#------------------------------------------------------------------------------
#$Date: 2025-11-29 22:26:49 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303838 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/09/7250921.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_7250921
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 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.34(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.314(6)
_cell_length_b                   12.846(9)
_cell_length_c                   10.041(8)
_cell_measurement_reflns_used    810
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.233
_cell_measurement_theta_min      3.380
_cell_volume                     942.6(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4153
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.172
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_target            Mo
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.8049.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0625
_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)+(0.0916P)²+0.0308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                783
_reflns_number_total             1655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5gc03649f2.cif
_cod_data_source_block           w_no
_cod_depositor_comments
'Adding full bibliography for 7250918--7250924.cif.'
_cod_original_cell_volume        942.7(12)
_cod_database_code               7250921
_shelx_shelxl_version_number     2019/3
_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_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with polybutenes oil (CAS: 9003-29-6) on a glass slide. A suitable single crystal coated with polybutenes oil as less as possible was sealed in capillary tube filled with argon. The capillary tube with single crystal was mounted on copper pin with solid paraffin.'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C6(H6), C5(H5), C3(H3), C4(H4)
2.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_file
;
TITL 1_a.res in P2(1)/n
    w_no.res
    created by SHELXL-2019/3 at 20:06:20 on 11-Dec-2023
CELL 0.71073 7.3141 12.8463 10.0413 90 92.34 90
ZERR 4 0.0057 0.0093 0.0078 0 0.021 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 40 44 4 8
EQIV $1 -1+X,+Y,+Z

L.S. 10
PLAN  2 0 0
SIZE 0.12 0.13 0.15
TEMP 23
CONF
HTAB O1 O2_$1
HTAB N1 O1
HTAB C3 O2
HTAB
BOND $H
MORE -1
fmap 2
acta
OMIT -3 50
REM <olex2.extras>
REM <HklSrc "%.\\W_NO.hkl">
REM </olex2.extras>

WGHT    0.091600    0.030800
FVAR       0.71387
O2    4    0.933578    0.430861    0.640929    11.00000    0.03149    0.09652 =
         0.08561   -0.00770    0.00180    0.00039
C9    1    1.005897    0.589235    0.827154    11.00000    0.05722    0.09898 =
         0.09767   -0.02289   -0.00900   -0.01059
AFIX  93
H9A   2    1.031997    0.635117    0.897007    11.00000   -1.20000
H9B   2    1.090427    0.579121    0.761655    11.00000   -1.20000
AFIX   0
O1    4    0.287836    0.418778    0.684714    11.00000    0.03052    0.09112 =
         0.07977   -0.00980    0.00254   -0.00155
AFIX 147
H1    2    0.176786    0.421402    0.670213    11.00000   -1.50000
AFIX   0
N1    3    0.635065    0.443775    0.678340    11.00000    0.03053    0.06664 =
         0.06136   -0.00771    0.00240   -0.00239
AFIX  43
H1A   2    0.559357    0.469655    0.732684    11.00000   -1.20000
AFIX   0
C10   1    0.711744    0.550849    0.919833    11.00000    0.08093    0.13997 =
         0.07752   -0.02094    0.00419   -0.01790
AFIX 137
H10A  2    0.763796    0.588557    0.994717    11.00000   -1.50000
H10B  2    0.671697    0.483665    0.948693    11.00000   -1.50000
H10C  2    0.609245    0.588782    0.881851    11.00000   -1.50000
AFIX   0
C8    1    0.847839    0.538133    0.820934    11.00000    0.04425    0.07160 =
         0.06249    0.00052   -0.00545   -0.00201
C7    1    0.810607    0.467357    0.705191    11.00000    0.03264    0.06668 =
         0.06112    0.00930   -0.00416   -0.00192
C2    1    0.555996    0.383980    0.576322    11.00000    0.03396    0.05687 =
         0.05944    0.00276   -0.00195   -0.00083
C1    1    0.367217    0.372380    0.580474    11.00000    0.03984    0.05357 =
         0.06820    0.00368    0.00001   -0.00091
C6    1    0.273198    0.317541    0.482591    11.00000    0.04104    0.06232 =
         0.08893   -0.00093   -0.01502   -0.00369
AFIX  43
H6    2    0.146927    0.309995    0.485100    11.00000   -1.20000
AFIX   0
C5    1    0.366782    0.273880    0.380914    11.00000    0.06928    0.06066 =
         0.07814   -0.01049   -0.01785   -0.00166
AFIX  43
H5    2    0.303176    0.236553    0.314566    11.00000   -1.20000
AFIX   0
C3    1    0.646911    0.339679    0.473695    11.00000    0.04466    0.07366 =
         0.07510   -0.00715    0.00299    0.00484
AFIX  43
H3    2    0.773132    0.346893    0.470094    11.00000   -1.20000
AFIX   0
C4    1    0.551107    0.284481    0.375936    11.00000    0.07085    0.07081 =
         0.07556   -0.01355   -0.00271    0.00766
AFIX  43
H4    2    0.612833    0.254458    0.306466    11.00000   -1.20000
AFIX   0
HKLF 4




REM  1_a.res in P2(1)/n
REM wR2 = 0.2066, GooF = S = 1.013, Restrained GooF = 1.013 for all data
REM R1 = 0.0625 for 783 Fo > 4sig(Fo) and 0.1526 for all 1655 data
REM 120 parameters refined using 0 restraints

END

WGHT      0.0918      0.0340

REM Instructions for potential hydrogen bonds
HTAB O1 O2_$1
HTAB N1 O1
HTAB C3 O2

REM Highest difference peak  0.239,  deepest hole -0.162,  1-sigma level  0.047
Q1    1   0.0999  0.3348  0.4728  11.00000  0.05    0.24
Q2    1   0.1000  0.4368  0.6821  11.00000  0.05    0.22
;
_shelx_res_checksum              22301
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.9336(3) 0.4309(2) 0.6409(3) 0.0712(10) Uani 1 1 d . . . . .
C9 C 1.0059(6) 0.5892(4) 0.8272(5) 0.0850(15) Uani 1 1 d . . . . .
H9A H 1.031997 0.635117 0.897007 0.102 Uiso 1 1 calc R U . . .
H9B H 1.090427 0.579121 0.761655 0.102 Uiso 1 1 calc R U . . .
O1 O 0.2878(3) 0.4188(2) 0.6847(3) 0.0671(9) Uani 1 1 d . . . . .
H1 H 0.176786 0.421402 0.670213 0.101 Uiso 1 1 calc R U . . .
N1 N 0.6351(4) 0.4438(2) 0.6783(3) 0.0528(9) Uani 1 1 d . . . . .
H1A H 0.559357 0.469655 0.732684 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7117(6) 0.5508(5) 0.9198(5) 0.0994(18) Uani 1 1 d . . . . .
H10A H 0.763796 0.588557 0.994717 0.149 Uiso 1 1 calc R U . . .
H10B H 0.671697 0.483665 0.948693 0.149 Uiso 1 1 calc R U . . .
H10C H 0.609245 0.588782 0.881851 0.149 Uiso 1 1 calc R U . . .
C8 C 0.8478(5) 0.5381(3) 0.8209(4) 0.0597(11) Uani 1 1 d . . . . .
C7 C 0.8106(5) 0.4674(3) 0.7052(4) 0.0536(11) Uani 1 1 d . . . . .
C2 C 0.5560(4) 0.3840(3) 0.5763(4) 0.0502(10) Uani 1 1 d . . . . .
C1 C 0.3672(5) 0.3724(3) 0.5805(4) 0.0539(11) Uani 1 1 d . . . . .
C6 C 0.2732(5) 0.3175(3) 0.4826(4) 0.0646(12) Uani 1 1 d . . . . .
H6 H 0.146927 0.309995 0.485100 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3668(6) 0.2739(3) 0.3809(4) 0.0699(13) Uani 1 1 d . . . . .
H5 H 0.303176 0.236553 0.314566 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6469(5) 0.3397(3) 0.4737(4) 0.0645(12) Uani 1 1 d . . . . .
H3 H 0.773132 0.346893 0.470094 0.077 Uiso 1 1 calc R U . . .
C4 C 0.5511(6) 0.2845(4) 0.3759(4) 0.0726(13) Uani 1 1 d . . . . .
H4 H 0.612833 0.254458 0.306466 0.087 Uiso 1 1 calc R U . . .
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
O2 0.0315(13) 0.097(2) 0.086(2) -0.0077(18) 0.0018(14) 0.0004(14)
C9 0.057(3) 0.099(4) 0.098(4) -0.023(3) -0.009(2) -0.011(3)
O1 0.0305(13) 0.091(2) 0.080(2) -0.0098(17) 0.0025(13) -0.0015(15)
N1 0.0305(15) 0.067(2) 0.061(2) -0.0077(18) 0.0024(14) -0.0024(15)
C10 0.081(3) 0.140(5) 0.078(4) -0.021(3) 0.004(3) -0.018(3)
C8 0.044(2) 0.072(3) 0.062(3) 0.001(2) -0.0055(19) -0.002(2)
C7 0.0326(19) 0.067(3) 0.061(3) 0.009(2) -0.0042(18) -0.0019(19)
C2 0.0340(19) 0.057(3) 0.059(3) 0.003(2) -0.0020(18) -0.0008(18)
C1 0.040(2) 0.054(3) 0.068(3) 0.004(2) 0.000(2) -0.0009(19)
C6 0.041(2) 0.062(3) 0.089(3) -0.001(3) -0.015(2) -0.004(2)
C5 0.069(3) 0.061(3) 0.078(3) -0.010(2) -0.018(2) -0.002(2)
C3 0.045(2) 0.074(3) 0.075(3) -0.007(3) 0.003(2) 0.005(2)
C4 0.071(3) 0.071(3) 0.076(3) -0.014(3) -0.003(2) 0.008(2)
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
H9A C9 H9B 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
C1 O1 H1 109.5 . . ?
C7 N1 H1A 115.0 . . ?
C7 N1 C2 130.0(3) . . ?
C2 N1 H1A 115.0 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
C9 C8 C10 122.3(4) . . ?
C9 C8 C7 117.9(4) . . ?
C10 C8 C7 119.7(4) . . ?
O2 C7 N1 121.9(4) . . ?
O2 C7 C8 122.0(3) . . ?
N1 C7 C8 116.0(3) . . ?
N1 C2 C1 114.9(3) . . ?
C3 C2 N1 125.7(3) . . ?
C3 C2 C1 119.3(4) . . ?
O1 C1 C2 115.7(3) . . ?
O1 C1 C6 124.1(3) . . ?
C6 C1 C2 120.2(4) . . ?
C1 C6 H6 120.2 . . ?
C1 C6 C5 119.5(4) . . ?
C5 C6 H6 120.2 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
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
O2 C7 1.222(4) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C9 C8 1.329(5) . ?
O1 H1 0.8200 . ?
O1 C1 1.356(4) . ?
N1 H1A 0.8600 . ?
N1 C7 1.336(4) . ?
N1 C2 1.388(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C8 1.444(6) . ?
C8 C7 1.492(6) . ?
C2 C1 1.391(5) . ?
C2 C3 1.373(5) . ?
C1 C6 1.371(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.372(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.358(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
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 O2 0.82 1.80 2.615(4) 178.3 1_455 yes
N1 H1A O1 0.86 2.13 2.563(4) 110.9 . yes
C3 H3 O2 0.93 2.31 2.881(5) 119.6 . 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
C9 C8 C7 O2 22.5(6) . . . . ?
C9 C8 C7 N1 -159.4(4) . . . . ?
O1 C1 C6 C5 179.7(4) . . . . ?
N1 C2 C1 O1 -1.5(5) . . . . ?
N1 C2 C1 C6 178.0(4) . . . . ?
N1 C2 C3 C4 -178.0(4) . . . . ?
C10 C8 C7 O2 -158.9(4) . . . . ?
C10 C8 C7 N1 19.2(6) . . . . ?
C7 N1 C2 C1 178.0(4) . . . . ?
C7 N1 C2 C3 -3.9(6) . . . . ?
C2 N1 C7 O2 -4.4(6) . . . . ?
C2 N1 C7 C8 177.5(3) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C1 C6 C5 C4 -0.1(7) . . . . ?
C6 C5 C4 C3 0.0(7) . . . . ?
C3 C2 C1 O1 -179.8(3) . . . . ?
C3 C2 C1 C6 -0.3(6) . . . . ?
