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_7117841
_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, 1.36(C2 H3 N), 0.64(C H2 Cl2)'
_chemical_formula_sum            'C75.36 H59.36 Cl1.28 N3.36 O8'
_chemical_formula_weight         1185.35
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.13 svn.r2834 for OlexSys, GUI svn.r4705)
;
_audit_update_record
;
2015-07-12 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.969(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.132(3)
_cell_length_b                   10.4771(16)
_cell_length_c                   17.718(3)
_cell_measurement_reflns_used    7671
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.878
_cell_measurement_theta_min      2.316
_cell_volume                     2906.0(8)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_min         2.146
_diffrn_source                   'sealed tube'
_diffrn_source_current           37.0
_diffrn_source_power             1.739
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5169
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0846
_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^)+(0.1244P)^2^+4.4388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2333
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                3840
_reflns_number_total             5169
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc06140g2.cif.txt
_cod_data_source_block           dfya53m
_cod_database_code               7117841
_shelxl_version_number           2013-4
_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
 N1S-C1S
 1.13 with sigma of 0.02
 C1S-C2S
 1.445 with sigma of 0.02
 C3S-Cl1S = C3S-Cl2S
 1.76 with sigma of 0.02
 Cl1S-Cl2S
 2.93 with sigma of 0.02
 C4S-Cl3S = C4S-Cl4S
 1.76 with sigma of 0.02
 Cl3S-Cl4S
 2.93 with sigma of 0.02
 N1S-C2S
 0.02 with sigma of 2.57
 C32A-C33A \\sim C32A-C34A \\sim C32A-C35A \\sim C32B-C33B \\sim C32B-C34B
\\sim C32B-C35B
 with sigma of 0.01
 C33A-C34A \\sim C34A-C35A \\sim C35A-C33A \\sim C33B-C34B \\sim C34B-C35B
\\sim C35B-C33B
 with sigma of 0.02
 C35A-C36A \\sim C35B-C36B
 with sigma of 0.01
 C32A-C36A \\sim C32B-C36B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32A) = Uanis(C32B)
Uiso(C33A) = Uiso(C33B)
Uiso(C2S) = Uiso(C3S) = Uiso(C4S)
5. Rigid body (RIGU) restrains
 C20, C26, C27, C28, C29, C30, C21, C19, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(N1S)+Sof(C1S)+Sof(C2S)+Sof(H2SA)+Sof(H2SB)+Sof(H2SC)]+1*[Sof(C3S)+
 Sof(H3SA)+Sof(H3SB)+Sof(Cl1S)+Sof(Cl2S)]+1*[Sof(C4S)+Sof(H4SA)+Sof(H4SB)+
 Sof(Cl3S)+Sof(Cl4S)]=1 with esd of 0.0001
 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(1)
 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(1)
 Sof(N1S)=Sof(C1S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(2)
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(Cl1S)=Sof(Cl2S)=FVAR(3)
 Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(Cl3S)=Sof(Cl4S)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C35A(H35A,H35B), C35B(H35C,H35D), C3S(H3SA,H3SB), C4S(H4SA,
 H4SB)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18(H18), C19(H19), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31)
7.c Idealised Me refined with riding coordinates:
 C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C), C36A(H36A,H36B,H36C), C33B(H33D,
 H33E,H33F), C34B(H34D,H34E,H34F), C36B(H36D,H36E,H36F), C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              279
_shelx_hkl_checksum              4111