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

data_7134696
_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         'C20 H21 N3 O2'
_chemical_formula_sum            'C20 H21 N3 O2'
_chemical_formula_weight         335.40
_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             2023-09-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-02-06 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.2480(13)
_cell_angle_beta                 91.2744(13)
_cell_angle_gamma                109.7446(13)
_cell_formula_units_Z            4
_cell_length_a                   12.27152(18)
_cell_length_b                   12.39856(18)
_cell_length_c                   12.5695(2)
_cell_measurement_reflns_used    23428
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.8870
_cell_measurement_theta_min      3.5160
_cell_volume                     1799.41(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (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      100.01(10)
_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 0.980
_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    -70.00  16.00   0.50    0.05    --  -47.11  77.00   0.00  172
  2  \w    -47.00  26.00   0.50    0.05    --  -47.11  37.00 -60.00  146
  3  \w    -47.00  26.00   0.50    0.05    --  -47.11  37.00-120.00  146
  4  \w    -53.00 -20.00   0.50    0.11    --  -91.75  45.00-180.00   66
  5  \w   -119.00 -34.00   0.50    0.05    --  -47.11 -43.00 -36.97  170
  6  \w   -160.00 -83.00   0.50    0.11    --  -91.75-112.00 -51.00  154
  7  \w   -163.00 -88.00   0.50    0.11    --  -91.75 -48.00  21.88  150
  8  \w   -163.00-110.00   0.50    0.11    --  -91.75 -77.00 150.00  106
  9  \w    -80.00  -5.00   0.50    0.05    --  -47.11 112.00  42.00  150
 10  \w    -81.00 -23.00   0.50    0.11    --  -91.75 112.00  42.00  116
 11  \w   -118.00 -34.00   0.50    0.05    --  -47.11 -46.00-152.26  168
 12  \w     42.00  69.00   0.50    0.11    --  113.25 -61.00-180.00   54
 13  \w     42.00  94.00   0.50    0.11    --  113.25 -77.00-120.00  104
 14  \w     42.00  94.00   0.50    0.11    --  113.25 -77.00  60.00  104
 15  \w     42.00  69.00   0.50    0.11    --  113.25 -61.00 150.00   54
 16  \w    105.00 178.00   0.50    0.11    --  113.25 112.00  42.00  146
 17  \w     97.00 178.00   0.50    0.11    --  113.25 125.00-120.00  162
 18  \w     42.00  69.00   0.50    0.11    --  113.25 -61.00-150.00   54
 19  \w     36.00  93.00   0.50    0.05    --   47.11-125.00  30.00  114
 20  \w     44.00 108.00   0.50    0.11    --  113.25-125.00 -90.00  128
 21  \w     44.00 108.00   0.50    0.11    --  113.25-125.00 -60.00  128
 22  \w     44.00 108.00   0.50    0.11    --  113.25-125.00 -30.00  128
 23  \w     44.00 108.00   0.50    0.11    --  113.25-125.00-150.00  128
 24  \w     27.00  85.00   0.50    0.05    --   47.11-112.00 -51.00  116
 25  \w     45.00 106.00   0.50    0.11    --  113.25-112.00 -51.00  122
 26  \w     43.00 105.00   0.50    0.11    --  113.25-104.00-133.08  124
 27  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00   0.00  124
 28  \w     44.00 108.00   0.50    0.11    --  113.25-125.00  30.00  128
 29  \w     44.00 108.00   0.50    0.11    --  113.25-125.00  90.00  128
 30  \w     44.00 108.00   0.50    0.11    --  113.25-125.00 150.00  128
 31  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00 150.00  124
 32  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00 120.00  124
 33  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00  90.00  124
 34  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00  60.00  124
 35  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00  30.00  124
 36  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00 -30.00  124
 37  \w     42.00 104.00   0.50    0.11    --  113.25 -94.00 -60.00  124
 38  \w    100.00 178.00   0.50    0.11    --  113.25  15.00 120.00  156
 39  \w    106.00 178.00   0.50    0.11    --  113.25  61.00 150.00  144
 40  \w    106.00 178.00   0.50    0.11    --  113.25  61.00  30.00  144
 41  \w    101.00 178.00   0.50    0.11    --  113.25  45.00 -30.00  154
 42  \w    101.00 178.00   0.50    0.11    --  113.25  45.00 -90.00  154
 43  \w    101.00 178.00   0.50    0.11    --  113.25  45.00-150.00  154
 44  \w    101.00 178.00   0.50    0.11    --  113.25  30.00-150.00  154
 45  \w    106.00 178.00   0.50    0.11    --  113.25  61.00 -60.00  144
 46  \w    100.00 178.00   0.50    0.11    --  113.25  15.00  30.00  156
 47  \w     34.00 119.00   0.50    0.05    --   47.11  47.00  77.36  170
 48  \w     34.00  79.00   0.50    0.05    --   47.11  47.00 155.66   90
;
_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      -0.0228572000
_diffrn_orient_matrix_UB_12      0.0102199000
_diffrn_orient_matrix_UB_13      -0.1199113000
_diffrn_orient_matrix_UB_21      -0.1214785000
_diffrn_orient_matrix_UB_22      -0.0904671000
_diffrn_orient_matrix_UB_23      0.0093384000
_diffrn_orient_matrix_UB_31      -0.0502237000
_diffrn_orient_matrix_UB_32      0.0956133000
_diffrn_orient_matrix_UB_33      0.0237832000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.313
_diffrn_reflns_theta_min         3.517
_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    0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0575P)^2^+0.3485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6997
_reflns_number_total             7712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02471d2.cif
_cod_data_source_block           ia923d
_cod_depositor_comments
'Adding full bibliography for 7134694--7134699.cif.'
_cod_original_cell_volume        1799.42(5)
_cod_database_code               7134696
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H21N3O2
_chemical_oxdiff_usercomment     DS-dma-v
_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:
 C13A(H13A,H13B), C13B(H13C,H13D)
2.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C6A(H6A), C8A(H8A), C9A(H9A), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A), C5B(H5B), C6B(H6B), C8B(H8B), C9B(H9B), C16B(H16B),
 C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
2.c Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C14A(H14A,H14B,H14C), C10B(H10D,
 H10E,H10F), C11B(H11D,H11E,H11F), C14B(H14D,H14E,H14F)
;
_shelx_res_checksum              15080
_shelx_hkl_checksum              21691
_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-dma-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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.862