# Supplementary Material (ESI) for Perkin Transactions

# This journal is © The Royal Society of Chemistry 2000

# CCDC Number: 207/388



data_global



_publ_contact_author_name            'Shigeyuki Yagi'

_publ_contact_author_adress           

;

Deapartment of Applied Materials 

Science College of Engineering, 

Osaka Prefecture University

1-1 Gakuen-cho, Sakai,

Osaka 599-8531, Japan

E-mail: yagi@ams.osakafu-u.ac.jp

;

_publ_requested_journal               ' J. Perkin Transactions 1'



_publ_section_title     

                

;

Synthesis of Novel Unsymmetrical Squarylium Dyes Absorbing in the

Near-infrared Region

;                                      



_publ_section_references

;

Molecular Structure Corporation. (1985). TEXSAN 

TEXRAY Structure Analysis Package.

;

data_1

#------------------------------------------------------------------------------

_audit_creation_date                    'Tue Aug 10, 1999'

_audit_creation_method                'from TEXRAY.INF file'

_audit_update_record                   ?

#------------------------------------------------------------------------------

_computing_data_collection            'MSC/AFC Diffractometer Control'

_computing_cell_refinement            'MSC/AFC Diffractometer Control'

_computing_data_reduction             'teXsan'

_computing_structure_solution          'teXsan'

_computing_structure_refinement       'teXsan'

_computing_publication_material       'teXsan'

_computing_molecular_graphics         'teXsan'

#------------------------------------------------------------------------------

_chemical_name_common            

;

4-(N-Hexylbenz[c,d]indolinylidenemethyl)-2-

(4-julolidinyl)-3-cyclobutene-1,3-dione

;

_chemical_formula_weight               559.73

_chemical_formula_sum                 'C37H39 N2O3 '

_chemical_formula_moiety               'C34 H34N2O2_H2O_1/2(C6H6) '

_chemical_melting_point                -

#------------------------------------------------------------------------------

_cell_length_a                         14.427(6)

_cell_length_b                         15.199(6)

_cell_length_c                           7.498(3)

_cell_angle_alpha                      98.72(3)

_cell_angle_beta                       99.51(3)

_cell_angle_gamma                    106.61(3)

_cell_volume                           1519(2)

_cell_formula_units_Z                  2

_cell_measurement_temperature          296

_cell_measurement_reflns_used          25

_cell_measurement_theta_min            7.46

_cell_measurement_theta_max            22.09

#------------------------------------------------------------------------------

_symmetry_cell_setting                 triclinic

_symmetry_space_group_name_H-M        P-1

_symmetry_Int_Tables_number            2

loop_

_symmetry_equiv_pos_as_xyz

x,y,z

-x,-y,-z

_exptl_crystal_description            'prismatic'

_exptl_crystal_colour                    'gold'

_exptl_crystal_size_max                0.4

_exptl_crystal_size_mid                0.13

_exptl_crystal_size_min                0.05

_exptl_crystal_density_diffrn          1.224

_exptl_crystal_density_meas            'not measured'

_exptl_crystal_F_000                     ?598

_exptl_absorpt_coefficient_mu          0.72

_exptl_absorpt_correction_type        none

#------------------------------------------------------------------------------

_diffrn_ambient_temperature            296

_diffrn_radiation_wavelength           0.7107

_diffrn_radiation_type                'Mo Kalpha'

_diffrn_radiation_source              'Rigaku rotating anode'

_diffrn_radiation_monochromator        'graphite'

_diffrn_radiation_detector            'scintillation counter'

_diffrn_measurement_device_type        'Rigaku AFC5R'

_diffrn_measurement_method            'omega-2theta scanning' 

_diffrn_standards_number              3

_diffrn_standards_interval_count      150

_diffrn_standards_decay_%             -2.9

_diffrn_reflns_number                  4056

_reflns_number_total                   3825

_reflns_observed_criterion             >2.0sigma(I)

_diffrn_reflns_av_R_equivalents        0.163

_diffrn_reflns_theta_max               25.1

_diffrn_reflns_limit_h_min             0

_diffrn_reflns_limit_h_max             13

_diffrn_reflns_limit_k_min             -15

_diffrn_reflns_limit_k_max             13

_diffrn_reflns_limit_l_min             -7

_diffrn_reflns_limit_l_max              7

#------------------------------------------------------------------------------

_refine_ls_structure_factor_coef       F

_refine_ls_matrix_type                 full

_refine_ls_weighting_scheme           '  unit weight'

_refine_ls_hydrogen_treatment      ' noref  (calculated position)'

_refine_ls_extinction_method         none 

_refine_ls_extinction_coef              ?

_refine_ls_abs_structure_details        ?

_refine_ls_abs_structure_Flack         ?

_refine_ls_number_reflns              1057

_refine_ls_number_parameters          169

_refine_ls_R_factor_all                0.127

_refine_ls_R_factor_obs               0.127

_refine_ls_wR_factor_all               0.095

_refine_ls_wR_factor_obs              0.095

_refine_ls_goodness_of_fit_all          2.67

_refine_ls_goodness_of_fit_obs      ?

_refine_ls_shift/esd_max               0.08

_refine_ls_shift/esd_mean      ?

_refine_diff_density_min               -0.44

_refine_diff_density_max               0.39

#-------------------------------------------------------------------------------

_atom_site_solution_primary        'Direct method'

_atom_site_solution_secondary      'Fourier Difference Synthesis'



loop_

_atom_site_label

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_thermal_displace_type

_atom_site_calc_flag

_atom_site_calc_attached_atom

_atom_site_occupancy

_atom_site_refinement_flags



 C(1)    0.139(2)    0.332(2)   0.709(3)   0.041(7)     Uiso d . 1.00 .

 C(2)    0.054(2)    0.262(1)   0.727(3)   0.048(7)     Uiso d . 1.00 .

 C(3)    0.010(2)    0.271(2)   0.873(3)   0.054(7)     Uiso d . 1.00 .

 C(4)  -0.075(2)    0.193(2)   0.902(3)   0.073(8)     Uiso d . 1.00 .

 C(5)  -0.138(2)    0.228(2)    1.011(4)   0.10(1)      Uiso d . 1.00 .

 C(6)  -0.079(2)    0.294(2)    1.188(3)   0.081(9)    Uiso d . 1.00 .

 C(7)    0.044(2)    0.451(2)   1.305(4)   0.09(1)       Uiso d . 1.00 .

 C(8)    0.116(3)    0.525(2)   1.266(4)   0.15(1)       Uiso d . 1.00 .

 C(9)    0.177(2)    0.517(2)   1.151(4)   0.10(1)       Uiso d . 1.00 .

 C(10)  0.136(2)    0.426(2)   0.996(3)   0.046(7)     Uiso d . 1.00 .

 C(11)  0.177(2)    0.413(2)   0.848(3)   0.057(7)     Uiso d . 1.00 .

 C(12)  0.051(2)    0.354(2)   1.018(3)   0.053(7)     Uiso d . 1.00 .

 C(13)  0.181(1)    0.319(1)   0.558(3)   0.037(6)     Uiso d . 1.00 .

 C(14)  0.158(2)    0.250(2)   0.388(3)   0.064(8)     Uiso d . 1.00 .

 C(15)  0.250(1)    0.308(1)   0.333(3)   0.036(6)     Uiso d . 1.00 .

 C(16)  0.269(2)    0.372(2)   0.508(3)   0.065(8)     Uiso d . 1.00 .

 C(17)  0.307(1)    0.313(1)   0.207(3)   0.039(6)     Uiso d . 1.00 .

 C(18)  0.301(1)    0.260(1)   0.035(3)   0.038(6)     Uiso d . 1.00 .

 C(19)  0.231(1)    0.168(1)  -0.071(3)   0.034(6)     Uiso d . 1.00 .

 C(20)  0.146(2)    0.106(2)  -0.034(3)   0.056(7)     Uiso d . 1.00 .

 C(21)  0.098(2)    0.026(2)  -0.181(3)   0.062(7)     Uiso d . 1.00 .

 C(22)  0.126(2)    0.007(2)  -0.345(3)   0.078(9)     Uiso d . 1.00 .

 C(23)  0.210(2)    0.069(2)  -0.387(3)   0.054(7)     Uiso d . 1.00 .

 C(24)  0.255(2)    0.066(2)  -0.536(3)   0.074(8)     Uiso d . 1.00 .

 C(25)  0.340(2)    0.137(2)  -0.541(3)   0.062(8)     Uiso d . 1.00 .

 C(26)  0.387(2)    0.215(1)  -0.390(3)   0.056(8)     Uiso d . 1.00 .

 C(27)  0.345(2)    0.218(1)  -0.242(3)   0.049(7)     Uiso d . 1.00 .

 C(28)  0.260(2)    0.147(1)  -0.238(3)   0.042(7)     Uiso d . 1.00 .

 C(29)  0.459(2)    0.371(1)  -0.027(3)   0.053(7)     Uiso d . 1.00 .

 C(30)  0.548(2)    0.345(2)    0.039(3)   0.082(9)     Uiso d . 1.00 .

 C(31)  0.553(2)    0.302(2)    0.201(4)   0.10(1)       Uiso d . 1.00 .

 C(32)  0.645(2)    0.275(2)    0.261(4)   0.11(1)       Uiso d . 1.00 .

 C(33)  0.638(2)    0.232(2)    0.425(4)   0.14(1)       Uiso d . 1.00 .

 C(34)  0.719(3)    0.197(2)    0.490(4)   0.18(1)       Uiso d . 1.00 .

 C(35)  0.461(3)    0.035(2)  -0.131(4)    0.11(1)       Uiso d . 1.00 .

 C(36)  0.409(2)    0.005(2)  -0.013(5)    0.12(1)       Uiso d . 1.00 .

 C(37)  0.443(3)   -0.029(2)   0.141(5)   0.14(1)        Uiso d . 1.00 .

 N(1)   0.003(1)    0.368(1)    1.158(3)    0.059(6)      Uiso d . 1.00 .

 N(2)   0.368(1)    0.283(1)  -0.075(2)    0.037(5)      Uiso d . 1.00 .

 O(1)   0.088(1)    0.179(1)     0.315(2)   0.065(5)      Uiso d . 1.00 .

 O(2)   0.339(1)    0.447(1)   0.582(2)     0.065(5)      Uiso d . 1.00 .

 O(3)   0.461(2)    0.545(2)   0.375(3)     0.25(1)        Uiso d . 1.00 .

 H(1)    0.0266     0.2070     0.6327      0.0557           Uiso calc . 1.00 .

 H(2)  -0.1151     0.1598     0.7840      0.0878           Uiso calc . 1.00 .

 H(3)  -0.0487     0.1529     0.9629      0.0878           Uiso calc . 1.00 .

 H(4)  -0.1731     0.2593     0.9412      0.1221           Uiso calc . 1.00 .

 H(5)  -0.1824     0.1759     1.0409      0.1221           Uiso calc . 1.00 .

 H(6)  -0.1207     0.3226     1.2432      0.1000           Uiso calc . 1.00 .

 H(7)  -0.0527     0.2607     1.2691      0.1000           Uiso calc . 1.00 .

 H(8)   0.0750     0.4335      1.4125      0.1066           Uiso calc . 1.00 .

 H(9)  -0.0083     0.4722     1.3351      0.1066           Uiso calc . 1.00 .

 H(10)  0.0779     0.5606     1.2121      0.1721           Uiso calc . 1.00 .

 H(11)  0.1563     0.5593     1.3796      0.1721           Uiso calc . 1.00 .

 H(12)  0.1903     0.5691     1.0954      0.1255           Uiso calc . 1.00 .

 H(13)  0.2374     0.5151     1.2240      0.1255           Uiso calc . 1.00 .

 H(14)  0.2332     0.4622     0.8395      0.0666           Uiso calc . 1.00 .

 H(15)  0.3657     0.3660     0.2441      0.0460           Uiso calc . 1.00 .

 H(16)  0.1235     0.1156     0.0759      0.0655           Uiso calc . 1.00 .

 H(17)  0.0406    -0.0183   -0.1636     0.0729           Uiso calc . 1.00 .

 H(18)  0.0872    -0.0488   -0.4328     0.0932           Uiso calc . 1.00 .

 H(19)  0.2271     0.0137    -0.6382     0.0888           Uiso calc . 1.00 .

 H(20)  0.3674     0.1331    -0.6467     0.0749           Uiso calc . 1.00 .

 H(21)  0.4451     0.2629    -0.3933     0.0678           Uiso calc . 1.00 .

 H(22)  0.4508     0.4155     0.0676      0.0622            Uiso calc . 1.00 .

 H(23)  0.4654     0.3964    -0.1334     0.0622            Uiso calc . 1.00 .

 H(24)  0.5544     0.3023    -0.0600     0.0966            Uiso calc . 1.00 .

 H(25)  0.6027     0.4011     0.0680      0.0966            Uiso calc . 1.00 .

 H(26)  0.5487     0.3452     0.3023      0.1219            Uiso calc . 1.00 .

 H(27)  0.4981     0.2465     0.1747      0.1219            Uiso calc . 1.00 .

 H(28)  0.6517     0.2317     0.1634      0.1326            Uiso calc . 1.00 .

 H(29)  0.7019     0.3300     0.2927      0.1326            Uiso calc . 1.00 .

 H(30)  0.6358     0.2775     0.5262      0.1634            Uiso calc . 1.00 .

 H(31)  0.5777     0.1805     0.3970      0.1634            Uiso calc . 1.00 .

 H(32)  0.7087     0.1707     0.5942      0.2135            Uiso calc . 1.00 .

 H(33)  0.7210     0.1491     0.3921      0.2135            Uiso calc . 1.00 .

 H(34)  0.7797     0.2465     0.5192      0.2135            Uiso calc . 1.00 .

 H(35)  0.4331     0.0646    -0.2321     0.1259            Uiso calc . 1.00 .

 H(36)  0.3450     0.0096    -0.0384     0.1428            Uiso calc . 1.00 .

 H(37)  0.3990    -0.0458     0.2312     0.1585            Uiso calc . 1.00 .

 H(38)  0.5170     0.6026     0.4372      0.2533            Uiso calc . 1.00 .

 H(39)  0.4021     0.5645     0.3984      0.2533            Uiso calc . 1.00 .





#------------------------------------------------------------------------------

_geom_special_details

;

;

loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_1

_geom_bond_site_symmetry_2

_geom_bond_publ_flag



C(1)       C(2)           1.41(2)         1_555 1_555 yes               

C(1)       C(11)         1.40(2)         1_555 1_555 yes

C(1)       C(13)         1.38(2)         1_555 1_555 yes               

C(2)       C(3)           1.37(2)         1_555 1_555 yes

C(3)       C(4)           1.51(2)         1_555 1_555 yes               

C(3)       C(12)         1.44(2)         1_555 1_555 yes

C(4)       C(5)          1.47(2)          1_555 1_555 yes               

C(5)       C(6)          1.49(2)          1_555 1_555 yes

C(6)       N(1)          1.46(2)          1_555 1_555 yes               

C(7)       C(8)          1.40(3)          1_555 1_555 yes

C(7)       N(1)          1.46(2)          1_555 1_555 yes               

C(8)       C(9)          1.34(3)          1_555 1_555 yes

C(9)       C(10)        1.56(3)          1_555 1_555 yes               

C(10)      C(11)       1.35(2)          1_555 1_555 yes

C(10)      C(12)       1.45(2)          1_555 1_555 yes               

C(12)      N(1)         1.37(2)          1_555 1_555 yes

C(13)      C(14)       1.45(2)          1_555 1_555 yes               

C(13)      C(16)       1.44(2)          1_555 1_555 yes

C(14)      C(15)       1.52(2)          1_555 1_555 yes               

C(14)      O(1)         1.23(2)          1_555 1_555 yes

C(15)      C(16)       1.45(2)          1_555 1_555 yes               

C(15)      C(17)       1.35(2)          1_555 1_555 yes

C(16)      O(2)         1.26(2)          1_555 1_555 yes               

C(17)      C(18)       1.38(2)          1_555 1_555 yes

C(18)      C(19)       1.48(2)          1_555 1_555 yes               

C(18)      N(2)         1.39(2)          1_555 1_555 yes

C(19)      C(20)       1.41(2)          1_555 1_555 yes               

C(19)      C(28)       1.40(2)          1_555 1_555 yes

C(20)   ?C(21)       1.42(2)          1_555 1_555 yes               

C(21)      C(22)       1.37(2)          1_555 1_555 yes

C(22)   ?C(23)       1.42(2)          1_555 1_555 yes               

C(23)   ?C(24)       1.39(2)          1_555 1_555 yes

C(23)   ?C(28)       1.42(2)          1_555 1_555 yes               

C(24)   ?C(25)       1.39(2)          1_555 1_555 yes

C(25)   ?C(26)       1.42(2)          1_555 1_555 yes               

C(26)      C(27)       1.34(2)          1_555 1_555 yes

C(27)      C(28)       1.40(2)          1_555 1_555 yes               

C(27)   ?N(2)         1.40(2)          1_555 1_555 yes

C(29)   ?C(30)       1.48(3)          1_555 1_555 yes               

C(29)      N(2)         1.52(2)          1_555 1_555 yes

C(30)   ?C(31)       1.47(3)          1_555 1_555 yes                       

C(31)   ?C(32)       1.51(3)          1_555 1_555 yes

C(32)   ?C(33)       1.49(3)          1_555 1_555 yes                       

C(33)      C(34)       1.46(4)          1_555 1_555 yes

C(35)   ?C(36)       1.31(3)          1_555 1_555 yes               

C(36)   ?C(37)       1.41(4)          1_555 1_555 yes

C(35)   ?C(37)       1.43(3)          1_555 2_655 yes



#------------------------------------------------------------------------------

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

_geom_angle_site_symmetry_2

_geom_angle_site_symmetry_3

_geom_angle_publ_flag



  C(2)    C(1)     C(11)    117(2)  1_555 1_555 1_555 yes 

  C(2)    C(1)     C(13)    121(2)   1_555 1_555 1_555 yes

  C(11)   C(1)     C(13)   122(2)   1_555 1_555 1_555 yes  

  C(1)    C(2)     C(3)     123(2)   1_555 1_555 1_555 yes

  C(2)    C(3)     C(4)     123(2)   1_555 1_555 1_555 yes      

  C(2)    C(3)     C(12)   119(2)   1_555 1_555 1_555 yes

  C(3)    C(4)     C(5)     113(2)   1_555 1_555 1_555 yes     

  C(4)    C(5)     C(6)     112(2)   1_555 1_555 1_555 yes

  C(5)    C(6)     N(1)     111(2)   1_555 1_555 1_555 yes      

  C(8)    C(7)     N(1)     115(2)   1_555 1_555 1_555 yes

  C(7)    C(8)     C(9)     126(3)   1_555 1_555 1_555 yes      

  C(8)    C(9)     C(10)    114(2)   1_555 1_555 1_555 yes

  C(9)    C(10)    C(11)   123(2)   1_555 1_555 1_555 yes      

  C(9)    C(10)    C(12)   116(2)   1_555 1_555 1_555 yes

  C(11)   C(10)    C(12)  121(2)   1_555 1_555 1_555 yes      

  C(1)    C(11)    C(10)   123(2)   1_555 1_555 1_555 yes

  C(3)    C(12)    N(1)     120(2)   1_555 1_555 1_555 yes      

  C(10)   C(12)    N(1)    122(2)   1_555 1_555 1_555 yes

  C(1)    C(13)    C(14)   137(2)   1_555 1_555 1_555 yes      

  C(1)    C(13)    C(16)   133(2)   1_555 1_555 1_555 yes

  C(13)   C(14)    C(15)   90(2)    1_555 1_555 1_555 yes      

  C(13)   C(14)    O(1)    133(2)   1_555 1_555 1_555 yes

  C(14)   C(15)    C(16)   87(2)    1_555 1_555 1_555 yes      

  C(14)   C(15)    C(17)  146(2)   1_555 1_555 1_555 yes

  C(16)   C(15)    C(17)  127(2)   1_555 1_555 1_555 yes      

  C(13)   C(16)    C(15)   93(2)    1_555 1_555 1_555 yes

  C(13)   C(16)    O(2)    136(2)   1_555 1_555 1_555 yes      

  C(15)   C(17)    C(18)  135(2)   1_555 1_555 1_555 yes

  C(17)   C(18)    C(19)  133(2)   1_555 1_555 1_555 yes      

  C(17)   C(18)    N(2)    125(2)   1_555 1_555 1_555 yes

  C(18)   C(19)    C(20)  132(2)   1_555 1_555 1_555 yes      

  C(18)   C(19)    C(28)  108(2)   1_555 1_555 1_555 yes

  C(20)   C(21)    C(22)  127(2)   1_555 1_555 1_555 yes      

  C(21)   C(22)    C(23)  122(2)   1_555 1_555 1_555 yes

  C(22)   C(23)    C(24)  133(2)   1_555 1_555 1_555 yes      

  C(22)   C(23)    C(28)  112(2)   1_555 1_555 1_555 yes

  C(23)   C(24)    C(25)  121(2)   1_555 1_555 1_555 yes      

  C(24)   C(25)    C(26)  122(2)   1_555 1_555 1_555 yes

  C(25)   C(26)    C(27)  117(2)   1_555 1_555 1_555 yes      

  C(26)   C(27)    C(28)  121(2)   1_555 1_555 1_555 yes

  C(19)   C(28)    C(23)  127(2)   1_555 1_555 1_555 yes      

  C(19)   C(28)    C(27)  109(2)   1_555 1_555 1_555 yes

  C(23)   C(28)    C(27)  123(2)   1_555 1_555 1_555 yes

  C(30)   C(29)    N(2)    109(2)   1_555 1_555 1_555 yes

  C(29)   C(30)    C(31)  119(2)   1_555 1_555 1_555 yes      

  C(30)   C(31)    C(32)  117(2)   1_555 1_555 1_555 yes

  C(31)   C(32)    C(33)  110(2)   1_555 1_555 1_555 yes      

  C(32)   C(33)    C(34)  116(2)   1_555 1_555 1_555 yes

  C(35)   C(36)    C(37)  125(3)   1_555 1_555 1_555 yes      

  C(6)    N(1)     C(7)      116(2)   1_555 1_555 1_555 yes

  C(6)    N(1)     C(12)    123(2)   1_555 1_555 1_555 yes      

  C(7)    N(1)     C(12)    120(2)   1_555 1_555 1_555 yes

  C(18)   N(2)     C(27)   114(2)   1_555 1_555 1_555 yes      

  C(27)   N(2)     C(29)   121(2)   1_555 1_555 1_555 yes



  #==END