# Supplementary Information (SI) for Faraday Discussions.
# 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. 
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data_mo_pdoc060821_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344727'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ADP-2AMN
_chemical_formula_moiety         '2(C3 H4 O2), 2(C10 H18 N)'
_chemical_formula_sum            'C26 H44 N2 O4'
_chemical_formula_weight         448.63
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 '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 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0058 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5625(4)
_cell_length_b                   13.4728(9)
_cell_length_c                   14.2734(8)
_cell_angle_alpha                75.183(2)
_cell_angle_beta                 78.290(2)
_cell_angle_gamma                80.854(2)
_cell_volume                     1186.97(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6562
_cell_measurement_temperature    146(2)
_cell_measurement_theta_max      32.91
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.4864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1219 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.6516.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_preparation       METHANOL
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15179
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         25.410
_diffrn_reflns_theta_min         1.902
_diffrn_ambient_temperature      146.55
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5745
_reflns_number_total             7620
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+0.3671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1675
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O -0.38556(14) 0.21414(7) 1.07835(7) 0.0217(2) Uani 1 1 d . . . . .
O4 O 1.08851(15) 0.68612(8) 0.57035(8) 0.0250(2) Uani 1 1 d . . . . .
O1 O -0.11988(15) 0.21481(8) 1.15416(7) 0.0239(2) Uani 1 1 d . . . . .
O3 O 0.74752(15) 0.70815(8) 0.63025(8) 0.0258(2) Uani 1 1 d . . . . .
N1 N 0.32796(18) 0.67348(8) 0.70837(8) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.73956(18) -0.18666(8) 0.77715(9) 0.0183(2) Uani 1 1 d . . . . .
C4 C 0.9010(2) 0.68058(9) 0.56874(9) 0.0172(2) Uani 1 1 d . . . . .
C3 C -0.19587(19) 0.19648(9) 1.08596(9) 0.0169(2) Uani 1 1 d . . . . .
C16 C 0.34383(18) 0.56281(9) 0.76429(9) 0.0158(2) Uani 1 1 d . . . . .
C2 C -0.0468(2) 0.14418(10) 1.01137(10) 0.0194(2) Uani 1 1 d . . . . .
C10 C 0.4556(2) 0.38074(10) 0.74903(10) 0.0200(3) Uani 1 1 d . . . . .
C26 C 0.70387(19) -0.07392(9) 0.72860(9) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.8546(2) 0.64069(10) 0.48502(10) 0.0191(2) Uani 1 1 d . . . . .
C14 C 0.12580(19) 0.53437(10) 0.81644(10) 0.0190(2) Uani 1 1 d . . . . .
C22 C 0.6168(2) 0.10402(10) 0.75867(10) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.5064(2) 0.43573(10) 0.89698(10) 0.0205(3) Uani 1 1 d . . . . .
C25 C 0.6558(2) -0.01135(10) 0.80772(10) 0.0187(2) Uani 1 1 d . . . . .
C23 C 0.4787(2) 0.05861(10) 0.62526(10) 0.0213(3) Uani 1 1 d . . . . .
C15 C 0.4370(2) 0.49429(9) 0.69206(9) 0.0177(2) Uani 1 1 d . . . . .
C6 C 1.0106(2) 0.55008(10) 0.46006(9) 0.0194(2) Uani 1 1 d . . . . .
C24 C 0.9003(2) -0.04130(10) 0.65574(10) 0.0204(3) Uani 1 1 d . . . . .
C18 C 0.5176(2) -0.05683(10) 0.67425(10) 0.0197(2) Uani 1 1 d . . . . .
C8 C 0.1443(2) 0.42085(10) 0.87356(10) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.4883(2) 0.54910(10) 0.83977(10) 0.0189(2) Uani 1 1 d . . . . .
C7 C 0.2882(2) 0.40638(11) 0.94974(10) 0.0232(3) Uani 1 1 d . . . . .
C19 C 0.6752(2) 0.09265(11) 0.55190(11) 0.0246(3) Uani 1 1 d . . . . .
C17 C 0.4301(2) 0.12137(10) 0.70440(11) 0.0229(3) Uani 1 1 d . . . . .
C20 C 0.8615(2) 0.07409(11) 0.60663(10) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.2379(2) 0.35111(10) 0.80179(11) 0.0215(3) Uani 1 1 d . . . . .
C11 C 0.5991(2) 0.36616(10) 0.82534(11) 0.0225(3) Uani 1 1 d . . . . .
C21 C 0.8128(2) 0.13780(11) 0.68504(11) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.989(3) 0.0979(14) 0.5581(13) 0.028(5) Uiso 1 1 d . . . . .
H22 H 0.591(3) 0.1419(13) 0.8099(13) 0.026(4) Uiso 1 1 d . . . . .
H5A H 0.707(3) 0.6214(13) 0.5010(13) 0.024(4) Uiso 1 1 d . . . . .
H14A H 0.035(3) 0.5441(14) 0.7660(13) 0.029(5) Uiso 1 1 d . . . . .
H24A H 0.934(3) -0.0839(13) 0.6043(13) 0.026(4) Uiso 1 1 d . . . . .
H25A H 0.533(3) -0.0374(12) 0.8564(12) 0.019(4) Uiso 1 1 d . . . . .
H10 H 0.520(3) 0.3362(13) 0.7026(13) 0.026(4) Uiso 1 1 d . . . . .
H18A H 0.395(3) -0.0816(13) 0.7213(13) 0.025(4) Uiso 1 1 d . . . . .
H21A H 0.940(3) 0.1265(14) 0.7179(13) 0.029(5) Uiso 1 1 d . . . . .
H15A H 0.344(3) 0.5053(13) 0.6421(12) 0.021(4) Uiso 1 1 d . . . . .
H14B H 0.063(3) 0.5826(14) 0.8607(13) 0.027(4) Uiso 1 1 d . . . . .
H18B H 0.550(3) -0.0999(14) 0.6237(14) 0.031(5) Uiso 1 1 d . . . . .
H19A H 0.650(3) 0.1675(15) 0.5196(14) 0.034(5) Uiso 1 1 d . . . . .
H8 H 0.004(3) 0.3988(15) 0.9082(14) 0.035(5) Uiso 1 1 d . . . . .
H25B H 0.782(3) -0.0263(14) 0.8417(13) 0.029(5) Uiso 1 1 d . . . . .
H17A H 0.302(3) 0.1012(14) 0.7505(14) 0.030(5) Uiso 1 1 d . . . . .
H15B H 0.577(3) 0.5142(13) 0.6574(13) 0.023(4) Uiso 1 1 d . . . . .
H11A H 0.743(3) 0.3839(14) 0.7904(13) 0.029(5) Uiso 1 1 d . . . . .
H13A H 0.630(3) 0.5687(15) 0.8045(14) 0.034(5) Uiso 1 1 d . . . . .
H12 H 0.599(3) 0.4259(13) 0.9466(13) 0.023(4) Uiso 1 1 d . . . . .
H7A H 0.301(3) 0.3325(14) 0.9874(14) 0.031(5) Uiso 1 1 d . . . . .
H5B H 0.867(3) 0.6992(15) 0.4260(14) 0.036(5) Uiso 1 1 d . . . . .
H7B H 0.221(3) 0.4504(14) 0.9992(13) 0.028(5) Uiso 1 1 d . . . . .
H1A H 0.466(3) 0.6918(15) 0.6727(14) 0.033(5) Uiso 1 1 d . . . . .
H9A H 0.144(3) 0.3581(14) 0.7525(13) 0.029(5) Uiso 1 1 d . . . . .
H11B H 0.615(3) 0.2913(14) 0.8631(14) 0.032(5) Uiso 1 1 d . . . . .
H1B H 0.240(3) 0.6835(14) 0.6622(14) 0.035(5) Uiso 1 1 d . . . . .
H13B H 0.430(3) 0.5942(14) 0.8843(14) 0.032(5) Uiso 1 1 d . . . . .
H23 H 0.359(3) 0.0699(14) 0.5884(13) 0.029(5) Uiso 1 1 d . . . . .
H24B H 1.020(3) -0.0554(13) 0.6914(13) 0.027(4) Uiso 1 1 d . . . . .
H19B H 0.706(3) 0.0522(15) 0.4997(15) 0.037(5) Uiso 1 1 d . . . . .
H17B H 0.395(3) 0.1959(14) 0.6749(13) 0.031(5) Uiso 1 1 d . . . . .
H21B H 0.793(3) 0.2135(15) 0.6510(14) 0.035(5) Uiso 1 1 d . . . . .
H2A H 0.618(3) -0.2077(14) 0.8298(14) 0.032(5) Uiso 1 1 d . . . . .
H2B H 0.763(3) -0.2254(16) 0.7302(15) 0.041(6) Uiso 1 1 d . . . . .
H2C H 0.855(3) -0.1988(15) 0.8082(14) 0.033(5) Uiso 1 1 d . . . . .
H9B H 0.249(3) 0.2779(15) 0.8388(14) 0.034(5) Uiso 1 1 d . . . . .
H1C H 0.271(3) 0.7163(16) 0.7507(15) 0.038(5) Uiso 1 1 d . . . . .
C1 C -0.0819(2) 0.03017(10) 1.03151(10) 0.0192(2) Uani 1 1 d . . . . .
H2D H 0.101(3) 0.1510(13) 1.0150(12) 0.023(4) Uiso 1 1 d . . . . .
H2E H -0.071(3) 0.1803(14) 0.9421(13) 0.030(5) Uiso 1 1 d . . . . .
H1D H -0.077(3) -0.0063(13) 1.1038(13) 0.021(4) Uiso 1 1 d . . . . .
H6A H 1.154(3) 0.5708(13) 0.4511(13) 0.026(4) Uiso 1 1 d . . . . .
H1E H -0.221(3) 0.0251(13) 1.0208(12) 0.021(4) Uiso 1 1 d . . . . .
H6B H 0.999(3) 0.5390(13) 0.3942(13) 0.024(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.2512(15) . ?
O4 C4 1.2494(15) . ?
O1 C3 1.2715(15) . ?
O3 C4 1.2699(15) . ?
N1 C16 1.4988(16) . ?
N1 H1A 0.98(2) . ?
N1 H1B 0.934(19) . ?
N1 H1C 0.93(2) . ?
N2 C26 1.5023(16) . ?
N2 H2A 1.00(2) . ?
N2 H2B 0.92(2) . ?
N2 H2C 0.924(19) . ?
C4 C5 1.5291(17) . ?
C3 C2 1.5260(17) . ?
C16 C14 1.5311(18) . ?
C16 C15 1.5299(16) . ?
C16 C13 1.5334(17) . ?
C2 C1 1.5345(18) . ?
C2 H2D 1.001(17) . ?
C2 H2E 1.016(18) . ?
C10 C15 1.5367(18) . ?
C10 C9 1.5358(19) . ?
C10 C11 1.5365(19) . ?
C10 H10 0.993(17) . ?
C26 C25 1.5306(17) . ?
C26 C24 1.5293(18) . ?
C26 C18 1.5337(17) . ?
C5 C6 1.5304(17) . ?
C5 H5A 1.008(18) . ?
C5 H5B 1.00(2) . ?
C14 C8 1.5369(18) . ?
C14 H14A 0.996(18) . ?
C14 H14B 1.004(18) . ?
C22 C25 1.5367(18) . ?
C22 C17 1.5355(18) . ?
C22 C21 1.536(2) . ?
C22 H22 0.968(17) . ?
C12 C13 1.5354(18) . ?
C12 C7 1.537(2) . ?
C12 C11 1.5333(18) . ?
C12 H12 0.995(17) . ?
C25 H25A 0.999(17) . ?
C25 H25B 1.009(18) . ?
C23 C18 1.5373(18) . ?
C23 C19 1.538(2) . ?
C23 C17 1.5327(19) . ?
C23 H23 1.005(18) . ?
C15 H15A 0.999(16) . ?
C15 H15B 0.993(18) . ?
C6 C6 1.532(3) 2_766 ?
C6 H6A 0.998(18) . ?
C6 H6B 1.009(17) . ?
C24 C20 1.5370(19) . ?
C24 H24A 1.014(17) . ?
C24 H24B 0.987(17) . ?
C18 H18A 0.981(18) . ?
C18 H18B 1.007(18) . ?
C8 C7 1.5367(19) . ?
C8 C9 1.5371(18) . ?
C8 H8 1.00(2) . ?
C13 H13A 1.01(2) . ?
C13 H13B 0.972(19) . ?
C7 H7A 1.003(19) . ?
C7 H7B 1.024(18) . ?
C19 C20 1.5357(19) . ?
C19 H19A 0.998(19) . ?
C19 H19B 1.00(2) . ?
C17 H17A 0.984(19) . ?
C17 H17B 0.994(18) . ?
C20 C21 1.5331(19) . ?
C20 H20 1.010(19) . ?
C9 H9A 1.002(18) . ?
C9 H9B 0.992(19) . ?
C11 H11A 1.007(19) . ?
C11 H11B 1.015(18) . ?
C21 H21A 1.013(18) . ?
C21 H21B 1.012(19) . ?
C1 C1 1.526(2) 2_557 ?
C1 H1D 1.028(17) . ?
C1 H1E 0.972(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 H1A 110.3(11) . . ?
C16 N1 H1B 109.9(12) . . ?
C16 N1 H1C 110.2(13) . . ?
H1A N1 H1B 107.8(16) . . ?
H1A N1 H1C 110.7(16) . . ?
H1B N1 H1C 107.8(17) . . ?
C26 N2 H2A 110.5(11) . . ?
C26 N2 H2B 109.6(13) . . ?
C26 N2 H2C 109.8(12) . . ?
H2A N2 H2B 111.5(16) . . ?
H2A N2 H2C 106.3(16) . . ?
H2B N2 H2C 109.1(17) . . ?
O4 C4 O3 124.45(12) . . ?
O4 C4 C5 117.32(11) . . ?
O3 C4 C5 118.20(11) . . ?
O2 C3 O1 124.55(11) . . ?
O2 C3 C2 117.83(11) . . ?
O1 C3 C2 117.54(11) . . ?
N1 C16 C14 109.63(9) . . ?
N1 C16 C15 108.80(10) . . ?
N1 C16 C13 108.64(10) . . ?
C14 C16 C13 110.19(10) . . ?
C15 C16 C14 109.93(10) . . ?
C15 C16 C13 109.63(10) . . ?
C3 C2 C1 110.27(11) . . ?
C3 C2 H2D 109.2(10) . . ?
C3 C2 H2E 110.1(10) . . ?
C1 C2 H2D 110.9(10) . . ?
C1 C2 H2E 109.3(10) . . ?
H2D C2 H2E 107.1(14) . . ?
C15 C10 H10 109.3(10) . . ?
C9 C10 C15 109.65(10) . . ?
C9 C10 C11 109.39(11) . . ?
C9 C10 H10 110.9(10) . . ?
C11 C10 C15 109.39(10) . . ?
C11 C10 H10 108.2(10) . . ?
N2 C26 C25 108.88(10) . . ?
N2 C26 C24 109.51(9) . . ?
N2 C26 C18 108.64(10) . . ?
C25 C26 C18 110.01(10) . . ?
C24 C26 C25 109.86(10) . . ?
C24 C26 C18 109.92(11) . . ?
C4 C5 C6 113.62(10) . . ?
C4 C5 H5A 109.9(10) . . ?
C4 C5 H5B 106.1(11) . . ?
C6 C5 H5A 110.5(10) . . ?
C6 C5 H5B 107.5(11) . . ?
H5A C5 H5B 109.1(15) . . ?
C16 C14 C8 109.10(10) . . ?
C16 C14 H14A 108.7(11) . . ?
C16 C14 H14B 109.0(10) . . ?
C8 C14 H14A 109.9(10) . . ?
C8 C14 H14B 112.1(10) . . ?
H14A C14 H14B 108.0(14) . . ?
C25 C22 H22 107.4(10) . . ?
C17 C22 C25 109.08(11) . . ?
C17 C22 C21 109.58(11) . . ?
C17 C22 H22 112.2(10) . . ?
C21 C22 C25 109.46(10) . . ?
C21 C22 H22 109.0(11) . . ?
C13 C12 C7 109.65(10) . . ?
C13 C12 H12 109.8(10) . . ?
C7 C12 H12 109.2(10) . . ?
C11 C12 C13 109.43(11) . . ?
C11 C12 C7 109.40(11) . . ?
C11 C12 H12 109.4(10) . . ?
C26 C25 C22 109.16(10) . . ?
C26 C25 H25A 108.0(9) . . ?
C26 C25 H25B 106.7(10) . . ?
C22 C25 H25A 112.8(9) . . ?
C22 C25 H25B 111.4(10) . . ?
H25A C25 H25B 108.6(14) . . ?
C18 C23 C19 109.49(11) . . ?
C18 C23 H23 109.2(10) . . ?
C19 C23 H23 108.6(10) . . ?
C17 C23 C18 109.29(11) . . ?
C17 C23 C19 109.50(11) . . ?
C17 C23 H23 110.7(10) . . ?
C16 C15 C10 109.08(10) . . ?
C16 C15 H15A 109.0(10) . . ?
C16 C15 H15B 109.5(10) . . ?
C10 C15 H15A 110.5(10) . . ?
C10 C15 H15B 110.3(10) . . ?
H15A C15 H15B 108.3(13) . . ?
C5 C6 C6 113.11(14) . 2_766 ?
C5 C6 H6A 107.2(10) . . ?
C5 C6 H6B 110.7(10) . . ?
C6 C6 H6A 109.7(10) 2_766 . ?
C6 C6 H6B 110.8(10) 2_766 . ?
H6A C6 H6B 105.0(14) . . ?
C26 C24 C20 108.94(10) . . ?
C26 C24 H24A 109.8(10) . . ?
C26 C24 H24B 108.9(11) . . ?
C20 C24 H24A 110.2(10) . . ?
C20 C24 H24B 111.3(10) . . ?
H24A C24 H24B 107.7(14) . . ?
C26 C18 C23 108.94(10) . . ?
C26 C18 H18A 109.0(10) . . ?
C26 C18 H18B 108.9(11) . . ?
C23 C18 H18A 111.9(10) . . ?
C23 C18 H18B 110.9(11) . . ?
H18A C18 H18B 107.2(14) . . ?
C14 C8 C9 109.54(11) . . ?
C14 C8 H8 111.6(11) . . ?
C7 C8 C14 109.37(11) . . ?
C7 C8 C9 109.35(11) . . ?
C7 C8 H8 109.1(11) . . ?
C9 C8 H8 107.8(11) . . ?
C16 C13 C12 108.94(10) . . ?
C16 C13 H13A 109.2(11) . . ?
C16 C13 H13B 109.3(11) . . ?
C12 C13 H13A 110.1(11) . . ?
C12 C13 H13B 110.4(11) . . ?
H13A C13 H13B 108.8(15) . . ?
C12 C7 H7A 109.5(11) . . ?
C12 C7 H7B 112.0(10) . . ?
C8 C7 C12 109.53(11) . . ?
C8 C7 H7A 109.8(10) . . ?
C8 C7 H7B 108.8(10) . . ?
H7A C7 H7B 107.2(15) . . ?
C23 C19 H19A 109.5(11) . . ?
C23 C19 H19B 109.4(11) . . ?
C20 C19 C23 109.42(11) . . ?
C20 C19 H19A 110.0(11) . . ?
C20 C19 H19B 110.2(11) . . ?
H19A C19 H19B 108.3(15) . . ?
C22 C17 H17A 110.9(11) . . ?
C22 C17 H17B 111.2(10) . . ?
C23 C17 C22 109.72(10) . . ?
C23 C17 H17A 109.8(10) . . ?
C23 C17 H17B 110.7(10) . . ?
H17A C17 H17B 104.5(15) . . ?
C24 C20 H20 110.7(10) . . ?
C19 C20 C24 109.66(11) . . ?
C19 C20 H20 108.9(10) . . ?
C21 C20 C24 109.75(11) . . ?
C21 C20 C19 109.22(11) . . ?
C21 C20 H20 108.6(10) . . ?
C10 C9 C8 109.40(10) . . ?
C10 C9 H9A 110.1(11) . . ?
C10 C9 H9B 110.0(11) . . ?
C8 C9 H9A 110.5(11) . . ?
C8 C9 H9B 109.4(11) . . ?
H9A C9 H9B 107.4(15) . . ?
C10 C11 H11A 109.2(10) . . ?
C10 C11 H11B 110.5(10) . . ?
C12 C11 C10 109.49(10) . . ?
C12 C11 H11A 110.6(10) . . ?
C12 C11 H11B 109.6(11) . . ?
H11A C11 H11B 107.4(15) . . ?
C22 C21 H21A 112.0(10) . . ?
C22 C21 H21B 111.8(11) . . ?
C20 C21 C22 109.47(11) . . ?
C20 C21 H21A 107.5(10) . . ?
C20 C21 H21B 108.5(11) . . ?
H21A C21 H21B 107.4(15) . . ?
C2 C1 H1D 111.0(9) . . ?
C2 C1 H1E 109.8(10) . . ?
C1 C1 C2 112.82(14) 2_557 . ?
C1 C1 H1D 107.2(9) 2_557 . ?
C1 C1 H1E 109.8(10) 2_557 . ?
H1D C1 H1E 106.0(13) . . ?

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
O2 C3 C2 C1 -72.15(15) . . . . ?
O4 C4 C5 C6 40.32(17) . . . . ?
O1 C3 C2 C1 104.75(14) . . . . ?
O3 C4 C5 C6 -141.39(12) . . . . ?
N1 C16 C14 C8 -179.93(10) . . . . ?
N1 C16 C15 C10 179.49(9) . . . . ?
N1 C16 C13 C12 -179.68(10) . . . . ?
N2 C26 C25 C22 -179.41(10) . . . . ?
N2 C26 C24 C20 179.96(10) . . . . ?
N2 C26 C18 C23 179.41(10) . . . . ?
C4 C5 C6 C6 70.24(18) . . . 2_766 ?
C3 C2 C1 C1 -172.17(13) . . . 2_557 ?
C16 C14 C8 C7 59.90(13) . . . . ?
C16 C14 C8 C9 -59.93(13) . . . . ?
C26 C24 C20 C19 -60.03(14) . . . . ?
C26 C24 C20 C21 59.96(13) . . . . ?
C14 C16 C15 C10 -60.45(13) . . . . ?
C14 C16 C13 C12 60.20(13) . . . . ?
C14 C8 C7 C12 -59.96(13) . . . . ?
C14 C8 C9 C10 59.75(13) . . . . ?
C25 C26 C24 C20 -60.49(13) . . . . ?
C25 C26 C18 C23 60.32(14) . . . . ?
C25 C22 C17 C23 -60.37(15) . . . . ?
C25 C22 C21 C20 59.64(14) . . . . ?
C23 C19 C20 C24 59.82(14) . . . . ?
C23 C19 C20 C21 -60.50(15) . . . . ?
C15 C16 C14 C8 60.52(13) . . . . ?
C15 C16 C13 C12 -60.91(13) . . . . ?
C15 C10 C9 C8 -59.75(14) . . . . ?
C15 C10 C11 C12 59.86(14) . . . . ?
C24 C26 C25 C22 60.67(13) . . . . ?
C24 C26 C18 C23 -60.78(13) . . . . ?
C24 C20 C21 C22 -59.79(14) . . . . ?
C18 C26 C25 C22 -60.46(14) . . . . ?
C18 C26 C24 C20 60.69(13) . . . . ?
C18 C23 C19 C20 -59.79(14) . . . . ?
C18 C23 C17 C22 60.48(14) . . . . ?
C13 C16 C14 C8 -60.42(13) . . . . ?
C13 C16 C15 C10 60.82(13) . . . . ?
C13 C12 C7 C8 60.01(13) . . . . ?
C13 C12 C11 C10 -60.07(14) . . . . ?
C7 C12 C13 C16 -59.66(13) . . . . ?
C7 C12 C11 C10 60.08(14) . . . . ?
C7 C8 C9 C10 -60.10(14) . . . . ?
C19 C23 C18 C26 60.00(14) . . . . ?
C19 C23 C17 C22 -59.45(14) . . . . ?
C19 C20 C21 C22 60.47(14) . . . . ?
C17 C22 C25 C26 59.96(13) . . . . ?
C17 C22 C21 C20 -59.94(13) . . . . ?
C17 C23 C18 C26 -59.93(14) . . . . ?
C17 C23 C19 C20 60.01(14) . . . . ?
C9 C10 C15 C16 59.90(13) . . . . ?
C9 C10 C11 C12 -60.26(14) . . . . ?
C9 C8 C7 C12 59.99(14) . . . . ?
C11 C10 C15 C16 -60.06(13) . . . . ?
C11 C10 C9 C8 60.21(13) . . . . ?
C11 C12 C13 C16 60.34(13) . . . . ?
C11 C12 C7 C8 -60.01(13) . . . . ?
C21 C22 C25 C26 -59.92(13) . . . . ?
C21 C22 C17 C23 59.44(14) . . . . ?

_olex2_exptl_crystal_mounting_method LOOP
_olex2_submission_original_sample_id ADP-AMN
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_pd050722_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344728'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ADIPIC-2TYRAMINE
_chemical_formula_moiety         '1.5(C6 H8 O4), 3(C8 H12 N O)'
_chemical_formula_sum            'C33 H48 N3 O9'
_chemical_formula_weight         630.74
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4038(8)
_cell_length_b                   12.7819(7)
_cell_length_c                   13.6007(8)
_cell_angle_alpha                88.897(2)
_cell_angle_beta                 70.005(2)
_cell_angle_gamma                65.733(2)
_cell_volume                     1681.25(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4565
_cell_measurement_temperature    145(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1156 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.8162.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             678
_exptl_crystal_preparation       'Methanol- diethylether mixture'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16204
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.469
_diffrn_reflns_theta_min         2.294
_diffrn_ambient_temperature      145.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4327
_reflns_number_total             6172
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.5083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C33(H33A,H33B), C32(H32A,H32B), C16(H16A,
 H16B), C13(H13A,H13B), C10(H10A,H10B), C11(H11A,H11B), C2(H2A,H2B), C1(H1D,
 H1E), C25(H25A,H25B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C31(H31), C27(H27), C30(H30), C5(H5), C4(H4), C7(H7), C8(H8),
 C22(H22), C23(H23), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N1(H1A,H1B,H1C), N2(H2C,H2D,H2E)
2.d Idealised tetrahedral OH refined as rotating group:
 O9(H9), O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O8 O 0.77423(13) 0.10816(10) 0.07738(10) 0.0313(3) Uani 1 1 d . . . . .
O7 O 0.83403(13) 0.24495(10) 0.10883(10) 0.0292(3) Uani 1 1 d . . . . .
O5 O 0.18999(14) 0.67156(11) 0.55275(10) 0.0354(4) Uani 1 1 d . . . . .
O6 O 0.15312(13) 0.53174(11) 0.49362(10) 0.0328(3) Uani 1 1 d . . . . .
N3 N 0.87741(16) -0.37652(12) 0.62680(12) 0.0274(4) Uani 1 1 d . . . . .
H3A H 0.969751 -0.402458 0.590065 0.033 Uiso 1 1 calc R U . . .
H3B H 0.844803 -0.419399 0.600838 0.033 Uiso 1 1 calc R U . . .
H3C H 0.862120 -0.383441 0.696284 0.033 Uiso 1 1 calc R U . . .
O9 O 0.63708(16) 0.23941(12) 0.44411(13) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.689247 0.267812 0.450282 0.067 Uiso 1 1 calc R U . . .
C17 C 0.74375(19) 0.20949(15) 0.11711(14) 0.0248(4) Uani 1 1 d . . . . .
C28 C 0.6886(2) -0.06036(17) 0.43948(15) 0.0332(5) Uani 1 1 d . . . . .
H28 H 0.655999 -0.108156 0.414900 0.040 Uiso 1 1 calc R U . . .
C15 C 0.55428(19) 0.39653(15) 0.24364(15) 0.0290(5) Uani 1 1 d . . . . .
H15A H 0.563650 0.454896 0.196451 0.035 Uiso 1 1 calc R U . . .
H15B H 0.617684 0.382839 0.282192 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2244(2) 0.58733(16) 0.48501(15) 0.0283(4) Uani 1 1 d . . . . .
C14 C 0.40612(19) 0.44193(15) 0.32207(15) 0.0281(4) Uani 1 1 d . . . . .
H14A H 0.344246 0.453513 0.282502 0.034 Uiso 1 1 calc R U . . .
H14B H 0.398185 0.382436 0.368241 0.034 Uiso 1 1 calc R U . . .
C33 C 0.8044(2) -0.25213(16) 0.61566(15) 0.0326(5) Uani 1 1 d . . . . .
H33A H 0.831271 -0.204236 0.651866 0.039 Uiso 1 1 calc R U . . .
H33B H 0.703319 -0.226038 0.650053 0.039 Uiso 1 1 calc R U . . .
C29 C 0.7829(2) -0.10788(16) 0.48854(15) 0.0307(5) Uani 1 1 d . . . . .
C31 C 0.7780(2) 0.08132(17) 0.51287(16) 0.0325(5) Uani 1 1 d . . . . .
H31 H 0.808035 0.129905 0.539479 0.039 Uiso 1 1 calc R U . . .
C27 C 0.6405(2) 0.05513(18) 0.42532(16) 0.0345(5) Uani 1 1 d . . . . .
H27 H 0.576379 0.085520 0.390659 0.041 Uiso 1 1 calc R U . . .
C26 C 0.6855(2) 0.12644(16) 0.46153(15) 0.0304(5) Uani 1 1 d . . . . .
C32 C 0.8395(2) -0.23499(17) 0.50085(16) 0.0368(5) Uani 1 1 d . . . . .
H32A H 0.800702 -0.273845 0.467192 0.044 Uiso 1 1 calc R U . . .
H32B H 0.941204 -0.271460 0.464140 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5929(2) 0.28450(16) 0.17850(17) 0.0336(5) Uani 1 1 d . . . . .
H16A H 0.555560 0.237276 0.226671 0.040 Uiso 1 1 calc R U . . .
H16B H 0.544761 0.304059 0.127727 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3571(2) 0.55443(17) 0.39072(16) 0.0376(5) Uani 1 1 d . . . . .
H13A H 0.430645 0.548760 0.416363 0.045 Uiso 1 1 calc R U . . .
H13B H 0.344013 0.617596 0.346466 0.045 Uiso 1 1 calc R U . . .
C30 C 0.8263(2) -0.03460(17) 0.52524(16) 0.0333(5) Uani 1 1 d . . . . .
H30 H 0.890707 -0.065040 0.559628 0.040 Uiso 1 1 calc R U . . .
O2 O 0.15445(13) 0.18547(11) 0.16395(11) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.19197(14) 0.34202(10) 0.15397(10) 0.0324(3) Uani 1 1 d . . . . .
C10 C 0.37977(18) 0.16370(15) 0.05319(14) 0.0246(4) Uani 1 1 d . . . . .
H10A H 0.442486 0.179436 0.079737 0.030 Uiso 1 1 calc R U . . .
H10B H 0.390302 0.190752 -0.016669 0.030 Uiso 1 1 calc R U . . .
C11 C 0.42585(17) 0.03287(14) 0.03822(14) 0.0230(4) Uani 1 1 d . . . . .
H11A H 0.416981 0.004835 0.107582 0.028 Uiso 1 1 calc R U . . .
H11B H 0.363833 0.016276 0.011445 0.028 Uiso 1 1 calc R U . . .
C9 C 0.23290(19) 0.23383(15) 0.12788(14) 0.0246(4) Uani 1 1 d . . . . .
N1 N 0.05714(15) 0.03994(12) 0.11361(11) 0.0252(4) Uani 1 1 d . . . . .
H1A H 0.103932 -0.027329 0.067827 0.030 Uiso 1 1 calc R U . . .
H1B H 0.117382 0.068416 0.116195 0.030 Uiso 1 1 calc R U . . .
H1C H -0.007663 0.092578 0.091272 0.030 Uiso 1 1 calc R U . . .
O1 O 0.33176(15) -0.53533(12) 0.06927(13) 0.0490(4) Uani 1 1 d . . . . .
H1 H 0.279415 -0.567608 0.095665 0.073 Uiso 1 1 calc R U . . .
C5 C 0.1327(2) -0.36972(16) 0.18358(16) 0.0325(5) Uani 1 1 d . . . . .
H5 H 0.077213 -0.410976 0.197476 0.039 Uiso 1 1 calc R U . . .
C2 C 0.0915(2) -0.06883(16) 0.26311(16) 0.0343(5) Uani 1 1 d . . . . .
H2A H 0.166695 -0.045001 0.253239 0.041 Uiso 1 1 calc R U . . .
H2B H 0.044837 -0.065205 0.340003 0.041 Uiso 1 1 calc R U . . .
C1 C -0.0120(2) 0.01729(16) 0.22093(15) 0.0304(5) Uani 1 1 d . . . . .
H1D H -0.077713 -0.013365 0.217881 0.036 Uiso 1 1 calc R U . . .
H1E H -0.065393 0.091104 0.269975 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0762(2) -0.25527(16) 0.22924(15) 0.0330(5) Uani 1 1 d . . . . .
H4 H -0.018635 -0.218745 0.273754 0.040 Uiso 1 1 calc R U . . .
C3 C 0.1546(2) -0.19261(16) 0.21161(15) 0.0289(5) Uani 1 1 d . . . . .
C7 C 0.3501(2) -0.36270(18) 0.09978(18) 0.0434(6) Uani 1 1 d . . . . .
H7 H 0.445071 -0.399438 0.055489 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2923(2) -0.24890(17) 0.14604(17) 0.0384(5) Uani 1 1 d . . . . .
H8 H 0.348439 -0.208264 0.132511 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2701(2) -0.42314(16) 0.11784(16) 0.0342(5) Uani 1 1 d . . . . .
O4 O 0.59126(14) 0.03224(11) 0.19978(11) 0.0342(3) Uani 1 1 d . . . . .
H4A H 0.649053 0.055057 0.161802 0.051 Uiso 1 1 calc R U . . .
N2 N 0.88499(15) -0.63147(12) 0.23904(12) 0.0266(4) Uani 1 1 d . . . . .
H2C H 0.849966 -0.659960 0.200994 0.032 Uiso 1 1 calc R U . . .
H2D H 0.866559 -0.654319 0.304205 0.032 Uiso 1 1 calc R U . . .
H2E H 0.978069 -0.658920 0.205038 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6498(2) -0.08606(16) 0.18655(14) 0.0270(4) Uani 1 1 d . . . . .
C22 C 0.6230(2) -0.26076(17) 0.22292(16) 0.0347(5) Uani 1 1 d . . . . .
H22 H 0.566006 -0.297659 0.257690 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5675(2) -0.14073(17) 0.23740(15) 0.0331(5) Uani 1 1 d . . . . .
H23 H 0.473805 -0.096246 0.281825 0.040 Uiso 1 1 calc R U . . .
C25 C 0.8204(2) -0.50305(15) 0.25026(15) 0.0294(5) Uani 1 1 d . . . . .
H25A H 0.871183 -0.472998 0.279071 0.035 Uiso 1 1 calc R U . . .
H25B H 0.723868 -0.472759 0.301177 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7870(2) -0.15245(16) 0.12362(15) 0.0297(5) Uani 1 1 d . . . . .
H19 H 0.844635 -0.115693 0.089784 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8402(2) -0.27209(16) 0.11002(15) 0.0309(5) Uani 1 1 d . . . . .
H20 H 0.934130 -0.316475 0.066028 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7600(2) -0.32870(17) 0.15888(15) 0.0314(5) Uani 1 1 d . . . . .
C24 C 0.8210(2) -0.45980(16) 0.14605(16) 0.0347(5) Uani 1 1 d . . . . .
H24A H 0.766710 -0.486705 0.118569 0.042 Uiso 1 1 calc R U . . .
H24B H 0.917117 -0.492298 0.094106 0.042 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
O8 C17 1.272(2) . ?
O7 C17 1.257(2) . ?
O5 C12 1.267(2) . ?
O6 C12 1.260(2) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C33 1.494(2) . ?
O9 H9 0.8400 . ?
O9 C26 1.367(2) . ?
C17 C16 1.506(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(3) . ?
C28 C27 1.383(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.521(2) . ?
C15 C16 1.514(2) . ?
C12 C13 1.510(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.512(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C32 1.509(3) . ?
C29 C32 1.512(3) . ?
C29 C30 1.393(3) . ?
C31 H31 0.9500 . ?
C31 C26 1.385(3) . ?
C31 C30 1.382(3) . ?
C27 H27 0.9500 . ?
C27 C26 1.383(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C30 H30 0.9500 . ?
O2 C9 1.251(2) . ?
O3 C9 1.277(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.527(2) . ?
C10 C9 1.509(2) . ?
C11 C11 1.520(3) 2_655 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.490(2) . ?
O1 H1 0.8400 . ?
O1 C6 1.370(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(3) . ?
C5 C6 1.381(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.518(3) . ?
C2 C3 1.508(3) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C4 H4 0.9500 . ?
C4 C3 1.390(3) . ?
C3 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(3) . ?
C7 C6 1.382(3) . ?
C8 H8 0.9500 . ?
O4 H4A 0.8400 . ?
O4 C18 1.365(2) . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
N2 H2E 0.9100 . ?
N2 C25 1.483(2) . ?
C18 C23 1.387(3) . ?
C18 C19 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C22 C21 1.391(3) . ?
C23 H23 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C24 1.510(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(3) . ?
C21 C24 1.514(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C33 N3 H3A 109.5 . . ?
C33 N3 H3B 109.5 . . ?
C33 N3 H3C 109.5 . . ?
C26 O9 H9 109.5 . . ?
O8 C17 C16 116.39(16) . . ?
O7 C17 O8 122.41(17) . . ?
O7 C17 C16 121.18(15) . . ?
C29 C28 H28 119.2 . . ?
C29 C28 C27 121.57(18) . . ?
C27 C28 H28 119.2 . . ?
H15A C15 H15B 108.2 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C16 C15 C14 109.98(15) . . ?
O5 C12 C13 117.26(17) . . ?
O6 C12 O5 122.82(17) . . ?
O6 C12 C13 119.92(16) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C13 C14 C15 114.12(15) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
N3 C33 H33A 109.4 . . ?
N3 C33 H33B 109.4 . . ?
N3 C33 C32 111.15(15) . . ?
H33A C33 H33B 108.0 . . ?
C32 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
C28 C29 C32 121.76(18) . . ?
C28 C29 C30 117.54(18) . . ?
C30 C29 C32 120.70(18) . . ?
C26 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C26 119.77(18) . . ?
C28 C27 H27 120.0 . . ?
C28 C27 C26 120.09(19) . . ?
C26 C27 H27 120.0 . . ?
O9 C26 C31 122.59(17) . . ?
O9 C26 C27 118.03(18) . . ?
C27 C26 C31 119.39(18) . . ?
C33 C32 C29 111.61(16) . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C29 C32 H32A 109.3 . . ?
C29 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C17 C16 C15 118.16(16) . . ?
C17 C16 H16A 107.8 . . ?
C17 C16 H16B 107.8 . . ?
C15 C16 H16A 107.8 . . ?
C15 C16 H16B 107.8 . . ?
H16A C16 H16B 107.1 . . ?
C12 C13 C14 115.21(16) . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C29 C30 H30 119.2 . . ?
C31 C30 C29 121.62(19) . . ?
C31 C30 H30 119.2 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 C11 115.12(15) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C11 C11 C10 112.65(18) 2_655 . ?
C11 C11 H11A 109.1 2_655 . ?
C11 C11 H11B 109.1 2_655 . ?
H11A C11 H11B 107.8 . . ?
O2 C9 O3 121.33(16) . . ?
O2 C9 C10 119.96(15) . . ?
O3 C9 C10 118.70(16) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C6 O1 H1 109.5 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.50(18) . . ?
H2A C2 H2B 107.6 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C3 C2 C1 114.57(17) . . ?
N1 C1 C2 111.85(16) . . ?
N1 C1 H1D 109.2 . . ?
N1 C1 H1E 109.2 . . ?
C2 C1 H1D 109.2 . . ?
C2 C1 H1E 109.2 . . ?
H1D C1 H1E 107.9 . . ?
C5 C4 H4 119.1 . . ?
C5 C4 C3 121.83(18) . . ?
C3 C4 H4 119.1 . . ?
C4 C3 C2 120.91(18) . . ?
C8 C3 C2 121.81(18) . . ?
C8 C3 C4 117.27(18) . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
C6 C7 H7 119.9 . . ?
C3 C8 H8 119.2 . . ?
C7 C8 C3 121.66(19) . . ?
C7 C8 H8 119.2 . . ?
O1 C6 C5 122.47(18) . . ?
O1 C6 C7 117.91(18) . . ?
C5 C6 C7 119.62(18) . . ?
C18 O4 H4A 109.5 . . ?
H2C N2 H2D 109.5 . . ?
H2C N2 H2E 109.5 . . ?
H2D N2 H2E 109.5 . . ?
C25 N2 H2C 109.5 . . ?
C25 N2 H2D 109.5 . . ?
C25 N2 H2E 109.5 . . ?
O4 C18 C23 118.22(17) . . ?
O4 C18 C19 122.35(16) . . ?
C19 C18 C23 119.43(17) . . ?
C23 C22 H22 119.1 . . ?
C23 C22 C21 121.85(18) . . ?
C21 C22 H22 119.1 . . ?
C18 C23 H23 120.3 . . ?
C22 C23 C18 119.49(19) . . ?
C22 C23 H23 120.3 . . ?
N2 C25 H25A 109.2 . . ?
N2 C25 H25B 109.2 . . ?
N2 C25 C24 111.96(15) . . ?
H25A C25 H25B 107.9 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.10(17) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.61(19) . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C24 121.52(17) . . ?
C20 C21 C22 117.51(18) . . ?
C20 C21 C24 120.93(18) . . ?
C25 C24 C21 110.88(16) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?

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
O8 C17 C16 C15 169.00(17) . . . . ?
O7 C17 C16 C15 -9.0(3) . . . . ?
O5 C12 C13 C14 170.16(18) . . . . ?
O6 C12 C13 C14 -9.9(3) . . . . ?
N3 C33 C32 C29 -171.88(16) . . . . ?
C28 C29 C32 C33 -119.2(2) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C28 C27 C26 O9 178.87(18) . . . . ?
C28 C27 C26 C31 -0.6(3) . . . . ?
C15 C14 C13 C12 -166.56(18) . . . . ?
C14 C15 C16 C17 -164.23(18) . . . . ?
C29 C28 C27 C26 -0.7(3) . . . . ?
C27 C28 C29 C32 -177.86(18) . . . . ?
C27 C28 C29 C30 1.2(3) . . . . ?
C26 C31 C30 C29 -0.9(3) . . . . ?
C32 C29 C30 C31 178.67(18) . . . . ?
C16 C15 C14 C13 -179.61(18) . . . . ?
C30 C29 C32 C33 61.8(2) . . . . ?
C30 C31 C26 O9 -178.07(18) . . . . ?
C30 C31 C26 C27 1.4(3) . . . . ?
C11 C10 C9 O2 -7.2(3) . . . . ?
C11 C10 C9 O3 171.96(16) . . . . ?
C9 C10 C11 C11 179.67(19) . . . 2_655 ?
C5 C4 C3 C2 -179.25(19) . . . . ?
C5 C4 C3 C8 0.2(3) . . . . ?
C2 C3 C8 C7 179.4(2) . . . . ?
C1 C2 C3 C4 -70.0(2) . . . . ?
C1 C2 C3 C8 110.6(2) . . . . ?
C4 C5 C6 O1 -179.19(19) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C3 C2 C1 N1 -73.3(2) . . . . ?
C8 C7 C6 O1 179.3(2) . . . . ?
C8 C7 C6 C5 -1.0(3) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C6 C7 C8 C3 0.4(4) . . . . ?
O4 C18 C23 C22 178.09(17) . . . . ?
O4 C18 C19 C20 -177.86(17) . . . . ?
N2 C25 C24 C21 -177.66(16) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C22 C21 C24 C25 -62.8(3) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?
C23 C22 C21 C20 0.4(3) . . . . ?
C23 C22 C21 C24 178.15(19) . . . . ?
C19 C18 C23 C22 -1.2(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C19 C20 C21 C24 -177.96(18) . . . . ?
C20 C21 C24 C25 114.9(2) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id ADP-2TYRAMINE
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_pd030921a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344733'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ADP-2MAFSALT
_chemical_formula_moiety         '2(C7 H11 N2 O2 S), 2(C3 O2)'
_chemical_formula_sum            'C20 H22 N4 O8 S2'
_chemical_formula_weight         510.53
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4623(3)
_cell_length_b                   5.9160(2)
_cell_length_c                   20.1437(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.9680(10)
_cell_angle_gamma                90
_cell_volume                     1204.49(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9032
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      31.68
_cell_measurement_theta_min      3.26
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.3697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1299 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.4954.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_preparation       'Methanol solution'
_exptl_crystal_recrystallization_method 'slow evaporation in beaker'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16545
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.704
_diffrn_reflns_theta_min         3.264
_diffrn_ambient_temperature      147.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3313
_reflns_number_total             3967
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0839P)²+1.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1671
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Others
 Fixed Sof: C10(0.4885) C11(0.5115)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.62872(4) 0.79980(8) 0.81464(2) 0.02021(14) Uani 1 1 d . . . . .
O4 O 0.16695(12) 0.3241(2) 0.52805(7) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.58804(15) 0.8676(3) 0.87477(7) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.23717(14) 0.0637(2) 0.46654(7) 0.0252(3) Uani 1 1 d . . . . .
O1 O 0.72355(14) 0.9402(3) 0.79350(7) 0.0319(3) Uani 1 1 d . . . . .
N2 N 0.10000(14) 0.7682(2) 0.53002(7) 0.0179(3) Uani 1 1 d . . . . .
H2A H 0.145109 0.870459 0.511026 0.027 Uiso 1 1 calc R U . . .
H2B H 0.014546 0.761183 0.504487 0.027 Uiso 1 1 calc R U . . .
H2C H 0.138297 0.629760 0.530928 0.027 Uiso 1 1 calc R U . . .
N1 N 0.67480(17) 0.5418(3) 0.82562(8) 0.0265(3) Uani 1 1 d . . . . .
H1A H 0.751040 0.499915 0.818712 0.032 Uiso 1 1 calc R U . . .
H1B H 0.623911 0.441615 0.838581 0.032 Uiso 1 1 calc R U . . .
C1 C 0.24616(16) 0.2558(3) 0.49401(8) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.24025(17) 0.8193(3) 0.64949(9) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.27642(18) 0.6245(3) 0.68897(9) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.217080 0.500132 0.683125 0.025 Uiso 1 1 calc R U . . .
C4 C 0.48510(17) 0.7940(3) 0.74523(8) 0.0184(3) Uani 1 1 d . . . . .
C5 C 0.10338(17) 0.8393(3) 0.60159(9) 0.0200(3) Uani 1 1 d . . . . .
H5A H 0.041377 0.743987 0.619050 0.024 Uiso 1 1 calc R U . . .
H5B H 0.073173 0.997984 0.601055 0.024 Uiso 1 1 calc R U . . .
C6 C 0.33011(18) 0.9985(3) 0.65685(9) 0.0215(3) Uani 1 1 d . . . . .
H6 H 0.307150 1.129670 0.629111 0.026 Uiso 1 1 calc R U . . .
C7 C 0.39881(18) 0.6110(3) 0.73685(9) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.423206 0.478045 0.763566 0.026 Uiso 1 1 calc R U . . .
C8 C 0.45308(18) 0.9863(3) 0.70456(9) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.514188 1.107766 0.709227 0.026 Uiso 1 1 calc R U . . .
C9 C 0.35747(19) 0.4152(4) 0.48955(12) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.4438(4) 0.3516(7) 0.4495(2) 0.0247(7) Uani 0.4885 1 d . . P A 1
C11 C 0.4538(4) 0.4618(7) 0.55432(19) 0.0286(8) Uani 0.5115 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4407(14) . ?
S1 O1 1.4402(15) . ?
S1 N1 1.5989(18) . ?
S1 C4 1.7687(17) . ?
O4 C1 1.270(2) . ?
O3 C1 1.257(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C5 1.493(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C1 C9 1.519(2) . ?
C2 C3 1.396(2) . ?
C2 C5 1.511(2) . ?
C2 C6 1.400(2) . ?
C3 H3 0.9500 . ?
C3 C7 1.392(3) . ?
C4 C7 1.392(2) . ?
C4 C8 1.392(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.408(4) . ?
C9 C11 1.454(4) . ?

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
O2 S1 N1 107.08(9) . . ?
O2 S1 C4 107.15(8) . . ?
O1 S1 O2 117.61(10) . . ?
O1 S1 N1 112.67(10) . . ?
O1 S1 C4 106.68(8) . . ?
N1 S1 C4 104.77(9) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 N2 H2A 109.5 . . ?
C5 N2 H2B 109.5 . . ?
C5 N2 H2C 109.5 . . ?
S1 N1 H1A 120.0 . . ?
S1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O4 C1 C9 116.86(16) . . ?
O3 C1 O4 122.67(15) . . ?
O3 C1 C9 120.43(16) . . ?
C3 C2 C5 120.09(15) . . ?
C3 C2 C6 119.31(16) . . ?
C6 C2 C5 120.56(15) . . ?
C2 C3 H3 119.8 . . ?
C7 C3 C2 120.49(16) . . ?
C7 C3 H3 119.8 . . ?
C7 C4 S1 120.21(13) . . ?
C7 C4 C8 120.97(16) . . ?
C8 C4 S1 118.40(13) . . ?
N2 C5 C2 112.14(14) . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C2 C5 H5A 109.2 . . ?
C2 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C2 C6 H6 119.7 . . ?
C8 C6 C2 120.58(16) . . ?
C8 C6 H6 119.7 . . ?
C3 C7 H7 120.3 . . ?
C4 C7 C3 119.43(16) . . ?
C4 C7 H7 120.3 . . ?
C4 C8 C6 119.13(16) . . ?
C4 C8 H8 120.4 . . ?
C6 C8 H8 120.4 . . ?
C10 C9 C1 118.9(2) . . ?
C11 C9 C1 115.4(2) . . ?

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
S1 C4 C7 C3 169.82(14) . . . . ?
S1 C4 C8 C6 -169.79(14) . . . . ?
O4 C1 C9 C10 -176.9(3) . . . . ?
O4 C1 C9 C11 65.0(3) . . . . ?
O2 S1 C4 C7 -79.33(16) . . . . ?
O2 S1 C4 C8 93.30(16) . . . . ?
O3 C1 C9 C10 5.1(3) . . . . ?
O3 C1 C9 C11 -113.1(3) . . . . ?
O1 S1 C4 C7 153.88(15) . . . . ?
O1 S1 C4 C8 -33.48(17) . . . . ?
N1 S1 C4 C7 34.20(17) . . . . ?
N1 S1 C4 C8 -153.17(15) . . . . ?
C2 C3 C7 C4 0.1(3) . . . . ?
C2 C6 C8 C4 -0.5(3) . . . . ?
C3 C2 C5 N2 -94.59(19) . . . . ?
C3 C2 C6 C8 -1.9(3) . . . . ?
C5 C2 C3 C7 -175.35(16) . . . . ?
C5 C2 C6 C8 175.51(16) . . . . ?
C6 C2 C3 C7 2.1(3) . . . . ?
C6 C2 C5 N2 88.0(2) . . . . ?
C7 C4 C8 C6 2.8(3) . . . . ?
C8 C4 C7 C3 -2.6(3) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id ADP-2MAF
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_pd020224_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344730'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-02-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        C16MAF
_chemical_formula_moiety         'C7 H11 N2 O2 S, C8 H14 O2, C8 H15 O2'
_chemical_formula_sum            'C23 H40 N2 O6 S'
_chemical_formula_weight         472.63
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8262(16)
_cell_length_b                   9.250(3)
_cell_length_c                   24.521(7)
_cell_angle_alpha                79.998(8)
_cell_angle_beta                 88.376(9)
_cell_angle_gamma                80.227(9)
_cell_volume                     1282.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    295.75
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1249 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.6892.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_preparation       'Methanol DCM mixture'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14756
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      295.75
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4316
_reflns_number_total             6313
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6313
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.1055
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+4.4435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2621
_refine_ls_wR_factor_ref         0.2829
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 H4-O4
 1 with sigma of 0.02
 H22B-C22B
 0.9 with sigma of 0.02
3. Others
 Fixed Sof: C23A(0.53781) H23A(0.53781) C22A(0.53781) H22A(0.53781)
 C20B(0.53781) H20B(0.53781) C21B(0.53781) H21B(0.53781) C22B(0.46219)
 H22B(0.46219) C23B(0.46219) H23B(0.46219) C20A(0.46219) H20A(0.46219)
 C21A(0.46219) H21A(0.46219)
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C13(H13A,H13B), C12(H12A,H12B), C3(H3A,H3B), C9(H9A,H9B),
 C6(H6A,H6B), C7(H7A,H7B), C5(H5A,H5B), C2(H2D,H2E), C10(H10A,H10B), C11(H11A,
 H11B), C4(H4A,H4B), C1(H1C,H1D), C14(H14A,H14B), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C23A(H23A), C22A(H22A), C20B(H20B), C21B(H21B), C23B(H23B), C20A(H20A),
 C21A(H21A)
4.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
4.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.5309(2) 0.32938(12) 0.91211(5) 0.0397(3) Uani 1 1 d . . . . .
O2 O 0.2913(6) 0.3383(4) 0.92864(17) 0.0563(10) Uani 1 1 d . . . . .
O6 O 0.5908(7) -0.3223(4) 0.82129(16) 0.0586(10) Uani 1 1 d . . . . .
O1 O 0.6728(7) 0.4088(4) 0.93842(16) 0.0585(10) Uani 1 1 d . . . . .
N2 N 1.0043(6) -0.3674(4) 0.88515(17) 0.0412(9) Uani 1 1 d . . . . .
H2A H 1.097931 -0.311728 0.865360 0.049 Uiso 1 1 calc R U . . .
H2B H 0.869594 -0.355836 0.867358 0.049 Uiso 1 1 calc R U . . .
H2C H 1.071066 -0.462679 0.889852 0.049 Uiso 1 1 calc R U . . .
O5 O 0.2515(7) -0.1740(4) 0.81630(19) 0.0682(12) Uani 1 1 d . . . . .
O3 O 0.2765(9) 0.2011(5) 0.80167(18) 0.0770(13) Uani 1 1 d . . . . .
O4 O 0.0162(8) 0.0860(5) 0.7721(2) 0.0769(13) Uani 1 1 d D . . . .
C19 C 0.6547(7) 0.1395(4) 0.92099(16) 0.0313(8) Uani 1 1 d . . . . .
N1 N 0.5525(9) 0.3813(5) 0.84679(17) 0.0573(12) Uani 1 1 d . . . . .
H1A H 0.638978 0.446183 0.834099 0.069 Uiso 1 1 calc R U . . .
H1B H 0.477677 0.344378 0.824331 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8528(8) -0.1585(5) 0.93309(19) 0.0392(10) Uani 1 1 d . . . . .
C8 C 0.4537(9) -0.2086(5) 0.8002(2) 0.0462(11) Uani 1 1 d . . . . .
C17 C 0.9611(9) -0.3205(5) 0.9402(2) 0.0483(12) Uani 1 1 d . . . . .
H17A H 1.107049 -0.336353 0.960154 0.058 Uiso 1 1 calc R U . . .
H17B H 0.857971 -0.380529 0.961678 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3107(10) 0.3664(6) 0.6667(2) 0.0570(14) Uani 1 1 d . . . . .
H13A H 0.413416 0.281152 0.686599 0.068 Uiso 1 1 calc R U . . .
H13B H 0.217420 0.330216 0.641486 0.068 Uiso 1 1 calc R U . . .
C16 C 0.1068(11) 0.2059(6) 0.7745(2) 0.0562(13) Uani 1 1 d . . . . .
C12 C 0.4577(10) 0.4716(6) 0.6331(2) 0.0536(13) Uani 1 1 d . . . . .
H12A H 0.354018 0.556269 0.613133 0.064 Uiso 1 1 calc R U . . .
H12B H 0.548557 0.508599 0.658512 0.064 Uiso 1 1 calc R U . . .
C3 C 1.1018(10) -0.0132(6) 0.5922(2) 0.0570(13) Uani 1 1 d . . . . .
H3A H 0.977371 0.041878 0.567667 0.068 Uiso 1 1 calc R U . . .
H3B H 1.158601 0.056984 0.611421 0.068 Uiso 1 1 calc R U . . .
C9 C 0.9291(10) 0.4454(6) 0.5168(2) 0.0555(13) Uani 1 1 d . . . . .
H9A H 0.840671 0.406587 0.491398 0.067 Uiso 1 1 calc R U . . .
H9B H 1.035879 0.362207 0.536693 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7286(11) -0.1743(6) 0.7160(2) 0.0570(14) Uani 1 1 d . . . . .
H6A H 0.673575 -0.251552 0.700382 0.068 Uiso 1 1 calc R U . . .
H6B H 0.862038 -0.220597 0.739303 0.068 Uiso 1 1 calc R U . . .
C7 C 0.5376(11) -0.1043(6) 0.7512(2) 0.0589(14) Uani 1 1 d . . . . .
H7A H 0.404944 -0.059391 0.727461 0.071 Uiso 1 1 calc R U . . .
H7B H 0.592810 -0.024666 0.765318 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8037(10) -0.0612(6) 0.6695(2) 0.0556(13) Uani 1 1 d . . . . .
H5A H 0.852296 0.018101 0.685159 0.067 Uiso 1 1 calc R U . . .
H5B H 0.671266 -0.017752 0.645527 0.067 Uiso 1 1 calc R U . . .
C2 C 1.2962(11) -0.0799(6) 0.5580(2) 0.0579(14) Uani 1 1 d . . . . .
H2D H 1.236980 -0.146201 0.537383 0.069 Uiso 1 1 calc R U . . .
H2E H 1.416819 -0.139354 0.582716 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7631(10) 0.5113(6) 0.5578(2) 0.0555(13) Uani 1 1 d . . . . .
H10A H 0.655810 0.594020 0.537868 0.067 Uiso 1 1 calc R U . . .
H10B H 0.851559 0.550814 0.583009 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6223(10) 0.4030(6) 0.5918(2) 0.0554(13) Uani 1 1 d . . . . .
H11A H 0.532309 0.363968 0.566803 0.066 Uiso 1 1 calc R U . . .
H11B H 0.729031 0.319877 0.611773 0.066 Uiso 1 1 calc R U . . .
C4 C 1.0018(11) -0.1277(6) 0.6350(2) 0.0589(14) Uani 1 1 d . . . . .
H4A H 0.946284 -0.198392 0.615799 0.071 Uiso 1 1 calc R U . . .
H4B H 1.126096 -0.182296 0.659692 0.071 Uiso 1 1 calc R U . . .
C1 C 1.4047(10) 0.0335(6) 0.5175(2) 0.0582(14) Uani 1 1 d . . . . .
H1C H 1.283469 0.094438 0.493327 0.070 Uiso 1 1 calc R U . . .
H1D H 1.467115 0.098396 0.538200 0.070 Uiso 1 1 calc R U . . .
C14 C 0.1496(11) 0.4389(6) 0.7080(2) 0.0633(16) Uani 1 1 d . . . . .
H14A H 0.243575 0.465127 0.735642 0.076 Uiso 1 1 calc R U . . .
H14B H 0.058911 0.530218 0.688705 0.076 Uiso 1 1 calc R U . . .
C15 C -0.0141(11) 0.3409(7) 0.7368(3) 0.0683(17) Uani 1 1 d . . . . .
H15A H -0.125060 0.398659 0.758288 0.082 Uiso 1 1 calc R U . . .
H15B H -0.100759 0.309126 0.709153 0.082 Uiso 1 1 calc R U . . .
C23A C 0.628(2) -0.1142(12) 0.9189(4) 0.039(2) Uani 0.5378 1 d . . P A 1
H23A H 0.536906 -0.184556 0.913913 0.047 Uiso 0.5378 1 calc R U P A 1
C22A C 0.5283(16) 0.0356(9) 0.9115(5) 0.0398(19) Uani 0.5378 1 d . . P A 1
H22A H 0.374129 0.064890 0.899955 0.048 Uiso 0.5378 1 calc R U P A 1
C20B C 0.8767(17) 0.1034(11) 0.9047(5) 0.046(2) Uani 0.5378 1 d . . P A 2
H20B H 0.961318 0.177128 0.889307 0.055 Uiso 0.5378 1 calc R U P A 2
C21B C 0.9767(16) -0.0457(10) 0.9114(5) 0.050(2) Uani 0.5378 1 d . . P A 2
H21B H 1.131081 -0.070969 0.901015 0.060 Uiso 0.5378 1 calc R U P A 2
C22B C 0.520(2) 0.0319(13) 0.9437(5) 0.040(2) Uani 0.4622 1 d D . P A 2
H22B H 0.376(9) 0.066(11) 0.956(4) 0.048 Uiso 0.4622 1 d D U P B 2
C23B C 0.622(2) -0.1182(13) 0.9462(5) 0.039(3) Uani 0.4622 1 d . . P A 2
H23B H 0.531572 -0.192010 0.957068 0.046 Uiso 0.4622 1 calc R U P A 2
C20A C 0.8872(16) 0.0931(10) 0.9405(5) 0.037(2) Uani 0.4622 1 d . . P A 1
H20A H 0.975767 0.162967 0.947213 0.045 Uiso 0.4622 1 calc R U P A 1
C21A C 0.9808(16) -0.0566(10) 0.9496(4) 0.0326(18) Uani 0.4622 1 d . . P A 1
H21A H 1.125919 -0.089901 0.966300 0.039 Uiso 0.4622 1 calc R U P A 1
H4 H 0.117(10) -0.006(5) 0.792(3) 0.09(2) Uiso 1 1 d 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
S1 O2 1.435(4) . ?
S1 O1 1.429(4) . ?
S1 C19 1.760(4) . ?
S1 N1 1.598(4) . ?
O6 C8 1.250(6) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C17 1.489(6) . ?
O5 C8 1.239(6) . ?
O3 C16 1.198(7) . ?
O4 C16 1.317(7) . ?
O4 H4 1.01(2) . ?
C19 C22A 1.360(10) . ?
C19 C20B 1.346(10) . ?
C19 C22B 1.403(12) . ?
C19 C20A 1.420(10) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C18 C17 1.506(6) . ?
C18 C23A 1.344(12) . ?
C18 C21B 1.391(11) . ?
C18 C23B 1.379(14) . ?
C18 C21A 1.413(10) . ?
C8 C7 1.529(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.524(7) . ?
C13 C14 1.525(7) . ?
C16 C15 1.499(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.519(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.502(7) . ?
C3 C4 1.533(7) . ?
C9 C9 1.529(10) 2_766 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.509(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.516(8) . ?
C6 C5 1.516(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.520(7) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C2 C1 1.521(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.524(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C1 C1 1.500(11) 2_856 ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.504(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C23A H23A 0.9300 . ?
C23A C22A 1.390(13) . ?
C22A H22A 0.9300 . ?
C20B H20B 0.9300 . ?
C20B C21B 1.386(13) . ?
C21B H21B 0.9300 . ?
C22B H22B 0.91(2) . ?
C22B C23B 1.407(17) . ?
C23B H23B 0.9300 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.382(13) . ?
C21A H21A 0.9300 . ?

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
O2 S1 C19 107.5(2) . . ?
O2 S1 N1 111.0(3) . . ?
O1 S1 O2 117.6(2) . . ?
O1 S1 C19 110.0(2) . . ?
O1 S1 N1 107.3(2) . . ?
N1 S1 C19 102.4(2) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C17 N2 H2A 109.5 . . ?
C17 N2 H2B 109.5 . . ?
C17 N2 H2C 109.5 . . ?
C16 O4 H4 111(4) . . ?
C22A C19 S1 121.0(4) . . ?
C22A C19 C20A 119.4(6) . . ?
C20B C19 S1 118.0(5) . . ?
C20B C19 C22B 122.6(7) . . ?
C22B C19 S1 119.4(5) . . ?
C20A C19 S1 119.6(5) . . ?
S1 N1 H1A 120.0 . . ?
S1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C23A C18 C17 120.8(6) . . ?
C23A C18 C21A 119.7(7) . . ?
C21B C18 C17 122.0(5) . . ?
C23B C18 C17 120.2(6) . . ?
C23B C18 C21B 117.8(7) . . ?
C21A C18 C17 118.8(5) . . ?
O6 C8 C7 118.7(5) . . ?
O5 C8 O6 124.2(5) . . ?
O5 C8 C7 117.1(5) . . ?
N2 C17 C18 110.3(4) . . ?
N2 C17 H17A 109.6 . . ?
N2 C17 H17B 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
H13A C13 H13B 107.7 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.4(5) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
O3 C16 O4 121.9(5) . . ?
O3 C16 C15 125.4(6) . . ?
O4 C16 C15 112.6(6) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C11 C12 C13 114.9(4) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H3A C3 H3B 107.6 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C2 C3 C4 114.1(5) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C9 C9 H9A 108.6 2_766 . ?
C9 C9 H9B 108.6 2_766 . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C9 114.5(6) . 2_766 ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C7 C6 C5 112.2(4) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C6 C7 C8 116.3(4) . . ?
C6 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C6 C5 C4 113.2(4) . . ?
H5A C5 H5B 107.8 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C3 C2 H2D 108.6 . . ?
C3 C2 H2E 108.6 . . ?
C3 C2 C1 114.5(5) . . ?
H2D C2 H2E 107.6 . . ?
C1 C2 H2D 108.6 . . ?
C1 C2 H2E 108.6 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C9 C10 C11 114.9(5) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C12 C11 C10 113.9(5) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 C3 114.4(5) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C2 C1 H1C 108.7 . . ?
C2 C1 H1D 108.7 . . ?
C1 C1 C2 114.4(6) 2_856 . ?
C1 C1 H1C 108.7 2_856 . ?
C1 C1 H1D 108.7 2_856 . ?
H1C C1 H1D 107.6 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.5(5) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C16 C15 C14 113.4(5) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C18 C23A H23A 119.6 . . ?
C18 C23A C22A 120.8(9) . . ?
C22A C23A H23A 119.6 . . ?
C19 C22A C23A 120.5(8) . . ?
C19 C22A H22A 119.7 . . ?
C23A C22A H22A 119.7 . . ?
C19 C20B H20B 120.6 . . ?
C19 C20B C21B 118.7(8) . . ?
C21B C20B H20B 120.6 . . ?
C18 C21B H21B 119.0 . . ?
C20B C21B C18 121.9(8) . . ?
C20B C21B H21B 119.0 . . ?
C19 C22B H22B 117(7) . . ?
C19 C22B C23B 116.9(10) . . ?
C23B C22B H22B 126(7) . . ?
C18 C23B C22B 121.6(10) . . ?
C18 C23B H23B 119.2 . . ?
C22B C23B H23B 119.2 . . ?
C19 C20A H20A 120.3 . . ?
C21A C20A C19 119.4(8) . . ?
C21A C20A H20A 120.3 . . ?
C18 C21A H21A 120.5 . . ?
C20A C21A C18 119.0(8) . . ?
C20A C21A H21A 120.5 . . ?

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
S1 C19 C22A C23A -179.7(8) . . . . ?
S1 C19 C20B C21B -179.9(8) . . . . ?
S1 C19 C22B C23B 175.7(8) . . . . ?
S1 C19 C20A C21A 177.4(8) . . . . ?
O2 S1 C19 C22A 35.2(7) . . . . ?
O2 S1 C19 C20B 175.9(6) . . . . ?
O2 S1 C19 C22B -3.1(7) . . . . ?
O2 S1 C19 C20A -142.2(6) . . . . ?
O6 C8 C7 C6 26.4(8) . . . . ?
O1 S1 C19 C22A 164.4(6) . . . . ?
O1 S1 C19 C20B -54.9(7) . . . . ?
O1 S1 C19 C22B 126.1(6) . . . . ?
O1 S1 C19 C20A -13.0(7) . . . . ?
O5 C8 C7 C6 -153.5(5) . . . . ?
O3 C16 C15 C14 35.3(9) . . . . ?
O4 C16 C15 C14 -140.2(6) . . . . ?
C19 C20B C21B C18 1.5(17) . . . . ?
C19 C22B C23B C18 7.3(17) . . . . ?
C19 C20A C21A C18 7.3(15) . . . . ?
N1 S1 C19 C22A -81.8(7) . . . . ?
N1 S1 C19 C20B 58.9(6) . . . . ?
N1 S1 C19 C22B -120.1(6) . . . . ?
N1 S1 C19 C20A 100.8(7) . . . . ?
C18 C23A C22A C19 -3.0(16) . . . . ?
C17 C18 C23A C22A -179.0(8) . . . . ?
C17 C18 C21B C20B 179.8(9) . . . . ?
C17 C18 C23B C22B 175.6(9) . . . . ?
C17 C18 C21A C20A 176.7(8) . . . . ?
C13 C12 C11 C10 178.6(5) . . . . ?
C13 C14 C15 C16 66.6(7) . . . . ?
C12 C13 C14 C15 173.7(5) . . . . ?
C3 C2 C1 C1 -178.7(7) . . . 2_856 ?
C9 C9 C10 C11 -179.6(6) 2_766 . . . ?
C9 C10 C11 C12 179.6(5) . . . . ?
C6 C5 C4 C3 -172.9(5) . . . . ?
C7 C6 C5 C4 177.7(5) . . . . ?
C5 C6 C7 C8 -178.6(5) . . . . ?
C2 C3 C4 C5 -179.6(5) . . . . ?
C4 C3 C2 C1 -177.0(5) . . . . ?
C14 C13 C12 C11 179.4(5) . . . . ?
C23A C18 C17 N2 75.3(8) . . . . ?
C23A C18 C21A C20A -12.6(13) . . . . ?
C22A C19 C20A C21A 0.0(14) . . . . ?
C20B C19 C22B C23B -3.3(14) . . . . ?
C21B C18 C17 N2 -69.3(8) . . . . ?
C21B C18 C23B C22B -6.8(15) . . . . ?
C22B C19 C20B C21B -1.0(14) . . . . ?
C23B C18 C17 N2 108.2(8) . . . . ?
C23B C18 C21B C20B 2.3(15) . . . . ?
C20A C19 C22A C23A -2.3(14) . . . . ?
C21A C18 C17 N2 -114.1(6) . . . . ?
C21A C18 C23A C22A 10.5(14) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dda-tyramine1_a
_database_code_depnum_ccdc_archive 'CCDC 2344731'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-02-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 O4, 2(C8 H12 N O)'
_chemical_formula_sum            'C28 H44 N2 O6'
_chemical_formula_weight         504.65
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   21.69(3)
_cell_length_b                   6.077(8)
_cell_length_c                   22.48(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2963(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3890
_cell_measurement_temperature    298.66
_cell_measurement_theta_max      20.02
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1235 before and 0.0671 after correction.
The Ratio of minimum to maximum transmission is 0.8107.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_preparation       'Methanol and DCM mixture'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24367
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.235
_diffrn_reflns_theta_max         25.235
_diffrn_reflns_theta_min         2.610
_diffrn_ambient_temperature      298.66
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                2956
_reflns_number_total             5191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5191
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+1.8610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1884
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C19, C18b, C17, C18a, C24, C27a, C27b, C28
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C24 \\sim C27a \\sim C28 \\sim C27b \\sim C17 \\sim C18a \\sim C18b \\sim C19:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C28) = Uanis(C8)
4. Others
 Fixed Sof: H19a(0.57398) H19b(0.57398) H19c(0.42602) H19d(0.42602)
 C18a(0.57398) H18a(0.57398) H18b(0.57398) C27a(0.57398) H27a(0.57398)
 H27b(0.57398) C27b(0.42602) H27c(0.42602) H27d(0.42602) C18b(0.42602)
 H18c(0.42602) H18d(0.42602) H28a(0.57398) H28b(0.57398) H28c(0.42602)
 H28d(0.42602)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C12(H12a,H12b), C13(H13a,H13b), C10(H10a,H10b), C15(H15a,H15b),
 C11(H11a,H11b), C14(H14a,H14b), C19(H19a,H19b), C19(H19c,H19d), C7(H7a,H7b),
 C16(H16a,H16b), C18a(H18a,H18b), C17(H17a,H17b), C27a(H27a,H27b), C27b(H27c,
 H27d), C18b(H18c,H18d), C28(H28a,H28b), C28(H28c,H28d)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6a), C5(H5), C22(H22), C26(H26), C23(H23), C25(H25)
5.c Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c), N2(H2a,H2b,H2c)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.3121(2) 0.6473(9) 0.3081(2) 0.0742(14) Uani 1 1 d . . . . .
O1 O 0.6688(2) -0.1889(9) 0.3812(3) 0.0811(16) Uani 1 1 d . . . . .
H1 H 0.695006 -0.099933 0.370524 0.122 Uiso 1 1 calc R U . . .
O5 O 0.6868(3) -0.1352(9) 0.6533(2) 0.0821(16) Uani 1 1 d . . . . .
O4 O 0.6449(3) -0.4338(10) 0.6149(3) 0.0906(17) Uani 1 1 d . . . . .
O3 O 0.2602(2) 0.9443(9) 0.3322(3) 0.0860(17) Uani 1 1 d . . . . .
N1 N 0.3431(2) 0.2129(9) 0.2734(3) 0.0605(15) Uani 1 1 d . . . . .
H1A H 0.334451 0.212619 0.234733 0.073 Uiso 1 1 calc R U . . .
H1B H 0.340694 0.349815 0.287343 0.073 Uiso 1 1 calc R U . . .
H1C H 0.316105 0.128171 0.292570 0.073 Uiso 1 1 calc R U . . .
O6 O 0.5654(2) 0.3649(11) 0.6890(3) 0.0953(18) Uani 1 1 d . . . . .
H6 H 0.584634 0.441108 0.665337 0.143 Uiso 1 1 calc R U . . .
C9 C 0.6686(3) -0.2430(16) 0.6090(4) 0.071(2) Uani 1 1 d . . . . .
C1 C 0.6112(3) -0.1006(12) 0.3729(3) 0.0608(18) Uani 1 1 d . . . . .
N2 N 0.2136(2) 0.7163(10) 0.6864(3) 0.0694(16) Uani 1 1 d . . . . .
H2A H 0.191878 0.618890 0.665538 0.083 Uiso 1 1 calc R U . . .
H2B H 0.203847 0.851787 0.674645 0.083 Uiso 1 1 calc R U . . .
H2C H 0.204929 0.701382 0.724898 0.083 Uiso 1 1 calc R U . . .
C8 C 0.4067(3) 0.1261(18) 0.2830(4) 0.094(2) Uani 1 1 d . . . . .
H8A H 0.435346 0.207544 0.258197 0.113 Uiso 1 1 calc R U . . .
H8B H 0.408170 -0.027045 0.270886 0.113 Uiso 1 1 calc R U . . .
C2 C 0.5607(3) -0.2238(12) 0.3913(3) 0.0664(19) Uani 1 1 d . . . . .
H2 H 0.566535 -0.360420 0.409062 0.080 Uiso 1 1 calc R U . . .
C20 C 0.2816(3) 0.7610(15) 0.3453(3) 0.0628(19) Uani 1 1 d . . . . .
C21 C 0.5051(3) 0.4297(13) 0.6898(3) 0.0646(19) Uani 1 1 d . . . . .
C3 C 0.5017(3) -0.1429(12) 0.3832(3) 0.0660(19) Uani 1 1 d . . . . .
H3 H 0.468317 -0.226948 0.395722 0.079 Uiso 1 1 calc R U . . .
C12 C 0.5693(3) 0.0341(14) 0.5466(3) 0.078(2) Uani 1 1 d . . . . .
H12A H 0.562175 0.017337 0.588915 0.093 Uiso 1 1 calc R U . . .
H12B H 0.555058 -0.098871 0.527071 0.093 Uiso 1 1 calc R U . . .
C13 C 0.5318(4) 0.2282(13) 0.5239(3) 0.073(2) Uani 1 1 d . . . . .
H13A H 0.545578 0.360908 0.543897 0.088 Uiso 1 1 calc R U . . .
H13B H 0.539409 0.246478 0.481705 0.088 Uiso 1 1 calc R U . . .
C4 C 0.4908(3) 0.0610(13) 0.3568(3) 0.0597(19) Uani 1 1 d . . . . .
C10 C 0.6749(4) -0.1512(14) 0.5471(3) 0.081(2) Uani 1 1 d . . . . .
H10A H 0.661752 -0.262512 0.518922 0.097 Uiso 1 1 calc R U . . .
H10B H 0.718078 -0.120768 0.539591 0.097 Uiso 1 1 calc R U . . .
C6 C 0.6007(3) 0.1034(13) 0.3473(3) 0.0646(19) Uani 1 1 d . . . . .
H6A H 0.634082 0.188877 0.335259 0.078 Uiso 1 1 calc R U . . .
C5 C 0.5416(3) 0.1816(13) 0.3392(3) 0.068(2) Uani 1 1 d . . . . .
H5 H 0.535748 0.318458 0.321597 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4237(4) 0.3931(15) 0.5116(4) 0.090(3) Uani 1 1 d . . . . .
H15A H 0.436893 0.526813 0.531440 0.108 Uiso 1 1 calc R U . . .
H15B H 0.430793 0.412012 0.469306 0.108 Uiso 1 1 calc R U . . .
C11 C 0.6378(4) 0.0591(13) 0.5358(4) 0.079(2) Uani 1 1 d . . . . .
H11A H 0.653460 0.174754 0.561415 0.094 Uiso 1 1 calc R U . . .
H11B H 0.644231 0.105002 0.494946 0.094 Uiso 1 1 calc R U . . .
C22 C 0.4641(4) 0.2995(16) 0.7214(4) 0.089(3) Uani 1 1 d . . . . .
H22 H 0.477974 0.172037 0.740045 0.107 Uiso 1 1 calc R U . . .
C14 C 0.4629(4) 0.2008(15) 0.5340(3) 0.085(2) Uani 1 1 d . . . . .
H14A H 0.455599 0.182114 0.576244 0.102 Uiso 1 1 calc R U . . .
H14B H 0.449462 0.067338 0.514186 0.102 Uiso 1 1 calc R U . . .
C26 C 0.4849(3) 0.6200(13) 0.6620(4) 0.074(2) Uani 1 1 d . . . . .
H26 H 0.512074 0.708352 0.640723 0.089 Uiso 1 1 calc R U . . .
C19 C 0.2705(5) 0.676(2) 0.4068(4) 0.132(4) Uani 1 1 d . U . . .
H19A H 0.268221 0.800834 0.433400 0.158 Uiso 0.574 1 calc R U P A 1
H19B H 0.230330 0.605257 0.407128 0.158 Uiso 0.574 1 calc R U P A 1
H19C H 0.261925 0.519355 0.403369 0.158 Uiso 0.426 1 calc R U P B 2
H19D H 0.233152 0.744703 0.421416 0.158 Uiso 0.426 1 calc R U P B 2
C7 C 0.4264(3) 0.1446(14) 0.3473(3) 0.070(2) Uani 1 1 d . . . . .
H7A H 0.424231 0.297455 0.359531 0.083 Uiso 1 1 calc R U . . .
H7B H 0.398156 0.061113 0.371943 0.083 Uiso 1 1 calc R U . . .
C16 C 0.3550(4) 0.3609(19) 0.5222(5) 0.115(3) Uani 1 1 d . . . . .
H16A H 0.342001 0.229072 0.501373 0.138 Uiso 1 1 calc R U . . .
H16B H 0.348548 0.335622 0.564372 0.138 Uiso 1 1 calc R U . . .
C18A C 0.3120(6) 0.531(3) 0.4298(6) 0.073(4) Uani 0.574 1 d . U P C 1
H18A H 0.352575 0.561814 0.413741 0.087 Uiso 0.574 1 calc R U P C 1
H18B H 0.300755 0.382318 0.418160 0.087 Uiso 0.574 1 calc R U P C 1
C17 C 0.3146(5) 0.546(2) 0.5033(5) 0.127(4) Uani 1 1 d . U . . .
H17A H 0.331672 0.685934 0.515851 0.152 Uiso 1 1 calc R U . C 1
H17B H 0.273611 0.530375 0.520105 0.152 Uiso 1 1 calc R U . C 1
C23 C 0.4042(4) 0.357(2) 0.7253(4) 0.127(5) Uani 1 1 d . . . . .
H23 H 0.377527 0.268538 0.747161 0.152 Uiso 1 1 calc R U . . .
C25 C 0.4228(4) 0.6758(19) 0.6667(4) 0.108(3) Uani 1 1 d . . . . .
H25 H 0.408566 0.803785 0.648635 0.129 Uiso 1 1 calc R U . . .
C24 C 0.3813(4) 0.542(3) 0.6982(5) 0.124(4) Uani 1 1 d . U . . .
C27A C 0.3071(6) 0.523(3) 0.7018(7) 0.082(4) Uani 0.574 1 d . U P D 1
H27A H 0.294326 0.385594 0.683514 0.098 Uiso 0.574 1 calc R U P D 1
H27B H 0.294771 0.518346 0.743254 0.098 Uiso 0.574 1 calc R U P D 1
C27B C 0.3222(8) 0.731(4) 0.7085(10) 0.094(6) Uani 0.426 1 d . U P D 2
H27C H 0.309240 0.731376 0.749833 0.112 Uiso 0.426 1 calc R U P D 2
H27D H 0.336360 0.877637 0.698319 0.112 Uiso 0.426 1 calc R U P D 2
C18B C 0.3192(14) 0.703(6) 0.4540(11) 0.136(8) Uani 0.426 1 d . U P C 2
H18C H 0.359476 0.687427 0.435646 0.163 Uiso 0.426 1 calc R U P C 2
H18D H 0.316512 0.851020 0.469946 0.163 Uiso 0.426 1 calc R U P C 2
C28 C 0.2797(4) 0.6782(18) 0.6768(4) 0.094(2) Uani 1 1 d . U . . .
H28A H 0.285610 0.659791 0.634278 0.113 Uiso 0.574 1 calc R U P D 1
H28B H 0.300938 0.812468 0.687904 0.113 Uiso 0.574 1 calc R U P D 1
H28C H 0.283803 0.520493 0.671448 0.113 Uiso 0.426 1 calc R U P D 2
H28D H 0.288692 0.743379 0.638336 0.113 Uiso 0.426 1 calc R U P D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C20 1.271(9) . ?
O1 H1 0.8200 . ?
O1 C1 1.372(8) . ?
O5 C9 1.257(10) . ?
O4 C9 1.275(10) . ?
O3 C20 1.243(9) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C8 1.493(9) . ?
O6 H6 0.8200 . ?
O6 C21 1.364(8) . ?
C9 C10 1.504(11) . ?
C1 C2 1.390(9) . ?
C1 C6 1.387(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C28 1.468(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.512(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(10) . ?
C20 C19 1.495(12) . ?
C21 C22 1.387(10) . ?
C21 C26 1.386(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(11) . ?
C12 C11 1.512(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.519(11) . ?
C4 C5 1.380(9) . ?
C4 C7 1.502(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.531(11) . ?
C6 H6A 0.9300 . ?
C6 C5 1.381(9) . ?
C5 H5 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.531(12) . ?
C15 C16 1.522(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C23 1.349(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C26 H26 0.9300 . ?
C26 C25 1.392(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C19 H19D 0.9700 . ?
C19 C18A 1.362(16) . ?
C19 C18B 1.51(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.489(14) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C17 1.654(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18B 1.47(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(15) . ?
C25 H25 0.9300 . ?
C25 C24 1.406(15) . ?
C24 C27A 1.615(15) . ?
C24 C27B 1.74(3) . ?
C27A H27A 0.9700 . ?
C27A H27B 0.9700 . ?
C27A C28 1.249(15) . ?
C27B H27C 0.9700 . ?
C27B H27D 0.9700 . ?
C27B C28 1.211(19) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C28 H28D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
C21 O6 H6 109.5 . . ?
O5 C9 O4 121.1(8) . . ?
O5 C9 C10 120.8(8) . . ?
O4 C9 C10 118.1(8) . . ?
O1 C1 C2 117.9(7) . . ?
O1 C1 C6 123.7(6) . . ?
C6 C1 C2 118.4(7) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C28 N2 H2A 109.5 . . ?
C28 N2 H2B 109.5 . . ?
C28 N2 H2C 109.5 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C7 111.9(6) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.0 . . ?
O2 C20 C19 120.2(9) . . ?
O3 C20 O2 121.7(7) . . ?
O3 C20 C19 118.1(9) . . ?
O6 C21 C22 117.1(7) . . ?
O6 C21 C26 122.6(7) . . ?
C26 C21 C22 120.3(7) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(6) . . ?
C4 C3 H3 119.0 . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C11 C12 C13 113.2(7) . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 113.0(7) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C3 C4 C7 121.3(7) . . ?
C5 C4 C3 117.3(6) . . ?
C5 C4 C7 121.4(7) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.6(7) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C1 C6 H6A 119.5 . . ?
C5 C6 C1 120.9(7) . . ?
C5 C6 H6A 119.5 . . ?
C4 C5 C6 121.4(7) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
H15A C15 H15B 107.7 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C16 C15 C14 113.2(8) . . ?
C12 C11 C10 113.9(7) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(9) . . ?
C23 C22 H22 119.9 . . ?
C13 C14 C15 114.4(7) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C21 C26 H26 120.8 . . ?
C21 C26 C25 118.4(8) . . ?
C25 C26 H26 120.8 . . ?
C20 C19 H19A 107.8 . . ?
C20 C19 H19B 107.8 . . ?
C20 C19 H19C 107.3 . . ?
C20 C19 H19D 107.3 . . ?
C20 C19 C18B 119.9(12) . . ?
H19A C19 H19B 107.1 . . ?
H19C C19 H19D 106.9 . . ?
C18A C19 C20 118.0(10) . . ?
C18A C19 H19A 107.8 . . ?
C18A C19 H19B 107.8 . . ?
C18B C19 H19C 107.3 . . ?
C18B C19 H19D 107.3 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C4 C7 C8 112.0(6) . . ?
C4 C7 H7A 109.2 . . ?
C4 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C15 C16 H16A 108.3 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C17 C16 C15 115.8(10) . . ?
C17 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C19 C18A H18A 109.3 . . ?
C19 C18A H18B 109.3 . . ?
C19 C18A C17 111.5(10) . . ?
H18A C18A H18B 108.0 . . ?
C17 C18A H18A 109.3 . . ?
C17 C18A H18B 109.3 . . ?
C16 C17 C18A 105.2(10) . . ?
C16 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C18A C17 H17A 110.7 . . ?
C18A C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C18B C17 C16 131.9(16) . . ?
C22 C23 H23 118.9 . . ?
C22 C23 C24 122.2(10) . . ?
C24 C23 H23 118.9 . . ?
C26 C25 H25 119.4 . . ?
C26 C25 C24 121.1(9) . . ?
C24 C25 H25 119.4 . . ?
C23 C24 C25 117.8(8) . . ?
C23 C24 C27A 106.3(12) . . ?
C23 C24 C27B 138.6(12) . . ?
C25 C24 C27A 134.8(11) . . ?
C25 C24 C27B 99.0(13) . . ?
C24 C27A H27A 108.9 . . ?
C24 C27A H27B 108.9 . . ?
H27A C27A H27B 107.7 . . ?
C28 C27A C24 113.4(12) . . ?
C28 C27A H27A 108.9 . . ?
C28 C27A H27B 108.9 . . ?
C24 C27B H27C 110.1 . . ?
C24 C27B H27D 110.1 . . ?
H27C C27B H27D 108.4 . . ?
C28 C27B C24 107.9(16) . . ?
C28 C27B H27C 110.1 . . ?
C28 C27B H27D 110.1 . . ?
C19 C18B H18C 108.7 . . ?
C19 C18B H18D 108.7 . . ?
C17 C18B C19 114(2) . . ?
C17 C18B H18C 108.7 . . ?
C17 C18B H18D 108.7 . . ?
H18C C18B H18D 107.6 . . ?
N2 C28 H28A 107.0 . . ?
N2 C28 H28B 107.0 . . ?
N2 C28 H28C 105.3 . . ?
N2 C28 H28D 105.3 . . ?
C27A C28 N2 121.1(10) . . ?
C27A C28 H28A 107.0 . . ?
C27A C28 H28B 107.0 . . ?
C27B C28 N2 128.0(13) . . ?
C27B C28 H28C 105.3 . . ?
C27B C28 H28D 105.3 . . ?
H28A C28 H28B 106.8 . . ?
H28C C28 H28D 106.0 . . ?

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
O2 C20 C19 C18A 26.8(16) . . . . ?
O2 C20 C19 C18B 83(2) . . . . ?
O1 C1 C2 C3 -179.2(7) . . . . ?
O1 C1 C6 C5 178.9(7) . . . . ?
O5 C9 C10 C11 -63.2(10) . . . . ?
O4 C9 C10 C11 117.4(8) . . . . ?
O3 C20 C19 C18A -153.4(12) . . . . ?
O3 C20 C19 C18B -97(2) . . . . ?
N1 C8 C7 C4 -179.0(7) . . . . ?
O6 C21 C22 C23 178.3(8) . . . . ?
O6 C21 C26 C25 -178.2(8) . . . . ?
C9 C10 C11 C12 -57.9(10) . . . . ?
C1 C2 C3 C4 0.0(11) . . . . ?
C1 C6 C5 C4 0.5(11) . . . . ?
C2 C1 C6 C5 -1.0(11) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C2 C3 C4 C7 178.8(7) . . . . ?
C20 C19 C18A C17 151.9(11) . . . . ?
C20 C19 C18B C17 -157.6(17) . . . . ?
C21 C22 C23 C24 0.7(15) . . . . ?
C21 C26 C25 C24 -0.7(14) . . . . ?
C3 C4 C5 C6 0.2(11) . . . . ?
C3 C4 C7 C8 -104.2(9) . . . . ?
C12 C13 C14 C15 -179.9(7) . . . . ?
C13 C12 C11 C10 -168.9(7) . . . . ?
C6 C1 C2 C3 0.7(11) . . . . ?
C5 C4 C7 C8 75.1(9) . . . . ?
C15 C16 C17 C18A 74.6(12) . . . . ?
C15 C16 C17 C18B 33(2) . . . . ?
C11 C12 C13 C14 179.1(7) . . . . ?
C22 C21 C26 C25 -0.1(12) . . . . ?
C22 C23 C24 C25 -1.5(17) . . . . ?
C22 C23 C24 C27A 168.2(11) . . . . ?
C22 C23 C24 C27B -151.4(15) . . . . ?
C14 C15 C16 C17 178.0(8) . . . . ?
C26 C21 C22 C23 0.1(13) . . . . ?
C26 C25 C24 C23 1.5(16) . . . . ?
C26 C25 C24 C27A -164.6(13) . . . . ?
C26 C25 C24 C27B 161.8(10) . . . . ?
C19 C18A C17 C16 172.8(11) . . . . ?
C7 C4 C5 C6 -179.1(7) . . . . ?
C16 C15 C14 C13 180.0(7) . . . . ?
C16 C17 C18B C19 112(2) . . . . ?
C23 C24 C27A C28 -177.7(13) . . . . ?
C23 C24 C27B C28 -98(2) . . . . ?
C25 C24 C27A C28 -11(2) . . . . ?
C25 C24 C27B C28 108.4(17) . . . . ?
C24 C27A C28 N2 -166.4(9) . . . . ?
C24 C27B C28 N2 150.8(11) . . . . ?

# end Validation Reply Form
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT340_dda-tyramine1_a     
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01213 Ang.  
RESPONSE: The data was collected several times from different sets of crystal
but the problem persists. 
;
####################################################################### 
# 
# 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_nr040324_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344729'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-03-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ddaamn
_chemical_formula_moiety         'C12 H21 O4, C10 H18 N'
_chemical_formula_sum            'C22 H39 N O4'
_chemical_formula_weight         381.54
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.657(4)
_cell_length_b                   13.210(7)
_cell_length_c                   13.286(7)
_cell_angle_alpha                106.992(8)
_cell_angle_beta                 91.051(8)
_cell_angle_gamma                96.242(8)
_cell_volume                     1109.2(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1894
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0888 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8631.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_preparation       'methanol solution'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9011
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.605
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2464
_reflns_number_total             3863
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.0788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00z), C00E(H2), C00I(H4)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00u,H00v), C009(H00w,H00x), C00A(H00y,H), C00C(H00,Ha), C00F(H00a,H00b),
  C00G(H00c,H00d), C00H(H3,Hb), C00J(H00e,H00f), C00K(H00g,H00h), C00L(H00i,
 H00j), C00M(H00k,H00l), C00N(H00m,H00n), C00O(H00o,H00p), C00P(H00q,H00r),
 C00Q(H5,Hc), C00R(H00s,H00t)
2.c Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.0913(2) 1.06988(11) 0.70420(11) 0.0496(4) Uani 1 1 d . . . . .
O002 O 0.3613(2) 1.00718(11) 0.62892(11) 0.0473(4) Uani 1 1 d . . . . .
N1 N 0.7482(2) 0.96401(12) 0.56992(13) 0.0398(4) Uani 1 1 d . . . . .
H1A H 0.638429 0.985183 0.603217 0.060 Uiso 1 1 calc R U . . .
H1B H 0.743444 0.973235 0.506228 0.060 Uiso 1 1 calc R U . . .
H1C H 0.858147 1.002272 0.606718 0.060 Uiso 1 1 calc R U . . .
O004 O 0.7519(3) 0.22813(15) 0.71845(16) 0.0856(6) Uani 1 1 d . . . . .
O1 O 1.0175(3) 0.25425(16) 0.82677(16) 0.0969(7) Uani 1 1 d . . . . .
H1 H 1.028624 0.192676 0.792467 0.145 Uiso 1 1 calc R U . . .
C1 C 0.7560(3) 0.84794(14) 0.55911(15) 0.0357(5) Uani 1 1 d . . . . .
C007 C 0.2725(3) 1.05130(14) 0.70882(16) 0.0382(5) Uani 1 1 d . . . . .
C008 C 0.9415(3) 0.81171(16) 0.50081(16) 0.0431(5) Uani 1 1 d . . . . .
H00U H 1.062662 0.853689 0.539252 0.052 Uiso 1 1 calc R U . . .
H00V H 0.935308 0.821951 0.431490 0.052 Uiso 1 1 calc R U . . .
C009 C 0.7672(3) 0.83429(16) 0.66862(16) 0.0452(5) Uani 1 1 d . . . . .
H00W H 0.648811 0.857923 0.705890 0.054 Uiso 1 1 calc R U . . .
H00X H 0.886387 0.877102 0.708356 0.054 Uiso 1 1 calc R U . . .
C00A C 0.5657(3) 0.78283(16) 0.49742(18) 0.0473(5) Uani 1 1 d . . . . .
H00Y H 0.557453 0.792616 0.427959 0.057 Uiso 1 1 calc R U . . .
H H 0.446548 0.806572 0.533812 0.057 Uiso 1 1 calc R U . . .
C00B C 0.9494(3) 0.69382(17) 0.49016(18) 0.0501(6) Uani 1 1 d . . . . .
H00Z H 1.069348 0.670294 0.452642 0.060 Uiso 1 1 calc R U . . .
C00C C 0.9619(3) 0.67907(18) 0.59939(18) 0.0567(6) Uani 1 1 d . . . . .
H00 H 0.968528 0.604523 0.593218 0.068 Uiso 1 1 calc R U . . .
HA H 1.083589 0.720084 0.638131 0.068 Uiso 1 1 calc R U . . .
C00D C 0.8611(4) 0.2855(2) 0.79001(19) 0.0580(6) Uani 1 1 d . . . . .
C00E C 0.7771(3) 0.71593(17) 0.65835(18) 0.0551(6) Uani 1 1 d . . . . .
H2 H 0.784929 0.706180 0.728602 0.066 Uiso 1 1 calc R U . . .
C00F C 0.2946(3) 0.91073(17) 0.86057(17) 0.0528(6) Uani 1 1 d . . . . .
H00A H 0.244514 0.878699 0.787917 0.063 Uiso 1 1 calc R U . . .
H00B H 0.436655 0.901057 0.864359 0.063 Uiso 1 1 calc R U . . .
C00G C 0.3791(3) 1.08482(18) 0.81714(16) 0.0521(6) Uani 1 1 d . . . . .
H00C H 0.382433 1.161332 0.847386 0.063 Uiso 1 1 calc R U . . .
H00D H 0.517710 1.068597 0.810309 0.063 Uiso 1 1 calc R U . . .
C00H C 0.7594(3) 0.62795(18) 0.42805(19) 0.0589(6) Uani 1 1 d . . . . .
H3 H 0.751756 0.637182 0.358340 0.071 Uiso 1 1 calc R U . . .
HB H 0.764356 0.552926 0.420198 0.071 Uiso 1 1 calc R U . . .
C00I C 0.5745(3) 0.66516(17) 0.48741(19) 0.0555(6) Uani 1 1 d . . . . .
H4 H 0.451974 0.622946 0.448495 0.067 Uiso 1 1 calc R U . . .
C00J C 0.2767(4) 1.02968(18) 0.89108(17) 0.0569(6) Uani 1 1 d . . . . .
H00E H 0.134602 1.039875 0.892068 0.068 Uiso 1 1 calc R U . . .
H00F H 0.336265 1.062971 0.961840 0.068 Uiso 1 1 calc R U . . .
C00K C 0.6197(4) 0.54978(18) 0.8793(2) 0.0613(6) Uani 1 1 d . . . . .
H00G H 0.654968 0.567566 0.954132 0.074 Uiso 1 1 calc R U . . .
H00H H 0.717943 0.591038 0.849470 0.074 Uiso 1 1 calc R U . . .
C00L C 0.4148(4) 0.58222(18) 0.86553(19) 0.0594(6) Uani 1 1 d . . . . .
H00I H 0.318125 0.544520 0.899667 0.071 Uiso 1 1 calc R U . . .
H00J H 0.375512 0.559852 0.790907 0.071 Uiso 1 1 calc R U . . .
C00M C 0.4012(3) 0.70045(18) 0.90915(19) 0.0586(6) Uani 1 1 d . . . . .
H00K H 0.441212 0.723047 0.983684 0.070 Uiso 1 1 calc R U . . .
H00L H 0.496816 0.738235 0.874599 0.070 Uiso 1 1 calc R U . . .
C00N C 0.1810(4) 0.85167(19) 0.92872(19) 0.0625(7) Uani 1 1 d . . . . .
H00M H 0.039738 0.863310 0.926893 0.075 Uiso 1 1 calc R U . . .
H00N H 0.234348 0.881989 1.001008 0.075 Uiso 1 1 calc R U . . .
C00O C 0.1935(4) 0.73216(19) 0.8955(2) 0.0612(6) Uani 1 1 d . . . . .
H00O H 0.100913 0.700000 0.936167 0.073 Uiso 1 1 calc R U . . .
H00P H 0.147730 0.702744 0.821965 0.073 Uiso 1 1 calc R U . . .
C00P C 0.6358(4) 0.43254(19) 0.8290(2) 0.0637(7) Uani 1 1 d . . . . .
H00Q H 0.535363 0.391215 0.857659 0.076 Uiso 1 1 calc R U . . .
H00R H 0.603738 0.415106 0.753956 0.076 Uiso 1 1 calc R U . . .
C00Q C 0.5873(3) 0.65035(18) 0.5967(2) 0.0648(7) Uani 1 1 d . . . . .
H5 H 0.591317 0.575572 0.590420 0.078 Uiso 1 1 calc R U . . .
HC H 0.468425 0.672893 0.634085 0.078 Uiso 1 1 calc R U . . .
C00R C 0.8381(4) 0.40006(19) 0.8450(2) 0.0701(7) Uani 1 1 d . . . . .
H00S H 0.866034 0.413469 0.919988 0.084 Uiso 1 1 calc R U . . .
H00T H 0.939242 0.444864 0.820731 0.084 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
O001 C007 1.261(2) . ?
O002 C007 1.246(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.504(2) . ?
O004 C00D 1.200(3) . ?
O1 H1 0.8200 . ?
O1 C00D 1.299(3) . ?
C1 C008 1.517(3) . ?
C1 C009 1.519(3) . ?
C1 C00A 1.526(3) . ?
C007 C00G 1.514(3) . ?
C008 H00U 0.9700 . ?
C008 H00V 0.9700 . ?
C008 C00B 1.529(3) . ?
C009 H00W 0.9700 . ?
C009 H00X 0.9700 . ?
C009 C00E 1.538(3) . ?
C00A H00Y 0.9700 . ?
C00A H 0.9700 . ?
C00A C00I 1.529(3) . ?
C00B H00Z 0.9800 . ?
C00B C00C 1.522(3) . ?
C00B C00H 1.530(3) . ?
C00C H00 0.9700 . ?
C00C HA 0.9700 . ?
C00C C00E 1.519(3) . ?
C00D C00R 1.502(3) . ?
C00E H2 0.9800 . ?
C00E C00Q 1.525(3) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00F C00J 1.523(3) . ?
C00F C00N 1.520(3) . ?
C00G H00C 0.9700 . ?
C00G H00D 0.9700 . ?
C00G C00J 1.515(3) . ?
C00H H3 0.9700 . ?
C00H HB 0.9700 . ?
C00H C00I 1.523(3) . ?
C00I H4 0.9800 . ?
C00I C00Q 1.523(3) . ?
C00J H00E 0.9700 . ?
C00J H00F 0.9700 . ?
C00K H00G 0.9700 . ?
C00K H00H 0.9700 . ?
C00K C00L 1.497(3) . ?
C00K C00P 1.513(3) . ?
C00L H00I 0.9700 . ?
C00L H00J 0.9700 . ?
C00L C00M 1.512(3) . ?
C00M H00K 0.9700 . ?
C00M H00L 0.9700 . ?
C00M C00O 1.510(3) . ?
C00N H00M 0.9700 . ?
C00N H00N 0.9700 . ?
C00N C00O 1.522(3) . ?
C00O H00O 0.9700 . ?
C00O H00P 0.9700 . ?
C00P H00Q 0.9700 . ?
C00P H00R 0.9700 . ?
C00P C00R 1.487(3) . ?
C00Q H5 0.9700 . ?
C00Q HC 0.9700 . ?
C00R H00S 0.9700 . ?
C00R H00T 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C00D O1 H1 109.5 . . ?
N1 C1 C008 109.32(15) . . ?
N1 C1 C009 108.57(15) . . ?
N1 C1 C00A 109.28(14) . . ?
C008 C1 C009 110.06(15) . . ?
C008 C1 C00A 109.62(17) . . ?
C009 C1 C00A 109.97(16) . . ?
O001 C007 C00G 116.73(18) . . ?
O002 C007 O001 122.34(18) . . ?
O002 C007 C00G 120.93(18) . . ?
C1 C008 H00U 109.8 . . ?
C1 C008 H00V 109.8 . . ?
C1 C008 C00B 109.22(16) . . ?
H00U C008 H00V 108.3 . . ?
C00B C008 H00U 109.8 . . ?
C00B C008 H00V 109.8 . . ?
C1 C009 H00W 109.9 . . ?
C1 C009 H00X 109.9 . . ?
C1 C009 C00E 108.93(16) . . ?
H00W C009 H00X 108.3 . . ?
C00E C009 H00W 109.9 . . ?
C00E C009 H00X 109.9 . . ?
C1 C00A H00Y 109.9 . . ?
C1 C00A H 109.9 . . ?
C1 C00A C00I 108.89(16) . . ?
H00Y C00A H 108.3 . . ?
C00I C00A H00Y 109.9 . . ?
C00I C00A H 109.9 . . ?
C008 C00B H00Z 109.3 . . ?
C008 C00B C00H 109.53(17) . . ?
C00C C00B C008 109.30(17) . . ?
C00C C00B H00Z 109.3 . . ?
C00C C00B C00H 109.97(19) . . ?
C00H C00B H00Z 109.3 . . ?
C00B C00C H00 109.7 . . ?
C00B C00C HA 109.7 . . ?
H00 C00C HA 108.2 . . ?
C00E C00C C00B 109.70(17) . . ?
C00E C00C H00 109.7 . . ?
C00E C00C HA 109.7 . . ?
O004 C00D O1 122.5(2) . . ?
O004 C00D C00R 125.0(2) . . ?
O1 C00D C00R 112.5(2) . . ?
C009 C00E H2 109.7 . . ?
C00C C00E C009 109.73(18) . . ?
C00C C00E H2 109.7 . . ?
C00C C00E C00Q 109.1(2) . . ?
C00Q C00E C009 108.99(18) . . ?
C00Q C00E H2 109.7 . . ?
H00A C00F H00B 107.6 . . ?
C00J C00F H00A 108.6 . . ?
C00J C00F H00B 108.6 . . ?
C00N C00F H00A 108.6 . . ?
C00N C00F H00B 108.6 . . ?
C00N C00F C00J 114.65(18) . . ?
C007 C00G H00C 109.1 . . ?
C007 C00G H00D 109.1 . . ?
C007 C00G C00J 112.61(18) . . ?
H00C C00G H00D 107.8 . . ?
C00J C00G H00C 109.1 . . ?
C00J C00G H00D 109.1 . . ?
C00B C00H H3 109.9 . . ?
C00B C00H HB 109.9 . . ?
H3 C00H HB 108.3 . . ?
C00I C00H C00B 108.74(18) . . ?
C00I C00H H3 109.9 . . ?
C00I C00H HB 109.9 . . ?
C00A C00I H4 109.3 . . ?
C00H C00I C00A 109.54(18) . . ?
C00H C00I H4 109.3 . . ?
C00Q C00I C00A 109.64(19) . . ?
C00Q C00I C00H 109.67(19) . . ?
C00Q C00I H4 109.3 . . ?
C00F C00J H00E 108.9 . . ?
C00F C00J H00F 108.9 . . ?
C00G C00J C00F 113.40(18) . . ?
C00G C00J H00E 108.9 . . ?
C00G C00J H00F 108.9 . . ?
H00E C00J H00F 107.7 . . ?
H00G C00K H00H 107.6 . . ?
C00L C00K H00G 108.6 . . ?
C00L C00K H00H 108.6 . . ?
C00L C00K C00P 114.5(2) . . ?
C00P C00K H00G 108.6 . . ?
C00P C00K H00H 108.6 . . ?
C00K C00L H00I 108.6 . . ?
C00K C00L H00J 108.6 . . ?
C00K C00L C00M 114.7(2) . . ?
H00I C00L H00J 107.6 . . ?
C00M C00L H00I 108.6 . . ?
C00M C00L H00J 108.6 . . ?
C00L C00M H00K 108.7 . . ?
C00L C00M H00L 108.7 . . ?
H00K C00M H00L 107.6 . . ?
C00O C00M C00L 114.3(2) . . ?
C00O C00M H00K 108.7 . . ?
C00O C00M H00L 108.7 . . ?
C00F C00N H00M 108.7 . . ?
C00F C00N H00N 108.7 . . ?
C00F C00N C00O 114.42(19) . . ?
H00M C00N H00N 107.6 . . ?
C00O C00N H00M 108.7 . . ?
C00O C00N H00N 108.7 . . ?
C00M C00O C00N 115.2(2) . . ?
C00M C00O H00O 108.5 . . ?
C00M C00O H00P 108.5 . . ?
C00N C00O H00O 108.5 . . ?
C00N C00O H00P 108.5 . . ?
H00O C00O H00P 107.5 . . ?
C00K C00P H00Q 108.7 . . ?
C00K C00P H00R 108.7 . . ?
H00Q C00P H00R 107.6 . . ?
C00R C00P C00K 114.3(2) . . ?
C00R C00P H00Q 108.7 . . ?
C00R C00P H00R 108.7 . . ?
C00E C00Q H5 109.7 . . ?
C00E C00Q HC 109.7 . . ?
C00I C00Q C00E 109.90(19) . . ?
C00I C00Q H5 109.7 . . ?
C00I C00Q HC 109.7 . . ?
H5 C00Q HC 108.2 . . ?
C00D C00R H00S 108.5 . . ?
C00D C00R H00T 108.5 . . ?
C00P C00R C00D 115.1(2) . . ?
C00P C00R H00S 108.5 . . ?
C00P C00R H00T 108.5 . . ?
H00S C00R H00T 107.5 . . ?

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
O001 C007 C00G C00J 60.6(2) . . . . ?
O002 C007 C00G C00J -119.1(2) . . . . ?
N1 C1 C008 C00B 179.86(15) . . . . ?
N1 C1 C009 C00E -179.51(15) . . . . ?
N1 C1 C00A C00I -179.68(16) . . . . ?
O004 C00D C00R C00P 17.9(4) . . . . ?
O1 C00D C00R C00P -163.6(2) . . . . ?
C1 C008 C00B C00C -60.2(2) . . . . ?
C1 C008 C00B C00H 60.3(2) . . . . ?
C1 C009 C00E C00C 59.2(2) . . . . ?
C1 C009 C00E C00Q -60.2(2) . . . . ?
C1 C00A C00I C00H -60.8(2) . . . . ?
C1 C00A C00I C00Q 59.6(2) . . . . ?
C007 C00G C00J C00F 68.5(2) . . . . ?
C008 C1 C009 C00E -59.9(2) . . . . ?
C008 C1 C00A C00I 60.5(2) . . . . ?
C008 C00B C00C C00E 60.0(2) . . . . ?
C008 C00B C00H C00I -60.4(2) . . . . ?
C009 C1 C008 C00B 60.7(2) . . . . ?
C009 C1 C00A C00I -60.6(2) . . . . ?
C009 C00E C00Q C00I 60.0(2) . . . . ?
C00A C1 C008 C00B -60.4(2) . . . . ?
C00A C1 C009 C00E 61.0(2) . . . . ?
C00A C00I C00Q C00E -60.0(2) . . . . ?
C00B C00C C00E C009 -59.7(2) . . . . ?
C00B C00C C00E C00Q 59.7(2) . . . . ?
C00B C00H C00I C00A 60.7(2) . . . . ?
C00B C00H C00I C00Q -59.6(2) . . . . ?
C00C C00B C00H C00I 59.8(2) . . . . ?
C00C C00E C00Q C00I -59.8(2) . . . . ?
C00F C00N C00O C00M 66.8(3) . . . . ?
C00H C00B C00C C00E -60.2(2) . . . . ?
C00H C00I C00Q C00E 60.3(2) . . . . ?
C00J C00F C00N C00O 178.03(19) . . . . ?
C00K C00L C00M C00O -179.5(2) . . . . ?
C00K C00P C00R C00D -176.3(2) . . . . ?
C00L C00K C00P C00R -178.6(2) . . . . ?
C00L C00M C00O C00N -174.1(2) . . . . ?
C00N C00F C00J C00G -175.90(19) . . . . ?
C00P C00K C00L C00M -176.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nr120522_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344732'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-07-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        DDA-2TRYPT
_chemical_formula_moiety         'C12 H20 O4, 2(C10 H13 N2)'
_chemical_formula_sum            'C32 H46 N4 O4'
_chemical_formula_weight         550.73
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4847(19)
_cell_length_b                   7.741(2)
_cell_length_c                   16.693(5)
_cell_angle_alpha                91.501(4)
_cell_angle_beta                 98.704(4)
_cell_angle_gamma                108.733(4)
_cell_volume                     781.9(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.46
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             298
_exptl_crystal_preparation       METHANOL
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12445
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.574
_diffrn_reflns_theta_min         2.477
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1680
_reflns_number_total             2934
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.0415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C7(H7A,H7B), C1(H1D,H1E), C2(H2A,H2B),
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C13(H13), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.0368(2) 0.8718(2) 0.61080(8) 0.0524(4) Uani 1 1 d . . . . .
O1 O 0.2937(2) 0.8013(2) 0.55873(9) 0.0599(5) Uani 1 1 d . . . . .
N1 N 0.6758(3) 0.8335(2) 0.49234(10) 0.0442(5) Uani 1 1 d . . . . .
H1A H 0.685039 0.937909 0.469656 0.053 Uiso 1 1 calc R U . . .
H1B H 0.795170 0.850013 0.529812 0.053 Uiso 1 1 calc R U . . .
H1C H 0.555714 0.798481 0.515574 0.053 Uiso 1 1 calc R U . . .
N2 N 0.1693(3) 0.9364(3) 0.29749(11) 0.0526(5) Uani 1 1 d . . . . .
H2 H 0.086610 1.003076 0.300033 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1780(3) 0.7919(3) 0.61330(12) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.3481(3) 0.7387(3) 0.33225(13) 0.0425(5) Uani 1 1 d . . . . .
C4 C 0.1017(3) 0.7045(3) 0.75615(12) 0.0429(5) Uani 1 1 d . . . . .
H4A H -0.055938 0.674096 0.737788 0.051 Uiso 1 1 calc R U . . .
H4B H 0.159164 0.832120 0.776831 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2097(3) 0.6803(3) 0.68424(12) 0.0432(5) Uani 1 1 d . . . . .
H5A H 0.366994 0.710575 0.703267 0.052 Uiso 1 1 calc R U . . .
H5B H 0.152995 0.551961 0.664614 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2784(3) 0.9237(3) 0.23445(13) 0.0474(6) Uani 1 1 d . . . . .
C12 C 0.3936(3) 0.8001(3) 0.25476(13) 0.0444(6) Uani 1 1 d . . . . .
C3 C 0.1389(4) 0.5874(3) 0.82495(12) 0.0488(6) Uani 1 1 d . . . . .
H3A H 0.082514 0.459777 0.804180 0.059 Uiso 1 1 calc R U . . .
H3B H 0.296498 0.618456 0.843632 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2132(3) 0.8261(3) 0.35559(13) 0.0476(6) Uani 1 1 d . . . . .
H10 H 0.158459 0.812766 0.404254 0.057 Uiso 1 1 calc R U . . .
C7 C 0.6618(3) 0.6898(3) 0.42876(13) 0.0469(6) Uani 1 1 d . . . . .
H7A H 0.707425 0.593971 0.454427 0.056 Uiso 1 1 calc R U . . .
H7B H 0.763218 0.742967 0.391938 0.056 Uiso 1 1 calc R U . . .
C1 C 0.0598(4) 0.4913(3) 0.96514(12) 0.0572(7) Uani 1 1 d . . . . .
H1D H 0.216345 0.523418 0.986137 0.069 Uiso 1 1 calc R U . . .
H1E H 0.007214 0.364543 0.943259 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0289(4) 0.6107(3) 0.89674(12) 0.0543(6) Uani 1 1 d . . . . .
H2A H 0.088027 0.737818 0.918155 0.065 Uiso 1 1 calc R U . . .
H2B H -0.128008 0.582763 0.877631 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4310(4) 0.6067(3) 0.38049(14) 0.0538(6) Uani 1 1 d . . . . .
H8A H 0.429068 0.507062 0.343580 0.065 Uiso 1 1 calc R U . . .
H8B H 0.330234 0.555150 0.417737 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5191(4) 0.7617(3) 0.19944(15) 0.0610(7) Uani 1 1 d . . . . .
H13 H 0.597686 0.681320 0.211137 0.073 Uiso 1 1 calc R U . . .
C16 C 0.2855(4) 1.0070(4) 0.16185(15) 0.0652(7) Uani 1 1 d . . . . .
H16 H 0.208916 1.088588 0.149458 0.078 Uiso 1 1 calc R U . . .
C15 C 0.4074(5) 0.9661(4) 0.10929(16) 0.0799(9) Uani 1 1 d . . . . .
H15 H 0.413015 1.020046 0.060177 0.096 Uiso 1 1 calc R U . . .
C14 C 0.5239(5) 0.8453(4) 0.12745(17) 0.0796(9) Uani 1 1 d . . . . .
H14 H 0.606454 0.820540 0.090428 0.096 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
O2 C6 1.256(2) . ?
O1 C6 1.254(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.489(2) . ?
N2 H2 0.8600 . ?
N2 C11 1.372(3) . ?
N2 C10 1.366(3) . ?
C6 C5 1.512(3) . ?
C9 C12 1.429(3) . ?
C9 C10 1.358(3) . ?
C9 C8 1.499(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.514(3) . ?
C4 C3 1.520(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C12 1.410(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.404(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.519(3) . ?
C10 H10 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.514(3) . ?
C1 C1 1.519(4) 2_567 ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.361(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(4) . ?
C14 H14 0.9300 . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
C11 N2 H2 125.5 . . ?
C10 N2 H2 125.5 . . ?
C10 N2 C11 109.06(17) . . ?
O2 C6 C5 119.04(17) . . ?
O1 C6 O2 122.12(19) . . ?
O1 C6 C5 118.83(17) . . ?
C12 C9 C8 128.34(19) . . ?
C10 C9 C12 106.22(19) . . ?
C10 C9 C8 125.4(2) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C5 C4 C3 113.60(16) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C6 C5 C4 116.43(16) . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
N2 C11 C12 106.94(18) . . ?
N2 C11 C16 131.1(2) . . ?
C16 C11 C12 122.0(2) . . ?
C11 C12 C9 107.37(18) . . ?
C13 C12 C9 134.2(2) . . ?
C13 C12 C11 118.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 C4 113.52(17) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
N2 C10 H10 124.8 . . ?
C9 C10 N2 110.41(19) . . ?
C9 C10 H10 124.8 . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
N1 C7 C8 112.45(17) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C1 C1 H1D 108.8 2_567 . ?
C1 C1 H1E 108.8 2_567 . ?
H1D C1 H1E 107.7 . . ?
C2 C1 C1 113.9(2) . 2_567 ?
C2 C1 H1D 108.8 . . ?
C2 C1 H1E 108.8 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 C3 114.22(18) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C9 C8 C7 114.33(19) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C11 C16 H16 120.9 . . ?
C15 C16 C11 118.2(2) . . ?
C15 C16 H16 120.9 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C5 C4 -12.2(3) . . . . ?
O1 C6 C5 C4 167.88(19) . . . . ?
N1 C7 C8 C9 63.5(2) . . . . ?
N2 C11 C12 C9 0.3(2) . . . . ?
N2 C11 C12 C13 179.65(19) . . . . ?
N2 C11 C16 C15 -179.1(2) . . . . ?
C9 C12 C13 C14 178.8(2) . . . . ?
C4 C3 C2 C1 178.6(2) . . . . ?
C5 C4 C3 C2 -179.54(19) . . . . ?
C11 N2 C10 C9 -0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 C16 C15 C14 -0.5(4) . . . . ?
C12 C9 C10 N2 0.7(2) . . . . ?
C12 C9 C8 C7 81.1(3) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C3 C4 C5 C6 179.62(18) . . . . ?
C10 N2 C11 C12 0.1(2) . . . . ?
C10 N2 C11 C16 179.5(2) . . . . ?
C10 C9 C12 C11 -0.6(2) . . . . ?
C10 C9 C12 C13 -179.8(2) . . . . ?
C10 C9 C8 C7 -98.1(3) . . . . ?
C1 C1 C2 C3 -177.2(2) 2_567 . . . ?
C8 C9 C12 C11 -180.0(2) . . . . ?
C8 C9 C12 C13 0.8(4) . . . . ?
C8 C9 C10 N2 -179.92(19) . . . . ?
C16 C11 C12 C9 -179.2(2) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C16 C15 C14 C13 0.3(4) . . . . ?

_olex2_exptl_crystal_mounting_method LOOP
_olex2_submission_original_sample_id DDA-2TRYPT
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nr290622_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344735'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ADP-2TRYPTSALT
_chemical_formula_moiety         'C6 H8 O4, 2(C10 H13 N2)'
_chemical_formula_sum            'C26 H34 N4 O4'
_chemical_formula_weight         466.57
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.788(6)
_cell_length_b                   6.098(4)
_cell_length_c                   21.090(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.993(9)
_cell_angle_gamma                90
_cell_volume                     1249.3(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5874
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.84
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1166 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.9387.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_preparation       'methanol solution'
_exptl_crystal_recrystallization_method 'slow evaporation in beaker'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.946
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1878
_reflns_number_total             2211
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.3101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1D,H1E), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C8(H8), C11(H11), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O2 O 0.72653(11) 1.07154(17) 0.32633(5) 0.0512(3) Uani 1 1 d . . . . .
O1 O 0.85423(12) 0.78488(18) 0.35114(6) 0.0637(4) Uani 1 1 d . . . . .
N1 N 0.65971(12) 0.49409(19) 0.29722(5) 0.0390(3) Uani 1 1 d . . . . .
H1A H 0.682570 0.358136 0.309690 0.058 Uiso 1 1 calc R U . . .
H1B H 0.723043 0.587354 0.315033 0.058 Uiso 1 1 calc R U . . .
H1C H 0.654979 0.502917 0.254884 0.058 Uiso 1 1 calc R U . . .
N2 N 0.43490(12) 0.98667(19) 0.15407(6) 0.0436(3) Uani 1 1 d . . . . .
H2 H 0.469238 1.108750 0.143093 0.052 Uiso 1 1 calc R U . . .
C6 C 0.40052(13) 0.6868(2) 0.21155(7) 0.0347(3) Uani 1 1 d . . . . .
C3 C 0.81049(13) 0.9692(2) 0.36461(6) 0.0348(3) Uani 1 1 d . . . . .
C12 C 0.30502(13) 0.6849(2) 0.15435(6) 0.0363(3) Uani 1 1 d . . . . .
C13 C 0.32941(14) 0.8745(2) 0.11935(7) 0.0383(3) Uani 1 1 d . . . . .
C7 C 0.47655(14) 0.8728(2) 0.20897(7) 0.0393(3) Uani 1 1 d . . . . .
H7 H 0.546846 0.916360 0.240097 0.047 Uiso 1 1 calc R U . . .
C2 C 0.86188(15) 1.0698(2) 0.42844(6) 0.0405(4) Uani 1 1 d . . . . .
H2A H 0.785159 1.080582 0.453372 0.049 Uiso 1 1 calc R U . . .
H2B H 0.892951 1.217755 0.421243 0.049 Uiso 1 1 calc R U . . .
C1 C 0.97802(15) 0.9471(2) 0.46770(6) 0.0400(3) Uani 1 1 d . . . . .
H1D H 1.056658 0.940750 0.443854 0.048 Uiso 1 1 calc R U . . .
H1E H 0.948633 0.797778 0.474327 0.048 Uiso 1 1 calc R U . . .
C4 C 0.52290(15) 0.5509(3) 0.31746(7) 0.0451(4) Uani 1 1 d . . . . .
H4A H 0.524718 0.702194 0.331790 0.054 Uiso 1 1 calc R U . . .
H4B H 0.506580 0.458898 0.353285 0.054 Uiso 1 1 calc R U . . .
C5 C 0.40574(15) 0.5217(2) 0.26439(7) 0.0453(4) Uani 1 1 d . . . . .
H5A H 0.412670 0.376565 0.246207 0.054 Uiso 1 1 calc R U . . .
H5B H 0.319658 0.528140 0.282746 0.054 Uiso 1 1 calc R U . . .
C8 C 0.25176(17) 0.9241(3) 0.06127(8) 0.0528(4) Uani 1 1 d . . . . .
H8 H 0.269449 1.049135 0.038373 0.063 Uiso 1 1 calc R U . . .
C11 C 0.19816(17) 0.5440(3) 0.13012(8) 0.0526(4) Uani 1 1 d . . . . .
H11 H 0.179485 0.418250 0.152472 0.063 Uiso 1 1 calc R U . . .
C9 C 0.14801(19) 0.7814(3) 0.03907(8) 0.0657(5) Uani 1 1 d . . . . .
H9 H 0.094424 0.810852 0.000508 0.079 Uiso 1 1 calc R U . . .
C10 C 0.12154(19) 0.5933(3) 0.07326(9) 0.0678(5) Uani 1 1 d . . . . .
H10 H 0.050617 0.499897 0.057108 0.081 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
O2 C3 1.2469(17) . ?
O1 C3 1.2478(18) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C4 1.495(2) . ?
N2 H2 0.8600 . ?
N2 C13 1.3734(19) . ?
N2 C7 1.369(2) . ?
C6 C12 1.433(2) . ?
C6 C7 1.361(2) . ?
C6 C5 1.498(2) . ?
C3 C2 1.509(2) . ?
C12 C13 1.407(2) . ?
C12 C11 1.401(2) . ?
C13 C8 1.394(2) . ?
C7 H7 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.519(2) . ?
C1 C1 1.522(3) 3_776 ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.512(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C9 1.375(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.396(3) . ?
C10 H10 0.9300 . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
C13 N2 H2 125.5 . . ?
C7 N2 H2 125.5 . . ?
C7 N2 C13 108.99(12) . . ?
C12 C6 C5 125.46(12) . . ?
C7 C6 C12 106.07(12) . . ?
C7 C6 C5 128.35(13) . . ?
O2 C3 O1 121.38(13) . . ?
O2 C3 C2 119.74(12) . . ?
O1 C3 C2 118.88(12) . . ?
C13 C12 C6 107.44(12) . . ?
C11 C12 C6 133.89(14) . . ?
C11 C12 C13 118.63(14) . . ?
N2 C13 C12 107.10(13) . . ?
N2 C13 C8 130.88(14) . . ?
C8 C13 C12 122.00(14) . . ?
N2 C7 H7 124.8 . . ?
C6 C7 N2 110.39(12) . . ?
C6 C7 H7 124.8 . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C3 C2 C1 115.60(12) . . ?
H2A C2 H2B 107.4 . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C2 C1 C1 112.97(15) . 3_776 ?
C2 C1 H1D 109.0 . . ?
C2 C1 H1E 109.0 . . ?
C1 C1 H1D 109.0 3_776 . ?
C1 C1 H1E 109.0 3_776 . ?
H1D C1 H1E 107.8 . . ?
N1 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
N1 C4 C5 112.72(13) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C5 C4 115.17(12) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C13 C8 H8 121.2 . . ?
C9 C8 C13 117.57(16) . . ?
C9 C8 H8 121.2 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.35(16) . . ?
C10 C11 H11 120.3 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.32(16) . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 121.13(16) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C2 C1 -171.93(13) . . . . ?
O1 C3 C2 C1 7.5(2) . . . . ?
N1 C4 C5 C6 -71.13(17) . . . . ?
N2 C13 C8 C9 -177.74(16) . . . . ?
C6 C12 C13 N2 -0.22(15) . . . . ?
C6 C12 C13 C8 -178.94(13) . . . . ?
C6 C12 C11 C10 178.02(16) . . . . ?
C3 C2 C1 C1 -178.19(15) . . . 3_776 ?
C12 C6 C7 N2 -0.01(15) . . . . ?
C12 C6 C5 C4 175.75(13) . . . . ?
C12 C13 C8 C9 0.6(2) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C13 N2 C7 C6 -0.12(16) . . . . ?
C13 C12 C11 C10 0.5(2) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 N2 C13 C12 0.21(15) . . . . ?
C7 N2 C13 C8 178.78(15) . . . . ?
C7 C6 C12 C13 0.14(15) . . . . ?
C7 C6 C12 C11 -177.62(16) . . . . ?
C7 C6 C5 C4 -8.7(2) . . . . ?
C5 C6 C12 C13 176.51(13) . . . . ?
C5 C6 C12 C11 -1.2(2) . . . . ?
C5 C6 C7 N2 -176.24(13) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C11 C12 C13 N2 177.94(13) . . . . ?
C11 C12 C13 C8 -0.8(2) . . . . ?

_olex2_exptl_crystal_mounting_method loop
_olex2_submission_original_sample_id ADP-2TRYPT
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nr01036_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2344734'
loop_
_audit_author_name
_audit_author_address
'NABANITA ROY'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        AZELAIC-2AMN
_chemical_formula_moiety         'C9 H14 O4, 2(C10 H18 N)'
_chemical_formula_sum            'C29 H50 N2 O4'
_chemical_formula_weight         490.71
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   20.775(19)
_cell_length_b                   6.448(6)
_cell_length_c                   21.727(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.79(3)
_cell_angle_gamma                90
_cell_volume                     2884(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.03
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1890 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.8925.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_preparation       METHANOL
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            42335
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.633
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2934
_reflns_number_total             5273
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0086(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+0.7486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C28(H28), C26(H26), C17(H17), C24(H24), C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C13(H13A,H13B), C18(H18A,H18B), C21(H21A,H21B), C20(H20A,
 H20B), C10(H10A,H10B), C25(H25A,H25B), C8(H8A,H8B), C27(H27A,H27B), C29(H29A,
 H29B), C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C12(H12A,H12B), C5(H5A,H5B),
 C3(H3A,H3B), C16(H16A,H16B), C4(H4A,H4B), C2(H2D,H2E)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O3 O 0.46324(9) 0.5385(3) 0.67984(9) 0.0527(5) Uani 1 1 d . . . . .
O2 O 0.07410(9) -0.3692(3) 0.73330(9) 0.0551(5) Uani 1 1 d . . . . .
N2 N 0.94478(11) 0.5439(3) 0.72722(10) 0.0478(6) Uani 1 1 d . . . . .
H2A H 0.987882 0.550552 0.730266 0.057 Uiso 1 1 calc R U . . .
H2B H 0.933099 0.419302 0.739401 0.057 Uiso 1 1 calc R U . . .
H2C H 0.930559 0.640775 0.751266 0.057 Uiso 1 1 calc R U . . .
O1 O 0.09655(11) -0.6703(3) 0.69002(10) 0.0727(7) Uani 1 1 d . . . . .
O4 O 0.41839(10) 0.8226(3) 0.63291(11) 0.0685(6) Uani 1 1 d . . . . .
N1 N 0.50277(10) 0.1244(3) 0.68730(10) 0.0473(6) Uani 1 1 d . . . . .
H1A H 0.474993 0.024680 0.673209 0.057 Uiso 1 1 calc R U . . .
H1B H 0.483679 0.247393 0.680520 0.057 Uiso 1 1 calc R U . . .
H1C H 0.514808 0.107305 0.727874 0.057 Uiso 1 1 calc R U . . .
C19 C 0.56054(12) 0.1141(4) 0.65460(12) 0.0415(6) Uani 1 1 d . . . . .
C23 C 0.91459(12) 0.5810(4) 0.65832(12) 0.0411(7) Uani 1 1 d . . . . .
C1 C 0.42207(14) 0.6311(4) 0.64017(13) 0.0484(7) Uani 1 1 d . . . . .
C9 C 0.10178(13) -0.4795(5) 0.69530(14) 0.0511(7) Uani 1 1 d . . . . .
C22 C 0.93763(14) 0.7889(4) 0.63507(13) 0.0485(7) Uani 1 1 d . . . . .
H22A H 0.984621 0.788647 0.637841 0.058 Uiso 1 1 calc R U . . .
H22B H 0.925183 0.900137 0.661111 0.058 Uiso 1 1 calc R U . . .
C13 C 0.58922(14) -0.1020(4) 0.66541(14) 0.0502(7) Uani 1 1 d . . . . .
H13A H 0.600968 -0.126825 0.709534 0.060 Uiso 1 1 calc R U . . .
H13B H 0.557692 -0.205821 0.648988 0.060 Uiso 1 1 calc R U . . .
C18 C 0.60729(13) 0.2800(4) 0.68392(13) 0.0492(7) Uani 1 1 d . . . . .
H18A H 0.587680 0.416463 0.678466 0.059 Uiso 1 1 calc R U . . .
H18B H 0.618983 0.254179 0.728001 0.059 Uiso 1 1 calc R U . . .
C21 C 0.93228(14) 0.4063(4) 0.61423(13) 0.0523(8) Uani 1 1 d . . . . .
H21A H 0.916780 0.274484 0.627912 0.063 Uiso 1 1 calc R U . . .
H21B H 0.979154 0.397828 0.616434 0.063 Uiso 1 1 calc R U . . .
C28 C 0.90636(15) 0.8283(4) 0.56470(13) 0.0533(8) Uani 1 1 d . . . . .
H28 H 0.921687 0.961770 0.550741 0.064 Uiso 1 1 calc R U . . .
C20 C 0.84328(13) 0.5862(4) 0.65603(15) 0.0560(8) Uani 1 1 d . . . . .
H20A H 0.830867 0.695336 0.682796 0.067 Uiso 1 1 calc R U . . .
H20B H 0.827845 0.454943 0.670238 0.067 Uiso 1 1 calc R U . . .
C10 C 0.54257(15) 0.1522(5) 0.58179(13) 0.0552(8) Uani 1 1 d . . . . .
H10A H 0.511000 0.049540 0.564652 0.066 Uiso 1 1 calc R U . . .
H10B H 0.522916 0.288133 0.574833 0.066 Uiso 1 1 calc R U . . .
C26 C 0.90117(15) 0.4475(4) 0.54401(14) 0.0561(8) Uani 1 1 d . . . . .
H26 H 0.913134 0.334909 0.517452 0.067 Uiso 1 1 calc R U . . .
C17 C 0.66622(14) 0.2658(5) 0.65069(14) 0.0590(8) Uani 1 1 d . . . . .
H17 H 0.698169 0.369383 0.668024 0.071 Uiso 1 1 calc R U . . .
C24 C 0.81240(15) 0.6279(5) 0.58634(15) 0.0612(8) Uani 1 1 d . . . . .
H24 H 0.765017 0.632061 0.584428 0.073 Uiso 1 1 calc R U . . .
C25 C 0.83051(16) 0.4539(5) 0.54206(16) 0.0664(9) Uani 1 1 d . . . . .
H25A H 0.814913 0.321138 0.554933 0.080 Uiso 1 1 calc R U . . .
H25B H 0.810174 0.481482 0.499986 0.080 Uiso 1 1 calc R U . . .
C15 C 0.64830(15) -0.1147(5) 0.63290(15) 0.0611(8) Uani 1 1 d . . . . .
H15 H 0.668270 -0.251747 0.640163 0.073 Uiso 1 1 calc R U . . .
C8 C 0.37240(16) 0.4939(5) 0.60066(15) 0.0648(9) Uani 1 1 d . . . . .
H8A H 0.394251 0.403782 0.574344 0.078 Uiso 1 1 calc R U . . .
H8B H 0.341635 0.579326 0.574299 0.078 Uiso 1 1 calc R U . . .
C27 C 0.92437(16) 0.6548(4) 0.52088(14) 0.0592(8) Uani 1 1 d . . . . .
H27A H 0.903747 0.680805 0.478809 0.071 Uiso 1 1 calc R U . . .
H27B H 0.971037 0.651620 0.520757 0.071 Uiso 1 1 calc R U . . .
C29 C 0.83552(15) 0.8362(4) 0.56308(15) 0.0615(9) Uani 1 1 d . . . . .
H29A H 0.814912 0.861807 0.520981 0.074 Uiso 1 1 calc R U . . .
H29B H 0.823847 0.947891 0.589349 0.074 Uiso 1 1 calc R U . . .
C11 C 0.60187(16) 0.1388(5) 0.54868(15) 0.0631(9) Uani 1 1 d . . . . .
H11 H 0.590079 0.164061 0.504097 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29134(15) 0.2072(5) 0.61127(15) 0.0660(9) Uani 1 1 d . . . . .
H6A H 0.315441 0.114125 0.587762 0.079 Uiso 1 1 calc R U . . .
H6B H 0.258845 0.277567 0.582371 0.079 Uiso 1 1 calc R U . . .
C7 C 0.33654(16) 0.3629(5) 0.64485(16) 0.0684(9) Uani 1 1 d . . . . .
H7A H 0.368319 0.291163 0.674133 0.082 Uiso 1 1 calc R U . . .
H7B H 0.311996 0.454701 0.668330 0.082 Uiso 1 1 calc R U . . .
C14 C 0.69546(15) 0.0502(5) 0.66173(17) 0.0680(9) Uani 1 1 d . . . . .
H14A H 0.735574 0.041709 0.643640 0.082 Uiso 1 1 calc R U . . .
H14B H 0.705560 0.025520 0.706022 0.082 Uiso 1 1 calc R U . . .
C12 C 0.64894(16) 0.3038(5) 0.57741(15) 0.0689(9) Uani 1 1 d . . . . .
H12A H 0.629576 0.439890 0.569973 0.083 Uiso 1 1 calc R U . . .
H12B H 0.688391 0.299182 0.558142 0.083 Uiso 1 1 calc R U . . .
C5 C 0.25787(16) 0.0821(5) 0.65832(16) 0.0725(10) Uani 1 1 d . . . . .
H5A H 0.290734 0.017510 0.688199 0.087 Uiso 1 1 calc R U . . .
H5B H 0.232849 0.175721 0.680767 0.087 Uiso 1 1 calc R U . . .
C3 C 0.18020(17) -0.1967(5) 0.67632(17) 0.0740(10) Uani 1 1 d . . . . .
H3A H 0.212872 -0.250113 0.708552 0.089 Uiso 1 1 calc R U . . .
H3B H 0.153216 -0.099898 0.695491 0.089 Uiso 1 1 calc R U . . .
C16 C 0.63100(18) -0.0775(5) 0.55990(16) 0.0724(10) Uani 1 1 d . . . . .
H16A H 0.669945 -0.089715 0.540081 0.087 Uiso 1 1 calc R U . . .
H16B H 0.600112 -0.181198 0.542120 0.087 Uiso 1 1 calc R U . . .
C4 C 0.21409(18) -0.0810(5) 0.62752(17) 0.0774(10) Uani 1 1 d . . . . .
H4A H 0.239092 -0.178371 0.606330 0.093 Uiso 1 1 calc R U . . .
H4B H 0.181707 -0.017823 0.596843 0.093 Uiso 1 1 calc R U . . .
C2 C 0.1396(2) -0.3699(5) 0.64894(18) 0.0840(11) Uani 1 1 d . . . . .
H2D H 0.167236 -0.470369 0.632062 0.101 Uiso 1 1 calc R U . . .
H2E H 0.109040 -0.317282 0.614804 0.101 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
O3 C1 1.277(3) . ?
O2 C9 1.283(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C23 1.561(4) . ?
O1 C9 1.239(4) . ?
O4 C1 1.246(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C19 1.477(3) . ?
C19 C13 1.521(4) . ?
C19 C18 1.525(4) . ?
C19 C10 1.594(4) . ?
C23 C22 1.532(4) . ?
C23 C21 1.555(4) . ?
C23 C20 1.476(4) . ?
C1 C8 1.531(4) . ?
C9 C2 1.532(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C28 1.598(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C15 1.499(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.506(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C26 1.596(4) . ?
C28 H28 0.9800 . ?
C28 C27 1.547(4) . ?
C28 C29 1.468(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C24 1.585(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(4) . ?
C26 H26 0.9800 . ?
C26 C25 1.463(5) . ?
C26 C27 1.529(4) . ?
C17 H17 0.9800 . ?
C17 C14 1.523(4) . ?
C17 C12 1.603(5) . ?
C24 H24 0.9800 . ?
C24 C25 1.557(4) . ?
C24 C29 1.535(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C15 H15 0.9800 . ?
C15 C14 1.522(4) . ?
C15 C16 1.596(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.544(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C12 1.520(4) . ?
C11 C16 1.527(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.496(4) . ?
C6 C5 1.540(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.489(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.542(4) . ?
C3 C2 1.475(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C23 N2 H2A 109.5 . . ?
C23 N2 H2B 109.5 . . ?
C23 N2 H2C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C19 N1 H1A 109.5 . . ?
C19 N1 H1B 109.5 . . ?
C19 N1 H1C 109.5 . . ?
N1 C19 C13 107.1(2) . . ?
N1 C19 C18 106.3(2) . . ?
N1 C19 C10 112.0(2) . . ?
C13 C19 C18 111.4(2) . . ?
C13 C19 C10 109.2(2) . . ?
C18 C19 C10 110.9(2) . . ?
C22 C23 N2 110.3(2) . . ?
C22 C23 C21 108.7(2) . . ?
C21 C23 N2 112.5(2) . . ?
C20 C23 N2 107.9(2) . . ?
C20 C23 C22 109.0(2) . . ?
C20 C23 C21 108.4(2) . . ?
O3 C1 C8 116.6(3) . . ?
O4 C1 O3 124.9(3) . . ?
O4 C1 C8 118.5(3) . . ?
O2 C9 C2 118.8(3) . . ?
O1 C9 O2 124.6(3) . . ?
O1 C9 C2 116.3(3) . . ?
C23 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
C23 C22 C28 110.5(2) . . ?
H22A C22 H22B 108.1 . . ?
C28 C22 H22A 109.6 . . ?
C28 C22 H22B 109.6 . . ?
C19 C13 H13A 110.1 . . ?
C19 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
C15 C13 C19 107.8(2) . . ?
C15 C13 H13A 110.1 . . ?
C15 C13 H13B 110.1 . . ?
C19 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
C17 C18 C19 105.7(2) . . ?
C17 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C23 C21 H21A 109.3 . . ?
C23 C21 H21B 109.3 . . ?
C23 C21 C26 111.7(2) . . ?
H21A C21 H21B 107.9 . . ?
C26 C21 H21A 109.3 . . ?
C26 C21 H21B 109.3 . . ?
C22 C28 H28 109.2 . . ?
C27 C28 C22 111.9(2) . . ?
C27 C28 H28 109.2 . . ?
C29 C28 C22 107.7(2) . . ?
C29 C28 H28 109.2 . . ?
C29 C28 C27 109.6(3) . . ?
C23 C20 H20A 110.1 . . ?
C23 C20 H20B 110.1 . . ?
C23 C20 C24 108.1(2) . . ?
H20A C20 H20B 108.4 . . ?
C24 C20 H20A 110.1 . . ?
C24 C20 H20B 110.1 . . ?
C19 C10 H10A 109.3 . . ?
C19 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C19 111.5(2) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C21 C26 H26 109.7 . . ?
C25 C26 C21 107.9(3) . . ?
C25 C26 H26 109.7 . . ?
C25 C26 C27 109.0(2) . . ?
C27 C26 C21 110.8(2) . . ?
C27 C26 H26 109.7 . . ?
C18 C17 H17 109.1 . . ?
C18 C17 C14 108.2(2) . . ?
C18 C17 C12 112.3(2) . . ?
C14 C17 H17 109.1 . . ?
C14 C17 C12 109.1(3) . . ?
C12 C17 H17 109.1 . . ?
C20 C24 H24 108.6 . . ?
C25 C24 C20 111.6(2) . . ?
C25 C24 H24 108.6 . . ?
C29 C24 C20 111.0(3) . . ?
C29 C24 H24 108.6 . . ?
C29 C24 C25 108.3(3) . . ?
C26 C25 C24 109.2(3) . . ?
C26 C25 H25A 109.8 . . ?
C26 C25 H25B 109.8 . . ?
C24 C25 H25A 109.8 . . ?
C24 C25 H25B 109.8 . . ?
H25A C25 H25B 108.3 . . ?
C13 C15 H15 109.2 . . ?
C13 C15 C14 106.9(2) . . ?
C13 C15 C16 111.8(3) . . ?
C14 C15 H15 109.2 . . ?
C14 C15 C16 110.5(3) . . ?
C16 C15 H15 109.2 . . ?
C1 C8 H8A 110.1 . . ?
C1 C8 H8B 110.1 . . ?
C1 C8 C7 108.2(3) . . ?
H8A C8 H8B 108.4 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C28 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
C26 C27 C28 108.4(2) . . ?
C26 C27 H27A 110.0 . . ?
C26 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C28 C29 C24 108.6(2) . . ?
C28 C29 H29A 110.0 . . ?
C28 C29 H29B 110.0 . . ?
C24 C29 H29A 110.0 . . ?
C24 C29 H29B 110.0 . . ?
H29A C29 H29B 108.3 . . ?
C10 C11 H11 110.5 . . ?
C10 C11 C12 106.6(3) . . ?
C10 C11 C16 107.9(3) . . ?
C12 C11 H11 110.5 . . ?
C12 C11 C16 110.8(3) . . ?
C16 C11 H11 110.5 . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C7 C6 C5 109.7(3) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 C8 112.8(3) . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C17 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
C15 C14 C17 110.6(3) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C17 C12 H12A 109.6 . . ?
C17 C12 H12B 109.6 . . ?
C11 C12 C17 110.3(2) . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 C6 112.0(3) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.2(3) . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
C11 C16 C15 109.1(2) . . ?
C11 C16 H16A 109.9 . . ?
C11 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C5 C4 C3 109.9(3) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C9 C2 H2D 108.8 . . ?
C9 C2 H2E 108.8 . . ?
C3 C2 C9 113.6(3) . . ?
C3 C2 H2D 108.8 . . ?
C3 C2 H2E 108.8 . . ?
H2D C2 H2E 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C8 C7 55.6(4) . . . . ?
O2 C9 C2 C3 42.7(5) . . . . ?
N2 C23 C22 C28 -179.5(2) . . . . ?
N2 C23 C21 C26 -179.8(2) . . . . ?
N2 C23 C20 C24 179.0(2) . . . . ?
O1 C9 C2 C3 -142.3(3) . . . . ?
O4 C1 C8 C7 -122.2(3) . . . . ?
N1 C19 C13 C15 -179.6(2) . . . . ?
N1 C19 C18 C17 179.3(2) . . . . ?
N1 C19 C10 C11 -179.3(2) . . . . ?
C19 C13 C15 C14 60.5(3) . . . . ?
C19 C13 C15 C16 -60.5(3) . . . . ?
C19 C18 C17 C14 -61.2(3) . . . . ?
C19 C18 C17 C12 59.3(3) . . . . ?
C19 C10 C11 C12 -59.3(3) . . . . ?
C19 C10 C11 C16 59.7(3) . . . . ?
C23 C22 C28 C27 -59.0(3) . . . . ?
C23 C22 C28 C29 61.6(3) . . . . ?
C23 C21 C26 C25 -60.4(3) . . . . ?
C23 C21 C26 C27 58.8(3) . . . . ?
C23 C20 C24 C25 60.5(3) . . . . ?
C23 C20 C24 C29 -60.4(3) . . . . ?
C1 C8 C7 C6 -174.2(3) . . . . ?
C22 C23 C21 C26 -57.4(3) . . . . ?
C22 C23 C20 C24 59.2(3) . . . . ?
C22 C28 C27 C26 58.0(3) . . . . ?
C22 C28 C29 C24 -60.4(3) . . . . ?
C13 C19 C18 C17 63.0(3) . . . . ?
C13 C19 C10 C11 -60.9(3) . . . . ?
C13 C15 C14 C17 -62.6(3) . . . . ?
C13 C15 C16 C11 60.8(3) . . . . ?
C18 C19 C13 C15 -63.8(3) . . . . ?
C18 C19 C10 C11 62.1(3) . . . . ?
C18 C17 C14 C15 64.0(3) . . . . ?
C18 C17 C12 C11 -61.7(3) . . . . ?
C21 C23 C22 C28 56.7(3) . . . . ?
C21 C23 C20 C24 -59.0(3) . . . . ?
C21 C26 C25 C24 58.4(3) . . . . ?
C21 C26 C27 C28 -57.3(3) . . . . ?
C20 C23 C22 C28 -61.3(3) . . . . ?
C20 C23 C21 C26 61.0(3) . . . . ?
C20 C24 C25 C26 -60.9(3) . . . . ?
C20 C24 C29 C28 61.8(3) . . . . ?
C10 C19 C13 C15 59.0(3) . . . . ?
C10 C19 C18 C17 -58.8(3) . . . . ?
C10 C11 C12 C17 58.1(3) . . . . ?
C10 C11 C16 C15 -58.0(3) . . . . ?
C25 C26 C27 C28 61.3(3) . . . . ?
C25 C24 C29 C28 -61.0(3) . . . . ?
C27 C28 C29 C24 61.6(3) . . . . ?
C27 C26 C25 C24 -61.9(3) . . . . ?
C29 C28 C27 C26 -61.4(3) . . . . ?
C29 C24 C25 C26 61.6(3) . . . . ?
C6 C5 C4 C3 -178.2(3) . . . . ?
C7 C6 C5 C4 -177.8(3) . . . . ?
C14 C17 C12 C11 58.3(3) . . . . ?
C14 C15 C16 C11 -58.1(3) . . . . ?
C12 C17 C14 C15 -58.5(3) . . . . ?
C12 C11 C16 C15 58.3(3) . . . . ?
C5 C6 C7 C8 179.6(3) . . . . ?
C16 C15 C14 C17 59.3(3) . . . . ?
C16 C11 C12 C17 -59.0(3) . . . . ?
C4 C3 C2 C9 -176.3(3) . . . . ?
C2 C3 C4 C5 -176.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method LOOP
_olex2_submission_original_sample_id AZL-2AMN
_olex2_submission_special_instructions 'No special instructions were received'
