#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:03:17 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272555 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565173.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_1565173
loop_
_publ_author_name
'Nesterova, Oksana V.'
'Kuznetsov, Maxim L.'
'Pombeiro, Armando J. L.'
'Shul'pin, Georgiy B.'
'Nesterov, Dmytro S.'
_publ_section_title
;
 Homogeneous oxidation of C--H bonds with m-CPBA catalysed by a Co/Fe
 system: mechanistic insights from the point of view of the oxidant
;
_journal_issue                   1
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              282
_journal_page_last               299
_journal_paper_doi               10.1039/D1CY01991K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'H4 N2 O3'
_chemical_formula_weight         80.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_Hall           '-P 2ab 2a'
_space_group_name_H-M_alt        'P m m n :2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-20 deposited with the CCDC.	2021-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4460(6)
_cell_length_b                   5.7605(8)
_cell_length_c                   4.9406(6)
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.02
_cell_measurement_theta_min      3.74
_cell_volume                     154.99(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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 0.959
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1535
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.916
_diffrn_reflns_theta_min         5.437
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       block
_exptl_crystal_F_000             84
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     25
_refine_ls_number_reflns         259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.268
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0354P)²+0.0684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                234
_reflns_number_total             259
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cy01991k2.cif
_cod_data_source_block           ss100
_cod_depositor_comments
'Adding full bibliography for 1565173--1565174.cif.'
_cod_original_sg_symbol_H-M      'P m m n'
_cod_database_code               1565173
_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_res_file
;
TITL ss100 in Pmmn
    ss100.res
    created by SHELXL-2018/3 at 17:58:17 on 20-Jul-2020
CELL  0.71073   5.4460   5.7605   4.9406   90.000   90.000   90.000
ZERR    2.000   0.0006   0.0008   0.0006    0.000    0.000    0.000
LATT  1
SYMM 1/2-X, 1/2-Y, Z
SYMM -X, 1/2+Y, -Z
SYMM 1/2+X, -Y, -Z
SFAC N H O
UNIT 4 8 6
TEMP 23
L.S. 5
BOND $H
LIST 6
FMAP 2
PLAN 10
ACTA
OMIT 0 60
EQIV $1 x,y,z-1
EQIV $2 0.5-x,0.5-y,z
HTAB N2 O2
HTAB N2 O1_$1
HTAB N2 O2_$2
WGHT    0.035400    0.068400
FVAR       1.86248
O1    3    0.250000    0.750000    0.764708    10.25000    0.04206    0.03016 =
         0.01419    0.00000    0.00000    0.00000
N1    1    0.250000    0.750000    0.507409    10.25000    0.02467    0.02766 =
         0.01542    0.00000    0.00000    0.00000
O2    3    0.250000    0.563783    0.383831    10.50000    0.07268    0.04349 =
         0.03699   -0.02190    0.00000    0.00000
N2    1    0.250000    0.250000   -0.083960    10.25000    0.03857    0.02127 =
         0.02319    0.00000    0.00000    0.00000
H1    2    0.139336    0.250000    0.023022    10.50000    0.05454
H2    2    0.250000    0.381025   -0.183287    10.50000    0.07237

HKLF 4




REM  ss100 in Pmmn
REM wR2 = 0.111416, GooF = S = 1.26796, Restrained GooF = 1.26796 for all data
REM R1 = 0.045829 for 234 Fo > 4sig(Fo) and 0.051242 for all 259 data
REM 25 parameters refined using 0 restraints

END

WGHT      0.0353      0.0683

REM Highest difference peak  0.176,  deepest hole -0.242,  1-sigma level  0.048
Q1    1   0.1487  0.5720  0.4531  11.00000  0.05    0.18
Q2    1   0.0913  0.2500 -0.0489  10.50000  0.05    0.17
Q3    1   0.2500  0.6127  0.7961  10.50000  0.05    0.15
Q4    1   0.1173  0.4068  0.3223  11.00000  0.05    0.13
Q5    1   0.1143  0.6188  0.9330  11.00000  0.05    0.12
Q6    1   0.0615  0.6630  0.5637  11.00000  0.05    0.12
Q7    1   0.1549  0.7500  0.2258  10.50000  0.05    0.11
Q8    1   0.1626  0.5519 -0.3218  11.00000  0.05    0.11
Q9    1   0.0743  0.6787  0.3176  11.00000  0.05    0.11
Q10   1   0.0773  0.5256  0.2539  11.00000  0.05    0.10
;
_shelx_res_checksum              41907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z'
'x+1/2, -y, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z'
'-x-1/2, y, z'
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 0.250000 0.750000 0.7647(3) 0.0288(6) Uani 1 4 d S T P . .
N1 N 0.250000 0.750000 0.5074(4) 0.0226(5) Uani 1 4 d S T P . .
O2 O 0.250000 0.5638(3) 0.3838(3) 0.0511(6) Uani 1 2 d S T P . .
N2 N 0.250000 0.250000 -0.0840(5) 0.0277(6) Uani 1 4 d S T P . .
H1 H 0.139(6) 0.250000 0.023(5) 0.055(8) Uiso 1 2 d S . P . .
H2 H 0.250000 0.381(7) -0.183(7) 0.072(10) Uiso 1 2 d S . P . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0421(11) 0.0302(10) 0.0142(8) 0.000 0.000 0.000
N1 0.0247(9) 0.0277(10) 0.0154(9) 0.000 0.000 0.000
O2 0.0727(12) 0.0435(10) 0.0370(9) -0.0219(7) 0.000 0.000
N2 0.0386(13) 0.0213(10) 0.0232(10) 0.000 0.000 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
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 N1 O2 120.7(2) . 2_565 ?
O2 N1 O1 119.65(11) . . ?
O2 N1 O1 119.65(11) 2_565 . ?
H1 N2 H2 111.1(17) . . ?
H1 N2 H1 97(4) . 2 ?
H2 N2 H1 111.1(17) . 2 ?
H1 N2 H2 111.1(17) . 2 ?
H2 N2 H2 114(4) . 2 ?
H1 N2 H2 111.1(17) 2 2 ?
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 N1 1.271(2) . ?
N1 O2 1.2343(18) . ?
N1 O2 1.2343(18) 2_565 ?
N2 H1 0.80(3) . ?
N2 H2 0.90(4) . ?
N2 H1 0.80(3) 2 ?
N2 H2 0.90(4) 2 ?
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
N2 H1 O2 0.80(3) 2.609(18) 2.934(2) 106.1(18) . yes
N2 H2 O1 0.90(4) 2.14(4) 2.9757(8) 154(3) 1_554 yes
N2 H1 O2 0.80(3) 2.609(18) 2.934(2) 106.1(18) 2 yes
