# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_170613LT_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2gryx3
_database_code_depnum_ccdc_archive 'CCDC 2287146'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3GC04062C 2024
loop_
_audit_author_name
_audit_author_address
'Mahima Gupta'
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H12 F2 N2'
_chemical_formula_weight         330.33

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.4478(6)
_cell_length_b                   17.5319(7)
_cell_length_c                   12.9774(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.180(2)
_cell_angle_gamma                90
_cell_volume                     3245.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3181
_cell_measurement_theta_min      2.8155
_cell_measurement_theta_max      22.6191

_exptl_crystal_description       Lump
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12325
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3321
_reflns_number_gt                2370
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0605P)²+1.2434P] 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         3321
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_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
F1 F 0.14485(14) -0.03143(8) 1.04522(16) 0.1383(7) Uani 1 1 d . . . . .
F2 F 0.11889(10) 0.16425(8) 0.29189(10) 0.0967(5) Uani 1 1 d . . . . .
N1 N 0.12007(9) 0.45583(8) 0.59912(9) 0.0436(3) Uani 1 1 d . . . . .
N2 N 0.12378(12) 0.43397(9) 0.77025(10) 0.0597(4) Uani 1 1 d . . . . .
C1 C 0.12045(14) 0.21661(11) 0.36954(14) 0.0629(5) Uani 1 1 d . . . . .
C2 C 0.17879(13) 0.27776(11) 0.37097(13) 0.0574(5) Uani 1 1 d . . . . .
H12 H 0.2175 0.2838 0.3188 0.069 Uiso 1 1 calc R U . . .
C3 C 0.18048(12) 0.33102(10) 0.45009(12) 0.0494(4) Uani 1 1 d . . . . .
H11 H 0.2210 0.3739 0.4524 0.059 Uiso 1 1 calc R U . . .
C4 C 0.12340(11) 0.32244(9) 0.52629(11) 0.0450(4) Uani 1 1 d . . . . .
C5 C 0.12399(11) 0.37749(9) 0.61162(11) 0.0445(4) Uani 1 1 d . . . . .
C6 C 0.12596(12) 0.36631(10) 0.71749(12) 0.0512(4) Uani 1 1 d . . . . .
C7 C 0.13227(13) 0.29526(11) 0.77171(12) 0.0548(4) Uani 1 1 d . . . . .
C8 C 0.13739(13) 0.23678(11) 0.81942(13) 0.0557(5) Uani 1 1 d . . . . .
C9 C 0.14095(12) 0.16681(10) 0.87689(14) 0.0543(4) Uani 1 1 d . . . . .
C10 C 0.12473(17) 0.09773(13) 0.82682(19) 0.0831(7) Uani 1 1 d . . . . .
H9 H 0.1120 0.0959 0.7527 0.100 Uiso 1 1 calc R U . . .
C11 C 0.1269(2) 0.03039(13) 0.8846(3) 0.1019(9) Uani 1 1 d . . . . .
H8 H 0.1164 -0.0176 0.8506 0.122 Uiso 1 1 calc R U . . .
C12 C 0.14431(18) 0.03496(13) 0.9902(2) 0.0871(7) Uani 1 1 d . . . . .
C13 C 0.06600(12) 0.25868(10) 0.52201(14) 0.0559(5) Uani 1 1 d . . . . .
H2 H 0.0271 0.2518 0.5738 0.067 Uiso 1 1 calc R U . . .
C14 C 0.06438(14) 0.20498(12) 0.44367(16) 0.0671(5) Uani 1 1 d . . . . .
H1 H 0.0254 0.1612 0.4414 0.081 Uiso 1 1 calc R U . . .
C15 C 0.11347(11) 0.50165(10) 0.51164(11) 0.0470(4) Uani 1 1 d . . . . .
H3 H 0.1133 0.4795 0.4448 0.056 Uiso 1 1 calc R U . . .
C16 C 0.10733(12) 0.57765(10) 0.52147(13) 0.0517(4) Uani 1 1 d . . . . .
H4 H 0.1038 0.6091 0.4613 0.062 Uiso 1 1 calc R U . . .
C17 C 0.10600(14) 0.61132(11) 0.61954(14) 0.0607(5) Uani 1 1 d . . . . .
H5 H 0.1014 0.6651 0.6253 0.073 Uiso 1 1 calc R U . . .
C18 C 0.11136(15) 0.56688(11) 0.70592(14) 0.0635(5) Uani 1 1 d . . . . .
H10 H 0.1099 0.5896 0.7721 0.076 Uiso 1 1 calc R U . . .
C19 C 0.11900(12) 0.48751(10) 0.69763(11) 0.0516(4) Uani 1 1 d . . . . .
C20 C 0.16232(15) 0.10080(13) 1.04192(18) 0.0740(6) Uani 1 1 d . . . . .
H7 H 0.1758 0.1015 1.1160 0.089 Uiso 1 1 calc R U . . .
C21 C 0.16098(13) 0.16746(11) 0.98545(14) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.1739 0.2145 1.0211 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C12 1.365(2) . ?
F2 C1 1.361(2) . ?
N1 C15 1.3815(19) . ?
N1 C5 1.383(2) . ?
N1 C19 1.3962(19) . ?
N2 C19 1.324(2) . ?
N2 C6 1.373(2) . ?
C1 C2 1.362(3) . ?
C1 C14 1.368(3) . ?
C2 C3 1.385(2) . ?
C2 H12 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H11 0.9500 . ?
C4 C13 1.388(2) . ?
C4 C5 1.468(2) . ?
C5 C6 1.384(2) . ?
C6 C7 1.426(2) . ?
C7 C8 1.194(2) . ?
C8 C9 1.432(2) . ?
C9 C10 1.377(3) . ?
C9 C21 1.392(3) . ?
C10 C11 1.396(3) . ?
C10 H9 0.9500 . ?
C11 C12 1.356(4) . ?
C11 H8 0.9500 . ?
C12 C20 1.339(3) . ?
C13 C14 1.383(2) . ?
C13 H2 0.9500 . ?
C14 H1 0.9500 . ?
C15 C16 1.343(2) . ?
C15 H3 0.9500 . ?
C16 C17 1.406(2) . ?
C16 H4 0.9500 . ?
C17 C18 1.357(3) . ?
C17 H5 0.9500 . ?
C18 C19 1.401(3) . ?
C18 H10 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H7 0.9500 . ?
C21 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C5 132.06(13) . . ?
C15 N1 C19 120.78(14) . . ?
C5 N1 C19 107.09(12) . . ?
C19 N2 C6 105.09(13) . . ?
F2 C1 C2 118.57(18) . . ?
F2 C1 C14 118.59(19) . . ?
C2 C1 C14 122.84(17) . . ?
C1 C2 C3 118.58(16) . . ?
C1 C2 H12 120.7 . . ?
C3 C2 H12 120.7 . . ?
C2 C3 C4 120.72(17) . . ?
C2 C3 H11 119.6 . . ?
C4 C3 H11 119.6 . . ?
C13 C4 C3 118.44(15) . . ?
C13 C4 C5 119.44(14) . . ?
C3 C4 C5 122.11(15) . . ?
N1 C5 C6 104.54(14) . . ?
N1 C5 C4 124.70(13) . . ?
C6 C5 C4 130.74(15) . . ?
N2 C6 C5 111.99(15) . . ?
N2 C6 C7 120.89(14) . . ?
C5 C6 C7 127.09(16) . . ?
C8 C7 C6 178.30(18) . . ?
C7 C8 C9 178.48(19) . . ?
C10 C9 C21 118.49(18) . . ?
C10 C9 C8 121.23(18) . . ?
C21 C9 C8 120.28(17) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H9 119.9 . . ?
C11 C10 H9 119.9 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H8 120.7 . . ?
C10 C11 H8 120.7 . . ?
C20 C12 C11 123.2(2) . . ?
C20 C12 F1 119.3(3) . . ?
C11 C12 F1 117.6(3) . . ?
C14 C13 C4 121.18(16) . . ?
C14 C13 H2 119.4 . . ?
C4 C13 H2 119.4 . . ?
C1 C14 C13 118.23(18) . . ?
C1 C14 H1 120.9 . . ?
C13 C14 H1 120.9 . . ?
C16 C15 N1 119.73(14) . . ?
C16 C15 H3 120.1 . . ?
N1 C15 H3 120.1 . . ?
C15 C16 C17 120.88(15) . . ?
C15 C16 H4 119.6 . . ?
C17 C16 H4 119.6 . . ?
C18 C17 C16 119.97(18) . . ?
C18 C17 H5 120.0 . . ?
C16 C17 H5 120.0 . . ?
C17 C18 C19 120.09(16) . . ?
C17 C18 H10 120.0 . . ?
C19 C18 H10 120.0 . . ?
N2 C19 N1 111.27(15) . . ?
N2 C19 C18 130.17(15) . . ?
N1 C19 C18 118.54(15) . . ?
C12 C20 C21 118.7(2) . . ?
C12 C20 H7 120.7 . . ?
C21 C20 H7 120.7 . . ?
C20 C21 C9 120.9(2) . . ?
C20 C21 H6 119.5 . . ?
C9 C21 H6 119.5 . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.037

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_230756l3_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2303798'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3GC04062C 2024
loop_
_audit_author_name
_audit_author_address
'Mahima Gupta'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-10-26 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H16 N2)'
_chemical_formula_sum            'C44 H32 N4'
_chemical_formula_weight         616.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H34 N4'
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'

_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                   16.7695(5)
_cell_length_b                   8.6997(3)
_cell_length_c                   11.0836(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.718(3)
_cell_angle_gamma                90
_cell_volume                     1616.26(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9209
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      72.6340
_cell_measurement_theta_min      2.6100
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.460
_diffrn_reflns_theta_min         2.636
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -26.00   0.50    5.40    --  -14.00 -56.00  -1.19   56
  2  ω    -71.00 -36.00   0.50    5.40    --  -22.00 -49.00  -2.21   70
  3  ω    -78.00 -43.00   0.50    5.40    --  -30.00 -51.00 -30.73   70
  4  ω    -83.00 -48.00   0.50    5.40    --  -34.00 -47.00 -26.45   70
  5  ω    -86.00 -51.00   0.50    5.40    --  -38.00 -51.00 -48.51   70
  6  ω    -90.00 -55.00   0.50    5.40    --  -42.00 -51.00   1.96   70
  7  ω    -90.00 -55.00   0.50    5.40    --  -42.00 -52.00  35.79   70
  8  ω    -92.00 -55.00   0.50    5.40    --  -42.00 -45.00   0.34   74
  9  ω    -94.00 -59.00   0.50    5.40    --  -46.00 -52.00 -54.26   70
 10  ω   -100.00 -62.00   0.50    5.40    --  -50.00 -43.00 160.65   76
 11  ω    -98.00 -63.00   0.50    5.40    --  -50.00 -52.00 -62.88   70
 12  ω   -102.00 -67.00   0.50    5.40    --  -54.00 -51.00 -63.38   70
 13  ω     13.00  64.00   0.50    5.40    --   56.05 -95.00 -60.00  102
 14  ω    -99.00 -73.00   0.50    5.40    --  -58.00 -52.00  -9.41   52
 15  ω    -98.00 -72.00   0.50    5.40    --  -58.00 -52.00 -25.77   52
 16  ω    -96.00 -71.00   0.50    5.40    --  -58.00 -51.00  30.46   50
 17  ω   -100.00 -74.00   0.50    5.40    --  -58.00 -52.00 -34.41   52
 18  ω     71.00  96.00   0.50    5.40    --   58.00  52.00  52.20   50
 19  ω   -103.00 -77.00   0.50    5.40    --  -62.00 -51.00   0.86   52
 20  ω   -103.00 -77.00   0.50    5.40    --  -62.00 -51.00 -30.26   52
 21  ω   -108.00 -81.00   0.50    5.40    --  -66.00 -47.00 -53.00   54
 22  ω   -106.00 -80.00   0.50    5.40    --  -66.00 -51.00  38.54   52
 23  ω   -109.00 -83.00   0.50    5.40    --  -66.00 -52.00 -63.74   52
 24  ω   -106.00 -80.00   0.50    5.40    --  -66.00 -51.00 -37.73   52
 25  ω     59.00  85.00   0.50    5.40    --   69.01  15.00  60.00   52
 26  ω     93.00 119.00   0.50    5.40    --   69.01  15.00  60.00   52
 27  ω   -119.00 -93.00   0.50    5.40    --  -70.00 -49.00-116.15   52
 28  ω   -121.00 -84.00   0.50    5.40    --  -70.00 -34.00-111.94   74
 29  ω   -113.00 -85.00   0.50    5.40    --  -70.00 -48.00 145.47   56
 30  ω   -109.00 -83.00   0.50    5.40    --  -70.00 -43.00  43.28   52
 31  ω   -119.00 -90.00   0.50    5.40    --  -74.00 -58.00 117.97   58
 32  ω   -114.00 -88.00   0.50    5.40    --  -74.00 -40.00  -5.69   52
 33  ω   -113.00 -87.00   0.50    5.40    --  -74.00 -55.00  27.32   52
 34  ω    -89.00 -35.00   0.50    5.40    --  -75.32 111.00  60.00  108
 35  ω    -55.00 -30.00   0.50    5.40    --  -75.32 111.00-180.00   50
 36  ω    -91.00 -60.00   0.50    5.40    --  -75.32 111.00-180.00   62
 37  ω     41.00  67.00   0.50    5.40    --   75.94-111.00  30.00   52
 38  ω     33.00  91.00   0.50    5.40    --   75.94-111.00 -60.00  116
 39  ω     39.00  67.00   0.50    5.40    --   75.94 -95.00  30.00   56
 40  ω   -117.00 -90.00   0.50    5.40    --  -78.00 -58.00 -40.45   54
 41  ω   -118.00 -92.00   0.50    5.40    --  -79.90 -56.00  35.62   52
 42  ω   -121.00 -95.00   0.50    5.40    --  -79.90 -47.00 128.51   52
 43  ω   -125.00-100.00   0.50    5.40    --  -79.90-126.00  45.86   50
 44  ω   -121.00 -95.00   0.50    5.40    --  -79.90 -51.00   3.00   52
 45  ω   -131.00 -92.00   0.50    5.40    --  -79.90 -40.00 150.31   78
 46  ω   -124.00 -98.00   0.50    5.40    --  -79.90 -59.00-164.28   52
 47  ω   -124.00 -91.00   0.50    5.40    --  -79.90-134.00 106.81   66
 48  ω   -123.00 -97.00   0.50    5.40    --  -79.90 -62.00 -44.32   52
 49  ω    -75.00 -33.00   0.50    5.40    --  -79.90 136.00  35.42   84
 50  ω   -120.00 -93.00   0.50    5.40    --  -79.90 -52.00  50.90   54
 51  ω   -124.00 -95.00   0.50    5.40    --  -79.90-119.00  62.42   58
 52  ω   -128.00 -94.00   0.50    5.40    --  -79.90 -52.00 -63.90   68
 53  ω   -118.00 -92.00   0.50    5.40    --  -79.90 -56.00 -35.41   52
 54  ω   -119.00 -92.00   0.50    5.40    --  -79.90 -62.00 138.16   54
 55  ω   -127.00-102.00   0.50    5.40    --  -79.90 -58.00 156.01   50
 56  ω   -129.00 -94.00   0.50    5.40    --  -79.90 -41.00 -30.01   70
 57  ω   -127.00-102.00   0.50    5.40    --  -79.90 -55.00 -84.52   50
 58  ω   -127.00-102.00   0.50    5.40    --  -79.90-122.00-129.03   50
 59  ω     93.00 119.00   0.50    5.40    --   79.90 138.00-124.57   52
 60  ω     94.00 124.00   0.50    5.40    --   79.90  59.00 -18.86   60
 61  ω     46.00  91.00   0.50    5.40    --   83.87 -95.00 120.00   90
 62  ω     40.00  84.00   0.50    5.40    --   83.87-111.00 -90.00   88
 63  ω     45.00  90.00   0.50    5.40    --   83.87 -95.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0716294000
_diffrn_orient_matrix_UB_12      -0.0809438000
_diffrn_orient_matrix_UB_13      -0.0562955000
_diffrn_orient_matrix_UB_21      0.0419883000
_diffrn_orient_matrix_UB_22      -0.0096492000
_diffrn_orient_matrix_UB_23      0.1253521000
_diffrn_orient_matrix_UB_31      -0.0394464000
_diffrn_orient_matrix_UB_32      -0.1571377000
_diffrn_orient_matrix_UB_33      0.0213426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3041
_reflns_number_total             3602
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.2067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5422(12)
 0.4578(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
C1 C 0.66481(8) 0.36834(16) 0.02215(13) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.64988(8) 0.43549(16) 0.13256(13) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.51902(8) 0.46105(16) 0.23734(12) 0.0208(3) Uani 1 1 d . . . . .
H3 H 0.540030 0.517636 0.304350 0.025 Uiso 1 1 calc R U . . .
C4 C 0.43964(8) 0.43064(16) 0.22791(13) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.40974(9) 0.34195(16) 0.12812(13) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.354584 0.317091 0.122904 0.028 Uiso 1 1 calc R U . . .
C6 C 0.45835(8) 0.29239(16) 0.04055(13) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.437273 0.233836 -0.025349 0.028 Uiso 1 1 calc R U . . .
C7 C 0.54064(8) 0.32842(16) 0.04794(12) 0.0206(3) Uani 1 1 d . . . . .
C8 C 0.73772(9) 0.37181(16) -0.04086(13) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.79534(9) 0.37845(17) -0.10242(13) 0.0234(3) Uani 1 1 d . . . . .
C10 C 0.86102(8) 0.39212(17) -0.18163(13) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.85251(9) 0.34156(18) -0.30140(14) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.804487 0.293012 -0.328467 0.032 Uiso 1 1 calc R U . . .
C12 C 0.91398(9) 0.36233(19) -0.38013(15) 0.0310(4) Uani 1 1 d . . . . .
H12 H 0.907805 0.329104 -0.461520 0.037 Uiso 1 1 calc R U . . .
C13 C 0.98457(10) 0.4314(2) -0.34089(15) 0.0333(4) Uani 1 1 d . . . . .
H13 H 1.026678 0.445116 -0.395341 0.040 Uiso 1 1 calc R U . . .
C14 C 0.99382(10) 0.4804(2) -0.22242(15) 0.0339(4) Uani 1 1 d . . . . .
H14 H 1.042329 0.527438 -0.195686 0.041 Uiso 1 1 calc R U . . .
C15 C 0.93266(9) 0.46105(19) -0.14301(15) 0.0291(4) Uani 1 1 d . . . . .
H15 H 0.939317 0.494731 -0.061794 0.035 Uiso 1 1 calc R U . . .
C16 C 0.38252(9) 0.49635(18) 0.31639(14) 0.0261(3) Uani 1 1 d . . . . .
H16A H 0.355018 0.585176 0.280116 0.039 Uiso 1 1 calc R U . . .
H16B H 0.412080 0.528740 0.389654 0.039 Uiso 1 1 calc R U . . .
H16C H 0.343250 0.417946 0.337040 0.039 Uiso 1 1 calc R U . . .
C17 C 0.70297(8) 0.52059(16) 0.21653(13) 0.0204(3) Uani 1 1 d . . . . .
C18 C 0.75507(8) 0.63051(17) 0.17029(13) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.754082 0.651379 0.086124 0.028 Uiso 1 1 calc R U . . .
C19 C 0.80798(9) 0.70890(18) 0.24653(14) 0.0268(3) Uani 1 1 d . . . . .
H19 H 0.842973 0.783448 0.214616 0.032 Uiso 1 1 calc R U . . .
C20 C 0.80983(9) 0.67850(18) 0.36935(14) 0.0271(3) Uani 1 1 d . . . . .
H20 H 0.846060 0.732253 0.421629 0.032 Uiso 1 1 calc R U . . .
C21 C 0.75876(8) 0.56954(18) 0.41590(13) 0.0244(3) Uani 1 1 d . . . . .
H21 H 0.760366 0.548582 0.500055 0.029 Uiso 1 1 calc R U . . .
C22 C 0.70529(8) 0.49088(16) 0.34029(13) 0.0217(3) Uani 1 1 d . . . . .
H22 H 0.670294 0.416827 0.372854 0.026 Uiso 1 1 calc R U . . .
N1 N 0.59780(7) 0.30058(13) -0.02953(11) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.56923(7) 0.40949(13) 0.14918(10) 0.0198(3) 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 1.386(2) . ?
C1 C8 1.427(2) . ?
C1 N1 1.3782(18) . ?
C2 C17 1.469(2) . ?
C2 N2 1.3890(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(2) . ?
C3 N2 1.3835(17) . ?
C4 C5 1.427(2) . ?
C4 C16 1.504(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.356(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.415(2) . ?
C7 N1 1.3281(18) . ?
C7 N2 1.3979(18) . ?
C8 C9 1.201(2) . ?
C9 C10 1.434(2) . ?
C10 C11 1.402(2) . ?
C10 C15 1.398(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.403(2) . ?
C17 C22 1.395(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(2) . ?
C22 H22 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
C2 C1 C8 127.13(14) . . ?
N1 C1 C2 112.38(12) . . ?
N1 C1 C8 120.38(13) . . ?
C1 C2 C17 130.55(13) . . ?
C1 C2 N2 104.53(12) . . ?
N2 C2 C17 124.90(12) . . ?
C4 C3 H3 120.1 . . ?
C4 C3 N2 119.89(13) . . ?
N2 C3 H3 120.1 . . ?
C3 C4 C5 119.06(13) . . ?
C3 C4 C16 121.18(13) . . ?
C5 C4 C16 119.66(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.44(13) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.61(14) . . ?
C7 C6 H6 120.2 . . ?
N1 C7 C6 130.07(13) . . ?
N1 C7 N2 111.97(12) . . ?
N2 C7 C6 117.94(12) . . ?
C9 C8 C1 174.44(16) . . ?
C8 C9 C10 176.21(16) . . ?
C11 C10 C9 119.71(13) . . ?
C15 C10 C9 121.12(14) . . ?
C15 C10 C11 119.11(14) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.02(15) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.32(15) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.09(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.16(15) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.30(15) . . ?
C14 C15 H15 119.8 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C2 118.98(13) . . ?
C22 C17 C2 121.88(13) . . ?
C22 C17 C18 119.09(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.46(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.99(14) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.98(14) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.45(14) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.03(13) . . ?
C21 C22 H22 120.0 . . ?
C7 N1 C1 104.39(11) . . ?
C2 N2 C7 106.71(11) . . ?
C3 N2 C2 131.03(12) . . ?
C3 N2 C7 121.95(12) . . ?

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 C17 C18 43.6(2) . . . . ?
C1 C2 C17 C22 -133.77(16) . . . . ?
C1 C2 N2 C3 -173.56(13) . . . . ?
C1 C2 N2 C7 0.01(14) . . . . ?
C2 C1 N1 C7 1.21(16) . . . . ?
C2 C17 C18 C19 -177.66(13) . . . . ?
C2 C17 C22 C21 177.31(13) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C4 C3 N2 C2 173.99(13) . . . . ?
C4 C3 N2 C7 1.2(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 N1 -175.54(14) . . . . ?
C5 C6 C7 N2 2.5(2) . . . . ?
C6 C7 N1 C1 176.98(15) . . . . ?
C6 C7 N2 C2 -177.65(12) . . . . ?
C6 C7 N2 C3 -3.36(19) . . . . ?
C8 C1 C2 C17 -2.9(3) . . . . ?
C8 C1 C2 N2 175.40(14) . . . . ?
C8 C1 N1 C7 -175.24(13) . . . . ?
C9 C10 C11 C12 176.33(14) . . . . ?
C9 C10 C15 C14 -176.63(15) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C10 C15 C14 0.7(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C15 C10 C11 C12 -1.0(2) . . . . ?
C16 C4 C5 C6 174.01(14) . . . . ?
C17 C2 N2 C3 4.9(2) . . . . ?
C17 C2 N2 C7 178.46(13) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C17 C22 C21 -0.1(2) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C20 C21 C22 C17 0.3(2) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
N1 C1 C2 C17 -179.08(14) . . . . ?
N1 C1 C2 N2 -0.76(16) . . . . ?
N1 C7 N2 C2 0.77(16) . . . . ?
N1 C7 N2 C3 175.06(12) . . . . ?
N2 C2 C17 C18 -134.40(14) . . . . ?
N2 C2 C17 C22 48.2(2) . . . . ?
N2 C3 C4 C5 1.6(2) . . . . ?
N2 C3 C4 C16 -174.73(12) . . . . ?
N2 C7 N1 C1 -1.19(15) . . . . ?

_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.895
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5422(12) 13205 9946 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4578(12) 0 9946 nmt -0.9997 -0.0009 -0.0913 0.0001 -1.0001 0.0001 0.0001
-0.0012 1.0006

_twin_special_details            
;
Component 2 rotated by 179.9878° 
around [-0.05 0.00 1.00] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
####################################################################### 
# 
# 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_mo_170754LT_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2grz18
_database_code_depnum_ccdc_archive 'CCDC 2287150'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3GC04062C 2024
loop_
_audit_author_name
_audit_author_address
'Mahima Gupta'
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2023-08-07 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H12 Br2 N2'
_chemical_formula_weight         452.15

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   3.8778(5)
_cell_length_b                   12.9392(17)
_cell_length_c                   16.735(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.968(3)
_cell_angle_gamma                90
_cell_volume                     838.57(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3000
_cell_measurement_theta_min      2.4373
_cell_measurement_theta_max      26.3010

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.839
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7232
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6578
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.218
_diffrn_reflns_theta_max         26.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3304
_reflns_number_gt                3059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.971

_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)] 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_abs_structure_details 
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(7)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3304
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.950
_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
Br1 Br -0.24778(14) 1.38958(5) -0.00834(3) 0.02031(16) Uani 1 1 d . . . . .
Br2 Br 0.62641(13) 0.61550(4) 0.12504(3) 0.01840(14) Uani 1 1 d . . . . .
N1 N 0.6927(11) 1.0831(3) 0.4695(2) 0.0139(10) Uani 1 1 d . . . . .
N2 N 0.8254(11) 0.9128(3) 0.4777(2) 0.0123(10) Uani 1 1 d . . . . .
C1 C -0.0615(13) 1.3072(5) 0.0782(3) 0.0140(12) Uani 1 1 d . . . . .
C2 C -0.0840(15) 1.2013(5) 0.0737(3) 0.0182(14) Uani 1 1 d . . . . .
H12 H -0.1853 1.1686 0.0274 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0437(14) 1.1434(4) 0.1379(3) 0.0178(13) Uani 1 1 d . . . . .
H1 H 0.0274 1.0702 0.1360 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1972(13) 1.1915(4) 0.2060(3) 0.0127(11) Uani 1 1 d . . . . .
C5 C 0.3324(13) 1.1325(4) 0.2739(3) 0.0131(12) Uani 1 1 d . . . . .
C6 C 0.4520(13) 1.0879(4) 0.3310(3) 0.0140(12) Uani 1 1 d . . . . .
C7 C 0.6050(14) 1.0332(4) 0.3982(3) 0.0136(12) Uani 1 1 d . . . . .
C8 C 0.6835(13) 0.9297(4) 0.4002(3) 0.0119(11) Uani 1 1 d . . . . .
C9 C 0.6599(13) 0.8521(4) 0.3366(3) 0.0132(11) Uani 1 1 d . . . . .
C10 C 0.5339(13) 0.7517(4) 0.3470(3) 0.0140(11) Uani 1 1 d . . . . .
H4 H 0.4566 0.7311 0.3975 0.017 Uiso 1 1 calc R U . . .
C11 C 0.5215(13) 0.6821(4) 0.2835(3) 0.0146(12) Uani 1 1 d . . . . .
H7 H 0.4372 0.6140 0.2906 0.018 Uiso 1 1 calc R U . . .
C12 C 0.6328(13) 0.7128(4) 0.2101(3) 0.0133(12) Uani 1 1 d . . . . .
C13 C 0.2174(13) 1.2986(4) 0.2081(3) 0.0141(12) Uani 1 1 d . . . . .
H3 H 0.3199 1.3318 0.2541 0.017 Uiso 1 1 calc R U . . .
C14 C 0.0908(13) 1.3576(4) 0.1444(3) 0.0156(12) Uani 1 1 d . . . . .
H2 H 0.1072 1.4308 0.1458 0.019 Uiso 1 1 calc R U . . .
C15 C 0.8287(13) 1.0086(4) 0.5156(3) 0.0123(11) Uani 1 1 d . . . . .
C16 C 0.7571(14) 0.8108(4) 0.1980(3) 0.0140(12) Uani 1 1 d . . . . .
H5 H 0.8328 0.8306 0.1472 0.017 Uiso 1 1 calc R U . . .
C17 C 0.7704(12) 0.8804(5) 0.2614(3) 0.0153(11) Uani 1 1 d . . . . .
H6 H 0.8559 0.9482 0.2535 0.018 Uiso 1 1 calc R U . . .
C18 C 0.9573(14) 0.8253(4) 0.5145(3) 0.0140(11) Uani 1 1 d . . . . .
H11 H 0.9490 0.7610 0.4871 0.017 Uiso 1 1 calc R U . . .
C19 C 1.0996(13) 0.8314(4) 0.5902(3) 0.0163(12) Uani 1 1 d . . . . .
H10 H 1.1894 0.7714 0.6165 0.020 Uiso 1 1 calc R U . . .
C20 C 1.1127(14) 0.9286(4) 0.6299(3) 0.0176(12) Uani 1 1 d . . . . .
H8 H 1.2166 0.9332 0.6824 0.021 Uiso 1 1 calc R U . . .
C21 C 0.9798(13) 1.0149(4) 0.5942(3) 0.0132(11) Uani 1 1 d . . . . .
H9 H 0.9882 1.0791 0.6217 0.016 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.910(5) . ?
Br2 C12 1.900(5) . ?
N1 C15 1.327(6) . ?
N1 C7 1.384(6) . ?
N2 C18 1.375(6) . ?
N2 C15 1.391(6) . ?
N2 C8 1.400(5) . ?
C1 C2 1.374(7) . ?
C1 C14 1.391(7) . ?
C2 C3 1.380(7) . ?
C2 H12 0.9500 . ?
C3 C4 1.403(7) . ?
C3 H1 0.9500 . ?
C4 C13 1.389(7) . ?
C4 C5 1.444(6) . ?
C5 C6 1.190(6) . ?
C6 C7 1.432(6) . ?
C7 C8 1.374(7) . ?
C8 C9 1.462(7) . ?
C9 C17 1.399(7) . ?
C9 C10 1.402(7) . ?
C10 C11 1.392(7) . ?
C10 H4 0.9500 . ?
C11 C12 1.381(7) . ?
C11 H7 0.9500 . ?
C12 C16 1.375(8) . ?
C13 C14 1.380(7) . ?
C13 H3 0.9500 . ?
C14 H2 0.9500 . ?
C15 C21 1.413(6) . ?
C16 C17 1.390(7) . ?
C16 H5 0.9500 . ?
C17 H6 0.9500 . ?
C18 C19 1.359(6) . ?
C18 H11 0.9500 . ?
C19 C20 1.421(8) . ?
C19 H10 0.9500 . ?
C20 C21 1.355(7) . ?
C20 H8 0.9500 . ?
C21 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C7 103.6(4) . . ?
C18 N2 C15 122.4(4) . . ?
C18 N2 C8 131.5(4) . . ?
C15 N2 C8 106.1(4) . . ?
C2 C1 C14 122.3(5) . . ?
C2 C1 Br1 119.7(4) . . ?
C14 C1 Br1 118.1(4) . . ?
C1 C2 C3 118.6(5) . . ?
C1 C2 H12 120.7 . . ?
C3 C2 H12 120.7 . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H1 119.6 . . ?
C4 C3 H1 119.6 . . ?
C13 C4 C3 118.9(4) . . ?
C13 C4 C5 119.4(4) . . ?
C3 C4 C5 121.7(5) . . ?
C6 C5 C4 176.9(5) . . ?
C5 C6 C7 178.2(6) . . ?
C8 C7 N1 113.0(4) . . ?
C8 C7 C6 125.7(4) . . ?
N1 C7 C6 121.3(5) . . ?
C7 C8 N2 104.5(4) . . ?
C7 C8 C9 130.3(4) . . ?
N2 C8 C9 125.1(4) . . ?
C17 C9 C10 118.6(5) . . ?
C17 C9 C8 117.7(5) . . ?
C10 C9 C8 123.7(5) . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H4 119.9 . . ?
C9 C10 H4 119.9 . . ?
C12 C11 C10 119.5(5) . . ?
C12 C11 H7 120.2 . . ?
C10 C11 H7 120.2 . . ?
C16 C12 C11 121.6(5) . . ?
C16 C12 Br2 119.5(4) . . ?
C11 C12 Br2 118.9(4) . . ?
C14 C13 C4 121.0(4) . . ?
C14 C13 H3 119.5 . . ?
C4 C13 H3 119.5 . . ?
C13 C14 C1 118.4(5) . . ?
C13 C14 H2 120.8 . . ?
C1 C14 H2 120.8 . . ?
N1 C15 N2 112.8(4) . . ?
N1 C15 C21 129.2(5) . . ?
N2 C15 C21 117.9(4) . . ?
C12 C16 C17 119.0(5) . . ?
C12 C16 H5 120.5 . . ?
C17 C16 H5 120.5 . . ?
C16 C17 C9 121.1(5) . . ?
C16 C17 H6 119.5 . . ?
C9 C17 H6 119.5 . . ?
C19 C18 N2 119.5(5) . . ?
C19 C18 H11 120.2 . . ?
N2 C18 H11 120.2 . . ?
C18 C19 C20 119.3(5) . . ?
C18 C19 H10 120.3 . . ?
C20 C19 H10 120.3 . . ?
C21 C20 C19 121.3(4) . . ?
C21 C20 H8 119.4 . . ?
C19 C20 H8 119.4 . . ?
C20 C21 C15 119.5(5) . . ?
C20 C21 H9 120.2 . . ?
C15 C21 H9 120.2 . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.074

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_230885lt_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2h1y8s
_database_code_depnum_ccdc_archive 'CCDC 2295775'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3GC04062C 2024
loop_
_audit_author_name
_audit_author_address
'Mahima Gupta'
;National Tsing Hua University
Taiwan
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C23 H18 N2)'
_chemical_formula_sum            'C46 H36 N4'
_chemical_formula_weight         644.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.92700(10)
_cell_length_b                   11.98670(10)
_cell_length_c                   36.2753(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3446.83(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11504
_cell_measurement_temperature    99.8(5)
_cell_measurement_theta_max      73.9730
_cell_measurement_theta_min      2.4140
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
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    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            21562
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.769
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  77.00   0.50    0.05    --   56.25-125.00 150.00  102
  2  ω     23.00  63.00   0.50    0.05    --   56.25-125.00 -90.00   80
  3  ω    -72.00 -33.00   0.50    0.05    --  -59.44 -15.00-150.00   78
  4  ω    -65.00 -38.00   0.50    0.05    --  -75.32 111.00  60.00   54
  5  ω    -96.00 -42.00   0.50    0.05    --  -75.32 -15.00  90.00  108
  6  ω     38.00  82.00   0.50    0.05    --   75.94 -95.00  30.00   88
  7  ω     39.00  82.00   0.50    0.05    --   83.87-111.00 -60.00   86
  8  ω     37.00  90.00   0.50    0.05    --   75.94-111.00-180.00  106
  9  ω     53.00  82.00   0.50    0.05    --   75.94 -95.00-120.00   58
 10  ω     35.00  70.00   0.50    0.05    --   75.94 -95.00 -60.00   70
 11  ω     53.00  91.00   0.50    0.05    --   83.87 -95.00 -30.00   76
 12  ω     35.00  62.00   0.50    0.05    --   75.94 -95.00   0.00   54
 13  ω     42.00  86.00   0.50    0.05    --   83.87 -95.00  90.00   88
 14  ω     51.00 130.00   0.50    0.05    --   83.87  15.00  60.00  158
 15  ω     92.00 126.00   0.50    0.05    --   75.94  15.00 150.00   68
 16  ω     40.00  85.00   0.50    0.05    --   75.94  15.00 150.00   90
 17  ω     95.00 120.00   0.50    0.05    --   83.87  15.00 -60.00   50
 18  ω     58.00  84.00   0.50    0.05    --   83.87  15.00 -60.00   52
 19  ω     48.00  82.00   0.50    0.05    --   83.87  15.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0664419000
_diffrn_orient_matrix_UB_12      -0.1140030000
_diffrn_orient_matrix_UB_13      -0.0131546000
_diffrn_orient_matrix_UB_21      -0.1285551000
_diffrn_orient_matrix_UB_22      -0.0008706000
_diffrn_orient_matrix_UB_23      0.0318627000
_diffrn_orient_matrix_UB_31      -0.1296497000
_diffrn_orient_matrix_UB_32      0.0593099000
_diffrn_orient_matrix_UB_33      -0.0248308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                6048
_reflns_number_total             6582
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       0.00080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.3139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(5)
 -0.0(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B), C35(H35A,H35B), C44(H44A,H44B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50)
;
_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
C1 C 0.6301(2) 0.68698(16) 0.66289(5) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.6931(2) 0.58478(16) 0.65303(5) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.6893(2) 0.58118(17) 0.71198(5) 0.0209(4) Uani 1 1 d . . . . .
C5 C 0.6988(3) 0.55861(19) 0.75033(5) 0.0257(5) Uani 1 1 d . . . . .
H5 H 0.740366 0.488924 0.758877 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6476(3) 0.63801(19) 0.77473(5) 0.0289(5) Uani 1 1 d . . . . .
H6 H 0.653290 0.623166 0.800429 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5855(3) 0.74296(18) 0.76231(6) 0.0272(5) Uani 1 1 d . . . . .
H7 H 0.549978 0.797268 0.779730 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5769(2) 0.76575(17) 0.72581(5) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.536879 0.835977 0.717401 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5711(2) 0.78356(16) 0.64040(5) 0.0192(4) Uani 1 1 d . . . . .
H10A H 0.609344 0.773179 0.614650 0.023 Uiso 1 1 calc R U . . .
H10B H 0.624420 0.852451 0.649935 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3810(2) 0.79877(16) 0.64055(5) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.3110(2) 0.89675(17) 0.65437(5) 0.0232(4) Uani 1 1 d . . . . .
H12 H 0.382670 0.954879 0.662824 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1370(3) 0.91013(19) 0.65590(5) 0.0284(5) Uani 1 1 d . . . . .
H13 H 0.090278 0.977304 0.665331 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0318(3) 0.82592(19) 0.64372(6) 0.0310(5) Uani 1 1 d . . . . .
H14 H -0.087109 0.834854 0.644983 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1004(3) 0.7282(2) 0.62963(6) 0.0308(5) Uani 1 1 d . . . . .
H15 H 0.028187 0.670279 0.621199 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2747(3) 0.71482(18) 0.62782(5) 0.0245(4) Uani 1 1 d . . . . .
H16 H 0.321095 0.648229 0.617884 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7141(2) 0.54735(16) 0.61575(5) 0.0201(4) Uani 1 1 d . . . . .
C18 C 0.7242(2) 0.51887(17) 0.58425(5) 0.0227(4) Uani 1 1 d . . . . .
C19 C 0.7323(3) 0.48082(18) 0.54590(6) 0.0289(5) Uani 1 1 d . . . . .
H19A H 0.673807 0.408075 0.544044 0.035 Uiso 1 1 calc R U . . .
H19B H 0.852066 0.468502 0.539304 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6551(2) 0.56038(16) 0.51794(5) 0.0220(4) Uani 1 1 d . . . . .
C21 C 0.6746(3) 0.53618(17) 0.48050(5) 0.0261(4) Uani 1 1 d . . . . .
H21 H 0.734011 0.470906 0.473264 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6083(3) 0.60646(18) 0.45378(6) 0.0316(5) Uani 1 1 d . . . . .
H22 H 0.623680 0.589717 0.428405 0.038 Uiso 1 1 calc R U . . .
C23 C 0.5195(3) 0.70112(18) 0.46410(6) 0.0316(5) Uani 1 1 d . . . . .
H23 H 0.474387 0.749503 0.445853 0.038 Uiso 1 1 calc R U . . .
C24 C 0.4969(3) 0.72473(17) 0.50104(6) 0.0290(5) Uani 1 1 d . . . . .
H24 H 0.434503 0.788848 0.508173 0.035 Uiso 1 1 calc R U . . .
C25 C 0.5652(3) 0.65504(16) 0.52789(5) 0.0241(4) Uani 1 1 d . . . . .
H25 H 0.550203 0.672465 0.553227 0.029 Uiso 1 1 calc R U . . .
N3 N 0.73121(19) 0.51878(14) 0.68311(5) 0.0216(3) Uani 1 1 d . . . . .
N9 N 0.62749(19) 0.68496(13) 0.70105(4) 0.0189(3) Uani 1 1 d . . . . .
C26 C 0.8333(2) 0.18569(16) 0.66244(5) 0.0187(4) Uani 1 1 d . . . . .
C28 C 0.9098(2) 0.26220(17) 0.72452(5) 0.0233(4) Uani 1 1 d . . . . .
H28 H 0.947644 0.332551 0.715747 0.028 Uiso 1 1 calc R U . . .
C29 C 0.9142(3) 0.23761(18) 0.76102(5) 0.0284(5) Uani 1 1 d . . . . .
H29 H 0.956694 0.291070 0.777977 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8560(3) 0.13274(19) 0.77416(5) 0.0295(5) Uani 1 1 d . . . . .
H30 H 0.860020 0.116888 0.799804 0.035 Uiso 1 1 calc R U . . .
C31 C 0.7944(3) 0.05462(19) 0.75038(5) 0.0266(5) Uani 1 1 d . . . . .
H31 H 0.755362 -0.015204 0.759356 0.032 Uiso 1 1 calc R U . . .
C32 C 0.7892(2) 0.07858(17) 0.71215(5) 0.0205(4) Uani 1 1 d . . . . .
C34 C 0.7640(2) 0.08404(17) 0.65329(5) 0.0187(4) Uani 1 1 d . . . . .
C35 C 0.8890(2) 0.28222(16) 0.63963(5) 0.0197(4) Uani 1 1 d . . . . .
H35A H 0.834837 0.350955 0.649074 0.024 Uiso 1 1 calc R U . . .
H35B H 0.850466 0.270968 0.613937 0.024 Uiso 1 1 calc R U . . .
C36 C 1.0788(2) 0.29787(16) 0.63977(5) 0.0191(4) Uani 1 1 d . . . . .
C37 C 1.1855(3) 0.21189(18) 0.62883(5) 0.0239(4) Uani 1 1 d . . . . .
H37 H 1.139407 0.142371 0.621311 0.029 Uiso 1 1 calc R U . . .
C38 C 1.3597(3) 0.2273(2) 0.62886(5) 0.0292(5) Uani 1 1 d . . . . .
H38 H 1.432080 0.168610 0.621125 0.035 Uiso 1 1 calc R U . . .
C39 C 1.4273(3) 0.3282(2) 0.64019(6) 0.0326(5) Uani 1 1 d . . . . .
H39 H 1.546085 0.338685 0.640153 0.039 Uiso 1 1 calc R U . . .
C40 C 1.3224(2) 0.41368(19) 0.65153(6) 0.0286(5) Uani 1 1 d . . . . .
H40 H 1.369151 0.482392 0.659650 0.034 Uiso 1 1 calc R U . . .
C41 C 1.1489(2) 0.39905(17) 0.65104(5) 0.0230(4) Uani 1 1 d . . . . .
H41 H 1.077135 0.458439 0.658452 0.028 Uiso 1 1 calc R U . . .
C42 C 0.7244(2) 0.04779(16) 0.61664(5) 0.0201(4) Uani 1 1 d . . . . .
C43 C 0.6892(2) 0.01696(16) 0.58635(5) 0.0226(4) Uani 1 1 d . . . . .
C44 C 0.6404(3) -0.02717(17) 0.55013(5) 0.0285(5) Uani 1 1 d . . . . .
H44A H 0.529771 -0.064812 0.552534 0.034 Uiso 1 1 calc R U . . .
H44B H 0.723909 -0.084210 0.542614 0.034 Uiso 1 1 calc R U . . .
C45 C 0.6279(2) 0.05996(16) 0.51984(5) 0.0234(4) Uani 1 1 d . . . . .
C46 C 0.6942(3) 0.03730(18) 0.48511(6) 0.0288(5) Uani 1 1 d . . . . .
H46 H 0.750825 -0.031328 0.480788 0.035 Uiso 1 1 calc R U . . .
C47 C 0.6782(3) 0.1149(2) 0.45655(6) 0.0328(5) Uani 1 1 d . . . . .
H47 H 0.724814 0.099297 0.432977 0.039 Uiso 1 1 calc R U . . .
C48 C 0.5943(3) 0.21437(19) 0.46265(5) 0.0305(5) Uani 1 1 d . . . . .
H48 H 0.582939 0.267015 0.443237 0.037 Uiso 1 1 calc R U . . .
C49 C 0.5268(3) 0.23731(18) 0.49707(6) 0.0281(5) Uani 1 1 d . . . . .
H49 H 0.468227 0.305316 0.501179 0.034 Uiso 1 1 calc R U . . .
C50 C 0.5450(3) 0.16076(16) 0.52555(5) 0.0247(4) Uani 1 1 d . . . . .
H50 H 0.500248 0.177460 0.549208 0.030 Uiso 1 1 calc R U . . .
N27 N 0.84895(19) 0.18268(13) 0.70044(4) 0.0192(3) Uani 1 1 d . . . . .
N33 N 0.73621(19) 0.01780(14) 0.68388(5) 0.0215(3) 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 1.371(3) . ?
C1 C10 1.491(3) . ?
C1 N9 1.385(2) . ?
C2 C17 1.434(3) . ?
C2 N3 1.381(2) . ?
C4 C5 1.419(3) . ?
C4 N3 1.329(2) . ?
C4 N9 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.362(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.424(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.354(3) . ?
C8 H8 0.9500 . ?
C8 N9 1.380(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.195(3) . ?
C18 C19 1.465(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(3) . ?
C20 C21 1.397(3) . ?
C20 C25 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9500 . ?
C26 C34 1.377(3) . ?
C26 C35 1.489(3) . ?
C26 N27 1.384(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.357(3) . ?
C28 N27 1.380(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.421(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.364(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.417(3) . ?
C32 N27 1.401(2) . ?
C32 N33 1.326(3) . ?
C34 C42 1.433(3) . ?
C34 N33 1.382(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.516(3) . ?
C36 C37 1.391(3) . ?
C36 C41 1.395(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.393(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.385(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.382(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.387(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.192(3) . ?
C43 C44 1.468(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.519(3) . ?
C45 C46 1.392(3) . ?
C45 C50 1.391(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.398(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.383(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.386(3) . ?
C49 H49 0.9500 . ?
C49 C50 1.389(3) . ?
C50 H50 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
C2 C1 C10 131.71(17) . . ?
C2 C1 N9 104.52(16) . . ?
N9 C1 C10 123.76(17) . . ?
C1 C2 C17 124.60(17) . . ?
C1 C2 N3 112.67(16) . . ?
N3 C2 C17 122.71(18) . . ?
N3 C4 C5 130.68(19) . . ?
N3 C4 N9 111.44(16) . . ?
N9 C4 C5 117.88(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.98(19) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.35(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 N9 118.71(19) . . ?
N9 C8 H8 120.6 . . ?
C1 C10 H10A 108.8 . . ?
C1 C10 H10B 108.8 . . ?
C1 C10 C11 113.75(16) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 119.90(18) . . ?
C16 C11 C10 120.90(18) . . ?
C16 C11 C12 119.18(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.86(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.2(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C2 176.7(2) . . ?
C17 C18 C19 178.0(2) . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C18 C19 C20 114.86(17) . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C21 C20 C19 118.25(17) . . ?
C25 C20 C19 123.08(17) . . ?
C25 C20 C21 118.66(18) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.71(19) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.03(19) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 C24 120.54(18) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C4 N3 C2 104.22(16) . . ?
C1 N9 C4 107.14(15) . . ?
C8 N9 C1 129.99(17) . . ?
C8 N9 C4 122.86(16) . . ?
C34 C26 C35 132.19(17) . . ?
C34 C26 N27 104.64(16) . . ?
N27 C26 C35 123.15(17) . . ?
C29 C28 H28 120.8 . . ?
C29 C28 N27 118.47(19) . . ?
N27 C28 H28 120.8 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.7(2) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.75(19) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 H31 120.3 . . ?
C30 C31 C32 119.4(2) . . ?
C32 C31 H31 120.3 . . ?
N27 C32 C31 117.89(18) . . ?
N33 C32 C31 130.91(19) . . ?
N33 C32 N27 111.21(16) . . ?
C26 C34 C42 125.40(18) . . ?
C26 C34 N33 112.23(16) . . ?
N33 C34 C42 122.38(18) . . ?
C26 C35 H35A 109.0 . . ?
C26 C35 H35B 109.0 . . ?
C26 C35 C36 112.85(16) . . ?
H35A C35 H35B 107.8 . . ?
C36 C35 H35A 109.0 . . ?
C36 C35 H35B 109.0 . . ?
C37 C36 C35 120.73(18) . . ?
C37 C36 C41 119.02(18) . . ?
C41 C36 C35 120.25(17) . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C38 120.3(2) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 C37 119.9(2) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.19(19) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.0 . . ?
C39 C40 C41 119.9(2) . . ?
C41 C40 H40 120.0 . . ?
C36 C41 H41 119.7 . . ?
C40 C41 C36 120.6(2) . . ?
C40 C41 H41 119.7 . . ?
C43 C42 C34 179.0(2) . . ?
C42 C43 C44 176.3(2) . . ?
C43 C44 H44A 108.6 . . ?
C43 C44 H44B 108.6 . . ?
C43 C44 C45 114.63(17) . . ?
H44A C44 H44B 107.6 . . ?
C45 C44 H44A 108.6 . . ?
C45 C44 H44B 108.6 . . ?
C46 C45 C44 119.73(18) . . ?
C50 C45 C44 121.36(17) . . ?
C50 C45 C46 118.86(18) . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.4(2) . . ?
C47 C46 H46 119.8 . . ?
C46 C47 H47 120.1 . . ?
C48 C47 C46 119.90(19) . . ?
C48 C47 H47 120.1 . . ?
C47 C48 H48 120.0 . . ?
C47 C48 C49 120.1(2) . . ?
C49 C48 H48 120.0 . . ?
C48 C49 H49 120.0 . . ?
C48 C49 C50 119.9(2) . . ?
C50 C49 H49 120.0 . . ?
C45 C50 H50 119.6 . . ?
C49 C50 C45 120.80(18) . . ?
C49 C50 H50 119.6 . . ?
C26 N27 C32 107.16(15) . . ?
C28 N27 C26 130.06(17) . . ?
C28 N27 C32 122.78(16) . . ?
C32 N33 C34 104.76(16) . . ?

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 N3 C4 0.6(2) . . . . ?
C1 C10 C11 C12 118.78(19) . . . . ?
C1 C10 C11 C16 -59.7(2) . . . . ?
C2 C1 C10 C11 107.2(2) . . . . ?
C2 C1 N9 C4 0.0(2) . . . . ?
C2 C1 N9 C8 179.62(18) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C4 N3 C2 179.7(2) . . . . ?
C5 C4 N9 C1 -179.88(17) . . . . ?
C5 C4 N9 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 N9 0.7(3) . . . . ?
C7 C8 N9 C1 179.53(19) . . . . ?
C7 C8 N9 C4 -0.9(3) . . . . ?
C10 C1 C2 C17 -1.0(3) . . . . ?
C10 C1 C2 N3 -179.34(18) . . . . ?
C10 C1 N9 C4 179.07(16) . . . . ?
C10 C1 N9 C8 -1.3(3) . . . . ?
C10 C11 C12 C13 -177.67(17) . . . . ?
C10 C11 C16 C15 177.21(18) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C17 C2 N3 C4 -177.83(18) . . . . ?
C18 C19 C20 C21 172.92(19) . . . . ?
C18 C19 C20 C25 -7.6(3) . . . . ?
C19 C20 C21 C22 -179.34(19) . . . . ?
C19 C20 C25 C24 -179.83(19) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C20 -0.8(3) . . . . ?
C25 C20 C21 C22 1.2(3) . . . . ?
N3 C4 C5 C6 179.8(2) . . . . ?
N3 C4 N9 C1 0.4(2) . . . . ?
N3 C4 N9 C8 -179.28(17) . . . . ?
N9 C1 C2 C17 178.03(17) . . . . ?
N9 C1 C2 N3 -0.3(2) . . . . ?
N9 C1 C10 C11 -71.6(2) . . . . ?
N9 C4 C5 C6 0.1(3) . . . . ?
N9 C4 N3 C2 -0.6(2) . . . . ?
C26 C34 N33 C32 -0.3(2) . . . . ?
C26 C35 C36 C37 56.7(2) . . . . ?
C26 C35 C36 C41 -123.11(19) . . . . ?
C28 C29 C30 C31 0.0(3) . . . . ?
C29 C28 N27 C26 -178.97(19) . . . . ?
C29 C28 N27 C32 1.1(3) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C30 C31 C32 N27 0.2(3) . . . . ?
C30 C31 C32 N33 180.0(2) . . . . ?
C31 C32 N27 C26 179.17(17) . . . . ?
C31 C32 N27 C28 -0.9(3) . . . . ?
C31 C32 N33 C34 -179.2(2) . . . . ?
C34 C26 C35 C36 -111.0(2) . . . . ?
C34 C26 N27 C28 -179.52(18) . . . . ?
C34 C26 N27 C32 0.44(19) . . . . ?
C35 C26 C34 C42 -1.5(3) . . . . ?
C35 C26 C34 N33 178.17(18) . . . . ?
C35 C26 N27 C28 2.0(3) . . . . ?
C35 C26 N27 C32 -178.05(17) . . . . ?
C35 C36 C37 C38 179.64(17) . . . . ?
C35 C36 C41 C40 179.48(18) . . . . ?
C36 C37 C38 C39 0.7(3) . . . . ?
C37 C36 C41 C40 -0.3(3) . . . . ?
C37 C38 C39 C40 0.1(3) . . . . ?
C38 C39 C40 C41 -1.0(3) . . . . ?
C39 C40 C41 C36 1.1(3) . . . . ?
C41 C36 C37 C38 -0.6(3) . . . . ?
C42 C34 N33 C32 179.44(17) . . . . ?
C43 C44 C45 C46 136.6(2) . . . . ?
C43 C44 C45 C50 -46.1(3) . . . . ?
C44 C45 C46 C47 177.59(19) . . . . ?
C44 C45 C50 C49 -176.64(18) . . . . ?
C45 C46 C47 C48 -0.7(3) . . . . ?
C46 C45 C50 C49 0.7(3) . . . . ?
C46 C47 C48 C49 0.2(3) . . . . ?
C47 C48 C49 C50 0.6(3) . . . . ?
C48 C49 C50 C45 -1.1(3) . . . . ?
C50 C45 C46 C47 0.2(3) . . . . ?
N27 C26 C34 C42 -179.81(17) . . . . ?
N27 C26 C34 N33 -0.1(2) . . . . ?
N27 C26 C35 C36 67.0(2) . . . . ?
N27 C28 C29 C30 -0.6(3) . . . . ?
N27 C32 N33 C34 0.5(2) . . . . ?
N33 C32 N27 C26 -0.6(2) . . . . ?
N33 C32 N27 C28 179.33(17) . . . . ?

_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.929
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(5)
2 -0.0(5)

####################################################################### 
# 
# 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_170449lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2303797'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3GC04062C 2024
loop_
_audit_author_name
_audit_author_address
'Mahima Gupta'
;NTHU
Taiwan
;
_audit_update_record             
;
2023-10-26 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C23 H18 N2)'
_chemical_formula_sum            'C46 H36 N4'
_chemical_formula_weight         644.79
_chemical_melting_point          ?
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'

_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                   9.6958(4)
_cell_length_b                   12.8863(5)
_cell_length_c                   14.1978(5)
_cell_angle_alpha                95.348(2)
_cell_angle_beta                 91.322(2)
_cell_angle_gamma                97.198(2)
_cell_volume                     1751.19(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3365
_cell_measurement_theta_min      2.4864
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabullar
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21609
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5554
_reflns_number_total             6900
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0059(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         6900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.5650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1069
_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.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C34(H34), C35(H35),
  C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45), C46(H46)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C24(H24A,H24B,H24C), C37(H37A,H37B,H37C)
;
_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
N1 N 1.12178(11) 0.38632(8) 0.71548(8) 0.0213(3) Uani 1 1 d . . . . .
N2 N 1.10691(12) 0.55685(9) 0.76041(9) 0.0263(3) Uani 1 1 d . . . . .
N3 N 0.11852(12) 0.88044(8) 0.67629(8) 0.0208(3) Uani 1 1 d . . . . .
N4 N 0.16870(13) 1.05186(9) 0.65516(9) 0.0273(3) Uani 1 1 d . . . . .
C1 C 0.69990(17) 0.02037(13) 0.91198(12) 0.0374(4) Uani 1 1 d . . . . .
H1A H 0.600721 0.028411 0.911776 0.056 Uiso 1 1 calc R U . . .
H1B H 0.732544 0.013280 0.976629 0.056 Uiso 1 1 calc R U . . .
H1C H 0.713948 -0.042521 0.870794 0.056 Uiso 1 1 calc R U . . .
C2 C 0.78071(14) 0.11574(11) 0.87620(11) 0.0260(3) Uani 1 1 d . . . . .
C3 C 0.80807(14) 0.11968(11) 0.78063(10) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.774131 0.061361 0.736741 0.029 Uiso 1 1 calc R U . . .
C4 C 0.88382(14) 0.20697(10) 0.74828(10) 0.0217(3) Uani 1 1 d . . . . .
H4 H 0.900319 0.208075 0.682666 0.026 Uiso 1 1 calc R U . . .
C5 C 0.93613(14) 0.29340(10) 0.81147(10) 0.0206(3) Uani 1 1 d . . . . .
C6 C 1.01803(14) 0.38714(10) 0.78105(10) 0.0213(3) Uani 1 1 d . . . . .
C7 C 1.01266(14) 0.49299(10) 0.80713(10) 0.0231(3) Uani 1 1 d . . . . .
C8 C 0.92013(15) 0.53685(10) 0.87174(10) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.84324(15) 0.57626(10) 0.92552(10) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.75781(14) 0.62483(11) 0.99337(10) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.68150(18) 0.56649(13) 1.05610(12) 0.0393(4) Uani 1 1 d . . . . .
H11 H 0.682724 0.492652 1.052994 0.047 Uiso 1 1 calc R U . . .
C12 C 0.60338(19) 0.61536(15) 1.12335(13) 0.0464(5) Uani 1 1 d . . . . .
H12 H 0.551644 0.574136 1.165720 0.056 Uiso 1 1 calc R U . . .
C13 C 0.59892(16) 0.72273(14) 1.13026(11) 0.0353(4) Uani 1 1 d . . . . .
C14 C 0.5162(2) 0.77646(18) 1.20490(13) 0.0549(6) Uani 1 1 d . . . . .
H14A H 0.430743 0.730332 1.215315 0.082 Uiso 1 1 calc R U . . .
H14B H 0.492315 0.842359 1.183583 0.082 Uiso 1 1 calc R U . . .
H14C H 0.571958 0.791499 1.264179 0.082 Uiso 1 1 calc R U . . .
C15 C 0.82895(15) 0.20334(11) 0.93822(10) 0.0268(3) Uani 1 1 d . . . . .
H15 H 0.808830 0.203228 1.003380 0.032 Uiso 1 1 calc R U . . .
C16 C 0.90579(14) 0.29087(11) 0.90702(10) 0.0247(3) Uani 1 1 d . . . . .
H16 H 0.938067 0.349576 0.950928 0.030 Uiso 1 1 calc R U . . .
C17 C 1.17562(14) 0.30395(11) 0.66614(10) 0.0238(3) Uani 1 1 d . . . . .
H17 H 1.142559 0.233337 0.675914 0.029 Uiso 1 1 calc R U . . .
C18 C 1.27579(15) 0.32524(11) 0.60391(11) 0.0273(3) Uani 1 1 d . . . . .
H18 H 1.312216 0.269024 0.568837 0.033 Uiso 1 1 calc R U . . .
C19 C 1.32775(15) 0.43091(12) 0.59003(11) 0.0306(3) Uani 1 1 d . . . . .
H19 H 1.397626 0.444585 0.545383 0.037 Uiso 1 1 calc R U . . .
C20 C 1.27773(15) 0.51235(11) 0.64044(11) 0.0291(3) Uani 1 1 d . . . . .
H20 H 1.313612 0.582802 0.632028 0.035 Uiso 1 1 calc R U . . .
C21 C 1.17226(14) 0.49127(10) 0.70523(10) 0.0245(3) Uani 1 1 d . . . . .
C22 C 0.75265(16) 0.73312(12) 0.99969(11) 0.0308(3) Uani 1 1 d . . . . .
H22 H 0.803599 0.774638 0.957171 0.037 Uiso 1 1 calc R U . . .
C23 C 0.67414(16) 0.78044(13) 1.06719(11) 0.0342(4) Uani 1 1 d . . . . .
H23 H 0.671912 0.854164 1.070227 0.041 Uiso 1 1 calc R U . . .
C24 C 0.57581(18) 1.29022(14) 0.13085(12) 0.0409(4) Uani 1 1 d . . . . .
H24A H 0.523862 1.347300 0.115436 0.061 Uiso 1 1 calc R U . . .
H24B H 0.579294 1.240834 0.074380 0.061 Uiso 1 1 calc R U . . .
H24C H 0.670645 1.319395 0.152530 0.061 Uiso 1 1 calc R U . . .
C25 C 0.50442(16) 1.23345(12) 0.20811(11) 0.0294(3) Uani 1 1 d . . . . .
C26 C 0.38786(17) 1.26719(11) 0.24990(11) 0.0325(4) Uani 1 1 d . . . . .
H26 H 0.351474 1.326396 0.228704 0.039 Uiso 1 1 calc R U . . .
C27 C 0.32339(17) 1.21612(11) 0.32205(11) 0.0318(4) Uani 1 1 d . . . . .
H27 H 0.243729 1.240696 0.349651 0.038 Uiso 1 1 calc R U . . .
C28 C 0.37470(15) 1.12903(11) 0.35431(10) 0.0257(3) Uani 1 1 d . . . . .
C29 C 0.31014(16) 1.07771(11) 0.43083(10) 0.0285(3) Uani 1 1 d . . . . .
C30 C 0.25786(16) 1.03615(11) 0.49556(11) 0.0281(3) Uani 1 1 d . . . . .
C31 C 0.19940(15) 0.98992(11) 0.57595(10) 0.0253(3) Uani 1 1 d . . . . .
C32 C 0.16978(14) 0.88370(10) 0.58615(10) 0.0215(3) Uani 1 1 d . . . . .
C33 C 0.19170(14) 0.78964(10) 0.52439(9) 0.0212(3) Uani 1 1 d . . . . .
C34 C 0.08882(14) 0.70332(11) 0.50748(10) 0.0235(3) Uani 1 1 d . . . . .
H34 H 0.000737 0.705420 0.535052 0.028 Uiso 1 1 calc R U . . .
C35 C 0.11418(15) 0.61442(11) 0.45069(10) 0.0260(3) Uani 1 1 d . . . . .
H35 H 0.043233 0.556212 0.440518 0.031 Uiso 1 1 calc R U . . .
C36 C 0.24128(16) 0.60900(11) 0.40850(10) 0.0271(3) Uani 1 1 d . . . . .
C37 C 0.26929(18) 0.51236(13) 0.34716(12) 0.0387(4) Uani 1 1 d . . . . .
H37A H 0.282173 0.529711 0.281925 0.058 Uiso 1 1 calc R U . . .
H37B H 0.190254 0.457168 0.348656 0.058 Uiso 1 1 calc R U . . .
H37C H 0.353623 0.487419 0.371056 0.058 Uiso 1 1 calc R U . . .
C38 C 0.31867(14) 0.78488(11) 0.48104(10) 0.0241(3) Uani 1 1 d . . . . .
H38 H 0.389609 0.843150 0.490572 0.029 Uiso 1 1 calc R U . . .
C39 C 0.34225(15) 0.69594(12) 0.42422(10) 0.0276(3) Uani 1 1 d . . . . .
H39 H 0.429454 0.694319 0.395329 0.033 Uiso 1 1 calc R U . . .
C40 C 0.08146(14) 0.79630(10) 0.72789(10) 0.0223(3) Uani 1 1 d . . . . .
H40 H 0.083674 0.726402 0.700559 0.027 Uiso 1 1 calc R U . . .
C41 C 0.04198(14) 0.81489(11) 0.81788(10) 0.0245(3) Uani 1 1 d . . . . .
H41 H 0.015372 0.757447 0.853759 0.029 Uiso 1 1 calc R U . . .
C42 C 0.03973(15) 0.91910(11) 0.85948(10) 0.0271(3) Uani 1 1 d . . . . .
H42 H 0.010515 0.930723 0.922578 0.033 Uiso 1 1 calc R U . . .
C43 C 0.07914(15) 1.00262(11) 0.80968(10) 0.0268(3) Uani 1 1 d . . . . .
H43 H 0.078617 1.072362 0.837921 0.032 Uiso 1 1 calc R U . . .
C44 C 0.12079(14) 0.98428(10) 0.71554(10) 0.0235(3) Uani 1 1 d . . . . .
C45 C 0.55395(15) 1.14545(12) 0.23985(11) 0.0310(3) Uani 1 1 d . . . . .
H45 H 0.632982 1.120546 0.211624 0.037 Uiso 1 1 calc R U . . .
C46 C 0.49067(15) 1.09359(12) 0.31146(11) 0.0291(3) Uani 1 1 d . . . . .
H46 H 0.526186 1.033562 0.331640 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.3866(17) . ?
N1 C17 1.3809(17) . ?
N1 C21 1.4014(17) . ?
N2 C7 1.3760(17) . ?
N2 C21 1.3277(18) . ?
N3 C32 1.3859(17) . ?
N3 C40 1.3799(16) . ?
N3 C44 1.3980(17) . ?
N4 C31 1.3777(19) . ?
N4 C44 1.3287(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.5085(19) . ?
C2 C3 1.393(2) . ?
C2 C15 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3858(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3978(19) . ?
C5 C6 1.4660(18) . ?
C5 C16 1.3972(19) . ?
C6 C7 1.3874(19) . ?
C7 C8 1.426(2) . ?
C8 C9 1.202(2) . ?
C9 C10 1.435(2) . ?
C10 C11 1.386(2) . ?
C10 C22 1.397(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 C14 1.512(2) . ?
C13 C23 1.380(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.3861(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.348(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.425(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.361(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.409(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(2) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C25 1.508(2) . ?
C25 C26 1.387(2) . ?
C25 C45 1.393(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.394(2) . ?
C28 C29 1.4391(19) . ?
C28 C46 1.397(2) . ?
C29 C30 1.197(2) . ?
C30 C31 1.4320(19) . ?
C31 C32 1.3847(19) . ?
C32 C33 1.4691(19) . ?
C33 C34 1.397(2) . ?
C33 C38 1.3945(19) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(2) . ?
C36 C37 1.509(2) . ?
C36 C39 1.390(2) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38 0.9500 . ?
C38 C39 1.385(2) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C40 C41 1.351(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.419(2) . ?
C42 H42 0.9500 . ?
C42 C43 1.3622(19) . ?
C43 H43 0.9500 . ?
C43 C44 1.413(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.382(2) . ?
C46 H46 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 C21 107.21(11) . . ?
C17 N1 C6 131.05(11) . . ?
C17 N1 C21 121.73(12) . . ?
C21 N2 C7 104.87(11) . . ?
C32 N3 C44 107.35(11) . . ?
C40 N3 C32 130.56(11) . . ?
C40 N3 C44 121.85(11) . . ?
C44 N4 C31 104.78(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.54(14) . . ?
C15 C2 C1 120.55(13) . . ?
C15 C2 C3 117.90(13) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.31(13) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.50(13) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 122.65(12) . . ?
C16 C5 C4 118.33(12) . . ?
C16 C5 C6 119.00(13) . . ?
N1 C6 C5 125.08(12) . . ?
N1 C6 C7 104.28(11) . . ?
C7 C6 C5 130.63(13) . . ?
N2 C7 C6 112.34(12) . . ?
N2 C7 C8 120.77(12) . . ?
C6 C7 C8 126.85(13) . . ?
C9 C8 C7 178.36(15) . . ?
C8 C9 C10 176.85(16) . . ?
C11 C10 C9 121.15(13) . . ?
C11 C10 C22 118.17(14) . . ?
C22 C10 C9 120.65(13) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.34(15) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.62(15) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 121.67(16) . . ?
C23 C13 C12 117.88(15) . . ?
C23 C13 C14 120.44(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15 119.3 . . ?
C16 C15 C2 121.41(13) . . ?
C16 C15 H15 119.3 . . ?
C5 C16 H16 119.8 . . ?
C15 C16 C5 120.48(13) . . ?
C15 C16 H16 119.8 . . ?
N1 C17 H17 120.5 . . ?
C18 C17 N1 119.01(13) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.89(14) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.29(14) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.44(13) . . ?
C21 C20 H20 120.3 . . ?
N1 C21 C20 118.59(13) . . ?
N2 C21 N1 111.30(12) . . ?
N2 C21 C20 130.10(13) . . ?
C10 C22 H22 119.7 . . ?
C23 C22 C10 120.66(14) . . ?
C23 C22 H22 119.7 . . ?
C13 C23 C22 121.33(15) . . ?
C13 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
C26 C25 C24 121.18(14) . . ?
C26 C25 C45 117.94(13) . . ?
C45 C25 C24 120.88(15) . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.27(14) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.45(14) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 120.49(13) . . ?
C27 C28 C46 118.57(13) . . ?
C46 C28 C29 120.94(13) . . ?
C30 C29 C28 178.90(18) . . ?
C29 C30 C31 177.32(17) . . ?
N4 C31 C30 120.84(12) . . ?
N4 C31 C32 112.34(12) . . ?
C32 C31 C30 126.80(14) . . ?
N3 C32 C33 123.59(11) . . ?
C31 C32 N3 104.26(12) . . ?
C31 C32 C33 132.02(12) . . ?
C34 C33 C32 122.01(12) . . ?
C38 C33 C32 119.78(12) . . ?
C38 C33 C34 118.21(13) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.58(13) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.27(13) . . ?
C36 C35 H35 119.4 . . ?
C35 C36 C37 121.37(14) . . ?
C35 C36 C39 117.82(13) . . ?
C39 C36 C37 120.80(14) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C33 C38 H38 119.7 . . ?
C39 C38 C33 120.57(13) . . ?
C39 C38 H38 119.7 . . ?
C36 C39 H39 119.2 . . ?
C38 C39 C36 121.53(13) . . ?
C38 C39 H39 119.2 . . ?
N3 C40 H40 120.5 . . ?
C41 C40 N3 118.96(12) . . ?
C41 C40 H40 120.5 . . ?
C40 C41 H41 119.6 . . ?
C40 C41 C42 120.84(13) . . ?
C42 C41 H41 119.6 . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 120.53(13) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 120.4 . . ?
C42 C43 C44 119.20(13) . . ?
C44 C43 H43 120.4 . . ?
N3 C44 C43 118.58(12) . . ?
N4 C44 N3 111.26(12) . . ?
N4 C44 C43 130.11(13) . . ?
C25 C45 H45 119.3 . . ?
C46 C45 C25 121.46(14) . . ?
C46 C45 H45 119.3 . . ?
C28 C46 H46 119.9 . . ?
C45 C46 C28 120.30(14) . . ?
C45 C46 H46 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 N2 0.46(15) . . . . ?
N1 C6 C7 C8 178.38(13) . . . . ?
N1 C17 C18 C19 1.1(2) . . . . ?
N3 C32 C33 C34 49.56(19) . . . . ?
N3 C32 C33 C38 -130.18(14) . . . . ?
N3 C40 C41 C42 -0.6(2) . . . . ?
N4 C31 C32 N3 -0.10(16) . . . . ?
N4 C31 C32 C33 -176.10(14) . . . . ?
C1 C2 C3 C4 -179.20(13) . . . . ?
C1 C2 C15 C16 178.67(13) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C15 C16 C5 0.4(2) . . . . ?
C3 C2 C15 C16 -2.0(2) . . . . ?
C3 C4 C5 C6 179.36(12) . . . . ?
C3 C4 C5 C16 -2.28(19) . . . . ?
C4 C5 C6 N1 -42.2(2) . . . . ?
C4 C5 C6 C7 137.15(15) . . . . ?
C4 C5 C16 C15 1.77(19) . . . . ?
C5 C6 C7 N2 -178.95(13) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 N1 C17 C18 178.48(13) . . . . ?
C6 N1 C21 N2 0.24(16) . . . . ?
C6 N1 C21 C20 -178.74(13) . . . . ?
C6 C5 C16 C15 -179.81(12) . . . . ?
C7 N2 C21 N1 0.05(15) . . . . ?
C7 N2 C21 C20 178.88(15) . . . . ?
C9 C10 C11 C12 177.73(16) . . . . ?
C9 C10 C22 C23 -177.76(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C10 C22 C23 C13 0.1(2) . . . . ?
C11 C10 C22 C23 0.4(2) . . . . ?
C11 C12 C13 C14 -178.68(17) . . . . ?
C11 C12 C13 C23 0.6(3) . . . . ?
C12 C13 C23 C22 -0.6(2) . . . . ?
C14 C13 C23 C22 178.68(16) . . . . ?
C15 C2 C3 C4 1.5(2) . . . . ?
C16 C5 C6 N1 139.49(14) . . . . ?
C16 C5 C6 C7 -41.2(2) . . . . ?
C17 N1 C6 C5 -1.8(2) . . . . ?
C17 N1 C6 C7 178.72(13) . . . . ?
C17 N1 C21 N2 -178.99(12) . . . . ?
C17 N1 C21 C20 2.0(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C19 C20 C21 -1.2(2) . . . . ?
C19 C20 C21 N1 -0.2(2) . . . . ?
C19 C20 C21 N2 -178.92(15) . . . . ?
C21 N1 C6 C5 179.05(12) . . . . ?
C21 N1 C6 C7 -0.41(14) . . . . ?
C21 N1 C17 C18 -2.5(2) . . . . ?
C21 N2 C7 C6 -0.32(16) . . . . ?
C21 N2 C7 C8 -178.39(13) . . . . ?
C22 C10 C11 C12 -0.4(2) . . . . ?
C24 C25 C26 C27 -178.93(15) . . . . ?
C24 C25 C45 C46 179.10(15) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C25 C45 C46 C28 -0.3(2) . . . . ?
C26 C25 C45 C46 -0.8(2) . . . . ?
C26 C27 C28 C29 178.34(15) . . . . ?
C26 C27 C28 C46 -1.0(2) . . . . ?
C27 C28 C46 C45 1.2(2) . . . . ?
C29 C28 C46 C45 -178.17(14) . . . . ?
C30 C31 C32 N3 178.65(14) . . . . ?
C30 C31 C32 C33 2.7(3) . . . . ?
C31 N4 C44 N3 -0.73(16) . . . . ?
C31 N4 C44 C43 176.83(15) . . . . ?
C31 C32 C33 C34 -135.10(16) . . . . ?
C31 C32 C33 C38 45.2(2) . . . . ?
C32 N3 C40 C41 175.82(13) . . . . ?
C32 N3 C44 N4 0.70(15) . . . . ?
C32 N3 C44 C43 -177.18(12) . . . . ?
C32 C33 C34 C35 -178.28(12) . . . . ?
C32 C33 C38 C39 178.60(12) . . . . ?
C33 C34 C35 C36 -0.6(2) . . . . ?
C33 C38 C39 C36 0.0(2) . . . . ?
C34 C33 C38 C39 -1.14(19) . . . . ?
C34 C35 C36 C37 179.72(13) . . . . ?
C34 C35 C36 C39 -0.6(2) . . . . ?
C35 C36 C39 C38 0.9(2) . . . . ?
C37 C36 C39 C38 -179.40(13) . . . . ?
C38 C33 C34 C35 1.46(19) . . . . ?
C40 N3 C32 C31 -174.69(13) . . . . ?
C40 N3 C32 C33 1.7(2) . . . . ?
C40 N3 C44 N4 175.65(12) . . . . ?
C40 N3 C44 C43 -2.23(19) . . . . ?
C40 C41 C42 C43 -0.8(2) . . . . ?
C41 C42 C43 C44 0.7(2) . . . . ?
C42 C43 C44 N3 0.7(2) . . . . ?
C42 C43 C44 N4 -176.69(15) . . . . ?
C44 N3 C32 C31 -0.34(15) . . . . ?
C44 N3 C32 C33 176.09(12) . . . . ?
C44 N3 C40 C41 2.18(19) . . . . ?
C44 N4 C31 C30 -178.32(14) . . . . ?
C44 N4 C31 C32 0.52(17) . . . . ?
C45 C25 C26 C27 0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
