#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:17:03 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289568 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247857.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_7247857
loop_
_publ_author_name
'Qi, Jing'
'Wang, Xiyan'
'Wang, Gan'
'Dubbaka, Srinivas Reddy'
'O'Neill, Patrick'
'Ang, Hwee Ting'
'Wu, Jie'
_publ_section_title
;
 Sustainable electrocatalytic oxidation of N-alkylamides to acyclic imides
 using H2O
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              306
_journal_page_last               311
_journal_paper_doi               10.1039/D3GC04010K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C9 H6 N2 O2'
_chemical_formula_weight         174.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'Dual Space'
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-07-10 deposited with the CCDC.	2023-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                94.101(2)
_cell_angle_beta                 93.691(2)
_cell_angle_gamma                96.948(2)
_cell_formula_units_Z            2
_cell_length_a                   3.7781(2)
_cell_length_b                   7.5804(3)
_cell_length_c                   14.7776(6)
_cell_measurement_reflns_used    5946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.51
_cell_measurement_theta_min      2.72
_cell_volume                     417.90(3)
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11723
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.553
_diffrn_reflns_theta_min         3.723
_diffrn_source                   'Microfocus Sealed Tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0870 before and 0.0486 after correction. 
The Ratio of minimum to maximum transmission is 0.9562. 
The λ/2 correction factor is Not present. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0385
_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)+(0.0672P)²+0.0785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2110
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc04010k2.cif
_cod_data_source_block           M266
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7247857.cif.
;
_cod_database_code               7247857
_shelx_shelxl_version_number     2019/1
_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. 
;
_computing_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -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 0.28030(19) 0.11039(9) 0.58259(5) 0.02292(17) Uani 1 1 d . . . . .
O2 O 0.22541(17) 0.47454(8) 0.40494(4) 0.02106(17) Uani 1 1 d . . . . .
N1 N 0.3737(2) 0.20622(10) 0.44271(5) 0.01774(17) Uani 1 1 d . . . . .
N2 N 0.9227(3) 0.22264(13) -0.04524(6) 0.0306(2) Uani 1 1 d . . . . .
H1 H 0.474(4) 0.108(2) 0.4279(10) 0.033(3) Uiso 1 1 d . . . . .
C1 C 0.2489(2) 0.22143(11) 0.52785(6) 0.01771(18) Uani 1 1 d . . . . .
H1A H 0.133854 0.322274 0.544698 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3462(2) 0.33739(11) 0.38275(6) 0.01644(18) Uani 1 1 d . . . . .
C3 C 0.4721(2) 0.30288(11) 0.29014(6) 0.01692(18) Uani 1 1 d . . . . .
C4 C 0.5226(2) 0.13384(12) 0.25357(6) 0.01958(19) Uani 1 1 d . . . . .
H4 H 0.478497 0.033704 0.288248 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6372(2) 0.11161(12) 0.16645(6) 0.0212(2) Uani 1 1 d . . . . .
H5 H 0.671529 -0.003352 0.141204 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7013(2) 0.26000(13) 0.11657(6) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.6509(3) 0.42985(13) 0.15251(6) 0.0235(2) Uani 1 1 d . . . . .
H7 H 0.695283 0.530046 0.117889 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5354(2) 0.45032(12) 0.23929(6) 0.0214(2) Uani 1 1 d . . . . .
H8 H 0.499078 0.565149 0.264301 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8238(3) 0.23828(13) 0.02636(7) 0.0244(2) Uani 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
C1 N1 C2 121.44(7) . . ?
C1 N1 H1 116.9(9) . . ?
C2 N1 H1 121.7(9) . . ?
O1 C1 N1 122.48(8) . . ?
O1 C1 H1A 118.8 . . ?
N1 C1 H1A 118.8 . . ?
O2 C2 N1 121.30(8) . . ?
O2 C2 C3 121.67(8) . . ?
N1 C2 C3 117.03(7) . . ?
C4 C3 C8 120.14(8) . . ?
C4 C3 C2 123.30(8) . . ?
C8 C3 C2 116.56(8) . . ?
C5 C4 C3 120.09(8) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.21(8) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.14(8) . . ?
C5 C6 C9 119.55(8) . . ?
C7 C6 C9 119.31(8) . . ?
C8 C7 C6 119.14(8) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 120.27(8) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
N2 C9 C6 179.35(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 C1 1.2192(11) . ?
O2 C2 1.2173(10) . ?
N1 C1 1.3737(11) . ?
N1 C2 1.3870(11) . ?
N1 H1 0.892(15) . ?
N2 C9 1.1477(13) . ?
C1 H1A 0.9500 . ?
C2 C3 1.4934(12) . ?
C3 C4 1.3941(12) . ?
C3 C8 1.3963(12) . ?
C4 C5 1.3900(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.3939(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.3966(13) . ?
C6 C9 1.4438(12) . ?
C7 C8 1.3853(12) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
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 O1 0.892(15) 1.998(15) 2.8814(10) 170.3(13) 2_656 yes
C1 H1A O2 0.95 2.29 3.2266(10) 168.9 2_566 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
C2 N1 C1 O1 -177.69(8) . . . . ?
C1 N1 C2 O2 3.43(13) . . . . ?
C1 N1 C2 C3 -176.74(7) . . . . ?
O2 C2 C3 C4 -162.53(9) . . . . ?
N1 C2 C3 C4 17.64(12) . . . . ?
O2 C2 C3 C8 16.66(12) . . . . ?
N1 C2 C3 C8 -163.17(8) . . . . ?
C8 C3 C4 C5 0.22(13) . . . . ?
C2 C3 C4 C5 179.38(8) . . . . ?
C3 C4 C5 C6 0.12(13) . . . . ?
C4 C5 C6 C7 -0.25(14) . . . . ?
C4 C5 C6 C9 179.41(8) . . . . ?
C5 C6 C7 C8 0.04(14) . . . . ?
C9 C6 C7 C8 -179.62(8) . . . . ?
C6 C7 C8 C3 0.31(14) . . . . ?
C4 C3 C8 C7 -0.44(14) . . . . ?
C2 C3 C8 C7 -179.66(8) . . . . ?
