# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4c
_database_code_depnum_ccdc_archive 'CCDC 2306336'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.325
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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

_symmetry_Int_Tables_number      14
_cell_length_a                   13.9261(3)
_cell_length_b                   7.8917(2)
_cell_length_c                   13.2129(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.325(2)
_cell_angle_gamma                90
_cell_volume                     1436.80(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.8680
_cell_measurement_theta_min      3.1940
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             618.142
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.9973
_diffrn_reflns_Laue_measured_fraction_max 0.9824
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15496
_diffrn_reflns_point_group_measured_fraction_full 0.9973
_diffrn_reflns_point_group_measured_fraction_max 0.9824
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.64
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  89.00   1.00    1.00    --    0.00  37.00-180.00   49
  2  ω    -30.00  25.00   1.00    1.00    --    0.00 -57.00 -60.00   55
  3  ω    -11.00  35.00   1.00    1.00    --    0.00  77.00 -60.00   46
  4  ω    -27.00  22.00   1.00    1.00    --    0.00  37.00-180.00   49
  5  ω     32.00  83.00   1.00    1.00    --    0.00  77.00   0.00   51
  6  ω    -89.00 -44.00   1.00    1.00    --    0.00 -57.00 -60.00   45
  7  ω    107.00 166.00   1.00    1.00    --   92.10  45.00   0.00   59
  8  ω     22.00 118.00   1.00    1.00    --   92.10 -45.00-180.00   96
  9  ω     86.00 112.00   1.00    1.00    --   92.10 -45.00  60.00   26
 10  ω     77.00 103.00   1.00    1.00    --   92.10  45.00-150.00   26
 11  ω     95.00 121.00   1.00    1.00    --   92.10 -82.00 -90.00   26
 12  ω      3.00 118.00   1.00    1.00    --   92.10 -61.00  60.00  115
 13  ω     68.00 181.00   1.00    1.00    --   92.10  30.00 -60.00  113
 14  ω     85.00 127.00   1.00    1.00    --   92.10 -82.00 150.00   42
 15  ω      6.00 128.00   1.00    1.00    --   92.10 -82.00  60.00  122
 16  ω     92.00 118.00   1.00    1.00    --   92.10 -82.00-150.00   26
 17  ω     49.00  86.00   1.00    1.00    --   92.10 -82.00-150.00   37
 18  ω     15.00  41.00   1.00    1.00    --   92.10 -82.00 150.00   26
 19  ω     58.00 104.00   1.00    1.00    --   92.10 -61.00 -60.00   46
 20  ω     26.00 108.00   1.00    1.00    --   92.10 -82.00 -30.00   82
 21  ω      5.00  30.00   1.00    1.00    --   92.10 -82.00-150.00   25
 22  ω    116.00 142.00   1.00    1.00    --   92.10  45.00-150.00   26
 23  ω     23.00  70.00   1.00    1.00    --   92.10 -82.00 -60.00   47
 24  ω      9.00 121.00   1.00    1.00    --   92.10 -30.00 -90.00  112
 25  ω     16.00  57.00   1.00    1.00    --   92.10 -45.00  60.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547170000
_diffrn_orient_matrix_UB_12      -0.0557978000
_diffrn_orient_matrix_UB_13      0.0877133000
_diffrn_orient_matrix_UB_21      0.0251140000
_diffrn_orient_matrix_UB_22      -0.1863528000
_diffrn_orient_matrix_UB_23      -0.0193027000
_diffrn_orient_matrix_UB_31      0.0941906000
_diffrn_orient_matrix_UB_32      0.0171449000
_diffrn_orient_matrix_UB_33      0.0762202000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2463
_reflns_number_total             2845
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1830
_refine_diff_density_min         -0.3225
_refine_diff_density_rms         0.0610
_refine_ls_d_res_high            0.8034
_refine_ls_d_res_low             13.7794
_refine_ls_goodness_of_fit_ref   1.0342
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.0342
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.3328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1049
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.73681(7) 0.50815(11) 0.74643(7) 0.0298(2) Uani 1.000000 .
O002 O 0.58567(7) -0.05152(11) 0.44066(7) 0.0326(2) Uani 1.000000 .
O003 O 0.78298(7) 0.64029(12) 0.60998(7) 0.0356(3) Uani 1.000000 .
N004 N 0.59971(7) 0.23894(13) 0.45509(8) 0.0230(2) Uani 1.000000 .
C005 C 0.64183(9) 0.38304(15) 0.50319(9) 0.0219(3) Uani 1.000000 .
C006 C 0.61036(9) 0.54303(15) 0.45929(9) 0.0240(3) Uani 1.000000 .
C007 C 0.73555(9) 0.20080(15) 0.62883(9) 0.0238(3) Uani 1.000000 .
C008 C 0.74822(9) 0.51935(15) 0.64781(9) 0.0242(3) Uani 1.000000 .
C009 C 0.70934(9) 0.36453(15) 0.59129(9) 0.0227(3) Uani 1.000000 .
C00A C 0.81365(9) 0.17837(15) 0.71708(9) 0.0253(3) Uani 1.000000 .
C00B C 0.54258(10) 0.55364(16) 0.37498(10) 0.0266(3) Uani 1.000000 .
C00C C 0.62394(9) 0.06882(15) 0.49096(10) 0.0255(3) Uani 1.000000 .
C00D C 0.69310(10) 0.05999(16) 0.57982(10) 0.0274(3) Uani 1.000000 .
C00E C 0.50167(10) 0.40317(17) 0.32797(10) 0.0293(3) Uani 1.000000 .
C00F C 0.53009(10) 0.25161(17) 0.36914(10) 0.0274(3) Uani 1.000000 .
C00G C 0.79528(10) 0.09390(17) 0.80455(10) 0.0301(3) Uani 1.000000 .
C00H C 0.90630(10) 0.24232(18) 0.71310(11) 0.0330(3) Uani 1.000000 .
C00I C 0.86829(11) 0.07427(19) 0.88733(11) 0.0367(3) Uani 1.000000 .
C00J C 0.77384(11) 0.64525(19) 0.81558(11) 0.0357(3) Uani 1.000000 .
C00K C 0.95981(11) 0.13832(19) 0.88241(12) 0.0396(4) Uani 1.000000 .
C00L C 0.97911(11) 0.2214(2) 0.79548(12) 0.0406(4) Uani 1.000000 .
C00M C 0.85219(14) 0.5786(2) 0.89498(13) 0.0472(4) Uani 1.000000 .
H006 H 0.6388(10) 0.6456(19) 0.4909(10) 0.023(3) Uiso 1.000000 .
H00D H 0.7146(11) -0.051(2) 0.6015(12) 0.033(4) Uiso 1.000000 .
H00B H 0.5205(10) 0.667(2) 0.3488(11) 0.030(4) Uiso 1.000000 .
H00F H 0.5057(11) 0.142(2) 0.3433(12) 0.035(4) Uiso 1.000000 .
H00G H 0.7284(12) 0.052(2) 0.8087(13) 0.041(4) Uiso 1.000000 .
H00E H 0.4531(11) 0.4065(19) 0.2664(12) 0.034(4) Uiso 1.000000 .
H00a H 0.7967(13) 0.736(2) 0.7751(13) 0.047(5) Uiso 1.000000 .
H00H H 0.9206(11) 0.303(2) 0.6508(13) 0.041(4) Uiso 1.000000 .
H00c H 0.7158(13) 0.682(2) 0.8466(13) 0.047(5) Uiso 1.000000 .
H00K H 1.0104(14) 0.126(2) 0.9396(14) 0.051(5) Uiso 1.000000 .
H00I H 0.8543(12) 0.014(2) 0.9496(14) 0.046(5) Uiso 1.000000 .
H00j H 0.8701(14) 0.665(3) 0.9511(15) 0.056(5) Uiso 1.000000 .
H00L H 1.0416(14) 0.273(2) 0.7920(13) 0.050(5) Uiso 1.000000 .
H00m H 0.8280(15) 0.475(3) 0.9281(16) 0.063(6) Uiso 1.000000 .
H00n H 0.9119(17) 0.550(3) 0.8654(17) 0.072(7) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.3382(15) . ?
O001 C00J 1.4612(15) . ?
O002 C00C 1.2350(15) . ?
O003 C008 1.2105(15) . ?
N004 C005 1.3904(15) . ?
N004 C00C 1.4473(15) . ?
N004 C00F 1.3860(16) . ?
C005 C006 1.4315(16) . ?
C005 C009 1.3940(17) . ?
C006 C00B 1.3545(18) . ?
C006 H006 0.969(15) . ?
C007 C009 1.4129(16) . ?
C007 C00A 1.4855(17) . ?
C007 C00D 1.3758(18) . ?
C008 C009 1.4922(16) . ?
C00A C00G 1.3897(18) . ?
C00A C00H 1.3935(19) . ?
C00B C00E 1.4205(18) . ?
C00B H00B 0.988(16) . ?
C00C C00D 1.4084(18) . ?
C00D H00D 0.954(16) . ?
C00E C00F 1.3494(19) . ?
C00E H00E 0.980(16) . ?
C00F H00F 0.971(17) . ?
C00G C00I 1.3899(19) . ?
C00G H00G 0.998(17) . ?
C00H C00L 1.386(2) . ?
C00H H00H 0.998(17) . ?
C00I C00K 1.381(2) . ?
C00I H00I 0.994(18) . ?
C00J C00M 1.495(2) . ?
C00J H00a 0.976(18) . ?
C00J H00c 0.999(18) . ?
C00K C00L 1.382(2) . ?
C00K H00K 0.960(19) . ?
C00L H00L 0.968(19) . ?
C00M H00j 1.01(2) . ?
C00M H00m 1.01(2) . ?
C00M H00n 0.99(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J O001 C008 118.62(10) . . ?
C00C N004 C005 123.10(10) . . ?
C00F N004 C005 120.95(10) . . ?
C00F N004 C00C 115.94(10) . . ?
C006 C005 N004 116.87(11) . . ?
C009 C005 N004 119.00(10) . . ?
C009 C005 C006 124.11(11) . . ?
C00B C006 C005 121.59(11) . . ?
H006 C006 C005 118.7(8) . . ?
H006 C006 C00B 119.7(8) . . ?
C00A C007 C009 120.47(11) . . ?
C00D C007 C009 120.13(11) . . ?
C00D C007 C00A 119.28(11) . . ?
O003 C008 O001 124.41(11) . . ?
C009 C008 O001 110.34(10) . . ?
C009 C008 O003 125.22(12) . . ?
C007 C009 C005 119.84(11) . . ?
C008 C009 C005 118.95(10) . . ?
C008 C009 C007 121.10(11) . . ?
C00G C00A C007 120.53(12) . . ?
C00H C00A C007 120.26(11) . . ?
C00H C00A C00G 119.21(12) . . ?
C00E C00B C006 119.70(11) . . ?
H00B C00B C006 119.2(9) . . ?
H00B C00B C00E 121.0(9) . . ?
N004 C00C O002 118.37(11) . . ?
C00D C00C O002 126.89(12) . . ?
C00D C00C N004 114.69(10) . . ?
C00C C00D C007 123.21(11) . . ?
H00D C00D C007 120.2(9) . . ?
H00D C00D C00C 116.3(9) . . ?
C00F C00E C00B 119.28(12) . . ?
H00E C00E C00B 121.7(9) . . ?
H00E C00E C00F 119.0(9) . . ?
C00E C00F N004 121.59(12) . . ?
H00F C00F N004 113.1(9) . . ?
H00F C00F C00E 125.3(9) . . ?
C00I C00G C00A 120.41(13) . . ?
H00G C00G C00A 119.4(10) . . ?
H00G C00G C00I 120.2(10) . . ?
C00L C00H C00A 120.23(13) . . ?
H00H C00H C00A 120.1(9) . . ?
H00H C00H C00L 119.6(9) . . ?
C00K C00I C00G 119.80(14) . . ?
H00I C00I C00G 119.7(10) . . ?
H00I C00I C00K 120.5(10) . . ?
C00M C00J O001 109.51(12) . . ?
H00a C00J O001 108.4(10) . . ?
H00a C00J C00M 112.3(10) . . ?
H00c C00J O001 103.6(10) . . ?
H00c C00J C00M 111.4(10) . . ?
H00c C00J H00a 111.2(15) . . ?
C00L C00K C00I 120.29(13) . . ?
H00K C00K C00I 120.2(11) . . ?
H00K C00K C00L 119.5(11) . . ?
C00K C00L C00H 120.06(14) . . ?
H00L C00L C00H 118.2(11) . . ?
H00L C00L C00K 121.6(11) . . ?
H00j C00M C00J 110.9(11) . . ?
H00m C00M C00J 109.5(12) . . ?
H00m C00M H00j 106.8(16) . . ?
H00n C00M C00J 111.8(13) . . ?
H00n C00M H00j 108.1(17) . . ?
H00n C00M H00m 109.7(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C008 C009 C005 126.75(10) . . . . ?
O001 C008 C009 C007 -49.56(12) . . . . ?
O002 C00C N004 C005 -177.00(11) . . . . ?
O002 C00C N004 C00F 3.70(14) . . . . ?
O002 C00C C00D C007 176.95(14) . . . . ?
O003 C008 C009 C005 -51.51(14) . . . . ?
O003 C008 C009 C007 132.18(13) . . . . ?
N004 C005 C006 C00B 0.14(13) . . . . ?
N004 C005 C009 C007 1.48(13) . . . . ?
N004 C005 C009 C008 -174.88(11) . . . . ?
N004 C00C C00D C007 -0.61(14) . . . . ?
N004 C00F C00E C00B -1.30(15) . . . . ?
C005 C006 C00B C00E -0.39(14) . . . . ?
C005 C009 C007 C00A 174.54(11) . . . . ?
C005 C009 C007 C00D -1.33(14) . . . . ?
C006 C00B C00E C00F 0.97(15) . . . . ?
C007 C00A C00G C00I -179.48(12) . . . . ?
C007 C00A C00H C00L 179.97(13) . . . . ?
C00A C00G C00I C00K -0.35(16) . . . . ?
C00A C00H C00L C00K -0.62(16) . . . . ?
C00G C00I C00K C00L -0.15(17) . . . . ?
C00H C00L C00K C00I 0.64(18) . . . . ?


_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 2.603
_oxdiff_exptl_absorpt_empirical_full_min 0.557
_chemical_name_systematic        
'Ethyl 4-oxo-2-phenyl-4H-quinolizine-1-carboxylate'
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 2306339'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C14 H12 O3'
_chemical_formula_sum            'C14 H12 O3'
_chemical_formula_weight         228.249
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.7106(2)
_cell_length_b                   7.7880(1)
_cell_length_c                   15.1238(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.369(2)
_cell_angle_gamma                90
_cell_volume                     1117.21(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6024
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.1660
_cell_measurement_theta_min      4.9560
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.27
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             481.705
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9822
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11073
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9822
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.64
_diffrn_reflns_theta_min         4.97
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9822
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -30.00   1.00    1.00    --    0.00 -82.00-150.00   55
  2  ω     12.00  48.00   1.00    1.00    --    0.00  57.00 -60.00   36
  3  ω     52.00  88.00   1.00    1.00    --    0.00  57.00 -60.00   36
  4  ω     24.00  79.00   1.00    1.00    --    0.00  57.00 150.00   55
  5  ω    -13.00  15.00   1.00    1.00    --    0.00 -82.00-150.00   28
  6  ω    -27.00   3.00   1.00    1.00    --    0.00  57.00 150.00   30
  7  ω      3.00 128.00   1.00    1.00    --   92.10 -82.00-120.00  125
  8  ω      6.00 120.00   1.00    1.00    --   92.10 -61.00  30.00  114
  9  ω     80.00 128.00   1.00    1.00    --   92.10 -82.00  30.00   48
 10  ω     86.00 112.00   1.00    1.00    --   92.10 -45.00-120.00   26
 11  ω     75.00 103.00   1.00    1.00    --   92.10 -82.00 120.00   28
 12  ω     37.00  63.00   1.00    1.00    --   92.10 -45.00-120.00   26
 13  ω      9.00  65.00   1.00    1.00    --   92.10 -30.00  90.00   56
 14  ω     96.00 121.00   1.00    1.00    --   92.10 -30.00  90.00   25
 15  ω    113.00 148.00   1.00    1.00    --   92.10  30.00   0.00   35
 16  ω     68.00 117.00   1.00    1.00    --   92.10 -30.00 -30.00   49
 17  ω      5.00  34.00   1.00    1.00    --   92.10 -30.00 -30.00   29
 18  ω      6.00  71.00   1.00    1.00    --   92.10 -61.00-180.00   65
 19  ω     29.00  95.00   1.00    1.00    --   92.10 -82.00-180.00   66
 20  ω      4.00 120.00   1.00    1.00    --   92.10 -61.00-120.00  116
 21  ω     74.00 107.00   1.00    1.00    --   92.10 -82.00 -30.00   33
 22  ω      4.00  29.00   1.00    1.00    --   92.10 -82.00 120.00   25
 23  ω     10.00  73.00   1.00    1.00    --   92.10 -82.00  30.00   63
 24  ω     92.00 180.00   1.00    1.00    --   92.10  30.00 -60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1236766000
_diffrn_orient_matrix_UB_12      -0.1256327000
_diffrn_orient_matrix_UB_13      -0.0041968000
_diffrn_orient_matrix_UB_21      -0.0796787000
_diffrn_orient_matrix_UB_22      0.1369792000
_diffrn_orient_matrix_UB_23      0.0428700000
_diffrn_orient_matrix_UB_31      -0.0688293000
_diffrn_orient_matrix_UB_32      0.0671863000
_diffrn_orient_matrix_UB_33      -0.0950905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -8
_reflns_number_gt                1990
_reflns_number_total             2213
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1742
_refine_diff_density_min         -0.3011
_refine_diff_density_rms         0.0499
_refine_ls_d_res_high            0.8035
_refine_ls_d_res_low             8.8947
_refine_ls_goodness_of_fit_ref   1.1532
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.1532
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1386
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.86667(9) 0.48368(11) 0.35922(6) 0.0303(3) Uani 1.000000 .
O002 O 0.73518(10) 0.93581(11) 0.52072(6) 0.0364(3) Uani 1.000000 .
O003 O 0.82179(11) 0.75246(12) 0.31628(7) 0.0407(3) Uani 1.000000 .
C004 C 0.75243(11) 0.66688(14) 0.45053(7) 0.0246(3) Uani 1.000000 .
C005 C 0.75859(11) 0.53804(14) 0.51258(8) 0.0243(3) Uani 1.000000 .
C006 C 0.56939(12) 0.62896(14) 0.59402(8) 0.0258(3) Uani 1.000000 .
C007 C 0.70020(12) 0.55199(14) 0.59521(8) 0.0245(3) Uani 1.000000 .
C008 C 0.81258(12) 0.64392(15) 0.37152(8) 0.0278(3) Uani 1.000000 .
C009 C 0.51626(13) 0.63649(14) 0.67200(8) 0.0285(3) Uani 1.000000 .
C00A C 0.86857(12) 0.35333(15) 0.41952(8) 0.0280(3) Uani 1.000000 .
C00B C 0.81983(12) 0.37676(15) 0.49548(8) 0.0270(3) Uani 1.000000 .
C00C C 0.77482(13) 0.48066(15) 0.67632(8) 0.0290(3) Uani 1.000000 .
C00D C 0.68881(12) 0.84176(15) 0.45762(8) 0.0279(3) Uani 1.000000 .
C00E C 0.72106(14) 0.48823(16) 0.75436(9) 0.0326(3) Uani 1.000000 .
C00F C 0.59207(13) 0.56698(15) 0.75202(8) 0.0297(3) Uani 1.000000 .
C00G C 0.92493(14) 0.19240(19) 0.38873(10) 0.0366(3) Uani 1.000000 .
C00H C 0.56580(17) 0.8904(2) 0.38363(11) 0.0439(4) Uani 1.000000 .
H006 H 0.5118(15) 0.673(2) 0.5360(10) 0.031(3) Uiso 1.000000 .
H009 H 0.4234(16) 0.691(2) 0.6696(10) 0.030(3) Uiso 1.000000 .
H00C H 0.8677(17) 0.421(2) 0.6785(11) 0.037(4) Uiso 1.000000 .
H00B H 0.8184(16) 0.280(2) 0.5390(10) 0.034(4) Uiso 1.000000 .
H00E H 0.774(2) 0.435(2) 0.8109(13) 0.053(5) Uiso 1.000000 .
H00F H 0.5532(18) 0.578(2) 0.8063(12) 0.041(4) Uiso 1.000000 .
H00a H 0.863(2) 0.148(3) 0.3293(13) 0.058(5) Uiso 1.000000 .
H00d H 0.927(2) 0.101(2) 0.4353(15) 0.058(5) Uiso 1.000000 .
H00g H 1.022(2) 0.217(2) 0.3790(12) 0.054(5) Uiso 1.000000 .
H00h H 0.531(3) 0.988(3) 0.4012(16) 0.077(7) Uiso 1.000000 .
H00i H 0.500(2) 0.789(3) 0.3664(14) 0.069(6) Uiso 1.000000 .
H00j H 0.601(4) 0.925(4) 0.329(2) 0.104(9) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.3820(14) . ?
O001 C00A 1.3622(15) . ?
O002 C00D 1.2107(15) . ?
O003 C008 1.2052(15) . ?
C004 C005 1.3664(16) . ?
C004 C008 1.4491(16) . ?
C004 C00D 1.5089(16) . ?
C005 C007 1.4828(16) . ?
C005 C00B 1.4367(16) . ?
C006 C007 1.4013(16) . ?
C006 C009 1.3860(16) . ?
C006 H006 0.994(15) . ?
C007 C00C 1.3991(16) . ?
C009 C00F 1.3849(18) . ?
C009 H009 0.989(15) . ?
C00A C00B 1.3454(17) . ?
C00A C00G 1.4820(17) . ?
C00B H00B 1.003(16) . ?
C00C C00E 1.3904(18) . ?
C00C H00C 1.010(17) . ?
C00D C00H 1.5000(18) . ?
C00E C00F 1.3883(18) . ?
C00E H00E 0.99(2) . ?
C00F H00F 0.978(18) . ?
C00G H00a 1.028(19) . ?
C00G H00d 1.00(2) . ?
C00G H00g 1.01(2) . ?
C00H H00h 0.89(3) . ?
C00H H00i 1.01(2) . ?
C00H H00j 0.99(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
C00A O001 C008 122.27(9) . . ?
C008 C004 C005 120.64(10) . . ?
C00D C004 C005 124.92(10) . . ?
C00D C004 C008 114.42(10) . . ?
C007 C005 C004 123.82(10) . . ?
C00B C005 C004 118.51(11) . . ?
C00B C005 C007 117.61(10) . . ?
C009 C006 C007 120.59(10) . . ?
H006 C006 C007 119.6(9) . . ?
H006 C006 C009 119.7(9) . . ?
C006 C007 C005 121.99(10) . . ?
C00C C007 C005 119.35(10) . . ?
C00C C007 C006 118.62(11) . . ?
O003 C008 O001 116.95(11) . . ?
C004 C008 O001 117.02(10) . . ?
C004 C008 O003 126.02(11) . . ?
C00F C009 C006 120.13(11) . . ?
H009 C009 C006 119.3(8) . . ?
H009 C009 C00F 120.6(8) . . ?
C00B C00A O001 120.92(11) . . ?
C00G C00A O001 111.89(11) . . ?
C00G C00A C00B 127.17(12) . . ?
C00A C00B C005 120.47(11) . . ?
H00B C00B C005 118.3(9) . . ?
H00B C00B C00A 121.0(9) . . ?
C00E C00C C007 120.61(11) . . ?
H00C C00C C007 120.2(9) . . ?
H00C C00C C00E 119.2(9) . . ?
C004 C00D O002 120.88(10) . . ?
C00H C00D O002 122.53(12) . . ?
C00H C00D C004 116.59(11) . . ?
C00F C00E C00C 119.87(12) . . ?
H00E C00E C00C 119.8(12) . . ?
H00E C00E C00F 120.3(11) . . ?
C00E C00F C009 120.18(11) . . ?
H00F C00F C009 118.0(10) . . ?
H00F C00F C00E 121.8(10) . . ?
H00a C00G C00A 111.9(11) . . ?
H00d C00G C00A 109.8(12) . . ?
H00d C00G H00a 107.2(17) . . ?
H00g C00G C00A 107.8(11) . . ?
H00g C00G H00a 109.2(15) . . ?
H00g C00G H00d 111.0(16) . . ?
H00h C00H C00D 106.4(15) . . ?
H00i C00H C00D 110.7(12) . . ?
H00i C00H H00h 119(2) . . ?
H00j C00H C00D 108.8(19) . . ?
H00j C00H H00h 104(2) . . ?
H00j C00H H00i 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C008 C004 C005 4.33(12) . . . . ?
O001 C008 C004 C00D -177.13(10) . . . . ?
O001 C00A C00B C005 2.89(12) . . . . ?
O002 C00D C004 C005 60.64(13) . . . . ?
O002 C00D C004 C008 -117.83(12) . . . . ?
O003 C008 C004 C005 -174.42(12) . . . . ?
O003 C008 C004 C00D 4.12(14) . . . . ?
C004 C005 C007 C006 41.95(13) . . . . ?
C004 C005 C007 C00C -140.55(11) . . . . ?
C004 C005 C00B C00A -0.65(12) . . . . ?
C005 C007 C006 C009 178.52(10) . . . . ?
C005 C007 C00C C00E -178.48(10) . . . . ?
C005 C00B C00A C00G -175.29(10) . . . . ?
C006 C007 C00C C00E -0.89(12) . . . . ?
C006 C009 C00F C00E -0.52(13) . . . . ?
C007 C00C C00E C00F 0.09(14) . . . . ?
C009 C00F C00E C00C 0.62(13) . . . . ?


_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.556
_chemical_name_systematic        5-Acetyl-6-methyl-4-phenyl-2H-pyran-2-one
####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 2306340'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C24 H16 O3'
_chemical_formula_sum            'C24 H16 O3'
_chemical_formula_weight         352.393
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   10.0411(2)
_cell_length_b                   16.9542(3)
_cell_length_c                   10.2605(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.799(2)
_cell_angle_gamma                90
_cell_volume                     1746.57(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8479
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.1710
_cell_measurement_theta_min      5.0200
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             738.473
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.9991
_diffrn_reflns_Laue_measured_fraction_max 0.9991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19280
_diffrn_reflns_point_group_measured_fraction_full 0.9308
_diffrn_reflns_point_group_measured_fraction_max 0.9308
_diffrn_reflns_theta_full        67.0802
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.31
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -11.00   1.00    1.00    --    0.00 -57.00 150.00   45
  2  ω    -20.00   9.00   1.00    1.00    --    0.00 -37.00-150.00   29
  3  ω     54.00  89.00   1.00    1.00    --    0.00  57.00 150.00   35
  4  ω     -6.00  27.00   1.00    1.00    --    0.00 -57.00 150.00   33
  5  ω    -89.00  -6.00   1.00    1.00    --    0.00 -37.00 -60.00   83
  6  ω    -83.00 -26.00   1.00    1.00    --    0.00 -37.00-150.00   57
  7  ω    153.00 179.00   1.00    1.00    --   92.10  30.00-120.00   26
  8  ω     70.00 127.00   1.00    1.00    --   92.10  30.00-120.00   57
  9  ω    102.00 182.00   1.00    1.00    --   92.10  45.00  30.00   80
 10  ω      9.00  35.00   1.00    1.00    --   92.10 -82.00-180.00   26
 11  ω     13.00  39.00   1.00    1.00    --   92.10 -45.00  30.00   26
 12  ω      4.00 124.00   1.00    1.00    --   92.10 -82.00-120.00  120
 13  ω     67.00 123.00   1.00    1.00    --   92.10  45.00 -30.00   56
 14  ω    126.00 164.00   1.00    1.00    --   92.10  45.00 -30.00   38
 15  ω     86.00 121.00   1.00    1.00    --   92.10 -82.00  90.00   35
 16  ω     22.00 117.00   1.00    1.00    --   92.10 -45.00 -60.00   95
 17  ω     24.00  76.00   1.00    1.00    --   92.10 -61.00-120.00   52
 18  ω      7.00  74.00   1.00    1.00    --   92.10 -82.00  90.00   67
 19  ω     81.00 120.00   1.00    1.00    --   92.10 -61.00-120.00   39
 20  ω     93.00 124.00   1.00    1.00    --   92.10 -82.00 -60.00   31
 21  ω     61.00 110.00   1.00    1.00    --   92.10 -82.00  30.00   49
 22  ω     72.00 122.00   1.00    1.00    --   92.10 -82.00-180.00   50
 23  ω     19.00  45.00   1.00    1.00    --   92.10 -82.00  30.00   26
 24  ω    101.00 166.00   1.00    1.00    --   92.10  45.00 -60.00   65
 25  ω     90.00 118.00   1.00    1.00    --   92.10 -45.00  30.00   28
 26  ω      4.00 118.00   1.00    1.00    --   92.10 -61.00  90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1414607000
_diffrn_orient_matrix_UB_12      -0.0338607000
_diffrn_orient_matrix_UB_13      -0.0118709000
_diffrn_orient_matrix_UB_21      0.0454366000
_diffrn_orient_matrix_UB_22      0.0487246000
_diffrn_orient_matrix_UB_23      0.1194401000
_diffrn_orient_matrix_UB_31      -0.0376600000
_diffrn_orient_matrix_UB_32      -0.0688402000
_diffrn_orient_matrix_UB_33      0.0904518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.857
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              20
_reflns_limit_k_min              -20
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                5221
_reflns_number_total             5801
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1233
_refine_diff_density_min         -0.1536
_refine_diff_density_rms         0.0311
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.07(14)
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             10.2595
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    64
_refine_ls_number_parameters     488
_refine_ls_number_reflns         5801
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.0563
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.0331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0826
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C38(H38), C39(H39),
 C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.28702(14) 0.50182(9) 0.83157(13) 0.0437(4) Uani 1.000000 .
O2 O 0.43230(13) 0.41052(8) 0.77540(12) 0.0343(3) Uani 1.000000 .
O3 O 0.15218(15) 0.54403(9) 0.50534(15) 0.0519(4) Uani 1.000000 .
C1 C 0.2648(2) 0.64327(12) 0.62537(18) 0.0315(4) Uani 1.000000 .
C2 C 0.3854(2) 0.66705(12) 0.68115(19) 0.0349(5) Uani 1.000000 .
H2 H 0.4556(2) 0.63005(12) 0.69262(19) 0.0418(6) Uiso 1.000000 R
C3 C 0.4030(2) 0.74465(12) 0.7200(2) 0.0391(5) Uani 1.000000 .
H3 H 0.4859(2) 0.76098(12) 0.7566(2) 0.0470(6) Uiso 1.000000 R
C4 C 0.3007(2) 0.79822(13) 0.7056(2) 0.0420(5) Uani 1.000000 .
H4 H 0.3129(2) 0.85133(13) 0.7327(2) 0.0504(6) Uiso 1.000000 R
C5 C 0.1802(2) 0.77476(13) 0.6517(2) 0.0446(5) Uani 1.000000 .
H5 H 0.1096(2) 0.81181(13) 0.6427(2) 0.0535(7) Uiso 1.000000 R
C6 C 0.1613(2) 0.69758(13) 0.6107(2) 0.0407(5) Uani 1.000000 .
H6 H 0.0786(2) 0.68181(13) 0.5729(2) 0.0488(6) Uiso 1.000000 R
C7 C 0.43459(18) 0.48964(11) 0.38179(18) 0.0307(4) Uani 1.000000 .
C8 C 0.4633(2) 0.56746(12) 0.3497(2) 0.0372(5) Uani 1.000000 .
H8 H 0.4776(2) 0.60511(12) 0.4170(2) 0.0446(6) Uiso 1.000000 R
C9 C 0.4712(2) 0.59057(13) 0.2206(2) 0.0425(5) Uani 1.000000 .
H9 H 0.4921(2) 0.64370(13) 0.1998(2) 0.0511(6) Uiso 1.000000 R
C10 C 0.4487(2) 0.53646(13) 0.1221(2) 0.0388(5) Uani 1.000000 .
H10 H 0.4531(2) 0.55242(13) 0.0335(2) 0.0466(6) Uiso 1.000000 R
C11 C 0.4199(2) 0.45951(13) 0.1526(2) 0.0404(5) Uani 1.000000 .
H11 H 0.4030(2) 0.42245(13) 0.0849(2) 0.0484(6) Uiso 1.000000 R
C12 C 0.4153(2) 0.43562(12) 0.28169(19) 0.0364(5) Uani 1.000000 .
H12 H 0.3988(2) 0.38183(12) 0.30178(19) 0.0437(6) Uiso 1.000000 R
C13 C 0.2467(2) 0.56170(12) 0.57531(19) 0.0340(5) Uani 1.000000 .
C14 C 0.35159(19) 0.47400(12) 0.7439(2) 0.0337(5) Uani 1.000000 .
C15 C 0.34895(18) 0.49940(11) 0.60923(18) 0.0306(4) Uani 1.000000 .
C16 C 0.42835(19) 0.46379(11) 0.52072(19) 0.0308(4) Uani 1.000000 .
C17 C 0.5147(2) 0.40158(11) 0.56219(18) 0.0324(4) Uani 1.000000 .
H17 H 0.5711(2) 0.37683(11) 0.50089(18) 0.0389(5) Uiso 1.000000 R
C18 C 0.5171(2) 0.37750(11) 0.68749(19) 0.0322(4) Uani 1.000000 .
C19 C 0.6093(2) 0.32083(12) 0.74707(19) 0.0336(5) Uani 1.000000 .
C20 C 0.6846(2) 0.27010(13) 0.6701(2) 0.0421(5) Uani 1.000000 .
H20 H 0.6717(2) 0.27035(13) 0.5782(2) 0.0505(6) Uiso 1.000000 R
C21 C 0.7774(2) 0.21972(14) 0.7250(2) 0.0452(6) Uani 1.000000 .
H21 H 0.8280(2) 0.18600(14) 0.6708(2) 0.0542(7) Uiso 1.000000 R
C22 C 0.7968(2) 0.21811(14) 0.8582(2) 0.0460(6) Uani 1.000000 .
H22 H 0.8603(2) 0.18317(14) 0.8962(2) 0.0552(7) Uiso 1.000000 R
C23 C 0.7233(2) 0.26767(15) 0.9358(2) 0.0506(6) Uani 1.000000 .
H23 H 0.7368(2) 0.26694(15) 1.0276(2) 0.0607(7) Uiso 1.000000 R
C24 C 0.6300(2) 0.31842(14) 0.8815(2) 0.0420(5) Uani 1.000000 .
H24 H 0.5797(2) 0.35192(14) 0.9364(2) 0.0504(6) Uiso 1.000000 R
O4 O 0.92680(13) 0.42160(8) 0.58402(12) 0.0326(3) Uani 1.000000 .
O5 O 0.76988(13) 0.50970(8) 0.53936(13) 0.0404(4) Uani 1.000000 .
O6 O 0.61705(14) 0.54018(8) 0.78816(15) 0.0420(4) Uani 1.000000 .
C25 C 1.13725(19) 0.33208(12) 0.47960(19) 0.0339(5) Uani 1.000000 .
H25 H 1.11114(19) 0.37657(12) 0.42907(19) 0.0406(5) Uiso 1.000000 R
C26 C 1.2143(2) 0.27357(12) 0.4243(2) 0.0387(5) Uani 1.000000 .
H26 H 1.2406(2) 0.27805(12) 0.3361(2) 0.0464(6) Uiso 1.000000 R
C27 C 1.2532(2) 0.20866(13) 0.4969(2) 0.0443(5) Uani 1.000000 .
H27 H 1.3058(2) 0.16853(13) 0.4586(2) 0.0531(7) Uiso 1.000000 R
C28 C 1.2151(2) 0.20240(13) 0.6255(2) 0.0480(6) Uani 1.000000 .
H28 H 1.2421(2) 0.15802(13) 0.6758(2) 0.0576(7) Uiso 1.000000 R
C29 C 1.1380(2) 0.26031(13) 0.6808(2) 0.0426(5) Uani 1.000000 .
H29 H 1.1120(2) 0.25541(13) 0.7691(2) 0.0511(6) Uiso 1.000000 R
C30 C 1.0978(2) 0.32614(12) 0.60857(19) 0.0325(4) Uani 1.000000 .
C31 C 1.01441(19) 0.38647(12) 0.66883(18) 0.0312(4) Uani 1.000000 .
C32 C 1.0181(2) 0.40736(12) 0.79515(18) 0.0342(5) Uani 1.000000 .
H32 H 1.0828(2) 0.38428(12) 0.85179(18) 0.0411(5) Uiso 1.000000 R
C33 C 0.92679(19) 0.46341(11) 0.84567(19) 0.0311(4) Uani 1.000000 .
C34 C 0.83822(18) 0.49836(11) 0.76168(18) 0.0292(4) Uani 1.000000 .
C35 C 0.83778(19) 0.47955(11) 0.62323(18) 0.0308(4) Uani 1.000000 .
C36 C 0.73499(19) 0.55626(11) 0.80321(18) 0.0306(4) Uani 1.000000 .
C37 C 0.93104(19) 0.48098(11) 0.98813(18) 0.0303(4) Uani 1.000000 .
C38 C 1.0528(2) 0.49469(12) 1.05103(18) 0.0339(5) Uani 1.000000 .
H38 H 1.1328(2) 0.49317(12) 1.00276(18) 0.0407(5) Uiso 1.000000 R
C39 C 1.0579(2) 0.51053(13) 1.1835(2) 0.0380(5) Uani 1.000000 .
H39 H 1.1413(2) 0.52049(13) 1.2252(2) 0.0456(6) Uiso 1.000000 R
C40 C 0.9425(2) 0.51192(12) 1.25525(19) 0.0374(5) Uani 1.000000 .
H40 H 0.9464(2) 0.52267(12) 1.34609(19) 0.0449(6) Uiso 1.000000 R
C41 C 0.8211(2) 0.49756(12) 1.19404(19) 0.0349(5) Uani 1.000000 .
H41 H 0.7417(2) 0.49815(12) 1.24324(19) 0.0418(5) Uiso 1.000000 R
C42 C 0.8149(2) 0.48237(11) 1.06167(19) 0.0345(5) Uani 1.000000 .
H42 H 0.7312(2) 0.47281(11) 1.02043(19) 0.0414(6) Uiso 1.000000 R
C43 C 0.7759(2) 0.63365(11) 0.85881(18) 0.0313(4) Uani 1.000000 .
C44 C 0.9039(2) 0.66258(13) 0.8455(2) 0.0418(5) Uani 1.000000 .
H44 H 0.9714(2) 0.63074(13) 0.8084(2) 0.0502(6) Uiso 1.000000 R
C45 C 0.9322(3) 0.73855(16) 0.8868(2) 0.0586(7) Uani 1.000000 .
H45 H 1.0194(3) 0.75924(16) 0.8766(2) 0.0704(9) Uiso 1.000000 R
C46 C 0.8351(3) 0.78450(15) 0.9427(2) 0.0633(8) Uani 1.000000 .
H46 H 0.8548(3) 0.83718(15) 0.9679(2) 0.0759(10) Uiso 1.000000 R
C47 C 0.7098(3) 0.75432(14) 0.9620(2) 0.0568(7) Uani 1.000000 .
H47 H 0.6445(3) 0.78505(14) 1.0049(2) 0.0682(8) Uiso 1.000000 R
C48 C 0.6793(2) 0.67946(12) 0.9192(2) 0.0414(5) Uani 1.000000 .
H48 H 0.5922(2) 0.65895(12) 0.9308(2) 0.0496(6) Uiso 1.000000 R


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 C14 1.211(2) . ?
O2 C14 1.383(2) . ?
O2 C18 1.368(2) . ?
O3 C13 1.220(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.395(3) . ?
C1 C13 1.486(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 C12 1.388(3) . ?
C7 C16 1.493(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C15 1.510(3) . ?
C14 C15 1.448(3) . ?
C15 C16 1.358(3) . ?
C16 C17 1.426(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.349(3) . ?
C18 C19 1.462(3) . ?
C19 C20 1.397(3) . ?
C19 C24 1.393(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9500 . ?
O4 C31 1.365(2) . ?
O4 C35 1.391(2) . ?
O5 C35 1.204(2) . ?
O6 C36 1.223(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.384(3) . ?
C25 C30 1.390(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.396(3) . ?
C30 C31 1.465(3) . ?
C31 C32 1.344(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.423(3) . ?
C33 C34 1.365(3) . ?
C33 C37 1.492(3) . ?
C34 C35 1.456(3) . ?
C34 C36 1.494(3) . ?
C36 C43 1.486(3) . ?
C37 C38 1.394(3) . ?
C37 C42 1.398(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.386(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.382(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.385(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.383(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.385(3) . ?
C43 C48 1.394(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.384(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.379(4) . ?
C46 H46 0.9500 . ?
C46 C47 1.375(4) . ?
C47 H47 0.9500 . ?
C47 C48 1.376(3) . ?
C48 H48 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O2 C14 122.16(15) . . ?
C6 C1 C2 119.72(19) . . ?
C13 C1 C2 120.91(18) . . ?
C13 C1 C6 119.31(18) . . ?
H2 C2 C1 119.98(12) . . ?
C3 C2 C1 120.04(19) . . ?
C3 C2 H2 119.98(13) . . ?
H3 C3 C2 119.91(13) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.91(13) . . ?
H4 C4 C3 119.97(13) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.97(13) . . ?
H5 C5 C4 119.73(13) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.73(13) . . ?
C5 C6 C1 119.5(2) . . ?
H6 C6 C1 120.27(12) . . ?
H6 C6 C5 120.27(13) . . ?
C12 C7 C8 118.54(18) . . ?
C16 C7 C8 121.06(17) . . ?
C16 C7 C12 120.37(18) . . ?
H8 C8 C7 119.67(11) . . ?
C9 C8 C7 120.66(19) . . ?
C9 C8 H8 119.67(13) . . ?
H9 C9 C8 119.96(13) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.96(13) . . ?
H10 C10 C9 120.12(13) . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.12(13) . . ?
H11 C11 C10 119.82(13) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.82(12) . . ?
C11 C12 C7 120.54(19) . . ?
H12 C12 C7 119.73(12) . . ?
H12 C12 C11 119.73(12) . . ?
C1 C13 O3 121.53(19) . . ?
C15 C13 O3 119.00(19) . . ?
C15 C13 C1 119.46(16) . . ?
O2 C14 O1 116.60(18) . . ?
C15 C14 O1 126.15(19) . . ?
C15 C14 O2 117.21(17) . . ?
C14 C15 C13 115.56(17) . . ?
C16 C15 C13 124.07(17) . . ?
C16 C15 C14 120.20(18) . . ?
C15 C16 C7 122.73(18) . . ?
C17 C16 C7 117.93(17) . . ?
C17 C16 C15 119.27(18) . . ?
H17 C17 C16 119.64(11) . . ?
C18 C17 C16 120.72(19) . . ?
C18 C17 H17 119.64(12) . . ?
C17 C18 O2 120.10(18) . . ?
C19 C18 O2 112.91(16) . . ?
C19 C18 C17 126.88(19) . . ?
C20 C19 C18 120.86(17) . . ?
C24 C19 C18 121.22(19) . . ?
C24 C19 C20 117.8(2) . . ?
H20 C20 C19 119.37(12) . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.37(13) . . ?
H21 C21 C20 119.90(13) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.90(14) . . ?
H22 C22 C21 120.30(14) . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.30(13) . . ?
H23 C23 C22 119.61(13) . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.61(13) . . ?
C23 C24 C19 120.5(2) . . ?
H24 C24 C19 119.73(13) . . ?
H24 C24 C23 119.73(13) . . ?
C35 O4 C31 122.31(15) . . ?
C26 C25 H25 119.80(12) . . ?
C30 C25 H25 119.80(12) . . ?
C30 C25 C26 120.40(19) . . ?
H26 C26 C25 119.82(12) . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26 119.82(13) . . ?
H27 C27 C26 120.16(13) . . ?
C28 C27 C26 119.7(2) . . ?
C28 C27 H27 120.16(13) . . ?
H28 C28 C27 119.89(13) . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.89(13) . . ?
H29 C29 C28 119.65(13) . . ?
C30 C29 C28 120.7(2) . . ?
C30 C29 H29 119.65(12) . . ?
C29 C30 C25 118.64(19) . . ?
C31 C30 C25 121.56(18) . . ?
C31 C30 C29 119.80(18) . . ?
C30 C31 O4 113.76(15) . . ?
C32 C31 O4 120.56(18) . . ?
C32 C31 C30 125.68(17) . . ?
H32 C32 C31 119.39(12) . . ?
C33 C32 C31 121.23(18) . . ?
C33 C32 H32 119.39(11) . . ?
C34 C33 C32 118.49(17) . . ?
C37 C33 C32 118.72(17) . . ?
C37 C33 C34 122.78(18) . . ?
C35 C34 C33 120.93(17) . . ?
C36 C34 C33 123.61(17) . . ?
C36 C34 C35 115.45(16) . . ?
O5 C35 O4 116.92(17) . . ?
C34 C35 O4 116.34(15) . . ?
C34 C35 O5 126.74(18) . . ?
C34 C36 O6 119.47(17) . . ?
C43 C36 O6 120.47(18) . . ?
C43 C36 C34 120.04(17) . . ?
C38 C37 C33 119.99(17) . . ?
C42 C37 C33 121.31(17) . . ?
C42 C37 C38 118.69(17) . . ?
H38 C38 C37 119.78(11) . . ?
C39 C38 C37 120.43(19) . . ?
C39 C38 H38 119.78(12) . . ?
H39 C39 C38 119.79(12) . . ?
C40 C39 C38 120.41(19) . . ?
C40 C39 H39 119.79(11) . . ?
H40 C40 C39 120.18(11) . . ?
C41 C40 C39 119.64(18) . . ?
C41 C40 H40 120.18(12) . . ?
H41 C41 C40 119.82(12) . . ?
C42 C41 C40 120.36(19) . . ?
C42 C41 H41 119.82(12) . . ?
C41 C42 C37 120.45(18) . . ?
H42 C42 C37 119.77(11) . . ?
H42 C42 C41 119.77(12) . . ?
C44 C43 C36 121.78(19) . . ?
C48 C43 C36 118.18(19) . . ?
C48 C43 C44 119.9(2) . . ?
H44 C44 C43 120.46(13) . . ?
C45 C44 C43 119.1(2) . . ?
C45 C44 H44 120.46(17) . . ?
H45 C45 C44 119.68(17) . . ?
C46 C45 C44 120.6(2) . . ?
C46 C45 H45 119.68(15) . . ?
H46 C46 C45 119.88(15) . . ?
C47 C46 C45 120.2(2) . . ?
C47 C46 H46 119.88(16) . . ?
H47 C47 C46 120.10(15) . . ?
C48 C47 C46 119.8(3) . . ?
C48 C47 H47 120.10(17) . . ?
C47 C48 C43 120.2(2) . . ?
H48 C48 C43 119.91(12) . . ?
H48 C48 C47 119.91(17) . . ?

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
O1 C14 O2 C18 -175.26(16) . . . . ?
O1 C14 C15 C13 -5.6(2) . . . . ?
O1 C14 C15 C16 178.9(2) . . . . ?
O2 C14 C15 C13 172.37(15) . . . . ?
O2 C14 C15 C16 -3.1(2) . . . . ?
O2 C18 C17 C16 2.7(2) . . . . ?
O2 C18 C19 C20 167.26(16) . . . . ?
O2 C18 C19 C24 -16.1(2) . . . . ?
O3 C13 C1 C2 -166.2(2) . . . . ?
O3 C13 C1 C6 10.9(2) . . . . ?
O3 C13 C15 C14 -111.1(2) . . . . ?
O3 C13 C15 C16 64.2(2) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C6 C5 C4 0.6(2) . . . . ?
C1 C13 C15 C14 70.2(2) . . . . ?
C1 C13 C15 C16 -114.50(18) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C7 C12 C11 C10 2.5(2) . . . . ?
C7 C16 C15 C13 7.7(2) . . . . ?
C7 C16 C15 C14 -177.22(17) . . . . ?
C7 C16 C17 C18 177.65(17) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C13 C15 C16 C17 -175.44(18) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C19 -173.02(17) . . . . ?
C17 C18 C19 C20 -16.8(2) . . . . ?
C17 C18 C19 C24 159.9(2) . . . . ?
C18 C19 C20 C21 176.2(2) . . . . ?
C18 C19 C24 C23 -176.2(2) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C19 C24 C23 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
O4 C31 C30 C25 32.2(2) . . . . ?
O4 C31 C30 C29 -146.93(18) . . . . ?
O4 C31 C32 C33 3.3(2) . . . . ?
O4 C35 C34 C33 3.4(2) . . . . ?
O4 C35 C34 C36 -175.58(16) . . . . ?
O5 C35 C34 C33 -175.5(2) . . . . ?
O5 C35 C34 C36 5.6(2) . . . . ?
O6 C36 C34 C33 -117.25(19) . . . . ?
O6 C36 C34 C35 61.7(2) . . . . ?
O6 C36 C43 C44 -162.37(19) . . . . ?
O6 C36 C43 C48 13.9(2) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C25 C30 C29 C28 -0.0(2) . . . . ?
C25 C30 C31 C32 -148.42(19) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
C28 C29 C30 C31 179.2(2) . . . . ?
C29 C30 C31 C32 32.4(2) . . . . ?
C30 C31 C32 C33 -176.0(2) . . . . ?
C31 C32 C33 C34 -2.7(2) . . . . ?
C31 C32 C33 C37 176.75(19) . . . . ?
C32 C33 C34 C35 -0.7(2) . . . . ?
C32 C33 C34 C36 178.16(17) . . . . ?
C32 C33 C37 C38 46.2(2) . . . . ?
C32 C33 C37 C42 -132.32(19) . . . . ?
C33 C34 C36 C43 64.5(2) . . . . ?
C33 C37 C38 C39 -179.56(18) . . . . ?
C33 C37 C42 C41 178.99(18) . . . . ?
C34 C36 C43 C44 15.9(2) . . . . ?
C34 C36 C43 C48 -167.84(18) . . . . ?
C36 C43 C44 C45 173.04(19) . . . . ?
C36 C43 C48 C47 -174.40(18) . . . . ?
C37 C38 C39 C40 0.8(2) . . . . ?
C37 C42 C41 C40 0.3(2) . . . . ?
C38 C39 C40 C41 -0.2(3) . . . . ?
C39 C40 C41 C42 -0.4(2) . . . . ?
C43 C44 C45 C46 1.1(2) . . . . ?
C43 C48 C47 C46 1.4(2) . . . . ?
C44 C45 C46 C47 2.2(3) . . . . ?
C45 C46 C47 C48 -3.5(3) . . . . ?


_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 4.001
_oxdiff_exptl_absorpt_empirical_full_min 0.544
_chemical_name_systematic        5-Benzoyl-4,6-diphenyl-2H-pyran-2-one
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2306338'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl 6-methyl-2-oxo-4-phenyl-2H-pyran-5-carboxylate'
_chemical_formula_moiety         'C15 H14 O4'
_chemical_formula_sum            'C15 H14 O4'
_chemical_formula_weight         258.26
_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'
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                   9.3720(2)
_cell_length_b                   19.4732(4)
_cell_length_c                   7.23890(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.595(2)
_cell_angle_gamma                90
_cell_volume                     1314.83(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      73.0260
_cell_measurement_theta_min      5.2500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6399
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.035
_diffrn_reflns_theta_max         67.035
_diffrn_reflns_theta_min         4.541
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -32.00   1.00    2.00    --    0.00 -37.00-150.00   55
  2  ω     -4.00  27.00   1.00    2.00    --    0.00 -37.00-150.00   31
  3  ω    -88.00 -47.00   1.00    2.00    --    0.00 -37.00 -60.00   41
  4  ω     -8.00  25.00   1.00    2.00    --    0.00 -37.00 -60.00   33
  5  ω     21.00 124.00   1.00    2.00    --   92.10 -82.00-120.00  103
  6  ω    139.00 182.00   1.00    2.00    --   92.10  82.00-180.00   43
  7  ω     72.00 181.00   1.00    2.00    --   92.10  30.00 120.00  109
  8  ω     62.00  89.00   1.00    2.00    --   92.10  30.00   0.00   27
  9  ω    130.00 176.00   1.00    2.00    --   92.10  30.00   0.00   46
 10  ω     59.00 117.00   1.00    2.00    --   92.10 -61.00 -90.00   58
 11  ω     46.00  86.00   1.00    2.00    --   92.10 -77.00-120.00   40
 12  ω     57.00 119.00   1.00    2.00    --   92.10  82.00-180.00   62
 13  ω     54.00  99.00   1.00    2.00    --   92.10 -82.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1383164000
_diffrn_orient_matrix_UB_12      0.0427670000
_diffrn_orient_matrix_UB_13      0.0012647000
_diffrn_orient_matrix_UB_21      0.0899025000
_diffrn_orient_matrix_UB_22      -0.0645206000
_diffrn_orient_matrix_UB_23      0.0530933000
_diffrn_orient_matrix_UB_31      0.0072953000
_diffrn_orient_matrix_UB_32      -0.0162642000
_diffrn_orient_matrix_UB_33      -0.2072217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                1941
_reflns_number_total             2332
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0082(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.093
_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)+(0.0729P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1305
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_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 0.60486(13) 0.47020(6) 0.68509(18) 0.0464(4) Uani 1 1 d . . . . .
O2 O 0.40865(12) 0.42175(5) 0.78338(15) 0.0355(3) Uani 1 1 d . . . . .
O3 O 0.75162(11) 0.26061(6) 0.72875(15) 0.0361(3) Uani 1 1 d . . . . .
O4 O 0.69836(14) 0.15024(6) 0.69605(19) 0.0482(4) Uani 1 1 d . . . . .
C1 C 0.32930(16) 0.31689(8) 0.51834(18) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.30998(18) 0.37356(8) 0.40096(19) 0.0313(4) Uani 1 1 d . . . . .
H2 H 0.390302 0.400265 0.374326 0.038 Uiso 1 1 calc R U . . .
C3 C 0.17411(19) 0.39103(9) 0.3231(2) 0.0387(4) Uani 1 1 d . . . . .
H3 H 0.161582 0.429957 0.244116 0.046 Uiso 1 1 calc R U . . .
C4 C 0.05667(19) 0.35233(9) 0.3594(2) 0.0408(4) Uani 1 1 d . . . . .
H4 H -0.036359 0.364488 0.305361 0.049 Uiso 1 1 calc R U . . .
C5 C 0.07516(18) 0.29568(9) 0.4748(2) 0.0378(4) Uani 1 1 d . . . . .
H5 H -0.005462 0.268957 0.500186 0.045 Uiso 1 1 calc R U . . .
C6 C 0.21037(17) 0.27786(8) 0.5533(2) 0.0312(4) Uani 1 1 d . . . . .
H6 H 0.222289 0.238737 0.631710 0.037 Uiso 1 1 calc R U . . .
C7 C 0.71311(18) 0.32804(8) 0.7322(2) 0.0321(4) Uani 1 1 d . . . . .
C8 C 0.57707(17) 0.34778(8) 0.67848(19) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.47434(16) 0.29695(8) 0.60208(18) 0.0259(4) Uani 1 1 d . . . . .
C10 C 0.51477(17) 0.23013(8) 0.60227(19) 0.0288(4) Uani 1 1 d . . . . .
H10 H 0.448350 0.196799 0.550774 0.035 Uiso 1 1 calc R U . . .
C11 C 0.65345(18) 0.20819(8) 0.6771(2) 0.0338(4) Uani 1 1 d . . . . .
C12 C 0.83740(19) 0.37170(10) 0.8026(3) 0.0433(5) Uani 1 1 d . . . . .
H12A H 0.893512 0.348010 0.904772 0.065 Uiso 1 1 calc R U . . .
H12B H 0.802375 0.415503 0.847235 0.065 Uiso 1 1 calc R U . . .
H12C H 0.897993 0.380275 0.702097 0.065 Uiso 1 1 calc R U . . .
C13 C 0.53448(18) 0.42002(8) 0.7126(2) 0.0313(4) Uani 1 1 d . . . . .
C14 C 0.3412(2) 0.48915(9) 0.7947(3) 0.0467(5) Uani 1 1 d . . . . .
H14A H 0.354558 0.516524 0.682444 0.056 Uiso 1 1 calc R U . . .
H14B H 0.384462 0.514486 0.904856 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1857(2) 0.47699(11) 0.8096(3) 0.0559(6) Uani 1 1 d . . . . .
H15A H 0.143152 0.454140 0.696775 0.084 Uiso 1 1 calc R U . . .
H15B H 0.137479 0.521021 0.824321 0.084 Uiso 1 1 calc R U . . .
H15C H 0.174270 0.447798 0.917440 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.2064(18) . ?
O2 C13 1.331(2) . ?
O2 C14 1.4626(19) . ?
O3 C7 1.3626(19) . ?
O3 C11 1.4005(19) . ?
O4 C11 1.2074(19) . ?
C1 C2 1.394(2) . ?
C1 C6 1.393(2) . ?
C1 C9 1.485(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.352(2) . ?
C7 C12 1.491(2) . ?
C8 C9 1.452(2) . ?
C8 C13 1.490(2) . ?
C9 C10 1.355(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.424(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.491(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 116.62(13) . . ?
C7 O3 C11 122.62(13) . . ?
C2 C1 C9 121.01(14) . . ?
C6 C1 C2 118.97(14) . . ?
C6 C1 C9 120.00(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.17(16) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.51(15) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.64(16) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(16) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.42(15) . . ?
C5 C6 H6 119.8 . . ?
O3 C7 C12 110.87(14) . . ?
C8 C7 O3 120.85(14) . . ?
C8 C7 C12 128.28(15) . . ?
C7 C8 C9 119.17(14) . . ?
C7 C8 C13 118.76(14) . . ?
C9 C8 C13 121.90(14) . . ?
C8 C9 C1 121.59(13) . . ?
C10 C9 C1 119.75(13) . . ?
C10 C9 C8 118.63(14) . . ?
C9 C10 H10 118.9 . . ?
C9 C10 C11 122.22(15) . . ?
C11 C10 H10 118.9 . . ?
O3 C11 C10 115.74(14) . . ?
O4 C11 O3 115.99(15) . . ?
O4 C11 C10 128.23(15) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 124.22(15) . . ?
O1 C13 C8 125.30(15) . . ?
O2 C13 C8 110.45(13) . . ?
O2 C14 H14A 110.3 . . ?
O2 C14 H14B 110.3 . . ?
O2 C14 C15 106.99(15) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O3 C7 C8 C9 -5.1(2) . . . . ?
O3 C7 C8 C13 170.43(13) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C1 C9 C10 C11 178.67(13) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C9 C8 42.83(19) . . . . ?
C2 C1 C9 C10 -134.86(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C6 C1 C9 C8 -138.61(15) . . . . ?
C6 C1 C9 C10 43.69(19) . . . . ?
C7 O3 C11 O4 -173.48(14) . . . . ?
C7 O3 C11 C10 8.8(2) . . . . ?
C7 C8 C9 C1 -171.94(13) . . . . ?
C7 C8 C9 C10 5.8(2) . . . . ?
C7 C8 C13 O1 43.9(2) . . . . ?
C7 C8 C13 O2 -134.37(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C1 C2 C3 179.50(13) . . . . ?
C9 C1 C6 C5 -179.47(13) . . . . ?
C9 C8 C13 O1 -140.76(16) . . . . ?
C9 C8 C13 O2 40.99(18) . . . . ?
C9 C10 C11 O3 -7.9(2) . . . . ?
C9 C10 C11 O4 174.71(16) . . . . ?
C11 O3 C7 C8 -2.5(2) . . . . ?
C11 O3 C7 C12 176.78(13) . . . . ?
C12 C7 C8 C9 175.86(15) . . . . ?
C12 C7 C8 C13 -8.6(2) . . . . ?
C13 O2 C14 C15 159.70(15) . . . . ?
C13 C8 C9 C1 12.7(2) . . . . ?
C13 C8 C9 C10 -169.57(13) . . . . ?
C14 O2 C13 O1 11.9(2) . . . . ?
C14 O2 C13 C8 -169.87(12) . . . . ?

_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 3.105
_oxdiff_exptl_absorpt_empirical_full_min 0.234
####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 2306341'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.298
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   7.3350(2)
_cell_length_b                   14.3799(3)
_cell_length_c                   24.5438(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2588.80(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7227
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      72.7150
_cell_measurement_theta_min      6.1420
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             1107.711
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24379
_diffrn_reflns_point_group_measured_fraction_full 0.9965
_diffrn_reflns_point_group_measured_fraction_max 0.9965
_diffrn_reflns_theta_full        67.0603
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00  27.00   1.00    1.00    --    0.00 -37.00 -30.00  115
  2  ω      2.00  27.00   1.00    1.00    --    0.00 -57.00  30.00   25
  3  ω    -48.00  25.00   1.00    1.00    --    0.00 -37.00 120.00   73
  4  ω    -85.00  -6.00   1.00    1.00    --    0.00 -37.00  90.00   79
  5  ω    -38.00 -12.00   1.00    1.00    --    0.00 -57.00 -90.00   26
  6  ω    -33.00  -5.00   1.00    1.00    --    0.00 -57.00  30.00   28
  7  ω      8.00 107.00   1.00    1.00    --   92.10 -61.00-150.00   99
  8  ω     64.00 103.00   1.00    1.00    --   92.10 -82.00 120.00   39
  9  ω      4.00  45.00   1.00    1.00    --   92.10 -77.00-180.00   41
 10  ω     66.00 172.00   1.00    1.00    --   92.10  45.00 -60.00  106
 11  ω     13.00 127.00   1.00    1.00    --   92.10 -82.00 -30.00  114
 12  ω      3.00  31.00   1.00    1.00    --   92.10 -61.00  30.00   28
 13  ω     95.00 121.00   1.00    1.00    --   92.10 -82.00  30.00   26
 14  ω      8.00  34.00   1.00    1.00    --   92.10 -82.00 120.00   26
 15  ω     24.00  50.00   1.00    1.00    --   92.10 -82.00  30.00   26
 16  ω      3.00 128.00   1.00    1.00    --   92.10 -82.00-150.00  125
 17  ω      4.00 118.00   1.00    1.00    --   92.10 -61.00  60.00  114
 18  ω    126.00 162.00   1.00    1.00    --   92.10  61.00 -30.00   36
 19  ω      6.00  31.00   1.00    1.00    --   92.10 -82.00 -90.00   25
 20  ω     93.00 119.00   1.00    1.00    --   92.10 -82.00 -90.00   26
 21  ω      3.00 107.00   1.00    1.00    --   92.10 -82.00  60.00  104
 22  ω     20.00  46.00   1.00    1.00    --   92.10 -30.00 -30.00   26
 23  ω     16.00  93.00   1.00    1.00    --   92.10 -61.00 -30.00   77
 24  ω     90.00 181.00   1.00    1.00    --   92.10  45.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0110790000
_diffrn_orient_matrix_UB_12      0.0349368000
_diffrn_orient_matrix_UB_13      -0.0592402000
_diffrn_orient_matrix_UB_21      0.0232297000
_diffrn_orient_matrix_UB_22      -0.1008533000
_diffrn_orient_matrix_UB_23      -0.0200461000
_diffrn_orient_matrix_UB_31      -0.2084174000
_diffrn_orient_matrix_UB_32      -0.0093606000
_diffrn_orient_matrix_UB_33      -0.0053802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                1926
_reflns_number_total             2302
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.2664
_refine_diff_density_min         -0.2909
_refine_diff_density_rms         0.0599
_refine_ls_d_res_high            0.8371
_refine_ls_d_res_low             12.2719
_refine_ls_goodness_of_fit_ref   1.0296
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.0296
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0804P)²+0.6282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1518
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.64668(17) 0.42427(8) 0.56821(5) 0.0378(4) Uani 1.000000 .
O2 O 0.5471(2) 0.54050(8) 0.70422(5) 0.0494(4) Uani 1.000000 .
C1 C 0.4823(2) 0.24620(10) 0.60582(7) 0.0284(4) Uani 1.000000 .
C2 C 0.5931(2) 0.16765(10) 0.60123(7) 0.0295(4) Uani 1.000000 .
H2 H 0.6737(2) 0.15173(10) 0.63006(7) 0.0354(5) Uiso 1.000000 R
C3 C 0.5862(2) 0.11277(10) 0.55486(7) 0.0310(4) Uani 1.000000 .
H3 H 0.6651(2) 0.06067(10) 0.55152(7) 0.0372(5) Uiso 1.000000 R
C4 C 0.4648(2) 0.13355(11) 0.51333(7) 0.0319(4) Uani 1.000000 .
H4 H 0.4591(2) 0.09528(11) 0.48182(7) 0.0383(5) Uiso 1.000000 R
C5 C 0.3519(2) 0.21017(11) 0.51792(7) 0.0334(4) Uani 1.000000 .
H5 H 0.2671(2) 0.22399(11) 0.48981(7) 0.0401(5) Uiso 1.000000 R
C6 C 0.3624(2) 0.26668(10) 0.56339(7) 0.0312(4) Uani 1.000000 .
H6 H 0.2869(2) 0.32020(10) 0.56576(7) 0.0375(5) Uiso 1.000000 R
C7 C 0.4915(2) 0.30440(11) 0.65575(7) 0.0277(4) Uani 1.000000 .
C8 C 0.5089(2) 0.40163(11) 0.65365(7) 0.0294(4) Uani 1.000000 .
C9 C 0.5195(2) 0.45557(12) 0.70176(7) 0.0334(4) Uani 1.000000 .
N10 N 0.5044(2) 0.40594(9) 0.75237(6) 0.0298(4) Uani 1.000000 .
C11 C 0.5112(3) 0.45714(12) 0.79997(7) 0.0368(5) Uani 1.000000 .
H11 H 0.5275(3) 0.52259(12) 0.79795(7) 0.0442(6) Uiso 1.000000 R
C12 C 0.4954(3) 0.41667(13) 0.84886(8) 0.0387(5) Uani 1.000000 .
H12 H 0.4998(3) 0.45334(13) 0.88103(8) 0.0464(6) Uiso 1.000000 R
C13 C 0.4722(2) 0.31877(13) 0.85256(7) 0.0357(4) Uani 1.000000 .
H13 H 0.4596(2) 0.28945(13) 0.88704(7) 0.0429(5) Uiso 1.000000 R
C14 C 0.4682(2) 0.26805(11) 0.80619(7) 0.0329(4) Uani 1.000000 .
H14 H 0.4549(2) 0.20246(11) 0.80855(7) 0.0394(5) Uiso 1.000000 R
C15 C 0.4835(2) 0.30995(11) 0.75431(7) 0.0282(4) Uani 1.000000 .
C16 C 0.4781(2) 0.26084(11) 0.70612(7) 0.0299(4) Uani 1.000000 .
H16 H 0.4648(2) 0.19516(11) 0.70738(7) 0.0358(5) Uiso 1.000000 R
C17 C 0.5362(2) 0.45218(11) 0.60100(7) 0.0314(4) Uani 1.000000 .
C18 C 0.4224(3) 0.53645(13) 0.58876(9) 0.0477(5) Uani 1.000000 .
H18a H 0.5023(3) 0.5896(3) 0.5814(6) 0.0715(8) Uiso 1.000000 GR
H18b H 0.3462(14) 0.5243(4) 0.5567(3) 0.0715(8) Uiso 1.000000 GR
H18c H 0.3443(14) 0.5505(6) 0.6201(2) 0.0715(8) Uiso 1.000000 GR


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 C17 1.211(2) . ?
O2 C9 1.239(2) . ?
C1 C2 1.396(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.485(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.405(2) . ?
C7 C16 1.389(2) . ?
C8 C9 1.415(2) . ?
C8 C17 1.496(2) . ?
C9 N10 1.437(2) . ?
N10 C11 1.382(2) . ?
N10 C15 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.339(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.421(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.352(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.413(2) . ?
C15 C16 1.378(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.502(2) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.53(15) . . ?
C7 C1 C2 119.74(14) . . ?
C7 C1 C6 121.71(14) . . ?
H2 C2 C1 119.81(9) . . ?
C3 C2 C1 120.38(15) . . ?
C3 C2 H2 119.81(9) . . ?
H3 C3 C2 119.85(9) . . ?
C4 C3 C2 120.30(15) . . ?
C4 C3 H3 119.85(9) . . ?
H4 C4 C3 120.11(9) . . ?
C5 C4 C3 119.77(15) . . ?
C5 C4 H4 120.11(10) . . ?
H5 C5 C4 119.98(10) . . ?
C6 C5 C4 120.04(15) . . ?
C6 C5 H5 119.98(9) . . ?
C5 C6 C1 120.92(15) . . ?
H6 C6 C1 119.54(9) . . ?
H6 C6 C5 119.54(9) . . ?
C8 C7 C1 122.31(14) . . ?
C16 C7 C1 118.48(14) . . ?
C16 C7 C8 119.19(15) . . ?
C9 C8 C7 121.32(15) . . ?
C17 C8 C7 121.83(14) . . ?
C17 C8 C9 116.56(15) . . ?
C8 C9 O2 126.14(16) . . ?
N10 C9 O2 117.38(15) . . ?
N10 C9 C8 116.42(15) . . ?
C11 N10 C9 117.61(14) . . ?
C15 N10 C9 122.12(14) . . ?
C15 N10 C11 120.27(14) . . ?
H11 C11 N10 119.23(10) . . ?
C12 C11 N10 121.55(16) . . ?
C12 C11 H11 119.23(10) . . ?
H12 C12 C11 120.05(10) . . ?
C13 C12 C11 119.89(16) . . ?
C13 C12 H12 120.05(10) . . ?
H13 C13 C12 120.56(10) . . ?
C14 C13 C12 118.89(16) . . ?
C14 C13 H13 120.56(10) . . ?
H14 C14 C13 119.11(10) . . ?
C15 C14 C13 121.79(16) . . ?
C15 C14 H14 119.11(9) . . ?
C14 C15 N10 117.60(14) . . ?
C16 C15 N10 118.86(15) . . ?
C16 C15 C14 123.54(15) . . ?
C15 C16 C7 122.05(15) . . ?
H16 C16 C7 118.98(9) . . ?
H16 C16 C15 118.98(9) . . ?
C8 C17 O1 120.17(15) . . ?
C18 C17 O1 120.44(16) . . ?
C18 C17 C8 119.38(15) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 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
O1 C17 C8 C7 -46.04(19) . . . . ?
O1 C17 C8 C9 127.91(17) . . . . ?
O2 C9 C8 C7 174.81(19) . . . . ?
O2 C9 C8 C17 0.8(2) . . . . ?
O2 C9 N10 C11 3.7(2) . . . . ?
O2 C9 N10 C15 -176.38(16) . . . . ?
C1 C2 C3 C4 -2.17(18) . . . . ?
C1 C6 C5 C4 -1.82(19) . . . . ?
C1 C7 C8 C9 -179.26(15) . . . . ?
C1 C7 C8 C17 -5.60(18) . . . . ?
C1 C7 C16 C15 -179.33(14) . . . . ?
C2 C3 C4 C5 0.91(19) . . . . ?
C3 C4 C5 C6 1.07(19) . . . . ?
C7 C8 C9 N10 -2.32(18) . . . . ?
C7 C8 C17 C18 132.59(17) . . . . ?
C7 C16 C15 N10 -0.50(19) . . . . ?
C7 C16 C15 C14 179.29(15) . . . . ?
C8 C9 N10 C11 -178.95(15) . . . . ?
C8 C9 N10 C15 1.0(2) . . . . ?
C9 N10 C11 C12 178.98(16) . . . . ?
C9 N10 C15 C14 -179.44(16) . . . . ?
C9 N10 C15 C16 0.37(18) . . . . ?
N10 C11 C12 C13 0.4(2) . . . . ?
N10 C15 C14 C13 0.53(18) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C13 C14 C15 C16 -179.27(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 3.800
_oxdiff_exptl_absorpt_empirical_full_min 0.340
_chemical_name_systematic        1-Acetyl-2-phenyl-4H-quinolizin-4-one
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2306337'
loop_
_audit_author_name
_audit_author_address
'Lin Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C16 H9 Cl N2 O'
_chemical_formula_sum            'C16 H9 Cl N2 O'
_chemical_formula_weight         280.715
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.36457 0.70364 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y,-z+1/2
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y+1/2,z
5 -x,-y,-z
6 -x-1/2,y,z-1/2
7 x,-y-1/2,z-1/2
8 x-1/2,y-1/2,-z

_symmetry_Int_Tables_number      56
_cell_length_a                   14.1800(2)
_cell_length_b                   19.7617(3)
_cell_length_c                   18.2437(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5112.27(12)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    20432
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.1660
_cell_measurement_theta_min      4.5110
_exptl_absorpt_coefficient_mu    2.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             2316.918
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9874
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            62477
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9874
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.38
_diffrn_reflns_theta_min         3.84
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  45.00   1.00    1.00    --    0.00  57.00 -90.00   26
  2  ω    -21.00   8.00   1.00    1.00    --    0.00  37.00  60.00   29
  3  ω    -89.00 -57.00   1.00    1.00    --    0.00 -37.00  60.00   32
  4  ω    -28.00  26.00   1.00    1.00    --    0.00 -37.00  60.00   54
  5  ω    -37.00  -9.00   1.00    1.00    --    0.00 -37.00 150.00   28
  6  ω     13.00  89.00   1.00    1.00    --    0.00  37.00  60.00   76
  7  ω     50.00  89.00   1.00    1.00    --    0.00  57.00 -60.00   39
  8  ω    -73.00  27.00   1.00    1.00    --    0.00 -37.00-150.00  100
  9  ω      4.00  29.00   1.00    1.00    --    0.00 -19.00 -90.00   25
 10  ω    -64.00 -16.00   1.00    1.00    --    0.00 -19.00 -90.00   48
 11  ω     66.00 176.00   1.00    2.00    --   92.10  45.00  90.00  110
 12  ω     21.00 128.00   1.00    2.00    --   92.10 -82.00-120.00  107
 13  ω     76.00 102.00   1.00    2.00    --   92.10 -82.00 -60.00   26
 14  ω     80.00 128.00   1.00    2.00    --   92.10 -82.00  60.00   48
 15  ω     73.00  98.00   1.00    2.00    --   92.10  45.00 -30.00   25
 16  ω     87.00 113.00   1.00    2.00    --   92.10 -61.00 120.00   26
 17  ω     66.00 162.00   1.00    2.00    --   92.10  45.00 120.00   96
 18  ω     66.00 145.00   1.00    2.00    --   92.10  45.00-150.00   79
 19  ω     35.00 121.00   1.00    2.00    --   92.10 -82.00 120.00   86
 20  ω     82.00 108.00   1.00    2.00    --   92.10 -82.00-180.00   26
 21  ω     66.00 182.00   1.00    2.00    --   92.10  45.00-180.00  116
 22  ω     15.00 128.00   1.00    2.00    --   92.10 -82.00 -30.00  113
 23  ω     90.00 124.00   1.00    2.00    --   92.10 -82.00  30.00   34
 24  ω      4.00  30.00   1.00    2.00    --   92.10 -82.00  30.00   26
 25  ω      4.00  92.00   1.00    2.00    --   92.10 -61.00-120.00   88
 26  ω      4.00  29.00   1.00    2.00    --   92.10 -82.00 -60.00   25
 27  ω     38.00  64.00   1.00    2.00    --   92.10 -61.00 120.00   26
 28  ω     80.00 105.00   1.00    2.00    --   92.10 -82.00 150.00   25
 29  ω     11.00 115.00   1.00    2.00    --   92.10 -61.00 -30.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0923448000
_diffrn_orient_matrix_UB_12      -0.0218436000
_diffrn_orient_matrix_UB_13      0.0375667000
_diffrn_orient_matrix_UB_21      0.0386122000
_diffrn_orient_matrix_UB_22      -0.0724967000
_diffrn_orient_matrix_UB_23      0.0078399000
_diffrn_orient_matrix_UB_31      0.0421377000
_diffrn_orient_matrix_UB_32      0.0185108000
_diffrn_orient_matrix_UB_33      0.0752700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4471
_reflns_number_total             5158
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.2628
_refine_diff_density_min         -0.5336
_refine_diff_density_rms         0.1064
_refine_ls_d_res_high            0.8005
_refine_ls_d_res_low             11.5209
_refine_ls_goodness_of_fit_ref   1.1098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.1098
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1446
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Cl01 Cl 0.66881(3) 0.478858(19) 0.20781(2) 0.03500(15) Uani 1.000000 .
Cl02 Cl 0.35640(3) 0.47579(2) -0.01445(2) 0.04084(16) Uani 1.000000 .
O003 O 0.38293(8) 0.59168(6) 0.46178(6) 0.0338(3) Uani 1.000000 .
O004 O 0.60873(8) 0.58837(6) 0.68763(6) 0.0330(3) Uani 1.000000 .
N005 N 0.38031(8) 0.69492(6) 0.40357(7) 0.0248(3) Uani 1.000000 .
N006 N 0.61879(9) 0.69119(6) 0.62910(7) 0.0246(3) Uani 1.000000 .
N007 N 0.38299(11) 0.77504(7) 0.15615(8) 0.0364(3) Uani 1.000000 .
N008 N 0.61405(10) 0.76819(7) 0.38066(8) 0.0371(3) Uani 1.000000 .
C009 C 0.63097(9) 0.62387(7) 0.49465(8) 0.0236(3) Uani 1.000000 .
C00A C 0.29768(11) 0.57217(8) 0.07959(8) 0.0281(3) Uani 1.000000 .
C00B C 0.62736(10) 0.69535(7) 0.49773(8) 0.0250(3) Uani 1.000000 .
C00C C 0.64133(10) 0.58756(7) 0.42380(8) 0.0241(3) Uani 1.000000 .
C00D C 0.70789(10) 0.60859(7) 0.37215(8) 0.0270(3) Uani 1.000000 .
C00E C 0.37490(10) 0.62904(7) 0.26838(8) 0.0238(3) Uani 1.000000 .
C00F C 0.71802(11) 0.57423(8) 0.30628(8) 0.0280(3) Uani 1.000000 .
C00G C 0.37004(10) 0.59251(7) 0.19752(8) 0.0244(3) Uani 1.000000 .
C00H C 0.30342(10) 0.60897(7) 0.14427(8) 0.0263(3) Uani 1.000000 .
C00I C 0.38144(10) 0.62185(7) 0.40288(8) 0.0258(3) Uani 1.000000 .
C00J C 0.62539(10) 0.58754(8) 0.55891(9) 0.0256(3) Uani 1.000000 .
C00K C 0.37668(10) 0.73374(7) 0.34023(8) 0.0250(3) Uani 1.000000 .
C00L C 0.37405(10) 0.70067(7) 0.27223(9) 0.0251(3) Uani 1.000000 .
C00M C 0.58641(11) 0.53070(8) 0.40904(8) 0.0264(3) Uani 1.000000 .
C00N C 0.59483(11) 0.49658(8) 0.34294(8) 0.0290(3) Uani 1.000000 .
C00O C 0.37947(10) 0.59207(8) 0.33228(8) 0.0256(3) Uani 1.000000 .
C00P C 0.62244(10) 0.72916(7) 0.56520(9) 0.0248(3) Uani 1.000000 .
C00Q C 0.62118(11) 0.73539(8) 0.43241(9) 0.0275(3) Uani 1.000000 .
C00R C 0.65981(11) 0.51950(7) 0.29230(8) 0.0264(3) Uani 1.000000 .
C00S C 0.61669(10) 0.61813(7) 0.62877(9) 0.0261(3) Uani 1.000000 .
C00T C 0.37800(11) 0.74144(7) 0.20758(9) 0.0273(3) Uani 1.000000 .
C00U C 0.61593(11) 0.72255(8) 0.69703(9) 0.0297(3) Uani 1.000000 .
C00V C 0.43035(11) 0.53770(8) 0.18519(9) 0.0292(3) Uani 1.000000 .
C00W C 0.38386(12) 0.72547(9) 0.47211(9) 0.0306(4) Uani 1.000000 .
C00X C 0.42675(12) 0.50172(8) 0.12046(9) 0.0336(4) Uani 1.000000 .
C00Y C 0.37499(12) 0.80486(8) 0.34828(10) 0.0327(4) Uani 1.000000 .
C00Z C 0.36064(11) 0.51999(7) 0.06827(9) 0.0284(3) Uani 1.000000 .
C010 C 0.62183(12) 0.80063(8) 0.57233(10) 0.0323(4) Uani 1.000000 .
C011 C 0.61669(13) 0.79044(9) 0.70306(10) 0.0348(4) Uani 1.000000 .
C012 C 0.37738(14) 0.83437(8) 0.41540(11) 0.0384(4) Uani 1.000000 .
C013 C 0.61955(13) 0.83093(8) 0.63925(10) 0.0375(4) Uani 1.000000 .
C014 C 0.38273(13) 0.79331(9) 0.47894(10) 0.0376(4) Uani 1.000000 .
H00V H 0.4759(13) 0.5266(8) 0.2224(10) 0.030(5) Uiso 1.000000 .
H00A H 0.2509(13) 0.5828(8) 0.0435(10) 0.032(5) Uiso 1.000000 .
H00M H 0.5395(13) 0.5158(8) 0.4456(10) 0.028(4) Uiso 1.000000 .
H00F H 0.7646(12) 0.5873(8) 0.2719(10) 0.033(5) Uiso 1.000000 .
H00D H 0.7494(13) 0.6468(9) 0.3828(10) 0.037(4) Uiso 1.000000 .
H00X H 0.4740(15) 0.4658(10) 0.1109(11) 0.050(6) Uiso 1.000000 .
H00O H 0.3786(12) 0.5401(9) 0.3315(9) 0.028(4) Uiso 1.000000 .
H00H H 0.2569(15) 0.6450(9) 0.1550(10) 0.045(5) Uiso 1.000000 .
H00N H 0.5566(13) 0.4571(9) 0.3317(10) 0.039(5) Uiso 1.000000 .
H00W H 0.3858(13) 0.6944(9) 0.5120(10) 0.030(5) Uiso 1.000000 .
H00U H 0.6127(12) 0.6912(9) 0.7364(11) 0.030(4) Uiso 1.000000 .
H00J H 0.6322(12) 0.5366(9) 0.5597(10) 0.024(4) Uiso 1.000000 .
H00Y H 0.3721(15) 0.8349(11) 0.3046(13) 0.049(6) Uiso 1.000000 .
H012 H 0.3782(14) 0.8835(10) 0.4209(12) 0.043(5) Uiso 1.000000 .
H010 H 0.6208(16) 0.8287(12) 0.5286(14) 0.057(7) Uiso 1.000000 .
H013 H 0.6180(14) 0.8807(10) 0.6436(11) 0.042(5) Uiso 1.000000 .
H014 H 0.3868(15) 0.8117(10) 0.5300(12) 0.048(6) Uiso 1.000000 .
H011 H 0.6125(13) 0.8097(10) 0.7549(12) 0.042(5) Uiso 1.000000 .


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
Cl01 C00R 1.7428(15) . ?
Cl02 C00Z 1.7446(16) . ?
O003 C00I 1.2291(18) . ?
O004 C00S 1.2295(18) . ?
N005 C00I 1.4441(19) . ?
N005 C00K 1.3879(19) . ?
N005 C00W 1.3895(19) . ?
N006 C00P 1.3874(19) . ?
N006 C00S 1.4441(19) . ?
N006 C00U 1.386(2) . ?
N007 C00T 1.152(2) . ?
N008 C00Q 1.150(2) . ?
C009 C00B 1.415(2) . ?
C009 C00C 1.486(2) . ?
C009 C00J 1.377(2) . ?
C00A C00H 1.388(2) . ?
C00A C00Z 1.380(2) . ?
C00A H00A 0.958(18) . ?
C00B C00P 1.402(2) . ?
C00B C00Q 1.433(2) . ?
C00C C00D 1.397(2) . ?
C00C C00M 1.393(2) . ?
C00D C00F 1.388(2) . ?
C00D H00D 0.977(18) . ?
C00E C00G 1.482(2) . ?
C00E C00L 1.417(2) . ?
C00E C00O 1.377(2) . ?
C00F C00R 1.384(2) . ?
C00F H00F 0.947(18) . ?
C00G C00H 1.394(2) . ?
C00G C00V 1.398(2) . ?
C00H H00H 0.99(2) . ?
C00I C00O 1.416(2) . ?
C00J C00S 1.416(2) . ?
C00J H00J 1.011(17) . ?
C00K C00L 1.403(2) . ?
C00K C00Y 1.413(2) . ?
C00L C00T 1.429(2) . ?
C00M C00N 1.387(2) . ?
C00M H00M 0.987(18) . ?
C00N C00R 1.381(2) . ?
C00N H00N 0.972(19) . ?
C00O H00O 1.027(18) . ?
C00P C010 1.418(2) . ?
C00U C011 1.346(2) . ?
C00U H00U 0.950(19) . ?
C00V C00X 1.379(2) . ?
C00V H00V 0.962(18) . ?
C00W C014 1.346(2) . ?
C00W H00W 0.953(19) . ?
C00X C00Z 1.384(2) . ?
C00X H00X 0.99(2) . ?
C00Y C012 1.357(2) . ?
C00Y H00Y 0.99(2) . ?
C010 C013 1.360(2) . ?
C010 H010 0.97(2) . ?
C011 C013 1.413(2) . ?
C011 H011 1.02(2) . ?
C012 C014 1.417(3) . ?
C012 H012 0.98(2) . ?
C013 H013 0.99(2) . ?
C014 H014 1.00(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00K N005 C00I 123.08(12) . . ?
C00W N005 C00I 116.22(13) . . ?
C00W N005 C00K 120.70(13) . . ?
C00S N006 C00P 122.55(12) . . ?
C00U N006 C00P 120.70(13) . . ?
C00U N006 C00S 116.75(13) . . ?
C00C C009 C00B 121.37(13) . . ?
C00J C009 C00B 118.99(14) . . ?
C00J C009 C00C 119.64(13) . . ?
C00Z C00A C00H 118.74(14) . . ?
H00A C00A C00H 120.7(10) . . ?
H00A C00A C00Z 120.6(10) . . ?
C00P C00B C009 120.83(13) . . ?
C00Q C00B C009 121.36(14) . . ?
C00Q C00B C00P 117.63(13) . . ?
C00D C00C C009 120.66(13) . . ?
C00M C00C C009 120.16(13) . . ?
C00M C00C C00D 119.15(14) . . ?
C00F C00D C00C 120.57(13) . . ?
H00D C00D C00C 120.2(11) . . ?
H00D C00D C00F 119.2(11) . . ?
C00L C00E C00G 121.95(13) . . ?
C00O C00E C00G 118.82(12) . . ?
C00O C00E C00L 119.23(14) . . ?
C00R C00F C00D 118.70(14) . . ?
H00F C00F C00D 120.9(11) . . ?
H00F C00F C00R 120.4(11) . . ?
C00H C00G C00E 121.72(13) . . ?
C00V C00G C00E 119.29(13) . . ?
C00V C00G C00H 118.90(14) . . ?
C00G C00H C00A 120.66(14) . . ?
H00H C00H C00A 120.3(11) . . ?
H00H C00H C00G 118.8(11) . . ?
N005 C00I O003 118.53(13) . . ?
C00O C00I O003 126.42(14) . . ?
C00O C00I N005 115.04(13) . . ?
C00S C00J C009 123.28(14) . . ?
H00J C00J C009 121.7(10) . . ?
H00J C00J C00S 114.9(10) . . ?
C00L C00K N005 118.67(13) . . ?
C00Y C00K N005 117.63(13) . . ?
C00Y C00K C00L 123.69(14) . . ?
C00K C00L C00E 120.59(13) . . ?
C00T C00L C00E 121.45(14) . . ?
C00T C00L C00K 117.78(13) . . ?
C00N C00M C00C 120.80(14) . . ?
H00M C00M C00C 119.2(10) . . ?
H00M C00M C00N 120.0(10) . . ?
C00R C00N C00M 118.66(14) . . ?
H00N C00N C00M 121.7(11) . . ?
H00N C00N C00R 119.6(11) . . ?
C00I C00O C00E 123.38(14) . . ?
H00O C00O C00E 121.2(10) . . ?
H00O C00O C00I 115.4(10) . . ?
C00B C00P N006 118.80(13) . . ?
C010 C00P N006 117.47(14) . . ?
C010 C00P C00B 123.73(14) . . ?
C00B C00Q N008 178.23(16) . . ?
C00F C00R Cl01 118.65(12) . . ?
C00N C00R Cl01 119.30(12) . . ?
C00N C00R C00F 122.05(14) . . ?
N006 C00S O004 118.45(13) . . ?
C00J C00S O004 126.15(14) . . ?
C00J C00S N006 115.39(13) . . ?
C00L C00T N007 178.40(17) . . ?
C011 C00U N006 121.23(15) . . ?
H00U C00U N006 112.7(11) . . ?
H00U C00U C011 126.1(11) . . ?
C00X C00V C00G 120.96(14) . . ?
H00V C00V C00G 118.3(10) . . ?
H00V C00V C00X 120.7(10) . . ?
C014 C00W N005 121.03(15) . . ?
H00W C00W N005 114.1(11) . . ?
H00W C00W C014 124.8(11) . . ?
C00Z C00X C00V 118.66(14) . . ?
H00X C00X C00V 119.7(12) . . ?
H00X C00X C00Z 121.5(12) . . ?
C012 C00Y C00K 121.38(16) . . ?
H00Y C00Y C00K 120.7(12) . . ?
H00Y C00Y C012 117.9(13) . . ?
C00A C00Z Cl02 118.78(12) . . ?
C00X C00Z Cl02 119.20(12) . . ?
C00X C00Z C00A 122.03(14) . . ?
C013 C010 C00P 121.39(15) . . ?
H010 C010 C00P 119.5(14) . . ?
H010 C010 C013 119.1(14) . . ?
C013 C011 C00U 119.82(16) . . ?
H011 C011 C00U 116.6(11) . . ?
H011 C011 C013 123.6(11) . . ?
C014 C012 C00Y 119.58(16) . . ?
H012 C012 C00Y 121.4(13) . . ?
H012 C012 C014 119.0(13) . . ?
C011 C013 C010 119.39(15) . . ?
H013 C013 C010 120.8(12) . . ?
H013 C013 C011 119.8(12) . . ?
C012 C014 C00W 119.67(16) . . ?
H014 C014 C00W 116.5(12) . . ?
H014 C014 C012 123.8(12) . . ?

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
Cl01 C00R C00F C00D 177.03(11) . . . . ?
Cl01 C00R C00N C00M -178.02(11) . . . . ?
Cl02 C00Z C00A C00H -177.59(11) . . . . ?
Cl02 C00Z C00X C00V 179.04(12) . . . . ?
O003 C00I N005 C00K -178.65(13) . . . . ?
O003 C00I N005 C00W 1.86(16) . . . . ?
O003 C00I C00O C00E 177.90(15) . . . . ?
O004 C00S N006 C00P -176.43(13) . . . . ?
O004 C00S N006 C00U 2.87(16) . . . . ?
O004 C00S C00J C009 177.79(15) . . . . ?
N005 C00I C00O C00E -1.26(15) . . . . ?
N005 C00K C00L C00E 0.13(16) . . . . ?
N005 C00K C00L C00T -175.07(13) . . . . ?
N005 C00K C00Y C012 0.39(17) . . . . ?
N005 C00W C014 C012 0.31(19) . . . . ?
N006 C00P C00B C009 -1.59(16) . . . . ?
N006 C00P C00B C00Q 173.66(12) . . . . ?
N006 C00P C010 C013 1.21(17) . . . . ?
N006 C00S C00J C009 -3.02(16) . . . . ?
N006 C00U C011 C013 0.61(18) . . . . ?
C009 C00B C00P C010 177.80(14) . . . . ?
C009 C00C C00D C00F 179.43(13) . . . . ?
C009 C00C C00M C00N 179.54(13) . . . . ?
C00A C00H C00G C00E -177.28(13) . . . . ?
C00A C00H C00G C00V -0.81(17) . . . . ?
C00A C00Z C00X C00V -1.01(17) . . . . ?
C00B C00P C010 C013 -178.19(16) . . . . ?
C00C C00D C00F C00R 1.09(17) . . . . ?
C00C C00M C00N C00R 0.92(17) . . . . ?
C00D C00F C00R C00N -2.58(17) . . . . ?
C00E C00G C00V C00X 178.85(14) . . . . ?
C00E C00L C00K C00Y -179.28(14) . . . . ?
C00F C00R C00N C00M 1.58(17) . . . . ?
C00G C00V C00X C00Z -1.40(18) . . . . ?
C00K C00Y C012 C014 0.7(2) . . . . ?
C00P C010 C013 C011 -0.7(2) . . . . ?
C00U C011 C013 C010 -0.2(2) . . . . ?
C00W C014 C012 C00Y -1.1(2) . . . . ?


_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 2.587
_oxdiff_exptl_absorpt_empirical_full_min 0.326
_chemical_name_systematic        
2-(3-Chlorophenyl)-4-oxo-4H-quinolizine-1-carbonitrile
