# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_sh0227-1
_database_code_depnum_ccdc_archive 'CCDC 2000637'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C H Cl3, 2(C26 H21 N O3)'
_chemical_formula_sum            'C53 H43 Cl3 N2 O6'
_chemical_formula_weight         910.24
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.82420(10)
_cell_length_b                   13.6944(2)
_cell_length_c                   17.0549(3)
_cell_angle_alpha                83.0810(10)
_cell_angle_beta                 83.3180(10)
_cell_angle_gamma                79.1050(10)
_cell_volume                     2226.41(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    22767
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8650
_cell_measurement_theta_min      1.8440
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49820
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50   22.14    --   10.60  82.00-120.00  234
  2  ω    -17.00 100.00   0.50   22.14    --   10.60  82.00 -60.00  234
  3  ω    -15.00 100.00   0.50   22.14    --   10.60  77.00 -60.00  230
  4  ω    -79.00  38.00   0.50   22.14    --   10.60 -82.00  60.00  234
  5  ω    -15.00 100.00   0.50   22.14    --   10.60  77.00 -30.00  230
  6  ω    -16.00  29.00   0.50   22.14    --   10.60  82.00 150.00   90
  7  ω    -20.00 100.00   0.50   22.14    --   10.60  57.00-120.00  240
  8  ω    -60.00 -24.00   0.50   22.14    --   10.60 -57.00-180.00   72
  9  ω    -13.00  17.00   0.50   22.14    --   10.60  57.00 120.00   60
 10  ω     32.00  59.00   0.50   22.14    --   10.60  57.00 120.00   54
 11  ω     61.00  87.00   0.50   22.14    --   10.60  57.00 120.00   52
 12  ω    -79.00  18.00   0.50   22.14    --   10.60 -38.00 120.00  194
 13  ω    -17.00   9.00   0.50   22.14    --   10.60  82.00   0.00   52
 14  ω     38.00  92.00   0.50   22.14    --   10.60  82.00   0.00  108
 15  ω     34.00  93.00   0.50   22.14    --   10.60  77.00-120.00  118
 16  ω    -97.00 -72.00   0.50   22.14    --  -10.90 -82.00 -60.00   50
 17  ω     -8.00  17.00   0.50   22.14    --  -10.90 -82.00  90.00   50
 18  ω    -82.00   4.00   0.50   22.14    --  -10.90 -82.00   0.00  172
 19  ω    -90.00 -64.00   0.50   22.14    --  -10.90 -82.00  90.00   52
 20  ω    -31.00  17.00   0.50   22.14    --  -10.90 -82.00 -60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137704000
_diffrn_orient_matrix_UB_12      -0.0373826000
_diffrn_orient_matrix_UB_13      0.0309271000
_diffrn_orient_matrix_UB_21      0.0135905000
_diffrn_orient_matrix_UB_22      0.0299773000
_diffrn_orient_matrix_UB_23      0.0283183000
_diffrn_orient_matrix_UB_31      -0.0712869000
_diffrn_orient_matrix_UB_32      0.0226864000
_diffrn_orient_matrix_UB_33      0.0036115000
_diffrn_oxdiff_digest_frames     
;
01158603f32e28b6ec1a96e8701814ca40000258219
;
_diffrn_oxdiff_digest_hkl        
;
01c179d4427678c9a692e448c57aea4bfa4ca3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_number_gt                7076
_reflns_number_total             8704
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.420
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         8704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0963P)²+3.0166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1861
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Others
 Sof(Cl4)=Sof(Cl5)=Sof(H53A)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl3)=Sof(H53)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C53(H53), C53(H53A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C32(H32), C34(H34), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C36(H36A,H36B,
 H36C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 1.04081(12) 0.76062(8) 1.04936(6) 0.0600(3) Uani 1 d . . .
Cl2 Cl 0.7604(6) 0.8394(7) 1.0184(4) 0.0794(15) Uani 0.706(15) d A 1 .
Cl3 Cl 0.9989(4) 0.90340(17) 0.9142(3) 0.0599(11) Uani 0.706(15) d A 1 .
Cl4 Cl 1.0063(7) 0.9134(5) 0.9561(12) 0.076(3) Uani 0.294(15) d A 2 .
Cl5 Cl 0.7593(12) 0.8733(7) 1.0082(8) 0.0471(17) Uani 0.294(15) d A 2 .
O1 O 0.2948(2) 0.77535(13) 0.14403(11) 0.0264(4) Uani 1 d . . .
O2 O 0.85483(18) 0.41984(12) 0.36939(10) 0.0206(4) Uani 1 d . . .
O3 O 0.77138(18) 0.32788(12) 0.26907(10) 0.0212(4) Uani 1 d . . .
O4 O 0.67634(18) 0.48804(13) 0.60219(11) 0.0221(4) Uani 1 d . . .
O5 O 1.10995(19) 0.56534(14) 0.93007(11) 0.0255(4) Uani 1 d . . .
O6 O 0.8364(2) 0.32618(13) 0.63708(12) 0.0292(5) Uani 1 d . . .
N1 N 0.4405(2) 0.77750(15) 0.24105(12) 0.0189(4) Uani 1 d . . .
N2 N 0.9425(2) 0.64482(15) 0.85575(12) 0.0196(4) Uani 1 d . . .
C1 C 0.7530(2) 0.47668(18) 0.32784(14) 0.0169(5) Uani 1 d . . .
C2 C 0.6975(2) 0.57441(17) 0.33482(14) 0.0161(5) Uani 1 d . . .
H2 H 0.7284 0.6086 0.3728 0.019 Uiso 1 calc . . R
C3 C 0.5933(2) 0.62590(17) 0.28556(14) 0.0154(5) Uani 1 d . . .
C4 C 0.5360(2) 0.72838(17) 0.28773(14) 0.0165(5) Uani 1 d . . .
C5 C 0.3947(3) 0.72581(19) 0.19091(14) 0.0195(5) Uani 1 d . . .
C6 C 0.4408(3) 0.62558(18) 0.18341(14) 0.0193(5) Uani 1 d . . .
H6 H 0.4037 0.5927 0.1471 0.023 Uiso 1 calc . . R
C7 C 0.5439(2) 0.57346(17) 0.23074(14) 0.0162(5) Uani 1 d . . .
C8 C 0.6021(2) 0.47084(17) 0.22516(14) 0.0171(5) Uani 1 d . . .
H8 H 0.5689 0.4347 0.1894 0.021 Uiso 1 calc . . R
C9 C 0.7052(2) 0.42397(17) 0.27083(14) 0.0178(5) Uani 1 d . . .
C10 C 0.8986(3) 0.4634(2) 0.43199(15) 0.0238(6) Uani 1 d . . .
H10A H 0.9339 0.5244 0.4104 0.036 Uiso 1 calc . . GR
H10B H 0.9725 0.4158 0.4570 0.036 Uiso 1 calc . . GR
H10C H 0.8193 0.4798 0.4716 0.036 Uiso 1 calc . . GR
C11 C 0.5803(2) 0.78951(17) 0.34404(14) 0.0165(5) Uani 1 d . . .
C12 C 0.5132(2) 0.79254(17) 0.42132(14) 0.0174(5) Uani 1 d . . .
C13 C 0.3993(3) 0.74098(18) 0.44784(15) 0.0205(5) Uani 1 d . . .
H13 H 0.3701 0.7012 0.4133 0.025 Uiso 1 calc . . R
C14 C 0.3328(3) 0.74848(19) 0.52187(16) 0.0257(6) Uani 1 d . . .
H14 H 0.2559 0.7153 0.5379 0.031 Uiso 1 calc . . R
C15 C 0.3764(3) 0.8052(2) 0.57581(16) 0.0281(6) Uani 1 d . . .
H15 H 0.3293 0.8091 0.6276 0.034 Uiso 1 calc . . R
C16 C 0.4850(3) 0.85390(19) 0.55359(16) 0.0261(6) Uani 1 d . . .
H16 H 0.5146 0.8903 0.5905 0.031 Uiso 1 calc . . R
C17 C 0.5553(3) 0.85122(18) 0.47555(15) 0.0200(5) Uani 1 d . . .
C18 C 0.6597(3) 0.90674(18) 0.44961(15) 0.0217(5) Uani 1 d . . .
H18 H 0.6888 0.9446 0.4856 0.026 Uiso 1 calc . . R
C19 C 0.7225(3) 0.90808(18) 0.37222(15) 0.0198(5) Uani 1 d . . .
C20 C 0.8236(3) 0.97047(19) 0.34397(17) 0.0249(6) Uani 1 d . . .
H20 H 0.8491 1.0114 0.3790 0.030 Uiso 1 calc . . R
C21 C 0.8832(3) 0.97206(19) 0.26839(18) 0.0266(6) Uani 1 d . . .
H21 H 0.9495 1.0142 0.2509 0.032 Uiso 1 calc . . R
C22 C 0.8473(3) 0.91122(19) 0.21496(17) 0.0253(6) Uani 1 d . . .
H22 H 0.8903 0.9127 0.1621 0.030 Uiso 1 calc . . R
C23 C 0.7516(3) 0.85058(19) 0.23905(15) 0.0215(5) Uani 1 d . . .
H23 H 0.7293 0.8099 0.2027 0.026 Uiso 1 calc . . R
C24 C 0.6844(2) 0.84736(17) 0.31814(14) 0.0175(5) Uani 1 d . . .
C25 C 0.2648(3) 0.8824(2) 0.14260(18) 0.0309(6) Uani 1 d . . .
H25A H 0.1934 0.9098 0.1063 0.046 Uiso 1 calc . . GR
H25B H 0.3497 0.9095 0.1244 0.046 Uiso 1 calc . . GR
H25C H 0.2307 0.9008 0.1961 0.046 Uiso 1 calc . . GR
C26 C 0.7344(3) 0.27183(19) 0.21160(16) 0.0261(6) Uani 1 d . . .
H26A H 0.7517 0.3055 0.1583 0.039 Uiso 1 calc . . GR
H26B H 0.6355 0.2671 0.2220 0.039 Uiso 1 calc . . GR
H26C H 0.7907 0.2045 0.2152 0.039 Uiso 1 calc . . GR
C27 C 0.7568(2) 0.49271(18) 0.66061(15) 0.0179(5) Uani 1 d . . .
C28 C 0.7581(2) 0.57425(18) 0.69871(14) 0.0171(5) Uani 1 d . . .
H28 H 0.6979 0.6354 0.6852 0.020 Uiso 1 calc . . R
C29 C 0.8494(2) 0.56810(17) 0.75882(14) 0.0173(5) Uani 1 d . . .
C30 C 0.8565(2) 0.65022(18) 0.80008(14) 0.0176(5) Uani 1 d . . .
C31 C 1.0282(2) 0.55738(19) 0.87272(14) 0.0190(5) Uani 1 d . . .
C32 C 1.0302(3) 0.47230(18) 0.83774(15) 0.0197(5) Uani 1 d . . .
H32 H 1.0913 0.4121 0.8527 0.024 Uiso 1 calc . . R
C33 C 0.9391(2) 0.47620(18) 0.77900(14) 0.0176(5) Uani 1 d . . .
C34 C 0.9353(3) 0.39190(18) 0.73873(15) 0.0205(5) Uani 1 d . . .
H34 H 0.9940 0.3299 0.7520 0.025 Uiso 1 calc . . R
C35 C 0.8475(3) 0.39990(18) 0.68102(15) 0.0206(5) Uani 1 d . . .
C36 C 0.5884(3) 0.57898(19) 0.57595(16) 0.0239(6) Uani 1 d . . .
H36A H 0.5372 0.5672 0.5330 0.036 Uiso 1 calc . . GR
H36B H 0.6455 0.6299 0.5566 0.036 Uiso 1 calc . . GR
H36C H 0.5223 0.6021 0.6203 0.036 Uiso 1 calc . . GR
C37 C 0.7627(2) 0.74884(18) 0.78594(14) 0.0182(5) Uani 1 d . . .
C38 C 0.7987(2) 0.81984(17) 0.72369(14) 0.0173(5) Uani 1 d . . .
C39 C 0.9201(3) 0.79914(18) 0.66888(15) 0.0198(5) Uani 1 d . . .
H39 H 0.9801 0.7361 0.6745 0.024 Uiso 1 calc . . R
C40 C 0.9501(3) 0.8688(2) 0.60900(16) 0.0240(6) Uani 1 d . . .
H40 H 1.0297 0.8532 0.5724 0.029 Uiso 1 calc . . R
C41 C 0.8649(3) 0.96457(19) 0.60016(16) 0.0257(6) Uani 1 d . . .
H41 H 0.8884 1.0126 0.5582 0.031 Uiso 1 calc . . R
C42 C 0.7496(3) 0.98805(19) 0.65135(16) 0.0247(6) Uani 1 d . . .
H42 H 0.6940 1.0528 0.6453 0.030 Uiso 1 calc . . R
C43 C 0.7111(3) 0.91622(18) 0.71433(15) 0.0208(5) Uani 1 d . . .
C44 C 0.5922(3) 0.93878(19) 0.76624(16) 0.0249(6) Uani 1 d . . .
H44 H 0.5357 1.0032 0.7601 0.030 Uiso 1 calc . . R
C45 C 0.5541(3) 0.8685(2) 0.82728(16) 0.0240(6) Uani 1 d . . .
C46 C 0.4321(3) 0.8903(2) 0.88058(18) 0.0329(7) Uani 1 d . . .
H46 H 0.3746 0.9543 0.8748 0.039 Uiso 1 calc . . R
C47 C 0.3965(3) 0.8211(3) 0.93957(18) 0.0384(7) Uani 1 d . . .
H47 H 0.3151 0.8374 0.9748 0.046 Uiso 1 calc . . R
C48 C 0.4796(3) 0.7251(3) 0.94886(18) 0.0366(7) Uani 1 d . . .
H48 H 0.4535 0.6772 0.9901 0.044 Uiso 1 calc . . R
C49 C 0.5973(3) 0.7007(2) 0.89900(16) 0.0287(6) Uani 1 d . . .
H49 H 0.6515 0.6355 0.9057 0.034 Uiso 1 calc . . R
C50 C 0.6399(3) 0.77152(19) 0.83695(15) 0.0217(5) Uani 1 d . . .
C51 C 1.1980(3) 0.4772(2) 0.95923(16) 0.0279(6) Uani 1 d . . .
H51A H 1.2650 0.4519 0.9159 0.042 Uiso 1 calc . . GR
H51B H 1.1416 0.4264 0.9805 0.042 Uiso 1 calc . . GR
H51C H 1.2482 0.4924 1.0014 0.042 Uiso 1 calc . . GR
C52 C 0.9206(3) 0.2307(2) 0.6551(2) 0.0360(7) Uani 1 d . . .
H52A H 0.9006 0.2076 0.7112 0.054 Uiso 1 calc . . GR
H52B H 1.0192 0.2362 0.6445 0.054 Uiso 1 calc . . GR
H52C H 0.8997 0.1827 0.6220 0.054 Uiso 1 calc . . GR
C53 C 0.9321(4) 0.8085(3) 0.9739(2) 0.0562(10) Uani 1 d A . .
H53 H 0.9338 0.7533 0.9401 0.067 Uiso 0.706(15) calc A 1 R
H53A H 0.9382 0.7673 0.9286 0.067 Uiso 0.294(15) calc A 2 R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Cl4 2.465(11) . ?
Cl1 C53 1.755(4) . ?
Cl2 C53 1.764(7) . ?
Cl3 C53 1.733(4) . ?
Cl4 C53 1.711(7) . ?
Cl5 C53 1.826(12) . ?
O1 C5 1.365(3) . ?
O1 C25 1.437(3) . ?
O2 C1 1.359(3) . ?
O2 C10 1.427(3) . ?
O3 C9 1.355(3) . ?
O3 C26 1.432(3) . ?
O4 C27 1.356(3) . ?
O4 C36 1.430(3) . ?
O5 C31 1.362(3) . ?
O5 C51 1.419(3) . ?
O6 C35 1.355(3) . ?
O6 C52 1.429(3) . ?
N1 C4 1.332(3) . ?
N1 C5 1.338(3) . ?
N2 C30 1.329(3) . ?
N2 C31 1.349(3) . ?
C1 C2 1.360(3) . ?
C1 C9 1.446(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.427(3) . ?
C3 C4 1.413(3) . ?
C3 C7 1.423(3) . ?
C4 C11 1.497(3) . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(3) . ?
C7 C8 1.424(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.405(3) . ?
C11 C24 1.409(3) . ?
C12 C13 1.435(3) . ?
C12 C17 1.437(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.359(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.423(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.356(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.428(4) . ?
C17 C18 1.391(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C19 C20 1.435(3) . ?
C19 C24 1.437(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.352(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.420(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.431(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.361(3) . ?
C27 C35 1.438(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.424(3) . ?
C29 C30 1.413(3) . ?
C29 C33 1.423(3) . ?
C30 C37 1.495(3) . ?
C31 C32 1.368(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.409(3) . ?
C33 C34 1.421(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.364(4) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.411(3) . ?
C37 C50 1.410(3) . ?
C38 C39 1.433(3) . ?
C38 C43 1.435(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.357(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.418(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.359(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.434(4) . ?
C43 C44 1.391(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.398(4) . ?
C45 C46 1.425(4) . ?
C45 C50 1.434(4) . ?
C46 H46 0.9500 . ?
C46 C47 1.359(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.412(5) . ?
C48 H48 0.9500 . ?
C48 C49 1.366(4) . ?
C49 H49 0.9500 . ?
C49 C50 1.428(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53 1.0000 . ?
C53 H53A 1.0000 . ?

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
C53 Cl1 Cl4 44.0(2) . . ?
C53 Cl4 Cl1 45.4(3) . . ?
C5 O1 C25 116.7(2) . . ?
C1 O2 C10 117.07(19) . . ?
C9 O3 C26 117.1(2) . . ?
C27 O4 C36 116.60(19) . . ?
C31 O5 C51 117.5(2) . . ?
C35 O6 C52 116.8(2) . . ?
C4 N1 C5 117.7(2) . . ?
C30 N2 C31 118.4(2) . . ?
O2 C1 C2 126.4(2) . . ?
O2 C1 C9 113.6(2) . . ?
C2 C1 C9 120.0(2) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 123.1(2) . . ?
C4 C3 C7 117.3(2) . . ?
C7 C3 C2 119.6(2) . . ?
N1 C4 C3 123.5(2) . . ?
N1 C4 C11 115.3(2) . . ?
C3 C4 C11 121.2(2) . . ?
O1 C5 C6 117.4(2) . . ?
N1 C5 O1 118.0(2) . . ?
N1 C5 C6 124.6(2) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.3(2) . . ?
C7 C6 H6 120.8 . . ?
C3 C7 C8 119.0(2) . . ?
C6 C7 C3 118.5(2) . . ?
C6 C7 C8 122.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C1 113.7(2) . . ?
O3 C9 C8 125.9(2) . . ?
C8 C9 C1 120.5(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 119.7(2) . . ?
C12 C11 C24 120.3(2) . . ?
C24 C11 C4 119.9(2) . . ?
C11 C12 C13 122.0(2) . . ?
C11 C12 C17 119.9(2) . . ?
C13 C12 C17 118.1(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.0(2) . . ?
C18 C17 C12 119.1(2) . . ?
C18 C17 C16 121.8(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 C24 119.9(2) . . ?
C20 C19 C24 118.6(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C11 C24 C19 119.1(2) . . ?
C11 C24 C23 122.7(2) . . ?
C23 C24 C19 118.2(2) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 C28 126.4(2) . . ?
O4 C27 C35 113.4(2) . . ?
C28 C27 C35 120.1(2) . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 122.9(2) . . ?
C30 C29 C33 117.4(2) . . ?
C33 C29 C28 119.7(2) . . ?
N2 C30 C29 123.0(2) . . ?
N2 C30 C37 115.2(2) . . ?
C29 C30 C37 121.8(2) . . ?
O5 C31 C32 125.1(2) . . ?
N2 C31 O5 110.7(2) . . ?
N2 C31 C32 124.2(2) . . ?
C31 C32 H32 120.9 . . ?
C31 C32 C33 118.3(2) . . ?
C33 C32 H32 120.9 . . ?
C32 C33 C29 118.7(2) . . ?
C32 C33 C34 122.2(2) . . ?
C34 C33 C29 119.1(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
O6 C35 C27 113.3(2) . . ?
O6 C35 C34 125.8(2) . . ?
C34 C35 C27 120.9(2) . . ?
O4 C36 H36A 109.5 . . ?
O4 C36 H36B 109.5 . . ?
O4 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C30 120.4(2) . . ?
C50 C37 C30 119.3(2) . . ?
C50 C37 C38 120.2(2) . . ?
C37 C38 C39 122.3(2) . . ?
C37 C38 C43 119.3(2) . . ?
C39 C38 C43 118.4(2) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 C38 120.6(2) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.2(2) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.4(2) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.7(2) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 C38 118.7(2) . . ?
C44 C43 C38 120.0(2) . . ?
C44 C43 C42 121.3(2) . . ?
C43 C44 H44 119.4 . . ?
C43 C44 C45 121.2(2) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C46 121.9(3) . . ?
C44 C45 C50 119.4(2) . . ?
C46 C45 C50 118.7(3) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.1(3) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 119.8 . . ?
C46 C47 C48 120.4(3) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 119.7 . . ?
C49 C48 C47 120.5(3) . . ?
C49 C48 H48 119.7 . . ?
C48 C49 H49 119.5 . . ?
C48 C49 C50 121.0(3) . . ?
C50 C49 H49 119.5 . . ?
C37 C50 C45 119.8(2) . . ?
C37 C50 C49 122.0(2) . . ?
C49 C50 C45 118.2(2) . . ?
O5 C51 H51A 109.5 . . ?
O5 C51 H51B 109.5 . . ?
O5 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O6 C52 H52A 109.5 . . ?
O6 C52 H52B 109.5 . . ?
O6 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
Cl1 C53 Cl2 108.0(3) . . ?
Cl1 C53 Cl5 114.8(5) . . ?
Cl1 C53 H53 107.4 . . ?
Cl1 C53 H53A 117.0 . . ?
Cl2 C53 Cl5 15.0(4) . . ?
Cl2 C53 H53 107.4 . . ?
Cl2 C53 H53A 112.6 . . ?
Cl3 C53 Cl1 109.7(3) . . ?
Cl3 C53 Cl2 116.5(4) . . ?
Cl3 C53 Cl5 101.5(4) . . ?
Cl3 C53 H53 107.4 . . ?
Cl3 C53 H53A 92.7 . . ?
Cl4 C53 Cl1 90.7(5) . . ?
Cl4 C53 Cl2 109.5(7) . . ?
Cl4 C53 Cl3 25.4(5) . . ?
Cl4 C53 Cl5 95.5(6) . . ?
Cl4 C53 H53 130.9 . . ?
Cl4 C53 H53A 117.0 . . ?
Cl5 C53 H53 115.6 . . ?
Cl5 C53 H53A 117.0 . . ?
H53 C53 H53A 15.1 . . ?


_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.761
####################################################################### 
# 
# 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_sh0211-2
_database_code_depnum_ccdc_archive 'CCDC 2000638'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-02-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O6'
_chemical_formula_sum            'C19 H18 N2 O6'
_chemical_formula_weight         370.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 N2 O6'
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                   10.5325(2)
_cell_length_b                   8.1523(2)
_cell_length_c                   19.8965(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.680(2)
_cell_angle_gamma                90
_cell_volume                     1702.70(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7850
_cell_measurement_theta_min      1.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.014
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  40.00   0.50   10.87    --   10.60  77.00 -90.00   60
  2  ω    -77.00  17.00   0.50   10.87    --   10.60 -38.00  60.00  188
  3  ω    -13.00  48.00   0.50   10.87    --   10.60 -38.00  90.00  122
  4  ω     60.00 100.00   0.50   10.87    --   10.60  77.00 -90.00   80
  5  ω    -86.00 -52.00   0.50   10.87    --  -10.90 -57.00 -30.00   68
  6  ω    -34.00   7.00   0.50   10.87    --  -10.90 -57.00 -30.00   82
  7  ω    -38.00  -5.00   0.50   10.87    --  -10.90  82.00  60.00   66
  8  ω    -24.00  10.00   0.50   10.87    --  -10.90  77.00 -30.00   68
  9  ω     42.00  67.00   0.50   10.87    --  -10.90  82.00  60.00   50
 10  ω    -17.00  78.00   0.50   10.87    --  -10.90  77.00   0.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0422832000
_diffrn_orient_matrix_UB_12      -0.0662012000
_diffrn_orient_matrix_UB_13      -0.0079700000
_diffrn_orient_matrix_UB_21      0.0215807000
_diffrn_orient_matrix_UB_22      -0.0392618000
_diffrn_orient_matrix_UB_23      0.0306354000
_diffrn_orient_matrix_UB_31      -0.0480777000
_diffrn_orient_matrix_UB_32      0.0405979000
_diffrn_orient_matrix_UB_33      0.0166485000
_diffrn_oxdiff_digest_frames     
;
01093e50bc978df131db035efeec0c360400025243a
;
_diffrn_oxdiff_digest_hkl        
;
01079d6a7905a75d102c6591f61e05c7e8a36f
;
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2987
_reflns_number_total             3558
_reflns_odcompleteness_completeness 99.63
_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 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0074(11)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.063
_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)+(0.0431P)²+0.5305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C15(H15), C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C)
;
_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 0.37067(8) 0.84399(11) 0.48449(5) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.97590(8) 0.54504(11) 0.62934(5) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.86645(8) 0.33620(11) 0.69803(5) 0.0222(2) Uani 1 1 d . . . . .
O4 O 0.47130(8) 0.51300(12) 0.75161(4) 0.0189(2) Uani 1 1 d . . . . .
O5 O 0.06475(9) 0.17911(13) 0.55139(5) 0.0297(3) Uani 1 1 d . . . . .
O6 O 0.02257(9) 0.05715(12) 0.64339(5) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.37577(9) 0.64012(13) 0.56657(5) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.08436(10) 0.15475(13) 0.61232(6) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.43811(11) 0.74250(16) 0.52817(6) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.56872(11) 0.75466(15) 0.53063(6) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.607409 0.831347 0.504354 0.020 Uiso 1 1 calc R . . . .
C3 C 0.64179(11) 0.64943(15) 0.57338(6) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.77771(11) 0.65504(16) 0.57831(6) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.819209 0.730702 0.552821 0.019 Uiso 1 1 calc R . . . .
C5 C 0.84675(11) 0.55054(16) 0.62000(6) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.78408(11) 0.43124(16) 0.65907(6) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.65453(11) 0.42333(16) 0.65521(6) 0.0166(3) Uani 1 1 d . . . . .
H7 H 0.614798 0.344636 0.680052 0.020 Uiso 1 1 calc R . . . .
C8 C 0.57908(11) 0.53464(15) 0.61340(6) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.44431(11) 0.53996(15) 0.60887(6) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.23442(11) 0.83695(18) 0.48218(7) 0.0232(3) Uani 1 1 d . . . . .
H10A H 0.198504 0.906396 0.446581 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.206825 0.873667 0.524458 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.206671 0.726062 0.473950 0.035 Uiso 1 1 calc GR . . . .
C11 C 1.04308(12) 0.65472(18) 0.58870(7) 0.0237(3) Uani 1 1 d . . . . .
H11A H 1.022207 0.630210 0.541906 0.036 Uiso 1 1 calc GR . . . .
H11B H 1.133101 0.641884 0.599251 0.036 Uiso 1 1 calc GR . . . .
H11C H 1.018991 0.765668 0.597667 0.036 Uiso 1 1 calc GR . . . .
C12 C 0.81247(13) 0.2088(2) 0.73553(8) 0.0321(4) Uani 1 1 d . . . . .
H12A H 0.762724 0.137614 0.705292 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.758881 0.255922 0.767208 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.879408 0.146939 0.759359 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.36489(11) 0.43039(15) 0.64873(6) 0.0150(3) Uani 1 1 d . . . . .
C14 C 0.38046(11) 0.41633(15) 0.71945(6) 0.0156(3) Uani 1 1 d . . . . .
C15 C 0.30124(12) 0.31346(16) 0.75353(7) 0.0180(3) Uani 1 1 d . . . . .
H15 H 0.314089 0.302604 0.800114 0.022 Uiso 1 1 calc R . . . .
C16 C 0.20398(12) 0.22779(16) 0.71849(7) 0.0185(3) Uani 1 1 d . . . . .
H16 H 0.150694 0.159780 0.741044 0.022 Uiso 1 1 calc R . . . .
C17 C 0.18745(11) 0.24509(15) 0.64940(6) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.26558(11) 0.34490(15) 0.61451(6) 0.0157(3) Uani 1 1 d . . . . .
H18 H 0.251509 0.354752 0.567930 0.019 Uiso 1 1 calc R . . . .
C19 C 0.50553(13) 0.48210(18) 0.82177(6) 0.0240(3) Uani 1 1 d . . . . .
H19A H 0.526288 0.368172 0.828068 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.435215 0.509548 0.847454 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.577998 0.547897 0.836703 0.036 Uiso 1 1 calc GR . . . .


_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 C1 1.3579(15) . ?
O1 C10 1.4331(14) . ?
O2 C5 1.3586(14) . ?
O2 C11 1.4309(15) . ?
O3 C6 1.3579(15) . ?
O3 C12 1.4241(16) . ?
O4 C14 1.3587(15) . ?
O4 C19 1.4351(15) . ?
O5 N2 1.2292(14) . ?
O6 N2 1.2265(14) . ?
N1 C1 1.3392(16) . ?
N1 C9 1.3405(16) . ?
N2 C17 1.4611(16) . ?
C1 C2 1.3761(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3946(18) . ?
C3 C4 1.4276(16) . ?
C3 C8 1.4254(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3580(18) . ?
C5 C6 1.4385(18) . ?
C6 C7 1.3619(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.4279(17) . ?
C8 C9 1.4156(16) . ?
C9 C13 1.4950(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.4080(17) . ?
C13 C18 1.3882(17) . ?
C14 C15 1.3969(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3808(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3786(18) . ?
C17 C18 1.3837(17) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C1 O1 C10 117.80(10) . . ?
C5 O2 C11 115.97(10) . . ?
C6 O3 C12 116.83(10) . . ?
C14 O4 C19 117.88(10) . . ?
C1 N1 C9 118.28(10) . . ?
O5 N2 C17 118.34(10) . . ?
O6 N2 O5 123.27(11) . . ?
O6 N2 C17 118.39(11) . . ?
O1 C1 C2 116.62(11) . . ?
N1 C1 O1 119.32(11) . . ?
N1 C1 C2 124.05(11) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.53(11) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.50(11) . . ?
C2 C3 C8 119.13(11) . . ?
C8 C3 C4 119.37(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.38(12) . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C6 113.72(11) . . ?
C4 C5 O2 125.77(11) . . ?
C4 C5 C6 120.52(11) . . ?
O3 C6 C5 113.22(10) . . ?
O3 C6 C7 126.56(12) . . ?
C7 C6 C5 120.21(11) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.68(12) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.78(11) . . ?
C9 C8 C3 116.88(11) . . ?
C9 C8 C7 124.34(11) . . ?
N1 C9 C8 123.00(11) . . ?
N1 C9 C13 113.64(10) . . ?
C8 C9 C13 123.33(11) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C9 123.66(11) . . ?
C18 C13 C9 118.14(11) . . ?
C18 C13 C14 118.10(11) . . ?
O4 C14 C13 116.33(11) . . ?
O4 C14 C15 123.04(11) . . ?
C15 C14 C13 120.56(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.43(12) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.67(12) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 N2 118.69(11) . . ?
C16 C17 C18 121.90(11) . . ?
C18 C17 N2 119.40(11) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.29(11) . . ?
C17 C18 H18 119.9 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C1 C2 C3 -178.18(11) . . . . ?
O2 C5 C6 O3 0.19(15) . . . . ?
O2 C5 C6 C7 179.49(11) . . . . ?
O3 C6 C7 C8 178.11(12) . . . . ?
O4 C14 C15 C16 174.86(12) . . . . ?
O5 N2 C17 C16 175.20(11) . . . . ?
O5 N2 C17 C18 -4.91(17) . . . . ?
O6 N2 C17 C16 -5.55(17) . . . . ?
O6 N2 C17 C18 174.34(11) . . . . ?
N1 C1 C2 C3 2.97(19) . . . . ?
N1 C9 C13 C14 -127.82(12) . . . . ?
N1 C9 C13 C18 48.35(15) . . . . ?
N2 C17 C18 C13 -179.32(11) . . . . ?
C1 N1 C9 C8 -1.72(18) . . . . ?
C1 N1 C9 C13 -179.54(10) . . . . ?
C1 C2 C3 C4 179.85(12) . . . . ?
C1 C2 C3 C8 -0.64(18) . . . . ?
C2 C3 C4 C5 -179.58(12) . . . . ?
C2 C3 C8 C7 177.76(11) . . . . ?
C2 C3 C8 C9 -2.49(17) . . . . ?
C3 C4 C5 O2 -179.46(11) . . . . ?
C3 C4 C5 C6 0.87(19) . . . . ?
C3 C8 C9 N1 3.80(18) . . . . ?
C3 C8 C9 C13 -178.60(11) . . . . ?
C4 C3 C8 C7 -2.72(17) . . . . ?
C4 C3 C8 C9 177.03(11) . . . . ?
C4 C5 C6 O3 179.90(11) . . . . ?
C4 C5 C6 C7 -0.81(19) . . . . ?
C5 C6 C7 C8 -1.07(19) . . . . ?
C6 C7 C8 C3 2.82(18) . . . . ?
C6 C7 C8 C9 -176.92(12) . . . . ?
C7 C8 C9 N1 -176.46(12) . . . . ?
C7 C8 C9 C13 1.14(19) . . . . ?
C8 C3 C4 C5 0.91(18) . . . . ?
C8 C9 C13 C14 54.38(17) . . . . ?
C8 C9 C13 C18 -129.45(13) . . . . ?
C9 N1 C1 O1 179.38(11) . . . . ?
C9 N1 C1 C2 -1.81(19) . . . . ?
C9 C13 C14 O4 1.86(17) . . . . ?
C9 C13 C14 C15 178.89(11) . . . . ?
C9 C13 C18 C17 -178.41(11) . . . . ?
C10 O1 C1 N1 0.50(17) . . . . ?
C10 O1 C1 C2 -178.40(11) . . . . ?
C11 O2 C5 C4 -3.21(18) . . . . ?
C11 O2 C5 C6 176.48(11) . . . . ?
C12 O3 C6 C5 -176.63(12) . . . . ?
C12 O3 C6 C7 4.13(19) . . . . ?
C13 C14 C15 C16 -1.96(19) . . . . ?
C14 C13 C18 C17 -2.02(18) . . . . ?
C14 C15 C16 C17 0.44(19) . . . . ?
C15 C16 C17 N2 -179.86(11) . . . . ?
C15 C16 C17 C18 0.25(19) . . . . ?
C16 C17 C18 C13 0.57(19) . . . . ?
C18 C13 C14 O4 -174.31(11) . . . . ?
C18 C13 C14 C15 2.71(17) . . . . ?
C19 O4 C14 C13 -169.29(11) . . . . ?
C19 O4 C14 C15 13.77(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_sh0205down
_database_code_depnum_ccdc_archive 'CCDC 2000639'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H21 N O5'
_chemical_formula_sum            'C20 H21 N O5'
_chemical_formula_weight         355.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6565(2)
_cell_length_b                   9.9527(2)
_cell_length_c                   20.7506(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.235(2)
_cell_angle_gamma                90.00
_cell_volume                     1777.20(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13673
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9150
_cell_measurement_theta_min      2.2690
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28695
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00 -14.00   0.50    8.60    --   10.60 -52.00 132.00   52
  2  ω      3.00  29.00   0.50    8.60    --  -10.90  52.00 -82.00   52
  3  ω    -64.00 -39.00   0.50    8.60    --  -10.90 -52.00 132.00   50
  4  ω    -15.00  40.00   0.50    8.60    --   10.60  82.00  60.00  110
  5  ω     43.00  73.00   0.50    8.60    --   10.60  19.00 120.00   60
  6  ω     21.00  87.00   0.50    8.60    --   10.60  82.00 150.00  132
  7  ω    -79.00  -8.00   0.50    8.60    --   10.60 -82.00 -90.00  142
  8  ω    -10.00  96.00   0.50    8.60    --   10.60  82.00 -30.00  212
  9  ω    -15.00 100.00   0.50    8.60    --   10.60  77.00 -90.00  230
 10  ω     22.00  49.00   0.50    8.60    --   10.60  77.00  30.00   54
 11  ω    -13.00  15.00   0.50    8.60    --   10.60  77.00  30.00   56
 12  ω    -15.00  12.00   0.50    8.60    --   10.60  82.00 150.00   54
 13  ω      5.00  31.00   0.50    8.60    --   10.60 -82.00 -90.00   52
 14  ω    -27.00  18.00   0.50    8.60    --   10.60  19.00 120.00   90
 15  ω    -84.00 -59.00   0.50    8.60    --  -10.90 -82.00 -30.00   50
 16  ω    -72.00 -18.00   0.50    8.60    --  -10.90 -82.00-150.00  108
 17  ω    -97.00  17.00   0.50    8.60    --  -10.90 -82.00 120.00  228
 18  ω    -49.00 -24.00   0.50    8.60    --  -10.90 -82.00  60.00   50
 19  ω    -18.00   7.00   0.50    8.60    --  -10.90 -82.00  90.00   50
 20  ω    -96.00 -69.00   0.50    8.60    --  -10.90 -82.00  60.00   54
 21  ω     -9.00  16.00   0.50    8.60    --  -10.90 -82.00 -30.00   50
 22  ω    -69.00 -28.00   0.50    8.60    --  -10.90 -82.00  90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0594768000
_diffrn_orient_matrix_UB_12      -0.0155805000
_diffrn_orient_matrix_UB_13      0.0197595000
_diffrn_orient_matrix_UB_21      0.0375976000
_diffrn_orient_matrix_UB_22      -0.0615148000
_diffrn_orient_matrix_UB_23      0.0090496000
_diffrn_orient_matrix_UB_31      0.0428949000
_diffrn_orient_matrix_UB_32      0.0323950000
_diffrn_orient_matrix_UB_33      0.0266701000
_diffrn_oxdiff_digest_frames     
;
0126b3a205291ef699f7e1abb21f8374d4000253e04
;
_diffrn_oxdiff_digest_hkl        
;
019a516f6cf94014a8a4bb4453f8688049f96f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_number_gt                2942
_reflns_number_total             3493
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0048(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0569P)²+2.3008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.7539(3) 0.10206(18) 0.47928(9) 0.0377(5) Uani 1 d . . .
O2 O 0.9247(2) 0.08285(16) 0.38527(8) 0.0285(4) Uani 1 d . . .
O3 O 0.8133(2) 0.55862(17) 0.27514(8) 0.0283(4) Uani 1 d . . .
O4 O 0.9863(2) 0.72655(16) 0.28733(8) 0.0247(4) Uani 1 d . . .
O5 O 0.7015(2) 0.58349(17) 0.53206(8) 0.0273(4) Uani 1 d . . .
N1 N 0.2979(3) 0.9386(3) 0.24144(11) 0.0371(6) Uani 1 d . . .
C1 C 0.8020(3) 0.2217(2) 0.45550(11) 0.0238(5) Uani 1 d . . .
C2 C 0.8943(3) 0.2106(2) 0.40428(11) 0.0213(5) Uani 1 d . . .
C3 C 0.9508(3) 0.3262(2) 0.37851(11) 0.0201(5) Uani 1 d . . .
H3 H 1.0141 0.3189 0.3440 0.024 Uiso 1 calc . . R
C4 C 0.9176(3) 0.4538(2) 0.40167(10) 0.0193(5) Uani 1 d . . .
C5 C 0.8223(3) 0.4640(2) 0.45127(11) 0.0202(5) Uani 1 d . . .
C6 C 0.7659(3) 0.3476(2) 0.47782(11) 0.0233(5) Uani 1 d . . .
H6 H 0.7015 0.3549 0.5119 0.028 Uiso 1 calc . . R
C7 C 0.7019(4) 0.1031(3) 0.54109(13) 0.0374(7) Uani 1 d . . .
H7A H 0.6042 0.1534 0.5395 0.056 Uiso 1 calc . . GR
H7B H 0.7803 0.1461 0.5720 0.056 Uiso 1 calc . . GR
H7C H 0.6849 0.0106 0.5549 0.056 Uiso 1 calc . . GR
C8 C 1.0093(3) 0.0683(3) 0.33025(12) 0.0276(6) Uani 1 d . . .
H8A H 0.9512 0.1106 0.2924 0.041 Uiso 1 calc . . GR
H8B H 1.0238 -0.0273 0.3215 0.041 Uiso 1 calc . . GR
H8C H 1.1110 0.1118 0.3391 0.041 Uiso 1 calc . . GR
C9 C 0.9930(3) 0.5729(2) 0.37298(11) 0.0210(5) Uani 1 d . . .
H9A H 1.1033 0.5510 0.3694 0.025 Uiso 1 calc . . R
H9B H 0.9908 0.6498 0.4031 0.025 Uiso 1 calc . . R
C10 C 0.9175(3) 0.6154(2) 0.30706(11) 0.0195(5) Uani 1 d . . .
C11 C 0.9256(3) 0.7765(3) 0.22424(12) 0.0312(6) Uani 1 d . . .
H11A H 0.9256 0.7041 0.1923 0.047 Uiso 1 calc . . GR
H11B H 0.9909 0.8506 0.2119 0.047 Uiso 1 calc . . GR
H11C H 0.8192 0.8089 0.2258 0.047 Uiso 1 calc . . GR
C12 C 0.7778(3) 0.6025(2) 0.47534(11) 0.0230(5) Uani 1 d . . .
H12 H 0.8746 0.6560 0.4869 0.028 Uiso 1 calc . . R
C13 C 0.6746(3) 0.6766(2) 0.42246(11) 0.0217(5) Uani 1 d . . .
C14 C 0.5410(3) 0.6155(2) 0.39225(12) 0.0248(5) Uani 1 d . . .
H14 H 0.5155 0.5269 0.4045 0.030 Uiso 1 calc . . R
C15 C 0.4450(3) 0.6812(3) 0.34493(12) 0.0264(5) Uani 1 d . . .
H15 H 0.3543 0.6385 0.3247 0.032 Uiso 1 calc . . R
C16 C 0.4834(3) 0.8122(2) 0.32718(11) 0.0239(5) Uani 1 d . . .
C17 C 0.6172(3) 0.8741(2) 0.35665(12) 0.0256(5) Uani 1 d . . .
H17 H 0.6438 0.9621 0.3441 0.031 Uiso 1 calc . . R
C18 C 0.7112(3) 0.8064(2) 0.40435(11) 0.0243(5) Uani 1 d . . .
H18 H 0.8017 0.8491 0.4249 0.029 Uiso 1 calc . . R
C19 C 0.3808(3) 0.8828(3) 0.27928(12) 0.0270(5) Uani 1 d . . .
C20 C 0.6691(3) 0.7069(3) 0.56213(12) 0.0288(6) Uani 1 d . . .
H20A H 0.5777 0.7488 0.5383 0.043 Uiso 1 calc . . GR
H20B H 0.7586 0.7671 0.5620 0.043 Uiso 1 calc . . GR
H20C H 0.6485 0.6900 0.6069 0.043 Uiso 1 calc . . GR


_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 C1 1.371(3) . ?
O1 C7 1.405(3) . ?
O2 C2 1.365(3) . ?
O2 C8 1.429(3) . ?
O3 C10 1.201(3) . ?
O4 C10 1.341(3) . ?
O4 C11 1.445(3) . ?
O5 C12 1.424(3) . ?
O5 C20 1.420(3) . ?
N1 C19 1.148(3) . ?
C1 C2 1.402(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.507(3) . ?
C5 C6 1.394(3) . ?
C5 C12 1.529(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 1.0000 . ?
C12 C13 1.528(3) . ?
C13 C14 1.394(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.404(3) . ?
C16 C17 1.393(3) . ?
C16 C19 1.442(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.5(2) . . ?
C2 O2 C8 117.17(18) . . ?
C10 O4 C11 115.54(18) . . ?
C20 O5 C12 112.36(18) . . ?
O1 C1 C2 115.1(2) . . ?
O1 C1 C6 125.3(2) . . ?
C6 C1 C2 119.6(2) . . ?
O2 C2 C1 115.9(2) . . ?
O2 C2 C3 125.2(2) . . ?
C3 C2 C1 118.9(2) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C9 117.7(2) . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C9 123.5(2) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 C12 119.9(2) . . ?
C6 C5 C12 120.5(2) . . ?
C1 C6 C5 121.3(2) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 108.6 . . ?
C4 C9 H9B 108.6 . . ?
C4 C9 C10 114.53(19) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
O3 C10 O4 123.5(2) . . ?
O3 C10 C9 126.3(2) . . ?
O4 C10 C9 110.19(19) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C5 107.86(18) . . ?
O5 C12 H12 108.9 . . ?
O5 C12 C13 111.70(19) . . ?
C5 C12 H12 108.9 . . ?
C13 C12 C5 110.43(19) . . ?
C13 C12 H12 108.9 . . ?
C14 C13 C12 120.3(2) . . ?
C18 C13 C12 120.6(2) . . ?
C18 C13 C14 119.1(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C19 119.2(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 C19 120.5(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
N1 C19 C16 179.3(3) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 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 C1 C2 O2 -0.4(3) . . . . ?
O1 C1 C2 C3 -178.5(2) . . . . ?
O1 C1 C6 C5 178.9(2) . . . . ?
O2 C2 C3 C4 -178.4(2) . . . . ?
O5 C12 C13 C14 -67.3(3) . . . . ?
O5 C12 C13 C18 111.9(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C9 176.3(2) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C3 C4 C5 C12 -177.1(2) . . . . ?
C3 C4 C9 C10 78.2(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C12 O5 -171.07(19) . . . . ?
C4 C5 C12 C13 66.6(3) . . . . ?
C4 C9 C10 O3 -5.3(3) . . . . ?
C4 C9 C10 O4 176.24(19) . . . . ?
C5 C4 C9 C10 -104.3(3) . . . . ?
C5 C12 C13 C14 52.7(3) . . . . ?
C5 C12 C13 C18 -128.1(2) . . . . ?
C6 C1 C2 O2 179.9(2) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C5 C12 O5 10.1(3) . . . . ?
C6 C5 C12 C13 -112.2(2) . . . . ?
C7 O1 C1 C2 161.7(2) . . . . ?
C7 O1 C1 C6 -18.6(4) . . . . ?
C8 O2 C2 C1 175.7(2) . . . . ?
C8 O2 C2 C3 -6.4(3) . . . . ?
C9 C4 C5 C6 -175.7(2) . . . . ?
C9 C4 C5 C12 5.4(3) . . . . ?
C11 O4 C10 O3 0.7(3) . . . . ?
C11 O4 C10 C9 179.2(2) . . . . ?
C12 C5 C6 C1 178.4(2) . . . . ?
C12 C13 C14 C15 179.2(2) . . . . ?
C12 C13 C18 C17 -179.6(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C13 C18 C17 -0.5(3) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C14 C15 C16 C19 -178.0(2) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C15 C16 C19 N1 44(28) . . . . ?
C16 C17 C18 C13 0.9(4) . . . . ?
C17 C16 C19 N1 -135(28) . . . . ?
C18 C13 C14 C15 0.0(4) . . . . ?
C19 C16 C17 C18 177.6(2) . . . . ?
C20 O5 C12 C5 174.06(19) . . . . ?
C20 O5 C12 C13 -64.4(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 1.319
_oxdiff_exptl_absorpt_empirical_full_min 0.754
