# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_840_auto
_database_code_depnum_ccdc_archive 'CCDC 2339682'
loop_
_audit_author_name
_audit_author_address
'dimethoxy-b-nitrostyrene '
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2025-01-08 downloaded from the CCDC.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H11NO4
_chemical_oxdiff_usercomment     94K
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   3.85270(10)
_cell_length_b                   15.8701(5)
_cell_length_c                   15.9967(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.588(3)
_cell_angle_gamma                90
_cell_volume                     974.95(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4868
_cell_measurement_temperature    93.9(7)
_cell_measurement_theta_max      30.2990
_cell_measurement_theta_min      2.5470
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.767
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      93.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  29.00   0.50   19.31    --   -5.79 -99.00  90.00   68
  2  ω    -64.00  22.00   0.50   19.31    --    6.10 -57.00 -60.00  172
  3  ω      4.00  72.00   0.50   19.31    --    6.10  57.00   0.00  136
  4  ω    -64.00  76.00   0.50   19.31    --    6.10   0.00  30.00  280
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0285755000
_diffrn_orient_matrix_UB_12      0.0430236000
_diffrn_orient_matrix_UB_13      -0.0104008000
_diffrn_orient_matrix_UB_21      -0.0119740000
_diffrn_orient_matrix_UB_22      -0.0104919000
_diffrn_orient_matrix_UB_23      -0.0432365000
_diffrn_orient_matrix_UB_31      -0.1820924000
_diffrn_orient_matrix_UB_32      -0.0060470000
_diffrn_orient_matrix_UB_33      0.0008702000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2122
_reflns_number_total             2546
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C8(H8), C9(H9), C2(H2)
1.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.1960(2) 0.75411(5) 0.69607(5) 0.0168(2) Uani 1 1 d . . . . .
O1 O 0.2739(2) 0.55226(6) 0.92410(6) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.9091(3) 0.58555(6) 0.41537(6) 0.0242(2) Uani 1 1 d . . . . .
O3 O 0.6726(3) 0.70545(6) 0.44220(6) 0.0272(2) Uani 1 1 d . . . . .
N1 N 0.7593(3) 0.63313(6) 0.46247(6) 0.0160(2) Uani 1 1 d . . . . .
C4 C 0.4506(3) 0.62101(7) 0.68023(7) 0.0134(2) Uani 1 1 d . . . . .
C5 C 0.2878(3) 0.67868(7) 0.73207(7) 0.0134(2) Uani 1 1 d . . . . .
C6 C 0.2279(3) 0.65880(7) 0.81459(7) 0.0146(2) Uani 1 1 d . . . . .
H6 H 0.124913 0.698769 0.849255 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5261(3) 0.64660(7) 0.59684(7) 0.0144(2) Uani 1 1 d . . . . .
H3 H 0.452156 0.701231 0.578847 0.017 Uiso 1 1 calc R U . . .
C7 C 0.3223(3) 0.57909(8) 0.84523(7) 0.0150(2) Uani 1 1 d . . . . .
C8 C 0.4780(3) 0.52019(7) 0.79456(8) 0.0158(2) Uani 1 1 d . . . . .
H8 H 0.538944 0.465840 0.815876 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5417(3) 0.54142(7) 0.71414(8) 0.0145(2) Uani 1 1 d . . . . .
H9 H 0.650086 0.501463 0.680474 0.017 Uiso 1 1 calc R U . . .
C2 C 0.6911(3) 0.59981(7) 0.54296(7) 0.0155(2) Uani 1 1 d . . . . .
H2 H 0.763688 0.544258 0.557997 0.019 Uiso 1 1 calc R U . . .
C10 C 0.0510(3) 0.81637(8) 0.74810(8) 0.0191(3) Uani 1 1 d . . . . .
H10A H -0.007935 0.866968 0.714811 0.029 Uiso 1 1 calc R U . . .
H10B H 0.221527 0.830803 0.794640 0.029 Uiso 1 1 calc R U . . .
H10C H -0.159842 0.793901 0.770397 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1341(4) 0.61084(9) 0.98085(8) 0.0219(3) Uani 1 1 d . . . . .
H11A H -0.095413 0.629994 0.957553 0.033 Uiso 1 1 calc R U . . .
H11B H 0.290685 0.659335 0.988852 0.033 Uiso 1 1 calc R U . . .
H11C H 0.111465 0.583215 1.034940 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C5 1.3629(14) . ?
O2 C10 1.4336(14) . ?
O1 C7 1.3585(14) . ?
O1 C11 1.4342(15) . ?
O4 N1 1.2411(13) . ?
O3 N1 1.2315(14) . ?
N1 C2 1.4354(15) . ?
C4 C5 1.4149(16) . ?
C4 C3 1.4461(16) . ?
C4 C9 1.4079(16) . ?
C5 C6 1.3943(16) . ?
C6 C7 1.3943(17) . ?
C3 C2 1.3366(16) . ?
C7 C8 1.4031(17) . ?
C8 C9 1.3708(17) . ?

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
C5 O2 C10 117.40(9) . . ?
C7 O1 C11 118.11(10) . . ?
O4 N1 C2 116.60(10) . . ?
O3 N1 O4 122.46(10) . . ?
O3 N1 C2 120.95(10) . . ?
C5 C4 C3 119.35(10) . . ?
C9 C4 C5 117.58(10) . . ?
C9 C4 C3 123.03(10) . . ?
O2 C5 C4 115.65(10) . . ?
O2 C5 C6 122.80(10) . . ?
C6 C5 C4 121.55(11) . . ?
C5 C6 C7 118.67(11) . . ?
C2 C3 C4 125.45(11) . . ?
O1 C7 C6 124.02(11) . . ?
O1 C7 C8 115.12(11) . . ?
C6 C7 C8 120.86(11) . . ?
C9 C8 C7 119.69(11) . . ?
C8 C9 C4 121.62(11) . . ?
C3 C2 N1 120.29(11) . . ?

_olex2_exptl_crystal_mounting_method 'MIteGen Micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.773
