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_7708774
_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         'C38 H36 Cu2 N8 O9'
_chemical_formula_sum            'C38 H36 Cu2 N8 O9'
_chemical_formula_weight         875.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2048(5)
_cell_length_b                   22.1257(6)
_cell_length_c                   22.3600(6)
_cell_measurement_reflns_used    23306
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.2290
_cell_measurement_theta_min      1.8860
_cell_volume                     8017.0(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   12.00    --  -20.00   0.00-180.00  270
  2  \w   -110.00  10.00   0.50   12.00    --  -20.00 -72.00-180.00  240
  3  \w    -69.00   4.00   0.50   12.00    --  -20.00 -72.00 -36.00  146
  4  \w    -59.00  -2.50   0.50   12.00    --  -20.00  72.00 108.00  113
  5  \w    -59.00 -28.50   0.50   12.00    --  -20.00  72.00 -36.00   61
  6  \w    -59.00 -28.50   0.50   12.00    --  -20.00  72.00-180.00   61
  7  \w   -110.00 -39.00   0.50   12.00    --  -20.00   0.00 -36.00  142
;
_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      0.0109003000
_diffrn_orient_matrix_UB_12      -0.0272470000
_diffrn_orient_matrix_UB_13      -0.0147113000
_diffrn_orient_matrix_UB_21      0.0365962000
_diffrn_orient_matrix_UB_22      -0.0016938000
_diffrn_orient_matrix_UB_23      0.0173587000
_diffrn_orient_matrix_UB_31      -0.0214298000
_diffrn_orient_matrix_UB_32      -0.0167906000
_diffrn_orient_matrix_UB_33      0.0220969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            78378
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.552
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78663
_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 yellowish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             3600
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Flack x determined using 3527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1037
_refine_ls_number_reflns         14111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+21.3485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                10829
_reflns_number_total             14111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03310g2.cif
_cod_data_source_block           1a
_cod_database_code               7708774
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOCu
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.839
_reflns_odcompleteness_completeness 94.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.15
_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, All O(H,H) groups
2.a Rotating group:
 O9(H,HA), O0AA(H0AA,H0AB)
2.b Ternary CH refined with riding coordinates:
 C2(HV), C16(HY), C40(H40), C54(H54)
2.c Aromatic/amide H refined with riding coordinates:
 C15(HB), C61(H61), C53(H53), C60(H60), C14(HC), C23(HD), C45(H45), C44(H44),
 C12(HE), C27(HF), C30(HG), C42(H42), C10(HH), C25(HI), C13(HJ), C9(HK),
 C46(H46), C58(H58), C28(HL), C59(H59), C47(H47), C29(HP), C63(H63), C68(H68),
 C50(H50), C56(H56), C7(HQ), C65(H65), C48(H48), C66(H66), C20(HR), C52(H52),
 C4(HS), C18(HT), C8(HU), C21(HW), C67(H67), C6(HX), C22(H3AA), C51(H51)
2.d Idealised Me refined as rotating group:
 C38(HM,HN,HO), C76(H76A,H76B,H76C), C36(HZ,H1AA,H2AA), C70(H70A,H70B,H70C),
 C72(H72A,H72B,H72C), C34(H4AA,H5AA,H6AA), C74(H74A,H74B,H74C), C32(H7AA,H8AA,
 H9AA)
;
_shelx_res_checksum              84709
_shelx_fab_checksum              23190
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.943
_oxdiff_exptl_absorpt_empirical_full_min 0.544