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_4064673
_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         'C50 H42 Ge1 O3'
_chemical_formula_sum            'C50 H42 Ge O3'
_chemical_formula_weight         763.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_cell_angle_alpha                90
_cell_angle_beta                 92.4250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.24330(10)
_cell_length_b                   18.0730(2)
_cell_length_c                   16.1476(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3861.40(7)
_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      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            98793
_diffrn_reflns_theta_full        32.294
_diffrn_reflns_theta_max         32.294
_diffrn_reflns_theta_min         1.692
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.238
_refine_diff_density_max         3.17
_refine_diff_density_min         -1.22
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9972
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         13642
_refine_ls_number_restraints     242
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0135408
_refine_ls_shift/su_mean         0.0005040
_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: 
 3.80 4.71 1.07 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1537
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1537
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                7425
_reflns_number_total             13676
_reflns_threshold_expression     I>2.0\s(I)
_oxford_refine_ls_r_factor_ref   0.0718
_oxford_refine_ls_scale          0.082874(16)
_oxford_reflns_number_all        13642
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            om200259n_si_005.cif
_cod_data_source_block           1
_cod_original_cell_volume        3861.41(7)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C50 H42 Ge1 O3'
_cod_database_code               4064673
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT GE   (    1 ,X'S,U'S)  UNTIL C    (   49 ) 
CONT H    (   51 ,X'S)  UNTIL H    (  491 ) 
CONT C    (   46 ,X'S,U'S)  UNTIL C    (   50 ) 
CONT H    (  461 ,X'S)  UNTIL H    (  502 ) 
END                                                                             
;
_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 0.026, 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            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 9) TO H(91) 
CONT C ( 9) TO H(92) 
CONT C ( 9) TO H(93) 
REST 0.048, 0.002 = H(91,U[ISO]) 
REST 0.048, 0.002 = H(92,U[ISO]) 
REST 0.048, 0.002 = H(93,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT O(8) TO C ( 9) TO H(91) 
CONT O(8) TO C ( 9) TO H(92) 
CONT O(8) TO C ( 9) TO H(93) 
ANGLE 0.0, 2.0 = MEAN H(91) TO C ( 9) TO H(92) 
CONT H(91) TO C ( 9) TO H(93) 
CONT H(92) TO C ( 9) TO H(93) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 10) TO H(101) 
REST 0.033, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(7) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(7) C(11) H(101) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 11) TO H(111) 
REST 0.033, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(4) 
CONT H(111) TO C ( 11) TO C(10) 
PLANAR C ( 11) C(4) C(10) H(111) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 17) TO H(171) 
REST 0.025, 0.002 = H(171,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(171) TO C ( 17) TO C(16) 
CONT H(171) TO C ( 17) TO C(18) 
PLANAR C ( 17) C(16) C(18) H(171) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 18) TO H(181) 
REST 0.031, 0.002 = H(181,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(181) TO C ( 18) TO C(17) 
CONT H(181) TO C ( 18) TO C(19) 
PLANAR C ( 18) C(17) C(19) H(181) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 19) TO H(191) 
REST 0.034, 0.002 = H(191,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(191) TO C ( 19) TO C(18) 
CONT H(191) TO C ( 19) TO C(20) 
PLANAR C ( 19) C(18) C(20) H(191) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 20) TO H(201) 
REST 0.035, 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 0.030, 0.002 = H(211,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(211) TO C ( 21) TO C(16) 
CONT H(211) TO C ( 21) TO C(20) 
PLANAR C ( 21) C(16) C(20) H(211) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 23) TO H(231) 
REST 0.024, 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 0.028, 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(25) 
PLANAR C ( 24) C(23) C(25) H(241) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 25) TO H(251) 
REST 0.029, 0.002 = H(251,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(251) TO C ( 25) TO C(24) 
CONT H(251) TO C ( 25) TO C(26) 
PLANAR C ( 25) C(24) C(26) H(251) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 26) TO H(261) 
REST 0.029, 0.002 = H(261,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(261) TO C ( 26) TO C(25) 
CONT H(261) TO C ( 26) TO C(27) 
PLANAR C ( 26) C(25) C(27) H(261) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 27) TO H(271) 
REST 0.023, 0.002 = H(271,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(271) TO C ( 27) TO C(26) 
CONT H(271) TO C ( 27) TO C(22) 
PLANAR C ( 27) C(26) C(22) H(271) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 29) TO H(291) 
REST 0.028, 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 0.033, 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 0.034, 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 0.032, 0.002 = H(321,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(321) TO C ( 32) TO C(31) 
CONT H(321) TO C ( 32) TO C(33) 
PLANAR C ( 32) C(31) C(33) H(321) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 33) TO H(331) 
REST 0.025, 0.002 = H(331,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(331) TO C ( 33) TO C(28) 
CONT H(331) TO C ( 33) TO C(32) 
PLANAR C ( 33) C(28) C(32) H(331) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 35) TO H(351) 
REST 0.027, 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 0.033, 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 0.043, 0.002 = H(381,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(381) TO C ( 38) TO C(37) 
CONT H(381) TO C ( 38) TO C(39) 
PLANAR C ( 38) C(37) C(39) H(381) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 39) TO H(391) 
REST 0.035, 0.002 = H(391,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(391) TO C ( 39) TO C(34) 
CONT H(391) TO C ( 39) TO C(38) 
PLANAR C ( 39) C(34) C(38) H(391) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 43) TO H(431) 
REST 0.030, 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 ( 44) TO H(441) 
REST 0.031, 0.002 = H(441,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(441) TO C ( 44) TO C(43) 
CONT H(441) TO C ( 44) TO C(45) 
PLANAR C ( 44) C(43) C(45) H(441) 
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 0.049, 0.002 = H(471,U[ISO]) 
REST 0.049, 0.002 = H(472,U[ISO]) 
REST 0.049, 0.002 = H(473,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT O(46) TO C ( 47) TO H(471) 
CONT O(46) TO C ( 47) TO H(472) 
CONT O(46) 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            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 48) TO H(481) 
REST 0.033, 0.002 = H(481,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(481) TO C ( 48) TO C(45) 
CONT H(481) TO C ( 48) TO C(49) 
PLANAR C ( 48) C(45) C(49) H(481) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 49) TO H(491) 
REST 0.032, 0.002 = H(491,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(491) TO C ( 49) TO C(42) 
CONT H(491) TO C ( 49) TO C(48) 
PLANAR C ( 49) C(42) C(48) H(491) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 46) TO H(461) 
CONT C ( 46) TO H(462) 
REST 0.070, 0.002 = H(461,U[ISO]) 
REST 0.070, 0.002 = H(462,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(461) TO C ( 46) TO C(8) 
CONT H(461) TO C ( 46) TO C(50) 
CONT H(462) TO C ( 46) TO C(8) 
CONT H(462) TO C ( 46) TO C(50) 
ANGLE 109.54, 2.0 = 
CONT H(461) TO C ( 46) TO H(462) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 1) TO H(11) 
CONT C ( 1) TO H(12) 
REST 0.090, 0.002 = H(11,U[ISO]) 
REST 0.090, 0.002 = H(12,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(11) TO C ( 1) TO O(3) 
CONT H(11) TO C ( 1) TO C(8) 
CONT H(12) TO C ( 1) TO O(3) 
CONT H(12) TO C ( 1) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(11) TO C ( 1) TO H(12) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 8) TO H(81) 
CONT C ( 8) TO H(82) 
REST 0.107, 0.002 = H(81,U[ISO]) 
REST 0.107, 0.002 = H(82,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(46) 
CONT H(81) TO C ( 8) TO C(1) 
CONT H(82) TO C ( 8) TO C(46) 
CONT H(82) TO C ( 8) TO C(1) 
ANGLE 109.54, 2.0 = 
CONT H(81) TO C ( 8) TO H(82) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 50) TO H(501) 
CONT C ( 50) TO H(502) 
REST 0.105, 0.002 = H(501,U[ISO]) 
REST 0.105, 0.002 = H(502,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(501) TO C ( 50) TO C(46) 
CONT H(501) TO C ( 50) TO O(3) 
CONT H(502) TO C ( 50) TO C(46) 
CONT H(502) TO C ( 50) TO O(3) 
ANGLE 109.54, 2.0 = 
CONT H(501) TO C ( 50) TO H(502) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;