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_4124477
_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         '6(C2 H2 Cl4), C88 H88 Pt4'
_chemical_formula_sum            'C100 H100 Cl24 Pt4'
_chemical_formula_weight         2932.95
_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             2015-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.301(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.3098(3)
_cell_length_b                   26.5227(4)
_cell_length_c                   12.8182(2)
_cell_measurement_reflns_used    31947
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.6730
_cell_measurement_theta_min      3.6960
_cell_volume                     5874.98(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega    0.00   84.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930   57.0000  -30.0000 168

  2 omega  -10.00   85.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930   77.0000   90.0000 190

  3 omega  -50.00   44.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930  -77.0000  -30.0000 188

  4 omega    0.00   84.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930   57.0000  -90.0000 168

  5 omega  -20.00   56.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930  -99.0000   30.0000 152

  6 omega    0.00   84.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930   57.0000 -180.0000 168

  7 omega   34.00   90.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930 -178.0000  -90.0000 112

  8 omega  -20.00   56.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930  -99.0000   60.0000 152

  9 omega  -12.00   89.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930   19.0000   90.0000 202

 10 omega  -54.00   47.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930  -19.0000  150.0000 202

 11 omega  -20.00   39.00   0.5000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       17.1930  -99.0000 -120.0000 118
;
_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      0.0123424000
_diffrn_orient_matrix_UB_12      0.0106443000
_diffrn_orient_matrix_UB_13      -0.0421409000
_diffrn_orient_matrix_UB_21      0.0388537000
_diffrn_orient_matrix_UB_22      -0.0062901000
_diffrn_orient_matrix_UB_23      0.0305607000
_diffrn_orient_matrix_UB_31      -0.0047589000
_diffrn_orient_matrix_UB_32      -0.0237102000
_diffrn_orient_matrix_UB_33      -0.0270006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            110111
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.291
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.334
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.1148
_exptl_crystal_size_mid          0.0634
_exptl_crystal_size_min          0.0425
_refine_diff_density_max         2.502
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         11973
_refine_ls_number_restraints     574
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+20.4930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10859
_reflns_number_total             11973
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06258_si_004.cif
_cod_data_source_block           acorr_a_sq_sq
_cod_depositor_comments
'Adding full bibliography for 4124476--4124478.cif.'
_cod_original_cell_volume        5874.99(19)
_cod_database_code               4124477
_chemical_oxdiff_formula         'c104 h104 cl32 pt4'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 0.8A with sigma of 0.02 and sigma
for terminal atoms of 0.04
3. Rigid body (RIGU) restrains
 C1_1, Cl2_1, Cl3_1, C4_1, Cl5_1, Cl6_1
 C1_3, Cl2_3, Cl3_3, C4_3, Cl5_3, Cl6_3
 C1_4, Cl2_4, Cl3_4, C4_4, Cl5_4, Cl6_4
 C1_6, Cl2_6, Cl3_6, C4_6, Cl5_6, Cl6_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_11, C2_11, C5_11, C6_11, C3A_11, C4A_11, C7A_11, C8A_11, C3B_11, C4B_11,
 C7B_11, C8B_11
 C1_12, C2_12, C5_12, C6_12, C3A_12, C4A_12, C7A_12, C8A_12, C3B_12, C4B_12,
 C7B_12, C8B_12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C1_3, Cl2_3, Cl3_3, C4_3, Cl5_3, Cl6_3}
{C1_4, Cl2_4, Cl3_4, C4_4, Cl5_4, Cl6_4}
{C1_6, Cl2_6, Cl3_6, C4_6, Cl5_6, Cl6_6}
as
{C1_1, Cl2_1, Cl3_1, C4_1, Cl5_1, Cl6_1} sigma for 1-2: 0.02 1-3: 0.04
{Pt1_12, C1_12, C2_12, C5_12, C6_12, C3A_12, C4A_12, C7A_12, C8A_12}
as
{Pt1_11, C1_11, C2_11, C5_11, C6_11, C3A_11, C4A_11, C7A_11, C8A_11} sigma for
1-2: 0.02 1-3: 0.04
{Pt1_12, C1_12, C2_12, C5_12, C6_12, C3B_12, C4B_12, C7B_12, C8B_12}
as
{Pt1_11, C1_11, C2_11, C5_11, C6_11, C3B_11, C4B_11, C7B_11, C8B_11} sigma for
1-2: 0.02 1-3: 0.04
5. Others
 Sof(C1)=Sof(H1)=Sof(Cl2)=Sof(Cl3)=Sof(C4)=Sof(H4)=Sof(Cl5)=Sof(Cl6)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(Cl2)=Sof(Cl3)=Sof(C4)=Sof(H4)=Sof(Cl5)=Sof(Cl6)=FVAR(1)
 Sof(H1B)=Sof(H2B)=Sof(H5B)=Sof(H6B)=Sof(C3B)=Sof(H3B1)=Sof(H3B2)=Sof(C4B)=
 Sof(H4B1)=Sof(H4B2)=Sof(C7B)=Sof(H7B1)=Sof(H7B2)=Sof(C8B)=Sof(H8B1)=Sof(H8B2)=
 1-FVAR(2)
 Sof(H1A)=Sof(H2A)=Sof(H5A)=Sof(H6A)=Sof(C3A)=Sof(H3A1)=Sof(H3A2)=Sof(C4A)=
 Sof(H4A1)=Sof(H4A2)=Sof(C7A)=Sof(H7A1)=Sof(H7A2)=Sof(C8A)=Sof(H8A1)=Sof(H8A2)=
 FVAR(2)
 Sof(H1B)=Sof(H2B)=Sof(H5B)=Sof(H6B)=Sof(C3B)=Sof(H3B1)=Sof(H3B2)=Sof(C4B)=
 Sof(H4B1)=Sof(H4B2)=Sof(C7B)=Sof(H7B1)=Sof(H7B2)=Sof(C8B)=Sof(H8B1)=Sof(H8B2)=
 1-FVAR(3)
 Sof(H1A)=Sof(H2A)=Sof(H5A)=Sof(H6A)=Sof(C3A)=Sof(H3A1)=Sof(H3A2)=Sof(C4A)=
 Sof(H4A1)=Sof(H4A2)=Sof(C7A)=Sof(H7A1)=Sof(H7A2)=Sof(C8A)=Sof(H8A1)=Sof(H8A2)=
 FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C1(H1), C4(H4), C1(H1), C4(H4), C1(H1), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C3A(H3A1,H3A2), C4A(H4A1,H4A2), C7A(H7A1,H7A2), C8A(H8A1,H8A2), C3B(H3B1,
 H3B2), C4B(H4B1,H4B2), C7B(H7B1,H7B2), C8B(H8B1,H8B2), C3A(H3A1,H3A2),
 C4A(H4A1,H4A2), C7A(H7A1,H7A2), C8A(H8A1,H8A2), C3B(H3B1,H3B2), C4B(H4B1,H4B2),
  C7B(H7B1,H7B2), C8B(H8B1,H8B2)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C1(H1B), C2(H2A), C2(H2B), C5(H5A), C5(H5B), C6(H6A), C6(H6B),
 C1(H1A), C1(H1B), C2(H2A), C2(H2B), C5(H5A), C5(H5B), C6(H6A), C6(H6B), C3(H3),
  C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15)
;
_shelx_res_checksum              59313
_shelx_hkl_checksum              9415
_shelx_fab_checksum              85143
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'