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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555917.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_1555917
loop_
_publ_author_name
'Peng, Jianwen'
'Gao, Yang'
'Hu, Weigao'
'Gao, Yinglan'
'Hu, Miao'
'Wu, Wanqing'
'Ren, Yanwei'
'Jiang, Huanfeng'
_publ_section_title
;
 Palladium-Catalyzed Multicomponent Reaction (MCR) of Propargylic
 Carbonates with Isocyanides.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5924
_journal_page_last               5927
_journal_paper_doi               10.1021/acs.orglett.6b02999
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H26 N2 O'
_chemical_formula_weight         298.42
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7863(4)
_cell_length_b                   19.6959(8)
_cell_length_c                   19.8100(7)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.47
_cell_measurement_theta_min      4.46
_cell_volume                     3428.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8290
_diffrn_reflns_theta_full        67.47
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         4.46
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_correction_T_min  0.9467
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0857P)²+1.6964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                2515
_reflns_number_total             3025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02999_si_003.cif
_cod_data_source_block           12163
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1555917
loop_
_symmetry_equiv_pos_as_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'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N 0.21848(18) 0.08516(8) 0.58513(8) 0.0244(4) Uani 1 1 d .
N1 N 0.08998(18) -0.00827(8) 0.62698(7) 0.0240(4) Uani 1 1 d .
C11 C 0.1056(2) 0.06422(9) 0.61857(8) 0.0216(4) Uani 1 1 d .
O1 O -0.10955(19) -0.07751(7) 0.66416(10) 0.0482(5) Uani 1 1 d .
C8 C -0.1243(2) 0.04385(9) 0.67032(9) 0.0263(4) Uani 1 1 d .
C1 C -0.0656(2) 0.16740(9) 0.66436(8) 0.0228(4) Uani 1 1 d .
C7 C -0.0325(2) 0.09474(9) 0.65192(9) 0.0232(4) Uani 1 1 d .
C2 C 0.0218(2) 0.20610(10) 0.70871(9) 0.0262(4) Uani 1 1 d .
H2A H 0.1039 0.1863 0.7308 0.031 Uiso 1 1 calc R
C5 C -0.2253(2) 0.26534(10) 0.64519(10) 0.0287(5) Uani 1 1 d .
H5A H -0.3095 0.2849 0.6244 0.034 Uiso 1 1 calc R
C3 C -0.0126(2) 0.27387(10) 0.72018(10) 0.0302(5) Uani 1 1 d .
H3A H 0.0471 0.2993 0.7495 0.036 Uiso 1 1 calc R
C4 C -0.1358(2) 0.30383(10) 0.68802(9) 0.0294(5) Uani 1 1 d .
H4A H -0.1580 0.3494 0.6952 0.035 Uiso 1 1 calc R
C19 C 0.1495(2) 0.20196(10) 0.53931(10) 0.0313(5) Uani 1 1 d .
H19A H 0.0854 0.2135 0.5768 0.047 Uiso 1 1 calc R
H19B H 0.0893 0.1814 0.5044 0.047 Uiso 1 1 calc R
H19C H 0.1971 0.2423 0.5221 0.047 Uiso 1 1 calc R
C10 C -0.0509(2) -0.02229(9) 0.65389(10) 0.0271(4) Uani 1 1 d .
C16 C 0.2719(2) 0.15199(10) 0.56253(10) 0.0279(4) Uani 1 1 d .
C9 C -0.2764(3) 0.04520(11) 0.70340(12) 0.0403(6) Uani 1 1 d .
H9A H -0.3071 0.0914 0.7105 0.060 Uiso 1 1 calc R
H9B H -0.2709 0.0222 0.7460 0.060 Uiso 1 1 calc R
H9C H -0.3494 0.0229 0.6750 0.060 Uiso 1 1 calc R
C6 C -0.1905(2) 0.19798(10) 0.63312(9) 0.0256(4) Uani 1 1 d .
H6A H -0.2509 0.1727 0.6038 0.031 Uiso 1 1 calc R
C14 C 0.1989(3) -0.05564(11) 0.52220(10) 0.0369(5) Uani 1 1 d .
H14A H 0.2251 -0.0108 0.5073 0.055 Uiso 1 1 calc R
H14B H 0.0984 -0.0668 0.5067 0.055 Uiso 1 1 calc R
H14C H 0.2705 -0.0877 0.5041 0.055 Uiso 1 1 calc R
C13 C 0.3617(2) -0.04335(11) 0.62651(11) 0.0360(5) Uani 1 1 d .
H13A H 0.3605 -0.0457 0.6749 0.054 Uiso 1 1 calc R
H13B H 0.3923 0.0013 0.6127 0.054 Uiso 1 1 calc R
H13C H 0.4323 -0.0762 0.6091 0.054 Uiso 1 1 calc R
C18 C 0.3703(3) 0.18226(11) 0.61860(12) 0.0392(5) Uani 1 1 d .
H18A H 0.3073 0.1935 0.6566 0.059 Uiso 1 1 calc R
H18B H 0.4196 0.2225 0.6023 0.059 Uiso 1 1 calc R
H18C H 0.4458 0.1497 0.6321 0.059 Uiso 1 1 calc R
C12 C 0.2032(2) -0.05836(9) 0.59932(10) 0.0280(5) Uani 1 1 d .
C17 C 0.3736(3) 0.13531(11) 0.50196(12) 0.0442(6) Uani 1 1 d .
H17A H 0.3126 0.1164 0.4664 0.066 Uiso 1 1 calc R
H17B H 0.4497 0.1030 0.5153 0.066 Uiso 1 1 calc R
H17C H 0.4220 0.1760 0.4863 0.066 Uiso 1 1 calc R
C15 C 0.1625(3) -0.13036(10) 0.62150(13) 0.0440(6) Uani 1 1 d .
H15A H 0.1646 -0.1330 0.6699 0.066 Uiso 1 1 calc R
H15B H 0.2348 -0.1618 0.6030 0.066 Uiso 1 1 calc R
H15C H 0.0623 -0.1415 0.6056 0.066 Uiso 1 1 calc R
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
C11 N2 C16 134.81(16)
C10 N1 C11 109.20(15)
C10 N1 C12 127.20(16)
C11 N1 C12 122.91(15)
N2 C11 N1 117.30(16)
N2 C11 C7 137.11(17)
N1 C11 C7 105.49(14)
C7 C8 C9 130.41(18)
C7 C8 C10 109.56(17)
C9 C8 C10 120.02(17)
C2 C1 C6 118.47(17)
C2 C1 C7 121.66(17)
C6 C1 C7 119.83(16)
C8 C7 C1 124.07(17)
C8 C7 C11 107.84(16)
C1 C7 C11 128.07(16)
C3 C2 C1 120.61(18)
C6 C5 C4 120.40(18)
C4 C3 C2 120.26(18)
C5 C4 C3 119.48(18)
O1 C10 N1 128.53(18)
O1 C10 C8 124.09(18)
N1 C10 C8 107.38(16)
N2 C16 C19 116.38(16)
N2 C16 C18 108.00(16)
C19 C16 C18 111.43(17)
N2 C16 C17 103.48(16)
C19 C16 C17 108.21(17)
C18 C16 C17 108.86(18)
C5 C6 C1 120.75(18)
N1 C12 C13 110.41(15)
N1 C12 C15 110.43(16)
C13 C12 C15 107.05(18)
N1 C12 C14 108.93(16)
C13 C12 C14 111.68(18)
C15 C12 C14 108.31(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C11 1.262(2)
N2 C16 1.467(2)
N1 C10 1.376(2)
N1 C11 1.444(2)
N1 C12 1.505(2)
C11 C7 1.507(3)
O1 C10 1.221(2)
C8 C7 1.337(3)
C8 C9 1.489(3)
C8 C10 1.489(3)
C1 C2 1.394(3)
C1 C6 1.396(3)
C1 C7 1.481(3)
C2 C3 1.387(3)
C5 C6 1.382(3)
C5 C4 1.383(3)
C3 C4 1.388(3)
C19 C16 1.528(3)
C16 C18 1.528(3)
C16 C17 1.531(3)
C14 C12 1.529(3)
C13 C12 1.522(3)
C12 C15 1.527(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305536
