#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:46:49 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/77/4517779.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_4517779
loop_
_publ_author_name
'Guo, Tao'
'Ding, Yalan'
'Zhou, Lili'
'Xu, Haiyan'
'Loh, Teck-Peng'
'Wu, Xiaojin'
_publ_section_title
;
 Palladium-Catalyzed anti-Michael Reductive Heck Reaction of
 α,β-Unsaturated Esters
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              7262
_journal_page_last               7268
_journal_paper_doi               10.1021/acscatal.0c02414
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C29 H29 N2 O3'
_chemical_formula_weight         453.54
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                94.540(5)
_cell_angle_beta                 111.210(4)
_cell_angle_gamma                115.903(4)
_cell_formula_units_Z            2
_cell_length_a                   10.548(3)
_cell_length_b                   11.960(3)
_cell_length_c                   13.948(3)
_cell_measurement_reflns_used    1716
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.97
_cell_measurement_theta_min      2.43
_cell_volume                     1415.3(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10420
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.632
_diffrn_reflns_theta_min         1.633
_exptl_absorpt_coefficient_mu    0.069
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6991
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.2061
_refine_ls_R_factor_gt           0.1036
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2640
_reflns_number_total             6991
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02414_si_003.cif
_cod_data_source_block           20190313zh_ngd_0m_sq
_cod_depositor_comments
;Adding full bibliography for 4517779.cif.

 Adding full bibliography for 4517779.cif.
;
_cod_database_code               4517779
_shelx_shelxl_version_number     2018/3
_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   0.987
_shelx_estimated_absorpt_t_max   0.990
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 -0.0694(7) 0.2021(6) 0.5938(4) 0.0761(15) Uani 1 1 d . . . . .
H1 H -0.092432 0.267184 0.578453 0.091 Uiso 1 1 calc R U . . .
C2 C -0.1790(8) 0.0904(7) 0.6042(5) 0.099(2) Uani 1 1 d . . . . .
H2 H -0.275285 0.081234 0.594912 0.119 Uiso 1 1 calc R U . . .
C3 C -0.1464(10) -0.0060(7) 0.6281(6) 0.105(2) Uani 1 1 d . . . . .
H3 H -0.220802 -0.080410 0.634176 0.126 Uiso 1 1 calc R U . . .
C4 C -0.0040(10) 0.0076(6) 0.6431(5) 0.100(2) Uani 1 1 d . . . . .
H4 H 0.019714 -0.056357 0.661361 0.121 Uiso 1 1 calc R U . . .
C5 C 0.1042(7) 0.1172(5) 0.6310(4) 0.0747(15) Uani 1 1 d . . . . .
H5 H 0.199625 0.124899 0.639652 0.090 Uiso 1 1 calc R U . . .
C6 C 0.0735(6) 0.2164(5) 0.6061(3) 0.0603(12) Uani 1 1 d . . . . .
C7 C 0.1943(6) 0.3367(5) 0.5945(3) 0.0588(12) Uani 1 1 d . . . . .
H7 H 0.280962 0.322990 0.598473 0.071 Uiso 1 1 calc R U . . .
C8 C 0.2605(6) 0.4529(5) 0.6892(4) 0.0583(12) Uani 1 1 d . . . . .
C9 C 0.1311(6) 0.3657(5) 0.4892(4) 0.0646(13) Uani 1 1 d . . . . .
H9A H 0.073176 0.286803 0.430837 0.078 Uiso 1 1 calc R U . . .
H9B H 0.058874 0.395252 0.489218 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2625(6) 0.4690(5) 0.4703(4) 0.0684(14) Uani 1 1 d . . . . .
H10A H 0.333448 0.438444 0.469094 0.082 Uiso 1 1 calc R U . . .
H10B H 0.321868 0.546981 0.529780 0.082 Uiso 1 1 calc R U . . .
C11 C 0.2030(6) 0.5021(5) 0.3673(4) 0.0605(12) Uani 1 1 d . . . . .
H11 H 0.129233 0.530175 0.369081 0.073 Uiso 1 1 calc R U . . .
C12 C 0.1157(6) 0.3871(5) 0.2679(4) 0.0571(12) Uani 1 1 d . . . . .
C13 C -0.0327(7) 0.3536(6) 0.1952(4) 0.0783(16) Uani 1 1 d . . . . .
H13 H -0.080742 0.398507 0.208080 0.094 Uiso 1 1 calc R U . . .
C14 C -0.1118(7) 0.2516(6) 0.1017(5) 0.0865(18) Uani 1 1 d . . . . .
H14 H -0.212034 0.230914 0.052995 0.104 Uiso 1 1 calc R U . . .
C15 C -0.0503(8) 0.1830(6) 0.0792(5) 0.0801(16) Uani 1 1 d . . . . .
C16 C 0.1012(8) 0.2171(6) 0.1522(5) 0.0861(18) Uani 1 1 d . . . . .
H16 H 0.148010 0.171641 0.138127 0.103 Uiso 1 1 calc R U . . .
C17 C 0.1840(7) 0.3191(5) 0.2468(4) 0.0736(15) Uani 1 1 d . . . . .
H17 H 0.284724 0.340650 0.295128 0.088 Uiso 1 1 calc R U . . .
C18 C -0.1424(9) 0.0746(7) -0.0240(5) 0.123(3) Uani 1 1 d . . . . .
H18A H -0.204126 -0.005108 -0.012119 0.184 Uiso 1 1 calc R U . . .
H18B H -0.071060 0.066149 -0.047337 0.184 Uiso 1 1 calc R U . . .
H18C H -0.210576 0.094122 -0.078082 0.184 Uiso 1 1 calc R U . . .
C19 C 0.3369(7) 0.6141(5) 0.3568(4) 0.0666(14) Uani 1 1 d . . . . .
C20 C 0.3950(9) 0.7816(6) 0.2759(6) 0.117(3) Uani 1 1 d . . . . .
H20A H 0.487830 0.835083 0.341829 0.176 Uiso 1 1 calc R U . . .
H20B H 0.350445 0.832548 0.245273 0.176 Uiso 1 1 calc R U . . .
H20C H 0.421807 0.746834 0.226709 0.176 Uiso 1 1 calc R U . . .
C21 C 0.4450(6) 0.6628(5) 0.9000(4) 0.0729(15) Uani 1 1 d . . . . .
H21 H 0.351617 0.657942 0.855053 0.088 Uiso 1 1 calc R U . . .
C22 C 0.5450(8) 0.7584(6) 1.0015(5) 0.0926(19) Uani 1 1 d . . . . .
H22 H 0.516490 0.816411 1.021814 0.111 Uiso 1 1 calc R U . . .
C23 C 0.6799(7) 0.7664(6) 1.0683(4) 0.0863(18) Uani 1 1 d . . . . .
H23 H 0.744439 0.830257 1.133726 0.104 Uiso 1 1 calc R U . . .
C24 C 0.7234(6) 0.6781(6) 1.0393(4) 0.0698(15) Uani 1 1 d . . . . .
C25 C 0.8635(7) 0.6799(7) 1.1050(5) 0.091(2) Uani 1 1 d . . . . .
H25 H 0.931221 0.741530 1.171443 0.109 Uiso 1 1 calc R U . . .
C26 C 0.8990(8) 0.5952(8) 1.0733(5) 0.098(2) Uani 1 1 d . U . . .
H26 H 0.989147 0.594976 1.117692 0.118 Uiso 1 1 calc R U . . .
C27 C 0.7972(8) 0.5045(7) 0.9702(5) 0.097(2) Uani 1 1 d . U . . .
H27 H 0.825525 0.447710 0.947123 0.117 Uiso 1 1 calc R U . . .
C28 C 0.6285(6) 0.5843(5) 0.9386(4) 0.0622(13) Uani 1 1 d . . . . .
C29 C 0.4870(6) 0.5787(5) 0.8695(4) 0.0610(13) Uani 1 1 d . . . . .
N1 N 0.3997(5) 0.4819(4) 0.7709(3) 0.0618(10) Uani 1 1 d . . . . .
H1A H 0.439254 0.435140 0.760863 0.074 Uiso 1 1 calc R U . . .
N2 N 0.6631(5) 0.4966(5) 0.9047(3) 0.0765(13) Uani 1 1 d . . . . .
O1 O 0.1924(4) 0.5132(4) 0.6895(3) 0.0730(10) Uani 1 1 d . . . . .
O2 O 0.4700(5) 0.6402(4) 0.3941(4) 0.1026(14) Uani 1 1 d . . . . .
O3 O 0.2830(5) 0.6775(4) 0.2967(3) 0.0923(12) 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
C6 C1 C2 120.2(6) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.8(7) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.6(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 117.9(5) . . ?
C1 C6 C7 121.2(5) . . ?
C5 C6 C7 120.9(5) . . ?
C6 C7 C8 109.1(4) . . ?
C6 C7 C9 113.7(4) . . ?
C8 C7 C9 110.3(4) . . ?
C6 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C9 C7 H7 107.8 . . ?
O1 C8 N1 123.8(5) . . ?
O1 C8 C7 121.8(4) . . ?
N1 C8 C7 114.3(4) . . ?
C10 C9 C7 111.9(4) . . ?
C10 C9 H9A 109.2 . . ?
C7 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C7 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.1(4) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C19 C11 C12 109.1(4) . . ?
C19 C11 C10 111.3(4) . . ?
C12 C11 C10 113.1(4) . . ?
C19 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C13 C12 C17 118.9(5) . . ?
C13 C12 C11 119.1(5) . . ?
C17 C12 C11 121.9(5) . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 123.0(6) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C16 117.7(6) . . ?
C14 C15 C18 120.0(7) . . ?
C16 C15 C18 122.3(6) . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 O3 123.6(5) . . ?
O2 C19 C11 126.1(5) . . ?
O3 C19 C11 110.3(5) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C29 C21 C22 119.6(5) . . ?
C29 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 121.2(6) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.0(6) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 123.6(6) . . ?
C23 C24 C28 120.0(5) . . ?
C25 C24 C28 116.4(6) . . ?
C26 C25 C24 120.9(6) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 118.9(6) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N2 C27 C26 123.3(7) . . ?
N2 C27 H27 118.4 . . ?
C26 C27 H27 118.4 . . ?
N2 C28 C29 118.0(5) . . ?
N2 C28 C24 123.4(5) . . ?
C29 C28 C24 118.6(5) . . ?
C21 C29 N1 124.8(5) . . ?
C21 C29 C28 120.5(5) . . ?
N1 C29 C28 114.6(5) . . ?
C8 N1 C29 128.2(4) . . ?
C8 N1 H1A 115.9 . . ?
C29 N1 H1A 115.9 . . ?
C27 N2 C28 117.0(5) . . ?
C19 O3 C20 116.2(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
C1 C6 1.384(7) . ?
C1 C2 1.395(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(7) . ?
C7 C8 1.536(6) . ?
C7 C9 1.516(6) . ?
C7 H7 0.9800 . ?
C8 O1 1.220(5) . ?
C8 N1 1.362(6) . ?
C9 C10 1.528(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.507(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C19 1.529(7) . ?
C11 C12 1.526(6) . ?
C11 H11 0.9800 . ?
C12 C13 1.371(7) . ?
C12 C17 1.376(7) . ?
C13 C14 1.399(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.328(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(8) . ?
C15 C18 1.513(8) . ?
C16 C17 1.405(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O2 1.185(6) . ?
C19 O3 1.316(6) . ?
C20 O3 1.431(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C29 1.358(7) . ?
C21 C22 1.426(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.346(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.406(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.419(8) . ?
C24 C28 1.410(7) . ?
C25 C26 1.320(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.420(9) . ?
C26 H26 0.9300 . ?
C27 N2 1.334(7) . ?
C27 H27 0.9300 . ?
C28 N2 1.355(6) . ?
C28 C29 1.423(7) . ?
C29 N1 1.408(6) . ?
N1 H1A 0.8600 . ?
