#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/70/4027055.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_4027055
loop_
_publ_author_name
'Kyoung A Jo'
'Muchchintala Maheswara'
'Eunyoung Yoon'
'Yun Yeong Lee'
'Hoseop Yun'
'Eun Joo Kang'
_publ_section_title
;
 N-Heterocyclic Carbene Catalyzed Domino Cyclization of Propargylic
 Alcohols and Benzoyl Isocyanates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2924
_journal_page_last               2928
_journal_paper_doi               10.1021/jo202102y
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.35
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-10-05 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.5963(17)
_cell_length_b                   10.1630(7)
_cell_length_c                   15.4331(11)
_cell_measurement_temperature    290(1)
_cell_volume                     3230.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(1)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku R-axis Rapid'
_diffrn_measurement_method       ω
_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  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19528
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             1296
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0520
_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)+(0.0513P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                1646
_reflns_number_total             3625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202102y_si_001.cif
_cod_data_source_block           l
_cod_original_sg_symbol_H-M      'P b c a'
_cod_database_code               4027055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, 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
O1 O 0.75170(7) 0.11655(16) 0.20837(10) 0.0716(5) Uani 1 1 d
O2 O 0.76548(8) 0.10605(19) 0.35156(11) 0.0885(6) Uani 1 1 d
O3 O 0.91215(9) -0.11956(15) 0.28256(9) 0.0768(5) Uani 1 1 d
N N 0.85057(8) 0.06182(16) 0.25609(10) 0.0484(4) Uani 1 1 d
C1 C 0.78709(11) 0.0967(2) 0.28014(15) 0.0623(6) Uani 1 1 d
C2 C 0.85531(10) 0.05639(19) 0.16432(12) 0.0492(5) Uani 1 1 d
C3 C 0.78720(10) 0.0771(2) 0.13075(13) 0.0579(6) Uani 1 1 d
C4 C 0.88902(10) -0.0204(2) 0.31200(13) 0.0519(5) Uani 1 1 d
C5 C 0.89874(9) 0.0231(2) 0.40208(12) 0.0504(5) Uani 1 1 d
C6 C 0.91530(10) -0.0733(2) 0.46235(14) 0.0581(6) Uani 1 1 d
C7 C 0.92653(12) -0.0384(3) 0.54751(16) 0.0687(7) Uani 1 1 d
C8 C 0.92231(12) 0.0915(3) 0.57239(17) 0.0733(7) Uani 1 1 d
C9 C 0.90751(12) 0.1876(3) 0.51303(16) 0.0680(7) Uani 1 1 d
C10 C 0.89532(10) 0.1546(2) 0.42731(15) 0.0561(6) Uani 1 1 d
C11 C 0.90845(10) 0.0387(2) 0.11656(14) 0.0556(6) Uani 1 1 d
C12 C 0.97719(9) 0.0301(2) 0.14351(12) 0.0493(5) Uani 1 1 d
C13 C 1.01772(12) -0.0648(2) 0.10801(15) 0.0617(6) Uani 1 1 d
C14 C 1.08272(13) -0.0706(3) 0.13005(17) 0.0711(7) Uani 1 1 d
C15 C 1.10868(13) 0.0196(3) 0.18631(16) 0.0715(7) Uani 1 1 d
C16 C 1.06919(12) 0.1153(3) 0.22109(15) 0.0660(7) Uani 1 1 d
C17 C 1.00402(11) 0.1196(2) 0.20064(13) 0.0553(6) Uani 1 1 d
C18 C 0.78078(17) 0.1912(4) 0.0671(2) 0.0946(11) Uani 1 1 d
C19 C 0.75783(19) -0.0478(4) 0.0964(4) 0.1122(14) Uani 1 1 d
H6 H 0.9180(10) -0.172(2) 0.4420(13) 0.077(7) Uiso 1 1 d
H7 H 0.9383(11) -0.106(2) 0.5901(15) 0.079(7) Uiso 1 1 d
H8 H 0.9294(11) 0.116(2) 0.6307(15) 0.079(7) Uiso 1 1 d
H9 H 0.9055(11) 0.279(2) 0.5275(13) 0.079(7) Uiso 1 1 d
H10 H 0.8838(10) 0.220(2) 0.3826(13) 0.072(7) Uiso 1 1 d
H11 H 0.9011(11) 0.034(2) 0.0565(14) 0.073(7) Uiso 1 1 d
H13 H 1.0002(10) -0.122(2) 0.0672(14) 0.068(7) Uiso 1 1 d
H14 H 1.1094(11) -0.142(2) 0.1055(13) 0.078(7) Uiso 1 1 d
H15 H 1.1542(13) 0.017(2) 0.2020(14) 0.089(8) Uiso 1 1 d
H16 H 1.0886(11) 0.179(2) 0.2591(13) 0.070(7) Uiso 1 1 d
H17 H 0.9791(11) 0.185(2) 0.2238(12) 0.066(7) Uiso 1 1 d
H18A H 0.7368(13) 0.208(2) 0.0545(14) 0.085(8) Uiso 1 1 d
H18B H 0.8050(17) 0.167(4) 0.014(2) 0.161(15) Uiso 1 1 d
H18C H 0.797(2) 0.274(4) 0.099(3) 0.20(2) Uiso 1 1 d
H19A H 0.7599(12) -0.122(3) 0.1417(16) 0.093(10) Uiso 1 1 d
H19B H 0.7170(16) -0.034(3) 0.0883(19) 0.116(11) Uiso 1 1 d
H19C H 0.785(2) -0.079(4) 0.041(2) 0.186(18) Uiso 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 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C3 111.36(16)
C1 N C2 109.71(16)
C1 N C4 120.04(17)
C2 N C4 122.51(16)
O2 C1 O1 123.3(2)
O2 C1 N 127.7(2)
O1 C1 N 109.00(19)
C11 C2 N 127.83(19)
C11 C2 C3 126.33(18)
N C2 C3 105.83(17)
O1 C3 C19 108.7(3)
O1 C3 C2 102.84(15)
C19 C3 C2 112.2(2)
O1 C3 C18 106.0(2)
C19 C3 C18 112.4(3)
C2 C3 C18 114.0(2)
O3 C4 N 118.54(18)
O3 C4 C5 123.63(19)
N C4 C5 117.83(18)
C6 C5 C10 120.0(2)
C6 C5 C4 116.93(19)
C10 C5 C4 123.00(19)
C7 C6 C5 119.7(2)
C8 C7 C6 120.0(2)
C9 C8 C7 120.6(3)
C8 C9 C10 120.3(3)
C9 C10 C5 119.3(2)
C2 C11 C12 129.8(2)
C17 C12 C13 118.0(2)
C17 C12 C11 121.57(19)
C13 C12 C11 120.4(2)
C14 C13 C12 121.0(2)
C15 C14 C13 120.3(2)
C14 C15 C16 119.3(3)
C15 C16 C17 120.5(3)
C16 C17 C12 120.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.341(3)
O1 C3 1.460(2)
O2 C1 1.192(2)
O3 C4 1.204(2)
N C1 1.405(3)
N C2 1.421(2)
N C4 1.439(3)
C2 C11 1.332(3)
C2 C3 1.510(3)
C3 C19 1.503(4)
C3 C18 1.525(4)
C4 C5 1.472(3)
C5 C6 1.393(3)
C5 C10 1.394(3)
C6 C7 1.381(3)
C7 C8 1.378(3)
C8 C9 1.373(4)
C9 C10 1.388(3)
C11 C12 1.478(3)
C12 C17 1.382(3)
C12 C13 1.388(3)
C13 C14 1.383(3)
C14 C15 1.371(3)
C15 C16 1.377(4)
C16 C17 1.379(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659478
