# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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__41a_dax43
_database_code_depnum_ccdc_archive 'CCDC 1936158'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2011-12-23
_audit_creation_method           
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H27 Cl N2 O5'
_chemical_formula_sum            'C21 H27 Cl N2 O5'
_chemical_formula_weight         422.90
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.9966(3)
_cell_length_b                   10.4109(3)
_cell_length_c                   22.3370(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.301(10)
_cell_angle_gamma                90.00
_cell_volume                     2090.46(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6100
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.90
_cell_measurement_theta_min      2.62
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0670 before and 0.0255 after correction.
The Ratio of minimum to maximum transmission is 0.6802.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 4.85 cm.
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36120
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.82
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4962
_reflns_number_total             6112
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02601(3) 0.54074(3) 0.378560(13) 0.02643(8) Uani 1 1 d . . .
O1 O 0.08147(10) 0.89598(8) 0.32193(4) 0.02568(17) Uani 1 1 d . . .
O2 O 0.17168(13) 0.84396(10) 0.51038(4) 0.0415(2) Uani 1 1 d . . .
O3 O 0.27419(10) 0.66006(8) 0.48044(4) 0.02672(18) Uani 1 1 d . . .
O4 O -0.08761(9) 0.65364(9) 0.26230(4) 0.02930(19) Uani 1 1 d . . .
O5 O 0.14609(8) 0.69854(8) 0.23640(4) 0.02318(17) Uani 1 1 d . . .
N1 N 0.34490(10) 0.73494(9) 0.37841(4) 0.01950(17) Uani 1 1 d . . .
N2 N 0.29518(11) 0.95393(9) 0.39850(4) 0.02228(19) Uani 1 1 d . . .
C1 C 0.24030(12) 0.82231(10) 0.40612(5) 0.0206(2) Uani 1 1 d . . .
C2 C 0.08630(12) 0.80495(10) 0.36899(5) 0.0216(2) Uani 1 1 d . . .
C3 C 0.11001(11) 0.66996(10) 0.33886(5) 0.0198(2) Uani 1 1 d . . .
C4 C 0.27774(11) 0.65341(10) 0.34425(5) 0.01811(19) Uani 1 1 d . . .
C5 C 0.36141(11) 0.55061(10) 0.31453(5) 0.01815(19) Uani 1 1 d . . .
C6 C 0.29144(12) 0.44858(10) 0.28428(5) 0.0218(2) Uani 1 1 d . . .
C7 C 0.37555(13) 0.35327(11) 0.25829(5) 0.0250(2) Uani 1 1 d . . .
C8 C 0.53005(13) 0.36028(12) 0.26141(5) 0.0260(2) Uani 1 1 d . . .
C9 C 0.60074(12) 0.46276(11) 0.29038(5) 0.0244(2) Uani 1 1 d . . .
C10 C 0.51715(12) 0.55688(10) 0.31722(5) 0.0207(2) Uani 1 1 d . . .
C11 C -0.05757(14) 0.81541(12) 0.40230(7) 0.0305(3) Uani 1 1 d . . .
C12 C 0.04171(12) 0.67185(10) 0.27494(5) 0.0214(2) Uani 1 1 d . . .
C13 C 0.09697(15) 0.70577(13) 0.17409(6) 0.0296(2) Uani 1 1 d . . .
C14 C 0.22480(13) 0.77969(11) 0.47217(5) 0.0243(2) Uani 1 1 d . . .
C15 C 0.24614(15) 0.60133(12) 0.53786(5) 0.0278(2) Uani 1 1 d . . .
C16 C 0.29858(18) 0.46485(13) 0.53465(7) 0.0348(3) Uani 1 1 d . . .
C17 C 0.45723(14) 0.96961(12) 0.40860(6) 0.0270(2) Uani 1 1 d . . .
C18 C 0.50687(15) 1.09934(13) 0.38462(7) 0.0335(3) Uani 1 1 d . . .
C19 C 0.42194(16) 1.21064(12) 0.41147(7) 0.0335(3) Uani 1 1 d . . .
C20 C 0.25555(15) 1.18607(12) 0.40335(7) 0.0320(3) Uani 1 1 d . . .
C21 C 0.21541(14) 1.05645(11) 0.42989(6) 0.0272(2) Uani 1 1 d . . .
H1 H 0.160(2) 0.9387(18) 0.3271(8) 0.047(5) Uiso 1 1 d . . .
H6 H 0.1871(17) 0.4409(14) 0.2821(7) 0.027(4) Uiso 1 1 d . . .
H7 H 0.3245(17) 0.2811(15) 0.2384(7) 0.028(4) Uiso 1 1 d . . .
H8 H 0.5873(17) 0.2948(16) 0.2434(7) 0.034(4) Uiso 1 1 d . . .
H9 H 0.7089(18) 0.4703(15) 0.2933(7) 0.032(4) Uiso 1 1 d . . .
H10 H 0.5641(16) 0.6284(14) 0.3378(6) 0.022(3) Uiso 1 1 d . . .
H11A H -0.0593(17) 0.7589(16) 0.4364(7) 0.031(4) Uiso 1 1 d . . .
H11B H -0.141(2) 0.7971(18) 0.3737(8) 0.045(5) Uiso 1 1 d . . .
H11C H -0.0681(19) 0.9025(18) 0.4163(8) 0.040(4) Uiso 1 1 d . . .
H13A H 0.1855(18) 0.7246(16) 0.1526(7) 0.035(4) Uiso 1 1 d . . .
H13B H 0.022(2) 0.7743(18) 0.1701(8) 0.043(5) Uiso 1 1 d . . .
H13C H 0.0572(19) 0.6275(18) 0.1628(8) 0.043(5) Uiso 1 1 d . . .
H15A H 0.1379(19) 0.6099(16) 0.5448(7) 0.037(4) Uiso 1 1 d . . .
H15B H 0.2988(18) 0.6509(16) 0.5700(8) 0.036(4) Uiso 1 1 d . . .
H16A H 0.2753(18) 0.4202(16) 0.5701(8) 0.037(4) Uiso 1 1 d . . .
H16B H 0.248(2) 0.423(2) 0.5005(9) 0.060(6) Uiso 1 1 d . . .
H16C H 0.407(2) 0.460(2) 0.5306(10) 0.063(6) Uiso 1 1 d . . .
H17A H 0.5067(18) 0.9002(17) 0.3874(7) 0.036(4) Uiso 1 1 d . . .
H17B H 0.4823(17) 0.9620(15) 0.4524(7) 0.031(4) Uiso 1 1 d . . .
H18A H 0.4900(19) 1.1004(18) 0.3410(9) 0.046(5) Uiso 1 1 d . . .
H18B H 0.6159(19) 1.1079(17) 0.3928(7) 0.040(4) Uiso 1 1 d . . .
H19A H 0.4499(18) 1.2166(16) 0.4540(7) 0.035(4) Uiso 1 1 d . . .
H19B H 0.4473(19) 1.2918(18) 0.3923(8) 0.041(4) Uiso 1 1 d . . .
H20A H 0.1982(18) 1.2519(17) 0.4237(7) 0.038(4) Uiso 1 1 d . . .
H20B H 0.2267(19) 1.1851(17) 0.3604(8) 0.042(5) Uiso 1 1 d . . .
H21A H 0.2414(17) 1.0565(15) 0.4725(7) 0.028(4) Uiso 1 1 d . . .
H21B H 0.1105(18) 1.0401(15) 0.4254(7) 0.030(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.7947(10) . ?
O1 C2 1.4146(14) . ?
O1 H1 0.84(2) . ?
O2 C14 1.1989(14) . ?
O3 C14 1.3327(14) . ?
O3 C15 1.4523(14) . ?
O4 C12 1.2012(13) . ?
O5 C12 1.3284(13) . ?
O5 C13 1.4453(15) . ?
N1 C1 1.4638(13) . ?
N1 C4 1.2771(14) . ?
N2 C1 1.4687(14) . ?
N2 C17 1.4753(15) . ?
N2 C21 1.4787(15) . ?
C1 C2 1.5962(16) . ?
C1 C14 1.5524(15) . ?
C2 C3 1.5763(15) . ?
C2 C11 1.5226(16) . ?
C3 C4 1.5188(14) . ?
C3 C12 1.5318(16) . ?
C4 C5 1.4808(14) . ?
C5 C6 1.3953(15) . ?
C5 C10 1.4015(15) . ?
C6 C7 1.3891(15) . ?
C6 H6 0.941(15) . ?
C7 C8 1.3909(16) . ?
C7 H7 0.977(16) . ?
C8 C9 1.3887(17) . ?
C8 H8 0.953(16) . ?
C9 C10 1.3861(15) . ?
C9 H9 0.976(16) . ?
C10 H10 0.964(15) . ?
C11 H11A 0.963(16) . ?
C11 H11B 0.987(18) . ?
C11 H11C 0.965(18) . ?
C13 H13A 0.967(17) . ?
C13 H13B 0.983(19) . ?
C13 H13C 0.921(19) . ?
C15 C16 1.4998(19) . ?
C15 H15A 0.997(17) . ?
C15 H15B 0.988(17) . ?
C16 H16A 0.948(17) . ?
C16 H16B 0.97(2) . ?
C16 H16C 0.98(2) . ?
C17 C18 1.5262(18) . ?
C17 H17A 0.981(17) . ?
C17 H17B 0.999(16) . ?
C18 C19 1.524(2) . ?
C18 H18A 0.981(19) . ?
C18 H18B 0.995(17) . ?
C19 C20 1.5223(19) . ?
C19 H19A 0.976(16) . ?
C19 H19B 0.978(18) . ?
C20 C21 1.5231(17) . ?
C20 H20A 0.980(17) . ?
C20 H20B 0.985(18) . ?
C21 H21A 0.971(16) . ?
C21 H21B 0.960(16) . ?

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 O1 H1 104.7(13) . . ?
C14 O3 C15 116.55(9) . . ?
C12 O5 C13 115.99(9) . . ?
C4 N1 C1 111.64(9) . . ?
C1 N2 C17 114.85(9) . . ?
C1 N2 C21 116.53(9) . . ?
C17 N2 C21 110.06(9) . . ?
N1 C1 N2 107.81(8) . . ?
N1 C1 C2 105.63(8) . . ?
N1 C1 C14 107.94(9) . . ?
N2 C1 C2 109.52(9) . . ?
N2 C1 C14 114.85(9) . . ?
C14 C1 C2 110.63(9) . . ?
O1 C2 C1 108.08(8) . . ?
O1 C2 C3 106.30(9) . . ?
O1 C2 C11 108.29(10) . . ?
C3 C2 C1 101.14(8) . . ?
C11 C2 C1 118.37(10) . . ?
C11 C2 C3 113.87(9) . . ?
C2 C3 Cl1 112.98(7) . . ?
C4 C3 Cl1 108.22(7) . . ?
C4 C3 C2 102.62(8) . . ?
C4 C3 C12 115.81(9) . . ?
C12 C3 Cl1 108.00(7) . . ?
C12 C3 C2 109.29(9) . . ?
N1 C4 C3 114.62(9) . . ?
N1 C4 C5 120.76(9) . . ?
C5 C4 C3 124.60(9) . . ?
C6 C5 C4 122.66(9) . . ?
C6 C5 C10 119.15(10) . . ?
C10 C5 C4 118.19(9) . . ?
C5 C6 H6 121.3(9) . . ?
C7 C6 C5 120.23(10) . . ?
C7 C6 H6 118.4(9) . . ?
C6 C7 C8 120.11(11) . . ?
C6 C7 H7 119.0(9) . . ?
C8 C7 H7 120.9(9) . . ?
C7 C8 H8 119.8(10) . . ?
C9 C8 C7 120.11(10) . . ?
C9 C8 H8 120.1(10) . . ?
C8 C9 H9 122.0(9) . . ?
C10 C9 C8 119.90(10) . . ?
C10 C9 H9 118.1(9) . . ?
C5 C10 H10 118.3(8) . . ?
C9 C10 C5 120.49(10) . . ?
C9 C10 H10 121.2(8) . . ?
C2 C11 H11A 112.6(9) . . ?
C2 C11 H11B 108.1(10) . . ?
C2 C11 H11C 108.8(10) . . ?
H11A C11 H11B 111.0(14) . . ?
H11A C11 H11C 108.2(14) . . ?
H11B C11 H11C 108.0(14) . . ?
O4 C12 O5 125.73(11) . . ?
O4 C12 C3 124.43(10) . . ?
O5 C12 C3 109.82(9) . . ?
O5 C13 H13A 105.3(10) . . ?
O5 C13 H13B 107.8(10) . . ?
O5 C13 H13C 108.6(11) . . ?
H13A C13 H13B 112.6(14) . . ?
H13A C13 H13C 111.2(15) . . ?
H13B C13 H13C 111.1(15) . . ?
O2 C14 O3 124.28(11) . . ?
O2 C14 C1 124.80(11) . . ?
O3 C14 C1 110.89(9) . . ?
O3 C15 C16 106.88(10) . . ?
O3 C15 H15A 107.8(10) . . ?
O3 C15 H15B 109.0(10) . . ?
C16 C15 H15A 113.8(10) . . ?
C16 C15 H15B 112.8(10) . . ?
H15A C15 H15B 106.4(14) . . ?
C15 C16 H16A 110.1(10) . . ?
C15 C16 H16B 108.6(12) . . ?
C15 C16 H16C 111.9(13) . . ?
H16A C16 H16B 108.9(16) . . ?
H16A C16 H16C 107.6(16) . . ?
H16B C16 H16C 109.8(17) . . ?
N2 C17 C18 110.22(10) . . ?
N2 C17 H17A 108.0(9) . . ?
N2 C17 H17B 108.9(9) . . ?
C18 C17 H17A 109.8(10) . . ?
C18 C17 H17B 110.9(9) . . ?
H17A C17 H17B 109.0(13) . . ?
C17 C18 H18A 108.9(11) . . ?
C17 C18 H18B 108.4(10) . . ?
C19 C18 C17 112.10(11) . . ?
C19 C18 H18A 108.8(11) . . ?
C19 C18 H18B 111.5(10) . . ?
H18A C18 H18B 107.0(14) . . ?
C18 C19 H19A 108.6(10) . . ?
C18 C19 H19B 110.8(10) . . ?
C20 C19 C18 109.36(10) . . ?
C20 C19 H19A 109.9(10) . . ?
C20 C19 H19B 109.8(10) . . ?
H19A C19 H19B 108.4(14) . . ?
C19 C20 C21 110.48(11) . . ?
C19 C20 H20A 111.2(10) . . ?
C19 C20 H20B 109.7(10) . . ?
C21 C20 H20A 107.5(10) . . ?
C21 C20 H20B 108.3(10) . . ?
H20A C20 H20B 109.6(14) . . ?
N2 C21 C20 109.13(10) . . ?
N2 C21 H21A 111.3(9) . . ?
N2 C21 H21B 108.4(9) . . ?
C20 C21 H21A 109.2(9) . . ?
C20 C21 H21B 111.4(9) . . ?
H21A C21 H21B 107.4(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84(2) 1.974(19) 2.5926(13) 130.0(17) .

####################################################################### 
# 
# 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_42b_dax48
_database_code_depnum_ccdc_archive 'CCDC 1936159'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2012-02-01
_audit_creation_method           
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H28 N2 O5'
_chemical_formula_sum            'C26 H28 N2 O5'
_chemical_formula_weight         448.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H28 N2 O5'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.8032(8)
_cell_length_b                   8.35859(13)
_cell_length_c                   19.6012(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.849(3)
_cell_angle_gamma                90.00
_cell_volume                     4565.24(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13716
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.6311
_cell_measurement_theta_min      2.6377
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            60028
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.64
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   26.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263   57.0000 -150.0000 118

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   13.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263   38.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega -109.00   10.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263    0.0000 -180.0000 238

#__ type_ start__ end____ width___ exp.time_
  4 omega  -30.00   44.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263   38.0000    0.0000 148

#__ type_ start__ end____ width___ exp.time_
  5 omega  -77.00  -27.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263  -38.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   48.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263    0.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   58.00   85.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513  179.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   58.00  105.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513  179.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00  101.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513 -134.0000   67.0000 154

#__ type_ start__ end____ width___ exp.time_
 10 omega   59.00  104.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513  179.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   66.00  113.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513  179.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
 12 omega -108.00    4.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263  -77.0000 -120.0000 224

#__ type_ start__ end____ width___ exp.time_
 13 omega -108.00    4.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263  -77.0000   60.0000 224

#__ type_ start__ end____ width___ exp.time_
 14 omega -119.00  -32.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263  179.0000 -180.0000 174

#__ type_ start__ end____ width___ exp.time_
 15 omega -105.00   -3.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.5263  -57.0000  120.0000 204

#__ type_ start__ end____ width___ exp.time_
 16 omega   -3.00   79.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513   77.0000  -90.0000 164

#__ type_ start__ end____ width___ exp.time_
 17 omega   56.00  120.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513  179.0000 -180.0000 128

#__ type_ start__ end____ width___ exp.time_
 18 omega   -3.00  109.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1513   77.0000    0.0000 224
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      -0.0114575000
_diffrn_orient_matrix_UB_12      -0.0280675000
_diffrn_orient_matrix_UB_13      0.0199176000
_diffrn_orient_matrix_UB_21      0.0095440000
_diffrn_orient_matrix_UB_22      0.0655971000
_diffrn_orient_matrix_UB_23      0.0269309000
_diffrn_orient_matrix_UB_31      -0.0206297000
_diffrn_orient_matrix_UB_32      0.0459086000
_diffrn_orient_matrix_UB_33      -0.0263130000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_type              'sealed tube'
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5748
_reflns_number_total             6943
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35979(3) 0.87907(8) 0.33423(4) 0.01549(14) Uani 1 1 d . . .
O2 O 0.38654(3) 0.41376(8) 0.38513(4) 0.01635(15) Uani 1 1 d . . .
O3 O 0.43538(3) 0.39720(9) 0.33695(5) 0.02011(16) Uani 1 1 d . . .
O4 O 0.28950(3) 0.58723(9) 0.36670(5) 0.01871(15) Uani 1 1 d . . .
O5 O 0.26415(3) 0.81124(10) 0.29145(5) 0.02371(17) Uani 1 1 d . . .
N1 N 0.42836(3) 0.68515(10) 0.46098(5) 0.01375(16) Uani 1 1 d . . .
N2 N 0.45815(3) 0.72455(10) 0.37023(5) 0.01364(16) Uani 1 1 d . . .
C1 C 0.42122(3) 0.65755(11) 0.38047(5) 0.01229(17) Uani 1 1 d . . .
C2 C 0.36969(3) 0.71803(11) 0.31913(5) 0.01241(17) Uani 1 1 d . . .
C3 C 0.34779(3) 0.74607(11) 0.36738(6) 0.01338(17) Uani 1 1 d . . .
C4 C 0.38840(3) 0.72288(11) 0.45386(6) 0.01365(17) Uani 1 1 d . . .
C5 C 0.50646(4) 0.66217(13) 0.42943(6) 0.01704(19) Uani 1 1 d . . .
C6 C 0.54174(4) 0.71185(14) 0.40526(7) 0.0212(2) Uani 1 1 d . . .
C7 C 0.54438(4) 0.89368(14) 0.40200(8) 0.0243(2) Uani 1 1 d . . .
C8 C 0.49406(4) 0.96194(14) 0.34777(7) 0.0233(2) Uani 1 1 d . . .
C9 C 0.45955(4) 0.90118(12) 0.37170(6) 0.01718(19) Uani 1 1 d . . .
C10 C 0.41689(3) 0.47323(12) 0.36543(5) 0.01373(17) Uani 1 1 d . . .
C11 C 0.37307(4) 0.24659(12) 0.36573(7) 0.0190(2) Uani 1 1 d . . .
C12 C 0.33724(4) 0.21025(13) 0.38938(7) 0.0210(2) Uani 1 1 d . . .
C13 C 0.34552(3) 0.66811(12) 0.23335(6) 0.01461(18) Uani 1 1 d . . .
C14 C 0.30855(4) 0.55657(14) 0.20013(6) 0.0214(2) Uani 1 1 d . . .
C15 C 0.28835(4) 0.50881(17) 0.12045(7) 0.0287(3) Uani 1 1 d . . .
C16 C 0.30505(5) 0.57173(18) 0.07427(7) 0.0318(3) Uani 1 1 d . . .
C17 C 0.34195(5) 0.68261(18) 0.10730(7) 0.0330(3) Uani 1 1 d . . .
C18 C 0.36241(4) 0.73069(15) 0.18684(7) 0.0247(2) Uani 1 1 d . . .
C19 C 0.29562(3) 0.72157(12) 0.33651(6) 0.01517(18) Uani 1 1 d . . .
C20 C 0.24016(4) 0.54988(15) 0.34082(7) 0.0224(2) Uani 1 1 d . . .
C21 C 0.38396(4) 0.75281(12) 0.52366(6) 0.01599(18) Uani 1 1 d . . .
C22 C 0.41893(4) 0.69390(13) 0.59910(6) 0.0219(2) Uani 1 1 d . . .
C23 C 0.41587(5) 0.72578(16) 0.66580(7) 0.0294(3) Uani 1 1 d . . .
C24 C 0.37847(5) 0.81812(17) 0.65784(8) 0.0319(3) Uani 1 1 d . . .
C25 C 0.34391(5) 0.87864(16) 0.58349(8) 0.0285(3) Uani 1 1 d . . .
C26 C 0.34634(4) 0.84485(13) 0.51608(7) 0.0204(2) Uani 1 1 d . . .
H5A H 0.5175(5) 0.7082(17) 0.4844(9) 0.021(3) Uiso 1 1 d . . .
H5B H 0.5052(5) 0.5470(17) 0.4325(8) 0.019(3) Uiso 1 1 d . . .
H6A H 0.5310(5) 0.6642(17) 0.3520(9) 0.023(3) Uiso 1 1 d . . .
H6B H 0.5736(5) 0.6655(17) 0.4443(9) 0.025(4) Uiso 1 1 d . . .
H7A H 0.5583(5) 0.9395(18) 0.4577(9) 0.029(4) Uiso 1 1 d . . .
H7B H 0.5658(6) 0.9285(19) 0.3828(10) 0.035(4) Uiso 1 1 d . . .
H8A H 0.4809(5) 0.9312(18) 0.2902(9) 0.029(4) Uiso 1 1 d . . .
H8B H 0.4950(6) 1.083(2) 0.3505(10) 0.039(4) Uiso 1 1 d . . .
H9A H 0.4691(5) 0.9442(17) 0.4272(8) 0.022(3) Uiso 1 1 d . . .
H9B H 0.4267(5) 0.9458(17) 0.3333(8) 0.023(3) Uiso 1 1 d . . .
H11A H 0.4025(5) 0.1812(18) 0.3943(9) 0.027(4) Uiso 1 1 d . . .
H11B H 0.3587(5) 0.2313(18) 0.3065(9) 0.028(4) Uiso 1 1 d . . .
H12A H 0.3522(6) 0.220(2) 0.4472(11) 0.045(5) Uiso 1 1 d . . .
H12B H 0.3253(5) 0.1021(19) 0.3730(9) 0.030(4) Uiso 1 1 d . . .
H12C H 0.3097(6) 0.281(2) 0.3621(11) 0.042(5) Uiso 1 1 d . . .
H14 H 0.2962(5) 0.5120(19) 0.2315(9) 0.031(4) Uiso 1 1 d . . .
H15 H 0.2640(6) 0.428(2) 0.0985(10) 0.038(4) Uiso 1 1 d . . .
H16 H 0.2907(6) 0.539(2) 0.0177(10) 0.043(4) Uiso 1 1 d . . .
H17 H 0.3546(7) 0.727(2) 0.0759(12) 0.053(5) Uiso 1 1 d . . .
H18 H 0.3891(6) 0.8080(19) 0.2104(10) 0.032(4) Uiso 1 1 d . . .
H20A H 0.2412(5) 0.4481(19) 0.3664(9) 0.031(4) Uiso 1 1 d . . .
H20B H 0.2207(6) 0.541(2) 0.2834(10) 0.036(4) Uiso 1 1 d . . .
H20C H 0.2281(6) 0.634(2) 0.3591(10) 0.036(4) Uiso 1 1 d . . .
H22 H 0.4459(6) 0.6317(19) 0.6041(9) 0.032(4) Uiso 1 1 d . . .
H23 H 0.4399(7) 0.682(2) 0.7175(11) 0.046(5) Uiso 1 1 d . . .
H24 H 0.3766(6) 0.840(2) 0.7056(11) 0.046(5) Uiso 1 1 d . . .
H25 H 0.3181(6) 0.945(2) 0.5776(10) 0.035(4) Uiso 1 1 d . . .
H26 H 0.3226(5) 0.8924(18) 0.4655(9) 0.029(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4514(11) . ?
O1 C3 1.4431(12) . ?
O2 C10 1.3390(12) . ?
O2 C11 1.4543(12) . ?
O3 C10 1.2003(12) . ?
O4 C19 1.3330(12) . ?
O4 C20 1.4518(13) . ?
O5 C19 1.2022(13) . ?
N1 C1 1.4860(12) . ?
N1 C4 1.2824(13) . ?
N2 C1 1.4417(12) . ?
N2 C5 1.4794(12) . ?
N2 C9 1.4769(13) . ?
C1 C2 1.5536(13) . ?
C1 C10 1.5610(14) . ?
C2 C3 1.4772(13) . ?
C2 C13 1.4909(13) . ?
C3 C4 1.5174(13) . ?
C3 C19 1.4980(13) . ?
C4 C21 1.4717(13) . ?
C5 C6 1.5216(15) . ?
C5 H5A 1.014(14) . ?
C5 H5B 0.967(14) . ?
C6 C7 1.5256(16) . ?
C6 H6A 0.991(15) . ?
C6 H6B 0.991(15) . ?
C7 C8 1.5259(16) . ?
C7 H7A 1.010(16) . ?
C7 H7B 0.999(16) . ?
C8 C9 1.5232(15) . ?
C8 H8A 1.006(15) . ?
C8 H8B 1.014(17) . ?
C9 H9A 1.025(14) . ?
C9 H9B 1.006(14) . ?
C11 C12 1.5045(15) . ?
C11 H11A 0.987(15) . ?
C11 H11B 1.004(16) . ?
C12 H12A 0.972(19) . ?
C12 H12B 0.970(16) . ?
C12 H12C 0.972(18) . ?
C13 C14 1.3894(14) . ?
C13 C18 1.3947(14) . ?
C14 C15 1.3948(15) . ?
C14 H14 0.972(15) . ?
C15 C16 1.3856(18) . ?
C15 H15 0.958(17) . ?
C16 C17 1.3841(19) . ?
C16 H16 0.988(17) . ?
C17 C18 1.3921(16) . ?
C17 H17 0.98(2) . ?
C18 H18 0.985(16) . ?
C20 H20A 0.979(16) . ?
C20 H20B 0.961(16) . ?
C20 H20C 0.962(17) . ?
C21 C22 1.3981(15) . ?
C21 C26 1.3941(15) . ?
C22 C23 1.3888(15) . ?
C22 H22 0.985(16) . ?
C23 C24 1.387(2) . ?
C23 H23 0.970(19) . ?
C24 C25 1.386(2) . ?
C24 H24 0.988(18) . ?
C25 C26 1.3938(15) . ?
C25 H25 0.968(16) . ?
C26 H26 0.966(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 61.37(6) . . ?
C10 O2 C11 116.79(8) . . ?
C19 O4 C20 115.30(8) . . ?
C4 N1 C1 110.08(8) . . ?
C1 N2 C5 112.63(8) . . ?
C1 N2 C9 113.91(8) . . ?
C9 N2 C5 109.13(8) . . ?
N1 C1 C2 105.60(7) . . ?
N1 C1 C10 107.54(7) . . ?
N2 C1 N1 114.48(8) . . ?
N2 C1 C2 114.64(8) . . ?
N2 C1 C10 110.89(8) . . ?
C2 C1 C10 102.80(7) . . ?
O1 C2 C1 114.40(7) . . ?
O1 C2 C3 59.04(6) . . ?
O1 C2 C13 116.52(8) . . ?
C3 C2 C1 104.72(7) . . ?
C3 C2 C13 128.14(8) . . ?
C13 C2 C1 119.71(8) . . ?
O1 C3 C2 59.59(6) . . ?
O1 C3 C4 108.32(8) . . ?
O1 C3 C19 116.63(8) . . ?
C2 C3 C4 104.97(8) . . ?
C2 C3 C19 123.88(8) . . ?
C19 C3 C4 125.17(8) . . ?
N1 C4 C3 113.41(8) . . ?
N1 C4 C21 122.52(9) . . ?
C21 C4 C3 123.90(9) . . ?
N2 C5 C6 109.60(8) . . ?
N2 C5 H5A 109.5(8) . . ?
N2 C5 H5B 109.7(8) . . ?
C6 C5 H5A 108.9(8) . . ?
C6 C5 H5B 110.7(8) . . ?
H5A C5 H5B 108.4(11) . . ?
C5 C6 C7 110.74(9) . . ?
C5 C6 H6A 108.1(8) . . ?
C5 C6 H6B 108.5(9) . . ?
C7 C6 H6A 110.7(9) . . ?
C7 C6 H6B 111.2(9) . . ?
H6A C6 H6B 107.5(12) . . ?
C6 C7 C8 109.71(9) . . ?
C6 C7 H7A 109.6(9) . . ?
C6 C7 H7B 111.9(9) . . ?
C8 C7 H7A 108.4(9) . . ?
C8 C7 H7B 110.2(9) . . ?
H7A C7 H7B 106.9(13) . . ?
C7 C8 H8A 110.6(9) . . ?
C7 C8 H8B 110.2(9) . . ?
C9 C8 C7 111.55(9) . . ?
C9 C8 H8A 108.2(9) . . ?
C9 C8 H8B 108.9(10) . . ?
H8A C8 H8B 107.4(13) . . ?
N2 C9 C8 110.34(9) . . ?
N2 C9 H9A 111.1(8) . . ?
N2 C9 H9B 110.2(8) . . ?
C8 C9 H9A 110.4(8) . . ?
C8 C9 H9B 108.9(8) . . ?
H9A C9 H9B 105.7(11) . . ?
O2 C10 C1 108.63(8) . . ?
O3 C10 O2 124.94(9) . . ?
O3 C10 C1 126.33(9) . . ?
O2 C11 C12 107.00(8) . . ?
O2 C11 H11A 108.2(9) . . ?
O2 C11 H11B 108.5(9) . . ?
C12 C11 H11A 113.8(9) . . ?
C12 C11 H11B 111.3(9) . . ?
H11A C11 H11B 107.9(12) . . ?
C11 C12 H12A 110.3(10) . . ?
C11 C12 H12B 109.3(9) . . ?
C11 C12 H12C 111.0(10) . . ?
H12A C12 H12B 109.1(14) . . ?
H12A C12 H12C 110.1(15) . . ?
H12B C12 H12C 106.9(14) . . ?
C14 C13 C2 121.97(9) . . ?
C14 C13 C18 119.66(9) . . ?
C18 C13 C2 118.30(9) . . ?
C13 C14 C15 119.89(10) . . ?
C13 C14 H14 120.9(9) . . ?
C15 C14 H14 119.2(9) . . ?
C14 C15 H15 119.8(10) . . ?
C16 C15 C14 120.32(11) . . ?
C16 C15 H15 119.8(10) . . ?
C15 C16 H16 120.8(10) . . ?
C17 C16 C15 119.87(11) . . ?
C17 C16 H16 119.4(10) . . ?
C16 C17 C18 120.21(11) . . ?
C16 C17 H17 121.0(12) . . ?
C18 C17 H17 118.8(12) . . ?
C13 C18 H18 120.1(9) . . ?
C17 C18 C13 120.04(11) . . ?
C17 C18 H18 119.9(9) . . ?
O4 C19 C3 110.09(8) . . ?
O5 C19 O4 125.40(9) . . ?
O5 C19 C3 124.51(9) . . ?
O4 C20 H20A 106.0(9) . . ?
O4 C20 H20B 110.9(9) . . ?
O4 C20 H20C 108.4(10) . . ?
H20A C20 H20B 110.6(13) . . ?
H20A C20 H20C 110.7(13) . . ?
H20B C20 H20C 110.2(14) . . ?
C22 C21 C4 119.66(9) . . ?
C26 C21 C4 120.74(9) . . ?
C26 C21 C22 119.55(10) . . ?
C21 C22 H22 118.9(9) . . ?
C23 C22 C21 120.11(11) . . ?
C23 C22 H22 121.0(9) . . ?
C22 C23 H23 119.2(11) . . ?
C24 C23 C22 119.99(12) . . ?
C24 C23 H23 120.8(11) . . ?
C23 C24 H24 119.4(11) . . ?
C25 C24 C23 120.36(11) . . ?
C25 C24 H24 120.2(11) . . ?
C24 C25 C26 119.90(12) . . ?
C24 C25 H25 121.0(10) . . ?
C26 C25 H25 119.1(10) . . ?
C21 C26 H26 121.7(9) . . ?
C25 C26 C21 120.07(11) . . ?
C25 C26 H26 118.1(9) . . ?

####################################################################### 
# 
# 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_smi12
_database_code_depnum_ccdc_archive 'CCDC 1936916'
loop_
_audit_author_name
_audit_author_address
'galina starova'
;Saint Petersburg state university
Russia
;
_audit_update_record             
;
2019-06-27 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 O8'
_chemical_formula_sum            'C20 H16 N2 O8'
_chemical_formula_weight         412.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h20 n2 o4 cl1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9680(4)
_cell_length_b                   11.1729(4)
_cell_length_c                   13.8802(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.759(3)
_cell_angle_gamma                90
_cell_volume                     1853.86(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2230
_cell_measurement_theta_min      3.8490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12802
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   29.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7161   57.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7161   77.0000 -120.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7161   57.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00    7.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7161  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -28.00   22.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7161  -19.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0222218000
_diffrn_orient_matrix_UB_12      0.0085464000
_diffrn_orient_matrix_UB_13      0.0477779000
_diffrn_orient_matrix_UB_21      -0.0547701000
_diffrn_orient_matrix_UB_22      -0.0028253000
_diffrn_orient_matrix_UB_23      0.0173438000
_diffrn_orient_matrix_UB_31      0.0054621000
_diffrn_orient_matrix_UB_32      -0.0628311000
_diffrn_orient_matrix_UB_33      0.0057055000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3364
_reflns_number_total             4254
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.54
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+0.8863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), N1(H1), C20(H20), C10(H10), C8(H8), C7(H7), C17(H17), C9(H9),
 C19(H19), C16(H16)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.80957(9) 0.87332(9) 0.07326(7) 0.0172(2) Uani 1 1 d . . . . .
O2 O 0.54328(9) 0.88895(10) -0.04012(8) 0.0223(3) Uani 1 1 d . . . . .
O4 O 0.98637(9) 1.01837(10) 0.19555(7) 0.0194(2) Uani 1 1 d . . . . .
O6 O 0.88181(9) 1.18787(9) 0.34742(7) 0.0180(2) Uani 1 1 d . . . . .
O1 O 0.70036(9) 0.80488(10) -0.09048(7) 0.0181(2) Uani 1 1 d . . . . .
O8 O 0.86470(10) 0.77345(11) 0.71140(7) 0.0261(3) Uani 1 1 d . . . . .
O5 O 0.88283(9) 1.11567(10) 0.08040(7) 0.0202(2) Uani 1 1 d . . . . .
O7 O 0.83164(11) 0.63343(11) 0.60661(8) 0.0319(3) Uani 1 1 d . . . . .
C6 C 0.59660(13) 1.14376(14) 0.33049(10) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.647133 1.206022 0.323472 0.020 Uiso 1 1 calc R . . . .
N1 N 0.65740(10) 0.98430(11) 0.11411(8) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.592572 1.007155 0.091848 0.017 Uiso 1 1 calc R . . . .
C20 C 0.86425(13) 1.02984(14) 0.50193(10) 0.0182(3) Uani 1 1 d . . . . .
H20 H 0.879514 1.109656 0.516292 0.022 Uiso 1 1 calc R . . . .
C2 C 0.64166(13) 0.86734(13) -0.03000(10) 0.0153(3) Uani 1 1 d . . . . .
C5 C 0.60414(12) 1.04050(14) 0.27429(10) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.69406(12) 1.02919(13) 0.20517(10) 0.0136(3) Uani 1 1 d . . . . .
C10 C 0.52648(12) 0.94846(14) 0.28427(10) 0.0175(3) Uani 1 1 d . . . . .
H10 H 0.530105 0.880001 0.246434 0.021 Uiso 1 1 calc R . . . .
C15 C 0.83734(12) 0.99618(13) 0.40666(10) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.43817(13) 1.06156(15) 0.40684(10) 0.0205(3) Uani 1 1 d . . . . .
H8 H 0.383027 1.068181 0.451512 0.025 Uiso 1 1 calc R . . . .
C14 C 0.84056(12) 1.09029(13) 0.32983(10) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.51366(13) 1.15354(15) 0.39686(10) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.509083 1.222061 0.434516 0.023 Uiso 1 1 calc R . . . .
C17 C 0.81935(13) 0.79155(14) 0.45781(11) 0.0205(3) Uani 1 1 d . . . . .
H17 H 0.804752 0.711444 0.444036 0.025 Uiso 1 1 calc R . . . .
N2 N 0.84791(11) 0.73802(12) 0.62838(9) 0.0197(3) Uani 1 1 d . . . . .
C3 C 0.71487(12) 0.90831(13) 0.05818(10) 0.0142(3) Uani 1 1 d . . . . .
C13 C 0.89180(12) 1.06731(14) 0.15807(10) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.44399(13) 0.95918(15) 0.35059(11) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.392535 0.897740 0.357398 0.025 Uiso 1 1 calc R . . . .
C19 C 0.86840(13) 0.94587(14) 0.57491(10) 0.0185(3) Uani 1 1 d . . . . .
H19 H 0.885909 0.967916 0.638465 0.022 Uiso 1 1 calc R . . . .
C12 C 1.08048(13) 1.02277(18) 0.13351(11) 0.0267(4) Uani 1 1 d . . . . .
H12A H 1.066378 0.970780 0.079207 0.040 Uiso 1 1 calc GR . . . .
H12B H 1.147024 0.997175 0.169045 0.040 Uiso 1 1 calc GR . . . .
H12C H 1.090281 1.103250 0.111217 0.040 Uiso 1 1 calc GR . . . .
C16 C 0.81500(13) 0.87668(14) 0.38530(10) 0.0191(3) Uani 1 1 d . . . . .
H16 H 0.797050 0.853876 0.322001 0.023 Uiso 1 1 calc R . . . .
C18 C 0.84580(12) 0.82824(14) 0.55083(10) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.80155(12) 1.05827(13) 0.22831(10) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.63789(14) 0.76641(16) -0.17732(10) 0.0232(4) Uani 1 1 d . . . . .
H1A H 0.682702 0.712142 -0.212693 0.035 Uiso 1 1 calc GR . . . .
H1B H 0.619116 0.834845 -0.216668 0.035 Uiso 1 1 calc GR . . . .
H1C H 0.570557 0.726803 -0.160001 0.035 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C3 1.2077(18) . ?
O2 C2 1.2034(18) . ?
O4 C13 1.3395(18) . ?
O4 C12 1.4512(18) . ?
O6 C14 1.2168(18) . ?
O1 C2 1.3199(18) . ?
O1 C1 1.4526(17) . ?
O8 N2 1.2258(16) . ?
O5 C13 1.2060(18) . ?
O7 N2 1.2203(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.398(2) . ?
C6 C7 1.391(2) . ?
N1 H1 0.8600 . ?
N1 C4 1.4101(17) . ?
N1 C3 1.3593(19) . ?
C20 H20 0.9300 . ?
C20 C15 1.3974(19) . ?
C20 C19 1.380(2) . ?
C2 C3 1.5401(19) . ?
C5 C4 1.481(2) . ?
C5 C10 1.398(2) . ?
C4 C11 1.351(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(2) . ?
C15 C14 1.499(2) . ?
C15 C16 1.391(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.380(2) . ?
C8 C9 1.389(2) . ?
C14 C11 1.5060(18) . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.384(2) . ?
C17 C18 1.377(2) . ?
N2 C18 1.4740(19) . ?
C13 C11 1.493(2) . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.380(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 H16 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C13 O4 C12 114.90(12) . . ?
C2 O1 C1 114.57(12) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C5 120.12(14) . . ?
C4 N1 H1 116.9 . . ?
C3 N1 H1 116.9 . . ?
C3 N1 C4 126.15(12) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C15 120.68(14) . . ?
O2 C2 O1 125.42(13) . . ?
O2 C2 C3 123.30(13) . . ?
O1 C2 C3 111.27(12) . . ?
C6 C5 C4 120.02(13) . . ?
C10 C5 C6 119.39(14) . . ?
C10 C5 C4 120.59(13) . . ?
N1 C4 C5 113.99(12) . . ?
C11 C4 N1 123.40(13) . . ?
C11 C4 C5 122.61(12) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.02(14) . . ?
C9 C10 H10 120.0 . . ?
C20 C15 C14 118.15(13) . . ?
C16 C15 C20 119.55(13) . . ?
C16 C15 C14 122.19(12) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.43(14) . . ?
C9 C8 H8 119.8 . . ?
O6 C14 C15 120.64(12) . . ?
O6 C14 C11 120.35(13) . . ?
C15 C14 C11 118.78(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.97(15) . . ?
C8 C7 H7 120.0 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C18 C17 C16 118.44(15) . . ?
O8 N2 C18 117.51(13) . . ?
O7 N2 O8 123.98(13) . . ?
O7 N2 C18 118.50(12) . . ?
O3 C3 N1 126.85(13) . . ?
O3 C3 C2 122.33(13) . . ?
N1 C3 C2 110.82(12) . . ?
O4 C13 C11 110.06(12) . . ?
O5 C13 O4 124.56(14) . . ?
O5 C13 C11 125.32(14) . . ?
C10 C9 C8 120.06(15) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C20 C19 H19 121.0 . . ?
C18 C19 C20 118.04(13) . . ?
C18 C19 H19 121.0 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.31(13) . . ?
C17 C16 H16 119.8 . . ?
C17 C18 N2 118.44(14) . . ?
C17 C18 C19 122.98(14) . . ?
C19 C18 N2 118.57(13) . . ?
C4 C11 C14 121.90(13) . . ?
C4 C11 C13 124.87(12) . . ?
C13 C11 C14 113.18(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 C2 C3 O3 170.37(15) . . . . ?
O2 C2 C3 N1 -8.4(2) . . . . ?
O4 C13 C11 C4 -138.31(15) . . . . ?
O4 C13 C11 C14 44.16(17) . . . . ?
O6 C14 C11 C4 -120.24(16) . . . . ?
O6 C14 C11 C13 57.38(18) . . . . ?
O1 C2 C3 O3 -8.5(2) . . . . ?
O1 C2 C3 N1 172.68(12) . . . . ?
O8 N2 C18 C17 -175.53(14) . . . . ?
O8 N2 C18 C19 3.3(2) . . . . ?
O5 C13 C11 C4 44.4(2) . . . . ?
O5 C13 C11 C14 -133.11(15) . . . . ?
O7 N2 C18 C17 3.6(2) . . . . ?
O7 N2 C18 C19 -177.56(15) . . . . ?
C6 C5 C4 N1 -135.54(14) . . . . ?
C6 C5 C4 C11 45.1(2) . . . . ?
C6 C5 C10 C9 -1.1(2) . . . . ?
N1 C4 C11 C14 -171.71(13) . . . . ?
N1 C4 C11 C13 11.0(2) . . . . ?
C20 C15 C14 O6 11.2(2) . . . . ?
C20 C15 C14 C11 -174.39(13) . . . . ?
C20 C15 C16 C17 0.0(2) . . . . ?
C20 C19 C18 C17 -0.1(2) . . . . ?
C20 C19 C18 N2 -178.88(13) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C5 C4 C11 C14 7.5(2) . . . . ?
C5 C4 C11 C13 -169.79(14) . . . . ?
C5 C10 C9 C8 0.3(2) . . . . ?
C4 N1 C3 O3 -5.8(2) . . . . ?
C4 N1 C3 C2 172.92(13) . . . . ?
C4 C5 C10 C9 178.75(13) . . . . ?
C10 C5 C4 N1 44.66(18) . . . . ?
C10 C5 C4 C11 -134.66(15) . . . . ?
C15 C20 C19 C18 0.3(2) . . . . ?
C15 C14 C11 C4 65.31(19) . . . . ?
C15 C14 C11 C13 -117.07(14) . . . . ?
C14 C15 C16 C17 176.16(14) . . . . ?
C7 C6 C5 C4 -178.66(13) . . . . ?
C7 C6 C5 C10 1.1(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C3 N1 C4 C5 -142.68(14) . . . . ?
C3 N1 C4 C11 36.6(2) . . . . ?
C9 C8 C7 C6 -0.3(2) . . . . ?
C19 C20 C15 C14 -176.59(14) . . . . ?
C19 C20 C15 C16 -0.3(2) . . . . ?
C12 O4 C13 O5 -2.3(2) . . . . ?
C12 O4 C13 C11 -179.63(12) . . . . ?
C16 C15 C14 O6 -165.04(14) . . . . ?
C16 C15 C14 C11 9.4(2) . . . . ?
C16 C17 C18 N2 178.62(14) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C18 C17 C16 C15 0.2(2) . . . . ?
C1 O1 C2 O2 3.1(2) . . . . ?
C1 O1 C2 C3 -178.00(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
