Investigating the effect of heteroatom substitution in 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic photovoltaics
Cameron, Joseph; Abed, Mahmoud Matar; Chapman, Steven J.; Findlay, Neil J.; Skabara, Peter J.; Horton, Peter N.; Coles, Simon J.; Journal of Materials Chemistry C 6 (2018) 3709–; doi:10.1039/C7TC05075E

data_7237016
_publ_section_title
;
 Investigating the effect of heteroatom substitution in
 2,1,3-benzoxadiazole and 2,1,3-benzothiadiazole compounds for organic
 photovoltaics
;
_journal_issue                   14
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3709
_journal_paper_doi               10.1039/C7TC05075E
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C54 H64 N2 O2 S3, C H Cl3'
_chemical_formula_sum            'C55 H65 Cl3 N2 O2 S3'
_chemical_formula_weight         988.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-10-23 deposited with the CCDC.
2017-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                72.963(6)
_cell_angle_beta                 76.859(5)
_cell_angle_gamma                76.620(6)
_cell_formula_units_Z            2
_cell_length_a                   11.6431(6)
_cell_length_b                   13.1881(11)
_cell_length_c                   18.3509(12)
_cell_measurement_reflns_used    12347
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.2480
_cell_measurement_theta_min      2.2320
_cell_volume                     2582.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_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 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -29.00  94.00   1.00   18.00    --    5.00  72.00 -60.00  123
  2  \w    -84.00  36.00   1.00   18.00    --    5.00 -57.00  60.00  120
  3  \w   -101.00  20.00   1.00   18.00    --  -11.20 -57.00  30.00  121
  4  \w    -93.00 -59.00   1.00   18.00    --  -11.20 -57.00-150.00   34
  5  \w    -93.00  20.00   1.00   18.00    --  -11.20 -57.00-150.00  113
  6  \w     -8.00  20.00   1.00   18.00    --  -11.20 -57.00-150.00   28
  7  \w     -6.00  55.00   1.00   18.00    --  -11.20  19.00   0.00   61
  8  \w    -46.00 -19.00   1.00   18.00    --  -11.20  19.00   0.00   27
  9  \w   -100.00  14.00   1.00   18.00    --  -11.20 -57.00-180.00  114
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041719000
_diffrn_orient_matrix_UB_12      -0.0567636000
_diffrn_orient_matrix_UB_13      0.0126295000
_diffrn_orient_matrix_UB_21      0.0137744000
_diffrn_orient_matrix_UB_22      -0.0032116000
_diffrn_orient_matrix_UB_23      -0.0390376000
_diffrn_orient_matrix_UB_31      0.0619107000
_diffrn_orient_matrix_UB_32      -0.0058457000
_diffrn_orient_matrix_UB_33      0.0006083000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52160
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         11647
_refine_ls_number_restraints     135
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0946
_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^)+(0.0589P)^2^+5.4161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.1983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9540
_reflns_number_total             11647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7tc05075e2.cif
_cod_data_source_block           BT-(TBF)2
_cod_database_code               7237016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C54 H64 N2 O2 S3'
_chemical_oxdiff_usercomment     MA006
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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
 C61-Cl61 = C61-Cl62 = C61-Cl63
 1.7 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C61 \\sim Cl61 \\sim Cl62 \\sim Cl63 \\sim Cl73 \\sim Cl71 \\sim Cl72 \\sim
C71: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C61, Cl61, Cl62, Cl63, Cl73, Cl71, Cl72, C71
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C61, Cl61, Cl62, Cl63} sigma for 1-2: 0.02, 1-3: 0.04
as
{C71, Cl71, Cl72, Cl73}
6. Others
 Sof(H2)=Sof(H3)=Sof(S3B)=Sof(N1B)=Sof(N2B)=1-FVAR(1)
 Sof(H5)=Sof(H6)=Sof(S3)=Sof(N1)=Sof(N2)=FVAR(1)
 Sof(C71)=Sof(H71)=Sof(Cl71)=Sof(Cl72)=Sof(Cl73)=1-FVAR(2)
 Sof(C61)=Sof(H61)=Sof(Cl61)=Sof(Cl62)=Sof(Cl63)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C61(H61), C71(H71)
7.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C40(H40A,H40B), C41(H41A,H41B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B),
  C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,
 H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30)
7.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              84767
_shelx_hkl_checksum              84828
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.868
_oxdiff_exptl_absorpt_empirical_full_min 0.608