Polymerization of acrylates based on n-type organic semiconductors using Cu(0)-RDRP
Tonge, Christopher M.; Sauvé, Ethan R.; Paisley, Nathan R.; Heyes, Jordan E.; Hudson, Zachary M.; Polymer Chemistry 9 (2018) 3359–; doi:10.1039/C8PY00670A

data_1549429
_publ_section_title
;
 Polymerization of acrylates based on n-type organic semiconductors using
 Cu(0)-RDRP
;
_journal_issue                   24
_journal_name_full               'Polymer Chemistry'
_journal_page_first              3359
_journal_paper_doi               10.1039/C8PY00670A
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C46 H36 Br2 Cu N4 O4, 2(C6 H6)'
_chemical_formula_sum            'C58 H48 Br2 Cu N4 O4'
_chemical_formula_weight         1088.36
_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     dual
_audit_creation_date             2017-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-19 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.172(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.4411(18)
_cell_length_b                   8.8490(10)
_cell_length_c                   18.948(2)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.38
_cell_volume                     2494.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25174
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.375
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0646 before and 0.0453 after correction. The Ratio of minimum to maximum transmission is 0.7657. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       plate
_exptl_crystal_F_000             1110
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and benzene by slow evaporation'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.535
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     313
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0174P)^2^+13.7222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4845
_reflns_number_total             6173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8py00670a2.cif
_cod_data_source_block           zh006
_cod_depositor_comments          'Adding full bibliography for 1549429.cif.'
_cod_original_cell_volume        2495.0(5)
_cod_database_code               1549429
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.460
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C23-C22A \\sim C23-C22
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C24A \\sim C25A
\\sim C26A \\sim C27A \\sim C28A \\sim C29A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C24, C25, C26, C27, C28, C29, C24A, C25A, C26A, C27A, C28A, C29A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2, O1, C20, C21, C22, C23, O2A, O1A, C22A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20, O1, O1A, O2, C21, O2A, C22A, C22, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=
 Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=FVAR(1)
 Sof(H20C)=Sof(H20D)=Sof(H23C)=Sof(H23D)=Sof(O2A)=Sof(O1A)=Sof(C22A)=Sof(H22A)=
 1-FVAR(2)
 Sof(O2)=Sof(O1)=Sof(H20A)=Sof(H20B)=Sof(C22)=Sof(H22)=Sof(H23A)=Sof(H23B)=
 FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20(H20C,H20D)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A),
 C28A(H28A), C29A(H29A), C22A(H22A)
6.c Fitted hexagon refined as free rotating group:
 C24(C25,C26,C27,C28,C29), C24A(C25A,C26A,C27A,C28A,C29A)
6.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B), C23(H23C,H23D)
;
_shelx_res_checksum              80784
_olex2_date_sample_data_collection 2017-11-21
_olex2_date_sample_submission    2017-11-20
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_original_sample_id ES-2-92
_olex2_submission_special_instructions 'No special instructions were received'