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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234646.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_7234646
loop_
_publ_author_name
'Chiara Botta'
'Sara Benedini'
'Lucia Carlucci'
'Alessandra Forni'
'Daniele Marinotto'
'Andrea Nitti'
'Dario Pasini'
'Stefania Righetto'
'Elena Cariati'
_publ_section_title
;
 Polymorphism-dependent aggregation induced emission of a push-pull dye
 and its multi-stimuli responsive behavior
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2979
_journal_page_last               2989
_journal_paper_doi               10.1039/C5TC03352G
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C20 H20 N4, C H2 Cl2'
_chemical_formula_sum            'C21 H22 Cl2 N4'
_chemical_formula_weight         401.33
_chemical_name_common
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_chemical_name_systematic
'1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene dichloromethane solvate'
_chemical_properties_physical
'The crystals decay in few days owing to co-crystallized solvent loss'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5444(8)
_cell_length_b                   22.3085(14)
_cell_length_c                   7.5898(5)
_cell_measurement_reflns_used    4027
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      21.834
_cell_measurement_theta_min      2.483
_cell_volume                     2048.2(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  'SHELXL-97,PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex II CCD area detector'
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23624
_diffrn_reflns_theta_full        23.41
_diffrn_reflns_theta_max         23.41
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0512P)²+2.7655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                2360
_reflns_number_total             2993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2979.cif
_cod_data_source_block           D
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7234646
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'
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
N1 N 1.0228(2) 0.75537(12) 0.1650(4) 0.0420(7) Uani 1 1 d . . .
N2 N 1.03805(19) 0.47184(10) 0.2512(3) 0.0309(6) Uani 1 1 d . . .
N3 N 0.7334(2) 0.83724(11) 0.2544(3) 0.0363(6) Uani 1 1 d . . .
N4 N 0.31828(19) 0.68175(12) 0.1390(4) 0.0383(6) Uani 1 1 d . . .
C1 C 0.9377(2) 0.74604(12) 0.1898(4) 0.0291(7) Uani 1 1 d . . .
C2 C 0.8292(2) 0.73767(12) 0.2129(4) 0.0253(6) Uani 1 1 d . . .
C3 C 0.7800(2) 0.68220(12) 0.2110(3) 0.0243(6) Uani 1 1 d . . .
C4 C 0.8450(2) 0.62716(12) 0.2306(4) 0.0244(6) Uani 1 1 d . . .
C5 C 0.9546(2) 0.62446(12) 0.3378(4) 0.0253(6) Uani 1 1 d . . .
H5 H 0.9864 0.6589 0.4049 0.030 Uiso 1 1 calc R . .
C6 C 1.0173(2) 0.57336(12) 0.3486(4) 0.0258(6) Uani 1 1 d . . .
H6 H 1.0909 0.5731 0.4243 0.031 Uiso 1 1 calc R . .
C7 C 0.9745(2) 0.52131(12) 0.2495(4) 0.0258(6) Uani 1 1 d . . .
C8 C 0.8626(2) 0.52329(12) 0.1471(4) 0.0281(6) Uani 1 1 d . . .
H8 H 0.8296 0.4886 0.0829 0.034 Uiso 1 1 calc R . .
C9 C 0.8007(2) 0.57459(12) 0.1389(4) 0.0272(6) Uani 1 1 d . . .
H9 H 0.7257 0.5744 0.0690 0.033 Uiso 1 1 calc R . .
C10 C 1.1546(2) 0.47190(13) 0.3494(4) 0.0356(7) Uani 1 1 d . . .
H10A H 1.1905 0.5073 0.3143 0.053 Uiso 1 1 calc R . .
H10B H 1.1898 0.4356 0.3188 0.053 Uiso 1 1 calc R . .
H10C H 1.1619 0.4729 0.4811 0.053 Uiso 1 1 calc R . .
C11 C 0.9901(3) 0.41616(13) 0.1670(4) 0.0383(8) Uani 1 1 d . . .
H11A H 0.9613 0.4220 0.0349 0.057 Uiso 1 1 calc R . .
H11B H 0.9297 0.4040 0.2189 0.057 Uiso 1 1 calc R . .
H11C H 1.0469 0.3849 0.1902 0.057 Uiso 1 1 calc R . .
C12 C 0.7740(2) 0.79258(13) 0.2337(4) 0.0269(6) Uani 1 1 d . . .
C13 C 0.6601(2) 0.67951(11) 0.1877(4) 0.0238(6) Uani 1 1 d . . .
C14 C 0.6125(2) 0.63955(12) 0.2864(4) 0.0262(6) Uani 1 1 d . . .
H14 H 0.6583 0.6116 0.3663 0.031 Uiso 1 1 calc R . .
C15 C 0.5004(2) 0.63983(12) 0.2706(4) 0.0290(7) Uani 1 1 d . . .
H15 H 0.4708 0.6125 0.3413 0.035 Uiso 1 1 calc R . .
C16 C 0.4289(2) 0.67972(12) 0.1518(4) 0.0281(6) Uani 1 1 d . . .
C17 C 0.4765(2) 0.71828(12) 0.0474(4) 0.0286(6) Uani 1 1 d . . .
H17 H 0.4305 0.7449 -0.0371 0.034 Uiso 1 1 calc R . .
C18 C 0.5887(2) 0.71806(12) 0.0655(4) 0.0265(6) Uani 1 1 d . . .
H18 H 0.6184 0.7447 -0.0068 0.032 Uiso 1 1 calc R . .
C19 C 0.2667(3) 0.63630(17) 0.2244(5) 0.0533(10) Uani 1 1 d . . .
H19A H 0.2722 0.5973 0.1678 0.080 Uiso 1 1 calc R . .
H19B H 0.1887 0.6464 0.2082 0.080 Uiso 1 1 calc R . .
H19C H 0.3042 0.6343 0.3551 0.080 Uiso 1 1 calc R . .
C20 C 0.2456(3) 0.71873(19) 0.0000(5) 0.0575(10) Uani 1 1 d . . .
H20A H 0.1694 0.7148 0.0094 0.086 Uiso 1 1 calc R . .
H20B H 0.2495 0.7055 -0.1213 0.086 Uiso 1 1 calc R . .
H20C H 0.2688 0.7607 0.0184 0.086 Uiso 1 1 calc R . .
C21 C 0.4919(3) 0.9128(2) 0.2997(6) 0.0687(12) Uani 1 1 d . . .
H21A H 0.5176 0.9068 0.4335 0.082 Uiso 1 1 calc R . .
H21B H 0.5194 0.8787 0.2406 0.082 Uiso 1 1 calc R . .
Cl1 Cl 0.34764(10) 0.91219(8) 0.23390(18) 0.1067(5) Uani 1 1 d . . .
Cl2 Cl 0.54756(15) 0.97758(7) 0.2440(3) 0.1463(8) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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
C7 N2 C11 121.1(2) . .
C7 N2 C10 120.8(2) . .
C11 N2 C10 118.0(2) . .
C16 N4 C19 120.8(3) . .
C16 N4 C20 120.0(3) . .
C19 N4 C20 117.0(3) . .
N1 C1 C2 176.3(3) . .
C3 C2 C1 123.5(2) . .
C3 C2 C12 122.6(2) . .
C1 C2 C12 113.8(2) . .
C2 C3 C4 121.1(2) . .
C2 C3 C13 118.6(2) . .
C4 C3 C13 120.3(2) . .
C5 C4 C9 116.9(2) . .
C5 C4 C3 122.1(2) . .
C9 C4 C3 121.0(2) . .
C6 C5 C4 121.9(3) . .
C5 C6 C7 121.3(2) . .
N2 C7 C6 121.6(2) . .
N2 C7 C8 121.7(2) . .
C6 C7 C8 116.7(2) . .
C9 C8 C7 121.2(3) . .
C8 C9 C4 121.9(3) . .
N3 C12 C2 177.6(3) . .
C14 C13 C18 117.2(2) . .
C14 C13 C3 122.1(2) . .
C18 C13 C3 120.7(2) . .
C15 C14 C13 121.4(3) . .
C14 C15 C16 121.4(3) . .
N4 C16 C17 121.0(3) . .
N4 C16 C15 122.0(3) . .
C17 C16 C15 117.0(2) . .
C18 C17 C16 121.1(3) . .
C17 C18 C13 121.7(3) . .
Cl2 C21 Cl1 113.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.150(4) .
N2 C7 1.360(3) .
N2 C11 1.453(4) .
N2 C10 1.454(4) .
N3 C12 1.149(4) .
N4 C16 1.366(4) .
N4 C19 1.445(4) .
N4 C20 1.455(4) .
C1 C2 1.430(4) .
C2 C3 1.381(4) .
C2 C12 1.436(4) .
C3 C4 1.459(4) .
C3 C13 1.468(4) .
C4 C5 1.401(4) .
C4 C9 1.402(4) .
C5 C6 1.375(4) .
C6 C7 1.410(4) .
C7 C8 1.413(4) .
C8 C9 1.376(4) .
C13 C14 1.397(4) .
C13 C18 1.402(4) .
C14 C15 1.379(4) .
C15 C16 1.408(4) .
C16 C17 1.405(4) .
C17 C18 1.377(4) .
C21 Cl2 1.707(4) .
C21 Cl1 1.746(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339034
