# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_tsukiyama020
_database_code_depnum_ccdc_archive 'CCDC 1912444'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-02-22
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H22 N2 O6'
_chemical_formula_sum            'C40 H22 N2 O6'
_chemical_formula_weight         626.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9135(14)
_cell_length_b                   16.740(3)
_cell_length_c                   10.714(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.788(19)
_cell_angle_gamma                90
_cell_volume                     1412.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    983
_cell_measurement_temperature    123
_cell_measurement_theta_max      24.4410
_cell_measurement_theta_min      2.7880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_unetI/netI     0.1686
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9337
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.859
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00-120.00  193
  2  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00   0.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0089482000
_diffrn_orient_matrix_UB_12      0.0421427000
_diffrn_orient_matrix_UB_13      0.0032747000
_diffrn_orient_matrix_UB_21      -0.0364864000
_diffrn_orient_matrix_UB_22      0.0006506000
_diffrn_orient_matrix_UB_23      -0.0631684000
_diffrn_orient_matrix_UB_31      -0.0818051000
_diffrn_orient_matrix_UB_32      -0.0048486000
_diffrn_orient_matrix_UB_33      0.0205295000
_diffrn_oxdiff_ac3_digest_frames 
;
011a35d802b18200c579e8fda30eb7a60e003861692
;
_diffrn_oxdiff_ac3_digest_hkl    
;
016ecd959d881d01fc50acd6cf4657eaba57d4
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1401
_reflns_number_total             2881
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      0.900
_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)+(0.0170P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_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 0.6881(3) 0.71246(15) 0.1679(2) 0.0245(6) Uani 1 1 d . . . . .
O2 O 0.4080(3) 0.52506(15) 0.3766(2) 0.0274(6) Uani 1 1 d . . . . .
O3 O 1.0526(3) 0.66817(16) 0.3537(2) 0.0287(7) Uani 1 1 d . . . . .
N1 N 0.5610(3) 0.61539(18) 0.2750(2) 0.0179(7) Uani 1 1 d . . . . .
C1 C 0.6320(4) 0.6289(2) -0.0617(3) 0.0217(8) Uani 1 1 d . . . . .
H1 H 0.678085 0.681148 -0.064918 0.026 Uiso 1 1 calc R . . . .
C2 C 0.5816(4) 0.6004(2) 0.0490(3) 0.0172(8) Uani 1 1 d . . . . .
C3 C 0.5084(4) 0.5245(2) 0.0545(3) 0.0164(8) Uani 1 1 d . . . . .
C4 C 0.4518(4) 0.4942(2) 0.1660(3) 0.0190(8) Uani 1 1 d . . . . .
C5 C 0.3840(5) 0.4190(2) 0.1709(3) 0.0227(9) Uani 1 1 d . . . . .
H5 H 0.348052 0.399324 0.247058 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6145(4) 0.6480(2) 0.1653(3) 0.0194(8) Uani 1 1 d . . . . .
C7 C 0.4676(4) 0.5444(2) 0.2816(3) 0.0206(8) Uani 1 1 d . . . . .
C8 C 0.6122(5) 0.6579(2) 0.3915(3) 0.0202(8) Uani 1 1 d . . . . .
C9 C 0.7864(4) 0.6631(2) 0.4322(3) 0.0205(8) Uani 1 1 d . . . . .
C10 C 0.8314(5) 0.7084(2) 0.5407(3) 0.0240(9) Uani 1 1 d . . . . .
H10 H 0.948170 0.714918 0.569337 0.029 Uiso 1 1 calc R . . . .
C11 C 0.7108(5) 0.7436(2) 0.6068(3) 0.0257(9) Uani 1 1 d . . . . .
H11 H 0.744843 0.772829 0.681088 0.031 Uiso 1 1 calc R . . . .
C12 C 0.5406(5) 0.7364(2) 0.5653(3) 0.0278(9) Uani 1 1 d . . . . .
H12 H 0.457520 0.760433 0.611364 0.033 Uiso 1 1 calc R . . . .
C13 C 0.4904(5) 0.6938(2) 0.4556(3) 0.0220(8) Uani 1 1 d . . . . .
H13 H 0.373635 0.689699 0.425567 0.026 Uiso 1 1 calc R . . . .
C14 C 0.9248(5) 0.6288(2) 0.3655(3) 0.0217(8) Uani 1 1 d . . . . .
C15 C 0.9092(4) 0.5455(2) 0.3153(3) 0.0212(8) Uani 1 1 d . . . . .
C16 C 0.9800(5) 0.5270(2) 0.2043(3) 0.0260(9) Uani 1 1 d . . . . .
H16 H 1.040921 0.566445 0.163317 0.031 Uiso 1 1 calc R . . . .
C17 C 0.9604(5) 0.4506(2) 0.1545(3) 0.0305(10) Uani 1 1 d . . . . .
H17 H 1.005778 0.438262 0.078005 0.037 Uiso 1 1 calc R . . . .
C18 C 0.8763(5) 0.3926(2) 0.2146(3) 0.0301(10) Uani 1 1 d . . . . .
H18 H 0.863873 0.340579 0.179517 0.036 Uiso 1 1 calc R . . . .
C19 C 0.8095(5) 0.4098(2) 0.3262(3) 0.0285(10) Uani 1 1 d . . . . .
H19 H 0.753105 0.369332 0.368233 0.034 Uiso 1 1 calc R . . . .
C20 C 0.8249(4) 0.4863(2) 0.3766(3) 0.0235(9) Uani 1 1 d . . . . .
H20 H 0.778093 0.498197 0.452715 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.225(4) . ?
O2 C7 1.208(4) . ?
O3 C14 1.224(4) . ?
N1 C6 1.400(4) . ?
N1 C7 1.405(4) . ?
N1 C8 1.459(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(4) . ?
C1 C5 1.413(5) 3_665 ?
C2 C3 1.401(5) . ?
C2 C6 1.480(5) . ?
C3 C3 1.422(6) 3_665 ?
C3 C4 1.411(4) . ?
C4 C5 1.371(5) . ?
C4 C7 1.492(5) . ?
C5 H5 0.9500 . ?
C8 C9 1.406(5) . ?
C8 C13 1.376(5) . ?
C9 C10 1.403(5) . ?
C9 C14 1.483(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.398(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.494(5) . ?
C15 C16 1.400(5) . ?
C15 C20 1.396(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(5) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 125.3(3) . . ?
C6 N1 C8 116.6(3) . . ?
C7 N1 C8 118.1(3) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C5 120.5(3) . 3_665 ?
C5 C1 H1 119.7 3_665 . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 C6 119.9(3) . . ?
C3 C2 C6 119.4(3) . . ?
C2 C3 C3 119.5(4) . 3_665 ?
C2 C3 C4 122.0(3) . . ?
C4 C3 C3 118.5(4) . 3_665 ?
C3 C4 C7 119.6(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 C7 119.0(3) . . ?
C1 C5 H5 120.3 3_665 . ?
C4 C5 C1 119.5(3) . 3_665 ?
C4 C5 H5 120.3 . . ?
O1 C6 N1 120.5(3) . . ?
O1 C6 C2 122.4(3) . . ?
N1 C6 C2 117.0(3) . . ?
O2 C7 N1 121.5(3) . . ?
O2 C7 C4 122.8(3) . . ?
N1 C7 C4 115.7(3) . . ?
C9 C8 N1 118.3(3) . . ?
C13 C8 N1 119.5(3) . . ?
C13 C8 C9 122.1(3) . . ?
C8 C9 C14 125.1(3) . . ?
C10 C9 C8 116.7(3) . . ?
C10 C9 C14 118.1(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.3(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O3 C14 C9 119.9(3) . . ?
O3 C14 C15 120.3(3) . . ?
C9 C14 C15 119.8(3) . . ?
C16 C15 C14 119.1(3) . . ?
C20 C15 C14 121.3(3) . . ?
C20 C15 C16 119.6(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.0 . . ?

_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.789
####################################################################### 
# 
# 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_ono013
_database_code_depnum_ccdc_archive 'CCDC 1912445'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2018-04-25
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H22 N2 O6, C7 H6 O'
_chemical_formula_sum            'C48 H22 N2 O7'
_chemical_formula_weight         738.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O '
_chemical_oxdiff_usercomment     'tsukiyama 2BP-NDI anisole'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.1404(7)
_cell_length_b                   28.690(4)
_cell_length_c                   8.7340(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.299(10)
_cell_angle_gamma                90
_cell_volume                     1788.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    955
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.0110
_cell_measurement_theta_min      2.7260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6525
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         2.731
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 109.00   1.00   30.00    --   30.00  54.00 -60.00  183
  2  ω      6.00  47.00   1.00   30.00    --   30.00  54.00-150.00   41
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0179254000
_diffrn_orient_matrix_UB_12      0.0166821000
_diffrn_orient_matrix_UB_13      0.0577658000
_diffrn_orient_matrix_UB_21      0.0397735000
_diffrn_orient_matrix_UB_22      0.0176798000
_diffrn_orient_matrix_UB_23      -0.0458091000
_diffrn_orient_matrix_UB_31      -0.0892691000
_diffrn_orient_matrix_UB_32      0.0045158000
_diffrn_orient_matrix_UB_33      -0.0341113000
_diffrn_oxdiff_ac3_digest_frames 
;
01162b404fb7ffd467d333dd1adbe86a1500224327f
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01ca2f06e3235874b7093851198e12392c74dd
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2099
_reflns_number_total             3286
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.021
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1187
_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
2. Others
 Sof(H0AA)=Sof(O4)=Sof(C2AA)=Sof(H2Aa)=Sof(H2Ab)=Sof(H2Ac)=0.5*(1-FVAR(2))
 Sof(H1AA)=Sof(O6)=Sof(C2AB)=Sof(H2Ad)=Sof(H2Ae)=Sof(H2Af)=0.5*FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C13(H13), C20(H20), C24(H24), C23(H23), C12(H12), C10(H10),
 C22(H22), C21(H21), C11(H11), C1(H1), C0AA(H0AA), C1AA(H1AA)
3.b Idealised Me refined as rotating group:
 C2AA(H2Aa,H2Ab,H2Ac), C2AB(H2Ad,H2Ae,H2Af)
;
_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
O17 O 0.3832(2) 0.35994(5) -0.10793(18) 0.0223(4) Uani 1 1 d . . . . .
O16 O 0.3671(2) 0.41701(5) 0.38035(18) 0.0236(4) Uani 1 1 d . . . . .
O15 O 0.7507(2) 0.36436(6) 0.1933(2) 0.0341(5) Uani 1 1 d . . . . .
N1 N 0.3723(3) 0.38861(6) 0.1358(2) 0.0165(4) Uani 1 1 d . . . . .
C18 C 0.4739(3) 0.47763(7) 0.0267(3) 0.0138(5) Uani 1 1 d . . . . .
C5 C 0.4957(3) 0.44678(7) -0.2308(3) 0.0167(5) Uani 1 1 d . . . . .
H5 H 0.486431 0.421344 -0.300151 0.020 Uiso 1 1 calc R . . . .
C6 C 0.4570(3) 0.44018(7) -0.0776(3) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.4514(3) 0.50905(8) 0.2838(3) 0.0175(5) Uani 1 1 d . . . . .
H4 H 0.425023 0.504776 0.388991 0.021 Uiso 1 1 calc R . . . .
C3 C 0.4374(3) 0.47173(7) 0.1841(3) 0.0156(5) Uani 1 1 d . . . . .
C7 C 0.4025(3) 0.39341(8) -0.0225(3) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.3893(3) 0.42473(8) 0.2442(3) 0.0182(5) Uani 1 1 d . . . . .
C8 C 0.3473(3) 0.34128(7) 0.1915(3) 0.0186(5) Uani 1 1 d . . . . .
C13 C 0.1813(3) 0.31820(8) 0.1610(3) 0.0213(6) Uani 1 1 d . . . . .
H13 H 0.082270 0.333531 0.106793 0.026 Uiso 1 1 calc R . . . .
C9 C 0.4929(3) 0.31974(8) 0.2755(3) 0.0219(6) Uani 1 1 d . . . . .
C19 C 0.7678(3) 0.34482(8) 0.4579(3) 0.0228(6) Uani 1 1 d . . . . .
C14 C 0.6772(3) 0.34478(8) 0.3018(3) 0.0235(6) Uani 1 1 d . . . . .
C20 C 0.9549(3) 0.35975(8) 0.4711(3) 0.0258(6) Uani 1 1 d . . . . .
H20 H 1.018317 0.369899 0.382637 0.031 Uiso 1 1 calc R . . . .
C24 C 0.6744(4) 0.33187(8) 0.5902(3) 0.0248(6) Uani 1 1 d . . . . .
H24 H 0.546710 0.322637 0.583418 0.030 Uiso 1 1 calc R . . . .
C23 C 0.7676(4) 0.33246(8) 0.7315(3) 0.0275(6) Uani 1 1 d . . . . .
H23 H 0.703392 0.323724 0.821174 0.033 Uiso 1 1 calc R . . . .
C12 C 0.1593(4) 0.27237(8) 0.2097(3) 0.0271(6) Uani 1 1 d . . . . .
H12 H 0.045982 0.256202 0.186682 0.033 Uiso 1 1 calc R . . . .
C10 C 0.4672(4) 0.27415(8) 0.3262(3) 0.0274(6) Uani 1 1 d . . . . .
H10 H 0.563589 0.259261 0.384857 0.033 Uiso 1 1 calc R . . . .
C22 C 0.9546(4) 0.34580(8) 0.7422(3) 0.0282(6) Uani 1 1 d . . . . .
H22 H 1.018836 0.345346 0.838595 0.034 Uiso 1 1 calc R . . . .
C21 C 1.0476(4) 0.35979(9) 0.6121(3) 0.0294(6) Uani 1 1 d . . . . .
H21 H 1.174852 0.369379 0.619770 0.035 Uiso 1 1 calc R . . . .
C11 C 0.3022(4) 0.25024(8) 0.2918(3) 0.0297(7) Uani 1 1 d . . . . .
H11 H 0.287408 0.218882 0.324315 0.036 Uiso 1 1 calc R . . . .
C1 C 0.9520(4) 0.45404(10) -0.0146(4) 0.0404(8) Uani 1 1 d . . . . .
H1 H 0.918902 0.422094 -0.024481 0.048 Uiso 1 1 calc R . . . .
C0AA C 0.9517(4) 0.47463(11) 0.1286(4) 0.0415(8) Uani 1 1 d . . . . .
H0AA H 0.918325 0.457053 0.216047 0.050 Uiso 0.332(5) 1 calc R . P A 2
C1AA C 0.9993(4) 0.47885(12) -0.1431(4) 0.0422(8) Uani 1 1 d . . . . .
H1AA H 0.998316 0.464196 -0.240669 0.051 Uiso 0.168(5) 1 calc R . P A 1
O4 O 0.9961(7) 0.46369(17) -0.2872(6) 0.0304(19) Uani 0.332(5) 1 d . . P A -2
O6 O 0.9183(15) 0.4620(4) 0.2710(15) 0.040(4) Uani 0.168(5) 1 d . . P A -1
C2AA C 1.040(3) 0.4913(5) -0.420(2) 0.037(4) Uani 0.332(5) 1 d . . P A -2
H2AA H 1.046814 0.471038 -0.510022 0.056 Uiso 0.332(5) 1 calc GR . P A -2
H2AB H 1.161458 0.506753 -0.402872 0.056 Uiso 0.332(5) 1 calc GR . P A -2
H2AC H 0.942776 0.514887 -0.437142 0.056 Uiso 0.332(5) 1 calc GR . P A -2
C2AB C 0.947(6) 0.4876(12) 0.404(4) 0.049(9) Uani 0.168(5) 1 d . . P A -1
H2AD H 0.869590 0.515845 0.399850 0.074 Uiso 0.168(5) 1 calc GR . P A -1
H2AE H 1.079298 0.496381 0.414104 0.074 Uiso 0.168(5) 1 calc GR . P A -1
H2AF H 0.912043 0.468775 0.492629 0.074 Uiso 0.168(5) 1 calc GR . 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
O17 C7 1.222(3) . ?
O16 C2 1.223(3) . ?
O15 C14 1.229(3) . ?
N1 C7 1.411(3) . ?
N1 C2 1.407(3) . ?
N1 C8 1.455(3) . ?
C18 C18 1.419(4) 3_665 ?
C18 C6 1.412(3) . ?
C18 C3 1.415(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C5 C4 1.404(3) 3_665 ?
C6 C7 1.480(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C3 C2 1.490(3) . ?
C8 C13 1.378(3) . ?
C8 C9 1.402(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.392(3) . ?
C9 C14 1.513(3) . ?
C9 C10 1.394(3) . ?
C19 C14 1.495(3) . ?
C19 C20 1.405(3) . ?
C19 C24 1.398(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.389(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.388(4) . ?
C21 H21 0.9500 . ?
C11 H11 0.9500 . ?
C1 H1 0.9500 . ?
C1 C0AA 1.383(4) . ?
C1 C1AA 1.378(4) . ?
C0AA H0AA 0.9500 . ?
C0AA C1AA 1.385(4) 3_765 ?
C0AA O6 1.322(12) . ?
C1AA H1AA 0.9500 . ?
C1AA O4 1.331(6) . ?
O4 C2AA 1.446(19) . ?
O6 C2AB 1.39(3) . ?
C2AA H2AA 0.9800 . ?
C2AA H2AB 0.9800 . ?
C2AA H2AC 0.9800 . ?
C2AB H2AD 0.9800 . ?
C2AB H2AE 0.9800 . ?
C2AB H2AF 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
C7 N1 C8 116.21(18) . . ?
C2 N1 C7 125.09(18) . . ?
C2 N1 C8 118.13(18) . . ?
C6 C18 C18 119.7(3) . 3_665 ?
C6 C18 C3 121.39(19) . . ?
C3 C18 C18 118.9(2) . 3_665 ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . 3_665 ?
C4 C5 H5 119.9 3_665 . ?
C18 C6 C7 120.0(2) . . ?
C5 C6 C18 120.2(2) . . ?
C5 C6 C7 119.8(2) . . ?
C5 C4 H4 119.7 3_665 . ?
C3 C4 C5 120.5(2) . 3_665 ?
C3 C4 H4 119.7 . . ?
C18 C3 C2 119.96(19) . . ?
C4 C3 C18 120.5(2) . . ?
C4 C3 C2 119.5(2) . . ?
O17 C7 N1 120.3(2) . . ?
O17 C7 C6 122.7(2) . . ?
N1 C7 C6 117.00(19) . . ?
O16 C2 N1 120.6(2) . . ?
O16 C2 C3 122.8(2) . . ?
N1 C2 C3 116.51(19) . . ?
C13 C8 N1 119.7(2) . . ?
C13 C8 C9 120.9(2) . . ?
C9 C8 N1 119.4(2) . . ?
C8 C13 H13 120.1 . . ?
C8 C13 C12 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C9 C14 120.2(2) . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 C14 121.2(2) . . ?
C20 C19 C14 117.8(2) . . ?
C24 C19 C14 123.3(2) . . ?
C24 C19 C20 118.9(2) . . ?
O15 C14 C9 119.0(2) . . ?
O15 C14 C19 121.3(2) . . ?
C19 C14 C9 119.7(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C24 C23 H23 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C0AA C1 H1 119.3 . . ?
C1AA C1 H1 119.3 . . ?
C1AA C1 C0AA 121.4(3) . . ?
C1 C0AA H0AA 120.4 . . ?
C1 C0AA C1AA 119.3(3) . 3_765 ?
C1AA C0AA H0AA 120.4 3_765 . ?
O6 C0AA C1 137.5(6) . . ?
O6 C0AA C1AA 103.2(6) . 3_765 ?
C1 C1AA C0AA 119.3(3) . 3_765 ?
C1 C1AA H1AA 120.3 . . ?
C0AA C1AA H1AA 120.3 3_765 . ?
O4 C1AA C1 127.0(4) . . ?
C1AA O4 C2AA 125.5(7) . . ?
C0AA O6 C2AB 128.1(19) . . ?
O4 C2AA H2AA 109.5 . . ?
O4 C2AA H2AB 109.5 . . ?
O4 C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
O6 C2AB H2AD 109.5 . . ?
O6 C2AB H2AE 109.5 . . ?
O6 C2AB H2AF 109.5 . . ?
H2AD C2AB H2AE 109.5 . . ?
H2AD C2AB H2AF 109.5 . . ?
H2AE C2AB H2AF 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.094
_oxdiff_exptl_absorpt_empirical_full_min 0.934
####################################################################### 
# 
# 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_tsukiyama027
_database_code_depnum_ccdc_archive 'CCDC 1912447'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H26 N2 O4, 2(C6 H8 O)'
_chemical_formula_sum            'C52 H42 N2 O6'
_chemical_formula_weight         790.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.5245(6)
_cell_length_b                   12.4197(12)
_cell_length_c                   15.5190(16)
_cell_angle_alpha                71.896(9)
_cell_angle_beta                 84.174(8)
_cell_angle_gamma                85.859(8)
_cell_volume                     1005.93(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1413
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.1980
_cell_measurement_theta_min      2.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.1066
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10542
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   50.00    --   30.00  54.00-180.00  193
  2  ω    -74.00 119.00   1.00   50.00    --   30.00  54.00-180.00  193
  3  ω    -72.00 112.00   1.00   50.00    --   30.00  54.00  30.00  184
  4  ω      2.00  40.00   1.00   50.00    --   30.00  54.00 -60.00   38
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241262000
_diffrn_orient_matrix_UB_12      0.0286379000
_diffrn_orient_matrix_UB_13      -0.0470499000
_diffrn_orient_matrix_UB_21      0.0081772000
_diffrn_orient_matrix_UB_22      -0.0526764000
_diffrn_orient_matrix_UB_23      -0.0092188000
_diffrn_orient_matrix_UB_31      -0.1266398000
_diffrn_orient_matrix_UB_32      0.0046932000
_diffrn_orient_matrix_UB_33      -0.0054540000
_diffrn_oxdiff_ac3_digest_frames 
;
015f5fc1a165e94e5972edcd958c1f6b7800608dbe1
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f97d0cc7b92e4b16cbc408dca751b430266f
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2178
_reflns_number_total             4108
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.079
_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)+(0.0540P)²+0.5980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.2045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C2A(H2A), C3A(H3A)
2.c Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C6A(H6AA,H6AB,H6AC)
;
_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 0.5077(5) 0.85596(19) 0.40109(17) 0.0371(6) Uani 1 1 d . . . . .
O2 O 1.0801(5) 0.6269(2) 0.30376(18) 0.0463(7) Uani 1 1 d . . . . .
N1 N 0.7826(5) 0.7402(2) 0.34830(19) 0.0298(7) Uani 1 1 d . . . . .
C1 C 0.2297(6) 0.4669(3) 0.5847(2) 0.0275(8) Uani 1 1 d . . . . .
C2 C 0.1419(6) 0.5749(3) 0.5824(2) 0.0331(9) Uani 1 1 d . . . . .
H2 H 0.000653 0.584527 0.620130 0.040 Uiso 1 1 calc R . . . .
C3 C 0.2603(6) 0.6700(3) 0.5248(2) 0.0325(9) Uani 1 1 d . . . . .
H3 H 0.199052 0.743845 0.523888 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4648(6) 0.6576(3) 0.4695(2) 0.0290(8) Uani 1 1 d . . . . .
C5 C 0.5585(6) 0.5479(3) 0.4707(2) 0.0257(7) Uani 1 1 d . . . . .
C6 C 0.5815(6) 0.7591(3) 0.4058(2) 0.0277(8) Uani 1 1 d . . . . .
C7 C 0.8950(7) 0.6334(3) 0.3521(2) 0.0337(9) Uani 1 1 d . . . . .
C8 C 0.8694(6) 0.8391(3) 0.2743(2) 0.0312(8) Uani 1 1 d . . . . .
C9 C 0.7729(6) 0.8633(3) 0.1906(3) 0.0339(9) Uani 1 1 d . . . . .
C10 C 0.8573(7) 0.9598(3) 0.1220(3) 0.0385(9) Uani 1 1 d . . . . .
H10 H 0.796734 0.978813 0.063726 0.046 Uiso 1 1 calc R . . . .
C11 C 1.0253(7) 1.0276(3) 0.1367(3) 0.0419(10) Uani 1 1 d . . . . .
H11 H 1.077295 1.092782 0.089030 0.050 Uiso 1 1 calc R . . . .
C12 C 1.1185(7) 1.0012(3) 0.2205(3) 0.0394(9) Uani 1 1 d . . . . .
H12 H 1.236309 1.047174 0.230420 0.047 Uiso 1 1 calc R . . . .
C13 C 1.0386(6) 0.9071(3) 0.2896(3) 0.0341(9) Uani 1 1 d . . . . .
H13 H 1.099564 0.888979 0.347760 0.041 Uiso 1 1 calc R . . . .
C14 C 0.5850(7) 0.7919(3) 0.1719(3) 0.0367(9) Uani 1 1 d . . . . .
H14A H 0.558001 0.724817 0.226057 0.044 Uiso 1 1 calc R . . . .
H14B H 0.428949 0.836803 0.162980 0.044 Uiso 1 1 calc R . . . .
C15 C 0.6548(7) 0.7517(3) 0.0896(3) 0.0379(9) Uani 1 1 d . . . . .
C16 C 0.8725(8) 0.6902(3) 0.0827(3) 0.0467(10) Uani 1 1 d . . . . .
H16 H 0.981741 0.675946 0.128851 0.056 Uiso 1 1 calc R . . . .
C17 C 0.9323(10) 0.6494(4) 0.0092(4) 0.0674(15) Uani 1 1 d . . . . .
H17 H 1.082833 0.608603 0.004906 0.081 Uiso 1 1 calc R . . . .
C18 C 0.7745(12) 0.6679(5) -0.0571(4) 0.085(2) Uani 1 1 d . . . . .
H18 H 0.812589 0.637760 -0.106396 0.102 Uiso 1 1 calc R . . . .
C19 C 0.5609(11) 0.7302(5) -0.0518(3) 0.0778(17) Uani 1 1 d . . . . .
H19 H 0.453659 0.744828 -0.098622 0.093 Uiso 1 1 calc R . . . .
C20 C 0.4989(8) 0.7725(4) 0.0216(3) 0.0515(11) Uani 1 1 d . . . . .
H20 H 0.350406 0.815331 0.024600 0.062 Uiso 1 1 calc R . . . .
O1A O 0.6621(5) 0.7157(2) 0.66564(18) 0.0394(7) Uani 1 1 d . . . . .
C1A C 0.4693(7) 0.6675(3) 0.7270(3) 0.0409(10) Uani 1 1 d . . . . .
C2A C 0.3039(7) 0.7497(3) 0.7348(3) 0.0407(10) Uani 1 1 d . . . . .
H2A H 0.154486 0.739729 0.771953 0.049 Uiso 1 1 calc R . . . .
C3A C 0.3956(7) 0.8554(3) 0.6765(3) 0.0372(9) Uani 1 1 d . . . . .
H3A H 0.318778 0.928445 0.668246 0.045 Uiso 1 1 calc R . . . .
C4A C 0.6114(7) 0.8315(3) 0.6355(3) 0.0357(9) Uani 1 1 d . . . . .
C5A C 0.4920(8) 0.5423(3) 0.7703(3) 0.0546(12) Uani 1 1 d . . . . .
H5AA H 0.516512 0.504682 0.722996 0.082 Uiso 1 1 calc GR . . . .
H5AB H 0.343075 0.516196 0.809049 0.082 Uiso 1 1 calc GR . . . .
H5AC H 0.631535 0.523753 0.807442 0.082 Uiso 1 1 calc GR . . . .
C6A C 0.7926(7) 0.9017(3) 0.5691(3) 0.0419(10) Uani 1 1 d . . . . .
H6AA H 0.948924 0.892358 0.595824 0.063 Uiso 1 1 calc GR . . . .
H6AB H 0.736224 0.981557 0.553120 0.063 Uiso 1 1 calc GR . . . .
H6AC H 0.812741 0.877712 0.514178 0.063 Uiso 1 1 calc GR . . . .


_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 C6 1.225(4) . ?
O2 C7 1.218(4) . ?
N1 C6 1.406(4) . ?
N1 C7 1.410(4) . ?
N1 C8 1.467(4) . ?
C1 C2 1.385(5) . ?
C1 C5 1.416(4) 2_666 ?
C1 C7 1.489(5) 2_666 ?
C2 H2 0.9500 . ?
C2 C3 1.400(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(5) . ?
C4 C5 1.417(4) . ?
C4 C6 1.482(5) . ?
C5 C5 1.407(6) 2_666 ?
C8 C9 1.391(5) . ?
C8 C13 1.389(5) . ?
C9 C10 1.405(5) . ?
C9 C14 1.518(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(5) . ?
C15 C16 1.391(5) . ?
C15 C20 1.380(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.399(6) . ?
C20 H20 0.9500 . ?
O1A C1A 1.390(4) . ?
O1A C4A 1.384(4) . ?
C1A C2A 1.346(5) . ?
C1A C5A 1.492(5) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.436(5) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.351(5) . ?
C4A C6A 1.477(5) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 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
C6 N1 C7 125.3(3) . . ?
C6 N1 C8 116.8(3) . . ?
C7 N1 C8 117.7(3) . . ?
C2 C1 C5 120.1(3) . 2_666 ?
C2 C1 C7 119.6(3) . 2_666 ?
C5 C1 C7 120.3(3) 2_666 2_666 ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 C6 120.0(3) . . ?
C5 C4 C6 119.8(3) . . ?
C1 C5 C4 121.2(3) 2_666 . ?
C5 C5 C1 119.4(4) 2_666 2_666 ?
C5 C5 C4 119.4(4) 2_666 . ?
O1 C6 N1 120.2(3) . . ?
O1 C6 C4 122.8(3) . . ?
N1 C6 C4 117.0(3) . . ?
O2 C7 N1 120.2(3) . . ?
O2 C7 C1 123.7(3) . 2_666 ?
N1 C7 C1 116.1(3) . 2_666 ?
C9 C8 N1 118.2(3) . . ?
C13 C8 N1 119.9(3) . . ?
C13 C8 C9 121.9(3) . . ?
C8 C9 C10 116.5(3) . . ?
C8 C9 C14 123.3(3) . . ?
C10 C9 C14 120.2(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.0(4) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C9 C14 H14A 108.7 . . ?
C9 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C9 114.3(3) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C16 C15 C14 120.7(4) . . ?
C20 C15 C14 120.3(4) . . ?
C20 C15 C16 118.9(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(5) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 119.6(5) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C4A O1A C1A 107.3(3) . . ?
O1A C1A C5A 115.9(3) . . ?
C2A C1A O1A 109.2(3) . . ?
C2A C1A C5A 134.8(4) . . ?
C1A C2A H2A 126.4 . . ?
C1A C2A C3A 107.2(3) . . ?
C3A C2A H2A 126.4 . . ?
C2A C3A H3A 126.4 . . ?
C4A C3A C2A 107.2(3) . . ?
C4A C3A H3A 126.4 . . ?
O1A C4A C6A 117.2(3) . . ?
C3A C4A O1A 109.1(3) . . ?
C3A C4A C6A 133.6(3) . . ?
C1A C5A H5AA 109.5 . . ?
C1A C5A H5AB 109.5 . . ?
C1A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.121
_oxdiff_exptl_absorpt_empirical_full_min 0.938
####################################################################### 
# 
# 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_tsukiyama006
_database_code_depnum_ccdc_archive 'CCDC 1912446'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-02-22
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H13 N O2), C7 H8'
_chemical_formula_sum            'C47 H34 N2 O4'
_chemical_formula_weight         690.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     isocorrole
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   20.032(4)
_cell_length_b                   5.7620(12)
_cell_length_c                   30.235(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.56(2)
_cell_angle_gamma                90
_cell_volume                     3430.8(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1033
_cell_measurement_temperature    123
_cell_measurement_theta_max      21.0340
_cell_measurement_theta_min      2.7070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1634
_diffrn_reflns_av_unetI/netI     0.1756
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            22322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00 120.00  193
  2  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00  30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0246460000
_diffrn_orient_matrix_UB_12      0.0317503000
_diffrn_orient_matrix_UB_13      -0.0189859000
_diffrn_orient_matrix_UB_21      0.0261918000
_diffrn_orient_matrix_UB_22      0.0233416000
_diffrn_orient_matrix_UB_23      -0.0122672000
_diffrn_orient_matrix_UB_31      -0.0014175000
_diffrn_orient_matrix_UB_32      -0.1167277000
_diffrn_orient_matrix_UB_33      -0.0076447000
_diffrn_oxdiff_ac3_digest_frames 
;
01859feff9b55ff59d557fabe1c9e255ba003863a12
;
_diffrn_oxdiff_ac3_digest_hkl    
;
017f93b983faac6c332b7b0fc9cd0497d2dd23
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                2758
_reflns_number_total             7001
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         7001
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.2081
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      0.946
_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)+(0.0310P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1698
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C01D \\sim C01D \\sim C01D \\sim C014 \\sim C014 \\sim C014 \\sim C01B \\sim
C01B \\sim C01B \\sim C019 \\sim C019 \\sim C019 \\sim C018 \\sim C018 \\sim
C018 \\sim C018 \\sim C01C \\sim C01C \\sim C01C \\sim C01E \\sim C01E \\sim
C01E \\sim C2 \\sim C2 \\sim C2 \\sim C0AA \\sim C0AA \\sim C0AA \\sim C3 \\sim
C3 \\sim C3 \\sim C0 \\sim C0 \\sim C0 \\sim C0 \\sim C1AA \\sim C1AA \\sim
C1AA \\sim C1 \\sim C1 \\sim C2AA \\sim C2AA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(C00X) \\sim Ueq, Uanis(C01G) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C01D, C01D, C01D, C014, C014, C014, C01B, C01B, C01B, C019, C019, C019, C018,
 C018, C018, C018, C01C, C01C, C01C, C01E, C01E, C01E, C2, C2, C2, C0AA, C0AA,
 C0AA, C3, C3, C3, C0, C0, C0, C0, C1AA, C1AA, C1AA, C1, C1, C2AA, C2AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C01E)=Sof(H01J)=Sof(C2)=Sof(H2)=Sof(C0AA)=Sof(H0AA)=Sof(C3)=Sof(H3)=
 Sof(C0)=Sof(C1AA)=Sof(H1AA)=Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(1)
 Sof(C01D)=Sof(H01D)=Sof(C014)=Sof(H014)=Sof(C01B)=Sof(H01C)=Sof(C019)=
 Sof(H019)=Sof(C018)=Sof(C01C)=Sof(H01E)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=
 FVAR(1)
 Sof(H01B)=Sof(C3AA)=Sof(H3AA)=Sof(C01I)=Sof(H01I)=Sof(C4AA)=Sof(H4AA)=1-FVAR(2)
 Sof(H01A)=Sof(C01F)=Sof(H01F)=Sof(C01G)=Sof(H01G)=Sof(C01H)=Sof(H01H)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C00T(H00C,H00D)
5.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C015(H015), C016(H016), C017(H017),
 C01A(H01A), C01A(H01B), C01D(H01D), C014(H014), C01B(H01C), C019(H019),
 C01C(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01E(H01J), C2(H2), C0AA(H0AA),
  C3(H3), C1AA(H1AA), C3AA(H3AA), C01I(H01I), C4AA(H4AA)
5.c Fitted hexagon refined as free rotating group:
 C01D(C014,C01B,C019,C018,C01C), C01E(C2,C0AA,C3,C0,C1AA)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2AA(H2AA,H2AB,H2AC)
;
_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
O001 O 0.67014(12) 0.0505(5) 0.60342(9) 0.0351(7) Uani 1 1 d . . . . .
O002 O 1.18378(12) 0.0053(4) 0.59179(9) 0.0354(7) Uani 1 1 d . . . . .
O003 O 0.51069(14) -0.5083(5) 0.60007(9) 0.0442(8) Uani 1 1 d . . . . .
O004 O 1.01868(13) -0.5277(5) 0.59683(10) 0.0403(8) Uani 1 1 d . . . . .
N005 N 0.58539(15) -0.2088(5) 0.60450(10) 0.0284(8) Uani 1 1 d . . . . .
N006 N 1.09880(15) -0.2462(5) 0.59687(10) 0.0277(8) Uani 1 1 d . . . . .
C007 C 0.51779(18) -0.0451(7) 0.52082(12) 0.0249(9) Uani 1 1 d . . . . .
C008 C 1.01984(17) -0.0508(7) 0.51900(12) 0.0254(9) Uani 1 1 d . . . . .
C009 C 0.91490(18) -0.0405(7) 0.46402(13) 0.0270(10) Uani 1 1 d . . . . .
C00A C 0.99544(18) -0.2446(6) 0.53937(13) 0.0263(10) Uani 1 1 d . . . . .
C00B C 1.12684(19) -0.0650(7) 0.57615(13) 0.0284(10) Uani 1 1 d . . . . .
C00C C 0.61919(19) -0.2971(7) 0.64794(13) 0.0290(10) Uani 1 1 d . . . . .
C00D C 0.57802(18) 0.0650(7) 0.54163(12) 0.0260(9) Uani 1 1 d . . . . .
C00E C 0.93166(18) -0.3315(7) 0.52209(13) 0.0297(10) Uani 1 1 d . . . . .
H00E H 0.915021 -0.462707 0.535701 0.036 Uiso 1 1 calc R . . . .
C00F C 0.5276(2) -0.3329(8) 0.58348(14) 0.0334(11) Uani 1 1 d . . . . .
C00G C 1.13694(18) -0.3312(7) 0.63914(14) 0.0309(10) Uani 1 1 d . . . . .
C00H C 0.61519(18) -0.0256(7) 0.58490(13) 0.0276(10) Uani 1 1 d . . . . .
C00I C 0.89147(19) -0.2269(7) 0.48461(13) 0.0309(10) Uani 1 1 d . . . . .
H00I H 0.847380 -0.286257 0.473353 0.037 Uiso 1 1 calc R . . . .
C00J C 0.49179(18) -0.2359(7) 0.54010(13) 0.0279(10) Uani 1 1 d . . . . .
C00K C 0.66461(19) -0.4754(7) 0.64896(14) 0.0343(11) Uani 1 1 d . . . . .
H00K H 0.675789 -0.532386 0.621748 0.041 Uiso 1 1 calc R . . . .
C00L C 1.17916(18) -0.5183(7) 0.63916(15) 0.0334(10) Uani 1 1 d . . . . .
H00L H 1.183467 -0.591194 0.611640 0.040 Uiso 1 1 calc R . . . .
C00M C 0.47865(19) -0.0627(7) 0.67395(13) 0.0293(10) Uani 1 1 d . . . . .
C00N C 0.60200(19) -0.2029(7) 0.68670(14) 0.0315(10) Uani 1 1 d . . . . .
C00O C 1.12904(19) -0.2196(7) 0.67825(14) 0.0330(10) Uani 1 1 d . . . . .
C00P C 0.43321(19) -0.3418(7) 0.51883(13) 0.0366(11) Uani 1 1 d . . . . .
H00P H 0.416788 -0.475095 0.531917 0.044 Uiso 1 1 calc R . . . .
C00Q C 0.6940(2) -0.5717(8) 0.68946(14) 0.0398(11) Uani 1 1 d . . . . .
H00Q H 0.725462 -0.695899 0.690452 0.048 Uiso 1 1 calc R . . . .
C00R C 1.03657(19) -0.3545(7) 0.57928(14) 0.0322(10) Uani 1 1 d . . . . .
C00S C 1.08046(18) -0.0195(7) 0.67925(14) 0.0333(10) Uani 1 1 d . . . . .
H00A H 1.080316 0.078684 0.652361 0.040 Uiso 1 1 calc R . . . .
H00B H 1.096957 0.076757 0.706154 0.040 Uiso 1 1 calc R . . . .
C00T C 0.55337(18) -0.0008(7) 0.68573(14) 0.0359(11) Uani 1 1 d . . . . .
H00C H 0.563582 0.114358 0.663599 0.043 Uiso 1 1 calc R . . . .
H00D H 0.561943 0.074641 0.715649 0.043 Uiso 1 1 calc R . . . .
C00U C 0.39756(19) -0.2552(7) 0.47813(13) 0.0331(11) Uani 1 1 d . . . . .
H00U H 0.356492 -0.327319 0.464045 0.040 Uiso 1 1 calc R . . . .
C00V C 0.3404(2) -0.1641(8) 0.65434(14) 0.0388(11) Uani 1 1 d . . . . .
H00V H 0.293219 -0.198589 0.647643 0.047 Uiso 1 1 calc R . . . .
C00W C 1.1676(2) -0.3030(8) 0.71834(15) 0.0422(12) Uani 1 1 d . . . . .
H00W H 1.164549 -0.228188 0.745897 0.051 Uiso 1 1 calc R . . . .
C00X C 1.0082(2) -0.0971(8) 0.68022(14) 0.0371(11) Uani 1 1 d . U . . .
C00Y C 1.2101(2) -0.4923(8) 0.71865(15) 0.0437(12) Uani 1 1 d . . . . .
H00Y H 1.235667 -0.546893 0.746302 0.052 Uiso 1 1 calc R . . . .
C00Z C 1.2155(2) -0.6007(8) 0.67945(15) 0.0401(12) Uani 1 1 d . . . . .
H00Z H 1.244072 -0.732415 0.679761 0.048 Uiso 1 1 calc R . . . .
C010 C 0.6774(2) -0.4863(8) 0.72856(15) 0.0423(12) Uani 1 1 d . . . . .
H010 H 0.696997 -0.553519 0.756642 0.051 Uiso 1 1 calc R . . . .
C011 C 0.6323(2) -0.3029(8) 0.72723(14) 0.0413(12) Uani 1 1 d . . . . .
H011 H 0.621893 -0.244474 0.754556 0.050 Uiso 1 1 calc R . . . .
C012 C 0.4334(2) 0.0911(8) 0.65024(15) 0.0482(13) Uani 1 1 d . . . . .
H012 H 0.449303 0.234152 0.640497 0.058 Uiso 1 1 calc R . . . .
C013 C 0.3643(2) 0.0399(9) 0.64030(15) 0.0512(13) Uani 1 1 d . . . . .
H013 H 0.333588 0.147490 0.623653 0.061 Uiso 1 1 calc R . . . .
C015 C 0.4539(2) -0.2682(8) 0.68776(16) 0.0535(14) Uani 1 1 d . . . . .
H015 H 0.484337 -0.377567 0.704109 0.064 Uiso 1 1 calc R . . . .
C016 C 0.3848(2) -0.3171(8) 0.67799(17) 0.0545(14) Uani 1 1 d . . . . .
H016 H 0.368438 -0.459028 0.687945 0.065 Uiso 1 1 calc R . . . .
C017 C 0.9934(2) -0.2994(9) 0.69915(15) 0.0527(14) Uani 1 1 d . . . . .
H017 H 1.029369 -0.402372 0.710891 0.063 Uiso 1 1 calc R . . . .
C01A C 0.9272(3) -0.3605(10) 0.70189(16) 0.0609(16) Uani 1 1 d . . . . .
H01A H 0.917809 -0.517085 0.708489 0.073 Uiso 0.44(2) 1 calc R . P A 1
H01B H 0.917540 -0.486228 0.720060 0.073 Uiso 0.56(2) 1 calc R . P A 2
C01D C 0.7508(5) 0.3365(13) 0.4756(4) 0.034(3) Uani 0.496(7) 1 d . U P B 2
H01D H 0.756117 0.203152 0.458048 0.040 Uiso 0.496(7) 1 calc R . P B 2
C014 C 0.7123(4) 0.523(2) 0.45607(19) 0.033(3) Uani 0.496(7) 1 d G U P B 2
H014 H 0.691317 0.517426 0.425251 0.039 Uiso 0.496(7) 1 calc R . P B 2
C01B C 0.7045(6) 0.7183(16) 0.4817(4) 0.031(3) Uani 0.496(7) 1 d G U P B 2
H01C H 0.678236 0.845925 0.468361 0.038 Uiso 0.496(7) 1 calc R . P B 2
C019 C 0.7353(7) 0.7268(17) 0.5268(4) 0.032(3) Uani 0.496(7) 1 d G U P B 2
H019 H 0.729957 0.860155 0.544268 0.038 Uiso 0.496(7) 1 calc R . P B 2
C018 C 0.7738(6) 0.540(2) 0.5462(2) 0.033(3) Uani 0.496(7) 1 d G U P B 2
C01C C 0.7815(4) 0.3450(14) 0.5206(4) 0.039(3) Uani 0.496(7) 1 d G U P B 2
H01E H 0.807838 0.217382 0.533957 0.047 Uiso 0.496(7) 1 calc R . P B 2
C01F C 0.8795(12) -0.218(5) 0.6960(7) 0.044(5) Uani 0.44(2) 1 d . . P A 1
H01F H 0.835471 -0.259092 0.700825 0.052 Uiso 0.44(2) 1 calc R . P A 1
C01G C 0.9590(7) 0.059(3) 0.6760(6) 0.033(4) Uani 0.44(2) 1 d . U P A 1
H01G H 0.967977 0.214965 0.668442 0.040 Uiso 0.44(2) 1 calc R . P A 1
C01H C 0.8931(6) -0.004(3) 0.6826(6) 0.041(4) Uani 0.44(2) 1 d . . P A 1
H01H H 0.857712 0.108366 0.677460 0.049 Uiso 0.44(2) 1 calc R . P A 1
C01E C 0.7341(5) 0.436(2) 0.4633(2) 0.034(3) Uani 0.504(7) 1 d . U P B 1
H01J H 0.724656 0.370005 0.433958 0.041 Uiso 0.504(7) 1 calc R . P B 1
C2 C 0.7097(6) 0.655(2) 0.4708(3) 0.034(3) Uani 0.504(7) 1 d G U P B 1
H2 H 0.683652 0.739764 0.446612 0.040 Uiso 0.504(7) 1 calc R . P B 1
C0AA C 0.7235(7) 0.7517(14) 0.5136(4) 0.033(3) Uani 0.504(7) 1 d G U P B 1
H0AA H 0.706888 0.901834 0.518766 0.040 Uiso 0.504(7) 1 calc R . P B 1
C3 C 0.7617(7) 0.628(2) 0.5490(2) 0.033(3) Uani 0.504(7) 1 d G U P B 1
H3 H 0.771127 0.694147 0.578265 0.039 Uiso 0.504(7) 1 calc R . P B 1
C0 C 0.7861(4) 0.4087(18) 0.5415(3) 0.031(3) Uani 0.504(7) 1 d G U P B 1
C1AA C 0.7722(5) 0.3124(10) 0.4986(4) 0.033(3) Uani 0.504(7) 1 d G U P B 1
H1AA H 0.788897 0.162314 0.493459 0.040 Uiso 0.504(7) 1 calc R . P B 1
C1 C 0.8071(4) 0.5595(19) 0.5945(3) 0.056(3) Uani 0.496(7) 1 d . U P B 2
H1A H 0.856534 0.554431 0.596857 0.083 Uiso 0.496(7) 1 calc GR . P B 2
H1B H 0.792557 0.430121 0.611535 0.083 Uiso 0.496(7) 1 calc GR . P B 2
H1C H 0.794121 0.706616 0.606824 0.083 Uiso 0.496(7) 1 calc GR . P B 2
C2AA C 0.8273(4) 0.2683(19) 0.5800(3) 0.075(4) Uani 0.504(7) 1 d . U P B 1
H2AA H 0.857727 0.372441 0.599987 0.112 Uiso 0.504(7) 1 calc GR . P B 1
H2AB H 0.854169 0.150759 0.567752 0.112 Uiso 0.504(7) 1 calc GR . P B 1
H2AC H 0.796364 0.191937 0.597096 0.112 Uiso 0.504(7) 1 calc GR . P B 1
C3AA C 0.9539(6) 0.029(2) 0.6514(8) 0.055(4) Uani 0.56(2) 1 d . . P A 2
H3AA H 0.964294 0.154835 0.633528 0.066 Uiso 0.56(2) 1 calc R . P A 2
C01I C 0.8878(5) -0.034(2) 0.6504(9) 0.071(6) Uani 0.56(2) 1 d . . P A 2
H01I H 0.851940 0.049907 0.632436 0.085 Uiso 0.56(2) 1 calc R . P A 2
C4AA C 0.8734(11) -0.223(4) 0.6756(8) 0.068(6) Uani 0.56(2) 1 d . . P A 2
H4AA H 0.827382 -0.262377 0.675691 0.081 Uiso 0.56(2) 1 calc R . 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
O001 C00H 1.221(4) . ?
O002 C00B 1.221(4) . ?
O003 C00F 1.205(4) . ?
O004 C00R 1.215(4) . ?
N005 C00C 1.454(4) . ?
N005 C00F 1.409(5) . ?
N005 C00H 1.397(5) . ?
N006 C00B 1.388(5) . ?
N006 C00G 1.449(5) . ?
N006 C00R 1.408(4) . ?
C007 C007 1.426(7) 3_656 ?
C007 C00D 1.406(5) . ?
C007 C00J 1.390(5) . ?
C008 C008 1.400(7) 3_756 ?
C008 C009 1.416(5) 3_756 ?
C008 C00A 1.405(5) . ?
C009 C00B 1.474(5) 3_756 ?
C009 C00I 1.367(5) . ?
C00A C00E 1.383(5) . ?
C00A C00R 1.474(5) . ?
C00C C00K 1.369(5) . ?
C00C C00N 1.391(5) . ?
C00D C00H 1.477(5) . ?
C00D C00U 1.380(5) 3_656 ?
C00E H00E 0.9500 . ?
C00E C00I 1.400(5) . ?
C00F C00J 1.484(5) . ?
C00G C00L 1.370(5) . ?
C00G C00O 1.380(5) . ?
C00I H00I 0.9500 . ?
C00J C00P 1.373(5) . ?
C00K H00K 0.9500 . ?
C00K C00Q 1.375(5) . ?
C00L H00L 0.9500 . ?
C00L C00Z 1.383(5) . ?
C00M C00T 1.516(5) . ?
C00M C012 1.373(5) . ?
C00M C015 1.378(5) . ?
C00N C00T 1.515(5) . ?
C00N C011 1.389(5) . ?
C00O C00S 1.513(5) . ?
C00O C00W 1.398(5) . ?
C00P H00P 0.9500 . ?
C00P C00U 1.397(5) . ?
C00Q H00Q 0.9500 . ?
C00Q C010 1.376(6) . ?
C00S H00A 0.9900 . ?
C00S H00B 0.9900 . ?
C00S C00X 1.520(5) . ?
C00T H00C 0.9900 . ?
C00T H00D 0.9900 . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C013 1.366(6) . ?
C00V C016 1.359(5) . ?
C00W H00W 0.9500 . ?
C00W C00Y 1.383(5) . ?
C00X C017 1.355(6) . ?
C00X C01G 1.324(15) . ?
C00X C3AA 1.457(14) . ?
C00Y H00Y 0.9500 . ?
C00Y C00Z 1.361(6) . ?
C00Z H00Z 0.9500 . ?
C010 H010 0.9500 . ?
C010 C011 1.387(5) . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C012 C013 1.393(5) . ?
C013 H013 0.9500 . ?
C015 H015 0.9500 . ?
C015 C016 1.391(5) . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?
C017 C01A 1.391(6) . ?
C01A H01A 0.9500 . ?
C01A H01B 0.9500 . ?
C01A C01F 1.25(3) . ?
C01A C4AA 1.45(2) . ?
C01D H01D 0.9500 . ?
C01D C014 1.3900 . ?
C01D C01C 1.3900 . ?
C014 H014 0.9500 . ?
C014 C01B 1.3900 . ?
C01B H01C 0.9500 . ?
C01B C019 1.3900 . ?
C019 H019 0.9500 . ?
C019 C018 1.3900 . ?
C018 C01C 1.3900 . ?
C018 C1 1.494(10) . ?
C01C H01E 0.9500 . ?
C01F H01F 0.9500 . ?
C01F C01H 1.34(3) . ?
C01G H01G 0.9500 . ?
C01G C01H 1.420(18) . ?
C01H H01H 0.9500 . ?
C01E H01J 0.9500 . ?
C01E C2 1.3900 . ?
C01E C1AA 1.3900 . ?
C2 H2 0.9500 . ?
C2 C0AA 1.3900 . ?
C0AA H0AA 0.9500 . ?
C0AA C3 1.3900 . ?
C3 H3 0.9500 . ?
C3 C0 1.3900 . ?
C0 C1AA 1.3900 . ?
C0 C2AA 1.531(9) . ?
C1AA H1AA 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2AA H2AA 0.9800 . ?
C2AA H2AB 0.9800 . ?
C2AA H2AC 0.9800 . ?
C3AA H3AA 0.9500 . ?
C3AA C01I 1.369(15) . ?
C01I H01I 0.9500 . ?
C01I C4AA 1.39(3) . ?
C4AA H4AA 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
C00F N005 C00C 116.0(3) . . ?
C00H N005 C00C 118.9(3) . . ?
C00H N005 C00F 124.9(3) . . ?
C00B N006 C00G 117.4(3) . . ?
C00B N006 C00R 124.5(3) . . ?
C00R N006 C00G 118.1(3) . . ?
C00D C007 C007 118.7(4) . 3_656 ?
C00J C007 C007 119.6(4) . 3_656 ?
C00J C007 C00D 121.8(3) . . ?
C008 C008 C009 119.3(4) 3_756 3_756 ?
C008 C008 C00A 120.1(4) 3_756 . ?
C00A C008 C009 120.6(3) . 3_756 ?
C008 C009 C00B 119.5(3) 3_756 3_756 ?
C00I C009 C008 119.9(3) . 3_756 ?
C00I C009 C00B 120.6(3) . 3_756 ?
C008 C00A C00R 120.9(3) . . ?
C00E C00A C008 119.6(3) . . ?
C00E C00A C00R 119.5(4) . . ?
O002 C00B N006 120.1(4) . . ?
O002 C00B C009 122.1(4) . 3_756 ?
N006 C00B C009 117.8(3) . 3_756 ?
C00K C00C N005 118.7(4) . . ?
C00K C00C C00N 122.7(4) . . ?
C00N C00C N005 118.6(4) . . ?
C007 C00D C00H 119.3(3) . . ?
C00U C00D C007 120.5(3) 3_656 . ?
C00U C00D C00H 120.2(3) 3_656 . ?
C00A C00E H00E 119.9 . . ?
C00A C00E C00I 120.3(4) . . ?
C00I C00E H00E 119.9 . . ?
O003 C00F N005 120.6(4) . . ?
O003 C00F C00J 123.8(4) . . ?
N005 C00F C00J 115.6(4) . . ?
C00L C00G N006 119.5(4) . . ?
C00L C00G C00O 122.3(4) . . ?
C00O C00G N006 118.3(4) . . ?
O001 C00H N005 119.7(4) . . ?
O001 C00H C00D 123.0(4) . . ?
N005 C00H C00D 117.2(3) . . ?
C009 C00I C00E 120.8(4) . . ?
C009 C00I H00I 119.6 . . ?
C00E C00I H00I 119.6 . . ?
C007 C00J C00F 120.7(3) . . ?
C00P C00J C007 120.6(4) . . ?
C00P C00J C00F 118.7(4) . . ?
C00C C00K H00K 120.1 . . ?
C00C C00K C00Q 119.8(4) . . ?
C00Q C00K H00K 120.1 . . ?
C00G C00L H00L 120.2 . . ?
C00G C00L C00Z 119.7(4) . . ?
C00Z C00L H00L 120.2 . . ?
C012 C00M C00T 120.0(4) . . ?
C012 C00M C015 118.2(4) . . ?
C015 C00M C00T 121.7(4) . . ?
C00C C00N C00T 122.8(4) . . ?
C011 C00N C00C 116.5(4) . . ?
C011 C00N C00T 120.8(4) . . ?
C00G C00O C00S 123.2(4) . . ?
C00G C00O C00W 116.8(4) . . ?
C00W C00O C00S 120.0(4) . . ?
C00J C00P H00P 119.7 . . ?
C00J C00P C00U 120.6(4) . . ?
C00U C00P H00P 119.7 . . ?
C00K C00Q H00Q 120.4 . . ?
C00K C00Q C010 119.3(4) . . ?
C010 C00Q H00Q 120.4 . . ?
O004 C00R N006 120.7(4) . . ?
O004 C00R C00A 123.0(4) . . ?
N006 C00R C00A 116.2(4) . . ?
C00O C00S H00A 108.9 . . ?
C00O C00S H00B 108.9 . . ?
C00O C00S C00X 113.2(3) . . ?
H00A C00S H00B 107.7 . . ?
C00X C00S H00A 108.9 . . ?
C00X C00S H00B 108.9 . . ?
C00M C00T H00C 108.4 . . ?
C00M C00T H00D 108.4 . . ?
C00N C00T C00M 115.3(3) . . ?
C00N C00T H00C 108.4 . . ?
C00N C00T H00D 108.4 . . ?
H00C C00T H00D 107.5 . . ?
C00D C00U C00P 120.0(4) 3_656 . ?
C00D C00U H00U 120.0 3_656 . ?
C00P C00U H00U 120.0 . . ?
C013 C00V H00V 120.4 . . ?
C016 C00V H00V 120.4 . . ?
C016 C00V C013 119.3(4) . . ?
C00O C00W H00W 119.4 . . ?
C00Y C00W C00O 121.3(4) . . ?
C00Y C00W H00W 119.4 . . ?
C017 C00X C00S 122.9(4) . . ?
C017 C00X C3AA 119.0(6) . . ?
C01G C00X C00S 119.5(8) . . ?
C01G C00X C017 114.2(8) . . ?
C3AA C00X C00S 116.8(7) . . ?
C00W C00Y H00Y 119.9 . . ?
C00Z C00Y C00W 120.2(4) . . ?
C00Z C00Y H00Y 119.9 . . ?
C00L C00Z H00Z 120.1 . . ?
C00Y C00Z C00L 119.8(4) . . ?
C00Y C00Z H00Z 120.1 . . ?
C00Q C010 H010 119.8 . . ?
C00Q C010 C011 120.4(4) . . ?
C011 C010 H010 119.8 . . ?
C00N C011 H011 119.4 . . ?
C010 C011 C00N 121.3(4) . . ?
C010 C011 H011 119.4 . . ?
C00M C012 H012 119.6 . . ?
C00M C012 C013 120.7(4) . . ?
C013 C012 H012 119.6 . . ?
C00V C013 C012 120.4(4) . . ?
C00V C013 H013 119.8 . . ?
C012 C013 H013 119.8 . . ?
C00M C015 H015 119.7 . . ?
C00M C015 C016 120.6(4) . . ?
C016 C015 H015 119.7 . . ?
C00V C016 C015 120.7(4) . . ?
C00V C016 H016 119.6 . . ?
C015 C016 H016 119.6 . . ?
C00X C017 H017 119.1 . . ?
C00X C017 C01A 121.9(5) . . ?
C01A C017 H017 119.1 . . ?
C017 C01A H01A 118.7 . . ?
C017 C01A H01B 121.6 . . ?
C017 C01A C4AA 116.7(10) . . ?
C01F C01A C017 122.6(15) . . ?
C01F C01A H01A 118.7 . . ?
C4AA C01A H01B 121.6 . . ?
C014 C01D H01D 120.0 . . ?
C014 C01D C01C 120.0 . . ?
C01C C01D H01D 120.0 . . ?
C01D C014 H014 120.0 . . ?
C01B C014 C01D 120.0 . . ?
C01B C014 H014 120.0 . . ?
C014 C01B H01C 120.0 . . ?
C014 C01B C019 120.0 . . ?
C019 C01B H01C 120.0 . . ?
C01B C019 H019 120.0 . . ?
C01B C019 C018 120.0 . . ?
C018 C019 H019 120.0 . . ?
C019 C018 C1 118.0(11) . . ?
C01C C018 C019 120.0 . . ?
C01C C018 C1 121.9(11) . . ?
C01D C01C H01E 120.0 . . ?
C018 C01C C01D 120.0 . . ?
C018 C01C H01E 120.0 . . ?
C01A C01F H01F 121.4 . . ?
C01A C01F C01H 117(2) . . ?
C01H C01F H01F 121.4 . . ?
C00X C01G H01G 119.8 . . ?
C00X C01G C01H 120.5(13) . . ?
C01H C01G H01G 119.8 . . ?
C01F C01H C01G 121.6(15) . . ?
C01F C01H H01H 119.2 . . ?
C01G C01H H01H 119.2 . . ?
C2 C01E H01J 120.0 . . ?
C2 C01E C1AA 120.0 . . ?
C1AA C01E H01J 120.0 . . ?
C01E C2 H2 120.0 . . ?
C01E C2 C0AA 120.0 . . ?
C0AA C2 H2 120.0 . . ?
C2 C0AA H0AA 120.0 . . ?
C3 C0AA C2 120.0 . . ?
C3 C0AA H0AA 120.0 . . ?
C0AA C3 H3 120.0 . . ?
C0AA C3 C0 120.0 . . ?
C0 C3 H3 120.0 . . ?
C3 C0 C1AA 120.0 . . ?
C3 C0 C2AA 120.9(11) . . ?
C1AA C0 C2AA 119.1(11) . . ?
C01E C1AA H1AA 120.0 . . ?
C0 C1AA C01E 120.0 . . ?
C0 C1AA H1AA 120.0 . . ?
C018 C1 H1A 109.5 . . ?
C018 C1 H1B 109.5 . . ?
C018 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C0 C2AA H2AA 109.5 . . ?
C0 C2AA H2AB 109.5 . . ?
C0 C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
C00X C3AA H3AA 120.2 . . ?
C01I C3AA C00X 119.6(11) . . ?
C01I C3AA H3AA 120.2 . . ?
C3AA C01I H01I 120.2 . . ?
C3AA C01I C4AA 119.6(13) . . ?
C4AA C01I H01I 120.2 . . ?
C01A C4AA H4AA 119.3 . . ?
C01I C4AA C01A 121.4(16) . . ?
C01I C4AA H4AA 119.3 . . ?

_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 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.724
