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

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

data_linear-ld-WW
_database_code_depnum_ccdc_archive 'CCDC 1853728'
loop_
_audit_author_name
_audit_author_address
'Linda Shimon'
;Weizmann Institute
Israel
;
_audit_update_record             
;
2018-07-05 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;
#data_eh54kaiWW
# Structure Linda JW Shimon
# Kai Tao Ehud Gait TAU

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H22 N4 O3), 7(H2 O)'
_chemical_formula_sum            'C44 H58 N8 O13'
_chemical_formula_weight         906.98

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   21.2554(3)
_cell_length_b                   5.93942(10)
_cell_length_c                   17.7277(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.6651(12)
_cell_angle_gamma                90
_cell_volume                     2237.88(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13304
_cell_measurement_theta_min      4.8280
_cell_measurement_theta_max      79.6170

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.834
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.28413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17266
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.160
_diffrn_reflns_theta_max         80.184
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             4524
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     0.842
_reflns_Friedel_fraction_full    0.882

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

_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2016/4 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+1.8815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4524
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63045(9) 0.5659(4) 0.86437(11) 0.0187(4) Uani 1 1 d . . . . .
O2 O 0.78008(8) 0.6481(4) 0.84798(11) 0.0178(4) Uani 1 1 d . . . . .
O3 O 0.74535(9) 0.9487(3) 0.78524(11) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.59972(10) 0.1825(4) 0.93805(13) 0.0174(5) Uani 1 1 d . . . . .
H1A H 0.564489 0.269571 0.937089 0.021 Uiso 1 1 calc R U . . .
H1B H 0.629407 0.247922 0.968265 0.021 Uiso 1 1 calc R U . . .
H1C H 0.590116 0.043752 0.956381 0.021 Uiso 1 1 calc R U . . .
N2 N 0.68753(9) 0.3839(4) 0.77614(12) 0.0154(4) Uani 1 1 d . . . . .
H2 H 0.699862 0.253146 0.758284 0.019 Uiso 1 1 calc R U . . .
N3 N 0.41138(10) 0.2663(5) 0.82633(14) 0.0247(6) Uani 1 1 d . . . . .
H3 H 0.373232 0.259899 0.844981 0.030 Uiso 1 1 calc R U . . .
N4 N 0.72184(11) 0.0519(5) 0.55038(14) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.744162 -0.001168 0.514360 0.027 Uiso 1 1 d R U . . .
C1 C 0.62446(11) 0.1602(5) 0.86034(15) 0.0166(5) Uani 1 1 d . . . . .
H1 H 0.661279 0.055412 0.862218 0.020 Uiso 1 1 calc R U . . .
C2 C 0.64777(11) 0.3896(5) 0.83467(14) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.57424(12) 0.0574(5) 0.80698(16) 0.0195(6) Uani 1 1 d . . . . .
H3A H 0.591425 0.052969 0.755338 0.023 Uiso 1 1 calc R U . . .
H3B H 0.566416 -0.099898 0.822752 0.023 Uiso 1 1 calc R U . . .
C4 C 0.51267(12) 0.1799(5) 0.80448(15) 0.0191(6) Uani 1 1 d . . . . .
C5 C 0.49656(11) 0.3776(5) 0.76175(15) 0.0191(5) Uani 1 1 d . . . . .
C6 C 0.52879(12) 0.5153(5) 0.71039(16) 0.0201(6) Uani 1 1 d . . . . .
H6 H 0.571232 0.483622 0.697976 0.024 Uiso 1 1 calc R U . . .
C7 C 0.49818(13) 0.6962(5) 0.67839(16) 0.0222(6) Uani 1 1 d . . . . .
H7 H 0.519880 0.790076 0.643949 0.027 Uiso 1 1 calc R U . . .
C8 C 0.43491(13) 0.7446(6) 0.69598(16) 0.0251(6) Uani 1 1 d . . . . .
H8 H 0.415071 0.872460 0.674013 0.030 Uiso 1 1 calc R U . . .
C9 C 0.40156(13) 0.6099(6) 0.74434(17) 0.0253(7) Uani 1 1 d . . . . .
H9 H 0.358762 0.640729 0.755235 0.030 Uiso 1 1 calc R U . . .
C10 C 0.43268(12) 0.4259(6) 0.77695(16) 0.0210(6) Uani 1 1 d . . . . .
C11 C 0.45949(13) 0.1174(5) 0.84194(17) 0.0218(6) Uani 1 1 d . . . . .
H11 H 0.456241 -0.010056 0.874030 0.026 Uiso 1 1 calc R U . . .
C12 C 0.71039(12) 0.5900(5) 0.74199(14) 0.0152(5) Uani 1 1 d . . . . .
H12 H 0.673817 0.676224 0.720857 0.018 Uiso 1 1 calc R U . . .
C13 C 0.74720(11) 0.7419(5) 0.79717(14) 0.0146(5) Uani 1 1 d . . . . .
C14 C 0.75580(12) 0.5324(5) 0.67743(15) 0.0173(5) Uani 1 1 d . . . . .
H14A H 0.766475 0.673136 0.650523 0.021 Uiso 1 1 calc R U . . .
H14B H 0.795220 0.471697 0.699677 0.021 Uiso 1 1 calc R U . . .
C15 C 0.73052(12) 0.3654(5) 0.62104(15) 0.0174(5) Uani 1 1 d . . . . .
C16 C 0.67667(12) 0.3902(5) 0.57154(15) 0.0181(6) Uani 1 1 d . . . . .
C17 C 0.63268(12) 0.5632(6) 0.55673(16) 0.0211(6) Uani 1 1 d . . . . .
H17 H 0.633638 0.698856 0.585121 0.025 Uiso 1 1 calc R U . . .
C18 C 0.58848(13) 0.5320(6) 0.50061(17) 0.0263(7) Uani 1 1 d . . . . .
H18 H 0.559132 0.648832 0.490091 0.032 Uiso 1 1 calc R U . . .
C19 C 0.58546(14) 0.3321(6) 0.45829(18) 0.0286(7) Uani 1 1 d . . . . .
H19 H 0.554032 0.316167 0.420120 0.034 Uiso 1 1 calc R U . . .
C20 C 0.62736(14) 0.1588(6) 0.47127(17) 0.0265(6) Uani 1 1 d . . . . .
H20 H 0.625429 0.023264 0.442898 0.032 Uiso 1 1 calc R U . . .
C21 C 0.67288(13) 0.1908(5) 0.52795(16) 0.0204(6) Uani 1 1 d . . . . .
C22 C 0.75647(12) 0.1607(5) 0.60560(15) 0.0194(6) Uani 1 1 d . . . . .
H22 H 0.793143 0.101539 0.629472 0.023 Uiso 1 1 calc R U . . .
O4 O 0.500000 0.4550(5) 1.000000 0.0225(6) Uani 1 2 d GS T P . .
H4V H 0.528360 0.583480 1.014709 0.02(2) Uiso 0.5 1 d G . P . .
H4W H 0.533869 0.517205 1.021362 0.05(4) Uiso 0.5 1 d G . P . .
O5 O 0.70845(9) 0.3078(4) 1.00625(12) 0.0236(5) Uani 1 1 d G . . . .
H5V H 0.714615 0.260919 1.051043 0.035 Uiso 1 1 d G U . . .
H5W H 0.736729 0.255173 0.977711 0.035 Uiso 1 1 d G U . . .
O6 O 0.60369(9) 0.7434(4) 1.00424(11) 0.0201(4) Uani 1 1 d G . . . .
H6V H 0.633685 0.725078 1.035829 0.030 Uiso 1 1 d G U . . .
H6W H 0.615684 0.675057 0.964812 0.030 Uiso 1 1 d G U . . .
O7 O 0.79839(9) 0.2287(4) 0.89632(11) 0.0212(4) Uani 1 1 d G . . . .
H7V H 0.789561 0.352219 0.874451 0.032 Uiso 1 1 d G U . . .
H7W H 0.786349 0.127876 0.865341 0.032 Uiso 1 1 d G U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.230(3) . ?
O2 C13 1.263(3) . ?
O3 C13 1.247(4) . ?
N1 C1 1.486(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C2 1.346(3) . ?
N2 C12 1.452(3) . ?
N2 H2 0.8800 . ?
N3 C10 1.371(4) . ?
N3 C11 1.377(4) . ?
N3 H3 0.8800 . ?
N4 C22 1.379(4) . ?
N4 C21 1.383(4) . ?
N4 H4 0.8598 . ?
C1 C2 1.522(4) . ?
C1 C3 1.544(4) . ?
C1 H1 1.0000 . ?
C3 C4 1.497(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.369(4) . ?
C4 C5 1.437(4) . ?
C5 C6 1.408(4) . ?
C5 C10 1.417(3) . ?
C6 C7 1.375(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(4) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.538(4) . ?
C12 C14 1.544(3) . ?
C12 H12 1.0000 . ?
C14 C15 1.503(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C22 1.364(4) . ?
C15 C16 1.442(4) . ?
C16 C17 1.412(4) . ?
C16 C21 1.416(4) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.406(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(4) . ?
C20 H20 0.9500 . ?
C22 H22 0.9500 . ?
O4 H4V 1.0050 . ?
O4 H4W 0.8898 . ?
O5 H5V 0.8502 . ?
O5 H5W 0.8497 . ?
O6 H6V 0.8506 . ?
O6 H6W 0.8501 . ?
O7 H7V 0.8497 . ?
O7 H7W 0.8499 . ?

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
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N2 C12 121.1(2) . . ?
C2 N2 H2 119.5 . . ?
C12 N2 H2 119.5 . . ?
C10 N3 C11 108.8(2) . . ?
C10 N3 H3 125.6 . . ?
C11 N3 H3 125.6 . . ?
C22 N4 C21 108.6(3) . . ?
C22 N4 H4 113.9 . . ?
C21 N4 H4 115.2 . . ?
N1 C1 C2 108.5(2) . . ?
N1 C1 C3 110.7(2) . . ?
C2 C1 C3 113.3(2) . . ?
N1 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
C3 C1 H1 108.0 . . ?
O1 C2 N2 123.0(3) . . ?
O1 C2 C1 122.3(2) . . ?
N2 C2 C1 114.7(2) . . ?
C4 C3 C1 115.1(2) . . ?
C4 C3 H3A 108.5 . . ?
C1 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C1 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C11 C4 C5 106.5(2) . . ?
C11 C4 C3 125.5(3) . . ?
C5 C4 C3 128.0(2) . . ?
C6 C5 C10 118.7(3) . . ?
C6 C5 C4 134.5(2) . . ?
C10 C5 C4 106.8(2) . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 117.9(3) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N3 C10 C9 130.2(2) . . ?
N3 C10 C5 107.8(3) . . ?
C9 C10 C5 122.0(3) . . ?
C4 C11 N3 110.1(3) . . ?
C4 C11 H11 124.9 . . ?
N3 C11 H11 124.9 . . ?
N2 C12 C13 113.6(2) . . ?
N2 C12 C14 109.7(2) . . ?
C13 C12 C14 106.5(2) . . ?
N2 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C14 C12 H12 109.0 . . ?
O3 C13 O2 124.9(3) . . ?
O3 C13 C12 117.1(2) . . ?
O2 C13 C12 117.9(2) . . ?
C15 C14 C12 114.7(2) . . ?
C15 C14 H14A 108.6 . . ?
C12 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C12 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C22 C15 C16 106.8(3) . . ?
C22 C15 C14 125.4(3) . . ?
C16 C15 C14 127.8(3) . . ?
C17 C16 C21 118.3(3) . . ?
C17 C16 C15 135.0(3) . . ?
C21 C16 C15 106.7(2) . . ?
C18 C17 C16 118.9(3) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 121.8(3) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 117.3(3) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
N4 C21 C20 129.6(3) . . ?
N4 C21 C16 107.7(2) . . ?
C20 C21 C16 122.7(3) . . ?
C15 C22 N4 110.3(3) . . ?
C15 C22 H22 124.9 . . ?
N4 C22 H22 124.9 . . ?
H4V O4 H4W 25.1 . . ?
H5V O5 H5W 109.5 . . ?
H6V O6 H6W 104.5 . . ?
H7V O7 H7W 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 C2 O1 -2.9(4) . . . . ?
C12 N2 C2 C1 175.8(2) . . . . ?
N1 C1 C2 O1 -20.1(3) . . . . ?
C3 C1 C2 O1 103.3(3) . . . . ?
N1 C1 C2 N2 161.3(2) . . . . ?
C3 C1 C2 N2 -75.3(3) . . . . ?
N1 C1 C3 C4 55.1(3) . . . . ?
C2 C1 C3 C4 -67.0(3) . . . . ?
C1 C3 C4 C11 -100.4(3) . . . . ?
C1 C3 C4 C5 81.8(4) . . . . ?
C11 C4 C5 C6 -177.1(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C11 C4 C5 C10 0.6(3) . . . . ?
C3 C4 C5 C10 178.8(3) . . . . ?
C10 C5 C6 C7 2.0(4) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 -1.4(5) . . . . ?
C7 C8 C9 C10 1.4(5) . . . . ?
C11 N3 C10 C9 179.5(3) . . . . ?
C11 N3 C10 C5 -0.8(3) . . . . ?
C8 C9 C10 N3 180.0(3) . . . . ?
C8 C9 C10 C5 0.3(5) . . . . ?
C6 C5 C10 N3 178.2(3) . . . . ?
C4 C5 C10 N3 0.1(3) . . . . ?
C6 C5 C10 C9 -2.1(4) . . . . ?
C4 C5 C10 C9 179.8(3) . . . . ?
C5 C4 C11 N3 -1.1(3) . . . . ?
C3 C4 C11 N3 -179.3(3) . . . . ?
C10 N3 C11 C4 1.2(4) . . . . ?
C2 N2 C12 C13 60.0(3) . . . . ?
C2 N2 C12 C14 179.0(2) . . . . ?
N2 C12 C13 O3 -150.3(2) . . . . ?
C14 C12 C13 O3 88.8(3) . . . . ?
N2 C12 C13 O2 34.1(3) . . . . ?
C14 C12 C13 O2 -86.8(3) . . . . ?
N2 C12 C14 C15 51.0(3) . . . . ?
C13 C12 C14 C15 174.2(2) . . . . ?
C12 C14 C15 C22 -119.3(3) . . . . ?
C12 C14 C15 C16 63.0(4) . . . . ?
C22 C15 C16 C17 -176.1(3) . . . . ?
C14 C15 C16 C17 2.0(5) . . . . ?
C22 C15 C16 C21 0.5(3) . . . . ?
C14 C15 C16 C21 178.5(2) . . . . ?
C21 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C18 175.8(3) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C22 N4 C21 C20 176.5(3) . . . . ?
C22 N4 C21 C16 -1.0(3) . . . . ?
C19 C20 C21 N4 -176.7(3) . . . . ?
C19 C20 C21 C16 0.5(4) . . . . ?
C17 C16 C21 N4 177.6(2) . . . . ?
C15 C16 C21 N4 0.3(3) . . . . ?
C17 C16 C21 C20 -0.2(4) . . . . ?
C15 C16 C21 C20 -177.4(3) . . . . ?
C16 C15 C22 N4 -1.1(3) . . . . ?
C14 C15 C22 N4 -179.2(2) . . . . ?
C21 N4 C22 C15 1.3(3) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.052


####################################################################### 
# 
# 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_eh149WW
_database_code_depnum_ccdc_archive 'CCDC 1939621'
loop_
_audit_author_name
_audit_author_address
'Kai Tao'
;Tel Aviv University
Israel
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2019-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H22 N4 O3), 6(H2 O), H O'
_chemical_formula_sum            'C44 H57 N8 O13'
_chemical_formula_weight         905.97

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   21.200(4)
_cell_length_b                   5.9359(9)
_cell_length_c                   17.737(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.692(5)
_cell_angle_gamma                90
_cell_volume                     2231.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14682
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             962
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker KappaApexII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14513
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4477
_reflns_number_gt                3141
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.973

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

_computing_data_collection       'Bruker Apex3'
_computing_cell_refinement       'Bruker Apex3'
_computing_data_reduction        'Bruker Apex3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4477
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63027(14) 0.6138(4) 0.86479(15) 0.0143(7) Uani 1 1 d . . . . .
O2 O 0.78001(13) 0.6966(4) 0.84818(15) 0.0135(7) Uani 1 1 d . . . . .
O3 O 0.74545(14) 0.9980(4) 0.78515(15) 0.0141(7) Uani 1 1 d . . . . .
O5 O 0.29844(15) 0.7763(5) 0.89612(15) 0.0173(7) Uani 1 1 d G . . . .
H5 H 0.291416 0.662100 0.868448 0.026 Uiso 1 1 d G U . . .
N1 N 0.59966(16) 0.2289(5) 0.93810(17) 0.0139(8) Uani 1 1 d . . . . .
H1A H 0.629553 0.292792 0.968512 0.017 Uiso 1 1 calc R U . . .
H1B H 0.589577 0.090168 0.956176 0.017 Uiso 1 1 calc R U . . .
H1C H 0.564604 0.317334 0.937138 0.017 Uiso 1 1 calc R U . . .
N2 N 0.41124(17) 0.3139(6) 0.82620(19) 0.0201(9) Uani 1 1 d . . . . .
H2 H 0.372984 0.307766 0.844807 0.024 Uiso 1 1 calc R U . . .
N3 N 0.68724(16) 0.4324(5) 0.77645(17) 0.0110(8) Uani 1 1 d . . . . .
H3 H 0.699506 0.301496 0.758524 0.013 Uiso 1 1 calc R U . . .
N4 N 0.72205(17) 0.1012(6) 0.55056(19) 0.0176(9) Uani 1 1 d . . . . .
H4 H 0.729845 -0.034077 0.532609 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6247(2) 0.2065(7) 0.8601(2) 0.0114(9) Uani 1 1 d . . . . .
H1 H 0.661736 0.102182 0.861967 0.014 Uiso 1 1 calc R U . . .
C2 C 0.64771(19) 0.4371(7) 0.8350(2) 0.0123(9) Uani 1 1 d . . . . .
C3 C 0.57441(19) 0.1038(7) 0.8068(2) 0.0138(10) Uani 1 1 d . . . . .
H3A H 0.591584 0.099421 0.755169 0.017 Uiso 1 1 calc R U . . .
H3B H 0.566470 -0.053526 0.822545 0.017 Uiso 1 1 calc R U . . .
C4 C 0.5127(2) 0.2277(7) 0.8045(2) 0.0146(10) Uani 1 1 d . . . . .
C5 C 0.4964(2) 0.4253(7) 0.7615(2) 0.0140(9) Uani 1 1 d . . . . .
C6 C 0.5287(2) 0.5627(7) 0.7104(2) 0.0150(10) Uani 1 1 d . . . . .
H6 H 0.571267 0.531013 0.697841 0.018 Uiso 1 1 calc R U . . .
C7 C 0.4978(2) 0.7440(7) 0.6787(2) 0.0192(10) Uani 1 1 d . . . . .
H7 H 0.519512 0.837861 0.644201 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4353(2) 0.7927(8) 0.6961(2) 0.0211(11) Uani 1 1 d . . . . .
H8 H 0.415678 0.921306 0.674285 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4014(2) 0.6580(7) 0.7446(2) 0.0191(11) Uani 1 1 d . . . . .
H9 H 0.358544 0.689027 0.755585 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4331(2) 0.4734(7) 0.7767(2) 0.0166(10) Uani 1 1 d . . . . .
C11 C 0.4595(2) 0.1658(7) 0.8416(2) 0.0178(10) Uani 1 1 d . . . . .
H11 H 0.456262 0.038072 0.873566 0.021 Uiso 1 1 calc R U . . .
C12 C 0.7103(2) 0.6383(6) 0.7419(2) 0.0112(9) Uani 1 1 d . . . . .
H12 H 0.673661 0.724884 0.720763 0.013 Uiso 1 1 calc R U . . .
C13 C 0.74742(19) 0.7897(7) 0.7968(2) 0.0113(9) Uani 1 1 d . . . . .
C14 C 0.7559(2) 0.5811(7) 0.6777(2) 0.0147(10) Uani 1 1 d . . . . .
H14A H 0.766635 0.721867 0.650830 0.018 Uiso 1 1 calc R U . . .
H14B H 0.795401 0.520359 0.700069 0.018 Uiso 1 1 calc R U . . .
C15 C 0.7305(2) 0.4134(7) 0.6212(2) 0.0130(9) Uani 1 1 d . . . . .
C16 C 0.6771(2) 0.4390(7) 0.5714(2) 0.0132(10) Uani 1 1 d . . . . .
C17 C 0.6332(2) 0.6112(7) 0.5569(2) 0.0174(10) Uani 1 1 d . . . . .
H17 H 0.634058 0.746689 0.585378 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5887(2) 0.5794(8) 0.5004(2) 0.0227(11) Uani 1 1 d . . . . .
H18 H 0.559361 0.696446 0.489696 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5854(2) 0.3801(8) 0.4582(2) 0.0243(11) Uani 1 1 d . . . . .
H19 H 0.553742 0.363890 0.420315 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6275(2) 0.2076(8) 0.4710(2) 0.0210(11) Uani 1 1 d . . . . .
H20 H 0.625741 0.072308 0.442406 0.025 Uiso 1 1 calc R U . . .
C21 C 0.6729(2) 0.2394(7) 0.5278(2) 0.0154(10) Uani 1 1 d . . . . .
C22 C 0.7569(2) 0.2091(7) 0.6059(2) 0.0155(10) Uani 1 1 d . . . . .
H22 H 0.793718 0.150123 0.629757 0.019 Uiso 1 1 calc R U . . .
H50 H 0.292(2) 0.904(7) 0.875(2) 0.015(12) Uiso 1 1 d . . . . .
O4 O 0.20846(14) 0.8570(5) 1.00585(15) 0.0195(7) Uani 1 1 d G . . . .
H4A H 0.214047 0.807001 1.050242 0.029 Uiso 1 1 d G U . . .
H4B H 0.240580 0.808044 0.974874 0.029 Uiso 1 1 d G U . . .
O6 O 0.60330(14) 0.7913(5) 1.00422(15) 0.0163(7) Uani 1 1 d G . . . .
H6A H 0.633050 0.773915 1.035779 0.024 Uiso 1 1 d G U . . .
H6B H 0.615336 0.719551 0.965368 0.024 Uiso 1 1 d G U . . .
O7 O 0.500000 0.5025(7) 1.000000 0.0187(10) Uani 1 2 d GS T P . .
H7A H 0.472102 0.598725 0.987921 0.028 Uiso 0.5 1 d G U P . .


_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 1.233(5) . ?
O2 C13 1.264(5) . ?
O3 C13 1.255(5) . ?
O5 H5 0.8488 . ?
O5 H50 0.85(4) . ?
N1 C1 1.494(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C11 1.374(5) . ?
N2 C10 1.375(5) . ?
N2 H2 0.8800 . ?
N3 C2 1.343(5) . ?
N3 C12 1.454(5) . ?
N3 H3 0.8800 . ?
N4 C22 1.379(5) . ?
N4 C21 1.382(5) . ?
N4 H4 0.8800 . ?
C1 C2 1.522(6) . ?
C1 C3 1.542(5) . ?
C1 H1 1.0000 . ?
C3 C4 1.501(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.362(6) . ?
C4 C5 1.439(5) . ?
C5 C6 1.404(5) . ?
C5 C10 1.403(6) . ?
C6 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(6) . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.535(5) . ?
C12 C14 1.541(6) . ?
C12 H12 1.0000 . ?
C14 C15 1.507(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C22 1.364(6) . ?
C15 C16 1.437(6) . ?
C16 C17 1.404(6) . ?
C16 C21 1.417(5) . ?
C17 C18 1.381(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(6) . ?
C20 H20 0.9500 . ?
C22 H22 0.9500 . ?
O4 H4A 0.8485 . ?
O4 H4B 0.9268 . ?
O6 H6A 0.8446 . ?
O6 H6B 0.8520 . ?
O7 H7A 0.8478 . ?

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
H5 O5 H50 115.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C11 N2 C10 108.2(4) . . ?
C11 N2 H2 125.9 . . ?
C10 N2 H2 125.9 . . ?
C2 N3 C12 121.6(3) . . ?
C2 N3 H3 119.2 . . ?
C12 N3 H3 119.2 . . ?
C22 N4 C21 109.1(3) . . ?
C22 N4 H4 125.5 . . ?
C21 N4 H4 125.5 . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 C3 110.6(3) . . ?
C2 C1 C3 113.4(3) . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C3 C1 H1 108.2 . . ?
O1 C2 N3 122.8(4) . . ?
O1 C2 C1 122.8(3) . . ?
N3 C2 C1 114.4(3) . . ?
C4 C3 C1 114.8(3) . . ?
C4 C3 H3A 108.6 . . ?
C1 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C1 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C11 C4 C5 106.4(4) . . ?
C11 C4 C3 125.5(4) . . ?
C5 C4 C3 128.1(4) . . ?
C6 C5 C10 118.8(4) . . ?
C6 C5 C4 134.5(4) . . ?
C10 C5 C4 106.7(4) . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.4(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 117.1(4) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 H9 121.5 . . ?
N2 C10 C9 129.4(4) . . ?
N2 C10 C5 108.2(4) . . ?
C9 C10 C5 122.4(4) . . ?
C4 C11 N2 110.5(4) . . ?
C4 C11 H11 124.7 . . ?
N2 C11 H11 124.7 . . ?
N3 C12 C13 113.4(3) . . ?
N3 C12 C14 110.0(3) . . ?
C13 C12 C14 106.0(3) . . ?
N3 C12 H12 109.1 . . ?
C13 C12 H12 109.1 . . ?
C14 C12 H12 109.1 . . ?
O3 C13 O2 124.5(4) . . ?
O3 C13 C12 117.2(4) . . ?
O2 C13 C12 118.2(4) . . ?
C15 C14 C12 114.5(3) . . ?
C15 C14 H14A 108.6 . . ?
C12 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C12 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C22 C15 C16 107.1(4) . . ?
C22 C15 C14 125.1(4) . . ?
C16 C15 C14 127.8(4) . . ?
C17 C16 C21 118.2(4) . . ?
C17 C16 C15 134.9(4) . . ?
C21 C16 C15 106.9(3) . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 122.1(4) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 117.2(4) . . ?
C19 C20 H20 121.4 . . ?
C21 C20 H20 121.4 . . ?
N4 C21 C20 129.8(4) . . ?
N4 C21 C16 107.2(3) . . ?
C20 C21 C16 122.9(4) . . ?
C15 C22 N4 109.7(4) . . ?
C15 C22 H22 125.1 . . ?
N4 C22 H22 125.1 . . ?
H4A O4 H4B 110.2 . . ?
H6A O6 H6B 104.3 . . ?

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
C12 N3 C2 O1 -2.6(6) . . . . ?
C12 N3 C2 C1 175.7(3) . . . . ?
N1 C1 C2 O1 -19.9(5) . . . . ?
C3 C1 C2 O1 103.1(4) . . . . ?
N1 C1 C2 N3 161.8(3) . . . . ?
C3 C1 C2 N3 -75.2(4) . . . . ?
N1 C1 C3 C4 55.1(4) . . . . ?
C2 C1 C3 C4 -66.5(5) . . . . ?
C1 C3 C4 C11 -100.7(5) . . . . ?
C1 C3 C4 C5 82.3(5) . . . . ?
C11 C4 C5 C6 -177.2(4) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C11 C4 C5 C10 0.9(4) . . . . ?
C3 C4 C5 C10 178.4(4) . . . . ?
C10 C5 C6 C7 2.1(6) . . . . ?
C4 C5 C6 C7 180.0(4) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 -1.6(6) . . . . ?
C7 C8 C9 C10 1.5(6) . . . . ?
C11 N2 C10 C9 179.8(4) . . . . ?
C11 N2 C10 C5 -0.7(5) . . . . ?
C8 C9 C10 N2 179.8(4) . . . . ?
C8 C9 C10 C5 0.4(6) . . . . ?
C6 C5 C10 N2 178.3(3) . . . . ?
C4 C5 C10 N2 -0.2(4) . . . . ?
C6 C5 C10 C9 -2.2(6) . . . . ?
C4 C5 C10 C9 179.4(4) . . . . ?
C5 C4 C11 N2 -1.4(5) . . . . ?
C3 C4 C11 N2 -178.9(4) . . . . ?
C10 N2 C11 C4 1.3(5) . . . . ?
C2 N3 C12 C13 60.0(5) . . . . ?
C2 N3 C12 C14 178.5(3) . . . . ?
N3 C12 C13 O3 -149.9(4) . . . . ?
C14 C12 C13 O3 89.3(4) . . . . ?
N3 C12 C13 O2 33.3(5) . . . . ?
C14 C12 C13 O2 -87.5(4) . . . . ?
N3 C12 C14 C15 51.2(4) . . . . ?
C13 C12 C14 C15 174.1(3) . . . . ?
C12 C14 C15 C22 -119.6(4) . . . . ?
C12 C14 C15 C16 63.6(5) . . . . ?
C22 C15 C16 C17 -176.4(5) . . . . ?
C14 C15 C16 C17 0.8(8) . . . . ?
C22 C15 C16 C21 1.2(5) . . . . ?
C14 C15 C16 C21 178.4(4) . . . . ?
C21 C16 C17 C18 -0.9(6) . . . . ?
C15 C16 C17 C18 176.6(5) . . . . ?
C16 C17 C18 C19 1.1(7) . . . . ?
C17 C18 C19 C20 -0.9(7) . . . . ?
C18 C19 C20 C21 0.4(7) . . . . ?
C22 N4 C21 C20 176.4(4) . . . . ?
C22 N4 C21 C16 -0.8(5) . . . . ?
C19 C20 C21 N4 -177.0(4) . . . . ?
C19 C20 C21 C16 -0.2(6) . . . . ?
C17 C16 C21 N4 177.8(4) . . . . ?
C15 C16 C21 N4 -0.2(5) . . . . ?
C17 C16 C21 C20 0.4(6) . . . . ?
C15 C16 C21 C20 -177.7(4) . . . . ?
C16 C15 C22 N4 -1.7(5) . . . . ?
C14 C15 C22 N4 -179.0(4) . . . . ?
C21 N4 C22 C15 1.6(5) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055



