Synthesis of phthalic acid derivatives via Pd-catalyzed alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates.
Liao, Gang; Chen, Hao-Ming; Shi, Bing-Feng; Chemical communications (Cambridge, England) 54 (2018) 10859–10862; doi:10.1039/c8cc06663a

data_7122285
_publ_section_title
;
 Synthesis of phthalic acid derivatives via Pd-catalyzed
 alkoxycarbonylation of aromatic C-H bonds with alkyl chloroformates.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10859
_journal_page_last               10862
_journal_paper_doi               10.1039/c8cc06663a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1m7vwl
_audit_creation_date             2016-03-23
_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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_audit_update_record
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2016-08-01 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.955(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2268(10)
_cell_length_b                   8.5916(5)
_cell_length_c                   15.6448(13)
_cell_measurement_reflns_used    1682
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.4965
_cell_measurement_theta_min      3.2504
_cell_volume                     1681.5(2)
_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      170
_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      0.0272817000
_diffrn_orient_matrix_UB_12      0.0384840000
_diffrn_orient_matrix_UB_13      0.0411639000
_diffrn_orient_matrix_UB_21      0.0491158000
_diffrn_orient_matrix_UB_22      -0.0102240000
_diffrn_orient_matrix_UB_23      -0.0084272000
_diffrn_orient_matrix_UB_31      -0.0075713000
_diffrn_orient_matrix_UB_32      0.0723116000
_diffrn_orient_matrix_UB_33      -0.0231127000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6492
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96755
_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    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0521P)^2^+0.3734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2326
_reflns_number_total             3061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc06663a2.cif
_cod_data_source_block           160323_lg4_138_3
_cod_depositor_comments          'Adding full bibliography for 7122285.cif.'
_cod_database_code               7122285
_chemical_oxdiff_formula         'C10 h10 O2 n2'
_reflns_odcompleteness_completeness 99.57
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;