#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238040.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238040
loop_
_publ_author_name
'Smith, Graham'
'Lynch, Daniel E.'
_publ_section_title
;
 2-[(3,3-Dimethylindolin-2-ylidene)methyl]-4-[(3,3-dimethyl-3H-indol-1-ium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate
 chloroform disolvate
;
_journal_coeditor_code           SU2588
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o786
_journal_page_last               o787
_journal_paper_doi               10.1107/S1600536813010386
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C26 H24 N2 O2, 2C H Cl3'
_chemical_formula_moiety         'C26 H24 N2 O2, 2(C H Cl3)'
_chemical_formula_sum            'C28 H26 Cl6 N2 O2'
_chemical_formula_weight         635.21
_chemical_name_systematic
;2-[(3,3-Dimethylindolin-2-ylidene)methyl]-4-[(3,3-dimethyl-3H-indol-1-ium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate
chloroform disolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.561(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.4270(11)
_cell_length_b                   13.5433(5)
_cell_length_c                   11.4259(5)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      3.27
_cell_volume                     2978.5(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10054
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.8884
_exptl_absorpt_correction_T_min  0.7937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.495
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0438
_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)+(0.0470P)²+4.0361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2415
_reflns_number_total             2926
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2588.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2238040
_cod_database_fobs_code          2238040
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
O O1 0.00000 0.35895(15) 0.75000 0.0420(8) Uani . . 1.000
O O2 0.00000 0.02418(14) 0.75000 0.0330(7) Uani . . 1.000
N N1 0.08460(9) 0.01681(12) 0.60326(15) 0.0292(5) Uani . . 1.000
C C1 0.00000 0.2681(2) 0.75000 0.0308(9) Uani . . 1.000
C C2 0.03058(10) 0.19196(14) 0.69306(18) 0.0283(6) Uani . . 1.000
C C3 0.00000 0.1172(2) 0.75000 0.0273(8) Uani . . 1.000
C C4 0.07197(11) 0.19354(15) 0.61835(19) 0.0300(6) Uani . . 1.000
C C5 0.09788(10) 0.11037(14) 0.57941(18) 0.0272(6) Uani . . 1.000
C C6 0.14808(11) 0.10979(15) 0.50618(19) 0.0298(6) Uani . . 1.000
C C7 0.19200(12) -0.05112(17) 0.4256(2) 0.0364(7) Uani . . 1.000
C C8 0.18945(12) -0.15368(18) 0.4251(2) 0.0400(8) Uani . . 1.000
C C9 0.15195(12) -0.20386(17) 0.4872(2) 0.0390(7) Uani . . 1.000
C C10 0.11502(12) -0.15347(15) 0.55071(19) 0.0333(7) Uani . . 1.000
C C11 0.11792(11) -0.05144(15) 0.54957(18) 0.0278(6) Uani . . 1.000
C C12 0.15568(10) -0.00001(15) 0.48861(18) 0.0293(6) Uani . . 1.000
C C13 0.21729(12) 0.15545(17) 0.5872(2) 0.0397(7) Uani . . 1.000
C C14 0.11833(13) 0.16552(17) 0.3829(2) 0.0400(8) Uani . . 1.000
Cl Cl1 0.10014(5) 0.46856(7) 0.50703(7) 0.0756(3) Uani . . 1.000
Cl Cl2 0.09549(5) 0.60290(5) 0.70002(8) 0.0724(3) Uani . . 1.000
Cl Cl3 0.17949(4) 0.42725(6) 0.76203(7) 0.0650(3) Uani . . 1.000
C C15 0.10219(14) 0.47904(18) 0.6610(2) 0.0444(8) Uani . . 1.000
H H1 0.05820 0.00030 0.64720 0.0350 Uiso . R 1.000
H H4 0.08300 0.25470 0.59290 0.0360 Uiso calc R 1.000
H H7 0.21760 -0.01770 0.38450 0.0440 Uiso calc R 1.000
H H8 0.21330 -0.18910 0.38230 0.0480 Uiso calc R 1.000
H H9 0.15150 -0.27250 0.48640 0.0470 Uiso calc R 1.000
H H10 0.08950 -0.18680 0.59210 0.0400 Uiso calc R 1.000
H H131 0.23420 0.12070 0.66480 0.0600 Uiso calc R 1.000
H H132 0.21030 0.22370 0.60240 0.0600 Uiso calc R 1.000
H H133 0.25060 0.15050 0.54490 0.0600 Uiso calc R 1.000
H H141 0.15020 0.16100 0.33750 0.0600 Uiso calc R 1.000
H H142 0.11160 0.23360 0.39920 0.0600 Uiso calc R 1.000
H H143 0.07460 0.13680 0.33480 0.0600 Uiso calc R 1.000
H H15 0.06270 0.44250 0.66990 0.0530 Uiso calc R 1.000
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C11 . 111.84(18) no
C11 N1 H1 . 124.00 no
C5 N1 H1 . 124.00 no
C2 C1 C2 2_556 90.59(19) no
O1 C1 C2 2_556 134.70(11) no
O1 C1 C2 . 134.70(11) no
C1 C2 C3 . 88.88(16) no
C1 C2 C4 . 134.41(18) no
C3 C2 C4 . 136.70(18) no
O2 C3 C2 . 134.18(11) no
C2 C3 C2 2_556 91.64(19) no
O2 C3 C2 2_556 134.18(11) no
C2 C4 C5 . 124.33(19) no
N1 C5 C4 . 125.4(2) no
N1 C5 C6 . 108.97(17) no
C4 C5 C6 . 125.59(18) no
C5 C6 C12 . 101.26(16) no
C12 C6 C13 . 111.12(18) no
C12 C6 C14 . 112.84(17) no
C13 C6 C14 . 110.92(18) no
C5 C6 C13 . 108.62(17) no
C5 C6 C14 . 111.66(19) no
C8 C7 C12 . 118.5(2) no
C7 C8 C9 . 121.0(2) no
C8 C9 C10 . 121.2(2) no
C9 C10 C11 . 117.0(2) no
N1 C11 C12 . 108.72(17) no
C10 C11 C12 . 122.6(2) no
N1 C11 C10 . 128.7(2) no
C7 C12 C11 . 119.8(2) no
C6 C12 C7 . 131.1(2) no
C6 C12 C11 . 109.10(18) no
C2 C4 H4 . 118.00 no
C5 C4 H4 . 118.00 no
C8 C7 H7 . 121.00 no
C12 C7 H7 . 121.00 no
C7 C8 H8 . 119.00 no
C9 C8 H8 . 120.00 no
C8 C9 H9 . 119.00 no
C10 C9 H9 . 119.00 no
C9 C10 H10 . 122.00 no
C11 C10 H10 . 122.00 no
C6 C13 H131 . 109.00 no
C6 C13 H132 . 110.00 no
C6 C13 H133 . 109.00 no
H131 C13 H132 . 110.00 no
H131 C13 H133 . 110.00 no
H132 C13 H133 . 109.00 no
C6 C14 H141 . 109.00 no
C6 C14 H142 . 109.00 no
C6 C14 H143 . 109.00 no
H141 C14 H142 . 109.00 no
H141 C14 H143 . 109.00 no
H142 C14 H143 . 110.00 no
Cl1 C15 Cl2 . 110.82(13) no
Cl1 C15 Cl3 . 109.94(16) no
Cl2 C15 Cl3 . 110.12(13) no
Cl1 C15 H15 . 109.00 no
Cl2 C15 H15 . 109.00 no
Cl3 C15 H15 . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C15 . 1.751(2) no
Cl2 C15 . 1.753(3) no
Cl3 C15 . 1.760(3) no
O1 C1 . 1.230(3) no
O2 C3 . 1.260(3) no
N1 C5 . 1.343(3) no
N1 C11 . 1.405(3) no
N1 H1 . 0.8800 no
C1 C2 2_556 1.466(3) no
C1 C2 . 1.466(3) no
C2 C4 . 1.388(3) no
C2 C3 . 1.453(3) no
C4 C5 . 1.380(3) no
C5 C6 . 1.525(3) no
C6 C12 . 1.516(3) no
C6 C13 . 1.537(3) no
C6 C14 . 1.533(3) no
C7 C12 . 1.380(3) no
C7 C8 . 1.390(3) no
C8 C9 . 1.384(3) no
C9 C10 . 1.389(3) no
C10 C11 . 1.383(3) no
C11 C12 . 1.387(3) no
C4 H4 . 0.9300 no
C7 H7 . 0.9300 no
C8 H8 . 0.9300 no
C9 H9 . 0.9300 no
C10 H10 . 0.9300 no
C13 H133 . 0.9600 no
C13 H131 . 0.9600 no
C13 H132 . 0.9600 no
C14 H141 . 0.9600 no
C14 H142 . 0.9600 no
C14 H143 . 0.9600 no
C15 H15 . 0.9800 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 0.88 1.96 2.7835(18) 156 yes
C15 H15 O1 0.98 2.13 3.075(3) 161 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C5 C4 . . . 179.2(2) no
C11 N1 C5 C6 . . . -2.7(2) no
C5 N1 C11 C10 . . . -177.9(2) no
C5 N1 C11 C12 . . . 0.8(2) no
O1 C1 C2 C3 . . . 180.00(2) no
O1 C1 C2 C4 . . . 0.9(3) no
C2 C1 C2 C3 2_556 . . 0.00(12) no
C2 C1 C2 C4 2_556 . . -179.1(2) no
C2 C1 C2 C3 . 2_556 . 0.02(16) no
C1 C2 C3 O2 . . . 180.000(10) no
C1 C2 C3 C2 . . 2_556 0.00(11) no
C4 C2 C3 O2 . . . -0.9(3) no
C4 C2 C3 C2 . . 2_556 179.1(3) no
C1 C2 C4 C5 . . . 176.79(19) no
C3 C2 C4 C5 . . . -1.9(4) no
C2 C4 C5 N1 . . . 3.0(3) no
C2 C4 C5 C6 . . . -174.8(2) no
N1 C5 C6 C12 . . . 3.3(2) no
N1 C5 C6 C13 . . . -113.77(19) no
N1 C5 C6 C14 . . . 123.59(19) no
C4 C5 C6 C12 . . . -178.6(2) no
C4 C5 C6 C13 . . . 64.3(3) no
C4 C5 C6 C14 . . . -58.3(3) no
C5 C6 C12 C7 . . . 177.2(2) no
C5 C6 C12 C11 . . . -2.8(2) no
C13 C6 C12 C7 . . . -67.6(3) no
C13 C6 C12 C11 . . . 112.4(2) no
C14 C6 C12 C7 . . . 57.7(3) no
C14 C6 C12 C11 . . . -122.3(2) no
C12 C7 C8 C9 . . . -0.6(3) no
C8 C7 C12 C6 . . . -179.9(2) no
C8 C7 C12 C11 . . . 0.1(3) no
C7 C8 C9 C10 . . . 0.8(4) no
C8 C9 C10 C11 . . . -0.4(3) no
C9 C10 C11 N1 . . . 178.4(2) no
C9 C10 C11 C12 . . . -0.1(3) no
N1 C11 C12 C6 . . . 1.5(2) no
N1 C11 C12 C7 . . . -178.52(19) no
C10 C11 C12 C6 . . . -179.7(2) no
C10 C11 C12 C7 . . . 0.2(3) no
