Three Ways Isolable Carbenes Can Modulate Emission of NH-Containing Fluorophores.
Kieser, Jerod M.; Kinney, Zacharias J.; Gaffen, Joshua R.; Evariste, Sloane; Harrison, Alexandra M.; Rheingold, Arnold L.; Protasiewicz, John D.; Journal of the American Chemical Society 141 (2019) 12055–12063; doi:10.1021/jacs.9b04864

data_4128591
_publ_section_title
;
 Three Ways Isolable Carbenes Can Modulate Emission of NH-Containing
 Fluorophores.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12055
_journal_page_last               12063
_journal_paper_doi               10.1021/jacs.9b04864
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C27 H37 N2, C13 H9 N2'
_chemical_formula_sum            'C40 H46 N4'
_chemical_formula_weight         582.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5479)
;
_cell_angle_alpha                106.262(2)
_cell_angle_beta                 94.104(2)
_cell_angle_gamma                100.781(2)
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_cell_length_a                   16.6802(7)
_cell_length_b                   22.0707(9)
_cell_length_c                   29.4908(11)
_cell_measurement_reflns_used    9360
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.412
_cell_measurement_theta_min      2.958
_cell_volume                     10149.7(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 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    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            157114
_diffrn_reflns_point_group_measured_fraction_full 0.988
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_diffrn_reflns_theta_max         68.474
_diffrn_reflns_theta_min         1.574
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker MicroStar FR-592'
_diffrn_standards_number         0
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_exptl_absorpt_correction_T_min  0.6828
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_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0754 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.9067. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.708
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_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     2424
_refine_ls_number_reflns         36662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1651
_refine_ls_R_factor_gt           0.0984
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1155P)^2^+22.2834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2505
_refine_ls_wR_factor_ref         0.3106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20182
_reflns_number_total             36662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04864_si_005.cif
_cod_data_source_block           large_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4128591
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10A(H10A), C13A(H13A), C22A(H22A), C26A(H26A), C10B(H10B), C13B(H13B),
 C22B(H22B), C26B(H26B), C10C(H10C), C19C(H19C), C22C(H22C), C048(H048),
 C10D(H10D), C13D(H13D), C22D(H22D), C26D(H26D), C10E(H10E), C13E(H13E),
 C22E(H22E), C26E(H26E), C10F(H10F), C13F(H13F), C22F(H22F), C26F(H26F)
2.b Me refined with riding coordinates:
 C12C(H12G,H12H,H12I)
2.c Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C6A(H6A), C7A(H7A), C8A(H8A), C18A(H18A),
 C19A(H19A), C20A(H20A), C29C(H29C), C30C(H30C), C31C(H31C), C32C(H32C),
 C36C(H36C), C37C(H37C), C38C(H38C), C39C(H39C), C40C(H40C), C29A(H29A),
 C30A(H30A), C31A(H31A), C32A(H32A), C36A(H36A), C37A(H37A), C38A(H38A),
 C39A(H39A), C40A(H40A), C1B(H1B), C2B(H2B), C3B(H3B), C6B(H6B), C7B(H7B),
 C8B(H8B), C18B(H18B), C19B(H19B), C20B(H20B), C29E(H29E), C30E(H30E),
 C31E(H31E), C32E(H32E), C36E(H36E), C37E(H37E), C38E(H38E), C39E(H39E),
 C40E(H40E), C1C(H1C), C2C(H2C), C3C(H3C), C6C(H6C), C7C(H7C), C8C(H8C),
 C15C(H15G), C16C(H16C), C17C(H17C), C29B(H29B), C30B(H30B), C31B(H31B),
 C32B(H32B), C36B(H36B), C37B(H37B), C38B(H38B), C39B(H39B), C40B(H40B),
 C1D(H1D), C2D(H2D), C3D(H3D), C6D(H6D), C7D(H7D), C8D(H8D), C18D(H18D),
 C19D(H19D), C20D(H20F), C29D(H29D), C30D(H30D), C31D(H31D), C32D(H32D),
 C36D(H36D), C37D(H37D), C38D(H38D), C39D(H39D), C40D(H40D), C1E(H1E), C2E(H2E),
  C3E(H3E), C6E(H6E), C7E(H7E), C8E(H8E), C18E(H18E), C19E(H19E), C20E(H20G),
 C29F(H29F), C30F(H30F), C31F(H31F), C32F(H32F), C36F(H36F), C37F(H37F),
 C38F(H38F), C39F(H39F), C40F(H40F), C1F(H1F), C2F(H2F), C3F(H3F), C6F(H6F),
 C7F(H7F), C8F(H8F), C18F(H18F), C19F(H19F), C20F(H20H)
2.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C14A(H14A,H14B,H14C), C15A(H15A,
 H15B,H15C), C23A(H23A,H23B,H23C), C24A(H24A,H24B,H24C), C25A(H25A,H25B,H25C),
 C27A(H27A,H27B,H27C), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F), C14B(H14D,
 H14E,H14F), C15B(H15D,H15E,H15F), C23B(H23D,H23E,H23F), C24B(H24D,H24E,H24F),
 C25B(H25D,H25E,H25F), C27B(H27D,H27E,H27F), C06F(H06A,H06B,H06C), C06W(H06D,
 H06E,H06F), C11C(H11G,H11H,H11I), C20C(H20C,H20D,H20E), C21C(H21A,H21B,H21C),
 C23C(H23G,H23H,H23I), C24C(H24G,H24H,H24I), C11D(H11J,H11K,H11L), C12D(H12J,
 H12K,H12L), C14D(H14G,H14H,H14I), C15D(H15H,H15I,H15J), C23D(H23J,H23K,H23L),
 C24D(H24J,H24K,H24L), C25D(H25G,H25H,H25I), C27D(H27G,H27H,H27I), C11E(H11M,
 H11N,H11O), C12E(H12M,H12N,H12O), C14E(H14J,H14K,H14L), C15E(H15K,H15L,H15M),
 C23E(H23M,H23N,H23O), C24E(H24M,H24N,H24O), C25E(H25J,H25K,H25L), C27E(H27J,
 H27K,H27L), C11F(H11P,H11Q,H11R), C12F(H12P,H12Q,H12R), C14F(H14M,H14N,H14O),
 C15F(H15N,H15O,H15P), C23F(H23P,H23Q,H23R), C24F(H24P,H24Q,H24R), C25F(H25M,
 H25N,H25O), C27F(H27M,H27N,H27O)
;
_shelx_res_checksum              76502
_shelx_hkl_checksum              9519
_olex2_submission_special_instructions 'No special instructions were received'