A low molecular weight OLED material: 2-(4-((2-hydroxyethyl)(methyl)amino)benzylidene)malononitrile. Synthesis, crystal structure, thin film morphology, spectroscopic characterization and DFT calculations
Percino, M. Judith; Cerón, Margarita; Venkatesan, Perumal; Pérez-Gutiérrez, Enrique; Santos, Pilar; Ceballos, Paulina; Castillo, Armando E.; Gordillo-Guerra, Paola; Anandhan, Karnambaram; Barbosa-García, Oracio; Bernal, Wilson; Thamotharan, Subbiah; RSC Advances 9 (2019) 28704–; doi:10.1039/C9RA05425A

data_7233819
_publ_section_title
;
 A low molecular weight OLED material:
 2-(4-((2-hydroxyethyl)(methyl)amino)benzylidene)malononitrile. Synthesis,
 crystal structure, thin film morphology, spectroscopic characterization
 and DFT calculations
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              28704
_journal_paper_doi               10.1039/C9RA05425A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_chemical_name_systematic
2-[[4-[hydroxymethyl(methyl)amino]phenyl]methylene]propanedinitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-09-17 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1370(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.24645(14)
_cell_length_b                   17.8507(4)
_cell_length_c                   9.27013(18)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      71.97
_cell_measurement_theta_min      4.93
_cell_volume                     1198.30(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.868
_diffrn_reflns_theta_min         4.955
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       lath
_exptl_crystal_F_000             480
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     728
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0344
_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/[\s^2^(Fo^2^)+(0.0443P)^2^+0.2481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1994
_reflns_number_total             2347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05425a2.cif
_cod_data_source_block           R2
_cod_database_code               7233819
_oxdiff_exptl_absorpt_empirical_full_min 0.730
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2014-3
_shelx_res_checksum              56073