Facile Incorporation of Pd(PPh3)2Hal Substituents into Polymethines, Merocyanines, and Perylene Diimides as a Means of Suppressing Intermolecular Interactions.
Davydenko, Iryna; Barlow, Stephen; Sharma, Rajesh; Benis, Sepehr; Simon, Janos; Allen, Taylor G.; Cooper, Matthew W.; Khrustalev, Victor; Jucov, Evgheni V.; Castañeda, Raúl; Ordonez, Carlos; Li, Zhong'an; Chi, San-Hui; Jang, Sei-Hum; Parker, Timothy C.; Timofeeva, Tatiana V.; Perry, Joseph W.; Jen, Alex K.-Y.; Hagan, David J.; Van Stryland, Eric W.; Marder, Seth R.; Journal of the American Chemical Society 138 (2016) 10112–10115; doi:10.1021/jacs.6b06361

data_4130749
_publ_section_title
;
 Facile Incorporation of Pd(PPh3)2Hal Substituents into Polymethines,
 Merocyanines, and Perylene Diimides as a Means of Suppressing
 Intermolecular Interactions.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10112
_journal_page_last               10115
_journal_paper_doi               10.1021/jacs.6b06361
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety
'0.5(C41 H41 Cl N4 O), 0.5(C41 H42 Cl N4 O), C H Cl3'
_chemical_formula_sum            'C42 H42.5 Cl4 N4 O'
_chemical_formula_weight         761.10
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.505(3)
_cell_angle_beta                 106.024(3)
_cell_angle_gamma                111.977(3)
_cell_formula_units_Z            4
_cell_length_a                   15.619(3)
_cell_length_b                   15.985(3)
_cell_length_c                   19.520(3)
_cell_measurement_reflns_used    8043
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.19
_cell_volume                     4309.3(13)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39842
_diffrn_reflns_theta_full        23.39
_diffrn_reflns_theta_max         23.39
_diffrn_reflns_theta_min         1.09
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0658 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.9254.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull greenish green'
_exptl_crystal_colour_lustre     dark
_exptl_crystal_colour_modifier   green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1594
_exptl_crystal_recrystallization_method 'Chloroform and hexane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.447
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     935
_refine_ls_number_reflns         12448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0953
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1822P)^2^+3.9384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2797
_refine_ls_wR_factor_ref         0.3037
_reflns_number_gt                8352
_reflns_number_total             12448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b06361_si_002.cif
_cod_data_source_block           7Cl_CHCl3
_cod_original_formula_sum        'C42 H42.50 Cl4 N4 O'
_cod_database_code               4130749
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C48(H48A,H48B), C72(H72A,H72B), C93(H93A,H93B), C58(H58A,H58B), C65(H65A,
 H65B), C74(H74A,H74B), C79(H79A,H79B), C91(H91A,H91B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C20(H20), C29(H29), C32(H32), C50(H50), C76(H76), C84(H84),
 C89(H89), C30(H30), C36(H36), C64(H64), C67(H67), C71(H71), C73(H73), C75(H75),
  C82(H82)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C35(H35A,H35B,H35C), C66(H66A,H66B,H66C), C68(H68A,H68B,
 H68C), C96(H96A,H96B,H96C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C), C47(H47A,
 H47B,H47C), C69(H69A,H69B,H69C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C),
 C87(H87A,H87B,H87C), C94(H94A,H94B,H94C), C99(H99A,H99B,H99C), C101(H10A,H10B,
 H10C), C2(H2A,H2B,H2C)
;
_olex2_submission_special_instructions 'No special instructions were received'