# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_CP-Py-2-DCB
_database_code_depnum_ccdc_archive 'CCDC 2255738'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        CP-Py-2-DCB
_chemical_formula_moiety         '2(C6 H4 Cl2), C44 H26 O8'
_chemical_formula_sum            'C56 H34 Cl4 O8'
_chemical_formula_weight         976.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5511(4)
_cell_length_b                   11.4435(8)
_cell_length_c                   26.3091(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.902(5)
_cell_angle_gamma                90
_cell_volume                     2270.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5135
_cell_measurement_temperature    113
_cell_measurement_theta_max      29.8470
_cell_measurement_theta_min      1.9600
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.593
_diffrn_reflns_theta_min         1.941
_diffrn_ambient_temperature      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  62.00   0.25    5.00    --  -10.00  45.00 264.00  648
  2  ω    -68.25  35.00   0.25    5.00    --  -10.00  45.00 157.00  413
  3  ω    -58.25  -6.00   0.25    5.00    --  -10.00  45.00  51.00  209
  4  ω      1.00  46.00   0.25    5.00    --  -10.00  45.00 228.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0389248000
_diffrn_orient_matrix_UB_12      -0.0185135000
_diffrn_orient_matrix_UB_13      -0.0226444000
_diffrn_orient_matrix_UB_21      0.0578527000
_diffrn_orient_matrix_UB_22      0.0488327000
_diffrn_orient_matrix_UB_23      0.0014470000
_diffrn_orient_matrix_UB_31      0.0631112000
_diffrn_orient_matrix_UB_32      -0.0333999000
_diffrn_orient_matrix_UB_33      0.0146181000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3463
_reflns_number_total             5753
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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         0.562
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5753
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.065
_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)+(0.0817P)²+2.0781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C3(H3), C14(H14), C1(H1), C13(H13), C17(H17), C2(H2A),
 C11(H11), C10(H10), C18(H18), C28(H28), C25(H25), C27(H27), C26(H26)
3.b Tetrahedral OH refined with riding coordinates:
 O4(H4)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.73345(13) -0.00107(10) 0.37128(5) 0.0581(3) Uani 1 1 d . . . . .
Cl2 Cl 0.42776(15) 0.05310(11) 0.44524(4) 0.0614(3) Uani 1 1 d . . . . .
O3 O 0.2204(2) 0.3055(2) 0.24679(7) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.0241(2) 0.7719(2) 0.32960(8) 0.0322(5) Uani 1 1 d . . . . .
H2 H -0.054066 0.779682 0.305959 0.048 Uiso 1 1 calc R U . . .
O1 O 0.1986(3) 0.7463(2) 0.26413(8) 0.0328(5) Uani 1 1 d . . . . .
O4 O 0.0241(3) 0.3156(2) 0.30712(8) 0.0344(6) Uani 1 1 d . U . . .
H4 H -0.046784 0.300356 0.282372 0.052 Uiso 1 1 calc R U . . .
C8 C 1.0019(3) 0.5617(3) 0.50234(9) 0.0165(6) Uani 1 1 d . . . . .
C5 C 0.7346(3) 0.5741(3) 0.44461(10) 0.0177(6) Uani 1 1 d . . . . .
C16 C 0.5901(3) 0.4011(3) 0.40518(10) 0.0192(6) Uani 1 1 d . . . . .
C6 C 0.7302(3) 0.4558(3) 0.44020(10) 0.0175(6) Uani 1 1 d . . . . .
C7 C 1.1384(3) 0.6175(2) 0.53322(10) 0.0178(6) Uani 1 1 d . . . . .
C9 C 0.6015(3) 0.6434(3) 0.41299(10) 0.0195(6) Uani 1 1 d . . . . .
C4 C 0.8708(3) 0.6319(3) 0.47593(10) 0.0180(6) Uani 1 1 d . . . . .
C20 C 0.5025(4) 0.3303(3) 0.32151(11) 0.0228(6) Uani 1 1 d . . . . .
H20 H 0.534041 0.304017 0.288933 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6334(3) 0.3593(3) 0.35801(10) 0.0226(6) Uani 1 1 d . . . . .
H21 H 0.754504 0.350303 0.350638 0.027 Uiso 1 1 calc R U . . .
C19 C 0.3252(3) 0.3397(3) 0.33245(11) 0.0218(6) Uani 1 1 d . . . . .
C3 C 0.8787(4) 0.7542(3) 0.48056(11) 0.0238(6) Uani 1 1 d . . . . .
H3 H 0.791876 0.801424 0.463112 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3258(3) 0.7234(3) 0.34760(10) 0.0213(6) Uani 1 1 d . . . . .
C22 C 0.1861(3) 0.3176(3) 0.29176(11) 0.0244(7) Uani 1 1 d . . . . .
C14 C 0.6243(3) 0.6545(3) 0.36147(10) 0.0237(7) Uani 1 1 d . . . . .
H14 H 0.735518 0.635300 0.348347 0.028 Uiso 1 1 calc R U . . .
C1 C 1.1409(4) 0.7393(3) 0.53681(11) 0.0243(7) Uani 1 1 d . . . . .
H1 H 1.231022 0.776710 0.557402 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1774(3) 0.7489(3) 0.31022(11) 0.0228(6) Uani 1 1 d . . . . .
C13 C 0.4881(4) 0.6931(3) 0.32872(11) 0.0249(7) Uani 1 1 d . . . . .
H13 H 0.505403 0.699054 0.293299 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4120(4) 0.4052(3) 0.41697(11) 0.0255(7) Uani 1 1 d . . . . .
H17 H 0.380734 0.429648 0.449840 0.031 Uiso 1 1 calc R U . . .
C2 C 1.0132(4) 0.8060(3) 0.51060(11) 0.0275(7) Uani 1 1 d . . . . .
H2A H 1.017838 0.888727 0.513248 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3063(4) 0.7237(3) 0.40002(11) 0.0262(7) Uani 1 1 d . . . . .
H11 H 0.198924 0.749978 0.413484 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4449(4) 0.6855(3) 0.43230(11) 0.0283(7) Uani 1 1 d . . . . .
H10 H 0.433261 0.687883 0.468071 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2806(4) 0.3737(3) 0.38081(11) 0.0285(7) Uani 1 1 d . . . . .
H18 H 0.159683 0.375465 0.389165 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5175(5) 0.0181(3) 0.34795(14) 0.0376(8) Uani 1 1 d . . . . .
C24 C 0.3826(5) 0.0400(3) 0.38025(14) 0.0384(8) Uani 1 1 d . . . . .
C28 C 0.4786(5) 0.0094(3) 0.29619(15) 0.0446(9) Uani 1 1 d . . . . .
H28 H 0.570575 -0.005044 0.273680 0.054 Uiso 1 1 calc R U . . .
C25 C 0.2109(5) 0.0531(3) 0.36109(15) 0.0439(9) Uani 1 1 d . . . . .
H25 H 0.119072 0.069122 0.383474 0.053 Uiso 1 1 calc R U . . .
C27 C 0.3057(5) 0.0218(3) 0.27726(15) 0.0444(9) Uani 1 1 d . . . . .
H27 H 0.279228 0.015415 0.241677 0.053 Uiso 1 1 calc R U . . .
C26 C 0.1713(5) 0.0431(3) 0.30944(15) 0.0451(9) Uani 1 1 d . . . . .
H26 H 0.052464 0.050983 0.296261 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.727(4) . ?
Cl2 C24 1.733(4) . ?
O3 C22 1.232(3) . ?
O2 H2 0.8400 . ?
O2 C15 1.315(3) . ?
O1 C15 1.232(3) . ?
O4 H4 0.8400 . ?
O4 C22 1.308(3) . ?
C8 C8 1.418(6) 3_766 ?
C8 C7 1.430(4) . ?
C8 C4 1.428(4) . ?
C5 C6 1.359(4) . ?
C5 C9 1.499(4) . ?
C5 C4 1.445(4) . ?
C16 C6 1.503(4) . ?
C16 C21 1.385(4) . ?
C16 C17 1.396(4) . ?
C6 C7 1.452(4) 3_766 ?
C7 C1 1.397(4) . ?
C9 C14 1.381(4) . ?
C9 C10 1.396(4) . ?
C4 C3 1.406(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(4) . ?
C20 C19 1.388(4) . ?
C21 H21 0.9500 . ?
C19 C22 1.483(4) . ?
C19 C18 1.389(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.388(4) . ?
C12 C15 1.482(4) . ?
C12 C13 1.390(4) . ?
C12 C11 1.394(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C2 H2A 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.385(4) . ?
C10 H10 0.9500 . ?
C18 H18 0.9500 . ?
C23 C24 1.382(5) . ?
C23 C28 1.382(5) . ?
C24 C25 1.375(5) . ?
C28 H28 0.9500 . ?
C28 C27 1.381(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(6) . ?
C27 H27 0.9500 . ?
C27 C26 1.376(6) . ?
C26 H26 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
C15 O2 H2 109.5 . . ?
C22 O4 H4 109.5 . . ?
C8 C8 C7 120.4(3) 3_766 . ?
C8 C8 C4 120.5(3) 3_766 . ?
C4 C8 C7 119.2(3) . . ?
C6 C5 C9 117.8(2) . . ?
C6 C5 C4 121.2(2) . . ?
C4 C5 C9 120.8(3) . . ?
C21 C16 C6 120.2(2) . . ?
C21 C16 C17 119.0(2) . . ?
C17 C16 C6 120.4(2) . . ?
C5 C6 C16 118.7(2) . . ?
C5 C6 C7 121.4(2) . 3_766 ?
C7 C6 C16 119.9(3) 3_766 . ?
C8 C7 C6 118.1(3) . 3_766 ?
C1 C7 C8 119.4(2) . . ?
C1 C7 C6 122.5(2) . 3_766 ?
C14 C9 C5 118.7(2) . . ?
C14 C9 C10 118.4(2) . . ?
C10 C9 C5 122.5(2) . . ?
C8 C4 C5 118.4(3) . . ?
C3 C4 C8 119.5(2) . . ?
C3 C4 C5 122.1(2) . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C20 C19 C22 119.5(2) . . ?
C20 C19 C18 119.5(2) . . ?
C18 C19 C22 120.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C13 C12 C15 117.6(2) . . ?
C13 C12 C11 119.5(2) . . ?
C11 C12 C15 122.8(2) . . ?
O3 C22 O4 122.7(2) . . ?
O3 C22 C19 122.4(2) . . ?
O4 C22 C19 114.8(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C7 C1 H1 119.7 . . ?
C2 C1 C7 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
O2 C15 C12 115.7(2) . . ?
O1 C15 O2 123.2(2) . . ?
O1 C15 C12 121.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2A 119.4 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C24 C23 Cl1 121.1(3) . . ?
C24 C23 C28 119.5(3) . . ?
C28 C23 Cl1 119.4(3) . . ?
C23 C24 Cl2 120.5(3) . . ?
C25 C24 Cl2 119.2(3) . . ?
C25 C24 C23 120.3(3) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.9(3) . . ?
C27 C28 H28 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(4) . . ?
C26 C25 H25 119.8 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C23 C24 Cl2 1.9(5) . . . . ?
Cl1 C23 C24 C25 -178.9(3) . . . . ?
Cl1 C23 C28 C27 178.4(3) . . . . ?
Cl2 C24 C25 C26 180.0(3) . . . . ?
C8 C8 C7 C6 -0.8(4) 3_766 . . 3_766 ?
C8 C8 C7 C1 179.2(3) 3_766 . . . ?
C8 C8 C4 C5 0.2(4) 3_766 . . . ?
C8 C8 C4 C3 -179.1(3) 3_766 . . . ?
C8 C7 C1 C2 -0.3(4) . . . . ?
C8 C4 C3 C2 0.0(4) . . . . ?
C5 C9 C14 C13 164.9(3) . . . . ?
C5 C9 C10 C11 -164.2(3) . . . . ?
C5 C4 C3 C2 -179.2(3) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C6 C5 C9 C14 -74.1(3) . . . . ?
C6 C5 C9 C10 98.2(3) . . . . ?
C6 C5 C4 C8 0.1(4) . . . . ?
C6 C5 C4 C3 179.3(3) . . . . ?
C6 C16 C21 C20 -167.1(3) . . . . ?
C6 C16 C17 C18 168.6(3) . . . . ?
C6 C7 C1 C2 179.7(3) 3_766 . . . ?
C7 C8 C4 C5 179.6(2) . . . . ?
C7 C8 C4 C3 0.3(4) . . . . ?
C7 C1 C2 C3 0.6(4) . . . . ?
C9 C5 C6 C16 -1.6(4) . . . . ?
C9 C5 C6 C7 175.8(2) . . . 3_766 ?
C9 C5 C4 C8 -175.5(2) . . . . ?
C9 C5 C4 C3 3.8(4) . . . . ?
C9 C14 C13 C12 1.1(5) . . . . ?
C4 C8 C7 C6 179.8(2) . . . 3_766 ?
C4 C8 C7 C1 -0.2(4) . . . . ?
C4 C5 C6 C16 -177.3(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . 3_766 ?
C4 C5 C9 C14 101.6(3) . . . . ?
C4 C5 C9 C10 -86.1(4) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
C20 C19 C22 O3 -9.3(5) . . . . ?
C20 C19 C22 O4 172.6(3) . . . . ?
C20 C19 C18 C17 4.0(5) . . . . ?
C21 C16 C6 C5 103.3(3) . . . . ?
C21 C16 C6 C7 -74.1(4) . . . 3_766 ?
C21 C16 C17 C18 -3.5(5) . . . . ?
C21 C20 C19 C22 175.1(3) . . . . ?
C21 C20 C19 C18 -2.6(5) . . . . ?
C19 C20 C21 C16 -2.0(5) . . . . ?
C12 C11 C10 C9 -1.9(5) . . . . ?
C22 C19 C18 C17 -173.6(3) . . . . ?
C14 C9 C10 C11 8.1(5) . . . . ?
C15 C12 C13 C14 -172.0(3) . . . . ?
C15 C12 C11 C10 172.3(3) . . . . ?
C13 C12 C15 O2 177.0(3) . . . . ?
C13 C12 C15 O1 -1.9(4) . . . . ?
C13 C12 C11 C10 -4.9(5) . . . . ?
C17 C16 C6 C5 -68.7(4) . . . . ?
C17 C16 C6 C7 113.9(3) . . . 3_766 ?
C17 C16 C21 C20 5.0(5) . . . . ?
C11 C12 C15 O2 -0.1(4) . . . . ?
C11 C12 C15 O1 -179.0(3) . . . . ?
C11 C12 C13 C14 5.3(5) . . . . ?
C10 C9 C14 C13 -7.7(5) . . . . ?
C18 C19 C22 O3 168.3(3) . . . . ?
C18 C19 C22 O4 -9.8(4) . . . . ?
C23 C24 C25 C26 0.8(6) . . . . ?
C23 C28 C27 C26 0.2(6) . . . . ?
C24 C23 C28 C27 -0.4(6) . . . . ?
C24 C25 C26 C27 -1.0(6) . . . . ?
C28 C23 C24 Cl2 -179.2(3) . . . . ?
C28 C23 C24 C25 -0.1(6) . . . . ?
C28 C27 C26 C25 0.5(6) . . . . ?

_olex2_submission_original_sample_id CP-Py-DCB-Form2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.837
_exptl_crystal_recrystallization_method 
'obtained by desolvation-triggered structural transformation'
####################################################################### 
# 
# 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_CP-Py-3
_database_code_depnum_ccdc_archive 'CCDC 2255739'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-08-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_PLAT082_CP-Py-3             
;
PROBLEM: High R1 Value ..................................       0.21 Report
RESPONSE: Because of low crystallinity of the crystal, 
which was obtained via 2-step structural transformation.
;
_vrf_PLAT084_CP-Py-3             
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.60 Report
RESPONSE: Because of low crystallinity of the crystal, 
which was obtained via 2-step structural transformation.
;
_vrf_PLAT934_CP-Py-3             
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..         20 Check 
RESPONSE: ...
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        CP-Py-3
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0035 0.0022 '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'
O O 0.0116 0.0081 '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                   7.5864(17)
_cell_length_b                   9.404(3)
_cell_length_c                   13.016(3)
_cell_angle_alpha                78.06(2)
_cell_angle_beta                 86.453(17)
_cell_angle_gamma                67.84(2)
_cell_volume                     841.2(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.3690
_cell_measurement_theta_min      2.7340
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8327
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        29.122
_diffrn_reflns_theta_max         33.101
_diffrn_reflns_theta_min         1.825
_diffrn_ambient_temperature      113
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00    5.00    --   25.00  45.00   0.00  180
  2  ω    -90.00  90.00   1.00    5.00    --   25.00  45.00  90.00  180
  3  ω    -90.00  90.00   1.00    5.00    --   25.00  45.00 180.00  180
  4  ω    -90.00  90.00   1.00    5.00    --   25.00  45.00 270.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0971248000
_diffrn_orient_matrix_UB_12      -0.0165114000
_diffrn_orient_matrix_UB_13      0.0138474000
_diffrn_orient_matrix_UB_21      -0.0553177000
_diffrn_orient_matrix_UB_22      0.0904250000
_diffrn_orient_matrix_UB_23      0.0057052000
_diffrn_orient_matrix_UB_31      -0.0289329000
_diffrn_orient_matrix_UB_32      0.0240504000
_diffrn_orient_matrix_UB_33      -0.0619122000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.81111
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1777
_reflns_number_total             3644
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2777
_refine_ls_R_factor_gt           0.2112
_refine_ls_restrained_S_all      2.114
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5583
_refine_ls_wR_factor_ref         0.5974
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q)
2.b Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_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
O001 O -0.1279(9) 0.8580(11) 0.8135(5) 0.092(3) Uani 1 1 d . . . . .
H001 H -0.202139 0.853374 0.863570 0.137 Uiso 1 1 calc R U . . .
O002 O 0.0562(9) 0.8678(9) 0.9366(5) 0.078(2) Uani 1 1 d . . . . .
O003 O 0.1878(9) 0.1397(10) 0.8982(5) 0.082(2) Uani 1 1 d . . . . .
H003 H 0.096423 0.162232 0.939591 0.122 Uiso 1 1 calc R U . . .
O004 O 0.3613(9) 0.1499(10) 1.0283(5) 0.083(2) Uani 1 1 d . . . . .
C005 C 1.2055(11) 0.3333(15) 0.4588(7) 0.072(3) Uani 1 1 d . . . . .
C006 C 0.7743(12) 0.4092(13) 0.6271(7) 0.065(2) Uani 1 1 d . . . . .
C007 C 0.9412(12) 0.3267(15) 0.5750(7) 0.073(3) Uani 1 1 d . . . . .
C008 C 1.0338(11) 0.4192(12) 0.5080(7) 0.067(2) Uani 1 1 d . . . . .
C009 C 0.0386(13) 0.8394(13) 0.8504(7) 0.073(3) Uani 1 1 d . . . . .
C00A C 0.3478(12) 0.6515(14) 0.6417(7) 0.079(3) Uani 1 1 d . . . . .
H00A H 0.336385 0.606324 0.584744 0.095 Uiso 1 1 calc R U . . .
C00B C 1.2718(12) 0.1751(14) 0.4744(7) 0.071(3) Uani 1 1 d . . . . .
H00B H 1.385378 0.121357 0.441070 0.086 Uiso 1 1 calc R U . . .
C00C C 0.6748(12) 0.3231(12) 0.7024(7) 0.071(3) Uani 1 1 d . . . . .
C00D C 0.3324(14) 0.1628(13) 0.9341(8) 0.076(3) Uani 1 1 d . . . . .
C00E C 0.4548(14) 0.2131(12) 0.8515(8) 0.074(3) Uani 1 1 d . . . . .
C00F C 0.3738(13) 0.7899(13) 0.8039(7) 0.075(3) Uani 1 1 d . . . . .
H00F H 0.384304 0.834583 0.861301 0.090 Uiso 1 1 calc R U . . .
C00G C 0.1990(13) 0.7879(13) 0.7818(8) 0.078(3) Uani 1 1 d . . . . .
C00H C 1.0142(13) 0.1689(14) 0.5887(7) 0.073(3) Uani 1 1 d . . . . .
H00H H 0.952851 0.109597 0.634167 0.087 Uiso 1 1 calc R U . . .
C00I C 0.7058(13) 0.3100(15) 0.8087(7) 0.083(3) Uani 1 1 d . . . . .
H00I H 0.800080 0.342214 0.829853 0.099 Uiso 1 1 calc R U . . .
C00J C 1.1797(14) 0.0912(17) 0.5366(8) 0.087(3) Uani 1 1 d . . . . .
H00J H 1.227028 -0.019621 0.544935 0.104 Uiso 1 1 calc R U . . .
C00K C 0.4317(14) 0.2110(15) 0.7465(8) 0.086(3) Uani 1 1 d . . . . .
H00K H 0.347339 0.168533 0.725553 0.103 Uiso 1 1 calc R U . . .
C00L C 0.6016(14) 0.2509(16) 0.8839(8) 0.088(3) Uani 1 1 d . . . . .
H00L H 0.628920 0.235966 0.956461 0.106 Uiso 1 1 calc R U . . .
C00M C 0.5337(13) 0.7297(13) 0.7462(7) 0.079(3) Uani 1 1 d . . . . .
H00M H 0.649581 0.739023 0.760687 0.094 Uiso 1 1 calc R U . . .
C00N C 0.5227(12) 0.6538(13) 0.6649(7) 0.073(3) Uani 1 1 d . . . . .
C00O C 0.7002(12) 0.5690(17) 0.6122(6) 0.084(4) Uani 1 1 d . . . . .
C00P C 0.5386(13) 0.2742(14) 0.6738(7) 0.081(3) Uani 1 1 d . . . . .
H00P H 0.516522 0.283968 0.601181 0.097 Uiso 1 1 calc R U . . .
C00Q C 0.1926(13) 0.7132(14) 0.6996(7) 0.081(3) Uani 1 1 d . . . . .
H00Q H 0.076025 0.705680 0.684211 0.097 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
O001 H001 0.8400 . ?
O001 C009 1.315(11) . ?
O002 C009 1.232(11) . ?
O003 H003 0.8400 . ?
O003 C00D 1.325(12) . ?
O004 C00D 1.233(12) . ?
C005 C008 1.441(12) . ?
C005 C00B 1.353(15) . ?
C005 C00O 1.507(13) 2_766 ?
C006 C007 1.427(13) . ?
C006 C00C 1.492(12) . ?
C006 C00O 1.367(16) . ?
C007 C008 1.443(12) . ?
C007 C00H 1.350(15) . ?
C008 C008 1.38(2) 2_766 ?
C009 C00G 1.453(13) . ?
C00A H00A 0.9500 . ?
C00A C00N 1.388(13) . ?
C00A C00Q 1.359(13) . ?
C00B H00B 0.9500 . ?
C00B C00J 1.359(14) . ?
C00C C00I 1.389(13) . ?
C00C C00P 1.376(14) . ?
C00D C00E 1.496(13) . ?
C00E C00K 1.394(14) . ?
C00E C00L 1.400(16) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.382(14) . ?
C00F C00M 1.379(12) . ?
C00G C00Q 1.408(16) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.407(13) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.379(12) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00K C00P 1.394(12) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.415(15) . ?
C00N C00O 1.491(13) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 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
C009 O001 H001 109.5 . . ?
C00D O003 H003 109.5 . . ?
C008 C005 C00O 115.8(11) . 2_766 ?
C00B C005 C008 120.9(8) . . ?
C00B C005 C00O 123.2(9) . 2_766 ?
C007 C006 C00C 120.9(10) . . ?
C00O C006 C007 122.0(8) . . ?
C00O C006 C00C 117.0(8) . . ?
C006 C007 C008 117.1(11) . . ?
C00H C007 C006 122.3(9) . . ?
C00H C007 C008 120.6(8) . . ?
C005 C008 C007 116.2(10) . . ?
C008 C008 C005 120.8(10) 2_766 . ?
C008 C008 C007 123.0(10) 2_766 . ?
O001 C009 C00G 115.8(9) . . ?
O002 C009 O001 121.9(8) . . ?
O002 C009 C00G 122.2(9) . . ?
C00N C00A H00A 119.7 . . ?
C00Q C00A H00A 119.7 . . ?
C00Q C00A C00N 120.6(10) . . ?
C005 C00B H00B 119.2 . . ?
C005 C00B C00J 121.6(9) . . ?
C00J C00B H00B 119.2 . . ?
C00I C00C C006 116.8(9) . . ?
C00P C00C C006 124.3(8) . . ?
C00P C00C C00I 118.4(8) . . ?
O003 C00D C00E 115.2(9) . . ?
O004 C00D O003 122.9(9) . . ?
O004 C00D C00E 121.8(9) . . ?
C00K C00E C00D 120.6(9) . . ?
C00K C00E C00L 121.2(9) . . ?
C00L C00E C00D 118.1(9) . . ?
C00G C00F H00F 118.7 . . ?
C00M C00F H00F 118.7 . . ?
C00M C00F C00G 122.7(10) . . ?
C00F C00G C009 120.9(10) . . ?
C00F C00G C00Q 116.6(9) . . ?
C00Q C00G C009 121.9(9) . . ?
C007 C00H H00H 119.6 . . ?
C007 C00H C00J 120.9(9) . . ?
C00J C00H H00H 119.6 . . ?
C00C C00I H00I 119.5 . . ?
C00L C00I C00C 121.0(9) . . ?
C00L C00I H00I 119.5 . . ?
C00B C00J C00H 119.8(12) . . ?
C00B C00J H00J 120.1 . . ?
C00H C00J H00J 120.1 . . ?
C00E C00K H00K 121.7 . . ?
C00P C00K C00E 116.6(10) . . ?
C00P C00K H00K 121.7 . . ?
C00E C00L H00L 120.5 . . ?
C00I C00L C00E 118.9(9) . . ?
C00I C00L H00L 120.5 . . ?
C00F C00M H00M 120.5 . . ?
C00F C00M C00N 119.1(9) . . ?
C00N C00M H00M 120.5 . . ?
C00A C00N C00M 118.7(8) . . ?
C00A C00N C00O 121.8(9) . . ?
C00M C00N C00O 119.4(8) . . ?
C006 C00O C005 121.2(8) . 2_766 ?
C006 C00O C00N 121.4(9) . . ?
C00N C00O C005 117.4(11) . 2_766 ?
C00C C00P C00K 123.0(9) . . ?
C00C C00P H00P 118.5 . . ?
C00K C00P H00P 118.5 . . ?
C00A C00Q C00G 122.2(10) . . ?
C00A C00Q H00Q 118.9 . . ?
C00G C00Q H00Q 118.9 . . ?

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
O001 C009 C00G C00F 168.9(10) . . . . ?
O001 C009 C00G C00Q -20.5(16) . . . . ?
O002 C009 C00G C00F -9.3(16) . . . . ?
O002 C009 C00G C00Q 161.3(10) . . . . ?
O003 C00D C00E C00K -9.4(14) . . . . ?
O003 C00D C00E C00L 175.3(10) . . . . ?
O004 C00D C00E C00K 173.2(10) . . . . ?
O004 C00D C00E C00L -2.1(15) . . . . ?
C005 C00B C00J C00H -1.7(15) . . . . ?
C006 C007 C008 C005 178.1(8) . . . . ?
C006 C007 C008 C008 -0.9(16) . . . 2_766 ?
C006 C007 C00H C00J -179.6(9) . . . . ?
C006 C00C C00I C00L 171.5(11) . . . . ?
C006 C00C C00P C00K -172.0(10) . . . . ?
C007 C006 C00C C00I 102.2(11) . . . . ?
C007 C006 C00C C00P -86.3(13) . . . . ?
C007 C006 C00O C005 -1.4(14) . . . 2_766 ?
C007 C006 C00O C00N 178.3(8) . . . . ?
C007 C00H C00J C00B 2.3(15) . . . . ?
C008 C005 C00B C00J 0.0(14) . . . . ?
C008 C007 C00H C00J -1.2(14) . . . . ?
C009 C00G C00Q C00A -173.6(10) . . . . ?
C00A C00N C00O C005 113.9(11) . . . 2_766 ?
C00A C00N C00O C006 -65.8(13) . . . . ?
C00B C005 C008 C007 1.0(13) . . . . ?
C00B C005 C008 C008 180.0(10) . . . 2_766 ?
C00C C006 C007 C008 -176.7(8) . . . . ?
C00C C006 C007 C00H 1.8(15) . . . . ?
C00C C006 C00O C005 177.5(8) . . . 2_766 ?
C00C C006 C00O C00N -2.8(13) . . . . ?
C00C C00I C00L C00E -4.0(18) . . . . ?
C00D C00E C00K C00P 173.9(10) . . . . ?
C00D C00E C00L C00I -174.6(10) . . . . ?
C00E C00K C00P C00C 6.2(17) . . . . ?
C00F C00G C00Q C00A -2.7(16) . . . . ?
C00F C00M C00N C00A 4.1(15) . . . . ?
C00F C00M C00N C00O -171.5(10) . . . . ?
C00G C00F C00M C00N -4.1(16) . . . . ?
C00H C007 C008 C005 -0.4(13) . . . . ?
C00H C007 C008 C008 -179.3(11) . . . 2_766 ?
C00I C00C C00P C00K -0.6(17) . . . . ?
C00K C00E C00L C00I 10.1(17) . . . . ?
C00L C00E C00K C00P -11.0(17) . . . . ?
C00M C00F C00G C009 174.3(10) . . . . ?
C00M C00F C00G C00Q 3.3(16) . . . . ?
C00M C00N C00O C005 -70.6(11) . . . 2_766 ?
C00M C00N C00O C006 109.7(11) . . . . ?
C00N C00A C00Q C00G 3.0(17) . . . . ?
C00O C005 C008 C007 179.2(7) 2_766 . . . ?
C00O C005 C008 C008 -1.8(15) 2_766 . . 2_766 ?
C00O C005 C00B C00J -178.0(8) 2_766 . . . ?
C00O C006 C007 C008 2.1(13) . . . . ?
C00O C006 C007 C00H -179.4(9) . . . . ?
C00O C006 C00C C00I -76.7(12) . . . . ?
C00O C006 C00C C00P 94.8(12) . . . . ?
C00P C00C C00I C00L -0.6(17) . . . . ?
C00Q C00A C00N C00M -3.6(16) . . . . ?
C00Q C00A C00N C00O 171.9(10) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.016 0.500 0.000 98 0 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_original_sample_id CPPy-Form3
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.474
_oxdiff_exptl_absorpt_empirical_full_min 0.525
_exptl_crystal_recrystallization_method 
'obtained by desolvation-triggered structural transformation'
####################################################################### 
# 
# 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_CP-Py-2-TCB
_database_code_depnum_ccdc_archive 'CCDC 2255741'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-10-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        CP-Py-2-TCB
_chemical_formula_moiety         '2(C6 H3 Cl3), C44 H26 O8'
_chemical_formula_sum            'C56 H32 Cl6 O8'
_chemical_formula_weight         1045.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   27.5399(14)
_cell_length_b                   11.8206(8)
_cell_length_c                   7.2355(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.898(5)
_cell_angle_gamma                90
_cell_volume                     2352.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4922
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.9510
_cell_measurement_theta_min      3.4540
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17520
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.675
_diffrn_reflns_theta_min         2.812
_diffrn_ambient_temperature      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  72.00   0.25    5.00    --    0.00  45.00  15.00  532
  2  ω    -85.25  44.00   0.25    5.00    --    0.00  45.00 193.00  517
  3  ω     -2.00  43.00   0.25    5.00    --    0.00  45.00 157.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0171931000
_diffrn_orient_matrix_UB_12      -0.0310452000
_diffrn_orient_matrix_UB_13      0.0558676000
_diffrn_orient_matrix_UB_21      -0.0174066000
_diffrn_orient_matrix_UB_22      -0.0068175000
_diffrn_orient_matrix_UB_23      0.0681328000
_diffrn_orient_matrix_UB_31      -0.0081591000
_diffrn_orient_matrix_UB_32      -0.0508963000
_diffrn_orient_matrix_UB_33      -0.0432576000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2596
_reflns_number_total             3735
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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         0.641
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+3.9835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C6-C7A \\sim C6-C7B
 with sigma of 0.02
 C6-C11A \\sim C6-C11B
 with sigma of 0.02
 C9-C8A \\sim C9-C8B
 with sigma of 0.02
 C9-C10A \\sim C9-C10B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9-C11A \\sim C9-C11B
 with sigma of 0.04
 C6-C10A \\sim C6-C10B
 with sigma of 0.04
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 C6-C8A \\sim C6-C8B
 with sigma of 0.04
 C9-C7A \\sim C9-C7B
 with sigma of 0.04
3. Restrained planarity
 C8B, C7B, C9, C10B, C11B, C6
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C11A \\sim C10A \\sim C9 \\sim C8A \\sim C7A \\sim C6: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C11B \\sim C7B \\sim C8B \\sim C10B: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.08 within 1.7A
C7A \\sim C8A \\sim C11A \\sim C10A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.08 within 1.7A
Uanis(C7A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C10A, C11A, C6, C8A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7B, C8B, C6, C11B, C10B, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C11B)=Sof(H11A)=Sof(C10B)=Sof(H10A)=Sof(C8B)=Sof(H8A)=Sof(C7B)=Sof(H7A)=1-
 FVAR(1)
 Sof(C11A)=Sof(H11)=Sof(C10A)=Sof(H10)=Sof(C8A)=Sof(H8)=Sof(C7A)=Sof(H7)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C11A(H11), C10A(H10), C8A(H8), C7A(H7), C11B(H11A), C10B(H10A), C8B(H8A),
 C7B(H7A), C1(H1), C2(H2A), C18(H18), C16(H16), C15(H15)
7.b Fitted hexagon refined as free rotating group:
 C6(C11A,C10A,C9,C8A,C7A)
7.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Cl3 Cl 0.25079(3) 0.500000 0.12313(12) 0.0367(2) Uani 1 2 d S T P . .
Cl2 Cl 0.40321(3) 0.500000 0.78925(13) 0.0415(2) Uani 1 2 d S T P . .
Cl1 Cl 0.43744(4) 0.500000 0.37764(19) 0.0880(6) Uani 1 2 d S T P . .
O2 O 0.31635(5) 0.25319(15) 0.02059(19) 0.0285(4) Uani 1 1 d . . . . .
H2 H 0.292261 0.265239 -0.052636 0.043 Uiso 1 1 calc R U . . .
O1 O 0.25816(5) 0.22147(14) 0.21919(19) 0.0253(3) Uani 1 1 d . . . . .
C5 C 0.500000 0.0599(2) 1.000000 0.0163(5) Uani 1 2 d S T P . .
C4 C 0.47127(6) 0.12093(17) 0.8640(2) 0.0176(4) Uani 1 1 d . . . . .
C3 C 0.44201(6) 0.05765(17) 0.7278(2) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.30122(7) 0.22657(17) 0.1845(3) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.40869(6) 0.11905(16) 0.5914(2) 0.0194(4) Uani 1 1 d DG U . . .
C11 C 0.41922(18) 0.1192(10) 0.4055(3) 0.0244(19) Uani 0.45(3) 1 d DG U P A 1
H11 H 0.449722 0.091881 0.368920 0.029 Uiso 0.45(3) 1 calc R U P A 1
C10 C 0.38513(19) 0.1593(10) 0.2732(3) 0.0244(19) Uani 0.45(3) 1 d DG U P A 1
H10 H 0.392323 0.159416 0.146196 0.029 Uiso 0.45(3) 1 calc R U P A 1
C9 C 0.34050(6) 0.19929(17) 0.3268(2) 0.0195(4) Uani 1 1 d DG U . A .
C8 C 0.32997(18) 0.1991(10) 0.5126(3) 0.0171(19) Uani 0.45(3) 1 d DG U P A 1
H8 H 0.299467 0.226460 0.549255 0.020 Uiso 0.45(3) 1 calc R U P A 1
C7 C 0.36406(19) 0.1590(10) 0.6450(3) 0.0195(19) Uani 0.45(3) 1 d DG U P A 1
H7 H 0.356866 0.158925 0.771983 0.023 Uiso 0.45(3) 1 calc R U P A 1
C11A C 0.42328(18) 0.1568(12) 0.4192(8) 0.0282(18) Uani 0.55(3) 1 d D U P A 2
H11A H 0.456750 0.155058 0.393443 0.034 Uiso 0.55(3) 1 calc R U P A 2
C10A C 0.38952(18) 0.1969(12) 0.2855(8) 0.0256(17) Uani 0.55(3) 1 d D U P A 2
H10A H 0.399559 0.222147 0.168781 0.031 Uiso 0.55(3) 1 calc R U P A 2
C8A C 0.32629(19) 0.1728(9) 0.5031(7) 0.0229(12) Uani 0.55(3) 1 d D U P A 2
H8A H 0.293298 0.181148 0.533153 0.027 Uiso 0.55(3) 1 calc R U P A 2
C7A C 0.36056(19) 0.1342(9) 0.6347(8) 0.0255(13) Uani 0.55(3) 1 d D U P A 2
H7A H 0.351048 0.117780 0.756249 0.031 Uiso 0.55(3) 1 calc R U P A 2
C1 C 0.47199(7) 0.23921(18) 0.8657(3) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.453222 0.280177 0.774468 0.027 Uiso 1 1 calc R U . . .
C2 C 0.500000 0.2973(3) 1.000000 0.0259(6) Uani 1 2 d S T P . .
H2A H 0.500001 0.377648 0.999998 0.031 Uiso 1 2 calc R U P . .
C17 C 0.29401(12) 0.500000 0.3078(5) 0.0289(7) Uani 1 2 d S T P . .
C14 C 0.36165(12) 0.500000 0.6001(5) 0.0304(7) Uani 1 2 d S T P . .
C18 C 0.34256(13) 0.500000 0.2726(5) 0.0359(8) Uani 1 2 d S T P . .
H18 H 0.352649 0.500000 0.149002 0.043 Uiso 1 2 calc R U P . .
C13 C 0.37675(12) 0.500000 0.4211(5) 0.0362(8) Uani 1 2 d S T P . .
C16 C 0.27824(13) 0.500000 0.4860(5) 0.0463(10) Uani 1 2 d S T P . .
H16 H 0.244493 0.500000 0.507590 0.056 Uiso 1 2 calc R U P . .
C15 C 0.31270(14) 0.500000 0.6333(5) 0.0453(10) Uani 1 2 d S T P . .
H15 H 0.302563 0.500000 0.756874 0.054 Uiso 1 2 calc R U P . .


_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
Cl3 C17 1.744(3) . ?
Cl2 C14 1.739(3) . ?
Cl1 C13 1.717(4) . ?
O2 H2 0.8400 . ?
O2 C12 1.315(2) . ?
O1 C12 1.226(2) . ?
C5 C5 1.417(6) 5_657 ?
C5 C4 1.427(2) . ?
C5 C4 1.427(2) 2_657 ?
C4 C3 1.449(2) . ?
C4 C1 1.398(3) . ?
C3 C3 1.363(4) 6 ?
C3 C6 1.500(2) . ?
C12 C9 1.490(2) . ?
C6 C11 1.3900 . ?
C6 C7 1.3900 . ?
C6 C11A 1.401(5) . ?
C6 C7A 1.389(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C9 1.3900 . ?
C9 C8 1.3900 . ?
C9 C10A 1.398(5) . ?
C9 C8A 1.389(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.3900 . ?
C7 H7 0.9500 . ?
C11A H11A 0.9500 . ?
C11A C10A 1.390(5) . ?
C10A H10A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C7A 1.384(6) . ?
C7A H7A 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.391(2) . ?
C2 H2A 0.9500 . ?
C17 C18 1.374(5) . ?
C17 C16 1.382(5) . ?
C14 C13 1.380(5) . ?
C14 C15 1.381(5) . ?
C18 H18 0.9500 . ?
C18 C13 1.392(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.391(5) . ?
C15 H15 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
C12 O2 H2 109.5 . . ?
C5 C5 C4 120.36(12) 5_657 2_657 ?
C5 C5 C4 120.35(12) 5_657 . ?
C4 C5 C4 119.3(2) . 2_657 ?
C5 C4 C3 118.57(18) . . ?
C1 C4 C5 119.48(18) . . ?
C1 C4 C3 121.95(17) . . ?
C4 C3 C6 119.88(17) . . ?
C3 C3 C4 121.08(11) 6 . ?
C3 C3 C6 118.93(11) 6 . ?
O2 C12 C9 115.01(16) . . ?
O1 C12 O2 123.37(16) . . ?
O1 C12 C9 121.60(18) . . ?
C11 C6 C3 119.10(17) . . ?
C11 C6 C7 120.0 . . ?
C7 C6 C3 120.07(17) . . ?
C11A C6 C3 123.1(3) . . ?
C7A C6 C3 118.2(3) . . ?
C7A C6 C11A 118.6(3) . . ?
C6 C11 H11 120.0 . . ?
C6 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 C12 120.14(16) . . ?
C10 C9 C8 120.0 . . ?
C8 C9 C12 119.26(16) . . ?
C10A C9 C12 122.1(2) . . ?
C8A C9 C12 117.1(3) . . ?
C8A C9 C10A 120.8(3) . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C6 C11A H11A 119.5 . . ?
C10A C11A C6 121.0(4) . . ?
C10A C11A H11A 119.5 . . ?
C9 C10A H10A 120.7 . . ?
C11A C10A C9 118.5(4) . . ?
C11A C10A H10A 120.7 . . ?
C9 C8A H8A 120.2 . . ?
C7A C8A C9 119.5(4) . . ?
C7A C8A H8A 120.2 . . ?
C6 C7A H7A 119.6 . . ?
C8A C7A C6 120.8(4) . . ?
C8A C7A H7A 119.6 . . ?
C4 C1 H1 119.8 . . ?
C2 C1 C4 120.44(19) . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C1 120.9(3) 2_657 . ?
C1 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 2_657 . ?
C18 C17 Cl3 119.4(3) . . ?
C18 C17 C16 121.9(3) . . ?
C16 C17 Cl3 118.7(3) . . ?
C13 C14 Cl2 121.4(3) . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 Cl2 118.2(3) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C13 118.9(3) . . ?
C13 C18 H18 120.5 . . ?
C14 C13 Cl1 121.0(3) . . ?
C14 C13 C18 120.0(3) . . ?
C18 C13 Cl1 119.0(3) . . ?
C17 C16 H16 120.6 . . ?
C17 C16 C15 118.7(3) . . ?
C15 C16 H16 120.6 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?

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
Cl3 C17 C18 C13 180.000(0) . . . . ?
Cl3 C17 C16 C15 180.000(0) . . . . ?
Cl2 C14 C13 Cl1 0.000(0) . . . . ?
Cl2 C14 C13 C18 180.000(0) . . . . ?
Cl2 C14 C15 C16 180.000(0) . . . . ?
O2 C12 C9 C10 -25.5(6) . . . . ?
O2 C12 C9 C8 163.3(6) . . . . ?
O2 C12 C9 C10A -3.0(7) . . . . ?
O2 C12 C9 C8A 178.8(6) . . . . ?
O1 C12 C9 C10 152.8(6) . . . . ?
O1 C12 C9 C8 -18.3(6) . . . . ?
O1 C12 C9 C10A 175.3(7) . . . . ?
O1 C12 C9 C8A -2.9(6) . . . . ?
C5 C5 C4 C3 0.5(2) 5_657 . . . ?
C5 C5 C4 C1 -179.63(14) 5_657 . . . ?
C5 C4 C3 C3 -0.5(2) . . . 6 ?
C5 C4 C3 C6 175.63(15) . . . . ?
C5 C4 C1 C2 -0.7(3) . . . . ?
C4 C5 C4 C3 -179.5(2) 2_657 . . . ?
C4 C5 C4 C1 0.37(14) 2_657 . . . ?
C4 C3 C6 C11 111.6(6) . . . . ?
C4 C3 C6 C7 -78.8(6) . . . . ?
C4 C3 C6 C11A 89.5(8) . . . . ?
C4 C3 C6 C7A -93.7(6) . . . . ?
C4 C1 C2 C1 0.38(14) . . . 2_657 ?
C3 C4 C1 C2 179.12(16) . . . . ?
C3 C3 C6 C11 -72.2(6) 6 . . . ?
C3 C3 C6 C7 97.4(6) 6 . . . ?
C3 C3 C6 C11A -94.3(7) 6 . . . ?
C3 C3 C6 C7A 82.5(6) 6 . . . ?
C3 C6 C11 C10 169.58(17) . . . . ?
C3 C6 C7 C8 -169.48(17) . . . . ?
C3 C6 C11A C10A 169.6(5) . . . . ?
C3 C6 C7A C8A -169.1(5) . . . . ?
C12 C9 C8 C7 171.17(17) . . . . ?
C12 C9 C10A C11A -171.9(5) . . . . ?
C12 C9 C8A C7A 172.6(5) . . . . ?
C6 C11 C10 C9 0.0 . . . . ?
C6 C11A C10A C9 0.3(9) . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
C11 C10 C9 C12 -171.09(17) . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C8 C7 C6 0.0 . . . . ?
C9 C8A C7A C6 -1.5(9) . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C11A C6 C7A C8A 7.9(9) . . . . ?
C10A C9 C8A C7A -5.7(8) . . . . ?
C8A C9 C10A C11A 6.2(8) . . . . ?
C7A C6 C11A C10A -7.2(9) . . . . ?
C1 C4 C3 C3 179.63(14) . . . 6 ?
C1 C4 C3 C6 -4.2(3) . . . . ?
C17 C18 C13 Cl1 180.000(0) . . . . ?
C17 C18 C13 C14 0.000(0) . . . . ?
C17 C16 C15 C14 0.000(1) . . . . ?
C18 C17 C16 C15 0.000(1) . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C16 C17 C18 C13 0.000(0) . . . . ?
C15 C14 C13 Cl1 180.000(0) . . . . ?
C15 C14 C13 C18 0.000(1) . . . . ?

_olex2_submission_original_sample_id TBAPy-DCB-TCB-3-1-1h-dry
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.820
_exptl_crystal_recrystallization_method 
'obtained by desolvation-triggered structural transformation'
####################################################################### 
# 
# 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_CP-Py-DMAni-1
_database_code_depnum_ccdc_archive 'CCDC 2255742'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-05-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'4,5,9,10-Tetrakis(4-carboxyphenyl)pyrene N,N-dimethylaniline solvate'
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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'
O O 0.0146 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   23.4820(13)
_cell_length_b                   17.2143(10)
_cell_length_c                   7.5294(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.013(5)
_cell_angle_gamma                90
_cell_volume                     3036.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      32.4390
_cell_measurement_theta_min      1.9730
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18358
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        29.117
_diffrn_reflns_theta_max         33.335
_diffrn_reflns_theta_min         1.675
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00   0.00  180
  2  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00  90.00  180
  3  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00 180.00  180
  4  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00 270.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0343908000
_diffrn_orient_matrix_UB_12      -0.0041976000
_diffrn_orient_matrix_UB_13      -0.0010020000
_diffrn_orient_matrix_UB_21      0.0028466000
_diffrn_orient_matrix_UB_22      0.0467986000
_diffrn_orient_matrix_UB_23      -0.0078425000
_diffrn_orient_matrix_UB_31      0.0029285000
_diffrn_orient_matrix_UB_32      0.0033757000
_diffrn_orient_matrix_UB_33      0.1077327000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.811
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2641
_reflns_number_total             3692
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     125
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0911
_refine_ls_restrained_S_all      1.235
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3094
_refine_ls_wR_factor_ref         0.3208
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O2A-C12A \\sim O2B-C12B
 with sigma of 0.02
 C4-C6A \\sim C4-C6B
 with sigma of 0.02
 C6A-C7A \\sim C6B-C7B
 with sigma of 0.02
 C6A-C11A \\sim C6B-C11B
 with sigma of 0.02
 O1A-C12A \\sim O1B-C12B
 with sigma of 0.02
 C7A-C8A \\sim C7B-C8B
 with sigma of 0.02
 C9A-C8A \\sim C9B-C8B
 with sigma of 0.02
 C9A-C12A \\sim C9B-C12B
 with sigma of 0.02
 C9A-C10A \\sim C9B-C10B
 with sigma of 0.02
 C10A-C11A \\sim C10B-C11B
 with sigma of 0.02
 O2A-O1A \\sim O2B-O1B
 with sigma of 0.04
 O2A-C9A \\sim O2B-C9B
 with sigma of 0.04
 C4-C7A \\sim C4-C7B
 with sigma of 0.04
 C4-C11A \\sim C4-C11B
 with sigma of 0.04
 C6A-C8A \\sim C6B-C8B
 with sigma of 0.04
 C6A-C10A \\sim C6B-C10B
 with sigma of 0.04
 O1A-C9A \\sim O1B-C9B
 with sigma of 0.04
 C7A-C9A \\sim C7B-C9B
 with sigma of 0.04
 C7A-C11A \\sim C7B-C11B
 with sigma of 0.04
 C9A-C11A \\sim C9B-C11B
 with sigma of 0.04
 C8A-C12A \\sim C8B-C12B
 with sigma of 0.04
 C8A-C10A \\sim C8B-C10B
 with sigma of 0.04
 C12A-C10A \\sim C12B-C10B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C7B \\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C6B: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
C10A \\sim C9A \\sim C8A \\sim C7A \\sim C6A \\sim C11A: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
O2B \\sim C12B \\sim O1B: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
O1A \\sim C12A \\sim O2A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
Uanis(O1B) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Others
 Sof(O2B)=Sof(H2B)=Sof(O1B)=Sof(C12B)=Sof(C10B)=Sof(H10B)=Sof(C9B)=Sof(C8B)=
 Sof(H8B)=Sof(C7B)=Sof(H7B)=Sof(C6B)=Sof(C11B)=Sof(H11B)=1-FVAR(1)
 Sof(O2A)=Sof(H2A)=Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=
 Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(H7A)=Sof(O1A)=Sof(C12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C11A(H11A), C10A(H10A), C8A(H8A), C7A(H7A), C10B(H10B),
 C8B(H8B), C7B(H7B), C11B(H11B)
5.b Fitted hexagon refined as free rotating group:
 C6A(C11A,C10A,C9A,C8A,C7A), C10B(C9B,C8B,C7B,C6B,C11B)
5.c Tetrahedral OH refined with riding coordinates:
 O2A(H2A), O2B(H2B)
;
_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
C5 C 0.500000 0.54118(11) 0.000000 0.0405(5) Uani 1 2 d S T P . .
C3 C 0.53352(6) 0.58249(9) 0.13293(17) 0.0443(4) Uani 1 1 d . . . . .
O2A O 0.6963(5) 0.6846(9) 0.9724(10) 0.084(3) Uani 0.378(17) 1 d D U P A 1
H2A H 0.722427 0.701684 1.043705 0.126 Uiso 0.378(17) 1 calc R U P A 1
C4 C 0.56667(6) 0.53984(9) 0.26921(17) 0.0442(4) Uani 1 1 d D . . . .
C2 C 0.53246(8) 0.66372(9) 0.1315(2) 0.0540(5) Uani 1 1 d . . . . .
H2 H 0.554101 0.691981 0.221172 0.065 Uiso 1 1 calc R U . . .
C1 C 0.500000 0.70307(13) 0.000000 0.0621(7) Uani 1 2 d S T P . .
H1 H 0.500001 0.758257 -0.000002 0.075 Uiso 1 2 calc R U P . .
C6A C 0.6002(3) 0.5860(4) 0.4066(8) 0.059(3) Uani 0.378(17) 1 d DG U P A 1
C11A C 0.5770(3) 0.6105(7) 0.5619(11) 0.062(2) Uani 0.378(17) 1 d DG U P A 1
H11A H 0.538042 0.600461 0.579504 0.075 Uiso 0.378(17) 1 calc R U P A 1
C10A C 0.6109(4) 0.6498(6) 0.6916(10) 0.066(2) Uani 0.378(17) 1 d DG U P A 1
H10A H 0.595009 0.666558 0.797704 0.079 Uiso 0.378(17) 1 calc R U P A 1
C9A C 0.6679(3) 0.6645(4) 0.6659(10) 0.071(3) Uani 0.378(17) 1 d DG U P A 1
C8A C 0.6911(3) 0.6400(7) 0.5105(12) 0.073(2) Uani 0.378(17) 1 d DG U P A 1
H8A H 0.730098 0.650027 0.492973 0.087 Uiso 0.378(17) 1 calc R U P A 1
C7A C 0.6573(3) 0.6007(7) 0.3809(10) 0.062(2) Uani 0.378(17) 1 d DG U P A 1
H7A H 0.673132 0.583930 0.274770 0.075 Uiso 0.378(17) 1 calc R U P A 1
O1A O 0.7592(4) 0.7146(6) 0.7789(16) 0.073(2) Uani 0.378(17) 1 d D U P A 1
C12A C 0.7125(5) 0.6876(9) 0.8115(14) 0.072(3) Uani 0.378(17) 1 d D U P A 1
O2B O 0.6775(3) 0.7149(4) 0.9692(7) 0.0760(14) Uani 0.622(17) 1 d D U P A 2
H2B H 0.701320 0.736705 1.041293 0.114 Uiso 0.622(17) 1 calc R U P A 2
O1B O 0.7427(4) 0.7420(7) 0.7815(9) 0.106(3) Uani 0.622(17) 1 d D U P A 2
C12B C 0.6976(4) 0.7111(5) 0.8165(8) 0.071(2) Uani 0.622(17) 1 d D U P A 2
C10B C 0.6172(2) 0.6228(4) 0.7179(4) 0.0727(15) Uani 0.622(17) 1 d DG U P A 2
H10B H 0.605534 0.622778 0.836197 0.087 Uiso 0.622(17) 1 calc R U P A 2
C9B C 0.6664(2) 0.6621(3) 0.6780(5) 0.077(2) Uani 0.622(17) 1 d DG U P A 2
C8B C 0.6834(2) 0.6621(4) 0.5049(6) 0.0645(13) Uani 0.622(17) 1 d DG U P A 2
H8B H 0.716993 0.689035 0.477681 0.077 Uiso 0.622(17) 1 calc R U P A 2
C7B C 0.6512(2) 0.6228(4) 0.3715(4) 0.0523(11) Uani 0.622(17) 1 d DG U P A 2
H7B H 0.662792 0.622799 0.253203 0.063 Uiso 0.622(17) 1 calc R U P A 2
C6B C 0.60197(17) 0.5834(2) 0.4114(4) 0.0473(16) Uani 0.622(17) 1 d DG U P A 2
C11B C 0.5850(2) 0.5834(4) 0.5845(5) 0.0603(13) Uani 0.622(17) 1 d DG U P A 2
H11B H 0.551332 0.556542 0.611715 0.072 Uiso 0.622(17) 1 calc R U P A 2


_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
C5 C5 1.418(4) 5_665 ?
C5 C3 1.4202(17) . ?
C5 C3 1.4202(17) 2_655 ?
C3 C4 1.4444(19) . ?
C3 C2 1.398(2) . ?
O2A H2A 0.8400 . ?
O2A C12A 1.297(11) . ?
C4 C4 1.372(3) 6_565 ?
C4 C6A 1.486(5) . ?
C4 C6B 1.507(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.3838(19) . ?
C1 H1 0.9500 . ?
C6A C11A 1.3900 . ?
C6A C7A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9500 . ?
C10A C9A 1.3900 . ?
C9A C8A 1.3900 . ?
C9A C12A 1.515(9) . ?
C8A H8A 0.9500 . ?
C8A C7A 1.3900 . ?
C7A H7A 0.9500 . ?
O1A C12A 1.231(11) . ?
O2B H2B 0.8400 . ?
O2B C12B 1.275(6) . ?
O1B C12B 1.229(7) . ?
C12B C9B 1.493(6) . ?
C10B H10B 0.9500 . ?
C10B C9B 1.3900 . ?
C10B C11B 1.3900 . ?
C9B C8B 1.3900 . ?
C8B H8B 0.9500 . ?
C8B C7B 1.3900 . ?
C7B H7B 0.9500 . ?
C7B C6B 1.3900 . ?
C6B C11B 1.3900 . ?
C11B H11B 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
C5 C5 C3 120.05(9) 5_665 . ?
C5 C5 C3 120.05(9) 5_665 2_655 ?
C3 C5 C3 119.90(19) . 2_655 ?
C5 C3 C4 119.38(15) . . ?
C2 C3 C5 119.12(14) . . ?
C2 C3 C4 121.47(14) . . ?
C12A O2A H2A 109.5 . . ?
C3 C4 C6A 117.1(3) . . ?
C3 C4 C6B 119.57(19) . . ?
C4 C4 C3 120.56(9) 6_565 . ?
C4 C4 C6A 122.3(3) 6_565 . ?
C4 C4 C6B 119.87(15) 6_565 . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.23(14) . . ?
C1 C2 H2 119.9 . . ?
C2 C1 C2 121.38(19) . 2_655 ?
C2 C1 H1 119.3 2_655 . ?
C2 C1 H1 119.3 . . ?
C11A C6A C4 121.9(4) . . ?
C11A C6A C7A 120.0 . . ?
C7A C6A C4 118.0(4) . . ?
C6A C11A H11A 120.0 . . ?
C10A C11A C6A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C9A C12A 124.8(7) . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A C12A 113.4(7) . . ?
C9A C8A H8A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
O2A C12A C9A 115.6(8) . . ?
O1A C12A O2A 121.7(10) . . ?
O1A C12A C9A 122.3(10) . . ?
C12B O2B H2B 109.5 . . ?
O2B C12B C9B 117.6(5) . . ?
O1B C12B O2B 123.4(6) . . ?
O1B C12B C9B 118.9(6) . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C10B C9B C12B 120.0(4) . . ?
C8B C9B C12B 119.7(4) . . ?
C8B C9B C10B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C9B C8B C7B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B C8B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C6B C4 120.9(2) . . ?
C7B C6B C11B 120.0 . . ?
C11B C6B C4 119.1(2) . . ?
C10B C11B H11B 120.0 . . ?
C6B C11B C10B 120.0 . . ?
C6B C11B H11B 120.0 . . ?

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
C5 C5 C3 C4 -1.06(14) 5_665 . . . ?
C5 C5 C3 C2 -179.37(11) 5_665 . . . ?
C5 C3 C4 C4 1.07(15) . . . 6_565 ?
C5 C3 C4 C6A -179.0(3) . . . . ?
C5 C3 C4 C6B -179.5(2) . . . . ?
C5 C3 C2 C1 -1.3(2) . . . . ?
C3 C5 C3 C4 178.94(14) 2_655 . . . ?
C3 C5 C3 C2 0.63(11) 2_655 . . . ?
C3 C4 C6A C11A 88.4(6) . . . . ?
C3 C4 C6A C7A -95.2(6) . . . . ?
C3 C4 C6B C7B -71.3(4) . . . . ?
C3 C4 C6B C11B 109.2(4) . . . . ?
C3 C2 C1 C2 0.65(11) . . . 2_655 ?
C4 C3 C2 C1 -179.55(12) . . . . ?
C4 C4 C6A C11A -91.7(6) 6_565 . . . ?
C4 C4 C6A C7A 84.7(6) 6_565 . . . ?
C4 C4 C6B C7B 108.1(4) 6_565 . . . ?
C4 C4 C6B C11B -71.4(4) 6_565 . . . ?
C4 C6A C11A C10A 176.4(6) . . . . ?
C4 C6A C7A C8A -176.5(6) . . . . ?
C4 C6B C11B C10B 179.5(3) . . . . ?
C2 C3 C4 C4 179.34(11) . . . 6_565 ?
C2 C3 C4 C6A -0.8(4) . . . . ?
C2 C3 C4 C6B -1.3(3) . . . . ?
C6A C11A C10A C9A 0.0 . . . . ?
C11A C6A C7A C8A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C11A C10A C9A C12A -163.7(10) . . . . ?
C10A C9A C8A C7A 0.0 . . . . ?
C10A C9A C12A O2A 7.8(15) . . . . ?
C10A C9A C12A O1A -165.5(12) . . . . ?
C9A C8A C7A C6A 0.0 . . . . ?
C8A C9A C12A O2A -156.8(11) . . . . ?
C8A C9A C12A O1A 29.9(17) . . . . ?
C7A C6A C11A C10A 0.0 . . . . ?
C12A C9A C8A C7A 165.4(8) . . . . ?
O2B C12B C9B C10B 0.0(8) . . . . ?
O2B C12B C9B C8B 173.7(6) . . . . ?
O1B C12B C9B C10B 176.1(6) . . . . ?
O1B C12B C9B C8B -10.1(10) . . . . ?
C12B C9B C8B C7B -173.7(6) . . . . ?
C10B C9B C8B C7B 0.0 . . . . ?
C9B C10B C11B C6B 0.0 . . . . ?
C9B C8B C7B C6B 0.0 . . . . ?
C8B C7B C6B C4 -179.5(3) . . . . ?
C8B C7B C6B C11B 0.0 . . . . ?
C7B C6B C11B C10B 0.0 . . . . ?
C11B C10B C9B C12B 173.7(6) . . . . ?
C11B C10B C9B C8B 0.0 . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.022 764 235 ' '
2 0.000 0.500 -0.078 764 235 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.588
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, N,N-dimethylaniline'
####################################################################### 
# 
# 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_CP-Py-1-TCB
_database_code_depnum_ccdc_archive 'CCDC 2255740'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-10-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        CP-Py-1-TCB
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7428(3)
_cell_length_b                   15.8023(9)
_cell_length_c                   27.6306(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.044(4)
_cell_angle_gamma                90
_cell_volume                     2939.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9361
_cell_measurement_temperature    113
_cell_measurement_theta_max      29.7890
_cell_measurement_theta_min      2.5650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.871
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_temperature      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00  78.00   0.25    5.00    --  -12.00  45.00  51.00  720
  2  ω   -102.00  78.00   0.25    5.00    --  -12.00  45.00 157.00  720
  3  ω    -74.25 -29.25   0.25    5.00    --  -12.00  45.00 300.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003619000
_diffrn_orient_matrix_UB_12      -0.0405036000
_diffrn_orient_matrix_UB_13      0.0110949000
_diffrn_orient_matrix_UB_21      0.1051697000
_diffrn_orient_matrix_UB_22      0.0010902000
_diffrn_orient_matrix_UB_23      0.0024281000
_diffrn_orient_matrix_UB_31      -0.0050368000
_diffrn_orient_matrix_UB_32      0.0193584000
_diffrn_orient_matrix_UB_33      0.0230661000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4789
_reflns_number_total             7603
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         7603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      1.044
_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)+(0.1805P)²+2.6401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3012
_refine_ls_wR_factor_ref         0.3294
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C11(H11), C2(H2A), C10(H10), C17(H17), C14(H14), C18(H18),
 C20(H20), C21(H21), C13(H13)
2.b Tetrahedral OH refined with riding coordinates:
 O4(H4), O2(H2)
;
_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
O4 O -0.0125(3) 0.72455(19) 0.31879(9) 0.0637(7) Uani 1 1 d . . . . .
H4 H -0.082045 0.744913 0.295503 0.096 Uiso 1 1 calc R U . . .
O1 O 0.2559(3) 0.2900(2) 0.24920(8) 0.0643(8) Uani 1 1 d . . . . .
O2 O 0.0200(3) 0.3006(2) 0.30035(9) 0.0760(9) Uani 1 1 d . . . . .
H2 H -0.046843 0.279066 0.276975 0.114 Uiso 1 1 calc R U . . .
C8 C 1.0056(3) 0.45491(16) 0.49816(8) 0.0252(5) Uani 1 1 d . . . . .
O3 O 0.2231(3) 0.7438(2) 0.26801(10) 0.0912(12) Uani 1 1 d . . . . .
C7 C 1.1467(3) 0.40933(16) 0.52822(8) 0.0270(5) Uani 1 1 d . . . . .
C4 C 0.8749(3) 0.41028(16) 0.46507(8) 0.0275(5) Uani 1 1 d . . . . .
C9 C 0.5976(4) 0.41346(17) 0.39874(9) 0.0307(5) Uani 1 1 d . . . . .
C16 C 0.5777(3) 0.59222(16) 0.40572(8) 0.0293(5) Uani 1 1 d . . . . .
C3 C 0.8864(4) 0.32244(17) 0.46284(9) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.799318 0.292322 0.440860 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7318(3) 0.45789(17) 0.43500(8) 0.0269(5) Uani 1 1 d . . . . .
C6 C 0.7218(3) 0.54496(16) 0.43830(8) 0.0273(5) Uani 1 1 d . . . . .
C1 C 1.1530(4) 0.32138(18) 0.52455(9) 0.0359(6) Uani 1 1 d . . . . .
H1 H 1.247028 0.290490 0.544351 0.043 Uiso 1 1 calc R U . . .
C19 C 0.3073(4) 0.6749(2) 0.34181(10) 0.0429(7) Uani 1 1 d . . . . .
C11 C 0.5326(4) 0.3575(2) 0.31802(9) 0.0421(7) Uani 1 1 d . . . . .
H11 H 0.579424 0.343025 0.287274 0.051 Uiso 1 1 calc R U . . .
C2 C 1.0238(4) 0.27821(18) 0.49238(10) 0.0390(6) Uani 1 1 d . . . . .
H2A H 1.029475 0.218228 0.490568 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3392(4) 0.3425(2) 0.32795(10) 0.0400(7) Uani 1 1 d . . . . .
C10 C 0.6607(4) 0.3943(2) 0.35347(9) 0.0407(7) Uani 1 1 d . . . . .
H10 H 0.793966 0.406207 0.346174 0.049 Uiso 1 1 calc R U . . .
C17 C 0.6309(4) 0.6149(2) 0.36005(10) 0.0439(7) Uani 1 1 d . . . . .
H17 H 0.759897 0.601379 0.350136 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1663(4) 0.7168(3) 0.30667(12) 0.0556(9) Uani 1 1 d . . . . .
C15 C 0.1991(4) 0.3071(2) 0.28965(11) 0.0491(8) Uani 1 1 d . . . . .
C14 C 0.4011(4) 0.3980(2) 0.40844(10) 0.0479(8) Uani 1 1 d . . . . .
H14 H 0.354519 0.411324 0.439388 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4982(4) 0.6574(2) 0.32814(11) 0.0528(9) Uani 1 1 d . . . . .
H18 H 0.538247 0.674316 0.297153 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2539(4) 0.6528(3) 0.38750(11) 0.0535(9) Uani 1 1 d . . . . .
H20 H 0.123264 0.664248 0.397015 0.064 Uiso 1 1 calc R U . . .
C21 C 0.3890(4) 0.6142(3) 0.41952(10) 0.0545(9) Uani 1 1 d . . . . .
H21 H 0.352690 0.602345 0.451575 0.065 Uiso 1 1 calc R U . . .
C13 C 0.2726(4) 0.3631(3) 0.37291(11) 0.0540(9) Uani 1 1 d . . . . .
H13 H 0.137733 0.353399 0.379560 0.065 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
O4 H4 0.8400 . ?
O4 C22 1.274(4) . ?
O1 C15 1.230(4) . ?
O2 H2 0.8400 . ?
O2 C15 1.263(4) . ?
C8 C8 1.431(5) 3_766 ?
C8 C7 1.425(3) . ?
C8 C4 1.423(3) . ?
O3 C22 1.231(4) . ?
C7 C6 1.441(3) 3_766 ?
C7 C1 1.394(4) . ?
C4 C3 1.392(4) . ?
C4 C5 1.450(3) . ?
C9 C5 1.490(3) . ?
C9 C10 1.377(4) . ?
C9 C14 1.387(4) . ?
C16 C6 1.489(3) . ?
C16 C17 1.377(4) . ?
C16 C21 1.392(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(4) . ?
C5 C6 1.381(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(4) . ?
C19 C22 1.479(4) . ?
C19 C18 1.388(4) . ?
C19 C20 1.376(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(4) . ?
C11 C10 1.398(3) . ?
C2 H2A 0.9500 . ?
C12 C15 1.490(3) . ?
C12 C13 1.382(4) . ?
C10 H10 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.395(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(4) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9500 . ?
C13 H13 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
C22 O4 H4 109.5 . . ?
C15 O2 H2 109.5 . . ?
C7 C8 C8 119.9(2) . 3_766 ?
C4 C8 C8 120.4(2) . 3_766 ?
C4 C8 C7 119.7(2) . . ?
C8 C7 C6 119.3(2) . 3_766 ?
C1 C7 C8 118.9(2) . . ?
C1 C7 C6 121.7(2) . 3_766 ?
C8 C4 C5 118.8(2) . . ?
C3 C4 C8 119.3(2) . . ?
C3 C4 C5 122.0(2) . . ?
C10 C9 C5 120.6(2) . . ?
C10 C9 C14 118.8(2) . . ?
C14 C9 C5 120.4(2) . . ?
C17 C16 C6 119.4(2) . . ?
C17 C16 C21 118.2(2) . . ?
C21 C16 C6 122.4(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C5 C9 120.2(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 C9 118.9(2) . . ?
C7 C6 C16 119.7(2) 3_766 . ?
C5 C6 C7 120.7(2) . 3_766 ?
C5 C6 C16 119.5(2) . . ?
C7 C1 H1 119.5 . . ?
C2 C1 C7 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C18 C19 C22 118.9(3) . . ?
C20 C19 C22 121.7(3) . . ?
C20 C19 C18 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.5(2) . . ?
C10 C11 H11 120.3 . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2A 119.9 . . ?
C11 C12 C15 119.9(2) . . ?
C11 C12 C13 119.9(2) . . ?
C13 C12 C15 120.2(3) . . ?
C9 C10 C11 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
O4 C22 C19 117.1(3) . . ?
O3 C22 O4 122.5(3) . . ?
O3 C22 C19 120.4(3) . . ?
O1 C15 O2 122.9(3) . . ?
O1 C15 C12 120.7(3) . . ?
O2 C15 C12 116.3(3) . . ?
C9 C14 H14 120.0 . . ?
C9 C14 C13 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?

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
C8 C8 C7 C6 -0.6(4) 3_766 . . 3_766 ?
C8 C8 C7 C1 179.1(3) 3_766 . . . ?
C8 C8 C4 C3 -178.8(3) 3_766 . . . ?
C8 C8 C4 C5 0.5(4) 3_766 . . . ?
C8 C7 C1 C2 -0.3(4) . . . . ?
C8 C4 C3 C2 -0.2(4) . . . . ?
C8 C4 C5 C9 177.9(2) . . . . ?
C8 C4 C5 C6 -0.1(3) . . . . ?
C7 C8 C4 C3 0.4(3) . . . . ?
C7 C8 C4 C5 179.7(2) . . . . ?
C7 C1 C2 C3 0.5(4) . . . . ?
C4 C8 C7 C6 -179.9(2) . . . 3_766 ?
C4 C8 C7 C1 -0.2(3) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . 3_766 ?
C4 C5 C6 C16 177.9(2) . . . . ?
C9 C5 C6 C7 -178.0(2) . . . 3_766 ?
C9 C5 C6 C16 0.0(3) . . . . ?
C9 C14 C13 C12 0.9(6) . . . . ?
C16 C17 C18 C19 -2.1(6) . . . . ?
C3 C4 C5 C9 -2.9(4) . . . . ?
C3 C4 C5 C6 179.2(2) . . . . ?
C5 C4 C3 C2 -179.4(2) . . . . ?
C5 C9 C10 C11 -175.9(3) . . . . ?
C5 C9 C14 C13 174.5(3) . . . . ?
C6 C7 C1 C2 179.4(3) 3_766 . . . ?
C6 C16 C17 C18 178.4(3) . . . . ?
C6 C16 C21 C20 -175.5(3) . . . . ?
C19 C20 C21 C16 -3.7(6) . . . . ?
C11 C12 C15 O1 0.9(5) . . . . ?
C11 C12 C15 O2 -175.1(3) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C12 C11 C10 C9 1.9(5) . . . . ?
C10 C9 C5 C4 -84.0(3) . . . . ?
C10 C9 C5 C6 94.0(3) . . . . ?
C10 C9 C14 C13 0.5(5) . . . . ?
C10 C11 C12 C15 177.1(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C17 C16 C6 C7 92.5(3) . . . 3_766 ?
C17 C16 C6 C5 -85.5(3) . . . . ?
C17 C16 C21 C20 4.0(5) . . . . ?
C22 C19 C18 C17 -177.5(3) . . . . ?
C22 C19 C20 C21 -179.7(4) . . . . ?
C15 C12 C13 C14 -178.5(3) . . . . ?
C14 C9 C5 C4 102.2(3) . . . . ?
C14 C9 C5 C6 -79.9(3) . . . . ?
C14 C9 C10 C11 -1.9(5) . . . . ?
C18 C19 C22 O4 173.5(4) . . . . ?
C18 C19 C22 O3 -7.7(6) . . . . ?
C18 C19 C20 C21 0.4(6) . . . . ?
C20 C19 C22 O4 -6.4(6) . . . . ?
C20 C19 C22 O3 172.4(4) . . . . ?
C20 C19 C18 C17 2.5(6) . . . . ?
C21 C16 C6 C7 -88.0(3) . . . 3_766 ?
C21 C16 C6 C5 94.0(3) . . . . ?
C21 C16 C17 C18 -1.1(5) . . . . ?
C13 C12 C15 O1 178.5(4) . . . . ?
C13 C12 C15 O2 2.5(5) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.049 0.500 0.000 778 156 ' '
2 -0.022 0.000 0.500 778 155 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_original_sample_id CP-Py-TCB-Form2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.832
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF, 1,2,4-trichlorobenzene'
####################################################################### 
# 
# 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_CP-Py-2-DMAni
_database_code_depnum_ccdc_archive 'CCDC 2255743'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-04-12 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_PLAT084_CP-Py-2-DMAni       
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: Because of sever disorder of the included N,N-dimethylaniline
;
_vrf_PLAT250_CP-Py-2-DMAni       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.6 Note  
RESPONSE: Because of sever disorder of the included N,N-dimethylaniline
;
_vrf_PLAT260_CP-Py-2-DMAni       
;
PROBLEM: Large Average Ueq of Residue Including        N1      0.370 Check 
RESPONSE: Because of sever disorder of the included N,N-dimethylaniline
;
# end Validation Reply Form


_chemical_name_common            ?
_chemical_name_systematic        CP-Py-2-DMAni
_chemical_formula_moiety         'C44 H26 O8, 3(C8 H11 N)'
_chemical_formula_sum            'C68 H59 N3 O8'
_chemical_formula_weight         1046.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0035 0.0022 '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 0.0065 0.0044 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0116 0.0081 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4693(4)
_cell_length_b                   14.233(2)
_cell_length_c                   24.1720(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.080(6)
_cell_angle_gamma                90
_cell_volume                     2563.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6649
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.6360
_cell_measurement_theta_min      1.8820
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32342
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        29.117
_diffrn_reflns_theta_max         33.848
_diffrn_reflns_theta_min         1.896
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00   0.00  180
  2  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00  90.00  180
  3  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00 180.00  180
  4  ω    -90.00  90.00   1.00    2.00    --   25.00  45.00 270.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334131000
_diffrn_orient_matrix_UB_12      -0.0043664000
_diffrn_orient_matrix_UB_13      0.0310946000
_diffrn_orient_matrix_UB_21      0.0245647000
_diffrn_orient_matrix_UB_22      -0.0554341000
_diffrn_orient_matrix_UB_23      0.0005372000
_diffrn_orient_matrix_UB_31      0.1007549000
_diffrn_orient_matrix_UB_32      0.0123015000
_diffrn_orient_matrix_UB_33      0.0127845000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.811
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2802
_reflns_number_total             6267
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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         0.238
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.2104
_refine_ls_R_factor_gt           0.1210
_refine_ls_restrained_S_all      1.273
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3631
_refine_ls_wR_factor_ref         0.4120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2-C38 = N2-C37 = N1-C30 = N1-C29
 1.46 with sigma of 0.02
 C30-C29
 2.495 with sigma of 0.02
 N2-C31 = N1-C23
 1.396 with sigma of 0.02
 C38-C37
 2.495 with sigma of 0.02
 C31-C38 \\sim C31-C37 \\sim C23-C29 \\sim C23-C30
 with sigma of 0.04
 C28-N1 \\sim C24-N1 \\sim C36-N2 \\sim C32-N2
 with sigma of 0.04
 O1-C15 \\sim O3-C22
 with sigma of 0.02
 O4-C22 \\sim O2-C15
 with sigma of 0.02
3. Restrained planarity
 N1, C23, C28, C27, C26, C25, C24
 with sigma of 0.1
 N1, C29, C30, C23
 with sigma of 0.1
4. Rigid bond restraints
 C29, C24, C25, C23, N1, C26, C28, C30, C27
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C37, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
N2 \\sim C38 \\sim C37 \\sim C36 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim
C35: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
1.7A
C38 \\sim N2 \\sim C37: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
C23 \\sim C28 \\sim C27 \\sim C26 \\sim C25 \\sim C24: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C36 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C27 \\sim C26 \\sim C25 \\sim C24 \\sim C28 \\sim C23: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C27 \\sim C26 \\sim C25 \\sim C24 \\sim C23 \\sim C28: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C34 \\sim C33 \\sim C32 \\sim C31 \\sim C36 \\sim C35: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C29 \\sim N1 \\sim C30: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
6. Others
 Fixed Sof: C24(0.5) H24(0.5) C25(0.5) H25(0.5) C26(0.5) H26(0.5) C27(0.5)
 H27(0.5) C28(0.5) H28(0.5) C23(0.5) N1(0.5) C29(0.5) H29A(0.5) H29B(0.5)
 H29C(0.5) C30(0.5) H30A(0.5) H30B(0.5) H30C(0.5)
7.a Me refined with riding coordinates:
 C38(H38A,H38B,H38C), C37(H37A,H37B,H37C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C2(H2A), C10(H10), C14(H14), C17(H17), C11(H11), C21(H21),
 C20(H20), C13(H13), C18(H18), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
  C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
7.c Fitted hexagon refined as free rotating group:
 C24(C25,C26,C27,C28,C23), C32(C33,C34,C35,C36,C31)
7.d Tetrahedral OH refined with riding coordinates:
 O2(H2), O4(H4)
;
_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
O1 O 0.1905(3) 0.3565(3) 0.23022(12) 0.1188(13) Uani 1 1 d D . . . .
O2 O 0.0002(4) 0.3807(4) 0.29257(13) 0.1531(19) Uani 1 1 d D . . . .
H2 H -0.072604 0.365084 0.266080 0.230 Uiso 1 1 calc R U . . .
C8 C 0.9912(4) 0.4520(3) 0.49454(12) 0.0686(11) Uani 1 1 d . . . . .
O4 O 0.0602(3) 0.8006(3) 0.34193(13) 0.1447(17) Uani 1 1 d D . . . .
H4 H -0.011323 0.826365 0.318208 0.217 Uiso 1 1 calc R U . . .
C5 C 0.7233(4) 0.4868(4) 0.43354(13) 0.0729(11) Uani 1 1 d . . . . .
C6 C 0.7410(4) 0.5789(4) 0.44482(12) 0.0736(11) Uani 1 1 d . . . . .
C4 C 0.8472(4) 0.4203(4) 0.45831(13) 0.0717(11) Uani 1 1 d . . . . .
O3 O 0.2496(4) 0.8337(4) 0.28047(17) 0.163(2) Uani 1 1 d D . . . .
C7 C 1.1145(4) 0.3878(3) 0.51880(13) 0.0701(11) Uani 1 1 d . . . . .
C3 C 0.8330(5) 0.3258(4) 0.44747(16) 0.0868(13) Uani 1 1 d . . . . .
H3 H 0.737751 0.303395 0.422820 0.104 Uiso 1 1 calc R U . . .
C9 C 0.5761(4) 0.4550(3) 0.39467(13) 0.0795(12) Uani 1 1 d . . . . .
C1 C 1.0937(5) 0.2937(4) 0.50642(16) 0.0845(12) Uani 1 1 d . . . . .
H1 H 1.177686 0.249516 0.522308 0.101 Uiso 1 1 calc R U . . .
C16 C 0.6130(4) 0.6460(3) 0.41773(14) 0.0818(12) Uani 1 1 d . . . . .
C12 C 0.3026(4) 0.4016(4) 0.31896(15) 0.0922(14) Uani 1 1 d . . . . .
C2 C 0.9543(5) 0.2634(4) 0.47172(17) 0.0892(12) Uani 1 1 d . . . . .
H2A H 0.940807 0.198158 0.464205 0.107 Uiso 1 1 calc R U . . .
C10 C 0.6062(4) 0.4335(4) 0.34113(14) 0.1019(16) Uani 1 1 d . . . . .
H10 H 0.725234 0.435725 0.329712 0.122 Uiso 1 1 calc R U . . .
C15 C 0.1562(5) 0.3765(4) 0.27751(17) 0.1037(16) Uani 1 1 d D . . . .
C14 C 0.4033(5) 0.4476(4) 0.40944(15) 0.1096(18) Uani 1 1 d . . . . .
H14 H 0.378615 0.459967 0.446760 0.132 Uiso 1 1 calc R U . . .
C17 C 0.6469(5) 0.6854(4) 0.36825(17) 0.1128(18) Uani 1 1 d . . . . .
H17 H 0.760521 0.676562 0.353692 0.135 Uiso 1 1 calc R U . . .
C11 C 0.4700(5) 0.4091(4) 0.30385(15) 0.1038(16) Uani 1 1 d . . . . .
H11 H 0.494250 0.397179 0.266447 0.125 Uiso 1 1 calc R U . . .
C19 C 0.3558(4) 0.7498(4) 0.35828(17) 0.1044(16) Uani 1 1 d . . . . .
C22 C 0.2150(5) 0.8008(5) 0.3250(2) 0.132(2) Uani 1 1 d D . . . .
C21 C 0.4539(5) 0.6663(4) 0.43821(17) 0.1117(18) Uani 1 1 d . . . . .
H21 H 0.430928 0.643500 0.473947 0.134 Uiso 1 1 calc R U . . .
C20 C 0.3257(5) 0.7181(4) 0.40971(18) 0.1162(19) Uani 1 1 d . . . . .
H20 H 0.215985 0.731966 0.425602 0.139 Uiso 1 1 calc R U . . .
C13 C 0.2677(5) 0.4234(5) 0.37289(16) 0.118(2) Uani 1 1 d . . . . .
H13 H 0.148266 0.421232 0.383993 0.141 Uiso 1 1 calc R U . . .
C18 C 0.5175(5) 0.7379(5) 0.3393(2) 0.138(2) Uani 1 1 d . . . . .
H18 H 0.543694 0.766160 0.305193 0.166 Uiso 1 1 calc R U . . .
N2 N 0.414(2) 0.1159(12) 0.3483(6) 0.326(6) Uani 1 1 d D U . . .
C24 C 1.028(4) -0.027(2) 0.4443(14) 0.381(13) Uani 0.5 1 d DG U P A -1
H24 H 1.139516 -0.026568 0.427760 0.457 Uiso 0.5 1 calc R U P A -1
C25 C 0.871(6) -0.049(2) 0.4125(12) 0.386(14) Uani 0.5 1 d G U P A -1
H25 H 0.875306 -0.062780 0.374149 0.463 Uiso 0.5 1 calc R U P A -1
C26 C 0.708(5) -0.050(2) 0.4367(16) 0.380(14) Uani 0.5 1 d G U P A -1
H26 H 0.600432 -0.064721 0.414926 0.456 Uiso 0.5 1 calc R U P A -1
C27 C 0.701(3) -0.030(2) 0.4928(16) 0.377(14) Uani 0.5 1 d G U P A -1
H27 H 0.589765 -0.030451 0.509314 0.453 Uiso 0.5 1 calc R U P A -1
C28 C 0.858(4) -0.008(2) 0.5246(11) 0.347(13) Uani 0.5 1 d DG U P A -1
H28 H 0.853973 0.005761 0.562925 0.416 Uiso 0.5 1 calc R U P A -1
C23 C 1.022(3) -0.0070(17) 0.5004(13) 0.360(13) Uani 0.5 1 d DG U P A -1
C32 C 0.2158(17) 0.0846(8) 0.2676(5) 0.299(6) Uani 1 1 d DG U . . .
H32 H 0.313333 0.056818 0.250422 0.359 Uiso 1 1 calc R U . . .
C33 C 0.046(2) 0.0855(9) 0.2403(3) 0.317(7) Uani 1 1 d G U . . .
H33 H 0.026915 0.058320 0.204411 0.380 Uiso 1 1 calc R U . . .
C34 C -0.0971(15) 0.1261(9) 0.2654(5) 0.310(6) Uani 1 1 d G U . . .
H34 H -0.213411 0.126705 0.246699 0.372 Uiso 1 1 calc R U . . .
C35 C -0.0698(15) 0.1658(8) 0.3178(5) 0.315(6) Uani 1 1 d G U . . .
H35 H -0.167320 0.193588 0.334997 0.378 Uiso 1 1 calc R U . . .
C36 C 0.1004(17) 0.1649(8) 0.3452(3) 0.304(6) Uani 1 1 d DG U . . .
H36 H 0.119096 0.192086 0.381008 0.365 Uiso 1 1 calc R U . . .
C31 C 0.2431(14) 0.1243(8) 0.3200(4) 0.278(6) Uani 1 1 d DG U . . .
C38 C 0.427(2) 0.1655(10) 0.3991(6) 0.308(8) Uani 1 1 d D U . . .
H38A H 0.548007 0.157456 0.417137 0.463 Uiso 1 1 calc R U . . .
H38B H 0.404560 0.232397 0.392046 0.463 Uiso 1 1 calc R U . . .
H38C H 0.338444 0.141060 0.423388 0.463 Uiso 1 1 calc R U . . .
C37 C 0.512(3) 0.0390(18) 0.3291(10) 0.416(12) Uani 1 1 d D U . . .
H37A H 0.629570 0.035844 0.349861 0.623 Uiso 1 1 calc R U . . .
H37B H 0.446077 -0.019374 0.334537 0.623 Uiso 1 1 calc R U . . .
H37C H 0.528941 0.047258 0.289545 0.623 Uiso 1 1 calc R U . . .
N1 N 1.175(3) 0.012(2) 0.5313(14) 0.359(14) Uani 0.5 1 d D U P A -1
C29 C 1.322(4) -0.046(2) 0.5151(18) 0.383(15) Uani 0.5 1 d D U P A -1
H29A H 1.431125 -0.030068 0.538329 0.574 Uiso 0.5 1 calc R U P A -1
H29B H 1.293126 -0.112097 0.519765 0.574 Uiso 0.5 1 calc R U P A -1
H29C H 1.342598 -0.033400 0.476092 0.574 Uiso 0.5 1 calc R U P A -1
C30 C 1.175(5) 0.072(3) 0.5749(19) 0.367(15) Uani 0.5 1 d D U P A -1
H30A H 1.296772 0.077679 0.592520 0.551 Uiso 0.5 1 calc R U P A -1
H30B H 1.133820 0.134400 0.561640 0.551 Uiso 0.5 1 calc R U P A -1
H30C H 1.094098 0.048904 0.601987 0.551 Uiso 0.5 1 calc R U P A -1


_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 C15 1.223(5) . ?
O2 H2 0.8400 . ?
O2 C15 1.246(5) . ?
C8 C8 1.396(8) 3_766 ?
C8 C4 1.412(4) . ?
C8 C7 1.396(5) . ?
O4 H4 0.8400 . ?
O4 C22 1.253(5) . ?
C5 C6 1.344(6) . ?
C5 C4 1.425(6) . ?
C5 C9 1.466(5) . ?
C6 C7 1.425(5) 3_766 ?
C6 C16 1.472(5) . ?
C4 C3 1.373(6) . ?
O3 C22 1.219(5) . ?
C7 C1 1.379(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.371(6) . ?
C9 C10 1.364(5) . ?
C9 C14 1.368(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.360(5) . ?
C16 C17 1.361(5) . ?
C16 C21 1.351(5) . ?
C12 C15 1.473(5) . ?
C12 C11 1.331(5) . ?
C12 C13 1.383(5) . ?
C2 H2A 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.356(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.341(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(6) . ?
C11 H11 0.9500 . ?
C19 C22 1.469(6) . ?
C19 C20 1.356(6) . ?
C19 C18 1.333(6) . ?
C21 H21 0.9500 . ?
C21 C20 1.357(5) . ?
C20 H20 0.9500 . ?
C13 H13 0.9500 . ?
C18 H18 0.9500 . ?
N2 C31 1.409(12) . ?
N2 C38 1.414(13) . ?
N2 C37 1.414(14) . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C24 C23 1.3900 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C23 1.3900 . ?
C23 N1 1.348(16) . ?
C32 H32 0.9500 . ?
C32 C33 1.3900 . ?
C32 C31 1.3900 . ?
C33 H33 0.9500 . ?
C33 C34 1.3900 . ?
C34 H34 0.9500 . ?
C34 C35 1.3900 . ?
C35 H35 0.9500 . ?
C35 C36 1.3900 . ?
C36 H36 0.9500 . ?
C36 C31 1.3900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
N1 C29 1.449(17) . ?
N1 C30 1.363(17) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 H2 109.5 . . ?
C8 C8 C4 119.1(4) 3_766 . ?
C8 C8 C7 120.7(4) 3_766 . ?
C7 C8 C4 120.1(4) . . ?
C22 O4 H4 109.5 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 C9 119.3(3) . . ?
C4 C5 C9 120.0(4) . . ?
C5 C6 C7 120.6(4) . 3_766 ?
C5 C6 C16 119.5(3) . . ?
C7 C6 C16 119.9(5) 3_766 . ?
C8 C4 C5 119.5(4) . . ?
C3 C4 C8 118.4(3) . . ?
C3 C4 C5 122.1(3) . . ?
C8 C7 C6 119.3(4) . 3_766 ?
C1 C7 C8 118.9(3) . . ?
C1 C7 C6 121.8(4) . 3_766 ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C10 C9 C5 120.7(3) . . ?
C10 C9 C14 116.9(3) . . ?
C14 C9 C5 122.3(3) . . ?
C7 C1 H1 119.6 . . ?
C2 C1 C7 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C17 C16 C6 120.2(3) . . ?
C21 C16 C6 122.4(3) . . ?
C21 C16 C17 117.2(4) . . ?
C11 C12 C15 119.9(3) . . ?
C11 C12 C13 119.0(3) . . ?
C13 C12 C15 121.0(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2A 119.6 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
O1 C15 O2 123.1(3) . . ?
O1 C15 C12 119.8(3) . . ?
O2 C15 C12 117.0(3) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 122.0(3) . . ?
C13 C14 H14 119.0 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C20 C19 C22 120.4(4) . . ?
C18 C19 C22 120.4(4) . . ?
C18 C19 C20 119.1(4) . . ?
O4 C22 C19 117.5(4) . . ?
O3 C22 O4 123.2(4) . . ?
O3 C22 C19 119.0(4) . . ?
C16 C21 H21 118.7 . . ?
C16 C21 C20 122.5(4) . . ?
C20 C21 H21 118.7 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C31 N2 C38 112.6(12) . . ?
C31 N2 C37 112.3(14) . . ?
C38 N2 C37 131.7(15) . . ?
C25 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C23 120.0 . . ?
C23 C28 H28 120.0 . . ?
C28 C23 C24 120.0 . . ?
N1 C23 C24 119.7(15) . . ?
N1 C23 C28 120.3(15) . . ?
C33 C32 H32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C35 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C31 120.0 . . ?
C31 C36 H36 120.0 . . ?
C32 C31 N2 118.5(9) . . ?
C36 C31 N2 121.3(9) . . ?
C36 C31 C32 120.0 . . ?
N2 C38 H38A 109.5 . . ?
N2 C38 H38B 109.5 . . ?
N2 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N2 C37 H37A 109.5 . . ?
N2 C37 H37B 109.5 . . ?
N2 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C23 N1 C29 111.7(18) . . ?
C23 N1 C30 120.6(19) . . ?
C30 N1 C29 127(2) . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
N1 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N1 C30 H30A 109.5 . . ?
N1 C30 H30B 109.5 . . ?
N1 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C8 C4 C5 0.2(5) 3_766 . . . ?
C8 C8 C4 C3 179.2(4) 3_766 . . . ?
C8 C8 C7 C6 0.2(5) 3_766 . . 3_766 ?
C8 C8 C7 C1 -179.2(4) 3_766 . . . ?
C8 C4 C3 C2 0.8(5) . . . . ?
C8 C7 C1 C2 -0.8(5) . . . . ?
C5 C6 C16 C17 -89.9(5) . . . . ?
C5 C6 C16 C21 85.6(5) . . . . ?
C5 C4 C3 C2 179.8(3) . . . . ?
C5 C9 C10 C11 -176.2(5) . . . . ?
C5 C9 C14 C13 176.3(5) . . . . ?
C6 C5 C4 C8 -0.8(5) . . . . ?
C6 C5 C4 C3 -179.8(3) . . . . ?
C6 C5 C9 C10 100.8(5) . . . . ?
C6 C5 C9 C14 -77.5(6) . . . . ?
C6 C7 C1 C2 179.8(3) 3_766 . . . ?
C6 C16 C17 C18 171.2(6) . . . . ?
C6 C16 C21 C20 -170.9(5) . . . . ?
C4 C8 C7 C6 179.9(3) . . . 3_766 ?
C4 C8 C7 C1 0.5(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . 3_766 ?
C4 C5 C6 C16 178.8(3) . . . . ?
C4 C5 C9 C10 -78.3(5) . . . . ?
C4 C5 C9 C14 103.3(5) . . . . ?
C4 C3 C2 C1 -1.2(6) . . . . ?
C7 C8 C4 C5 -179.5(3) . . . . ?
C7 C8 C4 C3 -0.5(5) . . . . ?
C7 C6 C16 C17 88.1(5) 3_766 . . . ?
C7 C6 C16 C21 -96.5(5) 3_766 . . . ?
C7 C1 C2 C3 1.2(6) . . . . ?
C9 C5 C6 C7 -178.2(3) . . . 3_766 ?
C9 C5 C6 C16 -0.3(5) . . . . ?
C9 C5 C4 C8 178.3(3) . . . . ?
C9 C5 C4 C3 -0.7(5) . . . . ?
C9 C10 C11 C12 -2.7(9) . . . . ?
C9 C14 C13 C12 2.5(9) . . . . ?
C16 C17 C18 C19 -1.3(10) . . . . ?
C16 C21 C20 C19 1.0(9) . . . . ?
C10 C9 C14 C13 -2.1(8) . . . . ?
C15 C12 C11 C10 179.0(5) . . . . ?
C15 C12 C13 C14 -178.8(5) . . . . ?
C14 C9 C10 C11 2.2(8) . . . . ?
C17 C16 C21 C20 4.7(8) . . . . ?
C11 C12 C15 O1 4.9(8) . . . . ?
C11 C12 C15 O2 -172.3(5) . . . . ?
C11 C12 C13 C14 -2.9(9) . . . . ?
C22 C19 C20 C21 176.1(6) . . . . ?
C22 C19 C18 C17 -175.9(7) . . . . ?
C21 C16 C17 C18 -4.5(9) . . . . ?
C20 C19 C22 O4 -11.1(10) . . . . ?
C20 C19 C22 O3 175.4(7) . . . . ?
C20 C19 C18 C17 7.2(11) . . . . ?
C13 C12 C15 O1 -179.2(6) . . . . ?
C13 C12 C15 O2 3.6(8) . . . . ?
C13 C12 C11 C10 3.0(8) . . . . ?
C18 C19 C22 O4 172.0(7) . . . . ?
C18 C19 C22 O3 -1.5(10) . . . . ?
C18 C19 C20 C21 -7.0(10) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C24 C23 N1 C29 -37(2) . . . . ?
C24 C23 N1 C30 148(3) . . . . ?
C25 C24 C23 C28 0.0 . . . . ?
C25 C24 C23 N1 178.6(9) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C26 C27 C28 C23 0.0 . . . . ?
C27 C28 C23 C24 0.0 . . . . ?
C27 C28 C23 N1 -178.6(9) . . . . ?
C28 C23 N1 C29 142(2) . . . . ?
C28 C23 N1 C30 -33(3) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C32 C31 N2 175.2(12) . . . . ?
C33 C32 C31 C36 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C35 C36 C31 N2 -175.1(12) . . . . ?
C35 C36 C31 C32 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C38 N2 C31 C32 175.4(12) . . . . ?
C38 N2 C31 C36 -9.5(19) . . . . ?
C37 N2 C31 C32 -23(2) . . . . ?
C37 N2 C31 C36 152.4(17) . . . . ?

_olex2_submission_original_sample_id CP-Py-DMA-Form2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.675
_exptl_crystal_recrystallization_method 
'obtained by desolvation-triggered structural transformation'
####################################################################### 
# 
# 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_CP-Py-1-MeNaph
_database_code_depnum_ccdc_archive 'CCDC 2262072'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        4,5,9,10-Tetrakis(4-carboxyphenyl)pyrene
_chemical_formula_moiety         'C44 H26 O8, 3(C11 H10)'
_chemical_formula_sum            'C77 H56 O8'
_chemical_formula_weight         1109.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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.
;

# start Validation Reply Form
_vrf_RINTA01_CP-Py-1-MeNaph      
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: because the crystal underwent two step structural transition, 
and therefore, the crystal quality became lower.
;
_vrf_PLAT020_CP-Py-1-MeNaph      
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.356 Report
RESPONSE: because the crystal underwent two step structural transition, 
and therefore, the crystal quality became lower.
;
_vrf_PLAT412_CP-Py-1-MeNaph      
;
PROBLEM: Short Intra XH3 .. XHn     H25      ..H33C     .       1.54 Ang.  
RESPONSE: Due to highly disordered methylnaphthalene guest molecule
;
# end Validation Reply Form


_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6554(13)
_cell_length_b                   15.342(3)
_cell_length_c                   24.524(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.763(18)
_cell_angle_gamma                90
_cell_volume                     2870.4(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    113
_cell_measurement_theta_max      24.8550
_cell_measurement_theta_min      2.6930
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3556
_diffrn_reflns_av_unetI/netI     0.3321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            43799
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.191
_diffrn_reflns_theta_min         2.655
_diffrn_ambient_temperature      113
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00  86.00   0.25   15.00    --   -4.00  45.00  86.00  720
  2  ω    -72.00  30.00   0.25   15.00    --   -4.00  45.00 122.00  408
  3  ω    -78.00  16.00   0.25   15.00    --   -4.00  45.00  15.00  376
  4  ω    -77.50 -32.50   0.25   15.00    --   -4.00  45.00  51.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042992000
_diffrn_orient_matrix_UB_12      0.0454670000
_diffrn_orient_matrix_UB_13      -0.0049916000
_diffrn_orient_matrix_UB_21      0.0501548000
_diffrn_orient_matrix_UB_22      -0.0080134000
_diffrn_orient_matrix_UB_23      -0.0225682000
_diffrn_orient_matrix_UB_31      -0.0780847000
_diffrn_orient_matrix_UB_32      -0.0026758000
_diffrn_orient_matrix_UB_33      -0.0175810000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2278
_reflns_number_total             7579
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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         0.531
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7579
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.3606
_refine_ls_R_factor_gt           0.1408
_refine_ls_restrained_S_all      1.018
_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)+(0.1983P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3410
_refine_ls_wR_factor_ref         0.4412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C34-H34
 0.95 with sigma of 0.005
 C35-H34 \\sim C38-H34
 with sigma of 0.02
3. Restrained planarity
 H34, C34, C35, C38, C37, C36, C39
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C28 \\sim C27 \\sim C26 \\sim C25 \\sim C24 \\sim C29 \\sim C30 \\sim C31 \\sim
C32 \\sim C23: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
5. Others
 Fixed Sof: C39(0.5) H39A(0.5) H39B(0.5) H39C(0.5) H34(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C1(H1), C17(H17), C21(H21), C11(H11), C10(H10), C13(H13),
 C2(H2A), C20(H20), C18(H18), C35(H35), C36(H36), C37(H37), C25(H25), C26(H26),
 C27(H27), C28(H28), C32(H32), C31(H31), C30(H30)
6.b Tetrahedral OH refined with riding coordinates:
 O4(H4), O2(H2)
6.c Naphthalene refined as free rotating group:
 C25(C26,C27,C28,C29,C24,C23,C32,C31,C30)
6.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   mixed
_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
O4 O 0.1985(6) 0.6875(4) 0.24339(19) 0.0536(15) Uani 1 1 d . . . . .
H4 H 0.108704 0.700479 0.222993 0.080 Uiso 1 1 calc R U . . .
O3 O 0.0001(6) 0.6408(4) 0.2980(2) 0.0553(15) Uani 1 1 d . . . . .
O1 O 0.0606(6) 0.2422(4) 0.3253(2) 0.0548(15) Uani 1 1 d . . . . .
O2 O 0.2550(6) 0.2087(4) 0.2664(2) 0.0599(16) Uani 1 1 d . . . . .
H2 H 0.165643 0.188487 0.248550 0.090 Uiso 1 1 calc R U . . .
C16 C 0.5731(7) 0.5623(4) 0.3987(2) 0.0292(14) Uani 1 1 d . . . . .
C4 C 0.8852(7) 0.3976(4) 0.4748(2) 0.0267(14) Uani 1 1 d . . . . .
C6 C 0.7227(7) 0.5231(4) 0.4354(2) 0.0291(15) Uani 1 1 d . . . . .
C9 C 0.6106(8) 0.3754(4) 0.4087(2) 0.0305(15) Uani 1 1 d . . . . .
C5 C 0.7395(7) 0.4353(4) 0.4404(2) 0.0293(15) Uani 1 1 d . . . . .
C7 C 1.1502(7) 0.4177(4) 0.5366(2) 0.0266(14) Uani 1 1 d . . . . .
C8 C 1.0084(8) 0.4543(4) 0.5028(2) 0.0280(14) Uani 1 1 d . . . . .
C14 C 0.4610(9) 0.3482(4) 0.4315(3) 0.0383(17) Uani 1 1 d . . . . .
H14 H 0.446696 0.359659 0.468915 0.046 Uiso 1 1 calc R U . . .
C3 C 0.9038(8) 0.3079(4) 0.4802(2) 0.0333(16) Uani 1 1 d . . . . .
H3 H 0.821769 0.270271 0.460862 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2116(8) 0.2417(5) 0.3104(3) 0.0387(17) Uani 1 1 d . . . . .
C12 C 0.3547(8) 0.2842(5) 0.3459(3) 0.0376(17) Uani 1 1 d . . . . .
C1 C 1.1644(8) 0.3264(4) 0.5411(2) 0.0328(15) Uani 1 1 d . . . . .
H1 H 1.259457 0.301726 0.563312 0.039 Uiso 1 1 calc R U . . .
C17 C 0.6075(8) 0.5997(4) 0.3499(2) 0.0343(16) Uani 1 1 d . . . . .
H17 H 0.725057 0.604151 0.340494 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4021(8) 0.5570(4) 0.4124(3) 0.0353(16) Uani 1 1 d . . . . .
H21 H 0.377771 0.532967 0.446685 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5088(8) 0.3076(5) 0.3237(3) 0.0441(18) Uani 1 1 d . . . . .
H11 H 0.527527 0.291886 0.287121 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1530(9) 0.6532(5) 0.2873(3) 0.0416(18) Uani 1 1 d . . . . .
C10 C 0.6380(8) 0.3551(4) 0.3559(3) 0.0367(16) Uani 1 1 d . . . . .
H10 H 0.742997 0.372689 0.340965 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3308(8) 0.3040(5) 0.3994(3) 0.0401(17) Uani 1 1 d . . . . .
H13 H 0.225381 0.287521 0.414552 0.048 Uiso 1 1 calc R U . . .
C2 C 1.0431(8) 0.2725(4) 0.5140(3) 0.0376(17) Uani 1 1 d . . . . .
H2A H 1.053443 0.211082 0.518097 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2668(8) 0.5865(4) 0.3768(3) 0.0385(17) Uani 1 1 d . . . . .
H20 H 0.149377 0.582188 0.386282 0.046 Uiso 1 1 calc R U . . .
C18 C 0.4721(8) 0.6309(5) 0.3142(3) 0.0415(17) Uani 1 1 d . . . . .
H18 H 0.496905 0.658174 0.280902 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3014(8) 0.6222(5) 0.3272(3) 0.0375(16) Uani 1 1 d . . . . .
C38 C -0.0943(15) 0.0127(7) 0.4976(5) 0.086(3) Uani 1 1 d D . . . .
C34 C -0.1486(18) 0.0677(7) 0.4519(6) 0.101(4) Uani 1 1 d D . . . .
C35 C -0.033(2) 0.0924(8) 0.4169(5) 0.103(4) Uani 1 1 d D . . . .
H35 H -0.073768 0.127134 0.386434 0.124 Uiso 1 1 calc R U . . .
C36 C -0.143(2) -0.0706(8) 0.5777(6) 0.108(4) Uani 1 1 d . . . . .
H36 H -0.221169 -0.090926 0.602956 0.129 Uiso 1 1 calc R U . . .
C37 C -0.200(2) -0.0169(8) 0.5333(6) 0.112(4) Uani 1 1 d . . . . .
H37 H -0.320587 -0.001273 0.528743 0.134 Uiso 1 1 calc R U . . .
C25 C 0.2320(12) 0.9530(4) 0.2807(3) 0.119(4) Uani 1 1 d G U . . .
H25 H 0.290282 0.992162 0.258291 0.143 Uiso 1 1 calc R U . . .
C26 C 0.0563(11) 0.9331(5) 0.2679(3) 0.110(4) Uani 1 1 d G U . . .
H26 H -0.005553 0.958608 0.236681 0.132 Uiso 1 1 calc R U . . .
C27 C -0.0289(9) 0.8758(6) 0.3006(4) 0.138(5) Uani 1 1 d G U . . .
H27 H -0.148997 0.862129 0.291872 0.165 Uiso 1 1 calc R U . . .
C28 C 0.0616(9) 0.8384(5) 0.3463(3) 0.128(5) Uani 1 1 d G U . . .
H28 H 0.003392 0.799205 0.368673 0.153 Uiso 1 1 calc R U . . .
C29 C 0.2374(9) 0.8583(3) 0.3591(2) 0.095(4) Uani 1 1 d G U . . .
C24 C 0.3226(9) 0.9156(3) 0.3263(2) 0.111(4) Uani 1 1 d G U . . .
C23 C 0.4983(9) 0.9355(5) 0.3392(3) 0.122(4) Uani 1 1 d G U . . .
C32 C 0.5888(9) 0.8982(6) 0.3848(4) 0.107(4) Uani 1 1 d G U . . .
H32 H 0.708930 0.911795 0.393549 0.128 Uiso 1 1 calc R U . . .
C31 C 0.5036(12) 0.8409(5) 0.4176(3) 0.133(5) Uani 1 1 d G U . . .
H31 H 0.565492 0.815316 0.448741 0.160 Uiso 1 1 calc R U . . .
C30 C 0.3279(12) 0.8209(4) 0.4047(2) 0.139(5) Uani 1 1 d G U . . .
H30 H 0.269659 0.781759 0.427133 0.166 Uiso 1 1 calc R U . . .
C33 C 0.569(3) 0.9962(10) 0.3068(7) 0.203(10) Uani 1 1 d . . . . .
H33A H 0.671536 0.971168 0.290944 0.304 Uiso 1 1 calc R U . . .
H33B H 0.605936 1.047298 0.328912 0.304 Uiso 1 1 calc R U . . .
H33C H 0.482038 1.013732 0.277412 0.304 Uiso 1 1 calc R U . . .
C39 C -0.345(3) 0.1015(15) 0.4371(12) 0.114(9) Uani 0.5 1 d . . P A 2
H39A H -0.418971 0.052576 0.423625 0.170 Uiso 0.5 1 calc R U P A 2
H39B H -0.345289 0.146492 0.408768 0.170 Uiso 0.5 1 calc R U P A 2
H39C H -0.391208 0.125917 0.469936 0.170 Uiso 0.5 1 calc R U P A 2
H34 H -0.269(2) 0.0842(18) 0.4491(11) 0.136 Uiso 0.5 1 d D U P B 1


_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
O4 H4 0.8400 . ?
O4 C22 1.273(8) . ?
O3 C22 1.235(8) . ?
O1 C15 1.241(8) . ?
O2 H2 0.8400 . ?
O2 C15 1.260(8) . ?
C16 C6 1.521(8) . ?
C16 C17 1.372(8) . ?
C16 C21 1.381(9) . ?
C4 C5 1.461(7) . ?
C4 C8 1.417(8) . ?
C4 C3 1.388(9) . ?
C6 C5 1.358(8) . ?
C6 C7 1.459(8) 3_766 ?
C9 C5 1.516(8) . ?
C9 C14 1.379(9) . ?
C9 C10 1.364(9) . ?
C7 C8 1.426(8) . ?
C7 C1 1.409(8) . ?
C8 C8 1.414(12) 3_766 ?
C14 H14 0.9500 . ?
C14 C13 1.394(9) . ?
C3 H3 0.9500 . ?
C3 C2 1.405(8) . ?
C15 C12 1.492(9) . ?
C12 C11 1.387(9) . ?
C12 C13 1.374(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(8) . ?
C21 H21 0.9500 . ?
C21 C20 1.375(8) . ?
C11 H11 0.9500 . ?
C11 C10 1.417(9) . ?
C22 C19 1.513(8) . ?
C10 H10 0.9500 . ?
C13 H13 0.9500 . ?
C2 H2A 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.378(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(9) . ?
C38 C38 1.49(2) 3_556 ?
C38 C34 1.438(18) . ?
C38 C37 1.322(16) . ?
C34 C35 1.339(16) . ?
C34 C39 1.60(3) . ?
C34 H34 0.950(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.378(17) 3_556 ?
C36 H36 0.9500 . ?
C36 C37 1.407(17) . ?
C37 H37 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.3900 . ?
C25 C24 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C29 1.3900 . ?
C29 C24 1.3900 . ?
C29 C30 1.3900 . ?
C24 C23 1.3900 . ?
C23 C32 1.3900 . ?
C23 C33 1.365(18) . ?
C32 H32 0.9500 . ?
C32 C31 1.3900 . ?
C31 H31 0.9500 . ?
C31 C30 1.3900 . ?
C30 H30 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O4 H4 109.5 . . ?
C15 O2 H2 109.5 . . ?
C17 C16 C6 119.5(5) . . ?
C17 C16 C21 119.5(5) . . ?
C21 C16 C6 120.9(6) . . ?
C8 C4 C5 118.7(5) . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 C8 120.3(5) . . ?
C5 C6 C16 120.4(5) . . ?
C5 C6 C7 121.3(5) . 3_766 ?
C7 C6 C16 118.2(5) 3_766 . ?
C14 C9 C5 120.2(6) . . ?
C10 C9 C5 118.7(6) . . ?
C10 C9 C14 120.9(5) . . ?
C4 C5 C9 119.3(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 C9 120.2(5) . . ?
C8 C7 C6 118.4(5) . 3_766 ?
C1 C7 C6 122.5(5) . 3_766 ?
C1 C7 C8 119.1(5) . . ?
C4 C8 C7 118.9(5) . . ?
C8 C8 C4 120.7(6) 3_766 . ?
C8 C8 C7 120.3(6) 3_766 . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
O1 C15 O2 125.0(6) . . ?
O1 C15 C12 118.8(6) . . ?
O2 C15 C12 116.2(6) . . ?
C11 C12 C15 119.4(6) . . ?
C13 C12 C15 120.3(6) . . ?
C13 C12 C11 120.2(6) . . ?
C7 C1 H1 119.5 . . ?
C2 C1 C7 121.1(5) . . ?
C2 C1 H1 119.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.3(6) . . ?
C20 C21 H21 119.9 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
O4 C22 C19 115.7(6) . . ?
O3 C22 O4 125.1(6) . . ?
O3 C22 C19 119.2(6) . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0(6) . . ?
C12 C13 H13 120.0 . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2A 119.9 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.1(6) . . ?
C19 C20 H20 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C22 120.4(6) . . ?
C18 C19 C22 119.7(6) . . ?
C18 C19 C20 119.9(6) . . ?
C34 C38 C38 115.5(14) . 3_556 ?
C37 C38 C38 120.1(16) . 3_556 ?
C37 C38 C34 124.4(13) . . ?
C38 C34 C39 124.8(15) . . ?
C38 C34 H34 115.2(17) . . ?
C35 C34 C38 120.1(13) . . ?
C35 C34 C39 115.1(16) . . ?
C35 C34 H34 124.7(18) . . ?
C34 C35 H35 117.9 . . ?
C34 C35 C36 124.2(14) . 3_556 ?
C36 C35 H35 117.9 3_556 . ?
C35 C36 H36 121.5 3_556 . ?
C35 C36 C37 117.1(14) 3_556 . ?
C37 C36 H36 121.5 . . ?
C38 C37 C36 123.0(14) . . ?
C38 C37 H37 118.5 . . ?
C36 C37 H37 118.5 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C24 120.0 . . ?
C28 C29 C30 120.0 . . ?
C24 C29 C30 120.0 . . ?
C29 C24 C25 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 C29 120.0 . . ?
C24 C23 C32 120.0 . . ?
C33 C23 C24 116.4(10) . . ?
C33 C23 C32 123.5(10) . . ?
C23 C32 H32 120.0 . . ?
C31 C32 C23 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C23 C33 H33A 109.5 . . ?
C23 C33 H33B 109.5 . . ?
C23 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C34 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
C34 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C22 C19 C20 178.0(6) . . . . ?
O4 C22 C19 C18 -1.1(10) . . . . ?
O3 C22 C19 C20 -4.8(11) . . . . ?
O3 C22 C19 C18 176.2(7) . . . . ?
O1 C15 C12 C11 -160.8(7) . . . . ?
O1 C15 C12 C13 16.0(10) . . . . ?
O2 C15 C12 C11 18.1(10) . . . . ?
O2 C15 C12 C13 -165.1(7) . . . . ?
C16 C6 C5 C4 178.7(5) . . . . ?
C16 C6 C5 C9 0.9(9) . . . . ?
C16 C17 C18 C19 -1.8(10) . . . . ?
C16 C21 C20 C19 -0.6(10) . . . . ?
C4 C3 C2 C1 -1.4(10) . . . . ?
C6 C16 C17 C18 176.0(6) . . . . ?
C6 C16 C21 C20 -174.8(6) . . . . ?
C6 C7 C8 C4 179.2(5) 3_766 . . . ?
C6 C7 C8 C8 -0.7(11) 3_766 . . 3_766 ?
C6 C7 C1 C2 -179.5(6) 3_766 . . . ?
C9 C14 C13 C12 2.8(10) . . . . ?
C5 C4 C8 C7 179.6(6) . . . . ?
C5 C4 C8 C8 -0.4(11) . . . 3_766 ?
C5 C4 C3 C2 -179.1(6) . . . . ?
C5 C9 C14 C13 170.5(6) . . . . ?
C5 C9 C10 C11 -172.7(6) . . . . ?
C7 C6 C5 C4 0.9(10) 3_766 . . . ?
C7 C6 C5 C9 -176.9(6) 3_766 . . . ?
C7 C1 C2 C3 1.3(10) . . . . ?
C8 C4 C5 C6 -0.1(9) . . . . ?
C8 C4 C5 C9 177.8(6) . . . . ?
C8 C4 C3 C2 1.0(10) . . . . ?
C8 C7 C1 C2 -0.7(10) . . . . ?
C14 C9 C5 C4 91.6(8) . . . . ?
C14 C9 C5 C6 -90.6(8) . . . . ?
C14 C9 C10 C11 1.8(10) . . . . ?
C3 C4 C5 C6 -179.9(6) . . . . ?
C3 C4 C5 C9 -2.1(9) . . . . ?
C3 C4 C8 C7 -0.5(9) . . . . ?
C3 C4 C8 C8 179.4(7) . . . 3_766 ?
C15 C12 C11 C10 174.2(6) . . . . ?
C15 C12 C13 C14 -176.3(6) . . . . ?
C12 C11 C10 C9 1.5(10) . . . . ?
C1 C7 C8 C4 0.3(9) . . . . ?
C1 C7 C8 C8 -179.6(7) . . . 3_766 ?
C17 C16 C6 C5 -107.1(7) . . . . ?
C17 C16 C6 C7 70.8(8) . . . 3_766 ?
C17 C16 C21 C20 2.1(10) . . . . ?
C17 C18 C19 C22 -177.7(6) . . . . ?
C17 C18 C19 C20 3.2(11) . . . . ?
C21 C16 C6 C5 69.8(8) . . . . ?
C21 C16 C6 C7 -112.4(7) . . . 3_766 ?
C21 C16 C17 C18 -0.9(10) . . . . ?
C21 C20 C19 C22 178.9(6) . . . . ?
C21 C20 C19 C18 -2.1(10) . . . . ?
C11 C12 C13 C14 0.4(11) . . . . ?
C10 C9 C5 C4 -93.9(7) . . . . ?
C10 C9 C5 C6 83.9(8) . . . . ?
C10 C9 C14 C13 -3.9(10) . . . . ?
C13 C12 C11 C10 -2.5(11) . . . . ?
C38 C38 C34 C35 0.3(16) 3_556 . . . ?
C38 C38 C34 C39 178.3(13) 3_556 . . . ?
C38 C38 C37 C36 1.9(19) 3_556 . . . ?
C38 C34 C35 C36 -2.1(16) . . . 3_556 ?
C34 C38 C37 C36 -179.9(10) . . . . ?
C35 C36 C37 C38 -0.2(17) 3_556 . . . ?
C37 C38 C34 C35 -178.0(11) . . . . ?
C37 C38 C34 C39 -0.1(18) . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C25 C24 C23 C32 180.0 . . . . ?
C25 C24 C23 C33 3.7(10) . . . . ?
C26 C25 C24 C29 0.0 . . . . ?
C26 C25 C24 C23 180.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
C27 C28 C29 C30 180.0 . . . . ?
C28 C29 C24 C25 0.0 . . . . ?
C28 C29 C24 C23 180.0 . . . . ?
C28 C29 C30 C31 180.0 . . . . ?
C29 C24 C23 C32 0.0 . . . . ?
C29 C24 C23 C33 -176.3(10) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C24 C29 C30 C31 0.0 . . . . ?
C24 C23 C32 C31 0.0 . . . . ?
C23 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C30 C29 C24 C25 180.0 . . . . ?
C30 C29 C24 C23 0.0 . . . . ?
C33 C23 C32 C31 176.0(11) . . . . ?
C39 C34 C35 C36 179.8(13) . . . 3_556 ?

_olex2_submission_original_sample_id CP-Py-2-DCB-dropped-Menaph
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.831
_exptl_crystal_recrystallization_method 
'obtained by solvent exchange-triggered structural transformation'
