# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_k11204-myc-f_auto
_database_code_depnum_ccdc_archive 'CCDC 2311931'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 F2 N2 O6'
_chemical_formula_sum            'C18 H12 F2 N2 O6'
_chemical_formula_weight         390.30
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8953(2)
_cell_length_b                   10.6880(2)
_cell_length_c                   10.9838(2)
_cell_angle_alpha                68.919(2)
_cell_angle_beta                 77.025(2)
_cell_angle_gamma                82.949(2)
_cell_volume                     841.86(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13449
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8400
_cell_measurement_theta_min      2.0220
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.971
_diffrn_reflns_theta_min         2.026
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  41.00   0.50    1.28    --   10.60 -57.00   0.00  240
  2  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00-120.00  234
  3  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00   0.00  234
  4  ω    -79.00  36.00   0.50    1.28    --   10.60 -62.00 148.83  230
  5  ω    -79.00  36.00   0.50    1.28    --   10.60 -77.00  90.00  230
  6  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00 -60.00  234
  7  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00  90.00  234
  8  ω    -20.00 100.00   0.50    1.28    --   10.60  57.00-120.00  240
  9  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00 150.00  234
 10  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 -90.00  234
 11  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00-150.00  234
 12  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 150.00  234
 13  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 -30.00  234
 14  ω    -38.00 -10.00   0.50    1.28    --  -10.90  82.00   0.00   56
;
_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      -0.0001171000
_diffrn_orient_matrix_UB_12      -0.0591781000
_diffrn_orient_matrix_UB_13      0.0565478000
_diffrn_orient_matrix_UB_21      -0.0271483000
_diffrn_orient_matrix_UB_22      0.0386918000
_diffrn_orient_matrix_UB_23      0.0421823000
_diffrn_orient_matrix_UB_31      -0.0882067000
_diffrn_orient_matrix_UB_32      -0.0083892000
_diffrn_orient_matrix_UB_33      0.0013218000
_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                3065
_reflns_number_total             3516
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.012(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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.068
_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)+(0.0474P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1035
_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), C3(H3), C17(H17), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_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 0.55304(13) 0.64053(9) 1.08092(9) 0.0304(2) Uani 1 1 d . . . . .
F2 F 0.65656(12) 0.92208(9) 0.48345(9) 0.0300(2) Uani 1 1 d . . . . .
O2 O 0.07252(14) 0.72630(10) 1.02441(10) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.04635(14) 0.91274(10) 0.76359(10) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.09302(14) 0.82701(11) 0.59846(10) 0.0254(3) Uani 1 1 d . . . . .
O1 O 0.26277(15) 0.86907(12) 1.01864(12) 0.0334(3) Uani 1 1 d . . . . .
O5 O 0.28783(18) 0.51729(12) 0.67143(14) 0.0425(3) Uani 1 1 d . . . . .
N1 N 0.43672(16) 0.73604(12) 0.66320(12) 0.0192(3) Uani 1 1 d . . . . .
O6 O 0.14196(19) 0.55961(16) 0.51483(15) 0.0522(4) Uani 1 1 d . . . . .
N2 N 0.26101(19) 0.58108(14) 0.55921(15) 0.0317(3) Uani 1 1 d . . . . .
C7 C 0.33164(18) 0.75132(13) 0.86608(14) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.29444(18) 0.77707(13) 0.74290(14) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.13555(19) 0.84015(14) 0.69156(14) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.22121(19) 0.78947(14) 0.97726(14) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.50406(19) 0.69165(14) 0.86359(14) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.56655(19) 0.68316(14) 0.73619(14) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.6131(2) 0.63866(14) 0.95603(14) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.7315(2) 0.62809(15) 0.69896(15) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.771543 0.624357 0.612003 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4599(2) 0.75768(15) 0.52522(14) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.7745(2) 0.58396(15) 0.92388(16) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.846981 0.549150 0.988019 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3752(2) 0.68971(16) 0.47098(16) 0.0249(3) Uani 1 1 d . . . . .
C18 C 0.5708(2) 0.85629(15) 0.43398(15) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.8328(2) 0.57960(15) 0.79437(16) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.945827 0.541908 0.772254 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5939(2) 0.88860(16) 0.29899(16) 0.0288(4) Uani 1 1 d . . . . .
H17 H 0.670525 0.956411 0.240403 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3953(2) 0.72095(17) 0.33491(16) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.334620 0.673719 0.300702 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5037(2) 0.82071(17) 0.24950(16) 0.0298(4) Uani 1 1 d . . . . .
H16 H 0.516665 0.843077 0.156102 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1210(2) 0.97037(18) 0.73038(17) 0.0307(4) Uani 1 1 d . . . . .
H12A H -0.102929 1.036432 0.640051 0.046 Uiso 1 1 calc R U . . .
H12B H -0.180913 1.014470 0.793539 0.046 Uiso 1 1 calc R U . . .
H12C H -0.191945 0.899061 0.735145 0.046 Uiso 1 1 calc R U . . .
C9 C -0.0485(2) 0.76768(18) 1.12455(18) 0.0361(4) Uani 1 1 d . . . . .
H9A H -0.079880 0.863547 1.087252 0.054 Uiso 1 1 calc R U . . .
H9B H 0.005834 0.751430 1.201122 0.054 Uiso 1 1 calc R U . . .
H9C H -0.153484 0.716080 1.153105 0.054 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 C5 1.3537(17) . ?
F2 C18 1.3434(17) . ?
O2 C8 1.3313(18) . ?
O2 C9 1.4467(18) . ?
O4 C11 1.3345(17) . ?
O4 C12 1.4537(18) . ?
O3 C11 1.2031(17) . ?
O1 C8 1.2048(18) . ?
O5 N2 1.227(2) . ?
N1 C10 1.3907(18) . ?
N1 C1 1.3834(19) . ?
N1 C13 1.4204(18) . ?
O6 N2 1.2300(19) . ?
N2 C14 1.468(2) . ?
C7 C10 1.3724(19) . ?
C7 C8 1.4868(19) . ?
C7 C6 1.429(2) . ?
C10 C11 1.477(2) . ?
C6 C1 1.4072(19) . ?
C6 C5 1.397(2) . ?
C1 C2 1.398(2) . ?
C5 C4 1.362(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.409(2) . ?
C14 C15 1.385(2) . ?
C18 C17 1.370(2) . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(2) . ?
C16 H16 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C8 O2 C9 115.28(12) . . ?
C11 O4 C12 115.56(11) . . ?
C10 N1 C13 127.44(12) . . ?
C1 N1 C10 108.69(11) . . ?
C1 N1 C13 123.44(12) . . ?
O5 N2 O6 123.64(15) . . ?
O5 N2 C14 119.41(14) . . ?
O6 N2 C14 116.96(15) . . ?
C10 C7 C8 126.77(13) . . ?
C10 C7 C6 107.00(12) . . ?
C6 C7 C8 126.01(13) . . ?
N1 C10 C11 121.38(12) . . ?
C7 C10 N1 109.30(12) . . ?
C7 C10 C11 129.31(13) . . ?
O4 C11 C10 110.29(12) . . ?
O3 C11 O4 125.17(14) . . ?
O3 C11 C10 124.55(13) . . ?
O2 C8 C7 112.27(12) . . ?
O1 C8 O2 124.46(13) . . ?
O1 C8 C7 123.27(14) . . ?
C1 C6 C7 107.51(12) . . ?
C5 C6 C7 135.35(13) . . ?
C5 C6 C1 117.08(13) . . ?
N1 C1 C6 107.50(12) . . ?
N1 C1 C2 129.44(13) . . ?
C2 C1 C6 123.05(14) . . ?
F1 C5 C6 118.20(13) . . ?
F1 C5 C4 120.08(13) . . ?
C4 C5 C6 121.71(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.73(14) . . ?
C3 C2 H2 121.6 . . ?
C14 C13 N1 124.73(14) . . ?
C14 C13 C18 115.87(14) . . ?
C18 C13 N1 119.37(13) . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.24(14) . . ?
C3 C4 H4 120.4 . . ?
C13 C14 N2 119.77(14) . . ?
C15 C14 N2 118.22(14) . . ?
C15 C14 C13 122.01(15) . . ?
F2 C18 C13 117.24(13) . . ?
F2 C18 C17 119.48(14) . . ?
C17 C18 C13 123.28(14) . . ?
C2 C3 C4 122.17(14) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C18 C17 H17 120.6 . . ?
C18 C17 C16 118.82(15) . . ?
C16 C17 H17 120.6 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.68(15) . . ?
C16 C15 H15 120.2 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.31(15) . . ?
C15 C16 H16 119.8 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C4 C3 178.26(13) . . . . ?
F2 C18 C17 C16 -179.50(14) . . . . ?
O5 N2 C14 C13 -27.2(2) . . . . ?
O5 N2 C14 C15 152.64(15) . . . . ?
N1 C10 C11 O4 -157.69(12) . . . . ?
N1 C10 C11 O3 22.6(2) . . . . ?
N1 C1 C2 C3 -178.38(14) . . . . ?
N1 C13 C14 N2 -4.1(2) . . . . ?
N1 C13 C14 C15 176.04(14) . . . . ?
N1 C13 C18 F2 2.9(2) . . . . ?
N1 C13 C18 C17 -176.55(14) . . . . ?
O6 N2 C14 C13 152.75(15) . . . . ?
O6 N2 C14 C15 -27.4(2) . . . . ?
N2 C14 C15 C16 -178.91(14) . . . . ?
C7 C10 C11 O4 20.9(2) . . . . ?
C7 C10 C11 O3 -158.76(15) . . . . ?
C7 C6 C1 N1 0.07(16) . . . . ?
C7 C6 C1 C2 -179.24(13) . . . . ?
C7 C6 C5 F1 -0.6(2) . . . . ?
C7 C6 C5 C4 178.24(16) . . . . ?
C10 N1 C1 C6 -0.10(15) . . . . ?
C10 N1 C1 C2 179.15(15) . . . . ?
C10 N1 C13 C14 -74.3(2) . . . . ?
C10 N1 C13 C18 103.71(18) . . . . ?
C10 C7 C8 O2 65.58(18) . . . . ?
C10 C7 C8 O1 -114.12(18) . . . . ?
C10 C7 C6 C1 -0.01(16) . . . . ?
C10 C7 C6 C5 -176.93(16) . . . . ?
C8 C7 C10 N1 174.71(13) . . . . ?
C8 C7 C10 C11 -4.0(2) . . . . ?
C8 C7 C6 C1 -174.83(13) . . . . ?
C8 C7 C6 C5 8.2(3) . . . . ?
C6 C7 C10 N1 -0.06(15) . . . . ?
C6 C7 C10 C11 -178.79(13) . . . . ?
C6 C7 C8 O2 -120.60(15) . . . . ?
C6 C7 C8 O1 59.7(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C5 C4 C3 -0.5(2) . . . . ?
C1 N1 C10 C7 0.10(16) . . . . ?
C1 N1 C10 C11 178.95(12) . . . . ?
C1 N1 C13 C14 114.05(17) . . . . ?
C1 N1 C13 C18 -67.94(19) . . . . ?
C1 C6 C5 F1 -177.29(12) . . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C5 C6 C1 N1 177.64(12) . . . . ?
C5 C6 C1 C2 -1.7(2) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C13 N1 C10 C7 -172.55(13) . . . . ?
C13 N1 C10 C11 6.3(2) . . . . ?
C13 N1 C1 C6 172.90(12) . . . . ?
C13 N1 C1 C2 -7.8(2) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C13 C18 C17 C16 -0.1(2) . . . . ?
C14 C13 C18 F2 -178.94(13) . . . . ?
C14 C13 C18 C17 1.6(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C18 C13 C14 N2 177.78(13) . . . . ?
C18 C13 C14 C15 -2.0(2) . . . . ?
C18 C17 C16 C15 -1.2(2) . . . . ?
C12 O4 C11 O3 4.9(2) . . . . ?
C12 O4 C11 C10 -174.73(12) . . . . ?
C9 O2 C8 O1 5.1(2) . . . . ?
C9 O2 C8 C7 -174.56(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.770
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# 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_k11204-myc-a_auto
_database_code_depnum_ccdc_archive 'CCDC 2311933'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Br Cl N O4'
_chemical_formula_sum            'C14 H13 Br Cl N O4'
_chemical_formula_weight         374.61
_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'
Br Br -0.2901 2.4595 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4292(3)
_cell_length_b                   16.5544(8)
_cell_length_c                   12.3299(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.297(4)
_cell_angle_gamma                90
_cell_volume                     1507.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10040
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.6450
_cell_measurement_theta_min      2.0620
_shelx_estimated_absorpt_T_max   0.593
_shelx_estimated_absorpt_T_min   0.323
_exptl_absorpt_coefficient_mu    2.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20549
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.083
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  38.00   0.50    2.67    --   10.60 -82.00 -83.00  234
  2  ω    -17.00 100.00   0.50    2.67    --   10.60  82.00  37.00  234
  3  ω    -38.00  73.00   0.50    2.67    --  -10.90  82.00  37.00  222
  4  ω    -49.00 -11.00   0.50    2.67    --  -10.90 -82.00 -83.00   76
  5  ω    -33.00  -1.00   0.50    2.67    --   10.60 -82.00-150.00   64
  6  ω     -8.00  18.00   0.50    2.67    --   10.60  77.00-150.00   52
  7  ω    -79.00 100.00   0.50    2.67    --   10.60  19.00  90.00  358
  8  ω    -85.00  20.00   0.50    2.67    --  -10.90 -57.00 -90.00  210
  9  ω    -38.00  47.00   0.50    2.67    --  -10.90  82.00-180.00  170
;
_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      0.0386230000
_diffrn_orient_matrix_UB_12      -0.0342161000
_diffrn_orient_matrix_UB_13      -0.0232177000
_diffrn_orient_matrix_UB_21      -0.0299611000
_diffrn_orient_matrix_UB_22      0.0144721000
_diffrn_orient_matrix_UB_23      -0.0530393000
_diffrn_orient_matrix_UB_31      0.0827086000
_diffrn_orient_matrix_UB_32      0.0212648000
_diffrn_orient_matrix_UB_33      -0.0010979000
_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                2704
_reflns_number_total             3138
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.253
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.024
_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)+(0.0347P)²+2.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10(H10A,H10B,H10C)
;
_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
Br1 Br 0.79411(4) 0.42922(2) 0.79841(2) 0.02683(11) Uani 1 1 d . . . . .
Cl1 Cl 0.77858(10) 0.73293(4) 0.61492(6) 0.02428(18) Uani 1 1 d . . . . .
O4 O 0.0257(2) 0.71806(12) 0.39243(15) 0.0192(4) Uani 1 1 d . . . . .
O2 O 0.3089(3) 0.81344(12) 0.54080(15) 0.0209(4) Uani 1 1 d . . . . .
O1 O 0.4483(3) 0.77823(13) 0.39435(16) 0.0250(5) Uani 1 1 d . . . . .
O3 O -0.0832(3) 0.59409(12) 0.41973(17) 0.0241(5) Uani 1 1 d . . . . .
N1 N 0.2413(3) 0.55497(14) 0.54627(19) 0.0187(5) Uani 1 1 d . . . . .
H1 H 0.162903 0.515006 0.544488 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4124(4) 0.55382(17) 0.5985(2) 0.0164(6) Uani 1 1 d . . . . .
C5 C 0.7601(4) 0.58255(18) 0.6943(2) 0.0210(6) Uani 1 1 d . . . . .
H5 H 0.879685 0.591180 0.728124 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4944(4) 0.62895(17) 0.5812(2) 0.0162(6) Uani 1 1 d . . . . .
C3 C 0.4992(4) 0.49238(18) 0.6619(2) 0.0193(6) Uani 1 1 d . . . . .
H3 H 0.442502 0.441916 0.671997 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6710(4) 0.50919(18) 0.7085(2) 0.0209(6) Uani 1 1 d . . . . .
C7 C 0.3632(4) 0.67659(17) 0.5166(2) 0.0163(6) Uani 1 1 d . . . . .
C11 C 0.2110(4) 0.62898(17) 0.4967(2) 0.0177(6) Uani 1 1 d . . . . .
C8 C 0.3805(4) 0.76053(17) 0.4755(2) 0.0174(6) Uani 1 1 d . . . . .
C6 C 0.6719(4) 0.64173(17) 0.6309(2) 0.0173(6) Uani 1 1 d . . . . .
C12 C 0.0358(4) 0.64412(18) 0.4326(2) 0.0188(6) Uani 1 1 d . . . . .
C13 C -0.1424(4) 0.74127(19) 0.3267(2) 0.0240(7) Uani 1 1 d . . . . .
H13A H -0.247130 0.713942 0.353853 0.029 Uiso 1 1 calc R U . . .
H13B H -0.137759 0.725736 0.249480 0.029 Uiso 1 1 calc R U . . .
C14 C -0.1601(4) 0.83089(19) 0.3363(3) 0.0261(7) Uani 1 1 d . . . . .
H14A H -0.267996 0.849158 0.289900 0.039 Uiso 1 1 calc R U . . .
H14B H -0.052509 0.857067 0.312977 0.039 Uiso 1 1 calc R U . . .
H14C H -0.171558 0.845181 0.412385 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3031(4) 0.89659(18) 0.5037(2) 0.0242(7) Uani 1 1 d . . . . .
H9A H 0.234954 0.900680 0.430211 0.029 Uiso 1 1 calc R U . . .
H9B H 0.427230 0.917318 0.499902 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2098(5) 0.9444(2) 0.5852(3) 0.0354(8) Uani 1 1 d . . . . .
H10A H 0.202970 1.001267 0.563154 0.053 Uiso 1 1 calc R U . . .
H10B H 0.278600 0.939735 0.657425 0.053 Uiso 1 1 calc R U . . .
H10C H 0.087242 0.923207 0.588037 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.896(3) . ?
Cl1 C6 1.727(3) . ?
O4 C12 1.319(3) . ?
O4 C13 1.464(3) . ?
O2 C8 1.339(3) . ?
O2 C9 1.450(3) . ?
O1 C8 1.205(3) . ?
O3 C12 1.209(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.361(3) . ?
N1 C11 1.377(4) . ?
C2 C1 1.412(4) . ?
C2 C3 1.397(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.403(4) . ?
C5 C6 1.374(4) . ?
C1 C7 1.427(4) . ?
C1 C6 1.408(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(4) . ?
C7 C11 1.378(4) . ?
C7 C8 1.489(4) . ?
C11 C12 1.468(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.495(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.506(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C12 O4 C13 117.5(2) . . ?
C8 O2 C9 115.5(2) . . ?
C2 N1 H1 125.6 . . ?
C2 N1 C11 108.8(2) . . ?
C11 N1 H1 125.6 . . ?
N1 C2 C1 108.2(2) . . ?
N1 C2 C3 128.7(3) . . ?
C3 C2 C1 123.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.1(3) . . ?
C2 C1 C7 106.9(2) . . ?
C6 C1 C2 117.8(2) . . ?
C6 C1 C7 135.2(3) . . ?
C2 C3 H3 122.0 . . ?
C4 C3 C2 116.0(3) . . ?
C4 C3 H3 122.0 . . ?
C5 C4 Br1 118.3(2) . . ?
C3 C4 Br1 118.1(2) . . ?
C3 C4 C5 123.6(3) . . ?
C1 C7 C8 128.8(2) . . ?
C11 C7 C1 106.3(2) . . ?
C11 C7 C8 124.9(2) . . ?
N1 C11 C7 109.8(2) . . ?
N1 C11 C12 118.9(2) . . ?
C7 C11 C12 131.3(3) . . ?
O2 C8 C7 110.5(2) . . ?
O1 C8 O2 124.8(3) . . ?
O1 C8 C7 124.7(3) . . ?
C5 C6 Cl1 119.5(2) . . ?
C5 C6 C1 120.4(3) . . ?
C1 C6 Cl1 120.1(2) . . ?
O4 C12 C11 111.8(2) . . ?
O3 C12 O4 125.1(3) . . ?
O3 C12 C11 123.1(3) . . ?
O4 C13 H13A 110.3 . . ?
O4 C13 H13B 110.3 . . ?
O4 C13 C14 107.1(2) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
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 . . ?
O2 C9 H9A 110.4 . . ?
O2 C9 H9B 110.4 . . ?
O2 C9 C10 106.7(3) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C1 C7 0.7(3) . . . . ?
N1 C2 C1 C6 178.3(2) . . . . ?
N1 C2 C3 C4 -177.5(3) . . . . ?
N1 C11 C12 O4 178.5(2) . . . . ?
N1 C11 C12 O3 -1.1(4) . . . . ?
C2 N1 C11 C7 0.0(3) . . . . ?
C2 N1 C11 C12 178.6(2) . . . . ?
C2 C1 C7 C11 -0.7(3) . . . . ?
C2 C1 C7 C8 -180.0(3) . . . . ?
C2 C1 C6 Cl1 -178.9(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C3 C4 Br1 178.51(19) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C1 C7 C11 N1 0.5(3) . . . . ?
C1 C7 C11 C12 -177.9(3) . . . . ?
C1 C7 C8 O2 -97.8(3) . . . . ?
C1 C7 C8 O1 82.7(4) . . . . ?
C3 C2 C1 C7 -177.8(2) . . . . ?
C3 C2 C1 C6 -0.2(4) . . . . ?
C4 C5 C6 Cl1 178.8(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C7 C1 C6 Cl1 -2.2(4) . . . . ?
C7 C1 C6 C5 176.5(3) . . . . ?
C7 C11 C12 O4 -3.2(4) . . . . ?
C7 C11 C12 O3 177.1(3) . . . . ?
C11 N1 C2 C1 -0.4(3) . . . . ?
C11 N1 C2 C3 178.0(3) . . . . ?
C11 C7 C8 O2 83.1(3) . . . . ?
C11 C7 C8 O1 -96.4(4) . . . . ?
C8 O2 C9 C10 177.1(2) . . . . ?
C8 C7 C11 N1 179.8(2) . . . . ?
C8 C7 C11 C12 1.4(5) . . . . ?
C6 C5 C4 Br1 -178.9(2) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C6 C1 C7 C11 -177.7(3) . . . . ?
C6 C1 C7 C8 3.0(5) . . . . ?
C12 O4 C13 C14 153.2(2) . . . . ?
C13 O4 C12 O3 -0.3(4) . . . . ?
C13 O4 C12 C11 -180.0(2) . . . . ?
C9 O2 C8 O1 4.8(4) . . . . ?
C9 O2 C8 C7 -174.7(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 5.429
_oxdiff_exptl_absorpt_empirical_full_min 0.489
####################################################################### 
# 
# 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_k11211-myc-g(chnf3047)_auto
_database_code_depnum_ccdc_archive 'CCDC 2311934'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cl2 N2 O3'
_chemical_formula_sum            'C18 H12 Cl2 N2 O3'
_chemical_formula_weight         375.20
_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                   8.2481(2)
_cell_length_b                   10.2725(2)
_cell_length_c                   10.6752(2)
_cell_angle_alpha                68.739(2)
_cell_angle_beta                 77.265(2)
_cell_angle_gamma                87.293(2)
_cell_volume                     821.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13779
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8030
_cell_measurement_theta_min      2.0940
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22394
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.044
_diffrn_reflns_theta_min         2.098
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_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    -23.00 100.00   0.50    1.11    --   10.60  50.00 -26.00  246
  2  ω    -79.00  44.00   0.50    1.11    --   10.60 -50.00-172.00  246
  3  ω    -44.00  78.00   0.50    1.11    --  -10.90  50.00 -26.00  244
  4  ω   -100.00  22.00   0.50    1.11    --  -10.90 -50.00-172.00  244
  5  ω    -17.00 100.00   0.50    1.11    --   10.60  82.00  90.00  234
  6  ω    -17.00 100.00   0.50    1.11    --   10.60  82.00  30.00  234
  7  ω    -17.00 100.00   0.50    1.11    --   10.60  82.00 -90.00  234
  8  ω    -17.00 100.00   0.50    1.11    --   10.60  82.00   0.00  234
  9  ω    -42.00  34.00   0.50    1.11    --   10.60 -82.00 127.72  152
 10  ω    -71.00 -45.00   0.50    1.11    --   10.60 -37.00-150.00   52
 11  ω    -19.00  16.00   0.50    1.11    --   10.60 -37.00-150.00   70
 12  ω     15.00 100.00   0.50    1.11    --   10.60  77.00-150.00  170
 13  ω    -17.00  33.00   0.50    1.11    --   10.60  82.00-120.00  100
 14  ω     75.00 100.00   0.50    1.11    --   10.60  82.00-120.00   50
 15  ω     -5.00 100.00   0.50    1.11    --   10.60  82.00 -60.00  210
 16  ω    -44.00  17.00   0.50    1.11    --  -10.90 -82.00  30.00  122
 17  ω   -100.00   8.00   0.50    1.11    --  -10.90 -82.00 150.00  216
 18  ω    -82.00 -47.00   0.50    1.11    --  -10.90 -77.00  90.00   70
;
_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      -0.0573779000
_diffrn_orient_matrix_UB_12      -0.0530358000
_diffrn_orient_matrix_UB_13      0.0075231000
_diffrn_orient_matrix_UB_21      0.0436604000
_diffrn_orient_matrix_UB_22      -0.0504124000
_diffrn_orient_matrix_UB_23      0.0445224000
_diffrn_orient_matrix_UB_31      -0.0508393000
_diffrn_orient_matrix_UB_32      0.0119342000
_diffrn_orient_matrix_UB_33      0.0574360000
_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                3060
_reflns_number_total             3443
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     402
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.071
_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)+(0.0517P)²+0.4544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C15 \\sim C14 \\sim C7 \\sim C12 \\sim C1 \\sim C13 \\sim C5 \\sim C9
\\sim C8 \\sim C2 \\sim C4 \\sim C10 \\sim C16 \\sim C3 \\sim C11 \\sim C17
\\sim C18: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 3.8A
3.a Secondary CH2 refined with riding coordinates:
 C17(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H005), C9(H00G), C8(H00H), C2(H00I), C4(H00J), C10(H00K), C3(H00M)
3.c Idealised Me refined as rotating group:
 C18(H00C,H00D,H00E)
;
_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
Cl01 Cl 0.84502(5) 0.60485(5) 0.76114(5) 0.02816(13) Uani 1 1 d . . . . .
Cl02 Cl 0.52963(7) 0.10429(5) 0.58254(6) 0.04534(17) Uani 1 1 d . . . . .
O003 O 0.07734(14) 0.35649(12) 0.94629(13) 0.0240(3) Uani 1 1 d . . . . .
O004 O 0.24418(17) 0.06918(13) 0.91691(15) 0.0382(3) Uani 1 1 d . . . . .
N005 N 0.20731(16) 0.56348(14) 0.90379(15) 0.0212(3) Uani 1 1 d . . . . .
H005 H 0.112135 0.600231 0.927033 0.025 Uiso 1 1 calc R U . . .
N006 N 0.49111(16) 0.49219(14) 0.76058(14) 0.0193(3) Uani 1 1 d . . . . .
O5 O 0.1523(2) 0.19817(17) 0.72732(15) 0.0476(4) Uani 1 1 d . . . . .
C008 C 0.5036(2) 0.60302(16) 0.80725(17) 0.0193(3) Uani 1 1 d . U . . .
C009 C 0.2032(2) 0.43417(17) 0.89830(17) 0.0201(3) Uani 1 1 d . U . . .
C00A C 0.35556(19) 0.39693(17) 0.82189(17) 0.0200(3) Uani 1 1 d . U . . .
C00B C 0.5929(2) 0.45188(17) 0.65919(17) 0.0206(3) Uani 1 1 d . U . . .
C00C C 0.5262(2) 0.32305(17) 0.66913(17) 0.0220(3) Uani 1 1 d . U . . .
C00D C 0.3539(2) 0.64218(17) 0.87470(17) 0.0202(3) Uani 1 1 d . U . . .
C00E C 0.3756(2) 0.29023(17) 0.77240(18) 0.0228(3) Uani 1 1 d . U . . .
C00F C 0.6504(2) 0.66884(17) 0.80380(17) 0.0216(3) Uani 1 1 d . U . . .
C00G C 0.7976(2) 0.45978(19) 0.46128(18) 0.0262(4) Uani 1 1 d . U . . .
H00G H 0.888995 0.505945 0.388826 0.031 Uiso 1 1 calc R U . . .
C00H C 0.7242(2) 0.52409(18) 0.55169(17) 0.0224(3) Uani 1 1 d . U . . .
H00H H 0.761604 0.614265 0.541227 0.027 Uiso 1 1 calc R U . . .
C00I C 0.3492(2) 0.75379(17) 0.91963(18) 0.0253(4) Uani 1 1 d . U . . .
H00I H 0.246094 0.781120 0.961396 0.030 Uiso 1 1 calc R U . . .
C00J C 0.6457(2) 0.78020(18) 0.84872(19) 0.0267(4) Uani 1 1 d . U . . .
H00J H 0.746374 0.826051 0.841922 0.032 Uiso 1 1 calc R U . . .
C00K C 0.7414(2) 0.3286(2) 0.47303(19) 0.0287(4) Uani 1 1 d . U . . .
H00K H 0.796823 0.285718 0.410879 0.034 Uiso 1 1 calc R U . . .
C00L C 0.2519(2) 0.17197(19) 0.81598(19) 0.0287(4) Uani 1 1 d . U . . .
C00M C 0.4949(2) 0.82479(18) 0.9034(2) 0.0288(4) Uani 1 1 d . U . . .
H00M H 0.491752 0.904038 0.929669 0.035 Uiso 1 1 calc R U . . .
C00N C 0.6060(2) 0.26163(19) 0.57446(19) 0.0271(4) Uani 1 1 d . U . . .
C00O C 0.0226(4) 0.0934(3) 0.7542(3) 0.0744(10) Uani 1 1 d . U . . .
H00A H 0.017119 0.020227 0.846281 0.089 Uiso 1 1 calc R U . . .
H00B H -0.086518 0.137930 0.754293 0.089 Uiso 1 1 calc R U . . .
C00P C 0.0552(5) 0.0317(5) 0.6535(4) 0.1180(18) Uani 1 1 d . U . . .
H00C H 0.074922 0.105115 0.561687 0.177 Uiso 1 1 calc R U . . .
H00D H -0.040501 -0.027956 0.665367 0.177 Uiso 1 1 calc R U . . .
H00E H 0.153920 -0.024841 0.663203 0.177 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
Cl01 C00F 1.7356(16) . ?
Cl02 C00N 1.7284(18) . ?
O003 C009 1.235(2) . ?
O004 C00L 1.196(2) . ?
N005 H005 0.8800 . ?
N005 C009 1.353(2) . ?
N005 C00D 1.398(2) . ?
N006 C008 1.414(2) . ?
N006 C00A 1.397(2) . ?
N006 C00B 1.393(2) . ?
O5 C00L 1.334(2) . ?
O5 C00O 1.461(2) . ?
C008 C00D 1.406(2) . ?
C008 C00F 1.401(2) . ?
C009 C00A 1.456(2) . ?
C00A C00E 1.368(2) . ?
C00B C00C 1.417(2) . ?
C00B C00H 1.396(2) . ?
C00C C00E 1.427(2) . ?
C00C C00N 1.408(2) . ?
C00D C00I 1.390(2) . ?
C00E C00L 1.494(2) . ?
C00F C00J 1.388(2) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.379(2) . ?
C00G C00K 1.399(3) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00I C00M 1.380(2) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.384(3) . ?
C00K H00K 0.9500 . ?
C00K C00N 1.376(3) . ?
C00M H00M 0.9500 . ?
C00O H00A 0.9900 . ?
C00O H00B 0.9900 . ?
C00O C00P 1.407(4) . ?
C00P H00C 0.9800 . ?
C00P H00D 0.9800 . ?
C00P H00E 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
C009 N005 H005 118.1 . . ?
C009 N005 C00D 123.86(14) . . ?
C00D N005 H005 118.1 . . ?
C00A N006 C008 119.81(13) . . ?
C00B N006 C008 132.67(14) . . ?
C00B N006 C00A 107.51(13) . . ?
C00L O5 C00O 117.96(19) . . ?
C00D C008 N006 116.13(14) . . ?
C00F C008 N006 126.67(14) . . ?
C00F C008 C00D 116.95(15) . . ?
O003 C009 N005 123.05(14) . . ?
O003 C009 C00A 121.99(15) . . ?
N005 C009 C00A 114.80(14) . . ?
N006 C00A C009 120.14(14) . . ?
C00E C00A N006 110.62(14) . . ?
C00E C00A C009 127.47(15) . . ?
N006 C00B C00C 107.21(14) . . ?
N006 C00B C00H 130.49(15) . . ?
C00H C00B C00C 121.80(15) . . ?
C00B C00C C00E 108.09(14) . . ?
C00N C00C C00B 118.11(15) . . ?
C00N C00C C00E 133.53(16) . . ?
N005 C00D C008 119.67(14) . . ?
C00I C00D N005 118.84(15) . . ?
C00I C00D C008 121.41(15) . . ?
C00A C00E C00C 106.23(15) . . ?
C00A C00E C00L 124.01(15) . . ?
C00C C00E C00L 129.61(15) . . ?
C008 C00F Cl01 122.10(13) . . ?
C00J C00F Cl01 116.48(13) . . ?
C00J C00F C008 121.08(15) . . ?
C00H C00G H00G 119.0 . . ?
C00H C00G C00K 121.98(16) . . ?
C00K C00G H00G 119.0 . . ?
C00B C00H H00H 121.2 . . ?
C00G C00H C00B 117.60(16) . . ?
C00G C00H H00H 121.2 . . ?
C00D C00I H00I 120.1 . . ?
C00M C00I C00D 119.83(16) . . ?
C00M C00I H00I 120.1 . . ?
C00F C00J H00J 119.9 . . ?
C00M C00J C00F 120.30(16) . . ?
C00M C00J H00J 119.9 . . ?
C00G C00K H00K 120.0 . . ?
C00N C00K C00G 120.08(16) . . ?
C00N C00K H00K 120.0 . . ?
O004 C00L O5 125.48(17) . . ?
O004 C00L C00E 124.07(18) . . ?
O5 C00L C00E 110.45(15) . . ?
C00I C00M C00J 119.82(16) . . ?
C00I C00M H00M 120.1 . . ?
C00J C00M H00M 120.1 . . ?
C00C C00N Cl02 119.87(14) . . ?
C00K C00N Cl02 119.94(14) . . ?
C00K C00N C00C 120.16(17) . . ?
O5 C00O H00A 109.5 . . ?
O5 C00O H00B 109.5 . . ?
H00A C00O H00B 108.1 . . ?
C00P C00O O5 110.7(2) . . ?
C00P C00O H00A 109.5 . . ?
C00P C00O H00B 109.5 . . ?
C00O C00P H00C 109.5 . . ?
C00O C00P H00D 109.5 . . ?
C00O C00P H00E 109.5 . . ?
H00C C00P H00D 109.5 . . ?
H00C C00P H00E 109.5 . . ?
H00D C00P H00E 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
Cl01 C00F C00J C00M -170.73(14) . . . . ?
O003 C009 C00A N006 175.24(15) . . . . ?
O003 C009 C00A C00E 11.9(3) . . . . ?
N005 C009 C00A N006 -0.3(2) . . . . ?
N005 C009 C00A C00E -163.64(17) . . . . ?
N005 C00D C00I C00M 174.02(16) . . . . ?
N006 C008 C00D N005 6.2(2) . . . . ?
N006 C008 C00D C00I -177.06(15) . . . . ?
N006 C008 C00F Cl01 -9.2(2) . . . . ?
N006 C008 C00F C00J 177.76(16) . . . . ?
N006 C00A C00E C00C -3.39(19) . . . . ?
N006 C00A C00E C00L -179.32(16) . . . . ?
N006 C00B C00C C00E 3.79(18) . . . . ?
N006 C00B C00C C00N 178.61(15) . . . . ?
N006 C00B C00H C00G -176.45(16) . . . . ?
C008 N006 C00A C009 20.5(2) . . . . ?
C008 N006 C00A C00E -173.60(14) . . . . ?
C008 N006 C00B C00C 173.54(16) . . . . ?
C008 N006 C00B C00H -14.7(3) . . . . ?
C008 C00D C00I C00M -2.7(3) . . . . ?
C008 C00F C00J C00M 2.7(3) . . . . ?
C009 N005 C00D C008 14.7(2) . . . . ?
C009 N005 C00D C00I -162.12(16) . . . . ?
C009 C00A C00E C00C 161.24(16) . . . . ?
C009 C00A C00E C00L -14.7(3) . . . . ?
C00A N006 C008 C00D -23.0(2) . . . . ?
C00A N006 C008 C00F 151.05(16) . . . . ?
C00A N006 C00B C00C -5.78(17) . . . . ?
C00A N006 C00B C00H 166.02(17) . . . . ?
C00A C00E C00L O004 -83.9(2) . . . . ?
C00A C00E C00L O5 95.8(2) . . . . ?
C00B N006 C008 C00D 157.77(16) . . . . ?
C00B N006 C008 C00F -28.2(3) . . . . ?
C00B N006 C00A C009 -160.09(15) . . . . ?
C00B N006 C00A C00E 5.83(18) . . . . ?
C00B C00C C00E C00A -0.29(19) . . . . ?
C00B C00C C00E C00L 175.34(17) . . . . ?
C00B C00C C00N Cl02 179.87(13) . . . . ?
C00B C00C C00N C00K -2.1(3) . . . . ?
C00C C00B C00H C00G -5.7(2) . . . . ?
C00C C00E C00L O004 101.2(2) . . . . ?
C00C C00E C00L O5 -79.2(2) . . . . ?
C00D N005 C009 O003 167.22(16) . . . . ?
C00D N005 C009 C00A -17.3(2) . . . . ?
C00D C008 C00F Cl01 164.78(13) . . . . ?
C00D C008 C00F C00J -8.3(2) . . . . ?
C00D C00I C00M C00J -3.2(3) . . . . ?
C00E C00C C00N Cl02 -6.9(3) . . . . ?
C00E C00C C00N C00K 171.08(19) . . . . ?
C00F C008 C00D N005 -168.41(15) . . . . ?
C00F C008 C00D C00I 8.3(2) . . . . ?
C00F C00J C00M C00I 3.2(3) . . . . ?
C00G C00K C00N Cl02 176.28(14) . . . . ?
C00G C00K C00N C00C -1.7(3) . . . . ?
C00H C00B C00C C00E -168.88(15) . . . . ?
C00H C00B C00C C00N 5.9(2) . . . . ?
C00H C00G C00K C00N 2.0(3) . . . . ?
C00K C00G C00H C00B 1.7(3) . . . . ?
C00L O5 C00O C00P -112.5(3) . . . . ?
C00N C00C C00E C00A -173.98(19) . . . . ?
C00N C00C C00E C00L 1.6(3) . . . . ?
C00O O5 C00L O004 -0.1(3) . . . . ?
C00O O5 C00L C00E -179.8(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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.662
####################################################################### 
# 
# 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_k11111-myc-h(chq3739)_auto
_database_code_depnum_ccdc_archive 'CCDC 2311932'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Cl2 N2 O6'
_chemical_formula_sum            'C20 H16 Cl2 N2 O6'
_chemical_formula_weight         451.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.0746(2)
_cell_length_b                   8.2867(3)
_cell_length_c                   16.9277(3)
_cell_angle_alpha                95.590(2)
_cell_angle_beta                 98.647(2)
_cell_angle_gamma                114.340(3)
_cell_volume                     1004.16(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14652
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8580
_cell_measurement_theta_min      2.4620
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.473
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_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    -17.00 100.00   0.50    3.10    --   10.60  82.00 -30.00  234
  2  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00   0.00  234
  3  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-150.00  234
  4  ω    -79.00  36.00   0.50    3.10    --   10.60 -77.00 150.00  230
  5  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-180.00  234
  6  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-120.00  234
  7  ω   -100.00  17.00   0.50    3.10    --  -10.90 -82.00 -30.00  234
  8  ω    -41.00  79.00   0.50    3.10    --  -10.90  57.00  60.00  240
  9  ω   -100.00  15.00   0.50    3.10    --  -10.90 -77.00  30.00  230
 10  ω    -48.00  79.00   0.50    3.10    --  -10.90  37.00 -90.00  254
 11  ω    -38.00  79.00   0.50    3.10    --  -10.90  82.00  60.00  234
 12  ω    -36.00  79.00   0.50    3.10    --  -10.90  77.00 120.00  230
 13  ω    -38.00   6.00   0.50    3.10    --  -10.90  82.00-150.00   88
 14  ω    -38.00  79.00   0.50    3.10    --  -10.90  82.00 -60.00  234
;
_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      0.0198737000
_diffrn_orient_matrix_UB_12      0.0025064000
_diffrn_orient_matrix_UB_13      0.0424883000
_diffrn_orient_matrix_UB_21      -0.0398742000
_diffrn_orient_matrix_UB_22      0.0609081000
_diffrn_orient_matrix_UB_23      0.0061671000
_diffrn_orient_matrix_UB_31      -0.0879753000
_diffrn_orient_matrix_UB_32      -0.0734491000
_diffrn_orient_matrix_UB_33      -0.0033379000
_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                3037
_reflns_number_total             3539
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.055
_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)+(0.0486P)²+0.8160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1073
_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. Rigid bond restraints
 O2, N2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C2(H2), C3(H3), C4(H4)
3.c 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
Cl2 Cl 1.07588(9) 1.04983(9) 0.60402(4) 0.04676(19) Uani 1 1 d . . . . .
O4 O 0.3697(2) 0.6245(2) 0.69134(9) 0.0333(4) Uani 1 1 d . . . . .
O6 O 0.6105(2) 0.7560(2) 0.56366(9) 0.0317(4) Uani 1 1 d . . . . .
O5 O 0.6376(3) 1.0062(2) 0.63998(10) 0.0411(4) Uani 1 1 d . . . . .
O3 O 0.4207(2) 0.5404(3) 0.81137(10) 0.0427(4) Uani 1 1 d . . . . .
N2 N 0.7437(3) 0.8956(2) 0.95423(10) 0.0272(4) Uani 1 1 d . U . . .
N1 N 0.8120(2) 0.7181(2) 0.81689(10) 0.0246(4) Uani 1 1 d . . . . .
O2 O 0.8615(3) 1.0103(2) 0.92781(11) 0.0452(4) Uani 1 1 d . U . . .
O1 O 0.6183(3) 0.9075(2) 0.97991(11) 0.0453(4) Uani 1 1 d . . . . .
C15 C 0.7872(3) 0.6378(3) 0.88756(12) 0.0233(4) Uani 1 1 d . . . . .
C20 C 0.7885(3) 0.4715(3) 0.89037(12) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.7581(3) 0.7212(3) 0.95611(12) 0.0240(4) Uani 1 1 d . . . . .
C9 C 0.6610(3) 0.8720(3) 0.63267(13) 0.0296(5) Uani 1 1 d . . . . .
C17 C 0.7341(3) 0.6464(3) 1.02554(12) 0.0270(5) Uani 1 1 d . . . . .
H17 H 0.712871 0.705736 1.071137 0.032 Uiso 1 1 calc R U . . .
C1 C 0.9828(3) 0.8190(3) 0.80030(13) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.7565(3) 0.8196(3) 0.70143(12) 0.0265(5) Uani 1 1 d . . . . .
C18 C 0.7418(3) 0.4833(3) 1.02684(13) 0.0284(5) Uani 1 1 d . . . . .
H18 H 0.729858 0.431657 1.074577 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6747(3) 0.7199(3) 0.75674(12) 0.0248(4) Uani 1 1 d . . . . .
C12 C 0.4769(3) 0.6191(3) 0.75781(12) 0.0278(5) Uani 1 1 d . . . . .
C19 C 0.7667(3) 0.3944(3) 0.95960(13) 0.0281(5) Uani 1 1 d . . . . .
H19 H 0.768828 0.280871 0.960696 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9525(3) 0.8821(3) 0.72757(13) 0.0266(5) Uani 1 1 d . . . . .
C2 C 1.1603(3) 0.8604(3) 0.84437(14) 0.0302(5) Uani 1 1 d . . . . .
H2 H 1.177760 0.818791 0.893885 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5183(3) 0.7990(3) 0.49369(13) 0.0342(5) Uani 1 1 d . . . . .
H10A H 0.604102 0.913929 0.480565 0.041 Uiso 1 1 calc R U . . .
H10B H 0.407764 0.811959 0.505757 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1094(3) 0.9831(3) 0.69701(14) 0.0339(5) Uani 1 1 d . . . . .
C3 C 1.3089(3) 0.9645(3) 0.81274(15) 0.0373(5) Uani 1 1 d . . . . .
H3 H 1.431543 0.997522 0.841903 0.045 Uiso 1 1 calc R U . . .
C4 C 1.2844(3) 1.0231(3) 0.73881(15) 0.0395(6) Uani 1 1 d . . . . .
H4 H 1.389510 1.090863 0.717621 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4611(4) 0.6497(3) 0.42335(14) 0.0388(6) Uani 1 1 d . . . . .
H11A H 0.406974 0.680422 0.374632 0.058 Uiso 1 1 calc R U . . .
H11B H 0.368752 0.538400 0.435168 0.058 Uiso 1 1 calc R U . . .
H11C H 0.570134 0.632380 0.414161 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1700(3) 0.5241(4) 0.68469(14) 0.0395(6) Uani 1 1 d . . . . .
H13A H 0.126366 0.584974 0.724303 0.047 Uiso 1 1 calc R U . . .
H13B H 0.139773 0.400814 0.695427 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0794(4) 0.5177(5) 0.59968(17) 0.0594(8) Uani 1 1 d . . . . .
H14A H 0.124963 0.458349 0.561205 0.089 Uiso 1 1 calc R U . . .
H14B H 0.109765 0.640550 0.590118 0.089 Uiso 1 1 calc R U . . .
H14C H -0.055660 0.450192 0.592136 0.089 Uiso 1 1 calc R U . . .
Cl1 Cl 0.80936(9) 0.35350(8) 0.80519(3) 0.03881(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C5 1.738(2) . ?
O4 C12 1.329(3) . ?
O4 C13 1.458(3) . ?
O6 C9 1.330(3) . ?
O6 C10 1.456(2) . ?
O5 C9 1.200(3) . ?
O3 C12 1.204(3) . ?
N2 O2 1.214(2) . ?
N2 O1 1.196(2) . ?
N2 C16 1.500(3) . ?
N1 C15 1.425(2) . ?
N1 C1 1.376(3) . ?
N1 C8 1.394(3) . ?
C15 C20 1.388(3) . ?
C15 C16 1.392(3) . ?
C20 C19 1.388(3) . ?
C20 Cl1 1.731(2) . ?
C16 C17 1.384(3) . ?
C9 C7 1.498(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(3) . ?
C1 C6 1.410(3) . ?
C1 C2 1.397(3) . ?
C7 C8 1.372(3) . ?
C7 C6 1.427(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(3) . ?
C8 C12 1.470(3) . ?
C19 H19 0.9500 . ?
C6 C5 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.496(3) . ?
C5 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.498(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C12 O4 C13 115.70(17) . . ?
C9 O6 C10 115.59(16) . . ?
O2 N2 C16 116.76(17) . . ?
O1 N2 O2 126.91(19) . . ?
O1 N2 C16 116.33(18) . . ?
C1 N1 C15 123.89(17) . . ?
C1 N1 C8 108.53(16) . . ?
C8 N1 C15 127.45(17) . . ?
C20 C15 N1 121.17(18) . . ?
C20 C15 C16 117.22(18) . . ?
C16 C15 N1 121.60(18) . . ?
C15 C20 C19 121.14(19) . . ?
C15 C20 Cl1 119.76(16) . . ?
C19 C20 Cl1 119.06(16) . . ?
C15 C16 N2 119.24(17) . . ?
C17 C16 N2 117.95(18) . . ?
C17 C16 C15 122.76(19) . . ?
O6 C9 C7 112.36(18) . . ?
O5 C9 O6 124.8(2) . . ?
O5 C9 C7 122.8(2) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.29(19) . . ?
C18 C17 H17 120.9 . . ?
N1 C1 C6 107.76(18) . . ?
N1 C1 C2 129.41(19) . . ?
C2 C1 C6 122.83(19) . . ?
C8 C7 C9 126.5(2) . . ?
C8 C7 C6 106.90(18) . . ?
C6 C7 C9 126.16(19) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.80(19) . . ?
C19 C18 H18 119.6 . . ?
N1 C8 C12 120.60(18) . . ?
C7 C8 N1 109.40(18) . . ?
C7 C8 C12 129.96(19) . . ?
O4 C12 C8 110.90(18) . . ?
O3 C12 O4 124.9(2) . . ?
O3 C12 C8 124.2(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.76(19) . . ?
C18 C19 H19 120.1 . . ?
C1 C6 C7 107.39(18) . . ?
C5 C6 C1 117.6(2) . . ?
C5 C6 C7 135.0(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
O6 C10 H10A 110.0 . . ?
O6 C10 H10B 110.0 . . ?
O6 C10 C11 108.34(18) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C6 C5 Cl2 118.68(18) . . ?
C4 C5 Cl2 120.90(17) . . ?
C4 C5 C6 120.4(2) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
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 . . ?
O4 C13 H13A 110.4 . . ?
O4 C13 H13B 110.4 . . ?
O4 C13 C14 106.5(2) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
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
Cl2 C5 C4 C3 -178.40(19) . . . . ?
O6 C9 C7 C8 -93.5(3) . . . . ?
O6 C9 C7 C6 94.6(3) . . . . ?
O5 C9 C7 C8 88.0(3) . . . . ?
O5 C9 C7 C6 -83.9(3) . . . . ?
N2 C16 C17 C18 178.17(18) . . . . ?
N1 C15 C20 C19 179.19(19) . . . . ?
N1 C15 C20 Cl1 -3.2(3) . . . . ?
N1 C15 C16 N2 2.9(3) . . . . ?
N1 C15 C16 C17 -179.84(19) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
N1 C1 C6 C5 -177.41(19) . . . . ?
N1 C1 C2 C3 179.5(2) . . . . ?
N1 C8 C12 O4 -173.95(18) . . . . ?
N1 C8 C12 O3 5.0(3) . . . . ?
O2 N2 C16 C15 -47.2(3) . . . . ?
O2 N2 C16 C17 135.4(2) . . . . ?
O1 N2 C16 C15 133.6(2) . . . . ?
O1 N2 C16 C17 -43.8(3) . . . . ?
C15 N1 C1 C6 -177.48(18) . . . . ?
C15 N1 C1 C2 1.7(3) . . . . ?
C15 N1 C8 C7 176.64(19) . . . . ?
C15 N1 C8 C12 -5.4(3) . . . . ?
C15 C20 C19 C18 0.5(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C20 C15 C16 N2 -176.28(18) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C16 C15 C20 C19 -1.7(3) . . . . ?
C16 C15 C20 Cl1 175.98(16) . . . . ?
C16 C17 C18 C19 -2.1(3) . . . . ?
C9 O6 C10 C11 -176.50(19) . . . . ?
C9 C7 C8 N1 -172.89(19) . . . . ?
C9 C7 C8 C12 9.4(4) . . . . ?
C9 C7 C6 C1 172.1(2) . . . . ?
C9 C7 C6 C5 -9.3(4) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C1 N1 C15 C20 -84.5(3) . . . . ?
C1 N1 C15 C16 96.4(2) . . . . ?
C1 N1 C8 C7 0.6(2) . . . . ?
C1 N1 C8 C12 178.61(18) . . . . ?
C1 C6 C5 Cl2 175.70(16) . . . . ?
C1 C6 C5 C4 -2.4(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C7 C8 C12 O4 3.5(3) . . . . ?
C7 C8 C12 O3 -177.5(2) . . . . ?
C7 C6 C5 Cl2 -2.8(4) . . . . ?
C7 C6 C5 C4 179.1(2) . . . . ?
C8 N1 C15 C20 100.1(3) . . . . ?
C8 N1 C15 C16 -79.1(3) . . . . ?
C8 N1 C1 C6 -1.3(2) . . . . ?
C8 N1 C1 C2 177.9(2) . . . . ?
C8 C7 C6 C1 -1.1(2) . . . . ?
C8 C7 C6 C5 177.5(2) . . . . ?
C12 O4 C13 C14 -169.0(2) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C7 C8 N1 0.3(2) . . . . ?
C6 C7 C8 C12 -177.4(2) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C2 C1 C6 C7 -177.8(2) . . . . ?
C2 C1 C6 C5 3.4(3) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
C10 O6 C9 O5 -0.9(3) . . . . ?
C10 O6 C9 C7 -179.37(18) . . . . ?
C13 O4 C12 O3 -0.7(3) . . . . ?
C13 O4 C12 C8 178.24(18) . . . . ?
Cl1 C20 C19 C18 -177.20(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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.629
