#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152008.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_7152008
loop_
_publ_author_name
'Devi, Rema B.'
'Henrot, Matthias'
'De Paolis, Michaël'
'Maddaluno, Jacques'
_publ_section_title
;
 Domino alkylation/oxa-Michael of 1,3-cyclohexanediones: Steering the
 C/O-chemoselectivity to reach tetrahydrobenzofuranones.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6509
_journal_page_last               6512
_journal_paper_doi               10.1039/c1ob05923h
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H11 N1 O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.2
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-10-04T16:01:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 107.780(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4105(17)
_cell_length_b                   5.6321(11)
_cell_length_c                   10.022(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     452.05(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2607
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1631
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                1573
_reflns_number_total             1631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05923h.txt
_cod_data_source_block           rdbcn
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7152008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.21257(17) -0.2664(3) 1.01666(12) 0.0623(4) Uani 1 1 d .
O2 O 0.16090(13) 0.3298(2) 0.69264(12) 0.0505(3) Uani 1 1 d .
N1 N 0.4254(3) -0.1194(4) 0.6028(2) 0.0777(6) Uani 1 1 d .
C1 C 0.12563(19) -0.1655(3) 0.91052(15) 0.0442(4) Uani 1 1 d .
C2 C -0.0516(2) -0.2438(4) 0.83683(19) 0.0538(5) Uani 1 1 d .
H2A H -0.1256 -0.1681 0.8816 0.065 Uiso 1 1 calc R
H2B H -0.0593 -0.414 0.8485 0.065 Uiso 1 1 calc R
C3 C -0.1115(2) -0.1860(4) 0.68126(18) 0.0576(5) Uani 1 1 d .
H3A H -0.2299 -0.2206 0.6446 0.069 Uiso 1 1 calc R
H3B H -0.0538 -0.2875 0.633 0.069 Uiso 1 1 calc R
C4 C -0.0824(2) 0.0719(4) 0.65051(18) 0.0548(5) Uani 1 1 d .
H4A H -0.0959 0.0912 0.5515 0.066 Uiso 1 1 calc R
H4B H -0.1635 0.1724 0.6742 0.066 Uiso 1 1 calc R
C5 C 0.08851(18) 0.1423(3) 0.73413(15) 0.0417(4) Uani 1 1 d .
C6 C 0.18284(19) 0.0366(3) 0.85133(15) 0.0410(4) Uani 1 1 d .
C7 C 0.3449(2) 0.1675(4) 0.90577(17) 0.0492(4) Uani 1 1 d .
H7A H 0.4395 0.0622 0.9175 0.059 Uiso 1 1 calc R
H7B H 0.3543 0.2449 0.9943 0.059 Uiso 1 1 calc R
C8 C 0.33202(18) 0.3505(3) 0.78835(16) 0.0442(4) Uani 1 1 d .
H8 H 0.3494 0.5106 0.8285 0.053 Uiso 1 1 calc R
C9 C 0.45193(19) 0.3074(3) 0.70372(17) 0.0468(4) Uani 1 1 d .
H9A H 0.4292 0.4211 0.6275 0.056 Uiso 1 1 calc R
H9B H 0.5655 0.333 0.7633 0.056 Uiso 1 1 calc R
C10 C 0.4372(2) 0.0675(4) 0.64646(19) 0.0515(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0676(8) 0.0679(10) 0.0492(7) 0.0153(6) 0.0145(6) 0.0029(7)
O2 0.0418(5) 0.0538(8) 0.0532(6) 0.0144(6) 0.0104(5) 0.0071(5)
N1 0.0934(14) 0.0523(13) 0.0999(13) -0.0118(10) 0.0482(11) 0.0026(10)
C1 0.0487(8) 0.0480(10) 0.0393(7) -0.0023(7) 0.0186(6) 0.0030(8)
C2 0.0544(9) 0.0551(12) 0.0563(9) -0.0052(8) 0.0235(8) -0.0080(8)
C3 0.0449(8) 0.0680(14) 0.0559(9) -0.0083(9) 0.0096(7) -0.0046(9)
C4 0.0385(8) 0.0691(13) 0.0519(9) 0.0044(9) 0.0066(7) 0.0082(9)
C5 0.0383(7) 0.0455(10) 0.0431(8) 0.0014(7) 0.0151(6) 0.0073(7)
C6 0.0376(7) 0.0492(10) 0.0363(7) 0.0001(6) 0.0112(6) 0.0033(7)
C7 0.0412(7) 0.0625(11) 0.0414(8) 0.0057(7) 0.0090(6) 0.0002(8)
C8 0.0426(8) 0.0411(9) 0.0483(8) -0.0012(7) 0.0131(6) -0.0016(7)
C9 0.0454(8) 0.0447(10) 0.0517(8) 0.0040(7) 0.0168(6) -0.0031(8)
C10 0.0513(10) 0.0504(12) 0.0581(10) 0.0042(9) 0.0246(8) 0.0076(8)
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 0 '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 0.006 '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
C5 O2 C8 107.79(12)
O1 C1 C6 122.60(15)
O1 C1 C2 121.59(17)
C6 C1 C2 115.78(14)
C1 C2 C3 113.99(14)
C1 C2 H2A 108.8
C3 C2 H2A 108.8
C1 C2 H2B 108.8
C3 C2 H2B 108.8
H2A C2 H2B 107.6
C2 C3 C4 112.91(16)
C2 C3 H3A 109
C4 C3 H3A 109
C2 C3 H3B 109
C4 C3 H3B 109
H3A C3 H3B 107.8
C5 C4 C3 109.28(15)
C5 C4 H4A 109.8
C3 C4 H4A 109.8
C5 C4 H4B 109.8
C3 C4 H4B 109.8
H4A C4 H4B 108.3
C6 C5 O2 114.61(14)
C6 C5 C4 126.19(16)
O2 C5 C4 119.20(14)
C5 C6 C1 122.14(14)
C5 C6 C7 109.29(15)
C1 C6 C7 128.55(14)
C6 C7 C8 101.92(12)
C6 C7 H7A 111.4
C8 C7 H7A 111.4
C6 C7 H7B 111.4
C8 C7 H7B 111.4
H7A C7 H7B 109.2
O2 C8 C9 107.87(13)
O2 C8 C7 105.75(13)
C9 C8 C7 114.48(15)
O2 C8 H8 109.5
C9 C8 H8 109.5
C7 C8 H8 109.5
C10 C9 C8 112.07(15)
C10 C9 H9A 109.2
C8 C9 H9A 109.2
C10 C9 H9B 109.2
C8 C9 H9B 109.2
H9A C9 H9B 107.9
N1 C10 C9 179.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.231(2)
O2 C5 1.347(2)
O2 C8 1.4704(18)
N1 C10 1.133(3)
C1 C6 1.433(2)
C1 C2 1.513(2)
C2 C3 1.520(3)
C2 H2A 0.97
C2 H2B 0.97
C3 C4 1.520(3)
C3 H3A 0.97
C3 H3B 0.97
C4 C5 1.480(2)
C4 H4A 0.97
C4 H4B 0.97
C5 C6 1.339(2)
C6 C7 1.498(2)
C7 C8 1.543(3)
C7 H7A 0.97
C7 H7B 0.97
C8 C9 1.522(2)
C8 H8 0.98
C9 C10 1.459(3)
C9 H9A 0.97
C9 H9B 0.97
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
O1 C1 C2 C3 -153.41(18)
C6 C1 C2 C3 28.4(2)
C1 C2 C3 C4 -50.6(2)
C2 C3 C4 C5 45.2(2)
C8 O2 C5 C6 3.72(18)
C8 O2 C5 C4 -176.47(15)
C3 C4 C5 C6 -21.7(2)
C3 C4 C5 O2 158.56(14)
O2 C5 C6 C1 179.99(14)
C4 C5 C6 C1 0.2(3)
O2 C5 C6 C7 1.68(19)
C4 C5 C6 C7 -178.12(16)
O1 C1 C6 C5 178.60(16)
C2 C1 C6 C5 -3.2(2)
O1 C1 C6 C7 -3.4(3)
C2 C1 C6 C7 174.73(17)
C5 C6 C7 C8 -5.91(18)
C1 C6 C7 C8 175.91(16)
C5 O2 C8 C9 115.65(15)
C5 O2 C8 C7 -7.26(17)
C6 C7 C8 O2 7.75(18)
C6 C7 C8 C9 -110.86(16)
O2 C8 C9 C10 -63.47(18)
C7 C8 C9 C10 53.9(2)
C8 C9 C10 N1 -3E1(3)
