Redox induced oxidative C-C coupling of non-innocent bis(heterocyclo)methanides
Lahiri, Goutam Kumar; Panda, Sanjib; Baliyan, Rupal; Dhara, Suman; Huang, Kuo-Wei; Dalton Transactions  (2021) –; doi:10.1039/D1DT03310G

data_7708779
_publ_section_title
;
 Redox induced oxidative C-C coupling of non-innocent
 bis(heterocyclo)methanides
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03310G
_journal_year                    2021
_chemical_formula_moiety         'C25 H22 N4 O4 Zn'
_chemical_formula_sum            'C25 H22 N4 O4 Zn'
_chemical_formula_weight         507.83
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                107.498(5)
_cell_angle_beta                 91.042(4)
_cell_angle_gamma                102.343(4)
_cell_formula_units_Z            4
_cell_length_a                   10.2232(4)
_cell_length_b                   15.4947(8)
_cell_length_c                   17.3250(9)
_cell_measurement_reflns_used    6212
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5990
_cell_measurement_theta_min      2.4000
_cell_volume                     2546.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -110.00  25.00   0.50    8.00    --  -20.00   0.00 -36.00  270
  2  \w   -110.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  258
  3  \w    -71.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  180
  4  \w    -77.50 -12.00   0.50    8.00    --  -20.00 -72.00-108.00  131
  5  \w    -54.00 -48.00   0.50    8.00    --  -20.00  72.00 108.00   12
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0590209000
_diffrn_orient_matrix_UB_12      0.0345069000
_diffrn_orient_matrix_UB_13      0.0016321000
_diffrn_orient_matrix_UB_21      -0.0117689000
_diffrn_orient_matrix_UB_22      -0.0075055000
_diffrn_orient_matrix_UB_23      -0.0422368000
_diffrn_orient_matrix_UB_31      -0.0382376000
_diffrn_orient_matrix_UB_32      0.0344283000
_diffrn_orient_matrix_UB_33      0.0084063000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.1243
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20123
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.017
_refine_diff_density_max         2.641
_refine_diff_density_min         -1.981
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         8902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.1004
_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^)+(0.1582P)^2^+4.4412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2536
_refine_ls_wR_factor_ref         0.3025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5440
_reflns_number_total             8902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03310g2.cif
_cod_data_source_block           2
_cod_original_cell_volume        2546.8(2)
_cod_database_code               7708779
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOZn
_reflns_odcompleteness_completeness 88.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.25
_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 Ternary CH refined with riding coordinates:
 C2(H2), C27(HG)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C31(H), C21(H21), C34(HA), C15(H15), C20(H20), C42(HB),
 C6(H6), C40(HC), C43(HD), C46(HE), C8(H8), C10(H10), C7(H7), C45(HF), C14(H14),
  C44(HH), C32(HI), C33(HJ), C19(H19), C13(H13), C12(H12), C29(HK), C18(H18),
 C17(H17), C39(HL), C35(HM), C37(HN), C38(HO)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C50(HP,HQ,HR), C23(H23A,H23B,H23C), C48(HS,HT,HU)
;
_shelx_res_checksum              88726
_shelx_fab_checksum              88246
_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 2.141
_oxdiff_exptl_absorpt_empirical_full_min 0.708