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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_datam
_database_code_depnum_ccdc_archive 'CCDC 2036851'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N2 O2, C5 H7 O4, O'
_chemical_formula_sum            'C25 H32 N2 O7'
_chemical_formula_weight         472.52
_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   20.206(7)
_cell_length_b                   6.6378(19)
_cell_length_c                   20.461(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.74(2)
_cell_angle_gamma                90
_cell_volume                     2450.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2164
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11284
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          'profile data from ω-scans'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3726
_reflns_number_total             5419
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;

_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    ?
_refine_diff_density_max         1.347
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0708
_refine_ls_restrained_S_all      1.003
_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)+(0.1266P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1952
_refine_ls_wR_factor_ref         0.2094
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 2(2)
 -1(2)
2. 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 C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O12(H12), N1(H1), O33(H33)
3.b Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C11(H11)
3.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C28(H28A,H28B), C29(H29A,
 H29B), C30(H30A,H30B)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24)
3.e X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.f Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.15408(17) 0.4965(5) 0.39072(18) 0.0434(8) Uani 1 1 d . . . . .
H12 H 0.131273 0.454251 0.405059 0.065 Uiso 1 1 d R U . . .
O21 O 0.0059(2) 1.2801(7) 0.1699(2) 0.0652(11) Uani 1 1 d . . . . .
N1 N 0.1727(2) 0.9312(6) 0.45804(19) 0.0382(9) Uani 1 1 d . . . . .
H1 H 0.122045 0.983833 0.432235 0.046 Uiso 1 1 d R U . . .
N16 N 0.1699(2) 0.6322(9) 0.1587(2) 0.0527(12) Uani 1 1 d . . . . .
C2 C 0.2240(3) 1.1032(8) 0.4956(3) 0.0443(11) Uani 1 1 d . . . . .
H2A H 0.205468 1.178700 0.524582 0.053 Uiso 1 1 calc R U . . .
H2B H 0.226373 1.193393 0.459452 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3013(3) 1.0216(9) 0.5452(3) 0.0441(11) Uani 1 1 d . . . . .
H3 H 0.309117 1.030923 0.595955 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3594(4) 1.1465(11) 0.5379(4) 0.0667(17) Uani 1 1 d . . . . .
H4 H 0.363139 1.138032 0.494289 0.080 Uiso 1 1 calc R U . . .
C5 C 0.4043(4) 1.2641(15) 0.5878(4) 0.100(3) Uani 1 1 d . . . . .
H5A H 0.402076 1.276044 0.632045 0.120 Uiso 1 1 calc R U . . .
H5B H 0.439203 1.337618 0.579792 0.120 Uiso 1 1 calc R U . . .
C6 C 0.3032(2) 0.7996(8) 0.5270(2) 0.0403(11) Uani 1 1 d . . . . .
H6 H 0.353894 0.748010 0.553342 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2521(3) 0.6838(9) 0.5502(3) 0.0467(12) Uani 1 1 d . . . . .
H7A H 0.271832 0.687106 0.603065 0.056 Uiso 1 1 calc R U . . .
H7B H 0.248693 0.544310 0.534931 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1755(3) 0.7817(9) 0.5146(2) 0.0436(11) Uani 1 1 d . . . . .
H8A H 0.137760 0.679289 0.491634 0.052 Uiso 1 1 calc R U . . .
H8B H 0.165906 0.849499 0.551475 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2752(2) 0.7711(9) 0.4439(2) 0.0400(10) Uani 1 1 d . . . . .
H9A H 0.306203 0.847302 0.427819 0.048 Uiso 1 1 calc R U . . .
H9B H 0.278248 0.629964 0.433234 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1944(2) 0.8436(7) 0.4024(2) 0.0345(10) Uani 1 1 d . . . . .
H10 H 0.193370 0.953462 0.369995 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1399(2) 0.6826(7) 0.3549(2) 0.0356(10) Uani 1 1 d . . . . .
H11 H 0.089490 0.725055 0.343656 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1464(2) 0.6664(8) 0.2842(2) 0.0369(10) Uani 1 1 d . . . . .
C14 C 0.1847(3) 0.5073(9) 0.2744(3) 0.0458(11) Uani 1 1 d . . . . .
H14 H 0.204691 0.407661 0.309939 0.055 Uiso 1 1 calc R U . . .
C15 C 0.1933(3) 0.4976(11) 0.2101(3) 0.0547(14) Uani 1 1 d . . . . .
H15 H 0.217744 0.385938 0.203871 0.066 Uiso 1 1 calc R U . . .
C17 C 0.1312(3) 0.7918(9) 0.1668(3) 0.0451(12) Uani 1 1 d . . . . .
C18 C 0.1170(2) 0.8145(8) 0.2285(2) 0.0377(10) Uani 1 1 d . . . . .
C19 C 0.0746(2) 0.9830(9) 0.2302(2) 0.0414(11) Uani 1 1 d . . . . .
H19 H 0.064864 1.000627 0.270154 0.050 Uiso 1 1 calc R U . . .
C20 C 0.0484(3) 1.1175(9) 0.1754(3) 0.0466(12) Uani 1 1 d . . . . .
C22 C -0.0180(4) 1.3044(13) 0.2246(4) 0.081(2) Uani 1 1 d . . . . .
H22A H -0.042711 1.431685 0.218142 0.122 Uiso 1 1 calc R U . . .
H22B H 0.024079 1.300216 0.271935 0.122 Uiso 1 1 calc R U . . .
H22C H -0.051614 1.197638 0.220791 0.122 Uiso 1 1 calc R U . . .
C23 C 0.0656(3) 1.0960(10) 0.1153(3) 0.0538(14) Uani 1 1 d . . . . .
H23 H 0.049055 1.192033 0.078224 0.065 Uiso 1 1 calc R U . . .
C24 C 0.1050(3) 0.9401(11) 0.1118(3) 0.0567(15) Uani 1 1 d . . . . .
H24 H 0.115468 0.928529 0.072171 0.068 Uiso 1 1 calc R U . . .
O25 O 0.4660(2) 0.5802(6) 0.0992(2) 0.0583(11) Uani 1 1 d . . . . .
O26 O 0.4635(2) 0.9087(6) 0.0907(2) 0.0571(10) Uani 1 1 d . . . . .
O32 O 0.7679(2) 0.7710(9) 0.2985(2) 0.0695(12) Uani 1 1 d . . . . .
O33 O 0.83351(19) 0.7541(8) 0.2366(2) 0.0712(12) Uani 1 1 d . . . . .
H33 H 0.866396 0.768356 0.271086 0.107 Uiso 1 1 d R U . . .
C27 C 0.4932(2) 0.7440(9) 0.0938(2) 0.0410(10) Uani 1 1 d . . . . .
C28 C 0.5676(2) 0.7423(9) 0.0942(3) 0.0446(11) Uani 1 1 d . . . . .
H28A H 0.570607 0.855335 0.065624 0.053 Uiso 1 1 calc R U . . .
H28B H 0.572385 0.619672 0.070881 0.053 Uiso 1 1 calc R U . . .
C29 C 0.6315(2) 0.7545(10) 0.1708(2) 0.0460(12) Uani 1 1 d . . . . .
H29A H 0.626292 0.874870 0.194964 0.055 Uiso 1 1 calc R U . . .
H29B H 0.630092 0.638711 0.199047 0.055 Uiso 1 1 calc R U . . .
C30 C 0.7054(2) 0.7599(10) 0.1682(2) 0.0443(11) Uani 1 1 d . . . . .
H30A H 0.708605 0.643246 0.141245 0.053 Uiso 1 1 calc R U . . .
H30B H 0.706899 0.879030 0.141484 0.053 Uiso 1 1 calc R U . . .
C31 C 0.7711(2) 0.7616(9) 0.2413(3) 0.0455(11) Uani 1 1 d . . . . .
O90 O 0.5480(4) 1.2415(13) 0.1363(4) 0.122(2) 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
O12 H12 0.7062 . ?
O12 C11 1.398(6) . ?
O21 C20 1.353(7) . ?
O21 C22 1.413(8) . ?
N1 H1 0.9801 . ?
N1 C2 1.501(6) . ?
N1 C8 1.506(6) . ?
N1 C10 1.508(5) . ?
N16 C15 1.296(8) . ?
N16 C17 1.371(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.528(7) . ?
C3 H3 0.9800 . ?
C3 C4 1.499(8) . ?
C3 C6 1.525(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.282(10) . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.524(7) . ?
C6 C9 1.543(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.529(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.540(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.529(6) . ?
C11 H11 0.9800 . ?
C11 C13 1.514(6) . ?
C13 C14 1.377(7) . ?
C13 C18 1.417(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(7) . ?
C15 H15 0.9300 . ?
C17 C18 1.423(6) . ?
C17 C24 1.406(8) . ?
C18 C19 1.418(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.342(7) . ?
C20 C23 1.429(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.326(9) . ?
C24 H24 0.9300 . ?
O25 C27 1.246(7) . ?
O26 C27 1.235(7) . ?
O32 C31 1.201(6) . ?
O33 H33 0.7257 . ?
O33 C31 1.308(6) . ?
C27 C28 1.499(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.520(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.517(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.488(6) . ?

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
C11 O12 H12 123.4 . . ?
C20 O21 C22 117.0(5) . . ?
C2 N1 H1 108.5 . . ?
C2 N1 C8 109.2(4) . . ?
C2 N1 C10 108.1(4) . . ?
C8 N1 H1 108.6 . . ?
C8 N1 C10 113.7(4) . . ?
C10 N1 H1 108.6 . . ?
C15 N16 C17 117.1(4) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.5(4) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 110.5(5) . . ?
C4 C3 H3 108.1 . . ?
C4 C3 C6 113.7(5) . . ?
C6 C3 C2 108.1(4) . . ?
C6 C3 H3 108.1 . . ?
C3 C4 H4 117.9 . . ?
C5 C4 C3 124.3(7) . . ?
C5 C4 H4 117.9 . . ?
C4 C5 H5A 120.0 . . ?
C4 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C3 C6 H6 109.8 . . ?
C3 C6 C9 110.5(4) . . ?
C7 C6 C3 108.4(4) . . ?
C7 C6 H6 109.8 . . ?
C7 C6 C9 108.6(4) . . ?
C9 C6 H6 109.8 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C6 C7 C8 108.7(4) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
N1 C8 C7 109.0(4) . . ?
N1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C9 H9A 109.7 . . ?
C6 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 C6 109.9(3) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
N1 C10 C9 107.6(3) . . ?
N1 C10 H10 107.4 . . ?
N1 C10 C11 112.3(3) . . ?
C9 C10 H10 107.4 . . ?
C11 C10 C9 114.4(4) . . ?
C11 C10 H10 107.4 . . ?
O12 C11 C10 111.4(3) . . ?
O12 C11 H11 108.9 . . ?
O12 C11 C13 110.7(4) . . ?
C10 C11 H11 108.9 . . ?
C13 C11 C10 108.1(4) . . ?
C13 C11 H11 108.9 . . ?
C14 C13 C11 119.3(4) . . ?
C14 C13 C18 118.3(4) . . ?
C18 C13 C11 122.3(4) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
N16 C15 C14 125.1(5) . . ?
N16 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
N16 C17 C18 122.9(5) . . ?
N16 C17 C24 118.3(4) . . ?
C24 C17 C18 118.8(5) . . ?
C13 C18 C17 117.5(4) . . ?
C13 C18 C19 124.5(4) . . ?
C19 C18 C17 118.1(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.3(4) . . ?
C20 C19 H19 119.3 . . ?
O21 C20 C23 113.5(5) . . ?
C19 C20 O21 126.8(5) . . ?
C19 C20 C23 119.7(5) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.7 . . ?
C24 C23 C20 120.5(5) . . ?
C24 C23 H23 119.7 . . ?
C17 C24 H24 119.2 . . ?
C23 C24 C17 121.5(5) . . ?
C23 C24 H24 119.2 . . ?
C31 O33 H33 114.5 . . ?
O25 C27 C28 118.4(5) . . ?
O26 C27 O25 123.6(4) . . ?
O26 C27 C28 118.0(5) . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C29 113.0(4) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 C28 111.0(4) . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C29 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C31 C30 C29 114.4(4) . . ?
C31 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
O32 C31 O33 123.4(5) . . ?
O32 C31 C30 124.3(4) . . ?
O33 C31 C30 112.3(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
O12 C11 C13 C14 -19.4(6) . . . . ?
O12 C11 C13 C18 163.5(4) . . . . ?
O21 C20 C23 C24 -177.9(5) . . . . ?
N1 C2 C3 C4 136.9(5) . . . . ?
N1 C2 C3 C6 11.7(5) . . . . ?
N1 C10 C11 O12 -81.1(5) . . . . ?
N1 C10 C11 C13 157.0(4) . . . . ?
N16 C17 C18 C13 1.7(7) . . . . ?
N16 C17 C18 C19 -178.4(4) . . . . ?
N16 C17 C24 C23 178.4(5) . . . . ?
C2 N1 C8 C7 -67.1(5) . . . . ?
C2 N1 C10 C9 59.8(5) . . . . ?
C2 N1 C10 C11 -173.5(4) . . . . ?
C2 C3 C4 C5 109.7(8) . . . . ?
C2 C3 C6 C7 -67.5(5) . . . . ?
C2 C3 C6 C9 51.4(5) . . . . ?
C3 C6 C7 C8 54.1(5) . . . . ?
C3 C6 C9 C10 -61.2(5) . . . . ?
C4 C3 C6 C7 169.3(4) . . . . ?
C4 C3 C6 C9 -71.8(5) . . . . ?
C6 C3 C4 C5 -128.4(8) . . . . ?
C6 C7 C8 N1 10.8(6) . . . . ?
C6 C9 C10 N1 3.9(6) . . . . ?
C6 C9 C10 C11 -121.6(4) . . . . ?
C7 C6 C9 C10 57.6(6) . . . . ?
C8 N1 C2 C3 53.7(5) . . . . ?
C8 N1 C10 C9 -61.6(5) . . . . ?
C8 N1 C10 C11 65.1(5) . . . . ?
C9 C6 C7 C8 -66.0(5) . . . . ?
C9 C10 C11 O12 41.8(5) . . . . ?
C9 C10 C11 C13 -80.0(4) . . . . ?
C10 N1 C2 C3 -70.6(4) . . . . ?
C10 N1 C8 C7 53.7(5) . . . . ?
C10 C11 C13 C14 102.9(5) . . . . ?
C10 C11 C13 C18 -74.2(5) . . . . ?
C11 C13 C14 C15 -177.3(5) . . . . ?
C11 C13 C18 C17 175.3(4) . . . . ?
C11 C13 C18 C19 -4.6(7) . . . . ?
C13 C14 C15 N16 2.5(8) . . . . ?
C13 C18 C19 C20 -179.9(5) . . . . ?
C14 C13 C18 C17 -1.9(6) . . . . ?
C14 C13 C18 C19 178.2(4) . . . . ?
C15 N16 C17 C18 0.6(7) . . . . ?
C15 N16 C17 C24 -179.9(5) . . . . ?
C17 N16 C15 C14 -2.8(8) . . . . ?
C17 C18 C19 C20 0.1(7) . . . . ?
C18 C13 C14 C15 0.0(7) . . . . ?
C18 C17 C24 C23 -2.1(8) . . . . ?
C18 C19 C20 O21 178.0(5) . . . . ?
C18 C19 C20 C23 -2.4(7) . . . . ?
C19 C20 C23 C24 2.5(8) . . . . ?
C20 C23 C24 C17 -0.2(9) . . . . ?
C22 O21 C20 C19 -4.8(8) . . . . ?
C22 O21 C20 C23 175.6(5) . . . . ?
C24 C17 C18 C13 -177.8(4) . . . . ?
C24 C17 C18 C19 2.1(7) . . . . ?
O25 C27 C28 C29 -88.1(6) . . . . ?
O26 C27 C28 C29 89.2(6) . . . . ?
C27 C28 C29 C30 -178.0(5) . . . . ?
C28 C29 C30 C31 -177.1(5) . . . . ?
C29 C30 C31 O32 -4.5(9) . . . . ?
C29 C30 C31 O33 176.2(5) . . . . ?

# start Validation Reply Form
_vrf_PLAT097_datam               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.35 eA-3  
RESPONSE: We couldn't fix the H-atoms on the lattice water molecule
;
_vrf_PLAT306_datam               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O90 Check 
RESPONSE: We couldn't fix the H-atoms on the lattice water molecule
;
_vrf_PLAT430_datam               
;
PROBLEM: Short Inter D...A Contact  O25      ..O90      .       2.69 Ang.  
RESPONSE: Hydeogen bonding exist between carboxylate and lattice water
;
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2(2)
2 -1(2)

####################################################################### 
# 
# 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_datam_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2036859'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N2 O2, C7 H5 O3, H2 O'
_chemical_formula_sum            'C27 H32 N2 O6'
_chemical_formula_weight         480.54
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.943(3)
_cell_length_b                   17.066(6)
_cell_length_c                   20.466(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2424.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3478
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21414
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         3.098
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3253
_reflns_number_total             5525
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_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    ?
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1034 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      0.831
_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)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0942
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C9(H9A,H9B)
2.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24), C27(H27), C28(H28),
 C29(H29), C30(H30)
2.e X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.7771(4) 0.48545(13) 0.54711(11) 0.0501(6) Uani 1 1 d . . . . .
H12 H 0.825(6) 0.530(2) 0.5349(18) 0.083(13) Uiso 1 1 d . . . . .
O21 O 0.0214(4) 0.41938(13) 0.35108(10) 0.0616(7) Uani 1 1 d . . . . .
N1 N 0.3645(4) 0.54254(13) 0.58500(11) 0.0380(6) Uani 1 1 d . . . . .
H1 H 0.338(5) 0.5714(16) 0.5434(14) 0.052(8) Uiso 1 1 d . . . . .
N16 N 0.6587(5) 0.24520(14) 0.41500(12) 0.0515(8) Uani 1 1 d . . . . .
C2 C 0.5062(5) 0.58945(15) 0.62385(13) 0.0453(8) Uani 1 1 d . . . . .
H2A H 0.444791 0.636458 0.640455 0.054 Uiso 1 1 calc R U . . .
H2B H 0.613073 0.605039 0.596224 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5798(5) 0.53997(17) 0.68050(14) 0.0498(9) Uani 1 1 d . . . . .
H3A H 0.711982 0.524315 0.672459 0.060 Uiso 1 1 calc R U . . .
H3B H 0.576177 0.570194 0.720620 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4531(5) 0.46803(16) 0.68704(13) 0.0423(8) Uani 1 1 d . . . . .
H4 H 0.488056 0.438938 0.726587 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2444(5) 0.49609(16) 0.69194(13) 0.0457(8) Uani 1 1 d . . . . .
H5 H 0.239778 0.538426 0.724250 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1879(5) 0.53075(17) 0.62541(13) 0.0451(8) Uani 1 1 d . . . . .
H6A H 0.100257 0.495480 0.603112 0.054 Uiso 1 1 calc R U . . .
H6B H 0.122817 0.580471 0.631697 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1073(6) 0.4337(2) 0.71339(18) 0.0609(10) Uani 1 1 d . . . . .
H7 H 0.101957 0.388229 0.688455 0.073 Uiso 1 1 calc R U . . .
C8 C -0.0053(7) 0.4378(3) 0.7641(2) 0.0841(13) Uani 1 1 d . . . . .
H8A H -0.004367 0.482346 0.790326 0.101 Uiso 1 1 calc R U . . .
H8B H -0.086731 0.396271 0.774134 0.101 Uiso 1 1 calc R U . . .
C9 C 0.4833(5) 0.41650(15) 0.62697(12) 0.0424(8) Uani 1 1 d . . . . .
H9A H 0.400389 0.370869 0.629617 0.051 Uiso 1 1 calc R U . . .
H9B H 0.615845 0.398575 0.625575 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4370(5) 0.46293(14) 0.56446(12) 0.0356(7) Uani 1 1 d . . . . .
H10 H 0.330225 0.436050 0.542616 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6023(5) 0.46876(15) 0.51509(13) 0.0382(7) Uani 1 1 d . . . . .
H11 H 0.574019 0.511122 0.484218 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6206(5) 0.39226(15) 0.47745(13) 0.0392(7) Uani 1 1 d . . . . .
C14 C 0.7745(5) 0.34452(16) 0.48815(14) 0.0452(8) Uani 1 1 d . . . . .
H14 H 0.870352 0.359626 0.517290 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7889(6) 0.27278(17) 0.45540(14) 0.0520(9) Uani 1 1 d . . . . .
H15 H 0.898218 0.242564 0.462779 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5036(5) 0.29246(17) 0.40345(13) 0.0446(8) Uani 1 1 d . . . . .
C18 C 0.4797(5) 0.36735(15) 0.43161(12) 0.0371(7) Uani 1 1 d . . . . .
C19 C 0.3166(5) 0.41216(16) 0.41368(12) 0.0424(8) Uani 1 1 d . . . . .
H19 H 0.301019 0.462428 0.430412 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1825(5) 0.38234(18) 0.37222(13) 0.0485(8) Uani 1 1 d . . . . .
C22 C -0.0128(6) 0.4963(2) 0.37481(17) 0.0685(11) Uani 1 1 d . . . . .
H22A H -0.130342 0.516105 0.356427 0.103 Uiso 1 1 calc R U . . .
H22B H -0.023403 0.495068 0.421571 0.103 Uiso 1 1 calc R U . . .
H22C H 0.092228 0.529786 0.362489 0.103 Uiso 1 1 calc R U . . .
C23 C 0.2043(6) 0.3064(2) 0.34663(15) 0.0581(10) Uani 1 1 d . . . . .
H23 H 0.110194 0.285915 0.319168 0.070 Uiso 1 1 calc R U . . .
C24 C 0.3601(6) 0.26316(18) 0.36152(15) 0.0574(10) Uani 1 1 d . . . . .
H24 H 0.373182 0.213222 0.343875 0.069 Uiso 1 1 calc R U . . .
O32 O 0.6508(4) 0.76638(16) 0.37506(15) 0.0809(9) Uani 1 1 d . . . . .
H32 H 0.649(7) 0.738(2) 0.420(2) 0.122(17) Uiso 1 1 d . . . . .
O33 O 0.5498(5) 0.68604(18) 0.47346(15) 0.0950(10) Uani 1 1 d . . . . .
O34 O 0.2720(4) 0.62482(12) 0.47588(10) 0.0574(6) Uani 1 1 d . . . . .
C25 C 0.3881(6) 0.67053(19) 0.44958(16) 0.0533(9) Uani 1 1 d . . . . .
C26 C 0.3362(5) 0.70939(16) 0.38642(13) 0.0428(8) Uani 1 1 d . . . . .
C27 C 0.1553(5) 0.69999(16) 0.35931(14) 0.0461(8) Uani 1 1 d . . . . .
H27 H 0.063038 0.671434 0.382074 0.055 Uiso 1 1 calc R U . . .
C28 C 0.1080(6) 0.73155(17) 0.29981(14) 0.0533(9) Uani 1 1 d . . . . .
H28 H -0.014859 0.724662 0.282592 0.064 Uiso 1 1 calc R U . . .
C29 C 0.2453(7) 0.77376(19) 0.26573(15) 0.0593(10) Uani 1 1 d . . . . .
H29 H 0.215912 0.794253 0.224816 0.071 Uiso 1 1 calc R U . . .
C30 C 0.4232(6) 0.78538(19) 0.29194(16) 0.0616(11) Uani 1 1 d . . . . .
H30 H 0.513456 0.815134 0.269304 0.074 Uiso 1 1 calc R U . . .
C31 C 0.4712(6) 0.75349(17) 0.35175(16) 0.0521(9) Uani 1 1 d . . . . .
O90 O 0.8963(6) 0.62287(18) 0.5103(2) 0.0896(11) Uani 1 1 d . . . . .
H90A H 0.796(10) 0.650(3) 0.499(3) 0.15(3) Uiso 1 1 d . . . . .
H90B H 0.980(10) 0.639(4) 0.494(3) 0.15(3) 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
O12 H12 0.87(4) . ?
O12 C11 1.408(4) . ?
O21 C20 1.356(4) . ?
O21 C22 1.420(4) . ?
N1 H1 1.00(3) . ?
N1 C2 1.497(4) . ?
N1 C6 1.493(4) . ?
N1 C10 1.509(3) . ?
N16 C15 1.312(4) . ?
N16 C17 1.366(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.529(5) . ?
C4 C9 1.526(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.535(4) . ?
C5 C7 1.494(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.301(5) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.539(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.532(4) . ?
C11 H11 0.9800 . ?
C11 C13 1.521(4) . ?
C13 C14 1.361(4) . ?
C13 C18 1.421(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.412(4) . ?
C17 C24 1.407(5) . ?
C18 C19 1.415(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.359(4) . ?
C20 C23 1.406(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.344(5) . ?
C24 H24 0.9300 . ?
O32 H32 1.04(4) . ?
O32 C31 1.353(4) . ?
O33 C25 1.253(4) . ?
O34 C25 1.244(4) . ?
C25 C26 1.497(4) . ?
C26 C27 1.383(5) . ?
C26 C31 1.396(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.372(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.384(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.362(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.380(5) . ?
O90 H90A 0.86(7) . ?
O90 H90B 0.73(7) . ?

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
C11 O12 H12 112(3) . . ?
C20 O21 C22 117.4(3) . . ?
C2 N1 H1 108.0(17) . . ?
C2 N1 C10 114.2(2) . . ?
C6 N1 H1 112.8(19) . . ?
C6 N1 C2 108.5(2) . . ?
C6 N1 C10 107.9(2) . . ?
C10 N1 H1 105.5(15) . . ?
C15 N16 C17 116.1(3) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.2(2) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C3 C4 H4 109.8 . . ?
C3 C4 C5 107.6(3) . . ?
C3 C4 C9 108.4(2) . . ?
C5 C4 H4 109.8 . . ?
C9 C4 H4 109.8 . . ?
C9 C4 C5 111.3(3) . . ?
C4 C5 H5 107.8 . . ?
C4 C5 C6 107.7(3) . . ?
C6 C5 H5 107.8 . . ?
C7 C5 C4 113.6(3) . . ?
C7 C5 H5 107.8 . . ?
C7 C5 C6 111.9(3) . . ?
N1 C6 C5 109.5(3) . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C5 C7 H7 117.3 . . ?
C8 C7 C5 125.4(4) . . ?
C8 C7 H7 117.3 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C4 C9 H9A 109.6 . . ?
C4 C9 H9B 109.6 . . ?
C4 C9 C10 110.1(2) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
N1 C10 C9 107.6(2) . . ?
N1 C10 H10 107.2 . . ?
N1 C10 C11 112.0(2) . . ?
C9 C10 H10 107.2 . . ?
C11 C10 C9 115.2(3) . . ?
C11 C10 H10 107.2 . . ?
O12 C11 C10 110.6(2) . . ?
O12 C11 H11 108.9 . . ?
O12 C11 C13 109.7(3) . . ?
C10 C11 H11 108.9 . . ?
C13 C11 C10 109.9(2) . . ?
C13 C11 H11 108.9 . . ?
C14 C13 C11 119.9(3) . . ?
C14 C13 C18 117.9(3) . . ?
C18 C13 C11 122.2(3) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
N16 C15 C14 124.5(3) . . ?
N16 C15 H15 117.7 . . ?
C14 C15 H15 117.7 . . ?
N16 C17 C18 123.8(3) . . ?
N16 C17 C24 117.0(3) . . ?
C24 C17 C18 119.2(3) . . ?
C17 C18 C13 117.3(3) . . ?
C17 C18 C19 118.5(3) . . ?
C19 C18 C13 124.1(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
O21 C20 C19 126.2(3) . . ?
O21 C20 C23 113.6(3) . . ?
C19 C20 C23 120.3(3) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.7 . . ?
C24 C23 C20 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C17 C24 H24 119.6 . . ?
C23 C24 C17 120.9(3) . . ?
C23 C24 H24 119.6 . . ?
C31 O32 H32 103(3) . . ?
O33 C25 C26 117.3(3) . . ?
O34 C25 O33 123.0(3) . . ?
O34 C25 C26 119.7(3) . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 C31 117.9(3) . . ?
C31 C26 C25 121.1(3) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 C26 121.9(3) . . ?
C28 C27 H27 119.0 . . ?
C27 C28 H28 120.4 . . ?
C27 C28 C29 119.1(4) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.7(3) . . ?
C31 C30 H30 119.6 . . ?
O32 C31 C26 121.8(3) . . ?
O32 C31 C30 118.1(3) . . ?
C30 C31 C26 120.1(4) . . ?
H90A O90 H90B 109(6) . . ?

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
O12 C11 C13 C14 12.2(4) . . . . ?
O12 C11 C13 C18 -168.9(2) . . . . ?
O21 C20 C23 C24 178.0(3) . . . . ?
N1 C2 C3 C4 -12.6(4) . . . . ?
N1 C10 C11 O12 79.6(3) . . . . ?
N1 C10 C11 C13 -159.1(2) . . . . ?
N16 C17 C18 C13 -3.8(4) . . . . ?
N16 C17 C18 C19 177.3(3) . . . . ?
N16 C17 C24 C23 -178.8(3) . . . . ?
C2 N1 C6 C5 -52.9(3) . . . . ?
C2 N1 C10 C9 60.6(3) . . . . ?
C2 N1 C10 C11 -67.0(3) . . . . ?
C2 C3 C4 C5 -53.4(3) . . . . ?
C2 C3 C4 C9 67.1(3) . . . . ?
C3 C4 C5 C6 68.4(3) . . . . ?
C3 C4 C5 C7 -167.1(2) . . . . ?
C3 C4 C9 C10 -57.6(3) . . . . ?
C4 C5 C6 N1 -13.3(3) . . . . ?
C4 C5 C7 C8 123.0(4) . . . . ?
C4 C9 C10 N1 -3.7(3) . . . . ?
C4 C9 C10 C11 122.0(3) . . . . ?
C5 C4 C9 C10 60.6(3) . . . . ?
C6 N1 C2 C3 68.7(3) . . . . ?
C6 N1 C10 C9 -60.2(3) . . . . ?
C6 N1 C10 C11 172.3(2) . . . . ?
C6 C5 C7 C8 -114.8(4) . . . . ?
C7 C5 C6 N1 -138.8(3) . . . . ?
C9 C4 C5 C6 -50.2(3) . . . . ?
C9 C4 C5 C7 74.3(3) . . . . ?
C9 C10 C11 O12 -43.7(3) . . . . ?
C9 C10 C11 C13 77.5(3) . . . . ?
C10 N1 C2 C3 -51.7(3) . . . . ?
C10 N1 C6 C5 71.3(3) . . . . ?
C10 C11 C13 C14 -109.6(3) . . . . ?
C10 C11 C13 C18 69.3(3) . . . . ?
C11 C13 C14 C15 177.7(3) . . . . ?
C11 C13 C18 C17 -175.0(3) . . . . ?
C11 C13 C18 C19 3.8(4) . . . . ?
C13 C14 C15 N16 -2.2(5) . . . . ?
C13 C18 C19 C20 -176.2(3) . . . . ?
C14 C13 C18 C17 3.8(4) . . . . ?
C14 C13 C18 C19 -177.4(3) . . . . ?
C15 N16 C17 C18 0.7(4) . . . . ?
C15 N16 C17 C24 -178.5(3) . . . . ?
C17 N16 C15 C14 2.4(5) . . . . ?
C17 C18 C19 C20 2.5(4) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C18 C17 C24 C23 1.9(5) . . . . ?
C18 C19 C20 O21 -179.5(3) . . . . ?
C18 C19 C20 C23 0.0(4) . . . . ?
C19 C20 C23 C24 -1.7(5) . . . . ?
C20 C23 C24 C17 0.6(5) . . . . ?
C22 O21 C20 C19 -0.8(5) . . . . ?
C22 O21 C20 C23 179.6(3) . . . . ?
C24 C17 C18 C13 175.4(3) . . . . ?
C24 C17 C18 C19 -3.5(4) . . . . ?
O33 C25 C26 C27 -175.2(3) . . . . ?
O33 C25 C26 C31 7.5(5) . . . . ?
O34 C25 C26 C27 5.0(5) . . . . ?
O34 C25 C26 C31 -172.3(3) . . . . ?
C25 C26 C27 C28 -176.4(3) . . . . ?
C25 C26 C31 O32 -3.4(5) . . . . ?
C25 C26 C31 C30 176.6(3) . . . . ?
C26 C27 C28 C29 0.3(4) . . . . ?
C27 C26 C31 O32 179.2(3) . . . . ?
C27 C26 C31 C30 -0.8(4) . . . . ?
C27 C28 C29 C30 -1.7(5) . . . . ?
C28 C29 C30 C31 1.9(5) . . . . ?
C29 C30 C31 O32 179.4(3) . . . . ?
C29 C30 C31 C26 -0.6(5) . . . . ?
C31 C26 C27 C28 1.0(4) . . . . ?

_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_datam_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2036854'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N2 O2, C3 H4 O2, 3(O)'
_chemical_formula_sum            'C23 H29 N2 O7'
_chemical_formula_weight         445.48
_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   19.945(10)
_cell_length_b                   6.698(4)
_cell_length_c                   18.303(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.980(9)
_cell_angle_gamma                90
_cell_volume                     2436(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1707
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.4
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9227
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         3.161
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                2566
_reflns_number_total             4214
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_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    ?
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0832
_refine_ls_restrained_S_all      0.945
_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)+(0.1585P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.2455
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C28(H28A,H28B),
 C29(H29A,H29B)
2.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C15(H15), C23(H23), C24(H24)
2.e X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.7973(3) 0.9360(8) 0.7315(3) 0.0499(13) Uani 1 1 d . . . . .
H12 H 0.838(5) 0.994(19) 0.766(6) 0.10(3) Uiso 1 1 d . . . . .
O21 O 0.9512(3) 0.1596(9) 0.5903(3) 0.0668(17) Uani 1 1 d . . . . .
N1 N 0.7714(3) 0.5002(10) 0.7851(3) 0.0441(15) Uani 1 1 d . . . . .
H1 H 0.817581 0.449806 0.792574 0.053 Uiso 1 1 calc R U . . .
N16 N 0.8294(3) 0.8254(11) 0.4649(3) 0.0559(18) Uani 1 1 d . . . . .
C2 C 0.7239(4) 0.3251(12) 0.7862(4) 0.053(2) Uani 1 1 d . . . . .
H2A H 0.733483 0.250084 0.831183 0.063 Uiso 1 1 calc R U . . .
H2B H 0.730397 0.237231 0.745252 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6515(4) 0.3979(12) 0.7809(4) 0.0473(19) Uani 1 1 d . . . . .
H3 H 0.634044 0.377609 0.828793 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6088(4) 0.2845(14) 0.7261(5) 0.065(2) Uani 1 1 d . . . . .
H4 H 0.616781 0.300815 0.677131 0.078 Uiso 1 1 calc R U . . .
C5 C 0.5610(5) 0.1640(18) 0.7403(7) 0.091(3) Uani 1 1 d . . . . .
H5A H 0.551360 0.143450 0.788531 0.109 Uiso 1 1 calc R U . . .
H5B H 0.536243 0.097734 0.702271 0.109 Uiso 1 1 calc R U . . .
C6 C 0.6533(4) 0.6239(13) 0.7662(4) 0.0503(19) Uani 1 1 d . . . . .
H6 H 0.607113 0.674440 0.758588 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6897(4) 0.7303(15) 0.8313(5) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.665079 0.714230 0.874384 0.074 Uiso 1 1 calc R U . . .
H7B H 0.693252 0.871749 0.821039 0.074 Uiso 1 1 calc R U . . .
C8 C 0.7603(4) 0.6376(13) 0.8449(4) 0.0504(19) Uani 1 1 d . . . . .
H8A H 0.794083 0.742022 0.847448 0.060 Uiso 1 1 calc R U . . .
H8B H 0.763976 0.566307 0.891243 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7617(3) 0.5977(11) 0.7086(3) 0.0387(16) Uani 1 1 d . . . . .
H9 H 0.767227 0.492242 0.672522 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6901(4) 0.6668(13) 0.6978(4) 0.050(2) Uani 1 1 d . . . . .
H10A H 0.667360 0.598728 0.655909 0.060 Uiso 1 1 calc R U . . .
H10B H 0.688977 0.808980 0.687790 0.060 Uiso 1 1 calc R U . . .
C11 C 0.8167(3) 0.7551(10) 0.6993(3) 0.0402(17) Uani 1 1 d . . . . .
H11 H 0.859547 0.709366 0.723908 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8236(3) 0.7787(11) 0.6171(4) 0.0387(17) Uani 1 1 d . . . . .
C14 C 0.7959(3) 0.9411(12) 0.5809(4) 0.0434(17) Uani 1 1 d . . . . .
H14 H 0.774348 1.038976 0.606318 0.052 Uiso 1 1 calc R U . . .
C15 C 0.8002(4) 0.9587(14) 0.5054(4) 0.053(2) Uani 1 1 d . . . . .
H15 H 0.781309 1.071167 0.481977 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8571(4) 0.6634(12) 0.5007(4) 0.0458(18) Uani 1 1 d . . . . .
C18 C 0.8573(3) 0.6335(11) 0.5777(4) 0.0389(16) Uani 1 1 d . . . . .
C19 C 0.8901(3) 0.4641(13) 0.6097(4) 0.0476(18) Uani 1 1 d . . . . .
H19 H 0.884(3) 0.410(12) 0.668(4) 0.05(2) Uiso 1 1 d . . . . .
C20 C 0.9174(4) 0.3287(13) 0.5669(4) 0.051(2) Uani 1 1 d . . . . .
C22 C 0.9573(5) 0.1192(17) 0.6662(5) 0.077(3) Uani 1 1 d . . . . .
H22A H 0.981945 -0.002763 0.675242 0.116 Uiso 1 1 calc R U . . .
H22B H 0.980918 0.226842 0.691729 0.116 Uiso 1 1 calc R U . . .
H22C H 0.913370 0.106050 0.683188 0.116 Uiso 1 1 calc R U . . .
C23 C 0.9140(4) 0.3560(16) 0.4893(4) 0.062(2) Uani 1 1 d . . . . .
H23 H 0.931683 0.259141 0.459994 0.074 Uiso 1 1 calc R U . . .
C24 C 0.8861(4) 0.5170(16) 0.4589(4) 0.060(2) Uani 1 1 d . . . . .
H24 H 0.885549 0.534009 0.408413 0.072 Uiso 1 1 calc R U . . .
O26 O 0.4011(3) 0.8859(8) 0.8160(3) 0.0539(14) Uani 1 1 d . . . . .
O27 O 0.3950(4) 0.5582(9) 0.8281(3) 0.076(2) Uani 1 1 d . . . . .
C25 C 0.4233(4) 0.7200(13) 0.8416(4) 0.0471(18) Uani 1 1 d . . . . .
C28 C 0.4866(4) 0.7216(13) 0.8937(4) 0.0478(18) Uani 1 1 d . . . . .
H28A H 0.513147 0.838702 0.884459 0.057 Uiso 1 1 calc R U . . .
H28B H 0.513333 0.604263 0.885244 0.057 Uiso 1 1 calc R U . . .
C29 C 0.4691(4) 0.7234(14) 0.9728(4) 0.0523(19) Uani 1 1 d . . . . .
H29A H 0.442335 0.841083 0.980870 0.063 Uiso 1 1 calc R U . . .
H29B H 0.441924 0.607028 0.981445 0.063 Uiso 1 1 calc R U . . .
O90 O 0.4502(3) 0.2205(10) 0.8913(3) 0.0712(17) Uani 1 1 d . . . . .
O91 O 0.5835(4) 0.2189(14) 0.9629(4) 0.094(2) Uani 1 1 d . . . . .
O92 O 0.7200(7) 0.291(3) 0.9771(8) 0.209(6) 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
O12 H12 1.06(11) . ?
O12 C11 1.417(8) . ?
O21 C20 1.368(10) . ?
O21 C22 1.410(11) . ?
N1 H1 0.9800 . ?
N1 C2 1.508(10) . ?
N1 C8 1.462(10) . ?
N1 C9 1.541(8) . ?
N16 C15 1.327(11) . ?
N16 C17 1.361(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.519(10) . ?
C3 H3 0.9800 . ?
C3 C4 1.471(12) . ?
C3 C6 1.538(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.292(13) . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.518(11) . ?
C6 C10 1.532(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.539(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.498(10) . ?
C9 C11 1.542(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C13 1.530(9) . ?
C13 C14 1.365(10) . ?
C13 C18 1.415(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(10) . ?
C15 H15 0.9300 . ?
C17 C18 1.422(9) . ?
C17 C24 1.400(12) . ?
C18 C19 1.411(11) . ?
C19 H19 1.14(7) . ?
C19 C20 1.345(11) . ?
C20 C23 1.428(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.315(13) . ?
C24 H24 0.9300 . ?
O26 C25 1.271(10) . ?
O27 C25 1.237(10) . ?
C25 C28 1.514(10) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.518(11) . ?
C29 C29 1.517(13) 2_657 ?
C29 H29A 0.9700 . ?
C29 H29B 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
C11 O12 H12 110(6) . . ?
C20 O21 C22 117.8(7) . . ?
C2 N1 H1 108.3 . . ?
C2 N1 C9 108.2(5) . . ?
C8 N1 H1 108.3 . . ?
C8 N1 C2 110.1(6) . . ?
C8 N1 C9 113.5(6) . . ?
C9 N1 H1 108.3 . . ?
C15 N16 C17 116.5(6) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C3 110.1(6) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3 108.0 . . ?
C2 C3 C6 106.9(6) . . ?
C4 C3 C2 111.6(7) . . ?
C4 C3 H3 108.0 . . ?
C4 C3 C6 114.2(7) . . ?
C6 C3 H3 108.0 . . ?
C3 C4 H4 117.3 . . ?
C5 C4 C3 125.4(9) . . ?
C5 C4 H4 117.3 . . ?
C4 C5 H5A 120.0 . . ?
C4 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C3 C6 H6 109.2 . . ?
C7 C6 C3 110.0(7) . . ?
C7 C6 H6 109.2 . . ?
C7 C6 C10 108.8(6) . . ?
C10 C6 C3 110.3(6) . . ?
C10 C6 H6 109.2 . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C6 C7 C8 107.8(7) . . ?
H7A C7 H7B 108.5 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
N1 C8 C7 109.2(6) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 H9 107.2 . . ?
N1 C9 C11 110.9(5) . . ?
C10 C9 N1 107.1(5) . . ?
C10 C9 H9 107.2 . . ?
C10 C9 C11 117.0(6) . . ?
C11 C9 H9 107.2 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C9 C10 C6 110.6(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O12 C11 C9 108.4(6) . . ?
O12 C11 H11 109.6 . . ?
O12 C11 C13 111.9(5) . . ?
C9 C11 H11 109.6 . . ?
C13 C11 C9 107.8(5) . . ?
C13 C11 H11 109.6 . . ?
C14 C13 C11 119.4(6) . . ?
C14 C13 C18 119.4(6) . . ?
C18 C13 C11 121.2(6) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(7) . . ?
C15 C14 H14 120.3 . . ?
N16 C15 C14 124.3(7) . . ?
N16 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
N16 C17 C18 123.8(7) . . ?
N16 C17 C24 117.7(7) . . ?
C24 C17 C18 118.5(7) . . ?
C13 C18 C17 116.6(6) . . ?
C19 C18 C13 124.3(6) . . ?
C19 C18 C17 119.1(7) . . ?
C18 C19 H19 124(4) . . ?
C20 C19 C18 119.7(7) . . ?
C20 C19 H19 114(4) . . ?
O21 C20 C23 113.4(7) . . ?
C19 C20 O21 126.1(7) . . ?
C19 C20 C23 120.5(8) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.8 . . ?
C24 C23 C20 120.5(8) . . ?
C24 C23 H23 119.8 . . ?
C17 C24 H24 119.2 . . ?
C23 C24 C17 121.5(7) . . ?
C23 C24 H24 119.2 . . ?
O26 C25 C28 118.1(7) . . ?
O27 C25 O26 123.7(6) . . ?
O27 C25 C28 118.2(7) . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 C29 110.6(6) . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C29 C29 C28 112.6(8) 2_657 . ?
C29 C29 H29A 109.1 2_657 . ?
C29 C29 H29B 109.1 2_657 . ?
H29A C29 H29B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 C11 C13 C14 -16.1(8) . . . . ?
O12 C11 C13 C18 165.0(6) . . . . ?
O21 C20 C23 C24 -176.5(8) . . . . ?
N1 C2 C3 C4 132.8(7) . . . . ?
N1 C2 C3 C6 7.3(8) . . . . ?
N1 C9 C10 C6 2.0(8) . . . . ?
N1 C9 C11 O12 -82.8(7) . . . . ?
N1 C9 C11 C13 156.0(5) . . . . ?
N16 C17 C18 C13 3.0(10) . . . . ?
N16 C17 C18 C19 -177.3(7) . . . . ?
N16 C17 C24 C23 179.9(8) . . . . ?
C2 N1 C8 C7 -65.8(8) . . . . ?
C2 N1 C9 C10 60.9(7) . . . . ?
C2 N1 C9 C11 -170.5(6) . . . . ?
C2 C3 C4 C5 112.2(11) . . . . ?
C2 C3 C6 C7 -64.6(7) . . . . ?
C2 C3 C6 C10 55.4(8) . . . . ?
C3 C6 C7 C8 56.4(8) . . . . ?
C3 C6 C10 C9 -61.9(8) . . . . ?
C4 C3 C6 C7 171.4(6) . . . . ?
C4 C3 C6 C10 -68.5(8) . . . . ?
C6 C3 C4 C5 -126.4(11) . . . . ?
C6 C7 C8 N1 7.8(10) . . . . ?
C7 C6 C10 C9 58.8(9) . . . . ?
C8 N1 C2 C3 57.2(8) . . . . ?
C8 N1 C9 C10 -61.6(7) . . . . ?
C8 N1 C9 C11 67.1(8) . . . . ?
C9 N1 C2 C3 -67.3(7) . . . . ?
C9 N1 C8 C7 55.6(9) . . . . ?
C9 C11 C13 C14 103.0(7) . . . . ?
C9 C11 C13 C18 -76.0(7) . . . . ?
C10 C6 C7 C8 -64.6(9) . . . . ?
C10 C9 C11 O12 40.4(7) . . . . ?
C10 C9 C11 C13 -80.9(7) . . . . ?
C11 C9 C10 C6 -123.1(7) . . . . ?
C11 C13 C14 C15 -177.7(6) . . . . ?
C11 C13 C18 C17 176.1(6) . . . . ?
C11 C13 C18 C19 -3.7(10) . . . . ?
C13 C14 C15 N16 0.6(11) . . . . ?
C13 C18 C19 C20 176.2(7) . . . . ?
C14 C13 C18 C17 -2.9(9) . . . . ?
C14 C13 C18 C19 177.4(7) . . . . ?
C15 N16 C17 C18 -1.2(11) . . . . ?
C15 N16 C17 C24 177.7(7) . . . . ?
C17 N16 C15 C14 -0.6(11) . . . . ?
C17 C18 C19 C20 -3.6(10) . . . . ?
C18 C13 C14 C15 1.2(10) . . . . ?
C18 C17 C24 C23 -1.1(12) . . . . ?
C18 C19 C20 O21 179.2(7) . . . . ?
C18 C19 C20 C23 0.6(11) . . . . ?
C19 C20 C23 C24 2.2(12) . . . . ?
C20 C23 C24 C17 -1.9(13) . . . . ?
C22 O21 C20 C19 1.3(12) . . . . ?
C22 O21 C20 C23 179.9(7) . . . . ?
C24 C17 C18 C13 -176.0(7) . . . . ?
C24 C17 C18 C19 3.8(10) . . . . ?
O26 C25 C28 C29 95.3(9) . . . . ?
O27 C25 C28 C29 -82.5(10) . . . . ?
C25 C28 C29 C29 179.6(5) . . . 2_657 ?
# start Validation Reply Form
_vrf_PLAT097_datam               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.83 eA-3  
RESPONSE: We were unable to fix the H-atoms on the lattice water
;
_vrf_PLAT306_datam               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O90 Check 
RESPONSE: We were unable to fix the H-atoms on the lattice water
;
_vrf_PLAT340_datam               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01105 Ang.  
RESPONSE: ...
;
_vrf_PLAT430_datam               
;
PROBLEM: Short Inter D...A Contact  O26      ..O90      .       2.77 Ang.  
RESPONSE: Hydrogen bonding existing between the carboxylate and lattice 
water
;
# end Validation Reply Form

_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_datam_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2036856'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N2 O2, C O2, 3(O)'
_chemical_formula_sum            'C21 H25 N2 O7'
_chemical_formula_weight         417.43
_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.387(10)
_cell_length_b                   6.419(3)
_cell_length_c                   18.467(8)
_cell_angle_alpha                90
_cell_angle_beta                 121.541(7)
_cell_angle_gamma                90
_cell_volume                     2160.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8062
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         3.114
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                2277
_reflns_number_total             3738
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;

_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    ?
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      0.950
_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)+(0.1330P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2199
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C10(H10A,H10B)
2.c Me refined with riding coordinates:
 C22(H22A,H22B,H22C)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24)
2.e Tetrahedral OH refined with riding coordinates:
 O12(H12)
2.f X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.6607(2) 0.5577(7) 0.7301(3) 0.0439(12) Uani 1 1 d . . . . .
H12 H 0.632747 0.576800 0.679053 0.066 Uiso 1 1 calc R U . . .
O21 O 0.5049(3) -0.2638(10) 0.7903(4) 0.0716(17) Uani 1 1 d . . . . .
N1 N 0.6973(3) 0.1190(9) 0.6843(3) 0.0394(13) Uani 1 1 d . . . . .
H1 H 0.643(4) 0.092(13) 0.653(5) 0.06(2) Uiso 1 1 d . . . . .
N16 N 0.6686(3) 0.3865(11) 0.9984(3) 0.0485(15) Uani 1 1 d . . . . .
C2 C 0.7096(4) 0.2757(13) 0.6340(4) 0.0507(19) Uani 1 1 d . . . . .
H2A H 0.673925 0.387000 0.616854 0.061 Uiso 1 1 calc R U . . .
H2B H 0.703357 0.211113 0.583138 0.061 Uiso 1 1 calc R U . . .
C3 C 0.7883(4) 0.3667(15) 0.6879(5) 0.056(2) Uani 1 1 d . . . . .
H3A H 0.814716 0.346889 0.658849 0.067 Uiso 1 1 calc R U . . .
H3B H 0.786123 0.514751 0.696899 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8273(4) 0.2517(11) 0.7733(4) 0.0445(17) Uani 1 1 d . . . . .
H4 H 0.877679 0.303671 0.808317 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7862(3) 0.2882(12) 0.8199(4) 0.0413(16) Uani 1 1 d . . . . .
H5A H 0.784031 0.436269 0.828912 0.050 Uiso 1 1 calc R U . . .
H5B H 0.811948 0.220162 0.874864 0.050 Uiso 1 1 calc R U . . .
C6 C 0.7079(3) 0.1998(10) 0.7663(4) 0.0338(14) Uani 1 1 d . . . . .
H6 H 0.704295 0.081060 0.797198 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8738(5) -0.1052(14) 0.8362(6) 0.066(2) Uani 1 1 d . . . . .
H7 H 0.855431 -0.121515 0.871642 0.079 Uiso 1 1 calc R U . . .
C8 C 0.9349(6) -0.190(2) 0.8588(9) 0.123(5) Uani 1 1 d . . . . .
H8A H 0.955068 -0.176620 0.824993 0.148 Uiso 1 1 calc R U . . .
H8B H 0.959648 -0.264529 0.909340 0.148 Uiso 1 1 calc R U . . .
C9 C 0.8289(3) 0.0190(12) 0.7565(4) 0.0430(17) Uani 1 1 d . . . . .
H9 H 0.850687 0.002517 0.721473 0.052 Uiso 1 1 calc R U . . .
C10 C 0.7488(4) -0.0589(11) 0.7044(5) 0.0451(17) Uani 1 1 d . . . . .
H10A H 0.739645 -0.122655 0.652107 0.054 Uiso 1 1 calc R U . . .
H10B H 0.740755 -0.163294 0.736675 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6477(3) 0.3615(11) 0.7522(4) 0.0362(15) Uani 1 1 d . . . . .
H11 H 0.599379 0.311271 0.707549 0.043 Uiso 1 1 calc R U . . .
C13 C 0.6503(3) 0.3736(11) 0.8352(4) 0.0347(15) Uani 1 1 d . . . . .
C14 C 0.6863(3) 0.5315(12) 0.8900(4) 0.0438(17) Uani 1 1 d . . . . .
H14 H 0.706457 0.639635 0.875248 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6927(4) 0.5292(13) 0.9701(4) 0.0486(18) Uani 1 1 d . . . . .
H15 H 0.716706 0.641532 1.005914 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6305(3) 0.2274(12) 0.9432(4) 0.0403(16) Uani 1 1 d . . . . .
C18 C 0.6180(3) 0.2142(11) 0.8600(4) 0.0376(15) Uani 1 1 d . . . . .
C19 C 0.5762(3) 0.0480(11) 0.8078(4) 0.0418(16) Uani 1 1 d . . . . .
H19 H 0.567473 0.038222 0.752976 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5483(4) -0.0990(12) 0.8360(5) 0.0503(19) Uani 1 1 d . . . . .
C22 C 0.4863(5) -0.2814(18) 0.7059(6) 0.081(3) Uani 1 1 d . . . . .
H22A H 0.455959 -0.402146 0.680723 0.122 Uiso 1 1 calc R U . . .
H22B H 0.459910 -0.159296 0.675030 0.122 Uiso 1 1 calc R U . . .
H22C H 0.530088 -0.295024 0.704038 0.122 Uiso 1 1 calc R U . . .
C23 C 0.5640(4) -0.0935(12) 0.9202(5) 0.0517(19) Uani 1 1 d . . . . .
H23 H 0.547416 -0.199113 0.940541 0.062 Uiso 1 1 calc R U . . .
C24 C 0.6035(4) 0.0678(14) 0.9712(5) 0.054(2) Uani 1 1 d . . . . .
H24 H 0.612999 0.072526 1.026441 0.064 Uiso 1 1 calc R U . . .
O25 O 0.5558(3) 0.9824(9) 0.5847(3) 0.0604(15) Uani 1 1 d . . . . .
O26 O 0.5735(4) 0.6617(11) 0.5610(4) 0.101(3) Uani 1 1 d . . . . .
C27 C 0.5381(4) 0.8213(12) 0.5420(4) 0.0493(18) Uani 1 1 d . . . . .
O91 O 0.3398(10) 0.308(3) 0.5811(11) 0.240(7) Uiso 1 1 d . . . . .
O92 O 0.1972(10) 0.241(4) 0.4966(12) 0.261(8) Uiso 1 1 d . . . . .
O90 O 0.5391(3) 0.3159(12) 0.4354(4) 0.0867(19) 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
O12 H12 0.8200 . ?
O12 C11 1.396(8) . ?
O21 C20 1.368(9) . ?
O21 C22 1.396(11) . ?
N1 H1 1.00(8) . ?
N1 C2 1.483(9) . ?
N1 C6 1.501(8) . ?
N1 C10 1.492(9) . ?
N16 C15 1.290(10) . ?
N16 C17 1.370(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.553(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(10) . ?
C4 H4 0.9800 . ?
C4 C5 1.536(9) . ?
C4 C9 1.529(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.539(8) . ?
C6 H6 0.9800 . ?
C6 C11 1.567(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.267(12) . ?
C7 C9 1.498(11) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.545(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C13 1.506(8) . ?
C13 C14 1.353(9) . ?
C13 C18 1.437(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.412(10) . ?
C15 H15 0.9300 . ?
C17 C18 1.417(9) . ?
C17 C24 1.402(11) . ?
C18 C19 1.402(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(10) . ?
C20 C23 1.410(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.357(12) . ?
C24 H24 0.9300 . ?
O25 C27 1.233(9) . ?
O26 C27 1.211(9) . ?
C27 C27 1.556(13) 2_656 ?

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
C11 O12 H12 109.5 . . ?
C20 O21 C22 117.2(6) . . ?
C2 N1 H1 107(4) . . ?
C2 N1 C6 114.5(5) . . ?
C2 N1 C10 109.0(5) . . ?
C6 N1 H1 99(4) . . ?
C10 N1 H1 119(5) . . ?
C10 N1 C6 108.1(5) . . ?
C15 N16 C17 115.8(6) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
N1 C2 C3 110.0(5) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.6(6) . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 H4 109.4 . . ?
C3 C4 C5 109.8(6) . . ?
C5 C4 H4 109.4 . . ?
C9 C4 C3 108.6(6) . . ?
C9 C4 H4 109.4 . . ?
C9 C4 C5 110.1(6) . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C4 C5 C6 109.4(5) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
N1 C6 C5 108.4(5) . . ?
N1 C6 H6 107.6 . . ?
N1 C6 C11 112.6(5) . . ?
C5 C6 H6 107.6 . . ?
C5 C6 C11 112.7(5) . . ?
C11 C6 H6 107.6 . . ?
C8 C7 H7 117.5 . . ?
C8 C7 C9 124.9(9) . . ?
C9 C7 H7 117.5 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C4 C9 H9 108.0 . . ?
C4 C9 C10 107.9(5) . . ?
C7 C9 C4 113.0(6) . . ?
C7 C9 H9 108.0 . . ?
C7 C9 C10 111.8(6) . . ?
C10 C9 H9 108.0 . . ?
N1 C10 C9 109.9(6) . . ?
N1 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O12 C11 C6 111.9(5) . . ?
O12 C11 H11 109.6 . . ?
O12 C11 C13 110.1(5) . . ?
C6 C11 H11 109.6 . . ?
C13 C11 C6 106.0(5) . . ?
C13 C11 H11 109.6 . . ?
C14 C13 C11 120.3(6) . . ?
C14 C13 C18 118.4(6) . . ?
C18 C13 C11 121.3(6) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.8(7) . . ?
C15 C14 H14 120.6 . . ?
N16 C15 C14 126.3(7) . . ?
N16 C15 H15 116.8 . . ?
C14 C15 H15 116.8 . . ?
N16 C17 C18 123.7(6) . . ?
N16 C17 C24 117.9(6) . . ?
C24 C17 C18 118.4(7) . . ?
C17 C18 C13 116.9(6) . . ?
C19 C18 C13 124.2(6) . . ?
C19 C18 C17 118.8(6) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(6) . . ?
C20 C19 H19 119.5 . . ?
O21 C20 C23 113.2(7) . . ?
C19 C20 O21 126.3(7) . . ?
C19 C20 C23 120.5(7) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 120.4 . . ?
C24 C23 C20 119.2(7) . . ?
C24 C23 H23 120.4 . . ?
C17 C24 H24 119.0 . . ?
C23 C24 C17 121.9(7) . . ?
C23 C24 H24 119.0 . . ?
O25 C27 C27 116.6(5) . 2_656 ?
O26 C27 O25 126.0(6) . . ?
O26 C27 C27 117.3(5) . 2_656 ?

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
O12 C11 C13 C14 -21.7(7) . . . . ?
O12 C11 C13 C18 161.1(5) . . . . ?
O21 C20 C23 C24 -176.8(7) . . . . ?
N1 C2 C3 C4 3.2(9) . . . . ?
N1 C6 C11 O12 -78.0(7) . . . . ?
N1 C6 C11 C13 162.0(5) . . . . ?
N16 C17 C18 C13 2.9(9) . . . . ?
N16 C17 C18 C19 -177.9(6) . . . . ?
N16 C17 C24 C23 178.6(6) . . . . ?
C2 N1 C6 C5 -57.2(7) . . . . ?
C2 N1 C6 C11 68.2(7) . . . . ?
C2 N1 C10 C9 60.1(7) . . . . ?
C2 C3 C4 C5 -61.2(8) . . . . ?
C2 C3 C4 C9 59.2(7) . . . . ?
C3 C4 C5 C6 61.7(8) . . . . ?
C3 C4 C9 C7 173.1(6) . . . . ?
C3 C4 C9 C10 -62.8(7) . . . . ?
C4 C5 C6 N1 -3.2(7) . . . . ?
C4 C5 C6 C11 -128.6(6) . . . . ?
C4 C9 C10 N1 3.0(7) . . . . ?
C5 C4 C9 C7 -66.7(7) . . . . ?
C5 C4 C9 C10 57.4(7) . . . . ?
C5 C6 C11 O12 45.0(7) . . . . ?
C5 C6 C11 C13 -75.0(6) . . . . ?
C6 N1 C2 C3 57.5(8) . . . . ?
C6 N1 C10 C9 -64.9(7) . . . . ?
C6 C11 C13 C14 99.5(7) . . . . ?
C6 C11 C13 C18 -77.6(6) . . . . ?
C7 C9 C10 N1 127.8(7) . . . . ?
C8 C7 C9 C4 -109.8(12) . . . . ?
C8 C7 C9 C10 128.2(12) . . . . ?
C9 C4 C5 C6 -57.8(7) . . . . ?
C10 N1 C2 C3 -63.7(7) . . . . ?
C10 N1 C6 C5 64.5(7) . . . . ?
C10 N1 C6 C11 -170.1(5) . . . . ?
C11 C13 C14 C15 -175.0(6) . . . . ?
C11 C13 C18 C17 173.0(5) . . . . ?
C11 C13 C18 C19 -6.2(9) . . . . ?
C13 C14 C15 N16 1.5(10) . . . . ?
C13 C18 C19 C20 178.9(6) . . . . ?
C14 C13 C18 C17 -4.1(8) . . . . ?
C14 C13 C18 C19 176.7(6) . . . . ?
C15 N16 C17 C18 0.5(9) . . . . ?
C15 N16 C17 C24 179.6(6) . . . . ?
C17 N16 C15 C14 -2.8(10) . . . . ?
C17 C18 C19 C20 -0.3(9) . . . . ?
C18 C13 C14 C15 2.2(9) . . . . ?
C18 C17 C24 C23 -2.2(10) . . . . ?
C18 C19 C20 O21 177.7(7) . . . . ?
C18 C19 C20 C23 -3.3(10) . . . . ?
C19 C20 C23 C24 4.1(10) . . . . ?
C20 C23 C24 C17 -1.3(11) . . . . ?
C22 O21 C20 C19 -1.2(11) . . . . ?
C22 O21 C20 C23 179.7(7) . . . . ?
C24 C17 C18 C13 -176.2(6) . . . . ?
C24 C17 C18 C19 3.0(9) . . . . ?

# start Validation Reply Form
_vrf_PLAT306_datam               
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O90 Check 
RESPONSE: We couldn't refine H-atoms on lattice water
;
_vrf_PLAT340_datam               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0111 Ang.  
RESPONSE: ...
;
_vrf_PLAT430_datam               
;
PROBLEM: Short Inter D...A Contact  O25      ..O90      .       2.84 Ang.  
RESPONSE: Due to hydrogen bonding existing between water and carboxylate
;
# end Validation Reply Form

_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_qn_mal
_database_code_depnum_ccdc_archive 'CCDC 2036853'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 O4, C20 H25 N2 O2'
_chemical_formula_sum            'C23 H28 N2 O6'
_chemical_formula_weight         428.47
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.6594(3)
_cell_length_b                   11.8450(5)
_cell_length_c                   26.3450(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2078.11(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4390
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1761 before and 0.1013 after correction.
The Ratio of minimum to maximum transmission is 0.5884.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17111
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.312
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3468
_reflns_number_total             3641
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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         0.407
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 
;
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.095
_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)+(0.0682P)²+0.5260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1224
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2B,H2C), C7(H7A,H7B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O -0.1123(3) 0.57766(17) 0.65348(8) 0.0198(5) Uani 1 1 d . . . . .
O2 O 0.2512(4) 0.70942(19) 0.61272(9) 0.0212(5) Uani 1 1 d . . . . .
O3 O 0.1852(4) 0.82555(19) 0.67717(8) 0.0245(5) Uani 1 1 d . . . . .
O4 O -0.3894(3) 0.67916(19) 0.64839(9) 0.0249(5) Uani 1 1 d . . . . .
O5 O 0.9509(3) 0.61697(19) 0.51217(8) 0.0208(5) Uani 1 1 d . . . . .
C25 C 0.9297(6) 0.0472(3) 0.72048(14) 0.0253(8) Uani 1 1 d . . . . .
O7 O 0.1902(3) 0.42997(18) 0.63695(8) 0.0173(5) Uani 1 1 d . . . . .
N1 N 0.2982(4) 0.3623(2) 0.44855(9) 0.0180(6) Uani 1 1 d . . . . .
N2 N 0.6345(4) 0.4012(2) 0.67642(9) 0.0144(5) Uani 1 1 d . . . . .
C1 C -0.2045(5) 0.6676(2) 0.64368(11) 0.0157(6) Uani 1 1 d . . . . .
C2 C -0.0856(5) 0.7682(3) 0.62302(12) 0.0190(7) Uani 1 1 d . . . . .
H2B H -0.086526 0.765205 0.585464 0.023 Uiso 1 1 calc R U . . .
H2C H -0.153454 0.838912 0.633415 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1292(5) 0.7716(2) 0.64114(11) 0.0155(6) Uani 1 1 d . . . . .
C4 C 0.8018(5) 0.1073(3) 0.69333(12) 0.0196(7) Uani 1 1 d . . . . .
H4 H 0.775410 0.084663 0.659387 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6958(5) 0.2103(2) 0.71372(11) 0.0163(6) Uani 1 1 d . . . . .
H5 H 0.711765 0.211469 0.751459 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4696(5) 0.2160(2) 0.70121(11) 0.0159(6) Uani 1 1 d . . . . .
H6 H 0.403414 0.143378 0.710897 0.019 Uiso 1 1 calc R U . . .
C7 C 0.4372(5) 0.2388(2) 0.64451(11) 0.0159(6) Uani 1 1 d . . . . .
H7A H 0.291759 0.237509 0.636690 0.019 Uiso 1 1 calc R U . . .
H7B H 0.503356 0.179050 0.624224 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5260(5) 0.3552(2) 0.63046(10) 0.0134(6) Uani 1 1 d . . . . .
H8 H 0.628862 0.342509 0.603402 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3718(5) 0.4405(2) 0.60940(10) 0.0140(6) Uani 1 1 d . . . . .
H9 H 0.425376 0.518792 0.613752 0.017 Uiso 1 1 calc R U . . .
C10 C 0.3435(5) 0.4168(2) 0.55328(11) 0.0138(6) Uani 1 1 d . . . . .
C11 C 0.4909(5) 0.4529(2) 0.51714(11) 0.0139(6) Uani 1 1 d . . . . .
C12 C 0.6614(5) 0.5172(2) 0.53058(11) 0.0146(6) Uani 1 1 d . . . . .
H12 H 0.683107 0.536832 0.565111 0.017 Uiso 1 1 calc R U . . .
C13 C 0.7962(5) 0.5518(2) 0.49430(11) 0.0160(6) Uani 1 1 d . . . . .
C14 C 1.1022(5) 0.6532(3) 0.47703(12) 0.0217(7) Uani 1 1 d . . . . .
H14A H 1.156640 0.587486 0.459111 0.033 Uiso 1 1 calc R U . . .
H14B H 1.210342 0.691329 0.495523 0.033 Uiso 1 1 calc R U . . .
H14C H 1.042858 0.705558 0.452434 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1800(5) 0.3581(2) 0.53520(11) 0.0162(6) Uani 1 1 d . . . . .
H15 H 0.077492 0.334124 0.557842 0.019 Uiso 1 1 calc R U . . .
C16 C 0.1655(5) 0.3337(2) 0.48328(11) 0.0175(7) Uani 1 1 d . . . . .
H16 H 0.050385 0.293195 0.472226 0.021 Uiso 1 1 calc R U . . .
C17 C 0.4620(5) 0.4229(2) 0.46538(11) 0.0152(6) Uani 1 1 d . . . . .
C18 C 0.6052(5) 0.4587(3) 0.42924(11) 0.0178(7) Uani 1 1 d . . . . .
H18 H 0.587553 0.438476 0.394634 0.021 Uiso 1 1 calc R U . . .
C19 C 0.7699(5) 0.5221(2) 0.44293(11) 0.0169(6) Uani 1 1 d . . . . .
H19 H 0.864494 0.545465 0.418076 0.020 Uiso 1 1 calc R U . . .
C20 C 0.3802(5) 0.3132(3) 0.73246(11) 0.0192(7) Uani 1 1 d . . . . .
H20A H 0.389094 0.295476 0.769117 0.023 Uiso 1 1 calc R U . . .
H20B H 0.236931 0.323660 0.723598 0.023 Uiso 1 1 calc R U . . .
C21 C 0.4986(5) 0.4223(3) 0.72083(11) 0.0176(6) Uani 1 1 d . . . . .
H21A H 0.404331 0.484427 0.712845 0.021 Uiso 1 1 calc R U . . .
H21B H 0.578969 0.444546 0.750812 0.021 Uiso 1 1 calc R U . . .
C22 C 0.7942(5) 0.3182(3) 0.69174(12) 0.0182(7) Uani 1 1 d . . . . .
H22A H 0.882940 0.352716 0.717576 0.022 Uiso 1 1 calc R U . . .
H22B H 0.877071 0.298264 0.661866 0.022 Uiso 1 1 calc R U . . .
H25A H 0.943(6) 0.060(3) 0.7533(16) 0.025(10) Uiso 1 1 d . . . . .
H25B H 0.995(5) -0.018(3) 0.7039(14) 0.024(9) Uiso 1 1 d . . . . .
H2A H 0.361(8) 0.716(4) 0.6242(18) 0.049(14) Uiso 1 1 d . . . . .
H7 H 0.105(8) 0.488(4) 0.6338(17) 0.050(13) Uiso 1 1 d . . . . .
H2 H 0.691(6) 0.470(3) 0.6702(14) 0.031(10) 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
O1 C1 1.256(4) . ?
O2 C3 1.328(4) . ?
O2 H2A 0.80(6) . ?
O3 C3 1.204(4) . ?
O4 C1 1.245(4) . ?
O5 C13 1.371(4) . ?
O5 C14 1.434(4) . ?
C25 C4 1.321(5) . ?
C25 H25A 0.88(4) . ?
C25 H25B 0.99(4) . ?
O7 C9 1.416(4) . ?
O7 H7 0.90(5) . ?
N1 C16 1.316(4) . ?
N1 C17 1.379(4) . ?
N2 C8 1.511(4) . ?
N2 C21 1.500(4) . ?
N2 C22 1.504(4) . ?
N2 H2 0.92(4) . ?
C1 C2 1.531(4) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C2 C3 1.508(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.508(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.544(4) . ?
C5 C22 1.548(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.533(4) . ?
C6 C20 1.535(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.546(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.544(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.516(4) . ?
C10 C11 1.433(4) . ?
C10 C15 1.377(4) . ?
C11 C12 1.412(4) . ?
C11 C17 1.422(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(4) . ?
C13 C19 1.409(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.401(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(5) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.544(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 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
C3 O2 H2A 107(4) . . ?
C13 O5 C14 118.3(2) . . ?
C4 C25 H25A 120(2) . . ?
C4 C25 H25B 118(2) . . ?
H25A C25 H25B 122(3) . . ?
C9 O7 H7 115(3) . . ?
C16 N1 C17 116.2(3) . . ?
C8 N2 H2 112(2) . . ?
C21 N2 C8 113.4(2) . . ?
C21 N2 C22 109.0(2) . . ?
C21 N2 H2 104(2) . . ?
C22 N2 C8 108.5(2) . . ?
C22 N2 H2 110(2) . . ?
O1 C1 C2 118.7(3) . . ?
O4 C1 O1 123.8(3) . . ?
O4 C1 C2 117.5(3) . . ?
C1 C2 H2B 108.9 . . ?
C1 C2 H2C 108.9 . . ?
H2B C2 H2C 107.7 . . ?
C3 C2 C1 113.5(2) . . ?
C3 C2 H2B 108.9 . . ?
C3 C2 H2C 108.9 . . ?
O2 C3 C2 112.8(3) . . ?
O3 C3 O2 123.4(3) . . ?
O3 C3 C2 123.8(3) . . ?
C25 C4 H4 118.5 . . ?
C25 C4 C5 123.0(3) . . ?
C5 C4 H4 118.5 . . ?
C4 C5 H5 108.4 . . ?
C4 C5 C6 114.6(3) . . ?
C4 C5 C22 109.6(2) . . ?
C6 C5 H5 108.4 . . ?
C6 C5 C22 107.3(2) . . ?
C22 C5 H5 108.4 . . ?
C5 C6 H6 109.7 . . ?
C7 C6 C5 110.7(2) . . ?
C7 C6 H6 109.7 . . ?
C7 C6 C20 109.7(2) . . ?
C20 C6 C5 107.3(3) . . ?
C20 C6 H6 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C6 C7 C8 109.6(2) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
N2 C8 C7 108.2(2) . . ?
N2 C8 H8 107.3 . . ?
N2 C8 C9 111.7(2) . . ?
C7 C8 H8 107.3 . . ?
C9 C8 C7 114.5(2) . . ?
C9 C8 H8 107.3 . . ?
O7 C9 C8 109.0(2) . . ?
O7 C9 H9 109.1 . . ?
O7 C9 C10 112.2(2) . . ?
C8 C9 H9 109.1 . . ?
C10 C9 C8 108.2(2) . . ?
C10 C9 H9 109.1 . . ?
C11 C10 C9 120.5(3) . . ?
C15 C10 C9 121.9(3) . . ?
C15 C10 C11 117.6(3) . . ?
C12 C11 C10 123.0(3) . . ?
C12 C11 C17 119.0(3) . . ?
C17 C11 C10 118.0(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
O5 C13 C12 114.8(3) . . ?
O5 C13 C19 124.3(3) . . ?
C12 C13 C19 120.8(3) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15 120.1 . . ?
C10 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
N1 C16 C15 125.4(3) . . ?
N1 C16 H16 117.3 . . ?
C15 C16 H16 117.3 . . ?
N1 C17 C11 123.1(3) . . ?
N1 C17 C18 118.3(3) . . ?
C18 C17 C11 118.7(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.7(3) . . ?
C19 C18 H18 119.2 . . ?
C13 C19 H19 120.4 . . ?
C18 C19 C13 119.1(3) . . ?
C18 C19 H19 120.4 . . ?
C6 C20 H20A 109.9 . . ?
C6 C20 H20B 109.9 . . ?
C6 C20 C21 108.8(2) . . ?
H20A C20 H20B 108.3 . . ?
C21 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
N2 C21 C20 108.9(2) . . ?
N2 C21 H21A 109.9 . . ?
N2 C21 H21B 109.9 . . ?
C20 C21 H21A 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
N2 C22 C5 109.9(2) . . ?
N2 C22 H22A 109.7 . . ?
N2 C22 H22B 109.7 . . ?
C5 C22 H22A 109.7 . . ?
C5 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?

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
O1 C1 C2 C3 -29.9(4) . . . . ?
O4 C1 C2 C3 152.2(3) . . . . ?
O5 C13 C19 C18 -178.2(3) . . . . ?
C25 C4 C5 C6 -135.3(3) . . . . ?
C25 C4 C5 C22 104.1(4) . . . . ?
O7 C9 C10 C11 162.4(2) . . . . ?
O7 C9 C10 C15 -19.2(4) . . . . ?
N1 C17 C18 C19 178.2(3) . . . . ?
N2 C8 C9 O7 -84.0(3) . . . . ?
N2 C8 C9 C10 153.7(2) . . . . ?
C1 C2 C3 O2 85.3(3) . . . . ?
C1 C2 C3 O3 -95.4(3) . . . . ?
C4 C5 C6 C7 -70.3(3) . . . . ?
C4 C5 C6 C20 170.1(2) . . . . ?
C4 C5 C22 N2 137.2(3) . . . . ?
C5 C6 C7 C8 -62.9(3) . . . . ?
C5 C6 C20 C21 55.3(3) . . . . ?
C6 C5 C22 N2 12.2(3) . . . . ?
C6 C7 C8 N2 6.1(3) . . . . ?
C6 C7 C8 C9 -119.3(3) . . . . ?
C6 C20 C21 N2 10.2(3) . . . . ?
C7 C6 C20 C21 -65.0(3) . . . . ?
C7 C8 C9 O7 39.5(3) . . . . ?
C7 C8 C9 C10 -82.8(3) . . . . ?
C8 N2 C21 C20 53.7(3) . . . . ?
C8 N2 C22 C5 -69.8(3) . . . . ?
C8 C9 C10 C11 -77.3(3) . . . . ?
C8 C9 C10 C15 101.1(3) . . . . ?
C9 C10 C11 C12 -3.9(4) . . . . ?
C9 C10 C11 C17 176.6(3) . . . . ?
C9 C10 C15 C16 -177.0(3) . . . . ?
C10 C11 C12 C13 -178.6(3) . . . . ?
C10 C11 C17 N1 0.8(4) . . . . ?
C10 C11 C17 C18 179.5(3) . . . . ?
C10 C15 C16 N1 0.2(5) . . . . ?
C11 C10 C15 C16 1.4(4) . . . . ?
C11 C12 C13 O5 177.8(2) . . . . ?
C11 C12 C13 C19 -1.2(4) . . . . ?
C11 C17 C18 C19 -0.5(4) . . . . ?
C12 C11 C17 N1 -178.7(3) . . . . ?
C12 C11 C17 C18 0.0(4) . . . . ?
C12 C13 C19 C18 0.7(4) . . . . ?
C14 O5 C13 C12 177.8(3) . . . . ?
C14 O5 C13 C19 -3.2(4) . . . . ?
C15 C10 C11 C12 177.6(3) . . . . ?
C15 C10 C11 C17 -1.8(4) . . . . ?
C16 N1 C17 C11 0.7(4) . . . . ?
C16 N1 C17 C18 -178.0(3) . . . . ?
C17 N1 C16 C15 -1.2(4) . . . . ?
C17 C11 C12 C13 0.8(4) . . . . ?
C17 C18 C19 C13 0.1(4) . . . . ?
C20 C6 C7 C8 55.3(3) . . . . ?
C21 N2 C8 C7 -63.2(3) . . . . ?
C21 N2 C8 C9 63.8(3) . . . . ?
C21 N2 C22 C5 54.1(3) . . . . ?
C22 N2 C8 C7 58.1(3) . . . . ?
C22 N2 C8 C9 -174.9(2) . . . . ?
C22 N2 C21 C20 -67.3(3) . . . . ?
C22 C5 C6 C7 51.6(3) . . . . ?
C22 C5 C6 C20 -68.0(3) . . . . ?

_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_datam_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2036852'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H25 N2 O2, C7 H5 O4'
_chemical_formula_sum            'C27 H30 N2 O6'
_chemical_formula_weight         478.53
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.978(4)
_cell_length_b                   9.713(5)
_cell_length_c                   28.903(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2520(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2778
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1155
_diffrn_reflns_av_unetI/netI     0.1201
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18342
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.244
_diffrn_reflns_theta_min         3.090
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1891
_reflns_number_total             4541
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.214
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      0.746
_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)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(2)
 1(2)
2. 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 C(H,H,H) groups, All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
5.a Ternary CH refined with riding coordinates:
 C32(H32), C34(H34), N38(H38), C43(H43), C47(H47)
5.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B)
5.c Me refined with riding coordinates:
 C45(H45A,H45B,H45C)
5.d Aromatic/amide H refined with riding coordinates:
 C31(H31), C39(H39), C44(H44), C46(H46), C48(H48), C10(H10), C11(H11),
 C12(H12), C91(H91)
5.e Tetrahedral OH refined with riding coordinates:
 O15(H15), O20(H20)
;
_atom_sites_solution_hydrogens   mixed
_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
O50 O 0.7788(4) 0.1925(3) 0.05355(12) 0.0743(10) Uani 1 1 d . U . . .
O51 O 0.9322(5) 0.8422(4) 0.10305(12) 0.0619(11) Uani 1 1 d . U . . .
N49 N 0.6592(5) 0.6757(5) -0.03784(14) 0.0737(13) Uani 1 1 d . U . . .
C30 C 0.8055(6) 0.8980(5) 0.20502(18) 0.0735(16) Uani 1 1 d . U . . .
H30A H 0.840312 0.968944 0.184015 0.088 Uiso 1 1 calc R U . . .
H30B H 0.809536 0.934012 0.236292 0.088 Uiso 1 1 calc R U . . .
C31 C 0.6888(6) 0.3144(6) -0.00955(18) 0.0817(18) Uani 1 1 d . U . . .
H31 H 0.663621 0.230346 -0.022815 0.098 Uiso 1 1 calc R U . . .
C32 C 0.8644(5) 0.7119(5) 0.09711(14) 0.0486(12) Uani 1 1 d . U . . .
H32 H 0.940541 0.640315 0.100590 0.058 Uiso 1 1 calc R U . . .
C33 C 0.7555(6) 0.3184(6) 0.03422(16) 0.0614(14) Uani 1 1 d . U . . .
C34 C 0.6465(6) 0.8575(5) 0.19293(16) 0.0592(14) Uani 1 1 d . U . . .
H34 H 0.580398 0.936645 0.197535 0.071 Uiso 1 1 calc R U . . .
C35 C 0.6938(6) 0.5614(6) -0.01288(16) 0.0606(14) Uani 1 1 d . U . . .
C36 C 0.7941(5) 0.6983(5) 0.04977(15) 0.0535(12) Uani 1 1 d . U . . .
C37 C 0.7617(5) 0.5658(5) 0.03105(15) 0.0507(12) Uani 1 1 d . U . . .
N38 N 0.8157(5) 0.6565(4) 0.18055(12) 0.0574(11) Uani 1 1 d . U . . .
H38 H 0.882417 0.577775 0.176025 0.069 Uiso 1 1 calc R U . . .
C39 C 0.6612(7) 0.4319(7) -0.03228(18) 0.0821(17) Uani 1 1 d . U . . .
H39 H 0.619371 0.427809 -0.061688 0.099 Uiso 1 1 calc R U . . .
C40 C 0.9038(6) 0.7712(6) 0.20103(16) 0.0706(16) Uani 1 1 d . U . . .
H40A H 0.989132 0.791236 0.181580 0.085 Uiso 1 1 calc R U . . .
H40B H 0.939881 0.744762 0.231390 0.085 Uiso 1 1 calc R U . . .
C41 C 0.6421(5) 0.8136(5) 0.14245(15) 0.0601(14) Uani 1 1 d . U . . .
H41A H 0.671151 0.890228 0.122923 0.072 Uiso 1 1 calc R U . . .
H41B H 0.541376 0.787028 0.134169 0.072 Uiso 1 1 calc R U . . .
C42 C 0.6952(6) 0.6143(5) 0.21338(17) 0.0716(16) Uani 1 1 d . U . . .
H42A H 0.738902 0.577542 0.241481 0.086 Uiso 1 1 calc R U . . .
H42B H 0.634250 0.543109 0.199426 0.086 Uiso 1 1 calc R U . . .
C43 C 0.5989(6) 0.7399(5) 0.22489(16) 0.0639(15) Uani 1 1 d . U . . .
H43 H 0.622583 0.767645 0.256651 0.077 Uiso 1 1 calc R U . . .
C44 C 0.6951(6) 0.7947(6) -0.01969(18) 0.0784(17) Uani 1 1 d . U . . .
H44 H 0.675612 0.873599 -0.036885 0.094 Uiso 1 1 calc R U . . .
C45 C 0.8486(6) 0.1890(5) 0.09780(16) 0.0741(16) Uani 1 1 d . U . . .
H45A H 0.858819 0.095222 0.107747 0.111 Uiso 1 1 calc R U . . .
H45B H 0.945222 0.230889 0.095789 0.111 Uiso 1 1 calc R U . . .
H45C H 0.788698 0.238702 0.119686 0.111 Uiso 1 1 calc R U . . .
C46 C 0.7608(6) 0.8110(5) 0.02394(16) 0.0652(15) Uani 1 1 d . U . . .
H46 H 0.781607 0.898631 0.035176 0.078 Uiso 1 1 calc R U . . .
C47 C 0.7475(5) 0.6926(5) 0.13449(14) 0.0511(12) Uani 1 1 d . U . . .
H47 H 0.685878 0.614092 0.125186 0.061 Uiso 1 1 calc R U . . .
C48 C 0.7920(5) 0.4399(5) 0.05424(14) 0.0507(12) Uani 1 1 d . U . . .
H48 H 0.837089 0.440903 0.083211 0.061 Uiso 1 1 calc R U . . .
O15 O 0.3841(6) 0.4911(7) 0.11402(17) 0.146(2) Uani 1 1 d . U . . .
H15 H 0.317509 0.544108 0.121767 0.219 Uiso 1 1 calc R U . . .
O18 O 0.1486(6) 0.5692(6) 0.14747(17) 0.1204(17) Uani 1 1 d . U . . .
O19 O -0.0115(5) 0.4216(5) 0.17721(14) 0.1021(15) Uani 1 1 d . U . . .
O20 O 0.0548(6) 0.1723(5) 0.18511(13) 0.1135(16) Uani 1 1 d . U . . .
H20 H 0.005504 0.242879 0.187964 0.170 Uiso 1 1 calc R U . . .
C10 C 0.4062(13) 0.1263(12) 0.1279(3) 0.156(4) Uani 1 1 d . U . . .
H10 H 0.470860 0.055648 0.119650 0.187 Uiso 1 1 calc R U . . .
C11 C 0.4403(10) 0.2579(13) 0.1154(3) 0.158(4) Uani 1 1 d . U . . .
H11 H 0.527744 0.276058 0.099270 0.189 Uiso 1 1 calc R U . . .
C12 C 0.2780(12) 0.0943(9) 0.1525(3) 0.128(3) Uani 1 1 d . U . . .
H12 H 0.256998 0.004752 0.161760 0.154 Uiso 1 1 calc R U . . .
C13 C 0.1085(9) 0.4498(9) 0.1597(2) 0.0822(18) Uani 1 1 d . U . . .
C14 C 0.3473(9) 0.3619(9) 0.1265(3) 0.103(2) Uani 1 1 d . U . . .
C16 C 0.2139(7) 0.3341(7) 0.14980(18) 0.0715(15) Uani 1 1 d . U . . .
C17 C 0.1838(9) 0.2016(8) 0.1624(2) 0.0874(18) Uani 1 1 d . U . . .
C91 C 0.4357(7) 0.7088(6) 0.2231(2) 0.0900(19) Uani 1 1 d . U . . .
H91 H 0.395655 0.674303 0.195770 0.108 Uiso 1 1 calc R U . . .
C90 C 0.3480(12) 0.7281(10) 0.2582(4) 0.142(4) Uani 1 1 d . U . . .
H51 H 1.003(5) 0.844(5) 0.0878(13) 0.038(16) Uiso 1 1 d . . . . .
H90A H 0.258(6) 0.724(6) 0.2563(18) 0.08(2) Uiso 1 1 d . . . . .
H90B H 0.33(3) 0.784(18) 0.288(7) 0.59(15) 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
O50 C33 1.360(5) . ?
O50 C45 1.425(5) . ?
O51 C32 1.415(5) . ?
O51 H51 0.77(4) . ?
N49 C35 1.360(6) . ?
N49 C44 1.309(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C34 1.522(7) . ?
C30 C40 1.519(6) . ?
C31 H31 0.9300 . ?
C31 C33 1.400(6) . ?
C31 C39 1.340(7) . ?
C32 H32 0.9800 . ?
C32 C36 1.513(6) . ?
C32 C47 1.518(6) . ?
C33 C48 1.355(6) . ?
C34 H34 0.9800 . ?
C34 C41 1.521(6) . ?
C34 C43 1.530(6) . ?
C35 C37 1.409(6) . ?
C35 C39 1.408(7) . ?
C36 C37 1.426(6) . ?
C36 C46 1.358(6) . ?
C37 C48 1.421(6) . ?
N38 H38 0.9800 . ?
N38 C40 1.488(5) . ?
N38 C42 1.496(6) . ?
N38 C47 1.507(5) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C47 1.526(6) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.532(6) . ?
C43 H43 0.9800 . ?
C43 C91 1.497(8) . ?
C44 H44 0.9300 . ?
C44 C46 1.401(6) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46 0.9300 . ?
C47 H47 0.9800 . ?
C48 H48 0.9300 . ?
O15 H15 0.8200 . ?
O15 C14 1.346(8) . ?
O18 C13 1.265(8) . ?
O19 C13 1.221(8) . ?
O20 H20 0.8200 . ?
O20 C17 1.361(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(12) . ?
C10 C12 1.388(12) . ?
C11 H11 0.9300 . ?
C11 C14 1.349(11) . ?
C12 H12 0.9300 . ?
C12 C17 1.372(9) . ?
C13 C16 1.497(9) . ?
C14 C16 1.401(9) . ?
C16 C17 1.365(8) . ?
C91 H91 0.9300 . ?
C91 C90 1.298(10) . ?
C90 H90A 0.81(5) . ?
C90 H90B 1.0(2) . ?

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
C33 O50 C45 117.2(4) . . ?
C32 O51 H51 108(3) . . ?
C44 N49 C35 116.9(5) . . ?
H30A C30 H30B 108.4 . . ?
C34 C30 H30A 110.0 . . ?
C34 C30 H30B 110.0 . . ?
C40 C30 H30A 110.0 . . ?
C40 C30 H30B 110.0 . . ?
C40 C30 C34 108.5(4) . . ?
C33 C31 H31 120.0 . . ?
C39 C31 H31 120.0 . . ?
C39 C31 C33 119.9(5) . . ?
O51 C32 H32 108.8 . . ?
O51 C32 C36 111.6(4) . . ?
O51 C32 C47 108.7(4) . . ?
C36 C32 H32 108.8 . . ?
C36 C32 C47 110.2(4) . . ?
C47 C32 H32 108.8 . . ?
O50 C33 C31 114.3(5) . . ?
C48 C33 O50 124.8(4) . . ?
C48 C33 C31 120.9(5) . . ?
C30 C34 H34 109.5 . . ?
C30 C34 C43 108.4(4) . . ?
C41 C34 C30 108.5(4) . . ?
C41 C34 H34 109.5 . . ?
C41 C34 C43 111.3(4) . . ?
C43 C34 H34 109.5 . . ?
N49 C35 C37 123.5(5) . . ?
N49 C35 C39 118.1(5) . . ?
C39 C35 C37 118.4(5) . . ?
C37 C36 C32 120.5(4) . . ?
C46 C36 C32 121.2(4) . . ?
C46 C36 C37 118.3(4) . . ?
C35 C37 C36 117.3(5) . . ?
C35 C37 C48 118.8(5) . . ?
C48 C37 C36 123.9(4) . . ?
C40 N38 H38 108.2 . . ?
C40 N38 C42 109.7(4) . . ?
C40 N38 C47 113.1(4) . . ?
C42 N38 H38 108.2 . . ?
C42 N38 C47 109.3(4) . . ?
C47 N38 H38 108.2 . . ?
C31 C39 C35 121.8(5) . . ?
C31 C39 H39 119.1 . . ?
C35 C39 H39 119.1 . . ?
C30 C40 H40A 109.8 . . ?
C30 C40 H40B 109.8 . . ?
N38 C40 C30 109.2(4) . . ?
N38 C40 H40A 109.8 . . ?
N38 C40 H40B 109.8 . . ?
H40A C40 H40B 108.3 . . ?
C34 C41 H41A 109.6 . . ?
C34 C41 H41B 109.6 . . ?
C34 C41 C47 110.1(4) . . ?
H41A C41 H41B 108.1 . . ?
C47 C41 H41A 109.6 . . ?
C47 C41 H41B 109.6 . . ?
N38 C42 H42A 109.9 . . ?
N38 C42 H42B 109.9 . . ?
N38 C42 C43 109.1(4) . . ?
H42A C42 H42B 108.3 . . ?
C43 C42 H42A 109.9 . . ?
C43 C42 H42B 109.9 . . ?
C34 C43 C42 107.8(4) . . ?
C34 C43 H43 107.5 . . ?
C42 C43 H43 107.5 . . ?
C91 C43 C34 113.8(5) . . ?
C91 C43 C42 112.6(5) . . ?
C91 C43 H43 107.5 . . ?
N49 C44 H44 117.8 . . ?
N49 C44 C46 124.3(5) . . ?
C46 C44 H44 117.8 . . ?
O50 C45 H45A 109.5 . . ?
O50 C45 H45B 109.5 . . ?
O50 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C36 C46 C44 119.7(5) . . ?
C36 C46 H46 120.1 . . ?
C44 C46 H46 120.1 . . ?
C32 C47 C41 116.2(4) . . ?
C32 C47 H47 106.9 . . ?
N38 C47 C32 112.1(4) . . ?
N38 C47 C41 107.4(4) . . ?
N38 C47 H47 106.9 . . ?
C41 C47 H47 106.9 . . ?
C33 C48 C37 120.1(4) . . ?
C33 C48 H48 119.9 . . ?
C37 C48 H48 119.9 . . ?
C14 O15 H15 109.5 . . ?
C17 O20 H20 109.5 . . ?
C11 C10 H10 118.9 . . ?
C11 C10 C12 122.1(9) . . ?
C12 C10 H10 118.9 . . ?
C10 C11 H11 120.0 . . ?
C14 C11 C10 120.0(10) . . ?
C14 C11 H11 120.0 . . ?
C10 C12 H12 121.7 . . ?
C17 C12 C10 116.6(9) . . ?
C17 C12 H12 121.7 . . ?
O18 C13 C16 117.1(7) . . ?
O19 C13 O18 124.9(8) . . ?
O19 C13 C16 118.0(7) . . ?
O15 C14 C11 118.9(9) . . ?
O15 C14 C16 121.2(8) . . ?
C11 C14 C16 119.9(9) . . ?
C14 C16 C13 119.2(7) . . ?
C17 C16 C13 122.1(7) . . ?
C17 C16 C14 118.7(7) . . ?
O20 C17 C12 117.8(8) . . ?
O20 C17 C16 119.6(7) . . ?
C16 C17 C12 122.6(8) . . ?
C43 C91 H91 118.7 . . ?
C90 C91 C43 122.5(8) . . ?
C90 C91 H91 118.7 . . ?
C91 C90 H90A 123(5) . . ?
C91 C90 H90B 147(10) . . ?
H90A C90 H90B 84(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O50 C33 C48 C37 -179.5(5) . . . . ?
O51 C32 C36 C37 160.3(4) . . . . ?
O51 C32 C36 C46 -19.4(6) . . . . ?
O51 C32 C47 N38 -77.2(5) . . . . ?
O51 C32 C47 C41 46.8(5) . . . . ?
N49 C35 C37 C36 0.3(7) . . . . ?
N49 C35 C37 C48 179.6(5) . . . . ?
N49 C35 C39 C31 -178.5(6) . . . . ?
N49 C44 C46 C36 1.4(9) . . . . ?
C30 C34 C41 C47 59.0(5) . . . . ?
C30 C34 C43 C42 -65.8(5) . . . . ?
C30 C34 C43 C91 168.6(5) . . . . ?
C31 C33 C48 C37 0.5(7) . . . . ?
C32 C36 C37 C35 178.9(4) . . . . ?
C32 C36 C37 C48 -0.3(7) . . . . ?
C32 C36 C46 C44 -179.7(5) . . . . ?
C33 C31 C39 C35 -1.8(9) . . . . ?
C34 C30 C40 N38 7.7(5) . . . . ?
C34 C41 C47 C32 -124.6(4) . . . . ?
C34 C41 C47 N38 1.8(5) . . . . ?
C34 C43 C91 C90 -114.2(7) . . . . ?
C35 N49 C44 C46 -2.4(8) . . . . ?
C35 C37 C48 C33 -0.2(7) . . . . ?
C36 C32 C47 N38 160.3(4) . . . . ?
C36 C32 C47 C41 -75.8(5) . . . . ?
C36 C37 C48 C33 179.0(5) . . . . ?
C37 C35 C39 C31 2.1(9) . . . . ?
C37 C36 C46 C44 0.6(7) . . . . ?
N38 C42 C43 C34 8.5(5) . . . . ?
N38 C42 C43 C91 134.8(5) . . . . ?
C39 C31 C33 O50 -179.5(5) . . . . ?
C39 C31 C33 C48 0.4(9) . . . . ?
C39 C35 C37 C36 179.7(5) . . . . ?
C39 C35 C37 C48 -1.0(7) . . . . ?
C40 C30 C34 C41 -64.6(5) . . . . ?
C40 C30 C34 C43 56.4(5) . . . . ?
C40 N38 C42 C43 56.4(5) . . . . ?
C40 N38 C47 C32 67.6(5) . . . . ?
C40 N38 C47 C41 -61.1(5) . . . . ?
C41 C34 C43 C42 53.5(6) . . . . ?
C41 C34 C43 C91 -72.1(6) . . . . ?
C42 N38 C40 C30 -66.4(5) . . . . ?
C42 N38 C47 C32 -169.9(4) . . . . ?
C42 N38 C47 C41 61.4(5) . . . . ?
C42 C43 C91 C90 122.7(7) . . . . ?
C43 C34 C41 C47 -60.1(5) . . . . ?
C44 N49 C35 C37 1.5(8) . . . . ?
C44 N49 C35 C39 -177.8(6) . . . . ?
C45 O50 C33 C31 179.0(4) . . . . ?
C45 O50 C33 C48 -0.9(7) . . . . ?
C46 C36 C37 C35 -1.4(7) . . . . ?
C46 C36 C37 C48 179.4(5) . . . . ?
C47 C32 C36 C37 -78.8(5) . . . . ?
C47 C32 C36 C46 101.5(5) . . . . ?
C47 N38 C40 C30 55.9(5) . . . . ?
C47 N38 C42 C43 -68.2(5) . . . . ?
O15 C14 C16 C13 2.0(9) . . . . ?
O15 C14 C16 C17 -178.7(6) . . . . ?
O18 C13 C16 C14 -2.2(8) . . . . ?
O18 C13 C16 C17 178.5(6) . . . . ?
O19 C13 C16 C14 175.1(6) . . . . ?
O19 C13 C16 C17 -4.2(8) . . . . ?
C10 C11 C14 O15 179.5(8) . . . . ?
C10 C11 C14 C16 -1.5(13) . . . . ?
C10 C12 C17 O20 177.8(6) . . . . ?
C10 C12 C17 C16 -1.2(11) . . . . ?
C11 C10 C12 C17 2.2(14) . . . . ?
C11 C14 C16 C13 -177.0(7) . . . . ?
C11 C14 C16 C17 2.4(10) . . . . ?
C12 C10 C11 C14 -0.8(16) . . . . ?
C13 C16 C17 O20 -0.7(8) . . . . ?
C13 C16 C17 C12 178.3(6) . . . . ?
C14 C16 C17 O20 180.0(5) . . . . ?
C14 C16 C17 C12 -0.9(9) . . . . ?
# start Validation Reply Form
_vrf_PLAT245_datam               
;
PROBLEM: U(iso) H90A      Smaller than U(eq) C90       by      0.061 Ang**2
RESPONSE: The terminal C-atom of the vinyl moiety is having higher
thermal vibration even at low temperature
;
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(2)
2 1(2)

####################################################################### 
# 
# 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_datam_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2036857'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H25 N2 O2), C4 H4 O4, C4 H2 O4, 3(H2 O)'
_chemical_formula_sum            'C48 H62 N4 O15'
_chemical_formula_weight         935.01
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.5187(3)
_cell_length_b                   10.9299(6)
_cell_length_c                   17.6311(9)
_cell_angle_alpha                99.531(2)
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                106.711(2)
_cell_volume                     1165.47(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3674
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24732
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.385
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                7393
_reflns_number_total             8372
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;

_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         0.571
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 3172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         8372
_refine_ls_number_restraints     569
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.023
_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)+(0.0541P)²+0.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1131
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O64-H64
 0.907 with sigma of 0.02
 H91A-O91
 1.004 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
5. Others
 Sof(C58A)=Sof(C59A)=1-FVAR(1)
 Sof(C58)=Sof(C59)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C11(H11), C28(H28), C30(H30), C32(H32), C35(H35)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C26(H26A,H26B), C27(H27A,
 H27B), C29(H29A,H29B), C31(H31A,H31B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24), C33(H33), C38(H38),
 C39(H39), C43(H43), C47(H47), C48(H48), C52(H52), C53(H53)
6.d Tetrahedral OH refined with riding coordinates:
 O62(H62)
6.e X=CH2 refined with riding coordinates:
 C8(H8A,H8B), C34(H34A,H34B)
6.f Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C46(H46A,H46B,H46C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 1.2028(4) 0.2038(3) 0.75837(17) 0.0162(6) Uani 1 1 d . U . . .
H12 H 1.227(8) 0.218(5) 0.721(3) 0.024(14) Uiso 1 1 d . . . . .
O21 O 0.6104(4) 0.6014(3) 0.83877(16) 0.0222(6) Uani 1 1 d . U . . .
N1 N 0.6863(5) 0.0986(3) 0.70920(18) 0.0157(7) Uani 1 1 d . U . . .
H1 H 0.660(7) 0.168(4) 0.690(3) 0.020(11) Uiso 1 1 d . . . . .
N16 N 1.3038(5) 0.5147(3) 1.01264(19) 0.0194(7) Uani 1 1 d . U . . .
C2 C 0.7796(6) 0.0213(4) 0.6528(2) 0.0194(8) Uani 1 1 d . U . . .
H2A H 0.911346 0.079979 0.640066 0.023 Uiso 1 1 calc R U . . .
H2B H 0.671456 -0.019821 0.603641 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8386(6) -0.0844(4) 0.6897(2) 0.0218(8) Uani 1 1 d . U . . .
H3A H 0.998761 -0.065720 0.699246 0.026 Uiso 1 1 calc R U . . .
H3B H 0.771008 -0.170779 0.653574 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7561(6) -0.0864(4) 0.7672(2) 0.0175(8) Uani 1 1 d . U . . .
H4 H 0.785259 -0.158970 0.790066 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4742(6) 0.0115(4) 0.7217(2) 0.0171(8) Uani 1 1 d . U . . .
H5A H 0.366612 -0.018047 0.672053 0.021 Uiso 1 1 calc R U . . .
H5B H 0.415790 0.060990 0.761025 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5095(6) -0.1082(4) 0.7504(2) 0.0175(8) Uani 1 1 d . U . . .
H6 H 0.439894 -0.187097 0.707097 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4014(7) -0.1293(4) 0.8197(2) 0.0231(9) Uani 1 1 d . U . . .
H7 H 0.469393 -0.070504 0.868428 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2201(7) -0.2228(4) 0.8178(3) 0.0309(10) Uani 1 1 d . U . . .
H8A H 0.147356 -0.283507 0.770174 0.037 Uiso 1 1 calc R U . . .
H8B H 0.161836 -0.229776 0.864206 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8771(6) 0.0459(4) 0.8240(2) 0.0176(8) Uani 1 1 d . U . . .
H9A H 0.824640 0.046906 0.874315 0.021 Uiso 1 1 calc R U . . .
H9B H 1.035372 0.058017 0.834661 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8369(6) 0.1581(4) 0.7881(2) 0.0141(7) Uani 1 1 d . U . . .
H10 H 0.758114 0.202495 0.822810 0.017 Uiso 1 1 calc R U . . .
C11 C 1.0465(6) 0.2630(3) 0.7807(2) 0.0147(7) Uani 1 1 d . U . . .
H11 H 1.010101 0.312498 0.740799 0.018 Uiso 1 1 calc R U . . .
C13 C 1.1382(6) 0.3558(3) 0.8599(2) 0.0134(7) Uani 1 1 d . U . . .
C14 C 1.3127(6) 0.3446(4) 0.9080(2) 0.0165(8) Uani 1 1 d . U . . .
H14 H 1.381054 0.282035 0.890542 0.020 Uiso 1 1 calc R U . . .
C15 C 1.3896(6) 0.4263(4) 0.9832(2) 0.0189(8) Uani 1 1 d . U . . .
H15 H 1.511471 0.416999 1.014757 0.023 Uiso 1 1 calc R U . . .
C17 C 1.1306(6) 0.5282(4) 0.9658(2) 0.0167(8) Uani 1 1 d . U . . .
C18 C 1.0417(6) 0.4521(3) 0.8881(2) 0.0143(7) Uani 1 1 d . U . . .
C19 C 0.8623(6) 0.4752(4) 0.8435(2) 0.0160(8) Uani 1 1 d . U . . .
H19 H 0.802528 0.426138 0.791603 0.019 Uiso 1 1 calc R U . . .
C20 C 0.7765(6) 0.5677(4) 0.8755(2) 0.0176(8) Uani 1 1 d . U . . .
C22 C 0.5209(7) 0.5351(4) 0.7590(2) 0.0248(9) Uani 1 1 d . U . . .
H22A H 0.632679 0.556832 0.726910 0.037 Uiso 1 1 calc R U . . .
H22B H 0.396910 0.562661 0.739886 0.037 Uiso 1 1 calc R U . . .
H22C H 0.471665 0.440480 0.755709 0.037 Uiso 1 1 calc R U . . .
C23 C 0.8601(6) 0.6398(4) 0.9535(2) 0.0201(8) Uani 1 1 d . U . . .
H23 H 0.795217 0.701233 0.975728 0.024 Uiso 1 1 calc R U . . .
C24 C 1.0342(6) 0.6212(4) 0.9967(2) 0.0198(8) Uani 1 1 d . U . . .
H24 H 1.091408 0.671737 1.048449 0.024 Uiso 1 1 calc R U . . .
O36 O 1.0027(4) 0.4631(3) 0.24474(16) 0.0179(6) Uani 1 1 d . U . . .
H36 H 1.051(10) 0.446(6) 0.286(4) 0.059(18) Uiso 1 1 d . . . . .
O45 O -0.0262(4) 0.0640(3) 0.15942(17) 0.0248(6) Uani 1 1 d . U . . .
N25 N 0.6347(5) 0.5727(3) 0.29514(18) 0.0164(7) Uani 1 1 d . U . . .
H25 H 0.554(7) 0.503(5) 0.318(3) 0.027(12) Uiso 1 1 d . . . . .
N40 N 0.6282(5) 0.1605(3) -0.01409(19) 0.0205(7) Uani 1 1 d . U . . .
C26 C 0.8466(6) 0.6543(4) 0.3491(2) 0.0223(9) Uani 1 1 d . U . . .
H26A H 0.933887 0.597669 0.362613 0.027 Uiso 1 1 calc R U . . .
H26B H 0.816771 0.698806 0.398119 0.027 Uiso 1 1 calc R U . . .
C27 C 0.9734(6) 0.7561(4) 0.3074(2) 0.0230(9) Uani 1 1 d . U . . .
H27A H 1.016754 0.844442 0.341548 0.028 Uiso 1 1 calc R U . . .
H27B H 1.107418 0.736922 0.296457 0.028 Uiso 1 1 calc R U . . .
C28 C 0.8294(6) 0.7521(4) 0.2308(2) 0.0181(8) Uani 1 1 d . U . . .
H28 H 0.907213 0.822518 0.205276 0.022 Uiso 1 1 calc R U . . .
C29 C 0.7791(6) 0.6189(4) 0.1764(2) 0.0175(8) Uani 1 1 d . U . . .
H29A H 0.916520 0.605730 0.164456 0.021 Uiso 1 1 calc R U . . .
H29B H 0.686008 0.615462 0.126554 0.021 Uiso 1 1 calc R U . . .
C30 C 0.6612(6) 0.5098(4) 0.2154(2) 0.0152(8) Uani 1 1 d . U . . .
H30 H 0.511953 0.465647 0.183076 0.018 Uiso 1 1 calc R U . . .
C31 C 0.4949(6) 0.6589(4) 0.2836(2) 0.0202(8) Uani 1 1 d . U . . .
H31A H 0.458970 0.691965 0.334280 0.024 Uiso 1 1 calc R U . . .
H31B H 0.356744 0.607574 0.247038 0.024 Uiso 1 1 calc R U . . .
C32 C 0.6175(6) 0.7751(4) 0.2502(2) 0.0193(8) Uani 1 1 d . U . . .
H32 H 0.658034 0.856458 0.291870 0.023 Uiso 1 1 calc R U . . .
C33 C 0.4752(7) 0.7914(4) 0.1814(3) 0.0249(9) Uani 1 1 d . U . . .
H33 H 0.432410 0.724111 0.135408 0.030 Uiso 1 1 calc R U . . .
C34 C 0.4058(8) 0.8922(5) 0.1805(3) 0.0396(12) Uani 1 1 d . U . . .
H34A H 0.445582 0.961141 0.225591 0.048 Uiso 1 1 calc R U . . .
H34B H 0.315624 0.896436 0.134839 0.048 Uiso 1 1 calc R U . . .
C35 C 0.7736(6) 0.4040(4) 0.2206(2) 0.0154(8) Uani 1 1 d . U . . .
H35 H 0.715673 0.352200 0.259304 0.018 Uiso 1 1 calc R U . . .
C37 C 0.7205(6) 0.3138(3) 0.1400(2) 0.0149(7) Uani 1 1 d . U . . .
C38 C 0.8733(6) 0.3265(4) 0.0924(2) 0.0172(8) Uani 1 1 d . U . . .
H38 H 1.014509 0.388488 0.110821 0.021 Uiso 1 1 calc R U . . .
C39 C 0.8208(6) 0.2481(4) 0.0169(2) 0.0191(8) Uani 1 1 d . U . . .
H39 H 0.930835 0.258585 -0.014162 0.023 Uiso 1 1 calc R U . . .
C41 C 0.4744(6) 0.1462(4) 0.0328(2) 0.0179(8) Uani 1 1 d . U . . .
C42 C 0.5121(6) 0.2191(3) 0.1107(2) 0.0159(8) Uani 1 1 d . U . . .
C43 C 0.3423(6) 0.1941(4) 0.1552(2) 0.0163(8) Uani 1 1 d . U . . .
H43 H 0.365539 0.241576 0.207502 0.020 Uiso 1 1 calc R U . . .
C44 C 0.1442(6) 0.1006(4) 0.1219(2) 0.0202(8) Uani 1 1 d . U . . .
C46 C 0.0046(7) 0.1259(4) 0.2396(3) 0.0274(9) Uani 1 1 d . U . . .
H46A H 0.122500 0.105614 0.270105 0.041 Uiso 1 1 calc R U . . .
H46B H -0.130463 0.093917 0.259278 0.041 Uiso 1 1 calc R U . . .
H46C H 0.042782 0.220717 0.244441 0.041 Uiso 1 1 calc R U . . .
C47 C 0.1047(6) 0.0319(4) 0.0433(2) 0.0196(8) Uani 1 1 d . U . . .
H47 H -0.034571 -0.029493 0.020360 0.024 Uiso 1 1 calc R U . . .
C48 C 0.2658(6) 0.0536(4) 0.0004(2) 0.0202(8) Uani 1 1 d . U . . .
H48 H 0.238297 0.005931 -0.052030 0.024 Uiso 1 1 calc R U . . .
O61 O 0.5243(7) 0.7327(4) 0.4831(2) 0.0556(10) Uani 1 1 d . U . . .
O62 O 0.3468(7) 0.8811(5) 0.4771(2) 0.0629(11) Uani 1 1 d . U . . .
H62 H 0.447620 0.914417 0.454340 0.094 Uiso 1 1 calc R U . . .
O63 O -0.1487(12) 0.5998(4) 0.6155(3) 0.0900(17) Uani 1 1 d . U . . .
O64 O -0.0038(6) 0.4401(5) 0.6073(2) 0.0583(11) Uani 1 1 d D U . . .
H64 H -0.139(7) 0.394(6) 0.621(4) 0.08(2) Uiso 1 1 d D . . . .
C57 C 0.3712(9) 0.7763(7) 0.4959(3) 0.0548(16) Uani 1 1 d . U . . .
C60 C -0.0048(12) 0.5487(8) 0.5989(4) 0.0659(19) Uani 1 1 d . U . . .
C58 C 0.1908(11) 0.7223(8) 0.5354(4) 0.039(2) Uani 0.765(17) 1 d . U P A 1
H58 H 0.067(8) 0.758(5) 0.546(3) 0.030(12) Uiso 1 1 d . . . . .
C59 C 0.1879(13) 0.6171(8) 0.5622(4) 0.039(2) Uani 0.765(17) 1 d . U P A 1
H59 H 0.332(9) 0.593(5) 0.560(3) 0.043(15) Uiso 1 1 d . . . . .
C58A C 0.060(3) 0.6720(17) 0.5616(10) 0.019(6) Uiso 0.235(17) 1 d . . P A 2
C59A C 0.251(4) 0.659(3) 0.5379(14) 0.028(6) Uiso 0.235(17) 1 d . . P A 2
O50 O 0.6444(4) 0.2959(3) 0.63990(15) 0.0230(6) Uani 1 1 d . U . . .
O51 O 0.2837(5) 0.2143(3) 0.61349(16) 0.0304(7) Uani 1 1 d . U . . .
O55 O 0.4428(4) 0.3860(3) 0.37155(16) 0.0237(6) Uani 1 1 d . U . . .
O56 O 0.1097(5) 0.3997(3) 0.37965(17) 0.0285(7) Uani 1 1 d . U . . .
C49 C 0.4603(7) 0.2746(4) 0.5973(2) 0.0210(8) Uani 1 1 d . U . . .
C52 C 0.4598(6) 0.3220(4) 0.5222(2) 0.0219(9) Uani 1 1 d . U . . .
H52 H 0.594679 0.353473 0.505683 0.026 Uiso 1 1 calc R U . . .
C53 C 0.2791(6) 0.3219(4) 0.4780(2) 0.0217(9) Uani 1 1 d . U . . .
H53 H 0.143831 0.288061 0.493798 0.026 Uiso 1 1 calc R U . . .
C54 C 0.2790(6) 0.3729(4) 0.4040(2) 0.0207(8) Uani 1 1 d . U . . .
O90 O 0.0271(7) 0.9982(5) 0.5028(3) 0.0533(10) Uani 1 1 d . U . . .
H90A H 0.123(10) 0.954(6) 0.482(4) 0.055(18) Uiso 1 1 d . . . . .
H90B H 0.122(15) 1.091(10) 0.534(6) 0.12(3) Uiso 1 1 d . . . . .
H91A H 0.814(5) 0.004(5) 0.446(3) 0.043(14) Uiso 1 1 d D . . . .
O91 O 0.6538(6) -0.0027(4) 0.4200(2) 0.0470(9) Uani 1 1 d D U . . .
H91B H 0.662(11) 0.086(8) 0.405(4) 0.08(2) Uiso 1 1 d . . . . .
O92 O 0.7005(6) 0.2241(4) 0.3737(2) 0.0381(8) Uani 1 1 d . U . . .
H92A H 0.604(13) 0.276(8) 0.376(5) 0.09(2) Uiso 1 1 d . . . . .
H92B H 0.826(13) 0.282(8) 0.378(4) 0.07(2) 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
O12 H12 0.73(5) . ?
O12 C11 1.418(4) . ?
O21 C20 1.361(5) . ?
O21 C22 1.431(5) . ?
N1 H1 0.93(5) . ?
N1 C2 1.498(5) . ?
N1 C5 1.503(5) . ?
N1 C10 1.517(5) . ?
N16 C15 1.318(5) . ?
N16 C17 1.368(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.534(5) . ?
C4 H4 1.0000 . ?
C4 C6 1.537(5) . ?
C4 C9 1.542(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.543(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.504(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.315(6) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.548(5) . ?
C11 H11 1.0000 . ?
C11 C13 1.518(5) . ?
C13 C14 1.375(5) . ?
C13 C18 1.428(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.409(5) . ?
C15 H15 0.9500 . ?
C17 C18 1.430(5) . ?
C17 C24 1.414(6) . ?
C18 C19 1.430(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.368(5) . ?
C20 C23 1.416(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.368(6) . ?
C24 H24 0.9500 . ?
O36 H36 0.83(7) . ?
O36 C35 1.420(4) . ?
O45 C44 1.362(5) . ?
O45 C46 1.423(5) . ?
N25 H25 0.98(5) . ?
N25 C26 1.509(5) . ?
N25 C30 1.513(5) . ?
N25 C31 1.507(5) . ?
N40 C39 1.323(5) . ?
N40 C41 1.371(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.536(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.530(5) . ?
C28 H28 1.0000 . ?
C28 C29 1.526(5) . ?
C28 C32 1.544(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.539(5) . ?
C30 H30 1.0000 . ?
C30 C35 1.546(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.544(6) . ?
C32 H32 1.0000 . ?
C32 C33 1.495(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.307(6) . ?
C34 H34A 0.9500 . ?
C34 H34B 0.9500 . ?
C35 H35 1.0000 . ?
C35 C37 1.524(5) . ?
C37 C38 1.375(5) . ?
C37 C42 1.420(5) . ?
C38 H38 0.9500 . ?
C38 C39 1.400(6) . ?
C39 H39 0.9500 . ?
C41 C42 1.422(5) . ?
C41 C48 1.419(5) . ?
C42 C43 1.427(5) . ?
C43 H43 0.9500 . ?
C43 C44 1.379(5) . ?
C44 C47 1.416(6) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47 0.9500 . ?
C47 C48 1.361(6) . ?
C48 H48 0.9500 . ?
O61 C57 1.253(8) . ?
O62 H62 0.8400 . ?
O62 C57 1.289(8) . ?
O63 C60 1.263(9) . ?
O63 C58A 1.827(19) . ?
O64 H64 0.97(3) . ?
O64 C60 1.222(9) . ?
C57 C58 1.472(9) . ?
C57 C59A 1.64(3) . ?
C60 C59 1.544(12) . ?
C60 C58A 1.569(19) . ?
C58 H58 1.02(5) . ?
C58 C59 1.310(12) . ?
C59 H59 1.05(6) . ?
C58A H58 1.01(5) . ?
C58A C59A 1.40(3) . ?
C59A H59 1.10(6) . ?
O50 C49 1.267(5) . ?
O51 C49 1.246(5) . ?
O55 C54 1.259(5) . ?
O56 C54 1.262(5) . ?
C49 C52 1.499(5) . ?
C52 H52 0.9500 . ?
C52 C53 1.325(5) . ?
C53 H53 0.9500 . ?
C53 C54 1.501(5) . ?
O90 H90A 0.96(7) . ?
O90 H90B 1.03(10) . ?
O91 H91A 1.06(3) . ?
O91 H91B 1.03(8) . ?
O92 H92A 0.97(9) . ?
O92 H92B 0.86(8) . ?

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
C11 O12 H12 109(4) . . ?
C20 O21 C22 116.7(3) . . ?
C2 N1 H1 112(3) . . ?
C2 N1 C5 109.4(3) . . ?
C2 N1 C10 113.2(3) . . ?
C5 N1 H1 108(3) . . ?
C5 N1 C10 108.5(3) . . ?
C10 N1 H1 106(3) . . ?
C15 N16 C17 117.0(3) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
N1 C2 C3 109.3(3) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C2 C3 C4 109.2(3) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C3 C4 H4 109.8 . . ?
C3 C4 C6 108.2(3) . . ?
C3 C4 C9 108.5(3) . . ?
C6 C4 H4 109.8 . . ?
C6 C4 C9 110.7(3) . . ?
C9 C4 H4 109.8 . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C6 110.0(3) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C6 C5 107.9(3) . . ?
C4 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
C7 C6 C4 113.8(3) . . ?
C7 C6 C5 110.2(3) . . ?
C7 C6 H6 108.3 . . ?
C6 C7 H7 117.5 . . ?
C8 C7 C6 125.0(4) . . ?
C8 C7 H7 117.5 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C4 C9 H9A 109.7 . . ?
C4 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 C4 109.9(3) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
N1 C10 C9 108.1(3) . . ?
N1 C10 H10 107.6 . . ?
N1 C10 C11 111.1(3) . . ?
C9 C10 H10 107.6 . . ?
C9 C10 C11 114.6(3) . . ?
C11 C10 H10 107.6 . . ?
O12 C11 C10 110.5(3) . . ?
O12 C11 H11 109.6 . . ?
O12 C11 C13 109.6(3) . . ?
C10 C11 H11 109.6 . . ?
C13 C11 C10 107.9(3) . . ?
C13 C11 H11 109.6 . . ?
C14 C13 C11 120.0(3) . . ?
C14 C13 C18 118.3(3) . . ?
C18 C13 C11 121.6(3) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
N16 C15 C14 124.4(3) . . ?
N16 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
N16 C17 C18 123.3(3) . . ?
N16 C17 C24 117.8(3) . . ?
C24 C17 C18 118.8(3) . . ?
C13 C18 C17 117.2(3) . . ?
C13 C18 C19 123.9(3) . . ?
C17 C18 C19 118.9(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
O21 C20 C19 125.9(3) . . ?
O21 C20 C23 113.4(3) . . ?
C19 C20 C23 120.8(3) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.9 . . ?
C24 C23 C20 120.1(4) . . ?
C24 C23 H23 119.9 . . ?
C17 C24 H24 119.4 . . ?
C23 C24 C17 121.2(4) . . ?
C23 C24 H24 119.4 . . ?
C35 O36 H36 113(5) . . ?
C44 O45 C46 117.2(3) . . ?
C26 N25 H25 111(3) . . ?
C26 N25 C30 114.2(3) . . ?
C30 N25 H25 108(3) . . ?
C31 N25 H25 107(3) . . ?
C31 N25 C26 108.5(3) . . ?
C31 N25 C30 108.2(3) . . ?
C39 N40 C41 116.4(3) . . ?
N25 C26 H26A 109.9 . . ?
N25 C26 H26B 109.9 . . ?
N25 C26 C27 108.7(3) . . ?
H26A C26 H26B 108.3 . . ?
C27 C26 H26A 109.9 . . ?
C27 C26 H26B 109.9 . . ?
C26 C27 H27A 109.8 . . ?
C26 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C28 C27 C26 109.3(3) . . ?
C28 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
C27 C28 H28 109.7 . . ?
C27 C28 C32 108.1(3) . . ?
C29 C28 C27 109.1(3) . . ?
C29 C28 H28 109.7 . . ?
C29 C28 C32 110.6(3) . . ?
C32 C28 H28 109.7 . . ?
C28 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C28 C29 C30 110.1(3) . . ?
H29A C29 H29B 108.2 . . ?
C30 C29 H29A 109.6 . . ?
C30 C29 H29B 109.6 . . ?
N25 C30 C29 108.2(3) . . ?
N25 C30 H30 107.5 . . ?
N25 C30 C35 111.8(3) . . ?
C29 C30 H30 107.5 . . ?
C29 C30 C35 114.0(3) . . ?
C35 C30 H30 107.5 . . ?
N25 C31 H31A 109.7 . . ?
N25 C31 H31B 109.7 . . ?
N25 C31 C32 109.9(3) . . ?
H31A C31 H31B 108.2 . . ?
C32 C31 H31A 109.7 . . ?
C32 C31 H31B 109.7 . . ?
C28 C32 C31 107.8(3) . . ?
C28 C32 H32 108.2 . . ?
C31 C32 H32 108.2 . . ?
C33 C32 C28 113.3(3) . . ?
C33 C32 C31 110.9(3) . . ?
C33 C32 H32 108.2 . . ?
C32 C33 H33 117.9 . . ?
C34 C33 C32 124.3(4) . . ?
C34 C33 H33 117.9 . . ?
C33 C34 H34A 120.0 . . ?
C33 C34 H34B 120.0 . . ?
H34A C34 H34B 120.0 . . ?
O36 C35 C30 110.2(3) . . ?
O36 C35 H35 109.4 . . ?
O36 C35 C37 110.5(3) . . ?
C30 C35 H35 109.4 . . ?
C37 C35 C30 108.1(3) . . ?
C37 C35 H35 109.4 . . ?
C38 C37 C35 120.0(3) . . ?
C38 C37 C42 118.3(3) . . ?
C42 C37 C35 121.7(3) . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 120.0(3) . . ?
C39 C38 H38 120.0 . . ?
N40 C39 C38 124.3(4) . . ?
N40 C39 H39 117.8 . . ?
C38 C39 H39 117.8 . . ?
N40 C41 C42 123.8(3) . . ?
N40 C41 C48 117.3(3) . . ?
C48 C41 C42 118.9(4) . . ?
C37 C42 C41 117.2(3) . . ?
C37 C42 C43 123.6(3) . . ?
C41 C42 C43 119.3(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.7(4) . . ?
C44 C43 H43 120.2 . . ?
O45 C44 C43 125.1(4) . . ?
O45 C44 C47 114.1(3) . . ?
C43 C44 C47 120.8(4) . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C44 C47 H47 119.9 . . ?
C48 C47 C44 120.1(4) . . ?
C48 C47 H47 119.9 . . ?
C41 C48 H48 119.4 . . ?
C47 C48 C41 121.1(4) . . ?
C47 C48 H48 119.4 . . ?
C57 O62 H62 109.5 . . ?
C60 O63 C58A 57.6(7) . . ?
C60 O64 H64 110(4) . . ?
O61 C57 O62 125.0(5) . . ?
O61 C57 C58 127.9(7) . . ?
O61 C57 C59A 95.1(11) . . ?
O62 C57 C58 107.1(6) . . ?
O62 C57 C59A 139.9(11) . . ?
O63 C60 C59 122.7(7) . . ?
O63 C60 C58A 79.5(9) . . ?
O64 C60 O63 125.0(7) . . ?
O64 C60 C59 112.3(7) . . ?
O64 C60 C58A 153.9(9) . . ?
C57 C58 H58 128(3) . . ?
C59 C58 C57 117.5(8) . . ?
C59 C58 H58 114(3) . . ?
C60 C59 H59 126(3) . . ?
C58 C59 C60 120.6(7) . . ?
C58 C59 H59 113(3) . . ?
O63 C58A H58 120(3) . . ?
C60 C58A O63 42.9(5) . . ?
C60 C58A H58 163(3) . . ?
C59A C58A O63 141.6(17) . . ?
C59A C58A C60 99.0(16) . . ?
C59A C58A H58 98(4) . . ?
C57 C59A H59 123(4) . . ?
C58A C59A C57 113(2) . . ?
C58A C59A H59 121(4) . . ?
O50 C49 C52 117.0(4) . . ?
O51 C49 O50 123.8(4) . . ?
O51 C49 C52 119.2(3) . . ?
C49 C52 H52 118.6 . . ?
C53 C52 C49 122.8(4) . . ?
C53 C52 H52 118.6 . . ?
C52 C53 H53 118.6 . . ?
C52 C53 C54 122.8(4) . . ?
C54 C53 H53 118.6 . . ?
O55 C54 O56 125.4(4) . . ?
O55 C54 C53 119.1(3) . . ?
O56 C54 C53 115.6(4) . . ?
H90A O90 H90B 108(6) . . ?
H91A O91 H91B 107(5) . . ?
H92A O92 H92B 102(6) . . ?

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
O12 C11 C13 C14 -18.6(5) . . . . ?
O12 C11 C13 C18 164.2(3) . . . . ?
O21 C20 C23 C24 -177.0(3) . . . . ?
N1 C2 C3 C4 7.1(4) . . . . ?
N1 C5 C6 C4 7.9(4) . . . . ?
N1 C5 C6 C7 132.7(3) . . . . ?
N1 C10 C11 O12 -84.2(4) . . . . ?
N1 C10 C11 C13 156.1(3) . . . . ?
N16 C17 C18 C13 1.4(5) . . . . ?
N16 C17 C18 C19 -179.1(3) . . . . ?
N16 C17 C24 C23 -179.8(4) . . . . ?
C2 N1 C5 C6 56.4(4) . . . . ?
C2 N1 C10 C9 -60.5(4) . . . . ?
C2 N1 C10 C11 66.0(4) . . . . ?
C2 C3 C4 C6 56.5(4) . . . . ?
C2 C3 C4 C9 -63.6(4) . . . . ?
C3 C4 C6 C5 -64.7(4) . . . . ?
C3 C4 C6 C7 172.7(3) . . . . ?
C3 C4 C9 C10 58.6(4) . . . . ?
C4 C6 C7 C8 -132.7(4) . . . . ?
C4 C9 C10 N1 1.3(4) . . . . ?
C4 C9 C10 C11 -123.2(3) . . . . ?
C5 N1 C2 C3 -65.2(4) . . . . ?
C5 N1 C10 C9 61.2(4) . . . . ?
C5 N1 C10 C11 -172.4(3) . . . . ?
C5 C6 C7 C8 106.0(5) . . . . ?
C6 C4 C9 C10 -59.9(4) . . . . ?
C9 C4 C6 C5 54.0(4) . . . . ?
C9 C4 C6 C7 -68.6(4) . . . . ?
C9 C10 C11 O12 38.6(4) . . . . ?
C9 C10 C11 C13 -81.1(4) . . . . ?
C10 N1 C2 C3 55.9(4) . . . . ?
C10 N1 C5 C6 -67.5(4) . . . . ?
C10 C11 C13 C14 101.7(4) . . . . ?
C10 C11 C13 C18 -75.5(4) . . . . ?
C11 C13 C14 C15 -176.6(3) . . . . ?
C11 C13 C18 C17 175.5(3) . . . . ?
C11 C13 C18 C19 -3.9(5) . . . . ?
C13 C14 C15 N16 0.8(6) . . . . ?
C13 C18 C19 C20 178.7(4) . . . . ?
C14 C13 C18 C17 -1.6(5) . . . . ?
C14 C13 C18 C19 178.9(3) . . . . ?
C15 N16 C17 C18 -0.1(5) . . . . ?
C15 N16 C17 C24 179.1(3) . . . . ?
C17 N16 C15 C14 -1.1(6) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
C18 C17 C24 C23 -0.6(5) . . . . ?
C18 C19 C20 O21 178.1(3) . . . . ?
C18 C19 C20 C23 -1.4(5) . . . . ?
C19 C20 C23 C24 2.6(6) . . . . ?
C20 C23 C24 C17 -1.6(6) . . . . ?
C22 O21 C20 C19 -1.1(5) . . . . ?
C22 O21 C20 C23 178.4(3) . . . . ?
C24 C17 C18 C13 -177.8(3) . . . . ?
C24 C17 C18 C19 1.8(5) . . . . ?
O36 C35 C37 C38 -18.5(4) . . . . ?
O36 C35 C37 C42 164.2(3) . . . . ?
O45 C44 C47 C48 -176.2(3) . . . . ?
N25 C26 C27 C28 7.6(4) . . . . ?
N25 C30 C35 O36 -79.7(4) . . . . ?
N25 C30 C35 C37 159.5(3) . . . . ?
N25 C31 C32 C28 6.9(4) . . . . ?
N25 C31 C32 C33 131.5(3) . . . . ?
N40 C41 C42 C37 1.5(5) . . . . ?
N40 C41 C42 C43 -178.4(3) . . . . ?
N40 C41 C48 C47 179.1(3) . . . . ?
C26 N25 C30 C29 -58.9(4) . . . . ?
C26 N25 C30 C35 67.5(4) . . . . ?
C26 N25 C31 C32 57.7(4) . . . . ?
C26 C27 C28 C29 -63.9(4) . . . . ?
C26 C27 C28 C32 56.4(4) . . . . ?
C27 C28 C29 C30 59.3(4) . . . . ?
C27 C28 C32 C31 -64.6(4) . . . . ?
C27 C28 C32 C33 172.2(3) . . . . ?
C28 C29 C30 N25 0.1(4) . . . . ?
C28 C29 C30 C35 -124.9(3) . . . . ?
C28 C32 C33 C34 -124.7(5) . . . . ?
C29 C28 C32 C31 54.7(4) . . . . ?
C29 C28 C32 C33 -68.4(4) . . . . ?
C29 C30 C35 O36 43.5(4) . . . . ?
C29 C30 C35 C37 -77.3(4) . . . . ?
C30 N25 C26 C27 54.4(4) . . . . ?
C30 N25 C31 C32 -66.8(4) . . . . ?
C30 C35 C37 C38 102.2(4) . . . . ?
C30 C35 C37 C42 -75.2(4) . . . . ?
C31 N25 C26 C27 -66.3(4) . . . . ?
C31 N25 C30 C29 62.1(4) . . . . ?
C31 N25 C30 C35 -171.5(3) . . . . ?
C31 C32 C33 C34 113.9(5) . . . . ?
C32 C28 C29 C30 -59.4(4) . . . . ?
C35 C37 C38 C39 -176.8(3) . . . . ?
C35 C37 C42 C41 175.7(3) . . . . ?
C35 C37 C42 C43 -4.4(5) . . . . ?
C37 C38 C39 N40 0.9(6) . . . . ?
C37 C42 C43 C44 179.7(3) . . . . ?
C38 C37 C42 C41 -1.7(5) . . . . ?
C38 C37 C42 C43 178.1(3) . . . . ?
C39 N40 C41 C42 -0.1(5) . . . . ?
C39 N40 C41 C48 179.4(3) . . . . ?
C41 N40 C39 C38 -1.1(5) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
C42 C37 C38 C39 0.7(5) . . . . ?
C42 C41 C48 C47 -1.5(5) . . . . ?
C42 C43 C44 O45 176.8(3) . . . . ?
C42 C43 C44 C47 -2.0(5) . . . . ?
C43 C44 C47 C48 2.7(5) . . . . ?
C44 C47 C48 C41 -1.0(6) . . . . ?
C46 O45 C44 C43 -0.9(5) . . . . ?
C46 O45 C44 C47 177.9(3) . . . . ?
C48 C41 C42 C37 -178.0(3) . . . . ?
C48 C41 C42 C43 2.2(5) . . . . ?
O61 C57 C58 C59 1.3(9) . . . . ?
O61 C57 C59A C58A -179.4(14) . . . . ?
O62 C57 C58 C59 -177.6(5) . . . . ?
O62 C57 C59A C58A 0(2) . . . . ?
O63 C60 C59 C58 -10.9(10) . . . . ?
O63 C60 C58A C59A 175.0(13) . . . . ?
O63 C58A C59A C57 -173.7(14) . . . . ?
O64 C60 C59 C58 167.1(6) . . . . ?
O64 C60 C58A O63 161.5(19) . . . . ?
O64 C60 C58A C59A -23(3) . . . . ?
C57 C58 C59 C60 -175.5(5) . . . . ?
C60 O63 C58A C59A -8(2) . . . . ?
C60 C58A C59A C57 -179.2(12) . . . . ?
C58A O63 C60 O64 -170.2(10) . . . . ?
O50 C49 C52 C53 -170.6(4) . . . . ?
O51 C49 C52 C53 11.3(6) . . . . ?
C49 C52 C53 C54 178.2(4) . . . . ?
C52 C53 C54 O55 18.3(6) . . . . ?
C52 C53 C54 O56 -161.5(4) . . . . ?

_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_datam_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2036858'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 N2 O2, 2(C2 F3 O2), H2 O'
_chemical_formula_sum            'C24 H28 F6 N2 O7'
_chemical_formula_weight         570.48
_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'
F F 0.0171 0.0103 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.722(2)
_cell_length_b                   19.671(6)
_cell_length_c                   20.290(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2683.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3674
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23898
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          'profile data from ω-scans'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3343
_reflns_number_total             6082
_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_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_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    ?
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      0.907
_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)+(0.1112P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1813
_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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O90(H90A,H90B)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24)
2.e X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.f Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.g Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.7525(4) 0.41936(14) 0.48545(15) 0.0551(8) Uani 1 1 d . . . . .
H12 H 0.764679 0.386195 0.461300 0.083 Uiso 1 1 calc R U . . .
O21 O 0.0009(6) 0.55484(18) 0.32324(18) 0.0795(11) Uani 1 1 d . . . . .
N1 N 0.3306(6) 0.37569(16) 0.53184(19) 0.0557(9) Uani 1 1 d . . . . .
H1 H 0.300(8) 0.364(2) 0.494(2) 0.064(15) Uiso 1 1 d . . . . .
N16 N 0.6474(6) 0.66469(18) 0.44597(19) 0.0582(10) Uani 1 1 d . . . . .
H16 H 0.675(10) 0.718(3) 0.443(3) 0.102(19) Uiso 1 1 d . . . . .
C2 C 0.4260(7) 0.44473(17) 0.52940(19) 0.0469(9) Uani 1 1 d . . . . .
H2 H 0.319187 0.477863 0.522417 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5136(8) 0.4587(2) 0.59781(19) 0.0558(11) Uani 1 1 d . . . . .
H3A H 0.657538 0.460746 0.595001 0.067 Uiso 1 1 calc R U . . .
H3B H 0.465999 0.502154 0.613988 0.067 Uiso 1 1 calc R U . . .
C4 C 0.4526(7) 0.4028(2) 0.6448(2) 0.0564(11) Uani 1 1 d . . . . .
H4 H 0.501947 0.413379 0.689107 0.068 Uiso 1 1 calc R U . . .
C5 C 0.2265(8) 0.3951(2) 0.6469(2) 0.0639(13) Uani 1 1 d . . . . .
H5 H 0.200(9) 0.356(3) 0.671(3) 0.083(16) Uiso 1 1 d . . . . .
C6 C 0.1179(11) 0.4553(3) 0.6732(3) 0.0928(18) Uani 1 1 d . . . . .
H6 H 0.139328 0.497155 0.653126 0.111 Uiso 1 1 calc R U . A 2
C8 C 0.1544(8) 0.3791(3) 0.5775(2) 0.0691(13) Uani 1 1 d . . . . .
H8A H 0.084537 0.335902 0.577341 0.083 Uiso 1 1 calc R U . . .
H8B H 0.062991 0.414067 0.562804 0.083 Uiso 1 1 calc R U . . .
C9 C 0.5423(9) 0.3360(2) 0.6217(2) 0.0676(13) Uani 1 1 d . . . . .
H9A H 0.686183 0.339405 0.621015 0.081 Uiso 1 1 calc R U . . .
H9B H 0.505586 0.299779 0.651812 0.081 Uiso 1 1 calc R U . . .
C10 C 0.4662(9) 0.32008(19) 0.5535(2) 0.0643(13) Uani 1 1 d . . . . .
H10A H 0.576923 0.316163 0.523104 0.077 Uiso 1 1 calc R U . . .
H10B H 0.395140 0.277166 0.553909 0.077 Uiso 1 1 calc R U . . .
C11 C 0.5700(7) 0.45198(18) 0.4720(2) 0.0443(9) Uani 1 1 d . . . . .
H11 H 0.520(7) 0.429(2) 0.436(2) 0.048(11) Uiso 1 1 d . . . . .
C13 C 0.6007(7) 0.52693(17) 0.45840(19) 0.0454(9) Uani 1 1 d . . . . .
C14 C 0.7629(7) 0.5598(2) 0.4838(2) 0.0559(11) Uani 1 1 d . . . . .
H14 H 0.859710 0.535091 0.506186 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7846(8) 0.6297(2) 0.4766(2) 0.0596(12) Uani 1 1 d . . . . .
H15 H 0.896220 0.651440 0.493533 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4858(7) 0.63561(19) 0.4175(2) 0.0495(10) Uani 1 1 d . . . . .
C18 C 0.4570(6) 0.56500(18) 0.42227(19) 0.0451(10) Uani 1 1 d . . . . .
C19 C 0.2916(7) 0.5365(2) 0.39085(19) 0.0506(10) Uani 1 1 d . . . . .
H19 H 0.269671 0.489839 0.393204 0.061 Uiso 1 1 calc R U . . .
C20 C 0.1623(8) 0.5768(2) 0.3567(2) 0.0613(12) Uani 1 1 d . . . . .
C22 C -0.0289(11) 0.4839(3) 0.3192(4) 0.099(2) Uani 1 1 d . . . . .
H22A H -0.144435 0.474723 0.292860 0.148 Uiso 1 1 calc R U . . .
H22B H -0.047993 0.465760 0.362669 0.148 Uiso 1 1 calc R U . . .
H22C H 0.085407 0.463032 0.299350 0.148 Uiso 1 1 calc R U . . .
C23 C 0.1921(9) 0.6475(2) 0.3546(2) 0.0694(14) Uani 1 1 d . . . . .
H23 H 0.100954 0.674553 0.332251 0.083 Uiso 1 1 calc R U . . .
C24 C 0.3473(9) 0.6767(2) 0.3838(2) 0.0647(13) Uani 1 1 d . . . . .
H24 H 0.364244 0.723567 0.381926 0.078 Uiso 1 1 calc R U . . .
C7 C -0.0056(12) 0.4527(6) 0.7228(4) 0.142(3) Uani 1 1 d . . . B 2
H7A H -0.029887 0.411487 0.743888 0.170 Uiso 1 1 calc R U . B 2
H7B H -0.069240 0.491963 0.737142 0.170 Uiso 1 1 calc R U . B 2
F29 F 0.5511(8) 0.6706(4) 0.6100(3) 0.195(3) Uani 1 1 d . . . . .
F30 F 0.3374(8) 0.72507(19) 0.6591(2) 0.1283(16) Uani 1 1 d . . . . .
F31 F 0.3699(10) 0.6227(2) 0.6769(2) 0.151(2) Uani 1 1 d . . . . .
O26 O 0.2043(7) 0.59170(14) 0.5609(2) 0.0852(12) Uani 1 1 d . . . . .
O27 O 0.1539(6) 0.70199(15) 0.5467(2) 0.0832(12) Uani 1 1 d . . . . .
C25 C 0.2295(8) 0.6512(2) 0.5734(2) 0.0589(12) Uani 1 1 d . . . . .
C28 C 0.3704(10) 0.6678(3) 0.6293(3) 0.0773(16) Uani 1 1 d . . . . .
F36 F 0.6059(19) 0.3621(3) 0.2554(3) 0.276(6) Uani 1 1 d . . . . .
F37 F 0.809(2) 0.2836(6) 0.2571(4) 0.308(8) Uani 1 1 d . . . . .
F38 F 0.5234(19) 0.2633(5) 0.2604(4) 0.254(5) Uani 1 1 d . . . . .
O32 O 0.7940(7) 0.3378(2) 0.3784(3) 0.1054(15) Uani 1 1 d . . . . .
O34 O 0.5245(9) 0.2811(3) 0.3847(3) 0.1220(17) Uani 1 1 d . . . . .
C33 C 0.6591(10) 0.3111(3) 0.3527(3) 0.0758(15) Uani 1 1 d . . . . .
C35 C 0.6449(19) 0.3095(4) 0.2821(3) 0.128(3) Uani 1 1 d . . . . .
O90 O 0.1847(7) 0.3454(3) 0.4092(2) 0.0945(13) Uani 1 1 d G . . . .
H90A H 0.264305 0.323264 0.384652 0.142 Uiso 1 1 d G U . . .
H90B H 0.073698 0.343386 0.389193 0.142 Uiso 1 1 d G 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
O12 H12 0.8200 . ?
O12 C11 1.411(5) . ?
O21 C20 1.351(6) . ?
O21 C22 1.412(7) . ?
N1 H1 0.84(5) . ?
N1 C2 1.503(5) . ?
N1 C8 1.506(7) . ?
N1 C10 1.490(6) . ?
N16 H16 1.07(6) . ?
N16 C15 1.308(6) . ?
N16 C17 1.357(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.533(6) . ?
C2 C11 1.520(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.512(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.528(8) . ?
C4 C9 1.520(6) . ?
C5 H5 0.92(6) . ?
C5 C6 1.490(8) . ?
C5 C8 1.522(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.306(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.92(4) . ?
C11 C13 1.514(5) . ?
C13 C14 1.369(6) . ?
C13 C18 1.425(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(6) . ?
C15 H15 0.9300 . ?
C17 C18 1.406(5) . ?
C17 C24 1.410(7) . ?
C18 C19 1.399(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(6) . ?
C20 C23 1.405(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.329(7) . ?
C24 H24 0.9300 . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
F29 C28 1.277(8) . ?
F30 C28 1.298(6) . ?
F31 C28 1.310(6) . ?
O26 C25 1.210(5) . ?
O27 C25 1.244(5) . ?
C25 C28 1.514(8) . ?
F36 C35 1.197(9) . ?
F37 C35 1.319(15) . ?
F38 C35 1.299(12) . ?
O32 C33 1.171(7) . ?
O34 C33 1.261(8) . ?
C33 C35 1.436(10) . ?
O90 H90A 0.8499 . ?
O90 H90B 0.8500 . ?

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
C11 O12 H12 109.5 . . ?
C20 O21 C22 117.4(4) . . ?
C2 N1 H1 109(3) . . ?
C2 N1 C8 108.4(3) . . ?
C8 N1 H1 113(4) . . ?
C10 N1 H1 103(3) . . ?
C10 N1 C2 114.3(4) . . ?
C10 N1 C8 109.4(3) . . ?
C15 N16 H16 115(4) . . ?
C15 N16 C17 123.0(4) . . ?
C17 N16 H16 122(4) . . ?
N1 C2 H2 107.1 . . ?
N1 C2 C3 107.2(3) . . ?
N1 C2 C11 112.4(3) . . ?
C3 C2 H2 107.1 . . ?
C11 C2 H2 107.1 . . ?
C11 C2 C3 115.6(4) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.7(4) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 H4 109.4 . . ?
C3 C4 C5 111.1(4) . . ?
C3 C4 C9 109.1(4) . . ?
C5 C4 H4 109.4 . . ?
C9 C4 H4 109.4 . . ?
C9 C4 C5 108.5(4) . . ?
C4 C5 H5 107(4) . . ?
C6 C5 C4 114.7(5) . . ?
C6 C5 H5 112(4) . . ?
C6 C5 C8 109.9(5) . . ?
C8 C5 C4 108.2(4) . . ?
C8 C5 H5 104(3) . . ?
C5 C6 H6 118.1 . . ?
C7 C6 C5 123.8(7) . . ?
C7 C6 H6 118.1 . . ?
N1 C8 C5 109.1(4) . . ?
N1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C5 C8 H8A 109.9 . . ?
C5 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C4 C9 H9A 109.9 . . ?
C4 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 C4 109.1(4) . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
N1 C10 C9 109.0(4) . . ?
N1 C10 H10A 109.9 . . ?
N1 C10 H10B 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O12 C11 C2 111.3(3) . . ?
O12 C11 H11 104(3) . . ?
O12 C11 C13 111.1(3) . . ?
C2 C11 H11 110(3) . . ?
C13 C11 C2 108.6(3) . . ?
C13 C11 H11 112(2) . . ?
C14 C13 C11 120.0(4) . . ?
C14 C13 C18 119.1(3) . . ?
C18 C13 C11 120.9(4) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
N16 C15 C14 119.8(4) . . ?
N16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N16 C17 C18 119.8(4) . . ?
N16 C17 C24 119.6(4) . . ?
C18 C17 C24 120.6(4) . . ?
C17 C18 C13 117.5(4) . . ?
C19 C18 C13 124.2(3) . . ?
C19 C18 C17 118.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
O21 C20 C19 125.4(4) . . ?
O21 C20 C23 114.6(4) . . ?
C19 C20 C23 120.0(5) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 119.1 . . ?
C24 C23 C20 121.7(5) . . ?
C24 C23 H23 119.1 . . ?
C17 C24 H24 120.4 . . ?
C23 C24 C17 119.1(4) . . ?
C23 C24 H24 120.4 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
O26 C25 O27 129.0(5) . . ?
O26 C25 C28 116.9(4) . . ?
O27 C25 C28 114.2(4) . . ?
F29 C28 F30 105.5(6) . . ?
F29 C28 F31 105.0(7) . . ?
F29 C28 C25 112.0(5) . . ?
F30 C28 F31 104.1(5) . . ?
F30 C28 C25 115.4(5) . . ?
F31 C28 C25 113.9(5) . . ?
O32 C33 O34 122.4(7) . . ?
O32 C33 C35 120.4(8) . . ?
O34 C33 C35 117.1(7) . . ?
F36 C35 F37 110.1(11) . . ?
F36 C35 F38 108.3(10) . . ?
F36 C35 C33 116.5(7) . . ?
F37 C35 C33 109.7(9) . . ?
F38 C35 F37 97.3(8) . . ?
F38 C35 C33 113.3(9) . . ?
H90A O90 H90B 104.5 . . ?

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
O12 C11 C13 C14 -25.4(5) . . . . ?
O12 C11 C13 C18 158.1(3) . . . . ?
O21 C20 C23 C24 -178.3(5) . . . . ?
N1 C2 C3 C4 -6.7(5) . . . . ?
N1 C2 C11 O12 -77.6(4) . . . . ?
N1 C2 C11 C13 159.9(4) . . . . ?
N16 C17 C18 C13 0.9(6) . . . . ?
N16 C17 C18 C19 -178.3(4) . . . . ?
N16 C17 C24 C23 178.3(4) . . . . ?
C2 N1 C8 C5 -63.7(5) . . . . ?
C2 N1 C10 C9 59.6(5) . . . . ?
C2 C3 C4 C5 -55.6(5) . . . . ?
C2 C3 C4 C9 63.9(5) . . . . ?
C2 C11 C13 C14 97.3(5) . . . . ?
C2 C11 C13 C18 -79.2(4) . . . . ?
C3 C2 C11 O12 46.0(4) . . . . ?
C3 C2 C11 C13 -76.6(4) . . . . ?
C3 C4 C5 C6 -64.2(6) . . . . ?
C3 C4 C5 C8 58.9(5) . . . . ?
C3 C4 C9 C10 -60.2(6) . . . . ?
C4 C5 C6 C7 -124.2(7) . . . . ?
C4 C5 C8 N1 0.6(5) . . . . ?
C4 C9 C10 N1 0.5(6) . . . . ?
C5 C4 C9 C10 60.8(5) . . . . ?
C6 C5 C8 N1 126.6(5) . . . . ?
C8 N1 C2 C3 66.8(5) . . . . ?
C8 N1 C2 C11 -165.1(4) . . . . ?
C8 N1 C10 C9 -62.2(5) . . . . ?
C8 C5 C6 C7 113.6(7) . . . . ?
C9 C4 C5 C6 176.0(5) . . . . ?
C9 C4 C5 C8 -61.0(5) . . . . ?
C10 N1 C2 C3 -55.5(5) . . . . ?
C10 N1 C2 C11 72.6(4) . . . . ?
C10 N1 C8 C5 61.6(5) . . . . ?
C11 C2 C3 C4 -132.9(4) . . . . ?
C11 C13 C14 C15 -174.4(4) . . . . ?
C11 C13 C18 C17 173.5(4) . . . . ?
C11 C13 C18 C19 -7.3(6) . . . . ?
C13 C14 C15 N16 0.9(7) . . . . ?
C13 C18 C19 C20 -179.4(4) . . . . ?
C14 C13 C18 C17 -3.0(6) . . . . ?
C14 C13 C18 C19 176.2(4) . . . . ?
C15 N16 C17 C18 2.3(6) . . . . ?
C15 N16 C17 C24 -178.3(4) . . . . ?
C17 N16 C15 C14 -3.2(7) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C13 C14 C15 2.2(7) . . . . ?
C18 C17 C24 C23 -2.2(7) . . . . ?
C18 C19 C20 O21 178.3(4) . . . . ?
C18 C19 C20 C23 -1.8(7) . . . . ?
C19 C20 C23 C24 1.8(8) . . . . ?
C20 C23 C24 C17 0.2(8) . . . . ?
C22 O21 C20 C19 -4.8(8) . . . . ?
C22 O21 C20 C23 175.3(6) . . . . ?
C24 C17 C18 C13 -178.6(4) . . . . ?
C24 C17 C18 C19 2.2(6) . . . . ?
O26 C25 C28 F29 86.0(7) . . . . ?
O26 C25 C28 F30 -153.3(5) . . . . ?
O26 C25 C28 F31 -33.0(8) . . . . ?
O27 C25 C28 F29 -94.5(7) . . . . ?
O27 C25 C28 F30 26.2(8) . . . . ?
O27 C25 C28 F31 146.6(6) . . . . ?
O32 C33 C35 F36 -71.7(14) . . . . ?
O32 C33 C35 F37 54.1(11) . . . . ?
O32 C33 C35 F38 161.7(9) . . . . ?
O34 C33 C35 F36 110.4(12) . . . . ?
O34 C33 C35 F37 -123.7(10) . . . . ?
O34 C33 C35 F38 -16.2(12) . . . . ?

_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_datam_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2036855'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N2 O2, C7 H5 O3, C H4 O'
_chemical_formula_sum            'C28 H34 N2 O6'
_chemical_formula_weight         494.57
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.5291(19)
_cell_length_b                   19.368(6)
_cell_length_c                   20.431(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2583.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    778
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.1294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18359
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         3.171
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2582
_reflns_number_total             4623
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.131
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      0.825
_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)+(0.0138P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0982
_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 C(H,H,H) groups
2. Restrained distances
 O35-H35
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
3.c Me refined with riding coordinates:
 C24(H24A,H24B,H24C)
3.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C29(H29), C30(H30),
 C32(H32), C33(H33)
3.e Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   mixed
_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
O12 O 0.2448(5) 0.45558(17) 0.56199(14) 0.0449(9) Uani 1 1 d . . . . .
O23 O 1.0472(6) 0.42989(18) 0.35988(14) 0.0613(11) Uani 1 1 d . . . . .
N1 N 0.6868(6) 0.49012(17) 0.61627(17) 0.0356(9) Uani 1 1 d . . . . .
H1 H 0.733(9) 0.527(3) 0.578(3) 0.11(2) Uiso 1 1 d . . . . .
N16 N 0.3897(7) 0.25984(19) 0.41022(18) 0.0497(11) Uani 1 1 d . . . . .
C2 C 0.8608(7) 0.4701(2) 0.6605(2) 0.0435(12) Uani 1 1 d . . . . .
H2A H 0.932148 0.511246 0.675098 0.052 Uiso 1 1 calc R U . . .
H2B H 0.957327 0.441537 0.636638 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7797(8) 0.4301(2) 0.72028(19) 0.0429(12) Uani 1 1 d . . . . .
H3 H 0.786728 0.460351 0.758649 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5532(7) 0.4128(2) 0.7069(2) 0.0418(12) Uani 1 1 d . . . . .
H4 H 0.499972 0.382813 0.741524 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5285(7) 0.3776(2) 0.64025(19) 0.0404(12) Uani 1 1 d . . . . .
H5A H 0.385777 0.365826 0.633274 0.048 Uiso 1 1 calc R U . . .
H5B H 0.607945 0.335305 0.639356 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6018(7) 0.4261(2) 0.58569(18) 0.0344(11) Uani 1 1 d . . . . .
H6 H 0.715452 0.402931 0.563388 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5339(7) 0.5297(2) 0.6564(2) 0.0451(12) Uani 1 1 d . . . . .
H7A H 0.429882 0.549400 0.628096 0.054 Uiso 1 1 calc R U . . .
H7B H 0.601891 0.567154 0.679283 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4346(8) 0.4805(2) 0.7058(2) 0.0494(13) Uani 1 1 d . . . . .
H8A H 0.435807 0.501256 0.749038 0.059 Uiso 1 1 calc R U . . .
H8B H 0.293355 0.471938 0.693572 0.059 Uiso 1 1 calc R U . . .
C9 C 0.9102(8) 0.3675(3) 0.7331(3) 0.0610(16) Uani 1 1 d . . . . .
H9 H 0.905358 0.331604 0.702842 0.073 Uiso 1 1 calc R U . . .
C10 C 1.0280(12) 0.3603(5) 0.7831(4) 0.091(2) Uani 1 1 d . . . . .
C11 C 0.4386(7) 0.4425(2) 0.53315(19) 0.0355(11) Uani 1 1 d . . . . .
H11 H 0.481702 0.483081 0.508036 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4229(7) 0.3811(2) 0.48782(19) 0.0363(12) Uani 1 1 d . . . . .
C14 C 0.2628(8) 0.3359(2) 0.4943(2) 0.0438(12) Uani 1 1 d . . . . .
H14 H 0.160315 0.344301 0.524899 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2538(8) 0.2766(2) 0.4545(2) 0.0516(13) Uani 1 1 d . . . . .
H15 H 0.142776 0.247112 0.460115 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5502(8) 0.3050(2) 0.4021(2) 0.0423(12) Uani 1 1 d . . . . .
C18 C 0.5719(7) 0.3667(2) 0.4386(2) 0.0379(11) Uani 1 1 d . . . . .
C19 C 0.7420(7) 0.4105(2) 0.42492(19) 0.0403(11) Uani 1 1 d . . . . .
H19 H 0.759412 0.451233 0.448305 0.048 Uiso 1 1 calc R U . . .
C20 C 0.8789(8) 0.3926(2) 0.3777(2) 0.0474(13) Uani 1 1 d . . . . .
C21 C 0.8573(8) 0.3303(3) 0.3428(2) 0.0545(14) Uani 1 1 d . . . . .
H21 H 0.953893 0.318281 0.311363 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6978(8) 0.2878(2) 0.3547(2) 0.0516(14) Uani 1 1 d . . . . .
H22 H 0.685343 0.246756 0.331410 0.062 Uiso 1 1 calc R U . . .
C24 C 1.0802(8) 0.4938(3) 0.3928(2) 0.0689(17) Uani 1 1 d . . . . .
H24A H 1.202376 0.515111 0.376197 0.103 Uiso 1 1 calc R U . . .
H24B H 0.965386 0.523738 0.385411 0.103 Uiso 1 1 calc R U . . .
H24C H 1.095117 0.485513 0.438851 0.103 Uiso 1 1 calc R U . . .
O26 O 0.8069(6) 0.56993(18) 0.52029(16) 0.0622(11) Uani 1 1 d . . . . .
O27 O 1.1134(5) 0.58675(15) 0.56519(14) 0.0510(9) Uani 1 1 d . . . . .
O34 O 1.1400(7) 0.7927(2) 0.3227(2) 0.0640(12) Uani 1 1 d . . . . .
C25 C 0.9780(9) 0.5993(2) 0.5223(2) 0.0438(13) Uani 1 1 d . . . . .
C28 C 1.0232(8) 0.6518(2) 0.4709(2) 0.0391(12) Uani 1 1 d . . . . .
C29 C 0.8768(8) 0.6698(2) 0.4246(2) 0.0498(13) Uani 1 1 d . . . . .
H29 H 0.748103 0.649326 0.426431 0.060 Uiso 1 1 calc R U . . .
C30 C 0.9167(8) 0.7168(2) 0.3764(2) 0.0559(15) Uani 1 1 d . . . . .
H30 H 0.816149 0.728047 0.345938 0.067 Uiso 1 1 calc R U . . .
C31 C 1.1075(8) 0.7476(2) 0.3731(2) 0.0440(13) Uani 1 1 d . . . . .
C32 C 1.2540(8) 0.7313(2) 0.4186(2) 0.0461(12) Uani 1 1 d . . . . .
H32 H 1.382076 0.752215 0.416750 0.055 Uiso 1 1 calc R U . . .
C33 C 1.2108(8) 0.6836(2) 0.4673(2) 0.0451(13) Uani 1 1 d . . . . .
H33 H 1.310788 0.672993 0.498114 0.054 Uiso 1 1 calc R U . . .
O35 O 1.0094(7) 0.6487(2) 0.6793(2) 0.0800(13) Uani 1 1 d D . . . .
H35 H 1.062(9) 0.633(3) 0.6449(19) 0.10(3) Uiso 1 1 d D . . . .
C36 C 1.1438(9) 0.6445(3) 0.7320(2) 0.0761(19) Uani 1 1 d . . . . .
H36A H 1.281695 0.640781 0.716072 0.114 Uiso 1 1 calc R U . . .
H36B H 1.111316 0.604644 0.757898 0.114 Uiso 1 1 calc R U . . .
H36C H 1.131230 0.685304 0.758429 0.114 Uiso 1 1 calc R U . . .
H10A H 1.024(8) 0.401(2) 0.818(2) 0.075(19) Uiso 1 1 d . . . . .
H10B H 1.104(9) 0.321(3) 0.787(3) 0.10(3) Uiso 1 1 d . . . . .
H12 H 0.225(8) 0.500(2) 0.561(2) 0.075(19) Uiso 1 1 d . . . . .
H34 H 1.247(7) 0.806(2) 0.329(2) 0.05(2) 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
O12 C11 1.419(5) . ?
O12 H12 0.88(5) . ?
O23 C20 1.364(5) . ?
O23 C24 1.424(5) . ?
N1 H1 1.10(5) . ?
N1 C2 1.503(5) . ?
N1 C6 1.495(5) . ?
N1 C7 1.503(5) . ?
N16 C15 1.308(6) . ?
N16 C17 1.375(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.540(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.541(6) . ?
C3 C9 1.505(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.531(5) . ?
C4 C8 1.523(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.534(5) . ?
C6 H6 0.9800 . ?
C6 C11 1.545(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.532(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.288(8) . ?
C10 H10A 1.06(5) . ?
C10 H10B 0.92(5) . ?
C11 H11 0.9800 . ?
C11 C13 1.511(5) . ?
C13 C14 1.370(6) . ?
C13 C18 1.427(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.408(5) . ?
C15 H15 0.9300 . ?
C17 C18 1.416(6) . ?
C17 C22 1.406(6) . ?
C18 C19 1.424(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(6) . ?
C20 C21 1.408(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.350(6) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O26 H1 1.53(6) . ?
O26 C25 1.255(6) . ?
O27 C25 1.268(5) . ?
O34 C31 1.367(5) . ?
O34 H34 0.75(5) . ?
C25 C28 1.492(6) . ?
C28 C29 1.389(6) . ?
C28 C33 1.373(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.366(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.383(6) . ?
C31 C32 1.370(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.387(5) . ?
C33 H33 0.9300 . ?
O35 H35 0.84(3) . ?
O35 C36 1.391(6) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O12 H12 107(3) . . ?
C20 O23 C24 117.1(4) . . ?
C2 N1 H1 113(3) . . ?
C6 N1 H1 110(2) . . ?
C6 N1 C2 108.6(3) . . ?
C6 N1 C7 113.9(4) . . ?
C7 N1 H1 104(3) . . ?
C7 N1 C2 107.8(3) . . ?
C15 N16 C17 116.3(4) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C3 110.3(4) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3 108.5 . . ?
C2 C3 C4 107.3(3) . . ?
C4 C3 H3 108.5 . . ?
C9 C3 C2 110.4(4) . . ?
C9 C3 H3 108.5 . . ?
C9 C3 C4 113.6(4) . . ?
C3 C4 H4 109.9 . . ?
C5 C4 C3 110.9(4) . . ?
C5 C4 H4 109.9 . . ?
C8 C4 C3 107.7(4) . . ?
C8 C4 H4 109.9 . . ?
C8 C4 C5 108.5(4) . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.9(3) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N1 C6 C5 108.7(3) . . ?
N1 C6 H6 107.0 . . ?
N1 C6 C11 112.1(3) . . ?
C5 C6 H6 107.0 . . ?
C5 C6 C11 114.5(4) . . ?
C11 C6 H6 107.0 . . ?
N1 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
N1 C7 C8 108.9(3) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C4 C8 C7 109.2(4) . . ?
C4 C8 H8A 109.8 . . ?
C4 C8 H8B 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C3 C9 H9 117.9 . . ?
C10 C9 C3 124.2(6) . . ?
C10 C9 H9 117.9 . . ?
C9 C10 H10A 116(3) . . ?
C9 C10 H10B 119(4) . . ?
H10A C10 H10B 125(5) . . ?
O12 C11 C6 111.3(3) . . ?
O12 C11 H11 109.3 . . ?
O12 C11 C13 109.5(4) . . ?
C6 C11 H11 109.3 . . ?
C13 C11 C6 108.1(3) . . ?
C13 C11 H11 109.3 . . ?
C14 C13 C11 119.7(4) . . ?
C14 C13 C18 117.7(4) . . ?
C18 C13 C11 122.6(4) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
N16 C15 C14 125.0(5) . . ?
N16 C15 H15 117.5 . . ?
C14 C15 H15 117.5 . . ?
N16 C17 C18 123.4(4) . . ?
N16 C17 C22 117.0(4) . . ?
C22 C17 C18 119.6(5) . . ?
C17 C18 C13 117.9(4) . . ?
C17 C18 C19 118.5(4) . . ?
C19 C18 C13 123.6(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
O23 C20 C21 113.6(4) . . ?
C19 C20 O23 125.7(4) . . ?
C19 C20 C21 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(5) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 O26 H1 120(2) . . ?
C31 O34 H34 103(4) . . ?
O26 C25 O27 123.8(4) . . ?
O26 C25 C28 117.5(4) . . ?
O27 C25 C28 118.7(5) . . ?
C29 C28 C25 121.0(4) . . ?
C33 C28 C25 121.3(4) . . ?
C33 C28 C29 117.7(4) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 C28 121.8(5) . . ?
C30 C29 H29 119.1 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.6(5) . . ?
C31 C30 H30 120.2 . . ?
O34 C31 C30 116.8(5) . . ?
O34 C31 C32 123.4(5) . . ?
C32 C31 C30 119.8(4) . . ?
C31 C32 H32 120.1 . . ?
C31 C32 C33 119.9(5) . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 121.2(5) . . ?
C28 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C36 O35 H35 112(5) . . ?
O35 C36 H36A 109.5 . . ?
O35 C36 H36B 109.5 . . ?
O35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 C11 C13 C14 -19.3(5) . . . . ?
O12 C11 C13 C18 162.2(4) . . . . ?
O23 C20 C21 C22 -179.8(4) . . . . ?
N1 C2 C3 C4 10.6(5) . . . . ?
N1 C2 C3 C9 134.8(4) . . . . ?
N1 C6 C11 O12 -81.5(4) . . . . ?
N1 C6 C11 C13 158.1(4) . . . . ?
N1 C7 C8 C4 11.3(5) . . . . ?
N16 C17 C18 C13 2.3(6) . . . . ?
N16 C17 C18 C19 -178.5(4) . . . . ?
N16 C17 C22 C21 178.4(4) . . . . ?
C2 N1 C6 C5 59.1(4) . . . . ?
C2 N1 C6 C11 -173.3(3) . . . . ?
C2 N1 C7 C8 -68.1(4) . . . . ?
C2 C3 C4 C5 51.9(5) . . . . ?
C2 C3 C4 C8 -66.7(4) . . . . ?
C2 C3 C9 C10 111.4(6) . . . . ?
C3 C4 C5 C6 -61.2(5) . . . . ?
C3 C4 C8 C7 54.4(4) . . . . ?
C4 C3 C9 C10 -128.0(6) . . . . ?
C4 C5 C6 N1 3.9(5) . . . . ?
C4 C5 C6 C11 -122.3(4) . . . . ?
C5 C4 C8 C7 -65.7(5) . . . . ?
C5 C6 C11 O12 42.9(5) . . . . ?
C5 C6 C11 C13 -77.5(4) . . . . ?
C6 N1 C2 C3 -68.6(4) . . . . ?
C6 N1 C7 C8 52.4(5) . . . . ?
C6 C11 C13 C14 102.2(5) . . . . ?
C6 C11 C13 C18 -76.4(5) . . . . ?
C7 N1 C2 C3 55.2(4) . . . . ?
C7 N1 C6 C5 -61.0(5) . . . . ?
C7 N1 C6 C11 66.6(4) . . . . ?
C8 C4 C5 C6 56.9(5) . . . . ?
C9 C3 C4 C5 -70.4(5) . . . . ?
C9 C3 C4 C8 171.0(4) . . . . ?
C11 C13 C14 C15 -176.6(4) . . . . ?
C11 C13 C18 C17 175.4(4) . . . . ?
C11 C13 C18 C19 -3.8(6) . . . . ?
C13 C14 C15 N16 0.2(7) . . . . ?
C13 C18 C19 C20 179.2(4) . . . . ?
C14 C13 C18 C17 -3.2(6) . . . . ?
C14 C13 C18 C19 177.7(4) . . . . ?
C15 N16 C17 C18 -0.2(7) . . . . ?
C15 N16 C17 C22 180.0(4) . . . . ?
C17 N16 C15 C14 -1.2(7) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C13 C14 C15 2.0(6) . . . . ?
C18 C17 C22 C21 -1.4(7) . . . . ?
C18 C19 C20 O23 179.9(4) . . . . ?
C18 C19 C20 C21 -1.5(7) . . . . ?
C19 C20 C21 C22 1.5(7) . . . . ?
C20 C21 C22 C17 0.0(8) . . . . ?
C22 C17 C18 C13 -177.8(4) . . . . ?
C22 C17 C18 C19 1.4(6) . . . . ?
C24 O23 C20 C19 -1.4(7) . . . . ?
C24 O23 C20 C21 179.9(4) . . . . ?
O26 C25 C28 C29 3.1(6) . . . . ?
O26 C25 C28 C33 -176.3(4) . . . . ?
O27 C25 C28 C29 -177.0(4) . . . . ?
O27 C25 C28 C33 3.5(6) . . . . ?
O34 C31 C32 C33 -178.3(4) . . . . ?
C25 C28 C29 C30 -178.7(4) . . . . ?
C25 C28 C33 C32 178.5(4) . . . . ?
C28 C29 C30 C31 0.1(7) . . . . ?
C29 C28 C33 C32 -0.9(6) . . . . ?
C29 C30 C31 O34 178.2(4) . . . . ?
C29 C30 C31 C32 -0.7(7) . . . . ?
C30 C31 C32 C33 0.6(7) . . . . ?
C31 C32 C33 C28 0.3(7) . . . . ?
C33 C28 C29 C30 0.8(7) . . . . ?

# start Validation Reply Form
_vrf_PLAT772_datam               
;
PROBLEM: Suspect O-H Bond in CIF: O26      --H1        ..       1.53 Ang.  
RESPONSE: Quinine is in salt form and a strong charge-assisted
N-H...O hydrogen bond exist between the NH moiety and carboxylate
;
_vrf_PLAT353_datam               
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.10 Ang.  
RESPONSE: Quinine is in salt form and a strong charge-assisted
N-H...O hydrogen bond exist between the NH moiety and carboxylate
;
# end Validation Reply Form

_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_datam_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2036860'
loop_
_audit_author_name
_audit_author_address
'SUNIL VARUGHESE'
;CHEMICAL SCIENCE AND TECHNOLOGY DIVISION
India
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C20 H25 N2 O2), 2(C7 H4 N O3 S), C4 O, 4(H2 O)'
_chemical_formula_sum            'C58 H66 N6 O15 S2'
_chemical_formula_weight         1151.28
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   15.5984(5)
_cell_length_b                   15.7897(5)
_cell_length_c                   23.5416(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5798.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3674
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson, Unpublished Results'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            69164
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                16878
_reflns_number_total             17621
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_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         1.407
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     737
_refine_ls_number_reflns         17621
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.035
_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)+(0.0665P)²+2.4572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.02(5)
 -0.02(5)
2. 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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
3. Restrained distances
 O90-H90B
 0.95 with sigma of 0.02
4.a Riding coordinates:
 O12(H12), N1(H1), O36(H36), N25(H25), O90(H90A), O93(H93A,H93B), O92(H92A,
 H92B), O91(H91A,H91B)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C11(H11), C27(H27), C28(H28), C30(H30), C35(H35)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C26(H26A,H26B), C29(H29A,
 H29B), C31(H31A,H31B), C32(H32A,H32B)
4.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C33(H33), C38(H38),
 C39(H39), C43(H43), C47(H47), C48(H48), C55(H55), C56(H56), C57(H57), C58(H58),
  C66(H66), C67(H67), C68(H68), C69(H69)
4.e X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C34(H34A,H34B)
4.f Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C46(H46A,H46B,H46C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O12 O 0.72932(11) 0.25399(11) 0.48204(8) 0.0269(4) Uani 1 1 d . . . . .
H12 H 0.732494 0.244529 0.517094 0.040 Uiso 1 1 d R U . . .
O23 O 0.38162(9) 0.01586(10) 0.42687(7) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.58461(12) 0.33808(11) 0.41669(8) 0.0177(3) Uani 1 1 d . . . . .
H1 H 0.543821 0.321279 0.446008 0.021 Uiso 1 1 d R U . . .
N16 N 0.72939(13) -0.05033(13) 0.42355(11) 0.0282(4) Uani 1 1 d . . . . .
C2 C 0.63137(13) 0.25602(13) 0.40443(9) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.590789 0.218075 0.383600 0.020 Uiso 1 1 calc R U . . .
C3 C 0.70682(15) 0.27571(16) 0.36406(11) 0.0253(4) Uani 1 1 d . . . . .
H3A H 0.761810 0.270461 0.384760 0.030 Uiso 1 1 calc R U . . .
H3B H 0.707193 0.234882 0.332139 0.030 Uiso 1 1 calc R U . . .
C4 C 0.69662(16) 0.36613(16) 0.34120(11) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.741379 0.377414 0.311746 0.031 Uiso 1 1 calc R U . . .
C5 C 0.70711(17) 0.42857(16) 0.39058(12) 0.0305(5) Uani 1 1 d . . . . .
H5A H 0.766245 0.425194 0.405677 0.037 Uiso 1 1 calc R U . . .
H5B H 0.697217 0.487058 0.376916 0.037 Uiso 1 1 calc R U . . .
C6 C 0.64294(16) 0.40743(14) 0.43773(10) 0.0244(4) Uani 1 1 d . . . . .
H6A H 0.673790 0.388419 0.472200 0.029 Uiso 1 1 calc R U . . .
H6B H 0.608919 0.458301 0.447539 0.029 Uiso 1 1 calc R U . . .
C7 C 0.54001(15) 0.36760(14) 0.36347(9) 0.0209(4) Uani 1 1 d . . . . .
H7A H 0.511213 0.422447 0.370621 0.025 Uiso 1 1 calc R U . . .
H7B H 0.495865 0.325825 0.352158 0.025 Uiso 1 1 calc R U . . .
C8 C 0.60678(17) 0.37780(15) 0.31508(10) 0.0247(4) Uani 1 1 d . . . . .
H8 H 0.602578 0.436918 0.300088 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5895(2) 0.31738(19) 0.26670(11) 0.0334(6) Uani 1 1 d . . . . .
H9 H 0.579372 0.259667 0.275903 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5875(2) 0.3388(2) 0.21290(13) 0.0424(7) Uani 1 1 d . . . . .
H10A H 0.597379 0.395977 0.202097 0.051 Uiso 1 1 calc R U . . .
H10B H 0.576230 0.297220 0.184732 0.051 Uiso 1 1 calc R U . . .
C11 C 0.65779(14) 0.21042(13) 0.45922(10) 0.0196(4) Uani 1 1 d . . . . .
H11 H 0.609318 0.211971 0.487000 0.024 Uiso 1 1 calc R U . . .
C13 C 0.68048(14) 0.11874(13) 0.44571(10) 0.0206(4) Uani 1 1 d . . . . .
C14 C 0.76528(15) 0.09418(16) 0.44386(13) 0.0300(5) Uani 1 1 d . . . . .
H14 H 0.809370 0.134722 0.449836 0.036 Uiso 1 1 calc R U . . .
C15 C 0.78647(16) 0.00916(17) 0.43313(15) 0.0339(6) Uani 1 1 d . . . . .
H15 H 0.845363 -0.006146 0.432785 0.041 Uiso 1 1 calc R U . . .
C17 C 0.64429(14) -0.02774(14) 0.42417(10) 0.0204(4) Uani 1 1 d . . . . .
C18 C 0.61566(13) 0.05593(13) 0.43541(9) 0.0174(4) Uani 1 1 d . . . . .
C19 C 0.52592(12) 0.07302(12) 0.43683(8) 0.0146(3) Uani 1 1 d . . . . .
H19 H 0.505621 0.128513 0.444737 0.017 Uiso 1 1 calc R U . . .
C20 C 0.46887(13) 0.00788(12) 0.42658(8) 0.0148(3) Uani 1 1 d . . . . .
C21 C 0.49752(14) -0.07519(13) 0.41480(9) 0.0172(4) Uani 1 1 d . . . . .
H21 H 0.457063 -0.118843 0.407523 0.021 Uiso 1 1 calc R U . . .
C22 C 0.58336(14) -0.09292(13) 0.41384(9) 0.0192(4) Uani 1 1 d . . . . .
H22 H 0.602317 -0.148966 0.406241 0.023 Uiso 1 1 calc R U . . .
C24 C 0.34657(14) 0.09588(14) 0.44436(10) 0.0210(4) Uani 1 1 d . . . . .
H24A H 0.366896 0.109475 0.482684 0.032 Uiso 1 1 calc R U . . .
H24B H 0.283833 0.092566 0.444429 0.032 Uiso 1 1 calc R U . . .
H24C H 0.365079 0.140182 0.417912 0.032 Uiso 1 1 calc R U . . .
O36 O 0.73580(9) 0.73069(10) 0.53132(7) 0.0184(3) Uani 1 1 d . . . . .
H36 H 0.752622 0.750303 0.500101 0.028 Uiso 1 1 d R U . . .
O45 O 0.39936(10) 0.99097(10) 0.56179(7) 0.0222(3) Uani 1 1 d . . . . .
N25 N 0.57613(11) 0.65649(11) 0.58714(7) 0.0166(3) Uani 1 1 d . . . . .
H25 H 0.539371 0.673289 0.558792 0.020 Uiso 1 1 d R U . . .
N40 N 0.74695(13) 1.03412(13) 0.59424(10) 0.0253(4) Uani 1 1 d . . . . .
C26 C 0.52409(14) 0.62793(14) 0.63759(9) 0.0206(4) Uani 1 1 d . . . . .
H26A H 0.490470 0.576977 0.627375 0.025 Uiso 1 1 calc R U . . .
H26B H 0.483508 0.673184 0.648725 0.025 Uiso 1 1 calc R U . . .
C27 C 0.58429(15) 0.60735(14) 0.68793(9) 0.0210(4) Uani 1 1 d . . . . .
H27 H 0.574015 0.547381 0.699773 0.025 Uiso 1 1 calc R U . . .
C28 C 0.67744(15) 0.61476(15) 0.66602(10) 0.0219(4) Uani 1 1 d . . . . .
H28 H 0.718130 0.598073 0.696883 0.026 Uiso 1 1 calc R U . . .
C29 C 0.69607(14) 0.70606(14) 0.64746(10) 0.0205(4) Uani 1 1 d . . . . .
H29A H 0.753983 0.709471 0.630411 0.025 Uiso 1 1 calc R U . . .
H29B H 0.694354 0.744139 0.680853 0.025 Uiso 1 1 calc R U . . .
C30 C 0.62819(12) 0.73390(12) 0.60363(9) 0.0153(3) Uani 1 1 d . . . . .
H30 H 0.588601 0.774573 0.622920 0.018 Uiso 1 1 calc R U . . .
C31 C 0.62992(15) 0.58395(14) 0.56651(10) 0.0217(4) Uani 1 1 d . . . . .
H31A H 0.664650 0.601866 0.533420 0.026 Uiso 1 1 calc R U . . .
H31B H 0.592683 0.536375 0.554619 0.026 Uiso 1 1 calc R U . . .
C32 C 0.68889(16) 0.55577(15) 0.61523(11) 0.0268(5) Uani 1 1 d . . . . .
H32A H 0.674753 0.496978 0.626436 0.032 Uiso 1 1 calc R U . . .
H32B H 0.749336 0.557050 0.602437 0.032 Uiso 1 1 calc R U . . .
C33 C 0.56881(19) 0.66405(17) 0.73859(11) 0.0297(5) Uani 1 1 d . . . . .
H33 H 0.557019 0.722142 0.731574 0.036 Uiso 1 1 calc R U . . .
C34 C 0.5705(3) 0.6384(2) 0.79192(12) 0.0435(7) Uani 1 1 d . . . . .
H34A H 0.582143 0.580748 0.800485 0.052 Uiso 1 1 calc R U . . .
H34B H 0.560201 0.677624 0.821749 0.052 Uiso 1 1 calc R U . . .
C35 C 0.66523(12) 0.77856(12) 0.55115(9) 0.0150(3) Uani 1 1 d . . . . .
H35 H 0.620412 0.780939 0.520818 0.018 Uiso 1 1 calc R U . . .
C37 C 0.69115(13) 0.86854(13) 0.56733(9) 0.0167(3) Uani 1 1 d . . . . .
C38 C 0.77667(14) 0.88686(15) 0.57625(11) 0.0233(4) Uani 1 1 d . . . . .
H38 H 0.818583 0.843419 0.573349 0.028 Uiso 1 1 calc R U . . .
C39 C 0.80148(15) 0.97038(16) 0.58969(12) 0.0288(5) Uani 1 1 d . . . . .
H39 H 0.860630 0.981454 0.595801 0.035 Uiso 1 1 calc R U . . .
C41 C 0.66172(14) 1.01727(13) 0.58611(9) 0.0189(4) Uani 1 1 d . . . . .
C42 C 0.63004(13) 0.93526(13) 0.57253(9) 0.0155(3) Uani 1 1 d . . . . .
C43 C 0.53998(12) 0.92406(12) 0.56359(8) 0.0145(3) Uani 1 1 d . . . . .
H43 H 0.517616 0.869869 0.554217 0.017 Uiso 1 1 calc R U . . .
C44 C 0.48596(13) 0.99297(12) 0.56874(8) 0.0162(3) Uani 1 1 d . . . . .
C46 C 0.36060(14) 0.91132(15) 0.54790(10) 0.0225(4) Uani 1 1 d . . . . .
H46A H 0.383776 0.890744 0.511751 0.034 Uiso 1 1 calc R U . . .
H46B H 0.298412 0.918584 0.544513 0.034 Uiso 1 1 calc R U . . .
H46C H 0.373103 0.870161 0.577937 0.034 Uiso 1 1 calc R U . . .
C47 C 0.51796(14) 1.07470(13) 0.58178(9) 0.0189(4) Uani 1 1 d . . . . .
H47 H 0.479675 1.121316 0.584539 0.023 Uiso 1 1 calc R U . . .
C48 C 0.60374(15) 1.08659(13) 0.59039(9) 0.0206(4) Uani 1 1 d . . . . .
H48 H 0.624822 1.141461 0.599288 0.025 Uiso 1 1 calc R U . . .
S49 S 0.52949(3) 0.64440(3) 0.39460(2) 0.01573(10) Uani 1 1 d . . . . .
O52 O 0.74673(11) 0.68767(13) 0.34616(7) 0.0292(4) Uani 1 1 d . . . . .
O59 O 0.47049(10) 0.71404(10) 0.40511(7) 0.0198(3) Uani 1 1 d . . . . .
O60 O 0.51087(11) 0.56876(10) 0.42717(7) 0.0232(3) Uani 1 1 d . . . . .
N50 N 0.62704(12) 0.67442(13) 0.40230(8) 0.0195(3) Uani 1 1 d . . . . .
C51 C 0.67028(14) 0.66884(15) 0.35242(9) 0.0212(4) Uani 1 1 d . . . . .
C53 C 0.61618(14) 0.63670(15) 0.30394(9) 0.0208(4) Uani 1 1 d . . . . .
C54 C 0.53321(14) 0.62058(14) 0.32131(9) 0.0191(4) Uani 1 1 d . . . . .
C55 C 0.47065(16) 0.58982(17) 0.28496(10) 0.0274(5) Uani 1 1 d . . . . .
H55 H 0.413971 0.578865 0.297780 0.033 Uiso 1 1 calc R U . . .
C56 C 0.49464(19) 0.5757(2) 0.22887(11) 0.0360(6) Uani 1 1 d . . . . .
H56 H 0.453668 0.554489 0.202626 0.043 Uiso 1 1 calc R U . . .
C57 C 0.57816(19) 0.5923(2) 0.21055(10) 0.0352(6) Uani 1 1 d . . . . .
H57 H 0.593039 0.582258 0.172010 0.042 Uiso 1 1 calc R U . . .
C58 C 0.64008(17) 0.62349(19) 0.24782(10) 0.0301(5) Uani 1 1 d . . . . .
H58 H 0.696711 0.635265 0.235245 0.036 Uiso 1 1 calc R U . . .
S61 S 0.50644(3) 0.34814(3) 0.60421(2) 0.01731(10) Uani 1 1 d . . . . .
O70 O 0.71732(11) 0.29823(13) 0.66116(7) 0.0270(4) Uani 1 1 d . . . . .
O71 O 0.44665(10) 0.28054(10) 0.58963(7) 0.0206(3) Uani 1 1 d . . . . .
O72 O 0.49279(13) 0.42578(11) 0.57285(8) 0.0288(4) Uani 1 1 d . . . . .
N62 N 0.60398(12) 0.31615(13) 0.60024(8) 0.0204(3) Uani 1 1 d . . . . .
C63 C 0.64223(14) 0.31818(14) 0.65185(9) 0.0195(4) Uani 1 1 d . . . . .
C64 C 0.58410(13) 0.34878(14) 0.69864(8) 0.0178(4) Uani 1 1 d . . . . .
C65 C 0.50326(14) 0.36812(14) 0.67789(9) 0.0193(4) Uani 1 1 d . . . . .
C66 C 0.43837(16) 0.39918(18) 0.71198(11) 0.0303(5) Uani 1 1 d . . . . .
H66 H 0.383404 0.412236 0.696976 0.036 Uiso 1 1 calc R U . . .
C67 C 0.45721(18) 0.4105(2) 0.76957(11) 0.0343(6) Uani 1 1 d . . . . .
H67 H 0.414371 0.431988 0.794386 0.041 Uiso 1 1 calc R U . . .
C68 C 0.53794(18) 0.39079(18) 0.79096(10) 0.0290(5) Uani 1 1 d . . . . .
H68 H 0.549202 0.398919 0.830241 0.035 Uiso 1 1 calc R U . . .
C69 C 0.60256(15) 0.35939(15) 0.75603(9) 0.0226(4) Uani 1 1 d . . . . .
H69 H 0.657453 0.345645 0.770887 0.027 Uiso 1 1 calc R U . . .
O73 O 0.3059(3) 0.5544(4) 0.7270(3) 0.132(2) Uani 1 1 d . . . . .
C74 C 0.2316(3) 0.5073(3) 0.7372(3) 0.0791(16) Uani 1 1 d . . . . .
C75 C 0.1664(3) 0.5606(4) 0.7566(3) 0.089(2) Uani 1 1 d . . . . .
C76 C 0.1955(6) 0.6463(4) 0.7426(4) 0.131(4) Uani 1 1 d . . . . .
C77 C 0.2882(7) 0.6397(4) 0.7450(5) 0.139(4) Uani 1 1 d . . . . .
O90 O 0.29773(10) 0.70901(10) 0.56919(7) 0.0185(3) Uani 1 1 d D . . . .
H90A H 0.279566 0.742505 0.593517 0.028 Uiso 1 1 d R U . . .
H90B H 0.282(3) 0.6581(17) 0.5768(17) 0.053(12) Uiso 1 1 d D . . . .
O93 O 0.29570(11) 0.29874(11) 0.41692(8) 0.0266(3) Uani 1 1 d . . . . .
H93A H 0.303462 0.351766 0.397657 0.040 Uiso 1 1 d R U . . .
H93B H 0.270842 0.260446 0.387537 0.040 Uiso 1 1 d R U . . .
O92 O 0.44751(10) 0.27517(11) 0.47034(7) 0.0219(3) Uani 1 1 d . . . . .
H92A H 0.407075 0.284724 0.455401 0.033 Uiso 1 1 d R U . . .
H92B H 0.440345 0.271734 0.502141 0.033 Uiso 1 1 d R U . . .
O91 O 0.45420(9) 0.72702(11) 0.52348(7) 0.0202(3) Uani 1 1 d . . . . .
H91A H 0.452955 0.722787 0.493392 0.030 Uiso 1 1 d R U . . .
H91B H 0.408345 0.715857 0.532892 0.030 Uiso 1 1 d 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
O12 H12 0.8400 . ?
O12 C11 1.417(2) . ?
O23 C20 1.367(2) . ?
O23 C24 1.437(3) . ?
N1 H1 0.9755 . ?
N1 C2 1.515(3) . ?
N1 C6 1.507(3) . ?
N1 C7 1.507(3) . ?
N16 C15 1.314(3) . ?
N16 C17 1.375(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.544(3) . ?
C2 C11 1.534(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.534(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.533(4) . ?
C4 C8 1.542(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.532(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.552(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.510(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.311(4) . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 H11 1.0000 . ?
C11 C13 1.524(3) . ?
C13 C14 1.379(3) . ?
C13 C18 1.437(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.405(4) . ?
C15 H15 0.9500 . ?
C17 C18 1.419(3) . ?
C17 C22 1.422(3) . ?
C18 C19 1.426(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C20 C21 1.413(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.368(3) . ?
C22 H22 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O36 H36 0.8396 . ?
O36 C35 1.414(2) . ?
O45 C44 1.361(2) . ?
O45 C46 1.433(3) . ?
N25 H25 0.9190 . ?
N25 C26 1.508(3) . ?
N25 C30 1.518(3) . ?
N25 C31 1.501(3) . ?
N40 C39 1.322(3) . ?
N40 C41 1.369(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.547(3) . ?
C27 H27 1.0000 . ?
C27 C28 1.546(3) . ?
C27 C33 1.511(3) . ?
C28 H28 1.0000 . ?
C28 C29 1.534(3) . ?
C28 C32 1.526(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.543(3) . ?
C30 H30 1.0000 . ?
C30 C35 1.535(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.536(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33 0.9500 . ?
C33 C34 1.319(4) . ?
C34 H34A 0.9500 . ?
C34 H34B 0.9500 . ?
C35 H35 1.0000 . ?
C35 C37 1.526(3) . ?
C37 C38 1.381(3) . ?
C37 C42 1.426(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.410(3) . ?
C39 H39 0.9500 . ?
C41 C42 1.422(3) . ?
C41 C48 1.423(3) . ?
C42 C43 1.431(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.382(3) . ?
C44 C47 1.417(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47 0.9500 . ?
C47 C48 1.366(3) . ?
C48 H48 0.9500 . ?
S49 O59 1.4551(16) . ?
S49 O60 1.4488(16) . ?
S49 N50 1.6040(19) . ?
S49 C54 1.767(2) . ?
O52 C51 1.238(3) . ?
N50 C51 1.357(3) . ?
C51 C53 1.507(3) . ?
C53 C54 1.381(3) . ?
C53 C58 1.389(3) . ?
C54 C55 1.386(3) . ?
C55 H55 0.9500 . ?
C55 C56 1.391(3) . ?
C56 H56 0.9500 . ?
C56 C57 1.397(4) . ?
C57 H57 0.9500 . ?
C57 C58 1.394(3) . ?
C58 H58 0.9500 . ?
S61 O71 1.4584(16) . ?
S61 O72 1.4468(17) . ?
S61 N62 1.6060(19) . ?
S61 C65 1.764(2) . ?
O70 C63 1.233(3) . ?
N62 C63 1.354(3) . ?
C63 C64 1.506(3) . ?
C64 C65 1.386(3) . ?
C64 C69 1.392(3) . ?
C65 C66 1.382(3) . ?
C66 H66 0.9500 . ?
C66 C67 1.399(4) . ?
C67 H67 0.9500 . ?
C67 C68 1.392(4) . ?
C68 H68 0.9500 . ?
C68 C69 1.392(3) . ?
C69 H69 0.9500 . ?
O73 C74 1.398(7) . ?
O73 C77 1.440(9) . ?
C74 C75 1.396(7) . ?
C75 C76 1.466(10) . ?
C76 C77 1.450(14) . ?
O90 H90A 0.8294 . ?
O90 H90B 0.86(2) . ?
O93 H93A 0.9599 . ?
O93 H93B 0.9971 . ?
O92 H92A 0.7377 . ?
O92 H92B 0.7589 . ?
O91 H91A 0.7118 . ?
O91 H91B 0.7692 . ?

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
C11 O12 H12 109.4 . . ?
C20 O23 C24 117.47(16) . . ?
C2 N1 H1 102.5 . . ?
C6 N1 H1 111.0 . . ?
C6 N1 C2 113.17(17) . . ?
C7 N1 H1 111.8 . . ?
C7 N1 C2 109.18(16) . . ?
C7 N1 C6 109.10(17) . . ?
C15 N16 C17 117.8(2) . . ?
N1 C2 H2 107.5 . . ?
N1 C2 C3 108.18(17) . . ?
N1 C2 C11 111.76(17) . . ?
C3 C2 H2 107.5 . . ?
C11 C2 H2 107.5 . . ?
C11 C2 C3 114.03(18) . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.91(19) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C3 C4 H4 109.7 . . ?
C3 C4 C8 110.22(19) . . ?
C5 C4 C3 108.8(2) . . ?
C5 C4 H4 109.7 . . ?
C5 C4 C8 108.8(2) . . ?
C8 C4 H4 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 C4 109.86(19) . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N1 C6 C5 108.34(18) . . ?
N1 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N1 C7 H7A 109.8 . . ?
N1 C7 H7B 109.8 . . ?
N1 C7 C8 109.43(18) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C4 C8 C7 107.75(18) . . ?
C4 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 C4 112.8(2) . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 H8 108.2 . . ?
C8 C9 H9 117.6 . . ?
C10 C9 C8 124.7(3) . . ?
C10 C9 H9 117.6 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
O12 C11 C2 107.62(17) . . ?
O12 C11 H11 109.6 . . ?
O12 C11 C13 110.94(17) . . ?
C2 C11 H11 109.6 . . ?
C13 C11 C2 109.45(18) . . ?
C13 C11 H11 109.6 . . ?
C14 C13 C11 119.77(19) . . ?
C14 C13 C18 118.4(2) . . ?
C18 C13 C11 121.83(19) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
N16 C15 C14 123.7(2) . . ?
N16 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
N16 C17 C18 123.2(2) . . ?
N16 C17 C22 117.1(2) . . ?
C18 C17 C22 119.69(19) . . ?
C17 C18 C13 116.90(19) . . ?
C17 C18 C19 119.30(18) . . ?
C19 C18 C13 123.79(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.16(18) . . ?
C20 C19 H19 120.4 . . ?
O23 C20 C19 124.88(18) . . ?
O23 C20 C21 113.67(17) . . ?
C19 C20 C21 121.45(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.17(19) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.22(19) . . ?
C21 C22 H22 119.9 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C35 O36 H36 109.6 . . ?
C44 O45 C46 117.80(16) . . ?
C26 N25 H25 108.8 . . ?
C26 N25 C30 109.12(16) . . ?
C30 N25 H25 106.7 . . ?
C31 N25 H25 109.5 . . ?
C31 N25 C26 109.14(17) . . ?
C31 N25 C30 113.47(16) . . ?
C39 N40 C41 117.7(2) . . ?
N25 C26 H26A 109.7 . . ?
N25 C26 H26B 109.7 . . ?
N25 C26 C27 109.85(17) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C26 C27 H27 108.4 . . ?
C28 C27 C26 107.41(17) . . ?
C28 C27 H27 108.4 . . ?
C33 C27 C26 112.5(2) . . ?
C33 C27 H27 108.4 . . ?
C33 C27 C28 111.6(2) . . ?
C27 C28 H28 109.5 . . ?
C29 C28 C27 110.13(18) . . ?
C29 C28 H28 109.5 . . ?
C32 C28 C27 108.97(19) . . ?
C32 C28 H28 109.5 . . ?
C32 C28 C29 109.15(19) . . ?
C28 C29 H29A 109.8 . . ?
C28 C29 H29B 109.8 . . ?
C28 C29 C30 109.17(17) . . ?
H29A C29 H29B 108.3 . . ?
C30 C29 H29A 109.8 . . ?
C30 C29 H29B 109.8 . . ?
N25 C30 C29 107.98(16) . . ?
N25 C30 H30 107.6 . . ?
N25 C30 C35 111.44(16) . . ?
C29 C30 H30 107.6 . . ?
C35 C30 C29 114.26(16) . . ?
C35 C30 H30 107.6 . . ?
N25 C31 H31A 110.0 . . ?
N25 C31 H31B 110.0 . . ?
N25 C31 C32 108.31(18) . . ?
H31A C31 H31B 108.4 . . ?
C32 C31 H31A 110.0 . . ?
C32 C31 H31B 110.0 . . ?
C28 C32 C31 109.77(18) . . ?
C28 C32 H32A 109.7 . . ?
C28 C32 H32B 109.7 . . ?
C31 C32 H32A 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C27 C33 H33 117.8 . . ?
C34 C33 C27 124.5(3) . . ?
C34 C33 H33 117.8 . . ?
C33 C34 H34A 120.0 . . ?
C33 C34 H34B 120.0 . . ?
H34A C34 H34B 120.0 . . ?
O36 C35 C30 108.24(16) . . ?
O36 C35 H35 109.2 . . ?
O36 C35 C37 111.95(16) . . ?
C30 C35 H35 109.2 . . ?
C37 C35 C30 109.05(16) . . ?
C37 C35 H35 109.2 . . ?
C38 C37 C35 119.28(18) . . ?
C38 C37 C42 118.55(19) . . ?
C42 C37 C35 122.16(17) . . ?
C37 C38 H38 120.2 . . ?
C37 C38 C39 119.7(2) . . ?
C39 C38 H38 120.2 . . ?
N40 C39 C38 123.6(2) . . ?
N40 C39 H39 118.2 . . ?
C38 C39 H39 118.2 . . ?
N40 C41 C42 123.07(19) . . ?
N40 C41 C48 117.23(19) . . ?
C42 C41 C48 119.68(19) . . ?
C37 C42 C43 123.51(18) . . ?
C41 C42 C37 117.36(18) . . ?
C41 C42 C43 119.11(18) . . ?
C42 C43 H43 120.4 . . ?
C44 C43 C42 119.23(18) . . ?
C44 C43 H43 120.4 . . ?
O45 C44 C43 125.20(18) . . ?
O45 C44 C47 113.37(18) . . ?
C43 C44 C47 121.43(19) . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C44 C47 H47 119.9 . . ?
C48 C47 C44 120.14(19) . . ?
C48 C47 H47 119.9 . . ?
C41 C48 H48 119.8 . . ?
C47 C48 C41 120.4(2) . . ?
C47 C48 H48 119.8 . . ?
O59 S49 N50 110.95(10) . . ?
O59 S49 C54 110.35(10) . . ?
O60 S49 O59 113.96(10) . . ?
O60 S49 N50 111.97(10) . . ?
O60 S49 C54 110.36(10) . . ?
N50 S49 C54 98.17(10) . . ?
C51 N50 S49 110.76(15) . . ?
O52 C51 N50 124.5(2) . . ?
O52 C51 C53 122.0(2) . . ?
N50 C51 C53 113.50(19) . . ?
C54 C53 C51 111.26(18) . . ?
C54 C53 C58 120.4(2) . . ?
C58 C53 C51 128.4(2) . . ?
C53 C54 S49 106.30(15) . . ?
C53 C54 C55 122.8(2) . . ?
C55 C54 S49 130.88(18) . . ?
C54 C55 H55 121.5 . . ?
C54 C55 C56 116.9(2) . . ?
C56 C55 H55 121.5 . . ?
C55 C56 H56 119.5 . . ?
C55 C56 C57 120.9(2) . . ?
C57 C56 H56 119.5 . . ?
C56 C57 H57 119.4 . . ?
C58 C57 C56 121.2(2) . . ?
C58 C57 H57 119.4 . . ?
C53 C58 C57 117.8(2) . . ?
C53 C58 H58 121.1 . . ?
C57 C58 H58 121.1 . . ?
O71 S61 N62 111.22(10) . . ?
O71 S61 C65 110.15(10) . . ?
O72 S61 O71 113.95(10) . . ?
O72 S61 N62 112.10(11) . . ?
O72 S61 C65 110.25(11) . . ?
N62 S61 C65 98.06(10) . . ?
C63 N62 S61 110.96(15) . . ?
O70 C63 N62 124.9(2) . . ?
O70 C63 C64 121.60(19) . . ?
N62 C63 C64 113.49(19) . . ?
C65 C64 C63 111.14(17) . . ?
C65 C64 C69 120.2(2) . . ?
C69 C64 C63 128.6(2) . . ?
C64 C65 S61 106.35(15) . . ?
C66 C65 S61 130.95(18) . . ?
C66 C65 C64 122.7(2) . . ?
C65 C66 H66 121.5 . . ?
C65 C66 C67 117.0(2) . . ?
C67 C66 H66 121.5 . . ?
C66 C67 H67 119.6 . . ?
C68 C67 C66 120.8(2) . . ?
C68 C67 H67 119.6 . . ?
C67 C68 H68 119.3 . . ?
C67 C68 C69 121.4(2) . . ?
C69 C68 H68 119.3 . . ?
C64 C69 C68 117.8(2) . . ?
C64 C69 H69 121.1 . . ?
C68 C69 H69 121.1 . . ?
C74 O73 C77 106.7(5) . . ?
C75 C74 O73 109.9(5) . . ?
C74 C75 C76 104.9(5) . . ?
C77 C76 C75 103.5(4) . . ?
O73 C77 C76 104.3(5) . . ?
H90A O90 H90B 111.0 . . ?
H93A O93 H93B 104.5 . . ?
H92A O92 H92B 111.0 . . ?
H91A O91 H91B 103.9 . . ?

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
O12 C11 C13 C14 -14.6(3) . . . . ?
O12 C11 C13 C18 164.6(2) . . . . ?
O23 C20 C21 C22 -179.15(19) . . . . ?
N1 C2 C3 C4 -11.6(2) . . . . ?
N1 C2 C11 O12 -75.6(2) . . . . ?
N1 C2 C11 C13 163.78(17) . . . . ?
N1 C7 C8 C4 -7.8(2) . . . . ?
N1 C7 C8 C9 116.5(2) . . . . ?
N16 C17 C18 C13 0.8(3) . . . . ?
N16 C17 C18 C19 -178.2(2) . . . . ?
N16 C17 C22 C21 178.9(2) . . . . ?
C2 N1 C6 C5 63.4(2) . . . . ?
C2 N1 C7 C8 -57.1(2) . . . . ?
C2 C3 C4 C5 66.3(2) . . . . ?
C2 C3 C4 C8 -52.9(3) . . . . ?
C2 C11 C13 C14 104.0(3) . . . . ?
C2 C11 C13 C18 -76.8(3) . . . . ?
C3 C2 C11 O12 47.5(2) . . . . ?
C3 C2 C11 C13 -73.1(2) . . . . ?
C3 C4 C5 C6 -56.0(3) . . . . ?
C3 C4 C8 C7 64.1(2) . . . . ?
C3 C4 C8 C9 -59.5(3) . . . . ?
C4 C5 C6 N1 -6.1(3) . . . . ?
C4 C8 C9 C10 -106.6(4) . . . . ?
C5 C4 C8 C7 -55.0(2) . . . . ?
C5 C4 C8 C9 -178.7(2) . . . . ?
C6 N1 C2 C3 -52.9(2) . . . . ?
C6 N1 C2 C11 73.4(2) . . . . ?
C6 N1 C7 C8 67.0(2) . . . . ?
C7 N1 C2 C3 68.8(2) . . . . ?
C7 N1 C2 C11 -164.86(17) . . . . ?
C7 N1 C6 C5 -58.3(2) . . . . ?
C7 C8 C9 C10 131.9(3) . . . . ?
C8 C4 C5 C6 64.1(3) . . . . ?
C11 C2 C3 C4 -136.6(2) . . . . ?
C11 C13 C14 C15 178.1(3) . . . . ?
C11 C13 C18 C17 -179.0(2) . . . . ?
C11 C13 C18 C19 0.0(3) . . . . ?
C13 C14 C15 N16 1.1(5) . . . . ?
C13 C18 C19 C20 -179.7(2) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C14 C13 C18 C19 179.2(2) . . . . ?
C15 N16 C17 C18 -0.9(4) . . . . ?
C15 N16 C17 C22 -179.9(3) . . . . ?
C17 N16 C15 C14 -0.1(5) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C18 C19 C20 O23 179.80(19) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C17 -0.6(3) . . . . ?
C22 C17 C18 C13 179.8(2) . . . . ?
C22 C17 C18 C19 0.8(3) . . . . ?
C24 O23 C20 C19 -6.2(3) . . . . ?
C24 O23 C20 C21 173.55(18) . . . . ?
O36 C35 C37 C38 -17.3(3) . . . . ?
O36 C35 C37 C42 161.43(18) . . . . ?
O45 C44 C47 C48 179.51(19) . . . . ?
N25 C26 C27 C28 -5.8(2) . . . . ?
N25 C26 C27 C33 117.5(2) . . . . ?
N25 C30 C35 O36 -76.08(19) . . . . ?
N25 C30 C35 C37 161.90(15) . . . . ?
N25 C31 C32 C28 -4.1(3) . . . . ?
N40 C41 C42 C37 0.0(3) . . . . ?
N40 C41 C42 C43 -178.7(2) . . . . ?
N40 C41 C48 C47 178.8(2) . . . . ?
C26 N25 C30 C29 67.5(2) . . . . ?
C26 N25 C30 C35 -166.23(16) . . . . ?
C26 N25 C31 C32 -59.5(2) . . . . ?
C26 C27 C28 C29 63.2(2) . . . . ?
C26 C27 C28 C32 -56.5(2) . . . . ?
C26 C27 C33 C34 140.7(3) . . . . ?
C27 C28 C29 C30 -54.6(2) . . . . ?
C27 C28 C32 C31 63.2(2) . . . . ?
C28 C27 C33 C34 -98.4(3) . . . . ?
C28 C29 C30 N25 -9.3(2) . . . . ?
C28 C29 C30 C35 -133.90(18) . . . . ?
C29 C28 C32 C31 -57.1(2) . . . . ?
C29 C30 C35 O36 46.7(2) . . . . ?
C29 C30 C35 C37 -75.4(2) . . . . ?
C30 N25 C26 C27 -58.6(2) . . . . ?
C30 N25 C31 C32 62.4(2) . . . . ?
C30 C35 C37 C38 102.5(2) . . . . ?
C30 C35 C37 C42 -78.8(2) . . . . ?
C31 N25 C26 C27 65.9(2) . . . . ?
C31 N25 C30 C29 -54.4(2) . . . . ?
C31 N25 C30 C35 71.8(2) . . . . ?
C32 C28 C29 C30 65.0(2) . . . . ?
C33 C27 C28 C29 -60.6(2) . . . . ?
C33 C27 C28 C32 179.71(19) . . . . ?
C35 C37 C38 C39 178.2(2) . . . . ?
C35 C37 C42 C41 -178.08(19) . . . . ?
C35 C37 C42 C43 0.5(3) . . . . ?
C37 C38 C39 N40 -0.3(4) . . . . ?
C37 C42 C43 C44 -178.97(19) . . . . ?
C38 C37 C42 C41 0.7(3) . . . . ?
C38 C37 C42 C43 179.2(2) . . . . ?
C39 N40 C41 C42 -0.7(4) . . . . ?
C39 N40 C41 C48 -179.2(2) . . . . ?
C41 N40 C39 C38 0.9(4) . . . . ?
C41 C42 C43 C44 -0.4(3) . . . . ?
C42 C37 C38 C39 -0.5(3) . . . . ?
C42 C41 C48 C47 0.3(3) . . . . ?
C42 C43 C44 O45 -179.49(19) . . . . ?
C42 C43 C44 C47 1.0(3) . . . . ?
C43 C44 C47 C48 -1.0(3) . . . . ?
C44 C47 C48 C41 0.3(3) . . . . ?
C46 O45 C44 C43 -0.1(3) . . . . ?
C46 O45 C44 C47 179.39(18) . . . . ?
C48 C41 C42 C37 178.41(19) . . . . ?
C48 C41 C42 C43 -0.2(3) . . . . ?
S49 N50 C51 O52 -179.7(2) . . . . ?
S49 N50 C51 C53 0.1(3) . . . . ?
S49 C54 C55 C56 -178.6(2) . . . . ?
O52 C51 C53 C54 -179.6(2) . . . . ?
O52 C51 C53 C58 -0.1(4) . . . . ?
O59 S49 N50 C51 -116.09(17) . . . . ?
O59 S49 C54 C53 116.84(17) . . . . ?
O59 S49 C54 C55 -64.7(3) . . . . ?
O60 S49 N50 C51 115.36(17) . . . . ?
O60 S49 C54 C53 -116.32(17) . . . . ?
O60 S49 C54 C55 62.2(3) . . . . ?
N50 S49 C54 C53 0.83(18) . . . . ?
N50 S49 C54 C55 179.3(2) . . . . ?
N50 C51 C53 C54 0.5(3) . . . . ?
N50 C51 C53 C58 -180.0(3) . . . . ?
C51 C53 C54 S49 -0.8(2) . . . . ?
C51 C53 C54 C55 -179.5(2) . . . . ?
C51 C53 C58 C57 179.5(3) . . . . ?
C53 C54 C55 C56 -0.3(4) . . . . ?
C54 S49 N50 C51 -0.54(18) . . . . ?
C54 C53 C58 C57 -1.1(4) . . . . ?
C54 C55 C56 C57 -0.2(5) . . . . ?
C55 C56 C57 C58 0.0(5) . . . . ?
C56 C57 C58 C53 0.6(5) . . . . ?
C58 C53 C54 S49 179.6(2) . . . . ?
C58 C53 C54 C55 1.0(4) . . . . ?
S61 N62 C63 O70 -178.9(2) . . . . ?
S61 N62 C63 C64 0.4(2) . . . . ?
S61 C65 C66 C67 -177.9(2) . . . . ?
O70 C63 C64 C65 179.4(2) . . . . ?
O70 C63 C64 C69 0.0(4) . . . . ?
O71 S61 N62 C63 -115.95(17) . . . . ?
O71 S61 C65 C64 116.82(16) . . . . ?
O71 S61 C65 C66 -65.2(3) . . . . ?
O72 S61 N62 C63 115.18(17) . . . . ?
O72 S61 C65 C64 -116.58(17) . . . . ?
O72 S61 C65 C66 61.4(3) . . . . ?
N62 S61 C65 C64 0.63(17) . . . . ?
N62 S61 C65 C66 178.6(3) . . . . ?
N62 C63 C64 C65 0.1(3) . . . . ?
N62 C63 C64 C69 -179.3(2) . . . . ?
C63 C64 C65 S61 -0.5(2) . . . . ?
C63 C64 C65 C66 -178.7(2) . . . . ?
C63 C64 C69 C68 178.5(2) . . . . ?
C64 C65 C66 C67 -0.2(4) . . . . ?
C65 S61 N62 C63 -0.59(18) . . . . ?
C65 C64 C69 C68 -0.9(4) . . . . ?
C65 C66 C67 C68 -0.3(5) . . . . ?
C66 C67 C68 C69 0.1(5) . . . . ?
C67 C68 C69 C64 0.4(4) . . . . ?
C69 C64 C65 S61 178.98(19) . . . . ?
C69 C64 C65 C66 0.8(4) . . . . ?
O73 C74 C75 C76 16.0(8) . . . . ?
C74 O73 C77 C76 -23.1(11) . . . . ?
C74 C75 C76 C77 -29.7(10) . . . . ?
C75 C76 C77 O73 32.3(11) . . . . ?
C77 O73 C74 C75 4.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.02(5)
2 -0.02(5)

