Structure-behavior study of a family of "hybrid cyanine" dyes which exhibit inverted solvatochromism.
Stock, Rafaela I.; de Melo, Carlos E. A.; Schramm, Adriana D. S.; Nicoleti, Celso R.; Bortoluzzi, Adailton J.; Heying, Renata da S; Machado, Vanderlei G.; Rezende, Marcos C.; Physical chemistry chemical physics : PCCP 18 (2016) 32256–32265; doi:10.1039/c6cp06708e

data_7226960
_publ_section_title
;
 Structure-behavior study of a family of &quot;hybrid cyanine&quot; dyes
 which exhibit inverted solvatochromism.
;
_journal_issue                   47
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              32256
_journal_page_last               32265
_journal_paper_doi               10.1039/c6cp06708e
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C13 H10 Cl2 N2 O4'
_chemical_formula_sum            'C13 H10 Cl2 N2 O4'
_chemical_formula_weight         329.13
_chemical_name_systematic
(E)--4--(4--Nitrophenylmethylenimino)--2,6--dichlorophenol
_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   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-09-16 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7179(3)
_cell_length_b                   13.5770(5)
_cell_length_c                   11.6351(4)
_cell_measurement_reflns_used    6646
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      3.00
_cell_volume                     1368.16(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14171
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.518
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_correction_T_min  0.8747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker APEX2, SAINT and SADABS, version 2011.8-0; Bruker AXS Inc., 
Madison, Wisconsin, USA
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       Block
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0504P)^2^+0.5913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3540
_reflns_number_total             4177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cp06708e2.cif
_cod_data_source_block           2e
_cod_depositor_comments
'Adding full bibliography for 7226957--7226961.cif.'
_cod_database_code               7226960
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2014/6
_shelx_res_checksum              66526