# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_MU39_P_R1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2259069'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2023-05-28 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C25 H21 F N2 O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         400.44
_chemical_melting_point          ?
_chemical_absolute_configuration ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   13.9745(6)
_cell_length_b                   20.9846(8)
_cell_length_c                   7.8209(4)
_cell_angle_alpha                90
_cell_angle_beta                 119.6450(10)
_cell_angle_gamma                90
_cell_volume                     1993.27(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6167
_cell_measurement_theta_min      2.7865
_cell_measurement_theta_max      26.344
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make '296 K'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           30.0
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            11556
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_theta_min         2.786
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4066
_reflns_number_gt                3500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.986
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.994
_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 BIS V6.2.16/2021-10-23 && APEX4 2022.10-0'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0357P)²+0.5586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     275
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.10686(16) 0.42195(12) 0.4441(3) 0.0842(7) Uani 1 1 d . . . . .
O1 O 0.53274(17) 0.52744(9) 0.4561(3) 0.0507(5) Uani 1 1 d . . . . .
O2 O 0.36969(16) 0.34533(11) 0.0206(3) 0.0577(6) Uani 1 1 d . . . . .
N1 N 0.56969(16) 0.42209(9) 0.4678(3) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.53981(18) 0.31150(10) 0.2544(3) 0.0401(5) Uani 1 1 d . . . . .
C1 C 0.6978(2) 0.49048(13) 0.7305(4) 0.0383(6) Uani 1 1 d . . . . .
C2 C 0.7586(2) 0.43792(13) 0.8382(4) 0.0400(6) Uani 1 1 d . . . . .
C3 C 0.8560(2) 0.44873(16) 1.0166(4) 0.0514(7) Uani 1 1 d . . . . .
H3 H 0.897460 0.414337 1.091740 0.062 Uiso 1 1 calc R U . . .
C4 C 0.8902(2) 0.50966(18) 1.0807(5) 0.0597(9) Uani 1 1 d . . . . .
H4 H 0.955388 0.516198 1.198238 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8294(3) 0.56140(17) 0.9732(5) 0.0597(9) Uani 1 1 d . . . . .
H5 H 0.853408 0.602505 1.018676 0.072 Uiso 1 1 calc R U . . .
C6 C 0.7330(2) 0.55221(14) 0.7986(4) 0.0483(7) Uani 1 1 d . . . . .
H6 H 0.691631 0.587036 0.726354 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5950(2) 0.48306(12) 0.5431(4) 0.0362(6) Uani 1 1 d . . . . .
C8 C 0.63457(19) 0.36927(11) 0.5646(4) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.7229(2) 0.37415(12) 0.7565(4) 0.0373(6) Uani 1 1 d . . . . .
C10 C 0.46130(19) 0.41272(12) 0.2945(4) 0.0355(6) Uani 1 1 d . . . . .
H10 H 0.450460 0.448478 0.206042 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4527(2) 0.35239(13) 0.1792(4) 0.0396(6) Uani 1 1 d . . . . .
C12 C 0.6118(2) 0.31123(12) 0.4624(4) 0.0385(6) Uani 1 1 d . . . . .
C13 C 0.6617(3) 0.25668(13) 0.5674(5) 0.0514(7) Uani 1 1 d . . . . .
H13 H 0.640155 0.217126 0.506387 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7434(3) 0.26029(14) 0.7627(5) 0.0564(8) Uani 1 1 d . . . . .
H14 H 0.775781 0.223172 0.832438 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7767(3) 0.31827(14) 0.8535(4) 0.0510(7) Uani 1 1 d . . . . .
H15 H 0.835750 0.320484 0.981123 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3676(2) 0.41627(11) 0.3406(4) 0.0357(6) Uani 1 1 d . . . . .
C17 C 0.3837(2) 0.40846(13) 0.5272(4) 0.0417(6) Uani 1 1 d . . . . .
H17 H 0.454670 0.401940 0.631029 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2965(2) 0.41008(15) 0.5641(5) 0.0514(7) Uani 1 1 d . . . . .
H18 H 0.307870 0.404714 0.690888 0.062 Uiso 1 1 calc R U . . .
C19 C 0.1934(2) 0.41979(16) 0.4091(5) 0.0551(8) Uani 1 1 d . . . . .
C20 C 0.1738(2) 0.42876(18) 0.2223(5) 0.0611(9) Uani 1 1 d . . . . .
H20 H 0.102620 0.435787 0.119798 0.073 Uiso 1 1 calc R U . . .
C21 C 0.2613(2) 0.42725(15) 0.1877(4) 0.0507(7) Uani 1 1 d . . . . .
H21 H 0.249181 0.433629 0.060835 0.061 Uiso 1 1 calc R U . . .
C22 C 0.5544(2) 0.26460(13) 0.1198(4) 0.0458(7) Uani 1 1 d . . . . .
C23 C 0.4890(3) 0.20422(15) 0.0984(6) 0.0667(10) Uani 1 1 d . . . . .
H23A H 0.491344 0.176830 0.002248 0.100 Uiso 1 1 calc R U . . .
H23B H 0.413956 0.215186 0.056913 0.100 Uiso 1 1 calc R U . . .
H23C H 0.520518 0.182550 0.222688 0.100 Uiso 1 1 calc R U . . .
C24 C 0.6765(3) 0.25148(16) 0.1990(5) 0.0567(8) Uani 1 1 d . . . . .
H24A H 0.685869 0.227828 0.103184 0.085 Uiso 1 1 calc R U . . .
H24B H 0.705036 0.227208 0.318342 0.085 Uiso 1 1 calc R U . . .
H24C H 0.715533 0.291151 0.225259 0.085 Uiso 1 1 calc R U . . .
C25 C 0.5138(3) 0.29529(17) -0.0826(5) 0.0604(8) Uani 1 1 d . . . . .
H25A H 0.537586 0.270120 -0.157121 0.091 Uiso 1 1 calc R U . . .
H25B H 0.543544 0.337521 -0.065904 0.091 Uiso 1 1 calc R U . . .
H25C H 0.434831 0.297445 -0.151290 0.091 Uiso 1 1 calc R U . . .


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 C19 1.366(3) . ?
O1 C7 1.225(3) . ?
O2 C11 1.217(3) . ?
N1 C7 1.379(3) . ?
N1 C8 1.394(3) . ?
N1 C10 1.463(3) . ?
N2 C11 1.362(3) . ?
N2 C12 1.429(3) . ?
N2 C22 1.526(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.395(4) . ?
C1 C7 1.467(3) . ?
C2 C3 1.404(4) . ?
C2 C9 1.461(4) . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.397(3) . ?
C8 C12 1.404(3) . ?
C9 C15 1.397(4) . ?
C10 C16 1.522(4) . ?
C10 C11 1.524(4) . ?
C10 H10 0.9800 . ?
C12 C13 1.380(4) . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 C21 1.390(4) . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(5) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.522(4) . ?
C22 C24 1.526(4) . ?
C22 C25 1.534(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 123.0(2) . . ?
C7 N1 C10 116.7(2) . . ?
C8 N1 C10 119.57(19) . . ?
C11 N2 C12 118.0(2) . . ?
C11 N2 C22 120.3(2) . . ?
C12 N2 C22 121.6(2) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 C7 121.5(2) . . ?
C6 C1 C7 117.8(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 C9 119.1(2) . . ?
C3 C2 C9 122.4(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 N1 120.4(2) . . ?
O1 C7 C1 123.3(2) . . ?
N1 C7 C1 116.2(2) . . ?
N1 C8 C9 121.1(2) . . ?
N1 C8 C12 118.5(2) . . ?
C9 C8 C12 120.4(2) . . ?
C15 C9 C8 118.3(2) . . ?
C15 C9 C2 123.8(2) . . ?
C8 C9 C2 117.8(2) . . ?
N1 C10 C16 113.0(2) . . ?
N1 C10 C11 113.7(2) . . ?
C16 C10 C11 110.8(2) . . ?
N1 C10 H10 106.2 . . ?
C16 C10 H10 106.2 . . ?
C11 C10 H10 106.2 . . ?
O2 C11 N2 124.1(2) . . ?
O2 C11 C10 117.4(2) . . ?
N2 C11 C10 118.4(2) . . ?
C13 C12 C8 118.4(2) . . ?
C13 C12 N2 123.0(2) . . ?
C8 C12 N2 118.6(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C9 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C9 C15 H15 119.6 . . ?
C17 C16 C21 118.6(2) . . ?
C17 C16 C10 122.6(2) . . ?
C21 C16 C10 118.8(2) . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 118.0(3) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
C20 C19 C18 122.6(3) . . ?
C20 C19 F1 118.9(3) . . ?
C18 C19 F1 118.5(3) . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C23 C22 C24 112.6(3) . . ?
C23 C22 N2 109.6(2) . . ?
C24 C22 N2 109.9(2) . . ?
C23 C22 C25 109.9(3) . . ?
C24 C22 C25 105.2(3) . . ?
N2 C22 C25 109.5(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 C9 -176.2(3) . . . . ?
C7 C1 C2 C9 3.9(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C9 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C7 C1 C6 C5 -179.6(3) . . . . ?
C8 N1 C7 O1 -176.9(2) . . . . ?
C10 N1 C7 O1 -6.5(4) . . . . ?
C8 N1 C7 C1 2.3(3) . . . . ?
C10 N1 C7 C1 172.7(2) . . . . ?
C2 C1 C7 O1 171.1(3) . . . . ?
C6 C1 C7 O1 -8.8(4) . . . . ?
C2 C1 C7 N1 -8.0(3) . . . . ?
C6 C1 C7 N1 172.1(2) . . . . ?
C7 N1 C8 C9 7.8(4) . . . . ?
C10 N1 C8 C9 -162.4(2) . . . . ?
C7 N1 C8 C12 -169.9(2) . . . . ?
C10 N1 C8 C12 19.9(3) . . . . ?
N1 C8 C9 C15 172.7(2) . . . . ?
C12 C8 C9 C15 -9.6(4) . . . . ?
N1 C8 C9 C2 -11.8(3) . . . . ?
C12 C8 C9 C2 165.9(2) . . . . ?
C1 C2 C9 C15 -178.8(3) . . . . ?
C3 C2 C9 C15 5.0(4) . . . . ?
C1 C2 C9 C8 6.0(4) . . . . ?
C3 C2 C9 C8 -170.2(2) . . . . ?
C7 N1 C10 C16 -72.0(3) . . . . ?
C8 N1 C10 C16 98.7(3) . . . . ?
C7 N1 C10 C11 160.5(2) . . . . ?
C8 N1 C10 C11 -28.8(3) . . . . ?
C12 N2 C11 O2 -157.6(3) . . . . ?
C22 N2 C11 O2 18.4(4) . . . . ?
C12 N2 C11 C10 25.8(3) . . . . ?
C22 N2 C11 C10 -158.2(2) . . . . ?
N1 C10 C11 O2 -171.3(2) . . . . ?
C16 C10 C11 O2 60.1(3) . . . . ?
N1 C10 C11 N2 5.5(3) . . . . ?
C16 C10 C11 N2 -123.1(3) . . . . ?
N1 C8 C12 C13 -168.2(3) . . . . ?
C9 C8 C12 C13 14.1(4) . . . . ?
N1 C8 C12 N2 12.9(3) . . . . ?
C9 C8 C12 N2 -164.8(2) . . . . ?
C11 N2 C12 C13 144.6(3) . . . . ?
C22 N2 C12 C13 -31.3(4) . . . . ?
C11 N2 C12 C8 -36.5(3) . . . . ?
C22 N2 C12 C8 147.6(2) . . . . ?
C8 C12 C13 C14 -8.8(4) . . . . ?
N2 C12 C13 C14 170.1(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C9 5.4(5) . . . . ?
C8 C9 C15 C14 -0.1(4) . . . . ?
C2 C9 C15 C14 -175.3(3) . . . . ?
N1 C10 C16 C17 -19.6(3) . . . . ?
C11 C10 C16 C17 109.4(3) . . . . ?
N1 C10 C16 C21 161.0(2) . . . . ?
C11 C10 C16 C21 -69.9(3) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?
C10 C16 C17 C18 -178.1(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C17 C18 C19 F1 -179.5(3) . . . . ?
C18 C19 C20 C21 0.8(6) . . . . ?
F1 C19 C20 C21 179.3(3) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
C10 C16 C21 C20 177.9(3) . . . . ?
C11 N2 C22 C23 -86.4(3) . . . . ?
C12 N2 C22 C23 89.5(3) . . . . ?
C11 N2 C22 C24 149.4(3) . . . . ?
C12 N2 C22 C24 -34.8(3) . . . . ?
C11 N2 C22 C25 34.3(3) . . . . ?
C12 N2 C22 C25 -149.9(2) . . . . ?

####################################################################### 
# 
# 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_MU_39_P_R2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2265884'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2023-05-28 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         416.46
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   9.0733(17)
_cell_length_b                   11.2285(18)
_cell_length_c                   21.135(4)
_cell_angle_alpha                85.568(7)
_cell_angle_beta                 87.255(8)
_cell_angle_gamma                81.710(7)
_cell_volume                     2122.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      2.712
_cell_measurement_theta_max      26.317
_exptl_crystal_description       Pyramid
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.192
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      296(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make '296 K'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           30.0
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            63534
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8660
_reflns_number_gt                6331
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS V6.2.16/2021-10-23 && APEX4 2022.10-0'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1238P)²+2.8016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8660
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.2705
_refine_ls_wR_factor_gt          0.2278
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9952(3) 0.4253(2) 0.93885(15) 0.0523(7) Uani 1 1 d . . . . .
O2 O 0.7422(4) 0.8192(3) 0.97673(15) 0.0586(8) Uani 1 1 d . . . . .
O3 O 0.9780(3) -0.0895(2) 0.56026(15) 0.0508(7) Uani 1 1 d . . . . .
O4 O 0.7259(4) 0.3134(3) 0.51770(15) 0.0608(8) Uani 1 1 d . . . . .
N1 N 0.7578(3) 0.5194(2) 0.92943(13) 0.0332(6) Uani 1 1 d . . . . .
N2 N 0.5568(3) 0.7320(3) 0.93857(14) 0.0396(7) Uani 1 1 d . . . . .
N3 N 0.7382(3) 0.0008(2) 0.56792(13) 0.0339(6) Uani 1 1 d . . . . .
N4 N 0.5368(3) 0.2148(3) 0.55765(14) 0.0421(7) Uani 1 1 d . . . . .
C1 C 0.6639(4) 0.2986(3) 0.90940(16) 0.0376(7) Uani 1 1 d . . . . .
C2 C 0.8089(4) 0.3022(3) 0.92624(16) 0.0373(7) Uani 1 1 d . . . . .
C3 C 0.9113(5) 0.1966(3) 0.9339(2) 0.0497(9) Uani 1 1 d . . . . .
H3 H 1.007994 0.200385 0.945438 0.060 Uiso 1 1 calc R U . . .
C4 C 0.8678(6) 0.0871(4) 0.9241(2) 0.0586(11) Uani 1 1 d . . . . .
H4 H 0.933364 0.016111 0.930984 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7261(6) 0.0837(4) 0.9040(2) 0.0577(11) Uani 1 1 d . . . . .
H5 H 0.698897 0.010075 0.895343 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6246(5) 0.1860(4) 0.89657(19) 0.0497(9) Uani 1 1 d . . . . .
H6 H 0.529667 0.181351 0.883048 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5569(4) 0.4092(3) 0.90788(16) 0.0364(7) Uani 1 1 d . . . . .
C8 C 0.6076(4) 0.5178(3) 0.91943(15) 0.0322(7) Uani 1 1 d . . . . .
C9 C 0.8634(4) 0.4174(3) 0.93237(16) 0.0364(7) Uani 1 1 d . . . . .
C10 C 0.4049(4) 0.4115(4) 0.89850(19) 0.0491(9) Uani 1 1 d . . . . .
H10 H 0.368783 0.340023 0.892271 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3084(5) 0.5173(4) 0.8983(2) 0.0571(11) Uani 1 1 d . . . . .
H11 H 0.208217 0.517552 0.890804 0.069 Uiso 1 1 calc R U . . .
C12 C 0.3598(4) 0.6242(4) 0.9094(2) 0.0499(9) Uani 1 1 d . . . . .
H12 H 0.293725 0.695734 0.908584 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5072(4) 0.6256(3) 0.92161(16) 0.0371(7) Uani 1 1 d . . . . .
C14 C 0.7009(4) 0.7349(3) 0.95215(17) 0.0406(8) Uani 1 1 d . . . . .
C15 C 0.8166(4) 0.6338(3) 0.93070(17) 0.0375(7) Uani 1 1 d . . . . .
H15 H 0.897982 0.622143 0.960393 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4501(5) 0.8408(4) 0.94677(18) 0.0479(9) Uani 1 1 d . . . . .
H16A H 0.491965 0.891210 0.974425 0.057 Uiso 1 1 calc R U . . .
H16B H 0.360249 0.817557 0.967921 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4081(4) 0.9144(3) 0.88610(18) 0.0426(8) Uani 1 1 d . . . . .
C18 C 0.3014(5) 1.0154(4) 0.8901(2) 0.0532(10) Uani 1 1 d . . . . .
H18 H 0.256920 1.034585 0.929253 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2608(6) 1.0876(5) 0.8363(3) 0.0707(14) Uani 1 1 d . . . . .
H19 H 0.189410 1.155380 0.839371 0.085 Uiso 1 1 calc R U . . .
C20 C 0.3247(6) 1.0604(5) 0.7784(3) 0.0756(15) Uani 1 1 d . . . . .
H20 H 0.295068 1.108423 0.742118 0.091 Uiso 1 1 calc R U . . .
C21 C 0.4318(6) 0.9628(5) 0.7739(2) 0.0743(15) Uani 1 1 d . . . . .
H21 H 0.477153 0.945581 0.734656 0.089 Uiso 1 1 calc R U . . .
C22 C 0.4737(5) 0.8886(4) 0.8279(2) 0.0603(11) Uani 1 1 d . . . . .
H22 H 0.546181 0.821581 0.824495 0.072 Uiso 1 1 calc R U . . .
C23 C 0.8776(4) 0.6780(3) 0.86572(18) 0.0403(8) Uani 1 1 d . . . . .
C24 C 0.9760(5) 0.7624(4) 0.8632(2) 0.0575(11) Uani 1 1 d . . . . .
H24 H 1.009001 0.786061 0.900670 0.069 Uiso 1 1 calc R U . . .
C25 C 1.0250(6) 0.8113(5) 0.8055(3) 0.0786(17) Uani 1 1 d . . . . .
H25 H 1.091008 0.867653 0.804185 0.094 Uiso 1 1 calc R U . . .
C26 C 0.9768(7) 0.7772(5) 0.7500(3) 0.0807(17) Uani 1 1 d . . . . .
H26 H 1.008970 0.811239 0.711189 0.097 Uiso 1 1 calc R U . . .
C27 C 0.8808(6) 0.6928(5) 0.7518(2) 0.0738(14) Uani 1 1 d . . . . .
H27 H 0.848650 0.669115 0.714204 0.089 Uiso 1 1 calc R U . . .
C28 C 0.8320(5) 0.6431(4) 0.8095(2) 0.0563(10) Uani 1 1 d . . . . .
H28 H 0.767741 0.585467 0.810416 0.068 Uiso 1 1 calc R U . . .
C29 C 0.6443(4) -0.2256(3) 0.59384(17) 0.0392(8) Uani 1 1 d . . . . .
C30 C 0.6045(5) -0.3419(4) 0.6090(2) 0.0530(10) Uani 1 1 d . . . . .
H30 H 0.507630 -0.350599 0.622910 0.064 Uiso 1 1 calc R U . . .
C31 C 0.7097(6) -0.4424(4) 0.6030(2) 0.0604(12) Uani 1 1 d . . . . .
H31 H 0.682707 -0.518375 0.613708 0.072 Uiso 1 1 calc R U . . .
C32 C 0.8534(6) -0.4334(4) 0.5816(2) 0.0606(12) Uani 1 1 d . . . . .
H32 H 0.920936 -0.502484 0.575562 0.073 Uiso 1 1 calc R U . . .
C33 C 0.8964(5) -0.3209(3) 0.5693(2) 0.0471(9) Uani 1 1 d . . . . .
H33 H 0.994316 -0.313531 0.556453 0.057 Uiso 1 1 calc R U . . .
C34 C 0.7917(4) -0.2174(3) 0.57615(16) 0.0369(7) Uani 1 1 d . . . . .
C35 C 0.8451(4) -0.1002(3) 0.56672(16) 0.0366(7) Uani 1 1 d . . . . .
C36 C 0.5873(4) -0.0041(3) 0.58010(15) 0.0341(7) Uani 1 1 d . . . . .
C37 C 0.5360(4) -0.1161(3) 0.59457(17) 0.0389(8) Uani 1 1 d . . . . .
C38 C 0.7961(4) 0.1165(3) 0.56344(17) 0.0374(7) Uani 1 1 d . . . . .
H38 H 0.880260 0.112190 0.532471 0.045 Uiso 1 1 calc R U . . .
C39 C 0.6825(4) 0.2218(3) 0.54294(17) 0.0415(8) Uani 1 1 d . . . . .
C40 C 0.4857(4) 0.1037(3) 0.57701(17) 0.0384(8) Uani 1 1 d . . . . .
C41 C 0.3369(4) 0.0980(4) 0.5913(2) 0.0543(10) Uani 1 1 d . . . . .
H41 H 0.269871 0.168942 0.591428 0.065 Uiso 1 1 calc R U . . .
C42 C 0.2858(5) -0.0120(5) 0.6055(2) 0.0616(12) Uani 1 1 d . . . . .
H42 H 0.184871 -0.014337 0.614544 0.074 Uiso 1 1 calc R U . . .
C43 C 0.3838(4) -0.1173(4) 0.6062(2) 0.0535(10) Uani 1 1 d . . . . .
H43 H 0.347992 -0.190663 0.614640 0.064 Uiso 1 1 calc R U . . .
C44 C 0.8505(4) 0.1461(3) 0.62699(18) 0.0403(8) Uani 1 1 d . . . . .
C45 C 0.8021(6) 0.0959(5) 0.6839(2) 0.0661(12) Uani 1 1 d . . . . .
H45 H 0.739867 0.036821 0.684725 0.079 Uiso 1 1 calc R U . . .
C46 C 0.8453(7) 0.1327(7) 0.7400(3) 0.0912(19) Uani 1 1 d . . . . .
H46 H 0.813563 0.097348 0.778561 0.109 Uiso 1 1 calc R U . . .
C47 C 0.9353(8) 0.2216(6) 0.7393(3) 0.096(2) Uani 1 1 d . . . . .
H47 H 0.960773 0.248381 0.777347 0.115 Uiso 1 1 calc R U . . .
C48 C 0.9875(7) 0.2709(5) 0.6826(4) 0.0855(19) Uani 1 1 d . . . . .
H48 H 1.050726 0.329203 0.682056 0.103 Uiso 1 1 calc R U . . .
C49 C 0.9455(5) 0.2334(4) 0.6270(3) 0.0592(11) Uani 1 1 d . . . . .
H49 H 0.980890 0.266590 0.588583 0.071 Uiso 1 1 calc R U . . .
C50 C 0.4312(5) 0.3258(4) 0.55077(19) 0.0498(9) Uani 1 1 d . . . . .
H50A H 0.343444 0.308316 0.530765 0.060 Uiso 1 1 calc R U . . .
H50B H 0.476108 0.383787 0.522473 0.060 Uiso 1 1 calc R U . . .
C51 C 0.3829(4) 0.3827(3) 0.61169(18) 0.0453(8) Uani 1 1 d . . . . .
C52 C 0.4441(6) 0.3418(5) 0.6689(2) 0.0650(12) Uani 1 1 d . . . . .
H52 H 0.516528 0.274140 0.671464 0.078 Uiso 1 1 calc R U . . .
C53 C 0.3973(7) 0.4020(6) 0.7229(2) 0.0846(17) Uani 1 1 d . . . . .
H53 H 0.439366 0.374577 0.761537 0.101 Uiso 1 1 calc R U . . .
C54 C 0.2899(7) 0.5012(5) 0.7200(3) 0.0801(16) Uani 1 1 d . . . . .
H54 H 0.258285 0.540068 0.756594 0.096 Uiso 1 1 calc R U . . .
C55 C 0.2293(6) 0.5430(5) 0.6629(3) 0.0695(13) Uani 1 1 d . . . . .
H55 H 0.157460 0.611092 0.660504 0.083 Uiso 1 1 calc R U . . .
C56 C 0.2754(5) 0.4838(4) 0.6093(2) 0.0543(10) Uani 1 1 d . . . . .
H56 H 0.233510 0.512125 0.570700 0.065 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.227(4) . ?
O2 C14 1.226(5) . ?
O3 C35 1.229(4) . ?
O4 C39 1.228(5) . ?
N1 C9 1.382(4) . ?
N1 C8 1.392(4) . ?
N1 C15 1.463(4) . ?
N2 C14 1.357(5) . ?
N2 C13 1.412(5) . ?
N2 C16 1.461(5) . ?
N3 C35 1.383(4) . ?
N3 C36 1.390(4) . ?
N3 C38 1.465(4) . ?
N4 C39 1.356(5) . ?
N4 C40 1.418(5) . ?
N4 C50 1.460(5) . ?
C1 C2 1.386(5) . ?
C1 C6 1.411(5) . ?
C1 C7 1.461(5) . ?
C2 C3 1.401(5) . ?
C2 C9 1.467(5) . ?
C3 C4 1.377(6) . ?
C4 C5 1.379(7) . ?
C5 C6 1.369(6) . ?
C7 C10 1.399(5) . ?
C7 C8 1.406(5) . ?
C8 C13 1.409(5) . ?
C10 C11 1.371(6) . ?
C11 C12 1.388(6) . ?
C12 C13 1.377(5) . ?
C14 C15 1.512(5) . ?
C15 C23 1.530(5) . ?
C16 C17 1.505(5) . ?
C17 C22 1.373(6) . ?
C17 C18 1.387(5) . ?
C18 C19 1.377(7) . ?
C19 C20 1.365(8) . ?
C20 C21 1.362(8) . ?
C21 C22 1.394(6) . ?
C23 C28 1.380(6) . ?
C23 C24 1.389(5) . ?
C24 C25 1.380(7) . ?
C25 C26 1.371(9) . ?
C26 C27 1.374(8) . ?
C27 C28 1.381(7) . ?
C29 C34 1.386(5) . ?
C29 C30 1.413(5) . ?
C29 C37 1.459(5) . ?
C30 C31 1.378(7) . ?
C31 C32 1.374(7) . ?
C32 C33 1.377(6) . ?
C33 C34 1.403(5) . ?
C34 C35 1.462(5) . ?
C36 C37 1.409(5) . ?
C36 C40 1.411(5) . ?
C37 C43 1.393(5) . ?
C38 C39 1.503(5) . ?
C38 C44 1.529(5) . ?
C40 C41 1.379(5) . ?
C41 C42 1.387(7) . ?
C42 C43 1.373(6) . ?
C44 C45 1.369(6) . ?
C44 C49 1.395(6) . ?
C45 C46 1.377(7) . ?
C46 C47 1.376(10) . ?
C47 C48 1.373(10) . ?
C48 C49 1.367(8) . ?
C50 C51 1.500(5) . ?
C51 C52 1.373(6) . ?
C51 C56 1.385(5) . ?
C52 C53 1.390(7) . ?
C53 C54 1.370(8) . ?
C54 C55 1.371(8) . ?
C55 C56 1.377(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C8 123.8(3) . . ?
C9 N1 C15 115.3(3) . . ?
C8 N1 C15 120.6(3) . . ?
C14 N2 C13 121.9(3) . . ?
C14 N2 C16 117.8(3) . . ?
C13 N2 C16 120.1(3) . . ?
C35 N3 C36 123.6(3) . . ?
C35 N3 C38 115.3(3) . . ?
C36 N3 C38 120.6(3) . . ?
C39 N4 C40 121.9(3) . . ?
C39 N4 C50 117.8(3) . . ?
C40 N4 C50 120.3(3) . . ?
C2 C1 C6 118.0(4) . . ?
C2 C1 C7 119.4(3) . . ?
C6 C1 C7 122.6(3) . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 C9 121.1(3) . . ?
C3 C2 C9 117.6(3) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 119.4(4) . . ?
C6 C5 C4 121.6(4) . . ?
C5 C6 C1 120.0(4) . . ?
C10 C7 C8 118.2(3) . . ?
C10 C7 C1 123.2(3) . . ?
C8 C7 C1 118.5(3) . . ?
N1 C8 C7 120.1(3) . . ?
N1 C8 C13 119.3(3) . . ?
C7 C8 C13 120.6(3) . . ?
O1 C9 N1 120.7(3) . . ?
O1 C9 C2 122.9(3) . . ?
N1 C9 C2 116.4(3) . . ?
C11 C10 C7 121.1(4) . . ?
C10 C11 C12 120.2(4) . . ?
C13 C12 C11 120.9(4) . . ?
C12 C13 C8 119.0(3) . . ?
C12 C13 N2 120.9(3) . . ?
C8 C13 N2 120.1(3) . . ?
O2 C14 N2 123.2(3) . . ?
O2 C14 C15 118.9(3) . . ?
N2 C14 C15 117.8(3) . . ?
N1 C15 C14 112.9(3) . . ?
N1 C15 C23 112.8(3) . . ?
C14 C15 C23 106.2(3) . . ?
N2 C16 C17 114.7(3) . . ?
C22 C17 C18 118.9(4) . . ?
C22 C17 C16 123.3(4) . . ?
C18 C17 C16 117.8(3) . . ?
C19 C18 C17 120.3(4) . . ?
C20 C19 C18 120.5(5) . . ?
C21 C20 C19 119.9(4) . . ?
C20 C21 C22 120.3(5) . . ?
C17 C22 C21 120.1(4) . . ?
C28 C23 C24 118.7(4) . . ?
C28 C23 C15 122.7(3) . . ?
C24 C23 C15 118.5(4) . . ?
C25 C24 C23 120.3(5) . . ?
C26 C25 C24 120.3(5) . . ?
C25 C26 C27 119.9(5) . . ?
C26 C27 C28 120.0(5) . . ?
C23 C28 C27 120.7(4) . . ?
C34 C29 C30 117.8(4) . . ?
C34 C29 C37 119.6(3) . . ?
C30 C29 C37 122.6(3) . . ?
C31 C30 C29 119.8(4) . . ?
C32 C31 C30 121.8(4) . . ?
C31 C32 C33 119.3(4) . . ?
C32 C33 C34 119.7(4) . . ?
C29 C34 C33 121.4(3) . . ?
C29 C34 C35 121.0(3) . . ?
C33 C34 C35 117.6(3) . . ?
O3 C35 N3 120.4(3) . . ?
O3 C35 C34 122.9(3) . . ?
N3 C35 C34 116.7(3) . . ?
N3 C36 C37 120.2(3) . . ?
N3 C36 C40 119.4(3) . . ?
C37 C36 C40 120.4(3) . . ?
C43 C37 C36 118.5(4) . . ?
C43 C37 C29 123.1(3) . . ?
C36 C37 C29 118.3(3) . . ?
N3 C38 C39 113.4(3) . . ?
N3 C38 C44 112.2(3) . . ?
C39 C38 C44 105.9(3) . . ?
O4 C39 N4 122.7(3) . . ?
O4 C39 C38 118.9(3) . . ?
N4 C39 C38 118.3(3) . . ?
C41 C40 C36 118.9(4) . . ?
C41 C40 N4 121.2(3) . . ?
C36 C40 N4 119.9(3) . . ?
C40 C41 C42 121.0(4) . . ?
C43 C42 C41 120.1(4) . . ?
C42 C43 C37 121.1(4) . . ?
C45 C44 C49 118.8(4) . . ?
C45 C44 C38 122.5(4) . . ?
C49 C44 C38 118.6(4) . . ?
C44 C45 C46 120.2(5) . . ?
C47 C46 C45 120.3(6) . . ?
C48 C47 C46 120.2(5) . . ?
C49 C48 C47 119.3(5) . . ?
C48 C49 C44 121.1(5) . . ?
N4 C50 C51 114.9(3) . . ?
C52 C51 C56 118.9(4) . . ?
C52 C51 C50 123.0(4) . . ?
C56 C51 C50 118.0(4) . . ?
C51 C52 C53 119.6(5) . . ?
C54 C53 C52 120.9(5) . . ?
C53 C54 C55 119.7(5) . . ?
C54 C55 C56 119.7(5) . . ?
C55 C56 C51 121.2(4) . . ?

