#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/59/4025962.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025962
loop_
_publ_author_name
'Kenta Kokado'
'Yoshiki Chujo'
_publ_contact_author_address
;
Department of Polymer Chemistry, Graduate School of Engineering,
Kyoto University,
;
_publ_contact_author_email       ' chujo_at_chujo.synchem.kyoto-u.ac.jp '
_publ_contact_author_fax         ' +81-75-383-2607 '
_publ_contact_author_name        ' Yoshiki Chujo '
_publ_contact_author_phone       ' +81-75-383-2604 '
_publ_section_title
;
 Multicolor Tuning of Aggregation-Induced Emission through Substituent
 Variation of Diphenyl-o-carborane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              316
_journal_page_last               319
_journal_paper_doi               10.1021/jo101999b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C31 H29 B10 Cl3'
_chemical_formula_weight         615.99
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.984(3)
_cell_angle_beta                 106.723(3)
_cell_angle_gamma                107.190(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4393(9)
_cell_length_b                   12.2198(13)
_cell_length_c                   14.1016(11)
_cell_measurement_temperature    93(2)
_cell_volume                     1587.6(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15482
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.9123
_exptl_absorpt_correction_T_min  0.8597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0956P)²+1.2599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.2145
_reflns_number_gt                4778
_reflns_number_total             7170
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo101999b_si_003.cif
_cod_data_source_block           h
_cod_original_sg_symbol_Hall     -p_1
_cod_database_code               4025962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6764(3) 0.1982(2) -0.1903(2) 0.0201(6) Uani 1 1 d .
C2 C 0.5260(3) 0.1697(3) -0.1563(2) 0.0227(6) Uani 1 1 d .
C3 C 0.6932(3) 0.1031(2) -0.2617(2) 0.0195(6) Uani 1 1 d .
C4 C 0.6553(3) 0.0972(3) -0.3658(2) 0.0256(6) Uani 1 1 d .
H1 H 0.616(4) 0.151(3) -0.393(3) 0.032(9) Uiso 1 1 d .
C5 C 0.6829(3) 0.0181(3) -0.4323(2) 0.0271(6) Uani 1 1 d .
H2 H 0.658(4) 0.018(4) -0.506(3) 0.051(11) Uiso 1 1 d .
C6 C 0.7491(3) -0.0586(3) -0.3949(2) 0.0233(6) Uani 1 1 d .
C7 C 0.7878(3) -0.0528(3) -0.2902(2) 0.0272(6) Uani 1 1 d .
H3 H 0.832(4) -0.106(3) -0.265(3) 0.030(9) Uiso 1 1 d .
C8 C 0.7601(3) 0.0270(3) -0.2248(2) 0.0249(6) Uani 1 1 d .
H4 H 0.7871 0.0300 -0.1538 0.030 Uiso 1 1 calc R
C9 C 0.4091(3) 0.0495(2) -0.2006(2) 0.0226(6) Uani 1 1 d .
C10 C 0.4210(3) -0.0490(3) -0.1664(2) 0.0279(7) Uani 1 1 d .
H5 H 0.505(4) -0.044(3) -0.117(3) 0.031(9) Uiso 1 1 d .
C11 C 0.3080(3) -0.1574(3) -0.2050(2) 0.0298(7) Uani 1 1 d .
H6 H 0.321(3) -0.224(3) -0.180(2) 0.024(8) Uiso 1 1 d .
C12 C 0.1793(3) -0.1696(3) -0.2775(2) 0.0244(6) Uani 1 1 d .
C13 C 0.1667(3) -0.0711(3) -0.3124(3) 0.0333(7) Uani 1 1 d .
H7 H 0.084(4) -0.078(3) -0.363(3) 0.041(10) Uiso 1 1 d .
C14 C 0.2802(3) 0.0365(3) -0.2748(3) 0.0318(7) Uani 1 1 d .
H8 H 0.267(4) 0.103(3) -0.296(3) 0.035(9) Uiso 1 1 d .
C15 C 0.7771(3) -0.1403(3) -0.4644(2) 0.0243(6) Uani 1 1 d .
C16 C 0.7997(3) -0.2057(3) -0.5254(2) 0.0246(6) Uani 1 1 d .
C17 C 0.8295(3) -0.2741(3) -0.6036(2) 0.0237(6) Uani 1 1 d .
C18 C 0.9314(3) -0.2143(3) -0.6424(2) 0.0265(6) Uani 1 1 d .
H9 H 0.986(3) -0.128(3) -0.609(2) 0.020(8) Uiso 1 1 d .
C19 C 0.9572(3) -0.2754(3) -0.7215(3) 0.0314(7) Uani 1 1 d .
H10 H 1.0267 -0.2344 -0.7473 0.038 Uiso 1 1 calc R
C20 C 0.8817(3) -0.3965(3) -0.7637(3) 0.0310(7) Uani 1 1 d .
H11 H 0.902(4) -0.434(3) -0.815(3) 0.033(9) Uiso 1 1 d .
C21 C 0.7819(3) -0.4566(3) -0.7257(2) 0.0299(7) Uani 1 1 d .
H12 H 0.7311 -0.5396 -0.7543 0.036 Uiso 1 1 calc R
C22 C 0.7553(3) -0.3962(3) -0.6454(2) 0.0274(6) Uani 1 1 d .
H13 H 0.682(3) -0.441(3) -0.618(2) 0.019(8) Uiso 1 1 d .
C23 C 0.0608(3) -0.2822(3) -0.3183(2) 0.0266(6) Uani 1 1 d .
C24 C 0.9622(3) -0.3746(3) -0.3552(2) 0.0249(6) Uani 1 1 d .
C25 C 0.8414(3) -0.4847(3) -0.4061(2) 0.0251(6) Uani 1 1 d .
C26 C 0.8601(3) -0.5836(3) -0.4574(3) 0.0280(7) Uani 1 1 d .
H14 H 0.953(4) -0.582(3) -0.458(2) 0.027(8) Uiso 1 1 d .
C27 C 0.7418(4) -0.6871(3) -0.5123(3) 0.0341(7) Uani 1 1 d .
H15 H 0.761(4) -0.752(3) -0.544(3) 0.034(9) Uiso 1 1 d .
C28 C 0.6068(4) -0.6919(3) -0.5146(3) 0.0349(8) Uani 1 1 d .
H16 H 0.530(4) -0.761(4) -0.551(3) 0.045(11) Uiso 1 1 d .
C29 C 0.5885(3) -0.5966(3) -0.4622(3) 0.0350(8) Uani 1 1 d .
H17 H 0.500(4) -0.600(3) -0.464(3) 0.044(11) Uiso 1 1 d .
C30 C 0.7056(3) -0.4916(3) -0.4075(3) 0.0294(7) Uani 1 1 d .
H18 H 0.688(4) -0.422(3) -0.371(3) 0.032(9) Uiso 1 1 d .
C31 C 0.7671(4) -0.2570(4) -0.0811(3) 0.0423(9) Uani 1 1 d .
H19 H 0.747(4) -0.322(4) -0.053(3) 0.049(11) Uiso 1 1 d .
B1 B 0.5487(3) 0.2584(3) -0.2390(3) 0.0217(6) Uani 1 1 d .
H20 H 0.484(3) 0.224(3) -0.316(2) 0.021(8) Uiso 1 1 d .
B2 B 0.6887(3) 0.1857(3) -0.0672(3) 0.0227(7) Uani 1 1 d .
H21 H 0.702(3) 0.106(3) -0.045(2) 0.019(7) Uiso 1 1 d .
B3 B 0.7350(3) 0.3424(3) -0.1970(3) 0.0236(7) Uani 1 1 d .
H22 H 0.781(3) 0.361(3) -0.253(2) 0.024(8) Uiso 1 1 d .
B4 B 0.8221(3) 0.2972(3) -0.0898(3) 0.0219(6) Uani 1 1 d .
H23 H 0.920(4) 0.285(3) -0.088(2) 0.027(8) Uiso 1 1 d .
B5 B 0.5711(4) 0.2499(3) -0.0332(3) 0.0249(7) Uani 1 1 d .
H24 H 0.512(3) 0.205(3) 0.011(2) 0.023(8) Uiso 1 1 d .
B6 B 0.4853(4) 0.2962(3) -0.1391(3) 0.0253(7) Uani 1 1 d .
H25 H 0.375(4) 0.285(3) -0.159(3) 0.034(9) Uiso 1 1 d .
B7 B 0.6162(4) 0.4059(3) -0.1642(3) 0.0268(7) Uani 1 1 d .
H26 H 0.592(3) 0.475(3) -0.195(2) 0.023(8) Uiso 1 1 d .
B8 B 0.7585(4) 0.3333(3) 0.0108(3) 0.0241(7) Uani 1 1 d .
H27 H 0.823(4) 0.352(3) 0.094(3) 0.034(9) Uiso 1 1 d .
B9 B 0.7872(4) 0.4317(3) -0.0694(3) 0.0282(7) Uani 1 1 d .
H28 H 0.877(4) 0.517(3) -0.043(3) 0.035(9) Uiso 1 1 d .
B10 B 0.6318(4) 0.4020(3) -0.0347(3) 0.0250(7) Uani 1 1 d .
H29 H 0.620(4) 0.466(3) 0.015(3) 0.029(9) Uiso 1 1 d .
Cl1 Cl 0.89881(11) -0.26057(10) -0.13526(8) 0.0498(3) Uani 1 1 d .
Cl2 Cl 0.60897(10) -0.26796(8) -0.17811(8) 0.0420(3) Uani 1 1 d .
Cl3 Cl 0.82704(12) -0.12713(10) 0.01822(9) 0.0612(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C3 C1 B4 120.2(2) .
C3 C1 B3 120.0(2) .
B4 C1 B3 62.83(18) .
C3 C1 C2 120.7(2) .
B4 C1 C2 109.7(2) .
B3 C1 C2 109.8(2) .
C3 C1 B1 118.9(2) .
B4 C1 B1 112.9(2) .
B3 C1 B1 62.05(18) .
C2 C1 B1 60.02(16) .
C3 C1 B2 118.8(2) .
B4 C1 B2 62.14(18) .
B3 C1 B2 113.2(2) .
C2 C1 B2 60.02(17) .
B1 C1 B2 111.2(2) .
C9 C2 B5 121.8(2) .
C9 C2 B6 120.6(2) .
B5 C2 B6 62.28(19) .
C9 C2 C1 119.7(2) .
B5 C2 C1 109.8(2) .
B6 C2 C1 109.4(2) .
C9 C2 B1 117.2(2) .
B5 C2 B1 112.8(2) .
B6 C2 B1 61.90(18) .
C1 C2 B1 60.19(16) .
C9 C2 B2 119.6(2) .
B5 C2 B2 62.04(19) .
B6 C2 B2 112.6(2) .
C1 C2 B2 60.33(16) .
B1 C2 B2 111.6(2) .
C4 C3 C8 118.3(3) .
C4 C3 C1 119.9(2) .
C8 C3 C1 121.4(2) .
C5 C4 C3 121.4(3) .
C4 C5 C6 120.0(3) .
C7 C6 C5 118.8(3) .
C7 C6 C15 121.6(3) .
C5 C6 C15 119.6(3) .
C8 C7 C6 120.5(3) .
C7 C8 C3 121.0(3) .
C10 C9 C14 118.2(3) .
C10 C9 C2 122.4(3) .
C14 C9 C2 119.3(3) .
C11 C10 C9 121.0(3) .
C12 C11 C10 120.7(3) .
C11 C12 C13 118.5(3) .
C11 C12 C23 121.2(3) .
C13 C12 C23 120.3(3) .
C14 C13 C12 120.6(3) .
C13 C14 C9 120.9(3) .
C16 C15 C6 177.2(3) .
C15 C16 C17 174.0(3) .
C22 C17 C18 119.3(3) .
C22 C17 C16 122.2(3) .
C18 C17 C16 118.4(3) .
C19 C18 C17 120.2(3) .
C18 C19 C20 120.2(3) .
C21 C20 C19 120.1(3) .
C20 C21 C22 120.3(3) .
C21 C22 C17 119.9(3) .
C24 C23 C12 177.8(3) 1_455
C23 C24 C25 176.4(3) 1_655
C30 C25 C26 119.8(3) .
C30 C25 C24 120.1(3) .
C26 C25 C24 120.0(3) .
C27 C26 C25 119.9(3) .
C28 C27 C26 119.6(3) .
C29 C28 C27 120.7(3) .
C28 C29 C30 120.5(3) .
C25 C30 C29 119.4(3) .
Cl3 C31 Cl1 111.5(2) .
Cl3 C31 Cl2 110.4(2) .
Cl1 C31 Cl2 109.4(2) .
C2 B1 C1 59.79(16) .
C2 B1 B7 106.3(2) .
C1 B1 B7 106.0(2) .
C2 B1 B6 58.81(18) .
C1 B1 B6 106.6(2) .
B7 B1 B6 60.17(19) .
C2 B1 B3 106.8(2) .
C1 B1 B3 58.47(17) .
B7 B1 B3 60.25(19) .
B6 B1 B3 108.3(2) .
C2 B2 C1 59.64(17) .
C2 B2 B8 105.8(2) .
C1 B2 B8 105.6(2) .
C2 B2 B5 58.34(18) .
C1 B2 B5 106.3(2) .
B8 B2 B5 60.38(19) .
C2 B2 B4 106.2(2) .
C1 B2 B4 58.17(17) .
B8 B2 B4 60.17(18) .
B5 B2 B4 108.3(2) .
C1 B3 B7 106.0(2) .
C1 B3 B1 59.49(17) .
B7 B3 B1 59.31(19) .
C1 B3 B4 58.47(17) .
B7 B3 B4 108.3(2) .
B1 B3 B4 107.4(2) .
C1 B3 B9 105.6(2) .
B7 B3 B9 60.7(2) .
B1 B3 B9 107.6(2) .
B4 B3 B9 59.96(19) .
C1 B4 B2 59.70(17) .
C1 B4 B8 106.4(2) .
B2 B4 B8 59.69(19) .
C1 B4 B3 58.70(17) .
B2 B4 B3 107.9(2) .
B8 B4 B3 108.5(2) .
C1 B4 B9 105.9(2) .
B2 B4 B9 108.0(2) .
B8 B4 B9 60.47(19) .
B3 B4 B9 60.1(2) .
C2 B5 B2 59.62(18) .
C2 B5 B6 59.19(18) .
B2 B5 B6 108.1(2) .
C2 B5 B8 106.3(2) .
B2 B5 B8 59.75(19) .
B6 B5 B8 108.0(2) .
C2 B5 B10 105.8(2) .
B2 B5 B10 107.8(2) .
B6 B5 B10 59.53(19) .
B8 B5 B10 60.27(19) .
C2 B6 B10 106.0(2) .
C2 B6 B7 106.1(2) .
B10 B6 B7 61.0(2) .
C2 B6 B5 58.53(19) .
B10 B6 B5 60.5(2) .
B7 B6 B5 109.1(2) .
C2 B6 B1 59.29(18) .
B10 B6 B1 108.1(2) .
B7 B6 B1 59.40(19) .
B5 B6 B1 107.6(2) .
B1 B7 B6 60.43(19) .
B1 B7 B3 60.44(19) .
B6 B7 B3 108.6(2) .
B1 B7 B10 107.6(2) .
B6 B7 B10 59.37(19) .
B3 B7 B10 107.6(2) .
B1 B7 B9 108.0(2) .
B6 B7 B9 107.3(2) .
B3 B7 B9 60.1(2) .
B10 B7 B9 59.4(2) .
B2 B8 B4 60.14(18) .
B2 B8 B5 59.87(19) .
B4 B8 B5 107.8(2) .
B2 B8 B10 107.6(2) .
B4 B8 B10 107.4(2) .
B5 B8 B10 59.88(19) .
B2 B8 B9 107.9(2) .
B4 B8 B9 59.92(19) .
B5 B8 B9 107.6(2) .
B10 B8 B9 59.52(19) .
B10 B9 B4 107.6(2) .
B10 B9 B3 107.6(2) .
B4 B9 B3 59.92(19) .
B10 B9 B8 60.10(19) .
B4 B9 B8 59.61(19) .
B3 B9 B8 107.6(2) .
B10 B9 B7 60.24(19) .
B4 B9 B7 107.1(2) .
B3 B9 B7 59.2(2) .
B8 B9 B7 107.9(2) .
B6 B10 B9 108.4(2) .
B6 B10 B5 59.97(19) .
B9 B10 B5 108.3(2) .
B6 B10 B8 108.0(2) .
B9 B10 B8 60.38(19) .
B5 B10 B8 59.85(19) .
B6 B10 B7 59.59(19) .
B9 B10 B7 60.4(2) .
B5 B10 B7 107.6(2) .
B8 B10 B7 108.2(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.500(4) .
C1 B4 1.710(4) .
C1 B3 1.714(4) .
C1 C2 1.725(4) .
C1 B1 1.732(4) .
C1 B2 1.737(4) .
C2 C9 1.502(4) .
C2 B5 1.709(5) .
C2 B6 1.721(4) .
C2 B1 1.730(4) .
C2 B2 1.732(4) .
C3 C4 1.391(4) .
C3 C8 1.396(4) .
C4 C5 1.389(4) .
C5 C6 1.402(4) .
C6 C7 1.398(4) .
C6 C15 1.440(4) .
C7 C8 1.388(4) .
C9 C10 1.390(4) .
C9 C14 1.394(4) .
C10 C11 1.387(4) .
C11 C12 1.384(4) .
C12 C13 1.397(4) .
C12 C23 1.446(4) .
C13 C14 1.383(4) .
C15 C16 1.203(4) .
C16 C17 1.441(4) .
C17 C22 1.397(4) .
C17 C18 1.401(4) .
C18 C19 1.381(4) .
C19 C20 1.389(5) .
C20 C21 1.380(5) .
C21 C22 1.394(4) .
C23 C24 1.195(4) 1_455
C24 C23 1.195(4) 1_655
C24 C25 1.445(4) .
C25 C30 1.390(4) .
C25 C26 1.404(4) .
C26 C27 1.394(5) .
C27 C28 1.384(5) .
C28 C29 1.373(5) .
C29 C30 1.399(5) .
C31 Cl3 1.757(4) .
C31 Cl1 1.762(4) .
C31 Cl2 1.768(4) .
B1 B7 1.756(5) .
B1 B6 1.775(5) .
B1 B3 1.776(5) .
B2 B8 1.771(5) .
B2 B5 1.773(5) .
B2 B4 1.779(4) .
B3 B7 1.773(5) .
B3 B4 1.784(5) .
B3 B9 1.788(5) .
B4 B8 1.780(5) .
B4 B9 1.785(5) .
B5 B6 1.774(5) .
B5 B8 1.782(5) .
B5 B10 1.783(5) .
B6 B10 1.766(5) .
B6 B7 1.770(5) .
B7 B10 1.796(5) .
B7 B9 1.799(5) .
B8 B10 1.790(5) .
B8 B9 1.795(5) .
B9 B10 1.780(5) .
