#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503197.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_1503197
loop_
_publ_author_name
'Miege, Frédéric'
'Meyer, Christophe'
'Cossy, Janine'
_publ_section_title
;
 Synthesis of 3-oxa- and 3-azabicyclo[4.1.0]heptanes by gold-catalyzed
 cycloisomerization of cyclopropenes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4144
_journal_page_last               4147
_journal_paper_doi               10.1021/ol101741f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C17 H19 N O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_chemical_name_systematic
;
 ?
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2353(5)
_cell_length_b                   13.2297(16)
_cell_length_c                   28.508(3)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      3
_cell_volume                     3106.0(5)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            25066
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0731
_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)+(0.1251P)²+0.1121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2253
_reflns_number_gt                2349
_reflns_number_total             4467
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol101741f_si_002.cif
_cod_data_source_block           fm532
_cod_depositor_comments
;
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_original_cell_volume        3105.9(5)
_cod_database_code               1503197
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
_atom_site_refinement_flags
O1 O 0.1996(3) 0.47293(16) -0.02436(8) 0.0806(7) Uani 1 1 d .
O2 O 0.2867(3) 0.58297(14) 0.02398(7) 0.0688(6) Uani 1 1 d .
O3 O 0.6324(2) 0.20821(13) 0.15779(7) 0.0643(6) Uani 1 1 d .
O4 O 0.5333(2) 0.09783(12) 0.10571(6) 0.0461(5) Uani 1 1 d .
O5 O 0.33262(18) 0.01743(12) 0.18091(6) 0.0453(4) Uani 1 1 d .
N1 N 0.2742(3) 0.49682(16) 0.01085(7) 0.0488(5) Uani 1 1 d .
C1 C 0.3537(3) 0.41679(17) 0.03786(7) 0.0361(5) Uani 1 1 d .
C2 C 0.3266(3) 0.31824(17) 0.02594(8) 0.0387(5) Uani 1 1 d .
H2 H 0.2624 0.3020 0.0002 0.046 Uiso 1 1 calc R
C3 C 0.4498(3) 0.44438(17) 0.07521(8) 0.0397(5) Uani 1 1 d .
H3 H 0.4676 0.5122 0.0821 0.048 Uiso 1 1 calc R
C4 C 0.3960(3) 0.24350(18) 0.05277(8) 0.0383(5) Uani 1 1 d .
H4 H 0.3796 0.1759 0.0451 0.046 Uiso 1 1 calc R
C5 C 0.5190(3) 0.36962(17) 0.10210(8) 0.0389(5) Uani 1 1 d .
H5 H 0.5847 0.3864 0.1275 0.047 Uiso 1 1 calc R
C6 C 0.4904(3) 0.26903(17) 0.09116(8) 0.0350(5) Uani 1 1 d .
C7 C 0.5602(3) 0.18968(18) 0.12238(9) 0.0409(6) Uani 1 1 d .
C8 C 0.5792(3) 0.01140(17) 0.13323(9) 0.0445(6) Uani 1 1 d .
H8A H 0.6425 0.0329 0.1601 0.053 Uiso 1 1 calc R
H8B H 0.6454 -0.0339 0.1145 0.053 Uiso 1 1 calc R
C9 C 0.4276(3) -0.04306(16) 0.14958(7) 0.0363(5) Uani 1 1 d .
H9 H 0.3608 -0.0561 0.1218 0.044 Uiso 1 1 calc R
C10 C 0.4688(2) -0.14361(17) 0.17081(8) 0.0342(5) Uani 1 1 d .
C11 C 0.4136(3) 0.0418(2) 0.22376(9) 0.0496(7) Uani 1 1 d .
H11A H 0.3391 0.0781 0.2440 0.059 Uiso 1 1 calc R
H11B H 0.5042 0.0863 0.2170 0.059 Uiso 1 1 calc R
C12 C 0.5056(3) -0.14218(18) 0.22149(8) 0.0405(6) Uani 1 1 d .
H12 H 0.6011 -0.1812 0.2311 0.049 Uiso 1 1 calc R
C13 C 0.4745(3) -0.0482(2) 0.24888(8) 0.0478(6) Uani 1 1 d .
H13 H 0.5528 -0.0343 0.2740 0.057 Uiso 1 1 calc R
C14 C 0.3708(3) -0.1379(2) 0.25632(9) 0.0558(7) Uani 1 1 d .
H14A H 0.2605 -0.1356 0.2444 0.067 Uiso 1 1 calc R
H14B H 0.3841 -0.1752 0.2854 0.067 Uiso 1 1 calc R
C15 C 0.4710(3) -0.22836(18) 0.14464(8) 0.0411(6) Uani 1 1 d .
C16 C 0.4393(4) -0.2297(2) 0.09282(8) 0.0589(8) Uani 1 1 d .
H16A H 0.4303 -0.1616 0.0815 0.088 Uiso 1 1 calc R
H16B H 0.3399 -0.2653 0.0867 0.088 Uiso 1 1 calc R
H16C H 0.5273 -0.2631 0.0771 0.088 Uiso 1 1 calc R
C17 C 0.4998(3) -0.3297(2) 0.16556(9) 0.0523(7) Uani 1 1 d .
H17A H 0.5178 -0.3228 0.1987 0.078 Uiso 1 1 calc R
H17B H 0.5935 -0.3600 0.1513 0.078 Uiso 1 1 calc R
H17C H 0.4067 -0.3719 0.1603 0.078 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 O4 C8 119.36(19)
C11 O5 C9 113.87(16)
O2 N1 O1 123.0(2)
O2 N1 C1 118.9(2)
O1 N1 C1 118.1(2)
C2 C1 C3 122.7(2)
C2 C1 N1 119.1(2)
C3 C1 N1 118.2(2)
C1 C2 C4 118.7(2)
C1 C2 H2 120.7
C4 C2 H2 120.7
C1 C3 C5 118.6(2)
C1 C3 H3 120.7
C5 C3 H3 120.7
C2 C4 C6 119.9(2)
C2 C4 H4 120.1
C6 C4 H4 120.1
C3 C5 C6 119.6(2)
C3 C5 H5 120.2
C6 C5 H5 120.2
C4 C6 C5 120.5(2)
C4 C6 C7 121.1(2)
C5 C6 C7 118.4(2)
O3 C7 O4 125.0(2)
O3 C7 C6 123.4(2)
O4 C7 C6 111.5(2)
O4 C8 C9 109.24(18)
O4 C8 H8A 109.8
C9 C8 H8A 109.8
O4 C8 H8B 109.8
C9 C8 H8B 109.8
H8A C8 H8B 108.3
O5 C9 C10 111.56(17)
O5 C9 C8 112.10(18)
C10 C9 C8 111.05(18)
O5 C9 H9 107.3
C10 C9 H9 107.3
C8 C9 H9 107.3
C15 C10 C12 123.4(2)
C15 C10 C9 121.2(2)
C12 C10 C9 115.46(19)
O5 C11 C13 113.0(2)
O5 C11 H11A 109.0
C13 C11 H11A 109.0
O5 C11 H11B 109.0
C13 C11 H11B 109.0
H11A C11 H11B 107.8
C10 C12 C14 120.0(2)
C10 C12 C13 119.2(2)
C14 C12 C13 59.45(17)
C10 C12 H12 115.5
C14 C12 H12 115.5
C13 C12 H12 115.5
C14 C13 C11 121.4(2)
C14 C13 C12 60.27(17)
C11 C13 C12 118.5(2)
C14 C13 H13 115.2
C11 C13 H13 115.2
C12 C13 H13 115.2
C13 C14 C12 60.28(16)
C13 C14 H14A 117.7
C12 C14 H14A 117.7
C13 C14 H14B 117.7
C12 C14 H14B 117.7
H14A C14 H14B 114.9
C10 C15 C17 122.1(2)
C10 C15 C16 123.6(2)
C17 C15 C16 114.3(2)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 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
O1 N1 1.219(3)
O2 N1 1.204(3)
O3 C7 1.197(3)
O4 C7 1.324(3)
O4 C8 1.437(3)
O5 C11 1.429(3)
O5 C9 1.432(3)
N1 C1 1.464(3)
C1 C2 1.366(3)
C1 C3 1.376(3)
C2 C4 1.375(3)
C2 H2 0.9300
C3 C5 1.375(3)
C3 H3 0.9300
C4 C6 1.384(3)
C4 H4 0.9300
C5 C6 1.387(3)
C5 H5 0.9300
C6 C7 1.492(3)
C8 C9 1.515(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.501(3)
C9 H9 0.9800
C10 C15 1.347(3)
C10 C12 1.476(3)
C11 C13 1.477(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C14 1.490(3)
C12 C13 1.491(3)
C12 H12 0.9800
C13 C14 1.478(4)
C13 H13 0.9800
C14 H14A 0.9700
C14 H14B 0.9700
C15 C17 1.487(4)
C15 C16 1.500(3)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
