#------------------------------------------------------------------------------
#$Date: 2024-10-02 00:36:32 +0200 (Wed 02 de Oct de 2024) $
#$Revision: 294970 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/94/7249410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249410
loop_
_publ_author_name
'Andrei, Churakov'
_publ_section_title
;
 Three peroxomorphic H2O2 adducts of antibiotic furacin: the first cases
 of 2D hydrogen-bonded peroxide layers and concerted flip-flop hydrogen
 disorder of peroxide species.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D4CE00822G
_journal_year                    2024
_chemical_formula_moiety         'C6 H6 N4 O4, H2 O2'
_chemical_formula_sum            'C6 H8 N4 O6'
_chemical_formula_weight         232.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.580(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3836(3)
_cell_length_b                   8.3568(3)
_cell_length_c                   15.1792(5)
_cell_measurement_reflns_used    6448
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.529
_cell_measurement_theta_min      2.714
_cell_volume                     926.12(6)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12635
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.714
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.9281
_exptl_transmission_factor_min   0.8937
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0037(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0315
_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)+(0.0383P)²+0.3966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1987
_reflns_number_total             2228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00822g3.cif
_cod_data_source_block           a1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249410
_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.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.994
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'
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 0.70820(12) 0.20900(11) 0.62786(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.53004(11) 0.13041(11) 0.60598(6) 0.0209(2) Uani 1 1 d . . . . .
H1 H 0.747(2) 0.201(2) 0.5781(13) 0.037(5) Uiso 1 1 d . . . . .
H2 H 0.556(2) 0.034(2) 0.6276(11) 0.031(4) Uiso 1 1 d . . . . .
O3 O 0.56307(12) 0.83625(10) 0.67347(5) 0.0203(2) Uani 1 1 d . . . . .
O4 O 0.81027(11) 0.30917(9) 0.43597(5) 0.01407(18) Uani 1 1 d . . . . .
O5 O 0.80393(12) 0.00958(10) 0.47353(5) 0.0198(2) Uani 1 1 d . . . . .
O6 O 0.91583(12) -0.05856(10) 0.35345(6) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.63447(14) 0.57187(12) 0.68546(7) 0.0170(2) Uani 1 1 d . . . . .
H11 H 0.675(2) 0.487(2) 0.6621(11) 0.028(4) Uiso 1 1 d . . . . .
H12 H 0.626(2) 0.577(2) 0.7410(12) 0.029(4) Uiso 1 1 d . . . . .
N2 N 0.65065(14) 0.71049(12) 0.55524(6) 0.0160(2) Uani 1 1 d . . . . .
H21 H 0.626(2) 0.794(2) 0.5261(11) 0.027(4) Uiso 1 1 d . . . . .
N3 N 0.71400(13) 0.57604(11) 0.51965(6) 0.0141(2) Uani 1 1 d . . . . .
N4 N 0.86373(13) 0.04207(12) 0.40348(6) 0.0157(2) Uani 1 1 d . . . . .
C1 C 0.61340(15) 0.70993(14) 0.64113(7) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.76173(15) 0.59318(14) 0.44194(7) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.82424(15) 0.45612(14) 0.39766(7) 0.0141(2) Uani 1 1 d . . . . .
C4 C 0.89460(16) 0.44181(15) 0.31952(7) 0.0163(2) Uani 1 1 d . . . . .
C5 C 0.92530(15) 0.27677(14) 0.30720(7) 0.0161(2) Uani 1 1 d . . . . .
C6 C 0.87206(15) 0.20457(14) 0.37929(7) 0.0148(2) Uani 1 1 d . . . . .
H3 H 0.757(2) 0.6934(18) 0.4109(10) 0.020(4) Uiso 1 1 d . . . . .
H4 H 0.919(2) 0.528(2) 0.2842(10) 0.026(4) Uiso 1 1 d . . . . .
H5 H 0.971(2) 0.2266(19) 0.2594(11) 0.024(4) Uiso 1 1 d . . . . .
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'
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
O2 O1 H1 99.8(12) . . ?
O1 O2 H2 100.7(11) . . ?
C6 O4 C3 104.81(8) . . ?
C1 N1 H11 121.6(11) . . ?
C1 N1 H12 115.8(11) . . ?
H11 N1 H12 121.6(16) . . ?
N3 N2 C1 120.29(10) . . ?
N3 N2 H21 123.0(11) . . ?
C1 N2 H21 116.6(11) . . ?
C2 N3 N2 115.42(10) . . ?
O6 N4 O5 124.22(10) . . ?
O6 N4 C6 117.83(9) . . ?
O5 N4 C6 117.95(9) . . ?
O3 C1 N1 123.67(10) . . ?
O3 C1 N2 119.08(10) . . ?
N1 C1 N2 117.24(10) . . ?
N3 C2 C3 119.33(10) . . ?
N3 C2 H3 123.5(9) . . ?
C3 C2 H3 117.2(9) . . ?
O4 C3 C4 110.60(10) . . ?
O4 C3 C2 117.77(9) . . ?
C4 C3 C2 131.60(11) . . ?
C3 C4 C5 106.78(10) . . ?
C3 C4 H4 124.3(10) . . ?
C5 C4 H4 128.9(10) . . ?
C6 C5 C4 104.79(10) . . ?
C6 C5 H5 127.1(10) . . ?
C4 C5 H5 128.1(10) . . ?
O4 C6 C5 113.02(10) . . ?
O4 C6 N4 115.13(9) . . ?
C5 C6 N4 131.81(11) . . ?
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 O2 1.4634(12) . ?
O1 H1 0.849(19) . ?
O2 H2 0.881(19) . ?
O3 C1 1.2441(14) . ?
O4 C6 1.3526(13) . ?
O4 C3 1.3693(13) . ?
O5 N4 1.2407(12) . ?
O6 N4 1.2326(13) . ?
N1 C1 1.3330(15) . ?
N1 H11 0.863(18) . ?
N1 H12 0.856(17) . ?
N2 N3 1.3596(13) . ?
N2 C1 1.3720(14) . ?
N2 H21 0.833(17) . ?
N3 C2 1.2884(14) . ?
N4 C6 1.4104(15) . ?
C2 C3 1.4385(16) . ?
C2 H3 0.960(15) . ?
C3 C4 1.3693(15) . ?
C4 C5 1.4146(17) . ?
C4 H4 0.929(16) . ?
C5 C6 1.3581(16) . ?
C5 H5 0.945(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
O1 H1 O4 0.849(19) 2.449(19) 3.2261(12) 152.5(16) . yes
O1 H1 O5 0.849(19) 2.334(19) 3.0429(13) 141.3(16) . yes
O2 H2 O3 0.881(19) 1.791(19) 2.6603(13) 168.8(16) 1_545 yes
N1 H11 O1 0.863(18) 2.404(18) 3.2246(14) 159.1(15) . yes
N1 H12 O6 0.856(17) 2.477(17) 3.2171(13) 145.2(14) 4_566 yes
N2 H21 O5 0.833(17) 2.433(17) 3.0798(13) 135.1(14) 1_565 yes
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
C1 N2 N3 C2 -173.46(10) . . . . ?
N3 N2 C1 O3 176.94(10) . . . . ?
N3 N2 C1 N1 -2.81(16) . . . . ?
N2 N3 C2 C3 -177.78(10) . . . . ?
C6 O4 C3 C4 -0.50(12) . . . . ?
C6 O4 C3 C2 177.94(10) . . . . ?
N3 C2 C3 O4 7.37(16) . . . . ?
N3 C2 C3 C4 -174.58(12) . . . . ?
O4 C3 C4 C5 0.56(13) . . . . ?
C2 C3 C4 C5 -177.59(12) . . . . ?
C3 C4 C5 C6 -0.38(13) . . . . ?
C3 O4 C6 C5 0.25(12) . . . . ?
C3 O4 C6 N4 -177.59(9) . . . . ?
C4 C5 C6 O4 0.08(13) . . . . ?
C4 C5 C6 N4 177.46(12) . . . . ?
O6 N4 C6 O4 178.95(9) . . . . ?
O5 N4 C6 O4 -0.81(15) . . . . ?
O6 N4 C6 C5 1.62(18) . . . . ?
O5 N4 C6 C5 -178.15(12) . . . . ?
H1 O1 O2 H2 98.3(17) . . . . ?
