Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism.
Okamoto, Yuta; Tanioka, Masaru; Muranaka, Atsuya; Miyamoto, Kazunori; Aoyama, Tetsuya; Ouyang, Xingmei; Kamino, Shinichiro; Sawada, Daisuke; Uchiyama, Masanobu; Journal of the American Chemical Society 140 (2018) 17857–17861; doi:10.1021/jacs.8b11092

data_4133554
_publ_section_title
;
 Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared
 Absorption/Emission and Two-Step Electrochromism.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17857
_journal_page_last               17861
_journal_paper_doi               10.1021/jacs.8b11092
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C27 H29 N O2, C H4 O'
_chemical_formula_sum            'C28 H33 N O3'
_chemical_formula_weight         431.55
_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             2018-10-04
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                84.370(3)
_cell_angle_beta                 88.502(4)
_cell_angle_gamma                70.429(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7628(4)
_cell_length_b                   9.6300(4)
_cell_length_c                   16.0084(6)
_cell_measurement_reflns_used    4430
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.6150
_cell_measurement_theta_min      2.7930
_cell_volume                     1122.11(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -95.00  -5.00   0.50   15.00    --  -39.70 118.00 -77.00  180
  2  \w     48.00 116.00   0.50   15.00    --   39.70 160.00  74.00  136
  3  \w     81.00 106.00   0.50   45.00    --  113.69 160.00  74.00   50
  4  \w    102.00 127.00   0.50   45.00    --  113.69 118.00 -77.00   50
  5  \w    109.00 167.00   0.50   45.00    --  113.69  30.00  60.00  116
  6  \w    101.00 136.00   0.50   45.00    --  113.69 -77.00   0.00   70
  7  \w     88.00 140.00   0.50   45.00    --  113.69-160.00  44.00  104
  8  \w     77.00 120.00   0.50   45.00    --  113.69 -77.00-120.00   86
  9  \w     60.00 111.00   0.50   45.00    --  113.69-118.00-164.00  102
 10  \w     58.00 113.00   0.50   45.00    --  113.69-125.00-180.00  110
 11  \w     52.00 103.00   0.50   45.00    --  113.69 -94.00-120.00  102
 12  \w     34.00  67.00   0.50   45.00    --  113.69 -30.00 -60.00   66
 13  \w     35.00  79.00   0.50   45.00    --  113.69 -45.00 -30.00   88
 14  \w     51.00  83.00   0.50   45.00    --  113.69 -77.00   0.00   64
 15  \w     42.00  69.00   0.50   45.00    --  113.69 -45.00  30.00   54
 16  \w     51.00  77.00   0.50   45.00    --  113.69 -45.00  90.00   52
 17  \w     35.00  95.00   0.50   45.00    --  113.69 -94.00  60.00  120
 18  \w     39.00  77.00   0.50   45.00    --  113.69 -45.00 150.00   76
 19  \w     33.00 177.00   0.50   45.00    --  113.69 -15.00  60.00  288
 20  \w     31.00  69.00   0.50   45.00    --  113.69 -30.00  60.00   76
 21  \w     32.00  59.00   0.50   45.00    --  113.69 -30.00 120.00   54
 22  \w     32.00  63.00   0.50   45.00    --  113.69 -30.00 150.00   62
 23  \w     31.00  65.00   0.50   45.00    --  113.69 -30.00  30.00   68
 24  \w     36.00 107.00   0.50   45.00    --  113.69 -94.00   0.00  142
 25  \w     41.00  81.00   0.50   45.00    --  113.69-125.00 -60.00   80
 26  \w     31.00  69.00   0.50   45.00    --  113.69 -30.00-150.00   76
 27  \w     40.00  67.00   0.50   45.00    --  113.69 -45.00-180.00   54
 28  \w     34.00  65.00   0.50   45.00    --  113.69 -30.00-120.00   62
 29  \w     34.00  69.00   0.50   45.00    --  113.69 -30.00 -90.00   70
 30  \w     31.00  56.00   0.50   45.00    --  113.69 -30.00-180.00   50
 31  \w      5.00  95.00   0.50   15.00    --   39.70-118.00-164.00  180
 32  \w     28.00 122.00   0.50   15.00    --   39.70-160.00  44.00  188
 33  \w     10.00  49.00   0.50   15.00    --   39.70 -57.00  60.00   78
 34  \w    -33.00  -4.00   0.50   15.00    --   39.70 -57.00  60.00   58
 35  \w   -116.00 -48.00   0.50   15.00    --  -39.70-160.00  44.00  136
 36  \w   -113.00  -8.00   0.50   15.00    --  -39.70 -77.00 120.00  210
 37  \w    -64.00  -7.00   0.50   45.00    --  -84.50  30.00 120.00  114
 38  \w    -97.00 -70.00   0.50   45.00    --  -84.50 160.00  74.00   54
 39  \w   -113.00 -73.00   0.50   15.00    --  -39.70 160.00  74.00   80
 40  \w   -112.00  -5.00   0.50   45.00    --  -84.50 118.00 -77.00  214
 41  \w    -91.00 -50.00   0.50   45.00    --  -84.50 -30.00-120.00   82
 42  \w    -62.00  -5.00   0.50   15.00    --  -39.70 -77.00-180.00  114
 43  \w   -102.00 -67.00   0.50   15.00    --  -39.70 -77.00-180.00   70
 44  \w   -132.00-105.00   0.50   45.00    --  -84.50 -30.00-120.00   54
 45  \w   -163.00 -75.00   0.50   45.00    --  -84.50-118.00-164.00  176
 46  \w   -166.00-140.00   0.50   45.00    --  -84.50 -30.00-120.00   52
 47  \w   -128.00-103.00   0.50   45.00    --  -84.50-160.00  44.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1603650000
_diffrn_orient_matrix_UB_12      -0.0971453000
_diffrn_orient_matrix_UB_13      -0.0497502000
_diffrn_orient_matrix_UB_21      -0.1122463000
_diffrn_orient_matrix_UB_22      0.0569045000
_diffrn_orient_matrix_UB_23      -0.0818017000
_diffrn_orient_matrix_UB_31      0.0777665000
_diffrn_orient_matrix_UB_32      0.1281139000
_diffrn_orient_matrix_UB_33      -0.0136017000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12596
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         2.774
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0750
_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^)+(0.1563P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1959
_refine_ls_wR_factor_ref         0.2082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3273
_reflns_number_total             4107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11092_si_003.cif
_cod_data_source_block           1Pen
_cod_database_code               4133554
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C56 H66 N2 O6'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00C), C00N(H00D,H00F), C00O(H00J,H00M), C00P(H00N,H00O), C00Q(H00P,
 H00Q), C00R(H00R,H00S), C00S(H00T,H00U), C00T(H00V,H00W)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K),
 C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00U(H00X,H00Y,H), C00V(H00,HA,HB), C00W(H00Z,HC,HD)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 3.180
_oxdiff_exptl_absorpt_empirical_full_min 0.426