Synthesis and characterization of fluorophthalocyanines bearing four 2-(2-thienyl)ethoxy moieties: from the optimization of the fluorine substitution to chemosensing
Wannebroucq, Amélie; Meunier-Prest, Rita; Chambron, Jean-Claude; Brachais, Claire-Hélène; Suisse, Jean-Moïse; Bouvet, Marcel; RSC Adv. 7 (2017) 41272–; doi:10.1039/C7RA05325H

data_7228980
_publ_section_title
;
 Synthesis and characterization of fluorophthalocyanines bearing four
 2-(2-thienyl)ethoxy moieties: from the optimization of the fluorine
 substitution to chemosensing
;
_journal_issue                   65
_journal_name_full               'RSC Adv.'
_journal_page_first              41272
_journal_paper_doi               10.1039/C7RA05325H
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C14 H7 F3 N2 O S'
_chemical_formula_sum            'C14 H7 F3 N2 O S'
_chemical_formula_weight         308.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-08-03 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.081(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9995(8)
_cell_length_b                   12.9029(8)
_cell_length_c                   10.0701(7)
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      3.158
_cell_volume                     1333.55(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         3.158
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.7992.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.068
_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_constraints    5
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0352P)^2^+2.4718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2158
_reflns_number_total             3059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra05325h2.cif
_cod_data_source_block           mo_15aw017_0ma
_cod_database_code               7228980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(C4A) = Uiso(S1A) = Uiso(C1A) = Uiso(C2A) = Uiso(C3A)
3. Rigid body (RIGU) restrains
 C4, C3, C2, C1, S1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: H5A(0.75) H5B(0.75) H5BC(0.25) H5BD(0.25) S1(0.75) C4(0.75)
 C1(0.75) H1(0.75) C2(0.75) H2(0.75) C3(0.75) H3(0.75) S1A(0.25) C1A(0.25)
 H1A(0.25) C4A(0.25) C3A(0.25) H3A(0.25) C2A(0.25) H2A(0.25)
5.a Free rotating group:
 S1(C4,C1,C2,C3), S1A(C1A,C4A,C3A,C2A)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C5(H5BC,H5BD), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C1A(H1A), C3A(H3A), C2A(H2A)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'