Alkyne hydrazones for Raman scattering spectroscopy
Sosnin, Daniil; Aprahamian, Ivan; Chemical Communications 61 (2025) 10119–10121; doi:10.1039/D5CC02471D

data_7134695
_publ_section_title
;
 Alkyne hydrazones for Raman scattering spectroscopy
;
_journal_issue                   55
_journal_name_full               'Chemical Communications'
_journal_page_first              10119
_journal_page_last               10121
_journal_paper_doi               10.1039/D5CC02471D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-02-05 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2541(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.24004(11)
_cell_length_b                   11.03585(11)
_cell_length_c                   20.65862(17)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.2140
_cell_measurement_theta_min      4.2770
_cell_volume                     3017.81(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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    -78.00   5.00   0.50    0.06    --  -47.10 103.00 -64.00  166
  2  \w     17.00  82.00   0.50    0.06    --   47.10-103.00-166.00  130
  3  \w   -162.00 -86.00   0.50    0.23    --  -91.75-103.00-166.00  152
  4  \w    -78.00 -21.00   0.50    0.23    --  -91.75 103.00 -64.00  114
  5  \w     43.00 104.00   0.50    0.23    --  113.25-103.00-166.00  122
  6  \w    108.00 178.00   0.50    0.23    --  113.25 103.00 -64.00  140
  7  \w    -47.00  26.00   0.50    0.06    --  -47.10  37.00-180.00  146
  8  \w    -83.00 -15.00   0.50    0.06    --  -47.10 125.00  90.00  136
  9  \w    -47.00  26.00   0.50    0.06    --  -47.10  37.00  60.00  146
 10  \w    -53.00 -20.00   0.50    0.23    --  -91.75  45.00-120.00   66
 11  \w    -53.00 -20.00   0.50    0.23    --  -91.75  45.00 150.00   66
 12  \w    -53.00 -20.00   0.50    0.23    --  -91.75  45.00 120.00   66
 13  \w    -53.00 -20.00   0.50    0.23    --  -91.75  45.00-150.00   66
 14  \w     42.00  69.00   0.50    0.23    --  113.25 -61.00-150.00   54
 15  \w    100.00 178.00   0.50    0.23    --  113.25  15.00 -60.00  156
 16  \w     42.00  69.00   0.50    0.23    --  113.25 -61.00  90.00   54
 17  \w     42.00  69.00   0.50    0.23    --  113.25 -61.00 -60.00   54
 18  \w    110.00 178.00   0.50    0.23    --  113.25  77.00 -90.00  136
 19  \w     42.00  94.00   0.50    0.23    --  113.25 -77.00  30.00  104
 20  \w     42.00  69.00   0.50    0.23    --  113.25 -61.00  30.00   54
 21  \w     42.00 104.00   0.50    0.23    --  113.25 -94.00-120.00  124
 22  \w    106.00 178.00   0.50    0.23    --  113.25  61.00-180.00  144
 23  \w     43.00  68.00   0.50    0.23    --  113.25 -61.00  60.00   50
 24  \w     42.00  67.00   0.50    0.23    --  113.25 -61.00   0.00   50
 25  \w     72.00  98.00   0.50    0.23    --  113.25 -94.00-150.00   52
 26  \w     46.00  89.00   0.50    0.23    --  113.25 -77.00  60.00   86
 27  \w     58.00  84.00   0.50    0.23    --  113.25 -77.00 -30.00   52
 28  \w     51.00 101.00   0.50    0.23    --  113.25 -94.00 -90.00  100
 29  \w     42.00  67.00   0.50    0.23    --  113.25 -61.00-180.00   50
 30  \w     43.00  69.00   0.50    0.23    --  113.25 -61.00-120.00   52
 31  \w    110.00 166.00   0.50    0.23    --  113.25  61.00 120.00  112
 32  \w    123.00 171.00   0.50    0.23    --  113.25 125.00  90.00   96
 33  \w     42.00  94.00   0.50    0.23    --  113.25 -77.00-180.00  104
 34  \w     42.00  67.00   0.50    0.23    --  113.25 -61.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0946654000
_diffrn_orient_matrix_UB_12      -0.0585234000
_diffrn_orient_matrix_UB_13      -0.0313819000
_diffrn_orient_matrix_UB_21      0.0574186000
_diffrn_orient_matrix_UB_22      -0.1207265000
_diffrn_orient_matrix_UB_23      -0.0062168000
_diffrn_orient_matrix_UB_31      -0.0359758000
_diffrn_orient_matrix_UB_32      -0.0384378000
_diffrn_orient_matrix_UB_33      0.0673792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16466
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.299
_diffrn_reflns_theta_min         4.281
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0491P)^2^+1.6145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2959
_reflns_number_total             3244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02471d2.cif
_cod_data_source_block           ia723b
_cod_depositor_comments
'Adding full bibliography for 7134694--7134699.cif.'
_cod_database_code               7134695
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H16N2O2
_chemical_oxdiff_usercomment     'DS-ben alk V'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.875
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              20218
_shelx_hkl_checksum              50932
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'DS-ben alk V'
_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.875