#------------------------------------------------------------------------------
#$Date: 2021-12-22 00:59:12 +0200 (Wed, 22 Dec 2021) $
#$Revision: 271564 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/94/7129451.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7129451
loop_
_publ_author_name
'Lu, Zhiqiang'
'li, yanzhi'
'ru, yi'
'yang, shujian'
'hao, chu'
'zuo, mengke'
'jiao, rongkai'
'Wu, Weilong'
'Zhou, Yan'
'Yao, Hui'
'huang, nianyu'
'Fu, Yuqin'
_publ_section_title
;
 Coordination Effect Enabled Palladium-Catalyzed Regioselective
 O-Alkylation of 2-Pyridones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06110K
_journal_year                    2022
_chemical_formula_moiety         'C21 H18 N2 O'
_chemical_formula_sum            'C21 H18 N2 O'
_chemical_formula_weight         314.37
_chemical_name_systematic        zqlu3i-7
_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     dual
_audit_creation_date             2021-08-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-02 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                101.494(3)
_cell_angle_beta                 94.001(3)
_cell_angle_gamma                110.869(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2919(3)
_cell_length_b                   8.7725(4)
_cell_length_c                   13.1099(5)
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9360
_cell_measurement_theta_min      4.1710
_cell_volume                     862.81(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  -3.00   1.00    8.66    --  -13.64 126.00  86.76   65
  2  ω    -52.00  32.00   1.00    8.66    --   15.05 -57.00-120.00   84
  3  ω     -2.00  82.00   1.00    8.66    --   15.05  57.00  60.00   84
  4  ω    -54.00  34.00   1.00    8.66    --   15.05 -38.00 150.00   88
  5  ω     -4.00  65.00   1.00    8.66    --   15.05-118.00 -31.00   69
  6  ω    -12.00  83.00   1.00    8.66    --   15.05  77.00 150.00   95
  7  ω     -4.00  84.00   1.00    8.66    --   15.05  38.00 -30.00   88
  8  ω    -20.00  54.00   1.00    8.66    --   15.05 -99.00  60.00   74
  9  ω    -54.00  84.00   1.00    8.66    --   15.05   0.00 -90.00  138
 10  ω    -20.00  25.00   1.00    8.66    --  -13.64 -99.00-180.00   45
 11  ω    -64.00   3.00   1.00    8.66    --  -13.64 119.00 139.12   67
 12  ω    -20.00  25.00   1.00    8.66    --  -13.64 -99.00 -90.00   45
 13  ω    -20.00  52.00   1.00    8.66    --   15.05 -99.00-120.00   72
 14  ω      5.00  71.00   1.00    8.66    --   15.05-129.00  37.36   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0227378000
_diffrn_orient_matrix_UB_12      0.0108222000
_diffrn_orient_matrix_UB_13      0.0548694000
_diffrn_orient_matrix_UB_21      -0.0657463000
_diffrn_orient_matrix_UB_22      0.0327013000
_diffrn_orient_matrix_UB_23      0.0100045000
_diffrn_orient_matrix_UB_31      -0.0611901000
_diffrn_orient_matrix_UB_32      -0.0822231000
_diffrn_orient_matrix_UB_33      -0.0033652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20397
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.466
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_preparation
'obtained by slow evaporation of their ether acetate/PE mixed solutions'
_exptl_crystal_recrystallization_method
'A crystal with approximate dimensions of 0.18*0.18*0.18mm^3'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0608
_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/[σ²(Fo²)+(0.0614P)²+0.1932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3113
_reflns_number_total             3916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06110k2.cif
_cod_data_source_block           lzq20210801-1
_cod_original_cell_volume        862.81(6)
_cod_database_code               7129451
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_date_sample_data_collection 2021-08-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.624
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7021(2) 0.40447(18) 0.80676(11) 0.0391(3) Uani 1 1 d . . . . .
C2 C 0.8257(2) 0.5441(2) 0.87710(14) 0.0499(4) Uani 1 1 d . . . . .
H2 H 0.7899 0.6191 0.9210 0.060 Uiso 1 1 calc R . . . .
C3 C 1.0012(2) 0.5728(2) 0.88260(15) 0.0584(5) Uani 1 1 d . . . . .
H3 H 1.0828 0.6658 0.9308 0.070 Uiso 1 1 calc R . . . .
C4 C 1.0551(3) 0.4643(3) 0.81708(16) 0.0658(5) Uani 1 1 d . . . . .
H4 H 1.1733 0.4832 0.8211 0.079 Uiso 1 1 calc R . . . .
C5 C 0.9351(3) 0.3284(3) 0.74590(16) 0.0677(6) Uani 1 1 d . . . . .
H5 H 0.9726 0.2568 0.7002 0.081 Uiso 1 1 calc R . . . .
C6 C 0.7588(2) 0.2962(2) 0.74107(14) 0.0530(4) Uani 1 1 d . . . . .
H6 H 0.6781 0.2016 0.6936 0.064 Uiso 1 1 calc R . . . .
C7 C 0.4252(2) 0.25368(18) 0.87477(12) 0.0417(4) Uani 1 1 d . . . . .
C8 C 0.5102(2) 0.2734(2) 0.97350(14) 0.0559(5) Uani 1 1 d . . . . .
H8 H 0.6218 0.3555 0.9962 0.067 Uiso 1 1 calc R . . . .
C9 C 0.4328(3) 0.1733(3) 1.03934(17) 0.0698(6) Uani 1 1 d . . . . .
H9 H 0.4924 0.1890 1.1057 0.084 Uiso 1 1 calc R . . . .
C10 C 0.2699(3) 0.0519(3) 1.00797(19) 0.0736(6) Uani 1 1 d . . . . .
H10 H 0.2187 -0.0165 1.0520 0.088 Uiso 1 1 calc R . . . .
C11 C 0.1827(3) 0.0319(3) 0.9112(2) 0.0808(7) Uani 1 1 d . . . . .
H11 H 0.0705 -0.0496 0.8898 0.097 Uiso 1 1 calc R . . . .
C12 C 0.2588(3) 0.1313(2) 0.84415(17) 0.0654(5) Uani 1 1 d . . . . .
H12 H 0.1976 0.1157 0.7782 0.078 Uiso 1 1 calc R . . . .
C13 C 0.5103(2) 0.36990(18) 0.80576(12) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.4960 0.4768 0.8297 0.049 Uiso 1 1 calc R . . . .
C14 C 0.37356(19) 0.3849(2) 0.64148(12) 0.0400(3) Uani 1 1 d . . . . .
C15 C 0.2754(2) 0.2946(2) 0.54204(12) 0.0447(4) Uani 1 1 d . . . . .
C16 C 0.2196(2) 0.3818(2) 0.47837(13) 0.0536(4) Uani 1 1 d . . . . .
C17 C 0.2669(3) 0.5525(3) 0.51833(15) 0.0602(5) Uani 1 1 d . . . . .
H17 H 0.2315 0.6148 0.4784 0.072 Uiso 1 1 calc R . . . .
C18 C 0.3654(2) 0.6315(2) 0.61620(14) 0.0532(4) Uani 1 1 d . . . . .
C19 C 0.4190(4) 0.8158(3) 0.66174(19) 0.0815(7) Uani 1 1 d . . . . .
H19A H 0.3543 0.8333 0.7179 0.122 Uiso 1 1 calc GR . . . .
H19B H 0.3954 0.8682 0.6079 0.122 Uiso 1 1 calc GR . . . .
H19C H 0.5416 0.8642 0.6887 0.122 Uiso 1 1 calc GR . . . .
C20 C 0.1137(3) 0.2924(3) 0.37136(16) 0.0778(7) Uani 1 1 d . . . . .
H20A H 0.1878 0.2661 0.3235 0.117 Uiso 1 1 calc GR . . . .
H20B H 0.0632 0.3635 0.3462 0.117 Uiso 1 1 calc GR . . . .
H20C H 0.0224 0.1905 0.3759 0.117 Uiso 1 1 calc GR . . . .
C21 C 0.2353(2) 0.1173(3) 0.51001(14) 0.0571(5) Uani 1 1 d . . . . .
N1 N 0.41925(17) 0.54689(17) 0.67817(10) 0.0454(3) Uani 1 1 d . . . . .
N2 N 0.2043(3) -0.0232(2) 0.48413(15) 0.0853(6) Uani 1 1 d . . . . .
O1 O 0.41756(15) 0.29122(13) 0.69991(8) 0.0507(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C13 120.03(14) . . ?
C6 C1 C2 118.56(15) . . ?
C6 C1 C13 121.37(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.70(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.98(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.94(18) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.66(18) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.12(16) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C12 117.77(17) . . ?
C8 C7 C13 120.10(14) . . ?
C12 C7 C13 122.05(15) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.19(18) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(2) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 120.4(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C1 C13 C7 113.66(12) . . ?
C1 C13 H13 108.8 . . ?
C7 C13 H13 108.8 . . ?
O1 C13 C1 109.78(12) . . ?
O1 C13 C7 106.97(12) . . ?
O1 C13 H13 108.8 . . ?
N1 C14 C15 124.32(14) . . ?
N1 C14 O1 120.85(13) . . ?
O1 C14 C15 114.82(14) . . ?
C14 C15 C21 119.17(14) . . ?
C16 C15 C14 118.23(16) . . ?
C16 C15 C21 122.60(15) . . ?
C15 C16 C20 120.83(18) . . ?
C17 C16 C15 117.00(16) . . ?
C17 C16 C20 122.17(17) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.95(16) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 122.34(17) . . ?
N1 C18 C17 122.10(17) . . ?
N1 C18 C19 115.56(17) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C15 179.5(2) . . ?
C14 N1 C18 117.40(14) . . ?
C14 O1 C13 119.43(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.383(2) . ?
C1 C13 1.507(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.365(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 C12 1.383(2) . ?
C7 C13 1.517(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 O1 1.4439(17) . ?
C14 C15 1.404(2) . ?
C14 N1 1.309(2) . ?
C14 O1 1.3496(18) . ?
C15 C16 1.396(2) . ?
C15 C21 1.434(3) . ?
C16 C17 1.382(3) . ?
C16 C20 1.501(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 C19 1.495(3) . ?
C18 N1 1.355(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.139(2) . ?
