Synthesis of Benzyl Esters via Functionalization of Multiple C-H Bonds by Palladium Catalysis.
Li, Danyang; Yu, Ming; Zhang, Jitan; Liu, Zhanxiang; Zhang, Yuhong; Organic letters 17 (2015) 5300–5303; doi:10.1021/acs.orglett.5b02518

data_1539135
_publ_section_title
;
 Synthesis of Benzyl Esters via Functionalization of Multiple C-H Bonds by
 Palladium Catalysis.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5300
_journal_page_last               5303
_journal_paper_doi               10.1021/acs.orglett.5b02518
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H15 Cl N2 O3'
_chemical_formula_sum            'C20 H15 Cl N2 O3'
_chemical_formula_weight         366.79
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-01
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90.00
_cell_angle_beta                 111.604(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5710(18)
_cell_length_b                   5.5448(5)
_cell_length_c                   20.450(2)
_cell_measurement_reflns_used    1716
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2788
_cell_measurement_theta_min      3.2078
_cell_volume                     1747.0(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0456782000
_diffrn_orient_matrix_UB_12      -0.0012754000
_diffrn_orient_matrix_UB_13      0.0093201000
_diffrn_orient_matrix_UB_21      -0.0054948000
_diffrn_orient_matrix_UB_22      0.0285611000
_diffrn_orient_matrix_UB_23      -0.0351795000
_diffrn_orient_matrix_UB_31      0.0017217000
_diffrn_orient_matrix_UB_32      0.1247235000
_diffrn_orient_matrix_UB_33      0.0081772000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6802
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0555P)^2^+0.2825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2116
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02518_si_002.cif
_cod_data_source_block           150601_ldy_6_129_136
_cod_depositor_comments          'Adding full bibliography for 1539135.cif.'
_cod_database_code               1539135
_chemical_oxdiff_formula         'c10 h10 n2 o8 cL1'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11), C16(H16),
  C17(H17), C18(H18), C19(H19), C20(H20)
;