Organic Redox Systems Based on Pyridinium-Carbene Hybrids.
Antoni, Patrick W.; Bruckhoff, Tim; Hansmann, Max M.; Journal of the American Chemical Society 141 (2019) 9701–9711; doi:10.1021/jacs.9b04249

data_4127441
_publ_section_title
;
 Organic Redox Systems Based on Pyridinium-Carbene Hybrids.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9701
_journal_page_last               9711
_journal_paper_doi               10.1021/jacs.9b04249
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C29 H35 N3'
_chemical_formula_sum            'C29 H35 N3'
_chemical_formula_weight         425.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.045(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8369(6)
_cell_length_b                   34.229(2)
_cell_length_c                   16.6943(11)
_cell_measurement_reflns_used    9697
_cell_measurement_temperature    99.98
_cell_measurement_theta_max      74.53
_cell_measurement_theta_min      2.58
_cell_volume                     4956.1(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.811
_diffrn_measured_fraction_theta_max 0.765
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.811
_diffrn_reflns_Laue_measured_fraction_max 0.765
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9114
_diffrn_reflns_point_group_measured_fraction_full 0.707
_diffrn_reflns_point_group_measured_fraction_max 0.654
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.431
_diffrn_reflns_theta_min         2.582
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.518255
_exptl_absorpt_correction_T_min  0.448399
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 53688 reflections, Rint = 0.0283
 (50978 with I > 3sig(I), Rint = 0.0281)
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_recrystallization_method
'The material was recrystallised from Diethylether by slow evaporation'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.128
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 4086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         9114
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0926P)^2^+0.5114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                9073
_reflns_number_total             9114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04249_si_004.cif
_cod_data_source_block           0605_cg_0m_4
_cod_database_code               4127441
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4546(16)
 0.5454(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C35(H35), C41(H41), C43(H43), C50(H50), C51(H51), C57(H57), C58(H58),
 C8(H8), C11(H11), C15(H15), C16(H16), C19(H19), C21(H21), C28(H28), C30(H30)
3.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C45(H45A,H45B,
 H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C56(H56A,H56B,H56C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_shelx_res_checksum              64582
_shelx_hkl_checksum              33576
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'