#------------------------------------------------------------------------------
#$Date: 2020-04-30 23:29:10 +0300 (Thu, 30 Apr 2020) $
#$Revision: 251328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038317.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_4038317
loop_
_publ_author_name
'Chen, Dianpeng'
'Yang, Min'
'Li, Jianming'
'Cui, Peiying'
'Su, Lei'
'Shan, Yingying'
'You, Jinmao'
'Rojsitthisak, Pornchai'
'Liu, Jin-Biao'
'Qiu, Guanyinsheng'
_publ_section_title
;
 Palladium-Catalyzed Cycloaddition of Alkynylimines, Double Isocyanides,
 and H2O/KOAc.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00323
_journal_year                    2020
_chemical_formula_sum            'C33 H37 N3 O2'
_chemical_formula_weight         507.66
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.914(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5651(6)
_cell_length_b                   20.5701(11)
_cell_length_c                   12.4399(7)
_cell_measurement_reflns_used    3486
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.23
_cell_volume                     2943.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13830
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5776
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0686P)²+1.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                3931
_reflns_number_total             5776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00323_si_003.cif
_cod_data_source_block           12
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4038317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.45523(17) 0.43181(10) 0.74221(17) 0.0395(5) Uani 1 1 d . . .
H1 H 0.4401 0.4467 0.8099 0.047 Uiso 1 1 calc R . .
C2 C 0.56222(17) 0.43079(10) 0.70368(16) 0.0381(5) Uani 1 1 d . . .
C3 C 0.54768(18) 0.40270(10) 0.59777(16) 0.0376(5) Uani 1 1 d . . .
C4 C 0.43249(18) 0.38805(10) 0.57617(16) 0.0379(5) Uani 1 1 d . . .
C5 C 0.3518(2) 0.28768(12) 0.4793(2) 0.0575(6) Uani 1 1 d U . .
C6 C 0.4397(4) 0.2565(2) 0.4198(5) 0.159(2) Uani 1 1 d . . .
H6A H 0.5110 0.2806 0.4306 0.239 Uiso 1 1 calc R . .
H6B H 0.4129 0.2555 0.3442 0.239 Uiso 1 1 calc R . .
H6C H 0.4527 0.2129 0.4457 0.239 Uiso 1 1 calc R . .
C7 C 0.2329(4) 0.2779(2) 0.4190(5) 0.164(2) Uani 1 1 d . . .
H7A H 0.1746 0.2832 0.4679 0.246 Uiso 1 1 calc R . .
H7B H 0.2277 0.2349 0.3889 0.246 Uiso 1 1 calc R . .
H7C H 0.2208 0.3093 0.3619 0.246 Uiso 1 1 calc R . .
C8 C 0.3467(5) 0.26010(19) 0.5874(3) 0.149(2) Uani 1 1 d U . .
H8A H 0.4242 0.2552 0.6224 0.223 Uiso 1 1 calc R . .
H8B H 0.3093 0.2184 0.5812 0.223 Uiso 1 1 calc R . .
H8C H 0.3034 0.2887 0.6292 0.223 Uiso 1 1 calc R . .
C9 C 0.25223(18) 0.40671(10) 0.67434(18) 0.0415(5) Uani 1 1 d . . .
C10 C 0.1737(2) 0.42266(13) 0.5864(2) 0.0565(6) Uani 1 1 d . . .
H10 H 0.1996 0.4339 0.5205 0.068 Uiso 1 1 calc R . .
C11 C 0.0559(2) 0.42154(14) 0.5987(3) 0.0682(8) Uani 1 1 d . . .
H11 H 0.0024 0.4312 0.5399 0.082 Uiso 1 1 calc R . .
C12 C 0.0172(2) 0.40654(15) 0.6958(3) 0.0720(8) Uani 1 1 d . . .
H12 H -0.0621 0.4059 0.7028 0.086 Uiso 1 1 calc R . .
C13 C 0.0961(2) 0.39237(15) 0.7832(3) 0.0677(8) Uani 1 1 d . . .
H13 H 0.0701 0.3830 0.8498 0.081 Uiso 1 1 calc R . .
C14 C 0.2142(2) 0.39196(12) 0.7724(2) 0.0510(6) Uani 1 1 d . . .
H14 H 0.2673 0.3818 0.8312 0.061 Uiso 1 1 calc R . .
C15 C 0.66767(18) 0.45886(12) 0.75642(18) 0.0453(5) Uani 1 1 d . . .
C16 C 0.7239(2) 0.43107(14) 0.9520(2) 0.0588(7) Uani 1 1 d . . .
C17 C 0.7313(3) 0.36384(16) 0.9017(3) 0.0915(10) Uani 1 1 d . . .
H17A H 0.6546 0.3492 0.8760 0.137 Uiso 1 1 calc R . .
H17B H 0.7658 0.3340 0.9551 0.137 Uiso 1 1 calc R . .
H17C H 0.7781 0.3660 0.8424 0.137 Uiso 1 1 calc R . .
C18 C 0.8462(3) 0.4555(2) 0.9876(3) 0.1041(13) Uani 1 1 d . . .
H18A H 0.8885 0.4601 0.9256 0.156 Uiso 1 1 calc R . .
H18B H 0.8854 0.4249 1.0371 0.156 Uiso 1 1 calc R . .
H18C H 0.8417 0.4969 1.0227 0.156 Uiso 1 1 calc R . .
C19 C 0.6504(4) 0.4257(2) 1.0459(3) 0.1094(14) Uani 1 1 d . . .
H19A H 0.6490 0.4669 1.0820 0.164 Uiso 1 1 calc R . .
H19B H 0.6832 0.3934 1.0958 0.164 Uiso 1 1 calc R . .
H19C H 0.5726 0.4134 1.0194 0.164 Uiso 1 1 calc R . .
C20 C 0.6480(2) 0.54097(13) 0.8923(2) 0.0564(6) Uani 1 1 d . . .
C21 C 0.6067(3) 0.58438(13) 0.7995(2) 0.0703(8) Uani 1 1 d . . .
H21A H 0.5662 0.6209 0.8257 0.105 Uiso 1 1 calc R . .
H21B H 0.5553 0.5606 0.7484 0.105 Uiso 1 1 calc R . .
H21C H 0.6723 0.5995 0.7651 0.105 Uiso 1 1 calc R . .
C22 C 0.63790(18) 0.38993(10) 0.52455(16) 0.0381(5) Uani 1 1 d . . .
C23 C 0.7165(2) 0.33896(12) 0.54200(19) 0.0503(6) Uani 1 1 d . . .
H23 H 0.7138 0.3125 0.6023 0.060 Uiso 1 1 calc R . .
C24 C 0.7983(2) 0.32693(12) 0.47155(19) 0.0508(6) Uani 1 1 d . . .
H24 H 0.8492 0.2922 0.4848 0.061 Uiso 1 1 calc R . .
C25 C 0.80645(19) 0.36551(10) 0.38123(17) 0.0416(5) Uani 1 1 d . . .
C26 C 0.7282(2) 0.41678(11) 0.36425(18) 0.0497(6) Uani 1 1 d . . .
H26 H 0.7317 0.4437 0.3046 0.060 Uiso 1 1 calc R . .
C27 C 0.6455(2) 0.42842(11) 0.43433(18) 0.0461(5) Uani 1 1 d . . .
H27 H 0.5938 0.4628 0.4207 0.055 Uiso 1 1 calc R . .
C28 C 0.89643(19) 0.35442(11) 0.30629(18) 0.0455(5) Uani 1 1 d . . .
C29 C 0.9155(2) 0.29365(14) 0.2631(2) 0.0651(7) Uani 1 1 d . . .
H29 H 0.8722 0.2582 0.2824 0.078 Uiso 1 1 calc R . .
C30 C 0.9982(3) 0.28516(18) 0.1917(3) 0.0801(9) Uani 1 1 d . . .
H30 H 1.0088 0.2443 0.1621 0.096 Uiso 1 1 calc R . .
C31 C 1.0644(3) 0.3364(2) 0.1643(2) 0.0788(9) Uani 1 1 d . . .
H31 H 1.1200 0.3305 0.1161 0.095 Uiso 1 1 calc R . .
C32 C 1.0488(2) 0.39639(17) 0.2079(2) 0.0704(8) Uani 1 1 d . . .
H32 H 1.0949 0.4311 0.1904 0.085 Uiso 1 1 calc R . .
C33 C 0.9654(2) 0.40552(13) 0.2773(2) 0.0571(6) Uani 1 1 d . . .
H33 H 0.9549 0.4467 0.3055 0.069 Uiso 1 1 calc R . .
N1 N 0.37495(14) 0.40736(8) 0.66492(13) 0.0381(4) Uani 1 1 d . . .
N2 N 0.37085(17) 0.35950(9) 0.48575(14) 0.0473(5) Uani 1 1 d . . .
H2A H 0.4082 0.3705 0.4284 0.057 Uiso 1 1 d R . .
N3 N 0.66598(15) 0.47703(9) 0.86912(14) 0.0441(5) Uani 1 1 d . . .
O1 O 0.75482(14) 0.46817(11) 0.71284(15) 0.0753(6) Uani 1 1 d . . .
O2 O 0.6632(2) 0.56307(11) 0.98342(16) 0.0920(7) 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
N1 C1 C2 108.74(18) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.62(17) . . ?
C1 C2 C15 125.78(19) . . ?
C3 C2 C15 126.34(19) . . ?
C4 C3 C2 106.84(18) . . ?
C4 C3 C22 125.18(18) . . ?
C2 C3 C22 127.97(18) . . ?
C3 C4 N2 131.1(2) . . ?
C3 C4 N1 108.35(17) . . ?
N2 C4 N1 120.53(18) . . ?
C6 C5 C8 112.9(4) . . ?
C6 C5 N2 110.8(3) . . ?
C8 C5 N2 110.7(2) . . ?
C6 C5 C7 109.5(4) . . ?
C8 C5 C7 106.4(4) . . ?
N2 C5 C7 106.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 120.6(2) . . ?
C14 C9 N1 118.99(19) . . ?
C10 C9 N1 120.4(2) . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.6(2) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O1 C15 C2 124.3(2) . . ?
O1 C15 N3 119.15(19) . . ?
C2 C15 N3 116.52(18) . . ?
N3 C16 C19 109.2(2) . . ?
N3 C16 C18 109.1(2) . . ?
C19 C16 C18 112.1(3) . . ?
N3 C16 C17 109.2(2) . . ?
C19 C16 C17 108.0(3) . . ?
C18 C16 C17 109.2(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 N3 123.0(3) . . ?
O2 C20 C21 119.9(3) . . ?
N3 C20 C21 117.0(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 117.6(2) . . ?
C27 C22 C3 120.41(19) . . ?
C23 C22 C3 121.99(19) . . ?
C24 C23 C22 121.2(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.4(2) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 117.3(2) . . ?
C24 C25 C28 122.1(2) . . ?
C26 C25 C28 120.5(2) . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C22 121.3(2) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C29 C28 C33 117.5(2) . . ?
C29 C28 C25 122.1(2) . . ?
C33 C28 C25 120.3(2) . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 121.3(3) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?
C1 N1 C4 108.40(16) . . ?
C1 N1 C9 123.59(17) . . ?
C4 N1 C9 127.89(17) . . ?
C4 N2 C5 121.23(18) . . ?
C4 N2 H2A 106.6 . . ?
C5 N2 H2A 106.6 . . ?
C20 N3 C15 117.9(2) . . ?
C20 N3 C16 121.80(19) . . ?
C15 N3 C16 116.75(18) . . ?
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 N1 1.362(3) . ?
C1 C2 1.372(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.433(3) . ?
C2 C15 1.444(3) . ?
C3 C4 1.365(3) . ?
C3 C22 1.478(3) . ?
C4 N2 1.398(3) . ?
C4 N1 1.404(3) . ?
C5 C6 1.465(5) . ?
C5 C8 1.466(4) . ?
C5 N2 1.495(3) . ?
C5 C7 1.511(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.373(3) . ?
C9 C10 1.387(3) . ?
C9 N1 1.436(3) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.208(3) . ?
C15 N3 1.453(3) . ?
C16 N3 1.504(3) . ?
C16 C19 1.518(4) . ?
C16 C18 1.523(4) . ?
C16 C17 1.524(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O2 1.217(3) . ?
C20 N3 1.367(3) . ?
C20 C21 1.498(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.383(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(3) . ?
C25 C28 1.485(3) . ?
C26 C27 1.380(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.387(3) . ?
C28 C33 1.390(3) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.366(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.372(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
N2 H2A 0.9000 . ?
