# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_211030nakagawa
_database_code_depnum_ccdc_archive 'CCDC 2346717'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-10-17 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-05-14
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2024.05.14 svn.rc2abdb5a for OlexSys, GUI svn.r6697)
;
_chemical_name_common            opp-dioxadiaza[8]circulene
_chemical_name_systematic        dioxadiaza[8]circulene
_chemical_formula_moiety         'C24 H10 N2 O2'
_chemical_formula_sum            'C24 H10 N2 O2'
_chemical_formula_weight         358.359
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.0418(4)
_cell_length_b                   14.1923(4)
_cell_length_c                   10.9180(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.166(3)
_cell_angle_gamma                90
_cell_volume                     1494.47(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5293
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      73.7990
_cell_measurement_theta_min      3.10000
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prism
_exptl_crystal_F_000             738.524
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.9902
_diffrn_reflns_Laue_measured_fraction_max 0.9902
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10108
_diffrn_reflns_point_group_measured_fraction_full 0.9902
_diffrn_reflns_point_group_measured_fraction_max 0.9902
_diffrn_reflns_theta_full        66.9844
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         4.58
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9902
_diffrn_measured_fraction_theta_max 0.9902
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2252
_reflns_number_total             2631
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_refine_diff_density_max         0.2453
_refine_diff_density_min         -0.1724
_refine_diff_density_rms         0.0491
_refine_ls_d_res_high            0.8376
_refine_ls_d_res_low             9.6447
_refine_ls_goodness_of_fit_ref   1.1139
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     343
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.1132
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.1915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1011
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 N1, H9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-05-14_18-20-44
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.77254(14) 0.46456(9) 0.41234(13) 0.0301(3) Uani 1.000000 . .
C2 C 0.81207(17) 0.54017(10) 0.34787(14) 0.0339(3) Uani 1.000000 . .
H1 H 0.926(2) 0.5544(13) 0.3672(19) 0.057(5) Uani 1.000000 . .
C3 C 0.70893(16) 0.59419(10) 0.26691(14) 0.0340(3) Uani 1.000000 . .
H2 H 0.7321(17) 0.6531(13) 0.2149(18) 0.056(5) Uani 1.000000 . .
C4 C 0.56872(15) 0.57112(9) 0.25299(13) 0.0301(3) Uani 1.000000 . .
C5 C 0.52989(14) 0.49542(9) 0.31964(12) 0.0264(3) Uani 1.000000 . .
C6 C 0.38186(14) 0.49230(9) 0.28293(12) 0.0263(3) Uani 1.000000 . .
C7 C 0.33465(15) 0.56623(9) 0.19426(13) 0.0307(3) Uani 1.000000 . .
C8 C 0.19321(16) 0.58220(10) 0.13646(14) 0.0351(3) Uani 1.000000 . .
H3 H 0.160(2) 0.6378(13) 0.0635(17) 0.062(6) Uani 1.000000 . .
C9 C 0.09517(17) 0.52548(10) 0.16940(14) 0.0344(3) Uani 1.000000 . .
H4 H -0.0134(18) 0.5345(13) 0.1261(17) 0.049(5) Uani 1.000000 . .
C10 C 0.14283(14) 0.45336(10) 0.25798(13) 0.0306(3) Uani 1.000000 . .
C11 C 0.28304(14) 0.43478(9) 0.31450(12) 0.0269(3) Uani 1.000000 . .
C12 C 0.28732(14) 0.35316(9) 0.39364(12) 0.0272(3) Uani 1.000000 . .
C13 C 0.14988(14) 0.32879(10) 0.37986(13) 0.0309(3) Uani 1.000000 . .
C14 C 0.10971(17) 0.25241(10) 0.44204(14) 0.0354(4) Uani 1.000000 . .
H5 H -0.0020(19) 0.2377(14) 0.4273(17) 0.053(5) Uani 1.000000 . .
C15 C 0.21308(17) 0.19823(11) 0.52239(14) 0.0363(4) Uani 1.000000 . .
H6 H 0.1882(19) 0.1392(14) 0.5708(19) 0.061(5) Uani 1.000000 . .
C16 C 0.35298(15) 0.22164(10) 0.53828(12) 0.0319(3) Uani 1.000000 . .
C17 C 0.39220(15) 0.29877(9) 0.47437(12) 0.0279(3) Uani 1.000000 . .
C18 C 0.54038(14) 0.30147(9) 0.51134(12) 0.0277(3) Uani 1.000000 . .
C19 C 0.58791(15) 0.22637(9) 0.59726(12) 0.0313(3) Uani 1.000000 . .
C20 C 0.73000(16) 0.20795(10) 0.65111(14) 0.0349(3) Uani 1.000000 . .
H7 H 0.7617(18) 0.1513(14) 0.7147(17) 0.056(5) Uani 1.000000 . .
C21 C 0.82708(17) 0.26579(11) 0.61920(14) 0.0346(3) Uani 1.000000 . .
H8 H 0.935(2) 0.2547(13) 0.6578(17) 0.056(5) Uani 1.000000 . .
C22 C 0.77930(14) 0.34031(9) 0.53444(12) 0.0304(3) Uani 1.000000 . .
C23 C 0.63914(14) 0.35950(9) 0.48005(12) 0.0271(3) Uani 1.000000 . .
C24 C 0.63459(14) 0.44088(9) 0.40065(12) 0.0262(3) Uani 1.000000 . .
N1 N 0.44961(13) 0.61330(8) 0.17826(11) 0.0337(3) Uani 1.000000 . U
H9 H 0.449(2) 0.6742(14) 0.130(2) 0.065(6) Uani 1.000000 . U
N2 N 0.47251(14) 0.17878(9) 0.61287(12) 0.0352(3) Uani 1.000000 . .
H10 H 0.473(2) 0.1210(14) 0.672(2) 0.067(7) Uani 1.000000 . .
O1 O 0.05951(10) 0.38955(7) 0.29738(9) 0.0332(3) Uani 1.000000 . .
O2 O 0.86231(10) 0.40374(7) 0.49420(9) 0.0328(3) Uani 1.000000 . .


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
C1 C2 1.400(2) . ?
C1 C24 1.3964(19) . ?
C1 O2 1.3812(17) . ?
C2 H1 1.121(18) . ?
C2 C3 1.390(2) . ?
C3 H2 1.073(16) . ?
C3 C4 1.412(2) . ?
C4 C5 1.4121(18) . ?
C4 N1 1.3825(18) . ?
C5 C6 1.4284(19) . ?
C5 C24 1.4032(18) . ?
C6 C7 1.4168(18) . ?
C6 C11 1.4002(19) . ?
C7 C8 1.403(2) . ?
C7 N1 1.3862(19) . ?
C8 H3 1.105(16) . ?
C8 C9 1.394(2) . ?
C9 H4 1.068(17) . ?
C9 C10 1.398(2) . ?
C10 C11 1.3960(19) . ?
C10 O1 1.3805(17) . ?
C11 C12 1.4385(18) . ?
C12 C13 1.3899(19) . ?
C12 C17 1.4018(19) . ?
C13 C14 1.397(2) . ?
C13 O1 1.3866(17) . ?
C14 H5 1.108(18) . ?
C14 C15 1.390(2) . ?
C15 H6 1.058(19) . ?
C15 C16 1.407(2) . ?
C16 C17 1.4119(18) . ?
C16 N2 1.3891(19) . ?
C17 C18 1.4297(19) . ?
C18 C19 1.4123(19) . ?
C18 C23 1.4025(19) . ?
C19 C20 1.408(2) . ?
C19 N2 1.3922(19) . ?
C20 H7 1.052(18) . ?
C20 C21 1.391(2) . ?
C21 H8 1.064(19) . ?
C21 C22 1.399(2) . ?
C22 C23 1.3937(19) . ?
C22 O2 1.3792(17) . ?
C23 C24 1.4372(18) . ?
N1 H9 1.012(18) . ?
N2 H10 1.05(2) . ?

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
C24 C1 C2 123.47(13) . . ?
O2 C1 C2 125.38(13) . . ?
O2 C1 C24 111.15(12) . . ?
H1 C2 C1 117.4(10) . . ?
C3 C2 C1 118.50(14) . . ?
C3 C2 H1 124.0(10) . . ?
H2 C3 C2 122.3(9) . . ?
C4 C3 C2 119.00(14) . . ?
C4 C3 H2 118.7(9) . . ?
C5 C4 C3 122.08(13) . . ?
N1 C4 C3 129.50(13) . . ?
N1 C4 C5 108.42(12) . . ?
C6 C5 C4 107.10(11) . . ?
C24 C5 C4 118.59(13) . . ?
C24 C5 C6 134.29(12) . . ?
C7 C6 C5 107.03(11) . . ?
C11 C6 C5 134.62(12) . . ?
C11 C6 C7 118.35(12) . . ?
C8 C7 C6 122.09(13) . . ?
N1 C7 C6 108.13(12) . . ?
N1 C7 C8 129.77(13) . . ?
H3 C8 C7 120.1(10) . . ?
C9 C8 C7 119.33(14) . . ?
C9 C8 H3 120.5(10) . . ?
H4 C9 C8 121.6(9) . . ?
C10 C9 C8 118.09(14) . . ?
C10 C9 H4 120.3(9) . . ?
C11 C10 C9 123.57(14) . . ?
O1 C10 C9 125.14(13) . . ?
O1 C10 C11 111.25(12) . . ?
C10 C11 C6 118.53(12) . . ?
C12 C11 C6 135.45(12) . . ?
C12 C11 C10 105.99(12) . . ?
C13 C12 C11 105.82(12) . . ?
C17 C12 C11 135.45(13) . . ?
C17 C12 C13 118.72(12) . . ?
C14 C13 C12 123.57(14) . . ?
O1 C13 C12 111.47(11) . . ?
O1 C13 C14 124.95(13) . . ?
H5 C14 C13 119.6(10) . . ?
C15 C14 C13 118.05(15) . . ?
C15 C14 H5 122.4(10) . . ?
H6 C15 C14 121.0(10) . . ?
C16 C15 C14 119.47(14) . . ?
C16 C15 H6 119.5(10) . . ?
C17 C16 C15 121.92(13) . . ?
N2 C16 C15 129.73(13) . . ?
N2 C16 C17 108.35(13) . . ?
C16 C17 C12 118.27(13) . . ?
C18 C17 C12 134.70(12) . . ?
C18 C17 C16 107.03(12) . . ?
C19 C18 C17 107.45(12) . . ?
C23 C18 C17 134.26(12) . . ?
C23 C18 C19 118.28(13) . . ?
C20 C19 C18 122.22(13) . . ?
N2 C19 C18 107.98(12) . . ?
N2 C19 C20 129.79(13) . . ?
H7 C20 C19 120.2(10) . . ?
C21 C20 C19 119.02(14) . . ?
C21 C20 H7 120.8(10) . . ?
H8 C21 C20 121.6(10) . . ?
C22 C21 C20 118.46(15) . . ?
C22 C21 H8 119.9(10) . . ?
C23 C22 C21 123.31(14) . . ?
O2 C22 C21 125.28(13) . . ?
O2 C22 C23 111.41(12) . . ?
C22 C23 C18 118.70(12) . . ?
C24 C23 C18 135.47(13) . . ?
C24 C23 C22 105.83(12) . . ?
C5 C24 C1 118.36(12) . . ?
C23 C24 C1 105.91(12) . . ?
C23 C24 C5 135.72(13) . . ?
C7 N1 C4 109.32(11) . . ?
H9 N1 C4 124.0(12) . . ?
H9 N1 C7 126.1(12) . . ?
C19 N2 C16 109.18(12) . . ?
H10 N2 C16 124.1(13) . . ?
H10 N2 C19 126.7(13) . . ?
C13 O1 C10 105.46(10) . . ?
C22 O2 C1 105.70(10) . . ?

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
C1 C2 C3 C4 0.18(15) . . . . ?
C1 C24 C5 C4 0.51(14) . . . . ?
C1 C24 C5 C6 179.03(11) . . . . ?
C1 C24 C23 C18 179.92(10) . . . . ?
C1 C24 C23 C22 0.35(11) . . . . ?
C1 O2 C22 C21 -179.85(10) . . . . ?
C1 O2 C22 C23 0.00(11) . . . . ?
C2 C3 C4 C5 0.61(16) . . . . ?
C2 C3 C4 N1 -179.37(12) . . . . ?
C3 C4 C5 C6 -179.85(14) . . . . ?
C3 C4 C5 C24 -0.96(15) . . . . ?
C3 C4 N1 C7 179.53(16) . . . . ?
C4 C5 C6 C7 0.23(11) . . . . ?
C4 C5 C6 C11 179.80(10) . . . . ?
C4 C5 C24 C23 -178.14(11) . . . . ?
C4 N1 C7 C6 0.59(12) . . . . ?
C4 N1 C7 C8 -178.47(11) . . . . ?
C5 C6 C7 C8 178.65(11) . . . . ?
C5 C6 C7 N1 -0.50(11) . . . . ?
C5 C6 C11 C10 179.98(16) . . . . ?
C5 C6 C11 C12 -2.2(2) . . . . ?
C5 C24 C23 C18 -1.3(2) . . . . ?
C5 C24 C23 C22 179.11(17) . . . . ?
C6 C7 C8 C9 1.81(16) . . . . ?
C6 C11 C10 C9 1.20(15) . . . . ?
C6 C11 C10 O1 178.96(12) . . . . ?
C6 C11 C12 C13 -178.33(16) . . . . ?
C6 C11 C12 C17 1.9(2) . . . . ?
C7 C8 C9 C10 -1.09(16) . . . . ?
C8 C9 C10 C11 -0.40(16) . . . . ?
C8 C9 C10 O1 -177.85(12) . . . . ?
C9 C10 C11 C12 -177.18(14) . . . . ?
C9 C10 O1 C13 177.16(14) . . . . ?
C10 C11 C12 C13 -0.36(12) . . . . ?
C10 C11 C12 C17 179.89(10) . . . . ?
C10 O1 C13 C12 0.33(10) . . . . ?
C10 O1 C13 C14 -179.67(10) . . . . ?
C11 C12 C13 C14 -179.98(10) . . . . ?
C11 C12 C13 O1 0.02(11) . . . . ?
C11 C12 C17 C16 179.60(15) . . . . ?
C11 C12 C17 C18 -0.5(2) . . . . ?
C12 C13 C14 C15 0.26(16) . . . . ?
C12 C17 C16 C15 0.36(15) . . . . ?
C12 C17 C16 N2 -179.60(13) . . . . ?
C12 C17 C18 C19 179.84(17) . . . . ?
C12 C17 C18 C23 -0.7(2) . . . . ?
C13 C14 C15 C16 -0.03(16) . . . . ?
C14 C15 C16 C17 -0.27(17) . . . . ?
C14 C15 C16 N2 179.68(12) . . . . ?
C15 C16 C17 C18 -179.53(14) . . . . ?
C15 C16 N2 C19 179.51(16) . . . . ?
C16 C17 C18 C19 -0.30(12) . . . . ?
C16 C17 C18 C23 179.15(10) . . . . ?
C16 N2 C19 C18 0.34(12) . . . . ?
C16 N2 C19 C20 -178.72(11) . . . . ?
C17 C18 C19 C20 179.12(11) . . . . ?
C17 C18 C19 N2 -0.02(11) . . . . ?
C17 C18 C23 C22 -179.11(15) . . . . ?
C17 C18 C23 C24 1.4(2) . . . . ?
C18 C19 C20 C21 0.27(16) . . . . ?
C18 C23 C22 C21 -0.03(15) . . . . ?
C18 C23 C22 O2 -179.88(12) . . . . ?
C19 C20 C21 C22 0.00(15) . . . . ?
C20 C21 C22 C23 -0.13(16) . . . . ?
C20 C21 C22 O2 179.70(12) . . . . ?
C21 C22 C23 C24 179.63(14) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
N1 H9 0.004000 0.001198 0.000566 0.002293

####################################################################### 
# 
# 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_210705nakagawa
_database_code_depnum_ccdc_archive 'CCDC 2346719'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-10-17 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
tetra-tert-butyl-N,N-diphenylethyldioxadiaza[8]circulene
_chemical_name_common            
tetra-tert-butyl-N,N-diphenylethyl-opp-dioxadiaza[8]circulene
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H58 N2 O2'
_chemical_formula_sum            'C56 H58 N2 O2'
_chemical_formula_weight         791.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.86080(10)
_cell_length_b                   13.42840(10)
_cell_length_c                   27.87400(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.7710(10)
_cell_angle_gamma                90
_cell_volume                     4439.13(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    40778
_cell_measurement_theta_min      3.2160
_cell_measurement_theta_max      74.1940

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.543
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.73229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            58942
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.654
_diffrn_reflns_theta_max         74.515
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8973
_reflns_number_gt                8260
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    CrystalMakerX
_computing_publication_material  CrystalMakerX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²+0.9950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8973
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.10709(8) 0.64188(8) 0.66529(3) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.16540(8) 0.59799(7) 0.70339(3) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.21954(8) 0.51093(7) 0.68458(3) 0.0193(2) Uani 1 1 d . . . . .
C4 C 0.19243(8) 0.50782(8) 0.63588(3) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.23114(9) 0.43448(8) 0.60374(3) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.29985(9) 0.36095(8) 0.62403(4) 0.0236(2) Uani 1 1 d . . . . .
H1 H 0.3283 0.3093 0.6043 0.028 Uiso 1 1 calc R U . . .
C7 C 0.32768(9) 0.36194(8) 0.67318(4) 0.0223(2) Uani 1 1 d . . . . .
C8 C 0.28853(8) 0.43619(8) 0.70443(3) 0.0202(2) Uani 1 1 d . . . . .
C9 C 0.33457(8) 0.41470(7) 0.75094(3) 0.0201(2) Uani 1 1 d . . . . .
C10 C 0.40052(9) 0.32807(8) 0.74650(4) 0.0224(2) Uani 1 1 d . . . . .
C11 C 0.46123(9) 0.28674(8) 0.78530(4) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.5053 0.2286 0.7805 0.029 Uiso 1 1 calc R U . . .
C12 C 0.45764(8) 0.33000(8) 0.83079(4) 0.0222(2) Uani 1 1 d . . . . .
C13 C 0.38963(8) 0.41612(8) 0.83441(3) 0.0204(2) Uani 1 1 d . . . . .
C14 C 0.33082(8) 0.45969(7) 0.79632(3) 0.0195(2) Uani 1 1 d . . . . .
C15 C 0.27764(8) 0.54721(7) 0.81500(3) 0.0195(2) Uani 1 1 d . . . . .
C16 C 0.30584(8) 0.55122(8) 0.86360(3) 0.0205(2) Uani 1 1 d . . . . .
C17 C 0.26975(9) 0.62618(8) 0.89549(4) 0.0227(2) Uani 1 1 d . . . . .
C18 C 0.20123(9) 0.69988(8) 0.87518(4) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.1744 0.7525 0.8948 0.029 Uiso 1 1 calc R U . . .
C19 C 0.17129(9) 0.69757(8) 0.82615(4) 0.0224(2) Uani 1 1 d . . . . .
C20 C 0.20882(8) 0.62221(8) 0.79514(3) 0.0202(2) Uani 1 1 d . . . . .
C21 C 0.16162(8) 0.64287(7) 0.74876(3) 0.0203(2) Uani 1 1 d . . . . .
C22 C 0.09636(9) 0.72991(8) 0.75312(4) 0.0224(2) Uani 1 1 d . . . . .
C23 C 0.03637(9) 0.77175(8) 0.71419(4) 0.0238(2) Uani 1 1 d . . . . .
H4 H -0.0075 0.8300 0.7190 0.029 Uiso 1 1 calc R U . . .
C24 C 0.04038(8) 0.72885(8) 0.66866(4) 0.0220(2) Uani 1 1 d . . . . .
C25 C 0.46334(9) 0.21614(8) 0.67909(4) 0.0267(2) Uani 1 1 d . . . . .
H15 H 0.5389 0.2162 0.6946 0.032 Uiso 1 1 calc R U . . .
H16 H 0.4734 0.2279 0.6443 0.032 Uiso 1 1 calc R U . . .
C26 C 0.40867(10) 0.11453(9) 0.68625(5) 0.0326(3) Uani 1 1 d . . . . .
H17 H 0.4572 0.0628 0.6719 0.039 Uiso 1 1 calc R U . . .
H18 H 0.4039 0.1008 0.7211 0.039 Uiso 1 1 calc R U . . .
C27 C 0.29262(10) 0.10738(8) 0.66420(4) 0.0309(3) Uani 1 1 d . . . . .
C28 C 0.19749(11) 0.10579(9) 0.69279(5) 0.0354(3) Uani 1 1 d . . . . .
H5 H 0.2059 0.1094 0.7267 0.042 Uiso 1 1 calc R U . . .
C29 C 0.09041(11) 0.09894(10) 0.67237(5) 0.0408(3) Uani 1 1 d . . . . .
H6 H 0.0262 0.0964 0.6924 0.049 Uiso 1 1 calc R U . . .
C30 C 0.07672(11) 0.09582(10) 0.62290(5) 0.0409(3) Uani 1 1 d . . . . .
H7 H 0.0033 0.0919 0.6090 0.049 Uiso 1 1 calc R U . . .
C31 C 0.17014(11) 0.09842(10) 0.59392(5) 0.0377(3) Uani 1 1 d . . . . .
H8 H 0.1611 0.0967 0.5600 0.045 Uiso 1 1 calc R U . . .
C32 C 0.27749(10) 0.10354(9) 0.61441(5) 0.0340(3) Uani 1 1 d . . . . .
H9 H 0.3415 0.1045 0.5943 0.041 Uiso 1 1 calc R U . . .
C33 C 0.03701(9) 0.84453(8) 0.81989(4) 0.0269(2) Uani 1 1 d . . . . .
H19 H 0.0300 0.8355 0.8550 0.032 Uiso 1 1 calc R U . . .
H20 H -0.0398 0.8433 0.8056 0.032 Uiso 1 1 calc R U . . .
C34 C 0.09070(10) 0.94567(9) 0.81005(4) 0.0328(3) Uani 1 1 d . . . . .
H21 H 0.0924 0.9567 0.7750 0.039 Uiso 1 1 calc R U . . .
H22 H 0.0433 0.9985 0.8242 0.039 Uiso 1 1 calc R U . . .
C35 C 0.20845(10) 0.95453(8) 0.83014(4) 0.0301(2) Uani 1 1 d . . . . .
C36 C 0.22733(11) 0.96179(9) 0.87961(4) 0.0337(3) Uani 1 1 d . . . . .
H10 H 0.1649 0.9618 0.9006 0.040 Uiso 1 1 calc R U . . .
C37 C 0.33590(11) 0.96905(10) 0.89855(5) 0.0366(3) Uani 1 1 d . . . . .
H11 H 0.3474 0.9733 0.9323 0.044 Uiso 1 1 calc R U . . .
C38 C 0.42706(11) 0.97016(10) 0.86833(5) 0.0384(3) Uani 1 1 d . . . . .
H12 H 0.5015 0.9754 0.8811 0.046 Uiso 1 1 calc R U . . .
C39 C 0.40956(11) 0.96368(10) 0.81929(5) 0.0392(3) Uani 1 1 d . . . . .
H13 H 0.4722 0.9654 0.7984 0.047 Uiso 1 1 calc R U . . .
C40 C 0.30145(11) 0.95467(9) 0.80034(4) 0.0349(3) Uani 1 1 d . . . . .
H14 H 0.2908 0.9485 0.7666 0.042 Uiso 1 1 calc R U . . .
C41 C 0.19851(9) 0.43369(8) 0.55040(4) 0.0256(2) Uani 1 1 d . . . . .
C42 C 0.22242(11) 0.53572(9) 0.52769(4) 0.0346(3) Uani 1 1 d . . . . .
H23 H 0.2012 0.5341 0.4936 0.052 Uiso 1 1 calc R U . . .
H24 H 0.1784 0.5870 0.5440 0.052 Uiso 1 1 calc R U . . .
H25 H 0.3029 0.5510 0.5310 0.052 Uiso 1 1 calc R U . . .
C43 C 0.07197(10) 0.40965(10) 0.54560(4) 0.0343(3) Uani 1 1 d . . . . .
H26 H 0.0499 0.4089 0.5116 0.051 Uiso 1 1 calc R U . . .
H27 H 0.0571 0.3442 0.5598 0.051 Uiso 1 1 calc R U . . .
H28 H 0.0283 0.4605 0.5624 0.051 Uiso 1 1 calc R U . . .
C44 C 0.26470(11) 0.35540(10) 0.52237(4) 0.0339(3) Uani 1 1 d . . . . .
H29 H 0.2414 0.3573 0.4885 0.051 Uiso 1 1 calc R U . . .
H30 H 0.3456 0.3697 0.5251 0.051 Uiso 1 1 calc R U . . .
H31 H 0.2495 0.2892 0.5355 0.051 Uiso 1 1 calc R U . . .
C45 C 0.52408(9) 0.28827(8) 0.87370(4) 0.0254(2) Uani 1 1 d . . . . .
C46 C 0.44154(10) 0.25399(9) 0.91250(4) 0.0327(3) Uani 1 1 d . . . . .
H32 H 0.4841 0.2273 0.9400 0.049 Uiso 1 1 calc R U . . .
H33 H 0.3960 0.3108 0.9229 0.049 Uiso 1 1 calc R U . . .
H34 H 0.3919 0.2021 0.8993 0.049 Uiso 1 1 calc R U . . .
C47 C 0.60273(10) 0.36966(9) 0.89377(4) 0.0320(3) Uani 1 1 d . . . . .
H35 H 0.6455 0.3433 0.9213 0.048 Uiso 1 1 calc R U . . .
H36 H 0.6550 0.3907 0.8688 0.048 Uiso 1 1 calc R U . . .
H37 H 0.5578 0.4269 0.9040 0.048 Uiso 1 1 calc R U . . .
C48 C 0.59836(10) 0.20003(9) 0.85932(4) 0.0332(3) Uani 1 1 d . . . . .
H38 H 0.6395 0.1753 0.8876 0.050 Uiso 1 1 calc R U . . .
H39 H 0.5508 0.1467 0.8461 0.050 Uiso 1 1 calc R U . . .
H40 H 0.6522 0.2217 0.8351 0.050 Uiso 1 1 calc R U . . .
C49 C 0.30195(10) 0.62623(8) 0.94885(4) 0.0267(2) Uani 1 1 d . . . . .
C50 C 0.43088(10) 0.63125(10) 0.95475(4) 0.0348(3) Uani 1 1 d . . . . .
H41 H 0.4510 0.6313 0.9890 0.052 Uiso 1 1 calc R U . . .
H42 H 0.4649 0.5733 0.9392 0.052 Uiso 1 1 calc R U . . .
H43 H 0.4589 0.6924 0.9398 0.052 Uiso 1 1 calc R U . . .
C51 C 0.25822(11) 0.53073(10) 0.97268(4) 0.0360(3) Uani 1 1 d . . . . .
H44 H 0.2790 0.5311 1.0068 0.054 Uiso 1 1 calc R U . . .
H45 H 0.1760 0.5277 0.9692 0.054 Uiso 1 1 calc R U . . .
H46 H 0.2918 0.4725 0.9572 0.054 Uiso 1 1 calc R U . . .
C52 C 0.25146(12) 0.71607(10) 0.97488(4) 0.0374(3) Uani 1 1 d . . . . .
H47 H 0.2736 0.7139 1.0089 0.056 Uiso 1 1 calc R U . . .
H48 H 0.2795 0.7777 0.9605 0.056 Uiso 1 1 calc R U . . .
H49 H 0.1691 0.7140 0.9719 0.056 Uiso 1 1 calc R U . . .
C53 C -0.02151(9) 0.77370(8) 0.62524(4) 0.0257(2) Uani 1 1 d . . . . .
C54 C -0.09473(10) 0.86281(9) 0.63941(4) 0.0329(3) Uani 1 1 d . . . . .
H50 H -0.1330 0.8895 0.6108 0.049 Uiso 1 1 calc R U . . .
H51 H -0.1511 0.8413 0.6626 0.049 Uiso 1 1 calc R U . . .
H52 H -0.0470 0.9146 0.6539 0.049 Uiso 1 1 calc R U . . .
C55 C 0.06588(11) 0.80892(10) 0.58863(4) 0.0362(3) Uani 1 1 d . . . . .
H53 H 0.0269 0.8378 0.5607 0.054 Uiso 1 1 calc R U . . .
H54 H 0.1149 0.8593 0.6035 0.054 Uiso 1 1 calc R U . . .
H55 H 0.1115 0.7521 0.5784 0.054 Uiso 1 1 calc R U . . .
C56 C -0.09984(11) 0.69577(9) 0.60223(5) 0.0363(3) Uani 1 1 d . . . . .
H56 H -0.1390 0.7252 0.5745 0.054 Uiso 1 1 calc R U . . .
H57 H -0.0552 0.6385 0.5918 0.054 Uiso 1 1 calc R U . . .
H58 H -0.1553 0.6739 0.6258 0.054 Uiso 1 1 calc R U . . .
N1 N 0.39656(8) 0.29693(7) 0.69900(3) 0.0240(2) Uani 1 1 d . . . . .
N2 N 0.10220(8) 0.76224(7) 0.80041(3) 0.0241(2) Uani 1 1 d . . . . .
O1 O 0.12266(6) 0.58730(5) 0.62334(2) 0.02108(16) Uani 1 1 d . . . . .
O2 O 0.37463(6) 0.47100(5) 0.87631(2) 0.02130(16) Uani 1 1 d . . . . .


_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
C1 C2 1.3906(13) . ?
C1 O1 1.3944(12) . ?
C1 C24 1.4145(14) . ?
C2 C21 1.4022(13) . ?
C2 C3 1.4363(13) . ?
C3 C4 1.3913(13) . ?
C3 C8 1.4039(14) . ?
C4 O1 1.3922(12) . ?
C4 C5 1.4123(14) . ?
C5 C6 1.3952(15) . ?
C5 C41 1.5313(13) . ?
C6 C7 1.4049(14) . ?
C6 H1 0.9500 . ?
C7 N1 1.3899(13) . ?
C7 C8 1.4069(14) . ?
C8 C9 1.4296(13) . ?
C9 C14 1.4029(13) . ?
C9 C10 1.4082(14) . ?
C10 N1 1.3887(13) . ?
C10 C11 1.4056(14) . ?
C11 C12 1.3958(14) . ?
C11 H2 0.9500 . ?
C12 C13 1.4144(14) . ?
C12 C45 1.5298(13) . ?
C13 C14 1.3915(13) . ?
C13 O2 1.3945(12) . ?
C14 C15 1.4349(14) . ?
C15 C16 1.3919(13) . ?
C15 C20 1.4054(14) . ?
C16 O2 1.3943(12) . ?
C16 C17 1.4130(14) . ?
C17 C18 1.3956(15) . ?
C17 C49 1.5308(13) . ?
C18 C19 1.4078(14) . ?
C18 H3 0.9500 . ?
C19 N2 1.3873(13) . ?
C19 C20 1.4071(14) . ?
C20 C21 1.4291(13) . ?
C21 C22 1.4080(14) . ?
C22 N2 1.3887(13) . ?
C22 C23 1.4066(14) . ?
C23 C24 1.3950(14) . ?
C23 H4 0.9500 . ?
C24 C53 1.5307(14) . ?
C25 N1 1.4574(13) . ?
C25 C26 1.5250(17) . ?
C25 H15 0.9900 . ?
C25 H16 0.9900 . ?
C26 C27 1.5030(16) . ?
C26 H17 0.9900 . ?
C26 H18 0.9900 . ?
C27 C28 1.3902(17) . ?
C27 C32 1.3981(17) . ?
C28 C29 1.3878(18) . ?
C28 H5 0.9500 . ?
C29 C30 1.387(2) . ?
C29 H6 0.9500 . ?
C30 C31 1.3805(19) . ?
C30 H7 0.9500 . ?
C31 C32 1.3901(18) . ?
C31 H8 0.9500 . ?
C32 H9 0.9500 . ?
C33 N2 1.4577(13) . ?
C33 C34 1.5264(17) . ?
C33 H19 0.9900 . ?
C33 H20 0.9900 . ?
C34 C35 1.5024(17) . ?
C34 H21 0.9900 . ?
C34 H22 0.9900 . ?
C35 C40 1.3897(17) . ?
C35 C36 1.3975(16) . ?
C36 C37 1.3886(18) . ?
C36 H10 0.9500 . ?
C37 C38 1.3796(19) . ?
C37 H11 0.9500 . ?
C38 C39 1.3827(19) . ?
C38 H12 0.9500 . ?
C39 C40 1.3856(19) . ?
C39 H13 0.9500 . ?
C40 H14 0.9500 . ?
C41 C44 1.5325(15) . ?
C41 C42 1.5372(16) . ?
C41 C43 1.5393(16) . ?
C42 H23 0.9800 . ?
C42 H24 0.9800 . ?
C42 H25 0.9800 . ?
C43 H26 0.9800 . ?
C43 H27 0.9800 . ?
C43 H28 0.9800 . ?
C44 H29 0.9800 . ?
C44 H30 0.9800 . ?
C44 H31 0.9800 . ?
C45 C48 1.5331(15) . ?
C45 C47 1.5373(15) . ?
C45 C46 1.5389(16) . ?
C46 H32 0.9800 . ?
C46 H33 0.9800 . ?
C46 H34 0.9800 . ?
C47 H35 0.9800 . ?
C47 H36 0.9800 . ?
C47 H37 0.9800 . ?
C48 H38 0.9800 . ?
C48 H39 0.9800 . ?
C48 H40 0.9800 . ?
C49 C52 1.5336(15) . ?
C49 C50 1.5373(16) . ?
C49 C51 1.5375(16) . ?
C50 H41 0.9800 . ?
C50 H42 0.9800 . ?
C50 H43 0.9800 . ?
C51 H44 0.9800 . ?
C51 H45 0.9800 . ?
C51 H46 0.9800 . ?
C52 H47 0.9800 . ?
C52 H48 0.9800 . ?
C52 H49 0.9800 . ?
C53 C54 1.5334(15) . ?
C53 C56 1.5340(16) . ?
C53 C55 1.5386(16) . ?
C54 H50 0.9800 . ?
C54 H51 0.9800 . ?
C54 H52 0.9800 . ?
C55 H53 0.9800 . ?
C55 H54 0.9800 . ?
C55 H55 0.9800 . ?
C56 H56 0.9800 . ?
C56 H57 0.9800 . ?
C56 H58 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
C2 C1 O1 110.34(8) . . ?
C2 C1 C24 124.89(9) . . ?
O1 C1 C24 124.77(9) . . ?
C1 C2 C21 119.01(9) . . ?
C1 C2 C3 106.64(8) . . ?
C21 C2 C3 134.35(9) . . ?
C4 C3 C8 119.27(9) . . ?
C4 C3 C2 106.38(8) . . ?
C8 C3 C2 134.35(9) . . ?
C3 C4 O1 110.54(8) . . ?
C3 C4 C5 124.54(9) . . ?
O1 C4 C5 124.92(9) . . ?
C6 C5 C4 115.44(9) . . ?
C6 C5 C41 121.82(9) . . ?
C4 C5 C41 122.73(9) . . ?
C5 C6 C7 121.12(9) . . ?
C5 C6 H1 119.4 . . ?
C7 C6 H1 119.4 . . ?
N1 C7 C6 128.89(9) . . ?
N1 C7 C8 108.73(9) . . ?
C6 C7 C8 122.36(9) . . ?
C3 C8 C7 117.27(9) . . ?
C3 C8 C9 135.67(9) . . ?
C7 C8 C9 107.05(9) . . ?
C14 C9 C10 117.36(9) . . ?
C14 C9 C8 135.59(9) . . ?
C10 C9 C8 107.02(8) . . ?
N1 C10 C11 128.70(9) . . ?
N1 C10 C9 108.73(9) . . ?
C11 C10 C9 122.54(9) . . ?
C12 C11 C10 120.88(10) . . ?
C12 C11 H2 119.6 . . ?
C10 C11 H2 119.6 . . ?
C11 C12 C13 115.42(9) . . ?
C11 C12 C45 122.42(9) . . ?
C13 C12 C45 122.15(9) . . ?
C14 C13 O2 110.40(9) . . ?
C14 C13 C12 124.75(9) . . ?
O2 C13 C12 124.83(9) . . ?
C13 C14 C9 119.02(9) . . ?
C13 C14 C15 106.60(8) . . ?
C9 C14 C15 134.38(9) . . ?
C16 C15 C20 119.10(9) . . ?
C16 C15 C14 106.49(8) . . ?
C20 C15 C14 134.41(9) . . ?
C15 C16 O2 110.46(8) . . ?
C15 C16 C17 124.67(9) . . ?
O2 C16 C17 124.87(9) . . ?
C18 C17 C16 115.45(9) . . ?
C18 C17 C49 122.01(9) . . ?
C16 C17 C49 122.54(9) . . ?
C17 C18 C19 121.06(9) . . ?
C17 C18 H3 119.5 . . ?
C19 C18 H3 119.5 . . ?
N2 C19 C20 108.78(9) . . ?
N2 C19 C18 128.89(9) . . ?
C20 C19 C18 122.31(9) . . ?
C15 C20 C19 117.40(9) . . ?
C15 C20 C21 135.55(9) . . ?
C19 C20 C21 107.03(9) . . ?
C2 C21 C22 117.32(9) . . ?
C2 C21 C20 135.69(9) . . ?
C22 C21 C20 106.99(9) . . ?
N2 C22 C23 128.73(9) . . ?
N2 C22 C21 108.72(9) . . ?
C23 C22 C21 122.54(9) . . ?
C24 C23 C22 120.91(10) . . ?
C24 C23 H4 119.5 . . ?
C22 C23 H4 119.5 . . ?
C23 C24 C1 115.30(9) . . ?
C23 C24 C53 122.35(9) . . ?
C1 C24 C53 122.34(9) . . ?
N1 C25 C26 112.45(9) . . ?
N1 C25 H15 109.1 . . ?
C26 C25 H15 109.1 . . ?
N1 C25 H16 109.1 . . ?
C26 C25 H16 109.1 . . ?
H15 C25 H16 107.8 . . ?
C27 C26 C25 113.09(9) . . ?
C27 C26 H17 109.0 . . ?
C25 C26 H17 109.0 . . ?
C27 C26 H18 109.0 . . ?
C25 C26 H18 109.0 . . ?
H17 C26 H18 107.8 . . ?
C28 C27 C32 118.30(11) . . ?
C28 C27 C26 120.83(11) . . ?
C32 C27 C26 120.86(11) . . ?
C29 C28 C27 120.75(12) . . ?
C29 C28 H5 119.6 . . ?
C27 C28 H5 119.6 . . ?
C30 C29 C28 120.27(12) . . ?
C30 C29 H6 119.9 . . ?
C28 C29 H6 119.9 . . ?
C31 C30 C29 119.80(12) . . ?
C31 C30 H7 120.1 . . ?
C29 C30 H7 120.1 . . ?
C30 C31 C32 119.92(12) . . ?
C30 C31 H8 120.0 . . ?
C32 C31 H8 120.0 . . ?
C31 C32 C27 120.95(12) . . ?
C31 C32 H9 119.5 . . ?
C27 C32 H9 119.5 . . ?
N2 C33 C34 112.52(9) . . ?
N2 C33 H19 109.1 . . ?
C34 C33 H19 109.1 . . ?
N2 C33 H20 109.1 . . ?
C34 C33 H20 109.1 . . ?
H19 C33 H20 107.8 . . ?
C35 C34 C33 113.05(9) . . ?
C35 C34 H21 109.0 . . ?
C33 C34 H21 109.0 . . ?
C35 C34 H22 109.0 . . ?
C33 C34 H22 109.0 . . ?
H21 C34 H22 107.8 . . ?
C40 C35 C36 118.15(11) . . ?
C40 C35 C34 121.25(11) . . ?
C36 C35 C34 120.59(11) . . ?
C37 C36 C35 121.03(11) . . ?
C37 C36 H10 119.5 . . ?
C35 C36 H10 119.5 . . ?
C38 C37 C36 119.94(12) . . ?
C38 C37 H11 120.0 . . ?
C36 C37 H11 120.0 . . ?
C37 C38 C39 119.63(12) . . ?
C37 C38 H12 120.2 . . ?
C39 C38 H12 120.2 . . ?
C38 C39 C40 120.55(12) . . ?
C38 C39 H13 119.7 . . ?
C40 C39 H13 119.7 . . ?
C39 C40 C35 120.68(12) . . ?
C39 C40 H14 119.7 . . ?
C35 C40 H14 119.7 . . ?
C5 C41 C44 112.04(9) . . ?
C5 C41 C42 110.37(9) . . ?
C44 C41 C42 107.63(9) . . ?
C5 C41 C43 108.61(9) . . ?
C44 C41 C43 108.50(10) . . ?
C42 C41 C43 109.65(10) . . ?
C41 C42 H23 109.5 . . ?
C41 C42 H24 109.5 . . ?
H23 C42 H24 109.5 . . ?
C41 C42 H25 109.5 . . ?
H23 C42 H25 109.5 . . ?
H24 C42 H25 109.5 . . ?
C41 C43 H26 109.5 . . ?
C41 C43 H27 109.5 . . ?
H26 C43 H27 109.5 . . ?
C41 C43 H28 109.5 . . ?
H26 C43 H28 109.5 . . ?
H27 C43 H28 109.5 . . ?
C41 C44 H29 109.5 . . ?
C41 C44 H30 109.5 . . ?
H29 C44 H30 109.5 . . ?
C41 C44 H31 109.5 . . ?
H29 C44 H31 109.5 . . ?
H30 C44 H31 109.5 . . ?
C12 C45 C48 111.74(9) . . ?
C12 C45 C47 109.13(9) . . ?
C48 C45 C47 107.25(9) . . ?
C12 C45 C46 109.46(9) . . ?
C48 C45 C46 109.02(9) . . ?
C47 C45 C46 110.22(9) . . ?
C45 C46 H32 109.5 . . ?
C45 C46 H33 109.5 . . ?
H32 C46 H33 109.5 . . ?
C45 C46 H34 109.5 . . ?
H32 C46 H34 109.5 . . ?
H33 C46 H34 109.5 . . ?
C45 C47 H35 109.5 . . ?
C45 C47 H36 109.5 . . ?
H35 C47 H36 109.5 . . ?
C45 C47 H37 109.5 . . ?
H35 C47 H37 109.5 . . ?
H36 C47 H37 109.5 . . ?
C45 C48 H38 109.5 . . ?
C45 C48 H39 109.5 . . ?
H38 C48 H39 109.5 . . ?
C45 C48 H40 109.5 . . ?
H38 C48 H40 109.5 . . ?
H39 C48 H40 109.5 . . ?
C17 C49 C52 111.48(9) . . ?
C17 C49 C50 109.80(9) . . ?
C52 C49 C50 108.00(10) . . ?
C17 C49 C51 109.76(9) . . ?
C52 C49 C51 108.40(10) . . ?
C50 C49 C51 109.35(10) . . ?
C49 C50 H41 109.5 . . ?
C49 C50 H42 109.5 . . ?
H41 C50 H42 109.5 . . ?
C49 C50 H43 109.5 . . ?
H41 C50 H43 109.5 . . ?
H42 C50 H43 109.5 . . ?
C49 C51 H44 109.5 . . ?
C49 C51 H45 109.5 . . ?
H44 C51 H45 109.5 . . ?
C49 C51 H46 109.5 . . ?
H44 C51 H46 109.5 . . ?
H45 C51 H46 109.5 . . ?
C49 C52 H47 109.5 . . ?
C49 C52 H48 109.5 . . ?
H47 C52 H48 109.5 . . ?
C49 C52 H49 109.5 . . ?
H47 C52 H49 109.5 . . ?
H48 C52 H49 109.5 . . ?
C24 C53 C54 111.74(9) . . ?
C24 C53 C56 110.09(9) . . ?
C54 C53 C56 107.34(9) . . ?
C24 C53 C55 108.98(9) . . ?
C54 C53 C55 108.66(9) . . ?
C56 C53 C55 110.01(10) . . ?
C53 C54 H50 109.5 . . ?
C53 C54 H51 109.5 . . ?
H50 C54 H51 109.5 . . ?
C53 C54 H52 109.5 . . ?
H50 C54 H52 109.5 . . ?
H51 C54 H52 109.5 . . ?
C53 C55 H53 109.5 . . ?
C53 C55 H54 109.5 . . ?
H53 C55 H54 109.5 . . ?
C53 C55 H55 109.5 . . ?
H53 C55 H55 109.5 . . ?
H54 C55 H55 109.5 . . ?
C53 C56 H56 109.5 . . ?
C53 C56 H57 109.5 . . ?
H56 C56 H57 109.5 . . ?
C53 C56 H58 109.5 . . ?
H56 C56 H58 109.5 . . ?
H57 C56 H58 109.5 . . ?
C10 N1 C7 108.46(8) . . ?
C10 N1 C25 125.14(9) . . ?
C7 N1 C25 126.09(8) . . ?
C19 N2 C22 108.47(8) . . ?
C19 N2 C33 126.47(9) . . ?
C22 N2 C33 124.79(9) . . ?
C4 O1 C1 106.10(7) . . ?
C16 O2 C13 106.03(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
O1 C1 C2 C21 179.06(8) . . . . ?
C24 C1 C2 C21 -1.61(16) . . . . ?
O1 C1 C2 C3 -0.54(11) . . . . ?
C24 C1 C2 C3 178.79(9) . . . . ?
C1 C2 C3 C4 0.93(11) . . . . ?
C21 C2 C3 C4 -178.58(11) . . . . ?
C1 C2 C3 C8 -179.47(11) . . . . ?
C21 C2 C3 C8 1.0(2) . . . . ?
C8 C3 C4 O1 179.32(8) . . . . ?
C2 C3 C4 O1 -1.00(11) . . . . ?
C8 C3 C4 C5 -1.08(15) . . . . ?
C2 C3 C4 C5 178.60(10) . . . . ?
C3 C4 C5 C6 0.86(15) . . . . ?
O1 C4 C5 C6 -179.59(9) . . . . ?
C3 C4 C5 C41 179.65(10) . . . . ?
O1 C4 C5 C41 -0.81(16) . . . . ?
C4 C5 C6 C7 -0.28(15) . . . . ?
C41 C5 C6 C7 -179.07(10) . . . . ?
C5 C6 C7 N1 -178.20(10) . . . . ?
C5 C6 C7 C8 -0.07(16) . . . . ?
C4 C3 C8 C7 0.65(14) . . . . ?
C2 C3 C8 C7 -178.91(10) . . . . ?
C4 C3 C8 C9 179.18(11) . . . . ?
C2 C3 C8 C9 -0.4(2) . . . . ?
N1 C7 C8 C3 178.35(9) . . . . ?
C6 C7 C8 C3 -0.12(15) . . . . ?
N1 C7 C8 C9 -0.57(12) . . . . ?
C6 C7 C8 C9 -179.04(10) . . . . ?
C3 C8 C9 C14 -0.6(2) . . . . ?
C7 C8 C9 C14 178.07(11) . . . . ?
C3 C8 C9 C10 -178.52(11) . . . . ?
C7 C8 C9 C10 0.12(11) . . . . ?
C14 C9 C10 N1 -178.01(9) . . . . ?
C8 C9 C10 N1 0.38(12) . . . . ?
C14 C9 C10 C11 -0.11(15) . . . . ?
C8 C9 C10 C11 178.28(10) . . . . ?
N1 C10 C11 C12 178.15(10) . . . . ?
C9 C10 C11 C12 0.71(17) . . . . ?
C10 C11 C12 C13 0.14(15) . . . . ?
C10 C11 C12 C45 -178.94(10) . . . . ?
C11 C12 C13 C14 -1.67(15) . . . . ?
C45 C12 C13 C14 177.42(10) . . . . ?
C11 C12 C13 O2 -179.71(9) . . . . ?
C45 C12 C13 O2 -0.63(16) . . . . ?
O2 C13 C14 C9 -179.41(8) . . . . ?
C12 C13 C14 C9 2.30(16) . . . . ?
O2 C13 C14 C15 0.95(11) . . . . ?
C12 C13 C14 C15 -177.34(9) . . . . ?
C10 C9 C14 C13 -1.30(14) . . . . ?
C8 C9 C14 C13 -179.10(11) . . . . ?
C10 C9 C14 C15 178.21(11) . . . . ?
C8 C9 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C16 -0.79(11) . . . . ?
C9 C14 C15 C16 179.65(11) . . . . ?
C13 C14 C15 C20 179.31(11) . . . . ?
C9 C14 C15 C20 -0.2(2) . . . . ?
C20 C15 C16 O2 -179.72(8) . . . . ?
C14 C15 C16 O2 0.37(11) . . . . ?
C20 C15 C16 C17 0.26(16) . . . . ?
C14 C15 C16 C17 -179.65(10) . . . . ?
C15 C16 C17 C18 -0.07(16) . . . . ?
O2 C16 C17 C18 179.90(9) . . . . ?
C15 C16 C17 C49 179.12(10) . . . . ?
O2 C16 C17 C49 -0.91(16) . . . . ?
C16 C17 C18 C19 0.15(15) . . . . ?
C49 C17 C18 C19 -179.04(10) . . . . ?
C17 C18 C19 N2 178.03(10) . . . . ?
C17 C18 C19 C20 -0.43(16) . . . . ?
C16 C15 C20 C19 -0.50(14) . . . . ?
C14 C15 C20 C19 179.38(10) . . . . ?
C16 C15 C20 C21 -178.90(11) . . . . ?
C14 C15 C20 C21 1.0(2) . . . . ?
N2 C19 C20 C15 -178.13(9) . . . . ?
C18 C19 C20 C15 0.60(15) . . . . ?
N2 C19 C20 C21 0.69(12) . . . . ?
C18 C19 C20 C21 179.43(10) . . . . ?
C1 C2 C21 C22 1.13(14) . . . . ?
C3 C2 C21 C22 -179.41(10) . . . . ?
C1 C2 C21 C20 -179.49(11) . . . . ?
C3 C2 C21 C20 0.0(2) . . . . ?
C15 C20 C21 C2 -1.2(2) . . . . ?
C19 C20 C21 C2 -179.73(11) . . . . ?
C15 C20 C21 C22 178.21(11) . . . . ?
C19 C20 C21 C22 -0.30(11) . . . . ?
C2 C21 C22 N2 179.35(9) . . . . ?
C20 C21 C22 N2 -0.19(12) . . . . ?
C2 C21 C22 C23 0.09(15) . . . . ?
C20 C21 C22 C23 -179.46(10) . . . . ?
N2 C22 C23 C24 179.94(10) . . . . ?
C21 C22 C23 C24 -0.95(17) . . . . ?
C22 C23 C24 C1 0.53(15) . . . . ?
C22 C23 C24 C53 -178.52(10) . . . . ?
C2 C1 C24 C23 0.75(15) . . . . ?
O1 C1 C24 C23 179.98(9) . . . . ?
C2 C1 C24 C53 179.80(10) . . . . ?
O1 C1 C24 C53 -0.97(16) . . . . ?
N1 C25 C26 C27 58.36(13) . . . . ?
C25 C26 C27 C28 -107.51(13) . . . . ?
C25 C26 C27 C32 71.61(14) . . . . ?
C32 C27 C28 C29 1.02(18) . . . . ?
C26 C27 C28 C29 -179.84(11) . . . . ?
C27 C28 C29 C30 -1.45(19) . . . . ?
C28 C29 C30 C31 0.7(2) . . . . ?
C29 C30 C31 C32 0.4(2) . . . . ?
C30 C31 C32 C27 -0.80(19) . . . . ?
C28 C27 C32 C31 0.10(18) . . . . ?
C26 C27 C32 C31 -179.04(11) . . . . ?
N2 C33 C34 C35 -58.33(13) . . . . ?
C33 C34 C35 C40 107.90(13) . . . . ?
C33 C34 C35 C36 -71.40(14) . . . . ?
C40 C35 C36 C37 0.07(18) . . . . ?
C34 C35 C36 C37 179.38(11) . . . . ?
C35 C36 C37 C38 0.64(19) . . . . ?
C36 C37 C38 C39 -0.22(19) . . . . ?
C37 C38 C39 C40 -0.9(2) . . . . ?
C38 C39 C40 C35 1.7(2) . . . . ?
C36 C35 C40 C39 -1.21(18) . . . . ?
C34 C35 C40 C39 179.48(11) . . . . ?
C6 C5 C41 C44 -9.34(15) . . . . ?
C4 C5 C41 C44 171.96(10) . . . . ?
C6 C5 C41 C42 -129.26(11) . . . . ?
C4 C5 C41 C42 52.03(14) . . . . ?
C6 C5 C41 C43 110.51(12) . . . . ?
C4 C5 C41 C43 -68.20(13) . . . . ?
C11 C12 C45 C48 3.75(15) . . . . ?
C13 C12 C45 C48 -175.27(10) . . . . ?
C11 C12 C45 C47 122.19(11) . . . . ?
C13 C12 C45 C47 -56.83(13) . . . . ?
C11 C12 C45 C46 -117.11(11) . . . . ?
C13 C12 C45 C46 63.87(13) . . . . ?
C18 C17 C49 C52 -0.91(15) . . . . ?
C16 C17 C49 C52 179.95(10) . . . . ?
C18 C17 C49 C50 -120.56(11) . . . . ?
C16 C17 C49 C50 60.30(14) . . . . ?
C18 C17 C49 C51 119.21(11) . . . . ?
C16 C17 C49 C51 -59.93(14) . . . . ?
C23 C24 C53 C54 -5.39(15) . . . . ?
C1 C24 C53 C54 175.62(10) . . . . ?
C23 C24 C53 C56 -124.57(11) . . . . ?
C1 C24 C53 C56 56.44(13) . . . . ?
C23 C24 C53 C55 114.70(11) . . . . ?
C1 C24 C53 C55 -64.29(13) . . . . ?
C11 C10 N1 C7 -178.47(11) . . . . ?
C9 C10 N1 C7 -0.75(12) . . . . ?
C11 C10 N1 C25 -4.51(18) . . . . ?
C9 C10 N1 C25 173.21(10) . . . . ?
C6 C7 N1 C10 179.16(11) . . . . ?
C8 C7 N1 C10 0.82(12) . . . . ?
C6 C7 N1 C25 5.28(18) . . . . ?
C8 C7 N1 C25 -173.06(10) . . . . ?
C26 C25 N1 C10 84.97(13) . . . . ?
C26 C25 N1 C7 -102.13(12) . . . . ?
C20 C19 N2 C22 -0.83(12) . . . . ?
C18 C19 N2 C22 -179.45(11) . . . . ?
C20 C19 N2 C33 173.47(10) . . . . ?
C18 C19 N2 C33 -5.15(18) . . . . ?
C23 C22 N2 C19 179.83(11) . . . . ?
C21 C22 N2 C19 0.63(12) . . . . ?
C23 C22 N2 C33 5.42(18) . . . . ?
C21 C22 N2 C33 -173.79(10) . . . . ?
C34 C33 N2 C19 103.80(12) . . . . ?
C34 C33 N2 C22 -82.79(13) . . . . ?
C3 C4 O1 C1 0.68(10) . . . . ?
C5 C4 O1 C1 -178.92(10) . . . . ?
C2 C1 O1 C4 -0.07(11) . . . . ?
C24 C1 O1 C4 -179.39(9) . . . . ?
C15 C16 O2 C13 0.19(11) . . . . ?
C17 C16 O2 C13 -179.78(10) . . . . ?
C14 C13 O2 C16 -0.72(11) . . . . ?
C12 C13 O2 C16 177.57(10) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.075



_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_210703nakagawa
_database_code_depnum_ccdc_archive 'CCDC 2346718'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2024-10-17 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-05-14
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2024.05.14 svn.rc2abdb5a for OlexSys, GUI svn.r6697)
;
_chemical_name_common            tetra-tert-butyl-opp-dioxadiaza[8]circulene
_chemical_name_systematic        tetra-tert-butyldioxadiaza[8]circulene
_chemical_formula_moiety         '2(C20 H21 N O), 2(C4 H8 O), 3.5[C4H8O]'
_chemical_formula_sum            'C62 H86 N2 O7.5'
_chemical_formula_weight         979.383
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.2049(1)
_cell_length_b                   16.5666(3)
_cell_length_c                   17.5296(2)
_cell_angle_alpha                109.901(2)
_cell_angle_beta                 90.100(1)
_cell_angle_gamma                106.501(2)
_cell_volume                     2655.85(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    40778
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      74.1940
_cell_measurement_theta_min      3.2160
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             1067.297
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.9815
_diffrn_reflns_Laue_measured_fraction_max 0.9815
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33819
_diffrn_reflns_point_group_measured_fraction_full 0.9815
_diffrn_reflns_point_group_measured_fraction_max 0.9815
_diffrn_reflns_theta_full        65.9949
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9815
_diffrn_measured_fraction_theta_max 0.9815
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       Â\/Yw
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              -19
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7752
_reflns_number_total             9071
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_refine_diff_density_max         0.2832
_refine_diff_density_min         -0.2865
_refine_diff_density_rms         0.0739
_refine_ls_d_res_high            0.8439
_refine_ls_d_res_low             13.6861
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0369
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    84
_refine_ls_number_parameters     500
_refine_ls_number_reflns         9071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.0369
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0970P)²+1.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1724
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
3. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed X: Hh(-10) Hi(10) Hj(10) Hk(-10) Hl(-10) Hm(-10) Ho(10) Hn(-10)
 Fixed Y: Hh(-10) Hi(-10) Hj(10) Hk(10) Hl(-10) Hm(10) Hn(10) Ho(10)
 Fixed Z: Hh(-10) Hi(-10) Hj(10) Hk(-10) Hl(10) Hm(10) Hn(-10) Ho(10)
6.a Secondary CH2 refined with riding coordinates:
 C41(H41a,H41b), C42(H42a,H42b), C43(H43a,H43b), C44(H44a,H44b), C45(H45a,
 H45b), C46(H46a,H46b), C47(H47a,H47b), C48(H48a,H48b)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), N1(H1), C24(H24), C29(H29), N2(H2)
6.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C18(H18a,H18b,
 H18c), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c), C34(H34a,H34b,H34c), C35(H35a,
 H35b,H35c), C36(H36a,H36b,H36c), C38(H38a,H38b,H38c), C39(H39a,H39b,H39c),
 C40(H40a,H40b,H40c)
;
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_refinement_flags_posn
C1 C 0.10270(19) 0.97106(13) 0.56894(11) 0.0295(4) Uani 1.000000 .
C2 C 0.1682(2) 0.95053(14) 0.62653(11) 0.0308(4) Uani 1.000000 .
C3 C 0.2825(2) 0.91717(14) 0.61413(12) 0.0326(4) Uani 1.000000 .
C4 C 0.3294(2) 0.90572(14) 0.53731(12) 0.0345(4) Uani 1.000000 .
H4 H 0.4066(2) 0.88416(14) 0.52496(12) 0.0414(5) Uiso 1.000000 R
C5 C 0.2648(2) 0.92545(14) 0.47823(12) 0.0324(4) Uani 1.000000 .
C6 C 0.15012(19) 0.95774(13) 0.49224(11) 0.0301(4) Uani 1.000000 .
C7 C 0.11060(19) 0.96886(13) 0.41890(11) 0.0297(4) Uani 1.000000 .
C8 C 0.2025(2) 0.94324(13) 0.36251(12) 0.0312(4) Uani 1.000000 .
C9 C 0.1932(2) 0.94535(13) 0.28366(11) 0.0314(4) Uani 1.000000 .
H9 H 0.2572(2) 0.92690(13) 0.24760(11) 0.0377(5) Uiso 1.000000 R
C10 C 0.09180(19) 0.97401(13) 0.25698(11) 0.0290(4) Uani 1.000000 .
C11 C 0.00185(19) 1.00031(13) 0.31513(11) 0.0293(4) Uani 1.000000 .
C12 C 0.00758(19) 0.99790(13) 0.39334(11) 0.0291(4) Uani 1.000000 .
O1 O 0.10543(13) 0.96796(9) 0.69860(8) 0.0313(3) Uani 1.000000 .
N1 N 0.29583(17) 0.91729(12) 0.39936(10) 0.0341(4) Uani 1.000000 .
H1 H 0.36371(17) 0.89868(12) 0.37643(10) 0.0410(5) Uiso 1.000000 R
C13 C 0.3484(2) 0.89496(15) 0.67965(12) 0.0356(5) Uani 1.000000 .
C14 C 0.4009(2) 0.97949(16) 0.75599(13) 0.0424(5) Uani 1.000000 .
H14a H 0.4641(13) 1.0275(4) 0.7415(2) 0.0636(8) Uiso 1.000000 GR
H14b H 0.3230(3) 0.9991(7) 0.7792(6) 0.0636(8) Uiso 1.000000 GR
H14c H 0.4494(15) 0.9661(3) 0.7963(4) 0.0636(8) Uiso 1.000000 GR
C15 C 0.2407(2) 0.82181(17) 0.70142(14) 0.0441(5) Uani 1.000000 .
H15a H 0.1614(8) 0.8428(5) 0.7194(10) 0.0661(8) Uiso 1.000000 GR
H15b H 0.2106(13) 0.7664(4) 0.6533(3) 0.0661(8) Uiso 1.000000 GR
H15c H 0.2816(6) 0.8097(8) 0.7454(7) 0.0661(8) Uiso 1.000000 GR
C16 C 0.4694(2) 0.85937(17) 0.65019(13) 0.0414(5) Uani 1.000000 .
H16a H 0.4372(4) 0.8050(6) 0.6012(6) 0.0621(8) Uiso 1.000000 GR
H16b H 0.5401(8) 0.9055(4) 0.6373(10) 0.0621(8) Uiso 1.000000 GR
H16c H 0.5082(11) 0.8448(11) 0.6932(4) 0.0621(8) Uiso 1.000000 GR
C17 C 0.0791(2) 0.97816(14) 0.17156(11) 0.0320(4) Uani 1.000000 .
C18 C 0.1841(2) 0.94129(14) 0.11943(12) 0.0354(4) Uani 1.000000 .
H18a H 0.2773(2) 0.9782(6) 0.1449(5) 0.0531(7) Uiso 1.000000 GR
H18b H 0.1704(10) 0.8789(4) 0.1154(8) 0.0531(7) Uiso 1.000000 GR
H18c H 0.1716(10) 0.9432(10) 0.0647(3) 0.0531(7) Uiso 1.000000 GR
C19 C -0.0644(2) 0.92118(17) 0.12772(13) 0.0437(5) Uani 1.000000 .
H19a H -0.0796(7) 0.8584(3) 0.1229(9) 0.0656(8) Uiso 1.000000 GR
H19b H -0.1338(2) 0.9442(7) 0.1590(5) 0.0656(8) Uiso 1.000000 GR
H19c H -0.0717(6) 0.9244(9) 0.0732(4) 0.0656(8) Uiso 1.000000 GR
C20 C 0.1047(2) 1.07654(15) 0.17920(14) 0.0424(5) Uani 1.000000 .
H20a H 0.0353(11) 1.1000(4) 0.2101(9) 0.0636(8) Uiso 1.000000 GR
H20b H 0.1964(7) 1.1125(3) 0.2077(9) 0.0636(8) Uiso 1.000000 GR
H20c H 0.0986(17) 1.0800(2) 0.12464(14) 0.0636(8) Uiso 1.000000 GR
C21 C 0.37100(19) 0.43707(13) 0.05103(11) 0.0289(4) Uani 1.000000 .
C22 C 0.28346(19) 0.38355(12) 0.08700(11) 0.0290(4) Uani 1.000000 .
C23 C 0.16212(19) 0.39878(13) 0.11984(11) 0.0300(4) Uani 1.000000 .
C24 C 0.1350(2) 0.47489(13) 0.11521(12) 0.0323(4) Uani 1.000000 .
H24 H 0.0558(2) 0.48937(13) 0.13668(12) 0.0388(5) Uiso 1.000000 R
C25 C 0.22243(19) 0.53055(13) 0.07949(12) 0.0305(4) Uani 1.000000 .
C26 C 0.34232(19) 0.51360(13) 0.04683(11) 0.0291(4) Uani 1.000000 .
C27 C 0.59584(19) 0.41790(13) -0.01504(11) 0.0289(4) Uani 1.000000 .
C28 C 0.32040(19) 0.63935(13) 0.02894(12) 0.0301(4) Uani 1.000000 .
C29 C 0.35123(19) 0.71492(13) 0.00556(12) 0.0307(4) Uani 1.000000 .
H29 H 0.29145(19) 0.75128(13) 0.01615(12) 0.0368(5) Uiso 1.000000 R
C30 C 0.46839(19) 0.73780(13) -0.03309(11) 0.0294(4) Uani 1.000000 .
C31 C 0.47854(19) 0.39659(13) 0.02498(11) 0.0282(4) Uani 1.000000 .
C32 C 0.45025(19) 0.32122(13) 0.04682(11) 0.0282(4) Uani 1.000000 .
O2 O 0.32940(13) 0.31109(8) 0.08464(8) 0.0291(3) Uani 1.000000 .
N2 N 0.20998(16) 0.60678(11) 0.06749(10) 0.0324(4) Uani 1.000000 .
H2 H 0.14290(16) 0.63058(11) 0.08199(10) 0.0389(4) Uiso 1.000000 R
C33 C 0.0656(2) 0.33401(13) 0.15472(12) 0.0321(4) Uani 1.000000 .
C34 C 0.0135(2) 0.23999(14) 0.08806(13) 0.0373(5) Uani 1.000000 .
H34a H -0.0369(14) 0.2433(2) 0.0421(4) 0.0560(7) Uiso 1.000000 GR
H34b H 0.0919(2) 0.2184(5) 0.0691(7) 0.0560(7) Uiso 1.000000 GR
H34c H -0.0477(13) 0.1983(3) 0.1104(3) 0.0560(7) Uiso 1.000000 GR
C35 C -0.0604(2) 0.36436(14) 0.18381(14) 0.0378(5) Uani 1.000000 .
H35a H -0.0303(2) 0.4229(5) 0.2284(7) 0.0568(7) Uiso 1.000000 GR
H35b H -0.1093(9) 0.3696(10) 0.1384(3) 0.0568(7) Uiso 1.000000 GR
H35c H -0.1219(8) 0.3199(5) 0.2032(9) 0.0568(7) Uiso 1.000000 GR
C36 C 0.1429(2) 0.32925(15) 0.22782(13) 0.0384(5) Uani 1.000000 .
H36a H 0.2202(10) 0.3062(10) 0.2096(2) 0.0576(7) Uiso 1.000000 GR
H36b H 0.1775(14) 0.3896(2) 0.2696(4) 0.0576(7) Uiso 1.000000 GR
H36c H 0.0801(5) 0.2890(8) 0.2509(6) 0.0576(7) Uiso 1.000000 GR
C37 C 0.50733(19) 0.82020(13) -0.05843(12) 0.0305(4) Uani 1.000000 .
C38 C 0.6451(2) 0.88467(13) -0.01020(13) 0.0355(4) Uani 1.000000 .
H38a H 0.6354(5) 0.9035(8) 0.04834(13) 0.0533(7) Uiso 1.000000 GR
H38b H 0.7158(4) 0.8539(3) -0.0219(7) 0.0533(7) Uiso 1.000000 GR
H38c H 0.6719(8) 0.9377(5) -0.0263(7) 0.0533(7) Uiso 1.000000 GR
C39 C 0.5205(2) 0.79219(14) -0.15022(12) 0.0355(4) Uani 1.000000 .
H39a H 0.5935(11) 0.7635(9) -0.16288(19) 0.0533(7) Uiso 1.000000 GR
H39b H 0.4332(5) 0.7496(8) -0.18059(12) 0.0533(7) Uiso 1.000000 GR
H39c H 0.5431(16) 0.84558(19) -0.1659(2) 0.0533(7) Uiso 1.000000 GR
C40 C 0.3998(2) 0.87088(14) -0.04036(14) 0.0366(5) Uani 1.000000 .
H40a H 0.3104(4) 0.8303(3) -0.0694(8) 0.0549(7) Uiso 1.000000 GR
H40b H 0.3927(12) 0.8923(9) 0.01847(17) 0.0549(7) Uiso 1.000000 GR
H40c H 0.4275(8) 0.9224(6) -0.0586(9) 0.0549(7) Uiso 1.000000 GR
C41 C -0.1697(2) 0.59349(16) 0.14701(14) 0.0452(5) Uani 1.000000 .
H41a H -0.1546(2) 0.53547(16) 0.11492(14) 0.0542(6) Uiso 1.000000 R
H41b H -0.2696(2) 0.58404(16) 0.14939(14) 0.0542(6) Uiso 1.000000 R
C42 C -0.0928(2) 0.63240(16) 0.23299(14) 0.0462(5) Uani 1.000000 .
H42a H -0.1539(2) 0.65049(16) 0.27503(14) 0.0554(6) Uiso 1.000000 R
H42b H -0.0546(2) 0.58823(16) 0.24391(14) 0.0554(6) Uiso 1.000000 R
C43 C 0.0215(3) 0.7138(2) 0.23126(16) 0.0606(7) Uani 1.000000 .
H43a H 0.0002(3) 0.7701(2) 0.26227(16) 0.0727(8) Uiso 1.000000 R
H43b H 0.1098(3) 0.7156(2) 0.25621(16) 0.0727(8) Uiso 1.000000 R
O3 O 0.03032(15) 0.70540(10) 0.14805(9) 0.0423(4) Uani 1.000000 .
C44 C -0.1083(2) 0.66415(16) 0.11052(15) 0.0456(5) Uani 1.000000 .
H44a H -0.1107(2) 0.63638(16) 0.05059(15) 0.0547(6) Uiso 1.000000 R
H44b H -0.1592(2) 0.70905(16) 0.12259(15) 0.0547(6) Uiso 1.000000 R
C45 C 0.5935(2) 0.81994(18) 0.34633(15) 0.0497(6) Uani 1.000000 .
H45a H 0.5771(2) 0.77221(18) 0.37026(15) 0.0596(7) Uiso 1.000000 R
H45b H 0.6391(2) 0.87883(18) 0.38957(15) 0.0596(7) Uiso 1.000000 R
C46 C 0.6810(3) 0.8019(2) 0.27626(16) 0.0593(7) Uani 1.000000 .
H46a H 0.7454(3) 0.8589(2) 0.27558(16) 0.0712(8) Uiso 1.000000 R
H46b H 0.7348(3) 0.7623(2) 0.28115(16) 0.0712(8) Uiso 1.000000 R
C47 C 0.5831(3) 0.7572(3) 0.20171(19) 0.0817(11) Uani 1.000000 .
H47a H 0.6093(3) 0.7885(3) 0.16238(19) 0.0981(13) Uiso 1.000000 R
H47b H 0.5817(3) 0.6937(3) 0.17536(19) 0.0981(13) Uiso 1.000000 R
C48 C 0.4457(3) 0.76193(19) 0.22801(15) 0.0540(6) Uani 1.000000 .
H48a H 0.4013(3) 0.78607(19) 0.19415(15) 0.0648(8) Uiso 1.000000 R
H48b H 0.3852(3) 0.70123(19) 0.22223(15) 0.0648(8) Uiso 1.000000 R
O4 O 0.46828(17) 0.82014(13) 0.31132(10) 0.0570(5) Uani 1.000000 .


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
C1 C2 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 C12 1.438(2) 2_576 ?
C2 C3 1.414(3) . ?
C2 O1 1.396(2) . ?
C3 C4 1.400(3) . ?
C3 C13 1.527(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(3) . ?
C5 C6 1.408(3) . ?
C5 N1 1.389(2) . ?
C6 C7 1.432(3) . ?
C7 C8 1.407(3) . ?
C7 C12 1.404(3) . ?
C8 C9 1.398(3) . ?
C8 N1 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(3) . ?
C10 C11 1.414(3) . ?
C10 C17 1.529(3) . ?
C11 C12 1.387(3) . ?
C11 O1 1.394(2) 2_576 ?
N1 H1 0.8800 . ?
C13 C14 1.528(3) . ?
C13 C15 1.544(3) . ?
C13 C16 1.532(3) . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C17 C18 1.533(3) . ?
C17 C19 1.530(3) . ?
C17 C20 1.534(3) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C21 C22 1.384(3) . ?
C21 C26 1.405(3) . ?
C21 C31 1.440(2) . ?
C22 C23 1.417(3) . ?
C22 O2 1.396(2) . ?
C23 C24 1.393(3) . ?
C23 C33 1.531(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.402(3) . ?
C25 C26 1.411(3) . ?
C25 N2 1.388(2) . ?
C26 C27 1.422(3) 2_665 ?
C27 C28 1.412(2) 2_665 ?
C27 C31 1.408(3) . ?
C28 C29 1.400(3) . ?
C28 N2 1.387(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.397(3) . ?
C30 C32 1.416(2) 2_665 ?
C30 C37 1.524(3) . ?
C31 C32 1.382(3) . ?
C32 O2 1.396(2) . ?
N2 H2 0.8800 . ?
C33 C34 1.537(3) . ?
C33 C35 1.536(2) . ?
C33 C36 1.540(3) . ?
C34 H34a 0.9800 . ?
C34 H34b 0.9800 . ?
C34 H34c 0.9800 . ?
C35 H35a 0.9800 . ?
C35 H35b 0.9800 . ?
C35 H35c 0.9800 . ?
C36 H36a 0.9800 . ?
C36 H36b 0.9800 . ?
C36 H36c 0.9800 . ?
C37 C38 1.536(3) . ?
C37 C39 1.533(3) . ?
C37 C40 1.534(2) . ?
C38 H38a 0.9800 . ?
C38 H38b 0.9800 . ?
C38 H38c 0.9800 . ?
C39 H39a 0.9800 . ?
C39 H39b 0.9800 . ?
C39 H39c 0.9800 . ?
C40 H40a 0.9800 . ?
C40 H40b 0.9800 . ?
C40 H40c 0.9800 . ?
C41 H41a 0.9900 . ?
C41 H41b 0.9900 . ?
C41 C42 1.533(3) . ?
C41 C44 1.505(3) . ?
C42 H42a 0.9900 . ?
C42 H42b 0.9900 . ?
C42 C43 1.521(4) . ?
C43 H43a 0.9900 . ?
C43 H43b 0.9900 . ?
C43 O3 1.423(3) . ?
O3 C44 1.429(3) . ?
C44 H44a 0.9900 . ?
C44 H44b 0.9900 . ?
C45 H45a 0.9900 . ?
C45 H45b 0.9900 . ?
C45 C46 1.517(3) . ?
C45 O4 1.418(3) . ?
C46 H46a 0.9900 . ?
C46 H46b 0.9900 . ?
C46 C47 1.473(4) . ?
C47 H47a 0.9900 . ?
C47 H47b 0.9900 . ?
C47 C48 1.492(4) . ?
C48 H48a 0.9900 . ?
C48 H48b 0.9900 . ?
C48 O4 1.425(3) . ?

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 C1 C2 119.19(17) . . ?
C12 C1 C2 106.37(16) 2_576 . ?
C12 C1 C6 134.44(18) 2_576 . ?
C3 C2 C1 124.95(17) . . ?
O1 C2 C1 110.44(15) . . ?
O1 C2 C3 124.61(16) . . ?
C4 C3 C2 114.81(17) . . ?
C13 C3 C2 122.27(17) . . ?
C13 C3 C4 122.93(17) . . ?
H4 C4 C3 119.36(11) . . ?
C5 C4 C3 121.27(17) . . ?
C5 C4 H4 119.36(11) . . ?
C6 C5 C4 122.51(17) . . ?
N1 C5 C4 129.13(17) . . ?
N1 C5 C6 108.36(16) . . ?
C5 C6 C1 117.27(17) . . ?
C7 C6 C1 135.62(17) . . ?
C7 C6 C5 107.11(16) . . ?
C8 C7 C6 107.16(16) . . ?
C12 C7 C6 135.55(17) . . ?
C12 C7 C8 117.29(17) . . ?
C9 C8 C7 122.47(17) . . ?
N1 C8 C7 108.36(16) . . ?
N1 C8 C9 129.17(16) . . ?
H9 C9 C8 119.39(10) . . ?
C10 C9 C8 121.22(17) . . ?
C10 C9 H9 119.39(11) . . ?
C11 C10 C9 115.14(17) . . ?
C17 C10 C9 122.81(16) . . ?
C17 C10 C11 122.04(16) . . ?
C12 C11 C10 124.88(17) . . ?
O1 C11 C10 124.47(16) 2_576 . ?
O1 C11 C12 110.65(15) 2_576 . ?
C7 C12 C1 134.39(17) . 2_576 ?
C11 C12 C1 106.62(16) . 2_576 ?
C11 C12 C7 118.98(16) . . ?
C11 O1 C2 105.92(13) 2_576 . ?
C8 N1 C5 109.01(15) . . ?
H1 N1 C5 125.50(10) . . ?
H1 N1 C8 125.50(10) . . ?
C14 C13 C3 109.74(17) . . ?
C15 C13 C3 109.44(17) . . ?
C15 C13 C14 109.35(17) . . ?
C16 C13 C3 111.57(16) . . ?
C16 C13 C14 108.53(17) . . ?
C16 C13 C15 108.18(17) . . ?
H14a C14 C13 109.5 . . ?
H14b C14 C13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15a C15 C13 109.5 . . ?
H15b C15 C13 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C13 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C13 109.5 . . ?
H16b C16 C13 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C13 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C18 C17 C10 111.42(16) . . ?
C19 C17 C10 110.06(16) . . ?
C19 C17 C18 107.64(16) . . ?
C20 C17 C10 108.94(16) . . ?
C20 C17 C18 108.69(16) . . ?
C20 C17 C19 110.08(18) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
H19a C19 C17 109.5 . . ?
H19b C19 C17 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C17 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H20a C20 C17 109.5 . . ?
H20b C20 C17 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C17 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
C26 C21 C22 119.44(16) . . ?
C31 C21 C22 106.43(16) . . ?
C31 C21 C26 134.13(17) . . ?
C23 C22 C21 124.81(17) . . ?
O2 C22 C21 110.53(15) . . ?
O2 C22 C23 124.64(16) . . ?
C24 C23 C22 115.08(17) . . ?
C33 C23 C22 122.15(16) . . ?
C33 C23 C24 122.73(16) . . ?
H24 C24 C23 119.36(11) . . ?
C25 C24 C23 121.28(17) . . ?
C25 C24 H24 119.36(10) . . ?
C26 C25 C24 122.51(17) . . ?
N2 C25 C24 129.26(17) . . ?
N2 C25 C26 108.22(16) . . ?
C25 C26 C21 116.87(17) . . ?
C27 C26 C21 135.77(17) 2_665 . ?
C27 C26 C25 107.34(16) 2_665 . ?
C28 C27 C26 107.13(16) 2_665 2_665 ?
C31 C27 C26 135.92(17) . 2_665 ?
C31 C27 C28 116.94(17) . 2_665 ?
C29 C28 C27 122.62(17) . 2_665 ?
N2 C28 C27 108.36(16) . 2_665 ?
N2 C28 C29 129.02(16) . . ?
H29 C29 C28 119.42(10) . . ?
C30 C29 C28 121.16(17) . . ?
C30 C29 H29 119.42(11) . . ?
C32 C30 C29 114.96(17) 2_665 . ?
C37 C30 C29 123.01(16) . . ?
C37 C30 C32 122.03(16) . 2_665 ?
C27 C31 C21 134.17(17) . . ?
C32 C31 C21 106.70(16) . . ?
C32 C31 C27 119.13(16) . . ?
C31 C32 C30 125.19(17) . 2_665 ?
O2 C32 C30 124.39(16) . 2_665 ?
O2 C32 C31 110.42(15) . . ?
C32 O2 C22 105.91(13) . . ?
C28 N2 C25 108.94(15) . . ?
H2 N2 C25 125.53(10) . . ?
H2 N2 C28 125.53(10) . . ?
C34 C33 C23 109.31(15) . . ?
C35 C33 C23 111.76(15) . . ?
C35 C33 C34 107.77(16) . . ?
C36 C33 C23 109.70(16) . . ?
C36 C33 C34 109.90(16) . . ?
C36 C33 C35 108.37(16) . . ?
H34a C34 C33 109.5 . . ?
H34b C34 C33 109.5 . . ?
H34b C34 H34a 109.5 . . ?
H34c C34 C33 109.5 . . ?
H34c C34 H34a 109.5 . . ?
H34c C34 H34b 109.5 . . ?
H35a C35 C33 109.5 . . ?
H35b C35 C33 109.5 . . ?
H35b C35 H35a 109.5 . . ?
H35c C35 C33 109.5 . . ?
H35c C35 H35a 109.5 . . ?
H35c C35 H35b 109.5 . . ?
H36a C36 C33 109.5 . . ?
H36b C36 C33 109.5 . . ?
H36b C36 H36a 109.5 . . ?
H36c C36 C33 109.5 . . ?
H36c C36 H36a 109.5 . . ?
H36c C36 H36b 109.5 . . ?
C38 C37 C30 108.54(16) . . ?
C39 C37 C30 110.37(16) . . ?
C39 C37 C38 109.87(16) . . ?
C40 C37 C30 112.07(15) . . ?
C40 C37 C38 108.22(16) . . ?
C40 C37 C39 107.74(16) . . ?
H38a C38 C37 109.5 . . ?
H38b C38 C37 109.5 . . ?
H38b C38 H38a 109.5 . . ?
H38c C38 C37 109.5 . . ?
H38c C38 H38a 109.5 . . ?
H38c C38 H38b 109.5 . . ?
H39a C39 C37 109.5 . . ?
H39b C39 C37 109.5 . . ?
H39b C39 H39a 109.5 . . ?
H39c C39 C37 109.5 . . ?
H39c C39 H39a 109.5 . . ?
H39c C39 H39b 109.5 . . ?
H40a C40 C37 109.5 . . ?
H40b C40 C37 109.5 . . ?
H40b C40 H40a 109.5 . . ?
H40c C40 C37 109.5 . . ?
H40c C40 H40a 109.5 . . ?
H40c C40 H40b 109.5 . . ?
H41b C41 H41a 109.0 . . ?
C42 C41 H41a 110.98(12) . . ?
C42 C41 H41b 110.98(12) . . ?
C44 C41 H41a 110.98(12) . . ?
C44 C41 H41b 110.98(12) . . ?
C44 C41 C42 103.91(19) . . ?
H42a C42 C41 111.10(12) . . ?
H42b C42 C41 111.10(12) . . ?
H42b C42 H42a 109.1 . . ?
C43 C42 C41 103.29(19) . . ?
C43 C42 H42a 111.10(13) . . ?
C43 C42 H42b 111.10(15) . . ?
H43a C43 C42 110.25(14) . . ?
H43b C43 C42 110.25(15) . . ?
H43b C43 H43a 108.5 . . ?
O3 C43 C42 107.3(2) . . ?
O3 C43 H43a 110.25(14) . . ?
O3 C43 H43b 110.25(13) . . ?
C44 O3 C43 104.66(17) . . ?
O3 C44 C41 105.10(18) . . ?
H44a C44 C41 110.72(13) . . ?
H44a C44 O3 110.72(11) . . ?
H44b C44 C41 110.72(12) . . ?
H44b C44 O3 110.72(11) . . ?
H44b C44 H44a 108.8 . . ?
H45b C45 H45a 108.8 . . ?
C46 C45 H45a 110.72(16) . . ?
C46 C45 H45b 110.72(15) . . ?
O4 C45 H45a 110.72(14) . . ?
O4 C45 H45b 110.72(13) . . ?
O4 C45 C46 105.1(2) . . ?
H46a C46 C45 110.65(15) . . ?
H46b C46 C45 110.65(15) . . ?
H46b C46 H46a 108.8 . . ?
C47 C46 C45 105.5(2) . . ?
C47 C46 H46a 110.7(2) . . ?
C47 C46 H46b 110.65(18) . . ?
H47a C47 C46 110.5(2) . . ?
H47b C47 C46 110.47(19) . . ?
H47b C47 H47a 108.7 . . ?
C48 C47 C46 106.3(2) . . ?
C48 C47 H47a 110.5(2) . . ?
C48 C47 H47b 110.47(19) . . ?
H48a C48 C47 110.35(19) . . ?
H48b C48 C47 110.3(2) . . ?
H48b C48 H48a 108.6 . . ?
O4 C48 C47 106.9(2) . . ?
O4 C48 H48a 110.35(13) . . ?
O4 C48 H48b 110.35(15) . . ?
C48 O4 C45 108.31(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.8800 1.979(2) 2.828(2) 161.64(8) .
N2 H2 O3 0.8800 2.008(2) 2.857(2) 161.75(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
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C13 -179.3(2) . . . . ?
C1 C2 O1 C11 0.25(19) . . . 2_576 ?
C1 C6 C5 C4 0.9(2) . . . . ?
C1 C6 C5 N1 -179.70(19) . . . . ?
C1 C6 C7 C8 179.9(3) . . . . ?
C1 C6 C7 C12 0.0(3) . . . . ?
C1 C12 C7 C6 -0.0(3) 2_576 . . . ?
C1 C12 C7 C8 -179.9(2) 2_576 . . . ?
C1 C12 C11 C10 -179.24(15) 2_576 . . . ?
C1 C12 C11 O1 -0.56(17) . 2_576 2_576 . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C13 C14 -60.1(2) . . . . ?
C2 C3 C13 C15 59.9(2) . . . . ?
C2 C3 C13 C16 179.5(2) . . . . ?
C2 O1 C11 C10 -179.60(15) . . 2_576 2_576 ?
C2 O1 C11 C12 0.20(16) . . 2_576 2_576 ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 N1 -179.18(19) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 N1 C8 179.0(2) . . . . ?
C5 C6 C7 C8 -0.14(18) . . . . ?
C5 C6 C7 C12 -179.98(16) . . . . ?
C5 N1 C8 C7 0.30(18) . . . . ?
C5 N1 C8 C9 -179.43(16) . . . . ?
C6 C7 C8 C9 179.66(16) . . . . ?
C6 C7 C8 N1 -0.10(18) . . . . ?
C6 C7 C12 C11 179.5(2) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C7 C12 C11 C10 1.1(2) . . . . ?
C7 C12 C11 O1 -179.12(18) . . . 2_576 ?
C8 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C17 179.39(18) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C9 C10 C11 O1 179.23(16) . . . 2_576 ?
C9 C10 C17 C18 3.8(2) . . . . ?
C9 C10 C17 C19 123.1(2) . . . . ?
C9 C10 C17 C20 -116.1(2) . . . . ?
C21 C22 C23 C24 -1.1(2) . . . . ?
C21 C22 C23 C33 176.64(19) . . . . ?
C21 C22 O2 C32 0.76(18) . . . . ?
C21 C26 C25 C24 0.4(2) . . . . ?
C21 C26 C25 N2 -178.27(18) . . . . ?
C21 C26 C27 C28 178.4(3) . . 2_665 . ?
C21 C26 C27 C31 -0.9(3) . . 2_665 2_665 ?
C21 C31 C27 C26 -0.4(3) . . . 2_665 ?
C21 C31 C27 C28 178.9(2) . . . 2_665 ?
C21 C31 C32 C30 -179.34(15) . . . 2_665 ?
C21 C31 C32 O2 0.65(17) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C22 C23 C33 C34 -59.0(2) . . . . ?
C22 C23 C33 C35 -178.2(2) . . . . ?
C22 C23 C33 C36 61.6(2) . . . . ?
C22 O2 C32 C30 179.12(14) . . . 2_665 ?
C22 O2 C32 C31 -0.87(15) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
C23 C24 C25 N2 177.96(18) . . . . ?
C24 C25 C26 C27 179.2(2) . . . 2_665 ?
C24 C25 N2 C28 -179.4(2) . . . . ?
C25 C26 C27 C28 -0.08(18) . . 2_665 . ?
C25 C26 C27 C31 -179.44(15) . . 2_665 2_665 ?
C25 N2 C28 C27 0.78(17) . . . 2_665 ?
C25 N2 C28 C29 -179.33(16) . . . . ?
C26 C27 C28 C29 179.68(15) . 2_665 . . ?
C26 C27 C28 N2 -0.43(17) . 2_665 . . ?
C26 C27 C31 C32 179.4(2) 2_665 . . . ?
C27 C28 C29 C30 -0.2(2) 2_665 . . . ?
C27 C31 C32 C30 0.8(2) . . . 2_665 ?
C27 C31 C32 O2 -179.23(18) . . . . ?
C28 C29 C30 C32 0.6(2) . . . 2_665 ?
C28 C29 C30 C37 -179.00(18) . . . . ?
C29 C30 C32 C31 -0.2(2) . . 2_665 2_665 ?
C29 C30 C32 O2 179.80(15) . . 2_665 2_665 ?
C29 C30 C37 C38 116.6(2) . . . . ?
C29 C30 C37 C39 -122.9(2) . . . . ?
C29 C30 C37 C40 -2.9(2) . . . . ?
C41 C42 C43 O3 -14.89(19) . . . . ?
C41 C44 O3 C43 -40.8(2) . . . . ?
C42 C43 O3 C44 34.8(2) . . . . ?
C45 C46 C47 C48 7.9(3) . . . . ?
C45 O4 C48 C47 -24.6(3) . . . . ?
C46 C47 C48 O4 9.5(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.447 0.500 0.500 837.5 284.5 '7 THF'
2 0.201 0.936 0.878 11.3 0.0 ?
3 0.799 0.064 0.122 11.3 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
