To bend or not to bend – are heteroatom interactions within conjugated molecules effective in dictating conformation and planarity?
Conboy, Gary; Spencer, Howard J.; Angioni, Enrico; Kanibolotsky, Alexander L.; Findlay, Neil J.; Coles, Simon J.; Wilson, Claire; Pitak, Mateusz B.; Risko, Chad; Coropceanu, Veaceslav; Brédas, Jean-Luc; Skabara, Peter J.; Mater. Horiz. 3 (2016) 333–; doi:10.1039/C6MH00051G

data_1543212
_publ_section_title
;
 To bend or not to bend -- are heteroatom interactions within conjugated
 molecules effective in dictating conformation and planarity?
;
_journal_issue                   4
_journal_name_full               'Mater. Horiz.'
_journal_page_first              333
_journal_paper_doi               10.1039/C6MH00051G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C34 H34 N4 O2 S2'
_chemical_formula_sum            'C34 H34 N4 O2 S2'
_chemical_formula_weight         594.77
_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_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-07 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.041(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.526(2)
_cell_length_b                   5.1215(7)
_cell_length_c                   20.577(3)
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      3.0
_cell_volume                     1447.1(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 133
               Slice: -60.0000 - 73.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 14.0000
                 Phi: -180.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 120
               Slice: -98.0000 - 22.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -129.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 104
               Slice: -82.0000 - 22.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 25.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 34
               Slice: -44.0000 - -10.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -180.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 10
               Slice: 0.0000 - 10.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -44.0000
                 Phi: -129.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 133
               Slice: -60.0000 - 73.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 14.0000
                 Phi: 77.0000
                 XTD: 44.9826
              2theta: -17.1738
scan:
    Number of images: 21
               Slice: -98.0000 - -77.0000
         Image width: 1.0000
            Exp time: 15.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 128.0000
                 XTD: 44.9826
              2theta: -17.1738
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.049974
_diffrn_orient_matrix_UB_12      -0.001924
_diffrn_orient_matrix_UB_13      0.011045
_diffrn_orient_matrix_UB_21      -0.019666
_diffrn_orient_matrix_UB_22      -0.184591
_diffrn_orient_matrix_UB_23      0.056834
_diffrn_orient_matrix_UB_31      0.036297
_diffrn_orient_matrix_UB_32      -0.021975
_diffrn_orient_matrix_UB_33      -0.058814
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.148
_diffrn_reflns_av_unetI/netI     0.260
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.058
_diffrn_reflns_theta_max         25.058
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_transf_matrix_11  0.049974
_diffrn_reflns_transf_matrix_12  -0.001924
_diffrn_reflns_transf_matrix_13  0.011045
_diffrn_reflns_transf_matrix_21  -0.019666
_diffrn_reflns_transf_matrix_22  -0.184591
_diffrn_reflns_transf_matrix_23  0.056834
_diffrn_reflns_transf_matrix_31  0.036297
_diffrn_reflns_transf_matrix_32  -0.021975
_diffrn_reflns_transf_matrix_33  -0.058814
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       Block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     291
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.3045
_refine_ls_R_factor_gt           0.1450
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3462
_refine_ls_wR_factor_ref         0.4364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                938
_reflns_number_total             2550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6mh00051g2.cif
_cod_data_source_block           2013ncs0660
_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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543209--1543212.cif.
;
_cod_original_cell_volume        1447.0(4)
_cod_database_code               1543212
_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
 C5-C6 = C7-C6 = C7-C8 = C8-C9 = C9-C10 = C11-C10
 1.51 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
4. 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
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              95190
_shelx_hkl_checksum              99355
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'