#------------------------------------------------------------------------------
#$Date: 2018-03-15 18:33:54 +0200 (Thu, 15 Mar 2018) $
#$Revision: 206958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/55/7105519.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_7105519
loop_
_publ_author_name
'Cui, Li'
'Ye, Longwu'
'Zhang, Liming'
_publ_section_title
;
 Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step
 [5 + 2] annulation
;
_journal_issue                   19
_journal_name_full               'Chemical Communications'
_journal_page_first              3351
_journal_page_last               3353
_journal_paper_doi               10.1039/c001314e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C19 H21 N O'
_chemical_formula_weight         279.37
_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                109.154(5)
_cell_angle_beta                 91.003(5)
_cell_angle_gamma                102.607(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7366(19)
_cell_length_b                   10.508(3)
_cell_length_c                   13.624(4)
_cell_measurement_temperature    293(2)
_cell_volume                     753.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega scan'
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6116
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Psi scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0498
_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)+(0.0524P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1789
_reflns_number_total             2958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c001314e.txt
_cod_data_source_block           l1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H42 N2 O2'
_cod_original_formula_weight         558.74
_cod_original_formula_units_Z            1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7105519
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1735(3) 0.82136(19) 0.15695(13) 0.0414(4) Uani 1 1 d . . .
C2 C 0.0238(3) 0.94875(18) 0.31834(13) 0.0383(4) Uani 1 1 d . . .
C3 C 0.2737(3) 1.0349(2) 0.36825(15) 0.0442(5) Uani 1 1 d . . .
C4 C 0.3837(4) 1.15446(19) 0.33334(14) 0.0501(5) Uani 1 1 d . . .
C5 C 0.2284(4) 1.2150(2) 0.28006(16) 0.0536(5) Uani 1 1 d . . .
C6 C 0.1545(4) 1.1209(2) 0.16668(15) 0.0533(5) Uani 1 1 d . . .
C7 C -0.0490(4) 0.99535(19) 0.15521(16) 0.0467(5) Uani 1 1 d . . .
C8 C -0.0630(3) 0.82690(17) 0.35684(12) 0.0389(4) Uani 1 1 d . . .
C9 C 0.0737(4) 0.79061(19) 0.42366(14) 0.0464(5) Uani 1 1 d . . .
C10 C -0.0182(4) 0.6776(2) 0.45424(16) 0.0550(5) Uani 1 1 d . . .
C11 C -0.2470(4) 0.6000(2) 0.42086(15) 0.0554(5) Uani 1 1 d . . .
C12 C -0.3869(4) 0.6358(2) 0.35529(16) 0.0568(6) Uani 1 1 d . . .
C13 C -0.2949(3) 0.7469(2) 0.32330(15) 0.0474(5) Uani 1 1 d . . .
C14 C 0.1033(3) 0.73233(16) 0.04380(12) 0.0379(4) Uani 1 1 d . . .
C15 C 0.2708(4) 0.7291(2) -0.02804(15) 0.0513(5) Uani 1 1 d . . .
C16 C 0.2123(4) 0.6409(2) -0.13061(16) 0.0598(6) Uani 1 1 d . . .
C17 C -0.0119(4) 0.5564(2) -0.16207(15) 0.0545(5) Uani 1 1 d . . .
C18 C -0.1819(4) 0.56028(19) -0.09133(15) 0.0498(5) Uani 1 1 d . . .
C19 C -0.1233(3) 0.64768(18) 0.01083(14) 0.0432(5) Uani 1 1 d . . .
H2 H -0.094(3) 1.0111(16) 0.3384(11) 0.037(4) Uiso 1 1 d . . .
H9 H 0.237(3) 0.8420(18) 0.4469(13) 0.054(5) Uiso 1 1 d . . .
H10 H 0.079(3) 0.6517(19) 0.4954(15) 0.057(6) Uiso 1 1 d . . .
H11 H -0.318(3) 0.5186(19) 0.4424(13) 0.055(5) Uiso 1 1 d . . .
H12 H -0.548(4) 0.583(2) 0.3343(15) 0.071(6) Uiso 1 1 d . . .
H13 H -0.401(3) 0.7724(18) 0.2755(14) 0.059(5) Uiso 1 1 d . . .
H15 H 0.431(4) 0.7919(19) -0.0036(15) 0.066(6) Uiso 1 1 d . . .
H16 H 0.338(3) 0.6430(19) -0.1796(15) 0.067(6) Uiso 1 1 d . . .
H17 H -0.056(4) 0.493(2) -0.2361(16) 0.074(6) Uiso 1 1 d . . .
H18 H -0.343(3) 0.4992(18) -0.1125(13) 0.053(5) Uiso 1 1 d . . .
H19 H -0.246(3) 0.6516(18) 0.0624(14) 0.054(5) Uiso 1 1 d . . .
H1A H 0.338(3) 0.8816(18) 0.1612(13) 0.049(5) Uiso 1 1 d . . .
H3A H 0.268(3) 1.0753(19) 0.4443(16) 0.062(6) Uiso 1 1 d . . .
H5A H 0.326(3) 1.305(2) 0.2823(14) 0.060(6) Uiso 1 1 d . . .
H6A H 0.098(3) 1.169(2) 0.1307(15) 0.063(6) Uiso 1 1 d . . .
H7A H -0.095(3) 0.9447(18) 0.0805(15) 0.052(5) Uiso 1 1 d . . .
H1B H 0.191(3) 0.7603(18) 0.1991(13) 0.050(5) Uiso 1 1 d . . .
H3B H 0.391(3) 0.9777(19) 0.3626(13) 0.052(5) Uiso 1 1 d . . .
H5B H 0.085(3) 1.2273(18) 0.3163(14) 0.055(5) Uiso 1 1 d . . .
H6B H 0.300(4) 1.091(2) 0.1316(15) 0.073(6) Uiso 1 1 d . . .
H7B H -0.196(3) 1.0260(18) 0.1879(13) 0.054(5) Uiso 1 1 d . . .
N N -0.0051(2) 0.89600(13) 0.20324(10) 0.0386(4) Uani 1 1 d . . .
O O 0.5992(3) 1.19953(17) 0.34695(12) 0.0811(5) 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
N C1 C14 113.26(14) . . ?
N C1 H1A 114.6(10) . . ?
C14 C1 H1A 107.3(10) . . ?
N C1 H1B 106.4(10) . . ?
C14 C1 H1B 109.2(9) . . ?
H1A C1 H1B 105.8(13) . . ?
N C2 C3 115.49(14) . . ?
N C2 C8 108.43(13) . . ?
C3 C2 C8 112.55(15) . . ?
N C2 H2 104.2(8) . . ?
C3 C2 H2 108.2(8) . . ?
C8 C2 H2 107.4(8) . . ?
C4 C3 C2 117.66(16) . . ?
C4 C3 H3A 105.7(10) . . ?
C2 C3 H3A 108.9(11) . . ?
C4 C3 H3B 107.8(10) . . ?
C2 C3 H3B 112.5(10) . . ?
H3A C3 H3B 103.1(15) . . ?
O C4 C5 120.47(18) . . ?
O C4 C3 119.22(19) . . ?
C5 C4 C3 120.29(18) . . ?
C4 C5 C6 110.27(17) . . ?
C4 C5 H5A 106.4(11) . . ?
C6 C5 H5A 109.8(11) . . ?
C4 C5 H5B 110.8(10) . . ?
C6 C5 H5B 109.5(10) . . ?
H5A C5 H5B 110.0(15) . . ?
C7 C6 C5 113.16(17) . . ?
C7 C6 H6A 105.8(12) . . ?
C5 C6 H6A 109.0(12) . . ?
C7 C6 H6B 111.0(11) . . ?
C5 C6 H6B 110.6(11) . . ?
H6A C6 H6B 107.0(16) . . ?
N C7 C6 117.60(17) . . ?
N C7 H7A 107.6(10) . . ?
C6 C7 H7A 108.2(10) . . ?
N C7 H7B 104.5(9) . . ?
C6 C7 H7B 110.5(9) . . ?
H7A C7 H7B 108.1(14) . . ?
C9 C8 C13 117.39(17) . . ?
C9 C8 C2 124.54(16) . . ?
C13 C8 C2 118.06(16) . . ?
C10 C9 C8 120.93(19) . . ?
C10 C9 H9 119.3(11) . . ?
C8 C9 H9 119.7(11) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.2(11) . . ?
C9 C10 H10 119.7(11) . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 H11 122.5(10) . . ?
C12 C11 H11 118.6(10) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 121.6(12) . . ?
C11 C12 H12 118.1(12) . . ?
C12 C13 C8 121.47(19) . . ?
C12 C13 H13 119.3(10) . . ?
C8 C13 H13 119.2(10) . . ?
C19 C14 C15 118.51(16) . . ?
C19 C14 C1 121.24(16) . . ?
C15 C14 C1 120.17(16) . . ?
C14 C15 C16 120.56(19) . . ?
C14 C15 H15 117.5(11) . . ?
C16 C15 H15 122.0(11) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 121.9(11) . . ?
C15 C16 H16 117.7(11) . . ?
C16 C17 C18 119.55(19) . . ?
C16 C17 H17 121.0(11) . . ?
C18 C17 H17 119.5(11) . . ?
C19 C18 C17 120.02(19) . . ?
C19 C18 H18 119.4(10) . . ?
C17 C18 H18 120.6(10) . . ?
C14 C19 C18 120.94(18) . . ?
C14 C19 H19 118.5(10) . . ?
C18 C19 H19 120.5(10) . . ?
C1 N C7 114.60(14) . . ?
C1 N C2 113.59(13) . . ?
C7 N C2 114.83(13) . . ?
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 N 1.453(2) . ?
C1 C14 1.510(2) . ?
C1 H1A 1.003(17) . ?
C1 H1B 1.010(18) . ?
C2 N 1.474(2) . ?
C2 C3 1.527(2) . ?
C2 C8 1.528(2) . ?
C2 H2 1.019(16) . ?
C3 C4 1.503(3) . ?
C3 H3A 0.987(19) . ?
C3 H3B 0.98(2) . ?
C4 O 1.211(2) . ?
C4 C5 1.501(3) . ?
C5 C6 1.528(3) . ?
C5 H5A 0.976(19) . ?
C5 H5B 0.980(19) . ?
C6 C7 1.521(3) . ?
C6 H6A 0.91(2) . ?
C6 H6B 1.02(2) . ?
C7 N 1.463(2) . ?
C7 H7A 0.981(18) . ?
C7 H7B 1.024(19) . ?
C8 C9 1.387(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.960(18) . ?
C10 C11 1.365(3) . ?
C10 H10 0.92(2) . ?
C11 C12 1.383(3) . ?
C11 H11 1.001(18) . ?
C12 C13 1.380(3) . ?
C12 H12 0.95(2) . ?
C13 H13 1.020(19) . ?
C14 C19 1.377(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.983(19) . ?
C16 C17 1.363(3) . ?
C16 H16 0.99(2) . ?
C17 C18 1.380(3) . ?
C17 H17 1.00(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.981(17) . ?
C19 H19 0.999(18) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N C2 C3 C4 52.2(2) . . . . ?
C8 C2 C3 C4 177.50(15) . . . . ?
C2 C3 C4 O -159.13(18) . . . . ?
C2 C3 C4 C5 19.5(3) . . . . ?
O C4 C5 C6 101.9(2) . . . . ?
C3 C4 C5 C6 -76.7(2) . . . . ?
C4 C5 C6 C7 78.6(2) . . . . ?
C5 C6 C7 N -62.5(2) . . . . ?
N C2 C8 C9 124.50(17) . . . . ?
C3 C2 C8 C9 -4.5(2) . . . . ?
N C2 C8 C13 -55.78(19) . . . . ?
C3 C2 C8 C13 175.20(16) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C2 C8 C9 C10 -179.46(16) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C2 C8 C13 C12 -179.51(16) . . . . ?
N C1 C14 C19 -46.1(2) . . . . ?
N C1 C14 C15 137.29(17) . . . . ?
C19 C14 C15 C16 -1.0(3) . . . . ?
C1 C14 C15 C16 175.77(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C1 C14 C19 C18 -175.98(16) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C14 C1 N C7 -62.48(19) . . . . ?
C14 C1 N C2 162.78(14) . . . . ?
C6 C7 N C1 -66.2(2) . . . . ?
C6 C7 N C2 67.9(2) . . . . ?
C3 C2 N C1 52.4(2) . . . . ?
C8 C2 N C1 -75.00(17) . . . . ?
C3 C2 N C7 -82.3(2) . . . . ?
C8 C2 N C7 150.37(15) . . . . ?
