Ring Expansion of a Ring Expanded Carbene
Hill, Michael; Dutton, Jason Laurence; Wilson, David John; Mahon, Mary F.; Garcia, Lucia; Al Furaiji, Khalidah; Dalton Trans.  (2017) –; doi:10.1039/C7DT03046K

data_7044006
_publ_section_title
;
 Ring Expansion of a Ring Expanded Carbene
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT03046K
_journal_year                    2017
_chemical_formula_moiety         'C28 H36 N2 Si'
_chemical_formula_sum            'C28 H36 N2 Si'
_chemical_formula_weight         428.68
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-07-17 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.900(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2680(3)
_cell_length_b                   15.1828(3)
_cell_length_c                   13.2770(3)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.5440
_cell_measurement_theta_min      4.5700
_cell_volume                     2530.39(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.635
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     118
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1111P)^2^+1.8455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2242
_refine_ls_wR_factor_ref         0.2308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4398
_reflns_number_total             5081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03046k2.cif
_cod_data_source_block           s17msh46
_cod_original_cell_volume        2530.39(10)
_cod_database_code               7044006
_shelxl_version_number           2014-3
_chemical_oxdiff_usercomment     'colorless plate'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C11 \\sim N2A-C11 \\sim N1A-C20A \\sim N1-C20
 with sigma of 0.005
 N1A-C8A \\sim N1-C8 \\sim N2A-C10A \\sim N2-C10
 with sigma of 0.005
 C9A-C8A \\sim C9-C8 \\sim C9-C10 \\sim C9A-C10A
 with sigma of 0.005
 Si1A-N1A \\sim Si1-N2
 with sigma of 0.005
 N2A-C1A \\sim N1-C1
 with sigma of 0.005
 Si1A-C1A \\sim Si1-C1
 with sigma of 0.005
 C28A-C25A \\sim C28-C25
 with sigma of 0.005
 C26-C21 \\sim C26A-C21A \\sim C27-C23 \\sim C27A-C23A
 with sigma of 0.005
 C9-C8 \\sim C9A-C8A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.01
C20A \\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim C26A \\sim
C27A \\sim C28A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(C10A) = Uanis(C10)
Uanis(C9A) = Uanis(C9)
Uanis(C8) = Uanis(C8A)
Uanis(N1) = Uanis(N1A)
Uanis(N2) = Uanis(N2A)
Uanis(C1) = Uanis(C1A)
4. Others
 Fixed Sof: Si1(0.66) H1A(0.66) H1B(0.66) Si1A(0.34) H1AA(0.34) N1A(0.34)
 N2A(0.34) C1A(0.34) H1AB(0.34) H1AC(0.34) C2A(0.34) C3A(0.34) H3A(0.34)
 C4A(0.34) H4A(0.34) C5A(0.34) H5A(0.34) C6A(0.34) H6A(0.34) C7A(0.34)
 H7A(0.34) C8A(0.34) H8AA(0.34) H8AB(0.34) C9A(0.34) H9AA(0.34) H9AB(0.34)
 C10A(0.34) H10A(0.34) H10B(0.34) C20A(0.34) C21A(0.34) C22A(0.34) H22A(0.34)
 C23A(0.34) C24A(0.34) H24A(0.34) C25A(0.34) C26A(0.34) H26A(0.34) H26B(0.34)
 H26C(0.34) C27A(0.34) H27A(0.34) H27B(0.34) H27C(0.34) C28A(0.34) H28A(0.34)
 H28B(0.34) H28C(0.34) N1(0.66) N2(0.66) C9(0.66) H9A(0.66) H9B(0.66) C20(0.66)
 C21(0.66) C22(0.66) H22(0.66) C23(0.66) C24(0.66) H24(0.66) C25(0.66)
 C26(0.66) H26D(0.66) H26E(0.66) H26F(0.66) C1(0.66) H1(0.66) C8(0.66)
 H8A(0.66) H8B(0.66) C2(0.66) C7(0.66) H7(0.66) C6(0.66) H6(0.66) C5(0.66)
 H5(0.66) C4(0.66) H4(0.66) C3(0.66) H3(0.66) C10(0.66) H10C(0.66) H10D(0.66)
 C27(0.66) H27D(0.66) H27E(0.66) H27F(0.66) C28(0.66) H28D(0.66) H28E(0.66)
 H28F(0.66)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C1A(H1AB,H1AC), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C9(H9A,H9B),
 C8(H8A,H8B), C10(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A),
 C22A(H22A), C24A(H24A), C22(H22), C24(H24), C7(H7), C6(H6), C5(H5), C4(H4),
 C3(H3)
5.d Fitted hexagon refined as free rotating group:
 C2A(C3A,C4A,C5A,C6A,C7A), C20A(C21A,C22A,C23A,C24A,C25A), C20(C21,C22,C23,C24,
 C25), C2(C7,C6,C5,C4,C3)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C26A(H26A,H26B,
 H26C), C27A(H27A,H27B,H27C), C28A(H28A,H28B,H28C), C26(H26D,H26E,H26F),
 C27(H27D,H27E,H27F), C28(H28D,H28E,H28F)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.748