#------------------------------------------------------------------------------
#$Date: 2023-07-04 04:53:55 +0300 (Tue, 04 Jul 2023) $
#$Revision: 284769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/94/1569410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1569410
loop_
_publ_author_name
'Bravetti, Federica'
'Tapmeyer, Lukas'
'Skorodumov, Kathrin'
'Alig, Edith'
'Habermehl, Stefan'
'Hühn, Robert'
'Bordignon, Simone'
'Gallo, Angelo'
'Nervi, Carlo'
'Chierotti, Michele R.'
'Schmidt, Martin U.'
_publ_section_title
;
 Leucopterin, the white pigment in butterfly wings: structural analysis by
 PDF fit, FIDEL fit, Rietveld refinement, solid-state NMR and DFT-D.
;
_journal_coeditor_code           LT5058
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first              448
_journal_page_last               463
_journal_paper_doi               10.1107/S2052252523004281
_journal_volume                  10
_journal_year                    2023
_chemical_formula_moiety         '2(C6 H5 N5 O3), H2 O'
_chemical_formula_sum            'C12 H12 N10 O7'
_chemical_formula_weight         408.32
_chemical_melting_point          'dehydration starting at 130 C'
_chemical_name_systematic        'Leucopterin hemihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.223(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0781(10)
_cell_length_b                   4.7930(6)
_cell_length_c                   18.345(2)
_cell_measurement_reflns_used    322
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.462
_cell_measurement_theta_min      4.821
_cell_volume                     710.28(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Siemens Bruker 3-circle diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3112
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        35.462
_diffrn_reflns_theta_max         35.462
_diffrn_reflns_theta_min         4.821
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_meas      'about 1.83'
_exptl_crystal_density_method    'suspension in iodobenzene does not separate'
_exptl_crystal_description       'small, thin square'
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method 'Recrystallisation from NaOH/HCl'
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.411
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     57
_refine_ls_number_reflns         309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.411
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.1413
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4417
_refine_ls_wR_factor_ref         0.4451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                288
_reflns_number_total             322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lt5058.cif
_cod_data_source_block           Leuco
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               1569410
_shelx_shelxl_version_number     2018/3
_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, -y, -z'
'x, -y, z-1/2'
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
O11 O 0.8883(16) 0.207(2) 0.1816(7) 0.041(7)
O61 O 0.5425(17) -0.339(3) -0.0842(7) 0.041(7)
O81 O 0.6770(17) -0.229(2) 0.1789(8) 0.032(7)
N02 N 0.873(2) 0.237(3) 0.0578(10) 0.045(9)
N03 N 0.874(2) 0.295(3) -0.0673(10) 0.031(8)
N05 N 0.7013(15) -0.012(3) -0.1400(9) 0.030(8)
N07 N 0.664(2) -0.200(3) 0.0551(10) 0.032(8)
N41 N 0.851(2) 0.350(3) -0.1912(10) 0.045(8)
C01 C 0.826(2) 0.112(4) 0.1207(11) 0.018(7)
C04 C 0.801(2) 0.207(4) -0.1291(11) 0.026(8)
C06 C 0.651(3) -0.141(4) -0.0781(14) 0.040(9)
C08 C 0.711(2) -0.118(4) 0.1218(12) 0.018(7)
C09 C 0.705(2) -0.066(4) -0.0116(11) 0.016(8)
C10 C 0.810(2) 0.146(4) -0.0110(10) 0.016(8)
O1W O 0.500000 0.286(3) 0.250000 0.048(8)
H1 H 0.5925 -0.3738 0.0518 0.03
H2 H 0.8028 0.2987 -0.2406 0.03
H3 H 0.9357 0.5057 -0.1871 0.03
H6 H 0.6662 -0.0764 -0.1904 0.03
H7 H 0.9544 0.3981 0.0597 0.03
H1W H 0.5716 0.4016 0.22126 0.03
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'
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
C01 N02 C10 121.2(18) . . ?
C04 N03 C10 108.1(18) . . ?
C04 N05 C06 114(2) . . ?
C08 N07 C09 126.1(18) . . ?
O11 C01 N02 117.7(18) . . ?
O11 C01 C08 120.1(19) . . ?
N02 C01 C08 122.2(19) . . ?
N03 C04 N05 129(2) . . ?
N03 C04 N41 114(2) . . ?
N05 C04 N41 116.2(19) . . ?
O61 C06 C09 119(2) . . ?
O61 C06 N05 118(2) . . ?
C09 C06 N05 123(2) . . ?
O81 C08 N07 126.7(18) . . ?
O81 C08 C01 119.9(19) . . ?
N07 C08 C01 113.1(19) . . ?
C10 C09 C06 115(2) . . ?
C10 C09 N07 119.2(19) . . ?
C06 C09 N07 126(2) . . ?
C09 C10 N03 130(2) . . ?
C09 C10 N02 117.8(19) . . ?
N03 C10 N02 112.2(17) . . ?
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
O11 C01 1.306(19) . ?
O61 C06 1.30(2) . ?
O81 C08 1.209(19) . ?
N02 C01 1.36(2) . ?
N02 C10 1.43(2) . ?
N03 C04 1.35(2) . ?
N03 C10 1.36(2) . ?
N05 C04 1.34(2) . ?
N05 C06 1.36(2) . ?
N07 C08 1.34(2) . ?
N07 C09 1.42(2) . ?
N41 C04 1.39(2) . ?
C01 C08 1.44(2) . ?
C06 C09 1.34(2) . ?
C09 C10 1.33(2) . ?
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
C10 N02 C01 O11 -179.6(13) . . . . ?
C10 N02 C01 C08 0(3) . . . . ?
C10 N03 C04 N05 -10(3) . . . . ?
C10 N03 C04 N41 177.9(13) . . . . ?
C06 N05 C04 N03 10(3) . . . . ?
C06 N05 C04 N41 -178.3(16) . . . . ?
C04 N05 C06 O61 173.8(15) . . . . ?
C04 N05 C06 C09 -4(3) . . . . ?
C09 N07 C08 O81 179.6(16) . . . . ?
C09 N07 C08 C01 -6(3) . . . . ?
O11 C01 C08 O81 -3(3) . . . . ?
N02 C01 C08 O81 177.4(17) . . . . ?
O11 C01 C08 N07 -177.1(15) . . . . ?
N02 C01 C08 N07 3(2) . . . . ?
O61 C06 C09 C10 -177.2(16) . . . . ?
N05 C06 C09 C10 0(3) . . . . ?
O61 C06 C09 N07 6(3) . . . . ?
N05 C06 C09 N07 -176.6(15) . . . . ?
C08 N07 C09 C10 7(3) . . . . ?
C08 N07 C09 C06 -176.6(17) . . . . ?
C06 C09 C10 N03 -1(3) . . . . ?
N07 C09 C10 N03 175.7(17) . . . . ?
C06 C09 C10 N02 -179.6(15) . . . . ?
N07 C09 C10 N02 -2(3) . . . . ?
C04 N03 C10 C09 5(3) . . . . ?
C04 N03 C10 N02 -176.3(12) . . . . ?
C01 N02 C10 C09 -1(3) . . . . ?
C01 N02 C10 N03 -179.1(14) . . . . ?
