Palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamines with alkyl chloroformates.
Shi, Yaqi; Yang, Fan; Wu, Yangjie; Organic & biomolecular chemistry 18 (2020) 4628–4637; doi:10.1039/d0ob00586j

data_7157533
_publ_section_title
;
 Palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamines with
 alkyl chloroformates.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4628
_journal_page_last               4637
_journal_paper_doi               10.1039/d0ob00586j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H17 Br N2 O3'
_chemical_formula_sum            'C20 H17 Br N2 O3'
_chemical_formula_weight         413.26
_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'
_atom_sites_solution_hydrogens   mixed
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Olex2 1.2
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2019-09-26 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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  1 omega  -55.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000   90.0000 93

  2 omega  -92.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -18.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  120.0000 35

  4 omega   -4.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 70

  5 omega   67.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 42

  6 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 26

  7 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 26

  8 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 26

  9 omega   63.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 27

 10 omega  127.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 30

 11 omega   93.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 79

 12 omega   50.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 70

 13 omega   42.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 39

 14 omega   42.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 58

 15 omega   65.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 111

 16 omega   48.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 42

 17 omega   57.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 55

 18 omega   42.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
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_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_theta_full        67.080
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_diffrn_reflns_theta_min         4.103
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_file            d0ob00586j2.cif
_cod_data_source_block           201907185
_cod_depositor_comments          'Adding full bibliography for 7157533.cif.'
_cod_original_cell_volume        1804.3(2)
_cod_database_code               7157533
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O6N4K1
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'