# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KA1162_0m
_database_code_depnum_ccdc_archive 'CCDC 2070274'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-12-06 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         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9944(19)
_cell_length_b                   10.698(2)
_cell_length_c                   11.488(2)
_cell_angle_alpha                116.186(6)
_cell_angle_beta                 111.602(6)
_cell_angle_gamma                90.504(7)
_cell_volume                     902.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_T_max  0.7457
_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            23581
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4518
_reflns_number_gt                3143
_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)+(0.0766P)²+0.3506P] 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       0.037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4518
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.3565(2) 0.95882(18) 0.73835(18) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.2883(3) 0.9335(2) 0.8182(2) 0.0498(5) Uani 1 1 d . . . . .
H2 H 0.243480 0.840844 0.790134 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2863(3) 1.0453(2) 0.9394(2) 0.0582(5) Uani 1 1 d . . . . .
H3 H 0.241140 1.027519 0.992879 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3514(3) 1.1829(2) 0.9806(2) 0.0576(6) Uani 1 1 d . . . . .
H4 H 0.349102 1.258112 1.061455 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4196(3) 1.2092(2) 0.9025(2) 0.0565(5) Uani 1 1 d . . . . .
H5 H 0.464132 1.302047 0.930885 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4221(2) 1.0974(2) 0.7814(2) 0.0489(5) Uani 1 1 d . . . . .
H6 H 0.468298 1.115768 0.728781 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3545(2) 0.83761(18) 0.60743(18) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.4802(2) 0.80780(18) 0.55802(17) 0.0375(4) Uani 1 1 d . . . . .
C9 C 0.4103(2) 0.68163(18) 0.43068(17) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.6491(2) 0.88708(19) 0.62445(19) 0.0435(4) Uani 1 1 d . . . . .
C11 C 0.8779(3) 0.9158(3) 0.5758(3) 0.0788(8) Uani 1 1 d . . . . .
H11A H 0.935541 0.839520 0.553285 0.118 Uiso 1 1 calc R U . . .
H11B H 0.924302 0.976952 0.677089 0.118 Uiso 1 1 calc R U . . .
H11C H 0.887072 0.969497 0.529434 0.118 Uiso 1 1 calc R U . . .
C12 C 0.4799(2) 0.59647(18) 0.32793(17) 0.0383(4) Uani 1 1 d . . . . .
C13 C 0.7033(3) 0.4878(3) 0.3100(3) 0.0759(8) Uani 1 1 d . . . . .
H13A H 0.646135 0.393244 0.235854 0.114 Uiso 1 1 calc R U . . .
H13B H 0.806845 0.483856 0.372694 0.114 Uiso 1 1 calc R U . . .
H13C H 0.720750 0.544057 0.268362 0.114 Uiso 1 1 calc R U . . .
C14 C 0.1348(2) 0.52020(18) 0.28941(17) 0.0389(4) Uani 1 1 d . . . . .
C15 C 0.1554(3) 0.3864(2) 0.2750(2) 0.0500(5) Uani 1 1 d . . . . .
H15 H 0.244597 0.376815 0.342229 0.060 Uiso 1 1 calc R U . . .
C16 C 0.0411(3) 0.2671(2) 0.1589(2) 0.0590(6) Uani 1 1 d . . . . .
H16 H 0.053648 0.176635 0.147107 0.071 Uiso 1 1 calc R U . . .
C17 C -0.0906(3) 0.2837(3) 0.0616(2) 0.0622(6) Uani 1 1 d . . . . .
H17 H -0.168033 0.204197 -0.015697 0.075 Uiso 1 1 calc R U . . .
C18 C -0.1088(3) 0.4172(3) 0.0776(2) 0.0576(6) Uani 1 1 d . . . . .
H18 H -0.198790 0.425927 0.010458 0.069 Uiso 1 1 calc R U . . .
C19 C 0.0038(2) 0.5397(2) 0.19183(19) 0.0452(4) Uani 1 1 d . . . . .
C20 C -0.0142(4) 0.6838(3) 0.2065(3) 0.0715(7) Uani 1 1 d . . . . .
H20A H -0.091689 0.674252 0.117553 0.107 Uiso 1 1 calc R U . . .
H20B H 0.089530 0.736723 0.231812 0.107 Uiso 1 1 calc R U . . .
H20C H -0.052216 0.733171 0.279450 0.107 Uiso 1 1 calc R U . . .
O1 O 0.70812(18) 0.85806(17) 0.52721(16) 0.0634(4) Uani 1 1 d . . . . .
O2 O 0.60687(18) 0.55202(16) 0.39020(15) 0.0563(4) Uani 1 1 d . . . . .
O3 O 0.7264(2) 0.9635(2) 0.74877(17) 0.0823(6) Uani 1 1 d . . . . .
O4 O 0.4278(2) 0.57132(19) 0.20692(15) 0.0662(5) Uani 1 1 d . . . . .
N1 N 0.25587(17) 0.64234(15) 0.40916(15) 0.0402(4) Uani 1 1 d . . . . .
N2 N 0.21882(19) 0.73715(16) 0.51683(16) 0.0449(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 C6 1.384(3) . ?
C1 C2 1.386(3) . ?
C1 C7 1.484(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.335(2) . ?
C7 C8 1.422(2) . ?
C8 C9 1.386(2) . ?
C8 C10 1.471(2) . ?
C9 N1 1.346(2) . ?
C9 C12 1.490(2) . ?
C10 O3 1.192(2) . ?
C10 O1 1.326(2) . ?
C11 O1 1.441(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.189(2) . ?
C12 O2 1.323(2) . ?
C13 O2 1.454(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.387(3) . ?
C14 C15 1.389(3) . ?
C14 N1 1.439(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.493(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.3682(19) . ?

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 118.96(16) . . ?
C6 C1 C7 121.52(17) . . ?
C2 C1 C7 119.50(16) . . ?
C3 C2 C1 120.47(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.08(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.47(19) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N2 C7 C8 110.88(14) . . ?
N2 C7 C1 119.49(15) . . ?
C8 C7 C1 129.63(16) . . ?
C9 C8 C7 104.56(14) . . ?
C9 C8 C10 125.93(15) . . ?
C7 C8 C10 129.49(15) . . ?
N1 C9 C8 107.43(14) . . ?
N1 C9 C12 122.19(15) . . ?
C8 C9 C12 130.37(15) . . ?
O3 C10 O1 123.71(18) . . ?
O3 C10 C8 125.56(18) . . ?
O1 C10 C8 110.69(15) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O2 124.93(16) . . ?
O4 C12 C9 124.68(17) . . ?
O2 C12 C9 110.39(14) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 122.48(17) . . ?
C19 C14 N1 119.24(16) . . ?
C15 C14 N1 118.28(16) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.51(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 121.9(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C14 C19 C18 116.53(19) . . ?
C14 C19 C20 121.87(19) . . ?
C18 C19 C20 121.6(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 O1 C11 117.96(18) . . ?
C12 O2 C13 116.24(17) . . ?
C9 N1 N2 111.80(14) . . ?
C9 N1 C14 127.60(14) . . ?
N2 N1 C14 120.58(14) . . ?
C7 N2 N1 105.32(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
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 C1 C2 C3 -178.90(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 178.67(18) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C7 N2 -134.9(2) . . . . ?
C2 C1 C7 N2 43.7(3) . . . . ?
C6 C1 C7 C8 44.9(3) . . . . ?
C2 C1 C7 C8 -136.4(2) . . . . ?
N2 C7 C8 C9 0.0(2) . . . . ?
C1 C7 C8 C9 -179.88(18) . . . . ?
N2 C7 C8 C10 -178.58(18) . . . . ?
C1 C7 C8 C10 1.6(3) . . . . ?
C7 C8 C9 N1 0.0(2) . . . . ?
C10 C8 C9 N1 178.57(17) . . . . ?
C7 C8 C9 C12 179.61(18) . . . . ?
C10 C8 C9 C12 -1.8(3) . . . . ?
C9 C8 C10 O3 -153.1(2) . . . . ?
C7 C8 C10 O3 25.2(3) . . . . ?
C9 C8 C10 O1 24.6(3) . . . . ?
C7 C8 C10 O1 -157.18(19) . . . . ?
N1 C9 C12 O4 60.6(3) . . . . ?
C8 C9 C12 O4 -119.0(2) . . . . ?
N1 C9 C12 O2 -118.93(19) . . . . ?
C8 C9 C12 O2 61.5(2) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
N1 C14 C15 C16 -179.01(17) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
N1 C14 C19 C18 179.59(16) . . . . ?
C15 C14 C19 C20 -178.23(19) . . . . ?
N1 C14 C19 C20 0.7(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C17 C18 C19 C20 178.3(2) . . . . ?
O3 C10 O1 C11 3.7(3) . . . . ?
C8 C10 O1 C11 -173.9(2) . . . . ?
O4 C12 O2 C13 10.3(3) . . . . ?
C9 C12 O2 C13 -170.16(18) . . . . ?
C8 C9 N1 N2 0.1(2) . . . . ?
C12 C9 N1 N2 -179.58(16) . . . . ?
C8 C9 N1 C14 178.39(17) . . . . ?
C12 C9 N1 C14 -1.3(3) . . . . ?
C19 C14 N1 C9 -108.1(2) . . . . ?
C15 C14 N1 C9 70.9(2) . . . . ?
C19 C14 N1 N2 70.0(2) . . . . ?
C15 C14 N1 N2 -110.98(19) . . . . ?
C8 C7 N2 N1 0.1(2) . . . . ?
C1 C7 N2 N1 179.96(15) . . . . ?
C9 N1 N2 C7 -0.1(2) . . . . ?
C14 N1 N2 C7 -178.54(16) . . . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_KA1166_0m
_database_code_depnum_ccdc_archive 'CCDC 2070275'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-03-15 deposited with the CCDC.	2021-12-06 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         'C17 H20 N2 O5'
_chemical_formula_sum            'C17 H20 N2 O5'
_chemical_formula_weight         332.35

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                   5.6344(3)
_cell_length_b                   34.6710(19)
_cell_length_c                   8.8274(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.1715(18)
_cell_angle_gamma                90
_cell_volume                     1723.20(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_absorpt_special_details   ?
_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            23948
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.350
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3501
_reflns_number_gt                2783
_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, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_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)+(0.0398P)²+0.5018P] 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       0.0199(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.5142(3) 0.33853(5) 0.11242(17) 0.0445(4) Uani 1 1 d . . . . .
C2 C 0.4700(3) 0.31162(5) -0.00113(19) 0.0581(5) Uani 1 1 d . . . . .
H2 H 0.340614 0.314626 -0.068637 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6189(4) 0.28040(6) -0.0134(2) 0.0620(5) Uani 1 1 d . . . . .
H3 H 0.590918 0.262491 -0.090492 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8098(3) 0.27543(5) 0.08783(18) 0.0493(4) Uani 1 1 d . . . . .
C5 C 0.8548(3) 0.30256(5) 0.19990(19) 0.0502(4) Uani 1 1 d . . . . .
H5 H 0.983418 0.299505 0.268054 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7078(3) 0.33421(5) 0.21007(18) 0.0490(4) Uani 1 1 d . . . . .
H6 H 0.740309 0.352813 0.283865 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2766(3) 0.38648(4) 0.25495(17) 0.0427(4) Uani 1 1 d . . . . .
C8 C 0.1170(3) 0.41493(4) 0.21061(18) 0.0457(4) Uani 1 1 d . . . . .
C9 C 0.1074(3) 0.41365(5) 0.04997(19) 0.0526(4) Uani 1 1 d . . . . .
C10 C 1.1211(4) 0.23399(6) 0.1799(2) 0.0686(5) Uani 1 1 d . . . . .
H10A H 1.196733 0.210192 0.154087 0.103 Uiso 1 1 calc R U . . .
H10B H 1.049126 0.231332 0.276140 0.103 Uiso 1 1 calc R U . . .
H10C H 1.237297 0.254244 0.185634 0.103 Uiso 1 1 calc R U . . .
C11 C 0.3345(3) 0.37078(5) 0.40956(17) 0.0445(4) Uani 1 1 d . . . . .
C12 C 0.5359(4) 0.38264(6) 0.6453(2) 0.0713(6) Uani 1 1 d . . . . .
H12A H 0.396485 0.371044 0.687699 0.086 Uiso 1 1 calc R U . . .
H12B H 0.574959 0.405685 0.703335 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7356(4) 0.35533(8) 0.6584(3) 0.0876(7) Uani 1 1 d . . . . .
H13A H 0.691478 0.331526 0.609403 0.131 Uiso 1 1 calc R U . . .
H13B H 0.774670 0.350555 0.763525 0.131 Uiso 1 1 calc R U . . .
H13C H 0.870970 0.366084 0.610787 0.131 Uiso 1 1 calc R U . . .
C14 C -0.0167(3) 0.43834(5) 0.31657(19) 0.0500(4) Uani 1 1 d . . . . .
C15 C -0.3242(4) 0.48450(6) 0.3391(2) 0.0701(6) Uani 1 1 d . . . . .
H15A H -0.230401 0.503276 0.396675 0.084 Uiso 1 1 calc R U . . .
H15B H -0.404466 0.467997 0.409595 0.084 Uiso 1 1 calc R U . . .
C16 C -0.5006(4) 0.50437(6) 0.2367(3) 0.0776(6) Uani 1 1 d . . . . .
H16A H -0.419871 0.522000 0.172465 0.116 Uiso 1 1 calc R U . . .
H16B H -0.611013 0.518324 0.296166 0.116 Uiso 1 1 calc R U . . .
H16C H -0.584726 0.485604 0.175382 0.116 Uiso 1 1 calc R U . . .
C17 C -0.0397(4) 0.43699(6) -0.0610(2) 0.0736(6) Uani 1 1 d . . . . .
H17A H 0.002357 0.430550 -0.162279 0.110 Uiso 1 1 calc R U . . .
H17B H -0.011083 0.463938 -0.043156 0.110 Uiso 1 1 calc R U . . .
H17C H -0.204846 0.431468 -0.048718 0.110 Uiso 1 1 calc R U . . .
N1 N 0.3543(2) 0.37021(4) 0.12741(14) 0.0472(3) Uani 1 1 d . . . . .
N2 N 0.2520(3) 0.38680(4) -0.00014(15) 0.0568(4) Uani 1 1 d . . . . .
O1 O 0.9442(3) 0.24317(4) 0.06719(15) 0.0675(4) Uani 1 1 d . . . . .
O2 O 0.4821(2) 0.39327(3) 0.48707(13) 0.0575(3) Uani 1 1 d . . . . .
O3 O -0.1722(2) 0.46163(4) 0.24444(14) 0.0647(4) Uani 1 1 d . . . . .
O4 O 0.2517(3) 0.34137(4) 0.45352(15) 0.0713(4) Uani 1 1 d . . . . .
O5 O 0.0080(2) 0.43665(4) 0.45277(14) 0.0678(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 C6 1.373(2) . ?
C1 C2 1.385(2) . ?
C1 N1 1.430(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 O1 1.367(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.3472(19) . ?
C7 C8 1.381(2) . ?
C7 C11 1.494(2) . ?
C8 C9 1.418(2) . ?
C8 C14 1.468(2) . ?
C9 N2 1.324(2) . ?
C9 C17 1.497(2) . ?
C10 O1 1.417(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O4 1.1923(19) . ?
C11 O2 1.3134(19) . ?
C12 O2 1.465(2) . ?
C12 C13 1.472(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O5 1.206(2) . ?
C14 O3 1.335(2) . ?
C15 O3 1.454(2) . ?
C15 C16 1.487(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.3719(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
C6 C1 C2 119.83(15) . . ?
C6 C1 N1 120.94(14) . . ?
C2 C1 N1 119.22(14) . . ?
C3 C2 C1 119.59(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.55(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
O1 C4 C5 124.41(15) . . ?
O1 C4 C3 115.90(15) . . ?
C5 C4 C3 119.69(16) . . ?
C6 C5 C4 119.58(15) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 120.71(15) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C7 C8 106.92(13) . . ?
N1 C7 C11 122.97(14) . . ?
C8 C7 C11 129.52(14) . . ?
C7 C8 C9 105.11(14) . . ?
C7 C8 C14 123.95(14) . . ?
C9 C8 C14 130.82(15) . . ?
N2 C9 C8 110.83(14) . . ?
N2 C9 C17 119.61(16) . . ?
C8 C9 C17 129.55(16) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O2 125.87(15) . . ?
O4 C11 C7 122.32(15) . . ?
O2 C11 C7 111.80(13) . . ?
O2 C12 C13 111.51(17) . . ?
O2 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O3 123.59(16) . . ?
O5 C14 C8 124.46(16) . . ?
O3 C14 C8 111.95(14) . . ?
O3 C15 C16 107.34(16) . . ?
O3 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O3 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
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 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 N2 111.74(13) . . ?
C7 N1 C1 128.68(13) . . ?
N2 N1 C1 119.53(12) . . ?
C9 N2 N1 105.39(13) . . ?
C4 O1 C10 117.93(14) . . ?
C11 O2 C12 116.82(14) . . ?
C14 O3 C15 116.48(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
C6 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 -178.01(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 O1 178.95(17) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
O1 C4 C5 C6 179.74(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C2 C1 C6 C5 -2.3(3) . . . . ?
N1 C1 C6 C5 176.73(15) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
N1 C7 C8 C9 0.43(17) . . . . ?
C11 C7 C8 C9 -170.80(15) . . . . ?
N1 C7 C8 C14 177.02(15) . . . . ?
C11 C7 C8 C14 5.8(3) . . . . ?
C7 C8 C9 N2 -0.7(2) . . . . ?
C14 C8 C9 N2 -176.95(17) . . . . ?
C7 C8 C9 C17 178.22(19) . . . . ?
C14 C8 C9 C17 2.0(3) . . . . ?
N1 C7 C11 O4 -70.8(2) . . . . ?
C8 C7 C11 O4 99.2(2) . . . . ?
N1 C7 C11 O2 109.68(17) . . . . ?
C8 C7 C11 O2 -80.3(2) . . . . ?
C7 C8 C14 O5 4.2(3) . . . . ?
C9 C8 C14 O5 179.82(18) . . . . ?
C7 C8 C14 O3 -175.10(15) . . . . ?
C9 C8 C14 O3 0.6(3) . . . . ?
C8 C7 N1 N2 -0.06(18) . . . . ?
C11 C7 N1 N2 171.88(14) . . . . ?
C8 C7 N1 C1 -177.37(15) . . . . ?
C11 C7 N1 C1 -5.4(2) . . . . ?
C6 C1 N1 C7 -38.4(2) . . . . ?
C2 C1 N1 C7 140.63(17) . . . . ?
C6 C1 N1 N2 144.43(16) . . . . ?
C2 C1 N1 N2 -36.5(2) . . . . ?
C8 C9 N2 N1 0.6(2) . . . . ?
C17 C9 N2 N1 -178.39(16) . . . . ?
C7 N1 N2 C9 -0.36(19) . . . . ?
C1 N1 N2 C9 177.22(14) . . . . ?
C5 C4 O1 C10 9.2(3) . . . . ?
C3 C4 O1 C10 -171.46(18) . . . . ?
O4 C11 O2 C12 -4.7(3) . . . . ?
C7 C11 O2 C12 174.81(14) . . . . ?
C13 C12 O2 C11 87.3(2) . . . . ?
O5 C14 O3 C15 -2.8(3) . . . . ?
C8 C14 O3 C15 176.49(16) . . . . ?
C16 C15 O3 C14 -173.26(17) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034

