Crystal structures, syntheses, and spectroscopic and electrochemical measurements of two push–pull chromophores: 2-[4-(dimethylamino)benzylidene]-1<i>H</i>-indene-1,3(2<i>H</i>)-dione and (<i>E</i>)-2-{3-[4-(dimethylamino)phenyl]allylidene}-1<i>H</i>-indene-1,3(2<i>H</i>)-dione
Bogdanov, Georgii; Tillotson, John P.; Timofeeva, Tatiana; Acta Crystallographica Section E 75 (2019) 1595–1599; doi:10.1107/S205698901901329X

data_2243135
_publ_section_title
;
 Crystal structures, syntheses, and spectroscopic and electrochemical
 measurements of two push--pull chromophores:
 2-[4-(dimethylamino)benzylidene]-1<i>H</i>-indene-1,3(2<i>H</i>)-dione
 and
 (<i>E</i>)-2-{3-[4-(dimethylamino)phenyl]allylidene}-1<i>H</i>-indene-1,3(2<i>H</i>)-dione
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1595
_journal_page_last               1599
_journal_paper_doi               10.1107/S205698901901329X
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C20 H17 N O2'
_chemical_formula_moiety         'C20 H17 N O2'
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_chemical_name_systematic
(<i>E</i>)-2-{3-[4-(Dimethylamino)phenyl]allylidene}-1<i>H</i>-indene-1,3(2<i>H</i>)-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.500(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.072(2)
_cell_length_b                   3.9664(8)
_cell_length_c                   17.557(4)
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.615
_cell_measurement_theta_min      2.397
_cell_volume                     746.5(3)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b), PLATON (Spek, 2009)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2017/1</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8685
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.696
_diffrn_reflns_theta_min         1.198
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.331
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1732 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0453
_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
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                4358
_reflns_number_total             4531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5515sup1.cif
_cod_data_source_block           ID2
_cod_database_code               2243135
_cod_database_fobs_code          2243135
_shelx_estimated_absorpt_t_min   0.5839
_shelx_estimated_absorpt_t_max   0.7463
_shelx_hkl_checksum              32378
_shelx_res_checksum              3582