#------------------------------------------------------------------------------
#$Date: 2025-11-29 22:26:49 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303838 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/09/7250922.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_7250922
loop_
_publ_author_name
'Wang, Zengping'
'Zhai, Xiaofang'
'Bai, Pengtao'
'Fang, Li'
'Zheng, Shaojun'
'Zhao, Jiajia'
'Yang, Fu'
'Xu, Chen'
'Song, Heng'
_publ_section_title
;
 An unconventional photochemical amide synthesis from excited-state
 nitroarenes
;
_journal_issue                   42
_journal_name_full               'Green Chemistry'
_journal_page_first              13427
_journal_page_last               13435
_journal_paper_doi               10.1039/D5GC03649F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H7 N O3'
_chemical_formula_sum            'C10 H7 N O3'
_chemical_formula_weight         189.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.35(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.158(4)
_cell_length_b                   16.263(13)
_cell_length_c                   11.109(10)
_cell_measurement_temperature    296(2)
_cell_volume                     919.5(13)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.937
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4212
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.009
_diffrn_reflns_theta_min         2.505
_exptl_absorpt_coefficient_mu    0.103
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             392
_refine_diff_density_max         1.133
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.690
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.690
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2590
_refine_ls_wR_factor_ref         0.2929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1218
_reflns_number_total             2084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5gc03649f2.cif
_cod_data_source_block           Y_a
_cod_depositor_comments
'Adding full bibliography for 7250918--7250924.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7250922
_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.
;
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'
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 0.5622(6) 0.21465(18) 0.46799(18) 0.0587(9) Uani 1 1 d . . . . .
O2 O 0.9093(6) 0.10179(17) 0.43236(19) 0.0594(9) Uani 1 1 d . . . . .
O3 O 0.4496(7) 0.35257(19) 0.5324(2) 0.0655(10) Uani 1 1 d . . . . .
N1 N 0.6026(6) 0.29036(18) 0.7100(2) 0.0415(8) Uani 1 1 d . . . . .
C1 C 0.0657(9) 0.4399(3) 0.6463(4) 0.0608(12) Uani 1 1 d . . . . .
H5 H 0.003553 0.421382 0.563631 0.073 Uiso 1 1 calc R U . . .
H1 H -0.071489 0.450722 0.694457 0.073 Uiso 1 1 calc R U . . .
C2 C 0.3218(8) 0.4050(2) 0.7112(3) 0.0493(10) Uani 1 1 d . . . . .
H7 H 0.337337 0.396399 0.799410 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4612(7) 0.3473(2) 0.6435(3) 0.0423(9) Uani 1 1 d . . . . .
C4 C 0.7769(7) 0.2299(2) 0.6764(3) 0.0391(9) Uani 1 1 d . . . . .
C5 C 0.9742(8) 0.2026(2) 0.7663(3) 0.0459(9) Uani 1 1 d . . . . .
H4 H 0.990604 0.226145 0.843456 0.055 Uiso 1 1 calc R U . . .
C6 C 1.1470(9) 0.1421(2) 0.7465(3) 0.0517(10) Uani 1 1 d . . . . .
H3 H 1.275338 0.124258 0.809740 0.062 Uiso 1 1 calc R U . . .
C7 C 1.1289(9) 0.1079(3) 0.6320(4) 0.0550(11) Uani 1 1 d . . . . .
H2 H 1.246442 0.067782 0.615105 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7520(8) 0.1950(2) 0.5616(3) 0.0444(9) Uani 1 1 d . . . . .
C9 C 0.9340(9) 0.1349(2) 0.5454(3) 0.0511(11) Uani 1 1 d . . . . .
C10 C 0.2986(9) 0.4919(3) 0.6668(4) 0.0643(12) Uani 1 1 d . . . . .
H6 H 0.376761 0.542636 0.658322 0.077 Uiso 1 1 calc R U . . .
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
C3 N1 C4 130.5(2) . . ?
C10 C1 C2 60.5(3) . . ?
C10 C1 H5 117.7 . . ?
C2 C1 H5 117.7 . . ?
C10 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
H5 C1 H1 114.8 . . ?
C3 C2 C10 117.1(3) . . ?
C3 C2 C1 117.4(3) . . ?
C10 C2 C1 58.0(3) . . ?
C3 C2 H7 117.0 . . ?
C10 C2 H7 117.0 . . ?
C1 C2 H7 117.0 . . ?
O3 C3 N1 122.7(3) . . ?
O3 C3 C2 121.6(3) . . ?
N1 C3 C2 115.7(3) . . ?
C5 C4 C8 118.9(3) . . ?
C5 C4 N1 117.1(3) . . ?
C8 C4 N1 123.9(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 H4 118.7 . . ?
C4 C5 H4 118.7 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H3 120.3 . . ?
C7 C6 H3 120.3 . . ?
C9 C7 C6 117.3(4) . . ?
C9 C7 H2 121.4 . . ?
C6 C7 H2 121.4 . . ?
O1 C8 C4 124.2(4) . . ?
O1 C8 C9 119.3(3) . . ?
C4 C8 C9 116.5(3) . . ?
C7 C9 O2 118.6(4) . . ?
C7 C9 C8 125.4(3) . . ?
O2 C9 C8 115.9(4) . . ?
C1 C10 C2 61.5(3) . . ?
C1 C10 H6 149.3 . . ?
C2 C10 H6 149.3 . . ?
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 C8 1.346(4) . ?
O2 C9 1.354(4) . ?
O3 C3 1.229(4) . ?
N1 C3 1.327(5) . ?
N1 C4 1.422(4) . ?
C1 C10 1.457(6) . ?
C1 C2 1.509(6) . ?
C1 H5 0.9700 . ?
C1 H1 0.9700 . ?
C2 C3 1.463(5) . ?
C2 C10 1.494(6) . ?
C2 H7 0.9800 . ?
C4 C5 1.379(5) . ?
C4 C8 1.382(4) . ?
C5 C6 1.369(5) . ?
C5 H4 0.9300 . ?
C6 C7 1.378(5) . ?
C6 H3 0.9300 . ?
C7 C9 1.347(6) . ?
C7 H2 0.9300 . ?
C8 C9 1.387(5) . ?
C10 H6 0.9300 . ?
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 C1 C2 C3 -106.4(4) . . . . ?
C4 N1 C3 O3 4.8(6) . . . . ?
C4 N1 C3 C2 -174.2(3) . . . . ?
C10 C2 C3 O3 -34.5(6) . . . . ?
C1 C2 C3 O3 31.7(6) . . . . ?
C10 C2 C3 N1 144.5(4) . . . . ?
C1 C2 C3 N1 -149.3(4) . . . . ?
C3 N1 C4 C5 153.7(4) . . . . ?
C3 N1 C4 C8 -29.3(6) . . . . ?
C8 C4 C5 C6 0.0(6) . . . . ?
N1 C4 C5 C6 177.1(3) . . . . ?
C4 C5 C6 C7 1.5(6) . . . . ?
C5 C6 C7 C9 -1.8(6) . . . . ?
C5 C4 C8 O1 177.7(3) . . . . ?
N1 C4 C8 O1 0.8(6) . . . . ?
C5 C4 C8 C9 -1.0(5) . . . . ?
N1 C4 C8 C9 -177.9(3) . . . . ?
C6 C7 C9 O2 -179.3(4) . . . . ?
C6 C7 C9 C8 0.8(7) . . . . ?
O1 C8 C9 C7 -178.2(4) . . . . ?
C4 C8 C9 C7 0.6(6) . . . . ?
O1 C8 C9 O2 1.9(5) . . . . ?
C4 C8 C9 O2 -179.3(3) . . . . ?
C3 C2 C10 C1 106.9(4) . . . . ?
