#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:26:50 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250103 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038127.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_4038127
loop_
_publ_author_name
'Rinaldi, Antonia'
'Langé, Vittoria'
'Scarpi, Dina'
'Occhiato, Ernesto G.'
_publ_section_title
;
 One-Pot Access to 1,7a-Dihydro-1,3a-ethano-indene and
 1,8a-Dihydro-1,3a-ethano-azulene Skeletons by a Sequential
 Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov
 Cyclization/[4+2] Cycloaddition Reaction.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5078
_journal_page_last               5086
_journal_paper_doi               10.1021/acs.joc.0c00088
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C17 H21 N O3'
_chemical_formula_sum            'C17 H21 N O3'
_chemical_formula_weight         287.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date
;
'Thu Dec 06 17:28:40 2018'
;
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_cell_angle_alpha                94.799(7)
_cell_angle_beta                 97.856(7)
_cell_angle_gamma                97.882(8)
_cell_formula_units_Z            2
_cell_length_a                   8.3484(9)
_cell_length_b                   8.5960(8)
_cell_length_c                   10.5662(8)
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5160
_cell_measurement_theta_min      5.1950
_cell_volume                     739.98(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012'
_computing_publication_material  'WinGX publication routines'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1241
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9734
_diffrn_measured_fraction_theta_max 0.9027
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074   77.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega   27.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -30.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -77.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -45.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   22.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -94.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074  -77.0000  120.0000 99

#__ type_ start__ end____ width___ exp.time_
  8 omega  -63.00  -36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega  -69.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega  -65.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 11 omega  -65.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega -116.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
 13 omega   87.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       45.9074  125.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  -52.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 15 omega  -50.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega  -95.00  -68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   61.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega  -97.00  -72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega -146.00  -78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -61.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
 19 omega  -98.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -45.9074 -125.0000 -180.0000 25

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4262
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         61.165
_diffrn_reflns_theta_min         5.223
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1810P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.3109
_reflns_number_gt                1370
_reflns_number_total             2223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00088_si_002.cif
_cod_data_source_block           exp-333
_cod_depositor_comments          'Adding full bibliography for 4038127.cif.'
_cod_database_code               4038127
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2353(5) -0.2112(5) 0.5222(3) 0.0414(11) Uani 1 1 d . . . . .
O1 O 0.2752(4) 0.0288(5) 0.4436(3) 0.0512(10) Uani 1 1 d . . . . .
O2 O 0.2470(4) -0.4668(4) 0.5722(3) 0.0484(10) Uani 1 1 d . . . . .
O3 O -0.2870(4) -0.1734(5) 0.2031(3) 0.0532(11) Uani 1 1 d . . . . .
C1 C 0.2876(5) -0.2295(6) 0.2066(4) 0.0389(12) Uani 1 1 d . . . . .
C2 C 0.3464(6) -0.3872(6) 0.1662(4) 0.0363(11) Uani 1 1 d . . . . .
H2 H 0.4662 -0.3728 0.1803 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2831(6) -0.4461(7) 0.0255(4) 0.0440(13) Uani 1 1 d . . . . .
H3A H 0.1652 -0.4747 0.0134 0.053 Uiso 1 1 calc R U . . .
H3B H 0.3303 -0.5391 0.0009 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3301(6) -0.3159(7) -0.0580(4) 0.0463(13) Uani 1 1 d . . . . .
H4A H 0.2901 -0.3532 -0.1474 0.056 Uiso 1 1 calc R U . . .
H4B H 0.4483 -0.2914 -0.0482 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2594(6) -0.1658(6) -0.0220(4) 0.0426(13) Uani 1 1 d . . . . .
H5A H 0.2913 -0.0860 -0.0772 0.051 Uiso 1 1 calc R U . . .
H5B H 0.1409 -0.1888 -0.0353 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3211(6) -0.1023(6) 0.1189(4) 0.0407(12) Uani 1 1 d . . . . .
H6A H 0.4378 -0.0654 0.1296 0.049 Uiso 1 1 calc R U . . .
H6B H 0.2670 -0.0134 0.1421 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3801(6) -0.1977(6) 0.3479(4) 0.0400(12) Uani 1 1 d . . . . .
H7 H 0.4933 -0.1471 0.3508 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3722(6) -0.3666(6) 0.3924(4) 0.0390(12) Uani 1 1 d . . . . .
H8 H 0.4824 -0.3918 0.4176 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2801(6) -0.4800(6) 0.2737(4) 0.0399(12) Uani 1 1 d . . . . .
C10 C 0.1005(5) -0.4496(5) 0.2562(4) 0.0360(11) Uani 1 1 d . . . . .
H10A H 0.0334 -0.5244 0.1895 0.043 Uiso 1 1 calc R U . . .
H10B H 0.0552 -0.4575 0.3356 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1104(6) -0.2841(6) 0.2182(4) 0.0387(12) Uani 1 1 d . . . . .
C12 C -0.0103(6) -0.1966(6) 0.2023(4) 0.0390(12) Uani 1 1 d . . . . .
H12 H 0.0137 -0.0961 0.1769 0.047 Uiso 1 1 calc R U . . .
C13 C -0.1762(6) -0.2500(7) 0.2225(4) 0.0454(13) Uani 1 1 d . . . . .
H13 H -0.1990 -0.3484 0.2519 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3058(6) -0.6496(6) 0.2754(5) 0.0420(12) Uani 1 1 d . . . . .
H14A H 0.4208 -0.6553 0.2867 0.063 Uiso 1 1 calc R U . . .
H14B H 0.2588 -0.6935 0.3450 0.063 Uiso 1 1 calc R U . . .
H14C H 0.2541 -0.7084 0.1956 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2798(6) -0.3611(6) 0.5066(4) 0.0386(12) Uani 1 1 d . . . . .
C16 C 0.2954(6) -0.1121(6) 0.4398(4) 0.0391(12) Uani 1 1 d . . . . .
C17 C 0.1299(7) -0.1680(7) 0.6154(5) 0.0497(14) Uani 1 1 d . . . . .
H17A H 0.1028 -0.2560 0.6628 0.075 Uiso 1 1 calc R U . . .
H17B H 0.1864 -0.0796 0.6736 0.075 Uiso 1 1 calc R U . . .
H17C H 0.0315 -0.1400 0.5709 0.075 Uiso 1 1 calc R U . . .
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'
N N 0.0311 0.0180 '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'
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
C16 N1 C15 113.2(4) . . ?
C16 N1 C17 124.1(4) . . ?
C15 N1 C17 122.6(4) . . ?
C6 C1 C11 117.0(4) . . ?
C6 C1 C2 114.1(4) . . ?
C11 C1 C2 101.9(4) . . ?
C6 C1 C7 116.8(4) . . ?
C11 C1 C7 105.6(3) . . ?
C2 C1 C7 99.0(3) . . ?
C3 C2 C9 119.4(4) . . ?
C3 C2 C1 111.8(4) . . ?
C9 C2 C1 96.3(4) . . ?
C3 C2 H2 109.5 . . ?
C9 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
C2 C3 C4 109.1(4) . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 C5 111.8(4) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 110.8(4) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C5 110.7(4) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C16 C7 C8 103.9(3) . . ?
C16 C7 C1 115.0(4) . . ?
C8 C7 C1 102.9(4) . . ?
C16 C7 H7 111.5 . . ?
C8 C7 H7 111.5 . . ?
C1 C7 H7 111.5 . . ?
C15 C8 C7 104.7(4) . . ?
C15 C8 C9 114.0(4) . . ?
C7 C8 C9 105.2(3) . . ?
C15 C8 H8 110.9 . . ?
C7 C8 H8 110.9 . . ?
C9 C8 H8 110.9 . . ?
C14 C9 C10 116.2(4) . . ?
C14 C9 C2 117.5(4) . . ?
C10 C9 C2 100.7(3) . . ?
C14 C9 C8 115.1(4) . . ?
C10 C9 C8 106.7(4) . . ?
C2 C9 C8 98.2(3) . . ?
C11 C10 C9 104.0(4) . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 127.8(4) . . ?
C12 C11 C1 125.4(5) . . ?
C10 C11 C1 106.8(4) . . ?
C11 C12 C13 123.6(5) . . ?
C11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
O3 C13 C12 123.6(5) . . ?
O3 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 N1 125.3(4) . . ?
O2 C15 C8 127.3(5) . . ?
N1 C15 C8 107.4(4) . . ?
O1 C16 N1 122.5(5) . . ?
O1 C16 C7 127.0(4) . . ?
N1 C16 C7 110.5(4) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
N1 C16 1.364(6) . ?
N1 C15 1.392(6) . ?
N1 C17 1.466(7) . ?
O1 C16 1.244(6) . ?
O2 C15 1.212(6) . ?
O3 C13 1.212(6) . ?
C1 C6 1.513(6) . ?
C1 C11 1.514(6) . ?
C1 C2 1.551(7) . ?
C1 C7 1.567(6) . ?
C2 C3 1.527(6) . ?
C2 C9 1.561(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.524(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.532(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.536(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C16 1.481(7) . ?
C7 C8 1.560(7) . ?
C7 H7 0.9800 . ?
C8 C15 1.520(6) . ?
C8 C9 1.562(7) . ?
C8 H8 0.9800 . ?
C9 C14 1.504(7) . ?
C9 C10 1.546(6) . ?
C10 C11 1.505(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.339(7) . ?
C12 C13 1.448(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
