An electron-transfer induced conformational transformation: from non-cofacial "sofa" to cofacial "boat" in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes.
Wang, Denan; Ivanov, Maxim V.; Mirzaei, Saber; Lindeman, Sergey V.; Rathore, Rajendra; Organic & biomolecular chemistry 16 (2018) 5712–5717; doi:10.1039/c8ob01118d

data_7156331
_publ_section_title
;
 An electron-transfer induced conformational transformation: from
 non-cofacial &quot;sofa&quot; to cofacial &quot;boat&quot; in
 cyclotetraveratrylene (CTTV) and formation of charge transfer complexes.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5712
_journal_page_last               5717
_journal_paper_doi               10.1039/c8ob01118d
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety
'C8 Cl2 N2 O2, 2(C18 H20 O4), 3.23(C H Cl3), 0.77(C3 H7)'
_chemical_formula_sum            'C49.55 H48.64 Cl11.68 N2 O10'
_chemical_formula_weight         1246.20
_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             2018-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-17 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                111.109(4)
_cell_angle_beta                 94.141(4)
_cell_angle_gamma                100.255(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0667(4)
_cell_length_b                   16.1954(7)
_cell_length_c                   19.0021(8)
_cell_measurement_reflns_used    9371
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.4760
_cell_measurement_theta_min      4.4920
_cell_volume                     2812.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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    -70.00  31.00   1.00   10.00    --  -41.96  57.00 -90.00  101
  2  \w   -114.00 -14.00   1.00   10.00    --  -41.96 -57.00 120.00  100
  3  \w    -66.00  33.00   1.00   10.00    --  -41.96  37.00  60.00   99
  4  \w      1.00  83.00   1.00   10.00    --   41.96 -99.00   0.00   82
  5  \w     94.00 173.00   1.00   40.00    --  100.00 125.00 120.00   79
  6  \w     94.00 173.00   1.00   40.00    --  100.00 125.00   0.00   79
  7  \w     71.00 172.00   1.00   40.00    --  100.00  61.00  90.00  101
  8  \w     74.00 173.00   1.00   40.00    --  100.00  45.00  60.00   99
  9  \w     94.00 173.00   1.00   40.00    --  100.00 125.00 -30.00   79
 10  \w     27.00 121.00   1.00   40.00    --  100.00-125.00   0.00   94
 11  \w     71.00 172.00   1.00   40.00    --  100.00  61.00 -60.00  101
 12  \w     24.00 133.00   1.00   40.00    --  100.00 -77.00  30.00  109
 13  \w     27.00 121.00   1.00   40.00    --  100.00-125.00 -60.00   94
 14  \w     27.00 121.00   1.00   40.00    --  100.00-125.00  90.00   94
 15  \w     67.00 176.00   1.00   40.00    --  100.00  77.00 120.00  109
 16  \w     27.00 121.00   1.00   40.00    --  100.00-125.00-150.00   94
 17  \w     74.00 173.00   1.00   40.00    --  100.00  45.00-180.00   99
 18  \w   -114.00 -14.00   1.00   10.00    --  -41.96 -57.00-150.00  100
 19  \w   -118.00  -9.00   1.00   10.00    --  -41.96 -77.00  30.00  109
 20  \w   -118.00  -9.00   1.00   10.00    --  -41.96 -77.00 -60.00  109
 21  \w     71.00 172.00   1.00   40.00    --  100.00  61.00-150.00  101
 22  \w     71.00 172.00   1.00   40.00    --  100.00  61.00   0.00  101
 23  \w     71.00 172.00   1.00   40.00    --  100.00  61.00 -90.00  101
 24  \w     71.00 172.00   1.00   40.00    --  100.00  61.00  60.00  101
 25  \w     71.00 172.00   1.00   40.00    --  100.00  61.00 -30.00  101
 26  \w     71.00 172.00   1.00   40.00    --  100.00  61.00-180.00  101
 27  \w     67.00 176.00   1.00   40.00    --  100.00  77.00   0.00  109
 28  \w     71.00 172.00   1.00   40.00    --  100.00  61.00-120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0499603000
_diffrn_orient_matrix_UB_12      -0.0324652000
_diffrn_orient_matrix_UB_13      -0.0781314000
_diffrn_orient_matrix_UB_21      0.0940453000
_diffrn_orient_matrix_UB_22      -0.0500304000
_diffrn_orient_matrix_UB_23      0.0289125000
_diffrn_orient_matrix_UB_31      -0.1157203000
_diffrn_orient_matrix_UB_32      -0.0858208000
_diffrn_orient_matrix_UB_33      -0.0279702000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52221
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        70.775
_diffrn_reflns_theta_max         70.775
_diffrn_reflns_theta_min         4.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.743
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       plate
_exptl_crystal_F_000             1277
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.017
_refine_diff_density_max         2.131
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     760
_refine_ls_number_reflns         10686
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0664
_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^)+(0.1359P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6636
_reflns_number_total             10686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01118d3.cif
_cod_data_source_block           raj29d4
_cod_depositor_comments
'Adding full bibliography for 7156330--7156331.cif.'
_cod_database_code               7156331
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula
'(C7 H10 O2)4 C8 Cl2 O2 N2 (C H Cl3)3.5 (C6 H14)0.5'
_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. Rigid bond restraints
 Cl5Q, C2Q, Cl4Q, Cl6Q
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl4S, C2S, Cl5S, Cl6S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl7Q, C3Q, Cl8Q, Cl9Q
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl7S, C3S, Cl8S, Cl9S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl1S, C1S, Cl2S, Cl3S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl12, C4S, Cl11, Cl13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11S, C12S, C13S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C2S) = Uanis(C2Q)
Uanis(Cl4S) = Uanis(Cl4Q)
Uanis(C3Q) = Uanis(C3S)
4. Same fragment restrains
{Cl1S, Cl2S, Cl3S, C1S} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl4S, Cl5S, Cl6S, C2S}
{Cl1S, Cl2S, Cl3S, C1S} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl4Q, Cl5Q, Cl6Q, C2Q}
{Cl1S, Cl2S, Cl3S, C1S} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl7S, Cl8S, Cl9S, C3S}
{Cl1S, Cl2S, Cl3S, C1S} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl7Q, Cl8Q, Cl9Q, C3Q}
{Cl1S, Cl2S, Cl3S, C1S} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl11, Cl12, Cl13, C4S}
5. Others
 Sof(C11S)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12S)=Sof(H12A)=Sof(H12B)=
 Sof(C13S)=Sof(H13A)=Sof(H13B)=1-FVAR(1)
 Sof(Cl11)=Sof(Cl12)=Sof(Cl13)=Sof(C4S)=Sof(H4S)=FVAR(1)
 Sof(Cl4Q)=Sof(Cl5Q)=Sof(Cl6Q)=Sof(C2Q)=Sof(H2Q)=1-FVAR(2)
 Sof(Cl4S)=Sof(Cl5S)=Sof(Cl6S)=Sof(C2S)=Sof(H2S)=FVAR(2)
 Sof(Cl7Q)=Sof(Cl8Q)=Sof(Cl9Q)=Sof(C3Q)=Sof(H3Q)=1-FVAR(3)
 Sof(Cl7S)=Sof(Cl8S)=Sof(Cl9S)=Sof(C3S)=Sof(H3S)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C1S(H1S), C2S(H2S), C2Q(H2Q), C3S(H3S), C3Q(H3Q), C4S(H4S)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C12S(H12A,H12B),
 C13S(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C22(H22), C25(H25), C32(H32), C35(H35), C42(H42), C45(H45)
6.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C11S(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2018-02-16
_olex2_date_sample_submission    2018-02-13
_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 2.023
_oxdiff_exptl_absorpt_empirical_full_min 0.714
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by 17.5698\% 
 around [-0.57 0.36 0.74] (reciprocal) or [-0.83 0.34 0.44] (direct)
;