Exo-Methylene-BEDT-TTF and Alkene-functionalised BEDT-TTF Derivatives: Synthesis and Radical Cation Salts
Zecchini, Matteo; Lopez, Jordan R.; Allen, Scott; Coles, Simon; Wilson, Claire; Akutsu, Hiroki; Martin, Lee; Wallis, John D.; RSC Adv.  (2015) –; doi:10.1039/C5RA03921E

data_7219997
_publ_section_title
;
 Exo-Methylene-BEDT-TTF and Alkene-functionalised BEDT-TTF Derivatives:
 Synthesis and Radical Cation Salts
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA03921E
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(Cl O4), C14 H14 O S8'
_chemical_formula_sum            'C14 H14 Cl2 O9 S8'
_chemical_formula_weight         653.63
_chemical_name_systematic
;
(Allyloxymethyl_BEDT-TTF) diperchlorate
;
_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
_audit_creation_date             2014-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4779)
;
_audit_update_record
;
2015-02-27 deposited with the CCDC.
2015-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(3)
_cell_angle_beta                 97.871(4)
_cell_angle_gamma                90.000(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9156(4)
_cell_length_b                   9.5177(7)
_cell_length_c                   21.3112(16)
_cell_measurement_reflns_used    11257
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.3
_cell_volume                     1188.58(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
    Number of images: 175
               Slice: -60.0000 - 115.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 59.6396
              2theta: 30.1352
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 0.0000
                 XTD: 59.6396
              2theta: 30.1352
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 120.0000
                 XTD: 59.6396
              2theta: 30.1352
scan:
    Number of images: 120
               Slice: -60.0000 - 60.0000
         Image width: 1.0000
            Exp time: 1.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -50.0000
                 Phi: 240.0000
                 XTD: 59.6396
              2theta: 30.1352
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.139118
_diffrn_orient_matrix_UB_12      -0.043472
_diffrn_orient_matrix_UB_13      -0.088763
_diffrn_orient_matrix_UB_21      0.060506
_diffrn_orient_matrix_UB_22      -0.027418
_diffrn_orient_matrix_UB_23      -0.081403
_diffrn_orient_matrix_UB_31      -0.002397
_diffrn_orient_matrix_UB_32      -0.045345
_diffrn_orient_matrix_UB_33      0.013492
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_radiation_monochromator  'double crystal silicon'
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.080
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11232
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.203
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_transf_matrix_11  -0.139118
_diffrn_reflns_transf_matrix_12  -0.043472
_diffrn_reflns_transf_matrix_13  -0.088763
_diffrn_reflns_transf_matrix_21  0.060506
_diffrn_reflns_transf_matrix_22  -0.027418
_diffrn_reflns_transf_matrix_23  -0.081403
_diffrn_reflns_transf_matrix_31  -0.002397
_diffrn_reflns_transf_matrix_32  -0.045345
_diffrn_reflns_transf_matrix_33  0.013492
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19'
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details
;
 Flack x determined using 1551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.14(15)
_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     295
_refine_ls_number_reflns         9058
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1586P)^2^+3.0982P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2176
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8296
_reflns_number_total             9058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra03921e1.cif
_cod_data_source_block           2013ncs0478_twin
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_cell_volume        1188.58(13)
_cod_database_code               7219997
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C13-C14
 1.5 with sigma of 0.02
 C14-C15
 1.316 with sigma of 0.02
 C11-O12 = C11A-O12
 1.4 with sigma of 0.02
 O12-C13 = C11-O12 = C11A-O12
 1.416 with sigma of 0.02
 C9A-C10A \\sim C9-C10
 with sigma of 0.02
 C11-C10 \\sim C11A-C9A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Uiso(C11A)=Uiso(C11)=FVAR(1)
 Fixed Sof: C9(0.5) H9A(0.5) H9B(0.5) C9A(0.5) H9AA(0.5) C10(0.5) H10(0.5)
 C10A(0.5) H10A(0.5) H10B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) C11(0.5) H11C(0.5)
 H11D(0.5)
5.a Ternary CH refined with riding coordinates:
 C9A(H9AA), C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C9(H9A,H9B), C10A(H10A,H10B), C11A(H11A,H11B),
 C11(H11C,H11D), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
5.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
;