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_7117839
_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'
_chemical_formula_sum            'C72 H54 N2 O8'
_chemical_formula_weight         1075.17
_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             2014-11-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-07-12 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                108.388(2)
_cell_angle_beta                 98.716(2)
_cell_angle_gamma                104.328(2)
_cell_formula_units_Z            1
_cell_length_a                   8.4849(7)
_cell_length_b                   12.6610(11)
_cell_length_c                   13.7331(12)
_cell_measurement_reflns_used    7606
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.043
_cell_measurement_theta_min      2.790
_cell_volume                     1313.5(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        29.200
_diffrn_reflns_theta_max         29.223
_diffrn_reflns_theta_min         2.089
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0886 before and 0.0484 after correction.
The Ratio of minimum to maximum transmission is 0.9041.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      .
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         5423
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0398P)^2^+0.7072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                3769
_reflns_number_total             5423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06140g2.cif.txt
_cod_data_source_block           usca048_0m
_cod_database_code               7117839
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_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. Shared sites
{C32A, C32B}
3. Restrained distances
 C9-O3A \\sim C9-O3B
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O4A) \\sim Ueq, Uanis(O4B) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C17A) = Uanis(C17B)
Uanis(O4A) = Uanis(O4B)
Uanis(O3A) = Uanis(O3B)
Uanis(C14A) = Uanis(C14B)
Uanis(C31A) = Uanis(C26B)
Uanis(C15A) = Uanis(C15B)
Uanis(C32A) = Uanis(C32B)
Uanis(C36A) = Uanis(C36B)
5. Same fragment restrains
{O3A, O4A, C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A,
C25A, C26A, C27A, C28A, C29A, C30A, C31A}
as
{O3B, O4B, C14B, C15B, C16B, C17B, C18B, C19B, C20B, C21B, C22B, C23B, C24B,
C25B, C26B, C27B, C28B, C29B, C30B, C31B}
{C32A, C33A, C34A, C35A, C36A}
as
{C32B, C33B, C34B, C35B, C36B}
6. Others
 Sof(O3B)=Sof(O4B)=Sof(C14B)=Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(C17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=
 Sof(C23B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=
 Sof(C27B)=Sof(H27B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(C30B)=Sof(H30B)=
 Sof(C31B)=Sof(H31B)=1-FVAR(1)
 Sof(O3A)=Sof(O4A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(C17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=
 Sof(C23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=
 Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=
 Sof(C31A)=Sof(H31A)=FVAR(1)
 Sof(C32B)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C34B)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=Sof(C35B)=Sof(H35C)=Sof(H35D)=Sof(C36B)=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)
7.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C15B(H15C,H15D), C35A(H35A,H35B), C35B(H35C,H35D)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18A(H18A), C19A(H19A),
 C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C30A(H30A),
 C31A(H31A), C18B(H18B), C19B(H19B), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C28B(H28B), C30B(H30B), C31B(H31B)
7.c Idealised Me refined as rotating group:
 C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C), C36A(H36A,H36B,H36C), C33B(H33D,
 H33E,H33F), C34B(H34D,H34E,H34F), C36B(H36D,H36E,H36F)
;
_shelx_res_checksum              22803
_shelx_hkl_checksum              79493
_olex2_submission_special_instructions 'No special instructions were received'