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_4130750
_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         'C77 H71 Cl N4 O P2 Pd'
_chemical_formula_sum            'C77 H71 Cl N4 O P2 Pd'
_chemical_formula_weight         1272.17
_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             2015-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                62.886(4)
_cell_angle_beta                 86.197(4)
_cell_angle_gamma                82.330(4)
_cell_formula_units_Z            2
_cell_length_a                   11.827(3)
_cell_length_b                   18.130(5)
_cell_length_c                   19.269(5)
_cell_measurement_reflns_used    9059
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.27
_cell_volume                     3644.7(17)
_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_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50401
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.19
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1305 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.9213.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull reddish green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1324
_exptl_crystal_recrystallization_method 'DCM hexane'
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     783
_refine_ls_number_reflns         15782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                12423
_reflns_number_total             15782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b06361_si_002.cif
_cod_data_source_block           7Pd
_cod_original_cell_volume        3644.6(17)
_cod_database_code               4130750
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C5(H5A,H5B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C49(H49), C53(H53), C50(H50), C51(H51), C52(H52), C65(H65), C62(H62),
 C61(H61), C30(H30), C8(H8), C7(H7), C31(H31), C43(H43), C63(H63), C77(H77),
 C71(H71), C47(H47), C73(H73), C20(H20), C46(H46), C45(H45), C44(H44), C76(H76),
  C75(H75), C19(H19), C59(H59), C55(H55), C67(H67), C74(H74), C64(H64),
 C17(H17), C58(H58), C70(H70), C27(H27), C56(H56), C57(H57), C69(H69), C68(H68),
  C24(H24)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C29(H29A,H29B,H29C), C35(H35A,H35B,
 H35C), C34(H34A,H34B,H34C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C11(H11A,
 H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'