Electropolymerizable N-heterocyclic carbene complexes of Rh and Ir with enantiotropic polymorphic phases.
Wang, Weiran; Lynch, Vincent M.; Guo, Hongyu; Datta, Anwesha; Jones, Richard A.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 2264–2272; doi:10.1039/c9dt04844h

data_7703412
_publ_section_title
;
 Electropolymerizable N-heterocyclic carbene complexes of Rh and Ir with
 enantiotropic polymorphic phases.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2264
_journal_page_last               2272
_journal_paper_doi               10.1039/c9dt04844h
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C22.96 H24 I Ir N2 S3'
_chemical_formula_sum            'C23 H24 I Ir N2 S3'
_chemical_formula_weight         743.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-05 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.778(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.425(2)
_cell_length_b                   9.2985(8)
_cell_length_c                   23.526(2)
_cell_measurement_reflns_used    8481
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.455
_cell_measurement_theta_min      2.371
_cell_volume                     4889.6(7)
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            52030
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.510
_diffrn_reflns_theta_min         1.822
_exptl_absorpt_coefficient_mu    6.994
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker Nonius Kappa CCD
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_description       prism
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.100
_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     388
_refine_ls_number_reflns         6150
_refine_ls_number_restraints     721
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+5.6292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4432
_reflns_number_total             6150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt04844h2.cif
_cod_data_source_block           Ir_298K_c2c
_cod_depositor_comments
'Adding full bibliography for 7703409--7703412.cif.'
_cod_original_cell_volume        4889.6(8)
_cod_database_code               7703412
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.463
_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
 S1-C4 \\sim S1A-C4
 with sigma of 0.02
 S1-C1 \\sim S1A-C1A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C2-C1 \\sim C2A-C1A
 with sigma of 0.02
 S1-C2 \\sim S1A-C2A
 with sigma of 0.04
 C3-C1 \\sim C3A-C1A
 with sigma of 0.04
 C4-C2 \\sim C4-C2A
 with sigma of 0.04
 C4-C1 \\sim C4-C1A
 with sigma of 0.04
 S3-C9 \\sim S3A-C9
 with sigma of 0.02
 S3-C11 \\sim S3A-C11A
 with sigma of 0.02
 C9-C11 \\sim C9-C11A
 with sigma of 0.02
 C10-C9 \\sim C10A-C9
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C11-C12 \\sim C11A-C12A
 with sigma of 0.02
 S3-C12 \\sim S3A-C12A
 with sigma of 0.02
 C9-C12 \\sim C9-C12A
 with sigma of 0.02
 C10-C12 \\sim C10A-C12A
 with sigma of 0.02
 Ir1-I1 \\sim Ir1A-I1A
 with sigma of 0.02
 Ir1-C14 \\sim Ir1A-C14
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C16-C23 \\sim C16A-C23A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 Ir1-C17 \\sim Ir1A-C17A
 with sigma of 0.04
 Ir1-C16 \\sim Ir1A-C16A
 with sigma of 0.04
 Ir1-C18 \\sim Ir1A-C18A
 with sigma of 0.04
 Ir1-C21 \\sim Ir1A-C21A
 with sigma of 0.04
 Ir1-C20 \\sim Ir1A-C20A
 with sigma of 0.04
 Ir1-C22 \\sim Ir1A-C22A
 with sigma of 0.04
 Ir1-C23 \\sim Ir1A-C23A
 with sigma of 0.04
 I1-C14 \\sim I1A-C14
 with sigma of 0.04
 I1-C17 \\sim I1A-C17A
 with sigma of 0.04
 I1-C16 \\sim I1A-C16A
 with sigma of 0.04
 I1-C21 \\sim I1A-C21A
 with sigma of 0.04
 I1-C20 \\sim I1A-C20A
 with sigma of 0.04
 C14-C17 \\sim C14-C17A
 with sigma of 0.04
 C14-C16 \\sim C14-C16A
 with sigma of 0.04
 C14-C21 \\sim C14-C21A
 with sigma of 0.04
 C14-C20 \\sim C14-C20A
 with sigma of 0.04
 C17-C16 \\sim C17A-C16A
 with sigma of 0.04
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C17-C20 \\sim C17A-C20A
 with sigma of 0.04
 C17-C23 \\sim C17A-C23A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C16-C21 \\sim C16A-C21A
 with sigma of 0.04
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 C16-C22 \\sim C16A-C22A
 with sigma of 0.04
 C21-C20 \\sim C21A-C20A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19
 with sigma of 0.02
 C20-C19 \\sim C20A-C19
 with sigma of 0.02
 Ir1-C19 \\sim Ir1A-C19
 with sigma of 0.04
 C17-C19 \\sim C17A-C19
 with sigma of 0.04
 C21-C19 \\sim C21A-C19
 with sigma of 0.04
3. Restrained planarity
 S1, C4, C3, C2, C1
 with sigma of 0.1
 S1A, C4, C3A, C2A, C1A
 with sigma of 0.1
 S3A, C11A, C12A, C10A, C9
 with sigma of 0.1
 S3, C11, C12, C10, C9
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C4 \\sim C3 \\sim C2 \\sim C1 \\sim S1: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C4 \\sim C3A \\sim C2A \\sim C1A \\sim S1A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C16 \\sim C23 \\sim C22 \\sim C21: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C16 \\sim C21: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
S3A \\sim C9 \\sim C10A \\sim C11A \\sim C12A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
S3 \\sim C9 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Ir1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Ir1 \\sim I1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
I1 \\sim Ir1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Ir1A \\sim I1A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Ir1 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim
C23: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Ir1 \\sim C21 \\sim C22 \\sim C23 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim
C20: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Ir1A \\sim C21A \\sim C22A \\sim C23A \\sim C16A \\sim C17A \\sim C18A \\sim
C19 \\sim C20A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(I1) = Uanis(I1A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C17A) = Uanis(C17)
Uanis(C18A) = Uanis(C18)
Uanis(C20) = Uanis(C20A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C10A)=Sof(H10A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(S3A)=1-FVAR(1)
 Sof(S3)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(1)
 Sof(S1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=1-FVAR(2)
 Sof(S1)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(C1)=Sof(H1)=FVAR(2)
 Sof(H19C)=Sof(H19D)=Sof(Ir1A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C22A)=
 Sof(H22C)=Sof(H22D)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(I1A)=1-FVAR(3)
 Sof(Ir1)=Sof(I1)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=Sof(C18)=Sof(H18A)=
 Sof(H18B)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)=Sof(H19A)=Sof(H19B)=Sof(C22)=
 Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C17(H17), C16(H16), C21(H21), C20(H20), C16A(H16A), C17A(H17A), C20A(H20A),
 C21A(H21A)
7.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C19(H19C,H19D), C22(H22A,H22B), C23(H23A,
 H23B), C18A(H18C,H18D), C23A(H23C,H23D), C22A(H22C,H22D)
7.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C2(H2), C1(H1), C11(H11), C12(H12), C10A(H10A), C12A(H12A),
 C11A(H11A), C1A(H1A), C2A(H2A), C3A(H3A)
7.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              80074
_olex2_submission_special_instructions 'No special instructions were received'