#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234644.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_7234644
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'
_chemical_formula_sum            'C20 H20 N4'
_chemical_formula_weight         316.40
_chemical_name_common
2-(bis(4-dimethylaminophenyl)methylene)malonitrile
_chemical_name_systematic
; 
1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.0620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4920(7)
_cell_length_b                   13.9497(11)
_cell_length_c                   15.0750(14)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.527
_cell_measurement_theta_min      2.744
_cell_volume                     1758.3(3)
_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      296(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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16782
_diffrn_reflns_theta_full        29.82
_diffrn_reflns_theta_max         29.82
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             672
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0462
_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)+(0.0608P)²+0.6116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                1782
_reflns_number_total             2531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2979.cif
_cod_data_source_block           B
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7234644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.78396(18) 1.29756(9) 0.65638(9) 0.0709(4) Uani 1 1 d . . .
N2 N 0.62956(15) 0.88502(9) 0.46382(8) 0.0613(3) Uani 1 1 d . . .
C1 C 0.87905(17) 1.24848(9) 0.69583(9) 0.0522(3) Uani 1 1 d . . .
C2 C 1.0000 1.19212(12) 0.7500 0.0467(4) Uani 1 2 d S . .
C3 C 1.0000 1.09251(12) 0.7500 0.0423(4) Uani 1 2 d S . .
C4 C 0.90331(15) 1.03984(8) 0.67616(8) 0.0422(3) Uani 1 1 d . . .
C5 C 0.88183(16) 1.07234(9) 0.58690(8) 0.0472(3) Uani 1 1 d . . .
H5 H 0.9295 1.1297 0.5745 0.057 Uiso 1 1 calc R . .
C6 C 0.79284(16) 1.02241(9) 0.51727(8) 0.0490(3) Uani 1 1 d . . .
H6 H 0.7825 1.0461 0.4589 0.059 Uiso 1 1 calc R . .
C7 C 0.71689(15) 0.93592(9) 0.53269(8) 0.0459(3) Uani 1 1 d . . .
C8 C 0.73759(16) 0.90314(9) 0.62244(9) 0.0508(3) Uani 1 1 d . . .
H8 H 0.6880 0.8466 0.6352 0.061 Uiso 1 1 calc R . .
C9 C 0.82948(16) 0.95291(9) 0.69138(8) 0.0474(3) Uani 1 1 d . . .
H9 H 0.8430 0.9283 0.7496 0.057 Uiso 1 1 calc R . .
C10 C 0.6075(2) 0.91861(15) 0.37169(10) 0.0803(5) Uani 1 1 d . . .
H10A H 0.5478 0.9774 0.3665 0.120 Uiso 1 1 calc R . .
H10B H 0.5500 0.8712 0.3326 0.120 Uiso 1 1 calc R . .
H10C H 0.7099 0.9295 0.3549 0.120 Uiso 1 1 calc R . .
C11 C 0.54271(19) 0.79927(12) 0.48118(11) 0.0696(4) Uani 1 1 d . . .
H11A H 0.6157 0.7539 0.5139 0.104 Uiso 1 1 calc R . .
H11B H 0.4927 0.7715 0.4250 0.104 Uiso 1 1 calc R . .
H11C H 0.4624 0.8158 0.5161 0.104 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'
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 C10 121.59(13) . .
C7 N2 C11 121.12(12) . .
C10 N2 C11 117.05(13) . .
N1 C1 C2 175.97(14) . .
C3 C2 C1 123.33(8) . .
C3 C2 C1 123.33(8) . 2_756
C1 C2 C1 113.34(15) . 2_756
C2 C3 C4 120.19(7) . 2_756
C2 C3 C4 120.20(7) . .
C4 C3 C4 119.61(14) 2_756 .
C5 C4 C9 116.74(11) . .
C5 C4 C3 122.04(11) . .
C9 C4 C3 121.20(11) . .
C6 C5 C4 122.17(12) . .
C5 C6 C7 121.10(11) . .
N2 C7 C6 121.64(12) . .
N2 C7 C8 121.42(12) . .
C6 C7 C8 116.93(11) . .
C9 C8 C7 121.41(12) . .
C8 C9 C4 121.62(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.1431(17) .
N2 C7 1.3649(16) .
N2 C10 1.447(2) .
N2 C11 1.453(2) .
C1 C2 1.4306(16) .
C2 C3 1.390(2) .
C2 C1 1.4306(16) 2_756
C3 C4 1.4607(14) 2_756
C3 C4 1.4607(14) .
C4 C5 1.4012(16) .
C4 C9 1.4023(17) .
C5 C6 1.3714(17) .
C6 C7 1.4064(18) .
C7 C8 1.4097(17) .
C8 C9 1.3740(17) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 291378
