# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1-PXZ-Nap
_database_code_depnum_ccdc_archive 'CCDC 2303516'
loop_
_audit_author_name
_audit_author_address
'Alexandra M. Z. Slawin'
;university of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           'by CrystalStructure 4.3'



_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_weight         309.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.7284(7)
_cell_length_b                   9.2222(7)
_cell_length_c                   11.3466(7)
_cell_angle_alpha                110.237(6)
_cell_angle_beta                 100.707(6)
_cell_angle_gamma                108.806(7)
_cell_volume                     764.42(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6483
_cell_measurement_theta_min      4.51
_cell_measurement_theta_max      67.90
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324.00
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.879

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            6908
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_theta_max         67.053
_diffrn_reflns_theta_min         4.407
_diffrn_reflns_theta_full        67.053
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2684
_reflns_number_gt                2524
_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          0.1148
_refine_ls_R_factor_gt           0.1110
_refine_ls_wR_factor_ref         0.3259
_refine_ls_wR_factor_gt          0.3173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2684
_refine_ls_number_parameters     218
_refine_ls_goodness_of_fit_ref   1.628
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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         0.67
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.097(16)

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
O8 O 0.39758(17) 0.14601(15) 0.22205(15) 0.0433(6) Uani 1 1 d . . . . .
N1 N 0.64529(19) 0.39759(18) 0.18886(15) 0.0354(6) Uani 1 1 d . . . . .
C2 C 0.5254(2) 0.4358(2) 0.24723(16) 0.0341(6) Uani 1 1 d . . . . .
C3 C 0.5222(2) 0.5937(2) 0.2890(2) 0.0405(6) Uani 1 1 d . . . . .
H3 H 0.603500 0.682161 0.278982 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3998(3) 0.6250(2) 0.3462(2) 0.0470(6) Uani 1 1 d . . . . .
H4 H 0.398637 0.734262 0.374513 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2814(3) 0.4978(3) 0.3613(2) 0.0468(7) Uani 1 1 d . . . . .
H5 H 0.198447 0.519218 0.399642 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2836(2) 0.3383(2) 0.3204(2) 0.0413(6) Uani 1 1 d . . . . .
H6 H 0.202135 0.250234 0.330699 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4053(2) 0.3082(2) 0.26446(18) 0.0361(6) Uani 1 1 d . . . . .
C9 C 0.5362(2) 0.1218(2) 0.18922(17) 0.0349(6) Uani 1 1 d . . . . .
C10 C 0.5411(2) -0.0315(2) 0.16882(18) 0.0368(6) Uani 1 1 d . . . . .
H10 H 0.454387 -0.114378 0.179947 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6744(2) -0.0658(2) 0.13146(18) 0.0389(6) Uani 1 1 d . . . . .
H11 H 0.677779 -0.172649 0.115840 0.047 Uiso 1 1 calc R U . . .
C12 C 0.8004(2) 0.0565(2) 0.11758(18) 0.0380(6) Uani 1 1 d . . . . .
H12 H 0.891932 0.034390 0.093383 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7949(2) 0.2120(2) 0.13866(18) 0.0361(6) Uani 1 1 d . . . . .
H13 H 0.883472 0.295748 0.129762 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6609(2) 0.2467(2) 0.17275(16) 0.0326(6) Uani 1 1 d . . . . .
C15 C 0.7713(2) 0.5266(2) 0.17152(18) 0.0338(6) Uani 1 1 d . . . . .
C16 C 0.7506(2) 0.5199(2) 0.04799(18) 0.0376(6) Uani 1 1 d . . . . .
H16 H 0.652222 0.431927 -0.024886 0.045 Uiso 1 1 calc R U . . .
C17 C 0.8745(2) 0.6432(2) 0.02642(18) 0.0400(6) Uani 1 1 d . . . . .
H17 H 0.859379 0.636560 -0.060679 0.048 Uiso 1 1 calc R U . . .
C18 C 1.0147(2) 0.7706(2) 0.13055(19) 0.0360(6) Uani 1 1 d . . . . .
H18 H 1.097244 0.852762 0.115768 0.043 Uiso 1 1 calc R U . . .
C19 C 1.0387(2) 0.7818(2) 0.26121(19) 0.0346(6) Uani 1 1 d . . . . .
C20 C 1.1816(2) 0.9136(2) 0.3726(2) 0.0402(6) Uani 1 1 d . . . . .
H20 H 1.264376 0.998697 0.360423 0.048 Uiso 1 1 calc R U . . .
C21 C 1.2028(3) 0.9209(3) 0.4974(2) 0.0483(6) Uani 1 1 d . . . . .
H21 H 1.299081 1.010989 0.570931 0.058 Uiso 1 1 calc R U . . .
C22 C 1.0831(3) 0.7960(3) 0.5168(2) 0.0473(7) Uani 1 1 d . . . . .
H22 H 1.099698 0.801217 0.603543 0.057 Uiso 1 1 calc R U . . .
C23 C 0.9438(2) 0.6678(2) 0.41374(19) 0.0385(6) Uani 1 1 d . . . . .
H23 H 0.863583 0.584665 0.429253 0.046 Uiso 1 1 calc R U . . .
C24 C 0.9160(2) 0.6559(2) 0.28219(18) 0.0341(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
O8 C7 1.378(2) . ?
O8 C9 1.392(2) . ?
N1 C14 1.394(2) . ?
N1 C2 1.412(2) . ?
N1 C15 1.436(2) . ?
C2 C3 1.378(2) . ?
C2 C7 1.400(3) . ?
C3 C4 1.405(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C9 C10 1.367(3) . ?
C9 C14 1.401(3) . ?
C10 C11 1.400(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.357(3) . ?
C15 C24 1.413(3) . ?
C16 C17 1.421(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.360(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.420(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.416(3) . ?
C19 C24 1.427(3) . ?
C20 C21 1.369(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.353(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.426(3) . ?
C23 H23 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
C7 O8 C9 117.44(13) . . ?
C14 N1 C2 118.88(13) . . ?
C14 N1 C15 120.13(14) . . ?
C2 N1 C15 119.83(14) . . ?
C3 C2 C7 118.58(16) . . ?
C3 C2 N1 122.82(15) . . ?
C7 C2 N1 118.59(16) . . ?
C2 C3 C4 120.56(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.24(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.90(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.65(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O8 C7 C6 116.95(15) . . ?
O8 C7 C2 121.93(16) . . ?
C6 C7 C2 121.06(17) . . ?
C10 C9 O8 116.97(15) . . ?
C10 C9 C14 121.83(17) . . ?
O8 C9 C14 121.15(16) . . ?
C9 C10 C11 119.77(16) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.42(16) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.51(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.81(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
N1 C14 C13 122.96(15) . . ?
N1 C14 C9 119.41(16) . . ?
C13 C14 C9 117.62(16) . . ?
C16 C15 C24 121.13(16) . . ?
C16 C15 N1 119.10(16) . . ?
C24 C15 N1 119.76(16) . . ?
C15 C16 C17 120.72(17) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.95(16) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.55(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 122.33(16) . . ?
C20 C19 C24 118.26(18) . . ?
C18 C19 C24 119.41(18) . . ?
C21 C20 C19 121.26(17) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.10(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.94(19) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.85(17) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C15 C24 C23 123.20(16) . . ?
C15 C24 C19 118.22(18) . . ?
C23 C24 C19 118.57(18) . . ?

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
C14 N1 C2 C3 167.99(16) . . . . ?
C15 N1 C2 C3 0.3(3) . . . . ?
C14 N1 C2 C7 -11.5(2) . . . . ?
C15 N1 C2 C7 -179.19(16) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
N1 C2 C3 C4 179.83(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C9 O8 C7 C6 -168.25(16) . . . . ?
C9 O8 C7 C2 14.4(3) . . . . ?
C5 C6 C7 O8 -178.02(17) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C3 C2 C7 O8 178.24(16) . . . . ?
N1 C2 C7 O8 -2.3(3) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
N1 C2 C7 C6 -179.52(16) . . . . ?
C7 O8 C9 C10 169.41(15) . . . . ?
C7 O8 C9 C14 -13.1(3) . . . . ?
O8 C9 C10 C11 178.02(15) . . . . ?
C14 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C2 N1 C14 C13 -168.26(15) . . . . ?
C15 N1 C14 C13 -0.6(3) . . . . ?
C2 N1 C14 C9 12.7(2) . . . . ?
C15 N1 C14 C9 -179.61(16) . . . . ?
C12 C13 C14 N1 -176.93(15) . . . . ?
C12 C13 C14 C9 2.1(3) . . . . ?
C10 C9 C14 N1 177.05(15) . . . . ?
O8 C9 C14 N1 -0.3(3) . . . . ?
C10 C9 C14 C13 -2.0(3) . . . . ?
O8 C9 C14 C13 -179.42(15) . . . . ?
C14 N1 C15 C16 88.0(2) . . . . ?
C2 N1 C15 C16 -104.48(18) . . . . ?
C14 N1 C15 C24 -90.83(19) . . . . ?
C2 N1 C15 C24 76.7(2) . . . . ?
C24 C15 C16 C17 0.1(3) . . . . ?
N1 C15 C16 C17 -178.65(15) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -179.16(14) . . . . ?
C17 C18 C19 C24 1.3(3) . . . . ?
C18 C19 C20 C21 -179.38(15) . . . . ?
C24 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C16 C15 C24 C23 -179.72(14) . . . . ?
N1 C15 C24 C23 -1.0(3) . . . . ?
C16 C15 C24 C19 1.2(3) . . . . ?
N1 C15 C24 C19 179.93(15) . . . . ?
C22 C23 C24 C15 -178.82(14) . . . . ?
C22 C23 C24 C19 0.3(3) . . . . ?
C20 C19 C24 C15 178.57(12) . . . . ?
C18 C19 C24 C15 -1.9(3) . . . . ?
C20 C19 C24 C23 -0.6(3) . . . . ?
C18 C19 C24 C23 178.99(13) . . . . ?


#==============================================================================
# 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
#==============================================================================
####################################################################### 
# 
# 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_2-PXZ-Nap
_database_code_depnum_ccdc_archive 'CCDC 2303517'
loop_
_audit_author_name
_audit_author_address
'Alexandra M. Z. Slawin'
;university of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2022-02-15
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_weight         309.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.1593(16)
_cell_length_b                   23.215(7)
_cell_length_c                   11.123(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.9870(10)
_cell_angle_gamma                90.0000
_cell_volume                     1528.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5353
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.999

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            10984
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_theta_max         25.386
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2784
_reflns_number_gt                2521
_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          0.0448
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1203
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0723P)²+0.4815P] 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         0.44
_refine_diff_density_min         -0.20
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
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
O8 O 0.39524(17) 0.07560(4) 0.37164(10) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.46145(19) 0.19340(5) 0.33474(12) 0.0313(3) Uani 1 1 d . . . . .
C2 C 0.6439(2) 0.15931(6) 0.40195(12) 0.0259(3) Uani 1 1 d . . . . .
C3 C 0.8590(2) 0.18112(6) 0.45584(13) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.888935 0.220656 0.445222 0.035 Uiso 1 1 calc R U . . .
C4 C 1.0308(2) 0.14588(7) 0.52506(14) 0.0330(3) Uani 1 1 d . . . . .
H4 H 1.176795 0.161492 0.561241 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9902(3) 0.08807(7) 0.54156(14) 0.0359(4) Uani 1 1 d . . . . .
H5 H 1.107480 0.064095 0.589384 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7765(3) 0.06547(6) 0.48752(14) 0.0330(3) Uani 1 1 d . . . . .
H6 H 0.747556 0.025842 0.497822 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6068(2) 0.10057(6) 0.41900(13) 0.0280(3) Uani 1 1 d . . . . .
C9 C 0.2382(2) 0.10655(6) 0.28124(13) 0.0276(3) Uani 1 1 d . . . . .
C10 C 0.0481(2) 0.07749(6) 0.21504(14) 0.0325(3) Uani 1 1 d . . . . .
H10 H 0.031789 0.037647 0.229973 0.039 Uiso 1 1 calc R U . . .
C11 C -0.1200(2) 0.10637(6) 0.12632(14) 0.0332(3) Uani 1 1 d . . . . .
H11 H -0.252139 0.086547 0.080981 0.040 Uiso 1 1 calc R U . . .
C12 C -0.0929(2) 0.16434(6) 0.10470(13) 0.0294(3) Uani 1 1 d . . . . .
H12 H -0.206659 0.184241 0.043703 0.035 Uiso 1 1 calc R U . . .
C13 C 0.0993(2) 0.19364(6) 0.17157(13) 0.0265(3) Uani 1 1 d . . . . .
H13 H 0.116144 0.233343 0.155498 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2673(2) 0.16540(6) 0.26176(12) 0.0246(3) Uani 1 1 d . . . . .
C15 C 0.4855(2) 0.25442(6) 0.32191(12) 0.0271(3) Uani 1 1 d . . . . .
C16 C 0.6281(2) 0.27553(6) 0.25053(14) 0.0327(3) Uani 1 1 d . . . . .
H16 H 0.705425 0.249160 0.211614 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6547(2) 0.33357(6) 0.23749(14) 0.0324(3) Uani 1 1 d . . . . .
H17 H 0.753808 0.347220 0.191807 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5352(2) 0.37320(6) 0.29170(12) 0.0273(3) Uani 1 1 d . . . . .
C19 C 0.5558(3) 0.43417(6) 0.27886(14) 0.0344(4) Uani 1 1 d . . . . .
H19 H 0.653577 0.448779 0.233314 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4376(3) 0.47143(6) 0.33082(14) 0.0365(4) Uani 1 1 d . . . . .
H20 H 0.452444 0.511745 0.320794 0.044 Uiso 1 1 calc R U . . .
C21 C 0.2917(3) 0.45044(6) 0.40015(15) 0.0368(4) Uani 1 1 d . . . . .
H21 H 0.210798 0.476867 0.436794 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2668(3) 0.39240(6) 0.41454(14) 0.0338(3) Uani 1 1 d . . . . .
H22 H 0.168421 0.378740 0.460698 0.041 Uiso 1 1 calc R U . . .
C23 C 0.3877(2) 0.35278(6) 0.36058(12) 0.0265(3) Uani 1 1 d . . . . .
C24 C 0.3686(2) 0.29179(6) 0.37544(13) 0.0292(3) Uani 1 1 d . . . . .
H24 H 0.273768 0.277296 0.422893 0.035 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
O8 C9 1.3884(17) . ?
O8 C7 1.3902(17) . ?
N1 C14 1.4059(17) . ?
N1 C2 1.4088(17) . ?
N1 C15 1.4356(17) . ?
C2 C3 1.3905(19) . ?
C2 C7 1.404(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C9 C10 1.376(2) . ?
C9 C14 1.4024(19) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3903(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3912(19) . ?
C13 H13 0.9500 . ?
C15 C24 1.365(2) . ?
C15 C16 1.423(2) . ?
C16 C17 1.370(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(2) . ?
C17 H17 0.9500 . ?
C18 C23 1.422(2) . ?
C18 C19 1.432(2) . ?
C19 C20 1.358(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.422(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.417(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.434(2) . ?
C24 H24 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
C9 O8 C7 116.86(11) . . ?
C14 N1 C2 118.27(11) . . ?
C14 N1 C15 119.58(11) . . ?
C2 N1 C15 121.19(11) . . ?
C3 C2 C7 117.81(12) . . ?
C3 C2 N1 123.38(12) . . ?
C7 C2 N1 118.79(12) . . ?
C2 C3 C4 120.94(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.35(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.45(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 119.99(13) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 O8 116.88(12) . . ?
C6 C7 C2 121.46(13) . . ?
O8 C7 C2 121.61(12) . . ?
C10 C9 O8 117.01(12) . . ?
C10 C9 C14 121.41(12) . . ?
O8 C9 C14 121.53(12) . . ?
C9 C10 C11 120.07(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.34(13) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.52(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.67(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 117.97(12) . . ?
C13 C14 N1 122.95(12) . . ?
C9 C14 N1 119.07(12) . . ?
C24 C15 C16 120.37(13) . . ?
C24 C15 N1 120.16(13) . . ?
C16 C15 N1 119.46(12) . . ?
C17 C16 C15 120.51(13) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.27(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C23 119.87(13) . . ?
C17 C18 C19 122.04(13) . . ?
C23 C18 C19 118.08(13) . . ?
C20 C19 C18 120.97(14) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.38(13) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.54(14) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.00(14) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.02(13) . . ?
C22 C23 C24 121.51(13) . . ?
C18 C23 C24 118.46(12) . . ?
C15 C24 C23 120.48(13) . . ?
C15 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?

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
C14 N1 C2 C3 166.29(13) . . . . ?
C15 N1 C2 C3 -2.5(2) . . . . ?
C14 N1 C2 C7 -15.60(19) . . . . ?
C15 N1 C2 C7 175.59(13) . . . . ?
C7 C2 C3 C4 -0.5(2) . . . . ?
N1 C2 C3 C4 177.65(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C5 C6 C7 O8 -177.65(13) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C9 O8 C7 C6 -166.42(12) . . . . ?
C9 O8 C7 C2 15.93(19) . . . . ?
C3 C2 C7 C6 0.5(2) . . . . ?
N1 C2 C7 C6 -177.74(13) . . . . ?
C3 C2 C7 O8 178.00(12) . . . . ?
N1 C2 C7 O8 -0.2(2) . . . . ?
C7 O8 C9 C10 166.39(12) . . . . ?
C7 O8 C9 C14 -16.18(19) . . . . ?
O8 C9 C10 C11 177.63(13) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C9 1.1(2) . . . . ?
C12 C13 C14 N1 -177.90(13) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
O8 C9 C14 C13 -178.35(12) . . . . ?
C10 C9 C14 N1 178.00(13) . . . . ?
O8 C9 C14 N1 0.7(2) . . . . ?
C2 N1 C14 C13 -165.61(13) . . . . ?
C15 N1 C14 C13 3.4(2) . . . . ?
C2 N1 C14 C9 15.40(19) . . . . ?
C15 N1 C14 C9 -175.61(13) . . . . ?
C14 N1 C15 C24 76.98(17) . . . . ?
C2 N1 C15 C24 -114.36(15) . . . . ?
C14 N1 C15 C16 -101.54(15) . . . . ?
C2 N1 C15 C16 67.12(17) . . . . ?
C24 C15 C16 C17 1.8(2) . . . . ?
N1 C15 C16 C17 -179.66(12) . . . . ?
C15 C16 C17 C18 -1.9(2) . . . . ?
C16 C17 C18 C23 0.3(2) . . . . ?
C16 C17 C18 C19 -179.13(13) . . . . ?
C17 C18 C19 C20 179.36(13) . . . . ?
C23 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C21 C22 C23 C24 178.98(13) . . . . ?
C17 C18 C23 C22 -179.68(13) . . . . ?
C19 C18 C23 C22 -0.22(19) . . . . ?
C17 C18 C23 C24 1.43(19) . . . . ?
C19 C18 C23 C24 -179.11(12) . . . . ?
C16 C15 C24 C23 -0.03(19) . . . . ?
N1 C15 C24 C23 -178.54(11) . . . . ?
C22 C23 C24 C15 179.57(12) . . . . ?
C18 C23 C24 C15 -1.56(19) . . . . ?


#==============================================================================
# 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
#==============================================================================
####################################################################### 
# 
# 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_PXZ-Nap-PXZ
_database_code_depnum_ccdc_archive 'CCDC 2303518'
loop_
_audit_author_name
_audit_author_address
'Alexandra M. Z. Slawin'
;university of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;

_audit_creation_date             2022-02-14
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C34 H22 N2 O2'
_chemical_formula_moiety         'C34 H22 N2 O2'
_chemical_formula_weight         490.56
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.065(4)
_cell_length_b                   11.616(5)
_cell_length_c                   11.685(4)
_cell_angle_alpha                95.103(11)
_cell_angle_beta                 90.394(6)
_cell_angle_gamma                102.932(12)
_cell_volume                     1194.0(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2669
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.60
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.997

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            13566
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4311
_reflns_number_gt                3469
_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          0.1007
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.3028
_refine_ls_wR_factor_gt          0.2844
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4311
_refine_ls_number_parameters     343
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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         0.59
_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 0.0033 0.0016
;
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 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
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
O8 O 0.4227(2) 0.88266(18) -0.10242(17) 0.0299(6) Uani 1 1 d . . . . .
O32 O 1.0328(2) 0.72551(19) 0.69214(16) 0.0307(6) Uani 1 1 d . . . . .
N1 N 0.5897(3) 0.8353(2) 0.08266(19) 0.0236(6) Uani 1 1 d . . . . .
N25 N 0.8936(3) 0.7634(2) 0.48741(19) 0.0245(6) Uani 1 1 d . . . . .
C2 C 0.6649(3) 0.8699(2) -0.0181(2) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.8201(3) 0.8852(2) -0.0301(2) 0.0272(7) Uani 1 1 d . . . . .
H3 H 0.880995 0.872026 0.031754 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8871(4) 0.9196(3) -0.1321(3) 0.0294(7) Uani 1 1 d . . . . .
H4 H 0.993679 0.930928 -0.139001 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7997(4) 0.9377(3) -0.2238(2) 0.0303(7) Uani 1 1 d . . . . .
H5 H 0.845640 0.960241 -0.293642 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6440(4) 0.9224(3) -0.2126(2) 0.0301(7) Uani 1 1 d . . . . .
H6 H 0.583320 0.934092 -0.275189 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5776(3) 0.8903(2) -0.1112(2) 0.0243(7) Uani 1 1 d . . . . .
C9 C 0.3498(3) 0.8150(2) -0.0186(2) 0.0243(7) Uani 1 1 d . . . . .
C10 C 0.1950(3) 0.7762(3) -0.0288(3) 0.0286(7) Uani 1 1 d . . . . .
H10 H 0.141964 0.794476 -0.092696 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1160(3) 0.7105(3) 0.0539(3) 0.0304(7) Uani 1 1 d . . . . .
H11 H 0.008965 0.684362 0.047456 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1951(3) 0.6834(3) 0.1463(3) 0.0301(7) Uani 1 1 d . . . . .
H12 H 0.142012 0.637509 0.202733 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3520(3) 0.7231(3) 0.1568(2) 0.0255(7) Uani 1 1 d . . . . .
H13 H 0.404760 0.703887 0.220359 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4321(3) 0.7903(2) 0.0755(2) 0.0229(6) Uani 1 1 d . . . . .
C15 C 0.6734(3) 0.8170(2) 0.1817(2) 0.0226(6) Uani 1 1 d . . . . .
C16 C 0.7069(3) 0.9052(2) 0.2699(2) 0.0253(7) Uani 1 1 d . . . . .
H16 H 0.680090 0.978814 0.262970 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7820(3) 0.8870(3) 0.3718(2) 0.0262(7) Uani 1 1 d . . . . .
H17 H 0.804523 0.948488 0.432874 0.031 Uiso 1 1 calc R U . . .
C18 C 0.8219(3) 0.7815(2) 0.3825(2) 0.0234(6) Uani 1 1 d . . . . .
C19 C 0.7924(3) 0.6887(2) 0.2904(2) 0.0224(7) Uani 1 1 d . . . . .
C20 C 0.8356(3) 0.5790(2) 0.2963(2) 0.0252(7) Uani 1 1 d . . . . .
H20 H 0.886740 0.565544 0.363337 0.030 Uiso 1 1 calc R U . . .
C21 C 0.8042(3) 0.4925(2) 0.2063(2) 0.0270(7) Uani 1 1 d . . . . .
H21 H 0.834275 0.419749 0.211396 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7281(3) 0.5103(2) 0.1067(2) 0.0275(7) Uani 1 1 d . . . . .
H22 H 0.706991 0.449399 0.045018 0.033 Uiso 1 1 calc R U . . .
C23 C 0.6842(3) 0.6140(2) 0.0973(2) 0.0233(6) Uani 1 1 d . . . . .
H23 H 0.632292 0.624438 0.029457 0.028 Uiso 1 1 calc R U . . .
C24 C 0.7155(3) 0.7072(2) 0.1887(2) 0.0217(6) Uani 1 1 d . . . . .
C26 C 1.0523(3) 0.7845(2) 0.4971(2) 0.0233(6) Uani 1 1 d . . . . .
C27 C 1.1471(3) 0.8265(2) 0.4095(2) 0.0262(7) Uani 1 1 d . . . . .
H27 H 1.104632 0.839294 0.338467 0.031 Uiso 1 1 calc R U . . .
C28 C 1.3037(3) 0.8500(2) 0.4253(2) 0.0285(7) Uani 1 1 d . . . . .
H28 H 1.366958 0.879976 0.365246 0.034 Uiso 1 1 calc R U . . .
C29 C 1.3685(3) 0.8303(3) 0.5273(2) 0.0289(7) Uani 1 1 d . . . . .
H29 H 1.475471 0.846758 0.537541 0.035 Uiso 1 1 calc R U . . .
C30 C 1.2748(3) 0.7859(3) 0.6148(2) 0.0271(7) Uani 1 1 d . . . . .
H30 H 1.317722 0.770407 0.684653 0.032 Uiso 1 1 calc R U . . .
C31 C 1.1199(3) 0.7645(2) 0.5999(2) 0.0250(7) Uani 1 1 d . . . . .
C33 C 0.8791(3) 0.6785(2) 0.6702(2) 0.0255(7) Uani 1 1 d . . . . .
C34 C 0.7989(4) 0.6178(3) 0.7544(2) 0.0299(7) Uani 1 1 d . . . . .
H34 H 0.849796 0.605323 0.822015 0.036 Uiso 1 1 calc R U . . .
C35 C 0.6436(4) 0.5749(3) 0.7404(3) 0.0338(8) Uani 1 1 d . . . . .
H35 H 0.587786 0.533812 0.798759 0.041 Uiso 1 1 calc R U . . .
C36 C 0.5705(3) 0.5919(3) 0.6415(3) 0.0316(7) Uani 1 1 d . . . . .
H36 H 0.464171 0.562428 0.631906 0.038 Uiso 1 1 calc R U . . .
C37 C 0.6515(3) 0.6522(3) 0.5557(2) 0.0275(7) Uani 1 1 d . . . . .
H37 H 0.600320 0.662673 0.487547 0.033 Uiso 1 1 calc R U . . .
C38 C 0.8067(3) 0.6969(2) 0.5692(2) 0.0239(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
O8 C9 1.389(3) . ?
O8 C7 1.391(4) . ?
O32 C31 1.388(3) . ?
O32 C33 1.391(4) . ?
N1 C14 1.406(4) . ?
N1 C2 1.409(4) . ?
N1 C15 1.437(3) . ?
N25 C26 1.407(4) . ?
N25 C38 1.414(4) . ?
N25 C18 1.437(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.408(4) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(4) . ?
C6 H6 0.9500 . ?
C9 C10 1.375(4) . ?
C9 C14 1.410(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C15 C16 1.368(4) . ?
C15 C24 1.420(4) . ?
C16 C17 1.423(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.369(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.433(4) . ?
C19 C20 1.421(4) . ?
C19 C24 1.431(4) . ?
C20 C21 1.370(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.404(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.364(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.430(4) . ?
C23 H23 0.9500 . ?
C26 C27 1.392(4) . ?
C26 C31 1.406(4) . ?
C27 C28 1.392(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.377(4) . ?
C30 H30 0.9500 . ?
C33 C34 1.378(4) . ?
C33 C38 1.403(4) . ?
C34 C35 1.387(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.393(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(4) . ?
C37 H37 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
C9 O8 C7 116.5(2) . . ?
C31 O32 C33 117.3(2) . . ?
C14 N1 C2 118.3(2) . . ?
C14 N1 C15 119.2(2) . . ?
C2 N1 C15 120.6(2) . . ?
C26 N25 C38 118.4(2) . . ?
C26 N25 C18 120.2(2) . . ?
C38 N25 C18 119.5(2) . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 N1 123.4(2) . . ?
C7 C2 N1 118.1(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 O8 117.9(3) . . ?
C6 C7 C2 120.8(3) . . ?
O8 C7 C2 121.2(2) . . ?
C10 C9 O8 117.8(2) . . ?
C10 C9 C14 121.5(3) . . ?
O8 C9 C14 120.7(2) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 N1 123.5(2) . . ?
C13 C14 C9 117.8(3) . . ?
N1 C14 C9 118.7(2) . . ?
C16 C15 C24 121.0(3) . . ?
C16 C15 N1 119.0(3) . . ?
C24 C15 N1 120.0(2) . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 N25 119.7(2) . . ?
C19 C18 N25 119.6(3) . . ?
C20 C19 C24 118.8(2) . . ?
C20 C19 C18 122.7(2) . . ?
C24 C19 C18 118.5(3) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C15 C24 C19 119.1(2) . . ?
C15 C24 C23 122.3(2) . . ?
C19 C24 C23 118.5(3) . . ?
C27 C26 C31 117.9(3) . . ?
C27 C26 N25 122.9(2) . . ?
C31 C26 N25 119.2(2) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 119.2(3) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 O32 117.2(2) . . ?
C30 C31 C26 121.6(3) . . ?
O32 C31 C26 121.2(2) . . ?
C34 C33 O32 117.3(2) . . ?
C34 C33 C38 121.1(3) . . ?
O32 C33 C38 121.6(2) . . ?
C33 C34 C35 119.9(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.4(3) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C38 C37 C36 120.4(3) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C33 118.3(3) . . ?
C37 C38 N25 122.9(3) . . ?
C33 C38 N25 118.7(2) . . ?

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
C14 N1 C2 C3 -162.3(3) . . . . ?
C15 N1 C2 C3 1.8(4) . . . . ?
C14 N1 C2 C7 18.0(4) . . . . ?
C15 N1 C2 C7 -177.9(2) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
N1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 O8 176.5(2) . . . . ?
C5 C6 C7 C2 -1.4(4) . . . . ?
C9 O8 C7 C6 159.6(2) . . . . ?
C9 O8 C7 C2 -22.5(4) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
N1 C2 C7 C6 -178.9(2) . . . . ?
C3 C2 C7 O8 -176.5(2) . . . . ?
N1 C2 C7 O8 3.2(4) . . . . ?
C7 O8 C9 C10 -161.0(2) . . . . ?
C7 O8 C9 C14 20.8(4) . . . . ?
O8 C9 C10 C11 -178.6(2) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 N1 178.4(2) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
C2 N1 C14 C13 160.9(3) . . . . ?
C15 N1 C14 C13 -3.4(4) . . . . ?
C2 N1 C14 C9 -19.6(4) . . . . ?
C15 N1 C14 C9 176.1(2) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
O8 C9 C14 C13 179.4(2) . . . . ?
C10 C9 C14 N1 -178.2(2) . . . . ?
O8 C9 C14 N1 -0.2(4) . . . . ?
C14 N1 C15 C16 -96.8(3) . . . . ?
C2 N1 C15 C16 99.3(3) . . . . ?
C14 N1 C15 C24 81.1(3) . . . . ?
C2 N1 C15 C24 -82.8(3) . . . . ?
C24 C15 C16 C17 -1.5(4) . . . . ?
N1 C15 C16 C17 176.4(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 1.6(4) . . . . ?
C16 C17 C18 N25 -178.2(2) . . . . ?
C26 N25 C18 C17 -95.5(3) . . . . ?
C38 N25 C18 C17 100.5(3) . . . . ?
C26 N25 C18 C19 84.8(3) . . . . ?
C38 N25 C18 C19 -79.2(3) . . . . ?
C17 C18 C19 C20 178.2(3) . . . . ?
N25 C18 C19 C20 -2.1(4) . . . . ?
C17 C18 C19 C24 -2.2(4) . . . . ?
N25 C18 C19 C24 177.5(2) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C18 C19 C20 C21 179.6(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C16 C15 C24 C19 0.8(4) . . . . ?
N1 C15 C24 C19 -177.0(2) . . . . ?
C16 C15 C24 C23 -179.0(2) . . . . ?
N1 C15 C24 C23 3.2(4) . . . . ?
C20 C19 C24 C15 -179.3(2) . . . . ?
C18 C19 C24 C15 1.0(4) . . . . ?
C20 C19 C24 C23 0.4(4) . . . . ?
C18 C19 C24 C23 -179.2(2) . . . . ?
C22 C23 C24 C15 179.2(2) . . . . ?
C22 C23 C24 C19 -0.6(4) . . . . ?
C38 N25 C26 C27 166.2(2) . . . . ?
C18 N25 C26 C27 2.0(4) . . . . ?
C38 N25 C26 C31 -14.8(4) . . . . ?
C18 N25 C26 C31 -179.0(2) . . . . ?
C31 C26 C27 C28 -1.4(4) . . . . ?
N25 C26 C27 C28 177.7(2) . . . . ?
C26 C27 C28 C29 1.1(4) . . . . ?
C27 C28 C29 C30 0.2(4) . . . . ?
C28 C29 C30 C31 -1.3(4) . . . . ?
C29 C30 C31 O32 -177.1(2) . . . . ?
C29 C30 C31 C26 1.0(4) . . . . ?
C33 O32 C31 C30 -165.8(2) . . . . ?
C33 O32 C31 C26 16.1(4) . . . . ?
C27 C26 C31 C30 0.3(4) . . . . ?
N25 C26 C31 C30 -178.8(2) . . . . ?
C27 C26 C31 O32 178.3(2) . . . . ?
N25 C26 C31 O32 -0.7(4) . . . . ?
C31 O32 C33 C34 166.9(2) . . . . ?
C31 O32 C33 C38 -16.3(4) . . . . ?
O32 C33 C34 C35 176.2(3) . . . . ?
C38 C33 C34 C35 -0.7(4) . . . . ?
C33 C34 C35 C36 0.8(5) . . . . ?
C34 C35 C36 C37 -0.1(5) . . . . ?
C35 C36 C37 C38 -0.7(4) . . . . ?
C36 C37 C38 C33 0.8(4) . . . . ?
C36 C37 C38 N25 -177.0(3) . . . . ?
C34 C33 C38 C37 -0.2(4) . . . . ?
O32 C33 C38 C37 -176.9(3) . . . . ?
C34 C33 C38 N25 177.8(3) . . . . ?
O32 C33 C38 N25 1.1(4) . . . . ?
C26 N25 C38 C37 -167.6(2) . . . . ?
C18 N25 C38 C37 -3.2(4) . . . . ?
C26 N25 C38 C33 14.6(4) . . . . ?
C18 N25 C38 C33 178.9(2) . . . . ?


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