#------------------------------------------------------------------------------
#$Date: 2020-10-06 09:04:00 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257226 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127117.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_7127117
loop_
_publ_author_name
'Li, Yan'
'Cheng, Xiu-Fen'
'Fei, Fan'
'Wu, Tian-Rui'
'Bian, Kang-Jie'
'Zhou, Xin'
'Wang, Xi-Sheng'
_publ_section_title
;
 Palladium(II)-catalyzed asymmetric C-H carbonylation to diverse
 isoquinoline derivatives bearing all-carbon quaternary stereocenters.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11605
_journal_page_last               11608
_journal_paper_doi               10.1039/d0cc05219a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2020-05-27 deposited with the CCDC.	2020-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.53180(10)
_cell_length_b                   9.34100(10)
_cell_length_c                   18.0021(2)
_cell_measurement_reflns_used    3817
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      71.1520
_cell_measurement_theta_min      4.8970
_cell_volume                     1434.69(3)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4843
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.260
_diffrn_reflns_theta_min         4.913
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_coef       0.0268(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0356
_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)+(0.0505P)²+0.1206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                2622
_reflns_number_total             2688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05219a2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7127117--7127120.cif.'
_cod_database_code               7127117
_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.
;
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.862
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O3 O -0.04151(19) 0.78901(16) 0.62237(10) 0.0691(5) Uani 1 1 d . . . . .
O1 O 0.1280(2) 0.6518(2) 0.71970(8) 0.0776(6) Uani 1 1 d . . . . .
N1 N 0.0431(2) 0.66848(18) 0.60173(9) 0.0516(4) Uani 1 1 d . . . . .
O2 O -0.0755(3) 0.6811(2) 0.48994(11) 0.0876(6) Uani 1 1 d . . . . .
C10 C 0.3734(2) 0.47203(19) 0.66561(10) 0.0431(4) Uani 1 1 d . . . . .
C5 C 0.1248(2) 0.6005(2) 0.65852(10) 0.0479(4) Uani 1 1 d . . . . .
C4 C 0.2021(2) 0.4568(2) 0.64045(10) 0.0434(4) Uani 1 1 d . . . . .
C2 C 0.1097(2) 0.4934(2) 0.50762(10) 0.0505(4) Uani 1 1 d . . . . .
C15 C 0.4696(3) 0.5644(2) 0.62700(12) 0.0569(5) Uani 1 1 d . . . . .
H15 H 0.4307 0.6138 0.5861 0.068 Uiso 1 1 calc R U . . .
C1 C 0.0175(3) 0.6199(2) 0.52972(12) 0.0563(5) Uani 1 1 d . . . . .
C3 C 0.1961(2) 0.4162(2) 0.55879(10) 0.0459(4) Uani 1 1 d . . . . .
C11 C 0.4330(3) 0.3990(3) 0.72612(12) 0.0601(5) Uani 1 1 d . . . . .
H11 H 0.3694 0.3369 0.7529 0.072 Uiso 1 1 calc R U . . .
C6 C 0.1058(3) 0.4519(3) 0.43282(12) 0.0707(7) Uani 1 1 d . . . . .
H6 H 0.0493 0.5058 0.3986 0.085 Uiso 1 1 calc R U . . .
C12 C 0.5888(3) 0.4188(3) 0.74677(16) 0.0774(8) Uani 1 1 d . . . . .
H12 H 0.6291 0.3684 0.7870 0.093 Uiso 1 1 calc R U . . .
C16 C 0.1095(3) 0.3445(3) 0.68512(13) 0.0638(6) Uani 1 1 d . . . . .
H16A H 0.1561 0.2519 0.6782 0.096 Uiso 1 1 calc R U . . .
H16B H 0.0029 0.3426 0.6682 0.096 Uiso 1 1 calc R U . . .
H16C H 0.1119 0.3691 0.7369 0.096 Uiso 1 1 calc R U . . .
C13 C 0.6828(3) 0.5110(3) 0.70879(16) 0.0783(8) Uani 1 1 d . . . . .
H13 H 0.7863 0.5244 0.7235 0.094 Uiso 1 1 calc R U . . .
C14 C 0.6250(3) 0.5840(3) 0.64885(17) 0.0740(7) Uani 1 1 d . . . . .
H14 H 0.6892 0.6467 0.6227 0.089 Uiso 1 1 calc R U . . .
C9 C 0.2740(3) 0.2938(3) 0.53425(15) 0.0680(6) Uani 1 1 d . . . . .
H9 H 0.3311 0.2389 0.5678 0.082 Uiso 1 1 calc R U . . .
C17 C 0.0434(4) 0.9164(3) 0.60392(18) 0.0792(8) Uani 1 1 d . . . . .
H17A H 0.0504 0.9252 0.5509 0.119 Uiso 1 1 calc R U . . .
H17B H 0.1469 0.9112 0.6246 0.119 Uiso 1 1 calc R U . . .
H17C H -0.0102 0.9982 0.6239 0.119 Uiso 1 1 calc R U . . .
C8 C 0.2673(3) 0.2534(3) 0.46082(17) 0.0833(9) Uani 1 1 d . . . . .
H8 H 0.3195 0.1712 0.4454 0.100 Uiso 1 1 calc R U . . .
C7 C 0.1848(3) 0.3325(4) 0.40999(15) 0.0867(9) Uani 1 1 d . . . . .
H7 H 0.1826 0.3052 0.3603 0.104 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N1 O3 C17 110.40(18) . . ?
O3 N1 C5 115.75(16) . . ?
O3 N1 C1 115.61(17) . . ?
C5 N1 C1 127.94(17) . . ?
C15 C10 C11 119.14(19) . . ?
C15 C10 C4 118.40(17) . . ?
C11 C10 C4 122.45(18) . . ?
O1 C5 N1 120.22(19) . . ?
O1 C5 C4 122.31(18) . . ?
N1 C5 C4 117.41(16) . . ?
C3 C4 C5 114.22(15) . . ?
C3 C4 C10 109.89(14) . . ?
C5 C4 C10 105.44(15) . . ?
C3 C4 C16 108.54(17) . . ?
C5 C4 C16 105.37(15) . . ?
C10 C4 C16 113.40(16) . . ?
C3 C2 C6 120.6(2) . . ?
C3 C2 C1 121.54(17) . . ?
C6 C2 C1 117.9(2) . . ?
C10 C15 C14 120.4(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O2 C1 N1 120.0(2) . . ?
O2 C1 C2 124.6(2) . . ?
N1 C1 C2 115.40(17) . . ?
C2 C3 C9 118.09(19) . . ?
C2 C3 C4 122.14(18) . . ?
C9 C3 C4 119.71(18) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C6 C2 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C8 C9 C3 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C3 C9 H9 119.7 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
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
O3 N1 1.388(2) . ?
O3 C17 1.432(3) . ?
O1 C5 1.201(2) . ?
N1 C5 1.391(3) . ?
N1 C1 1.391(3) . ?
O2 C1 1.212(3) . ?
C10 C15 1.379(3) . ?
C10 C11 1.382(3) . ?
C10 C4 1.537(2) . ?
C5 C4 1.530(3) . ?
C4 C3 1.519(3) . ?
C4 C16 1.540(3) . ?
C2 C3 1.383(3) . ?
C2 C6 1.402(3) . ?
C2 C1 1.474(3) . ?
C15 C14 1.394(3) . ?
C15 H15 0.9300 . ?
C3 C9 1.394(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C12 C13 1.361(5) . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C9 C8 1.376(3) . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 C7 1.371(5) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 O3 N1 C5 99.9(2) . . . . ?
C17 O3 N1 C1 -88.9(2) . . . . ?
O3 N1 C5 O1 -5.0(3) . . . . ?
C1 N1 C5 O1 -174.9(2) . . . . ?
O3 N1 C5 C4 172.29(15) . . . . ?
C1 N1 C5 C4 2.4(3) . . . . ?
O1 C5 C4 C3 -175.4(2) . . . . ?
N1 C5 C4 C3 7.4(2) . . . . ?
O1 C5 C4 C10 -54.6(2) . . . . ?
N1 C5 C4 C10 128.12(17) . . . . ?
O1 C5 C4 C16 65.6(2) . . . . ?
N1 C5 C4 C16 -111.7(2) . . . . ?
C15 C10 C4 C3 55.1(2) . . . . ?
C11 C10 C4 C3 -126.2(2) . . . . ?
C15 C10 C4 C5 -68.5(2) . . . . ?
C11 C10 C4 C5 110.2(2) . . . . ?
C15 C10 C4 C16 176.76(19) . . . . ?
C11 C10 C4 C16 -4.6(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C4 C10 C15 C14 178.6(2) . . . . ?
O3 N1 C1 O2 -1.0(3) . . . . ?
C5 N1 C1 O2 169.0(2) . . . . ?
O3 N1 C1 C2 178.95(17) . . . . ?
C5 N1 C1 C2 -11.1(3) . . . . ?
C3 C2 C1 O2 -170.3(2) . . . . ?
C6 C2 C1 O2 8.8(3) . . . . ?
C3 C2 C1 N1 9.8(3) . . . . ?
C6 C2 C1 N1 -171.1(2) . . . . ?
C6 C2 C3 C9 -2.2(3) . . . . ?
C1 C2 C3 C9 176.88(19) . . . . ?
C6 C2 C3 C4 -179.39(19) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C5 C4 C3 C2 -8.3(3) . . . . ?
C10 C4 C3 C2 -126.53(19) . . . . ?
C16 C4 C3 C2 108.9(2) . . . . ?
C5 C4 C3 C9 174.59(19) . . . . ?
C10 C4 C3 C9 56.3(2) . . . . ?
C16 C4 C3 C9 -68.2(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C4 C10 C11 C12 -179.1(2) . . . . ?
C3 C2 C6 C7 1.4(3) . . . . ?
C1 C2 C6 C7 -177.7(2) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C10 C15 C14 C13 0.2(4) . . . . ?
C2 C3 C9 C8 1.4(3) . . . . ?
C4 C3 C9 C8 178.6(2) . . . . ?
C3 C9 C8 C7 0.3(4) . . . . ?
C2 C6 C7 C8 0.3(4) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?
