# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_KB74_0m
_database_code_depnum_ccdc_archive 'CCDC 2154454'
loop_
_audit_author_name
_audit_author_address
'Dr Saibal Das'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-08 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 H17 N3 O3'
_chemical_formula_sum            'C16 H17 N3 O3'
_chemical_formula_weight         299.32

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.7220(3)
_cell_length_b                   19.1925(7)
_cell_length_c                   11.3024(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.638(2)
_cell_angle_gamma                90
_cell_volume                     1417.03(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9784
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      30.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18455
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.819
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3250
_reflns_number_gt                2722
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0471P)²+0.5953P] 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         3250
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.8727(3) 0.82950(10) 0.27027(18) 0.0537(5) Uani 1 1 d . . . . .
H1A H 0.899039 0.816947 0.192244 0.064 Uiso 1 1 calc R U . . .
H1AB H 0.998130 0.847128 0.322682 0.064 Uiso 1 1 calc R U . . .
C2 C 0.7023(4) 0.88369(10) 0.2543(2) 0.0660(6) Uani 1 1 d . . . . .
H2A H 0.667053 0.900534 0.171049 0.079 Uiso 1 1 calc R U . . .
H2AB H 0.746187 0.922969 0.308141 0.079 Uiso 1 1 calc R U . . .
C3 C 0.5179(3) 0.84796(9) 0.28547(17) 0.0508(4) Uani 1 1 d . . . . .
H3A H 0.501600 0.862405 0.364886 0.061 Uiso 1 1 calc R U . . .
H3AB H 0.393056 0.858262 0.224943 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5708(2) 0.77144(7) 0.28485(13) 0.0319(3) Uani 1 1 d . . . . .
C5 C 0.4831(2) 0.72618(8) 0.37055(12) 0.0350(3) Uani 1 1 d . . . . .
C6 C 0.5613(3) 0.61307(10) 0.48229(15) 0.0543(5) Uani 1 1 d . . . . .
H6 H 0.451989 0.611045 0.519572 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7095(4) 0.56564(11) 0.49230(18) 0.0654(6) Uani 1 1 d . . . . .
H7 H 0.720934 0.524746 0.537550 0.078 Uiso 1 1 calc R U . . .
C8 C 0.8461(3) 0.58825(10) 0.42222(17) 0.0550(5) Uani 1 1 d . . . . .
H8 H 0.962650 0.564736 0.413274 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7778(2) 0.65001(8) 0.37050(13) 0.0358(3) Uani 1 1 d . . . . .
C10 C 0.8461(2) 0.69978(8) 0.28728(13) 0.0330(3) Uani 1 1 d . . . . .
H10 H 0.992682 0.695126 0.291042 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7132(2) 0.69270(8) 0.15335(13) 0.0336(3) Uani 1 1 d . . . . .
H11 H 0.787467 0.710138 0.094486 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5257(2) 0.73756(7) 0.15325(12) 0.0304(3) Uani 1 1 d . . . . .
H12 H 0.510577 0.773896 0.090840 0.036 Uiso 1 1 calc R U . . .
C13 C 0.3470(2) 0.68819(8) 0.12394(12) 0.0313(3) Uani 1 1 d . . . . .
C14 C 0.6305(2) 0.62085(9) 0.11975(14) 0.0401(4) Uani 1 1 d . . . . .
C15 C 0.2883(3) 0.56075(9) 0.08621(17) 0.0517(5) Uani 1 1 d . . . . .
H15A H 0.337672 0.529403 0.032160 0.062 Uiso 1 1 calc R U . . .
H15B H 0.150380 0.574799 0.045826 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2832(4) 0.52300(12) 0.2012(2) 0.0839(8) Uani 1 1 d . . . . .
H16A H 0.196331 0.482842 0.182398 0.126 Uiso 1 1 calc R U . . .
H16B H 0.230776 0.553432 0.254114 0.126 Uiso 1 1 calc R U . . .
H16C H 0.419180 0.508497 0.241054 0.126 Uiso 1 1 calc R U . . .
N1 N 0.79565(18) 0.76906(6) 0.32648(11) 0.0334(3) Uani 1 1 d . . . . .
N2 N 0.5987(2) 0.66620(7) 0.40626(11) 0.0364(3) Uani 1 1 d . . . . .
N3 N 0.41991(19) 0.62242(7) 0.10873(11) 0.0362(3) Uani 1 1 d . . . . .
O1 O 0.32891(17) 0.73761(8) 0.40340(11) 0.0533(3) Uani 1 1 d . . . . .
O2 O 0.16949(16) 0.70202(7) 0.11633(11) 0.0464(3) Uani 1 1 d . . . . .
O3 O 0.7238(2) 0.56921(7) 0.10477(14) 0.0667(4) 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 N1 1.474(2) . ?
C1 C2 1.526(3) . ?
C1 H1A 0.9700 . ?
C1 H1AB 0.9700 . ?
C2 C3 1.529(3) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.511(2) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 N1 1.4742(18) . ?
C4 C5 1.519(2) . ?
C4 C12 1.5858(19) . ?
C5 O1 1.2009(18) . ?
C5 N2 1.394(2) . ?
C6 C7 1.334(3) . ?
C6 N2 1.394(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.353(2) . ?
C8 H8 0.9300 . ?
C9 N2 1.392(2) . ?
C9 C10 1.487(2) . ?
C10 N1 1.4665(19) . ?
C10 C11 1.5717(19) . ?
C10 H10 0.9800 . ?
C11 C14 1.502(2) . ?
C11 C12 1.526(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.504(2) . ?
C12 H12 0.9800 . ?
C13 O2 1.2057(17) . ?
C13 N3 1.3794(19) . ?
C14 O3 1.206(2) . ?
C14 N3 1.391(2) . ?
C15 N3 1.464(2) . ?
C15 C16 1.496(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
N1 C1 C2 104.91(15) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1AB 110.8 . . ?
C2 C1 H1AB 110.8 . . ?
H1A C1 H1AB 108.8 . . ?
C1 C2 C3 107.08(15) . . ?
C1 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
C1 C2 H2AB 110.3 . . ?
C3 C2 H2AB 110.3 . . ?
H2A C2 H2AB 108.6 . . ?
C4 C3 C2 103.33(15) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3AB 111.1 . . ?
C2 C3 H3AB 111.1 . . ?
H3A C3 H3AB 109.1 . . ?
N1 C4 C3 104.66(12) . . ?
N1 C4 C5 107.54(11) . . ?
C3 C4 C5 115.19(13) . . ?
N1 C4 C12 103.96(11) . . ?
C3 C4 C12 114.19(13) . . ?
C5 C4 C12 110.28(11) . . ?
O1 C5 N2 121.61(15) . . ?
O1 C5 C4 125.83(15) . . ?
N2 C5 C4 112.53(12) . . ?
C7 C6 N2 108.16(17) . . ?
C7 C6 H6 125.9 . . ?
N2 C6 H6 125.9 . . ?
C6 C7 C8 108.27(17) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 H7 125.9 . . ?
C9 C8 C7 108.15(18) . . ?
C9 C8 H8 125.9 . . ?
C7 C8 H8 125.9 . . ?
C8 C9 N2 107.37(15) . . ?
C8 C9 C10 135.38(16) . . ?
N2 C9 C10 117.23(13) . . ?
N1 C10 C9 105.26(11) . . ?
N1 C10 C11 104.47(11) . . ?
C9 C10 C11 111.31(12) . . ?
N1 C10 H10 111.8 . . ?
C9 C10 H10 111.8 . . ?
C11 C10 H10 111.8 . . ?
C14 C11 C12 105.14(12) . . ?
C14 C11 C10 114.55(12) . . ?
C12 C11 C10 103.53(11) . . ?
C14 C11 H11 111.1 . . ?
C12 C11 H11 111.1 . . ?
C10 C11 H11 111.1 . . ?
C13 C12 C11 105.15(12) . . ?
C13 C12 C4 115.52(11) . . ?
C11 C12 C4 104.81(11) . . ?
C13 C12 H12 110.3 . . ?
C11 C12 H12 110.3 . . ?
C4 C12 H12 110.3 . . ?
O2 C13 N3 124.55(14) . . ?
O2 C13 C12 127.06(14) . . ?
N3 C13 C12 108.38(12) . . ?
O3 C14 N3 123.85(16) . . ?
O3 C14 C11 128.02(15) . . ?
N3 C14 C11 108.12(13) . . ?
N3 C15 C16 112.17(15) . . ?
N3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 N1 C1 116.97(13) . . ?
C10 N1 C4 102.98(11) . . ?
C1 N1 C4 106.03(12) . . ?
C9 N2 C6 108.05(15) . . ?
C9 N2 C5 124.14(12) . . ?
C6 N2 C5 127.81(14) . . ?
C13 N3 C14 113.09(12) . . ?
C13 N3 C15 122.95(14) . . ?
C14 N3 C15 123.94(14) . . ?

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 C1 C2 C3 -8.2(2) . . . . ?
C1 C2 C3 C4 -14.6(2) . . . . ?
C2 C3 C4 N1 32.14(17) . . . . ?
C2 C3 C4 C5 150.00(14) . . . . ?
C2 C3 C4 C12 -80.86(17) . . . . ?
N1 C4 C5 O1 144.02(14) . . . . ?
C3 C4 C5 O1 27.8(2) . . . . ?
C12 C4 C5 O1 -103.25(16) . . . . ?
N1 C4 C5 N2 -38.11(15) . . . . ?
C3 C4 C5 N2 -154.34(13) . . . . ?
C12 C4 C5 N2 74.63(14) . . . . ?
N2 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 N2 -0.6(2) . . . . ?
C7 C8 C9 C10 -178.93(17) . . . . ?
C8 C9 C10 N1 -145.07(19) . . . . ?
N2 C9 C10 N1 36.68(16) . . . . ?
C8 C9 C10 C11 102.3(2) . . . . ?
N2 C9 C10 C11 -75.93(16) . . . . ?
N1 C10 C11 C14 -143.37(12) . . . . ?
C9 C10 C11 C14 -30.26(17) . . . . ?
N1 C10 C11 C12 -29.47(14) . . . . ?
C9 C10 C11 C12 83.64(14) . . . . ?
C14 C11 C12 C13 1.96(14) . . . . ?
C10 C11 C12 C13 -118.55(12) . . . . ?
C14 C11 C12 C4 124.18(12) . . . . ?
C10 C11 C12 C4 3.67(14) . . . . ?
N1 C4 C12 C13 138.15(12) . . . . ?
C3 C4 C12 C13 -108.43(15) . . . . ?
C5 C4 C12 C13 23.13(16) . . . . ?
N1 C4 C12 C11 22.95(14) . . . . ?
C3 C4 C12 C11 136.37(14) . . . . ?
C5 C4 C12 C11 -92.06(13) . . . . ?
C11 C12 C13 O2 178.96(14) . . . . ?
C4 C12 C13 O2 63.96(19) . . . . ?
C11 C12 C13 N3 0.03(14) . . . . ?
C4 C12 C13 N3 -114.97(13) . . . . ?
C12 C11 C14 O3 177.14(17) . . . . ?
C10 C11 C14 O3 -69.9(2) . . . . ?
C12 C11 C14 N3 -3.32(15) . . . . ?
C10 C11 C14 N3 109.63(13) . . . . ?
C9 C10 N1 C1 171.78(13) . . . . ?
C11 C10 N1 C1 -70.88(15) . . . . ?
C9 C10 N1 C4 -72.43(13) . . . . ?
C11 C10 N1 C4 44.92(13) . . . . ?
C2 C1 N1 C10 142.83(15) . . . . ?
C2 C1 N1 C4 28.73(18) . . . . ?
C3 C4 N1 C10 -162.09(12) . . . . ?
C5 C4 N1 C10 74.95(13) . . . . ?
C12 C4 N1 C10 -41.99(13) . . . . ?
C3 C4 N1 C1 -38.69(16) . . . . ?
C5 C4 N1 C1 -161.65(13) . . . . ?
C12 C4 N1 C1 81.40(14) . . . . ?
C8 C9 N2 C6 0.71(18) . . . . ?
C10 C9 N2 C6 179.43(13) . . . . ?
C8 C9 N2 C5 -179.78(14) . . . . ?
C10 C9 N2 C5 -1.1(2) . . . . ?
C7 C6 N2 C9 -0.59(19) . . . . ?
C7 C6 N2 C5 179.92(16) . . . . ?
O1 C5 N2 C9 179.59(14) . . . . ?
C4 C5 N2 C9 1.61(19) . . . . ?
O1 C5 N2 C6 -1.0(2) . . . . ?
C4 C5 N2 C6 -178.98(14) . . . . ?
O2 C13 N3 C14 178.75(14) . . . . ?
C12 C13 N3 C14 -2.28(16) . . . . ?
O2 C13 N3 C15 -2.6(2) . . . . ?
C12 C13 N3 C15 176.36(13) . . . . ?
O3 C14 N3 C13 -176.84(16) . . . . ?
C11 C14 N3 C13 3.60(16) . . . . ?
O3 C14 N3 C15 4.5(2) . . . . ?
C11 C14 N3 C15 -175.03(13) . . . . ?
C16 C15 N3 C13 -93.5(2) . . . . ?
C16 C15 N3 C14 84.9(2) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_KB361_0m
_database_code_depnum_ccdc_archive 'CCDC 2154458'
loop_
_audit_author_name
_audit_author_address
'Dr Saibal Das'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-08 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         ?
_chemical_formula_sum            'C19 H21 N3 O3'
_chemical_formula_weight         339.39

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                   10.6245(10)
_cell_length_b                   11.4523(17)
_cell_length_c                   14.3907(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.884(4)
_cell_angle_gamma                90
_cell_volume                     1747.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      30.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_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            32522
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         30.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5272
_reflns_number_gt                3938
_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0653P)²+0.3659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5272
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.57173(12) 0.29555(11) 0.68754(8) 0.0450(3) Uani 1 1 d . . . . .
C2 C 0.71406(14) 0.26933(15) 0.69402(13) 0.0655(4) Uani 1 1 d . . . . .
H2A H 0.729212 0.185851 0.697117 0.079 Uiso 1 1 calc R U . . .
H2B H 0.753450 0.300760 0.640527 0.079 Uiso 1 1 calc R U . . .
C3 C 0.76493(17) 0.32863(16) 0.78279(15) 0.0785(5) Uani 1 1 d . . . . .
H3A H 0.834592 0.284739 0.812557 0.094 Uiso 1 1 calc R U . . .
H3B H 0.793269 0.407260 0.770359 0.094 Uiso 1 1 calc R U . . .
C4 C 0.65480(17) 0.33029(15) 0.84203(12) 0.0711(5) Uani 1 1 d . . . . .
H4A H 0.642739 0.254794 0.870658 0.085 Uiso 1 1 calc R U . . .
H4B H 0.665228 0.389243 0.890344 0.085 Uiso 1 1 calc R U . . .
C5 C 0.48857(14) 0.18276(11) 0.68854(9) 0.0494(3) Uani 1 1 d . . . . .
H5 H 0.543640 0.114116 0.694141 0.059 Uiso 1 1 calc R U . . .
C6 C 0.41341(15) 0.19134(12) 0.77455(8) 0.0543(3) Uani 1 1 d . . . . .
H6 H 0.449950 0.141710 0.824883 0.065 Uiso 1 1 calc R U . . .
C7 C 0.42453(14) 0.32396(12) 0.80130(8) 0.0526(3) Uani 1 1 d . . . . .
H7 H 0.421374 0.332359 0.868871 0.063 Uiso 1 1 calc R U . . .
C8 C 0.38922(16) 0.16378(12) 0.60937(9) 0.0561(3) Uani 1 1 d . . . . .
C9 C 0.28245(16) 0.15183(13) 0.74305(10) 0.0608(4) Uani 1 1 d . . . . .
C10 C 0.53435(11) 0.37645(10) 0.60577(8) 0.0433(3) Uani 1 1 d . . . . .
C11 C 0.32447(11) 0.44488(10) 0.66407(8) 0.0418(3) Uani 1 1 d . . . . .
C12 C 0.32127(13) 0.39585(11) 0.75307(8) 0.0485(3) Uani 1 1 d . . . . .
C13 C 0.21130(17) 0.41212(17) 0.79954(12) 0.0718(5) Uani 1 1 d . . . . .
H13 H 0.207096 0.380237 0.858684 0.086 Uiso 1 1 calc R U . . .
C14 C 0.10946(18) 0.47305(18) 0.76161(16) 0.0816(6) Uani 1 1 d . . . . .
H14 H 0.037536 0.481199 0.794449 0.098 Uiso 1 1 calc R U . . .
C15 C 0.11416(15) 0.52194(15) 0.67501(15) 0.0704(5) Uani 1 1 d . . . . .
H15 H 0.045739 0.564129 0.649026 0.084 Uiso 1 1 calc R U . . .
C16 C 0.22083(13) 0.50827(12) 0.62658(11) 0.0540(3) Uani 1 1 d . . . . .
H16 H 0.223804 0.541860 0.567932 0.065 Uiso 1 1 calc R U . . .
C17 C 0.16019(17) 0.11843(14) 0.58953(12) 0.0691(4) Uani 1 1 d . . . . .
H17A H 0.109631 0.064045 0.622823 0.083 Uiso 1 1 calc R U . . .
H17B H 0.182157 0.080754 0.532464 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0835(2) 0.22465(19) 0.56554(17) 0.0962(7) Uani 1 1 d . . . . .
H18A H 0.133640 0.279144 0.532016 0.115 Uiso 1 1 calc R U . . .
H18B H 0.061023 0.262398 0.622442 0.115 Uiso 1 1 calc R U . . .
C19 C -0.0345(2) 0.1954(2) 0.50690(19) 0.1061(8) Uani 1 1 d . . . . .
H19A H -0.012614 0.157320 0.450798 0.159 Uiso 1 1 calc R U . . .
H19B H -0.080214 0.265821 0.491372 0.159 Uiso 1 1 calc R U . . .
H19C H -0.086203 0.144311 0.541042 0.159 Uiso 1 1 calc R U . . .
O1 O 0.60314(10) 0.38956(10) 0.54182(7) 0.0641(3) Uani 1 1 d . . . . .
O2 O 0.40454(14) 0.16175(14) 0.52764(8) 0.0883(4) Uani 1 1 d . . . . .
O3 O 0.19523(13) 0.13095(13) 0.78964(9) 0.0858(4) Uani 1 1 d . . . . .
N1 N 0.54834(11) 0.35918(10) 0.77419(7) 0.0500(3) Uani 1 1 d . . . . .
N2 N 0.27566(13) 0.14453(11) 0.64658(8) 0.0577(3) Uani 1 1 d . . . . .
N3 N 0.42515(10) 0.43748(9) 0.60520(7) 0.0445(2) Uani 1 1 d . . . . .
H3N H 0.4157(14) 0.4831(14) 0.5582(12) 0.052(4) Uiso 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 N1 1.4798(18) . ?
C1 C10 1.5288(15) . ?
C1 C2 1.5383(19) . ?
C1 C5 1.5657(18) . ?
C2 C3 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.494(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.4807(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.5154(19) . ?
C5 C6 1.521(2) . ?
C5 H5 0.9800 . ?
C6 C9 1.504(2) . ?
C6 C7 1.5693(19) . ?
C6 H6 0.9800 . ?
C7 N1 1.4542(18) . ?
C7 C12 1.503(2) . ?
C7 H7 0.9800 . ?
C8 O2 1.1984(17) . ?
C8 N2 1.371(2) . ?
C9 O3 1.2040(19) . ?
C9 N2 1.3877(19) . ?
C10 O1 1.2226(14) . ?
C10 N3 1.3540(15) . ?
C11 C16 1.3964(19) . ?
C11 C12 1.4010(17) . ?
C11 N3 1.4112(14) . ?
C12 C13 1.397(2) . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N2 1.460(2) . ?
C17 C18 1.492(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.501(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N3 H3N 0.855(17) . ?

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
N1 C1 C10 107.49(10) . . ?
N1 C1 C2 105.40(11) . . ?
C10 C1 C2 111.60(11) . . ?
N1 C1 C5 105.75(10) . . ?
C10 C1 C5 112.93(10) . . ?
C2 C1 C5 113.04(11) . . ?
C3 C2 C1 104.89(14) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C4 C3 C2 103.81(14) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C3 102.68(13) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C8 C5 C6 104.11(12) . . ?
C8 C5 C1 118.44(10) . . ?
C6 C5 C1 106.37(10) . . ?
C8 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C1 C5 H5 109.2 . . ?
C9 C6 C5 105.15(11) . . ?
C9 C6 C7 114.71(13) . . ?
C5 C6 C7 103.14(9) . . ?
C9 C6 H6 111.1 . . ?
C5 C6 H6 111.1 . . ?
C7 C6 H6 111.1 . . ?
N1 C7 C12 111.67(10) . . ?
N1 C7 C6 104.90(12) . . ?
C12 C7 C6 112.11(11) . . ?
N1 C7 H7 109.4 . . ?
C12 C7 H7 109.4 . . ?
C6 C7 H7 109.4 . . ?
O2 C8 N2 124.20(14) . . ?
O2 C8 C5 127.34(15) . . ?
N2 C8 C5 108.42(11) . . ?
O3 C9 N2 123.73(15) . . ?
O3 C9 C6 128.56(14) . . ?
N2 C9 C6 107.70(12) . . ?
O1 C10 N3 119.20(10) . . ?
O1 C10 C1 121.09(11) . . ?
N3 C10 C1 119.68(10) . . ?
C16 C11 C12 119.61(11) . . ?
C16 C11 N3 114.16(11) . . ?
C12 C11 N3 126.23(11) . . ?
C13 C12 C11 117.19(14) . . ?
C13 C12 C7 117.37(13) . . ?
C11 C12 C7 125.41(11) . . ?
C14 C13 C12 122.74(16) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C13 C14 C15 119.62(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.68(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 121.15(15) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N2 C17 C18 112.84(14) . . ?
N2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 111.74(18) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 N1 C1 107.22(10) . . ?
C7 N1 C4 115.19(11) . . ?
C1 N1 C4 106.33(12) . . ?
C8 N2 C9 113.19(12) . . ?
C8 N2 C17 122.78(13) . . ?
C9 N2 C17 124.03(14) . . ?
C10 N3 C11 135.35(10) . . ?
C10 N3 H3N 112.0(10) . . ?
C11 N3 H3N 112.6(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3.98(15) . . . . ?
C10 C1 C2 C3 112.40(14) . . . . ?
C5 C1 C2 C3 -119.00(13) . . . . ?
C1 C2 C3 C4 27.30(16) . . . . ?
C2 C3 C4 N1 -40.38(16) . . . . ?
N1 C1 C5 C8 120.28(13) . . . . ?
C10 C1 C5 C8 3.00(18) . . . . ?
C2 C1 C5 C8 -124.90(14) . . . . ?
N1 C1 C5 C6 3.66(13) . . . . ?
C10 C1 C5 C6 -113.62(12) . . . . ?
C2 C1 C5 C6 118.49(13) . . . . ?
C8 C5 C6 C9 11.69(13) . . . . ?
C1 C5 C6 C9 137.53(11) . . . . ?
C8 C5 C6 C7 -108.83(12) . . . . ?
C1 C5 C6 C7 17.01(13) . . . . ?
C9 C6 C7 N1 -146.32(11) . . . . ?
C5 C6 C7 N1 -32.57(13) . . . . ?
C9 C6 C7 C12 -24.95(14) . . . . ?
C5 C6 C7 C12 88.80(13) . . . . ?
C6 C5 C8 O2 173.30(16) . . . . ?
C1 C5 C8 O2 55.5(2) . . . . ?
C6 C5 C8 N2 -8.84(14) . . . . ?
C1 C5 C8 N2 -126.66(13) . . . . ?
C5 C6 C9 O3 170.19(17) . . . . ?
C7 C6 C9 O3 -77.2(2) . . . . ?
C5 C6 C9 N2 -10.92(15) . . . . ?
C7 C6 C9 N2 101.64(14) . . . . ?
N1 C1 C10 O1 133.45(14) . . . . ?
C2 C1 C10 O1 18.35(19) . . . . ?
C5 C1 C10 O1 -110.30(15) . . . . ?
N1 C1 C10 N3 -44.52(15) . . . . ?
C2 C1 C10 N3 -159.62(13) . . . . ?
C5 C1 C10 N3 71.73(16) . . . . ?
C16 C11 C12 C13 0.99(18) . . . . ?
N3 C11 C12 C13 -179.16(13) . . . . ?
C16 C11 C12 C7 178.84(12) . . . . ?
N3 C11 C12 C7 -1.3(2) . . . . ?
N1 C7 C12 C13 -151.09(13) . . . . ?
C6 C7 C12 C13 91.52(14) . . . . ?
N1 C7 C12 C11 31.06(17) . . . . ?
C6 C7 C12 C11 -86.33(15) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C7 C12 C13 C14 -178.10(16) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -1.1(2) . . . . ?
N3 C11 C16 C15 179.02(13) . . . . ?
N2 C17 C18 C19 180.0(2) . . . . ?
C12 C7 N1 C1 -85.49(12) . . . . ?
C6 C7 N1 C1 36.16(12) . . . . ?
C12 C7 N1 C4 156.39(12) . . . . ?
C6 C7 N1 C4 -81.95(14) . . . . ?
C10 C1 N1 C7 95.86(12) . . . . ?
C2 C1 N1 C7 -144.99(11) . . . . ?
C5 C1 N1 C7 -25.03(12) . . . . ?
C10 C1 N1 C4 -140.42(11) . . . . ?
C2 C1 N1 C4 -21.27(13) . . . . ?
C5 C1 N1 C4 98.70(12) . . . . ?
C3 C4 N1 C7 157.21(13) . . . . ?
C3 C4 N1 C1 38.60(14) . . . . ?
O2 C8 N2 C9 -179.90(16) . . . . ?
C5 C8 N2 C9 2.16(17) . . . . ?
O2 C8 N2 C17 0.4(2) . . . . ?
C5 C8 N2 C17 -177.53(13) . . . . ?
O3 C9 N2 C8 -175.37(16) . . . . ?
C6 C9 N2 C8 5.68(18) . . . . ?
O3 C9 N2 C17 4.3(3) . . . . ?
C6 C9 N2 C17 -174.64(13) . . . . ?
C18 C17 N2 C8 -93.7(2) . . . . ?
C18 C17 N2 C9 86.7(2) . . . . ?
O1 C10 N3 C11 179.39(14) . . . . ?
C1 C10 N3 C11 -2.6(2) . . . . ?
C16 C11 N3 C10 -170.50(14) . . . . ?
C12 C11 N3 C10 9.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N O1 0.855(17) 2.050(17) 2.8991(13) 172(2) 3_666 yes

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_KB312_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2154455'
loop_
_audit_author_name
_audit_author_address
'Dr Saibal Das'
;CSIR Indian Institute of Chemical Technology 
India
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-07-08 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         '2(C22 H18 F N3 O3), C H2 Cl2'
_chemical_formula_sum            'C45 H38 Cl2 F2 N6 O6'
_chemical_formula_weight         867.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

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

_cell_length_a                   22.524(2)
_cell_length_b                   24.034(7)
_cell_length_c                   7.426(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4020(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.4785
_cell_measurement_theta_max      23.621

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1800
_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    0.230
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_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            32846
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         30.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6106
_reflns_number_gt                4453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0374P)²+2.0770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6106
_refine_ls_number_parameters     290
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.962
_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 0.32147(14) 0.14221(11) 0.4251(4) 0.0528(7) Uani 1 1 d . . . . .
C2 C 0.35554(17) 0.17209(13) 0.5376(5) 0.0731(10) Uani 1 1 d . . . . .
H2 H 0.376337 0.155015 0.630619 0.088 Uiso 1 1 calc R U . . .
C3 C 0.35885(16) 0.22908(13) 0.5112(5) 0.0674(10) Uani 1 1 d . . . . .
H3 H 0.381826 0.250690 0.588248 0.081 Uiso 1 1 calc R U . . .
C4 C 0.32873(11) 0.25380(10) 0.3734(3) 0.0381(5) Uani 1 1 d . . . . .
C5 C 0.29529(17) 0.22206(12) 0.2610(5) 0.0698(10) Uani 1 1 d . . . . .
H5 H 0.274824 0.238531 0.166153 0.084 Uiso 1 1 calc R U . . .
C6 C 0.29172(18) 0.16492(13) 0.2879(6) 0.0785(11) Uani 1 1 d . . . . .
H6 H 0.268984 0.142849 0.211555 0.094 Uiso 1 1 calc R U . . .
C7 C 0.30276(10) 0.35050(10) 0.4650(3) 0.0361(5) Uani 1 1 d . . . . .
C8 C 0.31528(10) 0.40861(9) 0.3979(3) 0.0334(5) Uani 1 1 d . . . . .
H8 H 0.279001 0.424191 0.345306 0.040 Uiso 1 1 calc R U . . .
C9 C 0.36148(11) 0.40077(9) 0.2500(3) 0.0354(5) Uani 1 1 d . . . . .
H9 H 0.351256 0.422054 0.141753 0.042 Uiso 1 1 calc R U . . .
C10 C 0.36246(11) 0.33925(10) 0.2127(3) 0.0358(5) Uani 1 1 d . . . . .
C11 C 0.34249(10) 0.45165(9) 0.5332(3) 0.0313(4) Uani 1 1 d . . . . .
C12 C 0.42003(10) 0.42292(9) 0.3389(3) 0.0358(5) Uani 1 1 d . . . . .
H12 H 0.445888 0.438117 0.244810 0.043 Uiso 1 1 calc R U . . .
C13 C 0.30690(12) 0.50620(10) 0.5474(4) 0.0452(6) Uani 1 1 d D . . . .
H13A H 0.272111 0.504876 0.470543 0.054 Uiso 1 1 calc R U . A 1
H13B H 0.294195 0.512551 0.670510 0.054 Uiso 1 1 calc R U . A 1
C15 C 0.39245(14) 0.52278(11) 0.3674(4) 0.0569(7) Uani 1 1 d D . . . .
H15A H 0.376798 0.518391 0.246521 0.068 Uiso 1 1 calc R U . B 1
H15B H 0.429616 0.543091 0.361455 0.068 Uiso 1 1 calc R U . B 1
C16 C 0.35327(10) 0.42562(9) 0.7172(3) 0.0334(5) Uani 1 1 d D . . . .
C17 C 0.44215(10) 0.36515(10) 0.6240(3) 0.0343(5) Uani 1 1 d D . . . .
C18 C 0.47747(12) 0.32468(11) 0.7076(4) 0.0462(6) Uani 1 1 d . . . . .
H18 H 0.469896 0.315166 0.826830 0.055 Uiso 1 1 calc R U . . .
C19 C 0.52307(13) 0.29869(12) 0.6175(4) 0.0557(7) Uani 1 1 d . . . . .
H19 H 0.546176 0.272150 0.675821 0.067 Uiso 1 1 calc R U . . .
C20 C 0.53432(14) 0.31218(12) 0.4406(5) 0.0575(7) Uani 1 1 d . . . . .
H20 H 0.564692 0.294492 0.378056 0.069 Uiso 1 1 calc R U . . .
C21 C 0.50033(11) 0.35194(11) 0.3576(4) 0.0475(6) Uani 1 1 d . . . . .
H21 H 0.508489 0.360880 0.238246 0.057 Uiso 1 1 calc R U . . .
C22 C 0.45401(10) 0.37955(9) 0.4446(3) 0.0350(5) Uani 1 1 d . . . . .
C23 C 0.500000 0.500000 0.7798(6) 0.0659(12) Uani 1 2 d S T P . .
H23A H 0.526535 0.521158 0.703043 0.079 Uiso 0.5 1 calc R U P . .
H23B H 0.473465 0.478843 0.703041 0.079 Uiso 0.5 1 calc R U P . .
H3N H 0.3970(10) 0.3703(10) 0.843(4) 0.039(6) Uiso 1 1 d D . . . .
N1 N 0.33203(9) 0.31299(8) 0.3508(3) 0.0353(4) Uani 1 1 d . . . . .
N2 N 0.40057(9) 0.46811(8) 0.4561(3) 0.0359(4) Uani 1 1 d . . . . .
N3 N 0.39749(9) 0.38731(9) 0.7365(3) 0.0385(4) Uani 1 1 d . . . . .
O1 O 0.27222(8) 0.33683(8) 0.5905(3) 0.0540(5) Uani 1 1 d . . . . .
O2 O 0.38646(9) 0.31583(7) 0.0882(2) 0.0492(4) Uani 1 1 d . . . . .
O3 O 0.32299(7) 0.43800(8) 0.8478(2) 0.0466(4) Uani 1 1 d . . . . .
F1 F 0.31629(9) 0.08662(6) 0.4547(3) 0.0779(6) Uani 1 1 d . . . . .
Cl1 Cl 0.54108(7) 0.45474(7) 0.91121(19) 0.1283(5) Uani 1 1 d . . . . .
C14 C 0.3489(3) 0.55170(19) 0.4865(11) 0.060(2) Uani 0.650(16) 1 d D . P C 1
H14A H 0.327682 0.580360 0.420690 0.072 Uiso 0.650(16) 1 calc R U P C 1
H14B H 0.368717 0.568595 0.588712 0.072 Uiso 0.650(16) 1 calc R U P C 1
C14D C 0.3291(4) 0.5390(5) 0.3914(19) 0.056(3) Uani 0.350(16) 1 d D . P C 2
H14C H 0.325805 0.578562 0.415403 0.067 Uiso 0.350(16) 1 calc R U P C 2
H14D H 0.306357 0.530398 0.283932 0.067 Uiso 0.350(16) 1 calc R U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.336(5) . ?
C1 C2 1.343(4) . ?
C1 F1 1.359(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(4) . ?
C4 N1 1.434(3) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.204(3) . ?
C7 N1 1.402(3) . ?
C7 C8 1.509(3) . ?
C8 C9 1.525(3) . ?
C8 C11 1.567(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.504(3) . ?
C9 C12 1.568(3) . ?
C9 H9 0.9800 . ?
C10 O2 1.210(3) . ?
C10 N1 1.386(3) . ?
C11 N2 1.482(3) . ?
C11 C16 1.522(3) . ?
C11 C13 1.540(3) . ?
C12 N2 1.459(3) . ?
C12 C22 1.513(3) . ?
C12 H12 0.9800 . ?
C13 C14D 1.488(8) . ?
C13 C14 1.515(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 N2 1.481(3) . ?
C15 C14 1.493(6) . ?
C15 C14D 1.491(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.222(3) . ?
C16 N3 1.364(3) . ?
C17 C22 1.402(3) . ?
C17 C18 1.402(3) . ?
C17 N3 1.412(3) . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(3) . ?
C21 H21 0.9300 . ?
C23 Cl1 1.730(3) 2_665 ?
C23 Cl1 1.730(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
N3 H3N 0.89(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14D H14C 0.9700 . ?
C14D H14D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.9(3) . . ?
C6 C1 F1 118.8(3) . . ?
C2 C1 F1 118.3(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 N1 120.9(2) . . ?
C3 C4 N1 119.6(2) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 N1 124.1(2) . . ?
O1 C7 C8 127.9(2) . . ?
N1 C7 C8 107.89(19) . . ?
C7 C8 C9 104.54(18) . . ?
C7 C8 C11 118.16(18) . . ?
C9 C8 C11 106.06(18) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C11 C8 H8 109.2 . . ?
C10 C9 C8 105.31(19) . . ?
C10 C9 C12 113.50(19) . . ?
C8 C9 C12 103.22(17) . . ?
C10 C9 H9 111.5 . . ?
C8 C9 H9 111.5 . . ?
C12 C9 H9 111.5 . . ?
O2 C10 N1 125.1(2) . . ?
O2 C10 C9 127.2(2) . . ?
N1 C10 C9 107.71(19) . . ?
N2 C11 C16 108.41(18) . . ?
N2 C11 C13 104.98(18) . . ?
C16 C11 C13 111.78(18) . . ?
N2 C11 C8 105.89(17) . . ?
C16 C11 C8 111.52(18) . . ?
C13 C11 C8 113.72(19) . . ?
N2 C12 C22 110.80(19) . . ?
N2 C12 C9 104.55(18) . . ?
C22 C12 C9 114.21(18) . . ?
N2 C12 H12 109.0 . . ?
C22 C12 H12 109.0 . . ?
C9 C12 H12 109.0 . . ?
C14D C13 C11 102.9(4) . . ?
C14 C13 C11 105.6(3) . . ?
C14 C13 H13A 110.6 . . ?
C11 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C11 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
N2 C15 C14 103.3(3) . . ?
N2 C15 C14D 107.3(4) . . ?
N2 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
N2 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
O3 C16 N3 119.2(2) . . ?
O3 C16 C11 121.5(2) . . ?
N3 C16 C11 119.20(19) . . ?
C22 C17 C18 119.0(2) . . ?
C22 C17 N3 127.2(2) . . ?
C18 C17 N3 113.8(2) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 122.7(3) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C21 C22 C17 117.7(2) . . ?
C21 C22 C12 117.7(2) . . ?
C17 C22 C12 124.5(2) . . ?
Cl1 C23 Cl1 111.3(3) 2_665 . ?
Cl1 C23 H23A 109.4 2_665 . ?
Cl1 C23 H23A 109.4 . . ?
Cl1 C23 H23B 109.4 2_665 . ?
Cl1 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C10 N1 C7 112.80(19) . . ?
C10 N1 C4 124.3(2) . . ?
C7 N1 C4 122.86(19) . . ?
C12 N2 C11 107.27(17) . . ?
C12 N2 C15 115.60(19) . . ?
C11 N2 C15 107.44(18) . . ?
C16 N3 C17 135.5(2) . . ?
C16 N3 H3N 113.2(15) . . ?
C17 N3 H3N 111.2(15) . . ?
C15 C14 C13 104.5(3) . . ?
C15 C14 H14A 110.8 . . ?
C13 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
C13 C14D C15 106.0(5) . . ?
C13 C14D H14C 110.5 . . ?
C15 C14D H14C 110.5 . . ?
C13 C14D H14D 110.5 . . ?
C15 C14D H14D 110.5 . . ?
H14C C14D H14D 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(6) . . . . ?
F1 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 N1 178.9(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
N1 C4 C5 C6 -178.6(3) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
F1 C1 C6 C5 177.8(4) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
O1 C7 C8 C9 174.2(2) . . . . ?
N1 C7 C8 C9 -7.6(2) . . . . ?
O1 C7 C8 C11 56.6(3) . . . . ?
N1 C7 C8 C11 -125.2(2) . . . . ?
C7 C8 C9 C10 12.3(2) . . . . ?
C11 C8 C9 C10 137.92(18) . . . . ?
C7 C8 C9 C12 -106.95(19) . . . . ?
C11 C8 C9 C12 18.6(2) . . . . ?
C8 C9 C10 O2 168.6(2) . . . . ?
C12 C9 C10 O2 -79.2(3) . . . . ?
C8 C9 C10 N1 -13.1(2) . . . . ?
C12 C9 C10 N1 99.1(2) . . . . ?
C7 C8 C11 N2 119.0(2) . . . . ?
C9 C8 C11 N2 2.2(2) . . . . ?
C7 C8 C11 C16 1.2(3) . . . . ?
C9 C8 C11 C16 -115.5(2) . . . . ?
C7 C8 C11 C13 -126.3(2) . . . . ?
C9 C8 C11 C13 116.9(2) . . . . ?
C10 C9 C12 N2 -147.12(18) . . . . ?
C8 C9 C12 N2 -33.7(2) . . . . ?
C10 C9 C12 C22 -25.9(3) . . . . ?
C8 C9 C12 C22 87.6(2) . . . . ?
N2 C11 C13 C14D 32.3(7) . . . . ?
C16 C11 C13 C14D 149.6(7) . . . . ?
C8 C11 C13 C14D -83.0(7) . . . . ?
N2 C11 C13 C14 -3.2(4) . . . . ?
C16 C11 C13 C14 114.1(4) . . . . ?
C8 C11 C13 C14 -118.5(4) . . . . ?
N2 C11 C16 O3 134.7(2) . . . . ?
C13 C11 C16 O3 19.5(3) . . . . ?
C8 C11 C16 O3 -109.1(2) . . . . ?
N2 C11 C16 N3 -45.7(3) . . . . ?
C13 C11 C16 N3 -161.0(2) . . . . ?
C8 C11 C16 N3 70.4(3) . . . . ?
C22 C17 C18 C19 -0.4(4) . . . . ?
N3 C17 C18 C19 179.9(2) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
C20 C21 C22 C17 -0.5(4) . . . . ?
C20 C21 C22 C12 179.6(3) . . . . ?
C18 C17 C22 C21 0.9(3) . . . . ?
N3 C17 C22 C21 -179.5(2) . . . . ?
C18 C17 C22 C12 -179.2(2) . . . . ?
N3 C17 C22 C12 0.4(4) . . . . ?
N2 C12 C22 C21 -146.5(2) . . . . ?
C9 C12 C22 C21 95.8(2) . . . . ?
N2 C12 C22 C17 33.6(3) . . . . ?
C9 C12 C22 C17 -84.2(3) . . . . ?
O2 C10 N1 C7 -172.9(2) . . . . ?
C9 C10 N1 C7 8.8(3) . . . . ?
O2 C10 N1 C4 5.3(4) . . . . ?
C9 C10 N1 C4 -173.1(2) . . . . ?
O1 C7 N1 C10 177.7(2) . . . . ?
C8 C7 N1 C10 -0.6(3) . . . . ?
O1 C7 N1 C4 -0.4(4) . . . . ?
C8 C7 N1 C4 -178.8(2) . . . . ?
C5 C4 N1 C10 -72.4(4) . . . . ?
C3 C4 N1 C10 108.6(3) . . . . ?
C5 C4 N1 C7 105.6(3) . . . . ?
C3 C4 N1 C7 -73.4(3) . . . . ?
C22 C12 N2 C11 -87.2(2) . . . . ?
C9 C12 N2 C11 36.3(2) . . . . ?
C22 C12 N2 C15 153.0(2) . . . . ?
C9 C12 N2 C15 -83.5(2) . . . . ?
C16 C11 N2 C12 95.6(2) . . . . ?
C13 C11 N2 C12 -144.82(18) . . . . ?
C8 C11 N2 C12 -24.2(2) . . . . ?
C16 C11 N2 C15 -139.5(2) . . . . ?
C13 C11 N2 C15 -19.9(2) . . . . ?
C8 C11 N2 C15 100.7(2) . . . . ?
C14 C15 N2 C12 155.4(4) . . . . ?
C14D C15 N2 C12 119.6(7) . . . . ?
C14 C15 N2 C11 35.7(5) . . . . ?
C14D C15 N2 C11 -0.1(7) . . . . ?
O3 C16 N3 C17 -176.1(2) . . . . ?
C11 C16 N3 C17 4.3(4) . . . . ?
C22 C17 N3 C16 1.4(4) . . . . ?
C18 C17 N3 C16 -179.0(3) . . . . ?
N2 C15 C14 C13 -36.8(6) . . . . ?
C11 C13 C14 C15 24.7(6) . . . . ?
C11 C13 C14D C15 -32.4(11) . . . . ?
N2 C15 C14D C13 21.0(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N O2 0.89(3) 2.26(3) 3.136(3) 170(2) 1_556 yes

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036

