# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ar_a
_database_code_depnum_ccdc_archive 'CCDC 1998538'
loop_
_audit_author_name
_audit_author_address
'Alakbar Huseynzada'
;Baku State University
Azerbaijan
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O6'
_chemical_formula_sum            'C16 H20 N2 O6'
_chemical_formula_weight         336.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.6354(5)
_cell_length_b                   14.5969(5)
_cell_length_c                   9.3401(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.173(2)
_cell_angle_gamma                90
_cell_volume                     1570.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      30.38

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5637
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8627
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.768
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3771
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.5758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.87492(12) 0.40177(9) 0.32259(13) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.99396(16) 0.29797(12) 0.43862(15) 0.0448(5) Uani 1 1 d . . . . .
O3 O 0.86092(12) 0.56020(10) 0.92997(13) 0.0264(3) Uani 1 1 d . . . . .
O4 O 0.65867(11) 0.51313(9) 0.30264(13) 0.0233(3) Uani 1 1 d . . . . .
O5 O 0.36420(11) 0.31410(10) 0.42341(15) 0.0268(3) Uani 1 1 d . . . . .
O6 O 0.72606(11) 0.35725(9) 0.74387(13) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.81515(14) 0.53736(11) 0.68839(16) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.7688(18) 0.5810(13) 0.684(2) 0.014(5) Uiso 1 1 d . . . . .
N2 N 0.95635(14) 0.44968(11) 0.82210(16) 0.0189(3) Uani 1 1 d . . . . .
H2 H 1.006(2) 0.4445(15) 0.903(2) 0.030(6) Uiso 1 1 d . . . . .
C1 C 0.91219(15) 0.41523(12) 0.57279(18) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.80958(15) 0.48079(12) 0.55774(17) 0.0155(4) Uani 1 1 d . . . . .
H2A H 0.818044 0.522891 0.475429 0.019 Uiso 1 1 calc R U . . .
C3 C 0.87457(16) 0.51758(13) 0.81905(18) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.98154(15) 0.40426(12) 0.70052(18) 0.0163(4) Uani 1 1 d . . . . .
C5 C 0.93427(17) 0.36528(13) 0.44321(19) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.8863(2) 0.35549(15) 0.18860(19) 0.0286(5) Uani 1 1 d . . . . .
H6A H 0.846070 0.390795 0.107267 0.043 Uiso 1 1 calc R U . . .
H6B H 0.851764 0.294269 0.189218 0.043 Uiso 1 1 calc R U . . .
H6C H 0.968658 0.350010 0.178423 0.043 Uiso 1 1 calc R U . . .
C7 C 0.69173(15) 0.43346(12) 0.52260(18) 0.0157(4) Uani 1 1 d . . . . .
C8 C 0.61798(16) 0.45165(12) 0.39387(18) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.51005(16) 0.41007(13) 0.36214(19) 0.0196(4) Uani 1 1 d . . . . .
H9A H 0.462157 0.422106 0.273010 0.023 Uiso 1 1 calc R U . . .
C10 C 0.47302(15) 0.35072(13) 0.4622(2) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.54291(16) 0.33055(12) 0.59138(19) 0.0187(4) Uani 1 1 d . . . . .
H11A H 0.517497 0.289217 0.658927 0.022 Uiso 1 1 calc R U . . .
C12 C 0.65148(15) 0.37253(12) 0.61950(18) 0.0160(4) Uani 1 1 d . . . . .
C13 C 0.6023(2) 0.51682(17) 0.1574(2) 0.0366(6) Uani 1 1 d . . . . .
H13A H 0.648316 0.554234 0.099481 0.055 Uiso 1 1 calc R U . . .
H13B H 0.525055 0.544080 0.155137 0.055 Uiso 1 1 calc R U . . .
H13C H 0.594527 0.454686 0.117431 0.055 Uiso 1 1 calc R U . . .
C14 C 0.31929(18) 0.25719(16) 0.5275(2) 0.0319(5) Uani 1 1 d . . . . .
H14A H 0.240085 0.238101 0.489432 0.048 Uiso 1 1 calc R U . . .
H14B H 0.318440 0.291623 0.617438 0.048 Uiso 1 1 calc R U . . .
H14C H 0.368647 0.202925 0.546898 0.048 Uiso 1 1 calc R U . . .
C15 C 0.69226(18) 0.29594(14) 0.8484(2) 0.0261(4) Uani 1 1 d . . . . .
H15A H 0.756438 0.288490 0.927623 0.039 Uiso 1 1 calc R U . . .
H15B H 0.672626 0.236336 0.803084 0.039 Uiso 1 1 calc R U . . .
H15C H 0.624397 0.320680 0.886443 0.039 Uiso 1 1 calc R U . . .
C16 C 1.09003(16) 0.34831(14) 0.72919(19) 0.0213(4) Uani 1 1 d . . . . .
H16A H 1.155730 0.388255 0.764247 0.032 Uiso 1 1 calc R U . . .
H16B H 1.104311 0.318195 0.639603 0.032 Uiso 1 1 calc R U . . .
H16C H 1.081165 0.301800 0.802496 0.032 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
O1 C5 1.345(2) . ?
O1 C6 1.445(2) . ?
O2 C5 1.207(2) . ?
O3 C3 1.238(2) . ?
O4 C8 1.368(2) . ?
O4 C13 1.422(2) . ?
O5 C10 1.375(2) . ?
O5 C14 1.433(2) . ?
O6 C12 1.366(2) . ?
O6 C15 1.420(2) . ?
N1 C3 1.346(2) . ?
N1 C2 1.467(2) . ?
N1 H1 0.83(2) . ?
N2 C3 1.371(2) . ?
N2 C4 1.382(2) . ?
N2 H2 0.89(2) . ?
C1 C4 1.351(2) . ?
C1 C5 1.467(2) . ?
C1 C2 1.521(2) . ?
C2 C7 1.529(2) . ?
C2 H2A 1.0000 . ?
C4 C16 1.495(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.396(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.388(3) . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.387(2) . ?
C11 C12 1.395(2) . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 116.18(15) . . ?
C8 O4 C13 117.76(15) . . ?
C10 O5 C14 117.23(14) . . ?
C12 O6 C15 118.87(14) . . ?
C3 N1 C2 126.14(16) . . ?
C3 N1 H1 117.0(13) . . ?
C2 N1 H1 116.0(13) . . ?
C3 N2 C4 123.86(15) . . ?
C3 N2 H2 116.4(14) . . ?
C4 N2 H2 118.1(14) . . ?
C4 C1 C5 121.13(17) . . ?
C4 C1 C2 121.23(16) . . ?
C5 C1 C2 117.64(15) . . ?
N1 C2 C1 109.63(14) . . ?
N1 C2 C7 111.41(14) . . ?
C1 C2 C7 113.82(15) . . ?
N1 C2 H2A 107.2 . . ?
C1 C2 H2A 107.2 . . ?
C7 C2 H2A 107.2 . . ?
O3 C3 N1 122.73(18) . . ?
O3 C3 N2 121.13(16) . . ?
N1 C3 N2 116.06(16) . . ?
C1 C4 N2 119.92(16) . . ?
C1 C4 C16 127.28(16) . . ?
N2 C4 C16 112.78(15) . . ?
O2 C5 O1 121.46(17) . . ?
O2 C5 C1 127.08(18) . . ?
O1 C5 C1 111.41(16) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 117.15(16) . . ?
C12 C7 C2 121.46(15) . . ?
C8 C7 C2 121.36(15) . . ?
O4 C8 C9 122.45(15) . . ?
O4 C8 C7 115.81(15) . . ?
C9 C8 C7 121.73(16) . . ?
C10 C9 C8 119.17(16) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
O5 C10 C11 123.42(17) . . ?
O5 C10 C9 115.33(16) . . ?
C11 C10 C9 121.25(17) . . ?
C10 C11 C12 118.27(17) . . ?
C10 C11 H11A 120.9 . . ?
C12 C11 H11A 120.9 . . ?
O6 C12 C11 122.49(16) . . ?
O6 C12 C7 115.10(15) . . ?
C11 C12 C7 122.41(16) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C1 -20.5(2) . . . . ?
C3 N1 C2 C7 106.4(2) . . . . ?
C4 C1 C2 N1 10.5(2) . . . . ?
C5 C1 C2 N1 -168.66(15) . . . . ?
C4 C1 C2 C7 -115.06(18) . . . . ?
C5 C1 C2 C7 65.8(2) . . . . ?
C2 N1 C3 O3 -167.92(17) . . . . ?
C2 N1 C3 N2 15.2(3) . . . . ?
C4 N2 C3 O3 -175.13(17) . . . . ?
C4 N2 C3 N1 1.8(3) . . . . ?
C5 C1 C4 N2 -177.71(16) . . . . ?
C2 C1 C4 N2 3.2(3) . . . . ?
C5 C1 C4 C16 4.2(3) . . . . ?
C2 C1 C4 C16 -174.93(17) . . . . ?
C3 N2 C4 C1 -10.6(3) . . . . ?
C3 N2 C4 C16 167.78(17) . . . . ?
C6 O1 C5 O2 0.4(3) . . . . ?
C6 O1 C5 C1 -177.43(16) . . . . ?
C4 C1 C5 O2 17.6(3) . . . . ?
C2 C1 C5 O2 -163.3(2) . . . . ?
C4 C1 C5 O1 -164.73(16) . . . . ?
C2 C1 C5 O1 14.4(2) . . . . ?
N1 C2 C7 C12 -60.4(2) . . . . ?
C1 C2 C7 C12 64.2(2) . . . . ?
N1 C2 C7 C8 117.48(18) . . . . ?
C1 C2 C7 C8 -117.93(18) . . . . ?
C13 O4 C8 C9 -16.0(3) . . . . ?
C13 O4 C8 C7 164.49(17) . . . . ?
C12 C7 C8 O4 178.59(15) . . . . ?
C2 C7 C8 O4 0.6(2) . . . . ?
C12 C7 C8 C9 -1.0(3) . . . . ?
C2 C7 C8 C9 -178.98(16) . . . . ?
O4 C8 C9 C10 -177.85(16) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
C14 O5 C10 C11 4.3(3) . . . . ?
C14 O5 C10 C9 -176.00(16) . . . . ?
C8 C9 C10 O5 178.69(16) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
O5 C10 C11 C12 -179.47(16) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C15 O6 C12 C11 0.4(3) . . . . ?
C15 O6 C12 C7 -179.80(15) . . . . ?
C10 C11 C12 O6 179.71(16) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C8 C7 C12 O6 -179.66(15) . . . . ?
C2 C7 C12 O6 -1.7(2) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C2 C7 C12 C11 178.19(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O5 0.83(2) 2.30(2) 3.087(2) 157.0(18) 3_666 yes
N2 H2 O3 0.89(2) 2.03(2) 2.916(2) 171(2) 3_767 yes
C2 H2A O4 1.00 2.28 2.792(2) 110.3 . yes
C16 H16B O2 0.98 2.14 2.880(2) 131.1 . yes
C16 H16C O2 0.98 2.27 3.203(2) 159.6 4_566 yes

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052



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

data_DOR27
_database_code_depnum_ccdc_archive 'CCDC 1998547'
loop_
_audit_author_name
_audit_author_address
'Alakbar Huseynzada'
;Baku State University
Azerbaijan
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N2 O3'
_chemical_formula_sum            'C21 H16 N2 O3'
_chemical_formula_weight         344.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.918(2)
_cell_length_b                   13.013(3)
_cell_length_c                   12.9630(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.984(18)
_cell_angle_gamma                90
_cell_volume                     1672.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6
_cell_measurement_theta_max      11

_exptl_crystal_description       LAMINAR
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   PSI-SCAN
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  300
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3094
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2950
_reflns_number_gt                1641
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al.2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²+5.9951P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   DIFMAP
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0012(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2950
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1932
_refine_ls_R_factor_gt           0.1089
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6372(7) 0.5405(6) 0.8940(5) 0.0513(17) Uani 1 1 d . . . . .
C2 C 0.4530(7) 0.6220(5) 0.7985(5) 0.0466(16) Uani 1 1 d . . . . .
C3 C 0.5394(7) 0.6436(5) 0.7204(5) 0.0483(17) Uani 1 1 d . . . . .
C4 C 0.6769(7) 0.6153(5) 0.7357(5) 0.0495(17) Uani 1 1 d . . . . .
C5 C 0.7734(6) 0.6371(5) 0.6536(5) 0.0476(17) Uani 1 1 d . . . . .
C6 C 0.7600(7) 0.5870(6) 0.5620(5) 0.0530(18) Uani 1 1 d . . . . .
H6 H 0.685071 0.545301 0.549159 0.064 Uiso 1 1 calc R U . . .
C7 C 0.8590(7) 0.5970(5) 0.4849(5) 0.0511(17) Uani 1 1 d . . . . .
C8 C 0.8478(7) 0.5395(6) 0.3937(5) 0.0572(19) Uani 1 1 d . . . . .
H8 H 0.772984 0.497434 0.381857 0.069 Uiso 1 1 calc R U . . .
C9 C 0.9453(8) 0.5442(6) 0.3218(6) 0.066(2) Uani 1 1 d . . . . .
H9 H 0.937028 0.505134 0.261870 0.079 Uiso 1 1 calc R U . . .
C10 C 1.0565(8) 0.6074(6) 0.3383(6) 0.065(2) Uani 1 1 d . . . . .
H10 H 1.122163 0.611015 0.288910 0.078 Uiso 1 1 calc R U . . .
C11 C 1.0706(7) 0.6650(6) 0.4276(5) 0.061(2) Uani 1 1 d . . . . .
H11 H 1.146785 0.705681 0.438786 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9699(7) 0.6624(6) 0.5019(5) 0.0506(17) Uani 1 1 d . . . . .
C13 C 0.9814(6) 0.7211(5) 0.5966(5) 0.0469(16) Uani 1 1 d . . . . .
C14 C 1.0858(7) 0.7927(5) 0.6159(6) 0.0559(18) Uani 1 1 d . . . . .
H14 H 1.150530 0.802419 0.566562 0.067 Uiso 1 1 calc R U . . .
C15 C 1.0942(8) 0.8484(6) 0.7053(6) 0.067(2) Uani 1 1 d . . . . .
H15 H 1.164783 0.894579 0.716328 0.080 Uiso 1 1 calc R U . . .
C16 C 0.9975(8) 0.8363(6) 0.7804(6) 0.066(2) Uani 1 1 d . . . . .
H16 H 1.002369 0.874843 0.840878 0.080 Uiso 1 1 calc R U . . .
C17 C 0.8953(8) 0.7668(6) 0.7634(6) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.831295 0.758320 0.813404 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8844(7) 0.7082(5) 0.6731(5) 0.0511(17) Uani 1 1 d . . . . .
C19 C 0.3089(6) 0.6520(6) 0.8040(5) 0.0590(19) Uani 1 1 d . . . . .
H19A H 0.262641 0.603386 0.845836 0.088 Uiso 1 1 calc R U . . .
H19B H 0.268137 0.652681 0.735715 0.088 Uiso 1 1 calc R U . . .
H19C H 0.302703 0.719207 0.833927 0.088 Uiso 1 1 calc R U . . .
C20 C 0.4879(7) 0.7005(6) 0.6274(5) 0.0540(18) Uani 1 1 d . . . . .
C21 C 0.5210(10) 0.8514(7) 0.5245(6) 0.095(3) Uani 1 1 d . . . . .
H21A H 0.540938 0.814750 0.462562 0.143 Uiso 1 1 calc R U . . .
H21B H 0.572452 0.913857 0.527788 0.143 Uiso 1 1 calc R U . . .
H21C H 0.426474 0.867495 0.524037 0.143 Uiso 1 1 calc R U . . .
N1 N 0.7246(5) 0.5673(5) 0.8183(4) 0.0537(15) Uani 1 1 d . . . . .
N2 N 0.5044(5) 0.5712(4) 0.8826(4) 0.0474(14) Uani 1 1 d D . . . .
H2N H 0.444(5) 0.562(5) 0.932(3) 0.057 Uiso 1 1 d D U . . .
O1 O 0.6746(5) 0.4925(4) 0.9722(4) 0.0655(15) Uani 1 1 d . . . . .
O2 O 0.3984(6) 0.6732(5) 0.5700(4) 0.093(2) Uani 1 1 d . . . . .
O3 O 0.5561(5) 0.7874(4) 0.6147(4) 0.0660(15) Uani 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
C1 O1 1.237(8) . ?
C1 N1 1.376(8) . ?
C1 N2 1.379(8) . ?
C2 N2 1.359(8) . ?
C2 C3 1.378(8) . ?
C2 C19 1.486(8) . ?
C3 C4 1.420(9) . ?
C3 C20 1.490(9) . ?
C4 N1 1.314(8) . ?
C4 C5 1.483(8) . ?
C5 C6 1.356(9) . ?
C5 C18 1.454(9) . ?
C6 C7 1.432(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(9) . ?
C7 C12 1.403(9) . ?
C8 C9 1.368(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.411(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.446(9) . ?
C13 C14 1.409(9) . ?
C13 C18 1.417(9) . ?
C14 C15 1.367(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.399(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(9) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O2 1.192(8) . ?
C20 O3 1.331(8) . ?
C21 O3 1.468(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N2 H2N 0.902(10) . ?

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
O1 C1 N1 122.3(6) . . ?
O1 C1 N2 119.5(6) . . ?
N1 C1 N2 118.2(6) . . ?
N2 C2 C3 117.6(6) . . ?
N2 C2 C19 115.1(5) . . ?
C3 C2 C19 127.3(6) . . ?
C2 C3 C4 117.6(6) . . ?
C2 C3 C20 119.4(6) . . ?
C4 C3 C20 122.8(6) . . ?
N1 C4 C3 123.6(6) . . ?
N1 C4 C5 117.0(6) . . ?
C3 C4 C5 119.4(6) . . ?
C6 C5 C18 120.6(6) . . ?
C6 C5 C4 119.3(6) . . ?
C18 C5 C4 120.0(6) . . ?
C5 C6 C7 121.2(7) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C12 119.7(6) . . ?
C8 C7 C6 120.3(7) . . ?
C12 C7 C6 119.9(6) . . ?
C9 C8 C7 120.9(7) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.0(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.5(7) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.4(7) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.5(7) . . ?
C7 C12 C13 119.5(6) . . ?
C11 C12 C13 122.0(7) . . ?
C14 C13 C18 117.8(7) . . ?
C14 C13 C12 122.4(6) . . ?
C18 C13 C12 119.7(6) . . ?
C15 C14 C13 121.6(7) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 120.5(8) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.8(7) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 122.1(7) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C13 119.1(7) . . ?
C17 C18 C5 122.0(6) . . ?
C13 C18 C5 118.8(6) . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 O3 123.1(7) . . ?
O2 C20 C3 125.7(7) . . ?
O3 C20 C3 111.1(6) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 N1 C1 118.9(6) . . ?
C2 N2 C1 123.9(5) . . ?
C2 N2 H2N 114(4) . . ?
C1 N2 H2N 123(4) . . ?
C20 O3 C21 118.2(6) . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_DOR26
_database_code_depnum_ccdc_archive 'CCDC 1998539'
loop_
_audit_author_name
_audit_author_address
'Alakbar Huseynzada'
;Baku State University
Azerbaijan
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N2 O3'
_chemical_formula_sum            'C21 H18 N2 O3'
_chemical_formula_weight         346.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   25.515(5)
_cell_length_b                   7.710(3)
_cell_length_c                   18.240(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.277(17)
_cell_angle_gamma                90
_cell_volume                     3407.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      14

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  300
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3129
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3008
_reflns_number_gt                2200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al.2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+4.4503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     DIRECT
_atom_sites_solution_secondary   DIFMAP
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     243
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.46820(12) 0.5513(4) 0.09105(18) 0.0499(7) Uani 1 1 d . . . . .
C2 C 0.45426(12) 0.2406(4) 0.09854(18) 0.0514(7) Uani 1 1 d . . . . .
C3 C 0.43632(11) 0.2579(4) 0.16007(16) 0.0455(7) Uani 1 1 d . . . . .
C4 C 0.42714(11) 0.4352(4) 0.18975(17) 0.0470(7) Uani 1 1 d . . . . .
H4 H 0.445576 0.437375 0.245646 0.056 Uiso 1 1 calc R U . . .
C5 C 0.36609(11) 0.4798(4) 0.17491(16) 0.0447(7) Uani 1 1 d . . . . .
C6 C 0.33071(12) 0.4633(4) 0.10281(17) 0.0521(7) Uani 1 1 d . . . . .
H6 H 0.342896 0.408616 0.065698 0.063 Uiso 1 1 calc R U . . .
C7 C 0.27516(12) 0.5264(4) 0.08088(17) 0.0534(8) Uani 1 1 d . . . . .
C8 C 0.23997(13) 0.5113(5) 0.0052(2) 0.0674(10) Uani 1 1 d . . . . .
H8 H 0.251840 0.451668 -0.030994 0.081 Uiso 1 1 calc R U . . .
C9 C 0.18837(15) 0.5828(6) -0.0166(2) 0.0809(12) Uani 1 1 d . . . . .
H9 H 0.165105 0.571109 -0.067025 0.097 Uiso 1 1 calc R U . . .
C10 C 0.17105(15) 0.6735(6) 0.0379(3) 0.0810(12) Uani 1 1 d . . . . .
H10 H 0.136255 0.724425 0.023279 0.097 Uiso 1 1 calc R U . . .
C11 C 0.20420(14) 0.6882(5) 0.1117(2) 0.0692(10) Uani 1 1 d . . . . .
H11 H 0.191812 0.750172 0.146829 0.083 Uiso 1 1 calc R U . . .
C12 C 0.25692(12) 0.6123(4) 0.13676(19) 0.0527(8) Uani 1 1 d . . . . .
C13 C 0.29265(12) 0.6201(4) 0.21607(18) 0.0513(7) Uani 1 1 d . . . . .
C14 C 0.27514(14) 0.6929(4) 0.2761(2) 0.0634(9) Uani 1 1 d . . . . .
H14 H 0.239998 0.740722 0.264129 0.076 Uiso 1 1 calc R U . . .
C15 C 0.30871(16) 0.6942(5) 0.3506(2) 0.0709(10) Uani 1 1 d . . . . .
H15 H 0.296407 0.744090 0.388611 0.085 Uiso 1 1 calc R U . . .
C16 C 0.36099(16) 0.6222(5) 0.37033(19) 0.0691(10) Uani 1 1 d . . . . .
H16 H 0.383308 0.620099 0.421595 0.083 Uiso 1 1 calc R U . . .
C17 C 0.37959(14) 0.5537(5) 0.31347(17) 0.0582(8) Uani 1 1 d . . . . .
H17 H 0.415007 0.507424 0.327054 0.070 Uiso 1 1 calc R U . . .
C18 C 0.34696(12) 0.5513(4) 0.23558(16) 0.0477(7) Uani 1 1 d . . . . .
C19 C 0.46169(17) 0.0773(4) 0.0595(2) 0.0768(11) Uani 1 1 d . . . . .
H19A H 0.474226 -0.012844 0.097217 0.115 Uiso 1 1 calc R U . . .
H19B H 0.488501 0.095437 0.033250 0.115 Uiso 1 1 calc R U . . .
H19C H 0.427129 0.044057 0.022753 0.115 Uiso 1 1 calc R U . . .
C20 C 0.42544(12) 0.1048(4) 0.20106(18) 0.0536(8) Uani 1 1 d . . . . .
C21 C 0.3971(2) 0.0096(6) 0.3055(2) 0.0965(14) Uani 1 1 d . . . . .
H21A H 0.362963 -0.042446 0.275155 0.145 Uiso 1 1 calc R U . . .
H21B H 0.393235 0.052430 0.352945 0.145 Uiso 1 1 calc R U . . .
H21C H 0.425955 -0.075543 0.316589 0.145 Uiso 1 1 calc R U . . .
N1 N 0.45279(11) 0.5703(3) 0.15421(16) 0.0538(7) Uani 1 1 d D . . . .
H1N H 0.4503(13) 0.6825(17) 0.1660(18) 0.065 Uiso 1 1 d D U . . .
N2 N 0.46729(11) 0.3861(3) 0.06378(15) 0.0557(7) Uani 1 1 d D . . . .
H2N H 0.4802(12) 0.375(4) 0.0235(12) 0.067 Uiso 1 1 d D U . . .
O1 O 0.48376(10) 0.6721(3) 0.05874(14) 0.0688(7) Uani 1 1 d . . . . .
O2 O 0.42854(11) -0.0458(3) 0.18486(15) 0.0756(7) Uani 1 1 d . . . . .
O3 O 0.41072(10) 0.1524(3) 0.26262(13) 0.0710(7) Uani 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
C1 O1 1.233(3) . ?
C1 N1 1.337(4) . ?
C1 N2 1.365(4) . ?
C2 C3 1.345(4) . ?
C2 N2 1.380(4) . ?
C2 C19 1.488(4) . ?
C3 C20 1.470(4) . ?
C3 C4 1.515(4) . ?
C4 N1 1.483(4) . ?
C4 C5 1.534(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.348(4) . ?
C5 C18 1.451(4) . ?
C6 C7 1.432(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(4) . ?
C7 C12 1.411(4) . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.351(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.449(4) . ?
C13 C18 1.421(4) . ?
C13 C14 1.421(4) . ?
C14 C15 1.360(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(4) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O2 1.207(4) . ?
C20 O3 1.342(4) . ?
C21 O3 1.455(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1N 0.899(10) . ?
N2 H2N 0.899(10) . ?

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
O1 C1 N1 123.7(3) . . ?
O1 C1 N2 120.1(3) . . ?
N1 C1 N2 116.1(3) . . ?
C3 C2 N2 119.8(3) . . ?
C3 C2 C19 127.7(3) . . ?
N2 C2 C19 112.5(3) . . ?
C2 C3 C20 120.8(3) . . ?
C2 C3 C4 121.2(3) . . ?
C20 C3 C4 117.9(2) . . ?
N1 C4 C3 109.8(2) . . ?
N1 C4 C5 109.2(2) . . ?
C3 C4 C5 113.7(2) . . ?
N1 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
C6 C5 C18 119.8(3) . . ?
C6 C5 C4 118.9(2) . . ?
C18 C5 C4 121.1(2) . . ?
C5 C6 C7 122.8(3) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C8 C7 C12 119.9(3) . . ?
C8 C7 C6 121.4(3) . . ?
C12 C7 C6 118.6(3) . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.7(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 117.4(3) . . ?
C11 C12 C13 123.1(3) . . ?
C7 C12 C13 119.6(3) . . ?
C18 C13 C14 118.2(3) . . ?
C18 C13 C12 119.6(3) . . ?
C14 C13 C12 122.2(3) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 122.2(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C13 118.1(3) . . ?
C17 C18 C5 122.9(3) . . ?
C13 C18 C5 119.1(3) . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 O3 121.7(3) . . ?
O2 C20 C3 127.7(3) . . ?
O3 C20 C3 110.7(3) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 126.1(3) . . ?
C1 N1 H1N 112(2) . . ?
C4 N1 H1N 120(2) . . ?
C1 N2 C2 124.8(2) . . ?
C1 N2 H2N 115(2) . . ?
C2 N2 H2N 120(2) . . ?
C20 O3 C21 114.8(3) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_8RED
_database_code_depnum_ccdc_archive 'CCDC 1998546'
loop_
_audit_author_name
_audit_author_address
'Alakbar Huseynzada'
;Baku State University
Azerbaijan
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O6, 0.5(H2 O)'
_chemical_formula_sum            'C16 H19 N2 O6.50'
_chemical_formula_weight         343.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1493(12)
_cell_length_b                   9.6420(17)
_cell_length_c                   11.4398(10)
_cell_angle_alpha                74.396(10)
_cell_angle_beta                 88.752(10)
_cell_angle_gamma                78.900(17)
_cell_volume                     849.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      24

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             362
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  300
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5202
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4945
_reflns_number_gt                4128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'MERCURY (Macrae et al.2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Position of H atom belonging to the secondary amine was located in the final
 deltaF map and refined restraining the N-H distance to be 0.90 +- 0.01 Å.
 Water solvent molecule occurs in a partly populated atom site. 
 Occupancy for the O1W atom site was fixed at 0.5, whereas the H atoms
 belonging  to water molecules were placed at calculated positions and
 refined as riding atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.1859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4945
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1676
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66983(17) 0.12550(14) 0.19457(12) 0.0315(3) Uani 1 1 d . . . . .
C2 C 0.5563(2) -0.08366(14) 0.18104(13) 0.0373(3) Uani 1 1 d . . . . .
C3 C 0.67308(19) -0.08562(16) 0.36432(13) 0.0389(3) Uani 1 1 d . . . . .
C4 C 0.70542(17) 0.05882(15) 0.31678(12) 0.0342(3) Uani 1 1 d . . . . .
C5 C 0.69718(17) 0.27309(14) 0.12792(12) 0.0322(3) Uani 1 1 d . . . . .
C6 C 0.78983(18) 0.29413(14) 0.02224(12) 0.0345(3) Uani 1 1 d . . . . .
C7 C 0.81155(19) 0.43387(16) -0.04368(13) 0.0385(3) Uani 1 1 d . . . . .
H7 H 0.873046 0.446515 -0.113915 0.046 Uiso 1 1 calc R U . . .
C8 C 0.73939(19) 0.55281(15) -0.00192(13) 0.0393(3) Uani 1 1 d . . . . .
C9 C 0.6502(2) 0.53604(15) 0.10414(14) 0.0399(3) Uani 1 1 d . . . . .
H9 H 0.605173 0.617159 0.131868 0.048 Uiso 1 1 calc R U . . .
C10 C 0.62920(18) 0.39706(14) 0.16809(12) 0.0346(3) Uani 1 1 d . . . . .
C11 C 0.7201(3) -0.1727(2) 0.49312(15) 0.0566(5) Uani 1 1 d . . . . .
H11A H 0.632376 -0.147407 0.545460 0.085 Uiso 1 1 calc R U . . .
H11B H 0.822005 -0.150607 0.517378 0.085 Uiso 1 1 calc R U . . .
H11C H 0.735963 -0.275556 0.498813 0.085 Uiso 1 1 calc R U . . .
C12 C 0.78469(19) 0.13202(17) 0.39279(13) 0.0398(3) Uani 1 1 d . . . . .
C13 C 0.7812(3) 0.1840(3) 0.58320(18) 0.0697(6) Uani 1 1 d . . . . .
H13A H 0.890527 0.126140 0.608438 0.105 Uiso 1 1 calc R U . . .
H13B H 0.712093 0.179958 0.652611 0.105 Uiso 1 1 calc R U . . .
H13C H 0.790235 0.283978 0.545782 0.105 Uiso 1 1 calc R U . . .
C14 C 0.9553(3) 0.1814(2) -0.11517(17) 0.0624(5) Uani 1 1 d . . . . .
H14A H 0.885795 0.242432 -0.183536 0.094 Uiso 1 1 calc R U . . .
H14B H 0.993193 0.085701 -0.127002 0.094 Uiso 1 1 calc R U . . .
H14C H 1.050009 0.224460 -0.107512 0.094 Uiso 1 1 calc R U . . .
C15 C 0.8277(3) 0.7245(2) -0.17229(17) 0.0597(5) Uani 1 1 d . . . . .
H15A H 0.942126 0.673715 -0.162883 0.090 Uiso 1 1 calc R U . . .
H15B H 0.823630 0.828184 -0.202061 0.090 Uiso 1 1 calc R U . . .
H15C H 0.769659 0.692038 -0.229006 0.090 Uiso 1 1 calc R U . . .
C16 C 0.4800(3) 0.4913(2) 0.32035(19) 0.0654(6) Uani 1 1 d . . . . .
H16A H 0.572151 0.533418 0.335850 0.098 Uiso 1 1 calc R U . . .
H16B H 0.425192 0.457819 0.394868 0.098 Uiso 1 1 calc R U . . .
H16C H 0.402034 0.564073 0.263348 0.098 Uiso 1 1 calc R U . . .
N1 N 0.59874(16) 0.05200(12) 0.13067(10) 0.0352(3) Uani 1 1 d D . . . .
H1N H 0.574(2) 0.0936(19) 0.0513(9) 0.042 Uiso 1 1 d D U . . .
N2 N 0.60446(18) -0.15421(13) 0.29894(12) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.47592(18) -0.13689(12) 0.11991(10) 0.0509(3) Uani 1 1 d . . . . .
O2 O 0.90487(17) 0.18763(18) 0.36577(11) 0.0602(4) Uani 1 1 d . . . . .
O3 O 0.70741(16) 0.12703(15) 0.49742(10) 0.0514(3) Uani 1 1 d . . . . .
O4 O 0.86154(16) 0.16921(12) -0.00761(10) 0.0460(3) Uani 1 1 d . . . . .
O5 O 0.74996(18) 0.69410(12) -0.05812(12) 0.0542(3) Uani 1 1 d . . . . .
O6 O 0.54038(16) 0.37075(11) 0.27142(10) 0.0451(3) Uani 1 1 d . . . . .
O1W O 0.9388(10) 0.5236(7) 0.3590(6) 0.152(2) Uani 0.5 1 d . . P . .
H1WA H 1.052125 0.529263 0.375054 0.183 Uiso 0.5 1 d R U P . .
H1WB H 0.887340 0.511177 0.436502 0.183 Uiso 0.5 1 d R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3518(16) . ?
C1 C4 1.3835(18) . ?
C1 C5 1.4789(17) . ?
C2 O1 1.2345(17) . ?
C2 N2 1.3647(18) . ?
C2 N1 1.3867(17) . ?
C3 N2 1.3177(19) . ?
C3 C4 1.4256(19) . ?
C3 C11 1.503(2) . ?
C4 C12 1.4839(19) . ?
C5 C6 1.4001(19) . ?
C5 C10 1.4059(19) . ?
C6 O4 1.3603(17) . ?
C6 C7 1.3981(19) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9300 . ?
C8 O5 1.3595(17) . ?
C8 C9 1.388(2) . ?
C9 C10 1.3841(18) . ?
C9 H9 0.9300 . ?
C10 O6 1.3630(17) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O2 1.2008(19) . ?
C12 O3 1.3339(18) . ?
C13 O3 1.438(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O4 1.424(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O5 1.422(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O6 1.423(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1N 0.898(9) . ?
O1W H1WA 0.9601 . ?
O1W H1WB 0.9601 . ?

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
N1 C1 C4 117.53(11) . . ?
N1 C1 C5 116.68(11) . . ?
C4 C1 C5 125.75(12) . . ?
O1 C2 N2 121.80(13) . . ?
O1 C2 N1 120.06(13) . . ?
N2 C2 N1 118.13(12) . . ?
N2 C3 C4 123.11(12) . . ?
N2 C3 C11 115.02(13) . . ?
C4 C3 C11 121.85(14) . . ?
C1 C4 C3 117.53(12) . . ?
C1 C4 C12 120.73(12) . . ?
C3 C4 C12 121.62(12) . . ?
C6 C5 C10 117.89(11) . . ?
C6 C5 C1 121.16(12) . . ?
C10 C5 C1 120.94(12) . . ?
O4 C6 C7 123.21(13) . . ?
O4 C6 C5 115.15(11) . . ?
C7 C6 C5 121.58(13) . . ?
C8 C7 C6 118.40(13) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
O5 C8 C7 124.15(14) . . ?
O5 C8 C9 114.11(13) . . ?
C7 C8 C9 121.73(12) . . ?
C10 C9 C8 119.16(13) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O6 C10 C9 123.16(13) . . ?
O6 C10 C5 115.62(11) . . ?
C9 C10 C5 121.21(13) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O3 123.34(14) . . ?
O2 C12 C4 125.03(14) . . ?
O3 C12 C4 111.62(12) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C2 123.88(11) . . ?
C1 N1 H1N 119.0(12) . . ?
C2 N1 H1N 117.1(12) . . ?
C3 N2 C2 119.34(12) . . ?
C12 O3 C13 116.75(13) . . ?
C6 O4 C14 118.60(12) . . ?
C8 O5 C15 118.54(14) . . ?
C10 O6 C16 117.47(12) . . ?
H1WA O1W H1WB 104.7 . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_all_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1998557'
loop_
_audit_author_name
_audit_author_address
'Alakbar Huseynzada'
;Baku State University
Azerbaijan
;
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "'C14 H13 N3 O3 + C2H5OH"
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'

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

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

_cell_length_a                   23.7495(15)
_cell_length_b                   23.7495(15)
_cell_length_c                   4.8467(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2733.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53026
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         25.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2566
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+2.8664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001

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 0.19194(6) 0.59177(6) 1.1742(3) 0.0269(4) Uani 1 1 d . . . . .
O2 O 0.14949(8) 0.66137(6) 1.4019(4) 0.0392(4) Uani 1 1 d . . . . .
O3 O 0.01927(6) 0.44341(6) 1.7559(3) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.08807(7) 0.47198(7) 1.4627(3) 0.0186(4) Uani 1 1 d . . . . .
H1 H 0.0890(9) 0.4387(10) 1.391(5) 0.020(6) Uiso 1 1 d . . . . .
N2 N 0.05849(7) 0.52991(7) 1.8118(4) 0.0192(4) Uani 1 1 d . . . . .
H2 H 0.0344(10) 0.5365(9) 1.944(5) 0.028(6) Uiso 1 1 d . . . . .
N3 N 0.35552(8) 0.39691(8) 2.2216(4) 0.0340(5) Uani 1 1 d . . . . .
C1 C 0.12631(8) 0.56567(8) 1.5050(4) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.13956(8) 0.50480(8) 1.4340(4) 0.0180(4) Uani 1 1 d . . . . .
H2A H 0.151295 0.503372 1.236019 0.022 Uiso 1 1 calc R U . . .
C3 C 0.05380(8) 0.47891(8) 1.6798(4) 0.0178(4) Uani 1 1 d . . . . .
C4 C 0.08681(8) 0.57509(8) 1.6978(4) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.15559(9) 0.61144(9) 1.3630(4) 0.0242(5) Uani 1 1 d . . . . .
C6 C 0.22435(10) 0.63386(11) 1.0289(6) 0.0386(6) Uani 1 1 d . . . . .
H6A H 0.252009 0.615295 0.909586 0.058 Uiso 1 1 calc R U . . .
H6B H 0.243938 0.657858 1.162491 0.058 Uiso 1 1 calc R U . . .
H6C H 0.199086 0.656984 0.916110 0.058 Uiso 1 1 calc R U . . .
C7 C 0.18753(8) 0.48029(8) 1.6077(4) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.24221(9) 0.50048(9) 1.5785(5) 0.0250(5) Uani 1 1 d . . . . .
H8A H 0.249414 0.529932 1.450673 0.030 Uiso 1 1 calc R U . . .
C9 C 0.28619(9) 0.47875(9) 1.7307(4) 0.0260(5) Uani 1 1 d . . . . .
H9A H 0.323371 0.492622 1.706174 0.031 Uiso 1 1 calc R U . . .
C10 C 0.27533(8) 0.43632(8) 1.9201(4) 0.0222(4) Uani 1 1 d . . . . .
C11 C 0.22136(9) 0.41532(9) 1.9515(5) 0.0264(5) Uani 1 1 d . . . . .
H11A H 0.214068 0.386120 2.080652 0.032 Uiso 1 1 calc R U . . .
C12 C 0.17828(8) 0.43714(9) 1.7938(5) 0.0239(5) Uani 1 1 d . . . . .
H12A H 0.141388 0.422190 1.813333 0.029 Uiso 1 1 calc R U . . .
C13 C 0.32013(9) 0.41403(9) 2.0865(5) 0.0249(5) Uani 1 1 d . . . . .
C14 C 0.06676(9) 0.63018(9) 1.8091(5) 0.0277(5) Uani 1 1 d . . . . .
H14A H 0.063932 0.627896 2.010494 0.042 Uiso 1 1 calc R U . . .
H14B H 0.029690 0.638930 1.731300 0.042 Uiso 1 1 calc R U . . .
H14C H 0.093500 0.659861 1.758503 0.042 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
O1 C5 1.342(3) . ?
O1 C6 1.445(3) . ?
O2 C5 1.209(3) . ?
O3 C3 1.233(2) . ?
N1 C3 1.340(3) . ?
N1 C2 1.457(2) . ?
N1 H1 0.86(2) . ?
N2 C3 1.374(2) . ?
N2 C4 1.382(3) . ?
N2 H2 0.87(3) . ?
N3 C13 1.141(3) . ?
C1 C4 1.343(3) . ?
C1 C5 1.462(3) . ?
C1 C2 1.519(3) . ?
C2 C7 1.531(3) . ?
C2 H2A 1.0000 . ?
C4 C14 1.493(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.383(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.379(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.384(3) . ?
C10 C13 1.436(3) . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 115.74(18) . . ?
C3 N1 C2 121.26(16) . . ?
C3 N1 H1 116.4(15) . . ?
C2 N1 H1 115.4(14) . . ?
C3 N2 C4 122.53(18) . . ?
C3 N2 H2 116.6(15) . . ?
C4 N2 H2 118.2(15) . . ?
C4 C1 C5 122.40(18) . . ?
C4 C1 C2 117.44(17) . . ?
C5 C1 C2 120.16(17) . . ?
N1 C2 C1 108.28(15) . . ?
N1 C2 C7 111.63(16) . . ?
C1 C2 C7 113.04(15) . . ?
N1 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C7 C2 H2A 107.9 . . ?
O3 C3 N1 123.70(18) . . ?
O3 C3 N2 121.17(18) . . ?
N1 C3 N2 115.11(17) . . ?
C1 C4 N2 119.27(18) . . ?
C1 C4 C14 128.33(19) . . ?
N2 C4 C14 112.38(18) . . ?
O2 C5 O1 121.64(19) . . ?
O2 C5 C1 126.8(2) . . ?
O1 C5 C1 111.60(17) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.03(18) . . ?
C12 C7 C2 121.46(17) . . ?
C8 C7 C2 120.49(17) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 119.01(19) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C11 C10 C9 120.45(19) . . ?
C11 C10 C13 119.45(19) . . ?
C9 C10 C13 120.10(19) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C7 121.50(19) . . ?
C11 C12 H12A 119.3 . . ?
C7 C12 H12A 119.3 . . ?
N3 C13 C10 179.0(2) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C1 -44.1(2) . . . . ?
C3 N1 C2 C7 81.0(2) . . . . ?
C4 C1 C2 N1 32.8(2) . . . . ?
C5 C1 C2 N1 -146.44(17) . . . . ?
C4 C1 C2 C7 -91.4(2) . . . . ?
C5 C1 C2 C7 89.3(2) . . . . ?
C2 N1 C3 O3 -159.24(18) . . . . ?
C2 N1 C3 N2 22.4(3) . . . . ?
C4 N2 C3 O3 -164.87(18) . . . . ?
C4 N2 C3 N1 13.5(3) . . . . ?
C5 C1 C4 N2 176.20(18) . . . . ?
C2 C1 C4 N2 -3.0(3) . . . . ?
C5 C1 C4 C14 -2.1(3) . . . . ?
C2 C1 C4 C14 178.65(19) . . . . ?
C3 N2 C4 C1 -23.0(3) . . . . ?
C3 N2 C4 C14 155.57(18) . . . . ?
C6 O1 C5 O2 2.1(3) . . . . ?
C6 O1 C5 C1 -178.03(17) . . . . ?
C4 C1 C5 O2 1.7(3) . . . . ?
C2 C1 C5 O2 -179.1(2) . . . . ?
C4 C1 C5 O1 -178.21(18) . . . . ?
C2 C1 C5 O1 1.0(3) . . . . ?
N1 C2 C7 C12 -8.3(3) . . . . ?
C1 C2 C7 C12 114.1(2) . . . . ?
N1 C2 C7 C8 170.65(18) . . . . ?
C1 C2 C7 C8 -67.0(2) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C2 C7 C8 C9 -179.41(19) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C13 -178.32(19) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C13 C10 C11 C12 179.3(2) . . . . ?
C10 C11 C12 C7 -1.1(3) . . . . ?
C8 C7 C12 C11 1.5(3) . . . . ?
C2 C7 C12 C11 -179.55(19) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048




