# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_Form_A1
_database_code_depnum_ccdc_archive 'CCDC 2298736'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2024-02-22 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 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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                   6.7861(6)
_cell_length_b                   10.5591(9)
_cell_length_c                   14.6794(14)
_cell_angle_alpha                103.839(3)
_cell_angle_beta                 100.553(3)
_cell_angle_gamma                99.593(3)
_cell_volume                     979.34(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7549
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.57

_exptl_crystal_description       PLATE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            39408
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         29.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5536
_reflns_number_gt                3882
_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        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0680P)²+0.6069P] 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         5536
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.6166(2) 0.95414(15) 0.39409(11) 0.0272(4) Uani 1 1 d . . . . .
N1 N 0.3951(2) 0.70833(16) 0.49518(11) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.8399(3) 0.76614(18) 0.62405(13) 0.0134(4) Uani 1 1 d . . . . .
O2 O 0.6920(2) 0.51315(13) 0.74869(10) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.3047(3) 0.81359(17) 0.38209(12) 0.0207(4) Uani 1 1 d . . . . .
C2 C 1.0483(3) 0.81196(18) 0.67169(13) 0.0144(4) Uani 1 1 d . . . . .
H2 H 1.133420 0.879064 0.654452 0.017 Uiso 1 1 calc R U . . .
C3 C 1.1293(3) 0.75851(18) 0.74423(13) 0.0140(4) Uani 1 1 d . . . . .
O3 O 1.0903(2) 0.60077(13) 0.83684(10) 0.0173(3) Uani 1 1 d . . . . .
C4 C 1.0055(3) 0.65881(18) 0.76893(13) 0.0139(4) Uani 1 1 d . . . . .
O4 O 1.32827(19) 0.79565(14) 0.79588(10) 0.0195(3) Uani 1 1 d . . . . .
C6 C 0.7149(3) 0.66675(18) 0.64898(13) 0.0153(4) Uani 1 1 d . . . . .
H6 H 0.573853 0.635966 0.616819 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7978(3) 0.61355(18) 0.72065(13) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.7622(3) 0.82543(18) 0.54855(13) 0.0146(4) Uani 1 1 d . . . . .
H7 H 0.860041 0.891322 0.536596 0.018 Uiso 1 1 calc R U . . .
C8 C 0.5693(3) 0.79907(18) 0.49321(13) 0.0153(4) Uani 1 1 d . . . . .
C9 C 0.5129(3) 0.8690(2) 0.41908(14) 0.0189(4) Uani 1 1 d . . . . .
C10 C 0.2480(3) 0.72009(19) 0.42998(13) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.0330(3) 0.6417(2) 0.40581(15) 0.0217(4) Uani 1 1 d . . . . .
H11A H -0.007177 0.593574 0.337002 0.033 Uiso 1 1 calc R U . . .
H11B H -0.058691 0.702463 0.420426 0.033 Uiso 1 1 calc R U . . .
H11C H 0.023065 0.577515 0.444049 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1680(3) 0.8548(2) 0.31048(15) 0.0235(4) Uani 1 1 d . . . . .
H12A H 0.227326 0.947830 0.312258 0.028 Uiso 1 1 calc R U . . .
H12B H 0.033353 0.853170 0.327641 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1354(3) 0.7642(2) 0.20804(15) 0.0237(4) Uani 1 1 d . . . . .
H13A H 0.259179 0.785376 0.183044 0.028 Uiso 1 1 calc R U . . .
H13B H 0.114455 0.669630 0.209236 0.028 Uiso 1 1 calc R U . . .
C14 C -0.0501(3) 0.7837(2) 0.14194(14) 0.0200(4) Uani 1 1 d . . . . .
C15 C -0.0499(3) 0.9017(2) 0.11450(16) 0.0255(5) Uani 1 1 d . . . . .
H15 H 0.068402 0.972876 0.138748 0.031 Uiso 1 1 calc R U . . .
C19 C -0.2280(3) 0.6840(2) 0.10847(15) 0.0225(4) Uani 1 1 d . . . . .
H19 H -0.233601 0.604388 0.128204 0.027 Uiso 1 1 calc R U . . .
C20 C 0.4743(3) 0.4762(2) 0.71143(16) 0.0213(4) Uani 1 1 d . . . . .
H20A H 0.443583 0.448010 0.640772 0.032 Uiso 1 1 calc R U . . .
H20B H 0.414165 0.553091 0.733090 0.032 Uiso 1 1 calc R U . . .
H20C H 0.415875 0.402338 0.734904 0.032 Uiso 1 1 calc R U . . .
C21 C 1.0361(3) 0.6431(2) 0.92747(15) 0.0251(5) Uani 1 1 d . . . . .
H21A H 0.886222 0.622225 0.917585 0.038 Uiso 1 1 calc R U . . .
H21B H 1.088916 0.739704 0.954923 0.038 Uiso 1 1 calc R U . . .
H21C H 1.096237 0.596217 0.971889 0.038 Uiso 1 1 calc R U . . .
C22 C 1.4613(3) 0.8957(2) 0.77117(16) 0.0232(4) Uani 1 1 d . . . . .
H22A H 1.462333 0.865046 0.702799 0.035 Uiso 1 1 calc R U . . .
H22B H 1.600852 0.911874 0.810676 0.035 Uiso 1 1 calc R U . . .
H22C H 1.411651 0.978835 0.783134 0.035 Uiso 1 1 calc R U . . .
C18 C -0.3976(3) 0.6986(2) 0.04685(16) 0.0266(5) Uani 1 1 d . . . . .
H18 H -0.517957 0.628870 0.024463 0.032 Uiso 1 1 calc R U . . .
C17 C -0.3930(3) 0.8143(2) 0.01746(16) 0.0273(5) Uani 1 1 d . . . . .
H17 H -0.508378 0.822936 -0.026382 0.033 Uiso 1 1 calc R U . . .
C16 C -0.2201(3) 0.9167(2) 0.05230(17) 0.0283(5) Uani 1 1 d . . . . .
H16 H -0.217047 0.997206 0.033900 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.217(2) . ?
N1 C10 1.295(2) . ?
N1 C8 1.402(2) . ?
C1 C6 1.398(3) . ?
C1 C2 1.404(2) . ?
C1 C7 1.458(2) . ?
O2 C5 1.368(2) . ?
O2 C20 1.430(2) . ?
N2 C10 1.386(3) . ?
N2 C9 1.387(2) . ?
N2 C12 1.467(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 O4 1.363(2) . ?
C3 C4 1.394(3) . ?
O3 C4 1.379(2) . ?
O3 C21 1.433(2) . ?
C4 C5 1.402(3) . ?
O4 C22 1.431(2) . ?
C6 C5 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.354(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.483(3) . ?
C10 C11 1.485(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.386(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C19 C18 1.382(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C18 C17 1.387(3) . ?
C18 H18 0.9500 . ?
C17 C16 1.379(3) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C8 105.22(16) . . ?
C6 C1 C2 120.24(16) . . ?
C6 C1 C7 122.27(16) . . ?
C2 C1 C7 117.49(16) . . ?
C5 O2 C20 116.73(14) . . ?
C10 N2 C9 107.65(15) . . ?
C10 N2 C12 126.60(17) . . ?
C9 N2 C12 125.60(17) . . ?
C3 C2 C1 119.56(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
O4 C3 C2 124.82(16) . . ?
O4 C3 C4 114.77(16) . . ?
C2 C3 C4 120.40(16) . . ?
C4 O3 C21 113.14(14) . . ?
O3 C4 C3 119.89(16) . . ?
O3 C4 C5 120.49(16) . . ?
C3 C4 C5 119.53(16) . . ?
C3 O4 C22 116.42(14) . . ?
C5 C6 C1 119.64(17) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O2 C5 C6 124.67(17) . . ?
O2 C5 C4 114.68(16) . . ?
C6 C5 C4 120.63(17) . . ?
C8 C7 C1 128.63(17) . . ?
C8 C7 H7 115.7 . . ?
C1 C7 H7 115.7 . . ?
C7 C8 N1 128.22(17) . . ?
C7 C8 C9 122.39(17) . . ?
N1 C8 C9 109.38(15) . . ?
O1 C9 N2 126.32(17) . . ?
O1 C9 C8 130.75(18) . . ?
N2 C9 C8 102.93(16) . . ?
N1 C10 N2 114.82(17) . . ?
N1 C10 C11 124.40(18) . . ?
N2 C10 C11 120.79(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 112.42(17) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 110.52(17) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C19 C14 C15 117.95(18) . . ?
C19 C14 C13 120.05(18) . . ?
C15 C14 C13 121.99(18) . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C18 C19 C14 121.08(19) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C17 C18 119.56(19) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?

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 -0.4(3) . . . . ?
C7 C1 C2 C3 179.93(17) . . . . ?
C1 C2 C3 O4 -179.50(17) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C21 O3 C4 C3 106.5(2) . . . . ?
C21 O3 C4 C5 -76.9(2) . . . . ?
O4 C3 C4 O3 -3.7(3) . . . . ?
C2 C3 C4 O3 176.04(17) . . . . ?
O4 C3 C4 C5 179.67(16) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 O4 C22 -1.0(3) . . . . ?
C4 C3 O4 C22 178.69(17) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C7 C1 C6 C5 179.47(17) . . . . ?
C20 O2 C5 C6 -10.2(3) . . . . ?
C20 O2 C5 C4 171.66(17) . . . . ?
C1 C6 C5 O2 -177.72(17) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
O3 C4 C5 O2 1.7(3) . . . . ?
C3 C4 C5 O2 178.29(16) . . . . ?
O3 C4 C5 C6 -176.61(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C6 C1 C7 C8 0.8(3) . . . . ?
C2 C1 C7 C8 -179.57(19) . . . . ?
C1 C7 C8 N1 0.4(3) . . . . ?
C1 C7 C8 C9 179.57(18) . . . . ?
C10 N1 C8 C7 179.35(19) . . . . ?
C10 N1 C8 C9 0.1(2) . . . . ?
C10 N2 C9 O1 179.6(2) . . . . ?
C12 N2 C9 O1 -4.6(3) . . . . ?
C10 N2 C9 C8 -0.5(2) . . . . ?
C12 N2 C9 C8 175.33(18) . . . . ?
C7 C8 C9 O1 0.9(3) . . . . ?
N1 C8 C9 O1 -179.8(2) . . . . ?
C7 C8 C9 N2 -179.05(18) . . . . ?
N1 C8 C9 N2 0.2(2) . . . . ?
C8 N1 C10 N2 -0.4(2) . . . . ?
C8 N1 C10 C11 179.53(18) . . . . ?
C9 N2 C10 N1 0.6(2) . . . . ?
C12 N2 C10 N1 -175.13(18) . . . . ?
C9 N2 C10 C11 -179.36(18) . . . . ?
C12 N2 C10 C11 4.9(3) . . . . ?
C10 N2 C12 C13 -86.9(2) . . . . ?
C9 N2 C12 C13 98.1(2) . . . . ?
N2 C12 C13 C14 163.60(18) . . . . ?
C12 C13 C14 C19 -109.2(2) . . . . ?
C12 C13 C14 C15 69.4(3) . . . . ?
C19 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C16 178.7(2) . . . . ?
C15 C14 C19 C18 2.5(3) . . . . ?
C13 C14 C19 C18 -178.8(2) . . . . ?
C14 C19 C18 C17 -0.3(3) . . . . ?
C19 C18 C17 C16 -1.8(3) . . . . ?
C18 C17 C16 C15 1.7(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?

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
C2 H2 O1 0.95 2.56 3.504(2) 175.0 2_776 yes
C6 H6 N1 0.95 2.33 3.000(2) 127.4 . yes
C13 H13B O2 0.99 2.64 3.481(2) 143.3 2_666 yes
C21 H21A O2 0.98 2.48 3.031(3) 115.4 . yes

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_Form_B2
_database_code_depnum_ccdc_archive 'CCDC 2298739'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2024-02-22 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 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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                   7.1543(5)
_cell_length_b                   9.0388(6)
_cell_length_c                   15.8533(11)
_cell_angle_alpha                104.611(2)
_cell_angle_beta                 95.711(3)
_cell_angle_gamma                96.882(3)
_cell_volume                     975.85(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.15

_exptl_crystal_description       'THICK NEEDLE'
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube '
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            23110
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4000
_reflns_number_gt                3156
_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        'SAINT (Bruker, 2016)'
_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_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)+(0.0686P)²+0.6384P] 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         4000
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.1732
_refine_ls_wR_factor_gt          0.1629
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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
O1 O 0.8482(3) 0.0123(2) 0.86967(12) 0.0309(5) Uani 1 1 d . . . . .
N1 N 0.4202(3) 0.0305(2) 0.74216(13) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.5011(3) 0.3826(3) 0.85482(15) 0.0205(5) Uani 1 1 d . . . . .
C2 C 0.5783(3) 0.5324(3) 0.90666(16) 0.0207(5) Uani 1 1 d . . . . .
O3 O 0.1908(2) 0.7434(2) 0.85870(11) 0.0253(4) Uani 1 1 d . . . . .
C3 C 0.4776(4) 0.6555(3) 0.90986(16) 0.0213(5) Uani 1 1 d . . . . .
H3 H 0.530641 0.755849 0.945545 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2994(4) 0.6317(3) 0.86083(16) 0.0210(5) Uani 1 1 d . . . . .
O4 O 0.7548(2) 0.5471(2) 0.95170(12) 0.0269(4) Uani 1 1 d . . . . .
O2 O 0.0431(3) 0.4719(2) 0.76190(12) 0.0291(5) Uani 1 1 d . . . . .
N2 N 0.6189(3) -0.1395(2) 0.75782(13) 0.0225(5) Uani 1 1 d . . . . .
C5 C 0.2207(4) 0.4823(3) 0.80781(16) 0.0215(5) Uani 1 1 d . . . . .
C6 C 0.3196(4) 0.3613(3) 0.80513(16) 0.0215(5) Uani 1 1 d . . . . .
H6 H 0.265713 0.261268 0.769331 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6063(4) 0.2560(3) 0.85591(16) 0.0216(6) Uani 1 1 d . . . . .
H7 H 0.719527 0.282670 0.896675 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5710(4) 0.1068(3) 0.80897(16) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.8091(4) -0.2334(3) 0.59673(17) 0.0245(6) Uani 1 1 d . . . . .
C13 C 0.8715(4) -0.2637(3) 0.68340(18) 0.0282(6) Uani 1 1 d . . . . .
H13A H 0.971401 -0.178254 0.717596 0.034 Uiso 1 1 calc R U . . .
H13B H 0.928187 -0.360355 0.672346 0.034 Uiso 1 1 calc R U . . .
C12 C 0.7100(4) -0.2783(3) 0.73806(17) 0.0254(6) Uani 1 1 d . . . . .
H12A H 0.613754 -0.367882 0.705633 0.030 Uiso 1 1 calc R U . . .
H12B H 0.760456 -0.298339 0.793909 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3337(4) -0.2314(3) 0.64212(18) 0.0274(6) Uani 1 1 d . . . . .
H11A H 0.407987 -0.266605 0.594166 0.041 Uiso 1 1 calc R U . . .
H11B H 0.224905 -0.188851 0.620140 0.041 Uiso 1 1 calc R U . . .
H11C H 0.288174 -0.318794 0.664544 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4553(3) -0.1097(3) 0.71417(16) 0.0215(5) Uani 1 1 d . . . . .
C9 C 0.7024(4) -0.0041(3) 0.81955(16) 0.0226(6) Uani 1 1 d . . . . .
C17 C 0.6701(5) -0.1762(4) 0.4388(2) 0.0425(8) Uani 1 1 d . . . . .
H17 H 0.621734 -0.156587 0.385324 0.051 Uiso 1 1 calc R U . . .
C16 C 0.7373(5) -0.0561(4) 0.5116(2) 0.0443(8) Uani 1 1 d . . . . .
H16 H 0.736472 0.047429 0.508556 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8069(4) -0.0853(3) 0.59017(19) 0.0344(7) Uani 1 1 d . . . . .
H15 H 0.853631 -0.000864 0.640135 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6733(5) -0.3255(4) 0.4438(2) 0.0427(8) Uani 1 1 d . . . . .
H18 H 0.627317 -0.409252 0.393435 0.051 Uiso 1 1 calc R U . . .
C22 C 0.8471(4) 0.6983(3) 0.99992(17) 0.0264(6) Uani 1 1 d . . . . .
H22A H 0.973734 0.691527 1.027205 0.040 Uiso 1 1 calc R U . . .
H22B H 0.771787 0.742429 1.045742 0.040 Uiso 1 1 calc R U . . .
H22C H 0.859032 0.764571 0.959838 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2537(4) 0.8938(3) 0.91837(17) 0.0243(6) Uani 1 1 d . . . . .
H21A H 0.160521 0.962352 0.911292 0.037 Uiso 1 1 calc R U . . .
H21B H 0.376836 0.936617 0.905546 0.037 Uiso 1 1 calc R U . . .
H21C H 0.266761 0.885007 0.978969 0.037 Uiso 1 1 calc R U . . .
C20 C -0.0489(4) 0.3219(3) 0.71627(19) 0.0309(6) Uani 1 1 d . . . . .
H20A H -0.178050 0.327488 0.691358 0.046 Uiso 1 1 calc R U . . .
H20B H -0.054916 0.256507 0.757017 0.046 Uiso 1 1 calc R U . . .
H20C H 0.022234 0.277526 0.668761 0.046 Uiso 1 1 calc R U . . .
C19 C 0.7430(5) -0.3552(3) 0.52189(19) 0.0360(7) Uani 1 1 d . . . . .
H19 H 0.745706 -0.458814 0.524355 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.217(3) . ?
N1 C10 1.297(3) . ?
N1 C8 1.409(3) . ?
C1 C2 1.409(3) . ?
C1 C6 1.415(3) . ?
C1 C7 1.445(3) . ?
C2 O4 1.361(3) . ?
C2 C3 1.389(3) . ?
O3 C4 1.351(3) . ?
O3 C21 1.437(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.413(4) . ?
O4 C22 1.430(3) . ?
O2 C5 1.380(3) . ?
O2 C20 1.411(3) . ?
N2 C9 1.385(3) . ?
N2 C10 1.390(3) . ?
N2 C12 1.460(3) . ?
C5 C6 1.367(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.346(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.482(3) . ?
C14 C15 1.371(4) . ?
C14 C19 1.395(4) . ?
C14 C13 1.503(4) . ?
C13 C12 1.525(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.486(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C17 C16 1.369(5) . ?
C17 C18 1.374(5) . ?
C17 H17 0.9500 . ?
C16 C15 1.394(4) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C8 105.7(2) . . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 C7 119.3(2) . . ?
C6 C1 C7 122.4(2) . . ?
O4 C2 C3 123.4(2) . . ?
O4 C2 C1 115.8(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 O3 C21 117.90(19) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O3 C4 C3 124.6(2) . . ?
O3 C4 C5 115.4(2) . . ?
C3 C4 C5 120.0(2) . . ?
C2 O4 C22 118.5(2) . . ?
C5 O2 C20 116.6(2) . . ?
C9 N2 C10 107.9(2) . . ?
C9 N2 C12 122.9(2) . . ?
C10 N2 C12 128.7(2) . . ?
C6 C5 O2 124.9(2) . . ?
C6 C5 C4 120.0(2) . . ?
O2 C5 C4 115.1(2) . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 130.9(2) . . ?
C8 C7 H7 114.5 . . ?
C1 C7 H7 114.5 . . ?
C7 C8 N1 129.2(2) . . ?
C7 C8 C9 121.9(2) . . ?
N1 C8 C9 108.8(2) . . ?
C15 C14 C19 118.2(3) . . ?
C15 C14 C13 120.7(2) . . ?
C19 C14 C13 121.0(2) . . ?
C14 C13 C12 113.2(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N2 C12 C13 112.5(2) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C10 N2 114.2(2) . . ?
N1 C10 C11 124.3(2) . . ?
N2 C10 C11 121.5(2) . . ?
O1 C9 N2 125.9(2) . . ?
O1 C9 C8 130.7(2) . . ?
N2 C9 C8 103.4(2) . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

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 O4 -178.7(2) . . . . ?
C7 C1 C2 O4 3.0(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C7 C1 C2 C3 -177.4(2) . . . . ?
O4 C2 C3 C4 179.0(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C21 O3 C4 C3 -7.2(3) . . . . ?
C21 O3 C4 C5 173.4(2) . . . . ?
C2 C3 C4 O3 -179.4(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C2 O4 C22 -4.5(3) . . . . ?
C1 C2 O4 C22 175.1(2) . . . . ?
C20 O2 C5 C6 6.7(4) . . . . ?
C20 O2 C5 C4 -173.0(2) . . . . ?
O3 C4 C5 C6 179.8(2) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
O3 C4 C5 O2 -0.5(3) . . . . ?
C3 C4 C5 O2 -180.0(2) . . . . ?
O2 C5 C6 C1 -179.7(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 177.7(2) . . . . ?
C2 C1 C7 C8 -175.0(3) . . . . ?
C6 C1 C7 C8 6.7(4) . . . . ?
C1 C7 C8 N1 1.9(5) . . . . ?
C1 C7 C8 C9 178.6(2) . . . . ?
C10 N1 C8 C7 176.4(3) . . . . ?
C10 N1 C8 C9 -0.7(3) . . . . ?
C15 C14 C13 C12 88.2(3) . . . . ?
C19 C14 C13 C12 -88.6(3) . . . . ?
C9 N2 C12 C13 -74.6(3) . . . . ?
C10 N2 C12 C13 96.4(3) . . . . ?
C14 C13 C12 N2 -59.0(3) . . . . ?
C8 N1 C10 N2 1.3(3) . . . . ?
C8 N1 C10 C11 -179.0(2) . . . . ?
C9 N2 C10 N1 -1.4(3) . . . . ?
C12 N2 C10 N1 -173.5(2) . . . . ?
C9 N2 C10 C11 178.8(2) . . . . ?
C12 N2 C10 C11 6.8(4) . . . . ?
C10 N2 C9 O1 -180.0(2) . . . . ?
C12 N2 C9 O1 -7.4(4) . . . . ?
C10 N2 C9 C8 0.9(3) . . . . ?
C12 N2 C9 C8 173.5(2) . . . . ?
C7 C8 C9 O1 3.4(4) . . . . ?
N1 C8 C9 O1 -179.3(3) . . . . ?
C7 C8 C9 N2 -177.5(2) . . . . ?
N1 C8 C9 N2 -0.2(3) . . . . ?
C18 C17 C16 C15 -0.5(5) . . . . ?
C19 C14 C15 C16 1.2(4) . . . . ?
C13 C14 C15 C16 -175.6(3) . . . . ?
C17 C16 C15 C14 -0.3(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C15 C14 C19 C18 -1.4(4) . . . . ?
C13 C14 C19 C18 175.4(3) . . . . ?

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
C6 H6 N1 0.95 2.44 3.100(3) 126.4 . yes
C13 H13B O2 0.99 2.48 3.266(3) 136.2 1_645 yes
C21 H21A O1 0.98 2.39 3.298(3) 153.2 1_465 yes
C21 H21C O1 0.98 2.60 3.427(3) 142.4 2_667 yes

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Form_A2
_database_code_depnum_ccdc_archive 'CCDC 2298737'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2024-02-22 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 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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                   7.4983(6)
_cell_length_b                   25.712(2)
_cell_length_c                   10.1462(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.934(3)
_cell_angle_gamma                90
_cell_volume                     1941.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9758
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.68

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            54784
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         28.722
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5003
_reflns_number_gt                4468
_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        'SAINT (Bruker, 2016)'
_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_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)+(0.0415P)²+0.9298P] 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         5003
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22970(12) 0.50305(3) 0.42138(9) 0.0226(2) Uani 1 1 d . . . . .
N1 N 0.23116(14) 0.63021(4) 0.28397(10) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.67953(13) 0.77008(3) 0.30537(10) 0.0245(2) Uani 1 1 d . . . . .
N2 N 0.04556(14) 0.56147(4) 0.29376(10) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.61981(16) 0.63672(4) 0.42898(12) 0.0168(2) Uani 1 1 d . . . . .
C2 C 0.78543(16) 0.63089(5) 0.50829(12) 0.0183(2) Uani 1 1 d . . . . .
H2 H 0.814827 0.598905 0.552541 0.022 Uiso 1 1 calc R U . . .
C3 C 0.90658(16) 0.67222(5) 0.52185(12) 0.0191(2) Uani 1 1 d . . . . .
O3 O 0.97915(13) 0.76089(3) 0.47462(10) 0.0238(2) Uani 1 1 d . . . . .
C4 C 0.86546(17) 0.71899(5) 0.45479(12) 0.0192(2) Uani 1 1 d . . . . .
O4 O 1.06969(12) 0.67112(4) 0.59786(9) 0.0243(2) Uani 1 1 d . . . . .
C5 C 0.70367(17) 0.72374(5) 0.37117(12) 0.0189(2) Uani 1 1 d . . . . .
C6 C 0.57963(16) 0.68336(5) 0.35912(12) 0.0181(2) Uani 1 1 d . . . . .
H6 H 0.468550 0.687216 0.304147 0.022 Uiso 1 1 calc R U . . .
C7 C 0.49356(16) 0.59328(4) 0.42371(11) 0.0168(2) Uani 1 1 d . . . . .
H7 H 0.535568 0.562812 0.470529 0.020 Uiso 1 1 calc R U . . .
C8 C 0.32471(16) 0.59106(4) 0.36059(12) 0.0169(2) Uani 1 1 d . . . . .
C9 C 0.20402(16) 0.54527(5) 0.36653(12) 0.0174(2) Uani 1 1 d . . . . .
C11 C -0.07128(17) 0.63944(5) 0.16233(13) 0.0228(3) Uani 1 1 d . . . . .
H11A H -0.180514 0.640645 0.206417 0.034 Uiso 1 1 calc R U . . .
H11B H -0.096477 0.621097 0.077449 0.034 Uiso 1 1 calc R U . . .
H11C H -0.031551 0.674948 0.146371 0.034 Uiso 1 1 calc R U . . .
C10 C 0.07169(16) 0.61168(5) 0.24800(12) 0.0177(2) Uani 1 1 d . . . . .
C12 C -0.11977(16) 0.53099(5) 0.27613(12) 0.0193(2) Uani 1 1 d . . . . .
H12A H -0.223318 0.554313 0.282945 0.023 Uiso 1 1 calc R U . . .
H12B H -0.116586 0.504966 0.348280 0.023 Uiso 1 1 calc R U . . .
C13 C -0.14615(19) 0.50313(5) 0.14275(13) 0.0246(3) Uani 1 1 d . . . . .
H13A H -0.163467 0.529513 0.071267 0.030 Uiso 1 1 calc R U . . .
H13B H -0.035319 0.483539 0.131586 0.030 Uiso 1 1 calc R U . . .
C14 C -0.30357(17) 0.46595(5) 0.12621(12) 0.0204(2) Uani 1 1 d . . . . .
C15 C -0.31376(19) 0.42941(5) 0.02343(13) 0.0261(3) Uani 1 1 d . . . . .
H15 H -0.226637 0.430130 -0.037190 0.031 Uiso 1 1 calc R U . . .
C16 C -0.4484(2) 0.39213(6) 0.00818(15) 0.0303(3) Uani 1 1 d . . . . .
H16 H -0.452543 0.367531 -0.061978 0.036 Uiso 1 1 calc R U . . .
C17 C -0.57730(19) 0.39084(5) 0.09567(14) 0.0288(3) Uani 1 1 d . . . . .
H17 H -0.667327 0.364649 0.087720 0.035 Uiso 1 1 calc R U . . .
C18 C -0.57331(19) 0.42814(6) 0.19474(14) 0.0279(3) Uani 1 1 d . . . . .
H18 H -0.664042 0.428342 0.252493 0.033 Uiso 1 1 calc R U . . .
C20 C 0.53045(19) 0.77358(5) 0.20412(14) 0.0265(3) Uani 1 1 d . . . . .
H20A H 0.533602 0.807129 0.158615 0.040 Uiso 1 1 calc R U . . .
H20B H 0.418320 0.770669 0.244184 0.040 Uiso 1 1 calc R U . . .
H20C H 0.537050 0.745347 0.140002 0.040 Uiso 1 1 calc R U . . .
C19 C -0.43718(18) 0.46532(5) 0.21017(13) 0.0247(3) Uani 1 1 d . . . . .
H19 H -0.435589 0.490512 0.278789 0.030 Uiso 1 1 calc R U . . .
C21 C 1.1270(2) 0.75962(6) 0.39767(16) 0.0314(3) Uani 1 1 d . . . . .
H21A H 1.205954 0.789415 0.421305 0.047 Uiso 1 1 calc R U . . .
H21B H 1.081690 0.761285 0.303047 0.047 Uiso 1 1 calc R U . . .
H21C H 1.194703 0.727283 0.415987 0.047 Uiso 1 1 calc R U . . .
C22 C 1.1132(2) 0.62551(5) 0.67426(15) 0.0293(3) Uani 1 1 d . . . . .
H22A H 1.232800 0.629385 0.724158 0.044 Uiso 1 1 calc R U . . .
H22B H 1.112642 0.595401 0.614996 0.044 Uiso 1 1 calc R U . . .
H22C H 1.024265 0.620314 0.736295 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2244(15) . ?
N1 C10 1.2979(16) . ?
N1 C8 1.4065(15) . ?
O2 C5 1.3673(14) . ?
O2 C20 1.4268(16) . ?
N2 C9 1.3851(16) . ?
N2 C10 1.3938(15) . ?
N2 C12 1.4592(15) . ?
C1 C2 1.4039(17) . ?
C1 C6 1.4070(16) . ?
C1 C7 1.4610(16) . ?
C2 C3 1.3940(17) . ?
C2 H2 0.9500 . ?
C3 O4 1.3652(15) . ?
C3 C4 1.3977(17) . ?
O3 C4 1.3734(14) . ?
O3 C21 1.4316(17) . ?
C4 C5 1.3992(17) . ?
O4 C22 1.4219(16) . ?
C5 C6 1.3894(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3493(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4905(16) . ?
C11 C10 1.4796(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.5229(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5125(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.3913(18) . ?
C14 C15 1.3989(18) . ?
C15 C16 1.3873(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3934(18) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C10 N1 C8 105.89(10) . . ?
C5 O2 C20 116.91(10) . . ?
C9 N2 C10 108.06(10) . . ?
C9 N2 C12 124.42(10) . . ?
C10 N2 C12 127.45(10) . . ?
C2 C1 C6 120.04(11) . . ?
C2 C1 C7 117.63(11) . . ?
C6 C1 C7 122.33(11) . . ?
C3 C2 C1 119.72(11) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O4 C3 C2 124.66(11) . . ?
O4 C3 C4 115.00(11) . . ?
C2 C3 C4 120.34(11) . . ?
C4 O3 C21 114.22(10) . . ?
O3 C4 C3 120.46(11) . . ?
O3 C4 C5 119.86(11) . . ?
C3 C4 C5 119.62(11) . . ?
C3 O4 C22 117.13(10) . . ?
O2 C5 C6 124.09(11) . . ?
O2 C5 C4 115.22(11) . . ?
C6 C5 C4 120.69(11) . . ?
C5 C6 C1 119.48(11) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C1 128.06(11) . . ?
C8 C7 H7 116.0 . . ?
C1 C7 H7 116.0 . . ?
C7 C8 N1 127.51(11) . . ?
C7 C8 C9 123.63(11) . . ?
N1 C8 C9 108.84(10) . . ?
O1 C9 N2 125.91(11) . . ?
O1 C9 C8 130.97(11) . . ?
N2 C9 C8 103.12(10) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C10 N2 114.09(11) . . ?
N1 C10 C11 124.45(11) . . ?
N2 C10 C11 121.43(11) . . ?
N2 C12 C13 112.26(10) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 114.32(11) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C19 C14 C15 118.03(12) . . ?
C19 C14 C13 123.33(11) . . ?
C15 C14 C13 118.62(12) . . ?
C16 C15 C14 121.38(13) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.89(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.39(13) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.48(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C19 C18 120.74(13) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.65(18) . . . . ?
C7 C1 C2 C3 -176.75(11) . . . . ?
C1 C2 C3 O4 178.93(11) . . . . ?
C1 C2 C3 C4 -1.31(18) . . . . ?
C21 O3 C4 C3 82.55(15) . . . . ?
C21 O3 C4 C5 -100.13(14) . . . . ?
O4 C3 C4 O3 -4.46(17) . . . . ?
C2 C3 C4 O3 175.76(11) . . . . ?
O4 C3 C4 C5 178.21(11) . . . . ?
C2 C3 C4 C5 -1.57(18) . . . . ?
C2 C3 O4 C22 -3.86(18) . . . . ?
C4 C3 O4 C22 176.36(12) . . . . ?
C20 O2 C5 C6 -9.71(18) . . . . ?
C20 O2 C5 C4 170.54(11) . . . . ?
O3 C4 C5 O2 5.56(17) . . . . ?
C3 C4 C5 O2 -177.09(11) . . . . ?
O3 C4 C5 C6 -174.19(11) . . . . ?
C3 C4 C5 C6 3.15(18) . . . . ?
O2 C5 C6 C1 178.46(11) . . . . ?
C4 C5 C6 C1 -1.81(18) . . . . ?
C2 C1 C6 C5 -1.10(18) . . . . ?
C7 C1 C6 C5 178.28(11) . . . . ?
C2 C1 C7 C8 176.19(12) . . . . ?
C6 C1 C7 C8 -3.20(19) . . . . ?
C1 C7 C8 N1 0.5(2) . . . . ?
C1 C7 C8 C9 -177.26(11) . . . . ?
C10 N1 C8 C7 -177.29(12) . . . . ?
C10 N1 C8 C9 0.75(13) . . . . ?
C10 N2 C9 O1 -179.90(12) . . . . ?
C12 N2 C9 O1 2.86(19) . . . . ?
C10 N2 C9 C8 0.74(12) . . . . ?
C12 N2 C9 C8 -176.50(10) . . . . ?
C7 C8 C9 O1 -2.1(2) . . . . ?
N1 C8 C9 O1 179.77(12) . . . . ?
C7 C8 C9 N2 177.21(11) . . . . ?
N1 C8 C9 N2 -0.92(12) . . . . ?
C8 N1 C10 N2 -0.28(14) . . . . ?
C8 N1 C10 C11 -178.27(11) . . . . ?
C9 N2 C10 N1 -0.33(14) . . . . ?
C12 N2 C10 N1 176.79(11) . . . . ?
C9 N2 C10 C11 177.72(11) . . . . ?
C12 N2 C10 C11 -5.15(19) . . . . ?
C9 N2 C12 C13 -99.74(14) . . . . ?
C10 N2 C12 C13 83.57(15) . . . . ?
N2 C12 C13 C14 173.02(11) . . . . ?
C12 C13 C14 C19 13.92(19) . . . . ?
C12 C13 C14 C15 -164.46(12) . . . . ?
C19 C14 C15 C16 -2.6(2) . . . . ?
C13 C14 C15 C16 175.88(13) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 2.3(2) . . . . ?
C16 C17 C18 C19 -2.7(2) . . . . ?
C15 C14 C19 C18 2.2(2) . . . . ?
C13 C14 C19 C18 -176.20(13) . . . . ?
C17 C18 C19 C14 0.4(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
C2 H2 O1 0.95 2.66 3.5217(15) 151.1 3_666 yes
C6 H6 N1 0.95 2.30 2.9658(16) 127.0 . yes
C7 H7 O1 0.95 2.59 3.4820(15) 156.7 3_666 yes
C11 H11C O3 0.98 2.41 3.2423(16) 142.7 4_475 yes
C12 H12B O1 0.99 2.59 3.3876(16) 137.7 3_566 yes
C21 H21C O4 0.98 2.61 3.1142(18) 112.5 . yes

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_Form_B1
_database_code_depnum_ccdc_archive 'CCDC 2298738'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2024-02-22 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 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   5.0121(7)
_cell_length_b                   15.791(2)
_cell_length_c                   12.3050(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.364(4)
_cell_angle_gamma                90
_cell_volume                     954.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1568
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      20.68

_exptl_crystal_description       'THIN NEEDLE'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube '
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            21073
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_av_R_equivalents  0.1389
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.580
_diffrn_reflns_theta_max         24.702
_diffrn_reflns_theta_full        24.702
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3161
_reflns_number_gt                2100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.944

_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        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0506P)²] 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       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     258
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
O1 O 0.4972(8) 0.5947(3) 0.2924(3) 0.0322(11) Uani 1 1 d . . . . .
N1 N 0.6085(9) 0.6820(3) 0.5642(4) 0.0245(13) Uani 1 1 d . . . . .
C1 C 0.0987(12) 0.7955(4) 0.4597(5) 0.0251(15) Uani 1 1 d . . . . .
O2 O 0.1177(8) 0.9197(2) 0.7177(3) 0.0319(11) Uani 1 1 d . . . . .
N2 N 0.7920(9) 0.5858(3) 0.4630(4) 0.0234(12) Uani 1 1 d . . . . .
C2 C -0.1262(13) 0.8360(4) 0.3932(5) 0.0266(15) Uani 1 1 d . . . . .
O3 O -0.2984(8) 0.9897(3) 0.5923(4) 0.0355(12) Uani 1 1 d . . . . .
C3 C -0.2630(12) 0.9007(4) 0.4359(5) 0.0282(16) Uani 1 1 d . . . . .
H3 H -0.415087 0.927335 0.390497 0.034 Uiso 1 1 calc R U . . .
C4 C -0.1767(12) 0.9259(4) 0.5445(6) 0.0278(16) Uani 1 1 d . . . . .
O4 O -0.1988(8) 0.8082(3) 0.2865(3) 0.0325(12) Uani 1 1 d . . . . .
C5 C 0.0468(13) 0.8872(4) 0.6119(5) 0.0240(14) Uani 1 1 d . . . . .
C6 C 0.1813(12) 0.8232(4) 0.5696(5) 0.0231(15) Uani 1 1 d . . . . .
H6 H 0.333583 0.797162 0.615606 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2333(12) 0.7280(4) 0.4112(5) 0.0247(15) Uani 1 1 d . . . . .
H7 H 0.154675 0.715024 0.336420 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4534(12) 0.6806(4) 0.4556(5) 0.0234(15) Uani 1 1 d . . . . .
C14 C 1.1050(12) 0.3665(4) 0.4750(5) 0.0289(16) Uani 1 1 d . . . . .
C13 C 0.8850(12) 0.4315(4) 0.4736(5) 0.0309(16) Uani 1 1 d . . . . .
H13A H 0.838438 0.434728 0.548069 0.037 Uiso 1 1 calc R U . . .
H13B H 0.719722 0.413873 0.420334 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9747(13) 0.5197(4) 0.4409(6) 0.0298(16) Uani 1 1 d . . . . .
H12A H 1.160554 0.531608 0.482772 0.036 Uiso 1 1 calc R U . . .
H12B H 0.980681 0.519755 0.360930 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0165(12) 0.6053(4) 0.6617(5) 0.0338(17) Uani 1 1 d . . . . .
H11A H 1.195268 0.615408 0.643209 0.051 Uiso 1 1 calc R U . . .
H11B H 1.001207 0.545621 0.681376 0.051 Uiso 1 1 calc R U . . .
H11C H 0.995880 0.641066 0.724625 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7999(12) 0.6263(4) 0.5645(5) 0.0247(15) Uani 1 1 d . . . . .
C9 C 0.5710(12) 0.6170(4) 0.3895(5) 0.0251(15) Uani 1 1 d . . . . .
C15 C 1.1347(13) 0.3234(4) 0.3799(6) 0.0323(16) Uani 1 1 d . . . . .
H15 H 1.010641 0.334286 0.312419 0.039 Uiso 1 1 calc R U . . .
C17 C 1.5259(13) 0.2495(4) 0.4795(5) 0.0318(16) Uani 1 1 d . . . . .
H17 H 1.670713 0.210333 0.481312 0.038 Uiso 1 1 calc R U . . .
C16 C 1.3437(13) 0.2642(4) 0.3812(6) 0.0312(16) Uani 1 1 d . . . . .
H16 H 1.360002 0.234702 0.315606 0.037 Uiso 1 1 calc R U . . .
C18 C 1.4976(13) 0.2914(4) 0.5744(5) 0.0366(18) Uani 1 1 d . . . . .
H18 H 1.622930 0.280907 0.641704 0.044 Uiso 1 1 calc R U . . .
C19 C 1.2888(13) 0.3485(4) 0.5729(5) 0.0339(17) Uani 1 1 d . . . . .
H19 H 1.269803 0.375957 0.639610 0.041 Uiso 1 1 calc R U . . .
C21 C -0.5260(14) 1.0316(4) 0.5251(6) 0.0393(18) Uani 1 1 d . . . . .
H21A H -0.468866 1.057795 0.461169 0.059 Uiso 1 1 calc R U . . .
H21B H -0.594346 1.075444 0.568956 0.059 Uiso 1 1 calc R U . . .
H21C H -0.670396 0.990303 0.499179 0.059 Uiso 1 1 calc R U . . .
C20 C 0.3655(12) 0.8897(4) 0.7830(5) 0.0331(17) Uani 1 1 d . . . . .
H20A H 0.347759 0.829315 0.798700 0.050 Uiso 1 1 calc R U . . .
H20B H 0.406150 0.921269 0.852844 0.050 Uiso 1 1 calc R U . . .
H20C H 0.513361 0.897702 0.742425 0.050 Uiso 1 1 calc R U . . .
C22 C -0.4305(12) 0.8471(4) 0.2162(5) 0.0337(16) Uani 1 1 d . . . . .
H22A H -0.458320 0.821658 0.142144 0.051 Uiso 1 1 calc R U . . .
H22B H -0.397811 0.908004 0.210662 0.051 Uiso 1 1 calc R U . . .
H22C H -0.593000 0.838109 0.247852 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.231(7) . ?
N1 C10 1.301(8) . ?
N1 C8 1.407(7) . ?
C1 C6 1.403(8) . ?
C1 C2 1.409(8) . ?
C1 C7 1.451(8) . ?
O2 C5 1.380(7) . ?
O2 C20 1.421(7) . ?
N2 C9 1.375(8) . ?
N2 C10 1.397(7) . ?
N2 C12 1.450(7) . ?
C2 O4 1.364(7) . ?
C2 C3 1.389(8) . ?
O3 C4 1.369(7) . ?
O3 C21 1.432(7) . ?
C3 C4 1.380(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(9) . ?
O4 C22 1.442(7) . ?
C5 C6 1.373(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.356(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.485(8) . ?
C14 C15 1.386(8) . ?
C14 C19 1.394(8) . ?
C14 C13 1.505(8) . ?
C13 C12 1.540(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.486(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C15 C16 1.402(9) . ?
C15 H15 0.9500 . ?
C17 C18 1.374(8) . ?
C17 C16 1.384(8) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.379(8) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C10 N1 C8 105.1(5) . . ?
C6 C1 C2 117.9(6) . . ?
C6 C1 C7 123.5(6) . . ?
C2 C1 C7 118.6(6) . . ?
C5 O2 C20 116.3(5) . . ?
C9 N2 C10 107.5(5) . . ?
C9 N2 C12 126.2(5) . . ?
C10 N2 C12 126.2(5) . . ?
O4 C2 C3 122.8(6) . . ?
O4 C2 C1 116.4(5) . . ?
C3 C2 C1 120.8(6) . . ?
C4 O3 C21 117.6(5) . . ?
C4 C3 C2 119.6(6) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O3 C4 C3 123.2(6) . . ?
O3 C4 C5 116.1(6) . . ?
C3 C4 C5 120.6(6) . . ?
C2 O4 C22 118.1(5) . . ?
C6 C5 O2 125.3(6) . . ?
C6 C5 C4 119.6(6) . . ?
O2 C5 C4 115.1(5) . . ?
C5 C6 C1 121.4(6) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C8 C7 C1 130.4(6) . . ?
C8 C7 H7 114.8 . . ?
C1 C7 H7 114.8 . . ?
C7 C8 N1 128.8(5) . . ?
C7 C8 C9 122.2(5) . . ?
N1 C8 C9 109.0(5) . . ?
C15 C14 C19 117.8(6) . . ?
C15 C14 C13 121.7(6) . . ?
C19 C14 C13 120.4(6) . . ?
C14 C13 C12 111.6(5) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C12 C13 112.0(5) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C10 N2 114.6(5) . . ?
N1 C10 C11 125.1(5) . . ?
N2 C10 C11 120.3(5) . . ?
O1 C9 N2 125.8(5) . . ?
O1 C9 C8 130.5(6) . . ?
N2 C9 C8 103.7(5) . . ?
C14 C15 C16 121.5(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 C15 119.0(6) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C17 C18 C19 120.6(6) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.1(6) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O4 179.2(5) . . . . ?
C7 C1 C2 O4 -0.5(8) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
C7 C1 C2 C3 179.7(5) . . . . ?
O4 C2 C3 C4 -179.5(6) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C21 O3 C4 C3 -0.1(8) . . . . ?
C21 O3 C4 C5 179.1(5) . . . . ?
C2 C3 C4 O3 179.2(5) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C2 O4 C22 -1.0(8) . . . . ?
C1 C2 O4 C22 179.1(5) . . . . ?
C20 O2 C5 C6 6.6(8) . . . . ?
C20 O2 C5 C4 -171.7(5) . . . . ?
O3 C4 C5 C6 -179.4(5) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
O3 C4 C5 O2 -1.0(8) . . . . ?
C3 C4 C5 O2 178.2(5) . . . . ?
O2 C5 C6 C1 -178.4(6) . . . . ?
C4 C5 C6 C1 -0.1(9) . . . . ?
C2 C1 C6 C5 0.6(8) . . . . ?
C7 C1 C6 C5 -179.8(5) . . . . ?
C6 C1 C7 C8 -1.0(9) . . . . ?
C2 C1 C7 C8 178.7(6) . . . . ?
C1 C7 C8 N1 2.5(10) . . . . ?
C1 C7 C8 C9 -176.4(6) . . . . ?
C10 N1 C8 C7 -178.6(6) . . . . ?
C10 N1 C8 C9 0.4(6) . . . . ?
C15 C14 C13 C12 -85.9(7) . . . . ?
C19 C14 C13 C12 93.3(7) . . . . ?
C9 N2 C12 C13 -92.7(7) . . . . ?
C10 N2 C12 C13 83.6(7) . . . . ?
C14 C13 C12 N2 -167.2(5) . . . . ?
C8 N1 C10 N2 0.4(6) . . . . ?
C8 N1 C10 C11 179.8(5) . . . . ?
C9 N2 C10 N1 -1.2(6) . . . . ?
C12 N2 C10 N1 -178.0(5) . . . . ?
C9 N2 C10 C11 179.4(5) . . . . ?
C12 N2 C10 C11 2.6(8) . . . . ?
C10 N2 C9 O1 -178.6(6) . . . . ?
C12 N2 C9 O1 -1.7(9) . . . . ?
C10 N2 C9 C8 1.3(6) . . . . ?
C12 N2 C9 C8 178.1(5) . . . . ?
C7 C8 C9 O1 -2.1(10) . . . . ?
N1 C8 C9 O1 178.8(6) . . . . ?
C7 C8 C9 N2 178.0(5) . . . . ?
N1 C8 C9 N2 -1.1(6) . . . . ?
C19 C14 C15 C16 -0.6(9) . . . . ?
C13 C14 C15 C16 178.6(6) . . . . ?
C18 C17 C16 C15 1.2(10) . . . . ?
C14 C15 C16 C17 -0.8(10) . . . . ?
C16 C17 C18 C19 -0.1(9) . . . . ?
C17 C18 C19 C14 -1.4(10) . . . . ?
C15 C14 C19 C18 1.7(9) . . . . ?
C13 C14 C19 C18 -177.5(6) . . . . ?

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
C6 H6 N1 0.95 2.44 3.101(8) 126.6 . yes
C11 H11A N1 0.98 2.67 3.621(8) 163.4 1_655 yes
C11 H11B O1 0.98 2.60 3.554(8) 163.1 2_565 yes

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
