# 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_202012299
_database_code_depnum_ccdc_archive 'CCDC 2064372'
loop_
_audit_author_name
_audit_author_address
'Hui Liu'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 Cl N4 O4'
_chemical_formula_weight         496.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2734(2)
_cell_length_b                   12.5056(3)
_cell_length_c                   22.5981(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2620.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.603
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9257
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.912
_diffrn_reflns_theta_max         67.016
_diffrn_reflns_theta_full        67.016
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4660
_reflns_number_gt                4029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4660
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2095(2) 0.28669(14) 0.31177(7) 0.1151(6) Uani 1 1 d . . . . .
O1 O 0.4299(3) 0.6494(2) 0.65144(11) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.7488(3) 0.64417(18) 0.60056(12) 0.0577(6) Uani 1 1 d . . . . .
O3 O 0.8388(3) 0.5160(2) 0.66266(12) 0.0598(7) Uani 1 1 d . . . . .
O4 O 0.2944(4) 0.3067(3) 0.66417(16) 0.0890(11) Uani 1 1 d . . . . .
N1 N 0.3993(3) 0.6666(2) 0.55045(12) 0.0447(6) Uani 1 1 d . . . . .
N2 N 0.6415(3) 0.4834(2) 0.61406(13) 0.0490(7) Uani 1 1 d . . . . .
N3 N 0.2591(5) 0.2729(3) 0.6058(2) 0.0900(13) Uani 1 1 d . . . . .
N4 N 0.4179(5) 0.4410(4) 0.71083(17) 0.0797(11) Uani 1 1 d . . . . .
H4 H 0.451(5) 0.509(4) 0.7065(18) 0.064(12) Uiso 1 1 d . . . . .
C1 C 0.5848(4) 0.4552(3) 0.47508(17) 0.0534(8) Uani 1 1 d . . . . .
H1 H 0.6350 0.3941 0.4862 0.064 Uiso 1 1 calc R U . . .
C2 C 0.5737(5) 0.4837(3) 0.41594(18) 0.0626(10) Uani 1 1 d . . . . .
H2A H 0.6175 0.4419 0.3870 0.075 Uiso 1 1 calc R U . . .
C3 C 0.4977(5) 0.5739(3) 0.39996(17) 0.0647(10) Uani 1 1 d . . . . .
H3 H 0.4893 0.5910 0.3600 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4330(4) 0.6404(3) 0.44175(15) 0.0527(8) Uani 1 1 d . . . . .
H4A H 0.3817 0.7011 0.4307 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4488(3) 0.6117(2) 0.50025(15) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.5206(3) 0.5188(2) 0.51674(14) 0.0427(7) Uani 1 1 d . . . . .
C7 C 0.4434(3) 0.6168(2) 0.60090(14) 0.0424(7) Uani 1 1 d . . . . .
C8 C 0.5070(3) 0.5066(2) 0.58286(15) 0.0432(7) Uani 1 1 d . . . . .
C9 C 0.3385(4) 0.7747(3) 0.54986(17) 0.0531(8) Uani 1 1 d . . . . .
H9A H 0.2954 0.7896 0.5881 0.064 Uiso 1 1 calc R U . . .
H9B H 0.2627 0.7782 0.5203 0.064 Uiso 1 1 calc R U . . .
C10 C 0.4494(5) 0.8587(3) 0.5365(2) 0.0721(12) Uani 1 1 d . . . . .
H10A H 0.4844 0.8492 0.4969 0.108 Uiso 1 1 calc R U . . .
H10B H 0.5281 0.8522 0.5639 0.108 Uiso 1 1 calc R U . . .
H10C H 0.4066 0.9282 0.5403 0.108 Uiso 1 1 calc R U . . .
C11 C 0.7441(3) 0.5575(3) 0.62378(15) 0.0447(7) Uani 1 1 d . . . . .
C12 C 0.9578(4) 0.5774(3) 0.68792(18) 0.0563(9) Uani 1 1 d . . . . .
C13 C 1.0194(6) 0.4988(5) 0.7324(2) 0.0888(16) Uani 1 1 d . . . . .
H13A H 0.9475 0.4821 0.7616 0.133 Uiso 1 1 calc R U . . .
H13B H 1.1018 0.5300 0.7515 0.133 Uiso 1 1 calc R U . . .
H13C H 1.0480 0.4345 0.7124 0.133 Uiso 1 1 calc R U . . .
C14 C 0.8993(8) 0.6764(5) 0.7179(3) 0.109(2) Uani 1 1 d . . . . .
H14A H 0.8613 0.7242 0.6885 0.164 Uiso 1 1 calc R U . . .
H14B H 0.9754 0.7112 0.7392 0.164 Uiso 1 1 calc R U . . .
H14C H 0.8240 0.6565 0.7448 0.164 Uiso 1 1 calc R U . . .
C15 C 1.0660(5) 0.6024(5) 0.6412(2) 0.0917(16) Uani 1 1 d . . . . .
H15A H 1.0947 0.5375 0.6218 0.138 Uiso 1 1 calc R U . . .
H15B H 1.1488 0.6355 0.6589 0.138 Uiso 1 1 calc R U . . .
H15C H 1.0242 0.6503 0.6127 0.138 Uiso 1 1 calc R U . . .
C16 C 0.3643(5) 0.2485(4) 0.4748(3) 0.0809(14) Uani 1 1 d . . . . .
H16 H 0.4249 0.2012 0.4946 0.097 Uiso 1 1 calc R U . . .
C17 C 0.3407(6) 0.2362(4) 0.4149(3) 0.0858(15) Uani 1 1 d . . . . .
H17 H 0.3879 0.1827 0.3938 0.103 Uiso 1 1 calc R U . . .
C18 C 0.2464(6) 0.3039(4) 0.3868(2) 0.0776(12) Uani 1 1 d . . . . .
C19 C 0.1791(6) 0.3854(4) 0.4169(2) 0.0788(12) Uani 1 1 d . . . . .
H19 H 0.1158 0.4311 0.3974 0.095 Uiso 1 1 calc R U . . .
C20 C 0.2069(5) 0.3983(3) 0.4762(2) 0.0685(11) Uani 1 1 d . . . . .
H20 H 0.1629 0.4538 0.4968 0.082 Uiso 1 1 calc R U . . .
C21 C 0.2987(4) 0.3303(3) 0.5056(2) 0.0610(10) Uani 1 1 d . . . . .
C22 C 0.3220(4) 0.3423(3) 0.5705(2) 0.0609(10) Uani 1 1 d . . . . .
C23 C 0.3992(4) 0.4216(3) 0.60218(17) 0.0510(8) Uani 1 1 d . . . . .
C24 C 0.3761(4) 0.3948(3) 0.6601(2) 0.0670(11) Uani 1 1 d . . . . .
C25 C 0.4257(7) 0.3913(5) 0.7686(2) 0.1029(19) Uani 1 1 d . . . . .
H25A H 0.4272 0.3142 0.7643 0.124 Uiso 1 1 calc R U . . .
H25B H 0.3415 0.4106 0.7917 0.124 Uiso 1 1 calc R U . . .
C26 C 0.5600(9) 0.4280(7) 0.7997(3) 0.136(3) Uani 1 1 d . . . . .
H26A H 0.5724 0.5034 0.7938 0.204 Uiso 1 1 calc R U . . .
H26B H 0.6418 0.3905 0.7841 0.204 Uiso 1 1 calc R U . . .
H26C H 0.5515 0.4134 0.8413 0.204 Uiso 1 1 calc R U . . .
H2 H 0.6091 0.4512 0.6485 0.204 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C18 1.743(5) . ?
O1 C7 1.219(4) . ?
O2 C11 1.206(4) . ?
O3 C11 1.346(4) . ?
O3 C12 1.461(4) . ?
O4 C24 1.341(5) . ?
O4 N3 1.424(5) . ?
N1 C7 1.362(4) . ?
N1 C5 1.403(4) . ?
N1 C9 1.465(4) . ?
N2 C11 1.345(4) . ?
N2 C8 1.462(4) . ?
N2 H2 0.9268 . ?
N3 C22 1.315(5) . ?
N4 C24 1.341(6) . ?
N4 C25 1.447(6) . ?
N4 H4 0.92(5) . ?
C1 C6 1.369(5) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(4) . ?
C6 C8 1.507(5) . ?
C7 C8 1.554(4) . ?
C8 C23 1.523(4) . ?
C9 C10 1.500(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C15 1.491(6) . ?
C12 C14 1.511(7) . ?
C12 C13 1.518(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.379(6) . ?
C16 C17 1.380(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(7) . ?
C19 C20 1.374(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.491(6) . ?
C22 C23 1.417(5) . ?
C23 C24 1.367(6) . ?
C25 C26 1.502(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C11 O3 C12 123.0(3) . . ?
C24 O4 N3 108.1(3) . . ?
C7 N1 C5 110.8(3) . . ?
C7 N1 C9 123.0(3) . . ?
C5 N1 C9 124.7(3) . . ?
C11 N2 C8 123.1(3) . . ?
C11 N2 H2 113.0 . . ?
C8 N2 H2 102.4 . . ?
C22 N3 O4 105.3(3) . . ?
C24 N4 C25 126.9(5) . . ?
C24 N4 H4 114(3) . . ?
C25 N4 H4 119(3) . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 H4A 121.7 . . ?
C3 C4 H4A 121.7 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 N1 127.9(3) . . ?
C6 C5 N1 110.4(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 C8 131.2(3) . . ?
C5 C6 C8 108.1(3) . . ?
O1 C7 N1 126.9(3) . . ?
O1 C7 C8 125.5(3) . . ?
N1 C7 C8 107.5(3) . . ?
N2 C8 C6 115.2(3) . . ?
N2 C8 C23 106.5(2) . . ?
C6 C8 C23 114.2(3) . . ?
N2 C8 C7 111.9(3) . . ?
C6 C8 C7 101.6(2) . . ?
C23 C8 C7 107.2(3) . . ?
N1 C9 C10 112.6(3) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N2 125.0(3) . . ?
O2 C11 O3 127.4(3) . . ?
N2 C11 O3 107.6(3) . . ?
O3 C12 C15 110.0(4) . . ?
O3 C12 C14 109.5(4) . . ?
C15 C12 C14 112.8(5) . . ?
O3 C12 C13 101.7(3) . . ?
C15 C12 C13 110.6(4) . . ?
C14 C12 C13 111.6(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 120.5(5) . . ?
C21 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.1(5) . . ?
C17 C18 Cl1 119.9(4) . . ?
C19 C18 Cl1 118.9(5) . . ?
C20 C19 C18 119.0(5) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 119.3(4) . . ?
C20 C21 C22 120.2(4) . . ?
C16 C21 C22 120.5(4) . . ?
N3 C22 C23 112.4(4) . . ?
N3 C22 C21 117.8(4) . . ?
C23 C22 C21 129.8(3) . . ?
C24 C23 C22 103.5(3) . . ?
C24 C23 C8 123.2(3) . . ?
C22 C23 C8 132.5(4) . . ?
O4 C24 N4 117.3(4) . . ?
O4 C24 C23 110.8(4) . . ?
N4 C24 C23 131.9(4) . . ?
N4 C25 C26 109.5(5) . . ?
N4 C25 H25A 109.8 . . ?
C26 C25 H25A 109.8 . . ?
N4 C25 H25B 109.8 . . ?
C26 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C24 O4 N3 C22 0.3(5) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 -2.5(5) . . . . ?
C3 C4 C5 N1 177.5(3) . . . . ?
C7 N1 C5 C4 -176.2(3) . . . . ?
C9 N1 C5 C4 -9.5(5) . . . . ?
C7 N1 C5 C6 3.8(3) . . . . ?
C9 N1 C5 C6 170.5(3) . . . . ?
C2 C1 C6 C5 -1.7(5) . . . . ?
C2 C1 C6 C8 176.3(3) . . . . ?
C4 C5 C6 C1 3.4(5) . . . . ?
N1 C5 C6 C1 -176.6(3) . . . . ?
C4 C5 C6 C8 -175.0(3) . . . . ?
N1 C5 C6 C8 5.0(3) . . . . ?
C5 N1 C7 O1 172.6(3) . . . . ?
C9 N1 C7 O1 5.7(5) . . . . ?
C5 N1 C7 C8 -10.6(3) . . . . ?
C9 N1 C7 C8 -177.5(3) . . . . ?
C11 N2 C8 C6 74.7(4) . . . . ?
C11 N2 C8 C23 -157.6(3) . . . . ?
C11 N2 C8 C7 -40.8(4) . . . . ?
C1 C6 C8 N2 50.2(5) . . . . ?
C5 C6 C8 N2 -131.6(3) . . . . ?
C1 C6 C8 C23 -73.6(5) . . . . ?
C5 C6 C8 C23 104.6(3) . . . . ?
C1 C6 C8 C7 171.4(3) . . . . ?
C5 C6 C8 C7 -10.4(3) . . . . ?
O1 C7 C8 N2 -47.0(4) . . . . ?
N1 C7 C8 N2 136.2(3) . . . . ?
O1 C7 C8 C6 -170.5(3) . . . . ?
N1 C7 C8 C6 12.7(3) . . . . ?
O1 C7 C8 C23 69.4(4) . . . . ?
N1 C7 C8 C23 -107.5(3) . . . . ?
C7 N1 C9 C10 95.4(4) . . . . ?
C5 N1 C9 C10 -69.7(4) . . . . ?
C8 N2 C11 O2 -12.5(6) . . . . ?
C8 N2 C11 O3 168.5(3) . . . . ?
C12 O3 C11 O2 6.9(6) . . . . ?
C12 O3 C11 N2 -174.1(3) . . . . ?
C11 O3 C12 C15 -68.4(5) . . . . ?
C11 O3 C12 C14 56.1(5) . . . . ?
C11 O3 C12 C13 174.4(4) . . . . ?
C21 C16 C17 C18 -2.6(7) . . . . ?
C16 C17 C18 C19 2.1(7) . . . . ?
C16 C17 C18 Cl1 -177.5(4) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
Cl1 C18 C19 C20 179.3(4) . . . . ?
C18 C19 C20 C21 -0.9(7) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C19 C20 C21 C22 -177.0(4) . . . . ?
C17 C16 C21 C20 1.4(6) . . . . ?
C17 C16 C21 C22 178.8(4) . . . . ?
O4 N3 C22 C23 0.3(5) . . . . ?
O4 N3 C22 C21 -177.4(4) . . . . ?
C20 C21 C22 N3 104.5(5) . . . . ?
C16 C21 C22 N3 -72.9(5) . . . . ?
C20 C21 C22 C23 -72.6(6) . . . . ?
C16 C21 C22 C23 110.0(5) . . . . ?
N3 C22 C23 C24 -0.7(5) . . . . ?
C21 C22 C23 C24 176.6(4) . . . . ?
N3 C22 C23 C8 168.7(4) . . . . ?
C21 C22 C23 C8 -14.0(7) . . . . ?
N2 C8 C23 C24 48.5(5) . . . . ?
C6 C8 C23 C24 176.9(3) . . . . ?
C7 C8 C23 C24 -71.4(4) . . . . ?
N2 C8 C23 C22 -119.2(4) . . . . ?
C6 C8 C23 C22 9.2(5) . . . . ?
C7 C8 C23 C22 120.9(4) . . . . ?
N3 O4 C24 N4 178.3(4) . . . . ?
N3 O4 C24 C23 -0.8(5) . . . . ?
C25 N4 C24 O4 21.3(8) . . . . ?
C25 N4 C24 C23 -159.9(5) . . . . ?
C22 C23 C24 O4 0.9(5) . . . . ?
C8 C23 C24 O4 -169.8(3) . . . . ?
C22 C23 C24 N4 -178.0(5) . . . . ?
C8 C23 C24 N4 11.3(7) . . . . ?
C24 N4 C25 C26 139.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O1 0.92(5) 2.16(4) 2.934(5) 142(4) .
N2 H2 N4 0.93 2.27 3.060(5) 143.1 .

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_202012299_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2064373'
loop_
_audit_author_name
_audit_author_address
'Hui Liu'
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_audit_creation_date             2020-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H29 Cl N4 O4'
_chemical_formula_sum            'C26 H29 Cl N4 O4'
_chemical_formula_weight         496.98
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2734(2)
_cell_length_b                   12.5056(3)
_cell_length_c                   22.5981(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2620.69(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4880
_cell_measurement_theta_min      4.0220
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.016
_diffrn_reflns_theta_max         67.016
_diffrn_reflns_theta_min         3.912
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.50    --  -33.50  37.00 -90.00   93
  2  ω     63.00  89.00   1.00    1.50    --   36.47  57.00  60.00   26
  3  ω     71.00 110.00   1.00    1.50    --   36.47 178.00 120.00   39
  4  ω     19.00  52.00   1.00    1.50    --   36.47  57.00  60.00   33
  5  ω    -32.00  40.00   1.00    1.50    --   36.47 -77.00 -90.00   72
  6  ω     79.00 105.00   1.00    1.50    --   36.47 178.00-150.00   26
  7  ω     35.00  61.00   1.00    1.50    --   36.47 -99.00   0.00   26
  8  ω     35.00 105.00   1.00    1.50    --   36.47  57.00   0.00   70
  9  ω     -1.00  30.00   1.00    1.50    --   36.47 -99.00   0.00   31
 10  ω     37.00 105.00   1.00    7.50    --  108.00-111.00 120.00   68
 11  ω     84.00 110.00   1.00    7.50    --  108.00 -45.00 150.00   26
 12  ω     39.00  72.00   1.00    7.50    --  108.00 -45.00 150.00   33
 13  ω     48.00 112.00   1.00    7.50    --  108.00 -30.00  60.00   64
 14  ω     53.00  86.00   1.00    7.50    --  108.00 -94.00 -30.00   33
 15  ω    105.00 174.00   1.00    7.50    --  108.00  61.00-120.00   69
 16  ω    107.00 155.00   1.00    7.50    --  108.00 111.00 120.00   48
 17  ω     41.00 133.00   1.00    7.50    --  108.00 -77.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0304382000
_diffrn_orient_matrix_UB_12      -0.0194394000
_diffrn_orient_matrix_UB_13      0.0661702000
_diffrn_orient_matrix_UB_21      0.1171182000
_diffrn_orient_matrix_UB_22      -0.0820944000
_diffrn_orient_matrix_UB_23      -0.0164734000
_diffrn_orient_matrix_UB_31      0.1138305000
_diffrn_orient_matrix_UB_32      0.0897073000
_diffrn_orient_matrix_UB_33      -0.0007331000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4029
_reflns_number_total             4660
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1494 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(14)
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.037
_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)+(0.0568P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1208
_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, All C(H,H,H,H) groups
2.a Riding coordinates:
 C26(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4A), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.2095(2) 0.28669(14) 0.31177(7) 0.1151(6) Uani 1 1 d . . . . .
O1 O 0.4299(3) 0.6494(2) 0.65144(11) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.7488(3) 0.64417(18) 0.60056(12) 0.0577(6) Uani 1 1 d . . . . .
O3 O 0.8388(3) 0.5160(2) 0.66266(12) 0.0598(7) Uani 1 1 d . . . . .
O4 O 0.2944(4) 0.3067(3) 0.66417(16) 0.0890(11) Uani 1 1 d . . . . .
N1 N 0.3993(3) 0.6666(2) 0.55045(12) 0.0447(6) Uani 1 1 d . . . . .
N2 N 0.6415(3) 0.4834(2) 0.61406(13) 0.0490(7) Uani 1 1 d . . . . .
N3 N 0.2591(5) 0.2729(3) 0.6058(2) 0.0900(13) Uani 1 1 d . . . . .
N4 N 0.4179(5) 0.4410(4) 0.71083(17) 0.0797(11) Uani 1 1 d . . . . .
H4 H 0.451(5) 0.509(4) 0.7065(18) 0.064(12) Uiso 1 1 d . . . . .
C1 C 0.5848(4) 0.4552(3) 0.47508(17) 0.0534(8) Uani 1 1 d . . . . .
H1 H 0.6350 0.3941 0.4862 0.064 Uiso 1 1 calc R . . . .
C2 C 0.5737(5) 0.4837(3) 0.41594(18) 0.0626(10) Uani 1 1 d . . . . .
H2A H 0.6175 0.4419 0.3870 0.075 Uiso 1 1 calc R . . . .
C3 C 0.4977(5) 0.5739(3) 0.39996(17) 0.0647(10) Uani 1 1 d . . . . .
H3 H 0.4893 0.5910 0.3600 0.078 Uiso 1 1 calc R . . . .
C4 C 0.4330(4) 0.6404(3) 0.44175(15) 0.0527(8) Uani 1 1 d . . . . .
H4A H 0.3817 0.7011 0.4307 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4488(3) 0.6117(2) 0.50025(15) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.5206(3) 0.5188(2) 0.51674(14) 0.0427(7) Uani 1 1 d . . . . .
C7 C 0.4434(3) 0.6168(2) 0.60090(14) 0.0424(7) Uani 1 1 d . . . . .
C8 C 0.5070(3) 0.5066(2) 0.58286(15) 0.0432(7) Uani 1 1 d . . . . .
C9 C 0.3385(4) 0.7747(3) 0.54986(17) 0.0531(8) Uani 1 1 d . . . . .
H9A H 0.2954 0.7896 0.5881 0.064 Uiso 1 1 calc R . . . .
H9B H 0.2627 0.7782 0.5203 0.064 Uiso 1 1 calc R . . . .
C10 C 0.4494(5) 0.8587(3) 0.5365(2) 0.0721(12) Uani 1 1 d . . . . .
H10A H 0.4844 0.8492 0.4969 0.108 Uiso 1 1 calc GR . . . .
H10B H 0.5281 0.8522 0.5639 0.108 Uiso 1 1 calc GR . . . .
H10C H 0.4066 0.9282 0.5403 0.108 Uiso 1 1 calc GR . . . .
C11 C 0.7441(3) 0.5575(3) 0.62378(15) 0.0447(7) Uani 1 1 d . . . . .
C12 C 0.9578(4) 0.5774(3) 0.68792(18) 0.0563(9) Uani 1 1 d . . . . .
C13 C 1.0194(6) 0.4988(5) 0.7324(2) 0.0888(16) Uani 1 1 d . . . . .
H13A H 0.9475 0.4821 0.7616 0.133 Uiso 1 1 calc GR . . . .
H13B H 1.1018 0.5300 0.7515 0.133 Uiso 1 1 calc GR . . . .
H13C H 1.0480 0.4345 0.7124 0.133 Uiso 1 1 calc GR . . . .
C14 C 0.8993(8) 0.6764(5) 0.7179(3) 0.109(2) Uani 1 1 d . . . . .
H14A H 0.8613 0.7242 0.6885 0.164 Uiso 1 1 calc GR . . . .
H14B H 0.9754 0.7112 0.7392 0.164 Uiso 1 1 calc GR . . . .
H14C H 0.8240 0.6565 0.7448 0.164 Uiso 1 1 calc GR . . . .
C15 C 1.0660(5) 0.6024(5) 0.6412(2) 0.0917(16) Uani 1 1 d . . . . .
H15A H 1.0947 0.5375 0.6218 0.138 Uiso 1 1 calc GR . . . .
H15B H 1.1488 0.6355 0.6589 0.138 Uiso 1 1 calc GR . . . .
H15C H 1.0242 0.6503 0.6127 0.138 Uiso 1 1 calc GR . . . .
C16 C 0.3643(5) 0.2485(4) 0.4748(3) 0.0809(14) Uani 1 1 d . . . . .
H16 H 0.4249 0.2012 0.4946 0.097 Uiso 1 1 calc R . . . .
C17 C 0.3407(6) 0.2362(4) 0.4149(3) 0.0858(15) Uani 1 1 d . . . . .
H17 H 0.3879 0.1827 0.3938 0.103 Uiso 1 1 calc R . . . .
C18 C 0.2464(6) 0.3039(4) 0.3868(2) 0.0776(12) Uani 1 1 d . . . . .
C19 C 0.1791(6) 0.3854(4) 0.4169(2) 0.0788(12) Uani 1 1 d . . . . .
H19 H 0.1158 0.4311 0.3974 0.095 Uiso 1 1 calc R . . . .
C20 C 0.2069(5) 0.3983(3) 0.4762(2) 0.0685(11) Uani 1 1 d . . . . .
H20 H 0.1629 0.4538 0.4968 0.082 Uiso 1 1 calc R . . . .
C21 C 0.2987(4) 0.3303(3) 0.5056(2) 0.0610(10) Uani 1 1 d . . . . .
C22 C 0.3220(4) 0.3423(3) 0.5705(2) 0.0609(10) Uani 1 1 d . . . . .
C23 C 0.3992(4) 0.4216(3) 0.60218(17) 0.0510(8) Uani 1 1 d . . . . .
C24 C 0.3761(4) 0.3948(3) 0.6601(2) 0.0670(11) Uani 1 1 d . . . . .
C25 C 0.4257(7) 0.3913(5) 0.7686(2) 0.1029(19) Uani 1 1 d . . . . .
H25A H 0.4272 0.3142 0.7643 0.124 Uiso 1 1 calc R . . . .
H25B H 0.3415 0.4106 0.7917 0.124 Uiso 1 1 calc R . . . .
C26 C 0.5600(9) 0.4280(7) 0.7997(3) 0.136(3) Uani 1 1 d . . . . .
H26A H 0.5724 0.5034 0.7938 0.204 Uiso 1 1 calc GR . . . .
H26B H 0.6418 0.3905 0.7841 0.204 Uiso 1 1 calc GR . . . .
H26C H 0.5515 0.4134 0.8413 0.204 Uiso 1 1 calc GR . . . .
H2 H 0.6091 0.4512 0.6485 0.204 Uiso 1 1 d 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 C18 1.743(5) . ?
O1 C7 1.219(4) . ?
O2 C11 1.206(4) . ?
O3 C11 1.346(4) . ?
O3 C12 1.461(4) . ?
O4 N3 1.424(5) . ?
O4 C24 1.341(5) . ?
N1 C5 1.403(4) . ?
N1 C7 1.362(4) . ?
N1 C9 1.465(4) . ?
N2 C8 1.462(4) . ?
N2 C11 1.345(4) . ?
N2 H2 0.9268 . ?
N3 C22 1.315(5) . ?
N4 H4 0.92(5) . ?
N4 C24 1.341(6) . ?
N4 C25 1.447(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C1 C6 1.369(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.378(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(5) . ?
C4 H4A 0.9300 . ?
C4 C5 1.378(5) . ?
C5 C6 1.390(4) . ?
C6 C8 1.507(5) . ?
C7 C8 1.554(4) . ?
C8 C23 1.523(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.500(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C13 1.518(6) . ?
C12 C14 1.511(7) . ?
C12 C15 1.491(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.380(7) . ?
C16 C21 1.379(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(7) . ?
C18 C19 1.375(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(6) . ?
C21 C22 1.491(6) . ?
C22 C23 1.417(5) . ?
C23 C24 1.367(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.502(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C11 O3 C12 123.0(3) . . ?
C24 O4 N3 108.1(3) . . ?
C5 N1 C9 124.7(3) . . ?
C7 N1 C5 110.8(3) . . ?
C7 N1 C9 123.0(3) . . ?
C8 N2 H2 102.4 . . ?
C11 N2 C8 123.1(3) . . ?
C11 N2 H2 113.0 . . ?
C22 N3 O4 105.3(3) . . ?
C24 N4 H4 114(3) . . ?
C24 N4 C25 126.9(5) . . ?
C25 N4 H4 119(3) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C6 C1 C2 118.8(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.1(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4A 121.7 . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 H4A 121.7 . . ?
C4 C5 N1 127.9(3) . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 N1 110.4(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 C8 131.2(3) . . ?
C5 C6 C8 108.1(3) . . ?
O1 C7 N1 126.9(3) . . ?
O1 C7 C8 125.5(3) . . ?
N1 C7 C8 107.5(3) . . ?
N2 C8 C6 115.2(3) . . ?
N2 C8 C7 111.9(3) . . ?
N2 C8 C23 106.5(2) . . ?
C6 C8 C7 101.6(2) . . ?
C6 C8 C23 114.2(3) . . ?
C23 C8 C7 107.2(3) . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
N1 C9 C10 112.6(3) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
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 . . ?
O2 C11 O3 127.4(3) . . ?
O2 C11 N2 125.0(3) . . ?
N2 C11 O3 107.6(3) . . ?
O3 C12 C13 101.7(3) . . ?
O3 C12 C14 109.5(4) . . ?
O3 C12 C15 110.0(4) . . ?
C14 C12 C13 111.6(4) . . ?
C15 C12 C13 110.6(4) . . ?
C15 C12 C14 112.8(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16 119.7 . . ?
C21 C16 H16 119.7 . . ?
C21 C16 C17 120.5(5) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 Cl1 119.9(4) . . ?
C17 C18 C19 121.1(5) . . ?
C19 C18 Cl1 118.9(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(5) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C22 120.5(4) . . ?
C20 C21 C16 119.3(4) . . ?
C20 C21 C22 120.2(4) . . ?
N3 C22 C21 117.8(4) . . ?
N3 C22 C23 112.4(4) . . ?
C23 C22 C21 129.8(3) . . ?
C22 C23 C8 132.5(4) . . ?
C24 C23 C8 123.2(3) . . ?
C24 C23 C22 103.5(3) . . ?
O4 C24 N4 117.3(4) . . ?
O4 C24 C23 110.8(4) . . ?
N4 C24 C23 131.9(4) . . ?
N4 C25 H25A 109.8 . . ?
N4 C25 H25B 109.8 . . ?
N4 C25 C26 109.5(5) . . ?
H25A C25 H25B 108.2 . . ?
C26 C25 H25A 109.8 . . ?
C26 C25 H25B 109.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 O1 0.92(5) 2.16(4) 2.934(5) 142(4) .
N2 H2 N4 0.93 2.27 3.060(5) 143.1 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C18 C19 C20 179.3(4) . . . . ?
O1 C7 C8 N2 -47.0(4) . . . . ?
O1 C7 C8 C6 -170.5(3) . . . . ?
O1 C7 C8 C23 69.4(4) . . . . ?
O4 N3 C22 C21 -177.4(4) . . . . ?
O4 N3 C22 C23 0.3(5) . . . . ?
N1 C5 C6 C1 -176.6(3) . . . . ?
N1 C5 C6 C8 5.0(3) . . . . ?
N1 C7 C8 N2 136.2(3) . . . . ?
N1 C7 C8 C6 12.7(3) . . . . ?
N1 C7 C8 C23 -107.5(3) . . . . ?
N2 C8 C23 C22 -119.2(4) . . . . ?
N2 C8 C23 C24 48.5(5) . . . . ?
N3 O4 C24 N4 178.3(4) . . . . ?
N3 O4 C24 C23 -0.8(5) . . . . ?
N3 C22 C23 C8 168.7(4) . . . . ?
N3 C22 C23 C24 -0.7(5) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C1 C6 C8 N2 50.2(5) . . . . ?
C1 C6 C8 C7 171.4(3) . . . . ?
C1 C6 C8 C23 -73.6(5) . . . . ?
C2 C1 C6 C5 -1.7(5) . . . . ?
C2 C1 C6 C8 176.3(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 N1 177.5(3) . . . . ?
C3 C4 C5 C6 -2.5(5) . . . . ?
C4 C5 C6 C1 3.4(5) . . . . ?
C4 C5 C6 C8 -175.0(3) . . . . ?
C5 N1 C7 O1 172.6(3) . . . . ?
C5 N1 C7 C8 -10.6(3) . . . . ?
C5 N1 C9 C10 -69.7(4) . . . . ?
C5 C6 C8 N2 -131.6(3) . . . . ?
C5 C6 C8 C7 -10.4(3) . . . . ?
C5 C6 C8 C23 104.6(3) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C6 C8 C23 C22 9.2(5) . . . . ?
C6 C8 C23 C24 176.9(3) . . . . ?
C7 N1 C5 C4 -176.2(3) . . . . ?
C7 N1 C5 C6 3.8(3) . . . . ?
C7 N1 C9 C10 95.4(4) . . . . ?
C7 C8 C23 C22 120.9(4) . . . . ?
C7 C8 C23 C24 -71.4(4) . . . . ?
C8 N2 C11 O2 -12.5(6) . . . . ?
C8 N2 C11 O3 168.5(3) . . . . ?
C8 C23 C24 O4 -169.8(3) . . . . ?
C8 C23 C24 N4 11.3(7) . . . . ?
C9 N1 C5 C4 -9.5(5) . . . . ?
C9 N1 C5 C6 170.5(3) . . . . ?
C9 N1 C7 O1 5.7(5) . . . . ?
C9 N1 C7 C8 -177.5(3) . . . . ?
C11 O3 C12 C13 174.4(4) . . . . ?
C11 O3 C12 C14 56.1(5) . . . . ?
C11 O3 C12 C15 -68.4(5) . . . . ?
C11 N2 C8 C6 74.7(4) . . . . ?
C11 N2 C8 C7 -40.8(4) . . . . ?
C11 N2 C8 C23 -157.6(3) . . . . ?
C12 O3 C11 O2 6.9(6) . . . . ?
C12 O3 C11 N2 -174.1(3) . . . . ?
C16 C17 C18 Cl1 -177.5(4) . . . . ?
C16 C17 C18 C19 2.1(7) . . . . ?
C16 C21 C22 N3 -72.9(5) . . . . ?
C16 C21 C22 C23 110.0(5) . . . . ?
C17 C16 C21 C20 1.4(6) . . . . ?
C17 C16 C21 C22 178.8(4) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C18 C19 C20 C21 -0.9(7) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C19 C20 C21 C22 -177.0(4) . . . . ?
C20 C21 C22 N3 104.5(5) . . . . ?
C20 C21 C22 C23 -72.6(6) . . . . ?
C21 C16 C17 C18 -2.6(7) . . . . ?
C21 C22 C23 C8 -14.0(7) . . . . ?
C21 C22 C23 C24 176.6(4) . . . . ?
C22 C23 C24 O4 0.9(5) . . . . ?
C22 C23 C24 N4 -178.0(5) . . . . ?
C24 O4 N3 C22 0.3(5) . . . . ?
C24 N4 C25 C26 139.3(6) . . . . ?
C25 N4 C24 O4 21.3(8) . . . . ?
C25 N4 C24 C23 -159.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.912
