# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_KA921_0m
_database_code_depnum_ccdc_archive 'CCDC 2175625'
loop_
_audit_author_name
_audit_author_address
B.Sridhar
;CSIR IICT
India
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.12630(10)
_cell_length_b                   10.1687(2)
_cell_length_c                   19.2429(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.9070(5)
_cell_angle_gamma                90
_cell_volume                     1764.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      29.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6837
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25170
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         29.826
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4453
_reflns_number_gt                3018
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_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)+(0.0505P)²+0.3665P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4453
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.59096(17) 0.7416(2) 0.49081(10) 0.0670(5) Uani 1 1 d . . . . .
H1A H 0.674033 0.702827 0.473399 0.101 Uiso 1 1 calc R U . . .
H1B H 0.592167 0.716057 0.538919 0.101 Uiso 1 1 calc R U . . .
H1C H 0.597086 0.835687 0.487945 0.101 Uiso 1 1 calc R U . . .
C2 C 0.45088(15) 0.69573(15) 0.44770(8) 0.0450(3) Uani 1 1 d . . . . .
C3 C 0.29686(14) 0.74431(14) 0.45452(7) 0.0395(3) Uani 1 1 d . . . . .
C4 C 0.20389(15) 0.65384(14) 0.40122(7) 0.0413(3) Uani 1 1 d . . . . .
C5 C 0.27903(16) 0.49254(14) 0.31370(7) 0.0416(3) Uani 1 1 d . . . . .
C6 C 0.13932(18) 0.47907(16) 0.27397(7) 0.0496(4) Uani 1 1 d . . . . .
H6 H 0.060362 0.529577 0.284130 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1188(2) 0.39005(18) 0.21929(8) 0.0587(4) Uani 1 1 d . . . . .
H7 H 0.025145 0.379970 0.192919 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2349(2) 0.31613(18) 0.20328(9) 0.0623(5) Uani 1 1 d . . . . .
H8 H 0.219979 0.256716 0.166109 0.075 Uiso 1 1 calc R U . . .
C9 C 0.3732(2) 0.33033(16) 0.24244(9) 0.0572(4) Uani 1 1 d . . . . .
H9 H 0.451907 0.280472 0.231442 0.069 Uiso 1 1 calc R U . . .
C10 C 0.39665(18) 0.41775(15) 0.29791(8) 0.0487(4) Uani 1 1 d . . . . .
H10 H 0.490386 0.426431 0.324441 0.058 Uiso 1 1 calc R U . . .
C11 C 0.26651(15) 0.88259(14) 0.42439(7) 0.0401(3) Uani 1 1 d . . . . .
C12 C 0.3448(2) 0.93024(17) 0.37362(9) 0.0570(4) Uani 1 1 d . . . . .
H12 H 0.423631 0.881979 0.361446 0.068 Uiso 1 1 calc R U . . .
C13 C 0.3067(2) 1.04893(18) 0.34097(10) 0.0674(5) Uani 1 1 d . . . . .
H13 H 0.359545 1.079818 0.306687 0.081 Uiso 1 1 calc R U . . .
C14 C 0.1921(2) 1.12126(17) 0.35863(9) 0.0594(4) Uani 1 1 d . . . . .
H14 H 0.167048 1.201318 0.336579 0.071 Uiso 1 1 calc R U . . .
C15 C 0.11391(18) 1.07551(17) 0.40899(9) 0.0571(4) Uani 1 1 d . . . . .
H15 H 0.036247 1.124970 0.421412 0.069 Uiso 1 1 calc R U . . .
C16 C 0.15021(16) 0.95620(15) 0.44130(8) 0.0489(4) Uani 1 1 d . . . . .
H16 H 0.095597 0.925116 0.474853 0.059 Uiso 1 1 calc R U . . .
C17 C 0.26418(15) 0.72866(14) 0.52947(7) 0.0409(3) Uani 1 1 d . . . . .
C18 C 0.31291(17) 0.82234(15) 0.57958(8) 0.0481(4) Uani 1 1 d . . . . .
H18 H 0.363901 0.895566 0.566964 0.058 Uiso 1 1 calc R U . . .
C19 C 0.28742(19) 0.80946(19) 0.64813(9) 0.0580(4) Uani 1 1 d . . . . .
H19 H 0.320365 0.874153 0.681029 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2141(2) 0.7022(2) 0.66773(9) 0.0671(5) Uani 1 1 d . . . . .
H20 H 0.196115 0.693841 0.713793 0.080 Uiso 1 1 calc R U . . .
C21 C 0.1674(2) 0.6073(2) 0.61939(11) 0.0730(5) Uani 1 1 d . . . . .
H21 H 0.119029 0.533267 0.632871 0.088 Uiso 1 1 calc R U . . .
C22 C 0.19133(19) 0.62009(17) 0.55016(9) 0.0579(4) Uani 1 1 d . . . . .
H22 H 0.158007 0.555004 0.517564 0.070 Uiso 1 1 calc R U . . .
N1 N 0.45237(13) 0.60798(13) 0.40074(7) 0.0498(3) Uani 1 1 d . . . . .
N2 N 0.30393(12) 0.58347(12) 0.36989(6) 0.0445(3) Uani 1 1 d . . . . .
O1 O 0.06985(11) 0.64963(11) 0.38767(6) 0.0555(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 1.487(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.2716(19) . ?
C2 C3 1.5146(19) . ?
C3 C17 1.5256(19) . ?
C3 C11 1.530(2) . ?
C3 C4 1.5326(19) . ?
C4 O1 1.2114(16) . ?
C4 N2 1.3709(18) . ?
C5 C10 1.387(2) . ?
C5 C6 1.388(2) . ?
C5 N2 1.4141(18) . ?
C6 C7 1.379(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.378(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.379(2) . ?
C17 C18 1.379(2) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 N2 1.4144(16) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 120.92(14) . . ?
N1 C2 C3 113.74(12) . . ?
C1 C2 C3 125.34(14) . . ?
C2 C3 C17 111.58(11) . . ?
C2 C3 C11 112.51(12) . . ?
C17 C3 C11 113.81(11) . . ?
C2 C3 C4 99.86(11) . . ?
C17 C3 C4 113.64(11) . . ?
C11 C3 C4 104.42(11) . . ?
O1 C4 N2 127.30(13) . . ?
O1 C4 C3 126.96(13) . . ?
N2 C4 C3 105.67(11) . . ?
C10 C5 C6 120.08(14) . . ?
C10 C5 N2 119.20(13) . . ?
C6 C5 N2 120.72(13) . . ?
C7 C6 C5 119.31(15) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.87(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.65(16) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.75(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 119.34(15) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
C16 C11 C12 118.50(14) . . ?
C16 C11 C3 120.70(12) . . ?
C12 C11 C3 120.41(13) . . ?
C13 C12 C11 120.39(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.47(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.75(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.14(16) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.73(14) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C22 C17 C18 117.96(14) . . ?
C22 C17 C3 122.01(13) . . ?
C18 C17 C3 119.99(12) . . ?
C17 C18 C19 121.24(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 120.19(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.54(16) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.66(17) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.41(17) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C2 N1 N2 107.87(11) . . ?
C4 N2 C5 129.67(12) . . ?
C4 N2 N1 112.54(11) . . ?
C5 N2 N1 117.78(11) . . ?

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 C2 C3 C17 123.98(14) . . . . ?
C1 C2 C3 C17 -55.4(2) . . . . ?
N1 C2 C3 C11 -106.68(15) . . . . ?
C1 C2 C3 C11 73.90(19) . . . . ?
N1 C2 C3 C4 3.55(17) . . . . ?
C1 C2 C3 C4 -175.88(15) . . . . ?
C2 C3 C4 O1 177.65(15) . . . . ?
C17 C3 C4 O1 58.72(19) . . . . ?
C11 C3 C4 O1 -65.87(18) . . . . ?
C2 C3 C4 N2 -5.13(14) . . . . ?
C17 C3 C4 N2 -124.05(12) . . . . ?
C11 C3 C4 N2 111.36(12) . . . . ?
C10 C5 C6 C7 0.6(2) . . . . ?
N2 C5 C6 C7 179.65(13) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C5 -0.5(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
N2 C5 C10 C9 -179.04(14) . . . . ?
C2 C3 C11 C16 -163.35(13) . . . . ?
C17 C3 C11 C16 -35.17(18) . . . . ?
C4 C3 C11 C16 89.31(15) . . . . ?
C2 C3 C11 C12 23.90(19) . . . . ?
C17 C3 C11 C12 152.08(14) . . . . ?
C4 C3 C11 C12 -83.44(16) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C3 C11 C12 C13 172.97(15) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C3 C11 C16 C15 -173.71(14) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
C2 C3 C17 C22 -94.68(16) . . . . ?
C11 C3 C17 C22 136.66(14) . . . . ?
C4 C3 C17 C22 17.30(19) . . . . ?
C2 C3 C17 C18 82.79(16) . . . . ?
C11 C3 C17 C18 -45.87(17) . . . . ?
C4 C3 C17 C18 -165.23(13) . . . . ?
C22 C17 C18 C19 -1.2(2) . . . . ?
C3 C17 C18 C19 -178.74(14) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C18 C17 C22 C21 0.5(2) . . . . ?
C3 C17 C22 C21 178.06(15) . . . . ?
C20 C21 C22 C17 0.6(3) . . . . ?
C1 C2 N1 N2 178.94(14) . . . . ?
C3 C2 N1 N2 -0.51(18) . . . . ?
O1 C4 N2 C5 2.0(3) . . . . ?
C3 C4 N2 C5 -175.24(13) . . . . ?
O1 C4 N2 N1 -177.31(14) . . . . ?
C3 C4 N2 N1 5.47(15) . . . . ?
C10 C5 N2 C4 -170.02(14) . . . . ?
C6 C5 N2 C4 10.9(2) . . . . ?
C10 C5 N2 N1 9.24(19) . . . . ?
C6 C5 N2 N1 -169.87(13) . . . . ?
C2 N1 N2 C4 -3.32(17) . . . . ?
C2 N1 N2 C5 177.30(13) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_KA1013_0m
_database_code_depnum_ccdc_archive 'CCDC 2175627'
loop_
_audit_author_name
_audit_author_address
B.Sridhar
;CSIR IICT
India
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 F3 N2 O'
_chemical_formula_sum            'C16 H11 F3 N2 O'
_chemical_formula_weight         304.27

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'
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           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                   6.2516(2)
_cell_length_b                   12.1242(4)
_cell_length_c                   19.5002(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.0124(9)
_cell_angle_gamma                90
_cell_volume                     1477.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7697
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      23.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5192
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33792
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.681
_diffrn_reflns_theta_max         29.765
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7270
_reflns_number_gt                3290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.808
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.2256P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7270
_refine_ls_number_parameters     453
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.1941
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.079
_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
C1A C -0.4420(7) 0.4520(4) 0.9566(2) 0.0568(12) Uani 1 1 d . . . . .
C2A C -0.6187(7) 0.5198(4) 0.9579(3) 0.0706(14) Uani 1 1 d . . . . .
H2A H -0.633723 0.576913 0.926327 0.085 Uiso 1 1 calc R U . . .
C3A C -0.7741(8) 0.5022(5) 1.0067(3) 0.0833(17) Uani 1 1 d . . . . .
H3A H -0.892654 0.548451 1.008292 0.100 Uiso 1 1 calc R U . . .
C4A C -0.7538(11) 0.4179(6) 1.0522(3) 0.0907(18) Uani 1 1 d . . . . .
H4A H -0.859355 0.405968 1.084365 0.109 Uiso 1 1 calc R U . . .
C5A C -0.5779(11) 0.3503(5) 1.0507(3) 0.0908(17) Uani 1 1 d . . . . .
H5A H -0.564822 0.292684 1.082022 0.109 Uiso 1 1 calc R U . . .
C6A C -0.4196(9) 0.3670(4) 1.0030(3) 0.0746(15) Uani 1 1 d . . . . .
H6A H -0.299874 0.321535 1.002241 0.090 Uiso 1 1 calc R U . . .
C7A C -0.1716(7) 0.3997(4) 0.8685(3) 0.0680(14) Uani 1 1 d . . . . .
C8A C -0.0401(8) 0.4571(5) 0.8261(3) 0.0758(15) Uani 1 1 d . . . . .
H8A H 0.056126 0.429535 0.794519 0.091 Uiso 1 1 calc R U . . .
C9A C -0.0849(8) 0.5662(5) 0.8415(3) 0.0744(14) Uani 1 1 d . . . . .
C10A C -0.0511(8) 0.2161(4) 0.8626(3) 0.0615(13) Uani 1 1 d . . . . .
C11A C -0.0938(8) 0.1325(4) 0.8175(2) 0.0643(13) Uani 1 1 d . . . . .
H11A H -0.224345 0.129242 0.793923 0.077 Uiso 1 1 calc R U . . .
C12A C 0.0602(9) 0.0528(4) 0.8075(3) 0.0759(15) Uani 1 1 d . . . . .
H12A H 0.034230 -0.004826 0.776973 0.091 Uiso 1 1 calc R U . . .
C13A C 0.2522(9) 0.0590(5) 0.8427(3) 0.0810(15) Uani 1 1 d . . . . .
H13A H 0.356064 0.005420 0.835879 0.097 Uiso 1 1 calc R U . . .
C14A C 0.2919(8) 0.1429(5) 0.8876(3) 0.0812(15) Uani 1 1 d . . . . .
H14A H 0.422041 0.146354 0.911419 0.097 Uiso 1 1 calc R U . . .
C15A C 0.1395(8) 0.2223(5) 0.8977(3) 0.0770(15) Uani 1 1 d . . . . .
H15A H 0.165677 0.279961 0.928114 0.092 Uiso 1 1 calc R U . . .
C16A C 0.0108(14) 0.6649(7) 0.8085(5) 0.106(2) Uani 1 1 d . U . . .
F1A F 0.1281(17) 0.7225(7) 0.8554(6) 0.150(3) Uani 0.691(7) 1 d . U P A 1
F2A F 0.0355(10) 0.6524(5) 0.7405(3) 0.116(2) Uani 0.691(7) 1 d . U P A 1
F3A F -0.1410(13) 0.7477(7) 0.7981(4) 0.119(2) Uani 0.691(7) 1 d . U P A 1
F1' F 0.244(3) 0.663(2) 0.8178(9) 0.101(5) Uani 0.309(7) 1 d . U P A 2
F2' F 0.189(5) 0.645(2) 0.7870(14) 0.144(6) Uani 0.309(7) 1 d . U P A 2
F3' F -0.046(4) 0.753(2) 0.8286(13) 0.145(6) Uani 0.309(7) 1 d . U P A 2
O1A O -0.2176(5) 0.2914(3) 0.8746(2) 0.0936(13) Uani 1 1 d . . . . .
N1A N -0.2833(6) 0.4728(3) 0.9067(2) 0.0607(10) Uani 1 1 d . . . . .
N2A N -0.2318(6) 0.5782(3) 0.8886(2) 0.0715(11) Uani 1 1 d . . . . .
C1B C 0.9401(7) 0.6695(4) 0.5332(2) 0.0590(12) Uani 1 1 d . . . . .
C2B C 1.1174(7) 0.7372(5) 0.5357(3) 0.0710(14) Uani 1 1 d . . . . .
H2B H 1.130819 0.792055 0.568815 0.085 Uiso 1 1 calc R U . . .
C3B C 1.2778(8) 0.7212(6) 0.4868(3) 0.0846(17) Uani 1 1 d . . . . .
H3B H 1.398382 0.766200 0.487401 0.101 Uiso 1 1 calc R U . . .
C4B C 1.2575(10) 0.6406(6) 0.4388(3) 0.0903(18) Uani 1 1 d . . . . .
H4B H 1.363685 0.631185 0.406532 0.108 Uiso 1 1 calc R U . . .
C5B C 1.0820(10) 0.5731(5) 0.4376(3) 0.0865(17) Uani 1 1 d . . . . .
H5B H 1.071717 0.516866 0.405222 0.104 Uiso 1 1 calc R U . . .
C6B C 0.9186(8) 0.5879(4) 0.4845(3) 0.0753(15) Uani 1 1 d . . . . .
H6B H 0.797304 0.543457 0.482870 0.090 Uiso 1 1 calc R U . . .
C7B C 0.6515(7) 0.6140(4) 0.6160(3) 0.0675(14) Uani 1 1 d . . . . .
C8B C 0.5280(8) 0.6704(4) 0.6600(3) 0.0696(14) Uani 1 1 d . . . . .
H8B H 0.426376 0.642329 0.689569 0.083 Uiso 1 1 calc R U . . .
C9B C 0.5871(7) 0.7796(4) 0.6511(3) 0.0691(14) Uani 1 1 d . . . . .
C10B C 0.5189(7) 0.4354(4) 0.6286(3) 0.0585(12) Uani 1 1 d D . . . .
C11B C 0.5692(10) 0.3767(6) 0.6857(3) 0.0918(19) Uani 1 1 d D . . . .
H11B H 0.700465 0.385567 0.708237 0.110 Uiso 1 1 calc R U . . .
C12B C 0.4185(13) 0.3031(6) 0.7094(4) 0.113(2) Uani 1 1 d D . . . .
H12B H 0.449223 0.261205 0.748321 0.135 Uiso 1 1 calc R U . . .
C13B C 0.2282(12) 0.2912(6) 0.6770(5) 0.104(2) Uani 1 1 d D . . . .
H13B H 0.128757 0.241067 0.693416 0.125 Uiso 1 1 calc R U . . .
C14B C 0.1822(10) 0.3513(7) 0.6214(4) 0.101(2) Uani 1 1 d D . . . .
H14B H 0.049832 0.343338 0.599381 0.122 Uiso 1 1 calc R U . . .
C15B C 0.3282(9) 0.4245(5) 0.5963(3) 0.0817(15) Uani 1 1 d D . . . .
H15B H 0.295902 0.466122 0.557476 0.098 Uiso 1 1 calc R U . . .
C16B C 0.5010(12) 0.8782(6) 0.6853(4) 0.0930(19) Uani 1 1 d . U . . .
F1B F 0.445(2) 0.8520(7) 0.7502(5) 0.158(3) Uani 0.691(7) 1 d . U P A 1
F2B F 0.3971(14) 0.9474(6) 0.6395(4) 0.124(2) Uani 0.691(7) 1 d . U P A 1
F3B F 0.649(2) 0.9440(11) 0.7110(6) 0.125(4) Uani 0.691(7) 1 d . U P A 1
F1" F 0.314(3) 0.8563(13) 0.7157(11) 0.092(5) Uani 0.309(7) 1 d . U P A 2
F2" F 0.310(4) 0.897(2) 0.6784(14) 0.122(5) Uani 0.309(7) 1 d . U P A 2
F3" F 0.606(5) 0.966(3) 0.6856(14) 0.122(7) Uani 0.309(7) 1 d . U P A 2
O1B O 0.6747(6) 0.5055(3) 0.6016(2) 0.0971(14) Uani 1 1 d . . . . .
N1B N 0.7766(6) 0.6880(3) 0.5828(2) 0.0599(10) Uani 1 1 d . . . . .
N2B N 0.7390(6) 0.7920(3) 0.6050(2) 0.0664(11) 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
C1A C6A 1.376(7) . ?
C1A C2A 1.377(6) . ?
C1A N1A 1.425(6) . ?
C2A C3A 1.389(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.357(8) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.373(9) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.386(8) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A O1A 1.350(6) . ?
C7A N1A 1.358(6) . ?
C7A C8A 1.367(7) . ?
C8A C9A 1.386(8) . ?
C8A H8A 0.9300 . ?
C9A N2A 1.319(6) . ?
C9A C16A 1.489(9) . ?
C10A C15A 1.365(7) . ?
C10A C11A 1.366(6) . ?
C10A O1A 1.407(5) . ?
C11A C12A 1.380(7) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.375(7) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.362(8) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.371(7) . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9300 . ?
C16A F3' 1.20(2) . ?
C16A F2' 1.22(2) . ?
C16A F2A 1.346(10) . ?
C16A F1A 1.357(11) . ?
C16A F3A 1.394(12) . ?
C16A F1' 1.46(2) . ?
F1' F2' 0.72(3) . ?
N1A N2A 1.366(5) . ?
C1B C6B 1.377(7) . ?
C1B C2B 1.380(6) . ?
C1B N1B 1.437(6) . ?
C2B C3B 1.409(7) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.357(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.369(8) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.395(7) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B C8B 1.349(6) . ?
C7B O1B 1.354(6) . ?
C7B N1B 1.362(6) . ?
C8B C9B 1.386(7) . ?
C8B H8B 0.9300 . ?
C9B N2B 1.328(6) . ?
C9B C16B 1.475(8) . ?
C10B C15B 1.345(7) . ?
C10B C11B 1.354(8) . ?
C10B O1B 1.402(5) . ?
C11B C12B 1.383(9) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.345(9) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.335(9) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.369(8) . ?
C14B H14B 0.9300 . ?
C15B H15B 0.9300 . ?
C16B F2" 1.218(19) . ?
C16B F3" 1.25(3) . ?
C16B F3B 1.314(14) . ?
C16B F1" 1.344(17) . ?
C16B F1B 1.357(10) . ?
C16B F2B 1.380(11) . ?
F1" F2" 0.88(3) . ?
N1B N2B 1.355(5) . ?

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
C6A C1A C2A 120.5(5) . . ?
C6A C1A N1A 121.1(4) . . ?
C2A C1A N1A 118.4(4) . . ?
C1A C2A C3A 119.5(5) . . ?
C1A C2A H2A 120.3 . . ?
C3A C2A H2A 120.3 . . ?
C4A C3A C2A 120.3(6) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C5A 120.1(6) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C4A C5A C6A 120.5(6) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A C5A 119.0(5) . . ?
C1A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
O1A C7A N1A 118.3(4) . . ?
O1A C7A C8A 132.8(5) . . ?
N1A C7A C8A 108.7(5) . . ?
C7A C8A C9A 103.2(4) . . ?
C7A C8A H8A 128.4 . . ?
C9A C8A H8A 128.4 . . ?
N2A C9A C8A 113.7(5) . . ?
N2A C9A C16A 120.1(6) . . ?
C8A C9A C16A 126.1(6) . . ?
C15A C10A C11A 121.5(5) . . ?
C15A C10A O1A 121.5(4) . . ?
C11A C10A O1A 116.8(4) . . ?
C10A C11A C12A 118.8(5) . . ?
C10A C11A H11A 120.6 . . ?
C12A C11A H11A 120.6 . . ?
C13A C12A C11A 119.7(5) . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C14A C13A C12A 120.7(5) . . ?
C14A C13A H13A 119.7 . . ?
C12A C13A H13A 119.7 . . ?
C13A C14A C15A 119.8(5) . . ?
C13A C14A H14A 120.1 . . ?
C15A C14A H14A 120.1 . . ?
C10A C15A C14A 119.5(5) . . ?
C10A C15A H15A 120.2 . . ?
C14A C15A H15A 120.2 . . ?
F3' C16A F2' 124.4(18) . . ?
F2A C16A F1A 130.8(9) . . ?
F2A C16A F3A 91.5(7) . . ?
F1A C16A F3A 94.9(8) . . ?
F3' C16A F1' 105.7(17) . . ?
F2' C16A F1' 29.4(14) . . ?
F3' C16A C9A 116.9(13) . . ?
F2' C16A C9A 111.6(13) . . ?
F2A C16A C9A 112.9(7) . . ?
F1A C16A C9A 109.8(7) . . ?
F3A C16A C9A 111.4(7) . . ?
F1' C16A C9A 110.1(9) . . ?
F2' F1' C16A 56(3) . . ?
F1' F2' C16A 95(4) . . ?
C7A O1A C10A 117.2(3) . . ?
C7A N1A N2A 110.1(4) . . ?
C7A N1A C1A 129.1(4) . . ?
N2A N1A C1A 120.8(4) . . ?
C9A N2A N1A 104.3(4) . . ?
C6B C1B C2B 121.4(5) . . ?
C6B C1B N1B 121.0(4) . . ?
C2B C1B N1B 117.7(5) . . ?
C1B C2B C3B 118.4(5) . . ?
C1B C2B H2B 120.8 . . ?
C3B C2B H2B 120.8 . . ?
C4B C3B C2B 120.4(5) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C5B 120.6(6) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C4B C5B C6B 120.5(6) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C1B C6B C5B 118.8(5) . . ?
C1B C6B H6B 120.6 . . ?
C5B C6B H6B 120.6 . . ?
C8B C7B O1B 133.5(5) . . ?
C8B C7B N1B 108.0(4) . . ?
O1B C7B N1B 118.5(4) . . ?
C7B C8B C9B 104.4(4) . . ?
C7B C8B H8B 127.8 . . ?
C9B C8B H8B 127.8 . . ?
N2B C9B C8B 112.8(4) . . ?
N2B C9B C16B 119.0(5) . . ?
C8B C9B C16B 128.1(5) . . ?
C15B C10B C11B 121.6(5) . . ?
C15B C10B O1B 120.0(5) . . ?
C11B C10B O1B 118.3(5) . . ?
C10B C11B C12B 117.7(6) . . ?
C10B C11B H11B 121.2 . . ?
C12B C11B H11B 121.2 . . ?
C13B C12B C11B 121.0(6) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
C14B C13B C12B 120.0(6) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 120.5(6) . . ?
C13B C14B H14B 119.7 . . ?
C15B C14B H14B 119.7 . . ?
C10B C15B C14B 119.2(6) . . ?
C10B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
F2" C16B F3" 110.8(19) . . ?
F2" C16B F1" 39.8(13) . . ?
F3" C16B F1" 128.8(15) . . ?
F3B C16B F1B 88.9(10) . . ?
F3B C16B F2B 101.3(8) . . ?
F1B C16B F2B 128.3(8) . . ?
F2" C16B C9B 117.8(10) . . ?
F3" C16B C9B 119.6(14) . . ?
F3B C16B C9B 113.8(8) . . ?
F1" C16B C9B 111.4(8) . . ?
F1B C16B C9B 109.5(7) . . ?
F2B C16B C9B 111.8(6) . . ?
F2" F1" C16B 62.3(18) . . ?
F1" F2" C16B 78(2) . . ?
C7B O1B C10B 115.7(4) . . ?
N2B N1B C7B 110.9(4) . . ?
N2B N1B C1B 119.3(4) . . ?
C7B N1B C1B 129.7(4) . . ?
C9B N2B N1B 104.0(4) . . ?

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
C6A C1A C2A C3A 0.4(7) . . . . ?
N1A C1A C2A C3A -179.1(4) . . . . ?
C1A C2A C3A C4A -1.0(8) . . . . ?
C2A C3A C4A C5A 0.8(9) . . . . ?
C3A C4A C5A C6A -0.1(9) . . . . ?
C2A C1A C6A C5A 0.4(7) . . . . ?
N1A C1A C6A C5A 179.8(4) . . . . ?
C4A C5A C6A C1A -0.5(8) . . . . ?
O1A C7A C8A C9A 173.6(6) . . . . ?
N1A C7A C8A C9A -0.7(5) . . . . ?
C7A C8A C9A N2A -0.5(6) . . . . ?
C7A C8A C9A C16A -178.4(6) . . . . ?
C15A C10A C11A C12A 0.0(7) . . . . ?
O1A C10A C11A C12A -176.0(4) . . . . ?
C10A C11A C12A C13A 0.0(7) . . . . ?
C11A C12A C13A C14A 0.1(8) . . . . ?
C12A C13A C14A C15A -0.2(8) . . . . ?
C11A C10A C15A C14A -0.1(8) . . . . ?
O1A C10A C15A C14A 175.7(5) . . . . ?
C13A C14A C15A C10A 0.2(8) . . . . ?
N2A C9A C16A F3' 3(2) . . . . ?
C8A C9A C16A F3' -179.6(18) . . . . ?
N2A C9A C16A F2' 154.8(17) . . . . ?
C8A C9A C16A F2' -27.5(19) . . . . ?
N2A C9A C16A F2A -138.5(7) . . . . ?
C8A C9A C16A F2A 39.2(10) . . . . ?
N2A C9A C16A F1A 66.6(11) . . . . ?
C8A C9A C16A F1A -115.6(10) . . . . ?
N2A C9A C16A F3A -37.2(10) . . . . ?
C8A C9A C16A F3A 140.5(7) . . . . ?
N2A C9A C16A F1' 123.3(13) . . . . ?
C8A C9A C16A F1' -59.0(15) . . . . ?
F3' C16A F1' F2' -134(4) . . . . ?
C9A C16A F1' F2' 99(3) . . . . ?
F3' C16A F2' F1' 57(4) . . . . ?
C9A C16A F2' F1' -93(3) . . . . ?
N1A C7A O1A C10A -151.2(4) . . . . ?
C8A C7A O1A C10A 34.9(8) . . . . ?
C15A C10A O1A C7A 55.1(7) . . . . ?
C11A C10A O1A C7A -128.9(5) . . . . ?
O1A C7A N1A N2A -173.6(4) . . . . ?
C8A C7A N1A N2A 1.7(5) . . . . ?
O1A C7A N1A C1A 3.3(7) . . . . ?
C8A C7A N1A C1A 178.5(4) . . . . ?
C6A C1A N1A C7A 40.9(7) . . . . ?
C2A C1A N1A C7A -139.6(5) . . . . ?
C6A C1A N1A N2A -142.5(5) . . . . ?
C2A C1A N1A N2A 36.9(6) . . . . ?
C8A C9A N2A N1A 1.5(6) . . . . ?
C16A C9A N2A N1A 179.5(5) . . . . ?
C7A N1A N2A C9A -2.0(5) . . . . ?
C1A N1A N2A C9A -179.1(4) . . . . ?
C6B C1B C2B C3B 0.2(7) . . . . ?
N1B C1B C2B C3B -179.1(4) . . . . ?
C1B C2B C3B C4B -0.3(8) . . . . ?
C2B C3B C4B C5B -0.6(9) . . . . ?
C3B C4B C5B C6B 1.7(9) . . . . ?
C2B C1B C6B C5B 0.9(7) . . . . ?
N1B C1B C6B C5B -179.8(4) . . . . ?
C4B C5B C6B C1B -1.9(8) . . . . ?
O1B C7B C8B C9B 177.9(6) . . . . ?
N1B C7B C8B C9B -0.3(6) . . . . ?
C7B C8B C9B N2B -0.4(6) . . . . ?
C7B C8B C9B C16B 178.8(6) . . . . ?
C15B C10B C11B C12B 1.1(9) . . . . ?
O1B C10B C11B C12B -176.3(6) . . . . ?
C10B C11B C12B C13B -0.5(11) . . . . ?
C11B C12B C13B C14B -0.3(12) . . . . ?
C12B C13B C14B C15B 0.7(11) . . . . ?
C11B C10B C15B C14B -0.7(8) . . . . ?
O1B C10B C15B C14B 176.5(5) . . . . ?
C13B C14B C15B C10B -0.2(9) . . . . ?
N2B C9B C16B F2" 120(2) . . . . ?
C8B C9B C16B F2" -59(2) . . . . ?
N2B C9B C16B F3" -19.6(19) . . . . ?
C8B C9B C16B F3" 161.2(17) . . . . ?
N2B C9B C16B F3B -50.0(11) . . . . ?
C8B C9B C16B F3B 130.8(9) . . . . ?
N2B C9B C16B F1" 163.4(13) . . . . ?
C8B C9B C16B F1" -15.8(17) . . . . ?
N2B C9B C16B F1B -147.7(8) . . . . ?
C8B C9B C16B F1B 33.2(12) . . . . ?
N2B C9B C16B F2B 64.1(8) . . . . ?
C8B C9B C16B F2B -115.1(8) . . . . ?
F3" C16B F1" F2" 75(3) . . . . ?
C9B C16B F1" F2" -108.1(17) . . . . ?
F3" C16B F2" F1" -126(2) . . . . ?
C9B C16B F2" F1" 90.7(18) . . . . ?
C8B C7B O1B C10B 12.1(9) . . . . ?
N1B C7B O1B C10B -169.9(5) . . . . ?
C15B C10B O1B C7B 81.1(6) . . . . ?
C11B C10B O1B C7B -101.5(6) . . . . ?
C8B C7B N1B N2B 0.8(6) . . . . ?
O1B C7B N1B N2B -177.7(5) . . . . ?
C8B C7B N1B C1B 177.3(4) . . . . ?
O1B C7B N1B C1B -1.2(8) . . . . ?
C6B C1B N1B N2B -146.3(4) . . . . ?
C2B C1B N1B N2B 32.9(6) . . . . ?
C6B C1B N1B C7B 37.5(7) . . . . ?
C2B C1B N1B C7B -143.3(5) . . . . ?
C8B C9B N2B N1B 0.9(5) . . . . ?
C16B C9B N2B N1B -178.4(5) . . . . ?
C7B N1B N2B C9B -1.1(5) . . . . ?
C1B N1B N2B C9B -177.9(4) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_KA935_0m
_database_code_depnum_ccdc_archive 'CCDC 2175626'
loop_
_audit_author_name
_audit_author_address
B.Sridhar
;CSIR IICT
India
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2023-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9291(3)
_cell_length_b                   8.5789(2)
_cell_length_c                   15.4251(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.4620(8)
_cell_angle_gamma                90
_cell_volume                     1748.38(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6890
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21077
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         30.697
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5395
_reflns_number_gt                2877
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.3634P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5395
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.33736(13) 0.4538(2) 0.82126(11) 0.0496(4) Uani 1 1 d . . . . .
C2 C 0.35040(12) 0.61616(18) 0.81236(10) 0.0435(4) Uani 1 1 d . . . . .
C3 C 0.25548(12) 0.66695(18) 0.76443(10) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.41165(16) 0.3358(2) 0.87345(14) 0.0711(6) Uani 1 1 d . . . . .
H4A H 0.376278 0.244007 0.882092 0.107 Uiso 1 1 calc R U . . .
H4B H 0.449631 0.377966 0.931890 0.107 Uiso 1 1 calc R U . . .
H4C H 0.456931 0.309199 0.840025 0.107 Uiso 1 1 calc R U . . .
C5 C 0.44385(12) 0.70787(19) 0.84200(10) 0.0457(4) Uani 1 1 d . . . . .
C6 C 0.53306(13) 0.6462(2) 0.83437(13) 0.0589(5) Uani 1 1 d . . . . .
H6 H 0.533118 0.545828 0.811570 0.071 Uiso 1 1 calc R U . . .
C7 C 0.62101(15) 0.7310(3) 0.85992(15) 0.0712(6) Uani 1 1 d . . . . .
H7 H 0.680064 0.687641 0.854572 0.085 Uiso 1 1 calc R U . . .
C8 C 0.62239(16) 0.8788(3) 0.89320(15) 0.0712(6) Uani 1 1 d . . . . .
H8 H 0.682201 0.935942 0.910666 0.085 Uiso 1 1 calc R U . . .
C9 C 0.53516(16) 0.9424(2) 0.90070(14) 0.0687(5) Uani 1 1 d . . . . .
H9 H 0.535794 1.043228 0.922972 0.082 Uiso 1 1 calc R U . . .
C10 C 0.44648(14) 0.8579(2) 0.87547(12) 0.0575(5) Uani 1 1 d . . . . .
H10 H 0.387766 0.902190 0.881013 0.069 Uiso 1 1 calc R U . . .
C11 C 0.21341(11) 0.86234(17) 0.65108(10) 0.0399(3) Uani 1 1 d . . . . .
C12 C 0.27645(13) 0.8067(2) 0.60584(11) 0.0509(4) Uani 1 1 d . . . . .
H12 H 0.324616 0.730951 0.632171 0.061 Uiso 1 1 calc R U . . .
C13 C 0.26691(16) 0.8654(2) 0.52062(12) 0.0654(5) Uani 1 1 d . . . . .
H13 H 0.309173 0.828969 0.488952 0.078 Uiso 1 1 calc R U . . .
C14 C 0.19616(17) 0.9764(3) 0.48190(12) 0.0701(6) Uani 1 1 d . . . . .
H14 H 0.190196 1.014765 0.424029 0.084 Uiso 1 1 calc R U . . .
C15 C 0.13418(15) 1.0312(2) 0.52804(13) 0.0648(5) Uani 1 1 d . . . . .
H15 H 0.086224 1.107232 0.501622 0.078 Uiso 1 1 calc R U . . .
C16 C 0.14243(13) 0.9742(2) 0.61381(12) 0.0529(4) Uani 1 1 d . . . . .
H16 H 0.100490 1.011245 0.645641 0.063 Uiso 1 1 calc R U . . .
C17 C 0.08718(12) 0.5361(2) 0.69405(11) 0.0480(4) Uani 1 1 d . . . . .
C18 C 0.02083(14) 0.6428(2) 0.70917(13) 0.0639(5) Uani 1 1 d . . . . .
H18 H 0.043952 0.722888 0.751265 0.077 Uiso 1 1 calc R U . . .
C19 C -0.08082(16) 0.6293(3) 0.66083(16) 0.0787(6) Uani 1 1 d . . . . .
H19 H -0.126634 0.700779 0.670368 0.094 Uiso 1 1 calc R U . . .
C20 C -0.11451(17) 0.5116(3) 0.59913(16) 0.0833(7) Uani 1 1 d . . . . .
H20 H -0.183154 0.502807 0.567060 0.100 Uiso 1 1 calc R U . . .
C21 C -0.04743(18) 0.4065(3) 0.58437(15) 0.0803(6) Uani 1 1 d . . . . .
H21 H -0.070624 0.326641 0.542103 0.096 Uiso 1 1 calc R U . . .
C22 C 0.05376(15) 0.4183(2) 0.63163(13) 0.0635(5) Uani 1 1 d . . . . .
H22 H 0.099379 0.347078 0.621456 0.076 Uiso 1 1 calc R U . . .
N1 N 0.19187(10) 0.54346(15) 0.74444(9) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.24267(11) 0.41003(16) 0.78011(10) 0.0521(4) Uani 1 1 d . . . . .
O1 O 0.22015(8) 0.81318(12) 0.73888(7) 0.0472(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 N2 1.324(2) . ?
C1 C2 1.417(2) . ?
C1 C4 1.489(2) . ?
C2 C3 1.366(2) . ?
C2 C5 1.465(2) . ?
C3 N1 1.353(2) . ?
C3 O1 1.3595(18) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.383(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.367(2) . ?
C11 C12 1.369(2) . ?
C11 O1 1.3929(17) . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.371(3) . ?
C17 C18 1.372(2) . ?
C17 N1 1.420(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 N2 1.3664(18) . ?

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
N2 C1 C2 111.77(14) . . ?
N2 C1 C4 118.87(16) . . ?
C2 C1 C4 129.23(16) . . ?
C3 C2 C1 103.55(14) . . ?
C3 C2 C5 127.58(15) . . ?
C1 C2 C5 128.77(14) . . ?
N1 C3 O1 120.38(14) . . ?
N1 C3 C2 109.00(14) . . ?
O1 C3 C2 130.60(15) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 117.87(17) . . ?
C10 C5 C2 122.16(15) . . ?
C6 C5 C2 119.94(15) . . ?
C7 C6 C5 121.00(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.38(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.70(18) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 121.71(15) . . ?
C16 C11 O1 116.01(13) . . ?
C12 C11 O1 122.24(14) . . ?
C11 C12 C13 118.47(17) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 120.80(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.04(17) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.21(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 118.77(17) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C22 C17 C18 120.91(17) . . ?
C22 C17 N1 118.59(15) . . ?
C18 C17 N1 120.48(16) . . ?
C17 C18 C19 118.9(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C3 N1 N2 110.24(13) . . ?
C3 N1 C17 130.14(13) . . ?
N2 N1 C17 119.61(13) . . ?
C1 N2 N1 105.42(13) . . ?
C3 O1 C11 117.91(11) . . ?

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
N2 C1 C2 C3 1.36(17) . . . . ?
C4 C1 C2 C3 -174.40(17) . . . . ?
N2 C1 C2 C5 -175.19(14) . . . . ?
C4 C1 C2 C5 9.0(3) . . . . ?
C1 C2 C3 N1 -1.51(16) . . . . ?
C5 C2 C3 N1 175.09(14) . . . . ?
C1 C2 C3 O1 176.75(15) . . . . ?
C5 C2 C3 O1 -6.6(2) . . . . ?
C3 C2 C5 C10 40.2(2) . . . . ?
C1 C2 C5 C10 -144.07(17) . . . . ?
C3 C2 C5 C6 -137.91(17) . . . . ?
C1 C2 C5 C6 37.9(2) . . . . ?
C10 C5 C6 C7 0.5(3) . . . . ?
C2 C5 C6 C7 178.67(16) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C9 -0.3(2) . . . . ?
C2 C5 C10 C9 -178.41(16) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
O1 C11 C12 C13 -177.81(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
O1 C11 C16 C15 178.05(15) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
N1 C17 C18 C19 -178.11(16) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C18 C17 C22 C21 -0.6(3) . . . . ?
N1 C17 C22 C21 178.01(17) . . . . ?
O1 C3 N1 N2 -177.24(12) . . . . ?
C2 C3 N1 N2 1.23(16) . . . . ?
O1 C3 N1 C17 3.4(2) . . . . ?
C2 C3 N1 C17 -178.09(14) . . . . ?
C22 C17 N1 C3 135.75(17) . . . . ?
C18 C17 N1 C3 -45.7(2) . . . . ?
C22 C17 N1 N2 -43.5(2) . . . . ?
C18 C17 N1 N2 135.08(17) . . . . ?
C2 C1 N2 N1 -0.65(17) . . . . ?
C4 C1 N2 N1 175.60(15) . . . . ?
C3 N1 N2 C1 -0.34(16) . . . . ?
C17 N1 N2 C1 179.06(13) . . . . ?
N1 C3 O1 C11 -85.58(17) . . . . ?
C2 C3 O1 C11 96.32(18) . . . . ?
C16 C11 O1 C3 153.64(14) . . . . ?
C12 C11 O1 C3 -28.7(2) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.042

