# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_sjw-20191009
_database_code_depnum_ccdc_archive 'CCDC 2018326'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O5'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4068(5)
_cell_length_b                   21.5669(9)
_cell_length_c                   9.8567(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.988(5)
_cell_angle_gamma                90
_cell_volume                     1992.11(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3737
_cell_measurement_temperature    293.50(10)
_cell_measurement_theta_max      27.2020
_cell_measurement_theta_min      4.1670
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81419
_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    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12787
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.042
_diffrn_reflns_theta_min         3.437
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.50(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  54.00   1.00    4.83    --   16.29  64.00 140.00   29
  2  ω     57.00  83.00   1.00    4.83    --   16.29  64.00 140.00   26
  3  ω    -50.00 -13.00   1.00    4.83    --   16.29 -64.00   4.00   37
  4  ω     36.00  73.00   1.00    4.83    --   16.29 178.00   0.00   37
  5  ω    -53.00  35.00   1.00    4.83    --   16.29 -38.00  30.00   88
  6  ω     55.00  88.00   1.00    4.83    --   16.29 178.00 -90.00   33
  7  ω     53.00  78.00   1.00    4.83    --   16.29 178.00 -30.00   25
  8  ω     23.00  50.00   1.00    4.83    --  -16.91  64.00 140.00   27
;
_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      -0.0731251000
_diffrn_orient_matrix_UB_12      -0.0072789000
_diffrn_orient_matrix_UB_13      0.0034496000
_diffrn_orient_matrix_UB_21      0.0191759000
_diffrn_orient_matrix_UB_22      -0.0232815000
_diffrn_orient_matrix_UB_23      0.0489859000
_diffrn_orient_matrix_UB_31      -0.0039030000
_diffrn_orient_matrix_UB_32      0.0220651000
_diffrn_orient_matrix_UB_33      0.0529604000
_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                3083
_reflns_number_total             4606
_reflns_odcompleteness_completeness 99.67
_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 1.171.40.53 (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         0.263
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.8313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1536
_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 Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_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 0.53619(14) 0.37550(6) 0.26216(14) 0.0429(3) Uani 1 1 d . . . . .
O2 O 0.3390(2) 0.40204(8) 0.0661(2) 0.0820(6) Uani 1 1 d . . . . .
O3 O 0.20251(16) 0.32325(7) 0.12378(17) 0.0590(4) Uani 1 1 d . . . . .
O4 O 0.33457(16) 0.35090(6) 0.44009(15) 0.0514(4) Uani 1 1 d . . . . .
O5 O 0.3468(2) 0.25108(7) 0.3794(2) 0.0858(6) Uani 1 1 d . . . . .
N1 N 0.67582(18) 0.34443(7) 0.46035(18) 0.0435(4) Uani 1 1 d . . . . .
N2 N 0.6807(2) 0.28544(8) 0.5097(2) 0.0596(5) Uani 1 1 d . . . . .
N3 N 0.6699(2) 0.28749(9) 0.6399(2) 0.0679(6) Uani 1 1 d . . . . .
C1 C 0.6582(2) 0.38534(9) 0.5629(2) 0.0410(5) Uani 1 1 d . . . . .
C2 C 0.6423(2) 0.44959(9) 0.5679(2) 0.0511(5) Uani 1 1 d . . . . .
H2 H 0.645503 0.474231 0.490771 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6218(3) 0.47426(12) 0.6919(3) 0.0647(7) Uani 1 1 d . . . . .
H3 H 0.610492 0.516930 0.699361 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6172(3) 0.43767(15) 0.8080(3) 0.0748(8) Uani 1 1 d . . . . .
H4 H 0.602208 0.456599 0.890372 0.090 Uiso 1 1 calc R U . . .
C5 C 0.6340(3) 0.37459(15) 0.8043(3) 0.0720(8) Uani 1 1 d . . . . .
H5 H 0.631552 0.350329 0.882087 0.086 Uiso 1 1 calc R U . . .
C6 C 0.6551(2) 0.34856(11) 0.6778(2) 0.0523(5) Uani 1 1 d . . . . .
C7 C 0.6724(2) 0.35494(9) 0.3139(2) 0.0418(5) Uani 1 1 d . . . . .
H7 H 0.693863 0.315886 0.269134 0.050 Uiso 1 1 calc R U . . .
C8 C 0.7804(2) 0.40324(9) 0.2803(2) 0.0426(5) Uani 1 1 d . . . . .
C9 C 0.7480(2) 0.44603(10) 0.1790(2) 0.0514(5) Uani 1 1 d . . . . .
H9 H 0.657275 0.446531 0.133223 0.062 Uiso 1 1 calc R U . . .
C10 C 0.8493(3) 0.48835(11) 0.1447(3) 0.0629(6) Uani 1 1 d . . . . .
H10 H 0.826298 0.516953 0.075690 0.075 Uiso 1 1 calc R U . . .
C11 C 0.9825(3) 0.48851(12) 0.2113(3) 0.0651(7) Uani 1 1 d . . . . .
H11 H 1.049946 0.517318 0.188353 0.078 Uiso 1 1 calc R U . . .
C12 C 1.0162(3) 0.44611(14) 0.3118(3) 0.0762(8) Uani 1 1 d . . . . .
H12 H 1.107275 0.445801 0.356770 0.091 Uiso 1 1 calc R U . . .
C13 C 0.9159(3) 0.40372(12) 0.3471(3) 0.0670(7) Uani 1 1 d . . . . .
H13 H 0.939555 0.375262 0.416240 0.080 Uiso 1 1 calc R U . . .
C14 C 0.4325(2) 0.32887(9) 0.2336(2) 0.0448(5) Uani 1 1 d . . . . .
H14 H 0.477597 0.294001 0.190130 0.054 Uiso 1 1 calc R U . . .
C15 C 0.3666(2) 0.30481(9) 0.3589(2) 0.0499(5) Uani 1 1 d . . . . .
C16 C 0.2760(3) 0.33351(12) 0.5663(3) 0.0706(7) Uani 1 1 d . . . . .
H16A H 0.343645 0.307714 0.620555 0.085 Uiso 1 1 calc R U . . .
H16B H 0.188677 0.310061 0.546622 0.085 Uiso 1 1 calc R U . . .
C17 C 0.2467(4) 0.39018(14) 0.6417(3) 0.0829(9) Uani 1 1 d . . . . .
H17A H 0.173854 0.413792 0.590614 0.124 Uiso 1 1 calc R U . . .
H17B H 0.332141 0.414533 0.655189 0.124 Uiso 1 1 calc R U . . .
H17C H 0.214784 0.379245 0.728427 0.124 Uiso 1 1 calc R U . . .
C18 C 0.3209(2) 0.35684(10) 0.1312(2) 0.0510(5) Uani 1 1 d . . . . .
C19 C 0.0904(3) 0.34199(14) 0.0214(3) 0.0819(9) Uani 1 1 d . . . . .
H19A H 0.054463 0.382519 0.043988 0.098 Uiso 1 1 calc R U . . .
H19B H 0.128396 0.344771 -0.066775 0.098 Uiso 1 1 calc R U . . .
C20 C -0.0228(4) 0.29766(18) 0.0158(6) 0.167(2) Uani 1 1 d . . . . .
H20A H -0.104986 0.314314 -0.036281 0.251 Uiso 1 1 calc R U . . .
H20B H -0.046467 0.288573 0.106517 0.251 Uiso 1 1 calc R U . . .
H20C H 0.007010 0.260319 -0.026483 0.251 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 C7 1.408(2) . ?
O1 C14 1.412(2) . ?
O2 C18 1.187(3) . ?
O3 C18 1.326(3) . ?
O3 C19 1.452(3) . ?
O4 C15 1.327(3) . ?
O4 C16 1.452(3) . ?
O5 C15 1.194(2) . ?
N1 N2 1.361(2) . ?
N1 C1 1.363(3) . ?
N1 C7 1.459(3) . ?
N2 N3 1.297(3) . ?
N3 C6 1.379(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.512(3) . ?
C8 C9 1.374(3) . ?
C8 C13 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.520(3) . ?
C14 C18 1.516(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.469(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.429(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C7 O1 C14 116.02(14) . . ?
C18 O3 C19 116.3(2) . . ?
C15 O4 C16 116.49(17) . . ?
N2 N1 C1 110.04(17) . . ?
N2 N1 C7 119.72(17) . . ?
C1 N1 C7 129.77(15) . . ?
N3 N2 N1 108.57(18) . . ?
N2 N3 C6 108.63(18) . . ?
N1 C1 C2 133.60(19) . . ?
N1 C1 C6 104.38(17) . . ?
C6 C1 C2 122.0(2) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.9(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(2) . . ?
C6 C5 H5 121.7 . . ?
N3 C6 C1 108.4(2) . . ?
N3 C6 C5 130.6(2) . . ?
C1 C6 C5 121.0(2) . . ?
O1 C7 N1 110.40(16) . . ?
O1 C7 H7 108.9 . . ?
O1 C7 C8 108.13(15) . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C8 111.49(16) . . ?
C8 C7 H7 108.9 . . ?
C9 C8 C7 120.72(18) . . ?
C9 C8 C13 118.6(2) . . ?
C13 C8 C7 120.67(18) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
O1 C14 H14 108.4 . . ?
O1 C14 C15 113.84(17) . . ?
O1 C14 C18 105.99(15) . . ?
C15 C14 H14 108.4 . . ?
C18 C14 H14 108.4 . . ?
C18 C14 C15 111.64(18) . . ?
O4 C15 C14 111.37(16) . . ?
O5 C15 O4 125.3(2) . . ?
O5 C15 C14 123.4(2) . . ?
O4 C16 H16A 110.0 . . ?
O4 C16 H16B 110.0 . . ?
O4 C16 C17 108.7(2) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 O3 125.3(2) . . ?
O2 C18 C14 124.3(2) . . ?
O3 C18 C14 110.43(19) . . ?
O3 C19 H19A 109.8 . . ?
O3 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 O3 109.5(3) . . ?
C20 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 -19.3(3) . . . . ?
O1 C7 C8 C13 163.3(2) . . . . ?
O1 C14 C15 O4 44.1(2) . . . . ?
O1 C14 C15 O5 -136.1(2) . . . . ?
O1 C14 C18 O2 16.8(3) . . . . ?
O1 C14 C18 O3 -164.18(17) . . . . ?
N1 N2 N3 C6 1.0(3) . . . . ?
N1 C1 C2 C3 177.8(2) . . . . ?
N1 C1 C6 N3 -0.5(2) . . . . ?
N1 C1 C6 C5 -178.1(2) . . . . ?
N1 C7 C8 C9 -140.86(19) . . . . ?
N1 C7 C8 C13 41.7(3) . . . . ?
N2 N1 C1 C2 -177.7(2) . . . . ?
N2 N1 C1 C6 1.1(2) . . . . ?
N2 N1 C7 O1 108.05(19) . . . . ?
N2 N1 C7 C8 -131.74(19) . . . . ?
N2 N3 C6 C1 -0.3(3) . . . . ?
N2 N3 C6 C5 177.0(3) . . . . ?
C1 N1 N2 N3 -1.3(2) . . . . ?
C1 N1 C7 O1 -63.3(3) . . . . ?
C1 N1 C7 C8 56.9(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C1 C6 N3 178.5(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 N3 -177.2(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 O1 C14 C15 79.0(2) . . . . ?
C7 O1 C14 C18 -157.90(17) . . . . ?
C7 N1 N2 N3 -174.25(19) . . . . ?
C7 N1 C1 C2 -5.7(4) . . . . ?
C7 N1 C1 C6 173.06(19) . . . . ?
C7 C8 C9 C10 -177.2(2) . . . . ?
C7 C8 C13 C12 177.1(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C8 C13 C12 -0.4(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C14 O1 C7 N1 -82.5(2) . . . . ?
C14 O1 C7 C8 155.32(16) . . . . ?
C15 O4 C16 C17 -179.6(2) . . . . ?
C15 C14 C18 O2 141.3(2) . . . . ?
C15 C14 C18 O3 -39.7(2) . . . . ?
C16 O4 C15 O5 2.6(3) . . . . ?
C16 O4 C15 C14 -177.60(19) . . . . ?
C18 O3 C19 C20 173.7(3) . . . . ?
C18 C14 C15 O4 -75.9(2) . . . . ?
C18 C14 C15 O5 104.0(3) . . . . ?
C19 O3 C18 O2 3.8(4) . . . . ?
C19 O3 C18 C14 -175.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.739
####################################################################### 
# 
# 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_7828
_database_code_depnum_ccdc_archive 'CCDC 2040250'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-10-23
_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         'C19 H19 Cl N4 O5'
_chemical_formula_sum            'C19 H19 Cl N4 O5'
_chemical_formula_weight         418.83
_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'
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                   11.8048(9)
_cell_length_b                   15.1785(10)
_cell_length_c                   16.7524(12)
_cell_angle_alpha                89.985(6)
_cell_angle_beta                 87.821(6)
_cell_angle_gamma                80.497(6)
_cell_volume                     2958.3(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7241
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.8820
_cell_measurement_theta_min      2.3220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49757
_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    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23126
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.032
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  63.00   1.00    4.00    --  -11.27   0.00 -90.00  115
  2  ω     -9.00  23.00   1.00    4.00    --  -11.27 -99.00 -60.00   32
  3  ω     -2.00  27.00   1.00    4.00    --  -11.27 -99.00-107.00   29
  4  ω     11.00  50.00   1.00    4.00    --   11.90 -99.00 -90.00   39
  5  ω     67.00  94.00   1.00    4.00    --   11.90-178.00-120.00   27
  6  ω    -35.00  54.00   1.00    4.00    --  -11.27  37.00 150.00   89
  7  ω    -51.00 -24.00   1.00    4.00    --  -11.27  99.00  -1.00   27
;
_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      -0.0400948000
_diffrn_orient_matrix_UB_12      -0.0173712000
_diffrn_orient_matrix_UB_13      -0.0234391000
_diffrn_orient_matrix_UB_21      -0.0138974000
_diffrn_orient_matrix_UB_22      -0.0265058000
_diffrn_orient_matrix_UB_23      0.0326711000
_diffrn_orient_matrix_UB_31      -0.0437803000
_diffrn_orient_matrix_UB_32      0.0352252000
_diffrn_orient_matrix_UB_33      0.0133734000
_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                7712
_reflns_number_total             10386
_reflns_odcompleteness_completeness 99.76
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         10386
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0752
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0951P)²+2.9486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2015
_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. Restrained distances
 C58-C37 = C2A-C38
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C58) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C37) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C2A) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C38) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Sof(O0)=1-FVAR(1)
 Sof(O15)=FVAR(1)
 Sof(C38)=Sof(H38A)=Sof(H38B)=1-FVAR(2)
 Sof(C37)=Sof(H37A)=Sof(H37B)=FVAR(2)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(3)
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C13(H13), C25(H25), C32(H32), C45(H45), C51(H51)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B), C34(H34A,H34B), C37(H37A,H37B), C38(H38A,
 H38B), C53(H53A,H53B), C56(H56A,H56B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C21(H21),
 C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C40(H40), C41(H41),
  C42(H42), C43(H43), C44(H44), C46(H46), C49(H49)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C35(H35A,H35B,H35C), C58(H58A,H58B,
 H58C), C2A(H2AA,H2AB,H2AC), C54(H54A,H54B,H54C), C57(H57A,H57B,H57C)
;
_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 0.07623(9) 0.37662(6) 0.14597(6) 0.0380(3) Uani 1 1 d . . . . .
O1 O 0.5662(2) 0.16698(15) 0.34619(14) 0.0232(6) Uani 1 1 d . . . . .
O2 O 0.2939(2) 0.14235(16) 0.40220(16) 0.0295(6) Uani 1 1 d . . . . .
O3 O 0.3717(3) 0.26163(17) 0.43572(19) 0.0419(8) Uani 1 1 d . . . . .
O4 O 0.5021(3) 0.0928(2) 0.53846(18) 0.0451(8) Uani 1 1 d . . . . .
O5 O 0.6655(2) 0.10797(16) 0.47232(15) 0.0296(6) Uani 1 1 d . . . . .
N1 N 0.1428(3) 0.2033(2) 0.1438(2) 0.0343(8) Uani 1 1 d . . . . .
N2 N 0.3215(3) 0.12183(19) 0.18996(19) 0.0263(7) Uani 1 1 d . . . . .
N3 N 0.3265(3) 0.35319(19) 0.22708(19) 0.0266(7) Uani 1 1 d . . . . .
N4 N 0.4425(3) 0.22057(18) 0.24289(17) 0.0217(7) Uani 1 1 d . . . . .
C1 C 0.1723(3) 0.2801(2) 0.1647(2) 0.0278(9) Uani 1 1 d . . . . .
C2 C 0.2201(4) 0.1286(3) 0.1579(3) 0.0358(10) Uani 1 1 d . . . . .
H2 H 0.198555 0.074957 0.142828 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2742(3) 0.2843(2) 0.1997(2) 0.0246(8) Uani 1 1 d . . . . .
C4 C 0.3457(3) 0.2013(2) 0.2094(2) 0.0218(8) Uani 1 1 d . . . . .
C5 C 0.4253(3) 0.3123(2) 0.2517(2) 0.0268(9) Uani 1 1 d . . . . .
H5 H 0.479412 0.342495 0.273427 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5466(3) 0.1586(2) 0.2645(2) 0.0231(8) Uani 1 1 d . . . . .
H6 H 0.535428 0.097268 0.253595 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6519(3) 0.1766(2) 0.2177(2) 0.0229(8) Uani 1 1 d . . . . .
C8 C 0.6455(3) 0.2131(2) 0.1418(2) 0.0269(9) Uani 1 1 d . . . . .
H8 H 0.574302 0.228464 0.119079 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7442(4) 0.2270(3) 0.0994(2) 0.0319(9) Uani 1 1 d . . . . .
H9 H 0.738689 0.251613 0.048568 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8502(4) 0.2045(3) 0.1322(3) 0.0355(10) Uani 1 1 d . . . . .
H10 H 0.916292 0.214302 0.103930 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8576(4) 0.1673(3) 0.2077(3) 0.0393(11) Uani 1 1 d . . . . .
H11 H 0.929230 0.151379 0.229779 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7594(3) 0.1534(3) 0.2509(2) 0.0309(9) Uani 1 1 d . . . . .
H12 H 0.765233 0.128829 0.301732 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4959(3) 0.1238(2) 0.3997(2) 0.0237(8) Uani 1 1 d . . . . .
H13 H 0.483820 0.067039 0.376460 0.028 Uiso 1 1 calc R U . . .
C14 C 0.3800(3) 0.1843(2) 0.4156(2) 0.0264(9) Uani 1 1 d . . . . .
C15 C 0.1790(3) 0.1957(3) 0.4138(3) 0.0384(11) Uani 1 1 d . . . . .
H15A H 0.173893 0.250935 0.384044 0.046 Uiso 1 1 calc R U . . .
H15B H 0.163081 0.210282 0.469946 0.046 Uiso 1 1 calc R U . . .
C16 C 0.0954(4) 0.1415(3) 0.3848(4) 0.0554(14) Uani 1 1 d . . . . .
H16A H 0.114496 0.124785 0.330054 0.083 Uiso 1 1 calc R U . . .
H16B H 0.019455 0.175799 0.388838 0.083 Uiso 1 1 calc R U . . .
H16C H 0.098174 0.088655 0.416692 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5544(3) 0.1071(2) 0.4781(2) 0.0264(9) Uani 1 1 d . . . . .
C18 C 0.7277(4) 0.0914(3) 0.5454(2) 0.0343(10) Uani 1 1 d . . . . .
H18A H 0.724025 0.031590 0.564656 0.041 Uiso 1 1 calc R U . . .
H18B H 0.694867 0.134005 0.586482 0.041 Uiso 1 1 calc R U . . .
C19 C 0.8492(4) 0.1012(3) 0.5252(3) 0.0492(12) Uani 1 1 d . . . . .
H19A H 0.879125 0.060964 0.482415 0.074 Uiso 1 1 calc R U . . .
H19B H 0.894670 0.087611 0.571250 0.074 Uiso 1 1 calc R U . . .
H19C H 0.851896 0.161531 0.508891 0.074 Uiso 1 1 calc R U . . .
Cl2 Cl 0.23075(10) 0.09333(7) 0.62645(7) 0.0451(3) Uani 1 1 d . . . . .
O11 O 0.5389(2) 0.35233(17) 1.01674(16) 0.0316(7) Uani 1 1 d . . . . .
O12 O 0.3611(2) 0.39202(16) 0.96942(15) 0.0299(6) Uani 1 1 d . . . . .
O13 O 0.5806(2) 0.21355(16) 0.90456(15) 0.0283(6) Uani 1 1 d . . . . .
O14 O 0.3612(3) 0.1983(2) 1.0192(2) 0.0519(9) Uani 1 1 d . . . . .
N5 N 0.2764(3) 0.2551(2) 0.64493(19) 0.0320(8) Uani 1 1 d . . . . .
N6 N 0.4324(3) 0.29680(18) 0.71667(18) 0.0246(7) Uani 1 1 d . . . . .
N7 N 0.5552(3) 0.16751(18) 0.77207(17) 0.0221(7) Uani 1 1 d . . . . .
N8 N 0.4632(3) 0.05882(19) 0.72795(19) 0.0291(8) Uani 1 1 d . . . . .
C20 C 0.3106(3) 0.1695(2) 0.6605(2) 0.0288(9) Uani 1 1 d . . . . .
C21 C 0.3381(4) 0.3135(2) 0.6737(2) 0.0309(10) Uani 1 1 d . . . . .
H21 H 0.312204 0.373301 0.662399 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4079(3) 0.1417(2) 0.7030(2) 0.0227(8) Uani 1 1 d . . . . .
C23 C 0.4640(3) 0.2091(2) 0.7298(2) 0.0213(8) Uani 1 1 d . . . . .
C24 C 0.5480(3) 0.0774(2) 0.7689(2) 0.0263(9) Uani 1 1 d . . . . .
H24 H 0.599319 0.033903 0.793845 0.032 Uiso 1 1 calc R U . . .
C25 C 0.6271(3) 0.2093(2) 0.8254(2) 0.0239(8) Uani 1 1 d . . . . .
H25 H 0.631202 0.269920 0.806768 0.029 Uiso 1 1 calc R U . . .
C26 C 0.7478(3) 0.1561(2) 0.8266(2) 0.0254(9) Uani 1 1 d . . . . .
C27 C 0.8142(4) 0.1459(3) 0.7562(3) 0.0386(11) Uani 1 1 d . . . . .
H27 H 0.783987 0.170235 0.709067 0.046 Uiso 1 1 calc R U . . .
C28 C 0.9253(4) 0.0997(3) 0.7559(3) 0.0476(12) Uani 1 1 d . . . . .
H28 H 0.969434 0.093130 0.708457 0.057 Uiso 1 1 calc R U . . .
C29 C 0.9718(4) 0.0630(3) 0.8259(3) 0.0463(12) Uani 1 1 d . . . . .
H29 H 1.046161 0.030970 0.825433 0.056 Uiso 1 1 calc R U . . .
C30 C 0.9062(4) 0.0747(3) 0.8956(3) 0.0430(11) Uani 1 1 d . . . . .
H30 H 0.937328 0.051780 0.942970 0.052 Uiso 1 1 calc R U . . .
C31 C 0.7929(4) 0.1207(2) 0.8967(3) 0.0337(10) Uani 1 1 d . . . . .
H31 H 0.748666 0.127251 0.944140 0.040 Uiso 1 1 calc R U . . .
C32 C 0.4677(3) 0.2632(2) 0.9163(2) 0.0270(9) Uani 1 1 d . . . . .
H32 H 0.438046 0.285358 0.864870 0.032 Uiso 1 1 calc R U . . .
C33 C 0.4647(3) 0.3411(2) 0.9742(2) 0.0242(8) Uani 1 1 d . . . . .
C34 C 0.3367(4) 0.4665(2) 1.0271(2) 0.0356(10) Uani 1 1 d . . . . .
H34A H 0.398905 0.501082 1.025793 0.043 Uiso 1 1 calc R U . . .
H34B H 0.327768 0.444131 1.080852 0.043 Uiso 1 1 calc R U . . .
C35 C 0.2265(4) 0.5234(3) 1.0025(3) 0.0516(14) Uani 1 1 d . . . . .
H35A H 0.237593 0.546897 0.950126 0.077 Uiso 1 1 calc R U . . .
H35B H 0.205190 0.571774 1.039861 0.077 Uiso 1 1 calc R U . . .
H35C H 0.166623 0.487614 1.001918 0.077 Uiso 1 1 calc R U . . .
C36 C 0.3923(4) 0.1999(3) 0.9525(3) 0.0408(11) Uani 1 1 d . . . . .
O15 O 0.3507(8) 0.1595(6) 0.8901(4) 0.053(3) Uani 0.69(2) 1 d . . P A 1
C37 C 0.2690(10) 0.0975(10) 0.9130(7) 0.109(5) Uani 0.72(2) 1 d D U P A 1
H37A H 0.228247 0.080813 0.867610 0.131 Uiso 0.72(2) 1 calc R U P A 1
H37B H 0.214289 0.122195 0.955111 0.131 Uiso 0.72(2) 1 calc R U P A 1
C58 C 0.3554(15) 0.0209(10) 0.9418(10) 0.072(5) Uani 0.51(2) 1 d D U P A 1
H58A H 0.413968 0.003991 0.900743 0.108 Uiso 0.51(2) 1 calc R U P A 1
H58B H 0.317540 -0.028999 0.954154 0.108 Uiso 0.51(2) 1 calc R U P A 1
H58C H 0.389831 0.038951 0.988804 0.108 Uiso 0.51(2) 1 calc R U P A 1
O0 O 0.417(2) 0.1157(12) 0.9175(10) 0.059(8) Uani 0.31(2) 1 d . . P A 2
C2A C 0.2836(18) 0.0325(16) 0.9128(10) 0.106(7) Uani 0.49(2) 1 d D U P A 2
H2AA H 0.303833 0.037274 0.857154 0.159 Uiso 0.49(2) 1 calc R U P A 2
H2AB H 0.238465 0.087689 0.931327 0.159 Uiso 0.49(2) 1 calc R U P A 2
H2AC H 0.239776 -0.015036 0.920281 0.159 Uiso 0.49(2) 1 calc R U P A 2
C38 C 0.393(3) 0.013(3) 0.960(3) 0.132(16) Uani 0.28(2) 1 d D U P A 2
H38A H 0.447323 -0.039398 0.942388 0.159 Uiso 0.28(2) 1 calc R U P A 2
H38B H 0.380845 0.013770 1.017998 0.159 Uiso 0.28(2) 1 calc R U P A 2
Cl3 Cl 0.95913(9) 0.37471(6) 0.34927(5) 0.0328(3) Uani 1 1 d . . . . .
O6 O 0.5666(2) 0.42455(16) 0.58737(15) 0.0269(6) Uani 1 1 d . . . . .
O7 O 0.6801(2) 0.30071(16) 0.62998(16) 0.0331(7) Uani 1 1 d . . . . .
O8 O 0.7641(2) 0.39382(15) 0.74395(14) 0.0231(6) Uani 1 1 d . . . . .
O9 O 0.5745(2) 0.42068(15) 0.83470(14) 0.0241(6) Uani 1 1 d . . . . .
O10 O 0.4788(2) 0.50947(15) 0.74338(14) 0.0225(6) Uani 1 1 d . . . . .
N9 N 0.9073(3) 0.39973(18) 0.64222(17) 0.0208(7) Uani 1 1 d . . . . .
N10 N 0.9806(3) 0.31298(19) 0.53653(18) 0.0258(7) Uani 1 1 d . . . . .
N11 N 0.8478(3) 0.5145(2) 0.42719(18) 0.0258(7) Uani 1 1 d . . . . .
N12 N 0.8183(3) 0.53140(18) 0.56988(18) 0.0230(7) Uani 1 1 d . . . . .
C39 C 0.9544(3) 0.3856(2) 0.7843(2) 0.0219(8) Uani 1 1 d . . . . .
C40 C 1.0637(3) 0.4072(3) 0.7794(2) 0.0339(10) Uani 1 1 d . . . . .
H40 H 1.084766 0.441526 0.737143 0.041 Uiso 1 1 calc R U . . .
C41 C 1.1421(4) 0.3778(3) 0.8373(3) 0.0425(11) Uani 1 1 d . . . . .
H41 H 1.214888 0.393695 0.834364 0.051 Uiso 1 1 calc R U . . .
C42 C 1.1120(4) 0.3249(3) 0.8992(3) 0.0389(11) Uani 1 1 d . . . . .
H42 H 1.164291 0.305582 0.938240 0.047 Uiso 1 1 calc R U . . .
C43 C 1.0059(4) 0.3013(3) 0.9029(2) 0.0347(10) Uani 1 1 d . . . . .
H43 H 0.986214 0.264901 0.944103 0.042 Uiso 1 1 calc R U . . .
C44 C 0.9265(4) 0.3310(3) 0.8455(2) 0.0309(9) Uani 1 1 d . . . . .
H44 H 0.854196 0.314117 0.848380 0.037 Uiso 1 1 calc R U . . .
C45 C 0.8677(3) 0.4236(2) 0.7244(2) 0.0217(8) Uani 1 1 d . . . . .
H45 H 0.854934 0.488876 0.729355 0.026 Uiso 1 1 calc R U . . .
C46 C 0.9676(3) 0.3190(2) 0.6138(2) 0.0241(8) Uani 1 1 d . . . . .
H46 H 0.996538 0.272664 0.647474 0.029 Uiso 1 1 calc R U . . .
C47 C 0.9244(3) 0.3945(2) 0.5096(2) 0.0212(8) Uani 1 1 d . . . . .
C48 C 0.8786(3) 0.4486(2) 0.5741(2) 0.0209(8) Uani 1 1 d . . . . .
C49 C 0.8069(3) 0.5590(2) 0.4949(2) 0.0256(9) Uani 1 1 d . . . . .
H49 H 0.765737 0.616097 0.488123 0.031 Uiso 1 1 calc R U . . .
C50 C 0.9056(3) 0.4325(2) 0.4354(2) 0.0220(8) Uani 1 1 d . . . . .
C51 C 0.6663(3) 0.4375(2) 0.7056(2) 0.0202(8) Uani 1 1 d . . . . .
H51 H 0.680945 0.495022 0.684538 0.024 Uiso 1 1 calc R U . . .
C52 C 0.5688(3) 0.4530(2) 0.7697(2) 0.0182(8) Uani 1 1 d . . . . .
C53 C 0.3832(3) 0.5301(2) 0.8026(2) 0.0253(8) Uani 1 1 d . . . . .
H53A H 0.403377 0.567886 0.844722 0.030 Uiso 1 1 calc R U . . .
H53B H 0.365114 0.475571 0.826411 0.030 Uiso 1 1 calc R U . . .
C54 C 0.2825(3) 0.5774(3) 0.7594(2) 0.0308(9) Uani 1 1 d . . . . .
H54A H 0.266663 0.540933 0.715773 0.046 Uiso 1 1 calc R U . . .
H54B H 0.299725 0.633131 0.739242 0.046 Uiso 1 1 calc R U . . .
H54C H 0.216542 0.588624 0.795515 0.046 Uiso 1 1 calc R U . . .
C55 C 0.6389(3) 0.3786(2) 0.6371(2) 0.0231(8) Uani 1 1 d . . . . .
C56 C 0.5314(4) 0.3743(3) 0.5206(2) 0.0305(9) Uani 1 1 d . . . . .
H56A H 0.458609 0.404812 0.501901 0.037 Uiso 1 1 calc R U . . .
H56B H 0.520537 0.315454 0.538851 0.037 Uiso 1 1 calc R U . . .
C57 C 0.6199(4) 0.3648(3) 0.4531(2) 0.0404(11) Uani 1 1 d . . . . .
H57A H 0.595567 0.330547 0.410670 0.061 Uiso 1 1 calc R U . . .
H57B H 0.692070 0.334844 0.471620 0.061 Uiso 1 1 calc R U . . .
H57C H 0.628589 0.422904 0.433659 0.061 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 C1 1.734(3) . ?
O1 C6 1.406(4) . ?
O1 C13 1.430(4) . ?
O2 C14 1.312(5) . ?
O2 C15 1.467(4) . ?
O3 C14 1.209(4) . ?
O4 C17 1.203(5) . ?
O5 C17 1.313(5) . ?
O5 C18 1.452(5) . ?
N1 C1 1.321(5) . ?
N1 C2 1.360(5) . ?
N2 C2 1.319(5) . ?
N2 C4 1.329(5) . ?
N3 C3 1.386(5) . ?
N3 C5 1.309(5) . ?
N4 C4 1.365(5) . ?
N4 C5 1.380(4) . ?
N4 C6 1.476(4) . ?
C1 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.507(5) . ?
C7 C8 1.387(5) . ?
C7 C12 1.396(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.530(5) . ?
C13 C17 1.509(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.480(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.493(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cl2 C20 1.718(4) . ?
O11 C33 1.183(5) . ?
O12 C33 1.340(4) . ?
O12 C34 1.472(4) . ?
O13 C25 1.413(4) . ?
O13 C32 1.425(4) . ?
O14 C36 1.165(5) . ?
N5 C20 1.325(5) . ?
N5 C21 1.338(5) . ?
N6 C21 1.337(5) . ?
N6 C23 1.342(4) . ?
N7 C23 1.376(4) . ?
N7 C24 1.385(4) . ?
N7 C25 1.469(5) . ?
N8 C22 1.391(4) . ?
N8 C24 1.303(5) . ?
C20 C22 1.380(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9800 . ?
C25 C26 1.518(5) . ?
C26 C27 1.385(6) . ?
C26 C31 1.381(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.381(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.391(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.372(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.402(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9800 . ?
C32 C33 1.525(5) . ?
C32 C36 1.524(6) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.509(6) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 O15 1.360(7) . ?
C36 O0 1.387(15) . ?
O15 C37 1.494(15) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C58 1.507(9) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
O0 C38 1.78(5) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C2A C38 1.533(10) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
Cl3 C50 1.732(3) . ?
O6 C55 1.329(4) . ?
O6 C56 1.465(4) . ?
O7 C55 1.206(4) . ?
O8 C45 1.401(4) . ?
O8 C51 1.411(4) . ?
O9 C52 1.194(4) . ?
O10 C52 1.339(4) . ?
O10 C53 1.468(4) . ?
N9 C45 1.463(5) . ?
N9 C46 1.386(4) . ?
N9 C48 1.383(4) . ?
N10 C46 1.299(5) . ?
N10 C47 1.388(4) . ?
N11 C49 1.352(5) . ?
N11 C50 1.326(4) . ?
N12 C48 1.341(4) . ?
N12 C49 1.329(5) . ?
C39 C40 1.381(6) . ?
C39 C44 1.383(5) . ?
C39 C45 1.507(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.388(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(6) . ?
C42 H42 0.9300 . ?
C42 C43 1.357(6) . ?
C43 H43 0.9300 . ?
C43 C44 1.392(5) . ?
C44 H44 0.9300 . ?
C45 H45 0.9800 . ?
C46 H46 0.9300 . ?
C47 C48 1.394(5) . ?
C47 C50 1.380(5) . ?
C49 H49 0.9300 . ?
C51 H51 0.9800 . ?
C51 C52 1.533(5) . ?
C51 C55 1.532(5) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C53 C54 1.495(5) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C57 1.501(6) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 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
C6 O1 C13 115.8(3) . . ?
C14 O2 C15 115.6(3) . . ?
C17 O5 C18 116.3(3) . . ?
C1 N1 C2 116.3(3) . . ?
C2 N2 C4 111.7(3) . . ?
C5 N3 C3 103.7(3) . . ?
C4 N4 C5 105.8(3) . . ?
C4 N4 C6 128.6(3) . . ?
C5 N4 C6 125.6(3) . . ?
N1 C1 Cl1 117.2(3) . . ?
N1 C1 C3 121.9(3) . . ?
C3 C1 Cl1 120.8(3) . . ?
N1 C2 H2 115.6 . . ?
N2 C2 N1 128.9(4) . . ?
N2 C2 H2 115.6 . . ?
N3 C3 C4 110.5(3) . . ?
C1 C3 N3 134.4(3) . . ?
C1 C3 C4 115.1(3) . . ?
N2 C4 N4 128.3(3) . . ?
N2 C4 C3 126.1(4) . . ?
N4 C4 C3 105.6(3) . . ?
N3 C5 N4 114.4(3) . . ?
N3 C5 H5 122.8 . . ?
N4 C5 H5 122.8 . . ?
O1 C6 N4 110.2(3) . . ?
O1 C6 H6 108.9 . . ?
O1 C6 C7 108.0(3) . . ?
N4 C6 H6 108.9 . . ?
N4 C6 C7 111.9(3) . . ?
C7 C6 H6 108.9 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 C12 119.1(4) . . ?
C12 C7 C6 119.0(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.7(4) . . ?
C11 C12 H12 120.1 . . ?
O1 C13 H13 109.8 . . ?
O1 C13 C14 109.8(3) . . ?
O1 C13 C17 109.3(3) . . ?
C14 C13 H13 109.8 . . ?
C17 C13 H13 109.8 . . ?
C17 C13 C14 108.4(3) . . ?
O2 C14 C13 111.6(3) . . ?
O3 C14 O2 125.5(3) . . ?
O3 C14 C13 122.8(4) . . ?
O2 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
O2 C15 C16 107.3(3) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O5 125.0(4) . . ?
O4 C17 C13 121.7(4) . . ?
O5 C17 C13 113.3(3) . . ?
O5 C18 H18A 110.4 . . ?
O5 C18 H18B 110.4 . . ?
O5 C18 C19 106.6(3) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C33 O12 C34 115.2(3) . . ?
C25 O13 C32 116.1(3) . . ?
C20 N5 C21 117.4(3) . . ?
C21 N6 C23 111.9(3) . . ?
C23 N7 C24 105.1(3) . . ?
C23 N7 C25 127.5(3) . . ?
C24 N7 C25 125.9(3) . . ?
C24 N8 C22 104.1(3) . . ?
N5 C20 Cl2 118.3(3) . . ?
N5 C20 C22 121.1(4) . . ?
C22 C20 Cl2 120.6(3) . . ?
N5 C21 N6 128.2(3) . . ?
N5 C21 H21 115.9 . . ?
N6 C21 H21 115.9 . . ?
C20 C22 N8 133.8(4) . . ?
C20 C22 C23 115.8(3) . . ?
C23 C22 N8 110.4(3) . . ?
N6 C23 N7 128.2(3) . . ?
N6 C23 C22 125.6(3) . . ?
N7 C23 C22 106.2(3) . . ?
N7 C24 H24 122.9 . . ?
N8 C24 N7 114.3(3) . . ?
N8 C24 H24 122.9 . . ?
O13 C25 N7 110.7(3) . . ?
O13 C25 H25 109.1 . . ?
O13 C25 C26 107.6(3) . . ?
N7 C25 H25 109.1 . . ?
N7 C25 C26 111.0(3) . . ?
C26 C25 H25 109.1 . . ?
C27 C26 C25 118.9(3) . . ?
C31 C26 C25 121.1(4) . . ?
C31 C26 C27 120.0(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.6 . . ?
C30 C29 C28 118.9(4) . . ?
C30 C29 H29 120.6 . . ?
C29 C30 H30 119.5 . . ?
C29 C30 C31 121.1(4) . . ?
C31 C30 H30 119.5 . . ?
C26 C31 C30 119.2(4) . . ?
C26 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
O13 C32 H32 109.8 . . ?
O13 C32 C33 112.0(3) . . ?
O13 C32 C36 107.3(3) . . ?
C33 C32 H32 109.8 . . ?
C36 C32 H32 109.8 . . ?
C36 C32 C33 108.0(3) . . ?
O11 C33 O12 127.0(3) . . ?
O11 C33 C32 126.2(3) . . ?
O12 C33 C32 106.8(3) . . ?
O12 C34 H34A 110.5 . . ?
O12 C34 H34B 110.5 . . ?
O12 C34 C35 106.3(3) . . ?
H34A C34 H34B 108.7 . . ?
C35 C34 H34A 110.5 . . ?
C35 C34 H34B 110.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O14 C36 C32 126.0(4) . . ?
O14 C36 O15 126.4(5) . . ?
O14 C36 O0 113.2(8) . . ?
O15 C36 C32 106.4(4) . . ?
O0 C36 C32 111.5(6) . . ?
C36 O15 C37 114.9(7) . . ?
O15 C37 H37A 112.1 . . ?
O15 C37 H37B 112.1 . . ?
O15 C37 C58 98.1(11) . . ?
H37A C37 H37B 109.8 . . ?
C58 C37 H37A 112.1 . . ?
C58 C37 H37B 112.1 . . ?
C37 C58 H58A 109.5 . . ?
C37 C58 H58B 109.5 . . ?
C37 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C36 O0 C38 127.1(17) . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C38 C2A H2AA 109.5 . . ?
C38 C2A H2AB 109.5 . . ?
C38 C2A H2AC 109.5 . . ?
O0 C38 H38A 115.0 . . ?
O0 C38 H38B 115.0 . . ?
C2A C38 O0 82(2) . . ?
C2A C38 H38A 115.0 . . ?
C2A C38 H38B 115.0 . . ?
H38A C38 H38B 112.0 . . ?
C55 O6 C56 116.3(3) . . ?
C45 O8 C51 116.1(3) . . ?
C52 O10 C53 113.8(3) . . ?
C46 N9 C45 128.1(3) . . ?
C48 N9 C45 127.0(3) . . ?
C48 N9 C46 104.4(3) . . ?
C46 N10 C47 104.1(3) . . ?
C50 N11 C49 116.9(3) . . ?
C49 N12 C48 112.0(3) . . ?
C40 C39 C44 118.9(3) . . ?
C40 C39 C45 119.6(3) . . ?
C44 C39 C45 121.5(3) . . ?
C39 C40 H40 119.8 . . ?
C39 C40 C41 120.3(4) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.1(4) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.8(4) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.7 . . ?
C42 C43 C44 120.5(4) . . ?
C44 C43 H43 119.7 . . ?
C39 C44 C43 120.3(4) . . ?
C39 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
O8 C45 N9 111.5(3) . . ?
O8 C45 C39 108.1(3) . . ?
O8 C45 H45 108.3 . . ?
N9 C45 C39 112.3(3) . . ?
N9 C45 H45 108.3 . . ?
C39 C45 H45 108.3 . . ?
N9 C46 H46 122.5 . . ?
N10 C46 N9 114.9(3) . . ?
N10 C46 H46 122.5 . . ?
N10 C47 C48 110.2(3) . . ?
C50 C47 N10 134.7(3) . . ?
C50 C47 C48 115.1(3) . . ?
N9 C48 C47 106.4(3) . . ?
N12 C48 N9 127.5(3) . . ?
N12 C48 C47 126.2(3) . . ?
N11 C49 H49 116.0 . . ?
N12 C49 N11 128.1(3) . . ?
N12 C49 H49 116.0 . . ?
N11 C50 Cl3 117.5(3) . . ?
N11 C50 C47 121.7(3) . . ?
C47 C50 Cl3 120.7(3) . . ?
O8 C51 H51 109.8 . . ?
O8 C51 C52 106.2(3) . . ?
O8 C51 C55 109.2(3) . . ?
C52 C51 H51 109.8 . . ?
C55 C51 H51 109.8 . . ?
C55 C51 C52 111.9(3) . . ?
O9 C52 O10 125.2(3) . . ?
O9 C52 C51 124.2(3) . . ?
O10 C52 C51 110.6(3) . . ?
O10 C53 H53A 110.3 . . ?
O10 C53 H53B 110.3 . . ?
O10 C53 C54 106.9(3) . . ?
H53A C53 H53B 108.6 . . ?
C54 C53 H53A 110.3 . . ?
C54 C53 H53B 110.3 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O6 C55 C51 111.4(3) . . ?
O7 C55 O6 125.5(3) . . ?
O7 C55 C51 123.1(3) . . ?
O6 C56 H56A 109.4 . . ?
O6 C56 H56B 109.4 . . ?
O6 C56 C57 111.2(3) . . ?
H56A C56 H56B 108.0 . . ?
C57 C56 H56A 109.4 . . ?
C57 C56 H56B 109.4 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 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
Cl1 C1 C3 N3 -0.1(6) . . . . ?
Cl1 C1 C3 C4 -178.3(3) . . . . ?
O1 C6 C7 C8 -150.1(3) . . . . ?
O1 C6 C7 C12 31.8(4) . . . . ?
O1 C13 C14 O2 127.4(3) . . . . ?
O1 C13 C14 O3 -50.7(5) . . . . ?
O1 C13 C17 O4 161.0(3) . . . . ?
O1 C13 C17 O5 -20.5(4) . . . . ?
N1 C1 C3 N3 179.9(4) . . . . ?
N1 C1 C3 C4 1.7(5) . . . . ?
N3 C3 C4 N2 179.5(3) . . . . ?
N3 C3 C4 N4 -0.2(4) . . . . ?
N4 C6 C7 C8 -28.6(5) . . . . ?
N4 C6 C7 C12 153.3(3) . . . . ?
C1 N1 C2 N2 0.2(6) . . . . ?
C1 C3 C4 N2 -1.9(5) . . . . ?
C1 C3 C4 N4 178.4(3) . . . . ?
C2 N1 C1 Cl1 179.0(3) . . . . ?
C2 N1 C1 C3 -1.0(6) . . . . ?
C2 N2 C4 N4 -179.3(4) . . . . ?
C2 N2 C4 C3 1.1(5) . . . . ?
C3 N3 C5 N4 -0.2(4) . . . . ?
C4 N2 C2 N1 -0.2(6) . . . . ?
C4 N4 C5 N3 0.1(4) . . . . ?
C4 N4 C6 O1 -122.4(4) . . . . ?
C4 N4 C6 C7 117.4(4) . . . . ?
C5 N3 C3 C1 -178.0(4) . . . . ?
C5 N3 C3 C4 0.2(4) . . . . ?
C5 N4 C4 N2 -179.6(4) . . . . ?
C5 N4 C4 C3 0.1(4) . . . . ?
C5 N4 C6 O1 59.0(4) . . . . ?
C5 N4 C6 C7 -61.3(4) . . . . ?
C6 O1 C13 C14 -83.3(3) . . . . ?
C6 O1 C13 C17 158.0(3) . . . . ?
C6 N4 C4 N2 1.6(6) . . . . ?
C6 N4 C4 C3 -178.8(3) . . . . ?
C6 N4 C5 N3 178.9(3) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C6 C7 C12 C11 178.2(3) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C7 0.5(6) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
C13 O1 C6 N4 78.0(3) . . . . ?
C13 O1 C6 C7 -159.4(3) . . . . ?
C14 O2 C15 C16 171.9(4) . . . . ?
C14 C13 C17 O4 41.4(5) . . . . ?
C14 C13 C17 O5 -140.1(3) . . . . ?
C15 O2 C14 O3 -0.5(6) . . . . ?
C15 O2 C14 C13 -178.5(3) . . . . ?
C17 O5 C18 C19 -176.6(3) . . . . ?
C17 C13 C14 O2 -113.4(4) . . . . ?
C17 C13 C14 O3 68.6(5) . . . . ?
C18 O5 C17 O4 -0.8(5) . . . . ?
C18 O5 C17 C13 -179.4(3) . . . . ?
Cl2 C20 C22 N8 -0.2(6) . . . . ?
Cl2 C20 C22 C23 -178.1(3) . . . . ?
O13 C25 C26 C27 -177.0(3) . . . . ?
O13 C25 C26 C31 0.9(5) . . . . ?
O13 C32 C33 O11 -13.3(5) . . . . ?
O13 C32 C33 O12 168.8(3) . . . . ?
O13 C32 C36 O14 103.6(5) . . . . ?
O13 C32 C36 O15 -88.4(6) . . . . ?
O13 C32 C36 O0 -40.4(14) . . . . ?
O14 C36 O15 C37 -9.0(13) . . . . ?
O14 C36 O0 C38 7(3) . . . . ?
N5 C20 C22 N8 179.8(4) . . . . ?
N5 C20 C22 C23 1.9(5) . . . . ?
N7 C25 C26 C27 61.7(5) . . . . ?
N7 C25 C26 C31 -120.5(4) . . . . ?
N8 C22 C23 N6 -179.4(3) . . . . ?
N8 C22 C23 N7 -0.1(4) . . . . ?
C20 N5 C21 N6 0.5(6) . . . . ?
C20 C22 C23 N6 -1.1(5) . . . . ?
C20 C22 C23 N7 178.2(3) . . . . ?
C21 N5 C20 Cl2 178.3(3) . . . . ?
C21 N5 C20 C22 -1.6(6) . . . . ?
C21 N6 C23 N7 -179.2(3) . . . . ?
C21 N6 C23 C22 0.0(5) . . . . ?
C22 N8 C24 N7 -1.2(4) . . . . ?
C23 N6 C21 N5 0.4(6) . . . . ?
C23 N7 C24 N8 1.1(4) . . . . ?
C23 N7 C25 O13 89.8(4) . . . . ?
C23 N7 C25 C26 -150.7(3) . . . . ?
C24 N7 C23 N6 178.8(3) . . . . ?
C24 N7 C23 C22 -0.5(4) . . . . ?
C24 N7 C25 O13 -73.8(4) . . . . ?
C24 N7 C25 C26 45.7(5) . . . . ?
C24 N8 C22 C20 -177.2(4) . . . . ?
C24 N8 C22 C23 0.8(4) . . . . ?
C25 O13 C32 C33 -120.0(3) . . . . ?
C25 O13 C32 C36 121.6(3) . . . . ?
C25 N7 C23 N6 12.4(6) . . . . ?
C25 N7 C23 C22 -166.9(3) . . . . ?
C25 N7 C24 N8 167.8(3) . . . . ?
C25 C26 C27 C28 178.4(4) . . . . ?
C25 C26 C31 C30 -177.7(4) . . . . ?
C26 C27 C28 C29 0.0(7) . . . . ?
C27 C26 C31 C30 0.1(6) . . . . ?
C27 C28 C29 C30 -1.1(7) . . . . ?
C28 C29 C30 C31 1.8(7) . . . . ?
C29 C30 C31 C26 -1.2(6) . . . . ?
C31 C26 C27 C28 0.6(6) . . . . ?
C32 O13 C25 N7 -60.0(4) . . . . ?
C32 O13 C25 C26 178.5(3) . . . . ?
C32 C36 O15 C37 -177.0(8) . . . . ?
C32 C36 O0 C38 155.6(18) . . . . ?
C33 O12 C34 C35 170.6(3) . . . . ?
C33 C32 C36 O14 -17.2(6) . . . . ?
C33 C32 C36 O15 150.8(6) . . . . ?
C33 C32 C36 O0 -161.3(13) . . . . ?
C34 O12 C33 O11 -3.8(5) . . . . ?
C34 O12 C33 C32 174.1(3) . . . . ?
C36 C32 C33 O11 104.6(5) . . . . ?
C36 C32 C33 O12 -73.3(4) . . . . ?
C36 O15 C37 C58 -75.1(13) . . . . ?
C36 O0 C38 C2A 96(3) . . . . ?
O8 C51 C52 O9 -10.4(5) . . . . ?
O8 C51 C52 O10 167.7(3) . . . . ?
O8 C51 C55 O6 -164.6(3) . . . . ?
O8 C51 C55 O7 14.4(5) . . . . ?
N10 C47 C48 N9 0.2(4) . . . . ?
N10 C47 C48 N12 -179.5(3) . . . . ?
N10 C47 C50 Cl3 -0.4(6) . . . . ?
N10 C47 C50 N11 -179.4(4) . . . . ?
C39 C40 C41 C42 1.5(7) . . . . ?
C40 C39 C44 C43 2.5(6) . . . . ?
C40 C39 C45 O8 -178.3(3) . . . . ?
C40 C39 C45 N9 58.3(4) . . . . ?
C40 C41 C42 C43 0.5(7) . . . . ?
C41 C42 C43 C44 -1.0(7) . . . . ?
C42 C43 C44 C39 -0.5(6) . . . . ?
C44 C39 C40 C41 -3.0(6) . . . . ?
C44 C39 C45 O8 0.2(4) . . . . ?
C44 C39 C45 N9 -123.2(4) . . . . ?
C45 O8 C51 C52 -137.5(3) . . . . ?
C45 O8 C51 C55 101.7(3) . . . . ?
C45 N9 C46 N10 172.7(3) . . . . ?
C45 N9 C48 N12 7.2(6) . . . . ?
C45 N9 C48 C47 -172.5(3) . . . . ?
C45 C39 C40 C41 175.6(4) . . . . ?
C45 C39 C44 C43 -176.1(3) . . . . ?
C46 N9 C45 O8 -82.3(4) . . . . ?
C46 N9 C45 C39 39.2(5) . . . . ?
C46 N9 C48 N12 179.1(4) . . . . ?
C46 N9 C48 C47 -0.6(4) . . . . ?
C46 N10 C47 C48 0.4(4) . . . . ?
C46 N10 C47 C50 179.7(4) . . . . ?
C47 N10 C46 N9 -0.8(4) . . . . ?
C48 N9 C45 O8 87.7(4) . . . . ?
C48 N9 C45 C39 -150.8(3) . . . . ?
C48 N9 C46 N10 0.9(4) . . . . ?
C48 N12 C49 N11 0.0(6) . . . . ?
C48 C47 C50 Cl3 178.8(3) . . . . ?
C48 C47 C50 N11 -0.1(5) . . . . ?
C49 N11 C50 Cl3 -179.7(3) . . . . ?
C49 N11 C50 C47 -0.7(5) . . . . ?
C49 N12 C48 N9 179.5(4) . . . . ?
C49 N12 C48 C47 -0.9(5) . . . . ?
C50 N11 C49 N12 0.8(6) . . . . ?
C50 C47 C48 N9 -179.3(3) . . . . ?
C50 C47 C48 N12 1.0(6) . . . . ?
C51 O8 C45 N9 -69.4(3) . . . . ?
C51 O8 C45 C39 166.7(3) . . . . ?
C52 O10 C53 C54 -168.5(3) . . . . ?
C52 C51 C55 O6 78.1(4) . . . . ?
C52 C51 C55 O7 -102.9(4) . . . . ?
C53 O10 C52 O9 0.1(5) . . . . ?
C53 O10 C52 C51 -178.0(3) . . . . ?
C55 O6 C56 C57 -82.3(4) . . . . ?
C55 C51 C52 O9 108.6(4) . . . . ?
C55 C51 C52 O10 -73.2(3) . . . . ?
C56 O6 C55 O7 2.8(6) . . . . ?
C56 O6 C55 C51 -178.2(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 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.591
####################################################################### 
# 
# 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_sjw-20200721
_database_code_depnum_ccdc_archive 'CCDC 2018328'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Cl2 N3 O5'
_chemical_formula_sum            'C20 H19 Cl2 N3 O5'
_chemical_formula_weight         452.28
_chemical_absolute_configuration unk
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   14.9392(5)
_cell_length_b                   15.2205(4)
_cell_length_c                   19.0810(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4338.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6146
_cell_measurement_temperature    295.28(11)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      4.1110
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    3.011
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20770
_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    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.13
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13129
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.536
_diffrn_reflns_theta_min         3.715
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.28(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  25.00   1.00    1.00    --  -35.62  71.00  46.00   30
  2  ω   -102.00 -57.00   1.00    1.00    --  -35.62-150.00  44.00   45
  3  ω     69.00 130.00   1.00    3.39    --  107.12 -71.00 -84.00   61
  4  ω     62.00  88.00   1.00    3.39    --  107.12 -50.00  76.00   26
  5  ω    119.00 145.00   1.00    3.39    --  107.12  71.00  46.00   26
  6  ω    117.00 161.00   1.00    3.39    --  107.12  50.00-137.00   44
  7  ω     40.00 115.00   1.00    3.39    --  107.12-123.00-153.00   75
  8  ω   -103.00 -43.00   1.00    1.00    --  -35.62 -57.00  90.00   60
  9  ω    -60.00 -35.00   1.00    1.00    --  -35.62-178.00 -90.00   25
 10  ω   -108.00 -77.00   1.00    1.00    --  -35.62-178.00 -90.00   31
 11  ω     10.00  74.00   1.00    1.00    --   35.62 -99.00 -90.00   64
 12  ω    101.00 175.00   1.00    3.39    --  107.12 111.00-120.00   74
 13  ω     38.00 109.00   1.00    3.39    --  107.12 -95.00  60.00   71
 14  ω     78.00 110.00   1.00    3.39    --  107.12 -95.00-120.00   32
;
_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      -0.0392784000
_diffrn_orient_matrix_UB_12      0.0534796000
_diffrn_orient_matrix_UB_13      -0.0614124000
_diffrn_orient_matrix_UB_21      -0.0948599000
_diffrn_orient_matrix_UB_22      -0.0302646000
_diffrn_orient_matrix_UB_23      0.0204616000
_diffrn_orient_matrix_UB_31      -0.0096841000
_diffrn_orient_matrix_UB_32      0.0804180000
_diffrn_orient_matrix_UB_33      0.0482634000
_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         0.632
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                6247
_reflns_number_total             7494
_reflns_odcompleteness_completeness 99.63
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 1918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7494
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.034
_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)+(0.1556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2268
_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. Restrained distances
 C16-C17
 1.51 with sigma of 0.02
 C36-C37
 1.5 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C34(H34), C14(H14), C7(H7), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C39(H39A,H39B), C16(H16A,H16B), C36(H36A,H36B)
3.c Me refined with riding coordinates:
 C17(H17A,H17B,H17C)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C25(H25), C6(H6), C23(H23), C22(H22), C5(H5), C29(H29), C13(H13),
 C12(H12), C10(H10), C11(H11), C30(H30), C31(H31), C32(H32)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C40(H40A,H40B,H40C), C37(H37A,H37B,H37C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl4 Cl -0.61380(8) -0.12848(6) -0.59751(6) 0.0815(3) Uani 1 1 d . . . . .
Cl3 Cl -0.62888(9) -0.30037(8) -0.68954(4) 0.0826(3) Uani 1 1 d . . . . .
Cl1 Cl -0.34266(8) -0.30429(7) -0.49080(4) 0.0772(3) Uani 1 1 d . . . . .
Cl2 Cl -0.36350(10) -0.12945(6) -0.40246(7) 0.0905(3) Uani 1 1 d . . . . .
O3 O -0.36377(14) -0.54672(13) -0.30548(10) 0.0457(5) Uani 1 1 d . . . . .
O6 O -0.62053(14) -0.54693(12) -0.50808(9) 0.0452(5) Uani 1 1 d . . . . .
O5 O -0.26722(16) -0.67096(17) -0.23370(11) 0.0590(6) Uani 1 1 d . . . . .
O7 O -0.72614(18) -0.67100(17) -0.43607(13) 0.0651(7) Uani 1 1 d . . . . .
N4 N -0.62877(17) -0.48538(17) -0.39561(11) 0.0454(6) Uani 1 1 d . . . . .
O2 O -0.3904(2) -0.64334(19) -0.41896(12) 0.0748(8) Uani 1 1 d . . . . .
N1 N -0.34942(19) -0.48140(18) -0.19413(11) 0.0510(6) Uani 1 1 d . . . . .
O10 O -0.6125(3) -0.76724(17) -0.55380(15) 0.0826(10) Uani 1 1 d . . . . .
O8 O -0.5977(2) -0.7181(2) -0.39014(15) 0.0892(9) Uani 1 1 d . . . . .
O1 O -0.3904(3) -0.76425(17) -0.35242(14) 0.0793(9) Uani 1 1 d . . . . .
C26 C -0.6121(2) -0.3063(2) -0.60062(15) 0.0521(7) Uani 1 1 d . . . . .
O9 O -0.6135(3) -0.6487(2) -0.61990(13) 0.0937(12) Uani 1 1 d . . . . .
N5 N -0.5825(2) -0.5106(2) -0.33701(13) 0.0672(8) Uani 1 1 d . . . . .
O4 O -0.3962(2) -0.7237(2) -0.19321(15) 0.0971(9) Uani 1 1 d . . . . .
C34 C -0.5914(2) -0.63375(19) -0.49592(14) 0.0464(7) Uani 1 1 d . . . . .
H34 H -0.526864 -0.632752 -0.486820 0.056 Uiso 1 1 calc R U . . .
C3 C -0.3613(2) -0.3067(2) -0.40195(15) 0.0490(7) Uani 1 1 d . . . . .
C2 C -0.3686(2) -0.38927(19) -0.36878(14) 0.0457(7) Uani 1 1 d . . . . .
H2 H -0.363712 -0.440882 -0.394588 0.055 Uiso 1 1 calc R U . . .
C8 C -0.2614(2) -0.4647(2) -0.17883(15) 0.0547(8) Uani 1 1 d . . . . .
C14 C -0.3998(2) -0.6307(2) -0.29349(14) 0.0470(7) Uani 1 1 d . . . . .
H14 H -0.463543 -0.624112 -0.282410 0.056 Uiso 1 1 calc R U . . .
C24 C -0.59343(19) -0.39496(18) -0.49696(13) 0.0423(6) Uani 1 1 d . . . . .
C1 C -0.38315(19) -0.39214(19) -0.29722(13) 0.0437(6) Uani 1 1 d . . . . .
C7 C -0.3958(2) -0.4799(2) -0.26186(13) 0.0458(7) Uani 1 1 d . . . . .
H7 H -0.459836 -0.489220 -0.253826 0.055 Uiso 1 1 calc R U . . .
C38 C -0.6378(2) -0.6798(2) -0.43484(16) 0.0538(8) Uani 1 1 d . . . . .
C27 C -0.58370(19) -0.48366(19) -0.46230(14) 0.0435(6) Uani 1 1 d . . . . .
H27 H -0.520015 -0.496314 -0.455253 0.052 Uiso 1 1 calc R U . . .
C25 C -0.6058(2) -0.3886(2) -0.56930(14) 0.0486(7) Uani 1 1 d . . . . .
H25 H -0.609790 -0.439210 -0.596449 0.058 Uiso 1 1 calc R U . . .
C6 C -0.3924(2) -0.3146(2) -0.25974(15) 0.0533(8) Uani 1 1 d . . . . .
H6 H -0.404228 -0.316868 -0.211921 0.064 Uiso 1 1 calc R U . . .
C28 C -0.7168(2) -0.4679(2) -0.37891(15) 0.0484(7) Uani 1 1 d . . . . .
C15 C -0.3917(2) -0.6796(2) -0.36286(16) 0.0547(8) Uani 1 1 d . . . . .
N6 N -0.6362(3) -0.5094(2) -0.28426(14) 0.0813(11) Uani 1 1 d . . . . .
C20 C -0.3554(2) -0.6812(2) -0.23417(15) 0.0529(8) Uani 1 1 d . . . . .
C23 C -0.5863(2) -0.3187(2) -0.45730(16) 0.0529(8) Uani 1 1 d . . . . .
H23 H -0.577316 -0.322775 -0.409177 0.063 Uiso 1 1 calc R U . . .
C22 C -0.5924(2) -0.2371(2) -0.48825(18) 0.0566(8) Uani 1 1 d . . . . .
H22 H -0.587765 -0.186428 -0.461282 0.068 Uiso 1 1 calc R U . . .
C33 C -0.7195(3) -0.4834(3) -0.30662(17) 0.0679(10) Uani 1 1 d . . . . .
C9 C -0.2572(3) -0.4834(3) -0.10708(18) 0.0770(12) Uani 1 1 d . . . . .
N2 N -0.3944(3) -0.5079(3) -0.13579(15) 0.0836(11) Uani 1 1 d . . . . .
C5 C -0.3845(2) -0.2347(2) -0.29211(18) 0.0575(8) Uani 1 1 d . . . . .
H5 H -0.389082 -0.183167 -0.266200 0.069 Uiso 1 1 calc R U . . .
C35 C -0.6080(3) -0.6837(2) -0.56426(16) 0.0574(8) Uani 1 1 d . . . . .
C21 C -0.6055(2) -0.2314(2) -0.56047(19) 0.0554(8) Uani 1 1 d . . . . .
C4 C -0.3696(2) -0.2312(2) -0.36351(19) 0.0542(8) Uani 1 1 d . . . . .
N3 N -0.3388(4) -0.5092(3) -0.08369(16) 0.1017(15) Uani 1 1 d . . . . .
C29 C -0.7897(2) -0.4416(3) -0.4182(2) 0.0674(10) Uani 1 1 d . . . . .
H29 H -0.785756 -0.430931 -0.466068 0.081 Uiso 1 1 calc R U . . .
C13 C -0.1899(2) -0.4365(3) -0.2180(2) 0.0671(10) Uani 1 1 d . . . . .
H13 H -0.194916 -0.423632 -0.265445 0.081 Uiso 1 1 calc R U . . .
C18 C -0.2209(3) -0.7152(3) -0.1768(2) 0.0787(12) Uani 1 1 d . . . . .
H18A H -0.231969 -0.777881 -0.179025 0.094 Uiso 1 1 calc R U . . .
H18B H -0.242449 -0.693542 -0.132086 0.094 Uiso 1 1 calc R U . . .
C39 C -0.7747(3) -0.7137(3) -0.3783(2) 0.0821(12) Uani 1 1 d . . . . .
H39A H -0.763846 -0.776573 -0.378983 0.098 Uiso 1 1 calc R U . . .
H39B H -0.754287 -0.690729 -0.333651 0.098 Uiso 1 1 calc R U . . .
C12 C -0.1093(3) -0.4283(4) -0.1817(3) 0.0959(16) Uani 1 1 d . . . . .
H12 H -0.058491 -0.410324 -0.205938 0.115 Uiso 1 1 calc R U . . .
C19 C -0.1251(3) -0.6978(4) -0.1835(3) 0.0951(15) Uani 1 1 d . . . . .
H19A H -0.104321 -0.719292 -0.227939 0.143 Uiso 1 1 calc R U . . .
H19B H -0.093541 -0.727083 -0.146451 0.143 Uiso 1 1 calc R U . . .
H19C H -0.114612 -0.635717 -0.180602 0.143 Uiso 1 1 calc R U . . .
C40 C -0.8680(4) -0.6965(4) -0.3870(3) 0.1072(17) Uani 1 1 d . . . . .
H40A H -0.888902 -0.724408 -0.429042 0.161 Uiso 1 1 calc R U . . .
H40B H -0.877515 -0.634268 -0.390305 0.161 Uiso 1 1 calc R U . . .
H40C H -0.900342 -0.719261 -0.347477 0.161 Uiso 1 1 calc R U . . .
C10 C -0.1745(4) -0.4731(3) -0.0720(2) 0.1040(14) Uani 1 1 d . . . . .
H10 H -0.169241 -0.484166 -0.024262 0.125 Uiso 1 1 calc R U . . .
C11 C -0.1025(4) -0.4462(3) -0.1108(3) 0.1053(14) Uani 1 1 d . . . . .
H11 H -0.047352 -0.439668 -0.088865 0.126 Uiso 1 1 calc R U . . .
C16 C -0.3904(6) -0.8180(3) -0.4152(3) 0.117(2) Uani 1 1 d D . . . .
H16A H -0.448788 -0.815220 -0.437345 0.141 Uiso 1 1 calc R U . . .
H16B H -0.346508 -0.795541 -0.448066 0.141 Uiso 1 1 calc R U . . .
C36 C -0.6304(5) -0.8212(3) -0.6158(3) 0.119(2) Uani 1 1 d D . . . .
H36A H -0.686747 -0.803964 -0.636988 0.142 Uiso 1 1 calc R U . . .
H36B H -0.583205 -0.813352 -0.650153 0.142 Uiso 1 1 calc R U . . .
C17 C -0.3704(9) -0.9041(4) -0.3990(5) 0.194(5) Uani 1 1 d D . . . .
H17A H -0.370713 -0.938787 -0.441000 0.291 Uiso 1 1 calc R U . . .
H17B H -0.312310 -0.906954 -0.377640 0.291 Uiso 1 1 calc R U . . .
H17C H -0.414410 -0.926598 -0.366939 0.291 Uiso 1 1 calc R U . . .
C37 C -0.6342(9) -0.9083(3) -0.5948(5) 0.219(5) Uani 1 1 d D . . . .
H37A H -0.621891 -0.945704 -0.634193 0.329 Uiso 1 1 calc R U . . .
H37B H -0.692915 -0.921045 -0.577000 0.329 Uiso 1 1 calc R U . . .
H37C H -0.590609 -0.918526 -0.558826 0.329 Uiso 1 1 calc R U . . .
C30 C -0.8685(3) -0.4322(4) -0.3817(4) 0.1035(18) Uani 1 1 d . . . . .
H30 H -0.920210 -0.415965 -0.405455 0.124 Uiso 1 1 calc R U . . .
C31 C -0.8721(3) -0.4467(4) -0.3086(3) 0.1165(17) Uani 1 1 d . . . . .
H31 H -0.926070 -0.437316 -0.285565 0.140 Uiso 1 1 calc R U . . .
C32 C -0.8016(4) -0.4733(3) -0.2711(2) 0.1060(15) Uani 1 1 d . . . . .
H32 H -0.806505 -0.484709 -0.223327 0.127 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
Cl4 C21 1.724(3) . ?
Cl3 C26 1.717(3) . ?
Cl1 C3 1.718(3) . ?
Cl2 C4 1.720(3) . ?
O3 C14 1.405(4) . ?
O3 C7 1.399(3) . ?
O6 C34 1.410(3) . ?
O6 C27 1.412(3) . ?
O5 C20 1.326(4) . ?
O5 C18 1.453(4) . ?
O7 C38 1.327(4) . ?
O7 C39 1.472(5) . ?
N4 N5 1.370(3) . ?
N4 C27 1.440(3) . ?
N4 C28 1.379(4) . ?
O2 C15 1.204(4) . ?
N1 C8 1.371(4) . ?
N1 C7 1.466(3) . ?
N1 N2 1.362(4) . ?
O10 C35 1.289(4) . ?
O10 C36 1.465(6) . ?
O8 C38 1.194(4) . ?
O1 C15 1.304(4) . ?
O1 C16 1.451(5) . ?
C26 C25 1.392(4) . ?
C26 C21 1.376(5) . ?
O9 C35 1.191(4) . ?
N5 N6 1.288(5) . ?
O4 C20 1.184(4) . ?
C34 H34 0.9800 . ?
C34 C38 1.526(4) . ?
C34 C35 1.530(4) . ?
C3 C2 1.411(4) . ?
C3 C4 1.370(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.383(4) . ?
C8 C9 1.400(4) . ?
C8 C13 1.372(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.524(4) . ?
C14 C20 1.521(4) . ?
C24 C27 1.510(4) . ?
C24 C25 1.396(4) . ?
C24 C23 1.390(4) . ?
C1 C7 1.508(4) . ?
C1 C6 1.387(4) . ?
C7 H7 0.9800 . ?
C27 H27 0.9800 . ?
C25 H25 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.368(5) . ?
C28 C33 1.400(4) . ?
C28 C29 1.381(5) . ?
N6 C33 1.373(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.378(5) . ?
C22 H22 0.9300 . ?
C22 C21 1.395(5) . ?
C33 C32 1.410(6) . ?
C9 N3 1.356(7) . ?
C9 C10 1.414(7) . ?
N2 N3 1.295(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.375(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.395(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.460(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.428(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.383(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.369(8) . ?
C11 H11 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.379(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.386(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C30 H30 0.9300 . ?
C30 C31 1.412(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.337(8) . ?
C32 H32 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
C7 O3 C14 115.7(2) . . ?
C34 O6 C27 114.7(2) . . ?
C20 O5 C18 115.1(3) . . ?
C38 O7 C39 115.6(3) . . ?
N5 N4 C27 119.4(3) . . ?
N5 N4 C28 110.3(2) . . ?
C28 N4 C27 130.3(2) . . ?
C8 N1 C7 129.6(2) . . ?
N2 N1 C8 110.8(3) . . ?
N2 N1 C7 119.5(3) . . ?
C35 O10 C36 116.0(3) . . ?
C15 O1 C16 115.6(3) . . ?
C25 C26 Cl3 118.8(2) . . ?
C21 C26 Cl3 121.2(3) . . ?
C21 C26 C25 120.1(3) . . ?
N6 N5 N4 108.6(3) . . ?
O6 C34 H34 108.6 . . ?
O6 C34 C38 114.6(3) . . ?
O6 C34 C35 106.0(2) . . ?
C38 C34 H34 108.6 . . ?
C38 C34 C35 110.4(3) . . ?
C35 C34 H34 108.6 . . ?
C2 C3 Cl1 118.3(2) . . ?
C4 C3 Cl1 121.6(2) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
N1 C8 C9 102.3(3) . . ?
N1 C8 C13 133.5(3) . . ?
C13 C8 C9 124.1(4) . . ?
O3 C14 H14 108.4 . . ?
O3 C14 C15 105.8(2) . . ?
O3 C14 C20 114.4(2) . . ?
C15 C14 H14 108.4 . . ?
C20 C14 H14 108.4 . . ?
C20 C14 C15 111.4(3) . . ?
C25 C24 C27 120.5(2) . . ?
C23 C24 C27 120.1(2) . . ?
C23 C24 C25 119.4(3) . . ?
C2 C1 C7 119.3(3) . . ?
C2 C1 C6 119.8(3) . . ?
C6 C1 C7 120.7(2) . . ?
O3 C7 N1 110.6(2) . . ?
O3 C7 C1 109.6(2) . . ?
O3 C7 H7 108.7 . . ?
N1 C7 C1 110.5(2) . . ?
N1 C7 H7 108.7 . . ?
C1 C7 H7 108.7 . . ?
O7 C38 C34 113.0(3) . . ?
O8 C38 O7 124.1(3) . . ?
O8 C38 C34 122.8(3) . . ?
O6 C27 N4 110.6(2) . . ?
O6 C27 C24 107.5(2) . . ?
O6 C27 H27 109.2 . . ?
N4 C27 C24 111.0(2) . . ?
N4 C27 H27 109.2 . . ?
C24 C27 H27 109.2 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
N4 C28 C33 102.9(3) . . ?
N4 C28 C29 133.0(3) . . ?
C29 C28 C33 124.1(3) . . ?
O2 C15 O1 126.0(3) . . ?
O2 C15 C14 123.3(3) . . ?
O1 C15 C14 110.6(3) . . ?
N5 N6 C33 109.0(3) . . ?
O5 C20 C14 112.3(3) . . ?
O4 C20 O5 124.8(3) . . ?
O4 C20 C14 122.9(3) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 C24 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C23 C22 H22 120.4 . . ?
C23 C22 C21 119.3(3) . . ?
C21 C22 H22 120.4 . . ?
C28 C33 C32 118.8(4) . . ?
N6 C33 C28 109.2(3) . . ?
N6 C33 C32 132.0(4) . . ?
C8 C9 C10 118.6(4) . . ?
N3 C9 C8 109.9(4) . . ?
N3 C9 C10 131.5(4) . . ?
N3 N2 N1 108.4(4) . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
O10 C35 C34 111.5(3) . . ?
O9 C35 O10 125.2(3) . . ?
O9 C35 C34 123.2(3) . . ?
C26 C21 Cl4 121.3(3) . . ?
C26 C21 C22 120.6(3) . . ?
C22 C21 Cl4 118.1(3) . . ?
C3 C4 Cl2 121.3(3) . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 Cl2 118.0(3) . . ?
N2 N3 C9 108.6(3) . . ?
C28 C29 H29 122.3 . . ?
C30 C29 C28 115.5(4) . . ?
C30 C29 H29 122.3 . . ?
C8 C13 H13 122.3 . . ?
C8 C13 C12 115.5(4) . . ?
C12 C13 H13 122.3 . . ?
O5 C18 H18A 110.0 . . ?
O5 C18 H18B 110.0 . . ?
O5 C18 C19 108.5(4) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
O7 C39 H39A 110.1 . . ?
O7 C39 H39B 110.1 . . ?
H39A C39 H39B 108.4 . . ?
C40 C39 O7 108.2(4) . . ?
C40 C39 H39A 110.1 . . ?
C40 C39 H39B 110.1 . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 122.0(5) . . ?
C11 C12 H12 119.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.6(4) . . ?
C11 C10 H10 121.2 . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 122.0(5) . . ?
C10 C11 H11 119.0 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 O1 110.5(5) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
O10 C36 H36A 110.1 . . ?
O10 C36 H36B 110.1 . . ?
H36A C36 H36B 108.4 . . ?
C37 C36 O10 108.1(5) . . ?
C37 C36 H36A 110.1 . . ?
C37 C36 H36B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C29 C30 H30 119.5 . . ?
C29 C30 C31 121.1(5) . . ?
C31 C30 H30 119.5 . . ?
C30 C31 H31 118.4 . . ?
C32 C31 C30 123.1(5) . . ?
C32 C31 H31 118.4 . . ?
C33 C32 H32 121.3 . . ?
C31 C32 C33 117.4(4) . . ?
C31 C32 H32 121.3 . . ?

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
Cl3 C26 C25 C24 -179.1(2) . . . . ?
Cl3 C26 C21 Cl4 0.1(4) . . . . ?
Cl3 C26 C21 C22 179.7(3) . . . . ?
Cl1 C3 C2 C1 179.7(2) . . . . ?
Cl1 C3 C4 Cl2 1.0(4) . . . . ?
Cl1 C3 C4 C5 -180.0(3) . . . . ?
O3 C14 C15 O2 -26.9(5) . . . . ?
O3 C14 C15 O1 155.9(3) . . . . ?
O3 C14 C20 O5 -40.2(4) . . . . ?
O3 C14 C20 O4 139.0(3) . . . . ?
O6 C34 C38 O7 47.3(4) . . . . ?
O6 C34 C38 O8 -131.3(3) . . . . ?
O6 C34 C35 O10 -158.6(3) . . . . ?
O6 C34 C35 O9 23.2(5) . . . . ?
N4 N5 N6 C33 0.0(4) . . . . ?
N4 C28 C33 N6 -0.6(4) . . . . ?
N4 C28 C33 C32 -178.8(4) . . . . ?
N4 C28 C29 C30 179.0(4) . . . . ?
N1 C8 C9 N3 -0.1(4) . . . . ?
N1 C8 C9 C10 -179.8(4) . . . . ?
N1 C8 C13 C12 -179.4(4) . . . . ?
N1 N2 N3 C9 0.1(5) . . . . ?
N5 N4 C27 O6 114.5(3) . . . . ?
N5 N4 C27 C24 -126.2(3) . . . . ?
N5 N4 C28 C33 0.6(4) . . . . ?
N5 N4 C28 C29 -179.3(4) . . . . ?
N5 N6 C33 C28 0.3(5) . . . . ?
N5 N6 C33 C32 178.3(5) . . . . ?
C34 O6 C27 N4 -78.8(3) . . . . ?
C34 O6 C27 C24 159.8(2) . . . . ?
C3 C2 C1 C7 176.9(3) . . . . ?
C3 C2 C1 C6 1.6(4) . . . . ?
C2 C3 C4 Cl2 -178.5(2) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C1 C7 O3 17.8(4) . . . . ?
C2 C1 C7 N1 139.9(3) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
C8 N1 C7 O3 66.3(4) . . . . ?
C8 N1 C7 C1 -55.2(4) . . . . ?
C8 N1 N2 N3 -0.2(5) . . . . ?
C8 C9 N3 N2 0.0(5) . . . . ?
C8 C9 C10 C11 -0.8(7) . . . . ?
C8 C13 C12 C11 -1.0(7) . . . . ?
C14 O3 C7 N1 81.2(3) . . . . ?
C14 O3 C7 C1 -156.8(2) . . . . ?
C24 C23 C22 C21 -0.2(5) . . . . ?
C1 C6 C5 C4 1.9(5) . . . . ?
C7 O3 C14 C15 154.4(2) . . . . ?
C7 O3 C14 C20 -82.7(3) . . . . ?
C7 N1 C8 C9 -175.5(3) . . . . ?
C7 N1 C8 C13 4.8(6) . . . . ?
C7 N1 N2 N3 176.0(3) . . . . ?
C7 C1 C6 C5 -177.5(3) . . . . ?
C38 O7 C39 C40 179.0(4) . . . . ?
C38 C34 C35 O10 -34.0(4) . . . . ?
C38 C34 C35 O9 147.9(4) . . . . ?
C27 O6 C34 C38 79.1(3) . . . . ?
C27 O6 C34 C35 -158.8(2) . . . . ?
C27 N4 N5 N6 -178.3(3) . . . . ?
C27 N4 C28 C33 178.2(3) . . . . ?
C27 N4 C28 C29 -1.7(6) . . . . ?
C27 C24 C25 C26 -178.2(3) . . . . ?
C27 C24 C23 C22 178.1(3) . . . . ?
C25 C26 C21 Cl4 -179.6(3) . . . . ?
C25 C26 C21 C22 0.0(5) . . . . ?
C25 C24 C27 O6 -20.6(4) . . . . ?
C25 C24 C27 N4 -141.7(3) . . . . ?
C25 C24 C23 C22 0.8(5) . . . . ?
C6 C1 C7 O3 -166.8(3) . . . . ?
C6 C1 C7 N1 -44.8(4) . . . . ?
C6 C5 C4 Cl2 178.0(3) . . . . ?
C6 C5 C4 C3 -1.0(5) . . . . ?
C28 N4 N5 N6 -0.4(4) . . . . ?
C28 N4 C27 O6 -63.0(4) . . . . ?
C28 N4 C27 C24 56.3(4) . . . . ?
C28 C33 C32 C31 -1.9(7) . . . . ?
C28 C29 C30 C31 1.5(7) . . . . ?
C15 O1 C16 C17 167.5(7) . . . . ?
C15 C14 C20 O5 79.7(3) . . . . ?
C15 C14 C20 O4 -101.1(4) . . . . ?
N6 C33 C32 C31 -179.7(5) . . . . ?
C20 O5 C18 C19 179.9(4) . . . . ?
C20 C14 C15 O2 -151.8(4) . . . . ?
C20 C14 C15 O1 31.0(4) . . . . ?
C23 C24 C27 O6 162.1(3) . . . . ?
C23 C24 C27 N4 41.0(4) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C23 C22 C21 Cl4 179.4(3) . . . . ?
C23 C22 C21 C26 -0.2(5) . . . . ?
C33 C28 C29 C30 -0.9(6) . . . . ?
C9 C8 C13 C12 1.0(6) . . . . ?
C9 C10 C11 C12 0.8(8) . . . . ?
N2 N1 C8 C9 0.2(4) . . . . ?
N2 N1 C8 C13 -179.5(4) . . . . ?
N2 N1 C7 O3 -109.1(3) . . . . ?
N2 N1 C7 C1 129.4(3) . . . . ?
C35 O10 C36 C37 -179.1(7) . . . . ?
C35 C34 C38 O7 -72.3(4) . . . . ?
C35 C34 C38 O8 109.1(4) . . . . ?
C21 C26 C25 C24 0.5(5) . . . . ?
C4 C3 C2 C1 -0.7(5) . . . . ?
N3 C9 C10 C11 179.6(5) . . . . ?
C29 C28 C33 N6 179.4(4) . . . . ?
C29 C28 C33 C32 1.1(6) . . . . ?
C29 C30 C31 C32 -2.6(9) . . . . ?
C13 C8 C9 N3 179.6(4) . . . . ?
C13 C8 C9 C10 -0.1(6) . . . . ?
C13 C12 C11 C10 0.1(8) . . . . ?
C18 O5 C20 O4 -1.2(5) . . . . ?
C18 O5 C20 C14 178.0(3) . . . . ?
C39 O7 C38 O8 -1.2(5) . . . . ?
C39 O7 C38 C34 -179.8(3) . . . . ?
C10 C9 N3 N2 179.6(5) . . . . ?
C16 O1 C15 O2 -2.1(7) . . . . ?
C16 O1 C15 C14 175.0(4) . . . . ?
C36 O10 C35 O9 -3.3(7) . . . . ?
C36 O10 C35 C34 178.6(4) . . . . ?
C30 C31 C32 C33 2.7(9) . . . . ?

_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 3.140
_oxdiff_exptl_absorpt_empirical_full_min 0.497
####################################################################### 
# 
# 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_sjw-20200804
_database_code_depnum_ccdc_archive 'CCDC 2027379'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-07
_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         'C20 H20 F N3 O5'
_chemical_formula_sum            'C20 H20 F N3 O5'
_chemical_formula_weight         401.39
_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'
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                   9.5126(2)
_cell_length_b                   21.7936(4)
_cell_length_c                   9.7318(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.480(2)
_cell_angle_gamma                90
_cell_volume                     2008.32(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4416
_cell_measurement_temperature    295.75(10)
_cell_measurement_theta_max      71.2660
_cell_measurement_theta_min      4.6200
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61623
_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    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8495
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.424
_diffrn_reflns_theta_min         4.057
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00 -11.00   1.00    1.00    --  -35.62  28.00 141.00   44
  2  ω   -101.00 -55.00   1.00    1.00    --  -35.62 -28.00 -20.00   46
  3  ω    -12.00  13.00   1.00    1.00    --   35.62 -28.00 -20.00   25
  4  ω     77.00 106.00   1.00    1.00    --   35.62  28.00 141.00   29
  5  ω    101.00 127.00   1.00    1.50    --  107.12  28.00 141.00   26
  6  ω     40.00 122.00   1.00    1.50    --  107.12 -28.00 -20.00   82
  7  ω    -51.00  32.00   1.00    1.00    --  -35.62  57.00 150.00   83
  8  ω   -107.00 -35.00   1.00    1.00    --  -35.62-178.00 -90.00   72
  9  ω   -108.00 -39.00   1.00    1.00    --  -35.62 178.00-180.00   69
 10  ω     83.00 108.00   1.00    1.00    --   35.62 178.00  90.00   25
 11  ω     64.00 106.00   1.00    1.00    --   35.62 178.00   0.00   42
 12  ω     90.00 137.00   1.00    1.50    --  107.12  61.00 150.00   47
 13  ω     43.00  68.00   1.00    1.50    --  107.12 -77.00-180.00   25
 14  ω     38.00  87.00   1.00    1.50    --  107.12 -95.00 -90.00   49
 15  ω     62.00 124.00   1.00    1.50    --  107.12 -61.00  30.00   62
 16  ω    146.00 174.00   1.00    1.50    --  107.12  61.00 150.00   28
 17  ω     56.00 125.00   1.00    1.50    --  107.12 -45.00-120.00   69
 18  ω     79.00 105.00   1.00    1.50    --  107.12 -77.00-180.00   26
 19  ω     45.00 105.00   1.00    1.50    --  107.12 -77.00   0.00   60
 20  ω     67.00 111.00   1.00    1.50    --  107.12-111.00 -30.00   44
;
_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      -0.1529442000
_diffrn_orient_matrix_UB_12      0.0138049000
_diffrn_orient_matrix_UB_13      -0.0584699000
_diffrn_orient_matrix_UB_21      0.0534413000
_diffrn_orient_matrix_UB_22      0.0213068000
_diffrn_orient_matrix_UB_23      -0.1367272000
_diffrn_orient_matrix_UB_31      -0.0147759000
_diffrn_orient_matrix_UB_32      -0.0659789000
_diffrn_orient_matrix_UB_33      -0.0563448000
_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                3138
_reflns_number_total             3811
_reflns_odcompleteness_completeness 99.68
_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         0.355
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.105
_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)+(0.0737P)²+0.4407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1492
_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 Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_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 0.96048(16) 0.35189(8) 0.4135(2) 0.0973(7) Uani 1 1 d . . . . .
O2 O 0.54063(13) 0.37364(5) 0.25287(13) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.34188(19) 0.39953(8) 0.05520(19) 0.0699(5) Uani 1 1 d . . . . .
O4 O 0.20833(15) 0.32124(7) 0.11634(15) 0.0470(4) Uani 1 1 d . . . . .
O5 O 0.3576(2) 0.25012(6) 0.37614(19) 0.0644(5) Uani 1 1 d . . . . .
O6 O 0.34220(14) 0.34967(6) 0.43356(13) 0.0398(3) Uani 1 1 d . . . . .
N1 N 0.67522(16) 0.34527(6) 0.45848(15) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.68104(19) 0.28745(7) 0.51142(19) 0.0475(4) Uani 1 1 d . . . . .
N3 N 0.6723(2) 0.29080(9) 0.6439(2) 0.0563(5) Uani 1 1 d . . . . .
C1 C 0.66134(18) 0.38728(8) 0.56071(18) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.6469(2) 0.45096(9) 0.5627(2) 0.0427(5) Uani 1 1 d . . . . .
H2 H 0.648771 0.474465 0.483136 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6297(3) 0.47705(12) 0.6882(2) 0.0566(6) Uani 1 1 d . . . . .
H3 H 0.619689 0.519401 0.693807 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6266(3) 0.44197(15) 0.8079(2) 0.0671(7) Uani 1 1 d . . . . .
H4 H 0.614222 0.461552 0.890769 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6415(3) 0.37938(15) 0.8065(2) 0.0659(7) Uani 1 1 d . . . . .
H5 H 0.639820 0.356243 0.886657 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6593(2) 0.35174(10) 0.6793(2) 0.0452(5) Uani 1 1 d . . . . .
C7 C 0.67470(19) 0.35386(8) 0.30994(18) 0.0325(4) Uani 1 1 d . . . . .
H7 H 0.697729 0.314846 0.267288 0.039 Uiso 1 1 calc R U . . .
C8 C 0.78029(19) 0.40222(8) 0.27520(18) 0.0336(4) Uani 1 1 d . . . . .
C9 C 0.7435(2) 0.45001(9) 0.18544(19) 0.0406(4) Uani 1 1 d . . . . .
H9 H 0.650540 0.453658 0.146931 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8429(2) 0.49250(10) 0.1521(2) 0.0515(5) Uani 1 1 d . . . . .
H10 H 0.816236 0.524172 0.091047 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9800(3) 0.48833(11) 0.2080(2) 0.0558(6) Uani 1 1 d . . . . .
H11 H 1.045966 0.517289 0.185733 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0201(2) 0.44115(13) 0.2973(3) 0.0643(7) Uani 1 1 d . . . . .
H12 H 1.113038 0.437759 0.335833 0.077 Uiso 1 1 calc R U . . .
C13 C 0.9200(2) 0.39911(10) 0.3285(2) 0.0522(6) Uani 1 1 d . . . . .
C14 C 0.43811(19) 0.32701(8) 0.22480(18) 0.0343(4) Uani 1 1 d . . . . .
H14 H 0.482115 0.292444 0.180794 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3251(2) 0.35464(9) 0.1218(2) 0.0395(4) Uani 1 1 d . . . . .
C16 C 0.0958(3) 0.33876(13) 0.0120(3) 0.0671(7) Uani 1 1 d . . . . .
H16A H 0.128309 0.335720 -0.079205 0.080 Uiso 1 1 calc R U . . .
H16B H 0.067372 0.380828 0.026584 0.080 Uiso 1 1 calc R U . . .
C17 C -0.0237(3) 0.29728(15) 0.0232(5) 0.1109(15) Uani 1 1 d . . . . .
H17A H -0.100900 0.309267 -0.041967 0.166 Uiso 1 1 calc R U . . .
H17B H -0.052520 0.299337 0.114992 0.166 Uiso 1 1 calc R U . . .
H17C H 0.004113 0.256055 0.004012 0.166 Uiso 1 1 calc R U . . .
C18 C 0.3746(2) 0.30370(8) 0.3530(2) 0.0373(4) Uani 1 1 d . . . . .
C19 C 0.2879(2) 0.33268(10) 0.5635(2) 0.0496(5) Uani 1 1 d . . . . .
H19A H 0.356104 0.307325 0.617864 0.060 Uiso 1 1 calc R U . . .
H19B H 0.200903 0.309590 0.545707 0.060 Uiso 1 1 calc R U . . .
C20 C 0.2616(3) 0.39025(12) 0.6395(2) 0.0650(7) Uani 1 1 d . . . . .
H20A H 0.188846 0.413568 0.587997 0.098 Uiso 1 1 calc R U . . .
H20B H 0.346761 0.414068 0.651099 0.098 Uiso 1 1 calc R U . . .
H20C H 0.232069 0.380218 0.728423 0.098 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 C13 1.353(2) . ?
O2 C7 1.409(2) . ?
O2 C14 1.417(2) . ?
O3 C15 1.193(2) . ?
O4 C15 1.325(2) . ?
O4 C16 1.454(3) . ?
O5 C18 1.203(2) . ?
O6 C18 1.326(2) . ?
O6 C19 1.458(2) . ?
N1 N2 1.3605(19) . ?
N1 C1 1.368(2) . ?
N1 C7 1.457(2) . ?
N2 N3 1.301(3) . ?
N3 C6 1.381(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.391(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.516(2) . ?
C8 C9 1.383(3) . ?
C8 C13 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.522(3) . ?
C14 C18 1.524(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.464(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.490(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C7 O2 C14 115.91(13) . . ?
C15 O4 C16 116.25(17) . . ?
C18 O6 C19 116.24(15) . . ?
N2 N1 C1 110.36(15) . . ?
N2 N1 C7 119.39(15) . . ?
C1 N1 C7 130.11(14) . . ?
N3 N2 N1 108.59(16) . . ?
N2 N3 C6 108.47(16) . . ?
N1 C1 C2 133.83(17) . . ?
N1 C1 C6 103.92(16) . . ?
C6 C1 C2 122.22(18) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 C1 116.4(2) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
N3 C6 C1 108.66(18) . . ?
N3 C6 C5 130.9(2) . . ?
C1 C6 C5 120.4(2) . . ?
O2 C7 N1 110.33(14) . . ?
O2 C7 H7 109.2 . . ?
O2 C7 C8 107.06(13) . . ?
N1 C7 H7 109.2 . . ?
N1 C7 C8 111.77(14) . . ?
C8 C7 H7 109.2 . . ?
C9 C8 C7 122.08(17) . . ?
C13 C8 C7 121.09(16) . . ?
C13 C8 C9 116.78(17) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.95(19) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
F1 C13 C8 118.30(18) . . ?
F1 C13 C12 118.6(2) . . ?
C12 C13 C8 123.1(2) . . ?
O2 C14 H14 108.7 . . ?
O2 C14 C15 105.85(14) . . ?
O2 C14 C18 113.62(14) . . ?
C15 C14 H14 108.7 . . ?
C15 C14 C18 111.11(15) . . ?
C18 C14 H14 108.7 . . ?
O3 C15 O4 125.73(19) . . ?
O3 C15 C14 124.02(18) . . ?
O4 C15 C14 110.24(16) . . ?
O4 C16 H16A 110.1 . . ?
O4 C16 H16B 110.1 . . ?
O4 C16 C17 108.1(2) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 O6 125.42(18) . . ?
O5 C18 C14 123.20(18) . . ?
O6 C18 C14 111.38(14) . . ?
O6 C19 H19A 110.1 . . ?
O6 C19 H19B 110.1 . . ?
O6 C19 C20 107.88(17) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O2 C7 C8 C9 -8.8(2) . . . . ?
O2 C7 C8 C13 173.61(18) . . . . ?
O2 C14 C15 O3 17.2(3) . . . . ?
O2 C14 C15 O4 -163.72(15) . . . . ?
O2 C14 C18 O5 -135.1(2) . . . . ?
O2 C14 C18 O6 44.6(2) . . . . ?
N1 N2 N3 C6 0.5(2) . . . . ?
N1 C1 C2 C3 177.4(2) . . . . ?
N1 C1 C6 N3 0.2(2) . . . . ?
N1 C1 C6 C5 -177.9(2) . . . . ?
N1 C7 C8 C9 -129.75(18) . . . . ?
N1 C7 C8 C13 52.7(2) . . . . ?
N2 N1 C1 C2 -177.9(2) . . . . ?
N2 N1 C1 C6 0.1(2) . . . . ?
N2 N1 C7 O2 108.90(17) . . . . ?
N2 N1 C7 C8 -132.10(17) . . . . ?
N2 N3 C6 C1 -0.4(2) . . . . ?
N2 N3 C6 C5 177.4(2) . . . . ?
C1 N1 N2 N3 -0.4(2) . . . . ?
C1 N1 C7 O2 -66.3(2) . . . . ?
C1 N1 C7 C8 52.7(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 N3 178.50(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 N3 -177.7(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 O2 C14 C15 -160.77(14) . . . . ?
C7 O2 C14 C18 77.04(18) . . . . ?
C7 N1 N2 N3 -176.47(17) . . . . ?
C7 N1 C1 C2 -2.4(3) . . . . ?
C7 N1 C1 C6 175.64(18) . . . . ?
C7 C8 C9 C10 -177.96(18) . . . . ?
C7 C8 C13 F1 -0.4(3) . . . . ?
C7 C8 C13 C12 178.5(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C8 C13 F1 -178.1(2) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 F1 178.3(2) . . . . ?
C11 C12 C13 C8 -0.6(4) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C14 O2 C7 N1 -82.12(17) . . . . ?
C14 O2 C7 C8 156.05(14) . . . . ?
C15 O4 C16 C17 -179.4(2) . . . . ?
C15 C14 C18 O5 105.7(2) . . . . ?
C15 C14 C18 O6 -74.64(19) . . . . ?
C16 O4 C15 O3 5.0(3) . . . . ?
C16 O4 C15 C14 -174.10(18) . . . . ?
C18 O6 C19 C20 178.68(19) . . . . ?
C18 C14 C15 O3 141.0(2) . . . . ?
C18 C14 C15 O4 -39.9(2) . . . . ?
C19 O6 C18 O5 3.0(3) . . . . ?
C19 O6 C18 C14 -176.62(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.881
_oxdiff_exptl_absorpt_empirical_full_min 0.591
####################################################################### 
# 
# 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_sjw-20200720
_database_code_depnum_ccdc_archive 'CCDC 2018329'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N3 O5'
_chemical_formula_sum            'C22 H25 N3 O5'
_chemical_formula_weight         411.45
_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                   9.5779(5)
_cell_length_b                   11.3128(7)
_cell_length_c                   11.8490(8)
_cell_angle_alpha                61.499(7)
_cell_angle_beta                 78.529(5)
_cell_angle_gamma                86.047(5)
_cell_volume                     1105.24(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5472
_cell_measurement_temperature    290(4)
_cell_measurement_theta_max      71.2380
_cell_measurement_theta_min      4.7180
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64926
_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    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.13
_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  0.0193
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.479
_diffrn_reflns_theta_min         4.324
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_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    -77.00  17.00   1.00    1.00    --  -35.62 103.00  58.00   94
  2  ω     37.00 111.00   1.00    1.00    --  107.12-103.00 -43.00   74
  3  ω    101.00 177.00   1.00    1.00    --  107.12 103.00  58.00   76
  4  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00 -60.00   73
  5  ω     17.00 105.00   1.00    1.00    --   35.62  38.00 -60.00   88
  6  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
  7  ω    -34.00  55.00   1.00    1.00    --   35.62 -38.00  60.00   89
  8  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-180.00   94
  9  ω    -36.00  65.00   1.00    1.00    --   35.62 -19.00 -60.00  101
 10  ω      5.00  77.00   1.00    1.00    --   35.62-103.00 -43.00   72
 11  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 120.00   95
 12  ω     37.00 113.00   1.00    1.00    --  107.12-111.00 -90.00   76
 13  ω     39.00 125.00   1.00    1.00    --  107.12 -45.00   0.00   86
 14  ω     90.00 176.00   1.00    1.00    --  107.12  45.00  90.00   86
 15  ω     39.00 125.00   1.00    1.00    --  107.12 -45.00 -90.00   86
 16  ω     40.00 124.00   1.00    1.00    --  107.12 -45.00  90.00   84
 17  ω     73.00 108.00   1.00    1.00    --  107.12 -95.00 -60.00   35
 18  ω     98.00 175.00   1.00    1.00    --  107.12  45.00  30.00   77
 19  ω     40.00  90.00   1.00    1.00    --  107.12 -45.00-180.00   50
 20  ω     55.00 110.00   1.00    1.00    --  107.12 -95.00 120.00   55
 21  ω     58.00 110.00   1.00    1.00    --  107.12 -95.00  30.00   52
 22  ω     94.00 120.00   1.00    1.00    --  107.12 -77.00 120.00   26
 23  ω    111.00 138.00   1.00    1.00    --  107.12  61.00-150.00   27
 24  ω     98.00 165.00   1.00    1.00    --  107.12  61.00 -30.00   67
;
_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      0.0091164000
_diffrn_orient_matrix_UB_12      -0.0463813000
_diffrn_orient_matrix_UB_13      0.1434416000
_diffrn_orient_matrix_UB_21      0.0397333000
_diffrn_orient_matrix_UB_22      -0.1415854000
_diffrn_orient_matrix_UB_23      0.0184222000
_diffrn_orient_matrix_UB_31      0.1590578000
_diffrn_orient_matrix_UB_32      0.0428522000
_diffrn_orient_matrix_UB_33      -0.0422708000
_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                3715
_reflns_number_total             4210
_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 1.171.40.53 (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         0.440
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.048(3)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1102P)²+0.3499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.1923
_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. Restrained distances
 C19-C20
 1.55 with sigma of 0.02
3. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C19 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_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 0.47041(15) 0.24173(12) 0.24569(12) 0.0453(4) Uani 1 1 d . . . . .
O2 O 0.62459(19) 0.12050(19) 0.12524(19) 0.0734(5) Uani 1 1 d . . . . .
O3 O 0.4481(2) -0.03031(17) 0.19451(18) 0.0736(5) Uani 1 1 d . . . . .
O4 O 0.21338(17) 0.12502(16) 0.27947(16) 0.0656(5) Uani 1 1 d . . . . .
O5 O 0.2599(2) -0.03667(18) 0.47141(18) 0.0852(6) Uani 1 1 d . . . . .
N1 N 0.37294(17) 0.26768(15) 0.43087(15) 0.0454(4) Uani 1 1 d . . . . .
N2 N 0.3793(2) 0.18161(19) 0.55812(17) 0.0600(5) Uani 1 1 d . . . . .
N3 N 0.2543(2) 0.1724(2) 0.62937(19) 0.0698(6) Uani 1 1 d . . . . .
C1 C 0.2379(2) 0.31449(19) 0.42150(19) 0.0464(5) Uani 1 1 d . . . . .
C2 C 0.1722(2) 0.4016(2) 0.3178(2) 0.0565(5) Uani 1 1 d . . . . .
H2 H 0.222870 0.443633 0.232231 0.068 Uiso 1 1 calc R U . . .
C3 C 0.0285(3) 0.4232(3) 0.3472(3) 0.0680(7) Uani 1 1 d . . . . .
C4 C -0.0485(3) 0.3579(3) 0.4782(3) 0.0710(7) Uani 1 1 d . . . . .
C5 C 0.0181(3) 0.2754(3) 0.5775(3) 0.0717(7) Uani 1 1 d . . . . .
H5 H -0.031866 0.234626 0.663274 0.086 Uiso 1 1 calc R U . . .
C6 C 0.1636(2) 0.2520(2) 0.5493(2) 0.0570(5) Uani 1 1 d . . . . .
C7 C 0.49776(19) 0.28900(17) 0.33030(18) 0.0426(4) Uani 1 1 d . . . . .
H7 H 0.577006 0.239582 0.372062 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5420(2) 0.43672(18) 0.2461(2) 0.0466(5) Uani 1 1 d . . . . .
C9 C 0.6088(3) 0.4841(2) 0.1173(2) 0.0608(6) Uani 1 1 d . . . . .
H9 H 0.623730 0.425836 0.081491 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6536(3) 0.6175(3) 0.0412(3) 0.0800(8) Uani 1 1 d . . . . .
H10 H 0.697940 0.648613 -0.045717 0.096 Uiso 1 1 calc R U . . .
C11 C 0.6330(4) 0.7039(3) 0.0932(3) 0.0856(9) Uani 1 1 d . . . . .
H11 H 0.663296 0.793588 0.041725 0.103 Uiso 1 1 calc R U . . .
C12 C 0.5674(3) 0.6581(3) 0.2218(4) 0.0823(9) Uani 1 1 d . . . . .
H12 H 0.553522 0.716786 0.257083 0.099 Uiso 1 1 calc R U . . .
C13 C 0.5215(3) 0.5236(2) 0.2992(3) 0.0614(6) Uani 1 1 d . . . . .
H13 H 0.477409 0.492489 0.386173 0.074 Uiso 1 1 calc R U . . .
C14 C 0.4524(2) 0.09958(18) 0.30410(19) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.509014 0.057175 0.373161 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2979(3) 0.0529(2) 0.3631(2) 0.0582(6) Uani 1 1 d . . . . .
C16 C 0.0619(3) 0.0927(3) 0.3240(3) 0.0851(8) Uani 1 1 d . . . . .
H16A H 0.023897 0.119764 0.390134 0.102 Uiso 1 1 calc R U . . .
H16B H 0.044980 -0.003479 0.361854 0.102 Uiso 1 1 calc R U . . .
C17 C -0.0078(4) 0.1651(6) 0.2109(4) 0.1343(17) Uani 1 1 d . . . . .
H17A H 0.027012 0.134264 0.147926 0.201 Uiso 1 1 calc R U . . .
H17B H 0.012991 0.259789 0.171847 0.201 Uiso 1 1 calc R U . . .
H17C H -0.108929 0.148574 0.238658 0.201 Uiso 1 1 calc R U . . .
C18 C 0.5063(2) 0.0556(2) 0.2009(2) 0.0536(5) Uani 1 1 d . . . . .
C19 C 0.6893(4) 0.0806(5) 0.0281(4) 0.1253(14) Uani 1 1 d D U . . .
H19A H 0.725970 -0.009151 0.071027 0.150 Uiso 1 1 calc R U . . .
H19B H 0.617953 0.078039 -0.018456 0.150 Uiso 1 1 calc R U . . .
C20 C 0.7960(6) 0.1668(7) -0.0572(5) 0.1633(18) Uani 1 1 d D U . . .
H20A H 0.829935 0.144733 -0.126609 0.245 Uiso 1 1 calc R U . . .
H20B H 0.872445 0.160304 -0.013154 0.245 Uiso 1 1 calc R U . . .
H20C H 0.762047 0.256867 -0.092922 0.245 Uiso 1 1 calc R U . . .
C21 C -0.0464(4) 0.5155(4) 0.2377(4) 0.1018(11) Uani 1 1 d . . . . .
H21A H 0.021595 0.555686 0.157124 0.153 Uiso 1 1 calc R U . . .
H21B H -0.091335 0.584750 0.255712 0.153 Uiso 1 1 calc R U . . .
H21C H -0.117343 0.464872 0.230316 0.153 Uiso 1 1 calc R U . . .
C22 C -0.2072(3) 0.3807(4) 0.5073(5) 0.1068(12) Uani 1 1 d . . . . .
H22A H -0.222500 0.475228 0.474893 0.160 Uiso 1 1 calc R U . . .
H22B H -0.241577 0.333991 0.600105 0.160 Uiso 1 1 calc R U . . .
H22C H -0.257437 0.347253 0.465410 0.160 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 C7 1.412(2) . ?
O1 C14 1.423(2) . ?
O2 C18 1.307(3) . ?
O2 C19 1.445(3) . ?
O3 C18 1.193(3) . ?
O4 C15 1.327(3) . ?
O4 C16 1.450(3) . ?
O5 C15 1.195(3) . ?
N1 N2 1.361(2) . ?
N1 C1 1.369(2) . ?
N1 C7 1.451(2) . ?
N2 N3 1.299(3) . ?
N3 C6 1.367(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 C4 1.423(4) . ?
C3 C21 1.504(4) . ?
C4 C5 1.353(4) . ?
C4 C22 1.522(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.519(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.517(3) . ?
C14 C18 1.517(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.464(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.343(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C7 O1 C14 114.65(14) . . ?
C18 O2 C19 115.7(2) . . ?
C15 O4 C16 116.94(19) . . ?
N2 N1 C1 109.74(16) . . ?
N2 N1 C7 119.32(15) . . ?
C1 N1 C7 130.81(16) . . ?
N3 N2 N1 108.67(17) . . ?
N2 N3 C6 108.62(18) . . ?
N1 C1 C2 134.13(19) . . ?
N1 C1 C6 104.06(18) . . ?
C6 C1 C2 121.8(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 C21 118.9(3) . . ?
C4 C3 C21 120.1(3) . . ?
C3 C4 C22 119.9(3) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 C22 119.5(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
N3 C6 C1 108.92(19) . . ?
N3 C6 C5 131.0(2) . . ?
C1 C6 C5 120.1(2) . . ?
O1 C7 N1 110.46(15) . . ?
O1 C7 H7 109.0 . . ?
O1 C7 C8 107.01(14) . . ?
N1 C7 H7 109.0 . . ?
N1 C7 C8 112.42(14) . . ?
C8 C7 H7 109.0 . . ?
C9 C8 C7 120.10(17) . . ?
C9 C8 C13 119.4(2) . . ?
C13 C8 C7 120.39(19) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.7(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O1 C14 H14 108.8 . . ?
O1 C14 C15 112.37(16) . . ?
O1 C14 C18 108.92(15) . . ?
C15 C14 H14 108.8 . . ?
C15 C14 C18 109.05(17) . . ?
C18 C14 H14 108.8 . . ?
O4 C15 C14 110.97(17) . . ?
O5 C15 O4 125.6(2) . . ?
O5 C15 C14 123.4(2) . . ?
O4 C16 H16A 110.1 . . ?
O4 C16 H16B 110.1 . . ?
O4 C16 C17 107.9(3) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 C14 111.32(17) . . ?
O3 C18 O2 125.7(2) . . ?
O3 C18 C14 123.0(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 O2 110.9(4) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 -28.8(2) . . . . ?
O1 C7 C8 C13 154.15(17) . . . . ?
O1 C14 C15 O4 48.4(2) . . . . ?
O1 C14 C15 O5 -131.1(2) . . . . ?
O1 C14 C18 O2 41.2(2) . . . . ?
O1 C14 C18 O3 -140.8(2) . . . . ?
N1 N2 N3 C6 0.4(3) . . . . ?
N1 C1 C2 C3 178.7(2) . . . . ?
N1 C1 C6 N3 0.4(2) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
N1 C7 C8 C9 -150.20(18) . . . . ?
N1 C7 C8 C13 32.7(2) . . . . ?
N2 N1 C1 C2 -179.3(2) . . . . ?
N2 N1 C1 C6 -0.1(2) . . . . ?
N2 N1 C7 O1 115.33(18) . . . . ?
N2 N1 C7 C8 -125.22(18) . . . . ?
N2 N3 C6 C1 -0.5(3) . . . . ?
N2 N3 C6 C5 178.9(2) . . . . ?
C1 N1 N2 N3 -0.2(2) . . . . ?
C1 N1 C7 O1 -60.0(2) . . . . ?
C1 N1 C7 C8 59.5(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 C21 -179.4(2) . . . . ?
C2 C1 C6 N3 179.66(19) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C2 C3 C4 C22 -178.5(2) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 N3 -178.5(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 O1 C14 C15 90.81(19) . . . . ?
C7 O1 C14 C18 -148.25(16) . . . . ?
C7 N1 N2 N3 -176.44(18) . . . . ?
C7 N1 C1 C2 -3.6(4) . . . . ?
C7 N1 C1 C6 175.54(18) . . . . ?
C7 C8 C9 C10 -177.9(2) . . . . ?
C7 C8 C13 C12 177.7(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C14 O1 C7 N1 -68.09(19) . . . . ?
C14 O1 C7 C8 169.24(15) . . . . ?
C15 O4 C16 C17 -169.6(3) . . . . ?
C15 C14 C18 O2 164.16(18) . . . . ?
C15 C14 C18 O3 -17.9(3) . . . . ?
C16 O4 C15 O5 0.4(4) . . . . ?
C16 O4 C15 C14 -179.0(2) . . . . ?
C18 O2 C19 C20 170.0(4) . . . . ?
C18 C14 C15 O4 -72.5(2) . . . . ?
C18 C14 C15 O5 108.1(3) . . . . ?
C19 O2 C18 O3 -1.3(4) . . . . ?
C19 O2 C18 C14 176.6(3) . . . . ?
C21 C3 C4 C5 -179.6(3) . . . . ?
C21 C3 C4 C22 0.4(4) . . . . ?
C22 C4 C5 C6 178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_hn02
_database_code_depnum_ccdc_archive 'CCDC 2038626'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
Olex2 1.3-alpha
(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         'C22 H23 Cl N2 O5'
_chemical_formula_sum            'C22 H23 Cl N2 O5'
_chemical_formula_weight         430.87
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.756(4)
_cell_length_b                   14.590(3)
_cell_length_c                   9.628(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.67(2)
_cell_angle_gamma                90
_cell_volume                     2150.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      24.5750
_cell_measurement_theta_min      2.6390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81848
_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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.1431
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.586
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(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    -31.00  18.00   1.00    5.00    --   11.90   0.00   0.00   49
  2  ω      3.00  31.00   1.00    5.00    --  -11.27-106.00 -67.00   28
  3  ω    -52.00 -12.00   1.00    5.00    --  -11.27 106.00  31.00   40
  4  ω    -50.00  25.00   1.00    5.00    --   11.90 -37.00 150.00   75
;
_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      0.0426231000
_diffrn_orient_matrix_UB_12      -0.0145610000
_diffrn_orient_matrix_UB_13      -0.0022102000
_diffrn_orient_matrix_UB_21      -0.0140715000
_diffrn_orient_matrix_UB_22      -0.0463366000
_diffrn_orient_matrix_UB_23      -0.0040659000
_diffrn_orient_matrix_UB_31      -0.0115111000
_diffrn_orient_matrix_UB_32      0.0030144000
_diffrn_orient_matrix_UB_33      -0.0756673000
_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                2007
_reflns_number_total             3783
_reflns_odcompleteness_completeness 99.65
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.0789
_refine_ls_restrained_S_all      1.018
_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)+(0.1012P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.2389
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C10(H10A,H10B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C19(H19), C3(H3), C21(H21), C6(H6), C4(H4), C20(H20), C5(H5)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06646(9) 0.32106(9) 0.54023(12) 0.0483(4) Uani 1 1 d . . . . .
O2 O 0.2932(2) 0.4813(2) 0.7419(3) 0.0364(8) Uani 1 1 d . . . . .
O1 O 0.1543(2) 0.4519(3) 0.8663(3) 0.0473(10) Uani 1 1 d . . . . .
O3 O 0.0685(2) 0.5383(3) 0.6954(4) 0.0534(10) Uani 1 1 d . . . . .
N2 N 0.2764(3) 0.3820(2) 0.5428(3) 0.0302(9) Uani 1 1 d . . . . .
N1 N 0.2170(3) 0.3383(3) 0.3186(3) 0.0365(10) Uani 1 1 d . . . . .
C15 C 0.2178(3) 0.3267(3) 0.4545(4) 0.0290(10) Uani 1 1 d . . . . .
O5 O 0.2008(3) 0.6853(2) 0.6223(4) 0.0673(13) Uani 1 1 d . . . . .
C1 C 0.3807(3) 0.3480(3) 0.7762(4) 0.0304(11) Uani 1 1 d . . . . .
C7 C 0.2938(3) 0.3877(3) 0.6998(4) 0.0355(12) Uani 1 1 d . . . . .
H7 H 0.247341 0.355104 0.731459 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2155(3) 0.5303(3) 0.6903(4) 0.0336(11) Uani 1 1 d . . . . .
H8 H 0.195615 0.521480 0.586776 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1425(3) 0.5012(3) 0.7639(5) 0.0390(12) Uani 1 1 d . . . . .
C2 C 0.4301(3) 0.3892(3) 0.8979(4) 0.0356(11) Uani 1 1 d . . . . .
H2 H 0.410869 0.443208 0.931589 0.043 Uiso 1 1 calc R U . . .
C17 C 0.3161(3) 0.4356(3) 0.4554(4) 0.0324(11) Uani 1 1 d . . . . .
O4 O 0.2869(4) 0.6540(3) 0.8336(5) 0.099(2) Uani 1 1 d . . . . .
C18 C 0.2768(3) 0.4078(3) 0.3173(4) 0.0347(11) Uani 1 1 d . . . . .
C16 C 0.1596(3) 0.2613(3) 0.5041(4) 0.0361(12) Uani 1 1 d . . . . .
H16A H 0.191551 0.230834 0.590262 0.043 Uiso 1 1 calc R U . . .
H16B H 0.139770 0.214927 0.431441 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2404(4) 0.6304(3) 0.7224(5) 0.0410(13) Uani 1 1 d . . . . .
C22 C 0.3782(4) 0.5043(3) 0.4843(5) 0.0419(13) Uani 1 1 d . . . . .
H22 H 0.403529 0.522690 0.577296 0.050 Uiso 1 1 calc R U . . .
C19 C 0.2999(4) 0.4495(3) 0.2001(5) 0.0486(14) Uani 1 1 d . . . . .
H19 H 0.274738 0.431165 0.106910 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5080(4) 0.3504(4) 0.9695(5) 0.0452(14) Uani 1 1 d . . . . .
H3 H 0.541191 0.379430 1.050233 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4007(4) 0.5442(4) 0.3677(6) 0.0512(14) Uani 1 1 d . . . . .
H21 H 0.443301 0.589594 0.382040 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4109(4) 0.2673(4) 0.7286(5) 0.0516(15) Uani 1 1 d . . . . .
H6 H 0.379347 0.239419 0.645501 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5375(4) 0.2698(4) 0.9241(5) 0.0452(13) Uani 1 1 d . . . . .
H4 H 0.589867 0.243844 0.973376 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3598(4) 0.5171(4) 0.2276(5) 0.0515(15) Uani 1 1 d . . . . .
H20 H 0.374714 0.546873 0.151287 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4877(4) 0.2286(4) 0.8042(5) 0.0619(17) Uani 1 1 d . . . . .
H5 H 0.506120 0.173254 0.773285 0.074 Uiso 1 1 calc R U . . .
C10 C -0.0083(4) 0.5176(4) 0.7531(6) 0.0623(17) Uani 1 1 d . . . . .
H10A H -0.061300 0.519847 0.677590 0.075 Uiso 1 1 calc R U . . .
H10B H -0.003000 0.456852 0.795330 0.075 Uiso 1 1 calc R U . . .
C13 C 0.2186(6) 0.7843(4) 0.6466(7) 0.086(2) Uani 1 1 d . . . . .
H13A H 0.278781 0.793166 0.698341 0.103 Uiso 1 1 calc R U . . .
H13B H 0.209965 0.815700 0.555519 0.103 Uiso 1 1 calc R U . . .
C11 C -0.0108(5) 0.5866(5) 0.8611(7) 0.083(2) Uani 1 1 d . . . . .
H11A H -0.012640 0.646525 0.819171 0.125 Uiso 1 1 calc R U . . .
H11B H 0.040369 0.581282 0.937821 0.125 Uiso 1 1 calc R U . . .
H11C H -0.061967 0.577662 0.897410 0.125 Uiso 1 1 calc R U . . .
C14 C 0.1605(6) 0.8220(5) 0.7279(8) 0.099(3) Uani 1 1 d . . . . .
H14A H 0.101069 0.810104 0.678811 0.149 Uiso 1 1 calc R U . . .
H14B H 0.169588 0.886961 0.738125 0.149 Uiso 1 1 calc R U . . .
H14C H 0.172342 0.793988 0.820705 0.149 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 C16 1.811(5) . ?
O2 C7 1.425(5) . ?
O2 C8 1.403(5) . ?
O1 C9 1.198(5) . ?
O3 C9 1.314(6) . ?
O3 C10 1.477(7) . ?
N2 C15 1.362(5) . ?
N2 C7 1.473(5) . ?
N2 C17 1.400(6) . ?
N1 C15 1.316(5) . ?
N1 C18 1.386(6) . ?
C15 C16 1.478(6) . ?
O5 C12 1.295(6) . ?
O5 C13 1.479(7) . ?
C1 C7 1.508(6) . ?
C1 C2 1.382(6) . ?
C1 C6 1.388(6) . ?
C7 H7 0.9800 . ?
C8 H8 0.9800 . ?
C8 C9 1.546(7) . ?
C8 C12 1.526(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(7) . ?
C17 C18 1.387(6) . ?
C17 C22 1.382(7) . ?
O4 C12 1.196(6) . ?
C18 C19 1.404(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C21 1.383(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.348(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.407(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(8) . ?
C20 H20 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.455(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.447(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C8 O2 C7 116.8(3) . . ?
C9 O3 C10 115.9(4) . . ?
C15 N2 C7 127.4(4) . . ?
C15 N2 C17 106.8(3) . . ?
C17 N2 C7 125.7(4) . . ?
C15 N1 C18 104.9(3) . . ?
N2 C15 C16 124.1(3) . . ?
N1 C15 N2 112.9(4) . . ?
N1 C15 C16 122.9(4) . . ?
C12 O5 C13 116.5(5) . . ?
C2 C1 C7 120.8(4) . . ?
C2 C1 C6 118.7(4) . . ?
C6 C1 C7 120.5(4) . . ?
O2 C7 N2 109.5(3) . . ?
O2 C7 C1 107.2(3) . . ?
O2 C7 H7 108.7 . . ?
N2 C7 C1 114.0(4) . . ?
N2 C7 H7 108.7 . . ?
C1 C7 H7 108.7 . . ?
O2 C8 H8 109.7 . . ?
O2 C8 C9 112.3(3) . . ?
O2 C8 C12 104.8(4) . . ?
C9 C8 H8 109.7 . . ?
C12 C8 H8 109.7 . . ?
C12 C8 C9 110.7(4) . . ?
O1 C9 O3 127.4(5) . . ?
O1 C9 C8 123.6(4) . . ?
O3 C9 C8 109.0(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C18 C17 N2 104.5(4) . . ?
C22 C17 N2 132.8(4) . . ?
C22 C17 C18 122.6(4) . . ?
N1 C18 C19 129.0(4) . . ?
C17 C18 N1 110.8(4) . . ?
C17 C18 C19 120.1(5) . . ?
Cl1 C16 H16A 109.6 . . ?
Cl1 C16 H16B 109.6 . . ?
C15 C16 Cl1 110.1(3) . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O5 C12 C8 112.7(4) . . ?
O4 C12 O5 125.0(5) . . ?
O4 C12 C8 122.1(5) . . ?
C17 C22 H22 121.7 . . ?
C17 C22 C21 116.5(4) . . ?
C21 C22 H22 121.7 . . ?
C18 C19 H19 121.3 . . ?
C20 C19 C18 117.5(4) . . ?
C20 C19 H19 121.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C22 C21 H21 119.6 . . ?
C22 C21 C20 120.8(5) . . ?
C20 C21 H21 119.6 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(5) . . ?
C5 C6 H6 120.0 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 H4 120.9 . . ?
C19 C20 C21 122.3(5) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
O3 C10 H10A 110.3 . . ?
O3 C10 H10B 110.3 . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 O3 106.9(6) . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
O5 C13 H13A 109.7 . . ?
O5 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 O5 109.7(6) . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 C8 C9 O1 9.5(6) . . . . ?
O2 C8 C9 O3 -169.9(4) . . . . ?
O2 C8 C12 O5 142.4(4) . . . . ?
O2 C8 C12 O4 -42.4(7) . . . . ?
N2 C15 C16 Cl1 79.8(5) . . . . ?
N2 C17 C18 N1 -1.5(5) . . . . ?
N2 C17 C18 C19 178.5(4) . . . . ?
N2 C17 C22 C21 -178.4(5) . . . . ?
N1 C15 C16 Cl1 -99.0(4) . . . . ?
N1 C18 C19 C20 179.2(5) . . . . ?
C15 N2 C7 O2 -131.3(4) . . . . ?
C15 N2 C7 C1 108.7(5) . . . . ?
C15 N2 C17 C18 0.3(5) . . . . ?
C15 N2 C17 C22 178.3(5) . . . . ?
C15 N1 C18 C17 2.1(5) . . . . ?
C15 N1 C18 C19 -177.9(5) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C6 C5 C4 -2.5(9) . . . . ?
C7 O2 C8 C9 72.6(4) . . . . ?
C7 O2 C8 C12 -167.3(3) . . . . ?
C7 N2 C15 N1 179.3(4) . . . . ?
C7 N2 C15 C16 0.4(7) . . . . ?
C7 N2 C17 C18 -178.0(4) . . . . ?
C7 N2 C17 C22 0.0(8) . . . . ?
C7 C1 C2 C3 177.7(4) . . . . ?
C7 C1 C6 C5 -175.9(5) . . . . ?
C8 O2 C7 N2 60.0(5) . . . . ?
C8 O2 C7 C1 -175.9(3) . . . . ?
C9 O3 C10 C11 88.1(6) . . . . ?
C9 C8 C12 O5 -96.3(5) . . . . ?
C9 C8 C12 O4 78.8(7) . . . . ?
C2 C1 C7 O2 20.5(5) . . . . ?
C2 C1 C7 N2 141.8(4) . . . . ?
C2 C1 C6 C5 1.7(8) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C17 N2 C15 N1 1.1(5) . . . . ?
C17 N2 C15 C16 -177.8(4) . . . . ?
C17 N2 C7 O2 46.7(6) . . . . ?
C17 N2 C7 C1 -73.4(5) . . . . ?
C17 C18 C19 C20 -0.8(7) . . . . ?
C17 C22 C21 C20 1.7(8) . . . . ?
C18 N1 C15 N2 -2.0(5) . . . . ?
C18 N1 C15 C16 176.9(4) . . . . ?
C18 C17 C22 C21 -0.7(7) . . . . ?
C18 C19 C20 C21 1.9(8) . . . . ?
C12 O5 C13 C14 -85.7(8) . . . . ?
C12 C8 C9 O1 -107.1(5) . . . . ?
C12 C8 C9 O3 73.4(5) . . . . ?
C22 C17 C18 N1 -179.8(4) . . . . ?
C22 C17 C18 C19 0.3(7) . . . . ?
C22 C21 C20 C19 -2.5(9) . . . . ?
C3 C4 C5 C6 1.4(9) . . . . ?
C6 C1 C7 O2 -161.9(4) . . . . ?
C6 C1 C7 N2 -40.6(6) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C10 O3 C9 O1 0.9(8) . . . . ?
C10 O3 C9 C8 -179.7(4) . . . . ?
C13 O5 C12 C8 177.9(5) . . . . ?
C13 O5 C12 O4 3.0(9) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.943
_oxdiff_exptl_absorpt_empirical_full_min 0.430
####################################################################### 
# 
# 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_sjw-20191012
_database_code_depnum_ccdc_archive 'CCDC 2018327'
loop_
_audit_author_name
_audit_author_address
'Ji-Wei Sang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-22 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N3 O5'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3393(2)
_cell_length_b                   21.3081(6)
_cell_length_c                   11.1096(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.128(3)
_cell_angle_gamma                90
_cell_volume                     1943.35(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4857
_cell_measurement_temperature    292.8(4)
_cell_measurement_theta_max      71.2760
_cell_measurement_theta_min      4.1420
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87681
_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    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.13
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.470
_diffrn_reflns_theta_min         4.150
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_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    -72.00  26.00   1.00    1.00    --  -35.62  94.00-155.00   98
  2  ω     -4.00  72.00   1.00    1.00    --   35.62 -94.00  94.00   76
  3  ω     38.00 109.00   1.00    3.83    --  107.12 -94.00  94.00   71
  4  ω    101.00 176.00   1.00    3.83    --  107.12  94.00-155.00   75
  5  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00-120.00   84
  6  ω    -55.00  34.00   1.00    1.00    --  -35.62  38.00  60.00   89
  7  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  90.00   51
  8  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 -90.00   51
  9  ω     89.00 174.00   1.00    3.83    --  107.12  61.00-120.00   85
 10  ω     38.00  64.00   1.00    3.83    --  107.12 -30.00 -90.00   26
 11  ω    106.00 175.00   1.00    3.83    --  107.12 111.00 -60.00   69
 12  ω     60.00  86.00   1.00    3.83    --  107.12 178.00  90.00   26
 13  ω    103.00 128.00   1.00    3.83    --  107.12 -30.00 -90.00   25
 14  ω    122.00 148.00   1.00    3.83    --  107.12 178.00  90.00   26
 15  ω     56.00 113.00   1.00    3.83    --  107.12-111.00  60.00   57
 16  ω     40.00 122.00   1.00    3.83    --  107.12 -45.00 150.00   82
 17  ω     62.00  89.00   1.00    3.83    --  107.12 -95.00-180.00   27
 18  ω     90.00 176.00   1.00    3.83    --  107.12  45.00 -60.00   86
;
_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      0.0572062000
_diffrn_orient_matrix_UB_12      0.0577486000
_diffrn_orient_matrix_UB_13      -0.0641343000
_diffrn_orient_matrix_UB_21      -0.0385487000
_diffrn_orient_matrix_UB_22      -0.0344141000
_diffrn_orient_matrix_UB_23      -0.1238136000
_diffrn_orient_matrix_UB_31      -0.1745341000
_diffrn_orient_matrix_UB_32      0.0265338000
_diffrn_orient_matrix_UB_33      -0.0205036000
_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                3117
_reflns_number_total             3721
_reflns_odcompleteness_completeness 99.86
_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         0.361
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.055
_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)+(0.0447P)²+1.3070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1388
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_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 0.3105(2) 0.29865(8) 0.53307(14) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.289(3) 0.2753(14) 0.468(3) 0.065(9) Uiso 1 1 d . . . . .
O2 O 0.4023(3) 0.43497(9) 0.38550(15) 0.0668(6) Uani 1 1 d . . . . .
O3 O 0.3120(2) 0.34147(9) 0.31196(15) 0.0624(5) Uani 1 1 d . . . . .
O4 O 0.7108(2) 0.34962(8) 0.50736(15) 0.0523(4) Uani 1 1 d . . . . .
O5 O 0.5938(2) 0.25405(9) 0.47640(17) 0.0626(5) Uani 1 1 d . . . . .
N1 N 0.5630(2) 0.36316(8) 0.73469(15) 0.0354(4) Uani 1 1 d . . . . .
N2 N 0.5977(2) 0.30152(9) 0.75050(16) 0.0445(4) Uani 1 1 d . . . . .
N3 N 0.6910(2) 0.29397(9) 0.85735(17) 0.0464(5) Uani 1 1 d . . . . .
C1 C 0.6319(2) 0.39650(10) 0.83542(18) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.6317(3) 0.45959(11) 0.8672(2) 0.0517(6) Uani 1 1 d . . . . .
H2 H 0.573534 0.489510 0.816343 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7227(4) 0.47483(13) 0.9785(2) 0.0654(8) Uani 1 1 d . . . . .
H3 H 0.726072 0.516479 1.003854 0.079 Uiso 1 1 calc R U . . .
C4 C 0.8112(4) 0.42982(14) 1.0557(2) 0.0654(8) Uani 1 1 d . . . . .
H4 H 0.872827 0.442706 1.129530 0.078 Uiso 1 1 calc R U . . .
C5 C 0.8091(3) 0.36806(13) 1.0254(2) 0.0518(6) Uani 1 1 d . . . . .
H5 H 0.866678 0.338302 1.077010 0.062 Uiso 1 1 calc R U . . .
C6 C 0.7157(3) 0.35142(11) 0.91231(18) 0.0388(5) Uani 1 1 d . . . . .
C7 C 0.4545(2) 0.38861(10) 0.62718(17) 0.0353(4) Uani 1 1 d . . . . .
H7 H 0.506218 0.426400 0.601331 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2948(3) 0.40836(11) 0.66338(18) 0.0401(5) Uani 1 1 d . . . . .
C9 C 0.2221(3) 0.46444(13) 0.6221(2) 0.0544(6) Uani 1 1 d . . . . .
H9 H 0.271357 0.490644 0.572443 0.065 Uiso 1 1 calc R U . . .
C10 C 0.0751(4) 0.48150(17) 0.6553(3) 0.0755(10) Uani 1 1 d . . . . .
H10 H 0.024766 0.518711 0.625640 0.091 Uiso 1 1 calc R U . . .
C11 C 0.0035(4) 0.4443(2) 0.7310(4) 0.0874(12) Uani 1 1 d . . . . .
H11 H -0.094363 0.456354 0.753355 0.105 Uiso 1 1 calc R U . . .
C12 C 0.0767(4) 0.38884(19) 0.7739(3) 0.0786(10) Uani 1 1 d . . . . .
H12 H 0.028695 0.363526 0.825811 0.094 Uiso 1 1 calc R U . . .
C13 C 0.2206(3) 0.37085(14) 0.7400(2) 0.0541(6) Uani 1 1 d . . . . .
H13 H 0.269009 0.333139 0.768754 0.065 Uiso 1 1 calc R U . . .
C14 C 0.4297(2) 0.34213(10) 0.51828(18) 0.0362(4) Uani 1 1 d . . . . .
C15 C 0.5890(3) 0.30850(11) 0.50026(19) 0.0430(5) Uani 1 1 d . . . . .
C16 C 0.8647(3) 0.32594(16) 0.4801(3) 0.0659(8) Uani 1 1 d . . . . .
H16A H 0.881056 0.283093 0.509149 0.079 Uiso 1 1 calc R U . . .
H16B H 0.953790 0.351208 0.522558 0.079 Uiso 1 1 calc R U . . .
C17 C 0.8655(4) 0.32782(18) 0.3478(3) 0.0831(10) Uani 1 1 d . . . . .
H17A H 0.788175 0.298050 0.306927 0.125 Uiso 1 1 calc R U . . .
H17B H 0.972356 0.317463 0.332864 0.125 Uiso 1 1 calc R U . . .
H17C H 0.836594 0.369189 0.317203 0.125 Uiso 1 1 calc R U . . .
C18 C 0.3794(3) 0.38037(11) 0.39835(18) 0.0403(5) Uani 1 1 d . . . . .
C19 C 0.2688(4) 0.36382(15) 0.1869(2) 0.0635(8) Uani 1 1 d . . . . .
H19A H 0.233669 0.407209 0.187090 0.076 Uiso 1 1 calc R U . . .
H19B H 0.178928 0.339142 0.143807 0.076 Uiso 1 1 calc R U . . .
C20 C 0.4083(5) 0.35894(18) 0.1235(3) 0.0830(10) Uani 1 1 d . . . . .
H20A H 0.374355 0.369098 0.038681 0.124 Uiso 1 1 calc R U . . .
H20B H 0.450174 0.316876 0.130792 0.124 Uiso 1 1 calc R U . . .
H20C H 0.491854 0.387639 0.159590 0.124 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 H1 0.87(3) . ?
O1 C14 1.389(2) . ?
O2 C18 1.192(3) . ?
O3 C18 1.317(3) . ?
O3 C19 1.453(3) . ?
O4 C15 1.333(3) . ?
O4 C16 1.460(3) . ?
O5 C15 1.192(3) . ?
N1 N2 1.350(2) . ?
N1 C1 1.364(3) . ?
N1 C7 1.469(2) . ?
N2 N3 1.310(3) . ?
N3 C6 1.367(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.517(3) . ?
C7 C14 1.549(3) . ?
C8 C9 1.381(3) . ?
C8 C13 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.553(3) . ?
C14 C18 1.555(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.472(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.466(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C14 O1 H1 109.2(19) . . ?
C18 O3 C19 119.5(2) . . ?
C15 O4 C16 116.7(2) . . ?
N2 N1 C1 110.49(16) . . ?
N2 N1 C7 123.52(16) . . ?
C1 N1 C7 125.81(18) . . ?
N3 N2 N1 108.49(17) . . ?
N2 N3 C6 108.30(17) . . ?
N1 C1 C2 133.9(2) . . ?
N1 C1 C6 103.78(18) . . ?
C6 C1 C2 122.4(2) . . ?
C1 C2 H2 122.2 . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2 122.2 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.6(2) . . ?
C6 C5 H5 121.7 . . ?
N3 C6 C1 108.91(18) . . ?
N3 C6 C5 130.0(2) . . ?
C1 C6 C5 121.1(2) . . ?
N1 C7 H7 107.6 . . ?
N1 C7 C8 109.30(16) . . ?
N1 C7 C14 112.19(16) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C14 112.43(16) . . ?
C14 C7 H7 107.6 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 C13 119.0(2) . . ?
C13 C8 C7 120.6(2) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
O1 C14 C7 109.52(16) . . ?
O1 C14 C15 110.70(18) . . ?
O1 C14 C18 111.10(16) . . ?
C7 C14 C15 113.31(16) . . ?
C7 C14 C18 108.24(17) . . ?
C15 C14 C18 103.84(16) . . ?
O4 C15 C14 110.43(19) . . ?
O5 C15 O4 126.7(2) . . ?
O5 C15 C14 122.7(2) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 C17 110.9(2) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 O3 125.7(2) . . ?
O2 C18 C14 126.1(2) . . ?
O3 C18 C14 108.11(19) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 C20 110.6(2) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C14 C15 O4 -169.24(16) . . . . ?
O1 C14 C15 O5 14.8(3) . . . . ?
O1 C14 C18 O2 141.0(2) . . . . ?
O1 C14 C18 O3 -41.1(2) . . . . ?
N1 N2 N3 C6 0.6(3) . . . . ?
N1 C1 C2 C3 -178.0(2) . . . . ?
N1 C1 C6 N3 -1.5(2) . . . . ?
N1 C1 C6 C5 177.6(2) . . . . ?
N1 C7 C8 C9 136.8(2) . . . . ?
N1 C7 C8 C13 -42.2(3) . . . . ?
N1 C7 C14 O1 82.3(2) . . . . ?
N1 C7 C14 C15 -41.9(2) . . . . ?
N1 C7 C14 C18 -156.47(17) . . . . ?
N2 N1 C1 C2 -178.6(3) . . . . ?
N2 N1 C1 C6 1.9(2) . . . . ?
N2 N1 C7 C8 107.1(2) . . . . ?
N2 N1 C7 C14 -18.3(3) . . . . ?
N2 N3 C6 C1 0.6(3) . . . . ?
N2 N3 C6 C5 -178.4(2) . . . . ?
C1 N1 N2 N3 -1.7(2) . . . . ?
C1 N1 C7 C8 -67.5(3) . . . . ?
C1 N1 C7 C14 167.05(18) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C1 C6 N3 178.9(2) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 N3 179.7(3) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C7 N1 N2 N3 -177.03(18) . . . . ?
C7 N1 C1 C2 -3.4(4) . . . . ?
C7 N1 C1 C6 177.15(18) . . . . ?
C7 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C13 C12 179.4(2) . . . . ?
C7 C14 C15 O4 -45.8(2) . . . . ?
C7 C14 C15 O5 138.3(2) . . . . ?
C7 C14 C18 O2 20.7(3) . . . . ?
C7 C14 C18 O3 -161.40(18) . . . . ?
C8 C7 C14 O1 -41.4(2) . . . . ?
C8 C7 C14 C15 -165.55(17) . . . . ?
C8 C7 C14 C18 79.9(2) . . . . ?
C8 C9 C10 C11 1.8(4) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C13 C8 C9 C10 -1.6(3) . . . . ?
C14 C7 C8 C9 -98.0(2) . . . . ?
C14 C7 C8 C13 83.1(2) . . . . ?
C15 O4 C16 C17 85.6(3) . . . . ?
C15 C14 C18 O2 -99.9(3) . . . . ?
C15 C14 C18 O3 77.9(2) . . . . ?
C16 O4 C15 O5 1.7(3) . . . . ?
C16 O4 C15 C14 -174.08(18) . . . . ?
C18 O3 C19 C20 86.3(3) . . . . ?
C18 C14 C15 O4 71.5(2) . . . . ?
C18 C14 C15 O5 -104.5(2) . . . . ?
C19 O3 C18 O2 4.2(4) . . . . ?
C19 O3 C18 C14 -173.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.812
