# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_cu_20211217_ny_cn1_0m
_database_code_depnum_ccdc_archive 'CCDC 2190909'
loop_
_audit_author_name
_audit_author_address
'Zhengkun Ju'
;NJUPT
China
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2021-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 N2 O4, C24 H12, 2(C), [+ solvents]'
_chemical_formula_sum            'C42 H26 Cl2 N2 O4'
_chemical_formula_weight         693.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.2003(9)
_cell_length_b                   10.1086(13)
_cell_length_c                   11.0066(14)
_cell_angle_alpha                94.520(9)
_cell_angle_beta                 94.515(8)
_cell_angle_gamma                103.410(8)
_cell_volume                     772.95(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3785
_cell_measurement_temperature    197.00
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.05
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1282 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.6708.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9604
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_min         4.049
_diffrn_ambient_temperature      197.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             2832
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.515
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.062
_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)+(0.0853P)²+0.4151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.23553(13) 0.51982(9) 0.06615(9) 0.0862(4) Uani 1 1 d . . . . .
C21 C 0.4993(7) 0.5322(4) 0.0591(3) 0.0931(12) Uani 1 1 d . . . . .
H21A H 0.573612 0.628590 0.067411 0.112 Uiso 1 1 calc R U . . .
H21B H 0.550815 0.483258 0.123183 0.112 Uiso 1 1 calc R U . . .
O1 O -0.3830(3) -0.10338(19) 0.14225(14) 0.0508(5) Uani 1 1 d . . . . .
O2 O -0.3479(3) 0.33293(18) 0.29335(16) 0.0519(5) Uani 1 1 d . . . . .
N1 N -0.3592(3) 0.1150(2) 0.21991(16) 0.0416(5) Uani 1 1 d . . . . .
C1 C -0.2987(4) 0.1637(3) 0.1036(2) 0.0552(7) Uani 1 1 d . . . . .
H1A H -0.219166 0.106731 0.068560 0.083 Uiso 1 1 calc R U . . .
H1B H -0.224350 0.258799 0.118278 0.083 Uiso 1 1 calc R U . . .
H1C H -0.412225 0.157972 0.046286 0.083 Uiso 1 1 calc R U . . .
C2 C -0.3988(3) -0.0253(2) 0.22888(19) 0.0396(5) Uani 1 1 d . . . . .
C3 C -0.3767(3) 0.2132(2) 0.3118(2) 0.0403(5) Uani 1 1 d . . . . .
C4 C -0.4587(3) -0.0732(2) 0.34639(19) 0.0368(5) Uani 1 1 d . . . . .
C5 C -0.4720(3) 0.0231(2) 0.44395(19) 0.0341(5) Uani 1 1 d . . . . .
C6 C -0.5011(3) -0.2104(2) 0.3615(2) 0.0411(5) Uani 1 1 d . . . . .
H6 H -0.493838 -0.274825 0.295443 0.049 Uiso 1 1 calc R U . . .
C7 C -0.5549(3) -0.2561(2) 0.4735(2) 0.0414(5) Uani 1 1 d . . . . .
H7 H -0.581985 -0.351008 0.483104 0.050 Uiso 1 1 calc R U . . .
C8 C -0.5688(3) -0.1642(2) 0.56987(19) 0.0362(5) Uani 1 1 d . . . . .
C9 C 0.0720(4) -0.1402(3) 0.1878(2) 0.0510(6) Uani 1 1 d . . . . .
H9 H 0.077029 -0.203176 0.120064 0.061 Uiso 1 1 calc R U . . .
C10 C 0.1229(3) -0.0013(3) 0.1763(2) 0.0488(6) Uani 1 1 d . . . . .
H10 H 0.163400 0.029633 0.101196 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1152(3) 0.0949(3) 0.2748(2) 0.0436(6) Uani 1 1 d . . . . .
C12 C 0.1631(3) 0.2362(3) 0.2648(2) 0.0495(6) Uani 1 1 d . . . . .
H12 H 0.201178 0.268507 0.189640 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1558(3) 0.3291(3) 0.3625(2) 0.0480(6) Uani 1 1 d . . . . .
H13 H 0.188502 0.424141 0.353411 0.058 Uiso 1 1 calc R U . . .
C14 C 0.1000(3) 0.2843(2) 0.4759(2) 0.0442(6) Uani 1 1 d . . . . .
C15 C 0.0490(3) 0.1423(2) 0.4881(2) 0.0383(5) Uani 1 1 d . . . . .
C16 C 0.0575(3) 0.0480(2) 0.3872(2) 0.0391(5) Uani 1 1 d . . . . .
C17 C -0.0073(3) 0.0951(2) 0.6008(2) 0.0388(5) Uani 1 1 d . . . . .
C18 C -0.0129(3) 0.1899(3) 0.7016(2) 0.0453(6) Uani 1 1 d . . . . .
C19 C 0.0423(4) 0.3307(3) 0.6878(2) 0.0500(6) Uani 1 1 d . . . . .
H19 H 0.041811 0.395301 0.755314 0.060 Uiso 1 1 calc R U . . .
C20 C 0.0970(4) 0.3765(3) 0.5782(3) 0.0515(6) Uani 1 1 d . . . . .
H20 H 0.133376 0.471982 0.571516 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.882(5) . ?
C21 C21 1.410(8) 2_665 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
O1 C2 1.219(3) . ?
O2 C3 1.216(3) . ?
N1 C1 1.469(3) . ?
N1 C2 1.393(3) . ?
N1 C3 1.395(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.478(3) . ?
C3 C8 1.479(3) 2_456 ?
C4 C5 1.416(3) . ?
C4 C6 1.376(3) . ?
C5 C5 1.409(4) 2_456 ?
C5 C8 1.410(3) 2_456 ?
C6 H6 0.9500 . ?
C6 C7 1.401(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(4) . ?
C9 C18 1.412(4) 2_556 ?
C10 H10 0.9500 . ?
C10 C11 1.412(4) . ?
C11 C12 1.405(4) . ?
C11 C16 1.417(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.418(4) . ?
C14 C15 1.417(3) . ?
C14 C20 1.408(4) . ?
C15 C16 1.420(3) . ?
C15 C17 1.418(3) . ?
C16 C17 1.428(4) 2_556 ?
C17 C18 1.417(3) . ?
C18 C19 1.411(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9500 . ?

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
Cl1 C21 H21A 111.5 . . ?
Cl1 C21 H21B 111.5 . . ?
C21 C21 Cl1 101.5(4) 2_665 . ?
C21 C21 H21A 111.5 2_665 . ?
C21 C21 H21B 111.5 2_665 . ?
H21A C21 H21B 109.3 . . ?
C2 N1 C1 117.7(2) . . ?
C2 N1 C3 125.14(19) . . ?
C3 N1 C1 117.1(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 120.2(2) . . ?
O1 C2 C4 122.4(2) . . ?
N1 C2 C4 117.3(2) . . ?
O2 C3 N1 120.4(2) . . ?
O2 C3 C8 122.7(2) . 2_456 ?
N1 C3 C8 116.9(2) . 2_456 ?
C5 C4 C2 119.6(2) . . ?
C6 C4 C2 120.5(2) . . ?
C6 C4 C5 120.0(2) . . ?
C5 C5 C4 119.3(3) 2_456 . ?
C5 C5 C8 119.7(3) 2_456 2_456 ?
C8 C5 C4 121.0(2) 2_456 . ?
C4 C6 H6 119.7 . . ?
C4 C6 C7 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C5 C8 C3 120.0(2) 2_456 2_456 ?
C7 C8 C3 120.1(2) . 2_456 ?
C7 C8 C5 119.9(2) . 2_456 ?
C10 C9 H9 119.4 . . ?
C10 C9 C18 121.2(2) . 2_556 ?
C18 C9 H9 119.4 2_556 . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C16 119.3(2) . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 C16 118.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.2(2) . . ?
C20 C14 C13 122.2(2) . . ?
C20 C14 C15 118.6(2) . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 C17 120.2(2) . . ?
C17 C15 C16 120.5(2) . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 C17 119.8(2) . 2_556 ?
C15 C16 C17 119.6(2) . 2_556 ?
C15 C17 C16 119.9(2) . 2_556 ?
C18 C17 C15 120.1(2) . . ?
C18 C17 C16 119.9(2) . 2_556 ?
C9 C18 C17 119.0(2) 2_556 . ?
C19 C18 C9 122.4(2) . 2_556 ?
C19 C18 C17 118.6(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C14 C20 H20 119.4 . . ?
C19 C20 C14 121.2(2) . . ?
C19 C20 H20 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C4 C5 179.21(19) . . . . ?
O1 C2 C4 C6 -0.6(3) . . . . ?
N1 C2 C4 C5 -0.5(3) . . . . ?
N1 C2 C4 C6 179.67(18) . . . . ?
C1 N1 C2 O1 0.0(3) . . . . ?
C1 N1 C2 C4 179.74(19) . . . . ?
C1 N1 C3 O2 2.1(3) . . . . ?
C1 N1 C3 C8 -178.01(19) . . . 2_456 ?
C2 N1 C3 O2 -176.32(19) . . . . ?
C2 N1 C3 C8 3.6(3) . . . 2_456 ?
C2 C4 C5 C5 -179.6(2) . . . 2_456 ?
C2 C4 C5 C8 0.8(3) . . . 2_456 ?
C2 C4 C6 C7 178.94(19) . . . . ?
C3 N1 C2 O1 178.43(19) . . . . ?
C3 N1 C2 C4 -1.9(3) . . . . ?
C4 C6 C7 C8 0.9(3) . . . . ?
C5 C4 C6 C7 -0.9(3) . . . . ?
C6 C4 C5 C5 0.2(4) . . . 2_456 ?
C6 C4 C5 C8 -179.30(18) . . . 2_456 ?
C6 C7 C8 C3 -179.26(19) . . . 2_456 ?
C6 C7 C8 C5 -0.2(3) . . . 2_456 ?
C9 C10 C11 C12 -179.0(2) . . . . ?
C9 C10 C11 C16 1.0(3) . . . . ?
C9 C18 C19 C20 -179.1(2) 2_556 . . . ?
C10 C11 C12 C13 -179.7(2) . . . . ?
C10 C11 C16 C15 179.78(19) . . . . ?
C10 C11 C16 C17 -0.2(3) . . . 2_556 ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C11 C16 C17 179.69(18) . . . 2_556 ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C20 177.9(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C13 C14 C15 C17 180.00(19) . . . . ?
C13 C14 C20 C19 -180.0(2) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C14 C15 C16 C17 179.63(18) . . . 2_556 ?
C14 C15 C17 C16 -179.63(18) . . . 2_556 ?
C14 C15 C17 C18 0.1(3) . . . . ?
C15 C14 C20 C19 -1.2(4) . . . . ?
C15 C17 C18 C9 179.1(2) . . . 2_556 ?
C15 C17 C18 C19 -1.4(3) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C16 C15 C17 C16 -0.6(3) . . . 2_556 ?
C16 C15 C17 C18 179.16(18) . . . . ?
C16 C17 C18 C9 -1.2(3) 2_556 . . 2_556 ?
C16 C17 C18 C19 178.36(19) 2_556 . . . ?
C17 C15 C16 C11 -179.44(18) . . . . ?
C17 C15 C16 C17 0.6(3) . . . 2_556 ?
C17 C18 C19 C20 1.4(4) . . . . ?
C18 C9 C10 C11 -0.6(4) 2_556 . . . ?
C18 C19 C20 C14 -0.1(4) . . . . ?
C20 C14 C15 C16 -177.88(19) . . . . ?
C20 C14 C15 C17 1.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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# Please retain this information to preserve the provenance of 
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data_mo_20211223_ny_cn3_0m
_database_code_depnum_ccdc_archive 'CCDC 2190910'
loop_
_audit_author_name
_audit_author_address
'Zhengkun Ju'
;NJUPT
China
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2023-03-23 downloaded from the CCDC.
;
_audit_creation_date             2021-12-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O4, C24 H12'
_chemical_formula_sum            'C44 H30 N2 O4'
_chemical_formula_weight         650.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.5507(9)
_cell_length_b                   10.0972(13)
_cell_length_c                   10.5074(13)
_cell_angle_alpha                86.191(5)
_cell_angle_beta                 76.039(5)
_cell_angle_gamma                79.920(5)
_cell_volume                     765.18(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2203
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      26.958
_cell_measurement_theta_min      2.826
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1631 before and 0.0885 after correction.
The Ratio of minimum to maximum transmission is 0.8987.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_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            12719
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7410
_reflns_number_total             12719
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         12719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.019
_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)+(0.0417P)²+0.3878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6545(3) 0.6611(2) 0.1190(2) 0.0429(6) Uani 1 1 d . . . . .
O2 O 0.6750(3) 0.8753(2) 0.4806(2) 0.0392(6) Uani 1 1 d . . . . .
N1 N 0.6736(3) 0.7646(2) 0.2995(2) 0.0301(6) Uani 1 1 d . . . . .
C1 C 0.6615(5) 1.0873(3) 0.0864(3) 0.0466(9) Uani 1 1 d . . . . .
H1A H 0.738305 1.045052 0.005779 0.070 Uiso 1 1 calc R U . . .
H1B H 0.736037 1.135735 0.125600 0.070 Uiso 1 1 calc R U . . .
H1C H 0.557578 1.150690 0.065649 0.070 Uiso 1 1 calc R U . . .
C2 C 0.5876(4) 0.9793(3) 0.1830(3) 0.0366(7) Uani 1 1 d . . . . .
H2A H 0.511801 1.022144 0.264912 0.044 Uiso 1 1 calc R U . . .
H2B H 0.506914 0.933862 0.145087 0.044 Uiso 1 1 calc R U . . .
C3 C 0.7425(4) 0.8759(3) 0.2148(3) 0.0347(7) Uani 1 1 d . . . . .
H3A H 0.824420 0.839004 0.132133 0.042 Uiso 1 1 calc R U . . .
H3B H 0.816883 0.920372 0.259460 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6349(4) 0.6585(3) 0.2372(3) 0.0306(7) Uani 1 1 d . . . . .
C5 C 0.6427(4) 0.7771(3) 0.4354(3) 0.0290(6) Uani 1 1 d . . . . .
C6 C 0.5694(3) 0.6644(3) 0.5183(3) 0.0261(6) Uani 1 1 d . . . . .
C7 C 0.5369(4) 0.6694(3) 0.6529(3) 0.0303(7) Uani 1 1 d . . . . .
H7 H 0.561399 0.744467 0.691739 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4676(4) 0.5641(3) 0.7328(3) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.444663 0.568854 0.825480 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5351(3) 0.5538(3) 0.4593(3) 0.0245(6) Uani 1 1 d . . . . .
C10 C 0.4328(3) 0.4544(3) 0.6781(3) 0.0263(6) Uani 1 1 d . . . . .
C11 C 0.9733(4) 0.2226(3) 0.2907(4) 0.0448(8) Uani 1 1 d . . . . .
H11 H 0.954048 0.138773 0.265022 0.054 Uiso 1 1 calc R U . . .
C12 C 1.0403(4) 0.3118(4) 0.1971(3) 0.0465(8) Uani 1 1 d . . . . .
H12 H 1.066973 0.289142 0.107393 0.056 Uiso 1 1 calc R U . . .
C13 C 1.0714(4) 0.4384(3) 0.2302(3) 0.0355(7) Uani 1 1 d . . . . .
C14 C 1.1413(4) 0.5345(4) 0.1353(3) 0.0453(9) Uani 1 1 d . . . . .
H14 H 1.166836 0.515076 0.044783 0.054 Uiso 1 1 calc R U . . .
C15 C 1.1727(4) 0.6535(3) 0.1709(3) 0.0436(9) Uani 1 1 d . . . . .
H15 H 1.219016 0.715552 0.104456 0.052 Uiso 1 1 calc R U . . .
C16 C 1.1383(4) 0.6881(3) 0.3042(3) 0.0346(7) Uani 1 1 d . . . . .
C17 C 1.0692(3) 0.5943(3) 0.4023(3) 0.0267(6) Uani 1 1 d . . . . .
C18 C 1.0343(3) 0.4696(3) 0.3647(3) 0.0268(6) Uani 1 1 d . . . . .
C19 C 1.0349(3) 0.6248(3) 0.5372(3) 0.0268(6) Uani 1 1 d . . . . .
C20 C 1.0687(4) 0.7487(3) 0.5738(3) 0.0345(7) Uani 1 1 d . . . . .
C21 C 1.1414(4) 0.8400(3) 0.4734(4) 0.0430(9) Uani 1 1 d . . . . .
H21 H 1.167574 0.922696 0.496439 0.052 Uiso 1 1 calc R U . . .
C22 C 1.1735(4) 0.8093(3) 0.3447(4) 0.0424(9) Uani 1 1 d . . . . .
H22 H 1.221500 0.872066 0.279718 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.215(3) . ?
O2 C5 1.212(3) . ?
N1 C3 1.475(3) . ?
N1 C4 1.398(4) . ?
N1 C5 1.401(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.525(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C10 1.484(4) 2_666 ?
C5 C6 1.489(4) . ?
C6 C7 1.378(4) . ?
C6 C9 1.403(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(4) . ?
C8 H8 0.9500 . ?
C8 C10 1.373(4) . ?
C9 C9 1.432(5) 2_666 ?
C9 C10 1.411(4) 2_666 ?
C11 H11 0.9500 . ?
C11 C12 1.355(5) . ?
C11 C20 1.421(5) 2_766 ?
C12 H12 0.9500 . ?
C12 C13 1.419(5) . ?
C13 C14 1.419(4) . ?
C13 C18 1.419(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.358(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.418(5) . ?
C16 C17 1.419(4) . ?
C16 C22 1.410(4) . ?
C17 C18 1.429(4) . ?
C17 C19 1.423(4) . ?
C18 C19 1.425(4) 2_766 ?
C19 C20 1.414(4) . ?
C20 C21 1.425(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.362(5) . ?
C22 H22 0.9500 . ?

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
C4 N1 C3 117.0(2) . . ?
C4 N1 C5 125.4(2) . . ?
C5 N1 C3 117.5(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 C1 111.7(3) . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
N1 C3 C2 112.4(2) . . ?
N1 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 N1 120.6(2) . . ?
O1 C4 C10 122.2(3) . 2_666 ?
N1 C4 C10 117.2(3) . 2_666 ?
O2 C5 N1 120.7(2) . . ?
O2 C5 C6 123.0(3) . . ?
N1 C5 C6 116.3(2) . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 C9 120.5(2) . . ?
C9 C6 C5 120.0(3) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C10 C8 C7 120.6(3) . . ?
C10 C8 H8 119.7 . . ?
C6 C9 C9 119.2(3) . 2_666 ?
C6 C9 C10 121.9(2) . 2_666 ?
C10 C9 C9 118.9(3) 2_666 2_666 ?
C8 C10 C4 120.4(3) . 2_666 ?
C8 C10 C9 120.4(2) . 2_666 ?
C9 C10 C4 119.1(3) 2_666 2_666 ?
C12 C11 H11 119.2 . . ?
C12 C11 C20 121.6(3) . 2_766 ?
C20 C11 H11 119.2 2_766 . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 123.1(3) . . ?
C18 C13 C12 118.6(3) . . ?
C18 C13 C14 118.2(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.0 . . ?
C14 C15 C16 122.0(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 118.3(3) . . ?
C22 C16 C15 123.5(3) . . ?
C22 C16 C17 118.2(3) . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 C19 119.9(3) . . ?
C19 C17 C18 120.4(2) . . ?
C13 C18 C17 120.3(3) . . ?
C13 C18 C19 119.8(3) . 2_766 ?
C19 C18 C17 119.8(3) 2_766 . ?
C17 C19 C18 119.7(2) . 2_766 ?
C20 C19 C17 120.1(3) . . ?
C20 C19 C18 120.1(3) . 2_766 ?
C11 C20 C21 122.8(3) 2_766 . ?
C19 C20 C11 118.4(3) . 2_766 ?
C19 C20 C21 118.8(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C16 C22 H22 118.7 . . ?
C21 C22 C16 122.6(3) . . ?
C21 C22 H22 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C5 C6 C7 -0.5(4) . . . . ?
O2 C5 C6 C9 180.0(2) . . . . ?
N1 C5 C6 C7 179.6(2) . . . . ?
N1 C5 C6 C9 0.0(3) . . . . ?
C1 C2 C3 N1 -175.2(3) . . . . ?
C3 N1 C4 O1 -1.4(4) . . . . ?
C3 N1 C4 C10 179.5(2) . . . 2_666 ?
C3 N1 C5 O2 -1.2(4) . . . . ?
C3 N1 C5 C6 178.7(2) . . . . ?
C4 N1 C3 C2 84.7(3) . . . . ?
C4 N1 C5 O2 -177.5(2) . . . . ?
C4 N1 C5 C6 2.5(4) . . . . ?
C5 N1 C3 C2 -91.8(3) . . . . ?
C5 N1 C4 O1 174.8(3) . . . . ?
C5 N1 C4 C10 -4.3(4) . . . 2_666 ?
C5 C6 C7 C8 180.0(2) . . . . ?
C5 C6 C9 C9 179.9(3) . . . 2_666 ?
C5 C6 C9 C10 -0.4(4) . . . 2_666 ?
C6 C7 C8 C10 0.5(4) . . . . ?
C7 C6 C9 C9 0.3(4) . . . 2_666 ?
C7 C6 C9 C10 -179.9(3) . . . 2_666 ?
C7 C8 C10 C4 178.1(3) . . . 2_666 ?
C7 C8 C10 C9 -0.4(4) . . . 2_666 ?
C9 C6 C7 C8 -0.5(4) . . . . ?
C11 C12 C13 C14 180.0(3) . . . . ?
C11 C12 C13 C18 1.2(4) . . . . ?
C11 C20 C21 C22 -177.8(3) 2_766 . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C12 C13 C18 C17 178.1(3) . . . . ?
C12 C13 C18 C19 -0.8(4) . . . 2_766 ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C14 C13 C18 C19 -179.6(3) . . . 2_766 ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 C22 178.4(3) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C15 C16 C17 C19 179.3(2) . . . . ?
C15 C16 C22 C21 -179.3(3) . . . . ?
C16 C17 C18 C13 1.0(4) . . . . ?
C16 C17 C18 C19 179.9(2) . . . 2_766 ?
C16 C17 C19 C18 -179.9(2) . . . 2_766 ?
C16 C17 C19 C20 0.3(4) . . . . ?
C17 C16 C22 C21 -0.9(4) . . . . ?
C17 C19 C20 C11 177.8(2) . . . 2_766 ?
C17 C19 C20 C21 -1.5(4) . . . . ?
C18 C13 C14 C15 0.0(4) . . . . ?
C18 C17 C19 C18 0.1(4) . . . 2_766 ?
C18 C17 C19 C20 -179.6(2) . . . . ?
C18 C19 C20 C11 -1.9(4) 2_766 . . 2_766 ?
C18 C19 C20 C21 178.8(2) 2_766 . . . ?
C19 C17 C18 C13 -179.0(2) . . . . ?
C19 C17 C18 C19 -0.1(4) . . . 2_766 ?
C19 C20 C21 C22 1.5(4) . . . . ?
C20 C11 C12 C13 -0.1(5) 2_766 . . . ?
C20 C21 C22 C16 -0.3(4) . . . . ?
C22 C16 C17 C18 -179.2(2) . . . . ?
C22 C16 C17 C19 0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.771(7)
2 0.229(7)

