2-Pyridyl substituents enhance the activity of palladium-phospha-adamantane catalysts for the methoxycarbonylation of phenylacetylene.
Shuttleworth, Timothy A.; Miles-Hobbs, Alexandra M; Pringle, Paul G.; Sparkes, Hazel A.; Dalton transactions (Cambridge, England : 2003) 46 (2016) 125–137; doi:10.1039/c6dt03983a

data_7041341
_publ_section_title
;
 2-Pyridyl substituents enhance the activity of
 palladium-phospha-adamantane catalysts for the methoxycarbonylation of
 phenylacetylene.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              125
_journal_page_last               137
_journal_paper_doi               10.1039/c6dt03983a
_journal_volume                  46
_journal_year                    2016
_chemical_formula_moiety         'C16 H19 F3 N O3 P'
_chemical_formula_sum            'C16 H19 F3 N O3 P'
_chemical_formula_weight         361.29
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-27
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-08-05 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.305(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5819(9)
_cell_length_b                   10.5008(12)
_cell_length_c                   22.185(3)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    170
_cell_measurement_theta_max      66.523
_cell_measurement_theta_min      4.04
_cell_volume                     1743.0(4)
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      170
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33931
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.809
_diffrn_reflns_theta_min         4.038
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1339 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.4874.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+1.2866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt03983a2.cif
_cod_data_source_block           L6a
_cod_depositor_comments
'Adding full bibliography for 7041331--7041344.cif.'
_cod_original_cell_volume        1743.1(4)
_cod_database_code               7041341
_shelxl_version_number           2013-4
_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
 O1-C2 \\sim O1A-C2
 with sigma of 0.01
 O1A-C1 \\sim O1-C1
 with sigma of 0.01
 C7-C1 \\sim C7A-C1
 with sigma of 0.01
 F1A-C16 \\sim F2-C16 \\sim F2A-C16 \\sim F3-C16 \\sim F3A-C16 \\sim F1-C16
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C7 \\sim C7A: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
F1A \\sim F1 \\sim F2 \\sim F2A \\sim F3 \\sim F3A: within 1.7A with sigma of
0.004 and sigma for terminal atoms of 0.008
Uanis(O1) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
4. Others
 Fixed Sof: F1(0.42486) F2(0.42486) F3(0.42486) O1(0.50062) C7(0.50062)
 H7A(0.50062) H7B(0.50062) H7C(0.50062) F1A(0.57514) F2A(0.57514) F3A(0.57514)
 C7A(0.49938) H7AA(0.49938) H7AB(0.49938) H7AC(0.49938) O1A(0.49938)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C7A(H7AA,H7AB,H7AC)
;
_shelx_res_checksum              64209
_olex2_submission_special_instructions 'No special instructions were received'