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_4124478
_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_formula_moiety         'C56 H40, C H2 Cl2'
_chemical_formula_sum            'C57 H42 Cl2'
_chemical_formula_weight         797.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5877(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.73721(18)
_cell_length_b                   33.7850(3)
_cell_length_c                   9.62683(10)
_cell_measurement_reflns_used    23106
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.3610
_cell_measurement_theta_min      4.0790
_cell_volume                     4593.69(9)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1098
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -1.00   26.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   94.0000  -47.1014 36

  2 omega   55.00  106.75   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316 -178.0000  -60.0000 69

  3 omega   16.00  103.75   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   37.0000   30.0000 117

  4 omega   19.00  103.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000  -60.0000 112

  5 omega   57.00  108.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  178.0000  120.0000 68

  6 omega  -32.00   52.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -57.0000 -120.0000 112

  7 omega    1.00   73.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000 -120.0000 96

  8 omega  -32.00   61.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -77.0000 -150.0000 124

  9 omega  -32.00   52.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -57.0000   90.0000 112

 10 omega   38.00  116.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 104

 11 omega   57.00  150.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 124

 12 omega   37.00  109.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -20.0000  167.4031 96

 13 omega   41.00  125.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   60.0000 112

 14 omega   91.00  175.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 112

 15 omega   38.00   89.75   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 69

 16 omega   40.00  133.75   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 125

 17 omega  100.00  178.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 104

 18 omega   38.00  116.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 104

 19 omega   57.00  150.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -60.0000 124

 20 omega   87.00  177.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 120

 21 omega   39.00  108.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 92

 22 omega   39.00   93.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -40.0000  -42.7418 72

 23 omega  100.00  178.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 104

 24 omega   90.00  174.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 112

 25 omega   39.00  108.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 92

 26 omega   90.00  174.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 112

 27 omega  100.00  178.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 104

 28 omega   38.00  116.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 104

 29 omega   38.00   89.75   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 69

 30 omega   40.00   97.75   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 77

 31 omega   37.00   97.75   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -22.0000 -100.0753 81

 32 omega   19.00  103.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000   60.0000 112

 33 omega    9.00  102.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   77.0000   90.0000 124

 34 omega    9.00  102.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   77.0000 -180.0000 124

 35 omega    1.00   73.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -99.0000   60.0000 96

 36 omega  -32.00   52.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316  -57.0000  -30.0000 112

 37 omega   19.00  103.00   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   57.0000  150.0000 112

 38 omega   16.00  103.75   0.7500    5.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5316   37.0000  -90.0000 117

 39 omega   91.00  152.50   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 82

 40 omega   91.00  175.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 112

 41 omega   87.00  177.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 120

 42 omega   87.00  177.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 120

 43 omega   91.00  175.00   0.7500   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 112
;
_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      0.0904137000
_diffrn_orient_matrix_UB_12      0.0083838000
_diffrn_orient_matrix_UB_13      -0.0449862000
_diffrn_orient_matrix_UB_21      -0.0197156000
_diffrn_orient_matrix_UB_22      0.0447656000
_diffrn_orient_matrix_UB_23      0.0007428000
_diffrn_orient_matrix_UB_31      0.0577289000
_diffrn_orient_matrix_UB_32      0.0021149000
_diffrn_orient_matrix_UB_33      0.1608124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            73051
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.614
_diffrn_reflns_theta_min         4.969
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   gaussian
_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)
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_density_diffrn    1.154
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.1223
_exptl_crystal_size_mid          0.0656
_exptl_crystal_size_min          0.0381
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8941
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0627
_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^)+(0.0544P)^2^+3.9089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8090
_reflns_number_total             8941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06258_si_002.cif
_cod_data_source_block           w2corr_sq_sq
_cod_depositor_comments
'Adding full bibliography for 4124476--4124478.cif.'
_cod_database_code               4124478
_chemical_oxdiff_formula         'c58 h43 cl4'
_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
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C1_1, Cl1_1, Cl2_1
 C1_2, Cl1_2, Cl2_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C1_2, Cl1_2, Cl2_2}
as
{C1_1, Cl1_1, Cl2_1} sigma for 1-2: 0.02 1-3: 0.04
{C1_2, Cl2_2, Cl1_2}
as
{C1_1, Cl2_1, Cl1_1} sigma for 1-2: 0.02 1-3: 0.04
5. Others
 Sof(C1)=Sof(H1C)=Sof(H1D)=Sof(Cl1)=Sof(Cl2)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1(H1C,H1D)
6.b Aromatic/amide H refined with riding coordinates:
 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)
;
_shelx_res_checksum              23760
_shelx_hkl_checksum              11136
_shelx_fab_checksum              45743
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'