Organotin(IV) compounds catalyzed cyanide-free synthesis of α-iminonitriles.
Kumar, Manish; Chakraborty, Sudipta; Nayek, Hari Pada; Dalton transactions (Cambridge, England : 2003) 54 (2025) 8470–8482; doi:10.1039/d5dt00492f

data_7719040
_publ_section_title
;
 Organotin(IV) compounds catalyzed cyanide-free synthesis of
 &#x3b1;-iminonitriles.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8470
_journal_page_last               8482
_journal_paper_doi               10.1039/d5dt00492f
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C14 H10 I N3 O'
_chemical_formula_sum            'C14 H10 I N3 O'
_chemical_formula_weight         363.15
_chemical_name_systematic        C336
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_audit_update_record
;
2025-02-04 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.301(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1544(3)
_cell_length_b                   10.7973(9)
_cell_length_c                   30.5567(16)
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8030
_cell_measurement_theta_min      2.6640
_cell_volume                     1369.56(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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     20.00  82.00   1.00   12.37    --   14.45  38.00 -60.00   62
  2  \w     -2.00  65.00   1.00   12.37    --   14.45  57.00-150.00   67
  3  \w    -29.00   1.00   1.00   12.37    --  -16.48 -77.00 -60.00   30
  4  \w    -38.00   8.00   1.00   12.37    --  -16.48 -77.00  30.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0407131000
_diffrn_orient_matrix_UB_12      0.0607906000
_diffrn_orient_matrix_UB_13      0.0070154000
_diffrn_orient_matrix_UB_21      -0.1648449000
_diffrn_orient_matrix_UB_22      0.0123677000
_diffrn_orient_matrix_UB_23      0.0034198000
_diffrn_orient_matrix_UB_31      0.0201291000
_diffrn_orient_matrix_UB_32      -0.0214441000
_diffrn_orient_matrix_UB_33      0.0218860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            6038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         2.001
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.045
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2015
_reflns_number_total             2937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00492f2.cif
_cod_data_source_block           2l
_cod_database_code               7719040
_diffrn_oxdiff_digest_frames
;
019152dc0fa592f770181c5a2d4c7b5f7e00027b09e
;
_diffrn_oxdiff_digest_hkl
;
01def98f4bc253b7e0c637f83e5495ef573b40
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C4(H4), C7(H7), C12(H12), C5(H5), C14(H14)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_shelxl_version_number     2014/7
_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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.627