Atom economical coupling of benzophenone and N-heterocyclic aromatics with SmI<sub>2</sub>.
Jaoul, Arnaud; Yang, Yan; Casaretto, Nicolas; Clavaguéra, Carine; Maron, Laurent; Nocton, Grégory; Chemical communications (Cambridge, England) 56 (2020) 11875–11878; doi:10.1039/d0cc05164k

data_7127136
_publ_section_title
;
 Atom economical coupling of benzophenone and N-heterocyclic aromatics
 with SmI<sub>2</sub>.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11875
_journal_page_last               11878
_journal_paper_doi               10.1039/d0cc05164k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C38 H30 I2 N5 O Sm'
_chemical_formula_sum            'C38 H30 I2 N5 O Sm'
_chemical_formula_weight         976.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.769(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6323(9)
_cell_length_b                   12.3012(9)
_cell_length_c                   24.5249(18)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      21.715
_cell_measurement_theta_min      2.345
_cell_volume                     3507.6(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            92555
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         1.655
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.472
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.8875.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_description       block
_exptl_crystal_F_000             1876
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.908
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         7525
_refine_ls_number_restraints     288
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+78.6489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5996
_reflns_number_total             7525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05164k2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7127135--7127141.cif.'
_cod_database_code               7127136
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.769
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9501(9)
 0.0499(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 N3-C11 \\sim N3-C11A
 with sigma of 0.02
 N3-C15 \\sim N3-C15A
 with sigma of 0.02
 C13-C12 \\sim C13-C12A
 with sigma of 0.02
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C13-C11 \\sim C13-C11A
 with sigma of 0.04
 C13-C15 \\sim C13-C15A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16
 with sigma of 0.04
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16
 with sigma of 0.02
 N3-C14 \\sim N3-C14A
 with sigma of 0.04
 N3-C12 \\sim N3-C12A
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
N3 \\sim N4 \\sim C20 \\sim C13 \\sim C14 \\sim C15 \\sim C19 \\sim C12 \\sim
C18 \\sim C16 \\sim C11 \\sim C17: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008 within 2A
C39 \\sim C36 \\sim C37 \\sim C38 \\sim C35 \\sim N34: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008 within 2A
C33 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008 within 2A
C23 \\sim C22 \\sim C27 \\sim C26 \\sim C25 \\sim C24: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008 within 2A
N3 \\sim C13 \\sim C15 \\sim C14A \\sim C15A \\sim C14 \\sim C11A \\sim C11
\\sim C12 \\sim C12A: within 2A with sigma of 0.004 and sigma for terminal
atoms of 0.008 within 2A
5. Others
 Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=1-FVAR(1)
 Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C1(H1), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C7(H7), C27(H27), C26(H26), C25(H25), C24(H24), C23(H23), C9(H9), C39(H39),
 C3(H3), C2(H2), C20(H20), C19(H19), C18(H18), C17(H17), C36(H36), C37(H37),
 C13(H13), C13(H13A), C14(H14), C38(H38), C12(H12), C35(H35), C11(H11),
 C14A(H14A), C11A(H11A), C12A(H12A)
6.b Fitted hexagon refined as free rotating group:
 C28(C29,C30,C31,C32,C33), C22(C27,C26,C25,C24,C23), N4(C20,C19,C18,C17,C16)
;
_shelx_res_checksum              28
_shelx_hkl_checksum              66070
_olex2_submission_special_instructions 'No special instructions were received'