# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_sliu11cult_auto
_database_code_depnum_ccdc_archive 'CCDC 2289407'
loop_
_audit_author_name
_audit_author_address
'Huang Hai'
;changzhou university
China
;
_audit_update_record             
;
2023-08-18 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 Cl N O3'
_chemical_formula_sum            'C17 H12 Cl N O3'
_chemical_formula_weight         313.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H28 Cl O N'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.33774(13)
_cell_length_b                   12.11111(16)
_cell_length_c                   12.88123(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.4445(14)
_cell_angle_gamma                90
_cell_volume                     1397.15(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6190
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.9170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8023
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.102
_diffrn_reflns_theta_min         4.938
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00 115.00   1.00    2.00    --   39.95  37.00 150.00   99
  2  ω    -20.00  74.00   1.00    2.00    --   39.95 -77.00-120.00   94
  3  ω    -30.00  62.00   1.00    2.00    --   39.95 -37.00 -30.00   92
  4  ω     80.00 178.00   1.00    3.50    --  107.44  30.00  60.00   98
  5  ω     37.00 137.00   1.00    3.50    --  107.44 -61.00 -30.00  100
  6  ω     77.00 176.00   1.00    3.50    --  107.44  30.00 150.00   99
  7  ω     24.00  66.00   1.00    3.50    --  107.44 -94.00 -60.00   42
  8  ω     63.00 146.00   1.00    3.50    --  107.44 178.00 -60.00   83
  9  ω     79.00 109.00   1.00    3.50    --  107.44-111.00  60.00   30
 10  ω     79.00 104.00   1.00    3.50    --  107.44 -94.00 -60.00   25
 11  ω     29.00 109.00   1.00    3.50    --  107.44-111.00 -90.00   80
 12  ω     61.00 138.00   1.00    3.50    --  107.44 -61.00  60.00   77
 13  ω    110.00 165.00   1.00    3.50    --  107.44 111.00  90.00   55
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0702944000
_diffrn_orient_matrix_UB_12      0.0254561000
_diffrn_orient_matrix_UB_13      -0.0920519000
_diffrn_orient_matrix_UB_21      -0.0813597000
_diffrn_orient_matrix_UB_22      0.1119933000
_diffrn_orient_matrix_UB_23      -0.0190784000
_diffrn_orient_matrix_UB_31      0.1342149000
_diffrn_orient_matrix_UB_32      0.0547267000
_diffrn_orient_matrix_UB_33      0.0819836000
_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_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2632
_reflns_number_total             2780
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.10736(3) 0.52221(2) 0.28482(2) 0.02170(10) Uani 1 1 d . . . . .
O1 O 0.50261(10) 0.33694(7) 0.03483(7) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.32056(10) 0.33731(8) 0.32779(7) 0.0230(2) Uani 1 1 d . . . . .
O3 O 0.33384(9) 0.44793(7) 0.07912(7) 0.01542(18) Uani 1 1 d . . . . .
N1 N 0.43491(11) 0.31218(8) 0.19293(8) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.43336(13) 0.36083(10) 0.09649(10) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.33962(13) 0.36406(10) 0.24262(10) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.27230(13) 0.45436(10) 0.16514(9) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.16776(13) 0.52918(9) 0.16953(9) 0.0153(2) Uani 1 1 d . . . . .
C5 C 0.09782(12) 0.61486(9) 0.08949(9) 0.0146(2) Uani 1 1 d . . . . .
C6 C 0.15602(13) 0.64211(10) 0.00359(10) 0.0177(2) Uani 1 1 d . . . . .
H6 H 0.2433 0.6061 -0.0032 0.021 Uiso 1 1 calc R U . . .
C7 C 0.08619(14) 0.72165(10) -0.07152(10) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.1257 0.7391 -0.1299 0.024 Uiso 1 1 calc R U . . .
C8 C -0.04101(14) 0.77614(10) -0.06235(10) 0.0193(3) Uani 1 1 d . . . . .
H8 H -0.0885 0.8300 -0.1143 0.023 Uiso 1 1 calc R U . . .
C9 C -0.09765(13) 0.75102(10) 0.02323(10) 0.0195(2) Uani 1 1 d . . . . .
H9 H -0.1835 0.7887 0.0306 0.023 Uiso 1 1 calc R U . . .
C10 C -0.02953(13) 0.67093(10) 0.09842(10) 0.0178(2) Uani 1 1 d . . . . .
H10 H -0.0698 0.6540 0.1565 0.021 Uiso 1 1 calc R U . . .
C11 C 0.52200(13) 0.21291(10) 0.23602(10) 0.0187(2) Uani 1 1 d . . . . .
H11A H 0.5597 0.2184 0.3158 0.022 Uiso 1 1 calc R U . . .
H11B H 0.6091 0.2079 0.2068 0.022 Uiso 1 1 calc R U . . .
C12 C 0.42768(12) 0.11012(10) 0.20578(9) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.35785(13) 0.06575(10) 0.27862(10) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.3735 0.0980 0.3482 0.021 Uiso 1 1 calc R U . . .
C14 C 0.26512(14) -0.02587(10) 0.24949(11) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.2173 -0.0559 0.2991 0.025 Uiso 1 1 calc R U . . .
C15 C 0.24238(14) -0.07340(10) 0.14803(11) 0.0231(3) Uani 1 1 d . . . . .
H15 H 0.1786 -0.1356 0.1281 0.028 Uiso 1 1 calc R U . . .
C16 C 0.31283(15) -0.03002(11) 0.07597(10) 0.0232(3) Uani 1 1 d . . . . .
H16 H 0.2981 -0.0631 0.0069 0.028 Uiso 1 1 calc R U . . .
C17 C 0.40503(14) 0.06175(10) 0.10416(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.4526 0.0915 0.0542 0.024 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
Cl1 C4 1.7334(12) . ?
O1 C1 1.1931(15) . ?
O2 C2 1.2045(15) . ?
O3 C1 1.3816(14) . ?
O3 C3 1.3873(14) . ?
N1 C1 1.3713(15) . ?
N1 C2 1.3851(16) . ?
N1 C11 1.4694(15) . ?
C2 C3 1.4939(16) . ?
C3 C4 1.3448(17) . ?
C4 C5 1.4783(16) . ?
C5 C6 1.4032(17) . ?
C5 C10 1.4021(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3900(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3927(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3849(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3909(17) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5109(16) . ?
C12 C13 1.3932(17) . ?
C12 C17 1.3945(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3920(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3898(18) . ?
C17 H17 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
C1 O3 C3 108.98(9) . . ?
C1 N1 C2 112.35(10) . . ?
C1 N1 C11 123.81(10) . . ?
C2 N1 C11 123.77(10) . . ?
O1 C1 O3 122.94(11) . . ?
O1 C1 N1 129.06(11) . . ?
N1 C1 O3 108.00(10) . . ?
O2 C2 N1 125.36(11) . . ?
O2 C2 C3 131.50(11) . . ?
N1 C2 C3 103.14(10) . . ?
O3 C3 C2 107.54(10) . . ?
C4 C3 O3 122.76(10) . . ?
C4 C3 C2 129.67(11) . . ?
C3 C4 Cl1 114.79(9) . . ?
C3 C4 C5 128.78(11) . . ?
C5 C4 Cl1 116.43(9) . . ?
C6 C5 C4 121.45(10) . . ?
C10 C5 C4 120.02(11) . . ?
C10 C5 C6 118.53(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.12(11) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.84(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.37(11) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.34(11) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.79(11) . . ?
C9 C10 H10 119.6 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 C12 110.91(9) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C13 C12 C11 119.61(11) . . ?
C13 C12 C17 119.64(11) . . ?
C17 C12 C11 120.70(11) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.00(11) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.13(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.92(12) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.35(12) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 119.95(12) . . ?
C16 C17 H17 120.0 . . ?

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
Cl1 C4 C5 C6 168.04(9) . . . . ?
Cl1 C4 C5 C10 -11.95(14) . . . . ?
O2 C2 C3 O3 -179.84(12) . . . . ?
O2 C2 C3 C4 -1.9(2) . . . . ?
O3 C3 C4 Cl1 -179.82(8) . . . . ?
O3 C3 C4 C5 0.70(19) . . . . ?
N1 C2 C3 O3 -0.45(12) . . . . ?
N1 C2 C3 C4 177.54(12) . . . . ?
N1 C11 C12 C13 -95.59(13) . . . . ?
N1 C11 C12 C17 81.87(14) . . . . ?
C1 O3 C3 C2 0.26(12) . . . . ?
C1 O3 C3 C4 -177.90(11) . . . . ?
C1 N1 C2 O2 179.93(11) . . . . ?
C1 N1 C2 C3 0.49(13) . . . . ?
C1 N1 C11 C12 -94.88(13) . . . . ?
C2 N1 C1 O1 179.42(12) . . . . ?
C2 N1 C1 O3 -0.36(13) . . . . ?
C2 N1 C11 C12 81.91(14) . . . . ?
C2 C3 C4 Cl1 2.46(17) . . . . ?
C2 C3 C4 C5 -177.02(11) . . . . ?
C3 O3 C1 O1 -179.76(11) . . . . ?
C3 O3 C1 N1 0.05(12) . . . . ?
C3 C4 C5 C6 -12.49(19) . . . . ?
C3 C4 C5 C10 167.52(12) . . . . ?
C4 C5 C6 C7 178.84(11) . . . . ?
C4 C5 C10 C9 -179.37(11) . . . . ?
C5 C6 C7 C8 0.64(19) . . . . ?
C6 C5 C10 C9 0.64(17) . . . . ?
C6 C7 C8 C9 0.44(18) . . . . ?
C7 C8 C9 C10 -0.97(18) . . . . ?
C8 C9 C10 C5 0.43(18) . . . . ?
C10 C5 C6 C7 -1.17(17) . . . . ?
C11 N1 C1 O1 -3.46(19) . . . . ?
C11 N1 C1 O3 176.75(9) . . . . ?
C11 N1 C2 O2 2.82(19) . . . . ?
C11 N1 C2 C3 -176.62(10) . . . . ?
C11 C12 C13 C14 176.99(10) . . . . ?
C11 C12 C17 C16 -177.27(11) . . . . ?
C12 C13 C14 C15 0.20(18) . . . . ?
C13 C12 C17 C16 0.19(17) . . . . ?
C13 C14 C15 C16 0.41(19) . . . . ?
C14 C15 C16 C17 -0.72(19) . . . . ?
C15 C16 C17 C12 0.42(19) . . . . ?
C17 C12 C13 C14 -0.49(17) . . . . ?

_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.604
####################################################################### 
# 
# 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_20151201NGD_0m
_database_code_depnum_ccdc_archive 'CCDC 2289645'
loop_
_audit_author_name
_audit_author_address
Huanghai
;changzhou university
China
;
_audit_update_record             
;
2023-08-20 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 N2 O6'
_chemical_formula_weight         528.50

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.8680(10)
_cell_length_b                   8.3809(4)
_cell_length_c                   16.6626(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.2585(14)
_cell_angle_gamma                90
_cell_volume                     2488.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8557
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2189
_reflns_number_gt                1874
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+1.7255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2189
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.56575(9) 0.65697(19) 0.19919(11) 0.0318(4) Uani 1 1 d . . . . .
H1 H 0.5956 0.6330 0.2591 0.038 Uiso 1 1 calc R U . . .
C2 C 0.58727(9) 0.77816(19) 0.15951(12) 0.0348(4) Uani 1 1 d . . . . .
H2 H 0.6312 0.8347 0.1927 0.042 Uiso 1 1 calc R U . . .
C3 C 0.54413(9) 0.81566(18) 0.07120(11) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.5585 0.8976 0.0444 0.034 Uiso 1 1 calc R U . . .
C4 C 0.47929(9) 0.73055(19) 0.02260(11) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.4501 0.7549 -0.0374 0.038 Uiso 1 1 calc R U . . .
C5 C 0.45716(9) 0.60937(18) 0.06205(11) 0.0287(4) Uani 1 1 d . . . . .
H5 H 0.4130 0.5540 0.0285 0.034 Uiso 1 1 calc R U . . .
C6 C 0.50030(8) 0.56942(16) 0.15155(10) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.48003(7) 0.44407(16) 0.19966(9) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.42675(8) 0.33234(16) 0.16057(10) 0.0208(3) Uani 1 1 d . . . . .
C9 C 0.39736(8) 0.21032(16) 0.20081(10) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.33963(8) 0.18863(16) 0.04793(10) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.29998(8) -0.00433(16) 0.13098(10) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.31340(9) -0.15430(17) 0.10703(10) 0.0285(4) Uani 1 1 d . . . . .
H16 H 0.3508 -0.1701 0.0886 0.034 Uiso 1 1 calc R U . . .
C15 C 0.27002(10) -0.28115(18) 0.11104(11) 0.0344(4) Uani 1 1 d . . . . .
H15 H 0.2779 -0.3828 0.0945 0.041 Uiso 1 1 calc R U . . .
C14 C 0.21544(10) -0.2570(2) 0.13947(11) 0.0360(4) Uani 1 1 d . . . . .
H14 H 0.1872 -0.3428 0.1430 0.043 Uiso 1 1 calc R U . . .
C13 C 0.20249(9) -0.1057(2) 0.16280(12) 0.0356(4) Uani 1 1 d . . . . .
H13 H 0.1655 -0.0901 0.1819 0.043 Uiso 1 1 calc R U . . .
C12 C 0.24435(8) 0.02252(19) 0.15783(11) 0.0287(4) Uani 1 1 d . . . . .
H12 H 0.2352 0.1248 0.1723 0.034 Uiso 1 1 calc R U . . .
N1 N 0.34515(7) 0.12747(14) 0.12736(8) 0.0224(3) Uani 1 1 d . . . . .
O1 O 0.41228(6) 0.18437(12) 0.27822(7) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.30123(6) 0.14535(12) -0.02670(7) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.38831(6) 0.31440(12) 0.06790(7) 0.0240(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(2) . ?
C1 C6 1.395(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(2) . ?
C7 C8 1.346(2) . ?
C7 C7 1.505(3) 2_655 ?
C8 O3 1.3952(17) . ?
C8 C9 1.477(2) . ?
C9 O1 1.2085(18) . ?
C9 N1 1.3902(19) . ?
C10 O2 1.1919(18) . ?
C10 O3 1.3684(17) . ?
C10 N1 1.378(2) . ?
C11 C16 1.380(2) . ?
C11 C12 1.382(2) . ?
C11 N1 1.4412(18) . ?
C16 C15 1.389(2) . ?
C16 H16 0.9300 . ?
C15 C14 1.377(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.383(2) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.55(15) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C3 C2 C1 120.25(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.30(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.77(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.73(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 117.39(14) . . ?
C5 C6 C7 124.34(13) . . ?
C1 C6 C7 118.24(13) . . ?
C8 C7 C6 125.13(13) . . ?
C8 C7 C7 116.95(12) . 2_655 ?
C6 C7 C7 117.88(11) . 2_655 ?
C7 C8 O3 122.60(13) . . ?
C7 C8 C9 130.24(13) . . ?
O3 C8 C9 107.16(11) . . ?
O1 C9 N1 125.80(13) . . ?
O1 C9 C8 130.49(13) . . ?
N1 C9 C8 103.71(12) . . ?
O2 C10 O3 123.06(14) . . ?
O2 C10 N1 129.14(14) . . ?
O3 C10 N1 107.80(12) . . ?
C16 C11 C12 121.77(14) . . ?
C16 C11 N1 118.84(13) . . ?
C12 C11 N1 119.39(13) . . ?
C11 C16 C15 118.68(16) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C14 C15 C16 120.27(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C14 C13 120.26(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C12 C13 C14 120.24(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C11 C12 C13 118.75(15) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C10 N1 C9 111.79(12) . . ?
C10 N1 C11 122.61(12) . . ?
C9 N1 C11 125.58(12) . . ?
C10 O3 C8 109.52(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 178.57(14) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C1 C6 C7 -178.37(15) . . . . ?
C5 C6 C7 C8 14.0(2) . . . . ?
C1 C6 C7 C8 -167.92(14) . . . . ?
C5 C6 C7 C7 -163.76(15) . . . 2_655 ?
C1 C6 C7 C7 14.3(2) . . . 2_655 ?
C6 C7 C8 O3 5.5(2) . . . . ?
C7 C7 C8 O3 -176.68(12) 2_655 . . . ?
C6 C7 C8 C9 -174.55(13) . . . . ?
C7 C7 C8 C9 3.2(2) 2_655 . . . ?
C7 C8 C9 O1 2.6(3) . . . . ?
O3 C8 C9 O1 -177.49(14) . . . . ?
C7 C8 C9 N1 -178.23(14) . . . . ?
O3 C8 C9 N1 1.69(14) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
N1 C11 C16 C15 179.67(13) . . . . ?
C11 C16 C15 C14 -0.8(2) . . . . ?
C16 C15 C14 C13 1.1(2) . . . . ?
C15 C14 C13 C12 -0.1(3) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
N1 C11 C12 C13 -178.65(14) . . . . ?
C14 C13 C12 C11 -1.3(2) . . . . ?
O2 C10 N1 C9 179.21(15) . . . . ?
O3 C10 N1 C9 -0.27(16) . . . . ?
O2 C10 N1 C11 -2.1(2) . . . . ?
O3 C10 N1 C11 178.39(12) . . . . ?
O1 C9 N1 C10 178.35(14) . . . . ?
C8 C9 N1 C10 -0.88(15) . . . . ?
O1 C9 N1 C11 -0.3(2) . . . . ?
C8 C9 N1 C11 -179.50(12) . . . . ?
C16 C11 N1 C10 69.74(18) . . . . ?
C12 C11 N1 C10 -109.98(17) . . . . ?
C16 C11 N1 C9 -111.79(16) . . . . ?
C12 C11 N1 C9 68.49(19) . . . . ?
O2 C10 O3 C8 -178.11(13) . . . . ?
N1 C10 O3 C8 1.40(15) . . . . ?
C7 C8 O3 C10 177.99(13) . . . . ?
C9 C8 O3 C10 -1.94(14) . . . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046



