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_7127135
_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         'C50 H68 I4 O8 Sm2, C4 H8 O'
_chemical_formula_sum            'C54 H76 I4 O9 Sm2'
_chemical_formula_weight         1677.44
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1373(4)
_cell_length_b                   17.5042(4)
_cell_length_c                   21.1140(4)
_cell_measurement_reflns_used    6059
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     5964.1(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Kappa APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21322
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.327
_exptl_absorpt_coefficient_mu    4.070
_exptl_absorpt_correction_T_max  1.1196
_exptl_absorpt_correction_T_min  0.8754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   DENZO/SCALEPACK
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_description       plate
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         3.734
_refine_diff_density_min         -2.599
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         12058
_refine_ls_number_restraints     254
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0596P)^2^+48.3675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                11533
_reflns_number_total             12058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05164k2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7127135--7127141.cif.'
_cod_database_code               7127135
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.375
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.67(3)
 0.33(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
3. Restrained distances
 O3-C9 \\sim O3-C12
 with sigma of 0.02
 C9-C10 \\sim C10-C11B \\sim C11B-C12
 with sigma of 0.02
 C15-C16 \\sim C16-C17 \\sim C17-C18
 with sigma of 0.02
 O7-C19 \\sim O7-C22
 with sigma of 0.02
 C19-C20 \\sim C20-C21 \\sim C21-C22
 with sigma of 0.02
 C23-C24 \\sim C24-C25 \\sim C25-C26
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O3 \\sim C9 \\sim C10 \\sim C12 \\sim C11A \\sim C11B: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008 within 2A
O9 \\sim C51 \\sim C52 \\sim C53 \\sim C54: within 2A with sigma of 0.004 and
sigma for terminal atoms of 0.008 within 2A
O6 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of 0.004 and
sigma for terminal atoms of 0.008 within 2A
O7 \\sim C19 \\sim C20 \\sim C21 \\sim C22: within 2A with sigma of 0.004 and
sigma for terminal atoms of 0.008 within 2A
O8 \\sim C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.004 and
sigma for terminal atoms of 0.008 within 2A
C27 \\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
C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49 \\sim C50: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.004 within 2A
5. Others
 Sof(H10C)=Sof(H10D)=Sof(H12C)=Sof(H12D)=Sof(C11B)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(H12A)=Sof(H12B)=Sof(C11A)=Sof(H11A)=Sof(H11B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10C,H10D), C10(H10A,H10B),
 C12(H12C,H12D), C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C11A(H11A,H11B), C11B(H11C,H11D), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,
 H53B), C54(H54A,H54B)
6.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
  C46(H46), C47(H47), C48(H48), C49(H49), C50(H50)
;
_shelx_res_checksum              74248
_shelx_hkl_checksum              16719
_olex2_submission_special_instructions 'No special instructions were received'