Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable Polymer Blends.
Echeverri, Marcelo; Ruiz, Constanza; Gámez-Valenzuela, Sergio; Alonso-Navarro, Matias; Gutierrez-Puebla, Enrique; Serrano, José L; Ruiz Delgado, M. Carmen; Gómez-Lor, Berta; ACS applied materials & interfaces  (2020) –; doi:10.1021/acsami.9b21209

data_4517438
_publ_section_title
;
 Stimuli-Responsive Benzothiadiazole Derivative as a Dopant for Rewritable
 Polymer Blends.
;
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_paper_doi               10.1021/acsami.9b21209
_journal_year                    2020
_chemical_formula_moiety         'C36 H48 N2 S'
_chemical_formula_sum            'C36 H48 N2 S'
_chemical_formula_weight         540.82
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-06
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.667(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0246(4)
_cell_length_b                   17.2258(11)
_cell_length_c                   27.700(2)
_cell_measurement_reflns_used    2985
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.41
_cell_measurement_theta_min      3.03
_cell_volume                     3335.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker VANTEC 500 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker X8'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.1817
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30028
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        63.592
_diffrn_reflns_theta_max         63.592
_diffrn_reflns_theta_min         1.603
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       needle
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.752
_exptl_transmission_factor_min   0.582
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.63(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         10568
_refine_ls_number_restraints     742
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.1002
_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^)+(0.1190P)^2^+0.9212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2558
_refine_ls_wR_factor_ref         0.3358
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                5400
_reflns_number_total             10568
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am9b21209_si_001.cif
_cod_data_source_block           Compd1
_cod_depositor_comments
;

2020-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        3335.5(4)
_cod_original_formula_moiety     '2(C36 H48 N2 S)'
_cod_original_formula_sum        'C72 H96 N4 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1081.64
_cod_database_code               4517438
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1CA-C2DA
 1.5 with sigma of 0.02
 C3DA-C2DA
 1.5 with sigma of 0.02
 C6CA-C6 = C7-C2
 1.5 with sigma of 0.02
 C13-C28 = C28-C17
 1.5 with sigma of 0.02
 C4DA-C29 = C14-C3BA = C9CA-C4
 1.5 with sigma of 0.02
 C3CA-C4CA = C37-C6AA
 1.5 with sigma of 0.02
 C27-C1CA
 1.5 with sigma of 0.02
 C9CA-C3BA
 1.5 with sigma of 0.02
 C4-C8AA
 1.5 with sigma of 0.02
 C0DA-C21 = C21-C7
 1.5 with sigma of 0.02
 C2-C5DA
 1.5 with sigma of 0.02
 C0DA-C8DA = C8DA-C6
 1.5 with sigma of 0.02
 C32-C1
 1.5 with sigma of 0.02
 C1-C36
 1.5 with sigma of 0.02
 C39-C44
 1.5 with sigma of 0.02
 C44-C4DA
 1.5 with sigma of 0.02
 C6CA-C7BA
 1.5 with sigma of 0.02
 C6CA-C6
 1.5 with sigma of 0.02
 C2AA-C13
 1.5 with sigma of 0.02
 C13-C28
 1.5 with sigma of 0.02
 C27-C0EA = C0EA-C36
 1.5 with sigma of 0.02
 C6AA-C8BA
 1.5 with sigma of 0.02
 C29-C14
 1.5 with sigma of 0.02
 C5DA-C35
 1.5 with sigma of 0.02
 C17-C3CA
 1.38 with sigma of 0.02
 C8AA-C7CA
 1.5 with sigma of 0.02
 C3DA-C9DA = C9DA-C1DA
 1.5 with sigma of 0.02
 C3DA-C1DA
 2.3 with sigma of 0.02
 C8-C8BA
 1.4 with sigma of 0.02
 C17-C13 = C4DA-C14
 2.4 with sigma of 0.04
 C29-C3BA
 2.4 with sigma of 0.04
 C2DA-C9DA
 2.4 with sigma of 0.04
 C0DA-C6
 2.4 with sigma of 0.04
 C3CA-C28
 2.4 with sigma of 0.04
 C2-C35
 2.4 with sigma of 0.04
 C6AA-C8
 2.4 with sigma of 0.04
 C4-C7CA
 2.4 with sigma of 0.04
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.1 and sigma for 1-3 distances of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.12
5.a Secondary CH2 refined with riding coordinates:
 C44(H44A,H44B), C6AA(H6AA,H6AB), C4CA(H4CA,H4CB), C6CA(H6CA,H6CB), C6(H6A,
 H6B), C3CA(H3CA,H3CB), C1CA(H1CA,H1CB), C29(H29A,H29B), C37(H37A,H37B),
 C2DA(H2DA,H2DB), C3DA(H3DA,H3DB), C4DA(H4DA,H4DB), C27(H27A,H27B), C0DA(H0DA,
 H0DB), C36(H36A,H36B), C13(H13A,H13B), C17(H17A,H17B), C28(H28A,H28B),
 C3BA(H3BA,H3BB), C14(H14A,H14B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B),
 C9CA(H9CA,H9CB), C5DA(H5DA,H5DB), C9DA(H9DA,H9DB), C21(H21A,H21B), C8AA(H8AA,
 H8AB), C8DA(H8DA,H8DB), C1(H1A,H1B), C8BA(H8BA,H8BB), C0EA(H0EA,H0EB)
5.b Me refined with riding coordinates:
 C7CA(H7CA,H7CB,H7CC), C1DA(H1DA,H1DB,H1DC), C35(H35A,H35B,H35C), C8(H8A,H8B,
 H8C)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C6DA(H6DA), C18(H18), C4BA(H4BA), C5BA(H5BA), C22(H22), C23(H23),
 C24(H24), C25(H25), C8CA(H8CA), C5CA(H5CA), C7DA(H7DA), C0CA(H0CA), C30(H30),
 C31(H31), C33(H33), C34(H34), C40(H40), C12(H12), C3AA(H3AA)
;
_olex2_submission_special_instructions 'No special instructions were received'