A methyl-driven strategy enhances sensitivity through the modulation of aromaticity
Guo, Benyue; Hu, Lu; Pang, Siping; CrystEngComm 27 (2025) 7328–7332; doi:10.1039/D5CE00871A

data_7251079
_publ_section_title
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 A methyl-driven strategy enhances sensitivity through the modulation of
 aromaticity
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7328
_journal_page_last               7332
_journal_paper_doi               10.1039/D5CE00871A
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C6 H5 N8 O4, 2(H2 O), H4 N O'
_chemical_formula_sum            'C6 H13 N9 O7'
_chemical_formula_weight         323.25
_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
_audit_creation_date             2024-05-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-20 deposited with the CCDC.	2025-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                89.95(2)
_cell_angle_beta                 79.60(2)
_cell_angle_gamma                87.27(3)
_cell_formula_units_Z            8
_cell_length_a                   12.646(8)
_cell_length_b                   13.107(8)
_cell_length_c                   15.668(9)
_cell_measurement_reflns_used    5259
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.199
_cell_measurement_theta_min      2.319
_cell_volume                     2551(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28157
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_min         1.911
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0897 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.7958.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     843
_refine_ls_number_reflns         10370
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+15.8889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2476
_refine_ls_wR_factor_ref         0.2906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5806
_reflns_number_total             10370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00871a2.cif
_cod_data_source_block           mo_20240826_0m
_cod_depositor_comments
'Adding full bibliography for 7251074--7251079.cif.'
_cod_database_code               7251079
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9780(9)
 0.0220(9)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, {H00A,H00B,H00C} of N00V, H6 of O6, {H18A,H18B,H18C} of
  C18, {H24D,H24E,H24F} of N24, {H18D,H18E,H18F} of N18
 At 1.5 times of:
  All O(H,H) groups, {H9A,H9B,H9C} of N9, {H12A,H12B,H12C} of C12, H5 of O5,
  H23A of O23, H9 of O9, H16A of O16, {H6A,H6B,H6C} of C6, {H24A,H24B,H24C} of
  C24
3. Restrained distances
 N34-H34 = O23-H23B
 0.87 with sigma of 0.02
 O19-H19A = O19-H19B
 0.87 with sigma of 0.02
4.a Free rotating group:
 O22(H22A,H22B), O12(H12D,H12E), O23(H23A), O13(H13A,H13B), O20(H20A,H20B),
 O21(H21A,H21B), O24(H24G,H24H)
4.b Rotating group:
 O6(H6)
4.c Aromatic/amide H refined with riding coordinates:
 N27(H27), N15(H15), N7(H7), N21(H21), N16(H16), N3(H3), N32(H32)
4.d Idealised Me refined as rotating group:
 N00V(H00A,H00B,H00C), N9(H9A,H9B,H9C), N18(H18D,H18E,H18F), N24(H24D,H24E,
 H24F), C24(H24A,H24B,H24C), C6(H6A,H6B,H6C), C18(H18A,H18B,H18C), C12(H12A,
 H12B,H12C)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O9(H9), O16(H16A)
;
_olex2_submission_special_instructions 'No special instructions were received'