 d . . .
H5 H 0.0764 0.6569 0.1202 0.051 Uiso 1 calc . . R
C6 C -0.0034(6) 0.75731(9) 0.05578(16) 0.0389(5) Uani 1 d . . .
C7 C 0.4474(5) 0.86424(9) 0.29248(16) 0.0348(5) Uani 1 d . . .
C8 C 0.4054(6) 0.86317(9) 0.39477(17) 0.0392(5) Uani 1 d . . .
H8 H 0.2977 0.8337 0.4221 0.047 Uiso 1 calc . . R
C9 C 0.5249(6) 0.90665(10) 0.45907(17) 0.0436(6) Uani 1 d . . .
H9 H 0.5027 0.9050 0.5292 0.052 Uiso 1 calc . . R
C10 C 0.6716(6) 0.95079(10) 0.42034(19) 0.0450(6) Uani 1 d . . .
H10 H 0.7496 0.9790 0.4642 0.054 Uiso 1 calc . . R
C11 C 0.7081(6) 0.95454(9) 0.31428(19) 0.0414(5) Uani 1 d . . .
C12 C 0.8527(7) 1.00074(11) 0.2719(2) 0.0558(7) Uani 1 d . . .
H12 H 0.9281 1.0295 0.3147 0.067 Uiso 1 calc . . R
C13 C 0.8835(8) 1.00386(12) 0.1698(2) 0.0640(8) Uani 1 d . . .
H13 H 0.9762 1.0349 0.1430 0.077 Uiso 1 calc . . R
C14 C 0.7757(8) 0.96044(12) 0.1046(2) 0.0612(7) Uani 1 d . . .
H14 H 0.7984 0.9628 0.0346 0.073 Uiso 1 calc . . R
C15 C 0.6387(6) 0.91491(10) 0.14223(18) 0.0479(6) Uani 1 d . . .
H15 H 0.5704 0.8864 0.0978 0.058 Uiso 1 calc . . R
C16 C 0.5985(5) 0.91033(9) 0.24859(17) 0.0372(5) Uani 1 d . . .
O2 O -0.1368(5) 0.72307(7) -0.00711(12) 0.0525(5) Uani 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 C6 1.248(3) . ?
N1 C2 1.352(3) . ?
N1 C3 1.347(3) . ?
N2 C2 1.331(3) . ?
N2 C7 1.412(3) . ?
C1 C2 1.426(3) . ?
C1 C5 1.363(3) . ?
C1 C6 1.517(3) . ?
C3 C4 1.350(3) . ?
C4 C5 1.395(3) . ?
C6 O2 1.250(3) . ?
C7 C8 1.364(3) . ?
C7 C16 1.428(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.352(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.410(3) . ?
C11 C16 1.421(3) . ?
C12 C13 1.354(4) . ?
C13 C14 1.402(4) . ?
C14 C15 1.357(4) . ?
C15 C16 1.420(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
C3 N1 C2 122.65(18) . . ?
C2 N2 C7 130.62(18) . . ?
C2 C1 C6 122.06(19) . . ?
C5 C1 C2 118.23(19) . . ?
C5 C1 C6 119.70(19) . . ?
N1 C2 C1 117.91(19) . . ?
N2 C2 N1 122.10(18) . . ?
N2 C2 C1 119.99(18) . . ?
N1 C3 C4 121.3(2) . . ?
C3 C4 C5 118.0(2) . . ?
C1 C5 C4 121.9(2) . . ?
O1 C6 C1 118.65(18) . . ?
O1 C6 O2 125.7(2) . . ?
O2 C6 C1 115.7(2) . . ?
N2 C7 C16 117.24(19) . . ?
C8 C7 N2 122.0(2) . . ?
C8 C7 C16 120.6(2) . . ?
C7 C8 C9 120.1(2) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 120.9(2) . . ?
C10 C11 C16 119.1(2) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 C16 119.1(2) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C14 120.1(3) . . ?
C15 C14 C13 120.9(3) . . ?
C14 C15 C16 120.7(2) . . ?
C11 C16 C7 118.4(2) . . ?
C15 C16 C7 123.5(2) . . ?
C15 C16 C11 118.1(2) . . ?

_olex2_date_sample_data_collection 2020-10-27
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# 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_tangy_3
_database_code_depnum_ccdc_archive 'CCDC 2193457'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2020-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_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 0.0181 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.0931(3)
_cell_length_b                   14.2729(5)
_cell_length_c                   11.3085(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.304(4)
_cell_angle_gamma                90
_cell_volume                     1302.58(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2174
_cell_measurement_temperature    293.23(10)
_cell_measurement_theta_max      69.8100
_cell_measurement_theta_min      6.9600
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54185
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4653
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.532
_diffrn_reflns_theta_min         4.998
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.23(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  94.00   1.00    1.00    --   54.00  77.00  60.00   70
  2  ω    105.00 132.00   1.00    1.00    --  108.00 111.00 -30.00   27
  3  ω     92.00 178.00   1.00    1.00    --  108.00  50.00  60.00   86
  4  ω     97.00 167.00   1.00    1.00    --  108.00  63.00 120.00   70
  5  ω     83.00 129.00   1.00    1.00    --  108.00 -63.00  90.00   46
  6  ω     55.00 128.00   1.00    1.00    --  108.00 -63.00 -30.00   73
  7  ω     38.00  64.00   1.00    1.00    --   54.00-126.00 -92.00   26
  8  ω     27.00  88.00   1.00    1.00    --   54.00-125.00   0.00   61
  9  ω     40.00  67.00   1.00    1.00    --  108.00 -63.00  90.00   27
 10  ω     36.00 113.00   1.00    1.00    --  108.00-111.00 -30.00   77
 11  ω     36.00 101.00   1.00    1.00    --  108.00-111.00 -90.00   65
 12  ω     19.00  66.00   1.00    1.00    --    0.00  57.00-150.00   47
 13  ω     14.00  41.00   1.00    1.00    --    0.00  57.00 -30.00   27
 14  ω    -14.00  13.00   1.00    1.00    --    0.00  57.00-150.00   27
 15  ω    -18.00  96.00   1.00    1.00    --   54.00 -19.00-180.00  114
 16  ω    101.00 126.00   1.00    1.00    --  108.00  63.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1065024000
_diffrn_orient_matrix_UB_12      0.0629335000
_diffrn_orient_matrix_UB_13      0.0748718000
_diffrn_orient_matrix_UB_21      -0.0877318000
_diffrn_orient_matrix_UB_22      -0.0873052000
_diffrn_orient_matrix_UB_23      0.0449811000
_diffrn_orient_matrix_UB_31      0.1317082000
_diffrn_orient_matrix_UB_32      -0.0071605000
_diffrn_orient_matrix_UB_33      0.1052954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2069
_reflns_number_total             2378
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.057
_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)+(0.0814P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11160(19) 0.69585(8) 0.16388(14) 0.0588(4) Uani 1 1 d . . . . .
O2 O -0.0648(2) 0.63606(9) 0.28446(17) 0.0749(5) Uani 1 1 d . . . . .
H2 H -0.044275 0.587534 0.249603 0.112 Uiso 1 1 calc GR . . . .
N1 N 0.1679(2) 0.88174(10) 0.18032(16) 0.0547(5) Uani 1 1 d . . . . .
H1 H 0.183155 0.831233 0.141108 0.066 Uiso 1 1 calc R . . . .
N2 N 0.00499(19) 0.96489(9) 0.30271(14) 0.0465(4) Uani 1 1 d . . . . .
C1 C 0.2680(2) 0.96135(11) 0.15854(17) 0.0474(5) Uani 1 1 d . . . . .
C2 C 0.2574(2) 1.00384(11) 0.05229(17) 0.0451(4) Uani 1 1 d . . . . .
H2A H 0.183426 0.981132 -0.007877 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3575(2) 1.08315(11) 0.03019(16) 0.0427(4) Uani 1 1 d . . . . .
C4 C 0.3458(2) 1.13022(14) -0.07824(18) 0.0539(5) Uani 1 1 d . . . . .
H4 H 0.273785 1.108107 -0.139904 0.065 Uiso 1 1 calc R . . . .
C5 C 0.4380(3) 1.20772(14) -0.0950(2) 0.0622(6) Uani 1 1 d . . . . .
H5 H 0.426253 1.238911 -0.167341 0.075 Uiso 1 1 calc R . . . .
C6 C 0.5502(3) 1.24137(13) -0.0054(2) 0.0586(5) Uani 1 1 d . . . . .
H6 H 0.613483 1.294194 -0.018760 0.070 Uiso 1 1 calc R . . . .
C7 C 0.5677(2) 1.19711(13) 0.1018(2) 0.0550(5) Uani 1 1 d . . . . .
H7 H 0.643014 1.219663 0.161202 0.066 Uiso 1 1 calc R . . . .
C8 C 0.4697(2) 1.11568(11) 0.12301(16) 0.0442(4) Uani 1 1 d . . . . .
C9 C 0.4819(3) 1.06876(13) 0.23275(18) 0.0535(5) Uani 1 1 d . . . . .
H9 H 0.557531 1.089282 0.293179 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3835(3) 0.99338(13) 0.25106(19) 0.0547(5) Uani 1 1 d . . . . .
H10 H 0.391745 0.962876 0.323927 0.066 Uiso 1 1 calc R . . . .
C11 C 0.0507(2) 0.88149(10) 0.25924(16) 0.0416(4) Uani 1 1 d . . . . .
C12 C -0.0244(2) 0.79683(10) 0.29406(16) 0.0416(4) Uani 1 1 d . . . . .
C13 C -0.1398(2) 0.80239(12) 0.37769(18) 0.0507(5) Uani 1 1 d . . . . .
H13 H -0.188748 0.747933 0.403625 0.061 Uiso 1 1 calc R . . . .
C14 C -0.1833(3) 0.88808(13) 0.42338(19) 0.0571(5) Uani 1 1 d . . . . .
H14 H -0.260725 0.892234 0.479935 0.068 Uiso 1 1 calc R . . . .
C15 C -0.1088(2) 0.96647(12) 0.38257(18) 0.0512(5) Uani 1 1 d . . . . .
H15 H -0.139042 1.024300 0.412091 0.061 Uiso 1 1 calc R . . . .
C16 C 0.0154(2) 0.70547(10) 0.24037(18) 0.0444(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 C16 1.214(2) . ?
O2 C16 1.304(2) . ?
N1 C1 1.427(2) . ?
N1 C11 1.351(2) . ?
N2 C11 1.350(2) . ?
N2 C15 1.338(2) . ?
C1 C2 1.343(3) . ?
C1 C10 1.425(3) . ?
C2 C3 1.425(2) . ?
C3 C4 1.395(3) . ?
C3 C8 1.414(3) . ?
C4 C5 1.355(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.365(3) . ?
C7 C8 1.437(2) . ?
C8 C9 1.407(3) . ?
C9 C10 1.363(3) . ?
C11 C12 1.421(2) . ?
C12 C13 1.380(3) . ?
C12 C16 1.484(2) . ?
C13 C14 1.384(3) . ?
C14 C15 1.368(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
C11 N1 C1 123.49(14) . . ?
C15 N2 C11 118.82(14) . . ?
C2 C1 N1 121.00(18) . . ?
C2 C1 C10 120.42(16) . . ?
C10 C1 N1 118.56(17) . . ?
C1 C2 C3 121.10(17) . . ?
C4 C3 C2 122.32(17) . . ?
C4 C3 C8 119.46(16) . . ?
C8 C3 C2 118.20(16) . . ?
C5 C4 C3 120.9(2) . . ?
C4 C5 C6 121.0(2) . . ?
C7 C6 C5 120.29(18) . . ?
C6 C7 C8 120.05(19) . . ?
C3 C8 C7 118.25(17) . . ?
C9 C8 C3 119.82(16) . . ?
C9 C8 C7 121.93(18) . . ?
C10 C9 C8 120.42(18) . . ?
C9 C10 C1 120.01(18) . . ?
N1 C11 C12 121.43(14) . . ?
N2 C11 N1 117.62(14) . . ?
N2 C11 C12 120.94(16) . . ?
C11 C12 C16 121.54(16) . . ?
C13 C12 C11 117.79(15) . . ?
C13 C12 C16 120.64(14) . . ?
C12 C13 C14 120.75(16) . . ?
C15 C14 C13 117.76(17) . . ?
N2 C15 C14 123.89(16) . . ?
O1 C16 O2 123.41(15) . . ?
O1 C16 C12 124.15(14) . . ?
O2 C16 C12 112.44(15) . . ?

_olex2_date_sample_data_collection 2020-09-16
_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 2.484
_oxdiff_exptl_absorpt_empirical_full_min 0.502
####################################################################### 
# 
# 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_k08096
_database_code_depnum_ccdc_archive 'CCDC 2193487'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4169(2)
_cell_length_b                   14.166(3)
_cell_length_c                   11.8164(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1010(11)
_cell_angle_gamma                90.00
_cell_volume                     1218.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    2904
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5090
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2784
_reflns_number_gt                2461
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.4728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     202
_refine_ls_number_restraints     237
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.98332(12) 0.42833(6) 0.29272(8) 0.0181(2) Uani 1 1 d . A .
C2 C 0.95070(14) 0.51445(7) 0.24314(9) 0.0178(2) Uani 1 1 d . . .
C3 C 1.04901(14) 0.59574(7) 0.29365(9) 0.0166(2) Uani 1 1 d . A .
C4 C 1.17819(14) 0.58436(8) 0.39454(9) 0.0191(2) Uani 1 1 d . . .
H4 H 1.2456 0.6373 0.4293 0.023 Uiso 1 1 calc R A .
C5 C 1.20921(15) 0.49586(8) 0.44491(9) 0.0213(2) Uani 1 1 d . A .
H5 H 1.2966 0.4871 0.5143 0.026 Uiso 1 1 calc R . .
C6 C 1.10882(15) 0.42097(8) 0.39091(9) 0.0193(2) Uani 1 1 d . . .
H6 H 1.1297 0.3603 0.4253 0.023 Uiso 1 1 calc R A .
N7 N 0.82481(13) 0.52089(7) 0.14308(9) 0.0178(2) Uani 0.9375(13) 1 d PDU A 1
H7 H 0.8097 0.5763 0.1089 0.021 Uiso 0.9375(13) 1 calc PR A 1
C8 C 0.71507(14) 0.44391(8) 0.08943(9) 0.0159(2) Uani 0.9375(13) 1 d PDU A 1
C9 C 0.57004(15) 0.40886(8) 0.13701(9) 0.0179(2) Uani 0.9375(13) 1 d PDU A 1
C10 C 0.46637(17) 0.33322(9) 0.08108(10) 0.0197(3) Uani 0.9375(13) 1 d PDU A 1
C11 C 0.50715(16) 0.29722(9) -0.02049(10) 0.0199(3) Uani 0.9375(13) 1 d PDU A 1
H11 H 0.4366 0.2463 -0.0581 0.024 Uiso 0.9375(13) 1 calc PR A 1
C12 C 0.64841(16) 0.33418(9) -0.06783(10) 0.0227(3) Uani 0.9375(13) 1 d PDU A 1
H12 H 0.6733 0.3095 -0.1380 0.027 Uiso 0.9375(13) 1 calc PR A 1
C13 C 0.75369(19) 0.40765(11) -0.01217(11) 0.0214(3) Uani 0.9375(13) 1 d PDU A
1
H13 H 0.8519 0.4330 -0.0437 0.026 Uiso 0.9375(13) 1 calc PR A 1
C14 C 0.52575(19) 0.44953(12) 0.24608(12) 0.0274(3) Uani 0.9375(13) 1 d PDU A 1
H14A H 0.5704 0.4068 0.3106 0.041 Uiso 0.9375(13) 1 calc PR A 1
H14B H 0.3924 0.4571 0.2373 0.041 Uiso 0.9375(13) 1 calc PR A 1
H14C H 0.5855 0.5112 0.2614 0.041 Uiso 0.9375(13) 1 calc PR A 1
C15 C 0.3117(2) 0.29107(12) 0.13085(12) 0.0348(4) Uani 0.9375(13) 1 d PDU A 1
H15A H 0.2640 0.2351 0.0862 0.052 Uiso 0.9375(13) 1 calc PR A 1
H15B H 0.2131 0.3377 0.1273 0.052 Uiso 0.9375(13) 1 calc PR A 1
H15C H 0.3575 0.2731 0.2113 0.052 Uiso 0.9375(13) 1 calc PR A 1
N7' N 0.775(2) 0.5276(9) 0.1959(13) 0.0178(2) Uani 0.0625(13) 1 d PDU A 2
H7' H 0.7309 0.5854 0.1909 0.021 Uiso 0.0625(13) 1 calc PR A 2
C8' C 0.653(2) 0.4512(10) 0.1528(12) 0.0159(2) Uani 0.0625(13) 1 d PDU A 2
C9' C 0.655(2) 0.4071(11) 0.0490(12) 0.019(2) Uiso 0.0625(13) 1 d PDU A 2
C10' C 0.528(2) 0.3296(11) 0.0186(13) 0.015(2) Uiso 0.0625(13) 1 d PDU A 2
C11' C 0.409(2) 0.3059(12) 0.0902(13) 0.016(3) Uiso 0.0625(13) 1 d PDU A 2
H11' H 0.3252 0.2553 0.0684 0.019 Uiso 0.0625(13) 1 calc PR A 2
C12' C 0.405(2) 0.3517(11) 0.1902(13) 0.022(2) Uiso 0.0625(13) 1 d PDU A 2
H12' H 0.3205 0.3352 0.2380 0.026 Uiso 0.0625(13) 1 calc PR A 2
C13' C 0.532(3) 0.4244(13) 0.2192(16) 0.017(3) Uiso 0.0625(13) 1 d PDU A 2
H13' H 0.5334 0.4571 0.2896 0.020 Uiso 0.0625(13) 1 calc PR A 2
C14' C 0.788(3) 0.4339(15) -0.0254(17) 0.017(4) Uiso 0.0625(13) 1 d PDU A 2
H14D H 0.7664 0.3950 -0.0954 0.026 Uiso 0.0625(13) 1 calc PR A 2
H14E H 0.9138 0.4235 0.0170 0.026 Uiso 0.0625(13) 1 calc PR A 2
H14F H 0.7720 0.5006 -0.0467 0.026 Uiso 0.0625(13) 1 calc PR A 2
C15' C 0.542(2) 0.2778(12) -0.0922(13) 0.022(3) Uiso 0.0625(13) 1 d PDU A 2
H15D H 0.6346 0.3086 -0.1287 0.033 Uiso 0.0625(13) 1 calc PR A 2
H15E H 0.4228 0.2793 -0.1449 0.033 Uiso 0.0625(13) 1 calc PR A 2
H15F H 0.5783 0.2121 -0.0743 0.033 Uiso 0.0625(13) 1 calc PR A 2
C16 C 1.01640(14) 0.69013(7) 0.23933(9) 0.0169(2) Uani 1 1 d . . .
O17 O 1.11733(10) 0.75732(5) 0.29684(7) 0.0214(2) Uani 1 1 d . A .
H17 H 1.0878 0.8096 0.2651 0.032 Uiso 1 1 calc R . .
O18 O 0.90759(11) 0.70386(5) 0.14873(7) 0.0232(2) Uani 1 1 d . A .


_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
N1 C6 1.3445(13) . ?
N1 C2 1.3547(14) . ?
C2 N7' 1.330(14) . ?
C2 N7 1.3612(13) . ?
C2 C3 1.4306(14) . ?
C3 C4 1.3876(14) . ?
C3 C16 1.4827(14) . ?
C4 C5 1.3879(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3799(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.4335(14) . ?
N7 H7 0.8800 . ?
C8 C13 1.3854(17) . ?
C8 C9 1.3974(16) . ?
C9 C10 1.4073(17) . ?
C9 C14 1.5046(17) . ?
C10 C11 1.3899(17) . ?
C10 C15 1.5094(18) . ?
C11 C12 1.3822(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3884(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N7' C8' 1.437(14) . ?
N7' H7' 0.8800 . ?
C8' C13' 1.359(15) . ?
C8' C9' 1.378(14) . ?
C9' C10' 1.443(15) . ?
C9' C14' 1.495(15) . ?
C10' C11' 1.381(15) . ?
C10' C15' 1.521(15) . ?
C11' C12' 1.352(15) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.391(15) . ?
C12' H12' 0.9500 . ?
C13' H13' 0.9500 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16 O18 1.2258(13) . ?
C16 O17 1.3161(13) . ?
O17 H17 0.8400 . ?

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
C6 N1 C2 118.65(9) . . ?
N7' C2 N1 112.7(6) . . ?
N7' C2 N7 34.2(7) . . ?
N1 C2 N7 118.13(9) . . ?
N7' C2 C3 116.3(6) . . ?
N1 C2 C3 120.67(9) . . ?
N7 C2 C3 121.18(9) . . ?
C4 C3 C2 118.50(9) . . ?
C4 C3 C16 120.32(9) . . ?
C2 C3 C16 121.18(9) . . ?
C3 C4 C5 120.23(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 117.78(10) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N1 C6 C5 124.17(10) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C2 N7 C8 124.70(9) . . ?
C2 N7 H7 117.7 . . ?
C8 N7 H7 117.7 . . ?
C13 C8 C9 121.37(11) . . ?
C13 C8 N7 118.08(11) . . ?
C9 C8 N7 120.52(10) . . ?
C8 C9 C10 118.35(10) . . ?
C8 C9 C14 121.37(11) . . ?
C10 C9 C14 120.28(11) . . ?
C11 C10 C9 119.66(12) . . ?
C11 C10 C15 119.96(12) . . ?
C9 C10 C15 120.38(11) . . ?
C12 C11 C10 121.23(12) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.56(11) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 119.81(13) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C2 N7' C8' 122.8(12) . . ?
C2 N7' H7' 118.6 . . ?
C8' N7' H7' 118.6 . . ?
C13' C8' C9' 120.4(13) . . ?
C13' C8' N7' 116.5(12) . . ?
C9' C8' N7' 123.1(12) . . ?
C8' C9' C10' 116.8(11) . . ?
C8' C9' C14' 121.8(13) . . ?
C10' C9' C14' 121.2(13) . . ?
C11' C10' C9' 119.7(13) . . ?
C11' C10' C15' 124.7(13) . . ?
C9' C10' C15' 115.6(12) . . ?
C12' C11' C10' 122.9(15) . . ?
C12' C11' H11' 118.6 . . ?
C10' C11' H11' 118.6 . . ?
C11' C12' C13' 116.4(14) . . ?
C11' C12' H12' 121.8 . . ?
C13' C12' H12' 121.8 . . ?
C8' C13' C12' 123.8(15) . . ?
C8' C13' H13' 118.1 . . ?
C12' C13' H13' 118.1 . . ?
C9' C14' H14D 109.5 . . ?
C9' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C9' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C10' C15' H15D 109.5 . . ?
C10' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C10' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
O18 C16 O17 123.34(10) . . ?
O18 C16 C3 123.11(9) . . ?
O17 C16 C3 113.55(9) . . ?
C16 O17 H17 109.5 . . ?

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
C6 N1 C2 N7' -143.2(8) . . . . ?
C6 N1 C2 N7 179.30(9) . . . . ?
C6 N1 C2 C3 0.57(15) . . . . ?
N7' C2 C3 C4 142.5(8) . . . . ?
N1 C2 C3 C4 -0.08(15) . . . . ?
N7 C2 C3 C4 -178.76(10) . . . . ?
N7' C2 C3 C16 -38.3(8) . . . . ?
N1 C2 C3 C16 179.14(9) . . . . ?
N7 C2 C3 C16 0.45(16) . . . . ?
C2 C3 C4 C5 -0.43(16) . . . . ?
C16 C3 C4 C5 -179.65(10) . . . . ?
C3 C4 C5 C6 0.43(16) . . . . ?
C2 N1 C6 C5 -0.59(16) . . . . ?
C4 C5 C6 N1 0.09(17) . . . . ?
N7' C2 N7 C8 -85.5(10) . . . . ?
N1 C2 N7 C8 4.04(16) . . . . ?
C3 C2 N7 C8 -177.24(10) . . . . ?
C2 N7 C8 C13 -109.16(13) . . . . ?
C2 N7 C8 C9 72.75(15) . . . . ?
C13 C8 C9 C10 1.97(17) . . . . ?
N7 C8 C9 C10 179.99(10) . . . . ?
C13 C8 C9 C14 -178.77(12) . . . . ?
N7 C8 C9 C14 -0.75(17) . . . . ?
C8 C9 C10 C11 -1.63(17) . . . . ?
C14 C9 C10 C11 179.09(11) . . . . ?
C8 C9 C10 C15 178.29(11) . . . . ?
C14 C9 C10 C15 -0.98(18) . . . . ?
C9 C10 C11 C12 0.16(18) . . . . ?
C15 C10 C11 C12 -179.76(12) . . . . ?
C10 C11 C12 C13 1.03(19) . . . . ?
C9 C8 C13 C12 -0.80(19) . . . . ?
N7 C8 C13 C12 -178.87(11) . . . . ?
C11 C12 C13 C8 -0.72(19) . . . . ?
N1 C2 N7' C8' -27.8(16) . . . . ?
N7 C2 N7' C8' 79.2(15) . . . . ?
C3 C2 N7' C8' -173.3(11) . . . . ?
C2 N7' C8' C13' 104.1(19) . . . . ?
C2 N7' C8' C9' -77(2) . . . . ?
C13' C8' C9' C10' -3(3) . . . . ?
N7' C8' C9' C10' 178.2(15) . . . . ?
C13' C8' C9' C14' -179.1(18) . . . . ?
N7' C8' C9' C14' 2(3) . . . . ?
C8' C9' C10' C11' 3(2) . . . . ?
C14' C9' C10' C11' 179.1(17) . . . . ?
C8' C9' C10' C15' -175.9(15) . . . . ?
C14' C9' C10' C15' 1(2) . . . . ?
C9' C10' C11' C12' -1(3) . . . . ?
C15' C10' C11' C12' 177.6(17) . . . . ?
C10' C11' C12' C13' -1(3) . . . . ?
C9' C8' C13' C12' 1(3) . . . . ?
N7' C8' C13' C12' -179.9(18) . . . . ?
C11' C12' C13' C8' 1(3) . . . . ?
C4 C3 C16 O18 178.04(10) . . . . ?
C2 C3 C16 O18 -1.16(16) . . . . ?
C4 C3 C16 O17 -1.03(14) . . . . ?
C2 C3 C16 O17 179.77(9) . . . . ?

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
O17 H17 N1 0.84 1.85 2.6911(13) 174.8 2_755
N7 H7 O18 0.88 1.97 2.6614(13) 134.4 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_taoy_10
_database_code_depnum_ccdc_archive 'CCDC 2193456'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C16 H12 N2 O2), 2(H2 O)'
_chemical_formula_sum            'C32 H28 N4 O6'
_chemical_formula_weight         564.58
_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 0.0181 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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.4767(12)
_cell_length_b                   10.7575(17)
_cell_length_c                   17.909(3)
_cell_angle_alpha                75.646(14)
_cell_angle_beta                 83.673(13)
_cell_angle_gamma                79.935(14)
_cell_volume                     1370.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.3120
_cell_measurement_theta_min      5.5060
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94883
_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_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8684
_diffrn_reflns_theta_full        70.42
_diffrn_reflns_theta_max         70.42
_diffrn_reflns_theta_min         4.29
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 110.00   1.50    1.50    --   54.00-134.00 126.00   50
  2  ω    106.00 136.00   1.50    2.00    --  108.00 -91.00  90.00   20
  3  ω     71.00 116.00   1.50    2.00    --  108.00-111.00   0.00   30
  4  ω    110.00 137.00   1.50    2.00    --  108.00 -91.00 -60.00   18
  5  ω     59.00  93.50   1.50    2.00    --  108.00 -91.00  90.00   23
  6  ω     47.00 108.50   1.50    2.00    --  108.00-111.00 150.00   41
  7  ω     39.00 141.00   1.50    2.00    --  108.00 -25.00  60.00   68
  8  ω     90.00 126.00   1.50    2.00    --  108.00  38.00 120.00   24
  9  ω     76.00 178.00   1.50    2.00    --  108.00  25.00  60.00   68
 10  ω    116.00 143.00   1.50    2.00    --  108.00 111.00   0.00   18
 11  ω    106.00 169.00   1.50    2.00    --  108.00 135.00  12.00   42
 12  ω     85.00 160.00   1.50    2.00    --  108.00  25.00 -30.00   50
 13  ω     54.00  87.00   1.50    2.00    --  108.00 -91.00 -60.00   22
 14  ω     42.00 123.00   1.50    2.00    --  108.00 -50.00 -30.00   54
 15  ω     50.00  77.00   1.50    1.50    --   54.00 -38.00 -90.00   18
 16  ω     38.00 129.50   1.50    2.00    --  108.00 -50.00-120.00   61
 17  ω     45.00  72.00   1.50    1.50    --   54.00-125.00-180.00   18
 18  ω     12.00  72.00   1.50    1.50    --   54.00 -57.00 -90.00   40
 19  ω      4.00  95.50   1.50    1.50    --   54.00 -19.00 -30.00   61
 20  ω     41.00  68.00   1.50    1.50    --    0.00  77.00 -30.00   18
 21  ω     40.00 112.00   1.50    2.00    --  108.00 -50.00 120.00   48
 22  ω     39.00 111.00   1.50    1.50    --   54.00  57.00 150.00   48
 23  ω    -18.00   7.50   1.50    1.50    --   54.00 -38.00 -90.00   17
 24  ω    -12.00  69.00   1.50    1.50    --   54.00 -57.00-180.00   54
 25  ω    -21.00  15.00   1.50    1.50    --    0.00  77.00 -30.00   24
 26  ω    -61.00 -34.00   1.50    1.50    --    0.00 -57.00-150.00   18
 27  ω    -26.00   1.00   1.50    1.50    --    0.00 -57.00-150.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206615000
_diffrn_orient_matrix_UB_12      0.0795616000
_diffrn_orient_matrix_UB_13      -0.0837255000
_diffrn_orient_matrix_UB_21      -0.1020359000
_diffrn_orient_matrix_UB_22      0.1171213000
_diffrn_orient_matrix_UB_23      0.0302150000
_diffrn_orient_matrix_UB_31      0.1821312000
_diffrn_orient_matrix_UB_32      0.0482563000
_diffrn_orient_matrix_UB_33      0.0002410000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2795
_reflns_number_total             5056
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5056
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1740
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
  C14(H14), C15(H15), N4(H4A), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 1.3768(3) 0.8451(2) 0.08735(12) 0.0614(6) Uani 1 d . . .
O2 O 1.4181(4) 0.7243(2) 0.00031(11) 0.0645(7) Uani 1 d . . .
H2 H 1.4429 0.7921 -0.0285 0.097 Uiso 1 calc . . GR
N1 N 1.2519(3) 0.5128(2) 0.25808(14) 0.0497(6) Uani 1 d . . .
N2 N 1.3116(4) 0.7244(2) 0.23487(14) 0.0537(7) Uani 1 d . . .
H2A H 1.3353 0.7914 0.1999 0.064 Uiso 1 calc . . R
C1 C 1.3014(4) 0.6188(3) 0.20768(16) 0.0431(7) Uani 1 d . . .
C2 C 1.3386(4) 0.6216(3) 0.12807(16) 0.0414(6) Uani 1 d . . .
C3 C 1.3339(4) 0.5101(3) 0.10406(17) 0.0481(7) Uani 1 d . . .
H3 H 1.3629 0.5087 0.0524 0.058 Uiso 1 calc . . R
C4 C 1.2866(4) 0.4004(3) 0.15606(18) 0.0515(8) Uani 1 d . . .
H4 H 1.2834 0.3244 0.1407 0.062 Uiso 1 calc . . R
C5 C 1.2448(4) 0.4088(3) 0.23131(18) 0.0519(8) Uani 1 d . . .
H5 H 1.2087 0.3365 0.2663 0.062 Uiso 1 calc . . R
C6 C 1.3800(4) 0.7407(3) 0.07084(16) 0.0476(7) Uani 1 d . . .
C7 C 1.2897(4) 0.7420(3) 0.31041(16) 0.0463(7) Uani 1 d . . .
C8 C 1.3505(4) 0.6459(3) 0.37334(18) 0.0554(8) Uani 1 d . . .
H8 H 1.4051 0.5645 0.3665 0.066 Uiso 1 calc . . R
C9 C 1.3304(4) 0.6703(3) 0.44689(18) 0.0621(9) Uani 1 d . . .
H9 H 1.3678 0.6034 0.4887 0.075 Uiso 1 calc . . R
C10 C 1.2581(5) 0.7882(3) 0.45919(18) 0.0605(9) Uani 1 d . . .
H10 H 1.2489 0.8024 0.5087 0.073 Uiso 1 calc . . R
C11 C 1.1960(4) 0.8907(3) 0.39618(17) 0.0485(7) Uani 1 d . . .
C12 C 1.1207(4) 1.0152(3) 0.4063(2) 0.0583(9) Uani 1 d . . .
H12 H 1.1149 1.0318 0.4551 0.070 Uiso 1 calc . . R
C13 C 1.0567(4) 1.1112(3) 0.3471(2) 0.0612(9) Uani 1 d . . .
H13 H 1.0063 1.1924 0.3554 0.073 Uiso 1 calc . . R
C14 C 1.0662(4) 1.0883(3) 0.2730(2) 0.0577(8) Uani 1 d . . .
H14 H 1.0208 1.1543 0.2323 0.069 Uiso 1 calc . . R
C15 C 1.1414(4) 0.9702(3) 0.26035(18) 0.0508(7) Uani 1 d . . .
H15 H 1.1479 0.9569 0.2107 0.061 Uiso 1 calc . . R
C16 C 1.2102(4) 0.8669(3) 0.32130(17) 0.0442(7) Uani 1 d . . .
O3 O 1.5238(4) 0.9209(2) -0.09845(14) 0.0699(7) Uani 1 d . . .
H3A H 1.5425 0.9847 -0.0817 0.105 Uiso 1 d . . G
H3B H 1.4541 0.9486 -0.1354 0.105 Uiso 1 d . . G
O4 O 0.8418(3) 0.6539(2) 0.40991(12) 0.0632(6) Uani 1 d . . .
O5 O 0.7711(4) 0.7699(2) 0.49914(12) 0.0650(6) Uani 1 d . . .
H5A H 0.8256 0.7042 0.5262 0.097 Uiso 1 calc . . GR
N3 N 0.6366(3) 0.9896(2) 0.24260(14) 0.0496(6) Uani 1 d . . .
N4 N 0.7929(3) 0.7787(2) 0.26332(13) 0.0523(7) Uani 1 d . . .
H4A H 0.8357 0.7119 0.2976 0.063 Uiso 1 calc . . R
C17 C 0.7127(4) 0.8829(3) 0.29128(16) 0.0436(7) Uani 1 d . . .
C18 C 0.7076(4) 0.8772(3) 0.37229(16) 0.0415(6) Uani 1 d . . .
C19 C 0.6302(4) 0.9854(3) 0.39774(17) 0.0488(7) Uani 1 d . . .
H19 H 0.6272 0.9840 0.4500 0.059 Uiso 1 calc . . R
C20 C 0.5563(4) 1.0966(3) 0.34703(19) 0.0562(8) Uani 1 d . . .
H20 H 0.5055 1.1712 0.3636 0.067 Uiso 1 calc . . R
C21 C 0.5613(4) 1.0919(3) 0.27094(18) 0.0540(8) Uani 1 d . . .
H21 H 0.5084 1.1655 0.2366 0.065 Uiso 1 calc . . R
C22 C 0.7806(4) 0.7572(3) 0.42794(17) 0.0486(7) Uani 1 d . . .
C23 C 0.8166(4) 0.7632(3) 0.18684(17) 0.0474(7) Uani 1 d . . .
C24 C 0.8557(4) 0.8613(3) 0.12419(18) 0.0563(8) Uani 1 d . . .
H24 H 0.8655 0.9423 0.1316 0.068 Uiso 1 calc . . R
C25 C 0.8807(5) 0.8395(4) 0.04990(19) 0.0663(10) Uani 1 d . . .
H25 H 0.9037 0.9073 0.0082 0.080 Uiso 1 calc . . R
C26 C 0.8723(4) 0.7226(4) 0.03693(19) 0.0632(9) Uani 1 d . . .
H26 H 0.8909 0.7100 -0.0131 0.076 Uiso 1 calc . . R
C27 C 0.8347(4) 0.6183(3) 0.10019(18) 0.0530(8) Uani 1 d . . .
C28 C 0.8231(4) 0.4953(4) 0.0882(2) 0.0643(10) Uani 1 d . . .
H28 H 0.8435 0.4817 0.0385 0.077 Uiso 1 calc . . R
C29 C 0.7829(5) 0.3968(4) 0.1477(2) 0.0676(10) Uani 1 d . . .
H29 H 0.7768 0.3162 0.1387 0.081 Uiso 1 calc . . R
C30 C 0.7506(4) 0.4162(3) 0.2229(2) 0.0616(9) Uani 1 d . . .
H30 H 0.7215 0.3485 0.2636 0.074 Uiso 1 calc . . R
C31 C 0.7615(4) 0.5331(3) 0.23670(18) 0.0522(8) Uani 1 d . . .
H31 H 0.7400 0.5443 0.2869 0.063 Uiso 1 calc . . R
C32 C 0.8049(4) 0.6383(3) 0.17617(17) 0.0469(7) Uani 1 d . . .
O6 O 0.9289(4) 0.5762(2) 0.59643(14) 0.0696(7) Uani 1 d . . .
H6A H 0.8619 0.5448 0.6356 0.104 Uiso 1 d . . G
H6B H 0.9994 0.5147 0.5815 0.104 Uiso 1 d . . G


_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 C6 1.226(3) . ?
O2 C6 1.312(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.333(4) . ?
N2 C1 1.359(3) . ?
N2 C7 1.400(4) . ?
C1 C2 1.416(4) . ?
C2 C3 1.378(4) . ?
C2 C6 1.485(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.371(4) . ?
C7 C8 1.385(4) . ?
C7 C16 1.421(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.350(4) . ?
C10 C11 1.423(4) . ?
C11 C12 1.407(4) . ?
C11 C16 1.416(4) . ?
C12 C13 1.347(5) . ?
C13 C14 1.400(4) . ?
C14 C15 1.359(4) . ?
C15 C16 1.420(4) . ?
O4 C22 1.232(3) . ?
O5 C22 1.308(3) . ?
N3 C17 1.337(4) . ?
N3 C21 1.335(4) . ?
N4 C17 1.358(3) . ?
N4 C23 1.409(4) . ?
C17 C18 1.433(4) . ?
C18 C19 1.366(4) . ?
C18 C22 1.481(4) . ?
C19 C20 1.379(4) . ?
C20 C21 1.372(4) . ?
C23 C24 1.380(4) . ?
C23 C32 1.422(4) . ?
C24 C25 1.395(4) . ?
C25 C26 1.347(4) . ?
C26 C27 1.425(5) . ?
C27 C28 1.411(4) . ?
C27 C32 1.417(4) . ?
C28 C29 1.353(5) . ?
C29 C30 1.402(5) . ?
C30 C31 1.358(4) . ?
C31 C32 1.416(4) . ?

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
C5 N1 C1 118.1(3) . . ?
C1 N2 C7 130.6(3) . . ?
N1 C1 N2 118.3(3) . . ?
N1 C1 C2 121.2(3) . . ?
N2 C1 C2 120.5(3) . . ?
C1 C2 C6 121.9(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C6 119.9(3) . . ?
C2 C3 C4 120.6(3) . . ?
C5 C4 C3 116.9(3) . . ?
N1 C5 C4 124.9(3) . . ?
O1 C6 O2 122.9(3) . . ?
O1 C6 C2 123.5(3) . . ?
O2 C6 C2 113.6(3) . . ?
N2 C7 C16 117.7(3) . . ?
C8 C7 N2 122.9(3) . . ?
C8 C7 C16 119.3(3) . . ?
C7 C8 C9 120.4(3) . . ?
C10 C9 C8 121.9(3) . . ?
C9 C10 C11 119.8(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 C16 119.1(3) . . ?
C16 C11 C10 119.2(3) . . ?
C13 C12 C11 121.7(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 120.3(3) . . ?
C14 C15 C16 121.4(3) . . ?
C11 C16 C7 119.3(3) . . ?
C11 C16 C15 117.6(3) . . ?
C15 C16 C7 123.1(3) . . ?
C21 N3 C17 118.4(3) . . ?
C17 N4 C23 129.9(3) . . ?
N3 C17 N4 119.2(3) . . ?
N3 C17 C18 120.6(3) . . ?
N4 C17 C18 120.1(3) . . ?
C17 C18 C22 121.6(3) . . ?
C19 C18 C17 118.3(3) . . ?
C19 C18 C22 120.2(3) . . ?
C18 C19 C20 120.9(3) . . ?
C21 C20 C19 116.9(3) . . ?
N3 C21 C20 124.9(3) . . ?
O4 C22 O5 122.5(3) . . ?
O4 C22 C18 123.7(3) . . ?
O5 C22 C18 113.8(3) . . ?
N4 C23 C32 116.8(3) . . ?
C24 C23 N4 123.0(3) . . ?
C24 C23 C32 120.1(3) . . ?
C23 C24 C25 120.4(3) . . ?
C26 C25 C24 121.7(3) . . ?
C25 C26 C27 119.7(3) . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 C32 119.1(3) . . ?
C32 C27 C26 120.0(3) . . ?
C29 C28 C27 121.2(3) . . ?
C28 C29 C30 120.0(3) . . ?
C31 C30 C29 120.4(3) . . ?
C30 C31 C32 121.4(3) . . ?
C27 C32 C23 118.2(3) . . ?
C31 C32 C23 124.0(3) . . ?
C31 C32 C27 117.8(3) . . ?

_olex2_date_sample_data_collection 2020-10-27
_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 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.735
####################################################################### 
# 
# 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_taoya-6-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2193489'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2021-07-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_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 0.0181 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.81390(10)
_cell_length_b                   24.3841(5)
_cell_length_c                   7.44210(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.896(2)
_cell_angle_gamma                90
_cell_volume                     1233.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    300.42(10)
_cell_measurement_theta_max      77.0590
_cell_measurement_theta_min      6.2330
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8468
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.359
_diffrn_reflns_theta_min         6.231
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.42(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     99.00 170.00   0.50    0.05    --  107.75  57.00 -30.00  142
  2  ω    115.00 175.00   0.50    0.05    --  107.75  57.00  30.00  120
  3  ω     96.00 158.00   0.50    0.05    --  107.75  37.00  30.00  124
  4  ω     30.00  55.00   0.50    0.05    --   47.57-121.00 -37.00   50
  5  ω     72.00  97.00   0.50    0.05    --  107.75-121.00 -37.00   50
  6  ω     52.00  78.00   0.50    0.05    --  107.75 -99.00   0.00   52
  7  ω     46.00  71.00   0.50    0.05    --   47.57-151.00 161.00   50
  8  ω     58.00  83.00   0.50    0.05    --  107.75-151.00 161.00   50
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  30.00   50
 10  ω    -26.00  23.00   0.50    0.05    --   47.57 -19.00 120.00   98
 11  ω    -25.00  18.00   0.50    0.05    --   47.57 -19.00  60.00   86
 12  ω    -22.00  22.00   0.50    0.05    --   47.57 -19.00-180.00   88
 13  ω     82.00 144.00   0.50    0.05    --  107.75 121.00  44.00  124
 14  ω     62.00  92.00   0.50    0.05    --   47.57 151.00-154.00   60
 15  ω    101.00 126.00   0.50    0.05    --  107.75 151.00-154.00   50
 16  ω   -107.00 -82.00   0.50    0.05    -- -100.00 151.00-154.00   50
 17  ω   -119.00 -53.00   0.50    0.05    -- -100.00 135.00 -30.11  132
 18  ω    -83.00 -56.00   0.50    0.05    --  -47.57 121.00  44.00   54
 19  ω   -103.00 -51.00   0.50    0.05    -- -100.00 121.00  44.00  104
 20  ω   -109.00 -27.00   0.50    0.05    -- -100.00  77.00  60.00  164
 21  ω    -68.00 -39.00   0.50    0.05    -- -100.00  57.00   0.00   58
 22  ω    -59.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   62
 23  ω    -29.00   0.00   0.50    0.05    --  -47.57  19.00-180.00   58
 24  ω    -68.00 -38.00   0.50    0.05    -- -100.00  57.00-120.00   60
 25  ω   -129.00-104.00   0.50    0.05    -- -100.00-121.00 -37.00   50
 26  ω    -96.00 -68.00   0.50    0.05    --  -47.57-151.00 161.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147199000
_diffrn_orient_matrix_UB_12      -0.0626892000
_diffrn_orient_matrix_UB_13      0.0228213000
_diffrn_orient_matrix_UB_21      0.1084031000
_diffrn_orient_matrix_UB_22      -0.0039399000
_diffrn_orient_matrix_UB_23      -0.1745572000
_diffrn_orient_matrix_UB_31      0.1984694000
_diffrn_orient_matrix_UB_32      0.0067765000
_diffrn_orient_matrix_UB_33      0.1098182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2136
_reflns_number_total             2458
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+0.1114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.18306(12) 0.46528(4) 0.59604(13) 0.0567(3) Uani 1 1 d . . . . .
O2 O 0.15408(12) 0.55631(4) 0.58999(14) 0.0602(3) Uani 1 1 d . . . . .
H2 H 0.050236 0.548645 0.533430 0.090 Uiso 1 1 calc GR . . . .
N1 N 0.75814(14) 0.48609(4) 0.85159(14) 0.0484(3) Uani 1 1 d . . . . .
N2 N 0.52582(14) 0.42364(4) 0.73290(14) 0.0477(3) Uani 1 1 d . . . . .
H2A H 0.410474 0.420272 0.679566 0.057 Uiso 1 1 calc R . . . .
C1 C 0.57922(16) 0.47644(4) 0.77040(14) 0.0405(3) Uani 1 1 d . . . . .
C2 C 0.44694(16) 0.52019(5) 0.72223(15) 0.0426(3) Uani 1 1 d . . . . .
C3 C 0.50849(19) 0.57320(5) 0.76162(19) 0.0545(3) Uani 1 1 d . . . . .
H3 H 0.425311 0.602563 0.732246 0.065 Uiso 1 1 calc R . . . .
C4 C 0.69239(19) 0.58262(5) 0.8441(2) 0.0621(4) Uani 1 1 d . . . . .
H4 H 0.735961 0.618025 0.870797 0.074 Uiso 1 1 calc R . . . .
C5 C 0.80936(18) 0.53782(5) 0.88570(18) 0.0549(3) Uani 1 1 d . . . . .
H5 H 0.933400 0.544193 0.941796 0.066 Uiso 1 1 calc R . . . .
C6 C 0.25097(16) 0.51107(5) 0.63210(16) 0.0454(3) Uani 1 1 d . . . . .
C7 C 0.62449(17) 0.37363(4) 0.76531(15) 0.0437(3) Uani 1 1 d . . . . .
C8 C 0.51037(18) 0.32655(5) 0.73492(16) 0.0481(3) Uani 1 1 d . . . . .
H8 H 0.378189 0.330415 0.697098 0.058 Uiso 1 1 calc R . . . .
C9 C 0.58734(19) 0.27423(5) 0.75918(16) 0.0502(3) Uani 1 1 d . . . . .
C10 C 0.7853(2) 0.26780(5) 0.81701(16) 0.0509(3) Uani 1 1 d . . . . .
C11 C 0.89715(19) 0.31488(5) 0.84499(17) 0.0546(3) Uani 1 1 d . . . . .
H11 H 1.029420 0.311088 0.882609 0.065 Uiso 1 1 calc R . . . .
C12 C 0.82181(18) 0.36740(5) 0.81973(17) 0.0520(3) Uani 1 1 d . . . . .
H12 H 0.902394 0.397912 0.838992 0.062 Uiso 1 1 calc R . . . .
C13 C 0.4553(2) 0.22520(6) 0.7236(2) 0.0672(4) Uani 1 1 d . . . . .
H13A H 0.508333 0.202390 0.633615 0.101 Uiso 1 1 calc GR . . . .
H13B H 0.326253 0.237414 0.681787 0.101 Uiso 1 1 calc GR . . . .
H13C H 0.447312 0.204615 0.832829 0.101 Uiso 1 1 calc GR . . . .
C14 C 0.8761(2) 0.21163(5) 0.8460(2) 0.0667(4) Uani 1 1 d . . . . .
H14A H 0.805275 0.191747 0.932213 0.100 Uiso 1 1 calc GR . . . .
H14B H 1.011043 0.215473 0.890247 0.100 Uiso 1 1 calc GR . . . .
H14C H 0.869596 0.191998 0.733927 0.100 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2312(14) . ?
O2 C6 1.3127(13) . ?
N1 C1 1.3441(14) . ?
N1 C5 1.3285(15) . ?
N2 C1 1.3616(14) . ?
N2 C7 1.4054(14) . ?
C1 C2 1.4267(15) . ?
C2 C3 1.3841(16) . ?
C2 C6 1.4699(15) . ?
C3 C4 1.3767(18) . ?
C4 C5 1.3751(17) . ?
C7 C8 1.3964(15) . ?
C7 C12 1.3859(17) . ?
C8 C9 1.3864(16) . ?
C9 C10 1.3967(19) . ?
C9 C13 1.5087(18) . ?
C10 C11 1.3858(18) . ?
C10 C14 1.5124(16) . ?
C11 C12 1.3877(16) . ?

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
C5 N1 C1 118.08(10) . . ?
C1 N2 C7 131.85(9) . . ?
N1 C1 N2 118.65(9) . . ?
N1 C1 C2 121.35(10) . . ?
N2 C1 C2 120.01(10) . . ?
C1 C2 C6 122.71(10) . . ?
C3 C2 C1 117.90(10) . . ?
C3 C2 C6 119.39(10) . . ?
C4 C3 C2 120.25(11) . . ?
C5 C4 C3 117.64(11) . . ?
N1 C5 C4 124.79(11) . . ?
O1 C6 O2 122.32(10) . . ?
O1 C6 C2 123.57(10) . . ?
O2 C6 C2 114.10(10) . . ?
C8 C7 N2 115.53(10) . . ?
C12 C7 N2 126.05(10) . . ?
C12 C7 C8 118.40(10) . . ?
C9 C8 C7 122.27(11) . . ?
C8 C9 C10 119.49(11) . . ?
C8 C9 C13 119.37(12) . . ?
C10 C9 C13 121.14(12) . . ?
C9 C10 C14 121.51(12) . . ?
C11 C10 C9 117.59(11) . . ?
C11 C10 C14 120.89(12) . . ?
C10 C11 C12 123.33(12) . . ?
C7 C12 C11 118.90(11) . . ?

_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 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.698
####################################################################### 
# 
# 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_taoyang_4
_database_code_depnum_ccdc_archive 'CCDC 2193484'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: https://xray.uky.edu/Resources/scripts/ciffix 
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28

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           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                   19.3362(12)
_cell_length_b                   10.0456(6)
_cell_length_c                   14.1500(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.503(6)
_cell_angle_gamma                90
_cell_volume                     2621.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1808
_cell_measurement_theta_min      8.8150
_cell_measurement_theta_max      69.9100

_exptl_crystal_description       slab
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.733
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_T_max  0.000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
The crystals underwent a destructive phase transition when cooled to 90K. 
Visual inspection of crystal integrity and diffraction quality vs temperature 
established a safe temperature for data collection of 0° C. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            4848
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.796
_diffrn_reflns_theta_max         69.725
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.997

_reflns_number_total             2441
_reflns_number_gt                1899
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.4678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     278
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.005
_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 0.1444(1) 0.37441(14) 0.14623(9) 0.0900(5) Uani 1 1 d . . . . .
O2 O 0.17758(8) 0.56597(13) 0.09803(8) 0.0759(4) Uani 1 1 d . . . . .
H2A H 0.1680(12) 0.5210(15) 0.0376(17) 0.114 Uiso 1 1 calc R U . . .
N2 N 0.15040(7) 0.55193(15) 0.41997(9) 0.0587(4) Uani 1 1 d . . . . .
C11 C 0.14553(8) 0.49007(17) 0.33373(10) 0.0547(4) Uani 1 1 d . . . . .
C12 C 0.16491(9) 0.68180(19) 0.42790(11) 0.0630(4) Uani 1 1 d . . . . .
H12 H 0.166895 0.723600 0.487300 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1771(1) 0.75772(19) 0.35392(12) 0.0692(5) Uani 1 1 d . . . . .
H13 H 0.186025 0.848628 0.362022 0.083 Uiso 1 1 calc R U . . .
C14 C 0.17559(9) 0.69346(19) 0.26652(11) 0.0635(4) Uani 1 1 d . . . . .
H14 H 0.185029 0.741327 0.215504 0.076 Uiso 1 1 calc R U . . .
C15 C 0.16036(8) 0.56038(17) 0.25461(10) 0.0538(4) Uani 1 1 d . . . . .
C16 C 0.15952(9) 0.49077(18) 0.16191(11) 0.0590(4) Uani 1 1 d . . . . .
N1 N 0.1245(4) 0.3606(9) 0.3228(4) 0.0696(13) Uani 0.779(3) 1 d D . P A 1
H1 H 0.125126 0.318398 0.270146 0.084 Uiso 0.779(3) 1 calc R U P A 1
C1 C 0.1016(3) 0.2931(5) 0.3967(4) 0.0615(9) Uani 0.779(3) 1 d D . P A 1
C2 C 0.13953(16) 0.1884(3) 0.44532(18) 0.0600(6) Uani 0.779(3) 1 d D . P A 1
H2 H 0.180825 0.159987 0.430391 0.072 Uiso 0.779(3) 1 calc R U P A 1
C3 C 0.11680(17) 0.1206(3) 0.5196(2) 0.0561(8) Uani 0.779(3) 1 d D . P A 1
C4 C 0.15595(15) 0.0133(3) 0.57463(19) 0.0683(7) Uani 0.779(3) 1 d D . P A 1
H4 H 0.197038 -0.018049 0.560588 0.082 Uiso 0.779(3) 1 calc R U P A 1
C5 C 0.13458(19) -0.0450(3) 0.6478(3) 0.0740(8) Uani 0.779(3) 1 d D . P A 1
H5 H 0.161494 -0.115032 0.683704 0.089 Uiso 0.779(3) 1 calc R U P A 1
C6 C 0.0729(3) -0.0011(6) 0.6699(4) 0.0714(10) Uani 0.779(3) 1 d D . P A 1
H6 H 0.058845 -0.041598 0.720267 0.086 Uiso 0.779(3) 1 calc R U P A 1
C7 C 0.03345(17) 0.1008(3) 0.6175(2) 0.0687(7) Uani 0.779(3) 1 d D . P A 1
H7 H -0.007908 0.128966 0.632428 0.082 Uiso 0.779(3) 1 calc R U P A 1
C8 C 0.0536(3) 0.1657(5) 0.5407(4) 0.0572(10) Uani 0.779(3) 1 d D . P A 1
C9 C 0.01559(12) 0.2745(3) 0.48748(17) 0.0683(7) Uani 0.779(3) 1 d D . P A 1
H9 H -0.025959 0.304617 0.500906 0.082 Uiso 0.779(3) 1 calc R U P A 1
C10 C 0.03796(15) 0.3363(3) 0.41725(18) 0.0699(7) Uani 0.779(3) 1 d D . P A 1
H10 H 0.011533 0.407482 0.382280 0.084 Uiso 0.779(3) 1 calc R U P A 1
N1' N 0.1377(19) 0.359(3) 0.3369(19) 0.0696(13) Uani 0.221(3) 1 d D . P A 2
H1' H 0.142220 0.322340 0.284298 0.084 Uiso 0.221(3) 1 calc R U P A 2
C1' C 0.1238(9) 0.2615(17) 0.4028(13) 0.058(3) Uani 0.221(3) 1 d D . P A 2
C2' C 0.0692(5) 0.2732(9) 0.4427(6) 0.059(2) Uani 0.221(3) 1 d D . P A 2
H2' H 0.033717 0.337544 0.418670 0.071 Uiso 0.221(3) 1 calc R U P A 2
C3' C 0.0651(10) 0.1876(19) 0.5223(16) 0.056(3) Uani 0.221(3) 1 d D . P A 2
C4' C 0.0084(5) 0.2022(10) 0.5653(6) 0.074(3) Uani 0.221(3) 1 d D . P A 2
H4' H -0.026004 0.268840 0.543092 0.089 Uiso 0.221(3) 1 calc R U P A 2
C5' C 0.0041(6) 0.1189(13) 0.6392(9) 0.086(3) Uani 0.221(3) 1 d D . P A 2
H5' H -0.031668 0.130939 0.670010 0.103 Uiso 0.221(3) 1 calc R U P A 2
C6' C 0.0534(14) 0.017(3) 0.668(2) 0.095(6) Uani 0.221(3) 1 d D . P A 2
H6' H 0.049648 -0.041037 0.717498 0.114 Uiso 0.221(3) 1 calc R U P A 2
C7' C 0.1064(7) -0.0023(12) 0.6269(8) 0.074(3) Uani 0.221(3) 1 d D . P A 2
H7' H 0.137610 -0.074098 0.647579 0.089 Uiso 0.221(3) 1 calc R U P A 2
C8' C 0.1166(6) 0.0844(12) 0.5521(7) 0.056(3) Uani 0.221(3) 1 d D . P A 2
C9' C 0.1705(4) 0.0705(8) 0.5054(6) 0.066(2) Uani 0.221(3) 1 d D . P A 2
H9' H 0.203039 0.000011 0.523362 0.079 Uiso 0.221(3) 1 calc R U P A 2
C10' C 0.1767(6) 0.1567(9) 0.4347(6) 0.070(2) Uani 0.221(3) 1 d D . P A 2
H10' H 0.214526 0.148402 0.407189 0.084 Uiso 0.221(3) 1 calc R U P A 2


_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 C16 1.209(2) . ?
O2 C16 1.3037(19) . ?
O2 H2A 0.93(2) . ?
N2 C12 1.332(2) . ?
N2 C11 1.3473(18) . ?
C11 N1' 1.33(3) . ?
C11 N1 1.358(8) . ?
C11 C15 1.424(2) . ?
C12 C13 1.372(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.482(2) . ?
N1 C1 1.425(5) . ?
N1 H1 0.8600 . ?
C1 C2 1.348(4) . ?
C1 C10 1.414(4) . ?
C2 C3 1.427(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(4) . ?
C3 C8 1.417(4) . ?
C4 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.357(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(4) . ?
C9 C10 1.349(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N1' C1' 1.434(15) . ?
N1' H1' 0.8600 . ?
C1' C2' 1.343(12) . ?
C1' C10' 1.443(12) . ?
C2' C3' 1.438(12) . ?
C2' H2' 0.9300 . ?
C3' C8' 1.411(13) . ?
C3' C4' 1.412(11) . ?
C4' C5' 1.362(11) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.376(16) . ?
C5' H5' 0.9300 . ?
C6' C7' 1.334(15) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.429(12) . ?
C7' H7' 0.9300 . ?
C8' C9' 1.400(11) . ?
C9' C10' 1.355(10) . ?
C9' H9' 0.9300 . ?
C10' H10' 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
C16 O2 H2A 109.5 . . ?
C12 N2 C11 118.92(14) . . ?
N1' C11 N2 113.8(12) . . ?
N2 C11 N1 118.8(3) . . ?
N1' C11 C15 124.8(13) . . ?
N2 C11 C15 120.51(15) . . ?
N1 C11 C15 120.6(3) . . ?
N2 C12 C13 124.09(15) . . ?
N2 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C12 C13 C14 117.33(17) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 H13 121.3 . . ?
C15 C14 C13 120.69(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C11 118.33(13) . . ?
C14 C15 C16 120.96(14) . . ?
C11 C15 C16 120.70(15) . . ?
O1 C16 O2 122.23(14) . . ?
O1 C16 C15 123.79(14) . . ?
O2 C16 C15 113.98(16) . . ?
C11 N1 C1 121.4(7) . . ?
C11 N1 H1 119.3 . . ?
C1 N1 H1 119.3 . . ?
C2 C1 C10 120.6(3) . . ?
C2 C1 N1 120.3(5) . . ?
C10 C1 N1 119.2(5) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C8 118.8(3) . . ?
C4 C3 C2 122.6(3) . . ?
C8 C3 C2 118.6(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C3 118.8(3) . . ?
C9 C8 C7 123.3(3) . . ?
C3 C8 C7 117.9(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C1 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C1 C10 H10 119.9 . . ?
C11 N1' C1' 138(3) . . ?
C11 N1' H1' 110.8 . . ?
C1' N1' H1' 110.8 . . ?
C2' C1' N1' 122.5(19) . . ?
C2' C1' C10' 120.3(11) . . ?
N1' C1' C10' 116.7(18) . . ?
C1' C2' C3' 120.8(10) . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' H2' 119.6 . . ?
C8' C3' C4' 121.1(9) . . ?
C8' C3' C2' 118.2(10) . . ?
C4' C3' C2' 120.5(10) . . ?
C5' C4' C3' 120.1(9) . . ?
C5' C4' H4' 119.9 . . ?
C3' C4' H4' 119.9 . . ?
C4' C5' C6' 119.2(12) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C7' C6' C5' 122.2(15) . . ?
C7' C6' H6' 118.9 . . ?
C5' C6' H6' 118.9 . . ?
C6' C7' C8' 122.0(12) . . ?
C6' C7' H7' 119.0 . . ?
C8' C7' H7' 119.0 . . ?
C9' C8' C3' 119.4(9) . . ?
C9' C8' C7' 125.2(10) . . ?
C3' C8' C7' 115.3(9) . . ?
C10' C9' C8' 121.9(8) . . ?
C10' C9' H9' 119.1 . . ?
C8' C9' H9' 119.1 . . ?
C9' C10' C1' 119.(1) . . ?
C9' C10' H10' 120.5 . . ?
C1' C10' H10' 120.5 . . ?

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
C12 N2 C11 N1' 174.1(17) . . . . ?
C12 N2 C11 N1 -174.3(4) . . . . ?
C12 N2 C11 C15 4.1(2) . . . . ?
C11 N2 C12 C13 -1.6(3) . . . . ?
N2 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C13 C14 C15 C11 0.5(3) . . . . ?
C13 C14 C15 C16 -179.27(15) . . . . ?
N1' C11 C15 C14 -172.4(18) . . . . ?
N2 C11 C15 C14 -3.6(2) . . . . ?
N1 C11 C15 C14 174.8(5) . . . . ?
N1' C11 C15 C16 7.4(18) . . . . ?
N2 C11 C15 C16 176.20(14) . . . . ?
N1 C11 C15 C16 -5.4(5) . . . . ?
C14 C15 C16 O1 -177.79(18) . . . . ?
C11 C15 C16 O1 2.4(3) . . . . ?
C14 C15 C16 O2 3.0(2) . . . . ?
C11 C15 C16 O2 -176.76(14) . . . . ?
N2 C11 N1 C1 5.6(9) . . . . ?
C15 C11 N1 C1 -172.8(5) . . . . ?
C11 N1 C1 C2 -116.5(8) . . . . ?
C11 N1 C1 C10 64.4(9) . . . . ?
C10 C1 C2 C3 -1.0(7) . . . . ?
N1 C1 C2 C3 179.9(5) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C1 C2 C3 C8 0.1(6) . . . . ?
C8 C3 C4 C5 -1.1(6) . . . . ?
C2 C3 C4 C5 177.0(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C7 0.2(9) . . . . ?
C5 C6 C7 C8 -0.5(9) . . . . ?
C4 C3 C8 C9 178.6(4) . . . . ?
C2 C3 C8 C9 0.4(8) . . . . ?
C4 C3 C8 C7 0.7(7) . . . . ?
C2 C3 C8 C7 -177.4(4) . . . . ?
C6 C7 C8 C9 -177.6(6) . . . . ?
C6 C7 C8 C3 0.1(9) . . . . ?
C3 C8 C9 C10 0.0(8) . . . . ?
C7 C8 C9 C10 177.7(4) . . . . ?
C8 C9 C10 C1 -0.9(6) . . . . ?
C2 C1 C10 C9 1.4(7) . . . . ?
N1 C1 C10 C9 -179.5(5) . . . . ?
N2 C11 N1' C1' 10(5) . . . . ?
C15 C11 N1' C1' 179(3) . . . . ?
C11 N1' C1' C2' 50(5) . . . . ?
C11 N1' C1' C10' -123(4) . . . . ?
N1' C1' C2' C3' -168(2) . . . . ?
C10' C1' C2' C3' 4(3) . . . . ?
C1' C2' C3' C8' -5(3) . . . . ?
C1' C2' C3' C4' 178.7(18) . . . . ?
C8' C3' C4' C5' 2(3) . . . . ?
C2' C3' C4' C5' 178.7(15) . . . . ?
C3' C4' C5' C6' -3(3) . . . . ?
C4' C5' C6' C7' 1(4) . . . . ?
C5' C6' C7' C8' 2(4) . . . . ?
C4' C3' C8' C9' 177.9(16) . . . . ?
C2' C3' C8' C9' 1(3) . . . . ?
C4' C3' C8' C7' 0(3) . . . . ?
C2' C3' C8' C7' -176.0(16) . . . . ?
C6' C7' C8' C9' -180(2) . . . . ?
C6' C7' C8' C3' -2(3) . . . . ?
C3' C8' C9' C10' 3(2) . . . . ?
C7' C8' C9' C10' 179.8(11) . . . . ?
C8' C9' C10' C1' -3.5(17) . . . . ?
C2' C1' C10' C9' 0(2) . . . . ?
N1' C1' C10' C9' 172.7(18) . . . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028



