Synthesis, Characterization, and Crystal Structures of 1,1-Disubstituted-2,3,4,5-tetraphenylgermoles That Exhibit Aggregation-Induced Emission
Bandrowsky, Teresa L.; Carroll, James B.; Braddock-Wilking, Janet; Organometallics 30 (2011) 3559–; doi:10.1021/om200259n

data_4064672
_publ_section_title
;
 Synthesis, Characterization, and Crystal Structures of
 1,1-Disubstituted-2,3,4,5-tetraphenylgermoles That Exhibit
 Aggregation-Induced Emission
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3559
_journal_paper_doi               10.1021/om200259n
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C92 H68 Ge2'
_chemical_formula_sum            'C92 H68 Ge2'
_chemical_formula_weight         1318.73
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   direct
_cell_angle_alpha                93.0420(10)
_cell_angle_beta                 108.8100(10)
_cell_angle_gamma                111.5560(10)
_cell_formula_units_Z            1
_cell_length_a                   11.16560(10)
_cell_length_b                   11.16690(10)
_cell_length_c                   16.1687(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    173
_cell_measurement_theta_max      1
_cell_measurement_theta_min      1
_cell_volume                     1740.84(4)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45433
_diffrn_reflns_theta_full        31.935
_diffrn_reflns_theta_max         33.974
_diffrn_reflns_theta_min         1.356
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'USER DEFINED ABSORPTION METHOD'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.94
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         13136
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0030278
_refine_ls_shift/su_mean         0.0001303
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 5.10 6.47 1.59 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1243
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1243
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                9863
_reflns_number_total             13173
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0487
_oxford_refine_ls_scale          0.12788(3)
_oxford_reflns_number_all        13142
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            om200259n_si_003.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4064672
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT GE   (    1 ,X'S,U'S)  UNTIL C    (   47 ) 
CONT H    (   51 ,X'S)  UNTIL H    (  473 ) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 5) TO H(51) 
REST 0.027, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
PLANAR C ( 5) C(4) C(6) H(51) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 6) TO H(61) 
REST 0.032, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
PLANAR C ( 6) C(5) C(7) H(61) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 8) TO H(81) 
REST 0.029, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 9) TO H(91) 
REST 0.024, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(4) 
CONT H(91) TO C ( 9) TO C(8) 
PLANAR C ( 9) C(4) C(8) H(91) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 10) TO H(101) 
CONT C ( 10) TO H(102) 
CONT C ( 10) TO H(103) 
REST 0.056, 0.002 = H(101,U[ISO]) 
REST 0.056, 0.002 = H(102,U[ISO]) 
REST 0.056, 0.002 = H(103,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(7) TO C ( 10) TO H(101) 
CONT C(7) TO C ( 10) TO H(102) 
CONT C(7) TO C ( 10) TO H(103) 
ANGLE 0.0, 2.0 = MEAN H(101) TO C ( 10) TO H(102) 
CONT H(101) TO C ( 10) TO H(103) 
CONT H(102) TO C ( 10) TO H(103) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 13) TO H(131) 
REST 0.035, 0.002 = H(131,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(131) TO C ( 13) TO C(12) 
CONT H(131) TO C ( 13) TO C(14) 
PLANAR C ( 13) C(12) C(14) H(131) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 14) TO H(141) 
REST 0.042, 0.002 = H(141,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(141) TO C ( 14) TO C(13) 
CONT H(141) TO C ( 14) TO C(15) 
PLANAR C ( 14) C(13) C(15) H(141) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 15) TO H(151) 
REST 0.035, 0.002 = H(151,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(151) TO C ( 15) TO C(14) 
CONT H(151) TO C ( 15) TO C(16) 
PLANAR C ( 15) C(14) C(16) H(151) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 16) TO H(161) 
REST 0.032, 0.002 = H(161,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(161) TO C ( 16) TO C(15) 
CONT H(161) TO C ( 16) TO C(17) 
PLANAR C ( 16) C(15) C(17) H(161) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 17) TO H(171) 
REST 0.027, 0.002 = H(171,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(171) TO C ( 17) TO C(12) 
CONT H(171) TO C ( 17) TO C(16) 
PLANAR C ( 17) C(12) C(16) H(171) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 20) TO H(201) 
REST 0.029, 0.002 = H(201,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(201) TO C ( 20) TO C(19) 
CONT H(201) TO C ( 20) TO C(21) 
PLANAR C ( 20) C(19) C(21) H(201) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 21) TO H(211) 
REST 0.040, 0.002 = H(211,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(211) TO C ( 21) TO C(20) 
CONT H(211) TO C ( 21) TO C(22) 
PLANAR C ( 21) C(20) C(22) H(211) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 22) TO H(221) 
REST 0.045, 0.002 = H(221,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(221) TO C ( 22) TO C(21) 
CONT H(221) TO C ( 22) TO C(23) 
PLANAR C ( 22) C(21) C(23) H(221) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 23) TO H(231) 
REST 0.042, 0.002 = H(231,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(231) TO C ( 23) TO C(22) 
CONT H(231) TO C ( 23) TO C(24) 
PLANAR C ( 23) C(22) C(24) H(231) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 24) TO H(241) 
REST 0.032, 0.002 = H(241,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(241) TO C ( 24) TO C(23) 
CONT H(241) TO C ( 24) TO C(19) 
PLANAR C ( 24) C(23) C(19) H(241) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 28) TO H(281) 
REST 0.023, 0.002 = H(281,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(281) TO C ( 28) TO C(27) 
CONT H(281) TO C ( 28) TO C(29) 
PLANAR C ( 28) C(27) C(29) H(281) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 29) TO H(291) 
REST 0.029, 0.002 = H(291,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(291) TO C ( 29) TO C(28) 
CONT H(291) TO C ( 29) TO C(30) 
PLANAR C ( 29) C(28) C(30) H(291) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 30) TO H(301) 
REST 0.031, 0.002 = H(301,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(301) TO C ( 30) TO C(29) 
CONT H(301) TO C ( 30) TO C(31) 
PLANAR C ( 30) C(29) C(31) H(301) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 31) TO H(311) 
REST 0.030, 0.002 = H(311,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(311) TO C ( 31) TO C(30) 
CONT H(311) TO C ( 31) TO C(32) 
PLANAR C ( 31) C(30) C(32) H(311) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 32) TO H(321) 
REST 0.024, 0.002 = H(321,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(321) TO C ( 32) TO C(27) 
CONT H(321) TO C ( 32) TO C(31) 
PLANAR C ( 32) C(27) C(31) H(321) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 34) TO H(341) 
REST 0.029, 0.002 = H(341,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(341) TO C ( 34) TO C(33) 
CONT H(341) TO C ( 34) TO C(35) 
PLANAR C ( 34) C(33) C(35) H(341) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 35) TO H(351) 
REST 0.039, 0.002 = H(351,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(351) TO C ( 35) TO C(34) 
CONT H(351) TO C ( 35) TO C(36) 
PLANAR C ( 35) C(34) C(36) H(351) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 36) TO H(361) 
REST 0.043, 0.002 = H(361,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(361) TO C ( 36) TO C(35) 
CONT H(361) TO C ( 36) TO C(37) 
PLANAR C ( 36) C(35) C(37) H(361) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 37) TO H(371) 
REST 0.040, 0.002 = H(371,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(371) TO C ( 37) TO C(36) 
CONT H(371) TO C ( 37) TO C(38) 
PLANAR C ( 37) C(36) C(38) H(371) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 38) TO H(381) 
REST 0.029, 0.002 = H(381,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(381) TO C ( 38) TO C(33) 
CONT H(381) TO C ( 38) TO C(37) 
PLANAR C ( 38) C(33) C(37) H(381) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 42) TO H(421) 
REST 0.024, 0.002 = H(421,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(421) TO C ( 42) TO C(41) 
CONT H(421) TO C ( 42) TO C(43) 
PLANAR C ( 42) C(41) C(43) H(421) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 43) TO H(431) 
REST 0.026, 0.002 = H(431,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(431) TO C ( 43) TO C(42) 
CONT H(431) TO C ( 43) TO C(44) 
PLANAR C ( 43) C(42) C(44) H(431) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 45) TO H(451) 
REST 0.031, 0.002 = H(451,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(451) TO C ( 45) TO C(44) 
CONT H(451) TO C ( 45) TO C(46) 
PLANAR C ( 45) C(44) C(46) H(451) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 46) TO H(461) 
REST 0.032, 0.002 = H(461,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(461) TO C ( 46) TO C(41) 
CONT H(461) TO C ( 46) TO C(45) 
PLANAR C ( 46) C(41) C(45) H(461) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 47) TO H(471) 
CONT C ( 47) TO H(472) 
CONT C ( 47) TO H(473) 
REST 0.036, 0.002 = H(471,U[ISO]) 
REST 0.036, 0.002 = H(472,U[ISO]) 
REST 0.036, 0.002 = H(473,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(44) TO C ( 47) TO H(471) 
CONT C(44) TO C ( 47) TO H(472) 
CONT C(44) TO C ( 47) TO H(473) 
ANGLE 0.0, 2.0 = MEAN H(471) TO C ( 47) TO H(472) 
CONT H(471) TO C ( 47) TO H(473) 
CONT H(472) TO C ( 47) TO H(473) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;