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_7708777
_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         'C46 H44 Cu2 N4 O8'
_chemical_formula_sum            'C46 H44 Cu2 N4 O8'
_chemical_formula_weight         907.93
_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   geom
_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                90
_cell_angle_beta                 112.08(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.943(4)
_cell_length_b                   8.4666(11)
_cell_length_c                   23.193(4)
_cell_measurement_reflns_used    1954
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.4420
_cell_measurement_theta_min      1.9440
_cell_volume                     4174.8(13)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  70.00   1.00    8.00    --  -20.00   0.00 -36.00  180
  2  \w    -87.00 -32.00   1.00    8.00    --  -20.00 -72.00 -36.00   55
;
_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      -0.0331145000
_diffrn_orient_matrix_UB_12      -0.0015910000
_diffrn_orient_matrix_UB_13      -0.0159607000
_diffrn_orient_matrix_UB_21      -0.0033946000
_diffrn_orient_matrix_UB_22      -0.0333392000
_diffrn_orient_matrix_UB_23      0.0266228000
_diffrn_orient_matrix_UB_31      -0.0021600000
_diffrn_orient_matrix_UB_32      0.0767884000
_diffrn_orient_matrix_UB_33      0.0112695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1586
_diffrn_reflns_av_unetI/netI     0.2670
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.916
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86535
_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 bluish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.2161
_refine_ls_R_factor_gt           0.0996
_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^)+(0.0740P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1611
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03310g2.cif
_cod_data_source_block           1c
_cod_original_cell_volume        4174.7(13)
_cod_database_code               7708777
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOCu
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.866
_reflns_odcompleteness_completeness 88.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.93
_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. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C12) \\sim
Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of
0.0005
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C13(H13A,H13B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C7(H7), C10(H10), C9(H9), C8(H8), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              97253
_shelx_fab_checksum              77285
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.726