# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_66
_database_code_depnum_ccdc_archive 'CCDC 1907329'
loop_
_audit_author_name
_audit_author_address
'JAIS KURIAN'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2019-04-02 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H23 N O5'
_chemical_formula_sum            'C27 H23 N O5'
_chemical_formula_weight         441.46

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

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

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

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

_cell_length_a                   6.0337(2)
_cell_length_b                   12.7989(4)
_cell_length_c                   15.3967(5)
_cell_angle_alpha                83.2254(14)
_cell_angle_beta                 79.7254(12)
_cell_angle_gamma                82.5173(12)
_cell_volume                     1154.49(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6635
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.76

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13283
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4053
_reflns_number_gt                3315
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.6246P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4053
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2893(3) 0.78368(13) 0.90628(11) 0.0302(4) Uani 1 1 d . . . . .
C2 C 0.1645(3) 0.75077(14) 0.98461(12) 0.0349(4) Uani 1 1 d . . . . .
H2 H 0.0672 0.7988 1.0184 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1863(3) 0.64020(14) 1.01391(12) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.1394 0.6166 1.0730 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2766(3) 0.57056(14) 0.95391(11) 0.0323(4) Uani 1 1 d . . . . .
H4 H 0.2565 0.4993 0.9675 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3641(3) 0.58222(13) 0.78877(11) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.4267(3) 0.65952(14) 0.72560(12) 0.0345(4) Uani 1 1 d . . . . .
C7 C 0.5184(3) 0.74509(14) 0.76520(12) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.3782(3) 0.85239(14) 0.76142(13) 0.0400(5) Uani 1 1 d . . . . .
C9 C 0.2528(3) 0.87125(13) 0.84139(12) 0.0331(4) Uani 1 1 d . . . . .
C10 C 0.4820(3) 0.70798(13) 0.86564(11) 0.0308(4) Uani 1 1 d . . . . .
C11 C 0.2713(3) 0.48319(14) 0.78094(11) 0.0327(4) Uani 1 1 d . . . . .
C12 C 0.3696(3) 0.38612(14) 0.81432(13) 0.0418(5) Uani 1 1 d . . . . .
H12 H 0.4949 0.3833 0.8424 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2829(4) 0.29368(17) 0.80627(16) 0.0566(6) Uani 1 1 d . . . . .
H13 H 0.3501 0.2290 0.8287 0.068 Uiso 1 1 calc R U . . .
C14 C 0.0974(5) 0.29725(19) 0.76505(16) 0.0626(7) Uani 1 1 d . . . . .
H14 H 0.0401 0.2349 0.7592 0.075 Uiso 1 1 calc R U . . .
C15 C -0.0032(4) 0.3927(2) 0.73261(14) 0.0586(6) Uani 1 1 d . . . . .
H15 H -0.1290 0.3948 0.7050 0.070 Uiso 1 1 calc R U . . .
C16 C 0.0816(3) 0.48617(17) 0.74074(13) 0.0445(5) Uani 1 1 d . . . . .
H16 H 0.0115 0.5507 0.7193 0.053 Uiso 1 1 calc R U . . .
C17 C 0.4312(3) 0.66080(15) 0.62871(12) 0.0411(5) Uani 1 1 d . . . . .
C18 C 0.6216(5) 0.6191(2) 0.57513(15) 0.0637(7) Uani 1 1 d . . . . .
H18 H 0.7460 0.5883 0.6007 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6337(6) 0.6214(3) 0.48519(18) 0.0866(9) Uani 1 1 d . . . . .
H19 H 0.7659 0.5937 0.4507 0.104 Uiso 1 1 calc R U . . .
C20 C 0.4554(6) 0.6636(3) 0.44681(17) 0.0915(11) Uani 1 1 d . . . . .
H20 H 0.4635 0.6650 0.3858 0.110 Uiso 1 1 calc R U . . .
C21 C 0.2646(6) 0.7040(4) 0.4970(2) 0.1142(14) Uani 1 1 d . . . . .
H21 H 0.1403 0.7327 0.4706 0.137 Uiso 1 1 calc R U . . .
C22 C 0.2522(5) 0.7029(3) 0.58879(18) 0.0911(11) Uani 1 1 d . . . . .
H22 H 0.1198 0.7314 0.6228 0.109 Uiso 1 1 calc R U . . .
C23 C 0.3979(5) 0.92360(17) 0.67905(16) 0.0669(7) Uani 1 1 d . . . . .
C24 C 0.2421(10) 1.0748(3) 0.5984(2) 0.177(3) Uani 1 1 d . . . . .
H24A H 0.3761 1.1102 0.5909 0.265 Uiso 1 1 calc R U . . .
H24B H 0.1106 1.1262 0.6037 0.265 Uiso 1 1 calc R U . . .
H24C H 0.2466 1.0367 0.5479 0.265 Uiso 1 1 calc R U . . .
C25 C 0.0924(3) 0.96757(14) 0.86282(13) 0.0360(4) Uani 1 1 d . . . . .
C26 C -0.2865(4) 1.0424(2) 0.8768(3) 0.0875(10) Uani 1 1 d . . . . .
H26A H -0.2904 1.0570 0.9368 0.131 Uiso 1 1 calc R U . . .
H26B H -0.4316 1.0240 0.8703 0.131 Uiso 1 1 calc R U . . .
H26C H -0.2514 1.1040 0.8373 0.131 Uiso 1 1 calc R U . . .
C27 C 0.6912(3) 0.70165(16) 0.90881(15) 0.0457(5) Uani 1 1 d . . . . .
H27A H 0.6515 0.6840 0.9715 0.069 Uiso 1 1 calc R U . . .
H27B H 0.7508 0.7688 0.8980 0.069 Uiso 1 1 calc R U . . .
H27C H 0.8037 0.6481 0.8842 0.069 Uiso 1 1 calc R U . . .
N1 N 0.3980(2) 0.60379(10) 0.87307(9) 0.0302(3) Uani 1 1 d . . . . .
O1 O 0.7518(2) 0.75133(12) 0.72928(11) 0.0507(4) Uani 1 1 d . . . . .
O2 O 0.5527(5) 0.91298(17) 0.61844(14) 0.1161(10) Uani 1 1 d . . . . .
O3 O 0.2315(4) 1.00103(16) 0.67833(12) 0.1028(8) Uani 1 1 d . . . . .
O4 O 0.1456(3) 1.04434(12) 0.88718(13) 0.0656(5) Uani 1 1 d . . . . .
O5 O -0.1149(2) 0.95522(11) 0.85563(13) 0.0637(5) Uani 1 1 d . . . . .
H1O H 0.742(7) 0.797(3) 0.684(3) 0.131(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
C1 C2 1.356(2) . ?
C1 C9 1.433(2) . ?
C1 C10 1.508(2) . ?
C2 C3 1.430(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.377(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.344(2) . ?
C5 N1 1.413(2) . ?
C5 C11 1.476(2) . ?
C6 C17 1.485(3) . ?
C6 C7 1.521(3) . ?
C7 O1 1.427(2) . ?
C7 C8 1.517(3) . ?
C7 C10 1.549(2) . ?
C8 C9 1.355(3) . ?
C8 C23 1.468(3) . ?
C9 C25 1.496(2) . ?
C10 N1 1.472(2) . ?
C10 C27 1.517(3) . ?
C11 C12 1.388(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.357(3) . ?
C17 C18 1.375(3) . ?
C18 C19 1.371(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.341(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.346(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O2 1.204(3) . ?
C23 O3 1.316(3) . ?
C24 O3 1.458(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O4 1.192(2) . ?
C25 O5 1.306(2) . ?
C26 O5 1.445(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O1 H1O 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 132.54(17) . . ?
C2 C1 C10 118.13(15) . . ?
C9 C1 C10 108.08(15) . . ?
C1 C2 C3 118.21(16) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 118.69(16) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 N1 120.91(16) . . ?
C3 C4 H4 119.5 . . ?
N1 C4 H4 119.5 . . ?
C6 C5 N1 111.63(15) . . ?
C6 C5 C11 129.51(16) . . ?
N1 C5 C11 118.86(14) . . ?
C5 C6 C17 126.95(17) . . ?
C5 C6 C7 110.49(15) . . ?
C17 C6 C7 122.31(15) . . ?
O1 C7 C8 112.49(15) . . ?
O1 C7 C6 110.75(15) . . ?
C8 C7 C6 114.93(16) . . ?
O1 C7 C10 112.22(15) . . ?
C8 C7 C10 102.81(14) . . ?
C6 C7 C10 103.01(13) . . ?
C9 C8 C23 127.97(18) . . ?
C9 C8 C7 111.63(16) . . ?
C23 C8 C7 120.32(17) . . ?
C8 C9 C1 110.81(16) . . ?
C8 C9 C25 126.84(17) . . ?
C1 C9 C25 122.34(16) . . ?
N1 C10 C1 107.25(13) . . ?
N1 C10 C27 111.26(14) . . ?
C1 C10 C27 112.79(15) . . ?
N1 C10 C7 105.18(13) . . ?
C1 C10 C7 104.97(14) . . ?
C27 C10 C7 114.76(15) . . ?
C12 C11 C16 118.95(17) . . ?
C12 C11 C5 120.85(17) . . ?
C16 C11 C5 120.19(16) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 117.0(2) . . ?
C22 C17 C6 122.5(2) . . ?
C18 C17 C6 120.47(19) . . ?
C19 C18 C17 122.0(3) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.7(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
O2 C23 O3 123.2(2) . . ?
O2 C23 C8 123.2(2) . . ?
O3 C23 C8 113.5(2) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 O5 124.17(17) . . ?
O4 C25 C9 124.08(17) . . ?
O5 C25 C9 111.68(15) . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 N1 C5 126.65(14) . . ?
C4 N1 C10 116.56(13) . . ?
C5 N1 C10 109.40(13) . . ?
C7 O1 H1O 101(3) . . ?
C23 O3 C24 116.2(2) . . ?
C25 O5 C26 116.74(17) . . ?

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
C9 C1 C2 C3 151.21(19) . . . . ?
C10 C1 C2 C3 -14.3(2) . . . . ?
C1 C2 C3 C4 -18.2(3) . . . . ?
C2 C3 C4 N1 16.7(3) . . . . ?
N1 C5 C6 C17 175.31(17) . . . . ?
C11 C5 C6 C17 -4.2(3) . . . . ?
N1 C5 C6 C7 1.0(2) . . . . ?
C11 C5 C6 C7 -178.57(17) . . . . ?
C5 C6 C7 O1 116.18(17) . . . . ?
C17 C6 C7 O1 -58.5(2) . . . . ?
C5 C6 C7 C8 -114.99(17) . . . . ?
C17 C6 C7 C8 70.4(2) . . . . ?
C5 C6 C7 C10 -3.99(19) . . . . ?
C17 C6 C7 C10 -178.64(16) . . . . ?
O1 C7 C8 C9 -128.66(18) . . . . ?
C6 C7 C8 C9 103.37(19) . . . . ?
C10 C7 C8 C9 -7.7(2) . . . . ?
O1 C7 C8 C23 48.3(3) . . . . ?
C6 C7 C8 C23 -79.7(2) . . . . ?
C10 C7 C8 C23 169.2(2) . . . . ?
C23 C8 C9 C1 -176.8(2) . . . . ?
C7 C8 C9 C1 -0.2(2) . . . . ?
C23 C8 C9 C25 4.3(4) . . . . ?
C7 C8 C9 C25 -179.11(17) . . . . ?
C2 C1 C9 C8 -158.1(2) . . . . ?
C10 C1 C9 C8 8.5(2) . . . . ?
C2 C1 C9 C25 20.8(3) . . . . ?
C10 C1 C9 C25 -172.56(15) . . . . ?
C2 C1 C10 N1 44.5(2) . . . . ?
C9 C1 C10 N1 -124.36(15) . . . . ?
C2 C1 C10 C27 -78.4(2) . . . . ?
C9 C1 C10 C27 112.80(16) . . . . ?
C2 C1 C10 C7 156.00(16) . . . . ?
C9 C1 C10 C7 -12.84(18) . . . . ?
O1 C7 C10 N1 -113.84(15) . . . . ?
C8 C7 C10 N1 125.05(15) . . . . ?
C6 C7 C10 N1 5.31(17) . . . . ?
O1 C7 C10 C1 133.16(15) . . . . ?
C8 C7 C10 C1 12.06(17) . . . . ?
C6 C7 C10 C1 -107.68(15) . . . . ?
O1 C7 C10 C27 8.8(2) . . . . ?
C8 C7 C10 C27 -112.35(17) . . . . ?
C6 C7 C10 C27 127.91(16) . . . . ?
C6 C5 C11 C12 127.2(2) . . . . ?
N1 C5 C11 C12 -52.3(2) . . . . ?
C6 C5 C11 C16 -53.6(3) . . . . ?
N1 C5 C11 C16 126.90(18) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C5 C11 C12 C13 -179.56(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
C12 C11 C16 C15 -1.5(3) . . . . ?
C5 C11 C16 C15 179.21(17) . . . . ?
C5 C6 C17 C22 91.5(3) . . . . ?
C7 C6 C17 C22 -94.8(3) . . . . ?
C5 C6 C17 C18 -88.9(3) . . . . ?
C7 C6 C17 C18 84.8(3) . . . . ?
C22 C17 C18 C19 1.3(4) . . . . ?
C6 C17 C18 C19 -178.3(2) . . . . ?
C17 C18 C19 C20 -1.2(5) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C22 0.5(6) . . . . ?
C18 C17 C22 C21 -0.5(5) . . . . ?
C6 C17 C22 C21 179.0(3) . . . . ?
C20 C21 C22 C17 -0.4(6) . . . . ?
C9 C8 C23 O2 160.1(3) . . . . ?
C7 C8 C23 O2 -16.3(4) . . . . ?
C9 C8 C23 O3 -19.0(4) . . . . ?
C7 C8 C23 O3 164.6(2) . . . . ?
C8 C9 C25 O4 -90.0(3) . . . . ?
C1 C9 C25 O4 91.2(2) . . . . ?
C8 C9 C25 O5 93.0(2) . . . . ?
C1 C9 C25 O5 -85.8(2) . . . . ?
C3 C4 N1 C5 -128.80(19) . . . . ?
C3 C4 N1 C10 17.8(2) . . . . ?
C6 C5 N1 C4 151.28(17) . . . . ?
C11 C5 N1 C4 -29.1(2) . . . . ?
C6 C5 N1 C10 2.75(19) . . . . ?
C11 C5 N1 C10 -177.66(14) . . . . ?
C1 C10 N1 C4 -45.80(19) . . . . ?
C27 C10 N1 C4 77.99(19) . . . . ?
C7 C10 N1 C4 -157.18(14) . . . . ?
C1 C10 N1 C5 106.28(15) . . . . ?
C27 C10 N1 C5 -129.93(16) . . . . ?
C7 C10 N1 C5 -5.10(17) . . . . ?
O2 C23 O3 C24 0.6(5) . . . . ?
C8 C23 O3 C24 179.7(3) . . . . ?
O4 C25 O5 C26 1.6(3) . . . . ?
C9 C25 O5 C26 178.6(2) . . . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_44
_database_code_depnum_ccdc_archive 'CCDC 1908547'
loop_
_audit_author_name
_audit_author_address
'JAIS KURIAN'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65

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                   11.6409(14)
_cell_length_b                   11.8981(11)
_cell_length_c                   12.5461(14)
_cell_angle_alpha                67.133(5)
_cell_angle_beta                 76.352(5)
_cell_angle_gamma                89.759(5)
_cell_volume                     1548.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    701
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      21.07

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15502
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_av_R_equivalents  0.1131
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         22.629
_diffrn_reflns_theta_full        22.629
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4085
_reflns_number_gt                1991
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0089(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9193(4) 0.8709(3) 0.3369(4) 0.0388(11) Uani 1 1 d . . . . .
C2 C 0.8768(4) 0.7683(3) 0.3264(4) 0.0384(11) Uani 1 1 d . . . . .
C3 C 0.7646(4) 0.7256(4) 0.4122(4) 0.0449(12) Uani 1 1 d . . . . .
C4 C 0.7378(4) 0.8114(4) 0.4776(4) 0.0455(12) Uani 1 1 d . . . . .
C5 C 1.0247(4) 0.9583(3) 0.2616(4) 0.0386(11) Uani 1 1 d . . . . .
C6 C 1.0894(4) 1.0120(4) 0.3116(4) 0.0519(13) Uani 1 1 d . . . . .
H6 H 1.0680 0.9921 0.3935 0.062 Uiso 1 1 calc R U . . .
C7 C 1.1863(5) 1.0958(4) 0.2387(6) 0.0713(17) Uani 1 1 d . . . . .
H7 H 1.2306 1.1317 0.2721 0.086 Uiso 1 1 calc R U . . .
C8 C 1.2175(5) 1.1263(4) 0.1182(5) 0.0703(16) Uani 1 1 d . . . . .
H8 H 1.2834 1.1818 0.0701 0.084 Uiso 1 1 calc R U . . .
C9 C 1.1519(4) 1.0753(4) 0.0677(4) 0.0579(14) Uani 1 1 d . . . . .
H9 H 1.1716 1.0982 -0.0147 0.070 Uiso 1 1 calc R U . . .
C10 C 1.0571(4) 0.9902(3) 0.1394(4) 0.0439(12) Uani 1 1 d . . . . .
H10 H 1.0142 0.9537 0.1055 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9373(4) 0.7076(3) 0.2494(4) 0.0392(12) Uani 1 1 d . . . . .
C12 C 1.0572(4) 0.6901(4) 0.2363(4) 0.0495(13) Uani 1 1 d . . . . .
H12 H 1.1012 0.7185 0.2754 0.059 Uiso 1 1 calc R U . . .
C13 C 1.1111(5) 0.6306(4) 0.1654(5) 0.0634(15) Uani 1 1 d . . . . .
H13 H 1.1916 0.6206 0.1561 0.076 Uiso 1 1 calc R U . . .
C14 C 1.0478(5) 0.5862(4) 0.1088(5) 0.0685(16) Uani 1 1 d . . . . .
H14 H 1.0849 0.5457 0.0619 0.082 Uiso 1 1 calc R U . . .
C15 C 0.9298(5) 0.6017(4) 0.1215(5) 0.0660(16) Uani 1 1 d . . . . .
H15 H 0.8867 0.5721 0.0825 0.079 Uiso 1 1 calc R U . . .
C16 C 0.8739(4) 0.6613(4) 0.1920(4) 0.0504(13) Uani 1 1 d . . . . .
H16 H 0.7932 0.6703 0.2010 0.060 Uiso 1 1 calc R U . . .
C17 C 0.7919(5) 0.6699(4) 0.6489(5) 0.0752(16) Uani 1 1 d . . . . .
H17A H 0.7997 0.6092 0.6155 0.113 Uiso 1 1 calc R U . . .
H17B H 0.7646 0.6302 0.7344 0.113 Uiso 1 1 calc R U . . .
H17C H 0.8676 0.7154 0.6276 0.113 Uiso 1 1 calc R U . . .
C18 C 0.6327(4) 0.8819(4) 0.4497(4) 0.0611(15) Uani 1 1 d . . . . .
H18A H 0.5623 0.8259 0.4798 0.092 Uiso 1 1 calc R U . . .
H18B H 0.6464 0.9253 0.3647 0.092 Uiso 1 1 calc R U . . .
H18C H 0.6226 0.9394 0.4870 0.092 Uiso 1 1 calc R U . . .
C19 C 0.3344(4) 0.6268(3) 0.6632(4) 0.0383(11) Uani 1 1 d . . . . .
C20 C 0.2870(4) 0.7289(4) 0.6745(4) 0.0427(12) Uani 1 1 d . . . . .
C21 C 0.2187(4) 0.7745(4) 0.5894(4) 0.0465(13) Uani 1 1 d . . . . .
C22 C 0.2260(4) 0.6891(4) 0.5226(4) 0.0436(12) Uani 1 1 d . . . . .
C23 C 0.4021(4) 0.5399(3) 0.7388(4) 0.0405(12) Uani 1 1 d . . . . .
C24 C 0.4934(4) 0.4862(4) 0.6891(5) 0.0545(14) Uani 1 1 d . . . . .
H24 H 0.5131 0.5063 0.6071 0.065 Uiso 1 1 calc R U . . .
C25 C 0.5550(5) 0.4037(4) 0.7597(6) 0.0689(16) Uani 1 1 d . . . . .
H25 H 0.6163 0.3685 0.7252 0.083 Uiso 1 1 calc R U . . .
C26 C 0.5267(5) 0.3724(4) 0.8815(6) 0.0696(17) Uani 1 1 d . . . . .
H26 H 0.5690 0.3167 0.9289 0.084 Uiso 1 1 calc R U . . .
C27 C 0.4360(5) 0.4238(4) 0.9322(5) 0.0589(15) Uani 1 1 d . . . . .
H27 H 0.4156 0.4018 1.0145 0.071 Uiso 1 1 calc R U . . .
C28 C 0.3751(4) 0.5081(4) 0.8615(4) 0.0490(13) Uani 1 1 d . . . . .
H28 H 0.3150 0.5442 0.8963 0.059 Uiso 1 1 calc R U . . .
C29 C 0.3084(4) 0.7887(3) 0.7519(4) 0.0441(12) Uani 1 1 d . . . . .
C30 C 0.4220(4) 0.8103(4) 0.7616(4) 0.0490(13) Uani 1 1 d . . . . .
H30 H 0.4862 0.7845 0.7199 0.059 Uiso 1 1 calc R U . . .
C31 C 0.4409(5) 0.8693(4) 0.8317(4) 0.0585(14) Uani 1 1 d . . . . .
H31 H 0.5177 0.8837 0.8363 0.070 Uiso 1 1 calc R U . . .
C32 C 0.3475(6) 0.9073(4) 0.8952(5) 0.0678(16) Uani 1 1 d . . . . .
H32 H 0.3605 0.9465 0.9432 0.081 Uiso 1 1 calc R U . . .
C33 C 0.2350(5) 0.8867(4) 0.8868(4) 0.0631(15) Uani 1 1 d . . . . .
H33 H 0.1715 0.9125 0.9293 0.076 Uiso 1 1 calc R U . . .
C34 C 0.2142(4) 0.8282(4) 0.8160(4) 0.0532(13) Uani 1 1 d . . . . .
H34 H 0.1373 0.8152 0.8112 0.064 Uiso 1 1 calc R U . . .
C35 C 0.1062(4) 0.6204(4) 0.5481(4) 0.0582(14) Uani 1 1 d . . . . .
H35A H 0.0516 0.6779 0.5183 0.087 Uiso 1 1 calc R U . . .
H35B H 0.0762 0.5758 0.6329 0.087 Uiso 1 1 calc R U . . .
H35C H 0.1152 0.5643 0.5094 0.087 Uiso 1 1 calc R U . . .
C36 C 0.3688(4) 0.8311(4) 0.3517(4) 0.0748(17) Uani 1 1 d . . . . .
H36A H 0.3604 0.8911 0.3858 0.112 Uiso 1 1 calc R U . . .
H36B H 0.3853 0.8715 0.2662 0.112 Uiso 1 1 calc R U . . .
H36C H 0.4330 0.7838 0.3731 0.112 Uiso 1 1 calc R U . . .
N1 N 0.8493(3) 0.8921(3) 0.4293(3) 0.0469(11) Uani 1 1 d . . . . .
N2 N 0.3115(3) 0.6069(3) 0.5699(3) 0.0446(11) Uani 1 1 d . . . . .
O1 O 0.6958(3) 0.6347(3) 0.4375(3) 0.0616(10) Uani 1 1 d . . . . .
O2 O 0.7090(3) 0.7507(2) 0.6035(3) 0.0515(9) Uani 1 1 d . . . . .
O3 O 0.1620(3) 0.8656(3) 0.5640(3) 0.0617(10) Uani 1 1 d . . . . .
O4 O 0.2609(3) 0.7515(2) 0.3963(3) 0.0528(9) Uani 1 1 d . . . . .
H1N H 0.845(4) 0.970(4) 0.429(4) 0.062(14) Uiso 1 1 d . . . . .
H2N H 0.302(3) 0.530(4) 0.584(4) 0.052(14) 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
C1 N1 1.361(5) . ?
C1 C2 1.383(5) . ?
C1 C5 1.476(5) . ?
C2 C3 1.428(5) . ?
C2 C11 1.472(6) . ?
C3 O1 1.238(4) . ?
C3 C4 1.530(5) . ?
C4 O2 1.412(5) . ?
C4 N1 1.470(5) . ?
C4 C18 1.513(6) . ?
C5 C6 1.381(6) . ?
C5 C10 1.383(5) . ?
C6 C7 1.385(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.390(6) . ?
C11 C12 1.390(6) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.418(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N2 1.364(5) . ?
C19 C20 1.376(5) . ?
C19 C23 1.475(6) . ?
C20 C21 1.420(6) . ?
C20 C29 1.471(6) . ?
C21 O3 1.239(5) . ?
C21 C22 1.539(6) . ?
C22 O4 1.418(5) . ?
C22 N2 1.454(5) . ?
C22 C35 1.520(5) . ?
C23 C24 1.385(6) . ?
C23 C28 1.389(6) . ?
C24 C25 1.371(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.390(6) . ?
C29 C34 1.393(6) . ?
C30 C31 1.375(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.374(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.369(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.384(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 O4 1.432(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N1 H1N 0.93(4) . ?
N2 H2N 0.86(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.7(4) . . ?
N1 C1 C5 117.9(4) . . ?
C2 C1 C5 129.3(4) . . ?
C1 C2 C3 106.6(4) . . ?
C1 C2 C11 127.7(4) . . ?
C3 C2 C11 125.6(3) . . ?
O1 C3 C2 129.7(4) . . ?
O1 C3 C4 121.6(4) . . ?
C2 C3 C4 108.7(3) . . ?
O2 C4 N1 112.6(4) . . ?
O2 C4 C18 105.2(4) . . ?
N1 C4 C18 111.9(4) . . ?
O2 C4 C3 114.0(3) . . ?
N1 C4 C3 101.4(3) . . ?
C18 C4 C3 111.9(4) . . ?
C6 C5 C10 119.4(4) . . ?
C6 C5 C1 120.5(4) . . ?
C10 C5 C1 120.0(4) . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.5(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 118.2(4) . . ?
C16 C11 C2 120.3(4) . . ?
C12 C11 C2 121.4(4) . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.7(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C20 112.9(4) . . ?
N2 C19 C23 118.9(4) . . ?
C20 C19 C23 128.2(4) . . ?
C19 C20 C21 107.2(4) . . ?
C19 C20 C29 128.0(4) . . ?
C21 C20 C29 124.7(4) . . ?
O3 C21 C20 131.1(4) . . ?
O3 C21 C22 121.3(4) . . ?
C20 C21 C22 107.6(4) . . ?
O4 C22 N2 112.9(4) . . ?
O4 C22 C35 104.5(4) . . ?
N2 C22 C35 112.0(3) . . ?
O4 C22 C21 113.7(3) . . ?
N2 C22 C21 102.3(4) . . ?
C35 C22 C21 111.8(4) . . ?
C24 C23 C28 118.3(4) . . ?
C24 C23 C19 120.5(4) . . ?
C28 C23 C19 121.2(4) . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.5(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 119.7(5) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 120.0(5) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C23 120.9(5) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C30 C29 C34 118.0(4) . . ?
C30 C29 C20 121.7(4) . . ?
C34 C29 C20 120.3(4) . . ?
C31 C30 C29 121.0(5) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 120.7(5) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C33 C32 C31 119.1(5) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 121.1(5) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C29 120.1(5) . . ?
C33 C34 H34 119.9 . . ?
C29 C34 H34 119.9 . . ?
C22 C35 H35A 109.5 . . ?
C22 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C22 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O4 C36 H36A 109.5 . . ?
O4 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O4 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C1 N1 C4 109.7(3) . . ?
C1 N1 H1N 122(3) . . ?
C4 N1 H1N 117(3) . . ?
C19 N2 C22 109.1(4) . . ?
C19 N2 H2N 113(3) . . ?
C22 N2 H2N 121(3) . . ?
C4 O2 C17 114.6(3) . . ?
C22 O4 C36 114.4(3) . . ?

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
N1 C1 C2 C3 5.5(5) . . . . ?
C5 C1 C2 C3 -172.8(4) . . . . ?
N1 C1 C2 C11 -170.3(4) . . . . ?
C5 C1 C2 C11 11.5(7) . . . . ?
C1 C2 C3 O1 -177.7(5) . . . . ?
C11 C2 C3 O1 -1.9(8) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C11 C2 C3 C4 176.7(4) . . . . ?
O1 C3 C4 O2 51.3(6) . . . . ?
C2 C3 C4 O2 -127.4(4) . . . . ?
O1 C3 C4 N1 172.6(4) . . . . ?
C2 C3 C4 N1 -6.1(5) . . . . ?
O1 C3 C4 C18 -67.9(5) . . . . ?
C2 C3 C4 C18 113.3(4) . . . . ?
N1 C1 C5 C6 36.1(6) . . . . ?
C2 C1 C5 C6 -145.8(5) . . . . ?
N1 C1 C5 C10 -141.7(4) . . . . ?
C2 C1 C5 C10 36.5(7) . . . . ?
C10 C5 C6 C7 -0.7(7) . . . . ?
C1 C5 C6 C7 -178.5(4) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C8 C9 0.9(8) . . . . ?
C7 C8 C9 C10 -2.2(8) . . . . ?
C8 C9 C10 C5 2.0(7) . . . . ?
C6 C5 C10 C9 -0.6(6) . . . . ?
C1 C5 C10 C9 177.2(4) . . . . ?
C1 C2 C11 C16 -141.1(4) . . . . ?
C3 C2 C11 C16 43.9(6) . . . . ?
C1 C2 C11 C12 41.8(7) . . . . ?
C3 C2 C11 C12 -133.1(4) . . . . ?
C16 C11 C12 C13 1.5(6) . . . . ?
C2 C11 C12 C13 178.7(4) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C12 C13 C14 C15 0.6(8) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C14 C15 C16 C11 0.9(7) . . . . ?
C12 C11 C16 C15 -1.5(6) . . . . ?
C2 C11 C16 C15 -178.6(4) . . . . ?
N2 C19 C20 C21 5.4(5) . . . . ?
C23 C19 C20 C21 -173.5(4) . . . . ?
N2 C19 C20 C29 -170.0(4) . . . . ?
C23 C19 C20 C29 11.1(7) . . . . ?
C19 C20 C21 O3 -178.0(5) . . . . ?
C29 C20 C21 O3 -2.5(8) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C29 C20 C21 C22 176.3(4) . . . . ?
O3 C21 C22 O4 51.0(6) . . . . ?
C20 C21 C22 O4 -127.9(4) . . . . ?
O3 C21 C22 N2 173.0(4) . . . . ?
C20 C21 C22 N2 -5.9(4) . . . . ?
O3 C21 C22 C35 -67.0(5) . . . . ?
C20 C21 C22 C35 114.1(4) . . . . ?
N2 C19 C23 C24 35.9(6) . . . . ?
C20 C19 C23 C24 -145.2(4) . . . . ?
N2 C19 C23 C28 -142.9(4) . . . . ?
C20 C19 C23 C28 35.9(6) . . . . ?
C28 C23 C24 C25 0.1(6) . . . . ?
C19 C23 C24 C25 -178.8(4) . . . . ?
C23 C24 C25 C26 0.3(7) . . . . ?
C24 C25 C26 C27 0.3(8) . . . . ?
C25 C26 C27 C28 -1.3(7) . . . . ?
C26 C27 C28 C23 1.7(7) . . . . ?
C24 C23 C28 C27 -1.1(6) . . . . ?
C19 C23 C28 C27 177.8(4) . . . . ?
C19 C20 C29 C30 44.7(6) . . . . ?
C21 C20 C29 C30 -130.0(5) . . . . ?
C19 C20 C29 C34 -136.9(5) . . . . ?
C21 C20 C29 C34 48.5(6) . . . . ?
C34 C29 C30 C31 -0.3(6) . . . . ?
C20 C29 C30 C31 178.2(4) . . . . ?
C29 C30 C31 C32 0.7(7) . . . . ?
C30 C31 C32 C33 -0.6(7) . . . . ?
C31 C32 C33 C34 0.2(7) . . . . ?
C32 C33 C34 C29 0.2(7) . . . . ?
C30 C29 C34 C33 -0.1(6) . . . . ?
C20 C29 C34 C33 -178.6(4) . . . . ?
C2 C1 N1 C4 -9.9(5) . . . . ?
C5 C1 N1 C4 168.6(4) . . . . ?
O2 C4 N1 C1 131.7(4) . . . . ?
C18 C4 N1 C1 -110.1(4) . . . . ?
C3 C4 N1 C1 9.4(5) . . . . ?
C20 C19 N2 C22 -9.6(5) . . . . ?
C23 C19 N2 C22 169.4(3) . . . . ?
O4 C22 N2 C19 131.6(3) . . . . ?
C35 C22 N2 C19 -110.8(4) . . . . ?
C21 C22 N2 C19 9.0(4) . . . . ?
N1 C4 O2 C17 -63.1(5) . . . . ?
C18 C4 O2 C17 174.8(4) . . . . ?
C3 C4 O2 C17 51.8(5) . . . . ?
N2 C22 O4 C36 -62.7(4) . . . . ?
C35 C22 O4 C36 175.4(3) . . . . ?
C21 C22 O4 C36 53.2(5) . . . . ?

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046


# start Validation Reply Form
_vrf_THETM01_44                  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Even though crystal data was attempted to collect up to 0.78 \%A 
resolution, the crystal (the largest available) still diffracted quite 
weakly at high angle. On repeated recrystallisation we could get only 
small sized crystals.
 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_189
_database_code_depnum_ccdc_archive 'CCDC 1908557'
loop_
_audit_author_name
_audit_author_address
'JAIS KURIAN'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 N O6'
_chemical_formula_sum            'C24 H29 N O6'
_chemical_formula_weight         427.48

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.9320(3)
_cell_length_b                   12.9438(4)
_cell_length_c                   18.2127(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.2716(14)
_cell_angle_gamma                90
_cell_volume                     2339.55(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4166
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.11

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16671
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4118
_reflns_number_gt                2871
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.9382P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4118
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
O4 O 0.31910(13) 0.46594(12) 0.03622(7) 0.0421(4) Uani 1 1 d . . . . .
O3 O 0.59536(14) 0.46989(13) 0.09601(8) 0.0425(4) Uani 1 1 d . . . . .
O2 O 0.38128(17) 0.11122(15) 0.46006(8) 0.0512(5) Uani 1 1 d . . . . .
N1 N 0.52624(18) 0.32983(17) 0.16310(9) 0.0427(5) Uani 1 1 d . . . . .
O1 O -0.22704(16) 0.47574(16) 0.22475(10) 0.0613(5) Uani 1 1 d . . . . .
C7 C 0.30544(19) 0.37844(17) 0.15287(11) 0.0370(5) Uani 1 1 d . . . . .
C6 C 0.16596(19) 0.40212(17) 0.17289(10) 0.0355(5) Uani 1 1 d . . . . .
C14 C 0.3818(2) 0.16327(18) 0.39563(10) 0.0392(5) Uani 1 1 d . . . . .
C5 C 0.1349(2) 0.43989(18) 0.24159(11) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.2036 0.4485 0.2773 0.050 Uiso 1 1 calc R U . . .
C3 C -0.0987(2) 0.45256(17) 0.20542(12) 0.0408(5) Uani 1 1 d . . . . .
C12 C 0.2808(2) 0.21594(17) 0.28028(11) 0.0389(5) Uani 1 1 d . . . . .
H12 H 0.2078 0.2147 0.2467 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2744(2) 0.16178(17) 0.34500(11) 0.0393(5) Uani 1 1 d . . . . .
H13 H 0.1975 0.1240 0.3547 0.047 Uiso 1 1 calc R U . . .
C11 C 0.39488(19) 0.27239(17) 0.26461(10) 0.0380(5) Uani 1 1 d . . . . .
C1 C 0.0607(2) 0.39134(18) 0.12087(11) 0.0412(5) Uani 1 1 d . . . . .
H1 H 0.0787 0.3667 0.0743 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0041(2) 0.46492(19) 0.25802(12) 0.0451(6) Uani 1 1 d . . . . .
H4 H -0.0145 0.4900 0.3044 0.054 Uiso 1 1 calc R U . . .
C10 C 0.36617(19) 0.41184(17) 0.08846(11) 0.0362(5) Uani 1 1 d . . . . .
C8 C 0.4054(2) 0.32657(18) 0.19460(11) 0.0384(5) Uani 1 1 d . . . . .
C9 C 0.51471(19) 0.37864(17) 0.09197(11) 0.0369(5) Uani 1 1 d . . . . .
C2 C -0.0699(2) 0.41635(19) 0.13686(11) 0.0451(6) Uani 1 1 d . . . . .
H2 H -0.1387 0.4087 0.1011 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4951(2) 0.2210(2) 0.38145(12) 0.0531(7) Uani 1 1 d . . . . .
H15 H 0.5667 0.2238 0.4159 0.064 Uiso 1 1 calc R U . . .
C17 C 0.5592(2) 0.30919(18) 0.02988(12) 0.0444(6) Uani 1 1 d . . . . .
H17A H 0.5419 0.3461 -0.0159 0.053 Uiso 1 1 calc R U . . .
H17B H 0.6561 0.3007 0.0358 0.053 Uiso 1 1 calc R U . . .
O5 O 0.7521(2) 0.18873(18) 0.17027(12) 0.0857(7) Uani 1 1 d . . . . .
C16 C 0.5016(2) 0.2741(2) 0.31622(12) 0.0500(6) Uani 1 1 d . . . . .
H16 H 0.5786 0.3118 0.3066 0.060 Uiso 1 1 calc R U . . .
O6 O 0.9561(2) 0.1200(2) 0.18604(14) 0.1032(8) Uani 1 1 d . . . . .
C18 C 0.4978(3) 0.2021(2) 0.02101(14) 0.0635(7) Uani 1 1 d . . . . .
H18 H 0.5020 0.1680 0.0691 0.076 Uiso 1 1 calc R U . . .
C21 C 0.8497(3) 0.1697(2) 0.20876(18) 0.0739(9) Uani 1 1 d . . . . .
C20 C 0.3535(4) 0.2031(3) -0.0070(2) 0.1103(13) Uani 1 1 d . . . . .
H20A H 0.2989 0.2364 0.0283 0.165 Uiso 1 1 calc R U . . .
H20B H 0.3229 0.1334 -0.0145 0.165 Uiso 1 1 calc R U . . .
H20C H 0.3466 0.2401 -0.0527 0.165 Uiso 1 1 calc R U . . .
C22 C 0.8707(4) 0.2002(3) 0.28678(19) 0.0934(11) Uani 1 1 d . . . . .
H22A H 0.7851 0.2049 0.3093 0.140 Uiso 1 1 calc R U . . .
H22B H 0.9150 0.2660 0.2895 0.140 Uiso 1 1 calc R U . . .
H22C H 0.9255 0.1493 0.3121 0.140 Uiso 1 1 calc R U . . .
C19 C 0.5811(4) 0.1388(3) -0.0314(2) 0.1024(12) Uani 1 1 d . . . . .
H19A H 0.5437 0.0706 -0.0361 0.154 Uiso 1 1 calc R U . . .
H19B H 0.6724 0.1343 -0.0123 0.154 Uiso 1 1 calc R U . . .
H19C H 0.5795 0.1716 -0.0787 0.154 Uiso 1 1 calc R U . . .
C23 C 0.9488(5) 0.0897(5) 0.1094(3) 0.158(2) Uani 1 1 d . . . . .
H23A H 0.9235 0.1480 0.0784 0.189 Uiso 1 1 calc R U . . .
H23B H 0.8832 0.0350 0.1013 0.189 Uiso 1 1 calc R U . . .
H1N H 0.587(2) 0.2892(18) 0.1730(12) 0.044(7) Uiso 1 1 d . . . . .
H2O H 0.316(3) 0.067(2) 0.4593(15) 0.079(10) Uiso 1 1 d . . . . .
H1O H -0.278(3) 0.475(3) 0.1866(18) 0.095(12) Uiso 1 1 d . . . . .
H3O H 0.610(3) 0.493(2) 0.0518(15) 0.071(9) Uiso 1 1 d . . . . .
C24 C 1.0856(7) 0.0531(6) 0.0934(4) 0.225(3) Uani 1 1 d . . . . .
H24A H 1.1487 0.1088 0.1002 0.338 Uiso 1 1 calc R U . . .
H24B H 1.0866 0.0293 0.0435 0.338 Uiso 1 1 calc R U . . .
H24C H 1.1105 -0.0025 0.1260 0.338 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
O4 C10 1.256(2) . ?
O3 C9 1.427(3) . ?
O3 H3O 0.88(3) . ?
O2 C14 1.353(2) . ?
O2 H2O 0.87(3) . ?
N1 C8 1.351(3) . ?
N1 C9 1.442(3) . ?
N1 H1N 0.82(2) . ?
O1 C3 1.369(2) . ?
O1 H1O 0.84(3) . ?
C7 C8 1.398(3) . ?
C7 C10 1.408(3) . ?
C7 C6 1.479(3) . ?
C6 C5 1.389(3) . ?
C6 C1 1.390(3) . ?
C14 C13 1.382(3) . ?
C14 C15 1.383(3) . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C3 C2 1.374(3) . ?
C3 C4 1.382(3) . ?
C12 C13 1.375(3) . ?
C12 C11 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C11 C16 1.388(3) . ?
C11 C8 1.463(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C10 C9 1.535(3) . ?
C9 C17 1.524(3) . ?
C2 H2 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C17 C18 1.520(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O5 C21 1.199(3) . ?
C16 H16 0.9300 . ?
O6 C21 1.318(4) . ?
O6 C23 1.448(5) . ?
C18 C20 1.502(4) . ?
C18 C19 1.526(4) . ?
C18 H18 0.9800 . ?
C21 C22 1.481(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C23 C24 1.479(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C9 O3 H3O 110.2(18) . . ?
C14 O2 H2O 110.2(19) . . ?
C8 N1 C9 110.79(18) . . ?
C8 N1 H1N 123.2(16) . . ?
C9 N1 H1N 120.9(15) . . ?
C3 O1 H1O 109(2) . . ?
C8 C7 C10 106.37(17) . . ?
C8 C7 C6 128.15(17) . . ?
C10 C7 C6 125.33(18) . . ?
C5 C6 C1 117.48(18) . . ?
C5 C6 C7 122.59(18) . . ?
C1 C6 C7 119.86(17) . . ?
O2 C14 C13 122.85(19) . . ?
O2 C14 C15 117.49(19) . . ?
C13 C14 C15 119.65(19) . . ?
C4 C5 C6 121.41(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O1 C3 C2 122.6(2) . . ?
O1 C3 C4 117.82(19) . . ?
C2 C3 C4 119.62(19) . . ?
C13 C12 C11 120.69(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.30(19) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C12 C11 C16 118.48(18) . . ?
C12 C11 C8 121.27(18) . . ?
C16 C11 C8 120.22(18) . . ?
C2 C1 C6 121.39(19) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C4 C5 119.86(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
O4 C10 C7 130.02(18) . . ?
O4 C10 C9 121.03(17) . . ?
C7 C10 C9 108.78(17) . . ?
N1 C8 C7 112.20(18) . . ?
N1 C8 C11 118.73(18) . . ?
C7 C8 C11 129.07(18) . . ?
O3 C9 N1 106.97(17) . . ?
O3 C9 C17 110.34(16) . . ?
N1 C9 C17 113.15(19) . . ?
O3 C9 C10 107.87(17) . . ?
N1 C9 C10 101.66(15) . . ?
C17 C9 C10 116.16(17) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C18 C17 C9 119.32(18) . . ?
C18 C17 H17A 107.5 . . ?
C9 C17 H17A 107.5 . . ?
C18 C17 H17B 107.5 . . ?
C9 C17 H17B 107.5 . . ?
H17A C17 H17B 107.0 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C21 O6 C23 115.1(3) . . ?
C20 C18 C17 113.7(3) . . ?
C20 C18 C19 109.0(3) . . ?
C17 C18 C19 109.3(2) . . ?
C20 C18 H18 108.2 . . ?
C17 C18 H18 108.2 . . ?
C19 C18 H18 108.2 . . ?
O5 C21 O6 123.8(3) . . ?
O5 C21 C22 125.9(3) . . ?
O6 C21 C22 110.3(3) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C23 C24 105.4(4) . . ?
O6 C23 H23A 110.7 . . ?
C24 C23 H23A 110.7 . . ?
O6 C23 H23B 110.7 . . ?
C24 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C8 C7 C6 C5 44.2(3) . . . . ?
C10 C7 C6 C5 -130.7(2) . . . . ?
C8 C7 C6 C1 -138.9(2) . . . . ?
C10 C7 C6 C1 46.2(3) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C7 C6 C5 C4 177.6(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
O2 C14 C13 C12 -179.8(2) . . . . ?
C15 C14 C13 C12 1.1(3) . . . . ?
C13 C12 C11 C16 -0.9(3) . . . . ?
C13 C12 C11 C8 177.2(2) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C7 C6 C1 C2 -177.6(2) . . . . ?
O1 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C8 C7 C10 O4 -176.0(2) . . . . ?
C6 C7 C10 O4 -0.1(4) . . . . ?
C8 C7 C10 C9 -0.7(2) . . . . ?
C6 C7 C10 C9 175.1(2) . . . . ?
C9 N1 C8 C7 -4.9(3) . . . . ?
C9 N1 C8 C11 175.2(2) . . . . ?
C10 C7 C8 N1 3.4(3) . . . . ?
C6 C7 C8 N1 -172.3(2) . . . . ?
C10 C7 C8 C11 -176.7(2) . . . . ?
C6 C7 C8 C11 7.6(4) . . . . ?
C12 C11 C8 N1 -143.3(2) . . . . ?
C16 C11 C8 N1 34.9(3) . . . . ?
C12 C11 C8 C7 36.9(4) . . . . ?
C16 C11 C8 C7 -145.0(2) . . . . ?
C8 N1 C9 O3 117.04(19) . . . . ?
C8 N1 C9 C17 -121.2(2) . . . . ?
C8 N1 C9 C10 4.0(2) . . . . ?
O4 C10 C9 O3 61.5(2) . . . . ?
C7 C10 C9 O3 -114.27(19) . . . . ?
O4 C10 C9 N1 173.8(2) . . . . ?
C7 C10 C9 N1 -2.0(2) . . . . ?
O4 C10 C9 C17 -62.9(3) . . . . ?
C7 C10 C9 C17 121.3(2) . . . . ?
O1 C3 C2 C1 -178.1(2) . . . . ?
C4 C3 C2 C1 0.8(4) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
O2 C14 C15 C16 179.0(2) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
O3 C9 C17 C18 173.1(2) . . . . ?
N1 C9 C17 C18 53.3(3) . . . . ?
C10 C9 C17 C18 -63.8(3) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C8 C11 C16 C15 -178.0(2) . . . . ?
C9 C17 C18 C20 71.7(3) . . . . ?
C9 C17 C18 C19 -166.3(2) . . . . ?
C23 O6 C21 O5 0.7(5) . . . . ?
C23 O6 C21 C22 -177.8(4) . . . . ?
C21 O6 C23 C24 170.1(5) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.038

