# 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_ETB_FORM_I
_database_code_depnum_ccdc_archive 'CCDC 2052731'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_ETB_FORM_I          
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.96 eA-3
RESPONSE: This is due to the slight disorder exhibited by terminal
dimethoxyethane moiety. The disorder has not been modeled. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N3 O4'
_chemical_formula_sum            'C22 H23 N3 O4'
_chemical_formula_weight         393.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   13.9641(6)
_cell_length_b                   13.0136(5)
_cell_length_c                   11.2102(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.3410(10)
_cell_angle_gamma                90
_cell_volume                     1997.38(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9308
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      38.68

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            61579
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         38.889
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             20962
_reflns_number_gt                19979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.980

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²+0.3311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 8987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(11)
_chemical_absolute_configuration .
_refine_ls_number_reflns         20962
_refine_ls_number_parameters     527
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22849(8) 0.67963(8) 0.30326(10) 0.01516(17) Uani 1 1 d . . . . .
O2 O 0.13450(11) 0.75529(13) 0.06087(12) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.28451(8) 0.49693(8) 0.31776(10) 0.01517(18) Uani 1 1 d . . . . .
O4 O 0.15535(8) 0.34574(10) 0.22111(11) 0.01779(19) Uani 1 1 d . . . . .
N1 N 0.50040(9) 0.78747(9) 0.61309(11) 0.01337(18) Uani 1 1 d . . . . .
N2 N 0.60728(9) 0.65942(9) 0.72034(11) 0.01392(18) Uani 1 1 d . . . . .
N3 N 0.58446(9) 0.48635(9) 0.68147(11) 0.01350(18) Uani 1 1 d . . . . .
H3N H 0.550411 0.436791 0.639634 0.016 Uiso 1 1 calc R U . . .
C1 C 0.57671(11) 0.75621(10) 0.69352(13) 0.0151(2) Uani 1 1 d . . . . .
H1 H 0.615091 0.808817 0.738339 0.018 Uiso 1 1 calc R U . . .
C2 C 0.55599(9) 0.58419(10) 0.65633(11) 0.01083(17) Uani 1 1 d . . . . .
C3 C 0.41865(9) 0.53097(10) 0.48731(12) 0.01187(18) Uani 1 1 d . . . . .
H3 H 0.437043 0.460722 0.496909 0.014 Uiso 1 1 calc R U . . .
C4 C 0.33984(9) 0.55945(10) 0.40012(12) 0.01211(19) Uani 1 1 d . . . . .
C5 C 0.30956(9) 0.66490(10) 0.38847(12) 0.01178(18) Uani 1 1 d . . . . .
C6 C 0.36325(10) 0.73950(10) 0.45879(12) 0.01239(19) Uani 1 1 d . . . . .
H6 H 0.344476 0.809615 0.448743 0.015 Uiso 1 1 calc R U . . .
C7 C 0.44656(9) 0.71113(9) 0.54611(11) 0.01074(18) Uani 1 1 d . . . . .
C8 C 0.47253(9) 0.60674(9) 0.56300(11) 0.01037(17) Uani 1 1 d . . . . .
C9 C 0.66705(9) 0.45906(10) 0.77251(12) 0.01199(18) Uani 1 1 d . . . . .
C10 C 0.65228(10) 0.41210(11) 0.87910(12) 0.0147(2) Uani 1 1 d . . . . .
H10 H 0.587812 0.401038 0.891887 0.018 Uiso 1 1 calc R U . . .
C11 C 0.73204(11) 0.38140(12) 0.96681(13) 0.0162(2) Uani 1 1 d . . . . .
H11 H 0.721818 0.349834 1.039688 0.019 Uiso 1 1 calc R U . . .
C12 C 0.82649(11) 0.39666(12) 0.94841(13) 0.0161(2) Uani 1 1 d . . . . .
H12 H 0.880722 0.375934 1.008771 0.019 Uiso 1 1 calc R U . . .
C13 C 0.84164(10) 0.44268(11) 0.84063(13) 0.0140(2) Uani 1 1 d . . . . .
C14 C 0.76128(10) 0.47398(11) 0.75239(13) 0.0139(2) Uani 1 1 d . . . . .
H14 H 0.771130 0.505246 0.679174 0.017 Uiso 1 1 calc R U . . .
C15 C 0.93876(10) 0.45701(12) 0.81859(15) 0.0175(2) Uani 1 1 d . . . . .
C16 C 1.01997(11) 0.47105(14) 0.80075(17) 0.0219(3) Uani 1 1 d . . . . .
H16 H 1.084074 0.482130 0.786663 0.026 Uiso 1 1 calc R U . . .
C17 C 0.19103(10) 0.78209(11) 0.27980(13) 0.0147(2) Uani 1 1 d . . . . .
H17A H 0.242069 0.827983 0.259516 0.018 Uiso 1 1 calc R U . . .
H17B H 0.169183 0.809919 0.352191 0.018 Uiso 1 1 calc R U . . .
C18 C 0.10606(11) 0.77441(12) 0.17371(14) 0.0180(2) Uani 1 1 d . . . . .
H18A H 0.062313 0.718393 0.189748 0.022 Uiso 1 1 calc R U . . .
H18B H 0.068472 0.839355 0.167420 0.022 Uiso 1 1 calc R U . . .
C19 C 0.14282(16) 0.6497(2) 0.03296(18) 0.0314(4) Uani 1 1 d . . . . .
H19A H 0.203607 0.622059 0.081065 0.047 Uiso 1 1 calc R U . . .
H19B H 0.143488 0.642110 -0.053855 0.047 Uiso 1 1 calc R U . . .
H19C H 0.087118 0.611929 0.052387 0.047 Uiso 1 1 calc R U . . .
C20 C 0.31667(10) 0.39339(11) 0.30793(13) 0.0145(2) Uani 1 1 d . . . . .
H20A H 0.310916 0.353452 0.381360 0.017 Uiso 1 1 calc R U . . .
H20B H 0.385606 0.391999 0.298223 0.017 Uiso 1 1 calc R U . . .
C21 C 0.25083(11) 0.34978(11) 0.19715(12) 0.0151(2) Uani 1 1 d . . . . .
H21A H 0.252160 0.393896 0.125554 0.018 Uiso 1 1 calc R U . . .
H21B H 0.272873 0.280013 0.179847 0.018 Uiso 1 1 calc R U . . .
C22 C 0.08468(14) 0.31888(15) 0.11687(17) 0.0255(3) Uani 1 1 d . . . . .
H22A H 0.079154 0.374338 0.056759 0.038 Uiso 1 1 calc R U . . .
H22B H 0.021340 0.308340 0.140187 0.038 Uiso 1 1 calc R U . . .
H22C H 0.104671 0.255401 0.081578 0.038 Uiso 1 1 calc R U . . .
O1' O 0.76938(8) 0.18282(8) 0.43739(11) 0.01570(17) Uani 1 1 d . . . . .
O2' O 0.86897(12) 0.27073(14) 0.24850(14) 0.0299(3) Uani 1 1 d . . . . .
O3' O 0.71264(8) -0.00172(8) 0.42315(11) 0.01590(18) Uani 1 1 d . . . . .
O4' O 0.83842(9) -0.15319(10) 0.37745(12) 0.0199(2) Uani 1 1 d . . . . .
N1' N 0.49517(9) 0.28855(9) 0.61030(12) 0.01399(18) Uani 1 1 d . . . . .
N2' N 0.38954(9) 0.16010(9) 0.66738(12) 0.01489(19) Uani 1 1 d . . . . .
N3' N 0.41488(9) -0.01262(9) 0.64470(12) 0.01418(18) Uani 1 1 d . . . . .
H3'N H 0.450787 -0.062348 0.623380 0.017 Uiso 1 1 calc R U . . .
C1' C 0.41904(11) 0.25709(10) 0.65350(14) 0.0157(2) Uani 1 1 d . . . . .
H1' H 0.379859 0.309665 0.678058 0.019 Uiso 1 1 calc R U . . .
C2' C 0.44183(9) 0.08501(10) 0.63027(12) 0.01143(18) Uani 1 1 d . . . . .
C3' C 0.57922(9) 0.03193(10) 0.52770(12) 0.01224(19) Uani 1 1 d . . . . .
H3' H 0.561470 -0.038481 0.528903 0.015 Uiso 1 1 calc R U . . .
C4' C 0.65775(10) 0.06117(10) 0.47847(12) 0.01272(19) Uani 1 1 d . . . . .
C5' C 0.68753(9) 0.16658(10) 0.48154(12) 0.01222(19) Uani 1 1 d . . . . .
C6' C 0.63313(10) 0.24074(10) 0.52462(12) 0.01264(19) Uani 1 1 d . . . . .
H6' H 0.651345 0.310993 0.523104 0.015 Uiso 1 1 calc R U . . .
C7' C 0.54982(9) 0.21218(9) 0.57130(11) 0.01138(18) Uani 1 1 d . . . . .
C8' C 0.52486(9) 0.10767(9) 0.57671(12) 0.01091(18) Uani 1 1 d . . . . .
C9' C 0.33079(10) -0.03980(10) 0.69296(12) 0.01292(19) Uani 1 1 d . . . . .
C10' C 0.34271(11) -0.09000(12) 0.80459(13) 0.0161(2) Uani 1 1 d . . . . .
H10' H 0.406356 -0.103950 0.849781 0.019 Uiso 1 1 calc R U . . .
C11' C 0.26060(12) -0.11971(12) 0.84971(14) 0.0178(2) Uani 1 1 d . . . . .
H11' H 0.268658 -0.154239 0.925698 0.021 Uiso 1 1 calc R U . . .
C12' C 0.16743(12) -0.09933(12) 0.78477(14) 0.0177(2) Uani 1 1 d . . . . .
H12' H 0.111945 -0.118710 0.816825 0.021 Uiso 1 1 calc R U . . .
C13' C 0.15533(10) -0.05000(11) 0.67154(14) 0.0159(2) Uani 1 1 d . . . . .
C14' C 0.23777(10) -0.02012(11) 0.62598(13) 0.0150(2) Uani 1 1 d . . . . .
H14' H 0.230043 0.013511 0.549468 0.018 Uiso 1 1 calc R U . . .
C15' C 0.06012(11) -0.03061(13) 0.60036(16) 0.0204(3) Uani 1 1 d . . . . .
C16' C -0.01933(13) -0.01231(16) 0.53958(19) 0.0261(3) Uani 1 1 d . . . . .
H16' H -0.081909 0.002114 0.491706 0.031 Uiso 1 1 calc R U . . .
C17' C 0.80607(10) 0.28630(11) 0.43683(13) 0.0156(2) Uani 1 1 d . . . . .
H17C H 0.825172 0.312503 0.521065 0.019 Uiso 1 1 calc R U . . .
H17D H 0.755295 0.332195 0.391005 0.019 Uiso 1 1 calc R U . . .
C18' C 0.89379(11) 0.28274(13) 0.37652(16) 0.0203(3) Uani 1 1 d . . . . .
H18C H 0.931612 0.347045 0.395395 0.024 Uiso 1 1 calc R U . . .
H18D H 0.936362 0.224936 0.411322 0.024 Uiso 1 1 calc R U . . .
C19' C 0.85674(17) 0.1676(2) 0.2089(2) 0.0350(4) Uani 1 1 d . . . . .
H19D H 0.911122 0.126130 0.252367 0.052 Uiso 1 1 calc R U . . .
H19E H 0.855523 0.164377 0.121287 0.052 Uiso 1 1 calc R U . . .
H19F H 0.795094 0.140927 0.225612 0.052 Uiso 1 1 calc R U . . .
C20' C 0.67951(10) -0.10537(11) 0.39897(13) 0.0151(2) Uani 1 1 d . . . . .
H20C H 0.609430 -0.106464 0.360094 0.018 Uiso 1 1 calc R U . . .
H20D H 0.688592 -0.145507 0.475392 0.018 Uiso 1 1 calc R U . . .
C21' C 0.74053(11) -0.14933(11) 0.31467(13) 0.0160(2) Uani 1 1 d . . . . .
H21C H 0.717395 -0.219217 0.288571 0.019 Uiso 1 1 calc R U . . .
H21D H 0.735142 -0.105605 0.241382 0.019 Uiso 1 1 calc R U . . .
C22' C 0.90346(15) -0.17591(16) 0.2991(2) 0.0278(4) Uani 1 1 d . . . . .
H22D H 0.885569 -0.241930 0.258773 0.042 Uiso 1 1 calc R U . . .
H22E H 0.970265 -0.179857 0.346502 0.042 Uiso 1 1 calc R U . . .
H22F H 0.899639 -0.121698 0.237655 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3437(16) . ?
O1 C17 1.4376(17) . ?
O2 C19 1.419(3) . ?
O2 C18 1.420(2) . ?
O3 C4 1.3531(16) . ?
O3 C20 1.4314(17) . ?
O4 C21 1.4118(18) . ?
O4 C22 1.417(2) . ?
N1 C1 1.3176(18) . ?
N1 C7 1.3763(17) . ?
N2 C2 1.3357(17) . ?
N2 C1 1.3448(18) . ?
N3 C2 1.3471(17) . ?
N3 C9 1.4265(17) . ?
N3 H3N 0.8800 . ?
C1 H1 0.9500 . ?
C2 C8 1.4351(17) . ?
C3 C4 1.3714(17) . ?
C3 C8 1.4168(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4344(18) . ?
C5 C6 1.3760(18) . ?
C6 C7 1.4141(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4092(17) . ?
C9 C14 1.3916(19) . ?
C9 C10 1.3930(19) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4025(19) . ?
C13 C15 1.438(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.204(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.509(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5035(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1' C5' 1.3485(16) . ?
O1' C17' 1.4412(18) . ?
O2' C19' 1.413(3) . ?
O2' C18' 1.417(2) . ?
O3' C4' 1.3525(16) . ?
O3' C20' 1.4344(17) . ?
O4' C21' 1.410(2) . ?
O4' C22' 1.413(2) . ?
N1' C1' 1.3172(19) . ?
N1' C7' 1.3756(17) . ?
N2' C2' 1.3344(17) . ?
N2' C1' 1.3461(18) . ?
N3' C2' 1.3438(17) . ?
N3' C9' 1.4306(18) . ?
N3' H3'N 0.8800 . ?
C1' H1' 0.9500 . ?
C2' C8' 1.4373(17) . ?
C3' C4' 1.3748(18) . ?
C3' C8' 1.4190(18) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.4318(18) . ?
C5' C6' 1.3733(19) . ?
C6' C7' 1.4159(18) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.4083(17) . ?
C9' C14' 1.390(2) . ?
C9' C10' 1.392(2) . ?
C10' C11' 1.396(2) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.386(2) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.403(2) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.4031(19) . ?
C13' C15' 1.432(2) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.206(2) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.512(2) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' C21' 1.504(2) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C17 119.19(11) . . ?
C19 O2 C18 114.54(14) . . ?
C4 O3 C20 118.22(11) . . ?
C21 O4 C22 112.51(13) . . ?
C1 N1 C7 115.60(11) . . ?
C2 N2 C1 116.96(12) . . ?
C2 N3 C9 123.29(11) . . ?
C2 N3 H3N 118.4 . . ?
C9 N3 H3N 118.4 . . ?
N1 C1 N2 128.36(13) . . ?
N1 C1 H1 115.8 . . ?
N2 C1 H1 115.8 . . ?
N2 C2 N3 118.38(11) . . ?
N2 C2 C8 120.97(11) . . ?
N3 C2 C8 120.65(11) . . ?
C4 C3 C8 119.74(11) . . ?
C4 C3 H3 120.1 . . ?
C8 C3 H3 120.1 . . ?
O3 C4 C3 126.47(12) . . ?
O3 C4 C5 113.24(11) . . ?
C3 C4 C5 120.29(11) . . ?
O1 C5 C6 126.49(12) . . ?
O1 C5 C4 113.16(11) . . ?
C6 C5 C4 120.34(11) . . ?
C5 C6 C7 119.59(12) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
N1 C7 C8 121.60(11) . . ?
N1 C7 C6 118.43(11) . . ?
C8 C7 C6 119.97(11) . . ?
C7 C8 C3 119.87(11) . . ?
C7 C8 C2 116.47(11) . . ?
C3 C8 C2 123.63(11) . . ?
C14 C9 C10 120.30(12) . . ?
C14 C9 N3 120.42(12) . . ?
C10 C9 N3 119.19(12) . . ?
C11 C10 C9 119.94(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.38(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.86(13) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.78(13) . . ?
C12 C13 C15 120.73(13) . . ?
C14 C13 C15 119.48(13) . . ?
C9 C14 C13 119.74(12) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C13 178.69(17) . . ?
C15 C16 H16 180.0 . . ?
O1 C17 C18 106.51(12) . . ?
O1 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O1 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
O2 C18 C17 113.53(13) . . ?
O2 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
O2 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 105.59(11) . . ?
O3 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
O3 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.8 . . ?
O4 C21 C20 107.69(11) . . ?
O4 C21 H21A 110.2 . . ?
C20 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
C20 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5' O1' C17' 118.41(11) . . ?
C19' O2' C18' 114.41(16) . . ?
C4' O3' C20' 117.70(11) . . ?
C21' O4' C22' 112.06(14) . . ?
C1' N1' C7' 115.50(11) . . ?
C2' N2' C1' 116.87(12) . . ?
C2' N3' C9' 123.32(12) . . ?
C2' N3' H3'N 118.3 . . ?
C9' N3' H3'N 118.3 . . ?
N1' C1' N2' 128.42(13) . . ?
N1' C1' H1' 115.8 . . ?
N2' C1' H1' 115.8 . . ?
N2' C2' N3' 118.14(12) . . ?
N2' C2' C8' 121.05(11) . . ?
N3' C2' C8' 120.81(11) . . ?
C4' C3' C8' 119.52(12) . . ?
C4' C3' H3' 120.2 . . ?
C8' C3' H3' 120.2 . . ?
O3' C4' C3' 125.82(12) . . ?
O3' C4' C5' 113.74(11) . . ?
C3' C4' C5' 120.43(12) . . ?
O1' C5' C6' 125.89(12) . . ?
O1' C5' C4' 113.86(11) . . ?
C6' C5' C4' 120.23(12) . . ?
C5' C6' C7' 119.80(12) . . ?
C5' C6' H6' 120.1 . . ?
C7' C6' H6' 120.1 . . ?
N1' C7' C8' 121.77(11) . . ?
N1' C7' C6' 118.38(11) . . ?
C8' C7' C6' 119.85(11) . . ?
C7' C8' C3' 119.90(11) . . ?
C7' C8' C2' 116.29(11) . . ?
C3' C8' C2' 123.79(11) . . ?
C14' C9' C10' 120.37(12) . . ?
C14' C9' N3' 119.96(12) . . ?
C10' C9' N3' 119.61(13) . . ?
C9' C10' C11' 119.62(14) . . ?
C9' C10' H10' 120.2 . . ?
C11' C10' H10' 120.2 . . ?
C12' C11' C10' 120.66(14) . . ?
C12' C11' H11' 119.7 . . ?
C10' C11' H11' 119.7 . . ?
C11' C12' C13' 119.77(13) . . ?
C11' C12' H12' 120.1 . . ?
C13' C12' H12' 120.1 . . ?
C12' C13' C14' 119.65(14) . . ?
C12' C13' C15' 121.22(14) . . ?
C14' C13' C15' 119.12(14) . . ?
C9' C14' C13' 119.92(13) . . ?
C9' C14' H14' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C16' C15' C13' 178.58(19) . . ?
C15' C16' H16' 180.0 . . ?
O1' C17' C18' 107.05(12) . . ?
O1' C17' H17C 110.3 . . ?
C18' C17' H17C 110.3 . . ?
O1' C17' H17D 110.3 . . ?
C18' C17' H17D 110.3 . . ?
H17C C17' H17D 108.6 . . ?
O2' C18' C17' 113.44(13) . . ?
O2' C18' H18C 108.9 . . ?
C17' C18' H18C 108.9 . . ?
O2' C18' H18D 108.9 . . ?
C17' C18' H18D 108.9 . . ?
H18C C18' H18D 107.7 . . ?
O2' C19' H19D 109.5 . . ?
O2' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
O2' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O3' C20' C21' 105.95(11) . . ?
O3' C20' H20C 110.5 . . ?
C21' C20' H20C 110.5 . . ?
O3' C20' H20D 110.5 . . ?
C21' C20' H20D 110.5 . . ?
H20C C20' H20D 108.7 . . ?
O4' C21' C20' 108.26(12) . . ?
O4' C21' H21C 110.0 . . ?
C20' C21' H21C 110.0 . . ?
O4' C21' H21D 110.0 . . ?
C20' C21' H21D 110.0 . . ?
H21C C21' H21D 108.4 . . ?
O4' C22' H22D 109.5 . . ?
O4' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
O4' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 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
C7 N1 C1 N2 -1.7(2) . . . . ?
C2 N2 C1 N1 1.7(2) . . . . ?
C1 N2 C2 N3 -179.67(13) . . . . ?
C1 N2 C2 C8 0.33(19) . . . . ?
C9 N3 C2 N2 -0.4(2) . . . . ?
C9 N3 C2 C8 179.59(12) . . . . ?
C20 O3 C4 C3 -8.7(2) . . . . ?
C20 O3 C4 C5 170.43(12) . . . . ?
C8 C3 C4 O3 176.62(13) . . . . ?
C8 C3 C4 C5 -2.4(2) . . . . ?
C17 O1 C5 C6 -0.1(2) . . . . ?
C17 O1 C5 C4 -178.59(12) . . . . ?
O3 C4 C5 O1 4.03(17) . . . . ?
C3 C4 C5 O1 -176.81(12) . . . . ?
O3 C4 C5 C6 -174.59(13) . . . . ?
C3 C4 C5 C6 4.6(2) . . . . ?
O1 C5 C6 C7 179.17(13) . . . . ?
C4 C5 C6 C7 -2.41(19) . . . . ?
C1 N1 C7 C8 -0.32(19) . . . . ?
C1 N1 C7 C6 179.55(13) . . . . ?
C5 C6 C7 N1 178.37(12) . . . . ?
C5 C6 C7 C8 -1.76(19) . . . . ?
N1 C7 C8 C3 -176.25(12) . . . . ?
C6 C7 C8 C3 3.88(18) . . . . ?
N1 C7 C8 C2 2.01(18) . . . . ?
C6 C7 C8 C2 -177.86(11) . . . . ?
C4 C3 C8 C7 -1.75(19) . . . . ?
C4 C3 C8 C2 -179.88(12) . . . . ?
N2 C2 C8 C7 -2.01(18) . . . . ?
N3 C2 C8 C7 177.98(12) . . . . ?
N2 C2 C8 C3 176.18(13) . . . . ?
N3 C2 C8 C3 -3.83(19) . . . . ?
C2 N3 C9 C14 -74.37(18) . . . . ?
C2 N3 C9 C10 109.12(16) . . . . ?
C14 C9 C10 C11 1.0(2) . . . . ?
N3 C9 C10 C11 177.54(13) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C11 C12 C13 C15 -178.56(14) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
N3 C9 C14 C13 -177.26(12) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C15 C13 C14 C9 179.14(13) . . . . ?
C5 O1 C17 C18 175.29(12) . . . . ?
C19 O2 C18 C17 89.06(18) . . . . ?
O1 C17 C18 O2 -72.22(16) . . . . ?
C4 O3 C20 C21 -170.83(12) . . . . ?
C22 O4 C21 C20 171.96(13) . . . . ?
O3 C20 C21 O4 -65.29(14) . . . . ?
C7' N1' C1' N2' 2.0(2) . . . . ?
C2' N2' C1' N1' -1.9(2) . . . . ?
C1' N2' C2' N3' 179.03(13) . . . . ?
C1' N2' C2' C8' -0.8(2) . . . . ?
C9' N3' C2' N2' 2.7(2) . . . . ?
C9' N3' C2' C8' -177.47(13) . . . . ?
C20' O3' C4' C3' 8.7(2) . . . . ?
C20' O3' C4' C5' -170.61(12) . . . . ?
C8' C3' C4' O3' -176.32(13) . . . . ?
C8' C3' C4' C5' 2.9(2) . . . . ?
C17' O1' C5' C6' 1.5(2) . . . . ?
C17' O1' C5' C4' -179.70(12) . . . . ?
O3' C4' C5' O1' -4.92(17) . . . . ?
C3' C4' C5' O1' 175.77(13) . . . . ?
O3' C4' C5' C6' 173.93(13) . . . . ?
C3' C4' C5' C6' -5.4(2) . . . . ?
O1' C5' C6' C7' -178.41(13) . . . . ?
C4' C5' C6' C7' 2.9(2) . . . . ?
C1' N1' C7' C8' 0.5(2) . . . . ?
C1' N1' C7' C6' -179.55(13) . . . . ?
C5' C6' C7' N1' -178.04(13) . . . . ?
C5' C6' C7' C8' 1.92(19) . . . . ?
N1' C7' C8' C3' 175.59(12) . . . . ?
C6' C7' C8' C3' -4.36(19) . . . . ?
N1' C7' C8' C2' -2.72(18) . . . . ?
C6' C7' C8' C2' 177.32(12) . . . . ?
C4' C3' C8' C7' 1.91(19) . . . . ?
C4' C3' C8' C2' -179.91(13) . . . . ?
N2' C2' C8' C7' 2.86(19) . . . . ?
N3' C2' C8' C7' -176.93(12) . . . . ?
N2' C2' C8' C3' -175.38(13) . . . . ?
N3' C2' C8' C3' 4.8(2) . . . . ?
C2' N3' C9' C14' 68.99(19) . . . . ?
C2' N3' C9' C10' -113.83(16) . . . . ?
C14' C9' C10' C11' -0.6(2) . . . . ?
N3' C9' C10' C11' -177.79(13) . . . . ?
C9' C10' C11' C12' -0.3(2) . . . . ?
C10' C11' C12' C13' 1.1(2) . . . . ?
C11' C12' C13' C14' -1.1(2) . . . . ?
C11' C12' C13' C15' 178.07(15) . . . . ?
C10' C9' C14' C13' 0.7(2) . . . . ?
N3' C9' C14' C13' 177.81(13) . . . . ?
C12' C13' C14' C9' 0.2(2) . . . . ?
C15' C13' C14' C9' -178.98(14) . . . . ?
C5' O1' C17' C18' -176.79(12) . . . . ?
C19' O2' C18' C17' -86.34(19) . . . . ?
O1' C17' C18' O2' 74.68(17) . . . . ?
C4' O3' C20' C21' 167.96(12) . . . . ?
C22' O4' C21' C20' -169.32(14) . . . . ?
O3' C20' C21' O4' 64.58(15) . . . . ?

_refine_diff_density_max         0.960
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.071


####################################################################### 
# 
# 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_ETB_FORM_III
_database_code_depnum_ccdc_archive 'CCDC 2052732'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_ETB_FORM_III        
;
PROBLEM: Hirshfeld Test Diff for O1? --C5? . 7.5 s.u.
RESPONSE: No doubt, this is not due to wrong atom assignment.
However, it could be due to slight disorder. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N3 O4, H2O'
_chemical_formula_sum            'C22 H25 N3 O5'
_chemical_formula_weight         411.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.945(3)
_cell_length_b                   13.203(5)
_cell_length_c                   15.214(5)
_cell_angle_alpha                111.931(12)
_cell_angle_beta                 95.970(12)
_cell_angle_gamma                94.038(12)
_cell_volume                     2014.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7414
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      36.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7184
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            140498
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.368
_diffrn_reflns_theta_max         36.889
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             19237
_reflns_number_gt                16988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.2409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         19237
_refine_ls_number_parameters     570
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03487(3) -0.05825(3) 0.12227(3) 0.01359(6) Uani 1 1 d . . . . .
O2 O -0.06611(4) -0.20371(3) 0.20815(3) 0.02035(8) Uani 1 1 d . . . . .
O3 O 0.20956(3) 0.08688(3) 0.23107(2) 0.01598(7) Uani 1 1 d . . . . .
O4 O 0.20111(4) 0.15665(4) 0.42669(3) 0.02034(8) Uani 1 1 d . . . . .
N1 N 0.23212(4) -0.10610(4) -0.15713(3) 0.01417(7) Uani 1 1 d . . . . .
N2 N 0.41692(4) 0.01114(4) -0.14367(3) 0.01453(7) Uani 1 1 d . . . . .
N3 N 0.50015(4) 0.15714(3) -0.00087(3) 0.01235(7) Uani 1 1 d . . . . .
H3N H 0.4917(10) 0.1945(8) 0.0588(7) 0.029(2) Uiso 1 1 d . . . . .
C1 C 0.32680(4) -0.07322(4) -0.19076(3) 0.01536(8) Uani 1 1 d . . . . .
H1 H 0.332444 -0.113835 -0.256253 0.018 Uiso 1 1 calc R U . . .
C2 C 0.41352(4) 0.06836(4) -0.05068(3) 0.01120(7) Uani 1 1 d . . . . .
C3 C 0.31408(4) 0.08755(4) 0.09760(3) 0.01154(7) Uani 1 1 d . . . . .
H3 H 0.374970 0.145920 0.137749 0.014 Uiso 1 1 calc R U . . .
C4 C 0.22001(4) 0.05085(4) 0.13572(3) 0.01136(7) Uani 1 1 d . . . . .
C5 C 0.12381(4) -0.03336(4) 0.07550(3) 0.01132(7) Uani 1 1 d . . . . .
C6 C 0.12920(4) -0.08353(4) -0.02110(3) 0.01201(7) Uani 1 1 d . . . . .
H6 H 0.066531 -0.140375 -0.060973 0.014 Uiso 1 1 calc R U . . .
C7 C 0.22853(4) -0.05010(4) -0.06086(3) 0.01130(7) Uani 1 1 d . . . . .
C8 C 0.31957(4) 0.03750(4) -0.00238(3) 0.01066(7) Uani 1 1 d . . . . .
C9 C 0.59870(4) 0.20177(4) -0.03348(3) 0.01136(7) Uani 1 1 d . . . . .
C10 C 0.63068(4) 0.15737(4) -0.12648(3) 0.01339(7) Uani 1 1 d . . . . .
H10 H 0.584372 0.092567 -0.173078 0.016 Uiso 1 1 calc R U . . .
C11 C 0.73074(5) 0.20896(4) -0.14997(4) 0.01540(8) Uani 1 1 d . . . . .
H11 H 0.752559 0.177676 -0.212583 0.018 Uiso 1 1 calc R U . . .
C12 C 0.79941(4) 0.30506(4) -0.08403(4) 0.01517(8) Uani 1 1 d . . . . .
H12 H 0.866531 0.339579 -0.101526 0.018 Uiso 1 1 calc R U . . .
C13 C 0.76766(4) 0.35008(4) 0.00889(3) 0.01325(7) Uani 1 1 d . . . . .
C14 C 0.66862(4) 0.29825(4) 0.03400(3) 0.01284(7) Uani 1 1 d . . . . .
H14 H 0.648452 0.328530 0.097194 0.015 Uiso 1 1 calc R U . . .
C15 C 0.83459(5) 0.45115(4) 0.07749(4) 0.01663(8) Uani 1 1 d . . . . .
C16 C 0.88829(5) 0.53829(5) 0.13328(4) 0.02231(10) Uani 1 1 d . . . . .
H16 H 0.930496 0.606778 0.177125 0.027 Uiso 1 1 calc R U . . .
C17 C -0.05248(4) -0.15394(4) 0.06944(3) 0.01425(8) Uani 1 1 d . . . . .
H17A H -0.008334 -0.218775 0.040704 0.017 Uiso 1 1 calc R U . . .
H17B H -0.104035 -0.142386 0.017309 0.017 Uiso 1 1 calc R U . . .
C18 C -0.13296(5) -0.17262(5) 0.13824(4) 0.01812(9) Uani 1 1 d . . . . .
H18A H -0.169550 -0.104328 0.171262 0.022 Uiso 1 1 calc R U . . .
H18B H -0.201618 -0.231018 0.101604 0.022 Uiso 1 1 calc R U . . .
C19 C -0.01686(6) -0.11381(5) 0.29484(4) 0.02228(10) Uani 1 1 d . . . . .
H19A H -0.084170 -0.073369 0.322882 0.033 Uiso 1 1 calc R U . . .
H19B H 0.042822 -0.064564 0.281287 0.033 Uiso 1 1 calc R U . . .
H19C H 0.024621 -0.141690 0.339965 0.033 Uiso 1 1 calc R U . . .
C20 C 0.32038(4) 0.13313(4) 0.29954(3) 0.01473(8) Uani 1 1 d . . . . .
H20A H 0.333363 0.213947 0.319049 0.018 Uiso 1 1 calc R U . . .
H20B H 0.393517 0.101747 0.271497 0.018 Uiso 1 1 calc R U . . .
C21 C 0.30116(5) 0.10392(4) 0.38456(3) 0.01662(8) Uani 1 1 d . . . . .
H21A H 0.282543 0.023242 0.363666 0.020 Uiso 1 1 calc R U . . .
H21B H 0.377251 0.128407 0.431899 0.020 Uiso 1 1 calc R U . . .
C22 C 0.15853(6) 0.11446(5) 0.49292(4) 0.02298(10) Uani 1 1 d . . . . .
H22A H 0.226134 0.125504 0.544362 0.034 Uiso 1 1 calc R U . . .
H22B H 0.130416 0.035723 0.459904 0.034 Uiso 1 1 calc R U . . .
H22C H 0.089690 0.153088 0.520134 0.034 Uiso 1 1 calc R U . . .
O1' O 0.45500(3) 0.54554(3) 0.36997(3) 0.01509(7) Uani 1 1 d . . . . .
O2' O 0.55613(4) 0.69025(4) 0.28457(3) 0.02252(8) Uani 1 1 d . . . . .
O3' O 0.28523(4) 0.38842(4) 0.27015(3) 0.02224(9) Uani 1 1 d . . . . .
O4' O 0.29533(5) 0.35588(4) 0.07933(3) 0.02799(10) Uani 1 1 d . . . . .
N1' N 0.26249(4) 0.61341(4) 0.65566(3) 0.01440(7) Uani 1 1 d . . . . .
N2' N 0.07935(4) 0.49660(4) 0.64816(3) 0.01461(7) Uani 1 1 d . . . . .
N3' N -0.00132(4) 0.34392(3) 0.50883(3) 0.01311(7) Uani 1 1 d . . . . .
H3'N H 0.0073(10) 0.3042(8) 0.4493(7) 0.030(2) Uiso 1 1 d . . . . .
C1' C 0.16886(4) 0.58258(4) 0.69176(3) 0.01541(8) Uani 1 1 d . . . . .
H1' H 0.163593 0.626338 0.756661 0.018 Uiso 1 1 calc R U . . .
C2' C 0.08332(4) 0.43483(4) 0.55629(3) 0.01176(7) Uani 1 1 d . . . . .
C3' C 0.18165(4) 0.40516(4) 0.40674(3) 0.01271(7) Uani 1 1 d . . . . .
H3' H 0.121349 0.344840 0.369419 0.015 Uiso 1 1 calc R U . . .
C4' C 0.27450(4) 0.43736(4) 0.36524(3) 0.01295(7) Uani 1 1 d . . . . .
C5' C 0.36873(4) 0.52550(4) 0.42082(3) 0.01231(7) Uani 1 1 d . . . . .
C6' C 0.36407(4) 0.58257(4) 0.51697(3) 0.01288(7) Uani 1 1 d . . . . .
H6' H 0.425989 0.641601 0.554029 0.015 Uiso 1 1 calc R U . . .
C7' C 0.26630(4) 0.55255(4) 0.56011(3) 0.01173(7) Uani 1 1 d . . . . .
C8' C 0.17615(4) 0.46235(4) 0.50559(3) 0.01117(7) Uani 1 1 d . . . . .
C9' C -0.10004(4) 0.29997(4) 0.54152(3) 0.01247(7) Uani 1 1 d . . . . .
C10' C -0.13187(5) 0.34465(4) 0.63453(3) 0.01495(8) Uani 1 1 d . . . . .
H10' H -0.084481 0.408501 0.681579 0.018 Uiso 1 1 calc R U . . .
C11' C -0.23390(5) 0.29418(4) 0.65701(4) 0.01720(8) Uani 1 1 d . . . . .
H11' H -0.255936 0.325296 0.719567 0.021 Uiso 1 1 calc R U . . .
C12' C -0.30420(5) 0.19947(4) 0.59019(4) 0.01677(8) Uani 1 1 d . . . . .
H12' H -0.372939 0.166153 0.607004 0.020 Uiso 1 1 calc R U . . .
C13' C -0.27182(4) 0.15399(4) 0.49752(4) 0.01451(8) Uani 1 1 d . . . . .
C14' C -0.17051(4) 0.20418(4) 0.47360(3) 0.01417(8) Uani 1 1 d . . . . .
H14' H -0.149082 0.173237 0.410829 0.017 Uiso 1 1 calc R U . . .
C15' C -0.34305(5) 0.05627(4) 0.42693(4) 0.01804(9) Uani 1 1 d . . . . .
C16' C -0.40183(6) -0.02662(5) 0.36838(5) 0.02459(11) Uani 1 1 d . . . . .
H16' H -0.448063 -0.091822 0.322317 0.030 Uiso 1 1 calc R U . . .
C17' C 0.54825(4) 0.63775(4) 0.41784(4) 0.01570(8) Uani 1 1 d . . . . .
H17C H 0.600795 0.626543 0.469703 0.019 Uiso 1 1 calc R U . . .
H17D H 0.509611 0.706142 0.445965 0.019 Uiso 1 1 calc R U . . .
C18' C 0.62436(5) 0.64502(4) 0.34288(4) 0.01884(9) Uani 1 1 d . . . . .
H18C H 0.703413 0.692263 0.374005 0.023 Uiso 1 1 calc R U . . .
H18D H 0.643386 0.570901 0.303065 0.023 Uiso 1 1 calc R U . . .
C19' C 0.61898(7) 0.68964(7) 0.20728(5) 0.03231(14) Uani 1 1 d . . . . .
H19D H 0.628395 0.613723 0.166918 0.048 Uiso 1 1 calc R U . . .
H19E H 0.700816 0.732065 0.232446 0.048 Uiso 1 1 calc R U . . .
H19F H 0.571078 0.722731 0.169154 0.048 Uiso 1 1 calc R U . . .
C20' C 0.17411(5) 0.35709(4) 0.20148(3) 0.01636(8) Uani 1 1 d . . . . .
H20C H 0.102773 0.386890 0.233428 0.020 Uiso 1 1 calc R U . . .
H20D H 0.156283 0.275992 0.171233 0.020 Uiso 1 1 calc R U . . .
C21' C 0.19597(6) 0.40365(5) 0.12726(4) 0.02469(11) Uani 1 1 d . . . . .
H21C H 0.120078 0.387415 0.080501 0.030 Uiso 1 1 calc R U . . .
H21D H 0.216561 0.484475 0.158292 0.030 Uiso 1 1 calc R U . . .
C22' C 0.37742(7) 0.43164(7) 0.06398(7) 0.04069(19) Uani 1 1 d . . . . .
H22D H 0.444681 0.394313 0.032662 0.061 Uiso 1 1 calc R U . . .
H22E H 0.411789 0.490190 0.125489 0.061 Uiso 1 1 calc R U . . .
H22F H 0.333345 0.463514 0.023005 0.061 Uiso 1 1 calc R U . . .
O5 O 0.51731(4) 0.29619(4) 0.21013(3) 0.01991(8) Uani 1 1 d . . . . .
H5A H 0.5822(11) 0.3198(9) 0.2520(8) 0.036(3) Uiso 1 1 d . . . . .
H5B H 0.4639(11) 0.3413(9) 0.2288(8) 0.039(3) Uiso 1 1 d . . . . .
O6 O -0.01818(4) 0.19559(4) 0.29651(3) 0.02005(8) Uani 1 1 d . . . . .
H6A H -0.0825(10) 0.1706(9) 0.2519(8) 0.035(3) Uiso 1 1 d . . . . .
H6B H 0.0349(11) 0.1503(9) 0.2795(8) 0.037(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
O1 C5 1.3549(6) . ?
O1 C17 1.4379(7) . ?
O2 C19 1.4253(8) . ?
O2 C18 1.4289(8) . ?
O3 C4 1.3676(7) . ?
O3 C20 1.4447(7) . ?
O4 C21 1.4194(7) . ?
O4 C22 1.4225(7) . ?
N1 C1 1.3180(7) . ?
N1 C7 1.3786(7) . ?
N2 C2 1.3380(7) . ?
N2 C1 1.3523(7) . ?
N3 C2 1.3703(7) . ?
N3 C9 1.4132(7) . ?
N3 H3N 0.875(10) . ?
C1 H1 0.9500 . ?
C2 C8 1.4440(7) . ?
C3 C4 1.3767(7) . ?
C3 C8 1.4241(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.4344(7) . ?
C5 C6 1.3779(8) . ?
C6 C7 1.4182(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.4165(7) . ?
C9 C10 1.4072(8) . ?
C9 C14 1.4088(7) . ?
C10 C11 1.3962(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.3926(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.4057(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.4022(7) . ?
C13 C15 1.4386(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.2088(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.5120(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5114(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1' C5' 1.3527(6) . ?
O1' C17' 1.4361(7) . ?
O2' C19' 1.4206(8) . ?
O2' C18' 1.4219(8) . ?
O3' C4' 1.3682(7) . ?
O3' C20' 1.4436(7) . ?
O4' C22' 1.3978(10) . ?
O4' C21' 1.4247(8) . ?
N1' C1' 1.3201(7) . ?
N1' C7' 1.3804(7) . ?
N2' C2' 1.3367(7) . ?
N2' C1' 1.3544(7) . ?
N3' C2' 1.3701(7) . ?
N3' C9' 1.4109(7) . ?
N3' H3'N 0.880(10) . ?
C1' H1' 0.9500 . ?
C2' C8' 1.4420(7) . ?
C3' C4' 1.3731(7) . ?
C3' C8' 1.4187(8) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.4309(8) . ?
C5' C6' 1.3813(8) . ?
C6' C7' 1.4190(7) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.4164(7) . ?
C9' C10' 1.4070(8) . ?
C9' C14' 1.4082(8) . ?
C10' C11' 1.3975(8) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.3932(8) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.4055(8) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.4006(7) . ?
C13' C15' 1.4405(8) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.2077(8) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.5072(8) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' C21' 1.5048(9) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
O5 H5A 0.857(12) . ?
O5 H5B 0.857(12) . ?
O6 H6A 0.876(11) . ?
O6 H6B 0.852(11) . ?

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
C5 O1 C17 117.24(4) . . ?
C19 O2 C18 114.21(5) . . ?
C4 O3 C20 118.43(4) . . ?
C21 O4 C22 112.28(4) . . ?
C1 N1 C7 115.36(4) . . ?
C2 N2 C1 117.51(4) . . ?
C2 N3 C9 129.18(4) . . ?
C2 N3 H3N 116.4(7) . . ?
C9 N3 H3N 114.3(7) . . ?
N1 C1 N2 128.08(5) . . ?
N1 C1 H1 116.0 . . ?
N2 C1 H1 116.0 . . ?
N2 C2 N3 119.58(4) . . ?
N2 C2 C8 120.68(4) . . ?
N3 C2 C8 119.74(4) . . ?
C4 C3 C8 119.60(4) . . ?
C4 C3 H3 120.2 . . ?
C8 C3 H3 120.2 . . ?
O3 C4 C3 125.03(4) . . ?
O3 C4 C5 114.01(4) . . ?
C3 C4 C5 120.94(4) . . ?
O1 C5 C6 125.61(4) . . ?
O1 C5 C4 114.50(4) . . ?
C6 C5 C4 119.87(4) . . ?
C5 C6 C7 119.83(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N1 C7 C8 122.31(4) . . ?
N1 C7 C6 117.41(4) . . ?
C8 C7 C6 120.28(4) . . ?
C7 C8 C3 119.31(4) . . ?
C7 C8 C2 115.88(4) . . ?
C3 C8 C2 124.80(4) . . ?
C10 C9 C14 118.90(4) . . ?
C10 C9 N3 125.10(4) . . ?
C14 C9 N3 115.99(4) . . ?
C11 C10 C9 119.71(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 121.74(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.83(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 120.09(4) . . ?
C14 C13 C15 119.92(5) . . ?
C12 C13 C15 119.96(4) . . ?
C13 C14 C9 120.71(5) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C16 C15 C13 177.41(6) . . ?
C15 C16 H16 180.0 . . ?
O1 C17 C18 107.89(4) . . ?
O1 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O1 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
O2 C18 C17 112.70(5) . . ?
O2 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
O2 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 106.32(4) . . ?
O3 C20 H20A 110.5 . . ?
C21 C20 H20A 110.5 . . ?
O3 C20 H20B 110.5 . . ?
C21 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?
O4 C21 C20 108.73(4) . . ?
O4 C21 H21A 109.9 . . ?
C20 C21 H21A 109.9 . . ?
O4 C21 H21B 109.9 . . ?
C20 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5' O1' C17' 118.03(4) . . ?
C19' O2' C18' 111.10(5) . . ?
C4' O3' C20' 118.35(4) . . ?
C22' O4' C21' 113.43(6) . . ?
C1' N1' C7' 115.49(4) . . ?
C2' N2' C1' 117.06(4) . . ?
C2' N3' C9' 130.00(4) . . ?
C2' N3' H3'N 116.7(7) . . ?
C9' N3' H3'N 113.2(7) . . ?
N1' C1' N2' 128.33(5) . . ?
N1' C1' H1' 115.8 . . ?
N2' C1' H1' 115.8 . . ?
N2' C2' N3' 120.17(4) . . ?
N2' C2' C8' 120.87(5) . . ?
N3' C2' C8' 118.96(4) . . ?
C4' C3' C8' 119.72(4) . . ?
C4' C3' H3' 120.1 . . ?
C8' C3' H3' 120.1 . . ?
O3' C4' C3' 123.57(5) . . ?
O3' C4' C5' 115.38(4) . . ?
C3' C4' C5' 121.04(5) . . ?
O1' C5' C6' 126.23(4) . . ?
O1' C5' C4' 113.88(5) . . ?
C6' C5' C4' 119.87(4) . . ?
C5' C6' C7' 119.65(4) . . ?
C5' C6' H6' 120.2 . . ?
C7' C6' H6' 120.2 . . ?
N1' C7' C8' 121.73(4) . . ?
N1' C7' C6' 118.10(4) . . ?
C8' C7' C6' 120.18(5) . . ?
C7' C8' C3' 119.44(4) . . ?
C7' C8' C2' 116.36(4) . . ?
C3' C8' C2' 124.20(4) . . ?
C10' C9' C14' 119.20(4) . . ?
C10' C9' N3' 125.14(4) . . ?
C14' C9' N3' 115.65(5) . . ?
C11' C10' C9' 119.34(5) . . ?
C11' C10' H10' 120.3 . . ?
C9' C10' H10' 120.3 . . ?
C12' C11' C10' 121.81(5) . . ?
C12' C11' H11' 119.1 . . ?
C10' C11' H11' 119.1 . . ?
C11' C12' C13' 118.96(5) . . ?
C11' C12' H12' 120.5 . . ?
C13' C12' H12' 120.5 . . ?
C14' C13' C12' 119.92(5) . . ?
C14' C13' C15' 119.93(5) . . ?
C12' C13' C15' 120.15(5) . . ?
C13' C14' C9' 120.75(5) . . ?
C13' C14' H14' 119.6 . . ?
C9' C14' H14' 119.6 . . ?
C16' C15' C13' 179.00(6) . . ?
C15' C16' H16' 180.0 . . ?
O1' C17' C18' 106.33(5) . . ?
O1' C17' H17C 110.5 . . ?
C18' C17' H17C 110.5 . . ?
O1' C17' H17D 110.5 . . ?
C18' C17' H17D 110.5 . . ?
H17C C17' H17D 108.7 . . ?
O2' C18' C17' 108.82(5) . . ?
O2' C18' H18C 109.9 . . ?
C17' C18' H18C 109.9 . . ?
O2' C18' H18D 109.9 . . ?
C17' C18' H18D 109.9 . . ?
H18C C18' H18D 108.3 . . ?
O2' C19' H19D 109.5 . . ?
O2' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
O2' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O3' C20' C21' 107.21(5) . . ?
O3' C20' H20C 110.3 . . ?
C21' C20' H20C 110.3 . . ?
O3' C20' H20D 110.3 . . ?
C21' C20' H20D 110.3 . . ?
H20C C20' H20D 108.5 . . ?
O4' C21' C20' 109.25(5) . . ?
O4' C21' H21C 109.8 . . ?
C20' C21' H21C 109.8 . . ?
O4' C21' H21D 109.8 . . ?
C20' C21' H21D 109.8 . . ?
H21C C21' H21D 108.3 . . ?
O4' C22' H22D 109.5 . . ?
O4' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
O4' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
H5A O5 H5B 107.7(10) . . ?
H6A O6 H6B 106.7(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
C7 N1 C1 N2 -3.20(8) . . . . ?
C2 N2 C1 N1 1.64(8) . . . . ?
C1 N2 C2 N3 -177.53(4) . . . . ?
C1 N2 C2 C8 2.47(7) . . . . ?
C9 N3 C2 N2 0.39(7) . . . . ?
C9 N3 C2 C8 -179.61(4) . . . . ?
C20 O3 C4 C3 -24.42(7) . . . . ?
C20 O3 C4 C5 154.11(4) . . . . ?
C8 C3 C4 O3 175.25(4) . . . . ?
C8 C3 C4 C5 -3.19(7) . . . . ?
C17 O1 C5 C6 8.36(7) . . . . ?
C17 O1 C5 C4 -169.80(4) . . . . ?
O3 C4 C5 O1 3.86(6) . . . . ?
C3 C4 C5 O1 -177.54(4) . . . . ?
O3 C4 C5 C6 -174.42(4) . . . . ?
C3 C4 C5 C6 4.18(7) . . . . ?
O1 C5 C6 C7 -179.35(4) . . . . ?
C4 C5 C6 C7 -1.29(7) . . . . ?
C1 N1 C7 C8 0.67(7) . . . . ?
C1 N1 C7 C6 -179.19(4) . . . . ?
C5 C6 C7 N1 177.39(4) . . . . ?
C5 C6 C7 C8 -2.47(7) . . . . ?
N1 C7 C8 C3 -176.42(4) . . . . ?
C6 C7 C8 C3 3.43(7) . . . . ?
N1 C7 C8 C2 2.89(7) . . . . ?
C6 C7 C8 C2 -177.26(4) . . . . ?
C4 C3 C8 C7 -0.59(7) . . . . ?
C4 C3 C8 C2 -179.83(4) . . . . ?
N2 C2 C8 C7 -4.50(7) . . . . ?
N3 C2 C8 C7 175.51(4) . . . . ?
N2 C2 C8 C3 174.77(4) . . . . ?
N3 C2 C8 C3 -5.23(7) . . . . ?
C2 N3 C9 C10 -3.54(8) . . . . ?
C2 N3 C9 C14 176.42(4) . . . . ?
C14 C9 C10 C11 0.32(7) . . . . ?
N3 C9 C10 C11 -179.71(4) . . . . ?
C9 C10 C11 C12 -1.10(7) . . . . ?
C10 C11 C12 C13 0.85(7) . . . . ?
C11 C12 C13 C14 0.17(7) . . . . ?
C11 C12 C13 C15 -178.05(5) . . . . ?
C12 C13 C14 C9 -0.94(7) . . . . ?
C15 C13 C14 C9 177.29(4) . . . . ?
C10 C9 C14 C13 0.68(7) . . . . ?
N3 C9 C14 C13 -179.29(4) . . . . ?
C5 O1 C17 C18 173.78(4) . . . . ?
C19 O2 C18 C17 92.36(6) . . . . ?
O1 C17 C18 O2 -67.29(6) . . . . ?
C4 O3 C20 C21 -147.47(4) . . . . ?
C22 O4 C21 C20 166.62(4) . . . . ?
O3 C20 C21 O4 -64.17(6) . . . . ?
C7' N1' C1' N2' 2.88(8) . . . . ?
C2' N2' C1' N1' -1.16(8) . . . . ?
C1' N2' C2' N3' 177.34(4) . . . . ?
C1' N2' C2' C8' -2.63(7) . . . . ?
C9' N3' C2' N2' 0.16(7) . . . . ?
C9' N3' C2' C8' -179.88(4) . . . . ?
C20' O3' C4' C3' 40.35(7) . . . . ?
C20' O3' C4' C5' -140.39(5) . . . . ?
C8' C3' C4' O3' -178.56(4) . . . . ?
C8' C3' C4' C5' 2.21(7) . . . . ?
C17' O1' C5' C6' -3.18(7) . . . . ?
C17' O1' C5' C4' 175.44(4) . . . . ?
O3' C4' C5' O1' -0.74(6) . . . . ?
C3' C4' C5' O1' 178.54(4) . . . . ?
O3' C4' C5' C6' 177.97(4) . . . . ?
C3' C4' C5' C6' -2.75(7) . . . . ?
O1' C5' C6' C7' 179.14(4) . . . . ?
C4' C5' C6' C7' 0.60(7) . . . . ?
C1' N1' C7' C8' -0.81(7) . . . . ?
C1' N1' C7' C6' 179.30(4) . . . . ?
C5' C6' C7' N1' -178.12(4) . . . . ?
C5' C6' C7' C8' 1.99(7) . . . . ?
N1' C7' C8' C3' 177.61(4) . . . . ?
C6' C7' C8' C3' -2.51(7) . . . . ?
N1' C7' C8' C2' -2.48(6) . . . . ?
C6' C7' C8' C2' 177.40(4) . . . . ?
C4' C3' C8' C7' 0.40(7) . . . . ?
C4' C3' C8' C2' -179.51(4) . . . . ?
N2' C2' C8' C7' 4.28(7) . . . . ?
N3' C2' C8' C7' -175.69(4) . . . . ?
N2' C2' C8' C3' -175.82(4) . . . . ?
N3' C2' C8' C3' 4.22(7) . . . . ?
C2' N3' C9' C10' 0.36(8) . . . . ?
C2' N3' C9' C14' -179.97(5) . . . . ?
C14' C9' C10' C11' -1.10(7) . . . . ?
N3' C9' C10' C11' 178.57(4) . . . . ?
C9' C10' C11' C12' 1.04(8) . . . . ?
C10' C11' C12' C13' -0.38(8) . . . . ?
C11' C12' C13' C14' -0.22(7) . . . . ?
C11' C12' C13' C15' -179.85(5) . . . . ?
C12' C13' C14' C9' 0.14(7) . . . . ?
C15' C13' C14' C9' 179.77(4) . . . . ?
C10' C9' C14' C13' 0.53(7) . . . . ?
N3' C9' C14' C13' -179.17(4) . . . . ?
C5' O1' C17' C18' -175.77(4) . . . . ?
C19' O2' C18' C17' -174.68(5) . . . . ?
O1' C17' C18' O2' 75.84(6) . . . . ?
C4' O3' C20' C21' 129.05(5) . . . . ?
C22' O4' C21' C20' -137.77(7) . . . . ?
O3' C20' C21' O4' 62.53(6) . . . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.047


####################################################################### 
# 
# 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_ETB_FORM_IV
_database_code_depnum_ccdc_archive 'CCDC 2052733'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2020-12-28 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N3 O4, 3H2O'
_chemical_formula_sum            'C22 H29 N3 O7'
_chemical_formula_weight         447.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.88300(10)
_cell_length_b                   15.3530(5)
_cell_length_c                   30.0340(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.0870(10)
_cell_angle_gamma                90
_cell_volume                     2248.34(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.55

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            35385
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         30.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6801
_reflns_number_gt                6127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.9966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6801
_refine_ls_number_parameters     347
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.05914(14) 0.25731(4) 0.37050(2) 0.01517(13) Uani 1 1 d . . . A 4
O2 O 1.2557(2) 0.17236(6) 0.45199(3) 0.0318(2) Uani 1 1 d . . . B 4
O3 O 0.76657(15) 0.39437(5) 0.37340(2) 0.01702(14) Uani 1 1 d . . . A 4
O4 O 0.94265(17) 0.57432(5) 0.38334(2) 0.02163(16) Uani 1 1 d . . . C 4
N1 N 0.61524(17) 0.16933(5) 0.23049(3) 0.01552(15) Uani 1 1 d . . . A 4
N2 N 0.24224(17) 0.25407(5) 0.19857(3) 0.01611(16) Uani 1 1 d . . . A 4
N3 N 0.08597(16) 0.37980(5) 0.23197(3) 0.01388(15) Uani 1 1 d . . . A 4
H3N H 0.100182 0.413213 0.255787 0.017 Uiso 1 1 calc R U . A 4
C1 C 0.4194(2) 0.18700(6) 0.20004(3) 0.01725(18) Uani 1 1 d . . . A 4
H1 H 0.400639 0.147069 0.175899 0.021 Uiso 1 1 calc R U . A 4
C2 C 0.26193(18) 0.31096(6) 0.23202(3) 0.01274(16) Uani 1 1 d . . . A 4
C3 C 0.50141(18) 0.35746(6) 0.30496(3) 0.01348(16) Uani 1 1 d . . . A 4
H3 H 0.384082 0.406439 0.307231 0.016 Uiso 1 1 calc R U . A 4
C4 C 0.70579(18) 0.34246(6) 0.33735(3) 0.01315(16) Uani 1 1 d . . . A 4
C5 C 0.87646(18) 0.26725(6) 0.33505(3) 0.01289(16) Uani 1 1 d . . . A 4
C6 C 0.84639(18) 0.21169(6) 0.29934(3) 0.01327(16) Uani 1 1 d . . . A 4
H6 H 0.964084 0.162712 0.297424 0.016 Uiso 1 1 calc R U . A 4
C7 C 0.63975(18) 0.22733(6) 0.26530(3) 0.01251(16) Uani 1 1 d . . . A 4
C8 C 0.46556(17) 0.29997(6) 0.26821(3) 0.01212(16) Uani 1 1 d . . . A 4
C9 C -0.11556(18) 0.40508(6) 0.19918(3) 0.01482(17) Uani 1 1 d . . . A 4
C10 C -0.2883(2) 0.47365(6) 0.21065(3) 0.01810(18) Uani 1 1 d . . . A 4
H10 H -0.263316 0.500547 0.239066 0.022 Uiso 1 1 calc R U . A 4
C11 C -0.4953(2) 0.50241(7) 0.18076(4) 0.0226(2) Uani 1 1 d . . . A 4
H11 H -0.611178 0.548765 0.188965 0.027 Uiso 1 1 calc R U . A 4
C12 C -0.5350(2) 0.46436(7) 0.13908(4) 0.0249(2) Uani 1 1 d . . . A 4
H12 H -0.678987 0.483655 0.118922 0.030 Uiso 1 1 calc R U . A 4
C13 C -0.3612(2) 0.39753(7) 0.12717(4) 0.0252(2) Uani 1 1 d . . . A 4
C14 C -0.1501(2) 0.36760(7) 0.15694(3) 0.02057(19) Uani 1 1 d . . . A 4
H14 H -0.031828 0.322173 0.148369 0.025 Uiso 1 1 calc R U . A 4
C15 C -0.4212(8) 0.3554(3) 0.08659(14) 0.0249(6) Uani 0.65 1 d . . P D 1
C16 C -0.4686(7) 0.3203(2) 0.05159(10) 0.0401(7) Uani 0.65 1 d . . P D 1
H16 H -0.506289 0.292266 0.023721 0.048 Uiso 0.65 1 calc R U P D 1
C15' C -0.3424(16) 0.3589(6) 0.0787(3) 0.0311(15) Uani 0.35 1 d . . P E 2
C16' C -0.3406(15) 0.3262(4) 0.04339(19) 0.0444(14) Uani 0.35 1 d . . P E 2
H16' H -0.339119 0.299725 0.014819 0.053 Uiso 0.35 1 calc R U P E 2
C17 C 1.22941(19) 0.18115(6) 0.37074(3) 0.01638(17) Uani 1 1 d . . . . .
H17A H 1.344735 0.181352 0.344616 0.020 Uiso 1 1 calc R U . A 4
H17B H 1.115065 0.127864 0.369582 0.020 Uiso 1 1 calc R U . A 4
C18 C 1.4070(2) 0.18363(7) 0.41342(4) 0.0233(2) Uani 1 1 d . . . . .
H18A H 1.547122 0.137166 0.412530 0.028 Uiso 1 1 calc R U . B 4
H18B H 1.503891 0.240244 0.415443 0.028 Uiso 1 1 calc R U . B 4
C19 C 1.1913(4) 0.08438(10) 0.46118(5) 0.0470(4) Uani 1 1 d . . . . .
H19A H 1.075489 0.060540 0.436435 0.071 Uiso 1 1 calc R U . B 4
H19B H 1.092813 0.081377 0.488719 0.071 Uiso 1 1 calc R U . B 4
H19C H 1.360909 0.050390 0.464725 0.071 Uiso 1 1 calc R U . B 4
C20 C 0.5904(2) 0.46767(6) 0.38038(3) 0.01893(18) Uani 1 1 d . . . . .
H20A H 0.423837 0.448446 0.395013 0.023 Uiso 1 1 calc R U . A 4
H20B H 0.533301 0.494797 0.351446 0.023 Uiso 1 1 calc R U . A 4
C21 C 0.7473(2) 0.53222(7) 0.40948(3) 0.01870(18) Uani 1 1 d . . . . .
H21A H 0.620197 0.575724 0.421257 0.022 Uiso 1 1 calc R U . C 4
H21B H 0.841880 0.501920 0.435026 0.022 Uiso 1 1 calc R U . C 4
C22 C 1.0548(2) 0.65035(7) 0.40447(4) 0.0257(2) Uani 1 1 d . . . . .
H22A H 0.907905 0.692527 0.408752 0.039 Uiso 1 1 calc R U . C 4
H22B H 1.191423 0.676221 0.385718 0.039 Uiso 1 1 calc R U . C 4
H22C H 1.142341 0.634631 0.433493 0.039 Uiso 1 1 calc R U . C 4
O5 O 0.09467(16) 0.52414(5) 0.29733(3) 0.01919(15) Uani 1 1 d . . . . .
H5A H 0.041(3) 0.5385(11) 0.3227(6) 0.034(4) Uiso 1 1 d . . . . .
H5B H 0.165(3) 0.5690(11) 0.2871(5) 0.030(4) Uiso 1 1 d . . . . .
O6 O 0.9579(3) 0.33553(7) 0.46447(4) 0.0469(3) Uani 1 1 d D . . . .
H6A H 0.926(5) 0.3376(16) 0.4340(6) 0.018(6) Uiso 0.57 1 d D . P . .
H6C H 1.022(3) 0.3287(11) 0.4872(5) 0.026(4) Uiso 1 1 d D . . . .
H6B H 1.017(6) 0.2817(13) 0.4610(11) 0.019(7) Uiso 0.43 1 d D . P . .
O7 O 0.4763(5) 0.43225(18) 0.49141(9) 0.0339(5) Uani 0.5 1 d D . P F 1
H7A H 0.341(12) 0.406(5) 0.478(3) 0.24(4) Uiso 0.75 1 d D . P G 1
H7B H 0.500000 0.500000 0.500000 0.22(6) Uiso 0.5 2 d S . P H 1
O8 O 0.4665(5) 0.39104(19) 0.49220(8) 0.0354(5) Uani 0.5 1 d D . P I 2
H8B H 0.623(4) 0.388(2) 0.4834(9) 0.094(9) Uiso 1 1 d D . . J 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3602(10) . ?
O1 C17 1.4346(11) . ?
O2 C18 1.4175(15) . ?
O2 C19 1.4175(17) . ?
O3 C4 1.3642(11) . ?
O3 C20 1.4387(11) . ?
O4 C21 1.4229(13) . ?
O4 C22 1.4242(13) . ?
N1 C1 1.3155(12) . ?
N1 C7 1.3738(11) . ?
N2 C2 1.3309(12) . ?
N2 C1 1.3441(12) . ?
N3 C2 1.3620(12) . ?
N3 C9 1.4088(11) . ?
N3 H3N 0.8800 . ?
C1 H1 0.9500 . ?
C2 C8 1.4429(12) . ?
C3 C4 1.3750(12) . ?
C3 C8 1.4168(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.4279(12) . ?
C5 C6 1.3722(12) . ?
C6 C7 1.4177(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.4081(12) . ?
C9 C14 1.3949(13) . ?
C9 C10 1.4035(13) . ?
C10 C11 1.3874(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3856(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3906(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.4049(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.193(6) . ?
C16 H16 0.9500 . ?
C15' C16' 1.173(11) . ?
C16' H16' 0.9500 . ?
C17 C18 1.5089(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5038(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O5 H5A 0.849(18) . ?
O5 H5B 0.837(18) . ?
O6 H6A 0.920(16) . ?
O6 H6C 0.742(13) . ?
O6 H6B 0.884(18) . ?
O7 H7A 0.85(2) . ?
O7 H7B 1.076(3) . ?
O8 H8B 0.824(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C17 116.79(7) . . ?
C18 O2 C19 113.98(11) . . ?
C4 O3 C20 117.80(7) . . ?
C21 O4 C22 112.30(8) . . ?
C1 N1 C7 115.21(8) . . ?
C2 N2 C1 117.25(8) . . ?
C2 N3 C9 129.16(8) . . ?
C2 N3 H3N 115.4 . . ?
C9 N3 H3N 115.4 . . ?
N1 C1 N2 128.55(9) . . ?
N1 C1 H1 115.7 . . ?
N2 C1 H1 115.7 . . ?
N2 C2 N3 119.23(8) . . ?
N2 C2 C8 120.71(8) . . ?
N3 C2 C8 120.05(8) . . ?
C4 C3 C8 120.08(8) . . ?
C4 C3 H3 120.0 . . ?
C8 C3 H3 120.0 . . ?
O3 C4 C3 125.61(8) . . ?
O3 C4 C5 114.09(8) . . ?
C3 C4 C5 120.31(8) . . ?
O1 C5 C6 125.46(8) . . ?
O1 C5 C4 114.38(8) . . ?
C6 C5 C4 120.15(8) . . ?
C5 C6 C7 120.02(8) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N1 C7 C8 122.16(8) . . ?
N1 C7 C6 117.94(8) . . ?
C8 C7 C6 119.89(8) . . ?
C7 C8 C3 119.47(8) . . ?
C7 C8 C2 116.11(8) . . ?
C3 C8 C2 124.41(8) . . ?
C14 C9 C10 119.20(9) . . ?
C14 C9 N3 124.60(9) . . ?
C10 C9 N3 116.19(8) . . ?
C11 C10 C9 120.42(10) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.81(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.06(9) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 120.97(10) . . ?
C9 C14 C13 119.51(10) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C15 C16 H16 180.0 . . ?
C15' C16' H16' 180.0 . . ?
O1 C17 C18 106.85(8) . . ?
O1 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O1 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
O2 C18 C17 112.98(9) . . ?
O2 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
O2 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 108.07(8) . . ?
O3 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
O3 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
O4 C21 C20 108.32(8) . . ?
O4 C21 H21A 110.0 . . ?
C20 C21 H21A 110.0 . . ?
O4 C21 H21B 110.0 . . ?
C20 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H5A O5 H5B 105.8(16) . . ?
H6A O6 H6C 164(2) . . ?
H6A O6 H6B 87(3) . . ?
H6C O6 H6B 81(2) . . ?
H7A O7 H7B 129(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
C7 N1 C1 N2 0.22(15) . . . . ?
C2 N2 C1 N1 -0.37(16) . . . . ?
C1 N2 C2 N3 -179.79(8) . . . . ?
C1 N2 C2 C8 -0.21(13) . . . . ?
C9 N3 C2 N2 -4.23(14) . . . . ?
C9 N3 C2 C8 176.18(8) . . . . ?
C20 O3 C4 C3 5.06(13) . . . . ?
C20 O3 C4 C5 -174.91(8) . . . . ?
C8 C3 C4 O3 177.70(8) . . . . ?
C8 C3 C4 C5 -2.33(13) . . . . ?
C17 O1 C5 C6 -1.48(13) . . . . ?
C17 O1 C5 C4 177.86(8) . . . . ?
O3 C4 C5 O1 3.80(11) . . . . ?
C3 C4 C5 O1 -176.16(8) . . . . ?
O3 C4 C5 C6 -176.82(8) . . . . ?
C3 C4 C5 C6 3.21(13) . . . . ?
O1 C5 C6 C7 177.29(8) . . . . ?
C4 C5 C6 C7 -2.01(13) . . . . ?
C1 N1 C7 C8 0.52(13) . . . . ?
C1 N1 C7 C6 179.72(8) . . . . ?
C5 C6 C7 N1 -179.21(8) . . . . ?
C5 C6 C7 C8 0.01(13) . . . . ?
N1 C7 C8 C3 -179.96(8) . . . . ?
C6 C7 C8 C3 0.86(13) . . . . ?
N1 C7 C8 C2 -1.02(13) . . . . ?
C6 C7 C8 C2 179.80(8) . . . . ?
C4 C3 C8 C7 0.33(13) . . . . ?
C4 C3 C8 C2 -178.52(8) . . . . ?
N2 C2 C8 C7 0.85(12) . . . . ?
N3 C2 C8 C7 -179.57(8) . . . . ?
N2 C2 C8 C3 179.73(9) . . . . ?
N3 C2 C8 C3 -0.69(13) . . . . ?
C2 N3 C9 C14 -7.88(15) . . . . ?
C2 N3 C9 C10 172.91(9) . . . . ?
C14 C9 C10 C11 1.56(14) . . . . ?
N3 C9 C10 C11 -179.18(9) . . . . ?
C9 C10 C11 C12 -0.20(15) . . . . ?
C10 C11 C12 C13 -1.05(16) . . . . ?
C11 C12 C13 C14 0.93(17) . . . . ?
C10 C9 C14 C13 -1.66(15) . . . . ?
N3 C9 C14 C13 179.14(9) . . . . ?
C12 C13 C14 C9 0.43(17) . . . . ?
C5 O1 C17 C18 -178.57(8) . . . . ?
C19 O2 C18 C17 80.37(13) . . . . ?
O1 C17 C18 O2 67.52(11) . . . . ?
C4 O3 C20 C21 -158.79(8) . . . . ?
C22 O4 C21 C20 165.87(8) . . . . ?
O3 C20 C21 O4 74.15(10) . . . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.046



#===END
