Access to divalent lanthanide NHC complexes by redox-transmetallation from silver and CO2 insertion reactions
Simler, Thomas; Feuerstein, Thomas J.; Yadav, Ravi; Gamer, Michael T.; Roesky, Peter W.; Chemical Communications  (2019) –; doi:10.1039/C8CC08120D

data_7122712
_publ_section_title
;
 Access to divalent lanthanide NHC complexes by redox-transmetallation
 from silver and CO2 insertion reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08120D
_journal_year                    2019
_chemical_formula_moiety         'C92 H124 N6 O8 Yb, 2(I), C4 H8 O, 1[C5H12]'
_chemical_formula_sum            'C101 H144 I2 N6 O9 Yb'
_chemical_formula_weight         2013.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-13 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6152(2)
_cell_length_b                   42.7426(6)
_cell_length_c                   16.4556(2)
_cell_measurement_reflns_used    81219
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      1.33
_cell_volume                     10271.4(2)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
PLATON (A.L.Spek, 2009)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
PLATON (A.L.Spek, 2009)
;
_computing_molecular_graphics    'Diamond 4, Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
MS Word (Microsoft)
Olex2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
 291 frames, detector distance = 135 mm
;
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            74123
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.611
_diffrn_reflns_theta_max         25.611
_diffrn_reflns_theta_min         1.327
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.56
_exptl_absorpt_correction_T_max  0.8245
_exptl_absorpt_correction_T_min  0.6275
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
;
_exptl_crystal_colour            'orange brown'
_exptl_crystal_colour_modifier   orange
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4160
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.407
_exptl_crystal_size_min          0.327
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1212
_refine_ls_number_reflns         19227
_refine_ls_number_restraints     265
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+5.5290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15079
_reflns_number_total             19227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08120d2.cif
_cod_data_source_block           txs247-2
_cod_database_code               7122712
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.628
_shelx_estimated_absorpt_t_min   0.499
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C26B-C25
 1.52 with sigma of 0.02
 C26B-C27B = C28B-C26B = C28A-C26A = C27A-C26A
 1.54 with sigma of 0.02
 C54B-C53 = C54A-C53
 1.52 with sigma of 0.02
 C55B-C54B = C56B-C54B = C54A-C55A = C54A-C56A
 1.54 with sigma of 0.02
 O8B-C92B
 1.44 with sigma of 0.02
 C92B-C91B
 1.535 with sigma of 0.02
 O8A-C92A = O8B-C92B = O8A-C89A = O8B-C89B
 1.44 with sigma of 0.02
 C92B-C91B = C91B-C90 = C89B-C90
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C25 \\sim C26B \\sim C27B \\sim C28B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
O8A \\sim C89A \\sim C90 \\sim C91A \\sim C92A: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
C53 \\sim C54B \\sim C55B \\sim C56B: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C53 \\sim C54A \\sim C55A \\sim C56A: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C85B \\sim C86B \\sim C87B \\sim C88B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
O8B \\sim C89B \\sim C90 \\sim C91B \\sim C92B: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04
O8A \\sim O8B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O9A \\sim C93A \\sim C94A \\sim C95A \\sim C96A: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04
C93B \\sim C94B \\sim C95B \\sim C96B: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C25, C26B, C27B, C28B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O8A, C89A, C90, C91A, C92A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C53, C54B, C55B, C56B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C53, C54A, C55A, C56A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C85B, C86B, C87B, C88B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O9A, C93A, C94A, C95A, C96A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C93B, C94B, C95B, C96B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Fixed Sof: O5A(0.85) O5B(0.15) O6A(0.85) O6B(0.15) O8A(0.6) O8B(0.4)
 C26A(0.6) H26A(0.6) C26B(0.4) H26B(0.4) C27A(0.6) H27A(0.6) H27B(0.6)
 H27C(0.6) C27B(0.4) H27D(0.4) H27E(0.4) H27F(0.4) C28A(0.6) H28A(0.6)
 H28B(0.6) H28C(0.6) C28B(0.4) H28D(0.4) H28E(0.4) H28F(0.4) C54A(0.6)
 H54A(0.6) C54B(0.4) H54B(0.4) C55A(0.6) H55A(0.6) H55B(0.6) H55C(0.6)
 C55B(0.4) H55D(0.4) H55E(0.4) H55F(0.4) C56A(0.6) H56A(0.6) H56B(0.6)
 H56C(0.6) C56B(0.4) H56D(0.4) H56E(0.4) H56F(0.4) C85A(0.6) H85A(0.6)
 H85B(0.6) C85B(0.4) H85C(0.4) H85D(0.4) C86A(0.6) H86A(0.6) H86B(0.6)
 C86B(0.4) H86C(0.4) H86D(0.4) C87A(0.6) H87A(0.6) H87B(0.6) C87B(0.4)
 H87C(0.4) H87D(0.4) C88A(0.6) H88A(0.6) H88B(0.6) C88B(0.4) H88C(0.4)
 H88D(0.4) C89A(0.6) H89A(0.6) H89B(0.6) C89B(0.4) H89C(0.4) H89D(0.4)
 H90A(0.6) H90B(0.6) H90C(0.4) H90D(0.4) C91A(0.6) H91A(0.6) H91B(0.6)
 C91B(0.4) H91C(0.4) H91D(0.4) C92A(0.6) H92A(0.6) H92B(0.6) C92B(0.4)
 H92C(0.4) H92D(0.4) I2A(0.45) I2C(0.25) I2B(0.3) O9A(0.5) O9B(0.5) C93A(0.5)
 H93A(0.5) H93B(0.5) C93B(0.5) H93C(0.5) H93D(0.5) C94A(0.5) H94A(0.5)
 H94B(0.5) C94B(0.5) H94C(0.5) H94D(0.5) C95A(0.5) H95A(0.5) H95B(0.5)
 C95B(0.5) H95C(0.5) H95D(0.5) C96A(0.5) H96A(0.5) H96B(0.5) C96B(0.5)
 H96C(0.5) H96D(0.5)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C19(H19), C26A(H26A), C26B(H26B), C35(H35), C42(H42),
 C47(H47), C54A(H54A), C54B(H54B), C63(H63), C70(H70), C75(H75), C82(H82)
6.b Secondary CH2 refined with riding coordinates:
 C85A(H85A,H85B), C85B(H85C,H85D), C86A(H86A,H86B), C86B(H86C,H86D), C87A(H87A,
 H87B), C87B(H87C,H87D), C88A(H88A,H88B), C88B(H88C,H88D), C89A(H89A,H89B),
 C89B(H89C,H89D), C90(H90A,H90B), C90(H90C,H90D), C91A(H91A,H91B), C91B(H91C,
 H91D), C92A(H92A,H92B), C92B(H92C,H92D), C93A(H93A,H93B), C93B(H93C,H93D),
 C94A(H94A,H94B), C94B(H94C,H94D), C95A(H95A,H95B), C95B(H95C,H95D), C96A(H96A,
 H96B), C96B(H96C,H96D)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C22(H22), C23(H23), C24(H24),
 C31(H31), C32(H32), C38(H38), C39(H39), C40(H40), C50(H50), C51(H51), C52(H52),
  C59(H59), C60(H60), C66(H66), C67(H67), C68(H68), C78(H78), C79(H79), C80(H80)
6.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C27A(H27A,H27B,H27C), C27B(H27D,H27E,
 H27F), C28A(H28A,H28B,H28C), C28B(H28D,H28E,H28F), C36(H36A,H36B,H36C),
 C37(H37A,H37B,H37C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C55A(H55A,H55B,H55C), C55B(H55D,H55E,H55F),
 C56A(H56A,H56B,H56C), C56B(H56D,H56E,H56F), C64(H64A,H64B,H64C), C65(H65A,H65B,
 H65C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C76(H76A,H76B,H76C), C77(H77A,
 H77B,H77C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C)
;
_shelx_res_checksum              71748
_shelx_hkl_checksum              89410
_shelx_fab_checksum              70325
_olex2_submission_special_instructions 'No special instructions were received'