# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sxj-s-459-tm2
_database_code_depnum_ccdc_archive 'CCDC 1935306'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.06(C23 H14 N2 O2)'
_chemical_formula_sum            'C1.42 H0.86 N0.12 O0.12'
_chemical_formula_weight         21.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   13.7590(17)
_cell_length_b                   9.4936(8)
_cell_length_c                   13.7713(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.908(12)
_cell_angle_gamma                90
_cell_volume                     1738.3(3)
_cell_formula_units_Z            65
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.8590
_cell_measurement_theta_min      4.2950
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.705
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5862
_diffrn_reflns_point_group_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.846
_diffrn_reflns_theta_min         3.732
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6062
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.705
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  95.00   1.00  233.43    --   11.85-178.00 -60.00   41
  2  ω      2.00  62.00   1.00  233.43    --  -12.09  77.00  60.00   60
  3  ω    -36.00  -4.00   1.00  233.43    --  -12.09  77.00  60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0219118000
_diffrn_orient_matrix_UB_12      0.0545168000
_diffrn_orient_matrix_UB_13      0.0337800000
_diffrn_orient_matrix_UB_21      0.0086990000
_diffrn_orient_matrix_UB_22      -0.0484688000
_diffrn_orient_matrix_UB_23      0.0405174000
_diffrn_orient_matrix_UB_31      0.0478340000
_diffrn_orient_matrix_UB_32      -0.0161533000
_diffrn_orient_matrix_UB_33      -0.0076306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2317
_reflns_number_total             3530
_reflns_odcompleteness_completeness 85.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_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), C6(H6), C7(H7), C8(H8), C14(H14), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
C1 C 0.23982(15) 0.2446(2) 0.28030(15) 0.0391(5) Uani 1 1 d . . . . .
C2 C 0.25680(17) 0.2951(3) 0.19441(17) 0.0542(6) Uani 1 1 d . . . . .
H2 H 0.314151 0.348443 0.197203 0.065 Uiso 1 1 calc R . . . .
C3 C 0.1893(2) 0.2684(3) 0.10142(17) 0.0629(7) Uani 1 1 d . . . . .
H3 H 0.202059 0.303535 0.042874 0.075 Uiso 1 1 calc R . . . .
C4 C 0.10554(19) 0.1913(3) 0.09664(16) 0.0587(7) Uani 1 1 d . . . . .
H4 H 0.061225 0.173748 0.034429 0.070 Uiso 1 1 calc R . . . .
C5 C 0.08410(16) 0.1371(2) 0.18419(16) 0.0461(5) Uani 1 1 d . . . . .
C6 C -0.00311(18) 0.0616(3) 0.1850(2) 0.0656(7) Uani 1 1 d . . . . .
H6 H -0.050883 0.043141 0.125034 0.079 Uiso 1 1 calc R . . . .
C7 C -0.0176(2) 0.0159(3) 0.2723(2) 0.0790(9) Uani 1 1 d . . . . .
H7 H -0.075484 -0.034132 0.273278 0.095 Uiso 1 1 calc R . . . .
C8 C 0.0550(2) 0.0440(3) 0.3622(2) 0.0773(9) Uani 1 1 d . . . . .
H8 H 0.043812 0.010375 0.421854 0.093 Uiso 1 1 calc R . . . .
C9 C 0.15331(15) 0.1630(2) 0.27905(14) 0.0401(5) Uani 1 1 d . . . . .
C10 C 0.38351(15) 0.1957(2) 0.43074(15) 0.0414(5) Uani 1 1 d . . . . .
C11 C 0.29829(16) 0.4078(2) 0.42475(16) 0.0448(5) Uani 1 1 d . . . . .
C12 C 0.37978(15) 0.4041(2) 0.51954(15) 0.0403(5) Uani 1 1 d . . . . .
C13 C 0.43142(14) 0.2783(2) 0.52251(15) 0.0376(5) Uani 1 1 d . . . . .
C14 C 0.51273(15) 0.2470(2) 0.60197(15) 0.0415(5) Uani 1 1 d . . . . .
H14 H 0.547076 0.162295 0.603911 0.050 Uiso 1 1 calc R . . . .
C15 C 0.54233(15) 0.3457(2) 0.67957(15) 0.0399(5) Uani 1 1 d . . . . .
C16 C 0.48770(17) 0.4703(2) 0.67492(17) 0.0496(6) Uani 1 1 d . . . . .
H16 H 0.506532 0.534835 0.727229 0.060 Uiso 1 1 calc R . . . .
C17 C 0.40628(17) 0.5013(2) 0.59491(17) 0.0522(6) Uani 1 1 d . . . . .
H17 H 0.370925 0.585220 0.592596 0.063 Uiso 1 1 calc R . . . .
C18 C 0.63137(16) 0.3203(2) 0.76602(15) 0.0437(5) Uani 1 1 d . . . . .
C19 C 0.63566(18) 0.3747(2) 0.86107(16) 0.0511(6) Uani 1 1 d . . . . .
H19 H 0.580973 0.424316 0.871547 0.061 Uiso 1 1 calc R . . . .
C20 C 0.7201(2) 0.3558(3) 0.94001(18) 0.0621(7) Uani 1 1 d . . . . .
H20 H 0.722278 0.393400 1.002913 0.074 Uiso 1 1 calc R . . . .
C21 C 0.8007(2) 0.2812(3) 0.9251(2) 0.0725(8) Uani 1 1 d . . . . .
H21 H 0.857505 0.267782 0.978033 0.087 Uiso 1 1 calc R . . . .
C22 C 0.7974(2) 0.2267(3) 0.8324(2) 0.0758(9) Uani 1 1 d . . . . .
H22 H 0.852187 0.176395 0.822703 0.091 Uiso 1 1 calc R . . . .
C23 C 0.71363(18) 0.2457(3) 0.75273(19) 0.0606(7) Uani 1 1 d . . . . .
H23 H 0.712444 0.208232 0.690039 0.073 Uiso 1 1 calc R . . . .
N1 N 0.13867(15) 0.1159(2) 0.36692(13) 0.0571(5) Uani 1 1 d . . . . .
N2 N 0.30659(12) 0.28113(17) 0.37521(12) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.23607(13) 0.49713(17) 0.39447(13) 0.0674(5) Uani 1 1 d . . . . .
O2 O 0.40256(12) 0.07957(16) 0.40600(12) 0.0615(5) 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 1.351(3) . ?
C1 C9 1.416(3) . ?
C1 N2 1.434(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.353(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.410(3) . ?
C5 C6 1.400(3) . ?
C5 C9 1.426(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.341(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.402(4) . ?
C8 H8 0.9300 . ?
C8 N1 1.326(3) . ?
C9 N1 1.353(3) . ?
C10 C13 1.490(3) . ?
C10 N2 1.395(2) . ?
C10 O2 1.202(2) . ?
C11 C12 1.486(3) . ?
C11 N2 1.401(3) . ?
C11 O1 1.201(2) . ?
C12 C13 1.385(3) . ?
C12 C17 1.366(3) . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.400(3) . ?
C15 C16 1.395(3) . ?
C15 C18 1.492(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(3) . ?
C18 C23 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.367(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(3) . ?
C23 H23 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 C9 121.17(19) . . ?
C2 C1 N2 119.84(19) . . ?
C9 C1 N2 118.87(18) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C9 118.9(2) . . ?
C6 C5 C4 124.2(2) . . ?
C6 C5 C9 116.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 118.2 . . ?
N1 C8 C7 123.6(3) . . ?
N1 C8 H8 118.2 . . ?
C1 C9 C5 117.8(2) . . ?
N1 C9 C1 119.20(17) . . ?
N1 C9 C5 123.0(2) . . ?
N2 C10 C13 105.46(16) . . ?
O2 C10 C13 129.95(18) . . ?
O2 C10 N2 124.59(18) . . ?
N2 C11 C12 105.66(16) . . ?
O1 C11 C12 129.1(2) . . ?
O1 C11 N2 125.24(19) . . ?
C13 C12 C11 108.15(17) . . ?
C17 C12 C11 130.17(18) . . ?
C17 C12 C13 121.68(18) . . ?
C12 C13 C10 108.51(16) . . ?
C14 C13 C10 130.58(18) . . ?
C14 C13 C12 120.91(18) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.56(18) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C18 121.27(18) . . ?
C16 C15 C14 119.01(18) . . ?
C16 C15 C18 119.72(18) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.16(19) . . ?
C17 C16 H16 118.9 . . ?
C12 C17 C16 117.66(19) . . ?
C12 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C19 C18 C15 121.2(2) . . ?
C23 C18 C15 120.5(2) . . ?
C23 C18 C19 118.3(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C8 N1 C9 117.0(2) . . ?
C10 N2 C1 125.23(17) . . ?
C10 N2 C11 112.17(16) . . ?
C11 N2 C1 122.56(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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.860
####################################################################### 
# 
# 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_sxj-20170525-s-45-j
_database_code_depnum_ccdc_archive 'CCDC 1935307'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.57(C22 H14 N2 O)'
_chemical_formula_sum            'C12.57 H8 N1.14 O0.57'
_chemical_formula_weight         184.20
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.4387(7)
_cell_length_b                   9.6197(5)
_cell_length_c                   13.4146(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.572(6)
_cell_angle_gamma                90
_cell_volume                     1577.90(16)
_cell_formula_units_Z            7
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      72.7890
_cell_measurement_theta_min      7.1010
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4268
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.259
_diffrn_reflns_theta_min         7.074
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  41.00   1.00    1.50    --   40.30  77.00  90.00   33
  2  ω     95.00 154.00   1.00    5.00    --  107.14  77.00   0.00   59
  3  ω     94.00 178.00   1.00    5.00    --  107.14  30.00 -90.00   84
  4  ω     99.00 137.00   1.00    5.00    --  107.14 -77.00  60.00   38
  5  ω     76.00 129.00   1.00    5.00    --  107.14 -45.00  30.00   53
  6  ω     55.00  86.00   1.00    1.50    --   40.30-125.00   0.00   31
  7  ω     36.00 108.00   1.00    5.00    --  107.14 -61.00  30.00   72
  8  ω     41.00 109.00   1.00    5.00    --  107.14 -95.00 -30.00   68
  9  ω     35.00  60.00   1.00    5.00    --  107.14 -45.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0870856000
_diffrn_orient_matrix_UB_12      -0.0904865000
_diffrn_orient_matrix_UB_13      0.0369091000
_diffrn_orient_matrix_UB_21      -0.0360705000
_diffrn_orient_matrix_UB_22      -0.0575481000
_diffrn_orient_matrix_UB_23      -0.1081011000
_diffrn_orient_matrix_UB_31      0.0837242000
_diffrn_orient_matrix_UB_32      -0.1189601000
_diffrn_orient_matrix_UB_33      0.0240991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2034
_reflns_number_total             2664
_reflns_odcompleteness_completeness 83.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.051
_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)+(0.0596P)²+0.1593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1271
_refine_special_details          ?
_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), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.38930(13) 0.74531(18) 0.39028(12) 0.0478(4) Uani 1 1 d . . . . .
C2 C 0.48967(15) 0.7011(2) 0.37583(15) 0.0593(4) Uani 1 1 d . . . . .
H2 H 0.505753 0.606669 0.377120 0.071 Uiso 1 1 calc R . . . .
C3 C 0.56897(15) 0.7990(3) 0.35892(17) 0.0668(5) Uani 1 1 d . . . . .
H3 H 0.637008 0.768360 0.348646 0.080 Uiso 1 1 calc R . . . .
C4 C 0.54710(15) 0.9369(2) 0.35750(16) 0.0635(5) Uani 1 1 d . . . . .
H4 H 0.600279 0.999952 0.346283 0.076 Uiso 1 1 calc R . . . .
C5 C 0.44436(14) 0.98601(19) 0.37285(13) 0.0521(4) Uani 1 1 d . . . . .
C6 C 0.41753(18) 1.1283(2) 0.37300(16) 0.0636(5) Uani 1 1 d . . . . .
H6 H 0.468294 1.195515 0.363103 0.076 Uiso 1 1 calc R . . . .
C7 C 0.3167(2) 1.1657(2) 0.38777(19) 0.0708(5) Uani 1 1 d . . . . .
H7 H 0.296896 1.258976 0.387377 0.085 Uiso 1 1 calc R . . . .
C8 C 0.24286(17) 1.0626(2) 0.40358(19) 0.0675(5) Uani 1 1 d . . . . .
H8 H 0.174414 1.091049 0.414217 0.081 Uiso 1 1 calc R . . . .
C9 C 0.36360(13) 0.88878(17) 0.38958(12) 0.0471(4) Uani 1 1 d . . . . .
C10 C 0.22921(12) 0.60633(16) 0.31876(13) 0.0450(4) Uani 1 1 d . . . . .
C11 C 0.23616(14) 0.65754(18) 0.22256(14) 0.0527(4) Uani 1 1 d . . . . .
H11 H 0.291713 0.719283 0.215238 0.063 Uiso 1 1 calc R . . . .
C12 C 0.16166(16) 0.6175(2) 0.13876(14) 0.0582(4) Uani 1 1 d . . . . .
H12 H 0.167706 0.650928 0.074986 0.070 Uiso 1 1 calc R . . . .
C13 C 0.07728(18) 0.5270(2) 0.14917(16) 0.0638(5) Uani 1 1 d . . . . .
H13 H 0.026211 0.501004 0.092594 0.077 Uiso 1 1 calc R . . . .
C14 C 0.06956(15) 0.47599(19) 0.24324(15) 0.0570(4) Uani 1 1 d . . . . .
H14 H 0.012695 0.415698 0.249408 0.068 Uiso 1 1 calc R . . . .
C15 C 0.14527(13) 0.51253(16) 0.33038(14) 0.0472(4) Uani 1 1 d . . . . .
C16 C 0.14033(13) 0.46002(15) 0.43114(14) 0.0467(4) Uani 1 1 d . . . . .
C17 C 0.06104(15) 0.36379(17) 0.44933(16) 0.0554(4) Uani 1 1 d . . . . .
H17 H 0.010028 0.330112 0.395256 0.066 Uiso 1 1 calc R . . . .
C18 C 0.05801(16) 0.31891(19) 0.54605(18) 0.0616(5) Uani 1 1 d . . . . .
H18 H 0.004854 0.255413 0.556644 0.074 Uiso 1 1 calc R . . . .
C19 C 0.13349(17) 0.3673(2) 0.62827(17) 0.0629(5) Uani 1 1 d . . . . .
H19 H 0.130748 0.336402 0.693445 0.075 Uiso 1 1 calc R . . . .
C20 C 0.21223(16) 0.46119(19) 0.61268(15) 0.0572(4) Uani 1 1 d . . . . .
H20 H 0.262708 0.494204 0.667404 0.069 Uiso 1 1 calc R . . . .
C21 C 0.21630(13) 0.50685(16) 0.51463(14) 0.0472(4) Uani 1 1 d . . . . .
C22 C 0.30362(13) 0.60561(17) 0.50170(13) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.26231(12) 0.92855(16) 0.40464(13) 0.0566(4) Uani 1 1 d . . . . .
N2 N 0.30642(11) 0.64617(14) 0.40383(11) 0.0476(3) Uani 1 1 d . . . . .
O1 O 0.37111(12) 0.64848(16) 0.57353(10) 0.0666(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.366(2) . ?
C1 C9 1.416(2) . ?
C1 N2 1.440(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.413(3) . ?
C5 C6 1.409(3) . ?
C5 C9 1.420(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.354(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(3) . ?
C8 H8 0.9300 . ?
C8 N1 1.311(3) . ?
C9 N1 1.367(2) . ?
C10 C11 1.399(3) . ?
C10 C15 1.410(2) . ?
C10 N2 1.403(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(3) . ?
C15 C16 1.455(3) . ?
C16 C17 1.406(3) . ?
C16 C21 1.401(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.396(3) . ?
C21 C22 1.477(2) . ?
C22 N2 1.376(2) . ?
C22 O1 1.227(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
C2 C1 C9 120.88(16) . . ?
C2 C1 N2 120.40(16) . . ?
C9 C1 N2 118.70(14) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.95(18) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.75(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.71(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C9 119.19(17) . . ?
C6 C5 C4 123.10(17) . . ?
C6 C5 C9 117.71(17) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.96(18) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.13(19) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 117.4 . . ?
N1 C8 C7 125.17(19) . . ?
N1 C8 H8 117.4 . . ?
C1 C9 C5 118.52(15) . . ?
N1 C9 C1 119.00(15) . . ?
N1 C9 C5 122.47(16) . . ?
C11 C10 C15 119.98(16) . . ?
C11 C10 N2 120.34(15) . . ?
N2 C10 C15 119.67(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.62(17) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.12(18) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.81(18) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.73(18) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C16 118.90(15) . . ?
C14 C15 C10 117.72(17) . . ?
C14 C15 C16 123.37(16) . . ?
C17 C16 C15 122.71(16) . . ?
C21 C16 C15 119.60(15) . . ?
C21 C16 C17 117.69(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.81(18) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.79(17) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.66(19) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.96(19) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C22 121.05(16) . . ?
C20 C21 C16 121.08(16) . . ?
C20 C21 C22 117.87(16) . . ?
N2 C22 C21 116.25(15) . . ?
O1 C22 C21 122.39(16) . . ?
O1 C22 N2 121.36(15) . . ?
C8 N1 C9 116.54(16) . . ?
C10 N2 C1 118.50(14) . . ?
C22 N2 C1 116.88(14) . . ?
C22 N2 C10 124.41(14) . . ?

_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_sxj-s-503-tm1
_database_code_depnum_ccdc_archive 'CCDC 1935309'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.13(C23 H16 N2 O)'
_chemical_formula_sum            'C2.97 H2.06 N0.26 O0.13'
_chemical_formula_weight         43.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7470(4)
_cell_length_b                   7.5124(2)
_cell_length_c                   15.3583(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.412(3)
_cell_angle_gamma                90
_cell_volume                     1623.51(9)
_cell_formula_units_Z            31
_cell_measurement_reflns_used    3191
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.4200
_cell_measurement_theta_min      6.0190
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5733
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.693
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  32.00   1.00    2.54    --  -40.80  57.00 -30.00   56
  2  ω    -13.00  32.00   1.00    2.54    --  -40.80  38.00 -60.00   45
  3  ω    -65.00 -32.00   1.00    2.54    --  -40.80  38.00 -60.00   33
  4  ω    -62.00 -26.00   1.00    2.54    --  -40.80  57.00 -30.00   36
  5  ω     58.00  84.00   1.00    2.54    --   40.80-125.00  90.00   26
  6  ω     23.00  50.00   1.00    2.54    --   40.80-125.00  90.00   27
  7  ω     34.00 116.00   1.00   10.16    --  107.14 -45.00 -30.00   82
  8  ω    124.00 178.00   1.00   10.16    --  107.14  30.00   0.00   54
  9  ω    125.00 151.00   1.00   10.16    --  107.14 125.00 -30.00   26
 10  ω    129.00 171.00   1.00   10.16    --  107.14 125.00  30.00   42
 11  ω    137.00 163.00   1.00   10.16    --  107.14  45.00-150.00   26
 12  ω     72.00  97.00   1.00    2.54    --   40.80-125.00-180.00   25
 13  ω     29.00  54.00   1.00    2.54    --   40.80-125.00-180.00   25
 14  ω     34.00  78.00   1.00   10.16    --  107.14 -30.00-180.00   44
 15  ω     78.00 176.00   1.00   10.16    --  107.14  61.00 120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033713000
_diffrn_orient_matrix_UB_12      -0.1373566000
_diffrn_orient_matrix_UB_13      -0.0734096000
_diffrn_orient_matrix_UB_21      -0.1068600000
_diffrn_orient_matrix_UB_22      -0.0370181000
_diffrn_orient_matrix_UB_23      -0.0184042000
_diffrn_orient_matrix_UB_31      -0.0237057000
_diffrn_orient_matrix_UB_32      0.1476784000
_diffrn_orient_matrix_UB_33      -0.0729558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2685
_reflns_number_total             3102
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.026
_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)+(0.0565P)²+0.3237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          ?
_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:
 C11(H11), C21(H21), C13(H13), C20(H20), C12(H12), C2(H2), C18(H18), C19(H19),
 C4(H4), C3(H3), C8(H8), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
N1 N 0.70445(7) 0.20103(15) 0.45863(7) 0.0377(3) Uani 1 1 d . . . . .
O1 O 0.58766(8) 0.28752(19) 0.33333(7) 0.0634(3) Uani 1 1 d . . . . .
N2 N 0.80821(9) 0.51162(17) 0.47682(9) 0.0513(3) Uani 1 1 d . . . . .
C10 C 0.73724(9) 0.14220(17) 0.55024(8) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.77109(9) 0.2249(2) 0.40740(9) 0.0404(3) Uani 1 1 d . . . . .
C15 C 0.67337(9) 0.12620(17) 0.60288(8) 0.0352(3) Uani 1 1 d . . . . .
C17 C 0.57547(9) 0.18902(17) 0.56145(8) 0.0362(3) Uani 1 1 d . . . . .
C22 C 0.54628(9) 0.24107(17) 0.46954(8) 0.0368(3) Uani 1 1 d . . . . .
C14 C 0.70976(10) 0.04893(18) 0.69147(9) 0.0406(3) Uani 1 1 d . . . . .
C23 C 0.61171(9) 0.24454(19) 0.41395(9) 0.0409(3) Uani 1 1 d . . . . .
C11 C 0.83305(10) 0.0999(2) 0.58593(9) 0.0439(3) Uani 1 1 d . . . . .
H11 H 0.874109 0.116989 0.551020 0.053 Uiso 1 1 calc R . . . .
C9 C 0.82164(9) 0.3878(2) 0.41715(9) 0.0411(3) Uani 1 1 d . . . . .
C21 C 0.45412(10) 0.3014(2) 0.42707(10) 0.0450(3) Uani 1 1 d . . . . .
H21 H 0.436534 0.332765 0.365699 0.054 Uiso 1 1 calc R . . . .
C13 C 0.80474(10) 0.0039(2) 0.72321(9) 0.0465(3) Uani 1 1 d . . . . .
H13 H 0.827673 -0.047868 0.780634 0.056 Uiso 1 1 calc R . . . .
C5 C 0.88531(10) 0.4138(2) 0.36474(10) 0.0515(4) Uani 1 1 d . . . . .
C20 C 0.38913(10) 0.3150(2) 0.47463(11) 0.0500(4) Uani 1 1 d . . . . .
H20 H 0.327544 0.353942 0.445998 0.060 Uiso 1 1 calc R . . . .
C12 C 0.86701(10) 0.0326(2) 0.67311(10) 0.0498(4) Uani 1 1 d . . . . .
H12 H 0.931272 0.006742 0.697962 0.060 Uiso 1 1 calc R . . . .
C2 C 0.78303(11) 0.0957(2) 0.34987(10) 0.0533(4) Uani 1 1 d . . . . .
H2 H 0.749058 -0.010154 0.344266 0.064 Uiso 1 1 calc R . . . .
C18 C 0.50736(11) 0.2094(2) 0.60812(10) 0.0518(4) Uani 1 1 d . . . . .
H18 H 0.523947 0.181026 0.669839 0.062 Uiso 1 1 calc R . . . .
C19 C 0.41694(11) 0.2700(2) 0.56531(11) 0.0555(4) Uani 1 1 d . . . . .
H19 H 0.373819 0.280560 0.598517 0.067 Uiso 1 1 calc R . . . .
C16 C 0.65209(12) 0.0088(2) 0.75533(10) 0.0522(4) Uani 1 1 d . . . . .
H16A H 0.636214 0.118103 0.779703 0.078 Uiso 1 1 calc GR . . . .
H16B H 0.688523 -0.065091 0.804350 0.078 Uiso 1 1 calc GR . . . .
H16C H 0.594821 -0.052141 0.722574 0.078 Uiso 1 1 calc GR . . . .
C4 C 0.89622(13) 0.2769(3) 0.30620(12) 0.0658(5) Uani 1 1 d . . . . .
H4 H 0.938080 0.292874 0.272026 0.079 Uiso 1 1 calc R . . . .
C3 C 0.84720(13) 0.1222(3) 0.29843(11) 0.0668(5) Uani 1 1 d . . . . .
H3 H 0.855675 0.033451 0.259357 0.080 Uiso 1 1 calc R . . . .
C8 C 0.85632(13) 0.6612(2) 0.48395(15) 0.0678(5) Uani 1 1 d . . . . .
H8 H 0.847814 0.746161 0.524826 0.081 Uiso 1 1 calc R . . . .
C6 C 0.93353(13) 0.5797(3) 0.37516(14) 0.0701(5) Uani 1 1 d . . . . .
H6 H 0.974782 0.604566 0.341294 0.084 Uiso 1 1 calc R . . . .
C7 C 0.91914(14) 0.7013(3) 0.43463(17) 0.0751(6) Uani 1 1 d . . . . .
H7 H 0.950669 0.810103 0.442477 0.090 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.4147(16) . ?
N1 C1 1.4420(16) . ?
N1 C23 1.3734(17) . ?
O1 C23 1.2250(16) . ?
N2 C9 1.3615(19) . ?
N2 C8 1.316(2) . ?
C10 C15 1.4180(17) . ?
C10 C11 1.3909(19) . ?
C1 C9 1.417(2) . ?
C1 C2 1.359(2) . ?
C15 C17 1.4704(18) . ?
C15 C14 1.4280(18) . ?
C17 C22 1.4025(18) . ?
C17 C18 1.4061(19) . ?
C22 C23 1.4676(18) . ?
C22 C21 1.3954(19) . ?
C14 C13 1.380(2) . ?
C14 C16 1.5085(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(2) . ?
C9 C5 1.4213(18) . ?
C21 H21 0.9300 . ?
C21 C20 1.372(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(2) . ?
C5 C4 1.407(3) . ?
C5 C6 1.420(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.371(2) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.417(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(2) . ?
C19 H19 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.355(3) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.394(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.353(3) . ?
C7 H7 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
C10 N1 C1 119.70(10) . . ?
C23 N1 C10 124.34(10) . . ?
C23 N1 C1 115.92(10) . . ?
C8 N2 C9 117.13(14) . . ?
N1 C10 C15 120.39(11) . . ?
C11 C10 N1 117.90(11) . . ?
C11 C10 C15 121.71(12) . . ?
C9 C1 N1 118.19(12) . . ?
C2 C1 N1 120.55(14) . . ?
C2 C1 C9 121.25(13) . . ?
C10 C15 C17 117.37(11) . . ?
C10 C15 C14 116.96(12) . . ?
C14 C15 C17 125.67(12) . . ?
C22 C17 C15 119.40(11) . . ?
C22 C17 C18 115.58(12) . . ?
C18 C17 C15 124.96(12) . . ?
C17 C22 C23 122.22(12) . . ?
C21 C22 C17 121.59(12) . . ?
C21 C22 C23 116.12(12) . . ?
C15 C14 C16 125.21(13) . . ?
C13 C14 C15 119.24(13) . . ?
C13 C14 C16 115.55(12) . . ?
N1 C23 C22 115.78(11) . . ?
O1 C23 N1 120.77(12) . . ?
O1 C23 C22 123.42(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.86(13) . . ?
C12 C11 H11 120.1 . . ?
N2 C9 C1 118.90(12) . . ?
N2 C9 C5 122.75(14) . . ?
C1 C9 C5 118.35(13) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.88(13) . . ?
C20 C21 H21 119.6 . . ?
C14 C13 H13 118.7 . . ?
C12 C13 C14 122.61(13) . . ?
C12 C13 H13 118.7 . . ?
C4 C5 C9 118.84(16) . . ?
C4 C5 C6 124.38(16) . . ?
C6 C5 C9 116.78(16) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 C21 118.57(13) . . ?
C19 C20 H20 120.7 . . ?
C11 C12 C13 119.35(13) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.04(17) . . ?
C3 C2 H2 120.0 . . ?
C17 C18 H18 119.0 . . ?
C19 C18 C17 122.03(13) . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 121.30(14) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.57(14) . . ?
C3 C4 H4 119.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.95(16) . . ?
C4 C3 H3 120.0 . . ?
N2 C8 H8 117.6 . . ?
N2 C8 C7 124.70(19) . . ?
C7 C8 H8 117.6 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.63(16) . . ?
C7 C6 H6 120.2 . . ?
C8 C7 H7 120.5 . . ?
C6 C7 C8 118.99(18) . . ?
C6 C7 H7 120.5 . . ?

_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sxj-s-504-tm1
_database_code_depnum_ccdc_archive 'CCDC 1935311'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.08(C34 H25 N2 O P Pd)'
_chemical_formula_sum            'C2.67 H1.96 N0.16 O0.08 P0.08 Pd0.08'
_chemical_formula_weight         48.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.88834(18)
_cell_length_b                   18.6381(4)
_cell_length_c                   16.8048(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.007(2)
_cell_angle_gamma                90
_cell_volume                     2723.00(10)
_cell_formula_units_Z            51
_cell_measurement_reflns_used    6510
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.4350
_cell_measurement_theta_min      5.0730
_shelx_estimated_absorpt_T_max   0.314
_shelx_estimated_absorpt_T_min   0.292
_exptl_absorpt_coefficient_mu    6.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.503
_diffrn_reflns_theta_min         3.585
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  31.00   1.00    1.59    --  -40.80  38.00  30.00   81
  2  ω     44.00  95.00   1.00    1.59    --   40.80-125.00  60.00   51
  3  ω     31.00  71.00   1.00    6.36    --  107.14 -77.00 120.00   40
  4  ω     38.00 117.00   1.00    6.36    --  107.14-125.00  90.00   79
  5  ω    103.00 134.00   1.00    6.36    --  107.14 -77.00 120.00   31
  6  ω    128.00 177.00   1.00    6.36    --  107.14  45.00 -60.00   49
  7  ω    126.00 177.00   1.00    6.36    --  107.14  45.00-150.00   51
  8  ω    117.00 168.00   1.00    6.36    --  107.14  45.00 -90.00   51
  9  ω     83.00 109.00   1.00    6.36    --  107.14  45.00-150.00   26
 10  ω     81.00 112.00   1.00    6.36    --  107.14  45.00 -90.00   31
 11  ω     83.00 109.00   1.00    6.36    --  107.14  45.00 -60.00   26
 12  ω     38.00 102.00   1.00    6.36    --  107.14 -95.00-180.00   64
 13  ω   -102.00 -75.00   1.00    1.59    --  -40.80-143.00 -55.00   27
 14  ω   -106.00 -17.00   1.00    1.59    --  -40.80 -57.00-120.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181314000
_diffrn_orient_matrix_UB_12      -0.0723546000
_diffrn_orient_matrix_UB_13      0.0453737000
_diffrn_orient_matrix_UB_21      0.0129892000
_diffrn_orient_matrix_UB_22      0.0397325000
_diffrn_orient_matrix_UB_23      0.0815447000
_diffrn_orient_matrix_UB_31      -0.1757291000
_diffrn_orient_matrix_UB_32      -0.0045337000
_diffrn_orient_matrix_UB_33      -0.0089923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4789
_reflns_number_total             5342
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.054
_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)+(0.0361P)²+0.2055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_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), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21),
  C22(H22), C23(H23), C27(H27), C28(H28), C29(H29), C32(H32), C33(H33), C34(H34)
;
_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
C1 C 0.4910(3) 0.47394(14) 0.82866(15) 0.0394(5) Uani 1 1 d . . . . .
C2 C 0.5920(3) 0.52152(16) 0.87607(18) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.604264 0.567630 0.857244 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6745(4) 0.4999(2) 0.9517(2) 0.0616(8) Uani 1 1 d . . . . .
H3 H 0.743966 0.531363 0.982969 0.074 Uiso 1 1 calc R . . . .
C4 C 0.6542(4) 0.4319(2) 0.9811(2) 0.0645(9) Uani 1 1 d . . . . .
H4 H 0.709659 0.417804 1.031892 0.077 Uiso 1 1 calc R . . . .
C5 C 0.5522(4) 0.38535(19) 0.9352(2) 0.0616(8) Uani 1 1 d . . . . .
H5 H 0.537052 0.339989 0.955245 0.074 Uiso 1 1 calc R . . . .
C6 C 0.4720(4) 0.40590(16) 0.85911(19) 0.0505(6) Uani 1 1 d . . . . .
H6 H 0.404251 0.373790 0.827846 0.061 Uiso 1 1 calc R . . . .
C7 C 0.4777(3) 0.56704(15) 0.68496(16) 0.0391(5) Uani 1 1 d . . . . .
C8 C 0.5383(3) 0.55431(17) 0.61639(17) 0.0453(6) Uani 1 1 d . . . . .
H8 H 0.534001 0.508371 0.594422 0.054 Uiso 1 1 calc R . . . .
C9 C 0.4846(3) 0.63626(16) 0.71656(18) 0.0462(6) Uani 1 1 d . . . . .
H9 H 0.444426 0.645594 0.762378 0.055 Uiso 1 1 calc R . . . .
C10 C 0.5506(4) 0.69128(17) 0.6805(2) 0.0552(7) Uani 1 1 d . . . . .
H10 H 0.554550 0.737357 0.702082 0.066 Uiso 1 1 calc R . . . .
C11 C 0.6110(4) 0.67789(19) 0.6122(2) 0.0581(8) Uani 1 1 d . . . . .
H11 H 0.655284 0.714952 0.587901 0.070 Uiso 1 1 calc R . . . .
C12 C 0.6053(4) 0.60954(18) 0.5803(2) 0.0544(7) Uani 1 1 d . . . . .
H12 H 0.646332 0.600388 0.534759 0.065 Uiso 1 1 calc R . . . .
C13 C 0.2086(3) 0.53737(15) 0.74742(16) 0.0417(5) Uani 1 1 d . . . . .
C14 C 0.1343(4) 0.59146(18) 0.6972(2) 0.0561(7) Uani 1 1 d . . . . .
H14 H 0.175835 0.607686 0.654097 0.067 Uiso 1 1 calc R . . . .
C15 C -0.0007(4) 0.6215(2) 0.7106(3) 0.0701(10) Uani 1 1 d . . . . .
H15 H -0.049417 0.657494 0.676349 0.084 Uiso 1 1 calc R . . . .
C16 C -0.0624(4) 0.5985(3) 0.7739(3) 0.0808(13) Uani 1 1 d . . . . .
H16 H -0.153225 0.618706 0.782722 0.097 Uiso 1 1 calc R . . . .
C17 C 0.0096(4) 0.5455(3) 0.8245(3) 0.0818(12) Uani 1 1 d . . . . .
H17 H -0.032212 0.530152 0.867878 0.098 Uiso 1 1 calc R . . . .
C18 C 0.1449(3) 0.5145(2) 0.8113(2) 0.0568(7) Uani 1 1 d . . . . .
H18 H 0.192522 0.478277 0.845576 0.068 Uiso 1 1 calc R . . . .
C19 C 0.5754(3) 0.36422(15) 0.68214(16) 0.0405(5) Uani 1 1 d . . . . .
C20 C 0.7038(3) 0.40127(17) 0.72291(19) 0.0480(6) Uani 1 1 d . . . . .
H20 H 0.693486 0.448224 0.739734 0.058 Uiso 1 1 calc R . . . .
C21 C 0.8483(4) 0.3687(2) 0.7389(2) 0.0584(8) Uani 1 1 d . . . . .
H21 H 0.933034 0.394135 0.766683 0.070 Uiso 1 1 calc R . . . .
C22 C 0.8676(4) 0.29959(19) 0.7143(2) 0.0619(8) Uani 1 1 d . . . . .
H22 H 0.964467 0.278468 0.725712 0.074 Uiso 1 1 calc R . . . .
C23 C 0.7431(4) 0.26195(17) 0.6728(2) 0.0556(7) Uani 1 1 d . . . . .
H23 H 0.755229 0.215219 0.655802 0.067 Uiso 1 1 calc R . . . .
C24 C 0.5980(3) 0.29415(15) 0.65623(17) 0.0444(6) Uani 1 1 d . . . . .
C25 C 0.4636(4) 0.25429(16) 0.60947(17) 0.0467(6) Uani 1 1 d . . . . .
C26 C 0.1905(3) 0.27338(16) 0.55330(17) 0.0474(6) Uani 1 1 d . . . . .
C27 C 0.1542(5) 0.2083(2) 0.5131(2) 0.0691(9) Uani 1 1 d . . . . .
H27 H 0.229763 0.173549 0.514741 0.083 Uiso 1 1 calc R . . . .
C28 C 0.0033(5) 0.1952(2) 0.4700(3) 0.0848(13) Uani 1 1 d . . . . .
H28 H -0.019337 0.151512 0.443476 0.102 Uiso 1 1 calc R . . . .
C29 C -0.1101(5) 0.2448(3) 0.4660(3) 0.0806(12) Uani 1 1 d . . . . .
H29 H -0.208373 0.234807 0.436340 0.097 Uiso 1 1 calc R . . . .
C30 C -0.0799(4) 0.3118(2) 0.5068(2) 0.0595(8) Uani 1 1 d . . . . .
C31 C 0.0729(3) 0.32555(16) 0.55052(16) 0.0453(6) Uani 1 1 d . . . . .
C32 C 0.0027(3) 0.4386(2) 0.5869(2) 0.0552(7) Uani 1 1 d . . . . .
H32 H 0.028649 0.481985 0.613456 0.066 Uiso 1 1 calc R . . . .
C33 C -0.1504(4) 0.4283(2) 0.5442(2) 0.0651(9) Uani 1 1 d . . . . .
H33 H -0.223112 0.464429 0.542364 0.078 Uiso 1 1 calc R . . . .
C34 C -0.1897(4) 0.3648(2) 0.5060(2) 0.0686(10) Uani 1 1 d . . . . .
H34 H -0.290808 0.356759 0.479111 0.082 Uiso 1 1 calc R . . . .
N1 N 0.3353(3) 0.29486(12) 0.59545(14) 0.0451(5) Uani 1 1 d . . . . .
N2 N 0.1098(3) 0.38948(13) 0.59068(15) 0.0452(5) Uani 1 1 d . . . . .
O1 O 0.4733(3) 0.19129(12) 0.58674(15) 0.0654(6) Uani 1 1 d . . . . .
P1 P 0.38178(7) 0.49415(3) 0.72668(4) 0.03571(13) Uani 1 1 d . . . . .
Pd00 Pd 0.34930(2) 0.39223(2) 0.64973(2) 0.03607(7) 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 1.389(4) . ?
C1 C6 1.391(4) . ?
C1 P1 1.825(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(4) . ?
C7 C9 1.392(4) . ?
C7 P1 1.820(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(4) . ?
C13 C18 1.381(4) . ?
C13 P1 1.834(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(4) . ?
C19 C24 1.404(4) . ?
C19 Pd00 2.038(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.396(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.397(4) . ?
C24 C25 1.485(4) . ?
C25 N1 1.347(4) . ?
C25 O1 1.243(4) . ?
C26 C27 1.393(4) . ?
C26 C31 1.421(4) . ?
C26 N1 1.392(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.407(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.359(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.424(6) . ?
C30 C31 1.426(4) . ?
C30 C34 1.386(6) . ?
C31 N2 1.375(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.413(4) . ?
C32 N2 1.312(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.357(6) . ?
C34 H34 0.9300 . ?
N1 Pd00 2.023(2) . ?
N2 Pd00 2.154(2) . ?
P1 Pd00 2.2823(6) . ?

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 119.0(3) . . ?
C2 C1 P1 124.1(2) . . ?
C6 C1 P1 116.9(2) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C9 118.7(3) . . ?
C8 C7 P1 119.0(2) . . ?
C9 C7 P1 122.2(2) . . ?
C7 C8 H8 119.7 . . ?
C12 C8 C7 120.7(3) . . ?
C12 C8 H8 119.7 . . ?
C7 C9 H9 119.7 . . ?
C10 C9 C7 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C8 C12 H12 120.0 . . ?
C11 C12 C8 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 P1 121.0(2) . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 P1 120.5(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.2(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C24 117.4(3) . . ?
C20 C19 Pd00 132.0(2) . . ?
C24 C19 Pd00 110.6(2) . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.7(3) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 C25 118.6(2) . . ?
C23 C24 C19 121.5(3) . . ?
C23 C24 C25 119.9(3) . . ?
N1 C25 C24 111.7(2) . . ?
O1 C25 C24 122.4(3) . . ?
O1 C25 N1 125.9(3) . . ?
C27 C26 C31 119.0(3) . . ?
N1 C26 C27 126.4(3) . . ?
N1 C26 C31 114.6(2) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.1(4) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.2 . . ?
C29 C28 C27 121.7(4) . . ?
C29 C28 H28 119.2 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C31 118.0(4) . . ?
C34 C30 C29 123.9(3) . . ?
C34 C30 C31 118.1(3) . . ?
C26 C31 C30 120.6(3) . . ?
N2 C31 C26 118.6(2) . . ?
N2 C31 C30 120.8(3) . . ?
C33 C32 H32 118.6 . . ?
N2 C32 H32 118.6 . . ?
N2 C32 C33 122.8(3) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 C32 119.0(4) . . ?
C34 C33 H33 120.5 . . ?
C30 C34 H34 119.9 . . ?
C33 C34 C30 120.3(3) . . ?
C33 C34 H34 119.9 . . ?
C25 N1 C26 125.9(3) . . ?
C25 N1 Pd00 117.02(19) . . ?
C26 N1 Pd00 116.79(19) . . ?
C31 N2 Pd00 110.99(19) . . ?
C32 N2 C31 119.0(3) . . ?
C32 N2 Pd00 130.0(2) . . ?
C1 P1 C13 102.48(12) . . ?
C1 P1 Pd00 109.89(9) . . ?
C7 P1 C1 108.39(12) . . ?
C7 P1 C13 102.95(12) . . ?
C7 P1 Pd00 114.66(9) . . ?
C13 P1 Pd00 117.45(9) . . ?
C19 Pd00 N2 160.43(10) . . ?
C19 Pd00 P1 93.46(8) . . ?
N1 Pd00 C19 81.68(10) . . ?
N1 Pd00 N2 78.99(10) . . ?
N1 Pd00 P1 172.16(7) . . ?
N2 Pd00 P1 106.09(7) . . ?

_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.592
####################################################################### 
# 
# 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_sxj-s-462
_database_code_depnum_ccdc_archive 'CCDC 1935310'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.13(C23 H16 N2 O)'
_chemical_formula_sum            'C2.88 H2 N0.25 O0.12'
_chemical_formula_weight         42.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
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                   11.6498(8)
_cell_length_b                   11.4654(8)
_cell_length_c                   12.9919(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.440(7)
_cell_angle_gamma                90
_cell_volume                     1694.6(2)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.3770
_cell_measurement_theta_min      5.1770
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5897
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.690
_diffrn_reflns_theta_min         3.886
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  32.00   1.00    3.88    --  -40.80  38.00-120.00   85
  2  ω    -92.00 -35.00   1.00    3.88    --  -40.80 125.00-120.00   57
  3  ω   -114.00 -18.00   1.00    3.88    --  -40.80 -38.00 -90.00   96
  4  ω   -106.00 -81.00   1.00    3.88    --  -40.80 -38.00   0.00   25
  5  ω     45.00 119.00   1.00   15.55    --  107.14-125.00 -30.00   74
  6  ω     47.00 115.00   1.00   15.55    --  107.14 -45.00  30.00   68
  7  ω     55.00 105.00   1.00   15.55    --  107.14 -95.00 120.00   50
  8  ω     30.00  77.00   1.00   15.55    --  107.14 -95.00   0.00   47
  9  ω    101.00 177.00   1.00   15.55    --  107.14  45.00-150.00   76
 10  ω     75.00 125.00   1.00   15.55    --  107.14  77.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0617325000
_diffrn_orient_matrix_UB_12      0.0306574000
_diffrn_orient_matrix_UB_13      -0.0901583000
_diffrn_orient_matrix_UB_21      -0.0195528000
_diffrn_orient_matrix_UB_22      0.1306073000
_diffrn_orient_matrix_UB_23      0.0179703000
_diffrn_orient_matrix_UB_31      0.1188855000
_diffrn_orient_matrix_UB_32      0.0057489000
_diffrn_orient_matrix_UB_33      0.0794768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2491
_reflns_number_total             3154
_reflns_odcompleteness_completeness 95.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.179
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1835
_refine_special_details          ?
_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:
 C11(H11), C1(H1), C8(H8), C9(H9), C4(H4), C16(H16), C18(H18), C2(H2),
 C21(H21), C3(H3), C17(H17), C23(H23), C22(H22)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.09729(11) 0.44002(12) 0.42184(11) 0.0488(4) Uani 1 1 d . . . . .
N1 N 0.25577(13) 0.43734(13) 0.34698(12) 0.0428(4) Uani 1 1 d . . . . .
N2 N 0.27299(16) 0.20734(16) 0.42089(13) 0.0548(4) Uani 1 1 d . . . . .
C12 C 0.24416(14) 0.58346(15) 0.47983(13) 0.0398(4) Uani 1 1 d . . . . .
C7 C 0.35182(15) 0.63156(16) 0.46950(14) 0.0430(4) Uani 1 1 d . . . . .
C13 C 0.19293(14) 0.48251(15) 0.41713(13) 0.0393(4) Uani 1 1 d . . . . .
C6 C 0.36522(14) 0.48099(17) 0.33554(14) 0.0435(4) Uani 1 1 d . . . . .
C15 C 0.19969(15) 0.34269(17) 0.28168(14) 0.0443(4) Uani 1 1 d . . . . .
C5 C 0.41440(15) 0.57791(17) 0.39498(14) 0.0449(4) Uani 1 1 d . . . . .
C20 C 0.20551(15) 0.22831(16) 0.32385(14) 0.0437(4) Uani 1 1 d . . . . .
C19 C 0.13936(16) 0.14033(17) 0.25985(16) 0.0486(4) Uani 1 1 d . . . . .
C11 C 0.18140(16) 0.63126(16) 0.55076(14) 0.0444(4) Uani 1 1 d . . . . .
H11 H 0.109904 0.598316 0.555923 0.053 Uiso 1 1 calc R . . . .
C10 C 0.22371(19) 0.72626(17) 0.61303(16) 0.0522(5) Uani 1 1 d . . . . .
C1 C 0.42437(18) 0.4271(2) 0.26538(17) 0.0539(5) Uani 1 1 d . . . . .
H1 H 0.391888 0.362041 0.227184 0.065 Uiso 1 1 calc R . . . .
C8 C 0.39399(19) 0.72749(19) 0.53327(17) 0.0564(5) Uani 1 1 d . . . . .
H8 H 0.465476 0.760834 0.528654 0.068 Uiso 1 1 calc R . . . .
C9 C 0.3317(2) 0.77353(19) 0.60274(17) 0.0579(5) Uani 1 1 d . . . . .
H9 H 0.362107 0.837442 0.643754 0.069 Uiso 1 1 calc R . . . .
C4 C 0.52404(17) 0.6189(2) 0.38144(18) 0.0588(5) Uani 1 1 d . . . . .
H4 H 0.558904 0.682506 0.420472 0.071 Uiso 1 1 calc R . . . .
C16 C 0.13844(19) 0.3665(2) 0.18223(16) 0.0575(5) Uani 1 1 d . . . . .
H16 H 0.136202 0.442267 0.156340 0.069 Uiso 1 1 calc R . . . .
C18 C 0.07745(19) 0.1667(2) 0.15696(17) 0.0588(5) Uani 1 1 d . . . . .
H18 H 0.035634 0.108382 0.115235 0.071 Uiso 1 1 calc R . . . .
C2 C 0.53103(19) 0.4707(3) 0.25295(19) 0.0671(6) Uani 1 1 d . . . . .
H2 H 0.569633 0.435686 0.205368 0.080 Uiso 1 1 calc R . . . .
C21 C 0.1412(2) 0.0283(2) 0.3035(2) 0.0631(6) Uani 1 1 d . . . . .
H21 H 0.097460 -0.031473 0.265484 0.076 Uiso 1 1 calc R . . . .
C3 C 0.58042(19) 0.5655(3) 0.3106(2) 0.0680(7) Uani 1 1 d . . . . .
H3 H 0.652448 0.594088 0.301942 0.082 Uiso 1 1 calc R . . . .
C17 C 0.0783(2) 0.2764(2) 0.11821(18) 0.0650(6) Uani 1 1 d . . . . .
H17 H 0.039172 0.292360 0.049401 0.078 Uiso 1 1 calc R . . . .
C23 C 0.2729(3) 0.0992(2) 0.4558(2) 0.0706(6) Uani 1 1 d . . . . .
H23 H 0.320062 0.082656 0.521514 0.085 Uiso 1 1 calc R . . . .
C14 C 0.1566(3) 0.7763(2) 0.6892(2) 0.0748(7) Uani 1 1 d . . . . .
H14A H 0.153509 0.859710 0.682253 0.112 Uiso 1 1 calc GR . . . .
H14B H 0.195124 0.755852 0.759801 0.112 Uiso 1 1 calc GR . . . .
H14C H 0.078115 0.745491 0.674121 0.112 Uiso 1 1 calc GR . . . .
C22 C 0.2068(2) 0.0075(2) 0.4010(2) 0.0747(7) Uani 1 1 d . . . . .
H22 H 0.208062 -0.066207 0.431117 0.090 Uiso 1 1 calc R . . . .


_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 1.230(2) . ?
N1 C13 1.386(2) . ?
N1 C6 1.407(2) . ?
N1 C15 1.444(2) . ?
N2 C20 1.356(3) . ?
N2 C23 1.320(3) . ?
C12 C7 1.403(2) . ?
C12 C13 1.466(2) . ?
C12 C11 1.405(3) . ?
C7 C5 1.467(3) . ?
C7 C8 1.401(3) . ?
C6 C5 1.403(3) . ?
C6 C1 1.399(3) . ?
C15 C20 1.417(3) . ?
C15 C16 1.362(3) . ?
C5 C4 1.407(3) . ?
C20 C19 1.424(3) . ?
C19 C18 1.408(3) . ?
C19 C21 1.402(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(3) . ?
C10 C9 1.403(3) . ?
C10 C14 1.501(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.383(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.414(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.355(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.352(4) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.404(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22 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
C13 N1 C6 123.73(15) . . ?
C13 N1 C15 115.52(14) . . ?
C6 N1 C15 120.72(15) . . ?
C23 N2 C20 116.29(19) . . ?
C7 C12 C13 121.50(16) . . ?
C7 C12 C11 120.78(16) . . ?
C11 C12 C13 117.72(15) . . ?
C12 C7 C5 118.69(16) . . ?
C8 C7 C12 117.32(18) . . ?
C8 C7 C5 123.98(17) . . ?
O1 C13 N1 119.81(16) . . ?
O1 C13 C12 123.36(16) . . ?
N1 C13 C12 116.79(15) . . ?
C5 C6 N1 119.70(16) . . ?
C1 C6 N1 119.76(18) . . ?
C1 C6 C5 120.54(17) . . ?
C20 C15 N1 119.36(15) . . ?
C16 C15 N1 119.01(18) . . ?
C16 C15 C20 121.58(18) . . ?
C6 C5 C7 119.56(15) . . ?
C6 C5 C4 118.03(19) . . ?
C4 C5 C7 122.41(19) . . ?
N2 C20 C15 119.57(17) . . ?
N2 C20 C19 123.36(18) . . ?
C15 C20 C19 117.07(17) . . ?
C18 C19 C20 120.28(19) . . ?
C21 C19 C20 116.98(19) . . ?
C21 C19 C18 122.74(19) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.37(18) . . ?
C10 C11 H11 119.3 . . ?
C11 C10 C9 117.55(19) . . ?
C11 C10 C14 121.1(2) . . ?
C9 C10 C14 121.38(19) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 H1 120.1 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.39(19) . . ?
C9 C8 H8 119.3 . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.58(18) . . ?
C8 C9 H9 119.2 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.60(19) . . ?
C17 C18 H18 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C19 C21 H21 120.1 . . ?
C22 C21 C19 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
N2 C23 H23 117.6 . . ?
N2 C23 C22 124.8(2) . . ?
C22 C23 H23 117.6 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?

_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 2.113
_oxdiff_exptl_absorpt_empirical_full_min 0.384
####################################################################### 
# 
# 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_sxj-s463-tm1
_database_code_depnum_ccdc_archive 'CCDC 1935308'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.11(C22 H13 F N2 O), 0.11(C H2 Cl2)'
_chemical_formula_sum            'C2.59 H1.62 Cl0.22 F0.11 N0.22 O0.11'
_chemical_formula_weight         47.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.9904(4)
_cell_length_b                   7.6164(2)
_cell_length_c                   18.5537(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.644(2)
_cell_angle_gamma                90
_cell_volume                     1949.07(9)
_cell_formula_units_Z            37
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.1830
_cell_measurement_theta_min      4.8090
_shelx_estimated_absorpt_T_max   0.510
_shelx_estimated_absorpt_T_min   0.486
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6966
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.693
_diffrn_reflns_theta_min         3.676
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  28.00   1.00    5.85    --  -40.80  57.00 -90.00   92
  2  ω    -35.00  33.00   1.00    5.85    --  -40.80  38.00 150.00   68
  3  ω     24.00  84.00   1.00    5.85    --   40.80-125.00 -30.00   60
  4  ω     45.00 107.00   1.00   23.40    --  107.14 -45.00 -60.00   62
  5  ω     98.00 158.00   1.00   23.40    --  107.14  45.00-180.00   60
  6  ω    152.00 178.00   1.00   23.40    --  107.14 125.00-120.00   26
  7  ω     93.00 178.00   1.00   23.40    --  107.14  61.00-120.00   85
  8  ω    114.00 177.00   1.00   23.40    --  107.14  45.00 120.00   63
  9  ω     35.00 133.00   1.00   23.40    --  107.14 -45.00  90.00   98
 10  ω     33.00  58.00   1.00    5.85    --   40.80-125.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0122875000
_diffrn_orient_matrix_UB_12      -0.1421794000
_diffrn_orient_matrix_UB_13      -0.0567596000
_diffrn_orient_matrix_UB_21      0.1025921000
_diffrn_orient_matrix_UB_22      0.0692030000
_diffrn_orient_matrix_UB_23      -0.0035748000
_diffrn_orient_matrix_UB_31      0.0424786000
_diffrn_orient_matrix_UB_32      -0.1260667000
_diffrn_orient_matrix_UB_33      0.0621174000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2990
_reflns_number_total             3811
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.046
_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)+(0.1148P)²+1.1844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2230
_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:
 C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C19(H19), C20(H20), C21(H21)
;
_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
C1 C 0.41309(17) 0.1951(3) 0.72483(13) 0.0441(6) Uani 1 1 d . . . . .
C2 C 0.42220(18) 0.3480(4) 0.76905(13) 0.0451(6) Uani 1 1 d . . . . .
C3 C 0.3586(2) 0.0567(4) 0.73955(16) 0.0556(7) Uani 1 1 d . . . . .
H3 H 0.354138 -0.042345 0.709837 0.067 Uiso 1 1 calc R . . . .
C4 C 0.3141(2) 0.2064(5) 0.84257(15) 0.0604(8) Uani 1 1 d . . . . .
H4 H 0.280178 0.209551 0.881611 0.072 Uiso 1 1 calc R . . . .
C5 C 0.3085(2) 0.0615(5) 0.79984(17) 0.0629(8) Uani 1 1 d . . . . .
H5 H 0.271994 -0.034570 0.810017 0.075 Uiso 1 1 calc R . . . .
C6 C 0.3702(2) 0.3526(4) 0.82894(14) 0.0532(7) Uani 1 1 d . . . . .
C7 C 0.3775(3) 0.5060(5) 0.87097(19) 0.0763(10) Uani 1 1 d . . . . .
H7 H 0.343762 0.516833 0.909853 0.092 Uiso 1 1 calc R . . . .
C8 C 0.4347(4) 0.6392(5) 0.8542(2) 0.0895(12) Uani 1 1 d . . . . .
H8 H 0.440861 0.741589 0.881873 0.107 Uiso 1 1 calc R . . . .
C9 C 0.4843(3) 0.6217(5) 0.7951(2) 0.0761(10) Uani 1 1 d . . . . .
H9 H 0.523235 0.714443 0.785000 0.091 Uiso 1 1 calc R . . . .
C10 C 0.6032(2) 0.0653(4) 0.73753(17) 0.0575(7) Uani 1 1 d . . . . .
H10 H 0.571073 0.069866 0.777489 0.069 Uiso 1 1 calc R . . . .
C11 C 0.6958(2) -0.0027(5) 0.7458(2) 0.0709(9) Uani 1 1 d . . . . .
H11 H 0.725732 -0.044743 0.791054 0.085 Uiso 1 1 calc R . . . .
C12 C 0.7441(2) -0.0080(5) 0.6864(2) 0.0767(10) Uani 1 1 d . . . . .
H12 H 0.806585 -0.053623 0.691877 0.092 Uiso 1 1 calc R . . . .
C13 C 0.7003(2) 0.0535(4) 0.6201(2) 0.0663(8) Uani 1 1 d . . . . .
H13 H 0.734118 0.049354 0.581013 0.080 Uiso 1 1 calc R . . . .
C14 C 0.60598(19) 0.1230(3) 0.60844(16) 0.0500(6) Uani 1 1 d . . . . .
C15 C 0.55754(18) 0.1269(3) 0.66991(15) 0.0459(6) Uani 1 1 d . . . . .
C16 C 0.5551(2) 0.1912(3) 0.53902(15) 0.0503(6) Uani 1 1 d . . . . .
C17 C 0.4617(2) 0.2615(3) 0.53444(14) 0.0497(6) Uani 1 1 d . . . . .
C18 C 0.41197(19) 0.2628(4) 0.59914(14) 0.0483(6) Uani 1 1 d . . . . .
C19 C 0.4116(3) 0.3348(4) 0.47033(16) 0.0620(7) Uani 1 1 d . . . . .
H19 H 0.349797 0.380557 0.469485 0.074 Uiso 1 1 calc R . . . .
C20 C 0.4534(3) 0.3398(5) 0.40802(17) 0.0711(9) Uani 1 1 d . . . . .
H20 H 0.420376 0.390131 0.365315 0.085 Uiso 1 1 calc R . . . .
C21 C 0.5438(3) 0.2701(4) 0.40977(18) 0.0692(9) Uani 1 1 d . . . . .
H21 H 0.572729 0.272729 0.368161 0.083 Uiso 1 1 calc R . . . .
C22 C 0.5913(2) 0.1968(4) 0.47252(18) 0.0614(8) Uani 1 1 d . . . . .
F23 F 0.67940(16) 0.1240(3) 0.46907(13) 0.0917(7) Uani 1 1 d . . . . .
N1 N 0.47931(19) 0.4815(3) 0.75276(13) 0.0573(6) Uani 1 1 d . . . . .
N2 N 0.46215(14) 0.1910(3) 0.66222(11) 0.0443(5) Uani 1 1 d . . . . .
O1 O 0.33076(15) 0.3221(3) 0.59748(11) 0.0665(6) Uani 1 1 d . . . . .
C24 C 0.1334(4) 0.4275(8) 0.4940(3) 0.1120(17) Uani 1 1 d . . . . .
H24A H 0.089996 0.464396 0.526729 0.134 Uiso 1 1 calc R . . . .
H24B H 0.194275 0.393116 0.523762 0.134 Uiso 1 1 calc R . . . .
Cl1 Cl 0.15359(16) 0.5978(2) 0.44180(9) 0.1419(7) Uani 1 1 d . . . . .
Cl2 Cl 0.08312(15) 0.2445(3) 0.44418(8) 0.1532(8) 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 1.418(4) . ?
C1 C3 1.355(4) . ?
C1 N2 1.445(3) . ?
C2 C6 1.426(3) . ?
C2 N1 1.358(4) . ?
C3 H3 0.9300 . ?
C3 C5 1.416(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.353(5) . ?
C4 C6 1.410(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.398(6) . ?
C9 H9 0.9300 . ?
C9 N1 1.320(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(4) . ?
C10 C15 1.391(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(4) . ?
C14 C15 1.421(3) . ?
C14 C16 1.459(4) . ?
C15 N2 1.406(3) . ?
C16 C17 1.401(4) . ?
C16 C22 1.411(4) . ?
C17 C18 1.485(3) . ?
C17 C19 1.392(4) . ?
C18 N2 1.373(3) . ?
C18 O1 1.218(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.367(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.360(5) . ?
C22 F23 1.363(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 Cl1 1.671(6) . ?
C24 Cl2 1.753(6) . ?

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 N2 118.3(2) . . ?
C3 C1 C2 121.4(2) . . ?
C3 C1 N2 120.3(2) . . ?
C1 C2 C6 117.6(2) . . ?
N1 C2 C1 119.0(2) . . ?
N1 C2 C6 123.4(3) . . ?
C1 C3 H3 119.7 . . ?
C1 C3 C5 120.5(3) . . ?
C5 C3 H3 119.7 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C6 121.2(2) . . ?
C6 C4 H4 119.4 . . ?
C3 C5 H5 120.1 . . ?
C4 C5 C3 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C4 C6 C2 119.5(3) . . ?
C7 C6 C2 117.1(3) . . ?
C7 C6 C4 123.4(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 118.0 . . ?
N1 C9 C8 124.0(3) . . ?
N1 C9 H9 118.0 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C15 120.5(3) . . ?
C15 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 118.8 . . ?
C12 C13 C14 122.5(3) . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C15 116.5(3) . . ?
C13 C14 C16 125.2(2) . . ?
C15 C14 C16 118.2(2) . . ?
C10 C15 C14 120.5(2) . . ?
C10 C15 N2 119.6(2) . . ?
N2 C15 C14 119.9(2) . . ?
C17 C16 C14 120.1(2) . . ?
C17 C16 C22 113.8(3) . . ?
C22 C16 C14 126.1(3) . . ?
C16 C17 C18 120.8(2) . . ?
C19 C17 C16 122.4(2) . . ?
C19 C17 C18 116.8(3) . . ?
N2 C18 C17 116.4(2) . . ?
O1 C18 C17 122.9(3) . . ?
O1 C18 N2 120.7(2) . . ?
C17 C19 H19 119.9 . . ?
C20 C19 C17 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C16 124.4(3) . . ?
C21 C22 F23 116.3(3) . . ?
F23 C22 C16 119.3(3) . . ?
C9 N1 C2 116.6(3) . . ?
C15 N2 C1 119.8(2) . . ?
C18 N2 C1 115.6(2) . . ?
C18 N2 C15 124.5(2) . . ?
H24A C24 H24B 107.7 . . ?
Cl1 C24 H24A 108.8 . . ?
Cl1 C24 H24B 108.8 . . ?
Cl1 C24 Cl2 113.8(3) . . ?
Cl2 C24 H24A 108.8 . . ?
Cl2 C24 H24B 108.8 . . ?

_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_sxj-20170520-s-45
_database_code_depnum_ccdc_archive 'CCDC 1938632'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.17(C23 H16 N2 O3)'
_chemical_formula_sum            'C3.83 H2.67 N0.33 O0.50'
_chemical_formula_weight         61.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     CHOcu
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3599(9)
_cell_length_b                   9.1656(18)
_cell_length_c                   12.047(2)
_cell_angle_alpha                101.840(16)
_cell_angle_beta                 102.780(12)
_cell_angle_gamma                93.053(12)
_cell_volume                     876.4(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      71.8250
_cell_measurement_theta_min      3.8260
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.673
_diffrn_reflns_Laue_measured_fraction_max 0.647
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3074
_diffrn_reflns_point_group_measured_fraction_full 0.673
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.453
_diffrn_reflns_theta_min         3.859
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.673
_diffrn_measured_fraction_theta_max 0.647
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  36.00   1.00    2.50    --  -40.55  77.00   0.00  108
  2  ω     73.00 100.00   1.00    2.50    --   40.55  38.00  60.00   27
  3  ω     97.00 130.00   1.00   10.00    --  107.14 -30.00 120.00   33
  4  ω     53.00  81.00   1.00    2.50    --   40.55 -99.00  30.00   28
  5  ω     36.00 123.00   1.00   10.00    --  107.14 -61.00 -90.00   87
  6  ω     77.00 104.00   1.00   10.00    --  107.14 -95.00 -60.00   27
  7  ω     34.00 118.00   1.00   10.00    --  107.14-125.00-150.00   84
  8  ω     29.00  55.00   1.00   10.00    --  107.14 -95.00 -60.00   26
  9  ω     31.00 103.00   1.00   10.00    --  107.14 -95.00-120.00   72
 10  ω     54.00 154.00   1.00   10.00    --  107.14  15.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1338336000
_diffrn_orient_matrix_UB_12      0.0663025000
_diffrn_orient_matrix_UB_13      -0.0505709000
_diffrn_orient_matrix_UB_21      0.0059343000
_diffrn_orient_matrix_UB_22      -0.1557882000
_diffrn_orient_matrix_UB_23      -0.0761682000
_diffrn_orient_matrix_UB_31      -0.1347048000
_diffrn_orient_matrix_UB_32      0.0338433000
_diffrn_orient_matrix_UB_33      -0.0986575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1775
_reflns_number_total             2281
_reflns_odcompleteness_completeness 67.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1106
_refine_ls_restrained_S_all      1.148
_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)+(0.1883P)²+1.8698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3692
_refine_ls_wR_factor_ref         0.3836
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C2(H2), C3(H3), C4(H4), C5(H5),
 C16(H16), C17(H17), C18(H18), C21(H21), C23(H23), C22(H22)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_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
C9 C 0.4901(8) 0.1757(8) 0.7398(6) 0.0494(19) Uani 1 1 d . . . . .
C10 C 0.5336(10) 0.0705(10) 0.6537(7) 0.057(2) Uani 1 1 d . . . . .
H10 H 0.451135 0.007225 0.596977 0.068 Uiso 1 1 calc R . . . .
C11 C 0.6977(11) 0.0577(12) 0.6506(8) 0.070(3) Uani 1 1 d . . . . .
H11 H 0.723777 -0.013669 0.592128 0.084 Uiso 1 1 calc R . . . .
C12 C 0.8197(10) 0.1490(11) 0.7324(8) 0.066(2) Uani 1 1 d . . . . .
H12 H 0.929317 0.139912 0.730247 0.079 Uiso 1 1 calc R . . . .
C13 C 0.7811(9) 0.2560(10) 0.8195(7) 0.058(2) Uani 1 1 d . . . . .
H13 H 0.864638 0.320674 0.874072 0.069 Uiso 1 1 calc R . . . .
C14 C 0.6184(8) 0.2665(9) 0.8251(6) 0.0505(19) Uani 1 1 d . . . . .
C1 C 0.2793(7) 0.1479(10) 0.8574(7) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.2955(10) 0.0123(11) 0.8933(8) 0.068(3) Uani 1 1 d . . . . .
H2 H 0.331512 -0.069893 0.849833 0.082 Uiso 1 1 calc R . . . .
C3 C 0.2537(13) 0.0089(14) 0.9990(10) 0.089(4) Uani 1 1 d . . . . .
H3 H 0.263939 -0.078122 1.027266 0.107 Uiso 1 1 calc R . . . .
C4 C 0.1984(13) 0.1289(15) 1.0622(9) 0.084(3) Uani 1 1 d . . . . .
H4 H 0.171233 0.120994 1.131707 0.101 Uiso 1 1 calc R . . . .
C5 C 0.1817(10) 0.2625(12) 1.0250(7) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.143989 0.344553 1.067422 0.082 Uiso 1 1 calc R . . . .
C6 C 0.2252(8) 0.2658(10) 0.9202(7) 0.055(2) Uani 1 1 d . . . . .
C7 C 0.2202(7) 0.3926(9) 0.8586(6) 0.0497(18) Uani 1 1 d . . . . .
C15 C 0.2998(8) 0.4347(9) 0.6835(6) 0.0495(18) Uani 1 1 d . . . . .
C16 C 0.4041(10) 0.5619(10) 0.7293(8) 0.061(2) Uani 1 1 d . . . . .
H16 H 0.456537 0.583819 0.808212 0.073 Uiso 1 1 calc R . . . .
C17 C 0.4343(11) 0.6610(10) 0.6599(9) 0.072(3) Uani 1 1 d . . . . .
H17 H 0.509405 0.745591 0.692672 0.086 Uiso 1 1 calc R . . . .
C18 C 0.3552(13) 0.6346(11) 0.5458(9) 0.073(3) Uani 1 1 d . . . . .
H18 H 0.374047 0.702779 0.501464 0.088 Uiso 1 1 calc R . . . .
C19 C 0.2455(10) 0.5059(10) 0.4941(7) 0.061(2) Uani 1 1 d . . . . .
C20 C 0.2162(8) 0.4005(8) 0.5621(6) 0.0494(18) Uani 1 1 d . . . . .
C21 C 0.0295(11) 0.2462(11) 0.4049(7) 0.063(2) Uani 1 1 d . . . . .
H21 H -0.041972 0.158919 0.374044 0.075 Uiso 1 1 calc R . . . .
C8 C 0.3114(8) 0.1823(8) 0.7459(6) 0.0459(17) Uani 1 1 d . . . . .
C23 C 0.1548(14) 0.4714(13) 0.3764(8) 0.077(3) Uani 1 1 d . . . . .
H23 H 0.169089 0.535696 0.328108 0.092 Uiso 1 1 calc R . . . .
C22 C 0.0476(13) 0.3463(12) 0.3332(8) 0.071(3) Uani 1 1 d . . . . .
H22 H -0.013809 0.326399 0.256288 0.085 Uiso 1 1 calc R . . . .
N1 N 0.2638(6) 0.3384(7) 0.7571(5) 0.0448(15) Uani 1 1 d . . . . .
N2 N 0.1131(8) 0.2742(8) 0.5167(6) 0.0541(17) Uani 1 1 d . . . . .
O1 O 0.2031(6) 0.0824(6) 0.6504(5) 0.0551(14) Uani 1 1 d . . . . .
H1 H 0.166113 0.127769 0.599995 0.083 Uiso 1 1 calc GR . . . .
O2 O 0.5780(7) 0.3620(8) 0.9129(5) 0.0675(17) Uani 1 1 d . . . . .
H2A H 0.659778 0.418078 0.951462 0.101 Uiso 1 1 calc GR . . . .
O3 O 0.1830(7) 0.5185(7) 0.8927(5) 0.0630(16) 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
C9 C10 1.389(12) . ?
C9 C14 1.402(11) . ?
C9 C8 1.516(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.356(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(10) . ?
C14 O2 1.344(10) . ?
C1 C2 1.402(10) . ?
C1 C6 1.346(12) . ?
C1 C8 1.516(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(10) . ?
C6 C7 1.500(9) . ?
C7 N1 1.357(10) . ?
C7 O3 1.224(11) . ?
C15 C16 1.355(12) . ?
C15 C20 1.436(11) . ?
C15 N1 1.438(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.403(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.352(14) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(14) . ?
C19 C20 1.433(9) . ?
C19 C23 1.414(14) . ?
C20 N2 1.344(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.407(11) . ?
C21 N2 1.338(11) . ?
C8 N1 1.493(8) . ?
C8 O1 1.414(10) . ?
C23 H23 0.9300 . ?
C23 C22 1.352(15) . ?
C22 H22 0.9300 . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?

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
C10 C9 C14 117.4(6) . . ?
C10 C9 C8 120.7(8) . . ?
C14 C9 C8 121.7(7) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.5(9) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(9) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(9) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.8(8) . . ?
O2 C14 C9 117.8(6) . . ?
O2 C14 C13 121.5(8) . . ?
C2 C1 C8 127.0(8) . . ?
C6 C1 C2 121.8(7) . . ?
C6 C1 C8 111.2(6) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 C1 115.5(9) . . ?
C3 C2 H2 122.3 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(8) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(8) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 122.1 . . ?
C4 C5 C6 115.8(10) . . ?
C6 C5 H5 122.1 . . ?
C1 C6 C5 122.9(7) . . ?
C1 C6 C7 109.0(6) . . ?
C5 C6 C7 128.0(8) . . ?
N1 C7 C6 105.9(7) . . ?
O3 C7 C6 126.9(7) . . ?
O3 C7 N1 127.2(6) . . ?
C16 C15 C20 120.0(6) . . ?
C16 C15 N1 120.4(7) . . ?
C20 C15 N1 119.4(7) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.3(8) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(9) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(7) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 119.9(8) . . ?
C18 C19 C23 124.3(7) . . ?
C23 C19 C20 115.7(9) . . ?
C19 C20 C15 117.6(8) . . ?
N2 C20 C15 119.9(6) . . ?
N2 C20 C19 122.5(7) . . ?
C22 C21 H21 119.3 . . ?
N2 C21 H21 119.3 . . ?
N2 C21 C22 121.3(9) . . ?
C1 C8 C9 112.8(5) . . ?
N1 C8 C9 111.6(6) . . ?
N1 C8 C1 100.4(6) . . ?
O1 C8 C9 112.1(6) . . ?
O1 C8 C1 108.0(6) . . ?
O1 C8 N1 111.3(5) . . ?
C19 C23 H23 119.5 . . ?
C22 C23 C19 121.0(7) . . ?
C22 C23 H23 119.5 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(8) . . ?
C23 C22 H22 120.2 . . ?
C7 N1 C15 121.9(7) . . ?
C7 N1 C8 113.4(5) . . ?
C15 N1 C8 123.0(5) . . ?
C21 N2 C20 119.7(6) . . ?
C8 O1 H1 109.5 . . ?
C14 O2 H2A 109.5 . . ?

_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 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# 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_sxj-s-504-tm2
_database_code_depnum_ccdc_archive 'CCDC 1935313'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.06(C23 H16 N2 O2)'
_chemical_formula_sum            'C1.42 H0.98 N0.12 O0.12'
_chemical_formula_weight         21.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.585(3)
_cell_length_b                   7.8514(18)
_cell_length_c                   21.381(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.63(2)
_cell_angle_gamma                90
_cell_volume                     1726.9(7)
_cell_formula_units_Z            65
_cell_measurement_reflns_used    442
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      66.8020
_cell_measurement_theta_min      4.2810
_shelx_estimated_absorpt_T_max   0.850
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.558
_diffrn_reflns_Laue_measured_fraction_max 0.523
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2339
_diffrn_reflns_point_group_measured_fraction_full 0.558
_diffrn_reflns_point_group_measured_fraction_max 0.523
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.381
_diffrn_reflns_theta_min         4.323
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.558
_diffrn_measured_fraction_theta_max 0.523
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00   9.00   1.00   50.00    --  -40.80  57.00  60.00   77
  2  ω   -109.00 -82.00   1.00   50.00    --  -40.80-137.00 -18.00   27
  3  ω     49.00  96.00   1.00   50.00    --   40.80-125.00-120.00   47
  4  ω     52.00 128.00   1.00  215.00    --  107.14 -45.00  60.00   76
  5  ω     35.00  67.00   1.00  215.00    --  107.14-125.00 -60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284235000
_diffrn_orient_matrix_UB_12      -0.1912120000
_diffrn_orient_matrix_UB_13      -0.0127428000
_diffrn_orient_matrix_UB_21      0.1202624000
_diffrn_orient_matrix_UB_22      -0.0446149000
_diffrn_orient_matrix_UB_23      0.0536532000
_diffrn_orient_matrix_UB_31      -0.0847285000
_diffrn_orient_matrix_UB_32      0.0003584000
_diffrn_orient_matrix_UB_33      0.0494570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1060
_reflns_number_total             1819
_reflns_odcompleteness_completeness 54.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      1.118
_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)+(0.1247P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2391
_refine_ls_wR_factor_ref         0.2789
_refine_special_details          ?
_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:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
C1 C 0.4413(6) 0.5733(8) 0.3620(3) 0.0696(15) Uani 1 1 d . . . . .
C2 C 0.5208(7) 0.4291(9) 0.3495(3) 0.0786(18) Uani 1 1 d . . . . .
C3 C 0.3256(7) 0.6060(10) 0.3152(4) 0.0858(19) Uani 1 1 d . . . . .
H3 H 0.300462 0.535888 0.279359 0.103 Uiso 1 1 calc R . . . .
C4 C 0.2505(8) 0.7435(10) 0.3235(4) 0.097(2) Uani 1 1 d . . . . .
H4 H 0.173915 0.767874 0.293265 0.116 Uiso 1 1 calc R . . . .
C5 C 0.2905(9) 0.8445(10) 0.3772(5) 0.107(3) Uani 1 1 d . . . . .
H5 H 0.241290 0.939255 0.382383 0.128 Uiso 1 1 calc R . . . .
C6 C 0.3994(7) 0.8089(9) 0.4224(4) 0.092(2) Uani 1 1 d . . . . .
H6 H 0.422042 0.877572 0.458729 0.111 Uiso 1 1 calc R . . . .
C7 C 0.4797(7) 0.6702(8) 0.4159(3) 0.0725(16) Uani 1 1 d . . . . .
C8 C 0.5991(7) 0.6312(8) 0.4639(3) 0.0707(16) Uani 1 1 d . . . . .
C9 C 0.6373(8) 0.7235(9) 0.5204(3) 0.090(2) Uani 1 1 d . . . . .
H9 H 0.586077 0.813773 0.528115 0.108 Uiso 1 1 calc R . . . .
C10 C 0.7469(9) 0.6851(10) 0.5644(3) 0.097(2) Uani 1 1 d . . . . .
H10 H 0.770396 0.748998 0.601950 0.116 Uiso 1 1 calc R . . . .
C11 C 0.8253(7) 0.5515(9) 0.5544(3) 0.0844(19) Uani 1 1 d . . . . .
H11 H 0.901997 0.526868 0.584565 0.101 Uiso 1 1 calc R . . . .
C12 C 0.7882(6) 0.4558(9) 0.4993(3) 0.0745(16) Uani 1 1 d . . . . .
C13 C 0.6745(6) 0.4929(8) 0.4527(3) 0.0680(15) Uani 1 1 d . . . . .
C14 C 0.9622(9) 0.2588(12) 0.5354(4) 0.111(3) Uani 1 1 d . . . . .
H14A H 1.006924 0.171353 0.517792 0.166 Uiso 1 1 calc GR . . . .
H14B H 0.928010 0.211926 0.569514 0.166 Uiso 1 1 calc GR . . . .
H14C H 1.021771 0.349133 0.552128 0.166 Uiso 1 1 calc GR . . . .
C15 C 0.7131(7) 0.2579(8) 0.3771(3) 0.0686(16) Uani 1 1 d . . . . .
C16 C 0.6931(7) 0.0946(9) 0.3890(3) 0.0833(19) Uani 1 1 d . . . . .
H16 H 0.629910 0.065736 0.410911 0.100 Uiso 1 1 calc R . . . .
C17 C 0.7679(9) -0.0359(9) 0.3686(4) 0.094(2) Uani 1 1 d . . . . .
H17 H 0.755081 -0.149934 0.377067 0.113 Uiso 1 1 calc R . . . .
C18 C 0.8585(8) 0.0115(10) 0.3361(4) 0.090(2) Uani 1 1 d . . . . .
H18 H 0.909353 -0.071602 0.323018 0.108 Uiso 1 1 calc R . . . .
C19 C 0.8770(7) 0.1827(8) 0.3221(3) 0.0726(17) Uani 1 1 d . . . . .
C20 C 0.8025(6) 0.3095(8) 0.3425(3) 0.0640(15) Uani 1 1 d . . . . .
C21 C 0.8975(8) 0.5173(10) 0.2949(3) 0.086(2) Uani 1 1 d . . . . .
H21 H 0.905960 0.631267 0.284836 0.103 Uiso 1 1 calc R . . . .
C22 C 0.9731(8) 0.4014(12) 0.2721(4) 0.095(2) Uani 1 1 d . . . . .
H22 H 1.029339 0.437470 0.247322 0.114 Uiso 1 1 calc R . . . .
C23 C 0.9648(8) 0.2368(11) 0.2860(4) 0.090(2) Uani 1 1 d . . . . .
H23 H 1.017112 0.157656 0.271714 0.107 Uiso 1 1 calc R . . . .
N1 N 0.6323(5) 0.3916(7) 0.3963(2) 0.0726(14) Uani 1 1 d . . . . .
N2 N 0.8152(6) 0.4807(6) 0.3293(3) 0.0707(14) Uani 1 1 d . . . . .
O1 O 0.8602(6) 0.3228(8) 0.4872(2) 0.118(2) Uani 1 1 d . . . . .
O2 O 0.4929(5) 0.3441(7) 0.3000(2) 0.1042(17) 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 1.472(9) . ?
C1 C3 1.410(9) . ?
C1 C7 1.361(9) . ?
C2 N1 1.387(8) . ?
C2 O2 1.227(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.347(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(9) . ?
C7 C8 1.460(9) . ?
C8 C9 1.384(9) . ?
C8 C13 1.401(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.344(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(8) . ?
C12 C13 1.400(9) . ?
C12 O1 1.354(8) . ?
C13 N1 1.426(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 O1 1.399(9) . ?
C15 C16 1.334(9) . ?
C15 C20 1.392(9) . ?
C15 N1 1.472(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.425(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.362(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.401(10) . ?
C19 C20 1.402(8) . ?
C19 C23 1.407(10) . ?
C20 N2 1.386(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(10) . ?
C21 N2 1.297(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.334(10) . ?
C23 H23 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
C3 C1 C2 116.7(6) . . ?
C7 C1 C2 120.9(6) . . ?
C7 C1 C3 122.4(6) . . ?
N1 C2 C1 117.3(5) . . ?
O2 C2 C1 122.9(6) . . ?
O2 C2 N1 119.8(6) . . ?
C1 C3 H3 120.6 . . ?
C4 C3 C1 118.8(8) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(8) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(8) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.6(8) . . ?
C7 C6 H6 119.2 . . ?
C1 C7 C6 116.6(7) . . ?
C1 C7 C8 121.0(6) . . ?
C6 C7 C8 122.4(6) . . ?
C9 C8 C7 122.0(6) . . ?
C9 C8 C13 119.6(7) . . ?
C13 C8 C7 118.4(6) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(7) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(6) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(7) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 121.4(6) . . ?
O1 C12 C11 121.7(6) . . ?
O1 C12 C13 116.9(6) . . ?
C8 C13 N1 120.0(6) . . ?
C12 C13 C8 117.9(6) . . ?
C12 C13 N1 122.1(6) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
C16 C15 C20 122.7(6) . . ?
C16 C15 N1 120.2(6) . . ?
C20 C15 N1 116.9(5) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(6) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 121.0 . . ?
C18 C17 C16 118.0(7) . . ?
C18 C17 H17 121.0 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.5(7) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 119.8(6) . . ?
C18 C19 C23 123.4(6) . . ?
C20 C19 C23 116.7(6) . . ?
C15 C20 C19 117.5(6) . . ?
N2 C20 C15 120.1(5) . . ?
N2 C20 C19 122.4(5) . . ?
C22 C21 H21 117.3 . . ?
N2 C21 H21 117.3 . . ?
N2 C21 C22 125.4(7) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.2(7) . . ?
C23 C22 H22 120.4 . . ?
C19 C23 H23 120.0 . . ?
C22 C23 C19 120.1(7) . . ?
C22 C23 H23 120.0 . . ?
C2 N1 C13 122.3(5) . . ?
C2 N1 C15 113.7(5) . . ?
C13 N1 C15 123.2(5) . . ?
C21 N2 C20 116.1(6) . . ?
C12 O1 C14 120.5(6) . . ?

_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 2.864
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_sxj-s-468
_database_code_depnum_ccdc_archive 'CCDC 1935314'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.11(C26 H16 N2 O)'
_chemical_formula_sum            'C2.97 H1.83 N0.23 O0.11'
_chemical_formula_weight         42.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9197(8)
_cell_length_b                   11.2944(11)
_cell_length_c                   21.008(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.906(9)
_cell_angle_gamma                90
_cell_volume                     1861.3(3)
_cell_formula_units_Z            35
_cell_measurement_reflns_used    2559
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.7570
_cell_measurement_theta_min      4.4150
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.718
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_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  97.00   1.00   19.72    --   11.85-178.00-150.00   57
  2  ω     -8.00  42.00   1.00   19.72    --  -12.09  38.00  30.00   50
  3  ω    -87.00  17.00   1.00   19.72    --  -12.09 -77.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124513000
_diffrn_orient_matrix_UB_12      -0.0603527000
_diffrn_orient_matrix_UB_13      -0.0087012000
_diffrn_orient_matrix_UB_21      -0.0026851000
_diffrn_orient_matrix_UB_22      0.0154455000
_diffrn_orient_matrix_UB_23      -0.0328390000
_diffrn_orient_matrix_UB_31      0.0895851000
_diffrn_orient_matrix_UB_32      -0.0079134000
_diffrn_orient_matrix_UB_33      0.0025773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2536
_reflns_number_total             4507
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.043
_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)+(0.0453P)²+0.7667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25)
;
_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
C1 C 0.6483(3) 0.3755(2) 0.35761(10) 0.0452(5) Uani 1 1 d . . . . .
C2 C 0.7283(3) 0.47741(18) 0.39337(10) 0.0415(5) Uani 1 1 d . . . . .
C3 C 0.7951(3) 0.5656(2) 0.35908(11) 0.0484(6) Uani 1 1 d . . . . .
H3 H 0.788965 0.558180 0.314733 0.058 Uiso 1 1 calc R . . . .
C4 C 0.8722(3) 0.6661(2) 0.38943(11) 0.0483(6) Uani 1 1 d . . . . .
C5 C 0.9392(3) 0.7591(2) 0.35508(14) 0.0651(7) Uani 1 1 d . . . . .
H5 H 0.932114 0.754979 0.310582 0.078 Uiso 1 1 calc R . . . .
C6 C 1.0140(4) 0.8544(3) 0.38710(18) 0.0783(9) Uani 1 1 d . . . . .
H6 H 1.056608 0.915424 0.364193 0.094 Uiso 1 1 calc R . . . .
C7 C 1.0275(4) 0.8616(2) 0.45395(18) 0.0782(9) Uani 1 1 d . . . . .
H7 H 1.082433 0.926169 0.475085 0.094 Uiso 1 1 calc R . . . .
C8 C 0.9617(3) 0.7758(2) 0.48864(15) 0.0686(7) Uani 1 1 d . . . . .
H8 H 0.968869 0.783270 0.533013 0.082 Uiso 1 1 calc R . . . .
C9 C 0.8817(3) 0.6745(2) 0.45733(12) 0.0504(6) Uani 1 1 d . . . . .
C10 C 0.8126(3) 0.5836(2) 0.49148(11) 0.0511(6) Uani 1 1 d . . . . .
H10 H 0.818655 0.590151 0.535869 0.061 Uiso 1 1 calc R . . . .
C11 C 0.7359(3) 0.48487(19) 0.46121(10) 0.0415(5) Uani 1 1 d . . . . .
C12 C 0.6623(3) 0.3882(2) 0.49505(10) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.6617(3) 0.3879(2) 0.56180(11) 0.0542(6) Uani 1 1 d . . . . .
H13 H 0.709264 0.451493 0.586079 0.065 Uiso 1 1 calc R . . . .
C14 C 0.5923(3) 0.2955(3) 0.59210(12) 0.0630(7) Uani 1 1 d . . . . .
H14 H 0.593930 0.296825 0.636439 0.076 Uiso 1 1 calc R . . . .
C15 C 0.5204(3) 0.2009(3) 0.55678(12) 0.0642(7) Uani 1 1 d . . . . .
H15 H 0.472799 0.138797 0.577310 0.077 Uiso 1 1 calc R . . . .
C16 C 0.5190(3) 0.1981(2) 0.49138(12) 0.0571(6) Uani 1 1 d . . . . .
H16 H 0.470777 0.133951 0.467743 0.069 Uiso 1 1 calc R . . . .
C17 C 0.5895(3) 0.2911(2) 0.46032(10) 0.0456(5) Uani 1 1 d . . . . .
C18 C 0.5091(3) 0.1867(2) 0.35633(10) 0.0485(6) Uani 1 1 d . . . . .
C19 C 0.6033(3) 0.0918(2) 0.34347(12) 0.0553(6) Uani 1 1 d . . . . .
H19 H 0.718942 0.088517 0.359132 0.066 Uiso 1 1 calc R . . . .
C20 C 0.5236(4) -0.0034(2) 0.30558(13) 0.0711(8) Uani 1 1 d . . . . .
H20 H 0.587654 -0.068450 0.296000 0.085 Uiso 1 1 calc R . . . .
C21 C 0.3545(4) 0.0015(2) 0.28372(13) 0.0674(7) Uani 1 1 d . . . . .
H21 H 0.303095 -0.060939 0.259531 0.081 Uiso 1 1 calc R . . . .
C22 C 0.2561(3) 0.0991(2) 0.29698(11) 0.0542(6) Uani 1 1 d . . . . .
C23 C 0.0799(4) 0.1095(3) 0.27516(12) 0.0656(7) Uani 1 1 d . . . . .
H23 H 0.023647 0.049983 0.250035 0.079 Uiso 1 1 calc R . . . .
C24 C -0.0070(4) 0.2059(3) 0.29075(13) 0.0683(7) Uani 1 1 d . . . . .
H24 H -0.122794 0.213643 0.276266 0.082 Uiso 1 1 calc R . . . .
C25 C 0.0797(3) 0.2931(2) 0.32874(12) 0.0631(7) Uani 1 1 d . . . . .
H25 H 0.017235 0.357941 0.339636 0.076 Uiso 1 1 calc R . . . .
C26 C 0.3338(3) 0.1945(2) 0.33469(10) 0.0471(5) Uani 1 1 d . . . . .
N1 N 0.2431(2) 0.29083(17) 0.35042(9) 0.0521(5) Uani 1 1 d . . . . .
N2 N 0.5900(2) 0.28567(16) 0.39280(8) 0.0473(5) Uani 1 1 d . . . . .
O1 O 0.6347(2) 0.36805(14) 0.29843(7) 0.0620(5) 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 1.469(3) . ?
C1 N2 1.373(3) . ?
C1 O1 1.236(2) . ?
C2 C3 1.377(3) . ?
C2 C11 1.421(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(3) . ?
C4 C5 1.418(3) . ?
C4 C9 1.421(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.361(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.424(3) . ?
C9 C10 1.405(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C11 C12 1.466(3) . ?
C12 C13 1.403(3) . ?
C12 C17 1.397(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(3) . ?
C17 N2 1.420(3) . ?
C18 C19 1.355(3) . ?
C18 C26 1.403(3) . ?
C18 N2 1.453(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.432(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.356(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.400(4) . ?
C22 C23 1.412(4) . ?
C22 C26 1.426(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.352(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(4) . ?
C25 H25 0.9300 . ?
C25 N1 1.312(3) . ?
C26 N1 1.369(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
N2 C1 C2 117.19(18) . . ?
O1 C1 C2 122.67(19) . . ?
O1 C1 N2 120.1(2) . . ?
C3 C2 C1 117.93(19) . . ?
C3 C2 C11 121.0(2) . . ?
C11 C2 C1 121.02(19) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 122.6(2) . . ?
C3 C4 C9 118.0(2) . . ?
C5 C4 C9 119.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 118.4(2) . . ?
C10 C9 C4 119.6(2) . . ?
C10 C9 C8 122.0(2) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 H10 118.9 . . ?
C2 C11 C12 118.51(19) . . ?
C10 C11 C2 117.68(19) . . ?
C10 C11 C12 123.81(19) . . ?
C13 C12 C11 122.9(2) . . ?
C17 C12 C11 119.62(18) . . ?
C17 C12 C13 117.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 N2 119.84(19) . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 N2 119.5(2) . . ?
C19 C18 C26 122.2(2) . . ?
C19 C18 N2 119.9(2) . . ?
C26 C18 N2 117.9(2) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(2) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 123.6(2) . . ?
C21 C22 C26 119.7(2) . . ?
C23 C22 C26 116.7(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.8(3) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 117.6 . . ?
N1 C25 C24 124.9(3) . . ?
N1 C25 H25 117.6 . . ?
C18 C26 C22 117.7(2) . . ?
N1 C26 C18 120.0(2) . . ?
N1 C26 C22 122.2(2) . . ?
C25 N1 C26 117.2(2) . . ?
C1 N2 C17 123.61(18) . . ?
C1 N2 C18 116.18(17) . . ?
C17 N2 C18 119.88(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 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_sxj-s-465-TM
_database_code_depnum_ccdc_archive 'CCDC 1935312'
loop_
_audit_author_name
_audit_author_address
'Fen Xu'
;Zhengzhou University of Light Industry, Zhengzhou, Henan, China
China
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.17(C22 H13 Cl N2 O)'
_chemical_formula_sum            'C3.67 H2.17 Cl0.17 N0.33 O0.17'
_chemical_formula_weight         59.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'
Cl Cl 0.1484 0.1585 '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                   11.6827(13)
_cell_length_b                   11.2961(12)
_cell_length_c                   13.0187(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.779(10)
_cell_angle_gamma                90
_cell_volume                     1681.9(3)
_cell_formula_units_Z            24
_cell_measurement_reflns_used    2793
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.7840
_cell_measurement_theta_min      3.9340
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9692
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.681
_diffrn_reflns_theta_min         3.563
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  75.00   1.00   60.00    --   11.85  57.00 150.00   51
  2  ω    -20.00  16.00   1.00   60.00    --  -12.09 -99.00-180.00   36
  3  ω    -37.00  38.00   1.00   60.00    --  -12.09  38.00  30.00   75
  4  ω     27.00  62.00   1.00   60.00    --  -12.09  38.00  60.00   35
  5  ω     -4.00  28.00   1.00   60.00    --  -12.09 -99.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371370000
_diffrn_orient_matrix_UB_12      0.0426726000
_diffrn_orient_matrix_UB_13      -0.0162866000
_diffrn_orient_matrix_UB_21      -0.0322133000
_diffrn_orient_matrix_UB_22      0.0460090000
_diffrn_orient_matrix_UB_23      0.0180766000
_diffrn_orient_matrix_UB_31      0.0377979000
_diffrn_orient_matrix_UB_32      -0.0027159000
_diffrn_orient_matrix_UB_33      0.0500437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2593
_reflns_number_total             4050
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.060
_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)+(0.0787P)²+0.8300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C20(H20), C22(H22)
;
_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
C1 C 0.7312(3) 0.9040(3) 0.5491(3) 0.0735(9) Uani 1 1 d . . . . .
H1 H 0.685481 0.921947 0.483741 0.088 Uiso 1 1 calc R . . . .
C2 C 0.7963(3) 0.9965(3) 0.6050(3) 0.0775(10) Uani 1 1 d . . . . .
H2 H 0.794486 1.071988 0.576206 0.093 Uiso 1 1 calc R . . . .
C3 C 0.8614(3) 0.9742(3) 0.7014(3) 0.0640(8) Uani 1 1 d . . . . .
H3 H 0.905151 1.034195 0.739702 0.077 Uiso 1 1 calc R . . . .
C4 C 0.8624(2) 0.8596(2) 0.7428(2) 0.0494(6) Uani 1 1 d . . . . .
C5 C 0.7964(2) 0.7707(2) 0.67883(19) 0.0449(6) Uani 1 1 d . . . . .
C6 C 0.8015(2) 0.6538(2) 0.71886(19) 0.0452(6) Uani 1 1 d . . . . .
C7 C 0.8616(3) 0.6276(3) 0.8170(2) 0.0567(7) Uani 1 1 d . . . . .
H7 H 0.863578 0.550211 0.841628 0.068 Uiso 1 1 calc R . . . .
C8 C 0.9211(3) 0.7183(3) 0.8816(2) 0.0661(8) Uani 1 1 d . . . . .
H8 H 0.959492 0.700897 0.949797 0.079 Uiso 1 1 calc R . . . .
C9 C 0.9224(3) 0.8299(3) 0.8448(2) 0.0600(8) Uani 1 1 d . . . . .
H9 H 0.963589 0.888151 0.887466 0.072 Uiso 1 1 calc R . . . .
C10 C 0.6345(2) 0.5166(2) 0.66387(19) 0.0442(6) Uani 1 1 d . . . . .
C11 C 0.5761(2) 0.5713(3) 0.7353(2) 0.0572(7) Uani 1 1 d . . . . .
H11 H 0.609691 0.635711 0.774795 0.069 Uiso 1 1 calc R . . . .
C12 C 0.4687(3) 0.5288(3) 0.7465(3) 0.0700(9) Uani 1 1 d . . . . .
H12 H 0.429757 0.564690 0.793863 0.084 Uiso 1 1 calc R . . . .
C13 C 0.4185(3) 0.4333(3) 0.6878(3) 0.0709(9) Uani 1 1 d . . . . .
H13 H 0.346460 0.404624 0.696437 0.085 Uiso 1 1 calc R . . . .
C14 C 0.4740(2) 0.3809(3) 0.6173(2) 0.0611(8) Uani 1 1 d . . . . .
H14 H 0.438209 0.317831 0.577244 0.073 Uiso 1 1 calc R . . . .
C15 C 0.5836(2) 0.4197(2) 0.6039(2) 0.0472(6) Uani 1 1 d . . . . .
C16 C 0.8069(2) 0.5134(2) 0.58243(18) 0.0414(5) Uani 1 1 d . . . . .
C17 C 0.7538(2) 0.4121(2) 0.51917(18) 0.0418(5) Uani 1 1 d . . . . .
C18 C 0.6462(2) 0.3654(2) 0.52855(19) 0.0450(6) Uani 1 1 d . . . . .
C19 C 0.6026(3) 0.2692(3) 0.4641(2) 0.0581(7) Uani 1 1 d . . . . .
H19 H 0.530769 0.236456 0.468665 0.070 Uiso 1 1 calc R . . . .
C20 C 0.6640(3) 0.2227(3) 0.3945(2) 0.0619(8) Uani 1 1 d . . . . .
H20 H 0.633719 0.158960 0.352411 0.074 Uiso 1 1 calc R . . . .
C21 C 0.7704(3) 0.2703(2) 0.3868(2) 0.0541(7) Uani 1 1 d . . . . .
C22 C 0.8172(2) 0.3641(2) 0.44738(19) 0.0480(6) Uani 1 1 d . . . . .
H22 H 0.889066 0.395649 0.441512 0.058 Uiso 1 1 calc R . . . .
Cl1 Cl 0.84842(9) 0.21100(8) 0.29793(7) 0.0805(3) Uani 1 1 d . . . . .
N1 N 0.74400(17) 0.55913(18) 0.65282(16) 0.0431(5) Uani 1 1 d . . . . .
N2 N 0.7298(2) 0.7938(2) 0.58196(18) 0.0562(6) Uani 1 1 d . . . . .
O1 O 0.90239(15) 0.55550(16) 0.57687(14) 0.0510(5) 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 H1 0.9300 . ?
C1 C2 1.405(5) . ?
C1 N2 1.318(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.351(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(4) . ?
C4 C5 1.427(4) . ?
C4 C9 1.410(4) . ?
C5 C6 1.416(4) . ?
C5 N2 1.365(3) . ?
C6 C7 1.359(4) . ?
C6 N1 1.448(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.415(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.350(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.404(4) . ?
C10 C15 1.404(4) . ?
C10 N1 1.401(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(4) . ?
C15 C18 1.472(4) . ?
C16 C17 1.471(3) . ?
C16 N1 1.386(3) . ?
C16 O1 1.229(3) . ?
C17 C18 1.392(3) . ?
C17 C22 1.413(3) . ?
C18 C19 1.404(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(4) . ?
C21 C22 1.366(4) . ?
C21 Cl1 1.746(3) . ?
C22 H22 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 H1 117.4 . . ?
N2 C1 H1 117.4 . . ?
N2 C1 C2 125.2(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C9 123.1(3) . . ?
C9 C4 C5 119.2(3) . . ?
C6 C5 C4 117.7(2) . . ?
N2 C5 C4 122.9(2) . . ?
N2 C5 C6 119.4(2) . . ?
C5 C6 N1 119.4(2) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 N1 119.1(2) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C15 120.3(2) . . ?
N1 C10 C11 119.6(2) . . ?
N1 C10 C15 120.1(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C18 119.0(2) . . ?
C14 C15 C10 118.0(3) . . ?
C14 C15 C18 123.0(3) . . ?
N1 C16 C17 116.1(2) . . ?
O1 C16 C17 123.5(2) . . ?
O1 C16 N1 120.4(2) . . ?
C18 C17 C16 122.1(2) . . ?
C18 C17 C22 121.1(2) . . ?
C22 C17 C16 116.8(2) . . ?
C17 C18 C15 118.7(2) . . ?
C17 C18 C19 117.7(2) . . ?
C19 C18 C15 123.5(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 Cl1 120.0(2) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 Cl1 118.6(2) . . ?
C17 C22 H22 120.7 . . ?
C21 C22 C17 118.6(2) . . ?
C21 C22 H22 120.7 . . ?
C10 N1 C6 120.95(19) . . ?
C16 N1 C6 115.06(19) . . ?
C16 N1 C10 124.0(2) . . ?
C1 N2 C5 116.0(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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.522
