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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_SQ3-rac_01

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,3-bis[4-(N-sec-butyl-N-n-propylamino)-2,6-dihydroxyphenyl]squaraine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H40 N2 O6'
_chemical_formula_weight         524.64

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.6706(2)
_cell_length_b                   16.8421(7)
_cell_length_c                   14.3536(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.943(2)
_cell_angle_gamma                90.00
_cell_volume                     1357.69(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35437
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3371
_reflns_number_gt                2710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond Crystal Impact, 2010)'
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.9482P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     215
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1571
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.6920(2) 0.98338(8) 0.12651(9) 0.0254(3) Uani 1 1 d . A 1
O2 O -0.3941(3) 0.87076(8) 0.20108(9) 0.0308(3) Uani 1 1 d . B 1
H2 H -0.497(6) 0.9076(19) 0.181(2) 0.065(9) Uiso 1 1 d . C 1
O3 O -0.0169(3) 0.89656(9) -0.08189(10) 0.0314(3) Uani 1 1 d . B 1
H3 H -0.092(5) 0.9386(19) -0.096(2) 0.057(8) Uiso 1 1 d . D 1
N1 N 0.2111(4) 0.69320(12) 0.13794(14) 0.0199(4) Uani 0.80 1 d PD B 1
C1 C -0.5861(3) 0.99269(10) 0.05639(12) 0.0206(4) Uani 1 1 d . . 1
C2 C -0.3847(3) 0.95310(10) 0.02311(11) 0.0195(3) Uani 1 1 d . . 1
C3 C -0.2314(3) 0.88999(10) 0.05396(12) 0.0201(3) Uani 1 1 d . B 1
C4 C -0.2412(3) 0.84929(10) 0.14127(12) 0.0218(4) Uani 1 1 d . B 1
C5 C -0.0952(3) 0.78670(11) 0.16967(13) 0.0256(4) Uani 1 1 d . B 1
H5 H -0.1042 0.7627 0.2289 0.031 Uiso 1 1 calc R B 1
C6 C 0.0694(3) 0.75698(11) 0.11231(14) 0.0276(4) Uani 0.80 1 d P B 1
C7 C 0.0869(3) 0.79783(11) 0.02727(13) 0.0280(4) Uani 1 1 d . B 1
H7 H 0.1993 0.7803 -0.0116 0.034 Uiso 1 1 calc R B 1
C8 C -0.0543(3) 0.86209(11) -0.00043(12) 0.0230(4) Uani 1 1 d . B 1
C9 C 0.3946(4) 0.67001(13) 0.08037(15) 0.0226(4) Uani 0.80 1 d PD B 1
H9A H 0.5172 0.6386 0.1201 0.027 Uiso 0.80 1 calc PR B 1
H9B H 0.4726 0.7188 0.0612 0.027 Uiso 0.80 1 calc PR B 1
C10 C 0.3079(5) 0.62178(14) -0.00823(18) 0.0303(5) Uani 0.80 1 d PD B 1
H10A H 0.2369 0.5714 0.0100 0.036 Uiso 0.80 1 calc PR B 1
H10B H 0.1827 0.6520 -0.0482 0.036 Uiso 0.80 1 calc PR B 1
C11 C 0.5096(8) 0.6035(2) -0.0641(2) 0.0426(9) Uani 0.80 1 d PD B 1
H11A H 0.5821 0.6533 -0.0813 0.064 Uiso 0.80 1 calc PR B 1
H11B H 0.4473 0.5744 -0.1213 0.064 Uiso 0.80 1 calc PR B 1
H11C H 0.6299 0.5712 -0.0258 0.064 Uiso 0.80 1 calc PR B 1
C12 C 0.4320(5) 0.68238(19) 0.29850(19) 0.0327(6) Uani 0.80 1 d PD B 1
H12A H 0.5792 0.6628 0.2779 0.049 Uiso 0.80 1 calc PR B 1
H12B H 0.4206 0.6624 0.3618 0.049 Uiso 0.80 1 calc PR B 1
H12C H 0.4335 0.7406 0.2993 0.049 Uiso 0.80 1 calc PR B 1
C13 C 0.2192(4) 0.65338(14) 0.23086(17) 0.0277(5) Uani 0.80 1 d PD B 1
H13 H 0.0725 0.6695 0.2576 0.033 Uiso 0.80 1 calc PR B 1
C14 C 0.2163(5) 0.56325(15) 0.22312(19) 0.0344(6) Uani 0.80 1 d PD B 1
H14A H 0.2465 0.5402 0.2871 0.041 Uiso 0.80 1 calc PR B 1
H14B H 0.3471 0.5462 0.1886 0.041 Uiso 0.80 1 calc PR B 1
C15 C -0.0198(6) 0.53066(19) 0.1727(2) 0.0373(7) Uani 0.80 1 d PD B 1
H15A H -0.1476 0.5422 0.2102 0.056 Uiso 0.80 1 calc PR B 1
H15B H -0.0067 0.4731 0.1649 0.056 Uiso 0.80 1 calc PR B 1
H15C H -0.0560 0.5558 0.1108 0.056 Uiso 0.80 1 calc PR B 1
C6A C 0.0694(3) 0.75698(11) 0.11231(14) 0.0276(4) Uani 0.20 1 d P E 2
N1A N 0.1359(19) 0.6742(7) 0.1118(7) 0.036(3) Uiso 0.20 1 d PD E 2
C9A C 0.248(3) 0.6352(11) 0.0375(11) 0.081(5) Uiso 0.20 1 d PD E 2
H9C H 0.1474 0.6436 -0.0239 0.097 Uiso 0.20 1 calc PR E 2
H9D H 0.2566 0.5773 0.0496 0.097 Uiso 0.20 1 calc PR E 2
C10A C 0.498(3) 0.6672(14) 0.0325(16) 0.114(8) Uiso 0.20 1 d PD E 2
H10C H 0.4948 0.7253 0.0219 0.137 Uiso 0.20 1 calc PR E 2
H10D H 0.6059 0.6555 0.0912 0.137 Uiso 0.20 1 calc PR E 2
C11A C 0.577(4) 0.6238(13) -0.0505(15) 0.065(7) Uiso 0.20 1 d PD E 2
H11D H 0.7372 0.6415 -0.0593 0.097 Uiso 0.20 1 calc PR E 2
H11E H 0.4659 0.6354 -0.1074 0.097 Uiso 0.20 1 calc PR E 2
H11F H 0.5790 0.5665 -0.0385 0.097 Uiso 0.20 1 calc PR E 2
C12A C 0.072(3) 0.5439(6) 0.1768(10) 0.038(3) Uiso 0.20 1 d PD E 2
H12D H -0.0738 0.5425 0.1311 0.056 Uiso 0.20 1 calc PR E 2
H12E H 0.0461 0.5139 0.2331 0.056 Uiso 0.20 1 calc PR E 2
H12F H 0.2030 0.5200 0.1488 0.056 Uiso 0.20 1 calc PR E 2
C13A C 0.1326(17) 0.6294(5) 0.2037(7) 0.030(2) Uiso 0.20 1 d PD E 2
H13A H -0.0004 0.6514 0.2349 0.036 Uiso 0.20 1 calc PR E 2
C14A C 0.3582(17) 0.6317(6) 0.2749(7) 0.036(2) Uiso 0.20 1 d PD E 2
H14C H 0.4909 0.6105 0.2441 0.043 Uiso 0.20 1 calc PR E 2
H14D H 0.3363 0.5953 0.3272 0.043 Uiso 0.20 1 calc PR E 2
C15A C 0.433(3) 0.7131(7) 0.3171(11) 0.047(4) Uiso 0.20 1 d PD E 2
H15D H 0.5802 0.7074 0.3613 0.071 Uiso 0.20 1 calc PR E 2
H15E H 0.3069 0.7341 0.3503 0.071 Uiso 0.20 1 calc PR E 2
H15F H 0.4604 0.7497 0.2666 0.071 Uiso 0.20 1 calc PR E 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0275(6) 0.0269(7) 0.0234(6) 0.0015(5) 0.0097(5) 0.0058(5)
O2 0.0378(8) 0.0314(7) 0.0265(7) 0.0052(6) 0.0158(6) 0.0150(6)
O3 0.0357(8) 0.0332(7) 0.0289(7) 0.0098(6) 0.0170(6) 0.0146(6)
N1 0.0232(10) 0.0190(9) 0.0187(9) -0.0012(8) 0.0070(8) 0.0050(8)
C1 0.0200(8) 0.0196(8) 0.0222(8) -0.0043(6) 0.0030(6) 0.0002(6)
C2 0.0195(8) 0.0199(8) 0.0192(8) -0.0048(6) 0.0034(6) -0.0012(6)
C3 0.0202(8) 0.0198(8) 0.0205(8) -0.0029(6) 0.0042(6) 0.0013(6)
C4 0.0225(8) 0.0212(8) 0.0229(8) -0.0027(7) 0.0073(7) 0.0009(6)
C5 0.0297(9) 0.0233(9) 0.0256(9) 0.0034(7) 0.0108(7) 0.0054(7)
C6 0.0300(9) 0.0245(9) 0.0300(10) 0.0023(7) 0.0103(8) 0.0071(7)
C7 0.0293(9) 0.0283(9) 0.0292(10) 0.0007(7) 0.0139(8) 0.0082(7)
C8 0.0240(9) 0.0237(8) 0.0221(8) 0.0005(7) 0.0065(7) 0.0022(7)
C9 0.0243(10) 0.0239(10) 0.0221(10) 0.0032(8) 0.0117(8) 0.0104(9)
C10 0.0415(14) 0.0219(11) 0.0309(13) -0.0043(9) 0.0165(11) 0.0082(10)
C11 0.061(2) 0.0372(18) 0.0341(16) -0.0014(14) 0.0240(17) 0.0176(19)
C12 0.0394(15) 0.0372(17) 0.0215(12) 0.0006(12) 0.0039(10) 0.0027(13)
C13 0.0301(13) 0.0274(12) 0.0269(12) 0.0051(10) 0.0087(10) 0.0067(10)
C14 0.0396(14) 0.0291(12) 0.0364(14) 0.0049(11) 0.0116(12) 0.0081(11)
C15 0.0316(16) 0.0377(15) 0.0424(17) -0.0027(12) 0.0040(13) -0.0034(13)
C6A 0.0300(9) 0.0245(9) 0.0300(10) 0.0023(7) 0.0103(8) 0.0071(7)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.251(2) . ?
O2 C4 1.351(2) . ?
O3 C8 1.348(2) . ?
N1 C6 1.361(3) . ?
N1 C9 1.468(2) . ?
N1 C13 1.488(3) . ?
C1 C2 1.453(2) 3_475 ?
C1 C2 1.459(2) . ?
C1 C1 2.018(3) 3_475 ?
C2 C3 1.405(2) . ?
C2 C1 1.453(2) 3_475 ?
C3 C8 1.434(2) . ?
C3 C4 1.436(2) . ?
C4 C5 1.367(2) . ?
C5 C6 1.418(2) . ?
C6 C7 1.417(3) . ?
C7 C8 1.372(3) . ?
C9 C10 1.532(3) . ?
C10 C11 1.516(4) . ?
C12 C13 1.521(4) . ?
C13 C14 1.522(3) . ?
C14 C15 1.533(4) . ?
N1A C9A 1.469(3) . ?
N1A C13A 1.522(14) . ?
C9A C10A 1.531(4) . ?
C10A C11A 1.517(4) . ?
C12A C13A 1.520(4) . ?
C13A C14A 1.523(4) . ?
C14A C15A 1.534(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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C9 119.71(17) . . ?
C6 N1 C13 122.80(17) . . ?
C9 N1 C13 116.62(17) . . ?
O1 C1 C2 134.06(16) . 3_475 ?
O1 C1 C2 133.68(16) . . ?
C2 C1 C2 92.27(14) 3_475 . ?
O1 C1 C1 179.7(2) . 3_475 ?
C2 C1 C1 46.25(10) 3_475 3_475 ?
C2 C1 C1 46.02(9) . 3_475 ?
C3 C2 C1 136.15(16) . 3_475 ?
C3 C2 C1 136.11(16) . . ?
C1 C2 C1 87.73(14) 3_475 . ?
C2 C3 C8 121.71(15) . . ?
C2 C3 C4 122.62(15) . . ?
C8 C3 C4 115.67(15) . . ?
O2 C4 C5 115.61(16) . . ?
O2 C4 C3 122.16(15) . . ?
C5 C4 C3 122.23(15) . . ?
C4 C5 C6 121.26(17) . . ?
N1 C6 C7 120.46(17) . . ?
N1 C6 C5 122.20(17) . . ?
C7 C6 C5 117.32(16) . . ?
C8 C7 C6 121.68(16) . . ?
O3 C8 C7 115.83(16) . . ?
O3 C8 C3 122.48(16) . . ?
C7 C8 C3 121.69(16) . . ?
N1 C9 C10 115.9(2) . . ?
C11 C10 C9 111.6(3) . . ?
N1 C13 C12 110.5(2) . . ?
N1 C13 C14 112.7(2) . . ?
C12 C13 C14 111.5(2) . . ?
C13 C14 C15 113.0(2) . . ?
C9A N1A C13A 117.8(11) . . ?
N1A C9A C10A 111.8(13) . . ?
C11A C10A C9A 104.1(15) . . ?
C12A C13A N1A 106.2(9) . . ?
C12A C13A C14A 109.6(9) . . ?
N1A C13A C14A 117.3(9) . . ?
C13A C14A C15A 116.7(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.5(3) . . . . ?
C2 C1 C2 C3 -179.6(2) 3_475 . . . ?
C1 C1 C2 C3 -179.6(2) 3_475 . . . ?
O1 C1 C2 C1 -179.9(3) . . . 3_475 ?
C2 C1 C2 C1 0.0 3_475 . . 3_475 ?
C1 C2 C3 C8 -3.4(3) 3_475 . . . ?
C1 C2 C3 C8 176.04(18) . . . . ?
C1 C2 C3 C4 176.70(18) 3_475 . . . ?
C1 C2 C3 C4 -3.9(3) . . . . ?
C2 C3 C4 O2 -2.1(3) . . . . ?
C8 C3 C4 O2 177.90(16) . . . . ?
C2 C3 C4 C5 178.38(17) . . . . ?
C8 C3 C4 C5 -1.6(3) . . . . ?
O2 C4 C5 C6 178.42(17) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C9 N1 C6 C7 4.3(3) . . . . ?
C13 N1 C6 C7 173.3(2) . . . . ?
C9 N1 C6 C5 -173.9(2) . . . . ?
C13 N1 C6 C5 -4.9(4) . . . . ?
C4 C5 C6 N1 -177.9(2) . . . . ?
C4 C5 C6 C7 3.9(3) . . . . ?
N1 C6 C7 C8 179.8(2) . . . . ?
C5 C6 C7 C8 -2.0(3) . . . . ?
C6 C7 C8 O3 178.79(18) . . . . ?
C6 C7 C8 C3 -1.7(3) . . . . ?
C2 C3 C8 O3 3.0(3) . . . . ?
C4 C3 C8 O3 -177.09(16) . . . . ?
C2 C3 C8 C7 -176.50(17) . . . . ?
C4 C3 C8 C7 3.4(3) . . . . ?
C6 N1 C9 C10 -80.3(3) . . . . ?
C13 N1 C9 C10 110.1(2) . . . . ?
N1 C9 C10 C11 178.0(2) . . . . ?
C6 N1 C13 C12 -98.5(3) . . . . ?
C9 N1 C13 C12 70.9(3) . . . . ?
C6 N1 C13 C14 136.1(2) . . . . ?
C9 N1 C13 C14 -54.6(3) . . . . ?
N1 C13 C14 C15 -67.2(3) . . . . ?
C12 C13 C14 C15 167.9(2) . . . . ?
C13A N1A C9A C10A -101.6(18) . . . . ?
N1A C9A C10A C11A -176.9(17) . . . . ?
C9A N1A C13A C12A -41.8(14) . . . . ?
C9A N1A C13A C14A 81.1(13) . . . . ?
C12A C13A C14A C15A -174.4(11) . . . . ?
N1A C13A C14A C15A 64.4(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.051

_database_code_depnum_ccdc_archive 'CCDC 947470'