Design and synthesis of novel angular 4,5-pyranocoumarin fluorescent probes for detecting hydrazine and their applications
Zhou, Huafeng; Huang, Jiayong; Su, Jian; Su, Xiaowei; Chen, Qiujuan; Li, Rui; Zheng, Yuxiao; Chen, Rui; Huo, Lini; RSC Advances 15 (2025) 36525–36533; doi:10.1039/D5RA04433B

data_7250940
_publ_section_title
;
 Design and synthesis of novel angular 4,5-pyranocoumarin fluorescent
 probes for detecting hydrazine and their applications
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              36525
_journal_page_last               36533
_journal_paper_doi               10.1039/D5RA04433B
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C21 H17 Cl O6'
_chemical_formula_sum            'C21 H17 Cl O6'
_chemical_formula_weight         400.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-30
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2025-05-07 deposited with the CCDC.	2025-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.285(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.9515(14)
_cell_length_b                   9.1618(4)
_cell_length_c                   17.4802(9)
_cell_measurement_reflns_used    6264
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1500
_cell_measurement_theta_min      3.2060
_cell_volume                     3574.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -64.00  24.00   1.00    2.00    --   11.90 -77.00   0.00   88
  2  \w    -12.00  80.00   1.00    2.00    --   11.90  37.00 120.00   92
  3  \w    -11.00  26.00   1.00    5.00    --  -11.59 -99.00 -90.00   37
  4  \w    -14.00  44.00   1.00    5.00    --   11.74 -99.00 -90.00   58
  5  \w     19.00  44.00   1.00    5.00    --   11.74  77.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0129245000
_diffrn_orient_matrix_UB_12      0.0677421000
_diffrn_orient_matrix_UB_13      -0.0042097000
_diffrn_orient_matrix_UB_21      0.0004292000
_diffrn_orient_matrix_UB_22      0.0218036000
_diffrn_orient_matrix_UB_23      0.0391494000
_diffrn_orient_matrix_UB_31      0.0290277000
_diffrn_orient_matrix_UB_32      -0.0305027000
_diffrn_orient_matrix_UB_33      0.0186160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.403
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0356
_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/[\s^2^(Fo^2^)+(0.0511P)^2^+1.8862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2784
_reflns_number_total             3150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04433b2.cif
_cod_data_source_block           lz-1
_cod_original_cell_volume        3574.2(3)
_cod_database_code               7250940
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C9(H9), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_res_checksum              40933
_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 2.190
_oxdiff_exptl_absorpt_empirical_full_min 0.699