#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:45:15 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294465 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572139.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_1572139
loop_
_publ_author_name
'Zhang, Hao'
'Wen, Wei'
'Wang, Yu-Yang'
'Lu, Ze-Xi'
'Liu, Jin-Long'
'Wu, Zhu-Lian'
'Cai, Tian'
'Guo, Qi-Xiang'
_publ_section_title
;
 Asymmetric bifunctionalization of allenes with aryl iodides and amino
 acids enabled by chiral aldehyde/palladium combined catalysis.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              12983
_journal_page_last               12988
_journal_paper_doi               10.1039/d4sc03398a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2024-01-18 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                96.029(5)
_cell_angle_beta                 98.627(5)
_cell_angle_gamma                92.934(5)
_cell_formula_units_Z            2
_cell_length_a                   5.9905(4)
_cell_length_b                   8.0684(5)
_cell_length_c                   16.5496(9)
_cell_measurement_temperature    453(2)
_cell_volume                     784.65(8)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      453(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14056
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.767
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_min         5.443
_exptl_absorpt_coefficient_mu    0.638
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4770
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0835
_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)+(0.1612P)²+0.6616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2273
_refine_ls_wR_factor_ref         0.2314
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.587
_reflns_Friedel_fraction_max     0.558
_reflns_number_gt                4507
_reflns_number_total             4770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03398a2.cif
_cod_data_source_block           zh-a1409
_cod_depositor_comments          'Adding full bibliography for 1572139.cif.'
_cod_database_code               1572139
_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   0.780
_shelx_estimated_absorpt_t_max   0.847
_shelxl_version_number           2014-1
loop_
_space_group_symop_operation_xyz
'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
O1 O 0.7642(8) 0.8475(7) 0.6868(3) 0.0377(12) Uani 1 1 d . U . . .
O2 O 0.5023(8) 0.8160(5) 0.5735(3) 0.0297(10) Uani 1 1 d . . . . .
N1 N 0.5856(9) 1.0703(7) 0.6372(3) 0.0251(11) Uani 1 1 d . . . . .
H1 H 0.6644 1.1511 0.6684 0.030 Uiso 1 1 calc R U . . .
C1 C 0.6308(10) 0.9108(8) 0.6382(4) 0.0238(12) Uani 1 1 d . U . . .
C2 C 0.3800(12) 0.9267(8) 0.5226(4) 0.0287(14) Uani 1 1 d . . . . .
H2A H 0.2250 0.8824 0.5042 0.034 Uiso 1 1 calc R U . . .
H2B H 0.4516 0.9409 0.4747 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3867(9) 1.0938(7) 0.5770(3) 0.0183(11) Uani 1 1 d . . . . .
C4 C 0.1814(11) 1.1111(9) 0.6190(4) 0.0305(14) Uani 1 1 d . . . . .
H4A H 0.1461 1.0084 0.6403 0.046 Uiso 1 1 calc R U . . .
H4B H 0.0553 1.1358 0.5800 0.046 Uiso 1 1 calc R U . . .
H4C H 0.2118 1.2000 0.6633 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4338(10) 1.2480(7) 0.5323(3) 0.0199(11) Uani 1 1 d . . . . .
H5A H 0.4624 1.3458 0.5727 0.024 Uiso 1 1 calc R U . . .
H5B H 0.5704 1.2332 0.5082 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2452(9) 1.2810(7) 0.4653(3) 0.0186(11) Uani 1 1 d . . . . .
C7 C 0.2022(9) 1.1520(7) 0.3924(3) 0.0178(11) Uani 1 1 d . . . . .
C8 C 0.3596(10) 1.1270(8) 0.3396(3) 0.0234(12) Uani 1 1 d . . . . .
H8 H 0.4936 1.1945 0.3487 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3204(13) 1.0028(9) 0.2732(4) 0.0344(16) Uani 1 1 d . . . . .
H9 H 0.4279 0.9870 0.2385 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1187(13) 0.9018(9) 0.2589(4) 0.0368(16) Uani 1 1 d . . . . .
H10 H 0.0903 0.8189 0.2144 0.044 Uiso 1 1 calc R U . . .
C11 C -0.0372(12) 0.9263(9) 0.3112(4) 0.0330(15) Uani 1 1 d . . . . .
H11 H -0.1701 0.8577 0.3026 0.040 Uiso 1 1 calc R U . . .
C12 C 0.0007(10) 1.0511(8) 0.3763(4) 0.0236(12) Uani 1 1 d . . . . .
H12 H -0.1092 1.0682 0.4099 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1261(10) 1.4152(7) 0.4737(3) 0.0224(12) Uani 1 1 d . . . . .
H13 H 0.1659 1.4853 0.5226 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0622(10) 1.4662(7) 0.4146(3) 0.0193(11) Uani 1 1 d . U . . .
C15 C -0.0705(10) 1.4377(8) 0.3300(3) 0.0221(12) Uani 1 1 d . . . . .
H15 H 0.0470 1.3871 0.3083 0.027 Uiso 1 1 calc R U . . .
C16 C -0.2553(11) 1.4848(8) 0.2773(3) 0.0246(13) Uani 1 1 d . . . . .
H16 H -0.2611 1.4643 0.2207 0.030 Uiso 1 1 calc R U . . .
C17 C -0.4285(11) 1.5612(8) 0.3088(4) 0.0257(13) Uani 1 1 d . . . . .
H17 H -0.5528 1.5900 0.2735 0.031 Uiso 1 1 calc R U . . .
C18 C -0.4181(11) 1.5948(8) 0.3920(4) 0.0244(12) Uani 1 1 d . . . . .
H18 H -0.5343 1.6483 0.4131 0.029 Uiso 1 1 calc R U . . .
C19 C -0.2348(11) 1.5495(8) 0.4454(3) 0.0242(12) Uani 1 1 d . . . . .
H19 H -0.2277 1.5751 0.5019 0.029 Uiso 1 1 calc R U . . .
O3 O 0.6903(8) 1.3423(6) 0.7596(3) 0.0392(12) Uani 1 1 d . . . . .
O4 O 1.0588(7) 1.3544(5) 0.8139(3) 0.0266(9) Uani 1 1 d . U . . .
N2 N 0.9163(8) 1.5875(6) 0.7780(3) 0.0189(10) Uani 1 1 d . . . . .
H2 H 0.8136 1.6563 0.7676 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8730(10) 1.4255(8) 0.7815(4) 0.0215(12) Uani 1 1 d . . . . .
C21 C 1.2408(10) 1.4868(7) 0.8387(4) 0.0210(11) Uani 1 1 d . . . . .
H21A H 1.3811 1.4513 0.8222 0.025 Uiso 1 1 calc R U . . .
H21B H 1.2650 1.5164 0.8979 0.025 Uiso 1 1 calc R U . . .
C22 C 1.1585(9) 1.6351(7) 0.7941(3) 0.0169(11) Uani 1 1 d . . . . .
C23 C 1.2506(11) 1.6339(9) 0.7131(4) 0.0284(14) Uani 1 1 d . . . . .
H23A H 1.2244 1.5240 0.6835 0.043 Uiso 1 1 calc R U . . .
H23B H 1.4101 1.6643 0.7240 0.043 Uiso 1 1 calc R U . . .
H23C H 1.1752 1.7125 0.6807 0.043 Uiso 1 1 calc R U . . .
C24 C 1.2122(9) 1.8090(7) 0.8441(3) 0.0190(11) Uani 1 1 d . . . . .
H24A H 1.3712 1.8182 0.8678 0.023 Uiso 1 1 calc R U . . .
H24B H 1.1903 1.8927 0.8062 0.023 Uiso 1 1 calc R U . . .
C25 C 1.0779(9) 1.8518(7) 0.9122(3) 0.0150(11) Uani 1 1 d . . . . .
C26 C 1.1024(9) 1.7471(7) 0.9805(3) 0.0149(10) Uani 1 1 d . . . . .
C27 C 1.3145(9) 1.7436(7) 1.0309(3) 0.0185(11) Uani 1 1 d . . . . .
H27 H 1.4363 1.8137 1.0237 0.022 Uiso 1 1 calc R U . . .
C28 C 1.3412(11) 1.6362(8) 1.0909(3) 0.0253(13) Uani 1 1 d . . . . .
H28 H 1.4803 1.6359 1.1244 0.030 Uiso 1 1 calc R U . . .
C29 C 1.1623(11) 1.5288(8) 1.1015(4) 0.0283(13) Uani 1 1 d . U . . .
H29 H 1.1823 1.4557 1.1415 0.034 Uiso 1 1 calc R U . . .
C30 C 0.9533(11) 1.5306(8) 1.0523(4) 0.0254(13) Uani 1 1 d . . . . .
H30 H 0.8329 1.4588 1.0592 0.031 Uiso 1 1 calc R U . . .
C31 C 0.9247(10) 1.6402(7) 0.9928(3) 0.0216(12) Uani 1 1 d . . . . .
H31 H 0.7838 1.6419 0.9606 0.026 Uiso 1 1 calc R U . . .
C32 C 0.9434(10) 1.9803(7) 0.9080(3) 0.0216(12) Uani 1 1 d . . . . .
H32 H 0.9322 2.0310 0.8598 0.026 Uiso 1 1 calc R U . . .
C33 C 0.8121(10) 2.0503(7) 0.9699(3) 0.0186(11) Uani 1 1 d . . . . .
C34 C 0.8724(10) 2.0487(7) 1.0550(3) 0.0200(11) Uani 1 1 d . . . . .
H34 H 1.0058 2.0023 1.0749 0.024 Uiso 1 1 calc R U . . .
C35 C 0.7395(10) 2.1141(8) 1.1099(4) 0.0255(13) Uani 1 1 d . . . . .
H35 H 0.7831 2.1106 1.1660 0.031 Uiso 1 1 calc R U . . .
C36 C 0.5406(11) 2.1851(7) 1.0817(4) 0.0271(13) Uani 1 1 d . . . . .
H36 H 0.4489 2.2277 1.1184 0.032 Uiso 1 1 calc R U . . .
C37 C 0.4809(10) 2.1915(8) 0.9978(4) 0.0265(13) Uani 1 1 d . . . . .
H37 H 0.3485 2.2397 0.9783 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6136(11) 2.1281(8) 0.9435(4) 0.0241(12) Uani 1 1 d . . . . .
H38 H 0.5719 2.1366 0.8877 0.029 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'
N N 0.0311 0.0180 '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'
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
C1 O2 C2 108.1(5) . . ?
C1 N1 C3 112.8(5) . . ?
O1 C1 N1 129.2(6) . . ?
O1 C1 O2 120.8(6) . . ?
N1 C1 O2 110.0(5) . . ?
O2 C2 C3 105.8(4) . . ?
N1 C3 C4 110.1(5) . . ?
N1 C3 C2 98.1(5) . . ?
C4 C3 C2 112.9(5) . . ?
N1 C3 C5 109.7(5) . . ?
C4 C3 C5 111.6(5) . . ?
C2 C3 C5 113.6(4) . . ?
C6 C5 C3 115.0(5) . . ?
C13 C6 C7 123.8(5) . . ?
C13 C6 C5 121.0(5) . . ?
C7 C6 C5 115.2(5) . . ?
C8 C7 C12 118.3(5) . . ?
C8 C7 C6 121.6(5) . . ?
C12 C7 C6 120.1(5) . . ?
C7 C8 C9 121.1(6) . . ?
C8 C9 C10 119.7(6) . . ?
C11 C10 C9 119.3(6) . . ?
C10 C11 C12 120.9(6) . . ?
C11 C12 C7 120.7(6) . . ?
C6 C13 C14 127.9(5) . . ?
C15 C14 C19 118.7(5) . . ?
C15 C14 C13 122.7(5) . . ?
C19 C14 C13 118.5(5) . . ?
C14 C15 C16 120.1(5) . . ?
C17 C16 C15 120.4(5) . . ?
C18 C17 C16 120.0(6) . . ?
C17 C18 C19 120.5(6) . . ?
C18 C19 C14 120.3(5) . . ?
C20 O4 C21 107.7(4) . . ?
C20 N2 C22 112.1(5) . . ?
O3 C20 N2 127.8(6) . . ?
O3 C20 O4 121.0(6) . . ?
N2 C20 O4 111.3(5) . . ?
O4 C21 C22 104.9(4) . . ?
N2 C22 C23 109.9(5) . . ?
N2 C22 C21 99.1(4) . . ?
C23 C22 C21 110.1(5) . . ?
N2 C22 C24 112.1(5) . . ?
C23 C22 C24 109.7(5) . . ?
C21 C22 C24 115.6(5) . . ?
C25 C24 C22 117.2(4) . . ?
C32 C25 C26 123.8(5) . . ?
C32 C25 C24 119.4(5) . . ?
C26 C25 C24 116.8(5) . . ?
C31 C26 C27 118.4(5) . . ?
C31 C26 C25 121.2(5) . . ?
C27 C26 C25 120.2(5) . . ?
C28 C27 C26 120.1(5) . . ?
C27 C28 C29 120.6(6) . . ?
C28 C29 C30 119.9(5) . . ?
C31 C30 C29 119.7(5) . . ?
C26 C31 C30 121.3(6) . . ?
C25 C32 C33 128.2(5) . . ?
C34 C33 C38 116.6(5) . . ?
C34 C33 C32 124.6(5) . . ?
C38 C33 C32 118.8(5) . . ?
C35 C34 C33 121.8(5) . . ?
C34 C35 C36 120.1(5) . . ?
C35 C36 C37 118.9(6) . . ?
C38 C37 C36 120.9(6) . . ?
C37 C38 C33 121.6(5) . . ?
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
O1 C1 1.217(7) . ?
O2 C1 1.359(8) . ?
O2 C2 1.443(7) . ?
N1 C1 1.330(8) . ?
N1 C3 1.468(7) . ?
C2 C3 1.536(8) . ?
C3 C4 1.506(8) . ?
C3 C5 1.547(7) . ?
C5 C6 1.514(7) . ?
C6 C13 1.333(8) . ?
C6 C7 1.491(8) . ?
C7 C8 1.386(7) . ?
C7 C12 1.396(8) . ?
C8 C9 1.391(9) . ?
C9 C10 1.397(11) . ?
C10 C11 1.374(10) . ?
C11 C12 1.380(9) . ?
C13 C14 1.483(8) . ?
C14 C15 1.388(7) . ?
C14 C19 1.393(8) . ?
C15 C16 1.397(8) . ?
C16 C17 1.374(9) . ?
C17 C18 1.366(9) . ?
C18 C19 1.392(9) . ?
O3 C20 1.239(8) . ?
O4 C20 1.344(7) . ?
O4 C21 1.467(7) . ?
N2 C20 1.328(8) . ?
N2 C22 1.459(7) . ?
C21 C22 1.536(8) . ?
C22 C23 1.523(7) . ?
C22 C24 1.545(8) . ?
C24 C25 1.502(7) . ?
C25 C32 1.346(8) . ?
C25 C26 1.475(7) . ?
C26 C31 1.388(8) . ?
C26 C27 1.415(7) . ?
C27 C28 1.381(8) . ?
C28 C29 1.386(9) . ?
C29 C30 1.389(9) . ?
C30 C31 1.389(8) . ?
C32 C33 1.466(7) . ?
C33 C34 1.402(7) . ?
C33 C38 1.406(9) . ?
C34 C35 1.378(8) . ?
C35 C36 1.387(9) . ?
C36 C37 1.388(10) . ?
C37 C38 1.364(9) . ?
