# Supplementary Information (SI) for Molecular Systems Design & Engineering.
# 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_180509_CyC2BQQDI_1-108A
_database_code_depnum_ccdc_archive 'CCDC 2232687'
loop_
_audit_author_name
_audit_author_address
'Shohei Kumagai'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2022-12-24 deposited with the CCDC.	2024-09-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C38 H36 N4 O4'
_chemical_formula_moiety         'C38 H36 N4 O4'
_chemical_formula_weight         612.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.9724(2)
_cell_length_b                   7.7301(3)
_cell_length_c                   38.8902(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.514(6)
_cell_angle_gamma                90.0000
_cell_volume                     1494.77(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12377
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      68.38
_cell_measurement_temperature    295
#------------------------------------------------------------------------------
_exptl_crystal_description       red
_exptl_crystal_colour            platelet
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.005
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.996

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14338
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_min         4.548
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2718
_reflns_number_gt                1820
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2428
_refine_ls_wR_factor_gt          0.2171
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2711
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1530P)²+0.2104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3852(4) 0.6790(3) 0.42404(5) 0.0621(6) Uani 1 1 d . . . . .
O2 O 1.0523(5) 0.3506(3) 0.37904(5) 0.0693(7) Uani 1 1 d . . . . .
N3 N 0.2095(5) 0.3072(3) 0.49873(6) 0.0484(6) Uani 1 1 d . . . . .
N4 N 0.7216(5) 0.5163(3) 0.40183(6) 0.0507(6) Uani 1 1 d . . . . .
C5 C 0.9592(6) 0.0751(4) 0.42595(7) 0.0484(7) Uani 1 1 d . . . . .
H5 H 1.0931 0.0569 0.4098 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6111(5) 0.2535(3) 0.44973(7) 0.0438(7) Uani 1 1 d . . . . .
C7 C 0.3508(5) 0.1606(3) 0.49898(6) 0.0431(7) Uani 1 1 d . . . . .
C8 C 0.2655(6) 0.4251(3) 0.47454(7) 0.0497(7) Uani 1 1 d . . . . .
H8 H 0.1651 0.5267 0.4744 0.060 Uiso 1 1 calc R U . . .
C9 C 0.9072(6) -0.0525(3) 0.45051(7) 0.0483(7) Uani 1 1 d . . . . .
H9 H 1.0074 -0.1541 0.4505 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8159(5) 0.2265(3) 0.42531(6) 0.0448(7) Uani 1 1 d . . . . .
C11 C 0.5587(5) 0.1266(3) 0.47477(6) 0.0422(7) Uani 1 1 d . . . . .
C12 C 0.4599(6) 0.4071(3) 0.44996(7) 0.0459(7) Uani 1 1 d . . . . .
C13 C 0.7091(5) -0.0300(3) 0.47492(7) 0.0433(7) Uani 1 1 d . . . . .
C14 C 0.5123(6) 0.5445(4) 0.42486(7) 0.0498(7) Uani 1 1 d . . . . .
C15 C 0.8746(6) 0.3656(4) 0.40013(7) 0.0505(7) Uani 1 1 d . . . . .
C16 C 0.6128(7) 0.6530(4) 0.34514(7) 0.0595(8) Uani 1 1 d . . . . .
H16A H 0.4259 0.6352 0.3511 0.071 Uiso 1 1 calc R U . . .
H16B H 0.6693 0.5555 0.3313 0.071 Uiso 1 1 calc R U . . .
C17 C 0.7818(6) 0.6587(4) 0.37783(8) 0.0553(8) Uani 1 1 d . . . . .
H17A H 0.9705 0.6534 0.3718 0.066 Uiso 1 1 calc R U . . .
H17B H 0.7513 0.7681 0.3894 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6368(7) 0.8187(4) 0.32397(8) 0.0577(8) Uani 1 1 d . . . . .
H18 H 0.8287 0.8427 0.3210 0.069 Uiso 1 1 calc R U . . .
C19 C 0.5132(9) 0.9741(4) 0.34136(9) 0.0785(11) Uani 1 1 d . . . . .
H19A H 0.6002 0.9914 0.3635 0.094 Uiso 1 1 calc R U . . .
H19B H 0.3242 0.9514 0.3454 0.094 Uiso 1 1 calc R U . . .
C20 C 0.5129(9) 0.7971(5) 0.28849(9) 0.0810(11) Uani 1 1 d . . . . .
H20A H 0.3237 0.7691 0.2907 0.097 Uiso 1 1 calc R U . . .
H20B H 0.5997 0.7015 0.2769 0.097 Uiso 1 1 calc R U . . .
C21 C 0.5393(10) 1.1388(5) 0.32016(11) 0.0943(14) Uani 1 1 d . . . . .
H21A H 0.4448 1.2321 0.3315 0.113 Uiso 1 1 calc R U . . .
H21B H 0.7275 1.1707 0.3187 0.113 Uiso 1 1 calc R U . . .
C22 C 0.4256(10) 1.1152(6) 0.28434(12) 0.1000(15) Uani 1 1 d . . . . .
H22A H 0.2318 1.1027 0.2856 0.120 Uiso 1 1 calc R U . . .
H22B H 0.4636 1.2175 0.2708 0.120 Uiso 1 1 calc R U . . .
C23 C 0.5413(11) 0.9601(6) 0.26689(10) 0.1003(15) Uani 1 1 d . . . . .
H23A H 0.7302 0.9805 0.2624 0.120 Uiso 1 1 calc R U . . .
H23B H 0.4505 0.9432 0.2450 0.120 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C14 1.217(3) . ?
O2 C15 1.216(3) . ?
N3 C7 1.334(3) . ?
N3 C8 1.341(3) . ?
N4 C15 1.393(4) . ?
N4 C14 1.396(4) . ?
N4 C17 1.476(3) . ?
C5 C10 1.370(4) . ?
C5 C9 1.399(4) . ?
C5 H5 0.9300 . ?
C6 C12 1.405(4) . ?
C6 C11 1.408(4) . ?
C6 C10 1.414(4) . ?
C7 C11 1.429(4) . ?
C7 C13 1.464(4) 3_656 ?
C8 C12 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C13 1.385(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.485(4) . ?
C11 C13 1.423(4) . ?
C12 C14 1.468(4) . ?
C13 C7 1.464(4) 3_656 ?
C16 C17 1.518(5) . ?
C16 C18 1.528(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.512(4) . ?
C18 C20 1.515(5) . ?
C18 H18 0.9800 . ?
C19 C21 1.523(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.522(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.510(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.495(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N3 C8 118.1(2) . . ?
C15 N4 C14 124.9(2) . . ?
C15 N4 C17 118.7(2) . . ?
C14 N4 C17 116.5(2) . . ?
C10 C5 C9 121.0(2) . . ?
C10 C5 H5 119.5 . . ?
C9 C5 H5 119.5 . . ?
C12 C6 C11 118.8(2) . . ?
C12 C6 C10 121.2(2) . . ?
C11 C6 C10 120.0(2) . . ?
N3 C7 C11 122.4(2) . . ?
N3 C7 C13 118.7(2) . 3_656 ?
C11 C7 C13 118.9(2) . 3_656 ?
N3 C8 C12 124.8(2) . . ?
N3 C8 H8 117.6 . . ?
C12 C8 H8 117.6 . . ?
C13 C9 C5 121.1(3) . . ?
C13 C9 H9 119.5 . . ?
C5 C9 H9 119.5 . . ?
C5 C10 C6 119.4(2) . . ?
C5 C10 C15 121.7(2) . . ?
C6 C10 C15 118.9(2) . . ?
C6 C11 C13 119.7(2) . . ?
C6 C11 C7 117.9(2) . . ?
C13 C11 C7 122.5(2) . . ?
C8 C12 C6 118.1(2) . . ?
C8 C12 C14 121.3(2) . . ?
C6 C12 C14 120.6(2) . . ?
C9 C13 C11 118.7(2) . . ?
C9 C13 C7 122.6(2) . 3_656 ?
C11 C13 C7 118.6(2) . 3_656 ?
O1 C14 N4 120.5(3) . . ?
O1 C14 C12 122.7(3) . . ?
N4 C14 C12 116.8(2) . . ?
O2 C15 N4 120.8(3) . . ?
O2 C15 C10 121.6(3) . . ?
N4 C15 C10 117.6(2) . . ?
C17 C16 C18 112.4(3) . . ?
C17 C16 H16A 109.1 . . ?
C18 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C18 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N4 C17 C16 113.2(2) . . ?
N4 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
N4 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C20 109.3(3) . . ?
C19 C18 C16 113.0(2) . . ?
C20 C18 C16 111.4(3) . . ?
C19 C18 H18 107.6 . . ?
C20 C18 H18 107.6 . . ?
C16 C18 H18 107.6 . . ?
C18 C19 C21 112.6(3) . . ?
C18 C19 H19A 109.1 . . ?
C21 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C21 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C18 C20 C23 111.9(3) . . ?
C18 C20 H20A 109.2 . . ?
C23 C20 H20A 109.2 . . ?
C18 C20 H20B 109.2 . . ?
C23 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C19 111.4(3) . . ?
C22 C21 H21A 109.3 . . ?
C19 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C19 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 111.9(3) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C20 112.0(3) . . ?
C22 C23 H23A 109.2 . . ?
C20 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C20 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?

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
C8 N3 C7 C11 0.6(4) . . . . ?
C8 N3 C7 C13 -179.6(2) . . . 3_656 ?
C7 N3 C8 C12 -0.5(4) . . . . ?
C10 C5 C9 C13 0.1(4) . . . . ?
C9 C5 C10 C6 -0.4(4) . . . . ?
C9 C5 C10 C15 178.0(3) . . . . ?
C12 C6 C10 C5 179.9(2) . . . . ?
C11 C6 C10 C5 1.0(4) . . . . ?
C12 C6 C10 C15 1.5(4) . . . . ?
C11 C6 C10 C15 -177.4(2) . . . . ?
C12 C6 C11 C13 179.8(2) . . . . ?
C10 C6 C11 C13 -1.3(4) . . . . ?
C12 C6 C11 C7 0.7(4) . . . . ?
C10 C6 C11 C7 179.6(2) . . . . ?
N3 C7 C11 C6 -0.7(4) . . . . ?
C13 C7 C11 C6 179.5(2) 3_656 . . . ?
N3 C7 C11 C13 -179.8(2) . . . . ?
C13 C7 C11 C13 0.4(4) 3_656 . . . ?
N3 C8 C12 C6 0.6(4) . . . . ?
N3 C8 C12 C14 -178.6(3) . . . . ?
C11 C6 C12 C8 -0.7(4) . . . . ?
C10 C6 C12 C8 -179.6(3) . . . . ?
C11 C6 C12 C14 178.5(2) . . . . ?
C10 C6 C12 C14 -0.4(4) . . . . ?
C5 C9 C13 C11 -0.3(4) . . . . ?
C5 C9 C13 C7 -180.0(3) . . . 3_656 ?
C6 C11 C13 C9 0.9(4) . . . . ?
C7 C11 C13 C9 180.0(3) . . . . ?
C6 C11 C13 C7 -179.5(2) . . . 3_656 ?
C7 C11 C13 C7 -0.4(4) . . . 3_656 ?
C15 N4 C14 O1 -178.4(3) . . . . ?
C17 N4 C14 O1 1.8(4) . . . . ?
C15 N4 C14 C12 2.8(4) . . . . ?
C17 N4 C14 C12 -177.0(2) . . . . ?
C8 C12 C14 O1 -1.3(4) . . . . ?
C6 C12 C14 O1 179.6(3) . . . . ?
C8 C12 C14 N4 177.5(3) . . . . ?
C6 C12 C14 N4 -1.6(4) . . . . ?
C14 N4 C15 O2 179.3(3) . . . . ?
C17 N4 C15 O2 -0.9(4) . . . . ?
C14 N4 C15 C10 -1.8(4) . . . . ?
C17 N4 C15 C10 178.1(2) . . . . ?
C5 C10 C15 O2 0.1(4) . . . . ?
C6 C10 C15 O2 178.5(3) . . . . ?
C5 C10 C15 N4 -178.8(3) . . . . ?
C6 C10 C15 N4 -0.5(4) . . . . ?
C15 N4 C17 C16 93.2(3) . . . . ?
C14 N4 C17 C16 -86.9(3) . . . . ?
C18 C16 C17 N4 168.7(2) . . . . ?
C17 C16 C18 C19 -67.7(4) . . . . ?
C17 C16 C18 C20 168.7(3) . . . . ?
C20 C18 C19 C21 -55.6(4) . . . . ?
C16 C18 C19 C21 179.7(3) . . . . ?
C19 C18 C20 C23 55.6(4) . . . . ?
C16 C18 C20 C23 -178.7(3) . . . . ?
C18 C19 C21 C22 54.5(5) . . . . ?
C19 C21 C22 C23 -52.5(5) . . . . ?
C21 C22 C23 C20 53.3(5) . . . . ?
C18 C20 C23 C22 -55.6(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitrobenzene'
