#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:04:46 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180372 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/41/7204148.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_7204148
loop_
_publ_author_name
'Kay, A. J.'
'Woolhouse, A. D.'
'Gainsford, G. J.'
'Haskell, T. G.'
'Wyss, C. P.'
'Giffin, S. M.'
'McKinnie, I. T.'
'Barnes, T. H.'
_publ_section_title
;
 Simple zwitterionic merocyanines as potential NLO chromophores
;
_journal_issue                   9
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2271
_journal_paper_doi               10.1039/b103148c
_journal_volume                  11
_journal_year                    2001
_chemical_formula_sum            'C17 H16 N2 O4'
_chemical_formula_weight         312.32
_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                118.308(4)
_cell_angle_beta                 106.121(4)
_cell_angle_gamma                94.752(4)
_cell_formula_units_Z            2
_cell_length_a                   7.987(2)
_cell_length_b                   10.300(3)
_cell_length_c                   10.806(3)
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      23.65
_cell_measurement_theta_min      2.27
_cell_volume                     727.3(3)
_computing_cell_refinement       'Bruker SMART (Siemens, 1996)'
_computing_data_collection       'Bruker SMART (Siemens, 1996)'
_computing_data_reduction
;
Bruker SAINT (Siemens, 1996) & SADABS (Sheldrick, 1996)
;
_computing_molecular_graphics
;
ORTEP in WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      158(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8989
_diffrn_reflns_theta_full        26.34
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Blessing, Acta Cryst. (1995) A57, 33-38.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0392
_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)+(0.0685P)²+0.0946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                2490
_reflns_number_total             2897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103148c.txt
_cod_data_source_block           wffb
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        727.3(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204148
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25988(16) 0.57479(13) 1.54128(12) 0.0539(3) Uani 1 1 d . . .
H1 H 0.279(3) 0.570(2) 1.620(2) 0.065 Uiso 1 1 d . . .
O2 O 0.57027(16) 0.89004(12) 1.58879(13) 0.0512(3) Uani 1 1 d . . .
H2 H 0.616(3) 0.856(2) 1.521(2) 0.061 Uiso 1 1 d . . .
O3 O 0.32766(13) 0.56722(10) 0.80035(10) 0.0387(3) Uani 1 1 d . A .
O13 O 0.27749(13) 0.31197(10) 0.64991(10) 0.0354(2) Uani 1 1 d . A .
N1 N 0.22183(14) 0.67494(12) 1.30292(11) 0.0298(3) Uani 1 1 d . A .
N2 N 0.23771(15) 0.17622(12) 0.65622(12) 0.0330(3) Uani 1 1 d . A .
C3 C 0.2172(2) 0.77492(17) 1.45556(15) 0.0372(3) Uani 1 1 d . . .
H3A H 0.100(2) 0.7365(19) 1.4515(18) 0.045 Uiso 1 1 d . . .
H3B H 0.228(2) 0.8799(19) 1.4726(18) 0.045 Uiso 1 1 d . . .
C4 C 0.15598(17) 0.52143(14) 1.23113(14) 0.0304(3) Uani 1 1 d . . .
H4 H 0.1012 0.4803 1.2768 0.037 Uiso 1 1 calc R A .
C5 C 0.16706(17) 0.42517(13) 1.09448(13) 0.0280(3) Uani 1 1 d . A .
H5 H 0.1216 0.3183 1.0475 0.034 Uiso 1 1 calc R . .
C6 C 0.24560(15) 0.48273(13) 1.02186(13) 0.0242(3) Uani 1 1 d . . .
C7 C 0.30747(16) 0.64389(14) 1.09864(14) 0.0291(3) Uani 1 1 d . A .
H7 H 0.3577 0.6889 1.0537 0.035 Uiso 1 1 calc R . .
C8 C 0.29576(17) 0.73526(14) 1.23653(14) 0.0319(3) Uani 1 1 d . . .
H8 H 0.3401 0.8426 1.2866 0.038 Uiso 1 1 calc R A .
C11 C 0.25792(16) 0.38612(13) 0.87753(13) 0.0253(3) Uani 1 1 d . A .
C12 C 0.22556(16) 0.22344(13) 0.78921(13) 0.0261(3) Uani 1 1 d . . .
C14 C 0.29285(17) 0.43917(14) 0.78490(13) 0.0292(3) Uani 1 1 d . . .
C15 C 0.18952(16) 0.10395(13) 0.82632(13) 0.0267(3) Uani 1 1 d . A .
C16 C 0.30317(17) 0.11584(14) 0.95826(14) 0.0309(3) Uani 1 1 d . . .
H16 H 0.4008 0.2034 1.0282 0.037 Uiso 1 1 calc R A .
C17 C 0.27265(19) -0.00122(16) 0.98656(16) 0.0363(3) Uani 1 1 d . A .
H17 H 0.3489 0.0074 1.0764 0.044 Uiso 1 1 calc R . .
C18 C 0.13085(19) -0.13065(15) 0.88351(17) 0.0389(3) Uani 1 1 d . . .
H18 H 0.1117 -0.2106 0.9027 0.047 Uiso 1 1 calc R A .
C19 C 0.01746(19) -0.14314(15) 0.75284(16) 0.0388(3) Uani 1 1 d . A .
H19 H -0.0793 -0.2314 0.6829 0.047 Uiso 1 1 calc R . .
C20 C 0.04576(17) -0.02582(14) 0.72421(14) 0.0321(3) Uani 1 1 d . . .
H20 H -0.0327 -0.0341 0.6353 0.039 Uiso 1 1 calc R A .
C1A C 0.4297(4) 0.6598(3) 1.5660(3) 0.0383(9) Uani 0.535(5) 1 d P A 1
H1AA H 0.4701 0.6028 1.4808 0.046 Uiso 0.535(5) 1 calc PR A 1
H1AB H 0.5227 0.6801 1.6600 0.046 Uiso 0.535(5) 1 calc PR A 1
C2A C 0.3980(4) 0.8077(4) 1.5784(3) 0.0331(8) Uani 0.535(5) 1 d P A 1
H2A H 0.3840 0.8695 1.6777 0.040 Uiso 0.535(5) 1 calc PR A 1
C1B C 0.5179(4) 0.7448(3) 1.5785(3) 0.0317(9) Uani 0.465(5) 1 d P A 2
H1BA H 0.5972 0.7447 1.6669 0.038 Uiso 0.465(5) 1 calc PR A 2
H1BB H 0.5232 0.6589 1.4856 0.038 Uiso 0.465(5) 1 calc PR A 2
C2B C 0.3257(4) 0.7339(4) 1.5751(3) 0.0279(9) Uani 0.465(5) 1 d P A 2
H2B H 0.3269 0.8095 1.6771 0.034 Uiso 0.465(5) 1 calc PR A 2
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1 C2B 46.62(16) . . ?
C1A O1 H1 103.8(14) . . ?
C2B O1 H1 112.8(14) . . ?
C1B O2 C2A 47.72(15) . . ?
C1B O2 H2 96.0(13) . . ?
C2A O2 H2 124.5(13) . . ?
C14 O13 N2 109.59(9) . . ?
C8 N1 C4 119.81(11) . . ?
C8 N1 C3 120.55(11) . . ?
C4 N1 C3 119.61(11) . . ?
C12 N2 O13 105.73(10) . . ?
N1 C3 C2A 110.37(13) . . ?
N1 C3 C2B 112.36(13) . . ?
C2A C3 C2B 33.06(13) . . ?
N1 C3 H3A 105.8(10) . . ?
C2A C3 H3A 124.7(10) . . ?
C2B C3 H3A 94.6(10) . . ?
N1 C3 H3B 107.1(9) . . ?
C2A C3 H3B 97.9(10) . . ?
C2B C3 H3B 125.1(10) . . ?
H3A C3 H3B 109.8(14) . . ?
N1 C4 C5 121.30(11) . . ?
N1 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 120.89(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 115.89(11) . . ?
C5 C6 C11 122.80(11) . . ?
C7 C6 C11 121.29(11) . . ?
C8 C7 C6 120.94(12) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 C8 C7 121.13(11) . . ?
N1 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C14 C11 C6 124.01(11) . . ?
C14 C11 C12 104.97(10) . . ?
C6 C11 C12 130.82(11) . . ?
N2 C12 C11 112.56(11) . . ?
N2 C12 C15 116.55(10) . . ?
C11 C12 C15 130.83(11) . . ?
O3 C14 O13 118.68(11) . . ?
O3 C14 C11 134.19(11) . . ?
O13 C14 C11 107.11(11) . . ?
C20 C15 C16 119.43(11) . . ?
C20 C15 C12 119.58(11) . . ?
C16 C15 C12 120.91(11) . . ?
C17 C16 C15 119.92(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.26(13) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.18(13) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.99(12) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.22(12) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O1 C1A C2A 105.9(2) . . ?
O1 C1A H1AA 110.6 . . ?
C2A C1A H1AA 110.6 . . ?
O1 C1A H1AB 110.6 . . ?
C2A C1A H1AB 110.6 . . ?
H1AA C1A H1AB 108.7 . . ?
O2 C2A C1A 106.0(2) . . ?
O2 C2A C3 120.5(2) . . ?
C1A C2A C3 109.7(2) . . ?
O2 C2A H2A 106.6 . . ?
C1A C2A H2A 106.6 . . ?
C3 C2A H2A 106.6 . . ?
O2 C1B C2B 104.0(2) . . ?
O2 C1B H1BA 111.0 . . ?
C2B C1B H1BA 111.0 . . ?
O2 C1B H1BB 111.0 . . ?
C2B C1B H1BB 111.0 . . ?
H1BA C1B H1BB 109.0 . . ?
O1 C2B C1B 104.7(2) . . ?
O1 C2B C3 116.4(2) . . ?
C1B C2B C3 108.1(2) . . ?
O1 C2B H2B 109.1 . . ?
C1B C2B H2B 109.1 . . ?
C3 C2B H2B 109.1 . . ?
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 C1A 1.435(3) . ?
O1 C2B 1.510(4) . ?
O1 H1 0.85(2) . ?
O2 C1B 1.462(3) . ?
O2 C2A 1.502(4) . ?
O2 H2 0.85(2) . ?
O3 C14 1.2447(16) . ?
O13 C14 1.3859(15) . ?
O13 N2 1.4454(14) . ?
N1 C8 1.3589(17) . ?
N1 C4 1.3605(17) . ?
N1 C3 1.4872(16) . ?
N2 C12 1.3167(16) . ?
C3 C2A 1.546(3) . ?
C3 C2B 1.598(3) . ?
C3 H3A 0.965(18) . ?
C3 H3B 0.999(17) . ?
C4 C5 1.3674(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4191(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4207(17) . ?
C6 C11 1.4359(17) . ?
C7 C8 1.3698(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C14 1.4237(17) . ?
C11 C12 1.4352(17) . ?
C12 C15 1.4940(17) . ?
C15 C20 1.4021(18) . ?
C15 C16 1.4032(18) . ?
C16 C17 1.3962(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3983(19) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C1A C2A 1.514(5) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C2A H2A 1.0000 . ?
C1B C2B 1.519(5) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B H2B 1.0000 . ?
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
C14 O13 N2 C12 1.65(13) . . . . ?
C8 N1 C3 C2A -83.7(2) . . . . ?
C4 N1 C3 C2A 94.45(19) . . . . ?
C8 N1 C3 C2B -119.23(19) . . . . ?
C4 N1 C3 C2B 58.9(2) . . . . ?
C8 N1 C4 C5 1.88(18) . . . . ?
C3 N1 C4 C5 -176.30(11) . . . . ?
N1 C4 C5 C6 -0.92(19) . . . . ?
C4 C5 C6 C7 -1.01(18) . . . . ?
C4 C5 C6 C11 -179.15(11) . . . . ?
C5 C6 C7 C8 2.04(17) . . . . ?
C11 C6 C7 C8 -179.79(11) . . . . ?
C4 N1 C8 C7 -0.82(18) . . . . ?
C3 N1 C8 C7 177.34(11) . . . . ?
C6 C7 C8 N1 -1.18(19) . . . . ?
C5 C6 C11 C14 163.55(12) . . . . ?
C7 C6 C11 C14 -14.49(18) . . . . ?
C5 C6 C11 C12 -10.6(2) . . . . ?
C7 C6 C11 C12 171.37(12) . . . . ?
O13 N2 C12 C11 -0.98(13) . . . . ?
O13 N2 C12 C15 -178.42(10) . . . . ?
C14 C11 C12 N2 0.00(14) . . . . ?
C6 C11 C12 N2 174.97(12) . . . . ?
C14 C11 C12 C15 176.97(12) . . . . ?
C6 C11 C12 C15 -8.1(2) . . . . ?
N2 O13 C14 O3 179.76(11) . . . . ?
N2 O13 C14 C11 -1.66(13) . . . . ?
C6 C11 C14 O3 3.9(2) . . . . ?
C12 C11 C14 O3 179.30(14) . . . . ?
C6 C11 C14 O13 -174.37(10) . . . . ?
C12 C11 C14 O13 1.04(13) . . . . ?
N2 C12 C15 C20 -51.08(16) . . . . ?
C11 C12 C15 C20 132.05(13) . . . . ?
N2 C12 C15 C16 125.55(13) . . . . ?
C11 C12 C15 C16 -51.33(18) . . . . ?
C20 C15 C16 C17 0.14(18) . . . . ?
C12 C15 C16 C17 -176.49(11) . . . . ?
C15 C16 C17 C18 0.68(19) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C16 C15 C20 C19 -0.81(18) . . . . ?
C12 C15 C20 C19 175.87(11) . . . . ?
C2B O1 C1A C2A -5.64(17) . . . . ?
C1B O2 C2A C1A -1.66(18) . . . . ?
C1B O2 C2A C3 -126.8(3) . . . . ?
O1 C1A C2A O2 -174.50(15) . . . . ?
O1 C1A C2A C3 -42.9(3) . . . . ?
N1 C3 C2A O2 61.9(2) . . . . ?
C2B C3 C2A O2 161.9(4) . . . . ?
N1 C3 C2A C1A -61.5(3) . . . . ?
C2B C3 C2A C1A 38.5(3) . . . . ?
C2A O2 C1B C2B -1.23(17) . . . . ?
C1A O1 C2B C1B 3.19(18) . . . . ?
C1A O1 C2B C3 122.5(3) . . . . ?
O2 C1B C2B O1 171.88(16) . . . . ?
O2 C1B C2B C3 47.2(2) . . . . ?
N1 C3 C2B O1 -60.6(2) . . . . ?
C2A C3 C2B O1 -153.9(4) . . . . ?
N1 C3 C2B C1B 56.8(3) . . . . ?
C2A C3 C2B C1B -36.5(2) . . . . ?
