Solvent-induced reversible solid-state colour change of an intramolecular charge-transfer complex
Ping Li; Josef M. Maier; Jungwun Hwang; Mark D. Smith; Jeanette A. Krause; Brian T. Mullis; Sharon M. S. Strickland; Ken D. Shimizu; Chem.Commun. 51 (2015) 14809–; doi:10.1039/C5cc06140G

data_7117837
_publ_section_title
;
 Solvent-induced reversible solid-state colour change of an intramolecular
 charge-transfer complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              14809
_journal_paper_doi               10.1039/C5cc06140G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C72 H54 N2 O8, 2(C2 H5 N O2)'
_chemical_formula_sum            'C76 H64 N4 O12'
_chemical_formula_weight         1225.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-12 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                115.858(3)
_cell_angle_beta                 90.538(4)
_cell_angle_gamma                92.053(4)
_cell_formula_units_Z            2
_cell_length_a                   10.3369(14)
_cell_length_b                   17.1080(18)
_cell_length_c                   18.463(2)
_cell_measurement_reflns_used    9437
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.382
_cell_measurement_theta_min      2.352
_cell_volume                     2935.1(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_laue_measured_fraction_full 0.987
_diffrn_reflns_laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9684
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.300
_diffrn_reflns_theta_max         24.407
_diffrn_reflns_theta_min         2.221
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.862013
_exptl_absorpt_correction_T_min  0.506782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1463 before and 0.1182 after correction.
 The Ratio of minimum to maximum transmission is 0.5879.
 The \l/2 correction factor is Not present
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0042(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     811
_refine_ls_number_reflns         9684
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0765
_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^)+(0.1103P)^2^+3.5961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2059
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                7851
_reflns_number_total             9684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06140g2.cif.txt
_cod_data_source_block           twin5a
_cod_database_code               7117837
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5220(19) 0.4780(19)
2. 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
3. Shared sites
{C32B, C32D}
{C32A, C32C}
4. Restrained distances
 H11A-H35A
 2.1 with sigma of 0.015
 C32B-C33B \\sim C32B-C34B \\sim C32B-C35B \\sim C32D-C33D \\sim C32D-C34D
\\sim C32D-C35D
 with sigma of 0.015
 C35B-C36B \\sim C35D-C36D
 with sigma of 0.015
 C32B-C36B \\sim C32D-C36D
 with sigma of 0.015
 C33B-C34B \\sim C34B-C35B \\sim C35B-C33B \\sim C33D-C34D \\sim C34D-C35D
\\sim C35D-C33D
 with sigma of 0.02
 C32A-C35C \\sim C32A-C33C \\sim C32A-C35A \\sim C32C-C33A \\sim C32C-C34A
\\sim C32C-C34C
 with sigma of 0.015
 C35C-C33C \\sim C33C-C35A \\sim C35A-C35C \\sim C33A-C34A \\sim C34A-C34C
\\sim C34C-C33A
 with sigma of 0.02
5. Uiso/Uaniso restraints and constraints
Uanis(C8A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uiso(C35B) = Uiso(C35D)
Uiso(C36B) = Uiso(C36D)
Uiso(C32B) = Uiso(C32D)
Uiso(C34B) = Uiso(C34D)
Uiso(C33B) = Uiso(C33D)
Uiso(C32A) = Uiso(C32C)
Uiso(C35A) = Uiso(C34C)
Uiso(C34A) = Uiso(C33C)
6. Rigid body (RIGU) restrains
 C13B, C8B, C9B, N1B, C5B, C4B, C1B, C2B, C3B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
7. Others
 Sof(C32D)=Sof(C33D)=Sof(H33J)=Sof(H33K)=Sof(H33L)=Sof(C34D)=Sof(H34J)=
 Sof(H34K)=Sof(H34L)=Sof(C35D)=Sof(H35G)=Sof(H35H)=Sof(C36D)=Sof(H36J)=
 Sof(H36K)=Sof(H36L)=1-FVAR(1)
 Sof(C32B)=Sof(C33B)=Sof(H33G)=Sof(H33H)=Sof(H33I)=Sof(C34B)=Sof(H34G)=
 Sof(H34H)=Sof(H34I)=Sof(C35B)=Sof(H35E)=Sof(H35F)=Sof(C36B)=Sof(H36G)=
 Sof(H36H)=Sof(H36I)=FVAR(1)
 Sof(C32C)=Sof(C33C)=Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C34C)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=Sof(C35C)=Sof(H35C)=Sof(H35D)=Sof(C36C)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(C32A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C34A)=Sof(H34A)=
 Sof(H34B)=Sof(H34C)=Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(2)
8.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C35A(H35A,H35B), C35C(H35C,H35D), C15B(H15C,H15D), C35B(H35E,
 H35F), C35D(H35G,H35H), C3S(H3SA,H3SB), C1S(H1SA,H1SB)
8.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C10A(H10A), C11A(H11A), C13A(H13A), C18A(H18A),
 C19A(H19A), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A),
 C30A(H30A), C31A(H31A), C6B(H6B), C7B(H7B), C10B(H10B), C11B(H11B), C13B(H13B),
  C18B(H18B), C19B(H19B), C24B(H24B), C25B(H25B), C26B(H26B), C27B(H27B),
 C28B(H28B), C30B(H30B), C31B(H31B)
8.c Idealised Me refined with riding coordinates:
 C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C), C36A(H36A,H36B,H36C), C33C(H33D,
 H33E,H33F), C34C(H34D,H34E,H34F), C36C(H36D,H36E,H36F), C33B(H33G,H33H,H33I),
 C34B(H34G,H34H,H34I), C36B(H36G,H36H,H36I), C33D(H33J,H33K,H33L), C34D(H34J,
 H34K,H34L), C36D(H36J,H36K,H36L)
8.d Idealised Me refined as rotating group:
 C4S(H4SA,H4SB,H4SC), C2S(H2SA,H2SB,H2SC)
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_shelx_res_checksum              53003
_shelx_hkl_checksum              19848
_olex2_submission_special_instructions 'No special instructions were received'