# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

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

data_1aMeOH
_database_code_depnum_ccdc_archive 'CCDC 1985275'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
ivica.djilovic@chem.pmf.hr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O3, C H4 O'
_chemical_formula_sum            'C14 H15 N3 O4'
_chemical_formula_weight         289.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 N4 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4964(4)
_cell_length_b                   14.0972(6)
_cell_length_c                   11.1992(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.924(4)
_cell_angle_gamma                90
_cell_volume                     1334.23(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11502
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.4640
_cell_measurement_theta_min      4.2820
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            45731
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         4.293
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -37.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 12 omega  -44.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 13 omega    7.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
 14 omega   34.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  179.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 15 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 16 omega  -25.00   59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -99.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   -3.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   77.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 18 omega  -81.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  135.0000  116.0202 78

#__ type_ start__ end____ width___ exp.time_
 19 omega  -86.00   -8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  143.0000 -172.7514 78

#__ type_ start__ end____ width___ exp.time_
 20 omega  -63.00   19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  106.0000   13.0979 82

#__ type_ start__ end____ width___ exp.time_
 21 omega  -80.00   -3.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  134.0000  -78.1012 77

#__ type_ start__ end____ width___ exp.time_
 22 omega  -71.00    8.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  119.0000   34.8401 79

#__ type_ start__ end____ width___ exp.time_
 23 omega  -60.00  -17.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994  100.0000  154.7040 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0659397000
_diffrn_orient_matrix_UB_12      -0.0064189000
_diffrn_orient_matrix_UB_13      -0.0435456000
_diffrn_orient_matrix_UB_21      0.0486939000
_diffrn_orient_matrix_UB_22      -0.0246913000
_diffrn_orient_matrix_UB_23      -0.0373795000
_diffrn_orient_matrix_UB_31      -0.0179901000
_diffrn_orient_matrix_UB_32      -0.0433641000
_diffrn_orient_matrix_UB_33      0.0276202000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2092
_reflns_number_total             2464
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.020
_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)+(0.0660P)²+0.2108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C2(H2A), C8(H8), C6(H6), C10(H10), C11(H11), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), 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
O1 O 0.60942(12) 0.74726(7) 0.75137(9) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.66364(13) 0.70448(7) 0.51801(9) 0.0347(3) Uani 1 1 d . . . . .
H4 H 0.672712 0.724526 0.589018 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.51286(11) 0.47856(7) 0.78570(9) 0.0303(3) Uani 1 1 d . . . . .
H2 H 0.507033 0.537889 0.790572 0.045 Uiso 1 1 calc GR . . . .
O3 O 0.50852(13) 0.29051(7) 0.79899(10) 0.0368(3) Uani 1 1 d . . . . .
H3 H 0.498880 0.232039 0.810689 0.055 Uiso 1 1 calc GR . . . .
N1 N 0.40477(13) 0.73792(8) 0.86523(10) 0.0240(3) Uani 1 1 d . . . . .
H1 H 0.337144 0.767744 0.906425 0.029 Uiso 1 1 calc R . . . .
N2 N 0.40456(13) 0.64054(8) 0.85702(10) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.50033(14) 1.09133(8) 0.82666(10) 0.0288(3) Uani 1 1 d . . . . .
C9 C 0.50611(15) 0.89257(9) 0.81960(11) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.30821(15) 0.49215(9) 0.91997(12) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.40926(15) 0.43835(9) 0.85483(12) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.51220(16) 0.78646(10) 0.80801(11) 0.0237(3) Uani 1 1 d . . . . .
C13 C 0.63258(17) 0.94584(10) 0.78650(12) 0.0283(3) Uani 1 1 d . . . . .
H13 H 0.722944 0.915463 0.760659 0.034 Uiso 1 1 calc R . . . .
C2 C 0.31203(16) 0.59533(9) 0.92069(12) 0.0245(3) Uani 1 1 d . . . . .
H2A H 0.245542 0.629522 0.968644 0.029 Uiso 1 1 calc R . . . .
C5 C 0.40428(16) 0.33882(9) 0.86051(12) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.20276(16) 0.44607(10) 0.98852(13) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.135128 0.482373 1.033253 0.034 Uiso 1 1 calc R . . . .
C6 C 0.29724(17) 0.29568(9) 0.92771(13) 0.0281(3) Uani 1 1 d . . . . .
H6 H 0.292618 0.228382 0.930240 0.034 Uiso 1 1 calc R . . . .
C10 C 0.37835(16) 0.94104(10) 0.85764(12) 0.0256(3) Uani 1 1 d . . . . .
H10 H 0.290368 0.907380 0.882254 0.031 Uiso 1 1 calc R . . . .
C11 C 0.38088(17) 1.03907(10) 0.85923(13) 0.0281(3) Uani 1 1 d . . . . .
H11 H 0.292178 1.071230 0.885094 0.034 Uiso 1 1 calc R . . . .
C7 C 0.19613(17) 0.34824(10) 0.99172(13) 0.0310(3) Uani 1 1 d . . . . .
H7 H 0.123088 0.317193 1.037282 0.037 Uiso 1 1 calc R . . . .
C12 C 0.62451(17) 1.04391(10) 0.79186(13) 0.0300(3) Uani 1 1 d . . . . .
H12 H 0.711840 1.079506 0.769631 0.036 Uiso 1 1 calc R . . . .
C14 C 0.54359(19) 0.63364(11) 0.50421(15) 0.0384(4) Uani 1 1 d . . . . .
H14A H 0.498784 0.631028 0.420056 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.459933 0.649283 0.554970 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.589448 0.571858 0.528106 0.058 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
O1 C1 1.2241(16) . ?
O4 C14 1.4245(18) . ?
O2 C4 1.3550(16) . ?
O3 C5 1.3597(16) . ?
N1 N2 1.3759(15) . ?
N1 C1 1.3538(17) . ?
N2 C2 1.2839(17) . ?
N3 C11 1.3350(18) . ?
N3 C12 1.3405(18) . ?
C9 C1 1.5028(18) . ?
C9 C13 1.3923(19) . ?
C9 C10 1.3865(19) . ?
C3 C4 1.4049(18) . ?
C3 C2 1.4550(18) . ?
C3 C8 1.3986(18) . ?
C4 C5 1.4054(19) . ?
C13 C12 1.386(2) . ?
C5 C6 1.3801(19) . ?
C8 C7 1.381(2) . ?
C6 C7 1.389(2) . ?
C10 C11 1.3821(19) . ?

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 N2 117.97(11) . . ?
C2 N2 N1 117.05(11) . . ?
C11 N3 C12 116.59(12) . . ?
C13 C9 C1 118.66(12) . . ?
C10 C9 C1 123.52(12) . . ?
C10 C9 C13 117.79(12) . . ?
C4 C3 C2 121.88(12) . . ?
C8 C3 C4 119.65(12) . . ?
C8 C3 C2 118.46(12) . . ?
O2 C4 C3 122.59(12) . . ?
O2 C4 C5 117.90(12) . . ?
C3 C4 C5 119.51(12) . . ?
O1 C1 N1 122.76(12) . . ?
O1 C1 C9 121.68(12) . . ?
N1 C1 C9 115.55(11) . . ?
C12 C13 C9 118.92(13) . . ?
N2 C2 C3 120.52(12) . . ?
O3 C5 C4 116.92(12) . . ?
O3 C5 C6 123.78(12) . . ?
C6 C5 C4 119.29(12) . . ?
C7 C8 C3 120.54(13) . . ?
C5 C6 C7 121.60(12) . . ?
C11 C10 C9 119.02(12) . . ?
N3 C11 C10 124.02(13) . . ?
C8 C7 C6 119.38(13) . . ?
N3 C12 C13 123.65(13) . . ?

_olex2_date_sample_data_collection 2019-01-16
_olex2_exptl_crystal_mounting_method loop
_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_3c
_database_code_depnum_ccdc_archive 'CCDC 1985279'
_audit_update_record             
;
2020-02-25 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4

loop_
_audit_author_email
ivica.djilovic@chem.pmf.hr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N3 O5, C H4 O'
_chemical_formula_sum            'C22 H21 N3 O6'
_chemical_formula_weight         423.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.8673(7)
_cell_length_b                   10.0421(4)
_cell_length_c                   24.2618(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.637(4)
_cell_angle_gamma                90
_cell_volume                     3864.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1730
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.8010
_cell_measurement_theta_min      4.1510
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_recrystallization_method 'From methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7907
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         4.145
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -40.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -57.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542 -179.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -97.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1542  -19.0000 -150.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0352216000
_diffrn_orient_matrix_UB_12      0.0153543000
_diffrn_orient_matrix_UB_13      0.0175163000
_diffrn_orient_matrix_UB_21      -0.0146350000
_diffrn_orient_matrix_UB_22      -0.0454998000
_diffrn_orient_matrix_UB_23      0.0199436000
_diffrn_orient_matrix_UB_31      0.0233248000
_diffrn_orient_matrix_UB_32      -0.0517984000
_diffrn_orient_matrix_UB_33      -0.0123013000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2584
_reflns_number_total             3784
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.011
_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)+(0.0563P)²+2.8691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C22B-O22B
 1.45 with sigma of 0.0001
 C22A-O22A
 1.45 with sigma of 0.0001
 O4-H4
 0.82 with sigma of 0.001
 O3-H3
 0.82 with sigma of 0.0001
3. Rigid bond restraints
 C22B, C22A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C22B \\sim C22A: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(C22B) \\sim Ueq, Uanis(C22A) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
5. Others
 Sof(C22A)=Sof(H22E)=Sof(H22F)=Sof(H22G)=Sof(O22A)=Sof(H22H)=1-FVAR(1)
 Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(O22B)=Sof(H22D)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3A), C2(H2A), C6(H6), C14(H14), C11(H11), C8(H8), C21(H21), C7(H7),
 C19(H19), C13(H13), C12(H12), C20(H20)
6.c Idealised Me refined as rotating group:
 C22B(H22A,H22B,H22C), C22A(H22E,H22F,H22G)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O22B(H22D), O22A(H22H)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.34484(11) 0.08478(17) 0.42909(8) 0.0521(5) Uani 1 1 d . . . . .
H2 H 0.360032 0.158418 0.418668 0.078 Uiso 1 1 calc GR . . . .
O3 O 0.27842(11) -0.13324(16) 0.47461(8) 0.0555(5) Uani 1 1 d D . . . .
O1 O 0.47250(12) 0.34789(16) 0.35560(8) 0.0550(5) Uani 1 1 d . . . . .
N2 N 0.32297(13) 0.33680(18) 0.39951(8) 0.0406(5) Uani 1 1 d . . . . .
O4 O 0.17137(15) 0.7595(2) 0.35471(9) 0.0674(6) Uani 1 1 d D . . . .
O5 O 0.08466(13) 0.7789(2) 0.25697(9) 0.0703(6) Uani 1 1 d . . . . .
H5 H 0.051214 0.773515 0.282024 0.105 Uiso 1 1 calc GR . . . .
N1 N 0.35448(13) 0.45706(18) 0.38161(8) 0.0403(5) Uani 1 1 d . . . . .
N3 N 0.35325(14) 0.69138(19) 0.38571(8) 0.0465(5) Uani 1 1 d . . . . .
H3A H 0.338498 0.753063 0.408056 0.056 Uiso 1 1 calc R . . . .
C5 C 0.22724(16) -0.0241(2) 0.46568(9) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.26187(15) 0.0897(2) 0.44222(9) 0.0383(5) Uani 1 1 d . . . . .
C3 C 0.21223(15) 0.2023(2) 0.43362(9) 0.0399(6) Uani 1 1 d . . . . .
C16 C 0.25096(15) 0.5777(2) 0.32140(10) 0.0386(5) Uani 1 1 d . . . . .
C9 C 0.46801(16) 0.5833(2) 0.34317(9) 0.0393(6) Uani 1 1 d . . . . .
C10 C 0.42742(16) 0.7009(2) 0.35835(9) 0.0398(6) Uani 1 1 d . . . . .
C2 C 0.24511(17) 0.3254(2) 0.41106(10) 0.0449(6) Uani 1 1 d . . . . .
H2A H 0.208917 0.397027 0.404928 0.054 Uiso 1 1 calc R . . . .
C15 C 0.30024(16) 0.5760(2) 0.37640(10) 0.0408(6) Uani 1 1 d . . . . .
H15 H 0.259414 0.572786 0.405925 0.049 Uiso 1 1 calc R . . . .
C6 C 0.14435(17) -0.0256(3) 0.47941(10) 0.0484(6) Uani 1 1 d . . . . .
H6 H 0.121413 -0.101749 0.494786 0.058 Uiso 1 1 calc R . . . .
C17 C 0.18735(16) 0.6721(2) 0.31290(11) 0.0440(6) Uani 1 1 d . . . . .
C1 C 0.43382(16) 0.4538(2) 0.36000(9) 0.0401(6) Uani 1 1 d . . . . .
C14 C 0.54384(16) 0.5903(2) 0.31558(10) 0.0468(6) Uani 1 1 d . . . . .
H14 H 0.570295 0.512245 0.304840 0.056 Uiso 1 1 calc R . . . .
C11 C 0.46529(18) 0.8232(2) 0.34728(11) 0.0515(7) Uani 1 1 d . . . . .
H11 H 0.439798 0.901989 0.358160 0.062 Uiso 1 1 calc R . . . .
C8 C 0.12794(16) 0.1984(3) 0.44838(11) 0.0497(7) Uani 1 1 d . . . . .
H8 H 0.094099 0.273174 0.443100 0.060 Uiso 1 1 calc R . . . .
C18 C 0.14345(16) 0.6799(2) 0.26252(11) 0.0480(6) Uani 1 1 d . . . . .
C21 C 0.26642(17) 0.4906(3) 0.27859(11) 0.0517(7) Uani 1 1 d . . . . .
H21 H 0.307840 0.425744 0.283250 0.062 Uiso 1 1 calc R . . . .
C7 C 0.09458(17) 0.0851(3) 0.47060(11) 0.0551(7) Uani 1 1 d . . . . .
H7 H 0.038080 0.083116 0.479766 0.066 Uiso 1 1 calc R . . . .
C19 C 0.16044(18) 0.5939(3) 0.22115(12) 0.0573(7) Uani 1 1 d . . . . .
H19 H 0.130883 0.599640 0.187577 0.069 Uiso 1 1 calc R . . . .
C13 C 0.57982(18) 0.7111(3) 0.30411(11) 0.0553(7) Uani 1 1 d . . . . .
H13 H 0.630321 0.714953 0.285645 0.066 Uiso 1 1 calc R . . . .
C12 C 0.54045(19) 0.8271(3) 0.32021(12) 0.0567(7) Uani 1 1 d . . . . .
H12 H 0.565063 0.908924 0.312660 0.068 Uiso 1 1 calc R . . . .
C20 C 0.2214(2) 0.4984(3) 0.22905(12) 0.0638(8) Uani 1 1 d . . . . .
H20 H 0.232494 0.438556 0.200930 0.077 Uiso 1 1 calc R . . . .
C22B C 0.5554(7) 0.1154(12) 0.43999(11) 0.103(3) Uani 0.573(8) 1 d D U P A 1
H22A H 0.525570 0.038240 0.426589 0.155 Uiso 0.573(8) 1 calc GR . P A 1
H22B H 0.612706 0.111926 0.428409 0.155 Uiso 0.573(8) 1 calc GR . P A 1
H22C H 0.528751 0.194241 0.425418 0.155 Uiso 0.573(8) 1 calc GR . P A 1
O22B O 0.5541(3) 0.1182(6) 0.49971(10) 0.105(2) Uani 0.573(8) 1 d D . P A 1
H22D H 0.518983 0.065048 0.510434 0.157 Uiso 0.573(8) 1 calc GR . P A 1
C22A C 0.5426(6) 0.1574(4) 0.4481(3) 0.072(4) Uani 0.427(8) 1 d D U P A 2
H22E H 0.506382 0.143612 0.416167 0.108 Uiso 0.427(8) 1 calc GR . P A 2
H22F H 0.589168 0.212786 0.438362 0.108 Uiso 0.427(8) 1 calc GR . P A 2
H22G H 0.511358 0.200113 0.476406 0.108 Uiso 0.427(8) 1 calc GR . P A 2
O22A O 0.5739(4) 0.0301(4) 0.4680(3) 0.115(3) Uani 0.427(8) 1 d D . P A 2
H22H H 0.608480 0.042327 0.493263 0.172 Uiso 0.427(8) 1 calc GR . P A 2
H4 H 0.1252(11) 0.795(4) 0.3506(19) 0.15(2) Uiso 1 1 d D . . . .
H3 H 0.3279(2) -0.122(2) 0.4843(5) 0.21(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C4 1.364(3) . ?
C22Ba H22A 0.9600 . ?
C22Ba H22B 0.9600 . ?
C22Ba H22C 0.9600 . ?
C22Ba O22B 1.45000(13) . ?
O22Ba H22D 0.8200 . ?
C22Ab H22E 0.9600 . ?
C22Ab H22F 0.9600 . ?
C22Ab H22G 0.9600 . ?
C22Ab O22A 1.44999(12) . ?
O22Ab H22H 0.8200 . ?
O3 C5 1.377(3) . ?
O3 H3 0.82000(15) . ?
O1 C1 1.234(3) . ?
N2 N1 1.382(3) . ?
N2 C2 1.280(3) . ?
O4 C17 1.370(3) . ?
O4 H4 0.8200(11) . ?
O5 H5 0.8200 . ?
O5 C18 1.367(3) . ?
N1 C15 1.476(3) . ?
N1 C1 1.378(3) . ?
N3 H3A 0.8600 . ?
N3 C10 1.371(3) . ?
N3 C15 1.445(3) . ?
C5 C4 1.397(3) . ?
C5 C6 1.366(3) . ?
C4 C3 1.390(3) . ?
C3 C2 1.455(3) . ?
C3 C8 1.395(3) . ?
C16 C15 1.527(3) . ?
C16 C17 1.396(3) . ?
C16 C21 1.385(3) . ?
C9 C10 1.399(3) . ?
C9 C1 1.471(3) . ?
C9 C14 1.395(3) . ?
C10 C11 1.397(3) . ?
C2 H2A 0.9300 . ?
C15 H15 0.9800 . ?
C6 H6 0.9300 . ?
C6 C7 1.377(4) . ?
C17 C18 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.371(4) . ?
C18 C19 1.357(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(4) . ?
C7 H7 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.371(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C20 H20 0.9300 . ?

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 O2 H2 109.5 . . ?
C5 O3 H3 119.6(16) . . ?
O22Ba C22Ba H22A 109.5 . . ?
O22Ba C22Ba H22B 109.5 . . ?
C2 N2 N1 120.5(2) . . ?
C17 O4 H4 112(3) . . ?
C18 O5 H5 109.5 . . ?
N2 N1 C15 121.28(19) . . ?
C1 N1 N2 116.21(19) . . ?
H22Aa C22Ba H22B 109.5 . . ?
O22Ba C22Ba H22C 109.5 . . ?
H22Aa C22Ba H22C 109.5 . . ?
H22Ba C22Ba H22C 109.5 . . ?
C22Ba O22Ba H22D 109.5 . . ?
O22Ab C22Ab H22E 109.5 . . ?
H22Eb C22Ab H22F 109.5 . . ?
C1 N1 C15 121.56(19) . . ?
C10 N3 H3A 120.5 . . ?
C10 N3 C15 118.94(19) . . ?
C15 N3 H3A 120.5 . . ?
O3 C5 C4 118.6(2) . . ?
C6 C5 O3 121.4(2) . . ?
C6 C5 C4 120.1(2) . . ?
O2 C4 C5 117.3(2) . . ?
O2 C4 C3 122.8(2) . . ?
C3 C4 C5 119.9(2) . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 C8 118.8(2) . . ?
O22Ab C22Ab H22F 109.5 . . ?
O22Ab C22Ab H22G 109.5 . . ?
H22Eb C22Ab H22G 109.5 . . ?
H22Fb C22Ab H22G 109.5 . . ?
C22Ab O22Ab H22H 109.5 . . ?
C8 C3 C2 118.5(2) . . ?
C17 C16 C15 119.1(2) . . ?
C21 C16 C15 123.4(2) . . ?
C21 C16 C17 117.4(2) . . ?
C10 C9 C1 119.8(2) . . ?
C14 C9 C10 119.6(2) . . ?
C14 C9 C1 120.5(2) . . ?
N3 C10 C9 118.5(2) . . ?
N3 C10 C11 122.3(2) . . ?
C11 C10 C9 119.2(2) . . ?
N2 C2 C3 121.2(2) . . ?
N2 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
N1 C15 C16 111.50(18) . . ?
N1 C15 H15 107.8 . . ?
N3 C15 N1 107.46(19) . . ?
N3 C15 C16 114.13(19) . . ?
N3 C15 H15 107.8 . . ?
C16 C15 H15 107.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
O4 C17 C16 118.3(2) . . ?
O4 C17 C18 121.0(2) . . ?
C18 C17 C16 120.6(2) . . ?
O1 C1 N1 121.0(2) . . ?
O1 C1 C9 123.3(2) . . ?
N1 C1 C9 115.6(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
O5 C18 C17 116.8(2) . . ?
C19 C18 O5 122.6(2) . . ?
C19 C18 C17 120.6(2) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C3 C2 -1.5(4) . . . . ?
O2 C4 C3 C8 -179.9(2) . . . . ?
O3 C5 C4 O2 0.6(3) . . . . ?
O3 C5 C4 C3 -178.8(2) . . . . ?
O3 C5 C6 C7 179.4(2) . . . . ?
N2 N1 C15 N3 150.50(19) . . . . ?
N2 N1 C15 C16 -83.7(2) . . . . ?
N2 N1 C1 O1 2.2(3) . . . . ?
N2 N1 C1 C9 -177.62(18) . . . . ?
O4 C17 C18 O5 0.5(3) . . . . ?
O4 C17 C18 C19 179.2(2) . . . . ?
O5 C18 C19 C20 178.7(3) . . . . ?
N1 N2 C2 C3 -175.6(2) . . . . ?
N3 C10 C11 C12 179.2(2) . . . . ?
C5 C4 C3 C2 177.9(2) . . . . ?
C5 C4 C3 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C4 C3 C2 N2 -2.1(4) . . . . ?
C4 C3 C8 C7 -0.5(4) . . . . ?
C3 C8 C7 C6 1.0(4) . . . . ?
C16 C17 C18 O5 -177.3(2) . . . . ?
C16 C17 C18 C19 1.5(4) . . . . ?
C16 C21 C20 C19 0.5(4) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C9 C14 C13 C12 0.1(4) . . . . ?
C10 N3 C15 N1 48.4(3) . . . . ?
C10 N3 C15 C16 -75.8(3) . . . . ?
C10 C9 C1 O1 -168.6(2) . . . . ?
C10 C9 C1 N1 11.2(3) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C2 N2 N1 C15 1.3(3) . . . . ?
C2 N2 N1 C1 -167.7(2) . . . . ?
C2 C3 C8 C7 -179.0(2) . . . . ?
C15 N1 C1 O1 -166.8(2) . . . . ?
C15 N1 C1 C9 13.4(3) . . . . ?
C15 N3 C10 C9 -28.3(3) . . . . ?
C15 N3 C10 C11 154.5(2) . . . . ?
C15 C16 C17 O4 -0.4(3) . . . . ?
C15 C16 C17 C18 177.5(2) . . . . ?
C15 C16 C21 C20 -178.4(2) . . . . ?
C6 C5 C4 O2 -179.6(2) . . . . ?
C6 C5 C4 C3 1.0(4) . . . . ?
C17 C16 C15 N1 170.5(2) . . . . ?
C17 C16 C15 N3 -67.5(3) . . . . ?
C17 C16 C21 C20 1.0(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C1 N1 C15 N3 -41.1(3) . . . . ?
C1 N1 C15 C16 84.7(3) . . . . ?
C1 C9 C10 N3 -4.1(3) . . . . ?
C1 C9 C10 C11 173.2(2) . . . . ?
C1 C9 C14 C13 -174.2(2) . . . . ?
C14 C9 C10 N3 -179.6(2) . . . . ?
C14 C9 C10 C11 -2.3(3) . . . . ?
C14 C9 C1 O1 6.9(4) . . . . ?
C14 C9 C1 N1 -173.3(2) . . . . ?
C14 C13 C12 C11 -0.5(4) . . . . ?
C8 C3 C2 N2 176.3(2) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C21 C16 C15 N1 -10.2(3) . . . . ?
C21 C16 C15 N3 111.8(3) . . . . ?
C21 C16 C17 O4 -179.7(2) . . . . ?
C21 C16 C17 C18 -1.9(3) . . . . ?

_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_1bH2O
_database_code_depnum_ccdc_archive 'CCDC 1985276'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
ivica.djilovic@chem.pmf.hr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O3, H2 O'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H16 N3 O6 Cu1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3319(3)
_cell_length_b                   12.7546(6)
_cell_length_c                   12.3732(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.089(4)
_cell_angle_gamma                90
_cell_volume                     1298.39(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1457
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.5780
_cell_measurement_theta_min      4.1450
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4884
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         4.148
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   43.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542  179.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   30.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104   57.0000 -120.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega -107.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104  -19.0000  -90.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0422861000
_diffrn_orient_matrix_UB_12      0.0466667000
_diffrn_orient_matrix_UB_13      0.0178868000
_diffrn_orient_matrix_UB_21      0.0215223000
_diffrn_orient_matrix_UB_22      0.0066633000
_diffrn_orient_matrix_UB_23      -0.0528130000
_diffrn_orient_matrix_UB_31      -0.0720304000
_diffrn_orient_matrix_UB_32      0.0293982000
_diffrn_orient_matrix_UB_33      -0.0162728000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1606
_reflns_number_total             2403
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C8(H8), C2(H2A), C11(H11), C5(H5), C7(H7), C13(H13), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.59780(15) 0.53351(10) 0.21770(14) 0.0644(5) Uani 1 1 d . . . . .
H2 H 0.523135 0.558906 0.245000 0.097 Uiso 1 1 calc GR . . . .
O3 O 1.05015(15) 0.62219(10) 0.05873(14) 0.0623(4) Uani 1 1 d . . . . .
H3 H 1.110389 0.671228 0.049879 0.093 Uiso 1 1 calc GR . . . .
O1 O 0.21572(16) 0.55717(11) 0.36224(14) 0.0661(5) Uani 1 1 d . . . . .
O4 O 0.2103(2) 0.44399(13) 0.1721(2) 0.0693(5) Uani 1 1 d . . . . .
N1 N 0.29341(16) 0.72140(12) 0.32846(13) 0.0441(4) Uani 1 1 d . . . . .
H1 H 0.276088 0.787687 0.332079 0.053 Uiso 1 1 calc R . . . .
N3 N -0.21910(17) 0.75955(13) 0.50014(13) 0.0481(4) Uani 1 1 d . . . . .
N2 N 0.42511(16) 0.68366(12) 0.28524(13) 0.0456(4) Uani 1 1 d . . . . .
C9 C 0.05030(19) 0.69502(14) 0.40979(15) 0.0384(5) Uani 1 1 d . . . . .
C10 C 0.02398(19) 0.79958(14) 0.42868(15) 0.0429(5) Uani 1 1 d . . . . .
H10 H 0.095757 0.850388 0.411243 0.051 Uiso 1 1 calc R . . . .
C3 C 0.66187(19) 0.71732(14) 0.20679(15) 0.0391(4) Uani 1 1 d . . . . .
C4 C 0.69254(19) 0.61092(14) 0.18906(16) 0.0428(5) Uani 1 1 d . . . . .
C6 C 0.92616(19) 0.65740(15) 0.10808(16) 0.0431(5) Uani 1 1 d . . . . .
C1 C 0.1931(2) 0.65192(15) 0.36469(16) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.76820(19) 0.79090(15) 0.17477(15) 0.0442(5) Uani 1 1 d . . . . .
H8 H 0.750209 0.861629 0.186640 0.053 Uiso 1 1 calc R . . . .
C2 C 0.5235(2) 0.75055(15) 0.25520(15) 0.0423(5) Uani 1 1 d . . . . .
H2A H 0.505627 0.821710 0.264659 0.051 Uiso 1 1 calc R . . . .
C11 C -0.1105(2) 0.82736(15) 0.47383(16) 0.0472(5) Uani 1 1 d . . . . .
H11 H -0.126404 0.898129 0.486802 0.057 Uiso 1 1 calc R . . . .
C5 C 0.82424(19) 0.58200(14) 0.13989(16) 0.0471(5) Uani 1 1 d . . . . .
H5 H 0.844045 0.511463 0.128269 0.057 Uiso 1 1 calc R . . . .
C7 C 0.8992(2) 0.76242(15) 0.12607(16) 0.0455(5) Uani 1 1 d . . . . .
H7 H 0.968677 0.813174 0.105546 0.055 Uiso 1 1 calc R . . . .
C13 C -0.0628(2) 0.62401(15) 0.43583(16) 0.0488(5) Uani 1 1 d . . . . .
H13 H -0.050170 0.552833 0.423217 0.059 Uiso 1 1 calc R . . . .
C12 C -0.1942(2) 0.65884(17) 0.48045(17) 0.0520(5) Uani 1 1 d . . . . .
H12 H -0.268952 0.609834 0.497603 0.062 Uiso 1 1 calc R . . . .
H4A H 0.222(3) 0.479(2) 0.240(2) 0.111(11) Uiso 1 1 d . . . . .
H4B H 0.152(3) 0.479(2) 0.127(2) 0.104(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C4 1.346(2) . ?
O3 H3 0.8200 . ?
O3 C6 1.357(2) . ?
O1 C1 1.224(2) . ?
O4 H4A 0.94(3) . ?
O4 H4B 0.81(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.3811(19) . ?
N1 C1 1.343(2) . ?
N3 C11 1.329(2) . ?
N3 C12 1.330(2) . ?
N2 C2 1.278(2) . ?
C9 C10 1.377(2) . ?
C9 C1 1.496(2) . ?
C9 C13 1.382(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(2) . ?
C3 C4 1.405(2) . ?
C3 C8 1.390(2) . ?
C3 C2 1.445(2) . ?
C4 C5 1.386(2) . ?
C6 C5 1.381(2) . ?
C6 C7 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.376(2) . ?
C2 H2A 0.9300 . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.376(2) . ?
C12 H12 0.9300 . ?

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 O2 H2 109.5 . . ?
C6 O3 H3 109.5 . . ?
H4A O4 H4B 109(3) . . ?
N2 N1 H1 120.9 . . ?
C1 N1 H1 120.9 . . ?
C1 N1 N2 118.28(15) . . ?
C11 N3 C12 116.87(16) . . ?
C2 N2 N1 117.71(15) . . ?
C10 C9 C1 125.20(16) . . ?
C10 C9 C13 117.54(16) . . ?
C13 C9 C1 117.26(16) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.70(17) . . ?
C11 C10 H10 120.6 . . ?
C4 C3 C2 121.68(16) . . ?
C8 C3 C4 117.89(15) . . ?
C8 C3 C2 120.43(16) . . ?
O2 C4 C3 122.60(15) . . ?
O2 C4 C5 117.27(16) . . ?
C5 C4 C3 120.12(16) . . ?
O3 C6 C5 116.37(16) . . ?
O3 C6 C7 123.22(16) . . ?
C5 C6 C7 120.41(16) . . ?
O1 C1 N1 122.45(17) . . ?
O1 C1 C9 120.45(17) . . ?
N1 C1 C9 117.10(16) . . ?
C3 C8 H8 118.9 . . ?
C7 C8 C3 122.12(17) . . ?
C7 C8 H8 118.9 . . ?
N2 C2 C3 121.01(17) . . ?
N2 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
N3 C11 C10 124.19(18) . . ?
N3 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.33(17) . . ?
C6 C5 H5 119.8 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.11(17) . . ?
C8 C7 H7 120.4 . . ?
C9 C13 H13 120.1 . . ?
C12 C13 C9 119.84(18) . . ?
C12 C13 H13 120.1 . . ?
N3 C12 C13 122.84(18) . . ?
N3 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?

_olex2_date_sample_data_collection 2018-04-25
_olex2_exptl_crystal_mounting_method 'glass needle'
_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_5bH2O
_database_code_depnum_ccdc_archive 'CCDC 1985283'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O4, H2 O'
_chemical_formula_sum            'C14 H14 N2 O5'
_chemical_formula_weight         290.27
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2515(4)
_cell_length_b                   6.7577(2)
_cell_length_c                   13.2137(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.876(2)
_cell_angle_gamma                90
_cell_volume                     1332.72(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2819
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.9540
_cell_measurement_theta_min      2.9580
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.656
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5738
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.995
_diffrn_reflns_theta_max         66.995
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -67.00   1.00    1.00    --  -41.74 -38.00  30.00   48
  2  ω    -82.00 -48.00   1.00    1.00    --  -41.74 -57.00 -30.00   34
  3  ω    -93.00 -21.00   1.00    1.00    --  -41.74 126.00-150.00   72
  4  ω    -52.00 -24.00   1.00    1.00    --  -41.74 -38.00  30.00   28
  5  ω      9.00  70.00   1.00    1.00    --   41.74 -57.00   0.00   61
  6  ω     40.00 139.00   1.00    4.00    --  111.00 -61.00-180.00   99
  7  ω    103.00 154.00   1.00    4.00    --  111.00  30.00-120.00   51
  8  ω    146.00 175.00   1.00    4.00    --  111.00  61.00 -30.00   29
  9  ω     84.00 145.00   1.00    4.00    --  111.00  30.00  90.00   61
 10  ω     50.00 106.00   1.00    4.00    --  111.00 -95.00  60.00   56
 11  ω     88.00 138.00   1.00    4.00    --  111.00  61.00 -30.00   50
 12  ω     49.00 104.00   1.00    4.00    --  111.00 -95.00  90.00   55
 13  ω     51.00  88.00   1.00    4.00    --  111.00 -30.00-120.00   37
 14  ω    101.00 138.00   1.00    4.00    --  111.00 -30.00-120.00   37
 15  ω     93.00 166.00   1.00    4.00    --  111.00  30.00 -60.00   73
 16  ω    141.00 169.00   1.00    4.00    --  111.00  61.00 -60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147410000
_diffrn_orient_matrix_UB_12      0.0292279000
_diffrn_orient_matrix_UB_13      0.1179257000
_diffrn_orient_matrix_UB_21      -0.0698093000
_diffrn_orient_matrix_UB_22      -0.1621522000
_diffrn_orient_matrix_UB_23      0.0057790000
_diffrn_orient_matrix_UB_31      0.0745949000
_diffrn_orient_matrix_UB_32      -0.1574987000
_diffrn_orient_matrix_UB_33      0.0159370000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1991
_reflns_number_total             2347
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²+0.0756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C8(H8), C5(H5), C11(H11), C2(H2A), C14(H14), C1(H1A)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O -0.03889(6) 0.37612(14) 0.85922(7) 0.0503(3) Uani 1 1 d . . . . .
H2 H -0.071043 0.376468 0.801266 0.076 Uiso 1 1 calc R U . . .
O1 O 0.18653(6) 0.37333(14) 0.65862(7) 0.0506(3) Uani 1 1 d . . . . .
H1 H 0.241249 0.373623 0.666047 0.076 Uiso 1 1 calc R U . . .
O4 O 0.83982(6) 0.37224(13) 0.67878(7) 0.0450(3) Uani 1 1 d . . . . .
H4 H 0.847701 0.365830 0.619328 0.067 Uiso 1 1 calc R U . . .
O3 O 0.61276(6) 0.40142(16) 0.86935(7) 0.0533(3) Uani 1 1 d . . . . .
H3 H 0.558123 0.397326 0.862589 0.080 Uiso 1 1 calc R U . . .
N1 N 0.44586(7) 0.37921(13) 0.77066(9) 0.0397(3) Uani 1 1 d . . . . .
O5 O 0.89601(9) 0.37276(17) 0.50605(9) 0.0710(4) Uani 1 1 d G . . . .
H5A H 0.876230 0.459776 0.460653 0.107 Uiso 1 1 d G U . . .
H5B H 0.911276 0.276641 0.471930 0.107 Uiso 1 1 d G U . . .
N2 N 0.35284(7) 0.37609(13) 0.75766(9) 0.0393(3) Uani 1 1 d . . . . .
C4 C 0.16408(8) 0.37382(15) 0.75259(9) 0.0362(3) Uani 1 1 d . . . . .
C9 C 0.56875(8) 0.37317(15) 0.68420(10) 0.0354(3) Uani 1 1 d . . . . .
C3 C 0.23017(8) 0.37381(14) 0.84407(9) 0.0344(3) Uani 1 1 d . . . . .
C7 C 0.11272(8) 0.37308(17) 0.94320(9) 0.0416(3) Uani 1 1 d . . . . .
H7 H 0.095343 0.372354 1.006659 0.050 Uiso 1 1 calc R U . . .
C6 C 0.04872(8) 0.37438(15) 0.85101(10) 0.0379(3) Uani 1 1 d . . . . .
C10 C 0.63449(8) 0.38691(16) 0.77555(10) 0.0371(3) Uani 1 1 d . . . . .
C13 C 0.68675(8) 0.35865(17) 0.58539(9) 0.0401(3) Uani 1 1 d . . . . .
H13 H 0.704154 0.349575 0.522099 0.048 Uiso 1 1 calc R U . . .
C12 C 0.75063(8) 0.37265(15) 0.67761(10) 0.0359(3) Uani 1 1 d . . . . .
C8 C 0.20210(8) 0.37290(16) 0.93847(10) 0.0398(3) Uani 1 1 d . . . . .
H8 H 0.244992 0.372149 0.999714 0.048 Uiso 1 1 calc R U . . .
C5 C 0.07351(8) 0.37426(16) 0.75598(10) 0.0383(3) Uani 1 1 d . . . . .
H5 H 0.030161 0.374465 0.695126 0.046 Uiso 1 1 calc R U . . .
C11 C 0.72510(8) 0.38598(16) 0.77192(10) 0.0386(3) Uani 1 1 d . . . . .
H11 H 0.768300 0.394286 0.832723 0.046 Uiso 1 1 calc R U . . .
C2 C 0.32479(8) 0.37632(15) 0.84263(10) 0.0376(3) Uani 1 1 d . . . . .
H2A H 0.366287 0.378135 0.904977 0.045 Uiso 1 1 calc R U . . .
C14 C 0.59737(8) 0.35861(17) 0.59042(10) 0.0398(3) Uani 1 1 d . . . . .
H14 H 0.554588 0.348545 0.529353 0.048 Uiso 1 1 calc R U . . .
C1 C 0.47383(8) 0.37147(15) 0.68546(11) 0.0382(3) Uani 1 1 d . . . . .
H1A H 0.432341 0.364634 0.623210 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C6 1.3627(14) . ?
O1 H1 0.8200 . ?
O1 C4 1.3543(14) . ?
O4 H4 0.8200 . ?
O4 C12 1.3571(15) . ?
O3 H3 0.8200 . ?
O3 C10 1.3508(15) . ?
N1 N2 1.3938(16) . ?
N1 C1 1.2844(18) . ?
O5 H5A 0.8498 . ?
O5 H5B 0.8500 . ?
N2 C2 1.2811(17) . ?
C4 C3 1.4056(18) . ?
C4 C5 1.3912(16) . ?
C9 C10 1.405(2) . ?
C9 C14 1.3995(18) . ?
C9 C1 1.4512(16) . ?
C3 C8 1.3998(17) . ?
C3 C2 1.4471(16) . ?
C7 H7 0.9300 . ?
C7 C6 1.3955(19) . ?
C7 C8 1.3774(17) . ?
C6 C5 1.3839(17) . ?
C10 C11 1.3926(17) . ?
C13 H13 0.9300 . ?
C13 C12 1.3981(18) . ?
C13 C14 1.3783(17) . ?
C12 C11 1.3829(18) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C2 H2A 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1A 0.9300 . ?

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
C6 O2 H2 109.5 . . ?
C4 O1 H1 109.5 . . ?
C12 O4 H4 109.5 . . ?
C10 O3 H3 109.5 . . ?
C1 N1 N2 113.87(12) . . ?
H5A O5 H5B 104.5 . . ?
C2 N2 N1 114.02(11) . . ?
O1 C4 C3 121.10(11) . . ?
O1 C4 C5 118.00(11) . . ?
C5 C4 C3 120.89(11) . . ?
C10 C9 C1 121.88(12) . . ?
C14 C9 C10 117.90(11) . . ?
C14 C9 C1 120.22(12) . . ?
C4 C3 C2 121.96(11) . . ?
C8 C3 C4 118.01(11) . . ?
C8 C3 C2 120.03(11) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C8 C7 C6 118.78(11) . . ?
O2 C6 C7 116.85(11) . . ?
O2 C6 C5 121.85(11) . . ?
C5 C6 C7 121.29(11) . . ?
O3 C10 C9 121.78(11) . . ?
O3 C10 C11 117.68(11) . . ?
C11 C10 C9 120.53(12) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C14 C13 C12 118.47(11) . . ?
O4 C12 C13 121.80(11) . . ?
O4 C12 C11 117.21(11) . . ?
C11 C12 C13 120.99(11) . . ?
C3 C8 H8 119.1 . . ?
C7 C8 C3 121.83(11) . . ?
C7 C8 H8 119.1 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.19(11) . . ?
C6 C5 H5 120.4 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.79(12) . . ?
C12 C11 H11 120.1 . . ?
N2 C2 C3 121.68(12) . . ?
N2 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C9 C14 H14 118.8 . . ?
C13 C14 C9 122.32(11) . . ?
C13 C14 H14 118.8 . . ?
N1 C1 C9 121.45(12) . . ?
N1 C1 H1A 119.3 . . ?
C9 C1 H1A 119.3 . . ?

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
O2 C6 C5 C4 179.56(9) . . . . ?
O1 C4 C3 C8 -179.55(10) . . . . ?
O1 C4 C3 C2 0.95(15) . . . . ?
O1 C4 C5 C6 179.88(10) . . . . ?
O4 C12 C11 C10 -179.95(9) . . . . ?
O3 C10 C11 C12 -179.59(10) . . . . ?
N1 N2 C2 C3 179.85(8) . . . . ?
N2 N1 C1 C9 -179.98(8) . . . . ?
C4 C3 C8 C7 -0.35(16) . . . . ?
C4 C3 C2 N2 -0.91(15) . . . . ?
C9 C10 C11 C12 0.40(16) . . . . ?
C3 C4 C5 C6 -0.10(16) . . . . ?
C7 C6 C5 C4 -0.32(16) . . . . ?
C6 C7 C8 C3 -0.05(17) . . . . ?
C10 C9 C14 C13 -0.41(16) . . . . ?
C10 C9 C1 N1 -1.17(15) . . . . ?
C13 C12 C11 C10 -0.45(16) . . . . ?
C12 C13 C14 C9 0.37(17) . . . . ?
C8 C3 C2 N2 179.60(10) . . . . ?
C8 C7 C6 O2 -179.49(9) . . . . ?
C8 C7 C6 C5 0.40(17) . . . . ?
C5 C4 C3 C8 0.43(15) . . . . ?
C5 C4 C3 C2 -179.07(9) . . . . ?
C2 C3 C8 C7 179.15(9) . . . . ?
C14 C9 C10 O3 -179.99(10) . . . . ?
C14 C9 C10 C11 0.02(15) . . . . ?
C14 C9 C1 N1 178.08(10) . . . . ?
C14 C13 C12 O4 179.55(9) . . . . ?
C14 C13 C12 C11 0.07(16) . . . . ?
C1 N1 N2 C2 177.53(9) . . . . ?
C1 C9 C10 O3 -0.73(16) . . . . ?
C1 C9 C10 C11 179.28(9) . . . . ?
C1 C9 C14 C13 -179.69(9) . . . . ?

_olex2_exptl_crystal_mounting_method 'glass needle'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.720

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1985277'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3a                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.957 Why?
RESPONSE: The data collection was corrupted. 
;
# Added during the CSD deposition process: Thursday 20 February 2020 09:10 AM
# end Validation Reply Form

_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H13 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.7572(13)
_cell_length_b                   7.6282(5)
_cell_length_c                   13.3499(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2521.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.5900
_cell_measurement_theta_min      4.4130
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7090
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         4.139
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994   19.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432  -57.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega   27.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432   57.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.3432 -120.0000  -16.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -73.00  -38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4994 -179.0000   90.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0117535000
_diffrn_orient_matrix_UB_12      0.0831890000
_diffrn_orient_matrix_UB_13      0.0094398000
_diffrn_orient_matrix_UB_21      -0.0257430000
_diffrn_orient_matrix_UB_22      0.0399585000
_diffrn_orient_matrix_UB_23      -0.0048092000
_diffrn_orient_matrix_UB_31      -0.0045079000
_diffrn_orient_matrix_UB_32      -0.0113609000
_diffrn_orient_matrix_UB_33      0.0520528000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1173
_reflns_number_total             2117
_reflns_odcompleteness_completeness 96.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C6(H6), C8(H8), C14(H14), C13(H13), C12(H12), C11(H11), C7(H7)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.36179(8) 0.5644(3) 0.44719(12) 0.0618(6) Uani 1 1 d . . . . .
O2 O 0.48813(8) 0.7927(3) 0.29496(13) 0.0737(7) Uani 1 1 d . . . . .
H2 H 0.469567 0.739955 0.335939 0.111 Uiso 1 1 calc GR . . . .
O3 O 0.56318(9) 0.9240(3) 0.17753(12) 0.0759(7) Uani 1 1 d . . . . .
H3 H 0.588487 0.969351 0.147528 0.114 Uiso 1 1 calc GR . . . .
N2 N 0.45964(9) 0.6982(3) 0.48177(15) 0.0459(6) Uani 1 1 d . . . . .
N1 N 0.42674(9) 0.6372(3) 0.55732(15) 0.0469(6) Uani 1 1 d . . . . .
H1 H 0.437961 0.637899 0.618285 0.056 Uiso 1 1 calc R . . . .
N3 N 0.27711(10) 0.3691(3) 0.51270(16) 0.0686(8) Uani 1 1 d . . . . .
H3A H 0.244831 0.407535 0.501307 0.082 Uiso 1 1 d GR . . . .
H3B H 0.298561 0.412858 0.468098 0.082 Uiso 1 1 d GR . . . .
C3 C 0.54444(11) 0.8320(3) 0.44148(18) 0.0402(7) Uani 1 1 d . . . . .
C9 C 0.34242(10) 0.5243(3) 0.62114(18) 0.0408(7) Uani 1 1 d . . . . .
C1 C 0.37683(12) 0.5761(4) 0.53573(19) 0.0437(7) Uani 1 1 d . . . . .
C2 C 0.50443(12) 0.7638(3) 0.51106(19) 0.0449(7) Uani 1 1 d . . . . .
H2A H 0.511720 0.767958 0.579358 0.054 Uiso 1 1 calc R . . . .
C10 C 0.29556(11) 0.4243(4) 0.60559(18) 0.0458(7) Uani 1 1 d . . . . .
C5 C 0.57546(12) 0.9125(4) 0.27768(19) 0.0462(8) Uani 1 1 d . . . . .
C4 C 0.53534(11) 0.8442(3) 0.3390(2) 0.0469(7) Uani 1 1 d . . . . .
C6 C 0.62396(11) 0.9643(4) 0.3168(2) 0.0497(8) Uani 1 1 d . . . . .
H6 H 0.650740 1.007570 0.274648 0.060 Uiso 1 1 calc R . . . .
C8 C 0.59366(12) 0.8873(4) 0.47963(19) 0.0504(8) Uani 1 1 d . . . . .
H8 H 0.599913 0.879930 0.548192 0.061 Uiso 1 1 calc R . . . .
C14 C 0.35516(12) 0.5751(4) 0.71880(18) 0.0496(8) Uani 1 1 d . . . . .
H14 H 0.385726 0.643343 0.729776 0.059 Uiso 1 1 calc R . . . .
C13 C 0.32369(12) 0.5270(4) 0.7993(2) 0.0567(9) Uani 1 1 d . . . . .
H13 H 0.332633 0.563358 0.863724 0.068 Uiso 1 1 calc R . . . .
C12 C 0.27876(13) 0.4241(4) 0.7832(2) 0.0584(9) Uani 1 1 d . . . . .
H12 H 0.257629 0.389262 0.837201 0.070 Uiso 1 1 calc R . . . .
C11 C 0.26501(12) 0.3730(4) 0.6888(2) 0.0543(8) Uani 1 1 d . . . . .
H11 H 0.234727 0.302768 0.679479 0.065 Uiso 1 1 calc R . . . .
C7 C 0.63334(12) 0.9527(4) 0.4184(2) 0.0552(8) Uani 1 1 d . . . . .
H7 H 0.666204 0.988818 0.445077 0.066 Uiso 1 1 calc R . . . .


_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 C1 1.243(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.366(3) . ?
O3 H3 0.8200 . ?
O3 C5 1.374(3) . ?
N2 N1 1.378(3) . ?
N2 C2 1.278(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.351(3) . ?
N3 H3A 0.8648 . ?
N3 H3B 0.8650 . ?
N3 C10 1.387(3) . ?
C3 C2 1.454(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.386(3) . ?
C9 C1 1.477(3) . ?
C9 C10 1.404(3) . ?
C9 C14 1.396(3) . ?
C2 H2A 0.9300 . ?
C10 C11 1.400(3) . ?
C5 C4 1.389(3) . ?
C5 C6 1.368(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.372(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.362(3) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?

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 O2 H2 109.5 . . ?
C5 O3 H3 109.5 . . ?
C2 N2 N1 114.9(2) . . ?
N2 N1 H1 120.0 . . ?
C1 N1 N2 120.1(2) . . ?
C1 N1 H1 120.0 . . ?
H3A N3 H3B 108.4 . . ?
C10 N3 H3A 111.0 . . ?
C10 N3 H3B 107.2 . . ?
C4 C3 C2 122.8(2) . . ?
C8 C3 C2 118.2(2) . . ?
C8 C3 C4 118.9(2) . . ?
C10 C9 C1 120.5(2) . . ?
C14 C9 C1 121.1(3) . . ?
C14 C9 C10 118.4(2) . . ?
O1 C1 N1 120.1(2) . . ?
O1 C1 C9 122.8(3) . . ?
N1 C1 C9 117.0(2) . . ?
N2 C2 C3 122.4(2) . . ?
N2 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
N3 C10 C9 124.7(2) . . ?
N3 C10 C11 116.5(3) . . ?
C11 C10 C9 118.8(2) . . ?
O3 C5 C4 116.1(2) . . ?
C6 C5 O3 123.2(2) . . ?
C6 C5 C4 120.8(2) . . ?
O2 C4 C3 122.9(2) . . ?
O2 C4 C5 117.8(2) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C14 C13 H13 120.5 . . ?
C14 C13 C12 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?

_olex2_exptl_crystal_mounting_method 'glass needle'
_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_4bMeOH
_database_code_depnum_ccdc_archive 'CCDC 1985281'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_4bMeOH              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.951 Why?
RESPONSE: The data collection was corrupted. 
;
# Added during the CSD deposition process: Thursday 20 February 2020 09:10 AM
# end Validation Reply Form

_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
ivica.djilovic@chem.pmf.hr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O3, C H4 O'
_chemical_formula_sum            'C15 H17 N3 O4'
_chemical_formula_weight         303.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N5 O4 Mo'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.788(2)
_cell_length_b                   8.4727(10)
_cell_length_c                   18.273(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.86(2)
_cell_angle_gamma                90
_cell_volume                     1471.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    481
_cell_measurement_temperature    150
_cell_measurement_theta_max      20.0340
_cell_measurement_theta_min      4.5730
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 'cold methanol'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.1727
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7864
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         4.246
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   37.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1869  -57.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   88.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1869   57.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   62.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1869 -105.0000  174.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   92.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       22.1869  179.0000  120.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0517247000
_diffrn_orient_matrix_UB_12      -0.0569388000
_diffrn_orient_matrix_UB_13      -0.0026933000
_diffrn_orient_matrix_UB_21      -0.0354155000
_diffrn_orient_matrix_UB_22      -0.0568733000
_diffrn_orient_matrix_UB_23      0.0171994000
_diffrn_orient_matrix_UB_31      -0.0406529000
_diffrn_orient_matrix_UB_32      -0.0228708000
_diffrn_orient_matrix_UB_33      -0.0359692000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1205
_reflns_number_total             2611
_reflns_odcompleteness_completeness 92.01

_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1854
_refine_ls_R_factor_gt           0.0815
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1578
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.4996(3) 0.6247(3) 0.29145(18) 0.0347(9) Uani 1 1 d . . . . .
H2 H 0.472010 0.565802 0.321995 0.052 Uiso 1 1 calc GR . . . .
O1 O 0.2537(3) 0.3903(3) 0.40753(17) 0.0345(9) Uani 1 1 d . . . . .
O3 O 0.9102(3) 0.7155(3) 0.19955(19) 0.0384(9) Uani 1 1 d . . . . .
H3 H 0.855290 0.775929 0.169851 0.058 Uiso 1 1 calc GR . . . .
O4 O 0.2712(4) 0.7215(3) 0.42300(18) 0.0461(11) Uani 1 1 d . . . . .
H4 H 0.251192 0.628519 0.408400 0.069 Uiso 1 1 calc GR . . . .
N2 N 0.5259(4) 0.4188(4) 0.4038(2) 0.0299(10) Uani 1 1 d . . . . .
N1 N 0.4825(4) 0.3285(4) 0.4575(2) 0.0344(11) Uani 1 1 d . . . . .
H1 H 0.545520 0.280602 0.492979 0.041 Uiso 1 1 calc R . . . .
N3 N 0.1865(5) -0.0813(4) 0.6720(2) 0.0484(13) Uani 1 1 d . . . . .
H3A H 0.218971 -0.040713 0.716059 0.058 Uiso 1 1 d GR . . . .
H3B H 0.095957 -0.085584 0.662967 0.058 Uiso 1 1 d GR . . . .
C4 C 0.6406(5) 0.5998(5) 0.2973(3) 0.0285(12) Uani 1 1 d . . . . .
C1 C 0.3458(6) 0.3139(5) 0.4556(3) 0.0303(12) Uani 1 1 d . . . . .
C3 C 0.7179(5) 0.4965(5) 0.3525(3) 0.0271(12) Uani 1 1 d . . . . .
C9 C 0.3049(5) 0.2076(5) 0.5109(3) 0.0265(12) Uani 1 1 d . . . . .
C2 C 0.6576(5) 0.4107(5) 0.4056(3) 0.0321(13) Uani 1 1 d . . . . .
H2A H 0.717029 0.346801 0.442671 0.038 Uiso 1 1 calc R . . . .
C6 C 0.8418(6) 0.6514(5) 0.2494(3) 0.0298(12) Uani 1 1 d . . . . .
C12 C 0.2233(5) 0.0132(5) 0.6179(3) 0.0354(13) Uani 1 1 d . . . . .
C5 C 0.7016(5) 0.6775(5) 0.2467(3) 0.0284(12) Uani 1 1 d . . . . .
H5 H 0.647794 0.747986 0.210624 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9239(5) 0.5508(4) 0.3039(3) 0.0333(13) Uani 1 1 d . . . . .
H7 H 1.020596 0.533477 0.305924 0.040 Uiso 1 1 calc R . . . .
C8 C 0.8590(5) 0.4776(5) 0.3546(3) 0.0342(13) Uani 1 1 d . . . . .
H8 H 0.914046 0.411671 0.392449 0.041 Uiso 1 1 calc R . . . .
C10 C 0.4034(5) 0.1089(5) 0.5591(3) 0.0351(13) Uani 1 1 d . . . . .
H10 H 0.498488 0.106814 0.555230 0.042 Uiso 1 1 calc R . . . .
C11 C 0.3615(5) 0.0152(5) 0.6118(3) 0.0359(13) Uani 1 1 d . . . . .
H11 H 0.429092 -0.049100 0.644563 0.043 Uiso 1 1 calc R . . . .
C14 C 0.1672(6) 0.2035(5) 0.5170(3) 0.0394(14) Uani 1 1 d . . . . .
H14 H 0.099509 0.267903 0.484401 0.047 Uiso 1 1 calc R . . . .
C15 C 0.2273(6) 0.8275(5) 0.3607(3) 0.0451(15) Uani 1 1 d . . . . .
H15A H 0.290116 0.816859 0.326575 0.068 Uiso 1 1 calc GR . . . .
H15B H 0.230918 0.936240 0.379460 0.068 Uiso 1 1 calc GR . . . .
H15C H 0.130766 0.802091 0.333615 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.1243(6) 0.1092(5) 0.5689(3) 0.0405(14) Uani 1 1 d . . . . .
H13 H 0.028576 0.108986 0.571470 0.049 Uiso 1 1 calc R . . . .


_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
O2 H2 0.8400 . ?
O2 C4 1.375(5) . ?
O1 C1 1.274(5) . ?
O3 H3 0.8400 . ?
O3 C6 1.366(5) . ?
O4 H4 0.8400 . ?
O4 C15 1.432(5) . ?
N2 N1 1.388(5) . ?
N2 C2 1.284(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.337(6) . ?
N3 H3A 0.8628 . ?
N3 H3B 0.8623 . ?
N3 C12 1.385(5) . ?
C4 C3 1.410(6) . ?
C4 C5 1.382(6) . ?
C1 C9 1.479(6) . ?
C3 C2 1.446(6) . ?
C3 C8 1.381(6) . ?
C9 C10 1.413(6) . ?
C9 C14 1.379(6) . ?
C2 H2A 0.9500 . ?
C6 C5 1.379(6) . ?
C6 C7 1.407(6) . ?
C12 C11 1.384(6) . ?
C12 C13 1.410(6) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.389(6) . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.385(6) . ?
C11 H11 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.379(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 H13 0.9500 . ?

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 O2 H2 109.5 . . ?
C6 O3 H3 109.5 . . ?
C15 O4 H4 109.5 . . ?
C2 N2 N1 115.4(4) . . ?
N2 N1 H1 119.8 . . ?
C1 N1 N2 120.5(4) . . ?
C1 N1 H1 119.8 . . ?
H3A N3 H3B 109.1 . . ?
C12 N3 H3A 109.6 . . ?
C12 N3 H3B 108.6 . . ?
O2 C4 C3 120.5(4) . . ?
O2 C4 C5 117.5(4) . . ?
C5 C4 C3 122.0(5) . . ?
O1 C1 N1 120.6(4) . . ?
O1 C1 C9 121.2(5) . . ?
N1 C1 C9 118.2(4) . . ?
C4 C3 C2 123.8(5) . . ?
C8 C3 C4 116.9(4) . . ?
C8 C3 C2 119.3(4) . . ?
C10 C9 C1 122.0(5) . . ?
C14 C9 C1 120.0(4) . . ?
C14 C9 C10 118.0(4) . . ?
N2 C2 C3 121.7(4) . . ?
N2 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
O3 C6 C5 123.7(4) . . ?
O3 C6 C7 115.2(5) . . ?
C5 C6 C7 121.1(5) . . ?
N3 C12 C13 122.1(5) . . ?
C11 C12 N3 119.4(5) . . ?
C11 C12 C13 118.5(5) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.9(5) . . ?
C8 C7 H7 121.1 . . ?
C3 C8 C7 122.9(4) . . ?
C3 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C9 C14 H14 118.9 . . ?
C13 C14 C9 122.3(5) . . ?
C13 C14 H14 118.9 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.1 . . ?

_olex2_date_sample_data_collection 2019-02-14
_olex2_exptl_crystal_mounting_method loop
_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_4c
_database_code_depnum_ccdc_archive 'CCDC 1985282'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N3 O5'
_chemical_formula_sum            'C21 H17 N3 O5'
_chemical_formula_weight         391.38
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   39.4655(16)
_cell_length_b                   5.4865(3)
_cell_length_c                   16.4148(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.157(4)
_cell_angle_gamma                90
_cell_volume                     3539.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2722
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.7960
_cell_measurement_theta_min      4.5100
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8028
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.994
_diffrn_reflns_theta_max         66.994
_diffrn_reflns_theta_min         4.500
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  62.00   1.00   35.00    --   41.74 -38.00-150.00   95
  2  ω     26.00 110.00   1.00   35.00    --   41.74  38.00-180.00   84
  3  ω     21.00 106.00   1.00   35.00    --   41.74  57.00   0.00   85
  4  ω     38.00 116.00   1.00  140.00    --  111.00 -45.00 120.00   78
  5  ω     90.00 178.00   1.00  140.00    --  111.00  30.00 -60.00   88
  6  ω    135.00 177.00   1.00  140.00    --  111.00  15.00-150.00   42
  7  ω     36.00  84.00   1.00  140.00    --  111.00-112.00  60.00   48
  8  ω    117.00 144.00   1.00  140.00    --  111.00 -77.00 150.00   27
  9  ω     97.00 178.00   1.00  140.00    --  111.00  38.00-102.00   81
 10  ω     30.00 110.00   1.00  140.00    --  111.00 -95.00  90.00   80
 11  ω     58.00  88.00   1.00  140.00    --  111.00  15.00-150.00   30
 12  ω     95.00 122.00   1.00  140.00    --  111.00  15.00-150.00   27
 13  ω     94.00 140.00   1.00  140.00    --  111.00 -61.00-120.00   46
 14  ω     98.00 161.00   1.00  140.00    --  111.00  30.00   0.00   63
 15  ω    112.00 142.00   1.00  140.00    --  111.00 178.00  30.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011077000
_diffrn_orient_matrix_UB_12      0.1367226000
_diffrn_orient_matrix_UB_13      0.0817130000
_diffrn_orient_matrix_UB_21      0.0391794000
_diffrn_orient_matrix_UB_22      -0.0014616000
_diffrn_orient_matrix_UB_23      0.0117440000
_diffrn_orient_matrix_UB_31      0.0009059000
_diffrn_orient_matrix_UB_32      0.2452081000
_diffrn_orient_matrix_UB_33      -0.0454001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2467
_reflns_number_total             3157
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.054
_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)+(0.0778P)²+0.7431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C2(H2A), C6(H6), C11(H11), C10(H10), C14(H14), C7(H7),
 C8(H8), C13(H13), C19(H19), C21(H21), C20(H20)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4), O5(H5)
;
_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
O2 O 0.47189(3) 0.2529(3) 0.52102(9) 0.0604(4) Uani 1 1 d . . . . .
H2 H 0.489547 0.239531 0.551060 0.091 Uiso 1 1 calc R U . . .
O3 O 0.40995(4) 0.3267(3) 0.44302(9) 0.0672(4) Uani 1 1 d . . . . .
H3 H 0.425029 0.231284 0.433113 0.101 Uiso 1 1 calc R U . . .
O4 O 0.74199(4) 0.5524(3) 0.93220(10) 0.0712(4) Uani 1 1 d . . . . .
H4 H 0.724567 0.507580 0.905408 0.107 Uiso 1 1 calc R U . . .
O1 O 0.55753(4) -0.0074(3) 0.66104(10) 0.0749(5) Uani 1 1 d . . . . .
O5 O 0.80408(4) 0.6279(3) 1.01547(11) 0.0754(5) Uani 1 1 d . . . . .
H5 H 0.786198 0.703287 1.016794 0.113 Uiso 1 1 calc R U . . .
N3 N 0.70307(4) 0.2795(3) 0.83969(10) 0.0547(4) Uani 1 1 d . . . . .
N1 N 0.54936(4) 0.3928(4) 0.68356(10) 0.0604(4) Uani 1 1 d . . . . .
H1 H 0.557360 0.525123 0.705845 0.072 Uiso 1 1 calc R U . . .
N2 N 0.51714(4) 0.3911(4) 0.64348(9) 0.0578(4) Uani 1 1 d . . . . .
C4 C 0.45416(5) 0.4490(4) 0.54432(11) 0.0514(4) Uani 1 1 d . . . . .
C5 C 0.42210(5) 0.4843(4) 0.50287(11) 0.0553(5) Uani 1 1 d . . . . .
C9 C 0.60356(5) 0.2142(4) 0.72883(11) 0.0543(5) Uani 1 1 d . . . . .
C1 C 0.56840(5) 0.1886(4) 0.68805(11) 0.0574(5) Uani 1 1 d . . . . .
C3 C 0.46643(5) 0.6153(4) 0.60433(11) 0.0541(5) Uani 1 1 d . . . . .
C12 C 0.66997(5) 0.2450(4) 0.80271(11) 0.0523(4) Uani 1 1 d . . . . .
C15 C 0.72904(5) 0.1385(4) 0.83132(12) 0.0588(5) Uani 1 1 d . . . . .
H15 H 0.725968 -0.001055 0.799365 0.071 Uiso 1 1 calc R U . . .
C16 C 0.76205(5) 0.1918(4) 0.86969(12) 0.0564(5) Uani 1 1 d . . . . .
C17 C 0.76690(5) 0.3979(4) 0.92139(12) 0.0557(5) Uani 1 1 d . . . . .
C2 C 0.50024(5) 0.5895(4) 0.64643(11) 0.0569(5) Uani 1 1 d . . . . .
H2A H 0.509830 0.720394 0.676246 0.068 Uiso 1 1 calc R U . . .
C6 C 0.40243(5) 0.6824(4) 0.52136(13) 0.0624(5) Uani 1 1 d . . . . .
H6 H 0.381068 0.704881 0.493584 0.075 Uiso 1 1 calc R U . . .
C18 C 0.79931(5) 0.4387(4) 0.96261(12) 0.0589(5) Uani 1 1 d . . . . .
C11 C 0.64565(5) 0.4130(4) 0.82083(12) 0.0614(5) Uani 1 1 d . . . . .
H11 H 0.651467 0.537134 0.858060 0.074 Uiso 1 1 calc R U . . .
C10 C 0.61294(5) 0.3985(4) 0.78444(13) 0.0622(5) Uani 1 1 d . . . . .
H10 H 0.596908 0.513383 0.797170 0.075 Uiso 1 1 calc R U . . .
C14 C 0.62787(5) 0.0438(4) 0.71239(13) 0.0636(5) Uani 1 1 d . . . . .
H14 H 0.621862 -0.082881 0.676300 0.076 Uiso 1 1 calc R U . . .
C7 C 0.41444(6) 0.8473(4) 0.58100(14) 0.0660(5) Uani 1 1 d . . . . .
H7 H 0.401116 0.979460 0.593640 0.079 Uiso 1 1 calc R U . . .
C8 C 0.44614(6) 0.8146(4) 0.62143(13) 0.0628(5) Uani 1 1 d . . . . .
H8 H 0.454247 0.927024 0.660875 0.075 Uiso 1 1 calc R U . . .
C13 C 0.66071(5) 0.0570(4) 0.74810(14) 0.0644(5) Uani 1 1 d . . . . .
H13 H 0.676663 -0.059053 0.735868 0.077 Uiso 1 1 calc R U . . .
C19 C 0.82578(5) 0.2841(5) 0.95018(14) 0.0658(6) Uani 1 1 d . . . . .
H19 H 0.847110 0.312803 0.977361 0.079 Uiso 1 1 calc R U . . .
C21 C 0.78999(6) 0.0378(5) 0.85889(14) 0.0672(6) Uani 1 1 d . . . . .
H21 H 0.787001 -0.097627 0.824919 0.081 Uiso 1 1 calc R U . . .
C20 C 0.82121(6) 0.0854(5) 0.89762(14) 0.0710(6) Uani 1 1 d . . . . .
H20 H 0.839541 -0.014962 0.888976 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C4 1.357(3) . ?
O3 H3 0.8200 . ?
O3 C5 1.363(3) . ?
O4 H4 0.8200 . ?
O4 C17 1.322(3) . ?
O1 C1 1.226(3) . ?
O5 H5 0.8200 . ?
O5 C18 1.355(3) . ?
N3 C12 1.403(2) . ?
N3 C15 1.301(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.378(2) . ?
N1 C1 1.347(3) . ?
N2 C2 1.280(3) . ?
C4 C5 1.395(3) . ?
C4 C3 1.397(3) . ?
C5 C6 1.385(3) . ?
C9 C1 1.492(3) . ?
C9 C10 1.390(3) . ?
C9 C14 1.383(3) . ?
C3 C2 1.453(3) . ?
C3 C8 1.399(3) . ?
C12 C11 1.382(3) . ?
C12 C13 1.394(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.426(3) . ?
C16 C17 1.417(3) . ?
C16 C21 1.413(3) . ?
C17 C18 1.410(3) . ?
C2 H2A 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.385(3) . ?
C18 C19 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(3) . ?
C10 H10 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.360(3) . ?
C20 H20 0.9300 . ?

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 O2 H2 109.5 . . ?
C5 O3 H3 109.5 . . ?
C17 O4 H4 109.5 . . ?
C18 O5 H5 109.5 . . ?
C15 N3 C12 125.85(18) . . ?
N2 N1 H1 119.8 . . ?
C1 N1 H1 119.8 . . ?
C1 N1 N2 120.42(17) . . ?
C2 N2 N1 115.94(18) . . ?
O2 C4 C5 116.15(18) . . ?
O2 C4 C3 124.16(17) . . ?
C5 C4 C3 119.7(2) . . ?
O3 C5 C4 120.6(2) . . ?
O3 C5 C6 119.20(18) . . ?
C6 C5 C4 120.24(19) . . ?
C10 C9 C1 123.02(19) . . ?
C14 C9 C1 118.84(18) . . ?
C14 C9 C10 118.12(18) . . ?
O1 C1 N1 122.31(18) . . ?
O1 C1 C9 121.7(2) . . ?
N1 C1 C9 115.97(18) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 C8 118.92(18) . . ?
C8 C3 C2 119.89(19) . . ?
C11 C12 N3 117.04(17) . . ?
C11 C12 C13 119.00(18) . . ?
C13 C12 N3 123.94(19) . . ?
N3 C15 H15 119.0 . . ?
N3 C15 C16 121.93(19) . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 119.81(19) . . ?
C21 C16 C15 121.0(2) . . ?
C21 C16 C17 119.19(19) . . ?
O4 C17 C16 122.03(17) . . ?
O4 C17 C18 119.15(19) . . ?
C18 C17 C16 118.81(19) . . ?
N2 C2 C3 121.60(18) . . ?
N2 C2 H2A 119.2 . . ?
C3 C2 H2A 119.2 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.31(19) . . ?
C7 C6 H6 119.8 . . ?
O5 C18 C17 119.77(19) . . ?
O5 C18 C19 120.26(19) . . ?
C19 C18 C17 120.0(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.73(19) . . ?
C10 C11 H11 119.6 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.64(19) . . ?
C13 C14 H14 119.2 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.15(19) . . ?
C20 C19 H19 119.4 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C5 O3 0.4(3) . . . . ?
O2 C4 C5 C6 -178.71(17) . . . . ?
O2 C4 C3 C2 0.7(3) . . . . ?
O2 C4 C3 C8 178.17(17) . . . . ?
O3 C5 C6 C7 -178.97(19) . . . . ?
O4 C17 C18 O5 3.1(3) . . . . ?
O4 C17 C18 C19 -178.0(2) . . . . ?
O5 C18 C19 C20 178.5(2) . . . . ?
N3 C12 C11 C10 177.2(2) . . . . ?
N3 C12 C13 C14 -177.4(2) . . . . ?
N3 C15 C16 C17 2.7(3) . . . . ?
N3 C15 C16 C21 -179.2(2) . . . . ?
N1 N2 C2 C3 177.77(16) . . . . ?
N2 N1 C1 O1 -3.9(3) . . . . ?
N2 N1 C1 C9 176.76(16) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C4 C3 C2 N2 -14.9(3) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C5 C4 C3 C2 -177.54(16) . . . . ?
C5 C4 C3 C8 -0.1(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C9 C14 C13 C12 0.4(4) . . . . ?
C1 N1 N2 C2 176.11(17) . . . . ?
C1 C9 C10 C11 179.5(2) . . . . ?
C1 C9 C14 C13 -179.9(2) . . . . ?
C3 C4 C5 O3 178.72(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C12 N3 C15 C16 178.30(19) . . . . ?
C12 C11 C10 C9 0.2(4) . . . . ?
C15 N3 C12 C11 178.6(2) . . . . ?
C15 N3 C12 C13 -3.0(3) . . . . ?
C15 C16 C17 O4 -3.7(3) . . . . ?
C15 C16 C17 C18 176.19(18) . . . . ?
C15 C16 C21 C20 -178.0(2) . . . . ?
C16 C17 C18 O5 -176.74(19) . . . . ?
C16 C17 C18 C19 2.1(3) . . . . ?
C16 C21 C20 C19 1.6(4) . . . . ?
C17 C16 C21 C20 0.2(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C2 C3 C8 C7 178.23(19) . . . . ?
C6 C7 C8 C3 -0.9(3) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C10 C9 C1 O1 -156.3(2) . . . . ?
C10 C9 C1 N1 23.1(3) . . . . ?
C10 C9 C14 C13 -1.5(4) . . . . ?
C14 C9 C1 O1 22.0(3) . . . . ?
C14 C9 C1 N1 -158.59(19) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C3 C2 N2 167.59(18) . . . . ?
C13 C12 C11 C10 -1.3(3) . . . . ?
C21 C16 C17 O4 178.1(2) . . . . ?
C21 C16 C17 C18 -2.0(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'glass needle'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.818
_oxdiff_exptl_absorpt_empirical_full_min 0.488
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1985278'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
loop_
_audit_author_email
ivica.djilovic@chem.pmf.hr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.5511(6)
_cell_length_b                   22.351(3)
_cell_length_c                   9.0707(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.757(11)
_cell_angle_gamma                90
_cell_volume                     1316.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    775
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.2340
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method acetonitrile
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5134
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         4.164
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542   57.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega   81.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.6542  179.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -82.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104  -19.0000 -120.0000 116

#__ type_ start__ end____ width___ exp.time_
  4 omega -110.00  -75.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.3104 -179.0000 -150.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0047893000
_diffrn_orient_matrix_UB_12      -0.0105266000
_diffrn_orient_matrix_UB_13      -0.0742100000
_diffrn_orient_matrix_UB_21      -0.0293374000
_diffrn_orient_matrix_UB_22      0.0289709000
_diffrn_orient_matrix_UB_23      -0.0270320000
_diffrn_orient_matrix_UB_31      0.1050674000
_diffrn_orient_matrix_UB_32      0.0075417000
_diffrn_orient_matrix_UB_33      0.0001496000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1418
_reflns_number_total             2427
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.010
_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)+(0.0809P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1809
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C2(H2A), C7(H7), C8(H8), C14(H14), C13(H13), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.6539(3) 0.11863(8) 0.2311(2) 0.0589(6) Uani 1 1 d . . . . .
H3 H 0.547067 0.100297 0.203881 0.088 Uiso 1 1 calc GR . . . .
O2 O 0.8801(2) 0.30471(9) 0.4295(2) 0.0659(6) Uani 1 1 d . . . . .
H2 H 0.840174 0.333842 0.472528 0.099 Uiso 1 1 calc GR . . . .
O1 O 0.8660(2) 0.46125(9) 0.6367(3) 0.0714(7) Uani 1 1 d . . . . .
N2 N 0.6164(3) 0.37050(10) 0.5554(2) 0.0471(6) Uani 1 1 d . . . . .
N1 N 0.5507(3) 0.42132(10) 0.6195(2) 0.0496(6) Uani 1 1 d . . . . .
H1 H 0.423925 0.424676 0.633560 0.060 Uiso 1 1 calc R . . . .
C3 C 0.5318(3) 0.27453(12) 0.4503(3) 0.0433(6) Uani 1 1 d . . . . .
C6 C 0.6101(3) 0.16892(12) 0.3054(3) 0.0457(7) Uani 1 1 d . . . . .
C1 C 0.6842(4) 0.46586(12) 0.6605(3) 0.0478(7) Uani 1 1 d . . . . .
N3 N 0.8886(4) 0.58116(13) 0.6702(3) 0.0807(9) Uani 1 1 d . . . . .
H3A H 0.894883 0.552164 0.608580 0.097 Uiso 1 1 d GR . . . .
H3B H 0.874641 0.614454 0.622271 0.097 Uiso 1 1 d GR . . . .
C4 C 0.7256(3) 0.26384(12) 0.4048(3) 0.0460(7) Uani 1 1 d . . . . .
C9 C 0.6080(4) 0.51853(12) 0.7334(3) 0.0470(7) Uani 1 1 d . . . . .
C5 C 0.7623(4) 0.21160(12) 0.3329(3) 0.0482(7) Uani 1 1 d . . . . .
H5 H 0.890499 0.205018 0.302709 0.058 Uiso 1 1 calc R . . . .
C2 C 0.4813(4) 0.32990(12) 0.5190(3) 0.0486(7) Uani 1 1 d . . . . .
H2A H 0.346719 0.336230 0.537388 0.058 Uiso 1 1 calc R . . . .
C7 C 0.4205(3) 0.17740(13) 0.3532(3) 0.0506(7) Uani 1 1 d . . . . .
H7 H 0.319717 0.147891 0.338555 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3837(3) 0.22996(13) 0.4223(3) 0.0534(8) Uani 1 1 d . . . . .
H8 H 0.254609 0.236104 0.451537 0.064 Uiso 1 1 calc R . . . .
C10 C 0.7178(4) 0.57258(13) 0.7408(3) 0.0568(8) Uani 1 1 d . . . . .
C14 C 0.4299(4) 0.51565(14) 0.8024(3) 0.0624(8) Uani 1 1 d . . . . .
H14 H 0.356198 0.479998 0.798258 0.075 Uiso 1 1 calc R . . . .
C13 C 0.3602(5) 0.56331(17) 0.8757(4) 0.0770(10) Uani 1 1 d . . . . .
H13 H 0.240760 0.560289 0.920194 0.092 Uiso 1 1 calc R . . . .
C11 C 0.6459(5) 0.62068(14) 0.8190(4) 0.0708(9) Uani 1 1 d . . . . .
H11 H 0.719450 0.656379 0.827532 0.085 Uiso 1 1 calc R . . . .
C12 C 0.4702(6) 0.61575(17) 0.8824(4) 0.0809(10) Uani 1 1 d . . . . .
H12 H 0.423523 0.648559 0.931334 0.097 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3 0.8200 . ?
O3 C6 1.361(3) . ?
O2 H2 0.8200 . ?
O2 C4 1.360(3) . ?
O1 C1 1.243(3) . ?
N2 N1 1.372(3) . ?
N2 C2 1.280(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.344(3) . ?
C3 C4 1.408(3) . ?
C3 C2 1.444(4) . ?
C3 C8 1.390(3) . ?
C6 C5 1.378(3) . ?
C6 C7 1.383(3) . ?
C1 C9 1.470(4) . ?
N3 H3A 0.8602 . ?
N3 H3B 0.8604 . ?
N3 C10 1.376(4) . ?
C4 C5 1.374(3) . ?
C9 C10 1.403(4) . ?
C9 C14 1.398(4) . ?
C5 H5 0.9300 . ?
C2 H2A 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.368(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.404(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(5) . ?
C12 H12 0.9300 . ?

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
C6 O3 H3 109.5 . . ?
C4 O2 H2 109.5 . . ?
C2 N2 N1 116.8(2) . . ?
N2 N1 H1 120.0 . . ?
C1 N1 N2 120.0(2) . . ?
C1 N1 H1 120.0 . . ?
C4 C3 C2 122.7(2) . . ?
C8 C3 C4 117.4(2) . . ?
C8 C3 C2 119.9(2) . . ?
O3 C6 C5 117.8(2) . . ?
O3 C6 C7 121.8(2) . . ?
C5 C6 C7 120.4(2) . . ?
O1 C1 N1 119.6(2) . . ?
O1 C1 C9 122.4(2) . . ?
N1 C1 C9 118.0(2) . . ?
H3A N3 H3B 109.6 . . ?
C10 N3 H3A 108.1 . . ?
C10 N3 H3B 108.5 . . ?
O2 C4 C3 121.3(2) . . ?
O2 C4 C5 118.4(2) . . ?
C5 C4 C3 120.4(2) . . ?
C10 C9 C1 120.5(2) . . ?
C14 C9 C1 121.3(3) . . ?
C14 C9 C10 118.1(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
N2 C2 C3 121.9(2) . . ?
N2 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
C6 C7 H7 120.6 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C3 C8 H8 118.7 . . ?
C7 C8 C3 122.5(2) . . ?
C7 C8 H8 118.7 . . ?
N3 C10 C9 122.8(3) . . ?
N3 C10 C11 118.5(3) . . ?
C9 C10 C11 118.6(3) . . ?
C9 C14 H14 118.8 . . ?
C13 C14 C9 122.4(3) . . ?
C13 C14 H14 118.8 . . ?
C14 C13 H13 120.7 . . ?
C14 C13 C12 118.6(3) . . ?
C12 C13 H13 120.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?

_olex2_date_sample_data_collection 2018-05-29
_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_4a
_database_code_depnum_ccdc_archive 'CCDC 1985280'
loop_
_audit_author_name
_audit_author_address
'Dilovic I.'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O3'
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   24.7095(14)
_cell_length_b                   10.1996(7)
_cell_length_c                   20.7620(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.252(5)
_cell_angle_gamma                90
_cell_volume                     5164.5(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.4170
_cell_measurement_theta_min      4.4520
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2272
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21864
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         4.194
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667   19.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega   47.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.8104  179.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       28.8104  179.0000    0.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega  -77.00  -26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667  -57.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega  -92.00  -51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.4667 -179.0000   90.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0179852000
_diffrn_orient_matrix_UB_12      0.0546384000
_diffrn_orient_matrix_UB_13      -0.0040014000
_diffrn_orient_matrix_UB_21      -0.0055268000
_diffrn_orient_matrix_UB_22      -0.0089408000
_diffrn_orient_matrix_UB_23      0.0321980000
_diffrn_orient_matrix_UB_31      0.0221482000
_diffrn_orient_matrix_UB_32      0.0421455000
_diffrn_orient_matrix_UB_33      0.0120713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4915
_reflns_number_total             9550
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         9550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      0.985
_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)+(0.0399P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1427
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Rotating group:
 N13(H13A,H13B), N23(H23A,H23B), N33(H33A,H33B), N43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 N11(H11), N41(H41), N21(H21), N31(H31), C12(H12A), C210(H210), C32(H32A),
 C42(H42A), C214(H214), C48(H48), C22(H22A), C211(H211), C111(H111), C114(H114),
  C110(H110), C47(H47), C113(H113), C46(H46), C38(H38), C18(H18), C28(H28),
 C213(H213), C410(H410), C26(H26), C27(H27), C36(H36), C37(H37), C16(H16),
 C17(H17), C314(H314), C310(H310), C414(H414), C411(H411), C311(H311),
 C413(H413), C313(H313)
2.c Idealised tetrahedral OH refined as rotating group:
 O42(H42), O43(H43), O32(H32), O12(H12), O22(H22), O23(H23), O33(H33), O13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
O42 O 0.60016(6) 0.3442(2) 0.53641(8) 0.0461(5) Uani 1 1 d . . . . .
H42 H 0.580489 0.299084 0.555791 0.069 Uiso 1 1 calc GR . . . .
O11 O 0.94749(7) -0.03297(19) 0.36227(8) 0.0442(5) Uani 1 1 d . . . . .
O43 O 0.65108(6) 0.4969(2) 0.46483(8) 0.0455(5) Uani 1 1 d . . . . .
H43 H 0.666967 0.516586 0.434427 0.068 Uiso 1 1 calc GR . . . .
O32 O 0.64897(6) 0.81945(19) 0.45987(9) 0.0470(5) Uani 1 1 d . . . . .
H32 H 0.668389 0.763027 0.447114 0.070 Uiso 1 1 calc GR . . . .
O12 O 0.90295(7) -0.30788(19) 0.47053(10) 0.0486(5) Uani 1 1 d . . . . .
H12 H 0.920489 -0.247577 0.457837 0.073 Uiso 1 1 calc GR . . . .
O21 O 0.80437(6) 0.46443(18) 0.64579(8) 0.0439(5) Uani 1 1 d . . . . .
O22 O 0.84587(7) 0.1826(2) 0.52946(9) 0.0506(6) Uani 1 1 d . . . . .
H22 H 0.829575 0.241801 0.545012 0.076 Uiso 1 1 calc GR . . . .
O23 O 0.89071(7) 0.0145(2) 0.45886(9) 0.0488(5) Uani 1 1 d . . . . .
H23 H 0.904346 -0.012212 0.427828 0.073 Uiso 1 1 calc GR . . . .
O31 O 0.70459(7) 0.5241(2) 0.36620(9) 0.0516(5) Uani 1 1 d . . . . .
O33 O 0.59479(7) 0.9878(2) 0.52107(10) 0.0585(6) Uani 1 1 d . . . . .
H33 H 0.580178 1.024033 0.549060 0.088 Uiso 1 1 calc GR . . . .
O41 O 0.55153(7) 0.0402(2) 0.63639(10) 0.0567(6) Uani 1 1 d . . . . .
N11 N 1.02347(8) -0.0898(2) 0.43090(10) 0.0405(6) Uani 1 1 d . . . . .
H11 H 1.058102 -0.080820 0.443969 0.049 Uiso 1 1 calc R . . . .
O13 O 0.85472(7) -0.4849(2) 0.53249(11) 0.0671(7) Uani 1 1 d . . . . .
H13 H 0.841436 -0.522984 0.561035 0.101 Uiso 1 1 calc GR . . . .
N22 N 0.75803(8) 0.3213(2) 0.54504(11) 0.0394(6) Uani 1 1 d . . . . .
N12 N 0.99343(8) -0.1793(2) 0.46021(11) 0.0379(6) Uani 1 1 d . . . . .
N42 N 0.50893(8) 0.2232(2) 0.55134(11) 0.0403(6) Uani 1 1 d . . . . .
N41 N 0.47722(8) 0.1509(2) 0.58766(11) 0.0426(6) Uani 1 1 d . . . . .
H41 H 0.442343 0.162755 0.582763 0.051 Uiso 1 1 calc R . . . .
N21 N 0.72866(8) 0.4084(2) 0.57692(11) 0.0429(6) Uani 1 1 d . . . . .
H21 H 0.693736 0.415068 0.565523 0.052 Uiso 1 1 calc R . . . .
N31 N 0.77781(8) 0.6316(2) 0.41922(11) 0.0451(6) Uani 1 1 d . . . . .
H31 H 0.812845 0.640548 0.427541 0.054 Uiso 1 1 calc R . . . .
N32 N 0.74419(8) 0.7074(2) 0.45097(11) 0.0407(6) Uani 1 1 d . . . . .
N13 N 1.10867(9) 0.3789(2) 0.26499(11) 0.0511(7) Uani 1 1 d . . . . .
H13A H 1.085681 0.430067 0.240974 0.061 Uiso 1 1 d GR . . . .
H13B H 1.126271 0.426037 0.296174 0.061 Uiso 1 1 d GR . . . .
N23 N 0.64216(9) 0.8908(2) 0.73357(12) 0.0561(7) Uani 1 1 d . . . . .
H23A H 0.607177 0.880933 0.724150 0.067 Uiso 1 1 d GR . . . .
H23B H 0.651692 0.889418 0.775294 0.067 Uiso 1 1 d GR . . . .
C19 C 1.02866(9) 0.0811(3) 0.35153(12) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.99756(10) -0.0170(3) 0.38154(12) 0.0324(6) Uani 1 1 d . . . . .
C23 C 0.75754(10) 0.1638(3) 0.46057(12) 0.0343(6) Uani 1 1 d . . . . .
C45 C 0.59714(9) 0.4718(3) 0.44151(12) 0.0339(6) Uani 1 1 d . . . . .
C44 C 0.57022(10) 0.3909(3) 0.48021(12) 0.0345(6) Uani 1 1 d . . . . .
C29 C 0.72299(10) 0.5848(3) 0.65288(12) 0.0350(6) Uani 1 1 d . . . . .
C24 C 0.81311(10) 0.1318(3) 0.47644(12) 0.0341(6) Uani 1 1 d . . . . .
C43 C 0.51422(10) 0.3648(3) 0.46190(13) 0.0363(7) Uani 1 1 d . . . . .
C12 C 1.01917(10) -0.2512(3) 0.50548(13) 0.0372(7) Uani 1 1 d . . . . .
H12A H 1.056773 -0.240093 0.517720 0.045 Uiso 1 1 calc R . . . .
C21 C 0.75471(10) 0.4826(3) 0.62578(12) 0.0350(6) Uani 1 1 d . . . . .
C34 C 0.67848(10) 0.8868(3) 0.51017(13) 0.0358(6) Uani 1 1 d . . . . .
C33 C 0.73444(10) 0.8681(3) 0.53077(13) 0.0362(7) Uani 1 1 d . . . . .
C210 C 0.67295(10) 0.6347(3) 0.62070(13) 0.0396(7) Uani 1 1 d . . . . .
H210 H 0.657214 0.599417 0.580744 0.048 Uiso 1 1 calc R . . . .
C25 C 0.83667(10) 0.0428(3) 0.43859(12) 0.0351(6) Uani 1 1 d . . . . .
C32 C 0.76660(11) 0.7797(3) 0.49792(13) 0.0401(7) Uani 1 1 d . . . . .
H32A H 0.804342 0.775412 0.511218 0.048 Uiso 1 1 calc R . . . .
C42 C 0.48414(10) 0.2839(3) 0.50133(13) 0.0397(7) Uani 1 1 d . . . . .
H42A H 0.446304 0.276074 0.490094 0.048 Uiso 1 1 calc R . . . .
C112 C 1.08217(10) 0.2819(3) 0.29341(13) 0.0380(7) Uani 1 1 d . . . . .
C214 C 0.74424(10) 0.6397(3) 0.71232(13) 0.0424(7) Uani 1 1 d . . . . .
H214 H 0.777570 0.609154 0.734429 0.051 Uiso 1 1 calc R . . . .
C212 C 0.66817(10) 0.7891(3) 0.70755(13) 0.0392(7) Uani 1 1 d . . . . .
C14 C 0.93518(10) -0.3737(3) 0.51951(13) 0.0379(7) Uani 1 1 d . . . . .
C13 C 0.99126(10) -0.3491(3) 0.53803(12) 0.0351(6) Uani 1 1 d . . . . .
C48 C 0.48737(10) 0.4210(3) 0.40371(14) 0.0439(7) Uani 1 1 d . . . . .
H48 H 0.450063 0.406020 0.390936 0.053 Uiso 1 1 calc R . . . .
C22 C 0.73060(10) 0.2557(3) 0.49769(13) 0.0395(7) Uani 1 1 d . . . . .
H22A H 0.692895 0.267706 0.487296 0.047 Uiso 1 1 calc R . . . .
C31 C 0.75487(11) 0.5433(3) 0.37503(13) 0.0410(7) Uani 1 1 d . . . . .
C35 C 0.64999(10) 0.9764(3) 0.54277(13) 0.0394(7) Uani 1 1 d . . . . .
C211 C 0.64687(10) 0.7353(3) 0.64764(13) 0.0409(7) Uani 1 1 d . . . . .
H211 H 0.614104 0.767872 0.624978 0.049 Uiso 1 1 calc R . . . .
C111 C 1.10705(10) 0.2205(3) 0.34976(13) 0.0434(7) Uani 1 1 d . . . . .
H111 H 1.142020 0.246690 0.368839 0.052 Uiso 1 1 calc R . . . .
C114 C 1.00409(10) 0.1441(3) 0.29519(13) 0.0425(7) Uani 1 1 d . . . . .
H114 H 0.968783 0.119667 0.276493 0.051 Uiso 1 1 calc R . . . .
C110 C 1.08142(10) 0.1215(3) 0.37840(13) 0.0416(7) Uani 1 1 d . . . . .
H110 H 1.099442 0.081169 0.415995 0.050 Uiso 1 1 calc R . . . .
C41 C 0.50147(11) 0.0620(3) 0.63067(13) 0.0405(7) Uani 1 1 d . . . . .
C47 C 0.51460(11) 0.4967(3) 0.36561(14) 0.0466(8) Uani 1 1 d . . . . .
H47 H 0.495946 0.531854 0.326988 0.056 Uiso 1 1 calc R . . . .
C113 C 1.02985(11) 0.2405(3) 0.26624(13) 0.0455(7) Uani 1 1 d . . . . .
H113 H 1.012267 0.278951 0.227911 0.055 Uiso 1 1 calc R . . . .
C49 C 0.46606(10) -0.0070(3) 0.66997(13) 0.0406(7) Uani 1 1 d . . . . .
C15 C 0.90949(11) -0.4692(3) 0.55219(14) 0.0430(7) Uani 1 1 d . . . . .
C46 C 0.56979(10) 0.5218(3) 0.38396(13) 0.0422(7) Uani 1 1 d . . . . .
H46 H 0.588429 0.572375 0.357382 0.051 Uiso 1 1 calc R . . . .
N33 N 0.87384(11) 0.2824(3) 0.20296(13) 0.0730(8) Uani 1 1 d . . . . .
H33A H 0.851059 0.239600 0.174227 0.088 Uiso 1 1 d GR . . . .
H33B H 0.889949 0.340900 0.182357 0.088 Uiso 1 1 d GR . . . .
C39 C 0.78987(10) 0.4752(3) 0.33496(13) 0.0410(7) Uani 1 1 d . . . . .
C38 C 0.76022(11) 0.9397(3) 0.58449(14) 0.0447(7) Uani 1 1 d . . . . .
H38 H 0.797505 0.927590 0.598931 0.054 Uiso 1 1 calc R . . . .
C18 C 1.02029(12) -0.4216(3) 0.58895(14) 0.0473(8) Uani 1 1 d . . . . .
H18 H 1.057516 -0.405623 0.601813 0.057 Uiso 1 1 calc R . . . .
C28 C 0.72656(11) 0.1025(3) 0.40639(13) 0.0434(7) Uani 1 1 d . . . . .
H28 H 0.689364 0.121194 0.395627 0.052 Uiso 1 1 calc R . . . .
C213 C 0.71778(11) 0.7379(3) 0.73973(13) 0.0446(7) Uani 1 1 d . . . . .
H213 H 0.732999 0.771084 0.780337 0.054 Uiso 1 1 calc R . . . .
C410 C 0.42169(10) 0.0517(3) 0.69220(14) 0.0458(7) Uani 1 1 d . . . . .
H410 H 0.412782 0.138100 0.680837 0.055 Uiso 1 1 calc R . . . .
C26 C 0.80570(11) -0.0128(3) 0.38484(13) 0.0461(7) Uani 1 1 d . . . . .
H26 H 0.821873 -0.070007 0.358669 0.055 Uiso 1 1 calc R . . . .
C27 C 0.75006(11) 0.0161(3) 0.36936(13) 0.0491(8) Uani 1 1 d . . . . .
H27 H 0.728922 -0.023720 0.333585 0.059 Uiso 1 1 calc R . . . .
C36 C 0.67658(11) 1.0458(3) 0.59512(14) 0.0464(7) Uani 1 1 d . . . . .
H36 H 0.657261 1.105740 0.616437 0.056 Uiso 1 1 calc R . . . .
C37 C 0.73192(11) 1.0269(3) 0.61622(14) 0.0500(8) Uani 1 1 d . . . . .
H37 H 0.749840 1.073466 0.651905 0.060 Uiso 1 1 calc R . . . .
C16 C 0.93985(13) -0.5397(3) 0.60194(14) 0.0510(8) Uani 1 1 d . . . . .
H16 H 0.922951 -0.604244 0.623355 0.061 Uiso 1 1 calc R . . . .
C17 C 0.99525(12) -0.5154(3) 0.62031(14) 0.0529(8) Uani 1 1 d . . . . .
H17 H 1.015388 -0.563160 0.654096 0.063 Uiso 1 1 calc R . . . .
C312 C 0.84696(12) 0.3467(3) 0.24744(14) 0.0483(8) Uani 1 1 d . . . . .
C314 C 0.77260(12) 0.3548(3) 0.30886(14) 0.0521(8) Uani 1 1 d . . . . .
H314 H 0.741248 0.316557 0.320103 0.062 Uiso 1 1 calc R . . . .
C310 C 0.83726(11) 0.5301(3) 0.31744(14) 0.0508(8) Uani 1 1 d . . . . .
H310 H 0.850361 0.609695 0.335490 0.061 Uiso 1 1 calc R . . . .
C414 C 0.47748(13) -0.1368(3) 0.68743(15) 0.0546(8) Uani 1 1 d . . . . .
H414 H 0.507090 -0.177969 0.673402 0.066 Uiso 1 1 calc R . . . .
N43 N 0.37100(12) -0.2130(3) 0.78541(14) 0.0887(10) Uani 1 1 d . . . . .
H43A H 0.391713 -0.269323 0.808591 0.106 Uiso 1 1 d GR . . . .
H43B H 0.358024 -0.158841 0.810962 0.106 Uiso 1 1 d GR . . . .
C411 C 0.39082(11) -0.0156(3) 0.73059(14) 0.0511(8) Uani 1 1 d . . . . .
H411 H 0.361695 0.025901 0.745497 0.061 Uiso 1 1 calc R . . . .
C412 C 0.40281(13) -0.1448(3) 0.74721(15) 0.0563(9) Uani 1 1 d . . . . .
C311 C 0.86457(11) 0.4673(3) 0.27375(15) 0.0543(8) Uani 1 1 d . . . . .
H311 H 0.895422 0.506295 0.261582 0.065 Uiso 1 1 calc R . . . .
C413 C 0.44642(14) -0.2058(3) 0.72470(15) 0.0608(9) Uani 1 1 d . . . . .
H413 H 0.454479 -0.293145 0.734897 0.073 Uiso 1 1 calc R . . . .
C313 C 0.80116(13) 0.2901(3) 0.26626(15) 0.0571(9) Uani 1 1 d . . . . .
H313 H 0.789448 0.207992 0.250205 0.069 Uiso 1 1 calc R . . . .


_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
O42 H42 0.8200 . ?
O42 C44 1.363(3) . ?
O11 C11 1.248(3) . ?
O43 H43 0.8200 . ?
O43 C45 1.367(3) . ?
O32 H32 0.8200 . ?
O32 C34 1.360(3) . ?
O12 H12 0.8200 . ?
O12 C14 1.363(3) . ?
O21 C21 1.245(3) . ?
O22 H22 0.8200 . ?
O22 C24 1.360(3) . ?
O23 H23 0.8200 . ?
O23 C25 1.365(3) . ?
O31 C31 1.242(3) . ?
O33 H33 0.8200 . ?
O33 C35 1.371(3) . ?
O41 C41 1.244(3) . ?
N11 H11 0.8600 . ?
N11 N12 1.378(3) . ?
N11 C11 1.342(3) . ?
O13 H13 0.8200 . ?
O13 C15 1.359(3) . ?
N22 N21 1.382(3) . ?
N22 C22 1.288(3) . ?
N12 C12 1.278(3) . ?
N42 N41 1.384(3) . ?
N42 C42 1.278(3) . ?
N41 H41 0.8600 . ?
N41 C41 1.344(3) . ?
N21 H21 0.8600 . ?
N21 C21 1.344(3) . ?
N31 H31 0.8600 . ?
N31 N32 1.378(3) . ?
N31 C31 1.344(3) . ?
N32 C32 1.276(3) . ?
N13 H13A 0.8673 . ?
N13 H13B 0.8651 . ?
N13 C112 1.372(3) . ?
N23 H23A 0.8608 . ?
N23 H23B 0.8604 . ?
N23 C212 1.376(3) . ?
C19 C11 1.461(3) . ?
C19 C114 1.386(3) . ?
C19 C110 1.395(3) . ?
C23 C24 1.398(3) . ?
C23 C22 1.442(3) . ?
C23 C28 1.402(3) . ?
C45 C44 1.393(3) . ?
C45 C46 1.373(3) . ?
C44 C43 1.400(3) . ?
C29 C21 1.469(4) . ?
C29 C210 1.403(3) . ?
C29 C214 1.380(3) . ?
C24 C25 1.388(3) . ?
C43 C42 1.449(4) . ?
C43 C48 1.404(4) . ?
C12 H12A 0.9300 . ?
C12 C13 1.442(3) . ?
C34 C33 1.393(3) . ?
C34 C35 1.394(3) . ?
C33 C32 1.444(4) . ?
C33 C38 1.398(4) . ?
C210 H210 0.9300 . ?
C210 C211 1.377(3) . ?
C25 C26 1.370(3) . ?
C32 H32A 0.9300 . ?
C42 H42A 0.9300 . ?
C112 C111 1.381(3) . ?
C112 C113 1.391(3) . ?
C214 H214 0.9300 . ?
C214 C213 1.369(4) . ?
C212 C211 1.384(3) . ?
C212 C213 1.399(3) . ?
C14 C13 1.400(3) . ?
C14 C15 1.397(4) . ?
C13 C18 1.391(4) . ?
C48 H48 0.9300 . ?
C48 C47 1.359(4) . ?
C22 H22A 0.9300 . ?
C31 C39 1.468(4) . ?
C35 C36 1.373(4) . ?
C211 H211 0.9300 . ?
C111 H111 0.9300 . ?
C111 C110 1.377(3) . ?
C114 H114 0.9300 . ?
C114 C113 1.362(3) . ?
C110 H110 0.9300 . ?
C41 C49 1.469(4) . ?
C47 H47 0.9300 . ?
C47 C46 1.379(3) . ?
C113 H113 0.9300 . ?
C49 C410 1.391(4) . ?
C49 C414 1.389(4) . ?
C15 C16 1.378(4) . ?
C46 H46 0.9300 . ?
N33 H33A 0.8692 . ?
N33 H33B 0.8671 . ?
N33 C312 1.386(3) . ?
C39 C314 1.382(4) . ?
C39 C310 1.398(4) . ?
C38 H38 0.9300 . ?
C38 C37 1.365(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.361(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.360(4) . ?
C213 H213 0.9300 . ?
C410 H410 0.9300 . ?
C410 C411 1.372(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.392(3) . ?
C27 H27 0.9300 . ?
C36 H36 0.9300 . ?
C36 C37 1.381(4) . ?
C37 H37 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C312 C311 1.387(4) . ?
C312 C313 1.382(4) . ?
C314 H314 0.9300 . ?
C314 C313 1.384(4) . ?
C310 H310 0.9300 . ?
C310 C311 1.373(4) . ?
C414 H414 0.9300 . ?
C414 C413 1.369(4) . ?
N43 H43A 0.8625 . ?
N43 H43B 0.8628 . ?
N43 C412 1.390(4) . ?
C411 H411 0.9300 . ?
C411 C412 1.382(4) . ?
C412 C413 1.389(4) . ?
C311 H311 0.9300 . ?
C413 H413 0.9300 . ?
C313 H313 0.9300 . ?

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
C44 O42 H42 109.5 . . ?
C45 O43 H43 109.5 . . ?
C34 O32 H32 109.5 . . ?
C14 O12 H12 109.5 . . ?
C24 O22 H22 109.5 . . ?
C25 O23 H23 109.5 . . ?
C35 O33 H33 109.5 . . ?
N12 N11 H11 120.7 . . ?
C11 N11 H11 120.7 . . ?
C11 N11 N12 118.6(2) . . ?
C15 O13 H13 109.5 . . ?
C22 N22 N21 116.6(2) . . ?
C12 N12 N11 117.7(2) . . ?
C42 N42 N41 117.5(2) . . ?
N42 N41 H41 120.3 . . ?
C41 N41 N42 119.4(2) . . ?
C41 N41 H41 120.3 . . ?
N22 N21 H21 120.0 . . ?
C21 N21 N22 119.9(2) . . ?
C21 N21 H21 120.0 . . ?
N32 N31 H31 120.6 . . ?
C31 N31 H31 120.6 . . ?
C31 N31 N32 118.8(2) . . ?
C32 N32 N31 118.0(2) . . ?
H13A N13 H13B 107.5 . . ?
C112 N13 H13A 111.6 . . ?
C112 N13 H13B 107.2 . . ?
H23A N23 H23B 109.2 . . ?
C212 N23 H23A 109.8 . . ?
C212 N23 H23B 108.3 . . ?
C114 C19 C11 119.2(2) . . ?
C114 C19 C110 117.1(2) . . ?
C110 C19 C11 123.6(2) . . ?
O11 C11 N11 120.0(2) . . ?
O11 C11 C19 121.0(2) . . ?
N11 C11 C19 119.1(2) . . ?
C24 C23 C22 123.1(2) . . ?
C24 C23 C28 118.3(2) . . ?
C28 C23 C22 118.6(2) . . ?
O43 C45 C44 115.8(2) . . ?
O43 C45 C46 123.7(2) . . ?
C46 C45 C44 120.5(2) . . ?
O42 C44 C45 117.2(2) . . ?
O42 C44 C43 122.8(2) . . ?
C45 C44 C43 119.9(2) . . ?
C210 C29 C21 124.0(2) . . ?
C214 C29 C21 118.7(2) . . ?
C214 C29 C210 117.2(3) . . ?
O22 C24 C23 122.4(2) . . ?
O22 C24 C25 117.3(2) . . ?
C25 C24 C23 120.3(2) . . ?
C44 C43 C42 122.0(2) . . ?
C44 C43 C48 117.8(3) . . ?
C48 C43 C42 120.3(2) . . ?
N12 C12 H12A 119.2 . . ?
N12 C12 C13 121.5(2) . . ?
C13 C12 H12A 119.2 . . ?
O21 C21 N21 119.7(3) . . ?
O21 C21 C29 122.4(2) . . ?
N21 C21 C29 117.9(2) . . ?
O32 C34 C33 123.3(2) . . ?
O32 C34 C35 117.0(2) . . ?
C33 C34 C35 119.7(2) . . ?
C34 C33 C32 122.4(3) . . ?
C34 C33 C38 118.4(3) . . ?
C38 C33 C32 119.2(2) . . ?
C29 C210 H210 119.6 . . ?
C211 C210 C29 120.7(3) . . ?
C211 C210 H210 119.6 . . ?
O23 C25 C24 116.3(2) . . ?
O23 C25 C26 123.6(3) . . ?
C26 C25 C24 120.1(2) . . ?
N32 C32 C33 121.2(2) . . ?
N32 C32 H32A 119.4 . . ?
C33 C32 H32A 119.4 . . ?
N42 C42 C43 120.9(2) . . ?
N42 C42 H42A 119.6 . . ?
C43 C42 H42A 119.6 . . ?
N13 C112 C111 120.9(2) . . ?
N13 C112 C113 121.5(2) . . ?
C111 C112 C113 117.7(3) . . ?
C29 C214 H214 119.0 . . ?
C213 C214 C29 122.0(3) . . ?
C213 C214 H214 119.0 . . ?
N23 C212 C211 121.2(3) . . ?
N23 C212 C213 121.5(3) . . ?
C211 C212 C213 117.3(3) . . ?
O12 C14 C13 123.4(2) . . ?
O12 C14 C15 116.7(2) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C13 C12 121.5(2) . . ?
C18 C13 C12 119.8(2) . . ?
C18 C13 C14 118.7(3) . . ?
C43 C48 H48 119.2 . . ?
C47 C48 C43 121.6(2) . . ?
C47 C48 H48 119.2 . . ?
N22 C22 C23 120.9(2) . . ?
N22 C22 H22A 119.5 . . ?
C23 C22 H22A 119.5 . . ?
O31 C31 N31 120.5(3) . . ?
O31 C31 C39 120.6(3) . . ?
N31 C31 C39 118.8(2) . . ?
O33 C35 C34 116.7(2) . . ?
O33 C35 C36 122.8(3) . . ?
C36 C35 C34 120.5(2) . . ?
C210 C211 C212 121.7(3) . . ?
C210 C211 H211 119.2 . . ?
C212 C211 H211 119.2 . . ?
C112 C111 H111 119.2 . . ?
C110 C111 C112 121.7(3) . . ?
C110 C111 H111 119.2 . . ?
C19 C114 H114 118.8 . . ?
C113 C114 C19 122.3(2) . . ?
C113 C114 H114 118.8 . . ?
C19 C110 H110 119.7 . . ?
C111 C110 C19 120.6(3) . . ?
C111 C110 H110 119.7 . . ?
O41 C41 N41 120.9(3) . . ?
O41 C41 C49 122.3(3) . . ?
N41 C41 C49 116.8(2) . . ?
C48 C47 H47 119.9 . . ?
C48 C47 C46 120.3(3) . . ?
C46 C47 H47 119.9 . . ?
C112 C113 H113 119.7 . . ?
C114 C113 C112 120.7(3) . . ?
C114 C113 H113 119.7 . . ?
C410 C49 C41 123.4(3) . . ?
C414 C49 C41 119.2(3) . . ?
C414 C49 C410 117.5(3) . . ?
O13 C15 C14 116.4(3) . . ?
O13 C15 C16 124.0(3) . . ?
C16 C15 C14 119.6(3) . . ?
C45 C46 C47 119.9(3) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
H33A N33 H33B 107.8 . . ?
C312 N33 H33A 111.6 . . ?
C312 N33 H33B 108.1 . . ?
C314 C39 C31 118.0(3) . . ?
C314 C39 C310 118.2(3) . . ?
C310 C39 C31 123.5(3) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 C33 121.5(3) . . ?
C37 C38 H38 119.3 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.0(3) . . ?
C27 C28 H28 119.5 . . ?
C214 C213 C212 121.0(3) . . ?
C214 C213 H213 119.5 . . ?
C212 C213 H213 119.5 . . ?
C49 C410 H410 119.4 . . ?
C411 C410 C49 121.2(3) . . ?
C411 C410 H410 119.4 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.1(3) . . ?
C27 C26 H26 119.9 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.2(3) . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 119.7(3) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N33 C312 C311 121.9(3) . . ?
C313 C312 N33 119.5(3) . . ?
C313 C312 C311 118.6(3) . . ?
C39 C314 H314 119.4 . . ?
C39 C314 C313 121.1(3) . . ?
C313 C314 H314 119.4 . . ?
C39 C310 H310 119.8 . . ?
C311 C310 C39 120.4(3) . . ?
C311 C310 H310 119.8 . . ?
C49 C414 H414 119.1 . . ?
C413 C414 C49 121.9(3) . . ?
C413 C414 H414 119.1 . . ?
H43A N43 H43B 109.2 . . ?
C412 N43 H43A 108.2 . . ?
C412 N43 H43B 109.3 . . ?
C410 C411 H411 119.8 . . ?
C410 C411 C412 120.3(3) . . ?
C412 C411 H411 119.8 . . ?
C411 C412 N43 120.1(3) . . ?
C411 C412 C413 119.3(3) . . ?
C413 C412 N43 120.5(3) . . ?
C312 C311 H311 119.4 . . ?
C310 C311 C312 121.2(3) . . ?
C310 C311 H311 119.4 . . ?
C414 C413 C412 119.7(3) . . ?
C414 C413 H413 120.1 . . ?
C412 C413 H413 120.1 . . ?
C312 C313 C314 120.4(3) . . ?
C312 C313 H313 119.8 . . ?
C314 C313 H313 119.8 . . ?

_olex2_date_sample_data_collection 2018-05-29
_olex2_exptl_crystal_mounting_method 'glass needle'
_olex2_submission_special_instructions 'No special instructions were received'
