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_7237015
_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 O3 S2, 1(C H Cl3)'
_chemical_formula_sum            'C55 H65 Cl3 N2 O3 S2'
_chemical_formula_weight         972.56
_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                72.595(2)
_cell_angle_beta                 77.433(2)
_cell_angle_gamma                77.292(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6310(2)
_cell_length_b                   12.9034(4)
_cell_length_c                   18.3333(5)
_cell_measurement_reflns_used    17513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2670
_cell_measurement_theta_min      2.3050
_cell_volume                     2526.88(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -36.00  79.00   1.00   55.00    --  -10.40  38.00 120.00  115
  2  \w   -100.00  15.00   1.00   55.00    --  -10.40 -38.00-180.00  115
  3  \w   -100.00  20.00   1.00   55.00    --  -10.40 -57.00 120.00  120
  4  \w   -100.00  23.00   1.00   55.00    --  -10.40 -72.00 -60.00  123
  5  \w   -100.00  23.00   1.00   55.00    --  -10.40 -72.00   0.00  123
  6  \w    -44.00   7.00   1.00   55.00    --  -10.40  72.00   0.00   51
  7  \w    -41.00  79.00   1.00   55.00    --  -10.40  57.00 -90.00  120
;
_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      -0.0188542000
_diffrn_orient_matrix_UB_12      0.0494226000
_diffrn_orient_matrix_UB_13      0.0118889000
_diffrn_orient_matrix_UB_21      0.0199040000
_diffrn_orient_matrix_UB_22      -0.0272811000
_diffrn_orient_matrix_UB_23      0.0359257000
_diffrn_orient_matrix_UB_31      0.0571245000
_diffrn_orient_matrix_UB_32      0.0150402000
_diffrn_orient_matrix_UB_33      -0.0160263000
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            55199
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.260
_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    0.309
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55658
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     691
_refine_ls_number_reflns         11551
_refine_ls_number_restraints     289
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0696P)^2^+0.7344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8397
_reflns_number_total             11551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7tc05075e2.cif
_cod_data_source_block           BO-(TBF)2
_cod_database_code               7237015
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C54 H64 N2 O3 S2'
_chemical_oxdiff_usercomment     MA007
_reflns_odcompleteness_completeness 99.75
_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. Uiso/Uaniso restraints and constraints
C71 \\sim Cl71 \\sim Cl72 \\sim Cl73 \\sim C81 \\sim Cl81 \\sim Cl82 \\sim Cl83
\\sim C61 \\sim Cl62 \\sim Cl63 \\sim Cl61: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 C71, Cl71, Cl72, Cl73, C81, Cl81, Cl82, Cl83, C61, Cl62, Cl63, Cl61
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{Cl61, Cl62, Cl63, C61} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl71, Cl72, Cl73, C71}
{Cl61, Cl62, Cl63, C61} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl81, Cl82, Cl83, C81}
5. Others
 1*[Sof(Cl71)+Sof(Cl72)+Sof(Cl73)+Sof(C71)+Sof(H71)]+1*[Sof(Cl61)+Sof(Cl62)+
 Sof(Cl63)+Sof(C61)+Sof(H61)]+1*[Sof(Cl81)+Sof(Cl82)+Sof(Cl83)+Sof(C81)+
 Sof(H81)]=1 with esd of 0.000001
 Sof(H2)=Sof(H3)=Sof(O3B)=Sof(N1B)=Sof(N2B)=1-FVAR(1)
 Sof(H5)=Sof(H6)=Sof(O3)=Sof(N1)=Sof(N2)=FVAR(1)
 Sof(Cl71)=Sof(Cl72)=Sof(Cl73)=Sof(C71)=Sof(H71)=FVAR(2)
 Sof(Cl61)=Sof(Cl62)=Sof(Cl63)=Sof(C61)=Sof(H61)=FVAR(3)
 Sof(Cl81)=Sof(Cl82)=Sof(Cl83)=Sof(C81)=Sof(H81)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C71(H71), C61(H61), C81(H81)
6.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)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
6.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              63716
_shelx_hkl_checksum              15945
_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 2.118
_oxdiff_exptl_absorpt_empirical_full_min 0.554