# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1483760'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 - 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O5.(C H4 O)0.5'
_chemical_formula_sum            'C19.50 H18 N2 O5.50'
_chemical_formula_weight         368.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   7.7594(12)
_cell_length_b                   19.459(3)
_cell_length_c                   11.8044(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.142(2)
_cell_angle_gamma                90.00
_cell_volume                     1712.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    387
_cell_measurement_theta_min      12
_cell_measurement_theta_max      28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .1
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891243
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 - 
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9839
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3068
_reflns_number_gt                2502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0461P)²+1.3292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3068
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.46991(19) 0.64283(8) -0.02161(13) 0.0168(3) Uani 1 1 d . . .
C2 C 0.3329(2) 0.68758(10) 0.00460(17) 0.0194(4) Uani 1 1 d . . .
H2A H 0.3170 0.6746 0.0822 0.023 Uiso 1 1 calc R . .
H2B H 0.2170 0.6801 -0.0557 0.023 Uiso 1 1 calc R . .
C3 C 0.3818(2) 0.76367(10) 0.00675(16) 0.0190(4) Uani 1 1 d . . .
H3A H 0.3751 0.7782 -0.0747 0.023 Uiso 1 1 calc R . .
H3B H 0.2906 0.7902 0.0325 0.023 Uiso 1 1 calc R . .
C4 C 0.5666(2) 0.78264(10) 0.08628(16) 0.0174(4) Uani 1 1 d . . .
O4 O 0.58325(17) 0.75979(7) 0.20053(11) 0.0204(3) Uani 1 1 d D . .
H4O H 0.6980(17) 0.7774(12) 0.2498(18) 0.042(7) Uiso 1 1 d D . .
C5 C 0.5834(2) 0.86219(10) 0.07725(16) 0.0195(4) Uani 1 1 d . . .
O5 O 0.49383(19) 0.90192(7) 0.11570(13) 0.0291(4) Uani 1 1 d . . .
C6 C 0.7100(2) 0.87613(10) 0.00837(16) 0.0189(4) Uani 1 1 d . . .
C7 C 0.7568(3) 0.93823(10) -0.03418(17) 0.0230(4) Uani 1 1 d . . .
H7A H 0.7106 0.9806 -0.0154 0.028 Uiso 1 1 calc R . .
C8 C 0.8725(3) 0.93613(11) -0.10452(18) 0.0266(5) Uani 1 1 d . . .
H8A H 0.9079 0.9776 -0.1340 0.032 Uiso 1 1 calc R . .
C9 C 0.9376(3) 0.87328(11) -0.13249(18) 0.0266(5) Uani 1 1 d . . .
H9A H 1.0143 0.8730 -0.1827 0.032 Uiso 1 1 calc R . .
C10 C 0.8940(2) 0.81127(10) -0.08933(17) 0.0212(4) Uani 1 1 d . . .
H10A H 0.9394 0.7689 -0.1088 0.025 Uiso 1 1 calc R . .
C11 C 0.7802(2) 0.81392(10) -0.01585(15) 0.0171(4) Uani 1 1 d . . .
N12 N 0.71751(19) 0.75792(8) 0.03803(13) 0.0163(3) Uani 1 1 d . . .
C14 C 0.5956(2) 0.61085(10) 0.07725(16) 0.0176(4) Uani 1 1 d . . .
C15 C 0.5478(2) 0.54967(10) 0.12073(16) 0.0201(4) Uani 1 1 d . . .
H15A H 0.4342 0.5294 0.0852 0.024 Uiso 1 1 calc R . .
C16 C 0.6674(3) 0.51816(10) 0.21667(17) 0.0219(4) Uani 1 1 d . . .
H16A H 0.6357 0.4761 0.2464 0.026 Uiso 1 1 calc R . .
C17 C 0.8328(3) 0.54807(10) 0.26903(17) 0.0240(4) Uani 1 1 d . . .
H17A H 0.9138 0.5266 0.3349 0.029 Uiso 1 1 calc R . .
C18 C 0.8801(2) 0.60916(10) 0.22533(17) 0.0211(4) Uani 1 1 d . . .
H18A H 0.9942 0.6291 0.2606 0.025 Uiso 1 1 calc R . .
C19 C 0.7610(2) 0.64141(10) 0.12989(16) 0.0181(4) Uani 1 1 d . . .
C20 C 0.8290(2) 0.70246(10) 0.07849(16) 0.0183(4) Uani 1 1 d . . .
O20 O 0.98181(18) 0.70103(8) 0.06909(14) 0.0314(4) Uani 1 1 d . . .
C21 C 0.4999(2) 0.64778(10) -0.12851(16) 0.0183(4) Uani 1 1 d . . .
O21 O 0.40272(18) 0.67914(7) -0.21212(11) 0.0244(3) Uani 1 1 d . . .
O22 O 0.64707(17) 0.61379(7) -0.13452(11) 0.0227(3) Uani 1 1 d . . .
C22 C 0.6981(3) 0.62343(12) -0.24295(18) 0.0314(5) Uani 1 1 d . . .
H22A H 0.6023 0.6062 -0.3097 0.047 Uiso 1 1 calc R . .
H22B H 0.8091 0.5981 -0.2380 0.047 Uiso 1 1 calc R . .
H22C H 0.7172 0.6724 -0.2542 0.047 Uiso 1 1 calc R . .
O31 O 1.0000 0.5000 0.0000 0.0995(13) Uani 1 2 d S . .
C31 C 1.0978(5) 0.5560(2) 0.0169(5) 0.0386(13) Uani 0.50 1 d P . .
H31A H 1.1933 0.5521 0.0910 0.058 Uiso 0.50 1 calc PR . .
H31B H 1.0221 0.5958 0.0207 0.058 Uiso 0.50 1 calc PR . .
H31C H 1.1512 0.5620 -0.0486 0.058 Uiso 0.50 1 calc PR . .


_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
N1 C21 1.349(2) . ?
N1 C14 1.438(2) . ?
N1 C2 1.472(2) . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O4 1.392(2) . ?
C4 N12 1.516(2) . ?
C4 C5 1.559(3) . ?
O4 H4O 0.9799(11) . ?
C5 O5 1.209(2) . ?
C5 C6 1.464(3) . ?
C6 C11 1.390(3) . ?
C6 C7 1.395(3) . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.398(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10A 0.9500 . ?
C11 N12 1.415(2) . ?
N12 C20 1.383(2) . ?
C14 C15 1.387(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.391(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.495(3) . ?
C20 O20 1.221(2) . ?
C21 O21 1.225(2) . ?
C21 O22 1.339(2) . ?
O22 C22 1.453(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O31 C31 1.312(4) 3_765 ?
O31 C31 1.312(4) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N1 C14 122.39(15) . . ?
C21 N1 C2 118.48(15) . . ?
C14 N1 C2 116.88(14) . . ?
N1 C2 C3 112.72(15) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 115.59(15) . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
O4 C4 N12 112.94(14) . . ?
O4 C4 C3 109.71(14) . . ?
N12 C4 C3 112.59(14) . . ?
O4 C4 C5 113.35(15) . . ?
N12 C4 C5 101.64(14) . . ?
C3 C4 C5 106.26(15) . . ?
C4 O4 H4O 106.7(15) . . ?
O5 C5 C6 129.36(18) . . ?
O5 C5 C4 122.81(17) . . ?
C6 C5 C4 107.65(15) . . ?
C11 C6 C7 121.61(17) . . ?
C11 C6 C5 108.37(16) . . ?
C7 C6 C5 129.97(18) . . ?
C8 C7 C6 117.91(18) . . ?
C8 C7 H7A 121.0 . . ?
C6 C7 H7A 121.0 . . ?
C7 C8 C9 120.37(19) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C10 C9 C8 122.21(18) . . ?
C10 C9 H9A 118.9 . . ?
C8 C9 H9A 118.9 . . ?
C9 C10 C11 117.11(18) . . ?
C9 C10 H10A 121.4 . . ?
C11 C10 H10A 121.4 . . ?
C6 C11 C10 120.71(17) . . ?
C6 C11 N12 112.00(16) . . ?
C10 C11 N12 127.25(17) . . ?
C20 N12 C11 119.74(15) . . ?
C20 N12 C4 126.33(15) . . ?
C11 N12 C4 108.83(14) . . ?
C15 C14 C19 120.61(17) . . ?
C15 C14 N1 118.73(16) . . ?
C19 C14 N1 120.65(17) . . ?
C14 C15 C16 119.53(17) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C17 C16 C15 120.17(18) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C18 C17 C16 120.12(18) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 120.19(18) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C14 119.36(18) . . ?
C18 C19 C20 117.16(16) . . ?
C14 C19 C20 122.90(17) . . ?
O20 C20 N12 121.09(17) . . ?
O20 C20 C19 118.67(17) . . ?
N12 C20 C19 120.18(15) . . ?
O21 C21 O22 123.12(17) . . ?
O21 C21 N1 124.17(17) . . ?
O22 C21 N1 112.70(16) . . ?
C21 O22 C22 115.35(15) . . ?
O22 C22 H22A 109.5 . . ?
O22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 O31 C31 180.0(2) 3_765 . ?
O31 C31 H31A 109.5 . . ?
O31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C21 N1 C2 C3 -64.8(2) . . . . ?
C14 N1 C2 C3 98.53(19) . . . . ?
N1 C2 C3 C4 -52.7(2) . . . . ?
C2 C3 C4 O4 -55.3(2) . . . . ?
C2 C3 C4 N12 71.4(2) . . . . ?
C2 C3 C4 C5 -178.16(15) . . . . ?
O4 C4 C5 O5 -52.8(2) . . . . ?
N12 C4 C5 O5 -174.33(17) . . . . ?
C3 C4 C5 O5 67.7(2) . . . . ?
O4 C4 C5 C6 131.66(15) . . . . ?
N12 C4 C5 C6 10.17(17) . . . . ?
C3 C4 C5 C6 -107.78(16) . . . . ?
O5 C5 C6 C11 -179.85(19) . . . . ?
C4 C5 C6 C11 -4.74(19) . . . . ?
O5 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C6 C7 172.88(18) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
C5 C6 C7 C8 -175.62(18) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C7 C6 C11 C10 -3.3(3) . . . . ?
C5 C6 C11 C10 174.52(16) . . . . ?
C7 C6 C11 N12 178.74(16) . . . . ?
C5 C6 C11 N12 -3.4(2) . . . . ?
C9 C10 C11 C6 2.3(3) . . . . ?
C9 C10 C11 N12 179.89(17) . . . . ?
C6 C11 N12 C20 -145.91(16) . . . . ?
C10 C11 N12 C20 36.3(3) . . . . ?
C6 C11 N12 C4 10.4(2) . . . . ?
C10 C11 N12 C4 -167.34(17) . . . . ?
O4 C4 N12 C20 20.4(2) . . . . ?
C3 C4 N12 C20 -104.6(2) . . . . ?
C5 C4 N12 C20 142.14(17) . . . . ?
O4 C4 N12 C11 -133.99(15) . . . . ?
C3 C4 N12 C11 101.08(17) . . . . ?
C5 C4 N12 C11 -12.21(17) . . . . ?
C21 N1 C14 C15 -112.5(2) . . . . ?
C2 N1 C14 C15 84.8(2) . . . . ?
C21 N1 C14 C19 68.7(2) . . . . ?
C2 N1 C14 C19 -93.9(2) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
N1 C14 C15 C16 -179.70(16) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C17 C18 C19 C20 -172.91(17) . . . . ?
C15 C14 C19 C18 1.4(3) . . . . ?
N1 C14 C19 C18 -179.86(16) . . . . ?
C15 C14 C19 C20 172.39(17) . . . . ?
N1 C14 C19 C20 -8.9(3) . . . . ?
C11 N12 C20 O20 0.4(3) . . . . ?
C4 N12 C20 O20 -151.47(18) . . . . ?
C11 N12 C20 C19 -176.82(16) . . . . ?
C4 N12 C20 C19 31.3(3) . . . . ?
C18 C19 C20 O20 39.9(3) . . . . ?
C14 C19 C20 O20 -131.2(2) . . . . ?
C18 C19 C20 N12 -142.82(18) . . . . ?
C14 C19 C20 N12 46.0(3) . . . . ?
C14 N1 C21 O21 -174.22(18) . . . . ?
C2 N1 C21 O21 -11.8(3) . . . . ?
C14 N1 C21 O22 6.6(2) . . . . ?
C2 N1 C21 O22 169.01(15) . . . . ?
O21 C21 O22 C22 7.4(3) . . . . ?
N1 C21 O22 C22 -173.38(16) . . . . ?

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
O4 H4O O21 0.9799(11) 1.745(9) 2.6830(18) 159(2) 4_676

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_2i
_database_code_depnum_ccdc_archive 'CCDC 1483761'
_audit_update_record             
;
2016-06-06 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;
_audit_creation_date             2016-05-18
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C24 H26 N4 O4'
_chemical_formula_moiety         'C24 H26 N4 O4'
_chemical_formula_weight         434.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.843(3)
_cell_length_b                   19.280(5)
_cell_length_c                   11.337(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.215(5)
_cell_angle_gamma                90.0000
_cell_volume                     2209.5(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4161
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            16836
_diffrn_reflns_av_R_equivalents  0.1912
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3871
_reflns_number_gt                3192
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.2167
_refine_ls_wR_factor_gt          0.2014
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3871
_refine_ls_number_parameters     299
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0732P)²+2.2354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.005
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.8638(2) 0.23832(11) 0.2867(2) 0.0246(6) Uani 1 1 d D . . . .
O5 O 0.9568(2) 0.09489(12) 0.3626(2) 0.0313(6) Uani 1 1 d . . . . .
O20 O 0.6532(2) 0.29562(11) 0.5012(2) 0.0295(6) Uani 1 1 d . . . . .
O21 O 1.1309(2) 0.32512(12) 0.7202(2) 0.0267(6) Uani 1 1 d . . . . .
N1 N 1.0109(2) 0.35575(13) 0.5178(3) 0.0216(6) Uani 1 1 d . . . . .
N12 N 0.8270(2) 0.23523(12) 0.4849(2) 0.0198(6) Uani 1 1 d . . . . .
N22 N 0.9562(3) 0.39724(13) 0.6846(3) 0.0249(6) Uani 1 1 d D . . . .
N31 N 0.2690(3) 0.49357(17) 0.4446(3) 0.0395(8) Uani 1 1 d . . . . .
C2 C 1.0887(3) 0.30990(16) 0.4684(3) 0.0234(7) Uani 1 1 d . . . . .
H2A H 1.1839 0.3175 0.5172 0.028 Uiso 1 1 calc R U . . .
H2B H 1.0718 0.3222 0.3792 0.028 Uiso 1 1 calc R U . . .
C3 C 1.0563(3) 0.23290(15) 0.4757(3) 0.0237(7) Uani 1 1 d . . . . .
H3A H 1.1092 0.2053 0.4376 0.028 Uiso 1 1 calc R U . . .
H3B H 1.0844 0.2195 0.5659 0.028 Uiso 1 1 calc R U . . .
C4 C 0.9111(3) 0.21361(16) 0.4103(3) 0.0219(7) Uani 1 1 d . . . . .
C5 C 0.9081(3) 0.13299(16) 0.4198(3) 0.0231(7) Uani 1 1 d . . . . .
C6 C 0.8478(3) 0.11558(15) 0.5110(3) 0.0216(7) Uani 1 1 d . . . . .
C7 C 0.8357(3) 0.05084(17) 0.5609(3) 0.0259(7) Uani 1 1 d . . . . .
H7 H 0.8661 0.0099 0.5334 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7782(3) 0.04818(17) 0.6516(3) 0.0295(8) Uani 1 1 d . . . . .
H8 H 0.7676 0.0049 0.6869 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7358(3) 0.10912(17) 0.6911(3) 0.0278(8) Uani 1 1 d . . . . .
H9 H 0.6980 0.1063 0.7546 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7465(3) 0.17375(16) 0.6417(3) 0.0243(7) Uani 1 1 d . . . . .
H10 H 0.7160 0.2146 0.6694 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8040(3) 0.17640(16) 0.5492(3) 0.0208(7) Uani 1 1 d . . . . .
C14 C 0.8946(3) 0.38601(15) 0.4248(3) 0.0214(7) Uani 1 1 d . . . . .
C15 C 0.9073(3) 0.44687(16) 0.3645(3) 0.0225(7) Uani 1 1 d . . . . .
H15 H 0.9917 0.4681 0.3862 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7991(3) 0.47683(17) 0.2736(3) 0.0270(7) Uani 1 1 d . . . . .
H16 H 0.8088 0.5183 0.2325 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6745(3) 0.44556(16) 0.2423(3) 0.0248(7) Uani 1 1 d . . . . .
H17 H 0.5994 0.4656 0.1794 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6614(3) 0.38548(16) 0.3033(3) 0.0236(7) Uani 1 1 d . . . . .
H18 H 0.5763 0.3652 0.2832 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7706(3) 0.35416(15) 0.3936(3) 0.0210(7) Uani 1 1 d . . . . .
C20 C 0.7459(3) 0.29311(15) 0.4631(3) 0.0221(7) Uani 1 1 d . . . . .
C21 C 1.0367(3) 0.35739(15) 0.6449(3) 0.0213(7) Uani 1 1 d . . . . .
C22 C 0.9609(3) 0.39211(18) 0.8146(3) 0.0276(8) Uani 1 1 d . . . . .
H22A H 0.9281 0.4359 0.8382 0.033 Uiso 1 1 calc R U . . .
H22B H 1.0538 0.3857 0.8722 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8776(4) 0.33176(18) 0.8310(4) 0.0325(8) Uani 1 1 d . . . . .
H23A H 0.9021 0.2896 0.7948 0.039 Uiso 1 1 calc R U . . .
H23B H 0.7835 0.3418 0.7815 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8915(3) 0.31628(18) 0.9675(4) 0.0328(8) Uani 1 1 d . . . . .
H24A H 0.8352 0.2759 0.9677 0.039 Uiso 1 1 calc R U . . .
H24B H 0.9844 0.3032 1.0161 0.039 Uiso 1 1 calc R U . . .
C25 C 0.8538(4) 0.37633(19) 1.0343(4) 0.0396(9) Uani 1 1 d . . . . .
H25A H 0.8653 0.3626 1.1208 0.048 Uiso 1 1 calc R U . . .
H25B H 0.9107 0.4162 1.0368 0.048 Uiso 1 1 calc R U . . .
H25C H 0.7612 0.3889 0.9883 0.048 Uiso 1 1 calc R U . . .
C31 C 0.3477(4) 0.45487(19) 0.5005(4) 0.0342(8) Uani 1 1 d . . . . .
C32 C 0.4492(4) 0.4048(2) 0.5697(4) 0.0452(10) Uani 1 1 d . . . . .
H32A H 0.4598 0.3703 0.5105 0.054 Uiso 1 1 calc R U . . .
H32B H 0.4225 0.3815 0.6335 0.054 Uiso 1 1 calc R U . . .
H32C H 0.5333 0.4289 0.6113 0.054 Uiso 1 1 calc R U . . .
H4O H 0.779(2) 0.2164(19) 0.240(3) 0.048(12) Uiso 1 1 d D . . . .
H22N H 0.883(2) 0.4216(15) 0.620(2) 0.026(9) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.390(4) . ?
O4 H4O 0.978(5) . ?
O5 C5 1.220(4) . ?
O20 C20 1.230(4) . ?
O21 C21 1.237(4) . ?
N1 C21 1.365(4) . ?
N1 C14 1.442(4) . ?
N1 C2 1.465(4) . ?
N12 C20 1.386(4) . ?
N12 C11 1.418(4) . ?
N12 C4 1.510(4) . ?
N22 C21 1.356(4) . ?
N22 C22 1.460(4) . ?
N22 H22N 0.979(5) . ?
N31 C31 1.138(5) . ?
C2 C3 1.535(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.559(4) . ?
C5 C6 1.448(4) . ?
C6 C11 1.392(4) . ?
C6 C7 1.396(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(4) . ?
C10 H10 0.9500 . ?
C14 C15 1.390(4) . ?
C14 C19 1.402(4) . ?
C15 C16 1.377(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.494(4) . ?
C22 C23 1.525(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.529(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.518(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C31 C32 1.461(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O4 H4O 109(3) . . ?
C21 N1 C14 123.6(3) . . ?
C21 N1 C2 119.4(3) . . ?
C14 N1 C2 115.9(3) . . ?
C20 N12 C11 121.1(2) . . ?
C20 N12 C4 126.5(2) . . ?
C11 N12 C4 108.8(2) . . ?
C21 N22 C22 120.4(3) . . ?
C21 N22 H22N 118(2) . . ?
C22 N22 H22N 121(2) . . ?
N1 C2 C3 112.9(2) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 115.2(3) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
O4 C4 N12 113.1(2) . . ?
O4 C4 C3 110.3(2) . . ?
N12 C4 C3 112.8(2) . . ?
O4 C4 C5 113.7(3) . . ?
N12 C4 C5 101.8(2) . . ?
C3 C4 C5 104.7(2) . . ?
O5 C5 C6 129.4(3) . . ?
O5 C5 C4 122.7(3) . . ?
C6 C5 C4 107.9(3) . . ?
C11 C6 C7 122.3(3) . . ?
C11 C6 C5 108.7(3) . . ?
C7 C6 C5 129.0(3) . . ?
C8 C7 C6 117.9(3) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 122.8(3) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C11 117.4(3) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C6 C11 C10 119.8(3) . . ?
C6 C11 N12 111.7(3) . . ?
C10 C11 N12 128.5(3) . . ?
C15 C14 C19 120.2(3) . . ?
C15 C14 N1 119.0(3) . . ?
C19 C14 N1 120.8(3) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 118.6(3) . . ?
C18 C19 C20 117.5(3) . . ?
C14 C19 C20 123.4(3) . . ?
O20 C20 N12 121.0(3) . . ?
O20 C20 C19 118.7(3) . . ?
N12 C20 C19 120.3(3) . . ?
O21 C21 N22 121.7(3) . . ?
O21 C21 N1 121.3(3) . . ?
N22 C21 N1 117.0(3) . . ?
N22 C22 C23 111.6(3) . . ?
N22 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N22 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 115.2(3) . . ?
C22 C23 H23A 108.5 . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23B 108.5 . . ?
C24 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C25 C24 C23 114.2(3) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N31 C31 C32 178.8(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C21 N1 C2 C3 71.0(4) . . . . ?
C14 N1 C2 C3 -97.2(3) . . . . ?
N1 C2 C3 C4 55.8(4) . . . . ?
C20 N12 C4 O4 -25.4(4) . . . . ?
C11 N12 C4 O4 133.2(3) . . . . ?
C20 N12 C4 C3 100.6(3) . . . . ?
C11 N12 C4 C3 -100.8(3) . . . . ?
C20 N12 C4 C5 -147.7(3) . . . . ?
C11 N12 C4 C5 10.9(3) . . . . ?
C2 C3 C4 O4 51.8(4) . . . . ?
C2 C3 C4 N12 -75.7(3) . . . . ?
C2 C3 C4 C5 174.4(3) . . . . ?
O4 C4 C5 O5 52.2(4) . . . . ?
N12 C4 C5 O5 174.1(3) . . . . ?
C3 C4 C5 O5 -68.3(4) . . . . ?
O4 C4 C5 C6 -131.6(3) . . . . ?
N12 C4 C5 C6 -9.6(3) . . . . ?
C3 C4 C5 C6 108.0(3) . . . . ?
O5 C5 C6 C11 -179.0(3) . . . . ?
C4 C5 C6 C11 5.1(3) . . . . ?
O5 C5 C6 C7 3.2(6) . . . . ?
C4 C5 C6 C7 -172.7(3) . . . . ?
C11 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 C8 177.4(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C7 C6 C11 C10 0.6(5) . . . . ?
C5 C6 C11 C10 -177.4(3) . . . . ?
C7 C6 C11 N12 -179.9(3) . . . . ?
C5 C6 C11 N12 2.1(4) . . . . ?
C9 C10 C11 C6 -0.1(5) . . . . ?
C9 C10 C11 N12 -179.6(3) . . . . ?
C20 N12 C11 C6 151.3(3) . . . . ?
C4 N12 C11 C6 -8.7(3) . . . . ?
C20 N12 C11 C10 -29.3(5) . . . . ?
C4 N12 C11 C10 170.8(3) . . . . ?
C21 N1 C14 C15 107.0(3) . . . . ?
C2 N1 C14 C15 -85.4(3) . . . . ?
C21 N1 C14 C19 -74.1(4) . . . . ?
C2 N1 C14 C19 93.5(3) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
N1 C14 C15 C16 178.9(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 -1.6(5) . . . . ?
C17 C18 C19 C14 2.0(5) . . . . ?
C17 C18 C19 C20 174.6(3) . . . . ?
C15 C14 C19 C18 -1.1(5) . . . . ?
N1 C14 C19 C18 180.0(3) . . . . ?
C15 C14 C19 C20 -173.3(3) . . . . ?
N1 C14 C19 C20 7.8(5) . . . . ?
C11 N12 C20 O20 1.4(5) . . . . ?
C4 N12 C20 O20 157.6(3) . . . . ?
C11 N12 C20 C19 -179.2(3) . . . . ?
C4 N12 C20 C19 -23.0(4) . . . . ?
C18 C19 C20 O20 -43.3(4) . . . . ?
C14 C19 C20 O20 129.0(3) . . . . ?
C18 C19 C20 N12 137.3(3) . . . . ?
C14 C19 C20 N12 -50.4(4) . . . . ?
C22 N22 C21 O21 -12.8(4) . . . . ?
C22 N22 C21 N1 168.7(3) . . . . ?
C14 N1 C21 O21 173.0(3) . . . . ?
C2 N1 C21 O21 5.7(4) . . . . ?
C14 N1 C21 N22 -8.5(4) . . . . ?
C2 N1 C21 N22 -175.8(3) . . . . ?
C21 N22 C22 C23 -83.1(4) . . . . ?
N22 C22 C23 C24 172.0(3) . . . . ?
C22 C23 C24 C25 59.6(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4O O21 . . 4_565 2.657(3) 0.98(2) 1.73(3) 156(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


