#------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/12/4001223.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_4001223
loop_
_publ_author_name
'Beverina, Luca'
'Crippa, Maurizio'
'Salice, Patrizio'
'Ruffo, Riccardo'
'Ferrante, Camilla'
'Fortunati, Ilaria'
'Signorini, Raffaella'
'Mari, Claudio Maria'
'Bozio, Renato'
'Facchetti, Antonio'
'Pagani, Giorgio A.'
_publ_section_title
;
 Indolic Squaraines as Two-Photon Absorbing Dyes in the Visible Region:
 X-ray Structure, Electrochemical, and Nonlinear Optical Characterization
;
_journal_issue                   10
_journal_name_full               'Chemistry of Materials'
_journal_page_first              3242
_journal_paper_doi               10.1021/cm800714k
_journal_volume                  20
_journal_year                    2008
_chemical_formula_sum            'C36 H44 N2 O2'
_chemical_formula_weight         536.73
_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                95.784(6)
_cell_angle_beta                 97.426(6)
_cell_angle_gamma                111.029(6)
_cell_formula_units_Z            1
_cell_length_a                   7.9237(19)
_cell_length_b                   8.468(2)
_cell_length_c                   12.089(3)
_cell_measurement_reflns_used    1971
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.66
_cell_measurement_theta_min      2.61
_cell_volume                     741.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'CCD SMART-1000 area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3817
_diffrn_reflns_theta_full        28.77
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.514034
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'twinabs, Bruker'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0870
_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)+(0.0511P)²+1.7722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2052
_refine_ls_wR_factor_ref         0.2167
_reflns_number_gt                2772
_reflns_number_total             3817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cm800714k-file002.cif
_cod_data_source_block           s79vm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'const' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4001223
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
O1 O 1.4244(4) 1.2177(4) 1.0137(3) 0.0321(8) Uani 1 1 d .
N1 N 0.8831(5) 1.2587(4) 0.8604(3) 0.0232(8) Uani 1 1 d .
C1 C 1.0471(6) 1.2646(5) 0.9078(3) 0.0241(9) Uani 1 1 d .
H1 H 1.0700 1.1694 0.9316 0.029 Uiso 1 1 calc R
C2 C 1.1814(6) 1.4296(5) 0.9179(3) 0.0222(9) Uani 1 1 d .
C3 C 1.0832(5) 1.5324(5) 0.8716(3) 0.0199(8) Uani 1 1 d .
C4 C 1.1364(6) 1.7054(5) 0.8616(3) 0.0251(9) Uani 1 1 d .
H4 H 1.2594 1.7833 0.8878 0.030 Uiso 1 1 calc R
C5 C 1.0034(6) 1.7592(6) 0.8122(4) 0.0308(11) Uani 1 1 d .
H5 H 1.0365 1.8764 0.8042 0.037 Uiso 1 1 calc R
C6 C 0.8226(6) 1.6468(6) 0.7739(4) 0.0313(11) Uani 1 1 d .
H6 H 0.7361 1.6885 0.7389 0.038 Uiso 1 1 calc R
C7 C 0.7662(6) 1.4763(5) 0.7856(3) 0.0247(9) Uani 1 1 d .
H7 H 0.6425 1.3994 0.7607 0.030 Uiso 1 1 calc R
C8 C 0.9000(6) 1.4232(5) 0.8357(4) 0.0246(9) Uani 1 1 d .
C9 C 1.3645(5) 1.4736(5) 0.9648(3) 0.0207(9) Uani 1 1 d .
C10 C 1.4653(6) 1.3702(5) 1.0067(4) 0.0264(9) Uani 1 1 d .
C11 C 0.7099(6) 1.1086(5) 0.8395(4) 0.0268(10) Uani 1 1 d .
H11A H 0.6107 1.1446 0.8601 0.032 Uiso 1 1 calc R
H11B H 0.7224 1.0249 0.8883 0.032 Uiso 1 1 calc R
C12 C 0.6570(6) 1.0227(5) 0.7167(4) 0.0241(9) Uani 1 1 d .
H12A H 0.7561 0.9869 0.6957 0.029 Uiso 1 1 calc R
H12B H 0.6431 1.1058 0.6677 0.029 Uiso 1 1 calc R
C13 C 0.4772(6) 0.8664(5) 0.6972(4) 0.0251(9) Uani 1 1 d .
H13A H 0.4896 0.7873 0.7499 0.030 Uiso 1 1 calc R
H13B H 0.3776 0.9039 0.7149 0.030 Uiso 1 1 calc R
C14 C 0.4244(6) 0.7714(5) 0.5783(4) 0.0311(10) Uani 1 1 d .
H14A H 0.5317 0.7504 0.5567 0.037 Uiso 1 1 calc R
H14B H 0.3935 0.8449 0.5270 0.037 Uiso 1 1 calc R
C15 C 0.2609(6) 0.5992(5) 0.5611(4) 0.0324(11) Uani 1 1 d .
H15A H 0.1591 0.6175 0.5929 0.039 Uiso 1 1 calc R
H15B H 0.2175 0.5580 0.4790 0.039 Uiso 1 1 calc R
C16 C 0.3063(6) 0.4605(5) 0.6160(4) 0.0295(10) Uani 1 1 d .
H16A H 0.4131 0.4471 0.5879 0.035 Uiso 1 1 calc R
H16B H 0.3416 0.4981 0.6987 0.035 Uiso 1 1 calc R
C17 C 0.1465(7) 0.2876(6) 0.5918(4) 0.0372(11) Uani 1 1 d .
H17A H 0.1047 0.2540 0.5091 0.045 Uiso 1 1 calc R
H17B H 0.0429 0.2987 0.6253 0.045 Uiso 1 1 calc R
C18 C 0.1977(7) 0.1468(6) 0.6392(4) 0.0426(13) Uani 1 1 d .
H18A H 0.3011 0.1360 0.6069 0.064 Uiso 1 1 calc R
H18B H 0.0920 0.0377 0.6194 0.064 Uiso 1 1 calc R
H18C H 0.2328 0.1764 0.7216 0.064 Uiso 1 1 calc R
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'
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_3
C1 N1 C8 109.1(3) .
C1 N1 C11 126.2(3) .
C8 N1 C11 124.7(3) .
N1 C1 C2 111.1(3) .
N1 C1 H1 124.5 .
C2 C1 H1 124.5 .
C9 C2 C1 123.8(3) .
C9 C2 C3 131.2(4) .
C1 C2 C3 105.1(4) .
C8 C3 C4 119.5(4) .
C8 C3 C2 107.1(3) .
C4 C3 C2 133.4(4) .
C5 C4 C3 117.5(4) .
C5 C4 H4 121.3 .
C3 C4 H4 121.3 .
C4 C5 C6 121.9(4) .
C4 C5 H5 119.0 .
C6 C5 H5 119.0 .
C7 C6 C5 121.5(4) .
C7 C6 H6 119.3 .
C5 C6 H6 119.3 .
C6 C7 C8 116.4(4) .
C6 C7 H7 121.8 .
C8 C7 H7 121.8 .
C7 C8 C3 123.1(4) .
C7 C8 N1 129.2(4) .
C3 C8 N1 107.7(3) .
C2 C9 C10 131.5(4) .
C2 C9 C10 137.9(4) 2_887
C10 C9 C10 90.6(3) 2_887
O1 C10 C9 134.8(4) .
O1 C10 C9 135.8(4) 2_887
C9 C10 C9 89.4(3) 2_887
N1 C11 C12 112.1(3) .
N1 C11 H11A 109.2 .
C12 C11 H11A 109.2 .
N1 C11 H11B 109.2 .
C12 C11 H11B 109.2 .
H11A C11 H11B 107.9 .
C11 C12 C13 111.2(3) .
C11 C12 H12A 109.4 .
C13 C12 H12A 109.4 .
C11 C12 H12B 109.4 .
C13 C12 H12B 109.4 .
H12A C12 H12B 108.0 .
C14 C13 C12 113.1(4) .
C14 C13 H13A 108.9 .
C12 C13 H13A 108.9 .
C14 C13 H13B 108.9 .
C12 C13 H13B 108.9 .
H13A C13 H13B 107.8 .
C13 C14 C15 114.1(4) .
C13 C14 H14A 108.7 .
C15 C14 H14A 108.7 .
C13 C14 H14B 108.7 .
C15 C14 H14B 108.7 .
H14A C14 H14B 107.6 .
C16 C15 C14 113.6(4) .
C16 C15 H15A 108.8 .
C14 C15 H15A 108.8 .
C16 C15 H15B 108.8 .
C14 C15 H15B 108.8 .
H15A C15 H15B 107.7 .
C17 C16 C15 113.0(4) .
C17 C16 H16A 109.0 .
C15 C16 H16A 109.0 .
C17 C16 H16B 109.0 .
C15 C16 H16B 109.0 .
H16A C16 H16B 107.8 .
C16 C17 C18 112.6(4) .
C16 C17 H17A 109.1 .
C18 C17 H17A 109.1 .
C16 C17 H17B 109.1 .
C18 C17 H17B 109.1 .
H17A C17 H17B 107.8 .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.228(5) .
N1 C1 1.333(5) .
N1 C8 1.416(5) .
N1 C11 1.468(5) .
C1 C2 1.401(6) .
C1 H1 0.9500 .
C2 C9 1.386(6) .
C2 C3 1.466(5) .
C3 C8 1.394(6) .
C3 C4 1.394(6) .
C4 C5 1.383(6) .
C4 H4 0.9500 .
C5 C6 1.390(6) .
C5 H5 0.9500 .
C6 C7 1.378(6) .
C6 H6 0.9500 .
C7 C8 1.387(5) .
C7 H7 0.9500 .
C9 C10 1.466(5) .
C9 C10 1.481(6) 2_887
C10 C9 1.481(6) 2_887
C11 C12 1.520(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.528(6) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.502(6) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.536(6) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.532(6) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.523(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.530(6) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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_4
C8 N1 C1 C2 0.1(5) . .
C11 N1 C1 C2 -178.2(4) . .
N1 C1 C2 C9 179.7(4) . .
N1 C1 C2 C3 0.5(5) . .
C9 C2 C3 C8 -180.0(4) . .
C1 C2 C3 C8 -0.9(4) . .
C9 C2 C3 C4 -2.2(8) . .
C1 C2 C3 C4 177.0(4) . .
C8 C3 C4 C5 -2.3(6) . .
C2 C3 C4 C5 -179.8(4) . .
C3 C4 C5 C6 0.3(6) . .
C4 C5 C6 C7 1.4(7) . .
C5 C6 C7 C8 -1.0(7) . .
C6 C7 C8 C3 -1.0(6) . .
C6 C7 C8 N1 178.9(4) . .
C4 C3 C8 C7 2.7(6) . .
C2 C3 C8 C7 -179.1(4) . .
C4 C3 C8 N1 -177.2(4) . .
C2 C3 C8 N1 0.9(4) . .
C1 N1 C8 C7 179.4(4) . .
C11 N1 C8 C7 -2.3(7) . .
C1 N1 C8 C3 -0.6(5) . .
C11 N1 C8 C3 177.6(4) . .
C1 C2 C9 C10 4.1(7) . .
C3 C2 C9 C10 -176.9(4) . .
C1 C2 C9 C10 -176.1(5) . 2_887
C3 C2 C9 C10 2.9(8) . 2_887
C2 C9 C10 O1 0.5(8) . .
C10 C9 C10 O1 -179.3(7) 2_887 .
C2 C9 C10 C9 179.8(5) . 2_887
C10 C9 C10 C9 0.001(1) 2_887 2_887
C1 N1 C11 C12 -101.6(5) . .
C8 N1 C11 C12 80.4(5) . .
N1 C11 C12 C13 179.6(3) . .
C11 C12 C13 C14 -176.9(4) . .
C12 C13 C14 C15 171.2(4) . .
C13 C14 C15 C16 -71.1(5) . .
C14 C15 C16 C17 -176.3(4) . .
C15 C16 C17 C18 175.6(4) . .
