# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_NAR-INM
_database_code_depnum_ccdc_archive 'CCDC 1820077'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H6 N2 O), C15 H12 O5'
_chemical_formula_sum            'C27 H24 N4 O7'
_chemical_formula_weight         516.50
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   14.2424(8)
_cell_length_b                   5.0793(3)
_cell_length_c                   33.737(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.632(4)
_cell_angle_gamma                90
_cell_volume                     2428.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.49
_cell_measurement_theta_min      4.79
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.479
_diffrn_reflns_theta_min         4.788
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3325
_reflns_number_total             4204
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1065P)²+0.1295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=1-
 FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=FVAR(1)
 Sof(H3BC)=Sof(H3BD)=Sof(C2)=Sof(H2)=Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6')=
 Sof(C1')=Sof(C3')=Sof(H3')=Sof(C2')=Sof(H2')=1-FVAR(2)
 Sof(H3AA)=Sof(H3AB)=Sof(C2A)=Sof(H2A)=Sof(C6'A)=Sof(H6'A)=Sof(C1'A)=Sof(C5'A)=
 Sof(H5'A)=Sof(C3'A)=Sof(H3'A)=Sof(C2'A)=Sof(H2'A)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3BC,H3BD), C3(H3AA,H3AB)
3.c Aromatic/amide H refined with riding coordinates:
 C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C15A(H15A), C14A(H14A),
 C12A(H12A), C13A(H13A), C15(H15), C14(H14), C12(H12), C13(H13), C6(H6), C8(H8),
  C6'A(H6'A), C5'A(H5'A), C3'A(H3'A), C2'A(H2'A), C5'(H5'), C6'(H6'), C3'(H3'),
 C2'(H2')
3.d X=CH2 refined with riding coordinates:
 N2'(H2'B,H2'C), N2(H2B,H2C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C12' C 0.25334(11) 0.7868(4) 0.56050(5) 0.0257(4) Uani 1 1 d . . . . .
H12' H 0.3015 0.9043 0.5709 0.031 Uiso 1 1 calc R . . . .
C13' C 0.16136(12) 0.8188(4) 0.56949(5) 0.0296(4) Uani 1 1 d . . . . .
H13' H 0.1479 0.9605 0.5864 0.036 Uiso 1 1 calc R . . . .
C14' C 0.11110(12) 0.4596(4) 0.53280(5) 0.0290(4) Uani 1 1 d . . . . .
H14' H 0.0617 0.3438 0.5231 0.035 Uiso 1 1 calc R . . . .
C15' C 0.20127(12) 0.4104(4) 0.52252(5) 0.0262(4) Uani 1 1 d . . . . .
H15' H 0.2132 0.2629 0.5064 0.031 Uiso 1 1 calc R . . . .
C11' C 0.27366(11) 0.5791(4) 0.53599(4) 0.0217(4) Uani 1 1 d . . . . .
C16' C 0.37070(12) 0.5353(4) 0.52361(5) 0.0231(4) Uani 1 1 d . . . . .
C16 C 0.86274(11) 0.2193(4) 0.71950(4) 0.0251(4) Uani 1 1 d . . . . .
C11 C 0.95214(11) 0.2000(4) 0.69935(5) 0.0269(4) Uani 1 1 d . . . . .
C15A C 1.0160(5) 0.0214(17) 0.7040(2) 0.0451(18) Uani 0.468(6) 1 d . . P A 1
H15A H 1.0082 -0.1214 0.7216 0.054 Uiso 0.468(6) 1 calc R . P A 1
C14A C 1.0963(5) 0.0334(19) 0.6839(2) 0.048(2) Uani 0.468(6) 1 d . . P A 1
H14A H 1.1410 -0.1039 0.6893 0.057 Uiso 0.468(6) 1 calc R . P A 1
C12A C 0.9700(3) 0.4261(11) 0.67445(15) 0.0381(14) Uani 0.468(6) 1 d . . P A 1
H12A H 0.9274 0.5705 0.6717 0.046 Uiso 0.468(6) 1 calc R . P A 1
C13A C 1.0511(3) 0.4224(11) 0.65510(16) 0.0418(15) Uani 0.468(6) 1 d . . P A 1
H13A H 1.0650 0.5651 0.6384 0.050 Uiso 0.468(6) 1 calc R . P A 1
C15 C 1.0375(3) 0.0944(11) 0.71848(14) 0.0240(10) Uani 0.532(6) 1 d . . P A 2
H15 H 1.0396 0.0249 0.7447 0.029 Uiso 0.532(6) 1 calc R . P A 2
C14 C 1.1164(4) 0.0951(12) 0.69831(15) 0.0278(12) Uani 0.532(6) 1 d . . P A 2
H14 H 1.1733 0.0232 0.7109 0.033 Uiso 0.532(6) 1 calc R . P A 2
C12 C 0.9516(2) 0.2532(10) 0.65934(10) 0.0297(12) Uani 0.532(6) 1 d . . P A 2
H12 H 0.8940 0.2969 0.6441 0.036 Uiso 0.532(6) 1 calc R . P A 2
C13 C 1.0339(2) 0.2435(10) 0.64126(10) 0.0307(12) Uani 0.532(6) 1 d . . P A 2
H13 H 1.0307 0.2724 0.6133 0.037 Uiso 0.532(6) 1 calc R . P A 2
N1 N 1.11601(10) 0.1968(4) 0.66035(5) 0.0393(5) Uani 1 1 d . . . . .
C5 C 0.37509(12) 0.7710(4) 0.68945(5) 0.0287(4) Uani 1 1 d . . . . .
C6 C 0.31412(11) 0.5761(4) 0.67480(5) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.2570 0.5456 0.6865 0.032 Uiso 1 1 calc R . . . .
C7 C 0.33680(11) 0.4240(4) 0.64277(5) 0.0250(4) Uani 1 1 d . . . . .
C8 C 0.42121(11) 0.4644(4) 0.62540(5) 0.0247(4) Uani 1 1 d . . . . .
H8 H 0.4359 0.3603 0.6034 0.030 Uiso 1 1 calc R . . . .
C9 C 0.48223(11) 0.6570(4) 0.64066(5) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.46229(11) 0.8145(4) 0.67326(5) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.52860(12) 1.0071(4) 0.68970(5) 0.0288(4) Uani 1 1 d . . . . .
C3 C 0.61723(13) 1.0355(5) 0.66964(6) 0.0388(6) Uani 1 1 d . . . . .
H3BC H 0.6683 0.9347 0.6848 0.047 Uiso 0.534(4) 1 calc R . P B 2
H3BD H 0.6361 1.2232 0.6701 0.047 Uiso 0.534(4) 1 calc R . P B 2
H3AA H 0.6106 1.1915 0.6520 0.047 Uiso 0.466(4) 1 calc R . P B 1
H3AB H 0.6699 1.0711 0.6903 0.047 Uiso 0.466(4) 1 calc R . P B 1
C2A C 0.6419(3) 0.8207(10) 0.64711(12) 0.0294(11) Uani 0.466(4) 1 d . . P B 1
H2A H 0.6690 0.6865 0.6667 0.035 Uiso 0.466(4) 1 calc R . P B 1
C6'A C 0.6968(4) 1.0167(19) 0.5810(2) 0.051(2) Uani 0.466(4) 1 d . . P B 1
H6'A H 0.6350 1.0781 0.5726 0.061 Uiso 0.466(4) 1 calc R . P B 1
C1'A C 0.7178(4) 0.8757(13) 0.61979(18) 0.0255(13) Uani 0.466(4) 1 d . . P B 1
C5'A C 0.7705(4) 1.0544(13) 0.55784(15) 0.0329(13) Uani 0.466(4) 1 d . . P B 1
H5'A H 0.7592 1.1486 0.5335 0.039 Uiso 0.466(4) 1 calc R . P B 1
C4' C 0.86045(12) 0.9594(4) 0.56895(5) 0.0255(4) Uani 1 1 d . . . . .
C3'A C 0.8746(3) 0.8419(10) 0.60772(12) 0.0320(11) Uani 0.466(4) 1 d . . P B 1
H3'A H 0.9358 0.7823 0.6174 0.038 Uiso 0.466(4) 1 calc R . P B 1
C2'A C 0.8012(4) 0.8135(11) 0.63118(14) 0.0435(14) Uani 0.466(4) 1 d . . P B 1
H2'A H 0.8146 0.7435 0.6572 0.052 Uiso 0.466(4) 1 calc R . P B 1
C2 C 0.6064(2) 0.9393(7) 0.62684(10) 0.0233(9) Uani 0.534(4) 1 d . . P B 2
H2 H 0.5616 1.0638 0.6119 0.028 Uiso 0.534(4) 1 calc R . P B 2
C5' C 0.8434(3) 0.7330(10) 0.58750(14) 0.0414(12) Uani 0.534(4) 1 d . . P B 2
H5' H 0.8853 0.5877 0.5873 0.050 Uiso 0.534(4) 1 calc R . P B 2
C6' C 0.7614(4) 0.7189(11) 0.60716(16) 0.0564(15) Uani 0.534(4) 1 d . . P B 2
H6' H 0.7482 0.5639 0.6214 0.068 Uiso 0.534(4) 1 calc R . P B 2
C1' C 0.6953(4) 0.9438(12) 0.60591(18) 0.0281(12) Uani 0.534(4) 1 d . . P B 2
C3' C 0.7984(3) 1.1679(13) 0.56634(13) 0.0352(11) Uani 0.534(4) 1 d . . P B 2
H3' H 0.8114 1.3217 0.5518 0.042 Uiso 0.534(4) 1 calc R . P B 2
C2' C 0.7171(3) 1.1493(14) 0.58514(15) 0.0406(13) Uani 0.534(4) 1 d . . P B 2
H2' H 0.6744 1.2935 0.5830 0.049 Uiso 0.534(4) 1 calc R . P B 2
N2' N 0.42312(10) 0.7475(3) 0.51968(5) 0.0295(4) Uani 1 1 d . . . . .
H2'B H 0.4804 0.7314 0.5123 0.035 Uiso 1 1 calc R . . . .
H2'C H 0.4006 0.9045 0.5245 0.035 Uiso 1 1 calc R . . . .
N1' N 0.09023(10) 0.6615(4) 0.55566(4) 0.0305(4) Uani 1 1 d . . . . .
N2 N 0.85005(10) 0.0390(4) 0.74686(4) 0.0290(4) Uani 1 1 d . . . . .
H2B H 0.7986 0.0415 0.7593 0.035 Uiso 1 1 calc R . . . .
H2C H 0.8930 -0.0833 0.7525 0.035 Uiso 1 1 calc R . . . .
O6' O 0.39846(8) 0.3090(3) 0.51731(4) 0.0310(3) Uani 1 1 d . . . . .
O6 O 0.80577(8) 0.3977(3) 0.70978(3) 0.0320(4) Uani 1 1 d . . . . .
O5 O 0.27979(8) 0.2352(3) 0.62695(3) 0.0315(4) Uani 1 1 d . . . . .
H5 H 0.2291 0.2372 0.6377 0.047 Uiso 1 1 calc GR . . . .
O4 O 0.35056(9) 0.9220(4) 0.71972(4) 0.0436(4) Uani 1 1 d . . . . .
H4 H 0.3935 1.0320 0.7260 0.065 Uiso 1 1 calc GR . . . .
O2 O 0.51468(9) 1.1440(3) 0.71939(4) 0.0360(4) Uani 1 1 d . . . . .
O1 O 0.56388(8) 0.6881(3) 0.62296(3) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.93426(9) 0.9892(3) 0.54656(4) 0.0329(4) Uani 1 1 d . . . . .
H3 H 0.9737 0.8682 0.5520 0.049 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
C12' H12' 0.9500 . ?
C12' C13' 1.383(2) . ?
C12' C11' 1.388(3) . ?
C13' H13' 0.9500 . ?
C13' N1' 1.338(3) . ?
C14' H14' 0.9500 . ?
C14' C15' 1.385(2) . ?
C14' N1' 1.334(3) . ?
C15' H15' 0.9500 . ?
C15' C11' 1.383(3) . ?
C11' C16' 1.499(2) . ?
C16' N2' 1.325(2) . ?
C16' O6' 1.241(2) . ?
C16 C11 1.504(2) . ?
C16 N2 1.325(2) . ?
C16 O6 1.239(2) . ?
C11 C15A 1.284(7) . ?
C11 C12A 1.460(5) . ?
C11 C15 1.424(5) . ?
C11 C12 1.376(4) . ?
C15A H15A 0.9500 . ?
C15A C14A 1.388(9) . ?
C14A H14A 0.9500 . ?
C14A N1 1.200(8) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.382(6) . ?
C13A H13A 0.9500 . ?
C13A N1 1.472(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.370(8) . ?
C14 H14 0.9500 . ?
C14 N1 1.380(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(5) . ?
C13 H13 0.9500 . ?
C13 N1 1.300(4) . ?
C5 C6 1.376(3) . ?
C5 C10 1.422(2) . ?
C5 O4 1.350(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(3) . ?
C7 C8 1.403(2) . ?
C7 O5 1.334(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C9 C10 1.411(3) . ?
C9 O1 1.3676(19) . ?
C10 C4 1.433(3) . ?
C4 C3 1.497(2) . ?
C4 O2 1.251(2) . ?
C3 H3BC 0.9900 . ?
C3 H3BD 0.9900 . ?
C3 H3AA 0.9900 . ?
C3 H3AB 0.9900 . ?
C3 C2A 1.394(5) . ?
C3 C2 1.518(4) . ?
C2A H2A 1.0000 . ?
C2A C1'A 1.514(7) . ?
C2A O1 1.474(4) . ?
C6'A H6'A 0.9500 . ?
C6'A C1'A 1.496(10) . ?
C6'A C5'A 1.383(9) . ?
C1'A C2'A 1.253(8) . ?
C5'A H5'A 0.9500 . ?
C5'A C4' 1.386(6) . ?
C4' C3'A 1.434(4) . ?
C4' C5' 1.343(5) . ?
C4' C3' 1.377(6) . ?
C4' O3 1.362(2) . ?
C3'A H3'A 0.9500 . ?
C3'A C2'A 1.378(6) . ?
C2'A H2'A 0.9500 . ?
C2 H2 1.0000 . ?
C2 C1' 1.510(6) . ?
C2 O1 1.413(4) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.400(6) . ?
C6' H6' 0.9500 . ?
C6' C1' 1.478(8) . ?
C1' C2' 1.311(9) . ?
C3' H3' 0.9500 . ?
C3' C2' 1.377(7) . ?
C2' H2' 0.9500 . ?
N2' H2'B 0.8800 . ?
N2' H2'C 0.8800 . ?
N2 H2B 0.8800 . ?
N2 H2C 0.8800 . ?
O5 H5 0.8400 . ?
O4 H4 0.8400 . ?
O3 H3 0.8400 . ?

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' C12' H12' 120.7 . . ?
C13' C12' C11' 118.51(17) . . ?
C11' C12' H12' 120.7 . . ?
C12' C13' H13' 118.2 . . ?
N1' C13' C12' 123.68(19) . . ?
N1' C13' H13' 118.2 . . ?
C15' C14' H14' 118.4 . . ?
N1' C14' H14' 118.4 . . ?
N1' C14' C15' 123.22(17) . . ?
C14' C15' H15' 120.5 . . ?
C11' C15' C14' 119.04(18) . . ?
C11' C15' H15' 120.5 . . ?
C12' C11' C16' 122.05(16) . . ?
C15' C11' C12' 118.33(16) . . ?
C15' C11' C16' 119.63(16) . . ?
N2' C16' C11' 116.80(16) . . ?
O6' C16' C11' 120.21(17) . . ?
O6' C16' N2' 122.99(15) . . ?
N2 C16 C11 116.69(17) . . ?
O6 C16 C11 119.30(17) . . ?
O6 C16 N2 124.01(15) . . ?
C15A C11 C16 127.7(3) . . ?
C15A C11 C12A 117.7(4) . . ?
C12A C11 C16 114.3(2) . . ?
C15 C11 C16 122.8(2) . . ?
C12 C11 C16 120.48(19) . . ?
C12 C11 C15 116.2(3) . . ?
C11 C15A H15A 119.4 . . ?
C11 C15A C14A 121.1(6) . . ?
C14A C15A H15A 119.4 . . ?
C15A C14A H14A 116.2 . . ?
N1 C14A C15A 127.7(7) . . ?
N1 C14A H14A 116.2 . . ?
C11 C12A H12A 121.2 . . ?
C13A C12A C11 117.5(4) . . ?
C13A C12A H12A 121.2 . . ?
C12A C13A H13A 120.1 . . ?
C12A C13A N1 119.9(4) . . ?
N1 C13A H13A 120.1 . . ?
C11 C15 H15 120.7 . . ?
C14 C15 C11 118.6(4) . . ?
C14 C15 H15 120.7 . . ?
C15 C14 H14 118.9 . . ?
C15 C14 N1 122.2(5) . . ?
N1 C14 H14 118.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 118.3 . . ?
N1 C13 C12 123.5(3) . . ?
N1 C13 H13 118.3 . . ?
C14A N1 C13A 115.7(4) . . ?
C13 N1 C14 116.7(3) . . ?
C6 C5 C10 121.19(17) . . ?
O4 C5 C6 118.62(16) . . ?
O4 C5 C10 120.19(17) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.46(16) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 121.11(17) . . ?
O5 C7 C6 122.10(15) . . ?
O5 C7 C8 116.79(16) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.93(16) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 121.82(15) . . ?
O1 C9 C8 116.88(15) . . ?
O1 C9 C10 121.31(16) . . ?
C5 C10 C4 121.65(17) . . ?
C9 C10 C5 117.47(17) . . ?
C9 C10 C4 120.88(15) . . ?
C10 C4 C3 116.36(16) . . ?
O2 C4 C10 122.61(16) . . ?
O2 C4 C3 121.03(18) . . ?
C4 C3 H3BC 109.0 . . ?
C4 C3 H3BD 109.0 . . ?
C4 C3 H3AA 108.3 . . ?
C4 C3 H3AB 108.3 . . ?
C4 C3 C2 112.81(18) . . ?
H3BC C3 H3BD 107.8 . . ?
H3AA C3 H3AB 107.4 . . ?
C2A C3 C4 116.1(2) . . ?
C2A C3 H3AA 108.3 . . ?
C2A C3 H3AB 108.3 . . ?
C2 C3 H3BC 109.0 . . ?
C2 C3 H3BD 109.0 . . ?
C3 C2A H2A 106.0 . . ?
C3 C2A C1'A 114.9(4) . . ?
C3 C2A O1 116.3(3) . . ?
C1'A C2A H2A 106.0 . . ?
O1 C2A H2A 106.0 . . ?
O1 C2A C1'A 107.0(3) . . ?
C1'A C6'A H6'A 121.2 . . ?
C5'A C6'A H6'A 121.2 . . ?
C5'A C6'A C1'A 117.6(6) . . ?
C6'A C1'A C2A 121.8(5) . . ?
C2'A C1'A C2A 118.6(5) . . ?
C2'A C1'A C6'A 119.4(5) . . ?
C6'A C5'A H5'A 118.9 . . ?
C6'A C5'A C4' 122.1(6) . . ?
C4' C5'A H5'A 118.9 . . ?
C5'A C4' C3'A 115.8(3) . . ?
C5' C4' C3' 122.9(3) . . ?
C5' C4' O3 122.6(2) . . ?
O3 C4' C5'A 123.7(3) . . ?
O3 C4' C3'A 120.4(2) . . ?
O3 C4' C3' 113.9(3) . . ?
C4' C3'A H3'A 119.3 . . ?
C2'A C3'A C4' 121.4(4) . . ?
C2'A C3'A H3'A 119.3 . . ?
C1'A C2'A C3'A 123.1(5) . . ?
C1'A C2'A H2'A 118.4 . . ?
C3'A C2'A H2'A 118.4 . . ?
C3 C2 H2 106.1 . . ?
C1' C2 C3 115.4(3) . . ?
C1' C2 H2 106.1 . . ?
O1 C2 C3 112.4(2) . . ?
O1 C2 H2 106.1 . . ?
O1 C2 C1' 110.0(3) . . ?
C4' C5' H5' 121.2 . . ?
C4' C5' C6' 117.5(4) . . ?
C6' C5' H5' 121.2 . . ?
C5' C6' H6' 119.8 . . ?
C5' C6' C1' 120.3(5) . . ?
C1' C6' H6' 119.8 . . ?
C6' C1' C2 122.4(5) . . ?
C2' C1' C2 121.0(5) . . ?
C2' C1' C6' 116.6(5) . . ?
C4' C3' H3' 120.6 . . ?
C4' C3' C2' 118.8(5) . . ?
C2' C3' H3' 120.6 . . ?
C1' C2' C3' 123.6(5) . . ?
C1' C2' H2' 118.2 . . ?
C3' C2' H2' 118.2 . . ?
C16' N2' H2'B 120.0 . . ?
C16' N2' H2'C 120.0 . . ?
H2'B N2' H2'C 120.0 . . ?
C14' N1' C13' 117.18(15) . . ?
C16 N2 H2B 120.0 . . ?
C16 N2 H2C 120.0 . . ?
H2B N2 H2C 120.0 . . ?
C7 O5 H5 109.5 . . ?
C5 O4 H4 109.5 . . ?
C9 O1 C2A 115.98(18) . . ?
C9 O1 C2 116.03(18) . . ?
C4' O3 H3 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
C12' C13' N1' C14' 1.8(3) . . . . ?
C12' C11' C16' N2' -31.5(2) . . . . ?
C12' C11' C16' O6' 148.95(17) . . . . ?
C13' C12' C11' C15' -1.5(2) . . . . ?
C13' C12' C11' C16' 177.87(16) . . . . ?
C14' C15' C11' C12' 2.1(2) . . . . ?
C14' C15' C11' C16' -177.29(15) . . . . ?
C15' C14' N1' C13' -1.1(3) . . . . ?
C15' C11' C16' N2' 147.94(17) . . . . ?
C15' C11' C16' O6' -31.6(2) . . . . ?
C11' C12' C13' N1' -0.5(3) . . . . ?
C16 C11 C15A C14A -178.5(5) . . . . ?
C16 C11 C12A C13A 179.8(4) . . . . ?
C16 C11 C15 C14 -177.3(4) . . . . ?
C16 C11 C12 C13 178.0(3) . . . . ?
C11 C15A C14A N1 -1.3(13) . . . . ?
C11 C12A C13A N1 -0.6(7) . . . . ?
C11 C15 C14 N1 0.6(7) . . . . ?
C11 C12 C13 N1 -3.1(7) . . . . ?
C15A C11 C12A C13A 5.0(7) . . . . ?
C15A C14A N1 C13A 5.9(11) . . . . ?
C12A C11 C15A C14A -4.5(9) . . . . ?
C12A C13A N1 C14A -4.6(8) . . . . ?
C15 C11 C12 C13 -10.1(6) . . . . ?
C15 C14 N1 C13 -13.5(7) . . . . ?
C12 C11 C15 C14 10.9(6) . . . . ?
C12 C13 N1 C14 14.9(6) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 O5 -178.96(17) . . . . ?
C5 C10 C4 C3 -179.36(18) . . . . ?
C5 C10 C4 O2 1.3(3) . . . . ?
C6 C5 C10 C9 2.4(3) . . . . ?
C6 C5 C10 C4 -176.50(18) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 O1 179.57(15) . . . . ?
C8 C9 C10 C5 -1.4(3) . . . . ?
C8 C9 C10 C4 177.50(17) . . . . ?
C8 C9 O1 C2A -159.0(2) . . . . ?
C8 C9 O1 C2 155.4(2) . . . . ?
C9 C10 C4 C3 1.8(3) . . . . ?
C9 C10 C4 O2 -177.57(18) . . . . ?
C10 C5 C6 C7 -2.0(3) . . . . ?
C10 C9 O1 C2A 20.5(3) . . . . ?
C10 C9 O1 C2 -25.1(3) . . . . ?
C10 C4 C3 C2A -21.5(3) . . . . ?
C10 C4 C3 C2 22.8(3) . . . . ?
C4 C3 C2A C1'A 166.6(3) . . . . ?
C4 C3 C2A O1 40.6(4) . . . . ?
C4 C3 C2 C1' -175.6(3) . . . . ?
C4 C3 C2 O1 -48.4(3) . . . . ?
C3 C2A C1'A C6'A -78.1(7) . . . . ?
C3 C2A C1'A C2'A 98.0(6) . . . . ?
C3 C2A O1 C9 -40.6(4) . . . . ?
C3 C2 C1' C6' 89.0(6) . . . . ?
C3 C2 C1' C2' -91.8(6) . . . . ?
C3 C2 O1 C9 50.0(3) . . . . ?
C2A C1'A C2'A C3'A 176.3(5) . . . . ?
C6'A C1'A C2'A C3'A -7.5(9) . . . . ?
C6'A C5'A C4' C3'A -5.8(7) . . . . ?
C6'A C5'A C4' O3 178.9(5) . . . . ?
C1'A C2A O1 C9 -170.5(3) . . . . ?
C1'A C6'A C5'A C4' 2.1(9) . . . . ?
C5'A C6'A C1'A C2A -179.1(5) . . . . ?
C5'A C6'A C1'A C2'A 4.9(10) . . . . ?
C5'A C4' C3'A C2'A 3.5(7) . . . . ?
C4' C3'A C2'A C1'A 3.5(9) . . . . ?
C4' C5' C6' C1' 2.2(8) . . . . ?
C4' C3' C2' C1' 0.6(8) . . . . ?
C2 C1' C2' C3' 178.1(4) . . . . ?
C5' C4' C3' C2' 3.2(6) . . . . ?
C5' C6' C1' C2 -179.5(4) . . . . ?
C5' C6' C1' C2' 1.2(9) . . . . ?
C6' C1' C2' C3' -2.6(9) . . . . ?
C1' C2 O1 C9 -180.0(3) . . . . ?
C3' C4' C5' C6' -4.4(6) . . . . ?
N1' C14' C15' C11' -0.8(3) . . . . ?
N2 C16 C11 C15A 3.8(6) . . . . ?
N2 C16 C11 C12A -170.4(3) . . . . ?
N2 C16 C11 C15 -29.9(4) . . . . ?
N2 C16 C11 C12 141.6(3) . . . . ?
O6 C16 C11 C15A -175.8(5) . . . . ?
O6 C16 C11 C12A 10.0(3) . . . . ?
O6 C16 C11 C15 150.5(3) . . . . ?
O6 C16 C11 C12 -38.0(4) . . . . ?
O5 C7 C8 C9 179.95(16) . . . . ?
O4 C5 C6 C7 177.97(18) . . . . ?
O4 C5 C10 C9 -177.61(17) . . . . ?
O4 C5 C10 C4 3.5(3) . . . . ?
O2 C4 C3 C2A 157.9(3) . . . . ?
O2 C4 C3 C2 -157.8(2) . . . . ?
O1 C9 C10 C5 179.14(16) . . . . ?
O1 C9 C10 C4 -2.0(3) . . . . ?
O1 C2A C1'A C6'A 52.6(7) . . . . ?
O1 C2A C1'A C2'A -131.4(5) . . . . ?
O1 C2 C1' C6' -39.4(6) . . . . ?
O1 C2 C1' C2' 139.8(5) . . . . ?
O3 C4' C3'A C2'A 178.9(4) . . . . ?
O3 C4' C5' C6' -175.2(3) . . . . ?
O3 C4' C3' C2' 174.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xl_sq
_database_code_depnum_ccdc_archive 'CCDC 1820098'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H11 N O2, C15 H12 O5'
_chemical_formula_sum            'C20 H23 N O7'
_chemical_formula_weight         389.39
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.6006(7)
_cell_length_b                   6.6844(3)
_cell_length_c                   13.5560(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.0997(19)
_cell_angle_gamma                90
_cell_volume                     1956.00(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3847
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      68.55
_cell_measurement_theta_min      4.10
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7511
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.567
_diffrn_reflns_theta_min         4.096
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3067
_reflns_number_total             3430
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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-97 (Sheldrick 2008)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0670P)²+1.6902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7(6)
 0.3(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C1'A-C2A
 1.5 with sigma of 0.02
 C6'A-C2A \\sim C2A-C2'A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C2A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C1', C1'A, C2, C2', C2'A, C2A, C3, C3', C3'A, C3A, C4', C4'A, C5', C5'A, C6',
 C6'A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, C1', C1'A, C2, C2A, C3, C3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C6'A)=
 Sof(H6'A)=Sof(C5'A)=Sof(H5'A)=Sof(C4'A)=Sof(C3'A)=Sof(H3'A)=Sof(C2'A)=
 Sof(H2'A)=Sof(C1'A)=1-FVAR(1)
 Sof(O3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(C2')=Sof(H2')=Sof(C3')=Sof(H3')=Sof(C4')=
 Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6')=Sof(C1')=Sof(C3)=Sof(H3B)=Sof(H3C)=FVAR(1)
7.a Riding coordinates:
 O3(H3), O3A(H3A)
7.b Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
7.c Secondary CH2 refined with riding coordinates:
 C3(H3B,H3C), C3A(H3AA,H3AB), C11(H11A,H11B)
7.d Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C3'(H3'), C5'(H5'), C6'(H6'), C6(H6), C6'A(H6'A), C5'A(H5'A),
 C3'A(H3'A), C2'A(H2'A), C8(H8)
7.e Fitted hexagon refined as free rotating group:
 C2'(C3',C4',C5',C6',C1'), C6'A(C5'A,C4'A,C3'A,C2'A,C1'A)
7.f Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
7.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.37945(9) 0.4713(9) 0.87800(16) 0.0549(6) Uani 1 1 d . . . . .
O1 O 0.25740(9) 0.4698(10) 0.17633(14) 0.0581(7) Uani 1 1 d . U . . .
O2 O 0.06767(9) 0.4708(10) 0.16819(18) 0.0644(8) Uani 1 1 d . . . . .
O3 O 0.3991(4) 0.2320(18) 0.5640(7) 0.070(3) Uani 0.489(8) 1 d . . P A 1
H3 H 0.4019 0.3130 0.6093 0.104 Uiso 0.489(8) 1 d R . P A 1
O4 O 0.06839(8) 0.4711(8) -0.02212(16) 0.0497(6) Uani 1 1 d . . . . .
H4 H 0.0535 0.4818 0.0324 0.075 Uiso 1 1 calc GR . . . .
O5 O 0.26209(10) 0.4713(11) -0.16895(15) 0.0651(8) Uani 1 1 d . . . . .
H5 H 0.2992 0.4634 -0.1548 0.098 Uiso 1 1 calc GR . . . .
O3A O 0.3939(5) 0.6992(18) 0.5696(7) 0.085(3) Uani 0.511(8) 1 d . . P A 2
H3A H 0.4026 0.6057 0.6066 0.127 Uiso 0.511(8) 1 d R . P A 2
O7 O 0.40935(11) 0.4609(12) 0.72272(17) 0.0776(10) Uani 1 1 d . . . . .
N1 N 0.53742(11) 0.4742(10) 0.79009(19) 0.0492(7) Uani 1 1 d . . . . .
C2 C 0.2229(6) 0.387(3) 0.2612(10) 0.061(4) Uani 0.489(8) 1 d . U P A 1
H2 H 0.2096 0.2494 0.2467 0.073 Uiso 0.489(8) 1 calc R . P A 1
C2' C 0.2910(3) 0.1962(12) 0.3546(5) 0.068(3) Uani 0.489(8) 1 d . U P A 1
H2' H 0.2777 0.0991 0.3095 0.082 Uiso 0.489(8) 1 calc R . P A 1
C3' C 0.3347(3) 0.1484(10) 0.4287(6) 0.057(3) Uani 0.489(8) 1 d G U P A 1
H3' H 0.3506 0.0194 0.4332 0.069 Uiso 0.489(8) 1 calc R . P A 1
C4' C 0.3546(3) 0.2935(14) 0.4962(5) 0.052(3) Uani 0.489(8) 1 d G U P A 1
C5' C 0.3307(4) 0.4864(13) 0.4895(6) 0.055(3) Uani 0.489(8) 1 d G U P A 1
H5' H 0.3440 0.5835 0.5346 0.066 Uiso 0.489(8) 1 calc R . P A 1
C6' C 0.2870(4) 0.5342(11) 0.4154(7) 0.067(4) Uani 0.489(8) 1 d G U P A 1
H6' H 0.2711 0.6633 0.4110 0.081 Uiso 0.489(8) 1 calc R . P A 1
C1' C 0.2672(3) 0.3891(14) 0.3480(5) 0.074(3) Uani 0.489(8) 1 d G U P A 1
C2A C 0.2257(4) 0.4664(16) 0.2669(7) 0.0277(16) Uani 0.511(8) 1 d D U P A 2
H2A H 0.2130 0.6066 0.2597 0.033 Uiso 0.511(8) 1 calc R . P A 2
C3 C 0.1610(4) 0.537(2) 0.2666(8) 0.043(3) Uani 0.489(8) 1 d . U P A 1
H3B H 0.1374 0.5114 0.3248 0.051 Uiso 0.489(8) 1 calc R . P A 1
H3C H 0.1725 0.6775 0.2649 0.051 Uiso 0.489(8) 1 calc R . P A 1
C3A C 0.1636(5) 0.399(2) 0.2630(8) 0.050(3) Uani 0.511(8) 1 d . U P A 2
H3AA H 0.1434 0.4453 0.3215 0.060 Uiso 0.511(8) 1 calc R . P A 2
H3AB H 0.1635 0.2539 0.2642 0.060 Uiso 0.511(8) 1 calc R . P A 2
C4 C 0.12529(13) 0.4713(14) 0.1700(2) 0.0557(10) Uani 1 1 d . . . . .
C5 C 0.13144(11) 0.4718(8) -0.0121(2) 0.0372(6) Uani 1 1 d . . . . .
C6 C 0.16561(13) 0.4675(10) -0.0956(2) 0.0427(7) Uani 1 1 d . . . . .
H6 H 0.1459 0.4618 -0.1577 0.051 Uiso 1 1 calc R . . . .
C6'A C 0.2886(3) 0.7113(9) 0.3552(5) 0.054(2) Uani 0.511(8) 1 d D U P A 2
H6'A H 0.2737 0.8026 0.3083 0.065 Uiso 0.511(8) 1 calc R . P A 2
C5'A C 0.3303(3) 0.7728(9) 0.4296(6) 0.058(3) Uani 0.511(8) 1 d G U P A 2
H5'A H 0.3433 0.9054 0.4325 0.070 Uiso 0.511(8) 1 calc R . P A 2
C4'A C 0.3525(4) 0.6363(14) 0.4997(5) 0.060(3) Uani 0.511(8) 1 d G U P A 2
C3'A C 0.3330(4) 0.4382(13) 0.4953(6) 0.062(4) Uani 0.511(8) 1 d G U P A 2
H3'A H 0.3479 0.3469 0.5422 0.074 Uiso 0.511(8) 1 calc R . P A 2
C2'A C 0.2913(4) 0.3766(9) 0.4209(7) 0.063(3) Uani 0.511(8) 1 d DG U P A 2
H2'A H 0.2783 0.2441 0.4179 0.075 Uiso 0.511(8) 1 calc R . P A 2
C1'A C 0.2691(3) 0.5132(10) 0.3508(5) 0.043(2) Uani 0.511(8) 1 d DG U P A 2
C7 C 0.23028(12) 0.4717(10) -0.0863(2) 0.0394(7) Uani 1 1 d . . . . .
C8 C 0.26001(11) 0.4788(8) 0.0055(2) 0.0331(6) Uani 1 1 d . . . . .
H8 H 0.3030 0.4884 0.0111 0.040 Uiso 1 1 calc R . . . .
C9 C 0.22550(12) 0.4716(10) 0.0883(2) 0.0363(6) Uani 1 1 d . . . . .
C10 C 0.16021(12) 0.4746(9) 0.0829(2) 0.0342(6) Uani 1 1 d . . . . .
C11 C 0.48428(12) 0.4687(11) 0.85832(19) 0.0416(7) Uani 1 1 d . . . . .
H11A H 0.4884 0.5827 0.9023 0.050 Uiso 1 1 calc R . . . .
H11B H 0.4888 0.3494 0.8987 0.050 Uiso 1 1 calc R . . . .
C12 C 0.41860(13) 0.4704(12) 0.8135(2) 0.0475(8) Uani 1 1 d . . . . .
C13 C 0.5349(4) 0.6525(17) 0.7263(7) 0.103(3) Uani 1 1 d . . . . .
H13A H 0.4985 0.6468 0.6837 0.155 Uiso 1 1 calc GR . . . .
H13B H 0.5711 0.6564 0.6872 0.155 Uiso 1 1 calc GR . . . .
H13C H 0.5336 0.7705 0.7665 0.155 Uiso 1 1 calc GR . . . .
C14 C 0.59559(14) 0.4688(13) 0.8537(3) 0.0623(11) Uani 1 1 d . . . . .
H14A H 0.5982 0.5878 0.8934 0.094 Uiso 1 1 calc GR . . . .
H14B H 0.6308 0.4618 0.8127 0.094 Uiso 1 1 calc GR . . . .
H14C H 0.5950 0.3535 0.8959 0.094 Uiso 1 1 calc GR . . . .
C15 C 0.5382(3) 0.2830(12) 0.7300(5) 0.071(2) Uani 1 1 d . . . . .
H15A H 0.5373 0.1698 0.7735 0.106 Uiso 1 1 calc GR . . . .
H15B H 0.5752 0.2786 0.6929 0.106 Uiso 1 1 calc GR . . . .
H15C H 0.5026 0.2795 0.6855 0.106 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
O6 C12 1.239(3) . ?
O1 C2 1.500(15) . ?
O1 C2A 1.428(9) . ?
O1 C9 1.356(3) . ?
O2 C4 1.244(4) . ?
O3 C4' 1.369(11) . ?
O4 C5 1.364(3) . ?
O5 C7 1.335(3) . ?
O3A C4'A 1.346(12) . ?
O7 C12 1.241(4) . ?
N1 C11 1.501(4) . ?
N1 C13 1.472(10) . ?
N1 C14 1.498(4) . ?
N1 C15 1.516(8) . ?
C2 C1' 1.488(14) . ?
C2 C3 1.68(2) . ?
C2' C3' 1.3900 . ?
C2' C1' 1.3900 . ?
C3' C4' 1.3900 . ?
C4' C5' 1.3900 . ?
C5' C6' 1.3900 . ?
C6' C1' 1.3900 . ?
C2A C3A 1.413(15) . ?
C2A C1'A 1.482(10) . ?
C3 C4 1.560(11) . ?
C3A C4 1.559(13) . ?
C4 C10 1.423(4) . ?
C5 C6 1.375(4) . ?
C5 C10 1.409(4) . ?
C6 C7 1.398(4) . ?
C6'A C5'A 1.3900 . ?
C6'A C1'A 1.3900 . ?
C5'A C4'A 1.3900 . ?
C4'A C3'A 1.3900 . ?
C3'A C2'A 1.3900 . ?
C2'A C1'A 1.3900 . ?
C7 C8 1.381(4) . ?
C8 C9 1.370(4) . ?
C9 C10 1.410(3) . ?
C11 C12 1.523(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
C9 O1 C2 115.3(6) . . ?
C9 O1 C2A 120.8(4) . . ?
C11 N1 C15 109.5(5) . . ?
C13 N1 C11 111.7(5) . . ?
C13 N1 C14 111.7(6) . . ?
C13 N1 C15 111.6(4) . . ?
C14 N1 C11 106.8(2) . . ?
C14 N1 C15 105.3(5) . . ?
O1 C2 C3 103.4(11) . . ?
C1' C2 O1 106.2(9) . . ?
C1' C2 C3 116.7(10) . . ?
C3' C2' C1' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
O3 C4' C3' 115.1(8) . . ?
O3 C4' C5' 124.9(8) . . ?
C5' C4' C3' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C1' C6' C5' 120.0 . . ?
C2' C1' C2 105.5(9) . . ?
C6' C1' C2 134.5(9) . . ?
C6' C1' C2' 120.0 . . ?
O1 C2A C1'A 110.2(7) . . ?
C3A C2A O1 117.2(8) . . ?
C3A C2A C1'A 132.0(8) . . ?
C4 C3 C2 99.4(9) . . ?
C2A C3A C4 114.0(10) . . ?
O2 C4 C3 118.7(5) . . ?
O2 C4 C3A 121.1(5) . . ?
O2 C4 C10 123.0(3) . . ?
C10 C4 C3 115.5(5) . . ?
C10 C4 C3A 113.1(5) . . ?
O4 C5 C6 118.8(2) . . ?
O4 C5 C10 119.8(2) . . ?
C6 C5 C10 121.4(2) . . ?
C5 C6 C7 119.3(2) . . ?
C5'A C6'A C1'A 120.0 . . ?
C6'A C5'A C4'A 120.0 . . ?
O3A C4'A C5'A 118.7(8) . . ?
O3A C4'A C3'A 121.3(8) . . ?
C3'A C4'A C5'A 120.0 . . ?
C2'A C3'A C4'A 120.0 . . ?
C3'A C2'A C1'A 120.0 . . ?
C6'A C1'A C2A 114.6(6) . . ?
C2'A C1'A C2A 125.4(6) . . ?
C2'A C1'A C6'A 120.0 . . ?
O5 C7 C6 117.9(2) . . ?
O5 C7 C8 121.3(2) . . ?
C8 C7 C6 120.8(3) . . ?
C9 C8 C7 119.2(2) . . ?
O1 C9 C8 116.5(2) . . ?
O1 C9 C10 121.4(2) . . ?
C8 C9 C10 122.1(2) . . ?
C5 C10 C4 121.9(2) . . ?
C5 C10 C9 117.0(2) . . ?
C9 C10 C4 121.1(3) . . ?
N1 C11 C12 118.4(2) . . ?
O6 C12 O7 127.7(3) . . ?
O6 C12 C11 111.6(2) . . ?
O7 C12 C11 120.6(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
O1 C2 C1' C2' -97.8(10) . . . . ?
O1 C2 C1' C6' 81.6(12) . . . . ?
O1 C2 C3 C4 69.7(11) . . . . ?
O1 C2A C3A C4 -39.3(16) . . . . ?
O1 C2A C1'A C6'A 71.1(9) . . . . ?
O1 C2A C1'A C2'A -107.8(8) . . . . ?
O1 C9 C10 C4 -1.4(11) . . . . ?
O1 C9 C10 C5 -178.6(6) . . . . ?
O2 C4 C10 C5 -1.8(13) . . . . ?
O2 C4 C10 C9 -178.9(7) . . . . ?
O3 C4' C5' C6' 177.8(9) . . . . ?
O4 C5 C6 C7 178.9(6) . . . . ?
O4 C5 C10 C4 1.7(10) . . . . ?
O4 C5 C10 C9 178.9(5) . . . . ?
O5 C7 C8 C9 -177.7(6) . . . . ?
O3A C4'A C3'A C2'A -178.5(10) . . . . ?
N1 C11 C12 O6 -178.0(6) . . . . ?
N1 C11 C12 O7 5.5(11) . . . . ?
C2 O1 C9 C8 -158.1(8) . . . . ?
C2 O1 C9 C10 24.5(11) . . . . ?
C2 C3 C4 O2 146.1(10) . . . . ?
C2 C3 C4 C10 -52.2(12) . . . . ?
C2' C3' C4' O3 -178.0(8) . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C2' C1' C2 179.5(8) . . . . ?
C3' C2' C1' C6' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C5' C6' C1' C2 -179.3(11) . . . . ?
C5' C6' C1' C2' 0.0 . . . . ?
C1' C2 C3 C4 -174.1(11) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
C2A O1 C9 C8 178.8(7) . . . . ?
C2A O1 C9 C10 1.4(11) . . . . ?
C2A C3A C4 O2 -160.7(10) . . . . ?
C2A C3A C4 C10 37.8(15) . . . . ?
C3 C2 C1' C2' 147.7(11) . . . . ?
C3 C2 C1' C6' -32.9(17) . . . . ?
C3 C4 C10 C5 -162.7(8) . . . . ?
C3 C4 C10 C9 20.2(12) . . . . ?
C3A C2A C1'A C6'A -117.5(13) . . . . ?
C3A C2A C1'A C2'A 63.7(16) . . . . ?
C3A C4 C10 C5 159.3(8) . . . . ?
C3A C4 C10 C9 -17.8(12) . . . . ?
C5 C6 C7 O5 -178.7(6) . . . . ?
C5 C6 C7 C8 0.4(10) . . . . ?
C6 C5 C10 C4 -177.5(6) . . . . ?
C6 C5 C10 C9 -0.3(9) . . . . ?
C6 C7 C8 C9 3.3(10) . . . . ?
C6'A C5'A C4'A O3A 178.5(9) . . . . ?
C6'A C5'A C4'A C3'A 0.0 . . . . ?
C5'A C6'A C1'A C2A -178.9(8) . . . . ?
C5'A C6'A C1'A C2'A 0.0 . . . . ?
C5'A C4'A C3'A C2'A 0.0 . . . . ?
C4'A C3'A C2'A C1'A 0.0 . . . . ?
C3'A C2'A C1'A C2A 178.8(9) . . . . ?
C3'A C2'A C1'A C6'A 0.0 . . . . ?
C1'A C2A C3A C4 149.7(10) . . . . ?
C1'A C6'A C5'A C4'A 0.0 . . . . ?
C7 C8 C9 O1 177.0(6) . . . . ?
C7 C8 C9 C10 -5.6(10) . . . . ?
C8 C9 C10 C4 -178.6(6) . . . . ?
C8 C9 C10 C5 4.1(9) . . . . ?
C9 O1 C2 C1' 177.1(8) . . . . ?
C9 O1 C2 C3 -59.6(11) . . . . ?
C9 O1 C2A C3A 20.5(14) . . . . ?
C9 O1 C2A C1'A -166.6(7) . . . . ?
C10 C5 C6 C7 -1.8(10) . . . . ?
C13 N1 C11 C12 58.3(9) . . . . ?
C14 N1 C11 C12 -179.4(6) . . . . ?
C15 N1 C11 C12 -65.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(6)
2 0.3(6)

