Strain-Induced Stereoselective Formation of Blue-Emitting Cyclostilbenes.
Chen, Qishui; Trinh, M. Tuan; Paley, Daniel W.; Preefer, Molleigh B.; Zhu, Haiming; Fowler, Brandon S.; Zhu, X.-Y.; Steigerwald, Michael L.; Nuckolls, Colin; Journal of the American Chemical Society 137 (2015) 12282–12288; doi:10.1021/jacs.5b06258

data_4124476
_publ_section_title
;
 Strain-Induced Stereoselective Formation of Blue-Emitting Cyclostilbenes.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12282
_journal_page_last               12288
_journal_paper_doi               10.1021/jacs.5b06258
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C7 H8, C56 H40'
_chemical_formula_sum            'C63 H48'
_chemical_formula_weight         805.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9270(14)
_cell_length_b                   17.389(2)
_cell_length_c                   28.757(4)
_cell_measurement_reflns_used    2674
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.1470
_cell_measurement_theta_min      5.2720
_cell_volume                     4464.0(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega  -23.00   55.00   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -77.0000  -90.0000 52

  2 omega    1.00   29.50   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000   30.0000 19

  3 omega   35.00   69.50   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000   30.0000 23

  4 omega   19.00   97.00   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000   90.0000 52

  5 omega   59.00   86.00   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316 -127.0000 -149.0000 18

  6 omega  -29.00   53.50   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -37.0000  -60.0000 55

  7 omega   23.00   54.50   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -77.0000  150.0000 21

  8 omega   58.00   92.50   1.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   37.0000  -30.0000 23

  9 omega  120.00  150.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 20

 10 omega  148.00  175.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 18

 11 omega   69.00   96.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 18

 12 omega  123.00  169.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 31

 13 omega  102.00  129.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 18

 14 omega   92.00  162.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 47

 15 omega   41.00   89.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 32

 16 omega  129.00  162.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 22

 17 omega   96.00  121.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 17

 18 omega   80.00  125.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 30

 19 omega   45.00   72.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 18

 20 omega   50.00   84.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 23

 21 omega   82.00  109.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 18

 22 omega   92.00  117.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 17

 23 omega   91.00  172.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 54

 24 omega   58.00  103.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 30

 25 omega  120.00  178.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 39

 26 omega   72.00  112.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 27

 27 omega   89.00  116.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 18

 28 omega   56.00   96.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 27

 29 omega  112.00  139.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 18

 30 omega   84.00  111.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 18

 31 omega   42.00   88.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 31

 32 omega   49.00   74.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 17

 33 omega   60.00   85.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 17

 34 omega   49.00   92.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 29

 35 omega   56.00   81.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 17

 36 omega   45.00   70.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 17

 37 omega   89.00  114.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 17

 38 omega   84.00  109.50   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 17

 39 omega   47.00   74.00   1.5000   37.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0041418000
_diffrn_orient_matrix_UB_12      -0.0823652000
_diffrn_orient_matrix_UB_13      0.0197926000
_diffrn_orient_matrix_UB_21      0.0121057000
_diffrn_orient_matrix_UB_22      0.0327308000
_diffrn_orient_matrix_UB_23      0.0496924000
_diffrn_orient_matrix_UB_31      -0.1719078000
_diffrn_orient_matrix_UB_32      0.0003195000
_diffrn_orient_matrix_UB_33      0.0036485000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1269
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.783
_diffrn_reflns_theta_min         5.087
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.1673
_exptl_crystal_size_mid          0.0597
_exptl_crystal_size_min          0.0161
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_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     599
_refine_ls_number_reflns         8679
_refine_ls_number_restraints     597
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.1265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0248P)^2^+22.5762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2675
_refine_ls_wR_factor_ref         0.2849
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                6394
_reflns_number_total             8679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06258_si_003.cif
_cod_data_source_block           w21
_cod_depositor_comments
'Adding full bibliography for 4124476--4124478.cif.'
_cod_original_cell_volume        4464.1(11)
_cod_database_code               4124476
_chemical_oxdiff_formula         'c63 h48'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2
 C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C1_2 \\sim C2_2 \\sim C3_2 \\sim C4_2 \\sim C5_2 \\sim C6_2 \\sim C7_2 \\sim
C1_3 \\sim C2_3 \\sim C3_3 \\sim C4_3 \\sim C5_3 \\sim C6_3 \\sim C7_3: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3}
as
{C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2} sigma for 1-2: 0.02 1-3: 0.04
{C1_3, C2_3, C7_3, C6_3, C5_3, C4_3, C3_3}
as
{C1_2, C2_2, C7_2, C6_2, C5_2, C4_2, C3_2} sigma for 1-2: 0.02 1-3: 0.04
6. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C3(H3), C4(H4), C5(H5), C6(H6),
 C7(H7), C1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23),
  C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
 C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43),
  C45(H45), C46(H46), C48(H48), C49(H49), C51(H51), C52(H52), C54(H54),
 C55(H55), C56(H56)
7.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              65745
_shelx_hkl_checksum              78307
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'