# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_137-1
_database_code_depnum_ccdc_archive 'CCDC 2073613'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 Cl F N4 O2, C H2 Cl2'
_chemical_formula_sum            'C24 H18 Cl3 F N4 O2'
_chemical_formula_weight         519.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      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                   11.3994(5)
_cell_length_b                   12.1363(6)
_cell_length_c                   17.1162(6)
_cell_angle_alpha                102.133(3)
_cell_angle_beta                 91.902(3)
_cell_angle_gamma                98.107(4)
_cell_volume                     2287.10(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6644
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6380
_cell_measurement_theta_min      2.4350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.115
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  85.00   1.00    3.50    --   11.90  57.00  60.00   98
  2  ω     35.00  61.00   1.00    3.50    --   11.90 178.00-120.00   26
  3  ω    -15.00  78.00   1.00    3.50    --   11.90  77.00-180.00   93
  4  ω    -55.00  37.00   1.00    3.50    --   11.90 -57.00 -90.00   92
;
_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      0.0073195000
_diffrn_orient_matrix_UB_12      0.0109204000
_diffrn_orient_matrix_UB_13      -0.0387992000
_diffrn_orient_matrix_UB_21      0.0082804000
_diffrn_orient_matrix_UB_22      0.0594837000
_diffrn_orient_matrix_UB_23      0.0164951000
_diffrn_orient_matrix_UB_31      0.0620064000
_diffrn_orient_matrix_UB_32      0.0000722000
_diffrn_orient_matrix_UB_33      0.0051779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6482
_reflns_number_total             8068
_reflns_odcompleteness_completeness 99.96
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         8068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.032
_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)+(0.0354P)²+2.0688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1083
_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:
 C10(H10A,H10B), C17(H17A,H17B), C23(H23A,H23B), C31(H31A,H31B), C36(H36A,
 H36B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C45(H45), C47(H47)
;
_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
Cl1 Cl -0.17176(7) 0.85926(6) 0.98983(4) 0.03542(18) Uani 1 1 d . . . . .
F1 F -0.25446(13) 0.44569(13) 1.00906(9) 0.0296(4) Uani 1 1 d . . . . .
O1 O 0.08081(17) 0.23512(15) 0.81398(11) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.27998(16) 0.53442(15) 0.72667(11) 0.0287(4) Uani 1 1 d . . . . .
N1 N -0.07027(18) 0.39574(17) 0.90285(11) 0.0194(5) Uani 1 1 d . . . . .
N2 N -0.03211(17) 0.58436(16) 0.90151(11) 0.0169(4) Uani 1 1 d . . . . .
N3 N 0.17470(18) 0.38481(17) 0.76774(12) 0.0194(5) Uani 1 1 d . . . . .
N4 N 0.13631(18) 0.57509(16) 0.81244(12) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.0904(2) 0.3359(2) 0.81313(14) 0.0208(6) Uani 1 1 d . . . . .
C2 C 0.0216(2) 0.4174(2) 0.85609(14) 0.0177(5) Uani 1 1 d . . . . .
C3 C 0.0469(2) 0.5304(2) 0.85442(13) 0.0175(5) Uani 1 1 d . . . . .
C4 C 0.2016(2) 0.4999(2) 0.76581(14) 0.0206(6) Uani 1 1 d . . . . .
C5 C -0.1015(2) 0.4966(2) 0.92927(14) 0.0190(5) Uani 1 1 d . . . . .
C6 C -0.1911(2) 0.5298(2) 0.98030(14) 0.0219(6) Uani 1 1 d . . . . .
C7 C -0.2133(2) 0.6373(2) 1.00024(14) 0.0241(6) Uani 1 1 d . . . . .
H7 H -0.272758 0.656708 1.034133 0.029 Uiso 1 1 calc R U . . .
C8 C -0.1424(2) 0.7205(2) 0.96749(15) 0.0239(6) Uani 1 1 d . . . . .
C9 C -0.0544(2) 0.6959(2) 0.91932(14) 0.0201(5) Uani 1 1 d . . . . .
H9 H -0.009856 0.752153 0.898606 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1866(2) 0.6965(2) 0.82894(15) 0.0222(6) Uani 1 1 d . . . . .
H10A H 0.269561 0.702896 0.816886 0.027 Uiso 1 1 calc R U . . .
H10B H 0.183754 0.727833 0.885733 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1256(2) 0.7684(2) 0.78280(14) 0.0220(6) Uani 1 1 d . . . . .
C12 C 0.1521(3) 0.8861(2) 0.80682(17) 0.0361(7) Uani 1 1 d . . . . .
H12 H 0.205613 0.918897 0.850467 0.043 Uiso 1 1 calc R U . . .
C13 C 0.0988(3) 0.9551(3) 0.7657(2) 0.0484(9) Uani 1 1 d . . . . .
H13 H 0.116973 1.033966 0.781798 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0193(3) 0.9075(3) 0.7015(2) 0.0518(10) Uani 1 1 d . . . . .
H14 H -0.016276 0.954042 0.674189 0.062 Uiso 1 1 calc R U . . .
C15 C -0.0074(3) 0.7916(3) 0.6776(2) 0.0486(9) Uani 1 1 d . . . . .
H15 H -0.061713 0.759407 0.634293 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0463(3) 0.7214(2) 0.71794(17) 0.0354(7) Uani 1 1 d . . . . .
H16 H 0.028573 0.642599 0.700972 0.042 Uiso 1 1 calc R U . . .
C17 C 0.2455(2) 0.3066(2) 0.71910(15) 0.0246(6) Uani 1 1 d . . . . .
H17A H 0.272478 0.338179 0.674128 0.030 Uiso 1 1 calc R U . . .
H17B H 0.195264 0.234252 0.697847 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3518(2) 0.2859(2) 0.76579(15) 0.0252(6) Uani 1 1 d . . . . .
C19 C 0.4177(2) 0.3716(2) 0.82350(16) 0.0305(6) Uani 1 1 d . . . . .
H19 H 0.394811 0.443569 0.835269 0.037 Uiso 1 1 calc R U . . .
C20 C 0.5172(3) 0.3516(3) 0.86389(18) 0.0407(8) Uani 1 1 d . . . . .
H20 H 0.559851 0.409954 0.902785 0.049 Uiso 1 1 calc R U . . .
C21 C 0.5532(3) 0.2474(3) 0.8473(2) 0.0467(9) Uani 1 1 d . . . . .
H21 H 0.620102 0.234386 0.874513 0.056 Uiso 1 1 calc R U . . .
C22 C 0.4899(3) 0.1619(3) 0.7900(2) 0.0557(10) Uani 1 1 d . . . . .
H22 H 0.514829 0.090881 0.777873 0.067 Uiso 1 1 calc R U . . .
C24 C 0.3885(3) 0.1800(3) 0.74971(18) 0.0430(8) Uani 1 1 d . . . . .
H24 H 0.345330 0.120631 0.711802 0.052 Uiso 1 1 calc R U . . .
Cl2 Cl 0.20822(7) 0.87991(6) 1.02977(4) 0.0407(2) Uani 1 1 d . . . . .
Cl3 Cl 0.19477(7) 0.92822(7) 1.20244(4) 0.0441(2) Uani 1 1 d . . . . .
C23 C 0.1142(3) 0.8968(3) 1.10965(16) 0.0365(7) Uani 1 1 d . . . . .
H23A H 0.069094 0.957902 1.106388 0.044 Uiso 1 1 calc R U . . .
H23B H 0.058492 0.827217 1.105128 0.044 Uiso 1 1 calc R U . . .
Cl4 Cl 0.30416(7) 0.84907(6) 0.61125(4) 0.0401(2) Uani 1 1 d . . . . .
F2 F 0.22796(14) 0.44032(13) 0.45504(9) 0.0330(4) Uani 1 1 d . . . . .
O3 O 0.57594(16) 0.22788(14) 0.58889(10) 0.0261(4) Uani 1 1 d . . . . .
O4 O 0.77129(16) 0.52378(15) 0.77975(10) 0.0296(4) Uani 1 1 d . . . . .
N5 N 0.67029(18) 0.37624(17) 0.68542(11) 0.0198(5) Uani 1 1 d . . . . .
N6 N 0.62180(18) 0.56387(17) 0.70487(11) 0.0199(5) Uani 1 1 d . . . . .
N7 N 0.45005(18) 0.57492(17) 0.61474(11) 0.0184(4) Uani 1 1 d . . . . .
N8 N 0.41646(18) 0.38774(18) 0.54931(11) 0.0211(5) Uani 1 1 d . . . . .
C25 C 0.8552(2) 0.2968(2) 0.65265(14) 0.0205(5) Uani 1 1 d . . . . .
C26 C 0.9295(2) 0.3955(2) 0.64652(15) 0.0257(6) Uani 1 1 d . . . . .
H26 H 0.916604 0.465521 0.676589 0.031 Uiso 1 1 calc R U . . .
C27 C 1.0219(2) 0.3911(2) 0.59661(16) 0.0286(6) Uani 1 1 d . . . . .
H27 H 1.070184 0.458033 0.592864 0.034 Uiso 1 1 calc R U . . .
C28 C 1.0430(3) 0.2883(3) 0.55236(17) 0.0347(7) Uani 1 1 d . . . . .
H28 H 1.106049 0.285242 0.519269 0.042 Uiso 1 1 calc R U . . .
C29 C 0.9701(3) 0.1901(3) 0.55743(19) 0.0438(8) Uani 1 1 d . . . . .
H29 H 0.983280 0.120386 0.527100 0.053 Uiso 1 1 calc R U . . .
C30 C 0.8770(3) 0.1944(2) 0.60744(17) 0.0345(7) Uani 1 1 d . . . . .
H30 H 0.828533 0.127227 0.610572 0.041 Uiso 1 1 calc R U . . .
C31 C 0.7525(2) 0.3005(2) 0.70589(15) 0.0222(6) Uani 1 1 d . . . . .
H31A H 0.709442 0.224058 0.700215 0.027 Uiso 1 1 calc R U . . .
H31B H 0.782543 0.327664 0.761299 0.027 Uiso 1 1 calc R U . . .
C32 C 0.5829(2) 0.3276(2) 0.62307(14) 0.0206(5) Uani 1 1 d . . . . .
C33 C 0.5096(2) 0.4080(2) 0.60583(13) 0.0189(5) Uani 1 1 d . . . . .
C34 C 0.5320(2) 0.5200(2) 0.64583(13) 0.0187(5) Uani 1 1 d . . . . .
C35 C 0.6922(2) 0.4897(2) 0.72689(14) 0.0222(6) Uani 1 1 d . . . . .
C36 C 0.6598(2) 0.6865(2) 0.73786(14) 0.0230(6) Uani 1 1 d . . . . .
H36A H 0.649475 0.727708 0.695924 0.028 Uiso 1 1 calc R U . . .
H36B H 0.743702 0.698976 0.754250 0.028 Uiso 1 1 calc R U . . .
C37 C 0.5927(2) 0.7349(2) 0.80837(15) 0.0236(6) Uani 1 1 d . . . . .
C38 C 0.5586(2) 0.6715(2) 0.86457(15) 0.0300(6) Uani 1 1 d . . . . .
H38 H 0.573618 0.596817 0.857445 0.036 Uiso 1 1 calc R U . . .
C39 C 0.5025(3) 0.7184(3) 0.93109(17) 0.0388(7) Uani 1 1 d . . . . .
H39 H 0.479829 0.675064 0.968383 0.047 Uiso 1 1 calc R U . . .
C40 C 0.4800(3) 0.8287(3) 0.94249(18) 0.0419(8) Uani 1 1 d . . . . .
H40 H 0.443357 0.860352 0.987799 0.050 Uiso 1 1 calc R U . . .
C41 C 0.5118(3) 0.8920(3) 0.88662(18) 0.0436(8) Uani 1 1 d . . . . .
H41 H 0.495362 0.966212 0.893644 0.052 Uiso 1 1 calc R U . . .
C42 C 0.5681(3) 0.8454(2) 0.81999(17) 0.0362(7) Uani 1 1 d . . . . .
H42 H 0.589703 0.888904 0.782576 0.043 Uiso 1 1 calc R U . . .
C43 C 0.3822(2) 0.4882(2) 0.55558(14) 0.0203(5) Uani 1 1 d . . . . .
C44 C 0.2896(2) 0.5227(2) 0.51353(14) 0.0242(6) Uani 1 1 d . . . . .
C45 C 0.2637(2) 0.6291(2) 0.52907(15) 0.0272(6) Uani 1 1 d . . . . .
H45 H 0.201668 0.648694 0.500777 0.033 Uiso 1 1 calc R U . . .
C46 C 0.3348(2) 0.7111(2) 0.59053(15) 0.0264(6) Uani 1 1 d . . . . .
C47 C 0.4247(2) 0.6851(2) 0.63268(14) 0.0225(6) Uani 1 1 d . . . . .
H47 H 0.468960 0.740161 0.673022 0.027 Uiso 1 1 calc R U . . .
Cl5 Cl 0.33897(12) 0.07330(9) 0.37582(5) 0.0848(4) Uani 1 1 d . . . . .
Cl6 Cl 0.24352(9) 0.08617(8) 0.53112(6) 0.0609(3) Uani 1 1 d . . . . .
C48 C 0.3666(3) 0.0667(3) 0.47526(18) 0.0491(9) Uani 1 1 d . . . . .
H48A H 0.389042 -0.006962 0.477127 0.059 Uiso 1 1 calc R U . . .
H48B H 0.432670 0.124900 0.498959 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.729(3) . ?
F1 C6 1.354(3) . ?
O1 C1 1.216(3) . ?
O2 C4 1.214(3) . ?
N1 C2 1.368(3) . ?
N1 C5 1.315(3) . ?
N2 C3 1.372(3) . ?
N2 C5 1.409(3) . ?
N2 C9 1.385(3) . ?
N3 C1 1.401(3) . ?
N3 C4 1.395(3) . ?
N3 C17 1.474(3) . ?
N4 C3 1.380(3) . ?
N4 C4 1.396(3) . ?
N4 C10 1.468(3) . ?
C1 C2 1.444(4) . ?
C2 C3 1.368(3) . ?
C5 C6 1.413(4) . ?
C6 C7 1.339(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.424(4) . ?
C8 C9 1.346(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.377(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.508(4) . ?
C18 C19 1.386(4) . ?
C18 C24 1.382(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.361(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.368(5) . ?
C22 H22 0.9300 . ?
C22 C24 1.394(5) . ?
C24 H24 0.9300 . ?
Cl2 C23 1.761(3) . ?
Cl3 C23 1.749(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
Cl4 C46 1.724(3) . ?
F2 C44 1.353(3) . ?
O3 C32 1.219(3) . ?
O4 C35 1.219(3) . ?
N5 C31 1.484(3) . ?
N5 C32 1.407(3) . ?
N5 C35 1.393(3) . ?
N6 C34 1.380(3) . ?
N6 C35 1.387(3) . ?
N6 C36 1.473(3) . ?
N7 C34 1.376(3) . ?
N7 C43 1.415(3) . ?
N7 C47 1.382(3) . ?
N8 C33 1.372(3) . ?
N8 C43 1.316(3) . ?
C25 C26 1.391(4) . ?
C25 C30 1.379(4) . ?
C25 C31 1.507(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.378(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.374(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.385(4) . ?
C30 H30 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.439(3) . ?
C33 C34 1.371(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.508(4) . ?
C37 C38 1.386(4) . ?
C37 C42 1.384(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.382(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.372(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.375(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.383(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.417(3) . ?
C44 C45 1.339(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.425(4) . ?
C46 C47 1.345(4) . ?
C47 H47 0.9300 . ?
Cl5 C48 1.741(3) . ?
Cl6 C48 1.739(4) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 103.6(2) . . ?
C3 N2 C5 104.56(19) . . ?
C3 N2 C9 133.2(2) . . ?
C9 N2 C5 122.1(2) . . ?
C1 N3 C17 116.3(2) . . ?
C4 N3 C1 127.0(2) . . ?
C4 N3 C17 116.6(2) . . ?
C3 N4 C4 118.2(2) . . ?
C3 N4 C10 123.5(2) . . ?
C4 N4 C10 116.5(2) . . ?
O1 C1 N3 120.8(2) . . ?
O1 C1 C2 126.5(2) . . ?
N3 C1 C2 112.7(2) . . ?
N1 C2 C1 126.9(2) . . ?
C3 C2 N1 112.4(2) . . ?
C3 C2 C1 120.6(2) . . ?
N2 C3 N4 129.7(2) . . ?
C2 C3 N2 106.2(2) . . ?
C2 C3 N4 124.1(2) . . ?
O2 C4 N3 121.9(2) . . ?
O2 C4 N4 120.9(2) . . ?
N3 C4 N4 117.2(2) . . ?
N1 C5 N2 113.1(2) . . ?
N1 C5 C6 130.7(2) . . ?
N2 C5 C6 116.2(2) . . ?
F1 C6 C5 115.8(2) . . ?
C7 C6 F1 121.0(2) . . ?
C7 C6 C5 123.2(2) . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.3(2) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 Cl1 118.4(2) . . ?
C9 C8 Cl1 118.6(2) . . ?
C9 C8 C7 123.0(2) . . ?
N2 C9 H9 121.0 . . ?
C8 C9 N2 118.0(2) . . ?
C8 C9 H9 121.0 . . ?
N4 C10 H10A 108.4 . . ?
N4 C10 H10B 108.4 . . ?
N4 C10 C11 115.3(2) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C12 C11 C10 118.2(2) . . ?
C16 C11 C10 122.6(2) . . ?
C16 C11 C12 119.2(2) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.2(3) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N3 C17 H17A 109.0 . . ?
N3 C17 H17B 109.0 . . ?
N3 C17 C18 113.0(2) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C19 C18 C17 121.9(2) . . ?
C24 C18 C17 120.1(2) . . ?
C24 C18 C19 118.0(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.3(3) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C24 120.8(3) . . ?
C24 C22 H22 119.6 . . ?
C18 C24 C22 120.3(3) . . ?
C18 C24 H24 119.8 . . ?
C22 C24 H24 119.8 . . ?
Cl2 C23 H23A 109.3 . . ?
Cl2 C23 H23B 109.3 . . ?
Cl3 C23 Cl2 111.60(16) . . ?
Cl3 C23 H23A 109.3 . . ?
Cl3 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C32 N5 C31 116.6(2) . . ?
C35 N5 C31 116.47(19) . . ?
C35 N5 C32 126.8(2) . . ?
C34 N6 C35 118.1(2) . . ?
C34 N6 C36 124.3(2) . . ?
C35 N6 C36 116.9(2) . . ?
C34 N7 C43 104.06(19) . . ?
C34 N7 C47 133.7(2) . . ?
C47 N7 C43 122.2(2) . . ?
C43 N8 C33 103.6(2) . . ?
C26 C25 C31 121.6(2) . . ?
C30 C25 C26 118.0(3) . . ?
C30 C25 C31 120.3(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.4(3) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 C29 120.9(3) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
N5 C31 C25 111.45(19) . . ?
N5 C31 H31A 109.3 . . ?
N5 C31 H31B 109.3 . . ?
C25 C31 H31A 109.3 . . ?
C25 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
O3 C32 N5 120.6(2) . . ?
O3 C32 C33 126.6(2) . . ?
N5 C32 C33 112.7(2) . . ?
N8 C33 C32 127.3(2) . . ?
C34 C33 N8 112.2(2) . . ?
C34 C33 C32 120.5(2) . . ?
N7 C34 N6 129.1(2) . . ?
C33 C34 N6 124.3(2) . . ?
C33 C34 N7 106.6(2) . . ?
O4 C35 N5 121.8(2) . . ?
O4 C35 N6 120.7(2) . . ?
N6 C35 N5 117.5(2) . . ?
N6 C36 H36A 108.8 . . ?
N6 C36 H36B 108.8 . . ?
N6 C36 C37 113.9(2) . . ?
H36A C36 H36B 107.7 . . ?
C37 C36 H36A 108.8 . . ?
C37 C36 H36B 108.8 . . ?
C38 C37 C36 120.8(2) . . ?
C42 C37 C36 120.6(2) . . ?
C42 C37 C38 118.5(3) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 C37 120.5(3) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.4(3) . . ?
C40 C39 H39 119.8 . . ?
C39 C40 H40 120.2 . . ?
C39 C40 C41 119.7(3) . . ?
C41 C40 H40 120.2 . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.1(3) . . ?
C42 C41 H41 119.9 . . ?
C37 C42 H42 119.6 . . ?
C41 C42 C37 120.7(3) . . ?
C41 C42 H42 119.6 . . ?
N7 C43 C44 115.7(2) . . ?
N8 C43 N7 113.5(2) . . ?
N8 C43 C44 130.9(2) . . ?
F2 C44 C43 115.3(2) . . ?
C45 C44 F2 121.2(2) . . ?
C45 C44 C43 123.4(2) . . ?
C44 C45 H45 121.2 . . ?
C44 C45 C46 117.6(2) . . ?
C46 C45 H45 121.2 . . ?
C45 C46 Cl4 118.54(19) . . ?
C47 C46 Cl4 118.9(2) . . ?
C47 C46 C45 122.5(2) . . ?
N7 C47 H47 120.7 . . ?
C46 C47 N7 118.6(2) . . ?
C46 C47 H47 120.7 . . ?
Cl5 C48 H48A 109.2 . . ?
Cl5 C48 H48B 109.2 . . ?
Cl6 C48 Cl5 112.14(18) . . ?
Cl6 C48 H48A 109.2 . . ?
Cl6 C48 H48B 109.2 . . ?
H48A C48 H48B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C8 C9 N2 -179.65(16) . . . . ?
F1 C6 C7 C8 179.9(2) . . . . ?
O1 C1 C2 N1 -3.0(4) . . . . ?
O1 C1 C2 C3 175.3(2) . . . . ?
N1 C2 C3 N2 -0.5(3) . . . . ?
N1 C2 C3 N4 179.32(19) . . . . ?
N1 C5 C6 F1 1.9(3) . . . . ?
N1 C5 C6 C7 -178.4(2) . . . . ?
N2 C5 C6 F1 -177.68(18) . . . . ?
N2 C5 C6 C7 2.0(3) . . . . ?
N3 C1 C2 N1 177.2(2) . . . . ?
N3 C1 C2 C3 -4.4(3) . . . . ?
N3 C17 C18 C19 -37.3(4) . . . . ?
N3 C17 C18 C24 144.9(3) . . . . ?
N4 C10 C11 C12 167.1(2) . . . . ?
N4 C10 C11 C16 -13.6(4) . . . . ?
C1 N3 C4 O2 177.0(2) . . . . ?
C1 N3 C4 N4 -1.6(3) . . . . ?
C1 N3 C17 C18 -84.2(3) . . . . ?
C1 C2 C3 N2 -179.04(19) . . . . ?
C1 C2 C3 N4 0.7(3) . . . . ?
C2 N1 C5 N2 -0.4(2) . . . . ?
C2 N1 C5 C6 -179.9(2) . . . . ?
C3 N2 C5 N1 0.1(2) . . . . ?
C3 N2 C5 C6 179.72(19) . . . . ?
C3 N2 C9 C8 178.4(2) . . . . ?
C3 N4 C4 O2 178.8(2) . . . . ?
C3 N4 C4 N3 -2.6(3) . . . . ?
C3 N4 C10 C11 -89.9(3) . . . . ?
C4 N3 C1 O1 -174.8(2) . . . . ?
C4 N3 C1 C2 5.0(3) . . . . ?
C4 N3 C17 C18 93.6(3) . . . . ?
C4 N4 C3 N2 -177.3(2) . . . . ?
C4 N4 C3 C2 3.0(3) . . . . ?
C4 N4 C10 C11 105.8(2) . . . . ?
C5 N1 C2 C1 179.0(2) . . . . ?
C5 N1 C2 C3 0.5(2) . . . . ?
C5 N2 C3 N4 -179.5(2) . . . . ?
C5 N2 C3 C2 0.2(2) . . . . ?
C5 N2 C9 C8 2.8(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 Cl1 178.18(18) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 N2 -0.4(3) . . . . ?
C9 N2 C3 N4 4.2(4) . . . . ?
C9 N2 C3 C2 -176.0(2) . . . . ?
C9 N2 C5 N1 176.83(19) . . . . ?
C9 N2 C5 C6 -3.6(3) . . . . ?
C10 N4 C3 N2 18.7(4) . . . . ?
C10 N4 C3 C2 -161.0(2) . . . . ?
C10 N4 C4 O2 -16.0(3) . . . . ?
C10 N4 C4 N3 162.58(19) . . . . ?
C10 C11 C12 C13 179.5(3) . . . . ?
C10 C11 C16 C15 180.0(3) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C11 0.9(5) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C17 N3 C1 O1 2.8(3) . . . . ?
C17 N3 C1 C2 -177.44(19) . . . . ?
C17 N3 C4 O2 -0.6(3) . . . . ?
C17 N3 C4 N4 -179.15(19) . . . . ?
C17 C18 C19 C20 -178.0(3) . . . . ?
C17 C18 C24 C22 177.0(3) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
C19 C18 C24 C22 -0.9(4) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C24 -1.0(5) . . . . ?
C21 C22 C24 C18 1.5(5) . . . . ?
C24 C18 C19 C20 -0.1(4) . . . . ?
Cl4 C46 C47 N7 -178.86(18) . . . . ?
F2 C44 C45 C46 -178.7(2) . . . . ?
O3 C32 C33 N8 1.7(4) . . . . ?
O3 C32 C33 C34 -175.9(2) . . . . ?
N5 C32 C33 N8 -179.5(2) . . . . ?
N5 C32 C33 C34 3.0(3) . . . . ?
N6 C36 C37 C38 36.9(3) . . . . ?
N6 C36 C37 C42 -145.7(2) . . . . ?
N7 C43 C44 F2 177.6(2) . . . . ?
N7 C43 C44 C45 -1.9(4) . . . . ?
N8 C33 C34 N6 -179.0(2) . . . . ?
N8 C33 C34 N7 0.4(3) . . . . ?
N8 C43 C44 F2 -2.6(4) . . . . ?
N8 C43 C44 C45 177.9(3) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C26 C25 C30 C29 -0.1(4) . . . . ?
C26 C25 C31 N5 56.5(3) . . . . ?
C26 C27 C28 C29 0.9(4) . . . . ?
C27 C28 C29 C30 -0.8(4) . . . . ?
C28 C29 C30 C25 0.4(5) . . . . ?
C30 C25 C26 C27 0.2(4) . . . . ?
C30 C25 C31 N5 -122.6(2) . . . . ?
C31 N5 C32 O3 0.6(3) . . . . ?
C31 N5 C32 C33 -178.3(2) . . . . ?
C31 N5 C35 O4 -3.2(4) . . . . ?
C31 N5 C35 N6 175.6(2) . . . . ?
C31 C25 C26 C27 -178.9(2) . . . . ?
C31 C25 C30 C29 179.1(2) . . . . ?
C32 N5 C31 C25 84.9(3) . . . . ?
C32 N5 C35 O4 -179.3(2) . . . . ?
C32 N5 C35 N6 -0.4(4) . . . . ?
C32 C33 C34 N6 -1.2(4) . . . . ?
C32 C33 C34 N7 178.3(2) . . . . ?
C33 N8 C43 N7 0.1(3) . . . . ?
C33 N8 C43 C44 -179.7(3) . . . . ?
C34 N6 C35 O4 -178.6(2) . . . . ?
C34 N6 C35 N5 2.5(3) . . . . ?
C34 N6 C36 C37 89.0(3) . . . . ?
C34 N7 C43 N8 0.2(3) . . . . ?
C34 N7 C43 C44 180.0(2) . . . . ?
C34 N7 C47 C46 -178.7(3) . . . . ?
C35 N5 C31 C25 -91.6(2) . . . . ?
C35 N5 C32 O3 176.6(2) . . . . ?
C35 N5 C32 C33 -2.3(4) . . . . ?
C35 N6 C34 N7 178.9(2) . . . . ?
C35 N6 C34 C33 -1.8(4) . . . . ?
C35 N6 C36 C37 -100.4(3) . . . . ?
C36 N6 C34 N7 -10.6(4) . . . . ?
C36 N6 C34 C33 168.7(2) . . . . ?
C36 N6 C35 O4 10.2(4) . . . . ?
C36 N6 C35 N5 -168.7(2) . . . . ?
C36 C37 C38 C39 176.8(2) . . . . ?
C36 C37 C42 C41 -176.8(3) . . . . ?
C37 C38 C39 C40 -0.1(4) . . . . ?
C38 C37 C42 C41 0.6(4) . . . . ?
C38 C39 C40 C41 1.1(5) . . . . ?
C39 C40 C41 C42 -1.2(5) . . . . ?
C40 C41 C42 C37 0.3(5) . . . . ?
C42 C37 C38 C39 -0.7(4) . . . . ?
C43 N7 C34 N6 179.1(2) . . . . ?
C43 N7 C34 C33 -0.3(3) . . . . ?
C43 N7 C47 C46 -2.1(4) . . . . ?
C43 N8 C33 C32 -178.0(2) . . . . ?
C43 N8 C33 C34 -0.3(3) . . . . ?
C43 C44 C45 C46 0.9(4) . . . . ?
C44 C45 C46 Cl4 179.5(2) . . . . ?
C44 C45 C46 C47 -0.3(4) . . . . ?
C45 C46 C47 N7 0.9(4) . . . . ?
C47 N7 C34 N6 -3.9(4) . . . . ?
C47 N7 C34 C33 176.7(2) . . . . ?
C47 N7 C43 N8 -177.3(2) . . . . ?
C47 N7 C43 C44 2.6(3) . . . . ?

_olex2_date_sample_data_collection 2021-03-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_2-106-4
_database_code_depnum_ccdc_archive 'CCDC 2073618'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 Cl2 N4 O2'
_chemical_formula_weight         451.30

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8857(6)
_cell_length_b                   10.0289(7)
_cell_length_c                   11.4665(6)
_cell_angle_alpha                97.757(5)
_cell_angle_beta                 95.026(5)
_cell_angle_gamma                97.668(6)
_cell_volume                     997.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.356
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6910
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3512
_reflns_number_gt                2925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.3110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3512
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.73383(6) 0.47624(6) 1.14482(4) 0.02975(17) Uani 1 1 d . . . . .
Cl2 Cl 0.79495(9) -0.16184(9) -0.06070(6) 0.0661(3) Uani 1 1 d . . . . .
O1 O 0.70400(17) 0.09773(16) 0.50897(13) 0.0328(4) Uani 1 1 d . . . . .
O2 O 0.45267(16) 0.37080(16) 0.29804(12) 0.0291(4) Uani 1 1 d . . . . .
N1 N 0.84644(19) 0.57846(18) 0.57205(13) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.66913(19) 0.60916(18) 0.42662(14) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.78455(19) 0.32573(18) 0.55449(13) 0.0237(4) Uani 1 1 d . . . . .
N4 N 0.58454(19) 0.23502(18) 0.40138(14) 0.0230(4) Uani 1 1 d . . . . .
C1 C 0.7675(2) 0.4526(2) 0.52551(16) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.6620(2) 0.4738(2) 0.43839(16) 0.0216(5) Uani 1 1 d . . . . .
C3 C 0.5566(2) 0.3625(2) 0.37226(16) 0.0229(5) Uani 1 1 d . . . . .
C4 C 0.6917(2) 0.2124(2) 0.48952(17) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.4882(2) 0.1117(2) 0.33397(18) 0.0289(5) Uani 1 1 d . . . . .
H5A H 0.394592 0.137017 0.299141 0.035 Uiso 1 1 calc R U . . .
H5B H 0.460812 0.048115 0.387983 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5680(2) 0.0428(2) 0.23738(18) 0.0273(5) Uani 1 1 d . . . . .
C7 C 0.6101(2) 0.1106(2) 0.14460(18) 0.0286(5) Uani 1 1 d . . . . .
H7 H 0.589725 0.198941 0.143198 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6820(3) 0.0485(2) 0.05417(19) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.710903 0.094876 -0.007161 0.040 Uiso 1 1 calc R U . . .
C9 C 0.7100(3) -0.0822(3) 0.0564(2) 0.0390(6) Uani 1 1 d . . . . .
C10 C 0.6693(3) -0.1525(3) 0.1465(2) 0.0486(7) Uani 1 1 d . . . . .
H10 H 0.688781 -0.241282 0.146623 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5986(3) -0.0890(3) 0.2373(2) 0.0400(6) Uani 1 1 d . . . . .
H11 H 0.571489 -0.135583 0.298916 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7798(2) 0.6714(2) 0.50718(17) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.8380(2) 0.8113(2) 0.53512(18) 0.0296(5) Uani 1 1 d . . . . .
H13 H 0.797541 0.873856 0.493199 0.036 Uiso 1 1 calc R U . . .
C14 C 0.9534(3) 0.8541(3) 0.6236(2) 0.0367(6) Uani 1 1 d . . . . .
H14 H 0.992252 0.946164 0.641773 0.044 Uiso 1 1 calc R U . . .
C15 C 1.0152(3) 0.7591(3) 0.68852(19) 0.0345(6) Uani 1 1 d . . . . .
H15 H 1.093378 0.790135 0.749334 0.041 Uiso 1 1 calc R U . . .
C16 C 0.9628(2) 0.6256(2) 0.66374(17) 0.0292(5) Uani 1 1 d . . . . .
H16 H 1.003842 0.564860 0.707443 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8904(2) 0.3006(2) 0.65246(17) 0.0274(5) Uani 1 1 d . . . . .
H17A H 0.989885 0.352323 0.649065 0.033 Uiso 1 1 calc R U . . .
H17B H 0.901507 0.204964 0.641445 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8404(2) 0.3380(2) 0.77410(16) 0.0227(5) Uani 1 1 d . . . . .
C19 C 0.9277(2) 0.3087(2) 0.87132(17) 0.0256(5) Uani 1 1 d . . . . .
H19 H 1.009383 0.261137 0.859505 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8953(2) 0.3489(2) 0.98495(17) 0.0270(5) Uani 1 1 d . . . . .
H20 H 0.954449 0.329195 1.049687 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7728(2) 0.4191(2) 1.00081(17) 0.0247(5) Uani 1 1 d . . . . .
C22 C 0.6823(2) 0.4459(2) 0.90645(17) 0.0283(5) Uani 1 1 d . . . . .
H22 H 0.599022 0.491226 0.918595 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7161(2) 0.4047(2) 0.79265(18) 0.0282(5) Uani 1 1 d . . . . .
H23 H 0.654606 0.422068 0.728164 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.7529(19) . ?
Cl2 C9 1.749(2) . ?
O1 C4 1.217(3) . ?
O2 C3 1.219(2) . ?
N1 C1 1.373(3) . ?
N1 C16 1.394(3) . ?
N1 C12 1.425(3) . ?
N2 C12 1.316(3) . ?
N2 C2 1.376(3) . ?
N3 C1 1.382(3) . ?
N3 C4 1.393(3) . ?
N3 C17 1.471(2) . ?
N4 C4 1.390(3) . ?
N4 C3 1.411(3) . ?
N4 C5 1.484(3) . ?
C1 C2 1.367(3) . ?
C2 C3 1.438(3) . ?
C5 C6 1.507(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.384(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.413(3) . ?
C13 C14 1.359(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.423(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.340(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.515(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.383(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(3) . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
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
C1 N1 C16 134.38(18) . . ?
C1 N1 C12 105.08(16) . . ?
C16 N1 C12 120.50(19) . . ?
C12 N2 C2 104.40(16) . . ?
C1 N3 C4 118.34(17) . . ?
C1 N3 C17 124.89(18) . . ?
C4 N3 C17 116.73(17) . . ?
C4 N4 C3 126.59(18) . . ?
C4 N4 C5 115.84(17) . . ?
C3 N4 C5 117.55(17) . . ?
C2 C1 N1 106.24(18) . . ?
C2 C1 N3 123.7(2) . . ?
N1 C1 N3 130.05(18) . . ?
C1 C2 N2 112.27(19) . . ?
C1 C2 C3 121.00(19) . . ?
N2 C2 C3 126.71(18) . . ?
O2 C3 N4 121.0(2) . . ?
O2 C3 C2 126.34(19) . . ?
N4 C3 C2 112.67(17) . . ?
O1 C4 N4 121.2(2) . . ?
O1 C4 N3 121.36(19) . . ?
N4 C4 N3 117.48(18) . . ?
N4 C5 C6 112.32(17) . . ?
N4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C11 C6 C7 118.5(2) . . ?
C11 C6 C5 121.4(2) . . ?
C7 C6 C5 120.1(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 Cl2 118.7(2) . . ?
C10 C9 Cl2 119.7(2) . . ?
C9 C10 C11 119.0(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 120.9(2) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N2 C12 C13 129.5(2) . . ?
N2 C12 N1 112.00(19) . . ?
C13 C12 N1 118.52(19) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 N1 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
N1 C16 H16 120.2 . . ?
N3 C17 C18 114.14(16) . . ?
N3 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
N3 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C23 C18 C19 118.90(18) . . ?
C23 C18 C17 122.97(17) . . ?
C19 C18 C17 118.08(18) . . ?
C20 C19 C18 121.10(19) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 118.64(18) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C22 C21 C20 121.41(18) . . ?
C22 C21 Cl1 119.27(16) . . ?
C20 C21 Cl1 119.32(15) . . ?
C21 C22 C23 119.31(19) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 120.59(18) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 C2 177.67(19) . . . . ?
C12 N1 C1 C2 0.22(19) . . . . ?
C16 N1 C1 N3 -2.9(3) . . . . ?
C12 N1 C1 N3 179.61(18) . . . . ?
C4 N3 C1 C2 1.6(3) . . . . ?
C17 N3 C1 C2 -176.03(17) . . . . ?
C4 N3 C1 N1 -177.66(18) . . . . ?
C17 N3 C1 N1 4.7(3) . . . . ?
N1 C1 C2 N2 -0.1(2) . . . . ?
N3 C1 C2 N2 -179.56(16) . . . . ?
N1 C1 C2 C3 -178.67(16) . . . . ?
N3 C1 C2 C3 1.9(3) . . . . ?
C12 N2 C2 C1 0.0(2) . . . . ?
C12 N2 C2 C3 178.41(18) . . . . ?
C4 N4 C3 O2 -175.22(17) . . . . ?
C5 N4 C3 O2 3.1(3) . . . . ?
C4 N4 C3 C2 4.9(3) . . . . ?
C5 N4 C3 C2 -176.72(16) . . . . ?
C1 C2 C3 O2 175.36(18) . . . . ?
N2 C2 C3 O2 -3.0(3) . . . . ?
C1 C2 C3 N4 -4.8(3) . . . . ?
N2 C2 C3 N4 176.87(17) . . . . ?
C3 N4 C4 O1 178.32(17) . . . . ?
C5 N4 C4 O1 0.0(3) . . . . ?
C3 N4 C4 N3 -1.8(3) . . . . ?
C5 N4 C4 N3 179.84(16) . . . . ?
C1 N3 C4 O1 178.17(17) . . . . ?
C17 N3 C4 O1 -4.0(3) . . . . ?
C1 N3 C4 N4 -1.7(3) . . . . ?
C17 N3 C4 N4 176.14(15) . . . . ?
C4 N4 C5 C6 -81.4(2) . . . . ?
C3 N4 C5 C6 100.0(2) . . . . ?
N4 C5 C6 C11 118.3(2) . . . . ?
N4 C5 C6 C7 -62.9(2) . . . . ?
C11 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -179.23(19) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 Cl2 177.85(16) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
Cl2 C9 C10 C11 -178.45(19) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
C5 C6 C11 C10 178.6(2) . . . . ?
C9 C10 C11 C6 0.5(4) . . . . ?
C2 N2 C12 C13 179.76(19) . . . . ?
C2 N2 C12 N1 0.2(2) . . . . ?
C1 N1 C12 N2 -0.3(2) . . . . ?
C16 N1 C12 N2 -178.14(16) . . . . ?
C1 N1 C12 C13 -179.89(17) . . . . ?
C16 N1 C12 C13 2.2(3) . . . . ?
N2 C12 C13 C14 179.4(2) . . . . ?
N1 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 N1 0.5(3) . . . . ?
C1 N1 C16 C15 -179.11(19) . . . . ?
C12 N1 C16 C15 -2.0(3) . . . . ?
C1 N3 C17 C18 73.8(2) . . . . ?
C4 N3 C17 C18 -103.9(2) . . . . ?
N3 C17 C18 C23 -7.3(3) . . . . ?
N3 C17 C18 C19 175.47(19) . . . . ?
C23 C18 C19 C20 -2.2(3) . . . . ?
C17 C18 C19 C20 175.2(2) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C19 C20 C21 Cl1 -177.80(17) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
Cl1 C21 C22 C23 177.88(17) . . . . ?
C19 C18 C23 C22 2.3(3) . . . . ?
C17 C18 C23 C22 -175.0(2) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_4568
_database_code_depnum_ccdc_archive 'CCDC 2073616'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-01-15
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 F N4 O2'
_chemical_formula_sum            'C12 H11 F N4 O2'
_chemical_formula_weight         262.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5108(7)
_cell_length_b                   6.6696(5)
_cell_length_c                   20.015(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.966(9)
_cell_angle_gamma                90
_cell_volume                     1111.44(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3760
_cell_measurement_theta_min      4.4890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3422
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         4.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  34.00   1.00    1.00    --  -40.73  38.00  90.00   74
  2  ω     25.00  80.00   1.00    1.00    --   40.73 -99.00  30.00   55
  3  ω     29.00 107.00   1.00    2.00    --  107.58 -94.00   0.00   78
  4  ω     55.00 134.00   1.00    2.00    --  107.58 -61.00  30.00   79
  5  ω    125.00 165.00   1.00    2.00    --  107.58  15.00 150.00   40
  6  ω     99.00 171.00   1.00    2.00    --  107.58 125.00  60.00   72
  7  ω     87.00 170.00   1.00    2.00    --  107.58  45.00-150.00   83
  8  ω     30.00  56.00   1.00    2.00    --  107.58 -94.00 -30.00   26
  9  ω    -73.00  32.00   1.00    1.00    --  -40.73  77.00-180.00  105
;
_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      0.0755605000
_diffrn_orient_matrix_UB_12      -0.0262069000
_diffrn_orient_matrix_UB_13      0.0424459000
_diffrn_orient_matrix_UB_21      -0.0139897000
_diffrn_orient_matrix_UB_22      0.1063733000
_diffrn_orient_matrix_UB_23      0.0752781000
_diffrn_orient_matrix_UB_31      -0.0169030000
_diffrn_orient_matrix_UB_32      -0.2032527000
_diffrn_orient_matrix_UB_33      0.0337540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1755
_reflns_number_total             1952
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.120
_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)+(0.1263P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_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:
 C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
F1 F 0.48017(16) 0.8853(2) 0.86576(7) 0.0372(4) Uani 1 1 d . . . . .
O1 O -0.39076(18) 0.8499(2) 0.61096(8) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.01546(19) 0.7614(2) 0.49792(7) 0.0330(4) Uani 1 1 d . . . . .
N1 N -0.1833(2) 0.8344(2) 0.55544(9) 0.0246(5) Uani 1 1 d . . . . .
N2 N 0.0890(2) 0.7868(2) 0.61295(8) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.1215(2) 0.8309(2) 0.73891(8) 0.0208(4) Uani 1 1 d . . . . .
N4 N -0.1442(2) 0.8299(2) 0.74264(9) 0.0240(4) Uani 1 1 d . . . . .
C1 C -0.2473(2) 0.8352(3) 0.61500(10) 0.0231(5) Uani 1 1 d . . . . .
C2 C -0.0245(2) 0.7941(3) 0.55218(10) 0.0244(5) Uani 1 1 d . . . . .
C3 C 0.0343(2) 0.8165(3) 0.67294(10) 0.0206(5) Uani 1 1 d . . . . .
C4 C -0.1245(2) 0.8240(3) 0.67682(10) 0.0211(5) Uani 1 1 d . . . . .
C5 C 0.0039(2) 0.8287(3) 0.77977(10) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.0563(3) 0.8181(3) 0.85173(11) 0.0271(5) Uani 1 1 d . . . . .
H6 H -0.019574 0.806575 0.880269 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2150(3) 0.8245(3) 0.87927(10) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.252374 0.809746 0.927143 0.035 Uiso 1 1 calc R U . . .
C8 C 0.3251(3) 0.8534(3) 0.83597(11) 0.0275(5) Uani 1 1 d . . . . .
C9 C 0.2838(2) 0.8674(3) 0.76673(10) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.3942(3) 0.9488(3) 0.72438(11) 0.0307(5) Uani 1 1 d . . . . .
H10A H 0.448824 0.837727 0.706574 0.046 Uiso 1 1 calc R U . . .
H10B H 0.474173 1.036082 0.752547 0.046 Uiso 1 1 calc R U . . .
H10C H 0.332253 1.026093 0.686214 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2307(2) 0.6610(3) 0.61126(11) 0.0283(5) Uani 1 1 d . . . . .
H11A H 0.268763 0.599561 0.656177 0.042 Uiso 1 1 calc R U . . .
H11B H 0.316097 0.744242 0.599679 0.042 Uiso 1 1 calc R U . . .
H11C H 0.201276 0.555658 0.576804 0.042 Uiso 1 1 calc R U . . .
C12 C -0.2986(3) 0.8553(4) 0.49011(11) 0.0354(6) Uani 1 1 d . . . . .
H12A H -0.369679 0.738143 0.482898 0.053 Uiso 1 1 calc R U . . .
H12B H -0.240317 0.864674 0.452836 0.053 Uiso 1 1 calc R U . . .
H12C H -0.362781 0.976867 0.491031 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.348(3) . ?
O1 C1 1.211(3) . ?
O2 C2 1.223(3) . ?
N1 C1 1.409(3) . ?
N1 C2 1.393(3) . ?
N1 C12 1.470(3) . ?
N2 C2 1.389(3) . ?
N2 C3 1.389(3) . ?
N2 C11 1.475(3) . ?
N3 C3 1.378(3) . ?
N3 C5 1.417(2) . ?
N3 C9 1.399(3) . ?
N4 C4 1.362(3) . ?
N4 C5 1.324(3) . ?
C1 C4 1.447(3) . ?
C3 C4 1.370(3) . ?
C5 C6 1.418(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.349(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.415(3) . ?
C8 C9 1.361(3) . ?
C9 C10 1.493(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 116.64(18) . . ?
C2 N1 C1 126.10(17) . . ?
C2 N1 C12 116.86(18) . . ?
C2 N2 C3 117.06(17) . . ?
C2 N2 C11 115.05(17) . . ?
C3 N2 C11 121.55(16) . . ?
C3 N3 C5 104.35(16) . . ?
C3 N3 C9 133.22(17) . . ?
C9 N3 C5 121.92(17) . . ?
C5 N4 C4 104.42(17) . . ?
O1 C1 N1 120.32(18) . . ?
O1 C1 C4 126.96(19) . . ?
N1 C1 C4 112.69(18) . . ?
O2 C2 N1 121.82(19) . . ?
O2 C2 N2 120.03(19) . . ?
N2 C2 N1 118.12(18) . . ?
N3 C3 N2 128.89(18) . . ?
C4 C3 N2 124.44(19) . . ?
C4 C3 N3 106.55(18) . . ?
N4 C4 C1 127.84(19) . . ?
N4 C4 C3 112.10(18) . . ?
C3 C4 C1 119.97(19) . . ?
N3 C5 C6 118.39(19) . . ?
N4 C5 N3 112.32(17) . . ?
N4 C5 C6 129.2(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.18(19) . . ?
C8 C7 H7 120.4 . . ?
F1 C8 C7 117.55(19) . . ?
F1 C8 C9 117.5(2) . . ?
C9 C8 C7 124.7(2) . . ?
N3 C9 C10 121.56(18) . . ?
C8 C9 N3 114.74(19) . . ?
C8 C9 C10 122.91(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C8 C9 N3 179.46(16) . . . . ?
F1 C8 C9 C10 -10.6(3) . . . . ?
O1 C1 C4 N4 -0.8(3) . . . . ?
O1 C1 C4 C3 -177.1(2) . . . . ?
N1 C1 C4 N4 177.05(17) . . . . ?
N1 C1 C4 C3 0.8(2) . . . . ?
N2 C3 C4 N4 172.44(16) . . . . ?
N2 C3 C4 C1 -10.7(3) . . . . ?
N3 C3 C4 N4 -3.8(2) . . . . ?
N3 C3 C4 C1 172.99(16) . . . . ?
N3 C5 C6 C7 4.6(3) . . . . ?
N4 C5 C6 C7 -178.21(18) . . . . ?
C1 N1 C2 O2 166.79(19) . . . . ?
C1 N1 C2 N2 -11.7(3) . . . . ?
C2 N1 C1 O1 -171.59(19) . . . . ?
C2 N1 C1 C4 10.4(3) . . . . ?
C2 N2 C3 N3 -174.97(16) . . . . ?
C2 N2 C3 C4 9.6(3) . . . . ?
C3 N2 C2 O2 -177.21(17) . . . . ?
C3 N2 C2 N1 1.3(3) . . . . ?
C3 N3 C5 N4 -4.88(18) . . . . ?
C3 N3 C5 C6 172.78(16) . . . . ?
C3 N3 C9 C8 -174.85(17) . . . . ?
C3 N3 C9 C10 15.0(3) . . . . ?
C4 N4 C5 N3 2.58(19) . . . . ?
C4 N4 C5 C6 -174.77(18) . . . . ?
C5 N3 C3 N2 -171.06(18) . . . . ?
C5 N3 C3 C4 5.00(17) . . . . ?
C5 N3 C9 C8 14.7(2) . . . . ?
C5 N3 C9 C10 -155.41(18) . . . . ?
C5 N4 C4 C1 -175.73(17) . . . . ?
C5 N4 C4 C3 0.8(2) . . . . ?
C5 C6 C7 C8 3.6(3) . . . . ?
C6 C7 C8 F1 171.48(17) . . . . ?
C6 C7 C8 C9 -2.9(3) . . . . ?
C7 C8 C9 N3 -6.1(3) . . . . ?
C7 C8 C9 C10 163.8(2) . . . . ?
C9 N3 C3 N2 17.3(3) . . . . ?
C9 N3 C3 C4 -166.62(19) . . . . ?
C9 N3 C5 N4 167.93(16) . . . . ?
C9 N3 C5 C6 -14.4(2) . . . . ?
C11 N2 C2 O2 -24.7(3) . . . . ?
C11 N2 C2 N1 153.84(17) . . . . ?
C11 N2 C3 N3 34.4(3) . . . . ?
C11 N2 C3 C4 -141.0(2) . . . . ?
C12 N1 C1 O1 0.9(3) . . . . ?
C12 N1 C1 C4 -177.12(16) . . . . ?
C12 N1 C2 O2 -5.7(3) . . . . ?
C12 N1 C2 N2 175.80(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 3.268
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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 
# 
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# Please retain this information to preserve the provenance of 
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data_lyy-2-88-2
_database_code_depnum_ccdc_archive 'CCDC 2073630'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N4 O2'
_chemical_formula_sum            'C17 H14 N4 O2'
_chemical_formula_weight         306.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.2162(2)
_cell_length_b                   9.41800(10)
_cell_length_c                   30.1780(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2903.61(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1700
_cell_measurement_theta_min      5.2330
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6750
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.299
_diffrn_reflns_theta_min         5.229
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -21.00   1.00    1.10    --  -35.62 -23.00 -65.00   83
  2  ω     47.00  72.00   1.00    1.10    --   35.62-102.00 162.00   25
  3  ω     50.00  76.00   1.00    1.10    --   35.62-124.00  83.00   26
  4  ω    108.00 141.00   1.00    4.41    --  107.12 102.00 -94.00   33
  5  ω     84.00 158.00   1.00    4.41    --  107.12  23.00  99.00   74
  6  ω     46.00 112.00   1.00    4.41    --  107.12-124.00  83.00   66
  7  ω    -48.00  -4.00   1.00    1.10    --  -35.62  57.00  90.00   44
  8  ω     59.00  98.00   1.00    1.10    --   35.62 178.00-120.00   39
  9  ω     96.00 159.00   1.00    4.41    --  107.12  61.00-180.00   63
 10  ω     51.00 108.00   1.00    4.41    --  107.12 -95.00 120.00   57
 11  ω     43.00  91.00   1.00    4.41    --  107.12 -61.00 -90.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0817679000
_diffrn_orient_matrix_UB_12      0.0472094000
_diffrn_orient_matrix_UB_13      0.0402934000
_diffrn_orient_matrix_UB_21      -0.1260347000
_diffrn_orient_matrix_UB_22      0.0136311000
_diffrn_orient_matrix_UB_23      0.0277174000
_diffrn_orient_matrix_UB_31      0.0135547000
_diffrn_orient_matrix_UB_32      -0.1559612000
_diffrn_orient_matrix_UB_33      0.0146409000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2398
_reflns_number_total             2761
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.069
_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)+(0.0775P)²+3.0537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1785
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.4525(3) 0.3885(3) 0.45554(8) 0.0365(6) Uani 1 1 d . . . . .
C2 C 0.5480(3) 0.3074(3) 0.47839(9) 0.0479(7) Uani 1 1 d . . . . .
H2 H 0.521993 0.235522 0.497581 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6761(3) 0.3342(3) 0.47241(10) 0.0541(8) Uani 1 1 d . . . . .
H3 H 0.738181 0.281325 0.487778 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7173(3) 0.4425(4) 0.44281(10) 0.0538(8) Uani 1 1 d . . . . .
H4 H 0.806238 0.459308 0.438912 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6297(3) 0.5212(3) 0.42028(9) 0.0435(6) Uani 1 1 d . . . . .
H5 H 0.658028 0.591628 0.400927 0.052 Uiso 1 1 calc R U . . .
N6 N 0.4971(2) 0.4967(2) 0.42608(6) 0.0331(5) Uani 1 1 d . . . . .
C7 C 0.3850(2) 0.5550(2) 0.40898(7) 0.0298(5) Uani 1 1 d . . . . .
C8 C 0.2824(2) 0.4837(3) 0.42765(8) 0.0339(5) Uani 1 1 d . . . . .
N9 N 0.3243(2) 0.3804(2) 0.45648(7) 0.0404(5) Uani 1 1 d . . . . .
C10 C 0.1496(2) 0.5150(3) 0.41590(8) 0.0364(5) Uani 1 1 d . . . . .
N11 N 0.1409(2) 0.6186(2) 0.38207(7) 0.0381(5) Uani 1 1 d . . . . .
C12 C 0.2449(3) 0.6932(3) 0.36344(8) 0.0369(6) Uani 1 1 d . . . . .
N13 N 0.36975(19) 0.6612(2) 0.37774(6) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.4789(2) 0.7342(2) 0.35635(8) 0.0359(5) Uani 1 1 d . . . . .
H14A H 0.542517 0.760267 0.378786 0.043 Uiso 1 1 calc R U . . .
H14B H 0.446749 0.821119 0.342985 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5469(2) 0.6466(3) 0.32102(8) 0.0328(5) Uani 1 1 d . . . . .
C16 C 0.6646(3) 0.6946(3) 0.30399(10) 0.0496(7) Uani 1 1 d . . . . .
H16 H 0.702363 0.776938 0.315195 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7263(3) 0.6205(4) 0.27033(11) 0.0589(8) Uani 1 1 d . . . . .
H17 H 0.805647 0.652997 0.259124 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6707(3) 0.4988(3) 0.25338(10) 0.0543(8) Uani 1 1 d . . . . .
H18 H 0.711689 0.449787 0.230524 0.065 Uiso 1 1 calc R U . . .
C19 C 0.5547(3) 0.4505(3) 0.27035(10) 0.0505(7) Uani 1 1 d . . . . .
H19 H 0.517252 0.368070 0.259036 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4923(3) 0.5237(3) 0.30440(9) 0.0388(6) Uani 1 1 d . . . . .
H20 H 0.413906 0.489716 0.315931 0.047 Uiso 1 1 calc R U . . .
O21 O 0.2258(2) 0.7835(2) 0.33509(7) 0.0551(6) Uani 1 1 d . . . . .
O22 O 0.05138(19) 0.4607(2) 0.43109(7) 0.0533(5) Uani 1 1 d . . . . .
C23 C 0.0102(3) 0.6539(4) 0.36531(12) 0.0558(8) Uani 1 1 d . . . . .
H23A H -0.054298 0.600135 0.381203 0.084 Uiso 1 1 calc R U . . .
H23B H 0.005310 0.631292 0.334333 0.084 Uiso 1 1 calc R U . . .
H23C H -0.005868 0.753489 0.369403 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.418(4) . ?
C1 N6 1.427(3) . ?
C1 N9 1.312(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.345(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.419(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.347(4) . ?
C5 H5 0.9300 . ?
C5 N6 1.385(3) . ?
N6 C7 1.371(3) . ?
C7 C8 1.366(3) . ?
C7 N13 1.383(3) . ?
C8 N9 1.374(3) . ?
C8 C10 1.433(4) . ?
C10 N11 1.415(3) . ?
C10 O22 1.216(3) . ?
N11 C12 1.392(3) . ?
N11 C23 1.466(3) . ?
C12 N13 1.380(3) . ?
C12 O21 1.222(3) . ?
N13 C14 1.460(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(3) . ?
C15 C16 1.384(4) . ?
C15 C20 1.379(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 N6 117.8(2) . . ?
N9 C1 C2 130.2(2) . . ?
N9 C1 N6 112.0(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 N6 119.6(3) . . ?
N6 C5 H5 120.2 . . ?
C5 N6 C1 120.7(2) . . ?
C7 N6 C1 104.7(2) . . ?
C7 N6 C5 134.6(2) . . ?
N6 C7 N13 129.8(2) . . ?
C8 C7 N6 106.8(2) . . ?
C8 C7 N13 123.4(2) . . ?
C7 C8 N9 111.7(2) . . ?
C7 C8 C10 121.5(2) . . ?
N9 C8 C10 126.7(2) . . ?
C1 N9 C8 104.8(2) . . ?
N11 C10 C8 112.3(2) . . ?
O22 C10 C8 127.0(3) . . ?
O22 C10 N11 120.7(2) . . ?
C10 N11 C23 117.6(2) . . ?
C12 N11 C10 126.2(2) . . ?
C12 N11 C23 116.2(2) . . ?
N13 C12 N11 118.0(2) . . ?
O21 C12 N11 120.8(2) . . ?
O21 C12 N13 121.2(2) . . ?
C7 N13 C14 123.7(2) . . ?
C12 N13 C7 118.4(2) . . ?
C12 N13 C14 117.7(2) . . ?
N13 C14 H14A 108.8 . . ?
N13 C14 H14B 108.8 . . ?
N13 C14 C15 113.9(2) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C16 C15 C14 118.8(2) . . ?
C20 C15 C14 121.8(2) . . ?
C20 C15 C16 119.3(2) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.0(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N11 C23 H23A 109.5 . . ?
N11 C23 H23B 109.5 . . ?
N11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -0.8(5) . . . . ?
C1 N6 C7 C8 -0.1(2) . . . . ?
C1 N6 C7 N13 -177.8(2) . . . . ?
C2 C1 N6 C5 -0.1(4) . . . . ?
C2 C1 N6 C7 179.6(2) . . . . ?
C2 C1 N9 C8 -179.5(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 N6 0.2(5) . . . . ?
C4 C5 N6 C1 -0.3(4) . . . . ?
C4 C5 N6 C7 -179.9(3) . . . . ?
C5 N6 C7 C8 179.6(3) . . . . ?
C5 N6 C7 N13 1.9(5) . . . . ?
N6 C1 C2 C3 0.7(4) . . . . ?
N6 C1 N9 C8 -0.2(3) . . . . ?
N6 C7 C8 N9 0.0(3) . . . . ?
N6 C7 C8 C10 -178.0(2) . . . . ?
N6 C7 N13 C12 174.9(2) . . . . ?
N6 C7 N13 C14 -0.1(4) . . . . ?
C7 C8 N9 C1 0.1(3) . . . . ?
C7 C8 C10 N11 3.4(3) . . . . ?
C7 C8 C10 O22 -178.2(3) . . . . ?
C7 N13 C14 C15 75.5(3) . . . . ?
C8 C7 N13 C12 -2.6(3) . . . . ?
C8 C7 N13 C14 -177.6(2) . . . . ?
C8 C10 N11 C12 -4.7(3) . . . . ?
C8 C10 N11 C23 176.6(2) . . . . ?
N9 C1 C2 C3 -180.0(3) . . . . ?
N9 C1 N6 C5 -179.6(2) . . . . ?
N9 C1 N6 C7 0.1(3) . . . . ?
N9 C8 C10 N11 -174.2(2) . . . . ?
N9 C8 C10 O22 4.1(4) . . . . ?
C10 C8 N9 C1 177.9(2) . . . . ?
C10 N11 C12 N13 2.5(4) . . . . ?
C10 N11 C12 O21 -178.0(2) . . . . ?
N11 C12 N13 C7 1.4(3) . . . . ?
N11 C12 N13 C14 176.7(2) . . . . ?
C12 N13 C14 C15 -99.5(3) . . . . ?
N13 C7 C8 N9 177.9(2) . . . . ?
N13 C7 C8 C10 0.0(4) . . . . ?
N13 C14 C15 C16 -169.0(2) . . . . ?
N13 C14 C15 C20 13.4(3) . . . . ?
C14 C15 C16 C17 -177.2(3) . . . . ?
C14 C15 C20 C19 176.6(2) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C15 C20 C19 -1.0(4) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C15 0.6(4) . . . . ?
C20 C15 C16 C17 0.5(4) . . . . ?
O21 C12 N13 C7 -178.1(2) . . . . ?
O21 C12 N13 C14 -2.8(4) . . . . ?
O22 C10 N11 C12 176.8(2) . . . . ?
O22 C10 N11 C23 -1.9(4) . . . . ?
C23 N11 C12 N13 -178.8(2) . . . . ?
C23 N11 C12 O21 0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.683
_oxdiff_exptl_absorpt_empirical_full_min 0.249
####################################################################### 
# 
# 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_141-2
_database_code_depnum_ccdc_archive 'CCDC 2073614'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-25
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 N4 O2'
_chemical_formula_sum            'C27 H20 N4 O2'
_chemical_formula_weight         432.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.0682(7)
_cell_length_b                   10.7628(10)
_cell_length_c                   11.0063(10)
_cell_angle_alpha                82.013(8)
_cell_angle_beta                 80.721(7)
_cell_angle_gamma                85.528(7)
_cell_volume                     1048.17(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2611
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7770
_cell_measurement_theta_min      4.1020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.165
_diffrn_reflns_theta_min         4.104
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  27.00   1.00    1.00    --  -40.73  57.00  30.00   94
  2  ω    -51.00  33.00   1.00    1.00    --  -40.73  38.00-180.00   84
  3  ω      7.00  51.00   1.00    1.00    --   40.73 -99.00  90.00   44
  4  ω     39.00  81.00   1.00    1.00    --  107.58 -77.00 -30.00   42
  5  ω     74.00 108.00   1.00    1.00    --  107.58 -94.00   0.00   34
  6  ω    115.00 140.00   1.00    1.00    --  107.58 -77.00 -30.00   25
  7  ω     85.00 112.00   1.00    1.00    --  107.58-125.00 -30.00   27
  8  ω     44.00  95.00   1.00    1.00    --   40.73-125.00-150.00   51
  9  ω     41.00 121.00   1.00    1.00    --  107.58-125.00-180.00   80
 10  ω     61.00 140.00   1.00    1.00    --  107.58 -77.00-180.00   79
 11  ω     81.00 178.00   1.00    1.00    --  107.58  30.00-120.00   97
 12  ω     94.00 122.00   1.00    1.00    --  107.58 125.00 -60.00   28
 13  ω     83.00 171.00   1.00    1.00    --  107.58  30.00 -60.00   88
 14  ω    102.00 131.00   1.00    1.00    --  107.58 -45.00 120.00   29
 15  ω     40.00 117.00   1.00    1.00    --  107.58 -45.00   0.00   77
 16  ω     38.00  87.00   1.00    1.00    --  107.58 -45.00 120.00   49
 17  ω     31.00 121.00   1.00    1.00    --  107.58 -30.00 -90.00   90
 18  ω   -113.00 -19.00   1.00    1.00    --  -40.73 -57.00-120.00   94
;
_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      0.0404884000
_diffrn_orient_matrix_UB_12      0.0857834000
_diffrn_orient_matrix_UB_13      0.0892485000
_diffrn_orient_matrix_UB_21      -0.1194860000
_diffrn_orient_matrix_UB_22      0.0999875000
_diffrn_orient_matrix_UB_23      -0.0406853000
_diffrn_orient_matrix_UB_31      -0.1175213000
_diffrn_orient_matrix_UB_32      -0.0600269000
_diffrn_orient_matrix_UB_33      0.1040758000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3295
_reflns_number_total             4095
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.042
_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)+(0.0582P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1256
_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:
 C14(H14A,H14B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_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 0.71594(13) 0.55027(12) 0.13497(12) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.25764(14) 0.76305(12) 0.15286(12) 0.0286(3) Uani 1 1 d . . . . .
N1 N 0.55706(15) 0.31085(14) 0.17194(13) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.30564(15) 0.31941(13) 0.17124(13) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.25703(15) 0.55020(13) 0.16932(13) 0.0212(3) Uani 1 1 d . . . . .
N4 N 0.48619(16) 0.65554(13) 0.13761(13) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.17538(18) 0.26799(16) 0.14827(15) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.05906(18) 0.34283(16) 0.10090(15) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.064071 0.429698 0.085573 0.026 Uiso 1 1 calc R U . . .
C3 C -0.06285(19) 0.28659(17) 0.07720(16) 0.0258(4) Uani 1 1 d . . . . .
H3 H -0.141553 0.336001 0.047731 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0692(2) 0.15651(18) 0.09701(18) 0.0297(4) Uani 1 1 d . . . . .
H4 H -0.152810 0.119495 0.082235 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0480(2) 0.08233(17) 0.13844(17) 0.0271(4) Uani 1 1 d . . . . .
H5 H 0.043927 -0.004647 0.149409 0.033 Uiso 1 1 calc R U . . .
C6 C 0.17365(19) 0.13651(17) 0.16432(15) 0.0229(4) Uani 1 1 d . . . . .
C7 C 0.3035(2) 0.05959(17) 0.19593(17) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.297247 -0.026992 0.214516 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4330(2) 0.11101(16) 0.19892(17) 0.0257(4) Uani 1 1 d . . . . .
H8 H 0.517598 0.060022 0.213373 0.031 Uiso 1 1 calc R U . . .
C9 C 0.43965(18) 0.24398(16) 0.17982(16) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.49935(18) 0.43291(16) 0.16279(15) 0.0215(3) Uani 1 1 d . . . . .
C11 C 0.34700(18) 0.44026(16) 0.16676(15) 0.0196(3) Uani 1 1 d . . . . .
C12 C 0.58052(19) 0.54478(16) 0.14538(15) 0.0220(4) Uani 1 1 d . . . . .
C13 C 0.33032(19) 0.66273(16) 0.15181(15) 0.0225(4) Uani 1 1 d . . . . .
C14 C 0.5607(2) 0.77371(17) 0.12417(16) 0.0250(4) Uani 1 1 d . . . . .
H14A H 0.496111 0.841424 0.090412 0.030 Uiso 1 1 calc R U . . .
H14B H 0.652031 0.768475 0.065083 0.030 Uiso 1 1 calc R U . . .
C15 C 0.59902(19) 0.80526(16) 0.24455(16) 0.0225(4) Uani 1 1 d . . . . .
C16 C 0.7297(2) 0.86529(17) 0.24219(18) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.795756 0.878972 0.168314 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7628(2) 0.9049(2) 0.34828(19) 0.0340(4) Uani 1 1 d . . . . .
H17 H 0.849403 0.946999 0.344729 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6680(2) 0.8825(2) 0.45981(19) 0.0367(5) Uani 1 1 d . . . . .
H18 H 0.690724 0.909059 0.531157 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5390(2) 0.8200(2) 0.46420(18) 0.0366(5) Uani 1 1 d . . . . .
H19 H 0.475761 0.802987 0.539173 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5038(2) 0.78264(18) 0.35724(17) 0.0298(4) Uani 1 1 d . . . . .
H20 H 0.415973 0.742206 0.360615 0.036 Uiso 1 1 calc R U . . .
C21 C 0.11373(18) 0.55341(17) 0.26001(16) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.069915 0.472422 0.271382 0.029 Uiso 1 1 calc R U . . .
H21B H 0.043026 0.616295 0.226931 0.029 Uiso 1 1 calc R U . . .
C22 C 0.14268(19) 0.58383(18) 0.38339(16) 0.0263(4) Uani 1 1 d . . . . .
C23 C 0.2285(2) 0.4997(2) 0.45482(18) 0.0368(5) Uani 1 1 d . . . . .
H23 H 0.264965 0.423666 0.427384 0.044 Uiso 1 1 calc R U . . .
C24 C 0.2601(3) 0.5282(3) 0.5667(2) 0.0497(6) Uani 1 1 d . . . . .
H24 H 0.318585 0.471715 0.613276 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2055(2) 0.6393(3) 0.6090(2) 0.0470(6) Uani 1 1 d . . . . .
H25 H 0.227927 0.658333 0.683581 0.056 Uiso 1 1 calc R U . . .
C26 C 0.1168(3) 0.7232(2) 0.5405(2) 0.0458(6) Uani 1 1 d . . . . .
H26 H 0.077398 0.797708 0.569887 0.055 Uiso 1 1 calc R U . . .
C27 C 0.0871(2) 0.6950(2) 0.4270(2) 0.0373(5) Uani 1 1 d . . . . .
H27 H 0.029169 0.751909 0.380206 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.220(2) . ?
O2 C13 1.221(2) . ?
N1 C9 1.316(2) . ?
N1 C10 1.372(2) . ?
N2 C1 1.415(2) . ?
N2 C9 1.417(2) . ?
N2 C11 1.374(2) . ?
N3 C11 1.385(2) . ?
N3 C13 1.402(2) . ?
N3 C21 1.507(2) . ?
N4 C12 1.413(2) . ?
N4 C13 1.394(2) . ?
N4 C14 1.465(2) . ?
C1 C2 1.401(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(2) . ?
C6 C7 1.447(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.343(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.422(2) . ?
C10 C11 1.372(2) . ?
C10 C12 1.434(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.511(2) . ?
C15 C16 1.388(2) . ?
C15 C20 1.395(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.507(2) . ?
C22 C23 1.390(3) . ?
C22 C27 1.380(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.370(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.388(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.397(3) . ?
C27 H27 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
C9 N1 C10 104.13(14) . . ?
C1 N2 C9 121.05(14) . . ?
C11 N2 C1 133.33(14) . . ?
C11 N2 C9 104.48(13) . . ?
C11 N3 C13 116.66(14) . . ?
C11 N3 C21 119.71(14) . . ?
C13 N3 C21 112.87(13) . . ?
C12 N4 C14 115.77(14) . . ?
C13 N4 C12 126.60(14) . . ?
C13 N4 C14 117.39(14) . . ?
C2 C1 N2 122.25(15) . . ?
C2 C1 C6 120.82(15) . . ?
C6 C1 N2 116.68(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.39(16) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.54(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.19(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.79(17) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.14(16) . . ?
C1 C6 C7 120.49(16) . . ?
C5 C6 C7 121.15(16) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.17(17) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.51(16) . . ?
C9 C8 H8 120.2 . . ?
N1 C9 N2 112.74(15) . . ?
N1 C9 C8 128.31(16) . . ?
N2 C9 C8 118.92(15) . . ?
N1 C10 C12 127.37(15) . . ?
C11 C10 N1 111.94(15) . . ?
C11 C10 C12 120.63(16) . . ?
N2 C11 N3 128.67(15) . . ?
C10 C11 N2 106.47(14) . . ?
C10 C11 N3 124.83(15) . . ?
O1 C12 N4 120.73(16) . . ?
O1 C12 C10 126.61(16) . . ?
N4 C12 C10 112.65(14) . . ?
O2 C13 N3 120.01(15) . . ?
O2 C13 N4 121.86(16) . . ?
N4 C13 N3 118.10(15) . . ?
N4 C14 H14A 108.8 . . ?
N4 C14 H14B 108.8 . . ?
N4 C14 C15 113.60(14) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C16 C15 C14 118.94(16) . . ?
C16 C15 C20 118.56(17) . . ?
C20 C15 C14 122.41(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.75(17) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.52(18) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.36(18) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.23(18) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.54(17) . . ?
C19 C20 H20 119.7 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 C22 110.70(13) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C23 C22 C21 119.92(17) . . ?
C27 C22 C21 121.28(17) . . ?
C27 C22 C23 118.79(18) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.5(2) . . ?
C27 C26 H26 120.3 . . ?
C22 C27 C26 120.8(2) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C10 C11 N2 -3.59(19) . . . . ?
N1 C10 C11 N3 174.69(15) . . . . ?
N1 C10 C12 O1 0.4(3) . . . . ?
N1 C10 C12 N4 178.89(15) . . . . ?
N2 C1 C2 C3 178.12(15) . . . . ?
N2 C1 C6 C5 -178.00(15) . . . . ?
N2 C1 C6 C7 -3.4(2) . . . . ?
N3 C21 C22 C23 -65.9(2) . . . . ?
N3 C21 C22 C27 113.30(19) . . . . ?
N4 C14 C15 C16 144.95(16) . . . . ?
N4 C14 C15 C20 -38.7(2) . . . . ?
C1 N2 C9 N1 164.90(14) . . . . ?
C1 N2 C9 C8 -17.0(2) . . . . ?
C1 N2 C11 N3 19.0(3) . . . . ?
C1 N2 C11 C10 -162.85(16) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C1 C6 C7 C8 -6.5(3) . . . . ?
C2 C1 C6 C5 -3.7(2) . . . . ?
C2 C1 C6 C7 170.96(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -173.79(17) . . . . ?
C5 C6 C7 C8 167.95(17) . . . . ?
C6 C1 C2 C3 4.1(2) . . . . ?
C6 C7 C8 C9 4.7(3) . . . . ?
C7 C8 C9 N1 -175.51(18) . . . . ?
C7 C8 C9 N2 6.7(3) . . . . ?
C9 N1 C10 C11 0.81(19) . . . . ?
C9 N1 C10 C12 -176.46(16) . . . . ?
C9 N2 C1 C2 -159.31(15) . . . . ?
C9 N2 C1 C6 15.0(2) . . . . ?
C9 N2 C11 N3 -173.58(16) . . . . ?
C9 N2 C11 C10 4.61(17) . . . . ?
C10 N1 C9 N2 2.30(19) . . . . ?
C10 N1 C9 C8 -175.63(17) . . . . ?
C11 N2 C1 C2 6.5(3) . . . . ?
C11 N2 C1 C6 -179.25(16) . . . . ?
C11 N2 C9 N1 -4.48(18) . . . . ?
C11 N2 C9 C8 173.67(15) . . . . ?
C11 N3 C13 O2 179.92(15) . . . . ?
C11 N3 C13 N4 -2.2(2) . . . . ?
C11 N3 C21 C22 86.50(18) . . . . ?
C11 C10 C12 O1 -176.61(16) . . . . ?
C11 C10 C12 N4 1.8(2) . . . . ?
C12 N4 C13 O2 174.31(16) . . . . ?
C12 N4 C13 N3 -3.6(2) . . . . ?
C12 N4 C14 C15 -78.88(18) . . . . ?
C12 C10 C11 N2 173.89(14) . . . . ?
C12 C10 C11 N3 -7.8(3) . . . . ?
C13 N3 C11 N2 -174.25(15) . . . . ?
C13 N3 C11 C10 7.9(2) . . . . ?
C13 N3 C21 C22 -56.75(19) . . . . ?
C13 N4 C12 O1 -177.76(15) . . . . ?
C13 N4 C12 C10 3.7(2) . . . . ?
C13 N4 C14 C15 95.91(18) . . . . ?
C14 N4 C12 O1 -3.5(2) . . . . ?
C14 N4 C12 C10 177.93(13) . . . . ?
C14 N4 C13 O2 0.2(2) . . . . ?
C14 N4 C13 N3 -177.72(14) . . . . ?
C14 C15 C16 C17 174.70(17) . . . . ?
C14 C15 C20 C19 -176.06(18) . . . . ?
C15 C16 C17 C18 1.7(3) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -1.3(3) . . . . ?
C18 C19 C20 C15 1.3(3) . . . . ?
C20 C15 C16 C17 -1.8(3) . . . . ?
C21 N3 C11 N2 43.8(2) . . . . ?
C21 N3 C11 C10 -134.05(17) . . . . ?
C21 N3 C13 O2 -35.6(2) . . . . ?
C21 N3 C13 N4 142.28(15) . . . . ?
C21 C22 C23 C24 177.92(19) . . . . ?
C21 C22 C27 C26 -178.89(18) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C22 C27 C26 0.3(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C24 C25 C26 C27 -1.7(3) . . . . ?
C25 C26 C27 C22 1.2(3) . . . . ?
C27 C22 C23 C24 -1.3(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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_zyy-20200925
_database_code_depnum_ccdc_archive 'CCDC 2073617'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-05-04 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 N4 O2, H2 O'
_chemical_formula_sum            'C11 H12 N4 O3'
_chemical_formula_weight         248.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   7.5203(4)
_cell_length_b                   8.7465(4)
_cell_length_c                   9.6550(5)
_cell_angle_alpha                70.463(5)
_cell_angle_beta                 84.892(4)
_cell_angle_gamma                69.150(5)
_cell_volume                     558.99(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1660
_cell_measurement_theta_min      6.1960
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.619
_diffrn_reflns_theta_min         4.863
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -13.00   1.00    1.00    --  -35.62 147.00  16.00   89
  2  ω    -89.00  -2.00   1.00    1.00    --  -35.62 125.00-148.00   87
  3  ω     35.00 102.00   1.00    1.00    --   35.62-147.00 -32.00   67
  4  ω     38.00 118.00   1.00    1.00    --  107.12-125.00 132.00   80
  5  ω     39.00 134.00   1.00    1.00    --  107.12-147.00 -32.00   95
  6  ω     81.00 174.00   1.00    1.00    --  107.12 147.00  16.00   93
  7  ω     94.00 170.00   1.00    1.00    --  107.12 125.00-148.00   76
  8  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00  60.00   88
  9  ω    -59.00  36.00   1.00    1.00    --  -35.62  19.00  60.00   95
 10  ω     78.00 107.00   1.00    1.00    --   35.62 178.00  90.00   29
 11  ω     57.00 107.00   1.00    1.00    --   35.62 178.00 -90.00   50
 12  ω     12.00  37.00   1.00    1.00    --   35.62  19.00  30.00   25
 13  ω     51.00  77.00   1.00    1.00    --   35.62  19.00  30.00   26
 14  ω     41.00  83.00   1.00    1.00    --   35.62-125.00 132.00   42
 15  ω     61.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   47
 16  ω    102.00 140.00   1.00    1.00    --  107.12 111.00 -60.00   38
 17  ω     87.00 115.00   1.00    1.00    --  107.12  30.00 -60.00   28
 18  ω     49.00  92.00   1.00    1.00    --  107.12 -45.00  90.00   43
 19  ω     40.00  98.00   1.00    1.00    --  107.12 -61.00  30.00   58
 20  ω    139.00 165.00   1.00    1.00    --  107.12  30.00 -60.00   26
 21  ω    104.00 175.00   1.00    1.00    --  107.12 111.00 -30.00   71
 22  ω    110.00 172.00   1.00    1.00    --  107.12  77.00   0.00   62
 23  ω     44.00 134.00   1.00    1.00    --  107.12 -77.00 -90.00   90
 24  ω     85.00 110.00   1.00    1.00    --  107.12 -95.00 -30.00   25
 25  ω     81.00 174.00   1.00    1.00    --  107.12  77.00  30.00   93
 26  ω     39.00  65.00   1.00    1.00    --  107.12-111.00 150.00   26
 27  ω     69.00  98.00   1.00    1.00    --  107.12-111.00 150.00   29
 28  ω     59.00 136.00   1.00    1.00    --  107.12 -15.00 -30.00   77
 29  ω     37.00 128.00   1.00    1.00    --  107.12 -30.00-120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0359623000
_diffrn_orient_matrix_UB_12      0.0574808000
_diffrn_orient_matrix_UB_13      -0.1673150000
_diffrn_orient_matrix_UB_21      -0.2158121000
_diffrn_orient_matrix_UB_22      0.0475303000
_diffrn_orient_matrix_UB_23      0.0229712000
_diffrn_orient_matrix_UB_31      -0.0155013000
_diffrn_orient_matrix_UB_32      0.1848323000
_diffrn_orient_matrix_UB_33      -0.0132875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             2137
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0217(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1081
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8876(2) 0.65596(18) 0.08252(13) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.79839(18) 0.85898(15) 0.46896(14) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.70280(17) 0.54815(16) 0.64805(13) 0.0348(3) Uani 1 1 d . . . . .
N2 N 0.72676(15) 0.33976(14) 0.54946(13) 0.0292(3) Uani 1 1 d . . . . .
N3 N 0.82640(17) 0.48112(15) 0.30053(13) 0.0317(3) Uani 1 1 d . . . . .
N4 N 0.83892(17) 0.75609(16) 0.27644(14) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.68419(19) 0.39672(19) 0.67362(16) 0.0328(3) Uani 1 1 d . . . . .
C2 C 0.6290(2) 0.2906(2) 0.80287(17) 0.0424(4) Uani 1 1 d . . . . .
H2 H 0.600247 0.324720 0.886099 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6185(2) 0.1388(2) 0.80414(19) 0.0463(4) Uani 1 1 d . . . . .
H3 H 0.581864 0.068856 0.888905 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6625(2) 0.0847(2) 0.67852(19) 0.0435(4) Uani 1 1 d . . . . .
H4 H 0.654714 -0.020297 0.682163 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7153(2) 0.18288(19) 0.55410(18) 0.0374(4) Uani 1 1 d . . . . .
H5 H 0.743893 0.146351 0.472111 0.045 Uiso 1 1 calc R U . . .
C6 C 0.77408(17) 0.46843(17) 0.44317(15) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.75879(18) 0.59153(18) 0.50556(15) 0.0298(3) Uani 1 1 d . . . . .
C8 C 0.79819(19) 0.74565(18) 0.42280(16) 0.0325(3) Uani 1 1 d . . . . .
C9 C 0.8616(3) 0.9183(2) 0.1807(2) 0.0474(4) Uani 1 1 d . . . . .
H9A H 0.911982 0.904723 0.088900 0.071 Uiso 1 1 calc R U . . .
H9B H 0.947428 0.946232 0.227732 0.071 Uiso 1 1 calc R U . . .
H9C H 0.740011 1.009969 0.162860 0.071 Uiso 1 1 calc R U . . .
C10 C 0.8528(2) 0.6318(2) 0.21224(16) 0.0353(3) Uani 1 1 d . . . . .
C11 C 0.8579(3) 0.3430(2) 0.23695(19) 0.0479(4) Uani 1 1 d . . . . .
H11A H 0.943885 0.236332 0.300254 0.072 Uiso 1 1 calc R U . . .
H11B H 0.911620 0.372581 0.141927 0.072 Uiso 1 1 calc R U . . .
H11C H 0.738714 0.329781 0.227119 0.072 Uiso 1 1 calc R U . . .
O3 O 0.5874(2) 0.7121(2) 0.87607(16) 0.0637(4) Uani 1 1 d G . . . .
H3A H 0.628832 0.670834 0.806545 0.096 Uiso 1 1 d G U . . .
H3B H 0.685580 0.681898 0.929920 0.096 Uiso 1 1 d G U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2188(18) . ?
O2 C8 1.2157(17) . ?
N1 C1 1.3198(19) . ?
N1 C7 1.3694(18) . ?
N2 C1 1.4161(17) . ?
N2 C5 1.3908(18) . ?
N2 C6 1.3762(18) . ?
N3 C6 1.3770(17) . ?
N3 C10 1.3809(19) . ?
N3 C11 1.4695(19) . ?
N4 C8 1.3984(19) . ?
N4 C9 1.4711(19) . ?
N4 C10 1.392(2) . ?
C1 C2 1.413(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.416(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.344(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3670(19) . ?
C7 C8 1.437(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8502 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 104.47(12) . . ?
C5 N2 C1 121.00(12) . . ?
C6 N2 C1 104.90(11) . . ?
C6 N2 C5 134.10(12) . . ?
C6 N3 C10 118.18(12) . . ?
C6 N3 C11 123.88(13) . . ?
C10 N3 C11 117.94(12) . . ?
C8 N4 C9 116.04(13) . . ?
C10 N4 C8 126.53(13) . . ?
C10 N4 C9 117.38(13) . . ?
N1 C1 N2 112.15(12) . . ?
N1 C1 C2 129.36(14) . . ?
C2 C1 N2 118.49(13) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.26(15) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.07(15) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.01(15) . . ?
C5 C4 H4 119.5 . . ?
N2 C5 H5 120.4 . . ?
C4 C5 N2 119.18(15) . . ?
C4 C5 H5 120.4 . . ?
N2 C6 N3 129.84(12) . . ?
C7 C6 N2 106.35(12) . . ?
C7 C6 N3 123.81(13) . . ?
N1 C7 C8 127.20(13) . . ?
C6 C7 N1 112.12(13) . . ?
C6 C7 C8 120.68(13) . . ?
O2 C8 N4 120.92(14) . . ?
O2 C8 C7 126.27(14) . . ?
N4 C8 C7 112.81(12) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 N3 121.60(14) . . ?
O1 C10 N4 120.68(14) . . ?
N3 C10 N4 117.71(13) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H3A O3 H3B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179.67(15) . . . . ?
N1 C7 C8 O2 4.4(2) . . . . ?
N1 C7 C8 N4 -175.64(13) . . . . ?
N2 C1 C2 C3 0.0(2) . . . . ?
N2 C6 C7 N1 -0.20(15) . . . . ?
N2 C6 C7 C8 -179.75(11) . . . . ?
N3 C6 C7 N1 179.43(12) . . . . ?
N3 C6 C7 C8 -0.1(2) . . . . ?
C1 N1 C7 C6 0.22(15) . . . . ?
C1 N1 C7 C8 179.73(13) . . . . ?
C1 N2 C5 C4 0.2(2) . . . . ?
C1 N2 C6 N3 -179.51(13) . . . . ?
C1 N2 C6 C7 0.09(14) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 N2 0.0(2) . . . . ?
C5 N2 C1 N1 -179.92(12) . . . . ?
C5 N2 C1 C2 -0.19(19) . . . . ?
C5 N2 C6 N3 0.5(2) . . . . ?
C5 N2 C6 C7 -179.95(14) . . . . ?
C6 N2 C1 N1 0.05(15) . . . . ?
C6 N2 C1 C2 179.79(12) . . . . ?
C6 N2 C5 C4 -179.78(14) . . . . ?
C6 N3 C10 O1 -175.39(14) . . . . ?
C6 N3 C10 N4 4.78(19) . . . . ?
C6 C7 C8 O2 -176.10(14) . . . . ?
C6 C7 C8 N4 3.83(18) . . . . ?
C7 N1 C1 N2 -0.16(15) . . . . ?
C7 N1 C1 C2 -179.86(15) . . . . ?
C8 N4 C10 O1 179.34(14) . . . . ?
C8 N4 C10 N3 -0.8(2) . . . . ?
C9 N4 C8 O2 -6.1(2) . . . . ?
C9 N4 C8 C7 173.98(12) . . . . ?
C9 N4 C10 O1 2.0(2) . . . . ?
C9 N4 C10 N3 -178.22(13) . . . . ?
C10 N3 C6 N2 175.09(13) . . . . ?
C10 N3 C6 C7 -4.5(2) . . . . ?
C10 N4 C8 O2 176.49(13) . . . . ?
C10 N4 C8 C7 -3.4(2) . . . . ?
C11 N3 C6 N2 -5.6(2) . . . . ?
C11 N3 C6 C7 174.87(14) . . . . ?
C11 N3 C10 O1 5.2(2) . . . . ?
C11 N3 C10 N4 -174.58(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.570
####################################################################### 
# 
# 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_exp_2831
_database_code_depnum_ccdc_archive 'CCDC 2073615'
loop_
_audit_author_name
_audit_author_address
'Qi-Liang Yang'
;Henan normal university
China
;
_audit_update_record             
;
2021-03-27 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_audit_creation_date             2021-03-01
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N4 O4'
_chemical_formula_sum            'C13 H14 N4 O4'
_chemical_formula_weight         290.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.7843(4)
_cell_length_b                   13.7263(4)
_cell_length_c                   7.4329(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.219(3)
_cell_angle_gamma                90
_cell_volume                     1303.35(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1913
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.7710
_cell_measurement_theta_min      3.4340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4494
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.591
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_min         3.460
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  18.00   1.00    3.00    --  -40.73  77.00 -30.00   46
  2  ω    -45.00  -2.00   1.00    3.00    --  -40.73 125.00-150.00   43
  3  ω    -73.00 -41.00   1.00    3.00    --  -40.73  77.00 -30.00   32
  4  ω     18.00 105.00   1.00    3.00    --   40.73  77.00  90.00   87
  5  ω     97.00 123.00   1.00    4.00    --  106.95 125.00 -30.00   26
  6  ω    142.00 168.00   1.00    4.00    --  106.95 125.00 -30.00   26
  7  ω    106.00 172.00   1.00    4.00    --  106.95 108.00 103.00   66
  8  ω     79.00 167.00   1.00    4.00    --  106.95  61.00 150.00   88
  9  ω     49.00 128.00   1.00    4.00    --  106.95 -45.00 120.00   79
 10  ω     48.00 139.00   1.00    4.00    --  106.95 -77.00   0.00   91
 11  ω     56.00  93.00   1.00    4.00    --  106.95 -61.00-150.00   37
;
_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      -0.0938499000
_diffrn_orient_matrix_UB_12      -0.0633451000
_diffrn_orient_matrix_UB_13      0.0511392000
_diffrn_orient_matrix_UB_21      0.0729047000
_diffrn_orient_matrix_UB_22      -0.0891101000
_diffrn_orient_matrix_UB_23      0.0211273000
_diffrn_orient_matrix_UB_31      0.0213052000
_diffrn_orient_matrix_UB_32      0.0255827000
_diffrn_orient_matrix_UB_33      0.1995662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1894
_reflns_number_total             2292
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.053
_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)+(0.0564P)²+0.1796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78328(10) 0.07655(9) 0.40242(17) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.96077(10) 0.15282(10) 0.65995(16) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.91118(10) 0.37863(9) 0.54508(16) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.72282(10) 0.54178(9) 0.34740(18) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.57126(11) 0.33723(11) 0.27341(19) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.58547(11) 0.17209(11) 0.2641(2) 0.0225(3) Uani 1 1 d . . . . .
N3 N 0.84992(11) 0.22983(11) 0.45029(19) 0.0201(3) Uani 1 1 d . . . . .
N4 N 0.74512(12) 0.37309(11) 0.42216(19) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.52098(14) 0.42566(14) 0.2371(2) 0.0233(4) Uani 1 1 d . . . . .
H1 H 0.553841 0.484397 0.265735 0.028 Uiso 1 1 calc R U . . .
C2 C 0.42391(14) 0.42440(15) 0.1596(2) 0.0262(4) Uani 1 1 d . . . . .
H2 H 0.389874 0.483005 0.134565 0.031 Uiso 1 1 calc R U . . .
C3 C 0.37256(15) 0.33522(15) 0.1155(3) 0.0286(5) Uani 1 1 d . . . . .
H3 H 0.304909 0.336239 0.064807 0.034 Uiso 1 1 calc R U . . .
C4 C 0.42126(14) 0.24849(15) 0.1465(3) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.387470 0.190454 0.115998 0.032 Uiso 1 1 calc R U . . .
C5 C 0.52388(14) 0.24711(13) 0.2257(2) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.67422(13) 0.21357(13) 0.3395(2) 0.0199(4) Uani 1 1 d . . . . .
C7 C 0.66788(13) 0.31296(13) 0.3485(2) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.76903(14) 0.16479(13) 0.3994(2) 0.0204(4) Uani 1 1 d . . . . .
C9 C 0.84073(13) 0.33085(13) 0.4763(2) 0.0199(4) Uani 1 1 d . . . . .
C10 C 0.95299(14) 0.18812(14) 0.4815(2) 0.0230(4) Uani 1 1 d . . . . .
H10A H 0.963641 0.135308 0.397475 0.028 Uiso 1 1 calc R U . . .
H10B H 1.006176 0.237223 0.463769 0.028 Uiso 1 1 calc R U . . .
C11 C 1.05767(16) 0.10467(19) 0.6955(3) 0.0406(6) Uani 1 1 d . . . . .
H11A H 1.067371 0.055523 0.605740 0.061 Uiso 1 1 calc R U . . .
H11B H 1.057420 0.074833 0.812247 0.061 Uiso 1 1 calc R U . . .
H11C H 1.113727 0.151102 0.692382 0.061 Uiso 1 1 calc R U . . .
C12 C 0.72356(15) 0.47237(13) 0.4852(2) 0.0229(4) Uani 1 1 d . . . . .
H12A H 0.6529(16) 0.4749(14) 0.529(3) 0.023(5) Uiso 1 1 d . . . . .
H12B H 0.7787(15) 0.4847(14) 0.582(3) 0.020(5) Uiso 1 1 d . . . . .
C13 C 0.82465(16) 0.56202(16) 0.2818(3) 0.0330(5) Uani 1 1 d . . . . .
H13A H 0.820178 0.615821 0.199385 0.049 Uiso 1 1 calc R U . . .
H13B H 0.850213 0.505602 0.221114 0.049 Uiso 1 1 calc R U . . .
H13C H 0.871706 0.578172 0.381160 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.225(2) . ?
O2 C10 1.412(2) . ?
O2 C11 1.420(2) . ?
O3 C9 1.211(2) . ?
O4 C12 1.399(2) . ?
O4 C13 1.435(2) . ?
N1 C1 1.395(2) . ?
N1 C5 1.416(2) . ?
N1 C7 1.377(2) . ?
N2 C5 1.321(2) . ?
N2 C6 1.370(2) . ?
N3 C8 1.407(2) . ?
N3 C9 1.406(2) . ?
N3 C10 1.447(2) . ?
N4 C7 1.383(2) . ?
N4 C9 1.398(2) . ?
N4 C12 1.471(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.348(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.421(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.417(3) . ?
C6 C7 1.369(3) . ?
C6 C8 1.440(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.97(2) . ?
C12 H12B 1.001(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 O2 C11 111.32(14) . . ?
C12 O4 C13 113.58(14) . . ?
C1 N1 C5 121.47(15) . . ?
C7 N1 C1 133.52(16) . . ?
C7 N1 C5 104.99(14) . . ?
C5 N2 C6 103.99(15) . . ?
C8 N3 C10 116.57(15) . . ?
C9 N3 C8 126.76(15) . . ?
C9 N3 C10 116.66(15) . . ?
C7 N4 C9 117.98(15) . . ?
C7 N4 C12 122.63(15) . . ?
C9 N4 C12 117.73(15) . . ?
N1 C1 H1 120.6 . . ?
C2 C1 N1 118.77(17) . . ?
C2 C1 H1 120.6 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.27(18) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.72(17) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.52(18) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 118.19(16) . . ?
N2 C5 N1 112.41(15) . . ?
N2 C5 C4 129.40(17) . . ?
N2 C6 C8 127.39(17) . . ?
C7 C6 N2 112.64(16) . . ?
C7 C6 C8 119.93(16) . . ?
N1 C7 N4 129.17(16) . . ?
C6 C7 N1 105.97(15) . . ?
C6 C7 N4 124.85(16) . . ?
O1 C8 N3 121.02(16) . . ?
O1 C8 C6 126.02(17) . . ?
N3 C8 C6 112.91(15) . . ?
O3 C9 N3 121.83(16) . . ?
O3 C9 N4 121.64(17) . . ?
N4 C9 N3 116.52(15) . . ?
O2 C10 N3 108.49(14) . . ?
O2 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
N3 C10 H10A 110.0 . . ?
N3 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N4 113.20(14) . . ?
O4 C12 H12A 103.8(12) . . ?
O4 C12 H12B 113.2(11) . . ?
N4 C12 H12A 109.1(12) . . ?
N4 C12 H12B 104.5(11) . . ?
H12A C12 H12B 113.2(16) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(3) . . . . ?
N2 C6 C7 N1 -0.9(2) . . . . ?
N2 C6 C7 N4 178.40(15) . . . . ?
N2 C6 C8 O1 -4.7(3) . . . . ?
N2 C6 C8 N3 172.74(16) . . . . ?
C1 N1 C5 N2 177.25(15) . . . . ?
C1 N1 C5 C4 -2.8(2) . . . . ?
C1 N1 C7 N4 3.9(3) . . . . ?
C1 N1 C7 C6 -176.87(18) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 N1 1.3(3) . . . . ?
C3 C4 C5 N2 -178.66(18) . . . . ?
C5 N1 C1 C2 2.0(3) . . . . ?
C5 N1 C7 N4 -178.15(17) . . . . ?
C5 N1 C7 C6 1.06(18) . . . . ?
C5 N2 C6 C7 0.2(2) . . . . ?
C5 N2 C6 C8 -177.23(17) . . . . ?
C6 N2 C5 N1 0.48(19) . . . . ?
C6 N2 C5 C4 -179.51(18) . . . . ?
C7 N1 C1 C2 179.66(17) . . . . ?
C7 N1 C5 N2 -1.00(19) . . . . ?
C7 N1 C5 C4 178.99(16) . . . . ?
C7 N4 C9 O3 -178.52(16) . . . . ?
C7 N4 C9 N3 0.1(2) . . . . ?
C7 N4 C12 O4 -84.1(2) . . . . ?
C7 C6 C8 O1 177.99(17) . . . . ?
C7 C6 C8 N3 -4.6(2) . . . . ?
C8 N3 C9 O3 169.05(16) . . . . ?
C8 N3 C9 N4 -9.6(2) . . . . ?
C8 N3 C10 O2 -84.39(18) . . . . ?
C8 C6 C7 N1 176.82(15) . . . . ?
C8 C6 C7 N4 -3.9(3) . . . . ?
C9 N3 C8 O1 -170.80(16) . . . . ?
C9 N3 C8 C6 11.6(2) . . . . ?
C9 N3 C10 O2 94.76(18) . . . . ?
C9 N4 C7 N1 -174.60(16) . . . . ?
C9 N4 C7 C6 6.3(3) . . . . ?
C9 N4 C12 O4 110.97(17) . . . . ?
C10 N3 C8 O1 8.3(2) . . . . ?
C10 N3 C8 C6 -169.33(14) . . . . ?
C10 N3 C9 O3 -10.0(2) . . . . ?
C10 N3 C9 N4 171.33(14) . . . . ?
C11 O2 C10 N3 175.86(17) . . . . ?
C12 N4 C7 N1 20.5(3) . . . . ?
C12 N4 C7 C6 -158.63(17) . . . . ?
C12 N4 C9 O3 -12.8(2) . . . . ?
C12 N4 C9 N3 165.83(15) . . . . ?
C13 O4 C12 N4 -71.3(2) . . . . ?

_olex2_date_sample_data_collection 2021-03-01
_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 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.542
