Assembly and optical properties of 1D helical bundles induced by triphenylamine, side chains and solvents in crystals.
Pang, Zhi; Qi, Ting; Li, Baolin; Organic & biomolecular chemistry 19 (2021) 5555–5562; doi:10.1039/d1ob00389e

data_7158093
_publ_section_title
;
 Assembly and optical properties of 1D helical bundles induced by
 triphenylamine, side chains and solvents in crystals.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5555
_journal_page_last               5562
_journal_paper_doi               10.1039/d1ob00389e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C104 H101 N13 O14, 0.579(C H4 O)'
_chemical_formula_sum            'C104.58 H103.32 N13 O14.58'
_chemical_formula_weight         1775.55
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-06 deposited with the CCDC.	2021-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36860(10)
_cell_length_b                   31.9891(3)
_cell_length_c                   31.1143(2)
_cell_measurement_reflns_used    64912
_cell_measurement_temperature    170.00(15)
_cell_measurement_theta_max      74.1100
_cell_measurement_theta_min      3.1000
_cell_volume                     10274.17(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_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     -6.00  20.00   0.50    1.00    --  -47.07  15.00-144.00   52
  2  \w    -58.00 -33.00   0.50    1.00    --  -47.07 -67.00-102.45   50
  3  \w    -60.00 -32.00   0.50    1.00    --  -47.07 -57.00 -30.00   56
  4  \w    -23.00   3.00   0.50    1.00    --  -47.07  19.00   0.00   52
  5  \w    -51.00 -26.00   0.50    4.50    --  -99.00 125.00-120.00   50
  6  \w    -54.00 -26.00   0.50    4.50    --  -99.00 125.00 -60.00   56
  7  \w   -111.00 -64.00   0.50    4.50    --  -99.00 125.00-120.00   94
  8  \w   -111.00 -67.00   0.50    4.50    --  -99.00 125.00 -60.00   88
  9  \w   -120.00 -48.00   0.50    1.00    --  -47.07 -15.00  45.00  144
 10  \w    -26.00  -1.00   0.50    1.00    --   47.07 -15.00  45.00   50
 11  \w     36.00 103.00   0.50    1.00    --   47.07  19.00 -30.00  134
 12  \w     53.00  78.00   0.50    1.00    --   47.07  15.00-144.00   50
 13  \w     44.00  72.00   0.50    1.00    --   47.07  38.00 -90.00   56
 14  \w     32.00  59.00   0.50    1.00    --   47.07  57.00 -90.00   54
 15  \w     25.00  53.00   0.50    1.00    --   47.07  77.00 -30.00   56
 16  \w     34.00  76.00   0.50    1.00    --   47.07  57.00   0.00   84
 17  \w     27.00  95.00   0.50    1.00    --   47.07  77.00   0.00  136
 18  \w     27.00  90.00   0.50    1.00    --   47.07  77.00 -90.00  126
 19  \w     98.00 130.00   0.50    4.50    --  103.25  15.00-144.00   64
 20  \w     64.00 106.00   0.50    4.50    --  103.25 -94.00 -60.00   84
 21  \w     43.00  99.00   0.50    4.50    --  103.25 -94.00  30.00  112
 22  \w     31.00  72.00   0.50    4.50    --  103.25 -61.00 -90.00   82
 23  \w     35.00  61.00   0.50    4.50    --  103.25 -61.00 -30.00   52
 24  \w     33.00  72.00   0.50    4.50    --  103.25 -61.00 -60.00   78
 25  \w     33.00  75.00   0.50    4.50    --  103.25 -61.00-120.00   84
 26  \w     31.00  71.00   0.50    4.50    --  103.25 -61.00-180.00   80
 27  \w    -26.00  47.00   0.50    1.00    --   47.07 -38.00 -60.00  146
 28  \w     31.00  74.00   0.50    4.50    --  103.25 -61.00 120.00   86
 29  \w   -115.00 -74.00   0.50    1.00    --  -47.07-125.00-150.00   82
 30  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -74.00 -68.40   52
 31  \w   -106.00 -80.00   0.50    4.50    --  -99.00 -69.00 -45.71   52
 32  \w   -104.00 -78.00   0.50    4.50    --  -99.00 -72.00 -38.73   52
 33  \w   -107.00 -81.00   0.50    4.50    --  -99.00 -64.00 -34.26   52
 34  \w   -105.00 -78.00   0.50    4.50    --  -99.00 -72.00 -57.94   54
 35  \w   -104.00 -78.00   0.50    4.50    --  -99.00 -75.00  -5.07   52
 36  \w   -102.00 -76.00   0.50    4.50    --  -99.00 -77.00  30.00   52
 37  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -75.00   5.00   52
 38  \w   -104.00 -79.00   0.50    4.50    --  -99.00 -71.00  32.39   50
 39  \w   -110.00 -82.00   0.50    4.50    --  -99.00 -61.00   0.00   56
 40  \w   -101.00 -76.00   0.50    4.50    --  -99.00 -77.00 -30.00   50
 41  \w   -102.00 -76.00   0.50    4.50    --  -99.00 -78.00   4.45   52
 42  \w   -105.00 -79.00   0.50    4.50    --  -99.00 -75.00  47.18   52
 43  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -75.00  50.13   52
 44  \w   -105.00 -79.00   0.50    4.50    --  -99.00 -69.00   2.06   52
 45  \w   -102.00 -76.00   0.50    4.50    --  -99.00 -76.00 -60.47   52
 46  \w   -107.00 -77.00   0.50    4.50    --  -99.00 -75.00 -73.03   60
 47  \w   -105.00 -79.00   0.50    4.50    --  -99.00 -69.00 -30.78   52
 48  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -75.00  31.39   52
 49  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -77.00   0.00   52
 50  \w   -106.00 -80.00   0.50    4.50    --  -99.00 -67.00  30.73   52
 51  \w   -101.00 -76.00   0.50    4.50    --  -99.00 -78.00 -20.78   50
 52  \w   -103.00 -77.00   0.50    4.50    --  -99.00 -75.00 -68.90   52
 53  \w   -101.00 -75.00   0.50    4.50    --  -99.00 -79.00 -45.15   52
 54  \w   -104.00 -77.00   0.50    4.50    --  -99.00 -76.00 -42.72   54
 55  \w   -105.00 -79.00   0.50    4.50    --  -99.00 -69.00 -67.86   52
 56  \w   -101.00 -75.00   0.50    4.50    --  -99.00 -79.00 -79.41   52
 57  \w   -101.00 -75.00   0.50    4.50    --  -99.00 -80.00 -91.63   52
 58  \w   -116.00 -77.00   0.50    4.50    --  -99.00 -75.00 -76.59   78
 59  \w   -103.00 -78.00   0.50    4.50    --  -99.00 -73.00 -16.54   50
 60  \w   -109.00 -82.00   0.50    4.50    --  -99.00 -61.00 -60.00   54
 61  \w   -110.00 -82.00   0.50    4.50    --  -99.00 -61.00 -10.13   56
 62  \w   -110.00 -84.00   0.50    4.50    --  -99.00 -57.00 -53.48   52
 63  \w   -113.00 -79.00   0.50    4.50    --  -99.00 -71.00 -86.75   68
 64  \w   -114.00 -88.00   0.50    4.50    --  -99.00 -45.00  17.08   52
 65  \w   -127.00 -86.00   0.50    4.50    --  -99.00 -15.00  45.00   82
 66  \w   -155.00-110.00   0.50    4.50    --  -99.00 -71.00  32.39   90
 67  \w   -166.00-141.00   0.50    4.50    --  -99.00 -75.00  -5.07   50
 68  \w   -158.00 -76.00   0.50    4.50    --  -99.00 -80.00  30.29  164
 69  \w   -167.00-122.00   0.50    4.50    --  -99.00 -62.00-117.73   90
 70  \w   -166.00 -75.00   0.50    4.50    --  -99.00 -79.00 -83.43  182
 71  \w   -168.00 -88.00   0.50    4.50    --  -99.00 -46.00 -42.27  160
 72  \w   -164.00-138.00   0.50    4.50    --  -99.00 -73.00 -16.54   52
 73  \w   -167.00-142.00   0.50    4.50    --  -99.00 -76.00 -60.47   50
 74  \w   -162.00-136.00   0.50    4.50    --  -99.00 -77.00 -30.00   52
 75  \w   -166.00-140.00   0.50    4.50    --  -99.00 -80.00 -91.63   52
 76  \w   -167.00 -86.00   0.50    4.50    --  -99.00 -53.00 -83.23  162
 77  \w   -168.00 -78.00   0.50    4.50    --  -99.00 -72.00  11.03  180
 78  \w   -161.00-136.00   0.50    4.50    --  -99.00 -78.00 -20.78   50
 79  \w   -167.00 -85.00   0.50    4.50    --  -99.00 -50.00 -12.45  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0719404000
_diffrn_orient_matrix_UB_12      0.0063124000
_diffrn_orient_matrix_UB_13      -0.0451486000
_diffrn_orient_matrix_UB_21      -0.1303031000
_diffrn_orient_matrix_UB_22      -0.0073040000
_diffrn_orient_matrix_UB_23      0.0188125000
_diffrn_orient_matrix_UB_31      -0.0106903000
_diffrn_orient_matrix_UB_32      0.0471896000
_diffrn_orient_matrix_UB_33      0.0089984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            203504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.569
_diffrn_reflns_theta_min         3.110
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_description       plate
_exptl_crystal_F_000             3754
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.325
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1423
_refine_ls_number_reflns         20643
_refine_ls_number_restraints     342
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0862
_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^)+(0.1661P)^2^+4.6904P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2654
_refine_ls_wR_factor_ref         0.2779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16733
_reflns_number_total             20643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00389e2.cif
_cod_data_source_block           tx2226b_sq
_cod_depositor_comments
'Adding full bibliography for 7158091--7158093.cif.'
_cod_database_code               7158093
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C99A-C76A
 1.51 with sigma of 0.01
 C80A-C79A = C82A-C80A = C81A-C80A = C1B-C1D = C1B-C1A = C1E-C1B
 1.54 with sigma of 0.01
 C75A-C70A = C74A-C75A = C77A-C76A = C78A-C77A = C74A-C78A = C73A-C74A = C72A-
 C73A = C71A-C72A = C71A-C70A
 1.39 with sigma of 0.01
 O2-C79 = O2-C79A = O13A-C1C
 1.43 with sigma of 0.01
 O13A-C99A
 1.34 with sigma of 0.01
 C1E-C1D
 2.5 with sigma of 0.02
 C1E-C1A
 2.5 with sigma of 0.02
 C1C-C99A
 2.4 with sigma of 0.01
 C79A-C82A
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O12A \\sim O13A \\sim N13A \\sim C1C \\sim H53 \\sim C70A \\sim C71A \\sim C72A
\\sim C73A \\sim C74A \\sim C75A \\sim C76A \\sim C77A \\sim C78A \\sim C99A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
O14A \\sim C1A \\sim C1B \\sim C1D \\sim C1E \\sim C101 \\sim C102 \\sim C103
\\sim C104 \\sim O14: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 1.7A
Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C82)
\\sim Ueq, Uanis(C79A) \\sim Ueq, Uanis(C80A) \\sim Ueq, Uanis(C81A) \\sim Ueq,
Uanis(C82A) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1D)
\\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(O13A) \\sim Ueq, Uanis(C77A) \\sim Ueq, Uanis(C99A) \\sim Ueq,
Uanis(C76A) \\sim Ueq, Uanis(O12A) \\sim Ueq, Uanis(C1C) \\sim Ueq, Uanis(C74A)
\\sim Ueq, Uanis(C75A) \\sim Ueq, Uanis(N13A) \\sim Ueq, Uanis(C78A) \\sim Ueq,
Uanis(C73A) \\sim Ueq, Uanis(C72A) \\sim Ueq, Uanis(C71A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O12A)=Sof(O13A)=Sof(O14A)=Sof(H12A)=Sof(N13A)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=Sof(C1B)=Sof(H1B)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=Sof(C1D)=
 Sof(H1DA)=Sof(H1DB)=Sof(H1DC)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=Sof(C70A)=
 Sof(C71A)=Sof(H71A)=Sof(C72A)=Sof(H72A)=Sof(C73A)=Sof(H73A)=Sof(C74A)=
 Sof(C75A)=Sof(C76A)=Sof(C77A)=Sof(H77A)=Sof(C78A)=Sof(C99A)=1-FVAR(1)
 Sof(O12)=Sof(O13)=Sof(O14)=Sof(H12)=Sof(N13)=Sof(C70)=Sof(C71)=Sof(H71)=
 Sof(C72)=Sof(H72)=Sof(C73)=Sof(H73)=Sof(C74)=Sof(C75)=Sof(C76)=Sof(C77)=
 Sof(H77)=Sof(C78)=Sof(C99)=Sof(C100)=Sof(H10B)=Sof(H10C)=Sof(H10D)=Sof(C101)=
 Sof(H10E)=Sof(H10F)=Sof(C102)=Sof(H102)=Sof(C103)=Sof(H10G)=Sof(H10H)=
 Sof(H10I)=Sof(C104)=Sof(H10J)=Sof(H10K)=Sof(H10L)=Sof(O15)=Sof(H15A)=Sof(C105)=
 Sof(H10M)=Sof(H10N)=Sof(H10O)=FVAR(1)
 Sof(C79A)=Sof(H79C)=Sof(H79D)=Sof(C80A)=Sof(H80A)=Sof(C81A)=Sof(H81D)=
 Sof(H81E)=Sof(H81F)=Sof(C82A)=Sof(H82D)=Sof(H82E)=Sof(H82F)=1-FVAR(2)
 Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(C80)=Sof(H80)=Sof(C81)=Sof(H81A)=Sof(H81B)=
 Sof(H81C)=Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(H82C)=FVAR(2)
 Fixed Z: C1E(0.532)
5.a Riding coordinates:
 C1D(H1DA,H1DB,H1DC), C1E(H1EA,H1EB,H1EC), C82A(H82D,H82E,H82F)
5.b Ternary CH refined with riding coordinates:
 C1B(H1B), C80(H80), C80A(H80A), C84(H84), C88(H88), C92(H92), C96(H96),
 C102(H102)
5.c Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C79(H79A,H79B), C79A(H79C,H79D), C83(H83A,H83B), C87(H87A,
 H87B), C91(H91A,H91B), C95(H95A,H95B), C101(H10E,H10F)
5.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N6(H6), N8(H8), N10(H10), N12(H12), N12(H12A), C2(H2A),
 C3(H3), C4(H4A), C5(H5), C6(H6A), C8(H8A), C9(H9), C10(H10A), C11(H11),
 C12(H12B), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C27(H27), C31(H31), C32(H32), C33(H33), C37(H37), C41(H41), C42(H42),
  C43(H43), C47(H47), C51(H51), C52(H52), C53(H53), C57(H57), C61(H61),
 C62(H62), C63(H63), C66(H66), C71(H71), C71A(H71A), C72(H72), C72A(H72A),
 C73(H73), C73A(H73A), C77(H77), C77A(H77A)
5.e Idealised Me refined as rotating group:
 C1C(H1CA,H1CB,H1CC), C81(H81A,H81B,H81C), C81A(H81D,H81E,H81F), C82(H82A,H82B,
 H82C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C), C89(H89A,H89B,H89C), C90(H90A,
 H90B,H90C), C93(H93A,H93B,H93C), C94(H94A,H94B,H94C), C97(H97A,H97B,H97C),
 C98(H98A,H98B,H98C), C100(H10B,H10C,H10D), C103(H10G,H10H,H10I), C104(H10J,
 H10K,H10L), C105(H10M,H10N,H10O)
5.f Idealised tetrahedral OH refined as rotating group:
 O15(H15A)
;
_shelx_res_checksum              66018
_shelx_fab_checksum              12269
_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 1.598
_oxdiff_exptl_absorpt_empirical_full_min 0.528