#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:32:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178472 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/93/4029383.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_4029383
loop_
_publ_author_name
'Chen, Jian-Ming'
'Chang, Chin-Jung'
'Ke, Yao-Jin'
'Liu, Rai-Shung'
_publ_section_title
;
 Catalytic Formal [4 + 2] Cycloadditions between Unactivated Allenes and
 N-Hydroxyaniline Catalyzed by AuCl3/CuCl2/O2.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4306
_journal_page_last               4311
_journal_paper_doi               10.1021/jo500009x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.566(4)
_cell_angle_beta                 97.711(3)
_cell_angle_gamma                96.580(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6805(4)
_cell_length_b                   10.0159(6)
_cell_length_c                   15.1868(9)
_cell_measurement_reflns_used    3798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0491
_cell_measurement_theta_min      3.4680
_cell_volume                     849.80(9)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12960
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0397
_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)+(0.0860P)²+0.0772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2633
_reflns_number_total             3457
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500009x_si_001.cif
_cod_data_source_block           120946lt_0m
_cod_depositor_comments
;Adding full bibliography for 4029383.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4029383
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.0513(2) 0.47134(11) 0.27088(7) 0.0198(3) Uani 1 1 d .
N1 N 0.8068(2) 0.44566(13) 0.28905(9) 0.0183(3) Uani 1 1 d .
C1 C 0.4058(3) 1.02446(17) 0.23369(12) 0.0256(4) Uani 1 1 d .
H1 H 0.3273 1.1033 0.2329 0.031 Uiso 1 1 calc R
C2 C 0.6025(3) 1.01891(17) 0.18964(12) 0.0250(4) Uani 1 1 d .
H2 H 0.6595 1.0943 0.1585 0.030 Uiso 1 1 calc R
C3 C 0.7166(3) 0.90421(16) 0.19069(11) 0.0223(4) Uani 1 1 d .
H3 H 0.8517 0.9018 0.1602 0.027 Uiso 1 1 calc R
C4 C 0.6365(3) 0.79121(16) 0.23597(11) 0.0191(4) Uani 1 1 d .
C5 C 0.7594(3) 0.66747(15) 0.23739(11) 0.0186(4) Uani 1 1 d .
C6 C 0.8903(3) 0.63593(16) 0.17528(11) 0.0201(4) Uani 1 1 d .
H6 H 0.8918 0.6891 0.1245 0.024 Uiso 1 1 calc R
C7 C 1.0357(3) 0.51968(16) 0.18213(10) 0.0196(4) Uani 1 1 d .
H7 H 1.2019 0.5560 0.1732 0.024 Uiso 1 1 calc R
C8 C 0.9554(3) 0.40465(15) 0.11356(10) 0.0188(4) Uani 1 1 d .
C9 C 0.7345(3) 0.39221(17) 0.06035(11) 0.0230(4) Uani 1 1 d .
H9 H 0.6288 0.4580 0.0657 0.028 Uiso 1 1 calc R
C10 C 0.6670(3) 0.28422(17) -0.00071(12) 0.0260(4) Uani 1 1 d .
H10 H 0.5164 0.2772 -0.0373 0.031 Uiso 1 1 calc R
C11 C 0.8173(3) 0.18733(17) -0.00841(12) 0.0258(4) Uani 1 1 d .
H11 H 0.7700 0.1132 -0.0498 0.031 Uiso 1 1 calc R
C12 C 0.7261(3) 0.11829(17) 0.45460(12) 0.0245(4) Uani 1 1 d .
H12 H 0.7057 0.0432 0.4909 0.029 Uiso 1 1 calc R
C13 C 0.9121(3) 0.13274(16) 0.40453(12) 0.0246(4) Uani 1 1 d .
H13 H 1.0195 0.0665 0.4062 0.030 Uiso 1 1 calc R
C14 C 0.9447(3) 0.24219(16) 0.35187(11) 0.0213(4) Uani 1 1 d .
H14 H 1.0746 0.2509 0.3182 0.026 Uiso 1 1 calc R
C15 C 0.7880(3) 0.33942(15) 0.34818(11) 0.0188(4) Uani 1 1 d .
C16 C 0.3242(3) 0.91467(17) 0.27885(12) 0.0246(4) Uani 1 1 d .
H16 H 0.1890 0.9180 0.3091 0.030 Uiso 1 1 calc R
C17 C 0.4382(3) 0.79970(16) 0.28029(11) 0.0218(4) Uani 1 1 d .
H17 H 0.3806 0.7252 0.3120 0.026 Uiso 1 1 calc R
C18 C 0.7336(3) 0.57588(15) 0.31430(11) 0.0188(4) Uani 1 1 d .
H18 H 0.5598 0.5606 0.3208 0.023 Uiso 1 1 calc R
C19 C 0.8675(3) 0.63874(17) 0.40203(11) 0.0243(4) Uani 1 1 d .
H19A H 0.8246 0.5834 0.4510 0.036 Uiso 1 1 calc R
H19B H 0.8238 0.7295 0.4110 0.036 Uiso 1 1 calc R
H19C H 1.0402 0.6437 0.4005 0.036 Uiso 1 1 calc R
C20 C 1.0382(3) 0.19832(17) 0.04455(12) 0.0256(4) Uani 1 1 d .
H20 H 1.1421 0.1315 0.0395 0.031 Uiso 1 1 calc R
C21 C 1.1071(3) 0.30668(16) 0.10477(11) 0.0223(4) Uani 1 1 d .
H21 H 1.2593 0.3142 0.1404 0.027 Uiso 1 1 calc R
C22 C 0.5991(3) 0.32464(17) 0.39874(11) 0.0222(4) Uani 1 1 d .
H22 H 0.4904 0.3902 0.3971 0.027 Uiso 1 1 calc R
C23 C 0.5699(3) 0.21479(17) 0.45120(12) 0.0251(4) Uani 1 1 d .
H23 H 0.4409 0.2056 0.4853 0.030 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 0.0033 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
C7 O1 N1 105.59(11)
C15 N1 O1 109.47(12)
C15 N1 C18 118.70(13)
O1 N1 C18 107.02(11)
C16 C1 C2 119.56(16)
C16 C1 H1 120.2
C2 C1 H1 120.2
C3 C2 C1 120.28(16)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 121.17(17)
C2 C3 H3 119.4
C4 C3 H3 119.4
C17 C4 C3 117.39(15)
C17 C4 C5 121.31(15)
C3 C4 C5 121.30(15)
C6 C5 C4 122.89(15)
C6 C5 C18 119.62(14)
C4 C5 C18 117.49(14)
C5 C6 C7 122.70(15)
C5 C6 H6 118.7
C7 C6 H6 118.7
O1 C7 C6 109.70(13)
O1 C7 C8 110.80(12)
C6 C7 C8 115.91(14)
O1 C7 H7 106.6
C6 C7 H7 106.6
C8 C7 H7 106.6
C9 C8 C21 118.77(15)
C9 C8 C7 122.44(15)
C21 C8 C7 118.79(15)
C8 C9 C10 120.49(16)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.33(17)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C20 119.76(16)
C10 C11 H11 120.1
C20 C11 H11 120.1
C13 C12 C23 118.98(15)
C13 C12 H12 120.5
C23 C12 H12 120.5
C12 C13 C14 121.06(16)
C12 C13 H13 119.5
C14 C13 H13 119.5
C13 C14 C15 120.17(16)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C22 118.79(15)
C14 C15 N1 120.80(15)
C22 C15 N1 120.21(15)
C1 C16 C17 120.38(17)
C1 C16 H16 119.8
C17 C16 H16 119.8
C16 C17 C4 121.22(16)
C16 C17 H17 119.4
C4 C17 H17 119.4
N1 C18 C5 107.45(13)
N1 C18 C19 114.06(13)
C5 C18 C19 112.32(13)
N1 C18 H18 107.6
C5 C18 H18 107.6
C19 C18 H18 107.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C21 C20 C11 120.05(16)
C21 C20 H20 120.0
C11 C20 H20 120.0
C20 C21 C8 120.61(16)
C20 C21 H21 119.7
C8 C21 H21 119.7
C23 C22 C15 120.19(16)
C23 C22 H22 119.9
C15 C22 H22 119.9
C12 C23 C22 120.80(17)
C12 C23 H23 119.6
C22 C23 H23 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.4396(19)
O1 N1 1.4479(17)
N1 C15 1.415(2)
N1 C18 1.470(2)
C1 C16 1.380(3)
C1 C2 1.383(3)
C1 H1 0.9500
C2 C3 1.382(2)
C2 H2 0.9500
C3 C4 1.404(2)
C3 H3 0.9500
C4 C17 1.397(2)
C4 C5 1.490(2)
C5 C6 1.329(2)
C5 C18 1.517(2)
C6 C7 1.501(2)
C6 H6 0.9500
C7 C8 1.519(2)
C7 H7 1.0000
C8 C9 1.389(2)
C8 C21 1.393(2)
C9 C10 1.390(2)
C9 H9 0.9500
C10 C11 1.377(2)
C10 H10 0.9500
C11 C20 1.388(3)
C11 H11 0.9500
C12 C13 1.379(3)
C12 C23 1.383(2)
C12 H12 0.9500
C13 C14 1.385(2)
C13 H13 0.9500
C14 C15 1.390(2)
C14 H14 0.9500
C15 C22 1.398(2)
C16 C17 1.384(2)
C16 H16 0.9500
C17 H17 0.9500
C18 C19 1.524(2)
C18 H18 1.0000
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 C21 1.386(2)
C20 H20 0.9500
C21 H21 0.9500
C22 C23 1.384(2)
C22 H22 0.9500
C23 H23 0.9500
