#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:26:18 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178899 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/28/4112850.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_4112850
loop_
_publ_author_name
'Claude Spino'
'Hadi Rezaei'
'Kristina Dupont-Gaudet'
'Francis Bélanger'
_publ_section_title
;
 Inter- and Intramolecular [4 + 1]-Cycloadditions Between Electron-Poor
 Dienes and Electron-Rich Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9926
_journal_page_last               9927
_journal_paper_doi               10.1021/ja046344x
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C17 H19 N2 O6'
_chemical_formula_sum            'C17 H19 N2 O6'
_chemical_formula_weight         333.33
_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                94.160(8)
_cell_angle_beta                 100.234(8)
_cell_angle_gamma                112.484(8)
_cell_formula_units_Z            2
_cell_length_a                   7.6242(9)
_cell_length_b                   9.0590(9)
_cell_length_c                   12.9909(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      12.5
_cell_volume                     806.06(15)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_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-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.5100
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2854
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9495
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      1.37
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0459
_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)+(0.0369P)²+0.3467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2383
_reflns_number_total             2854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja046344xsi20040621_105651.cif
_cod_data_source_block           hr2-142
_cod_original_cell_volume        806.06(14)
_cod_database_code               4112850
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
C1 C 0.7234(3) 0.3276(2) 0.65105(15) 0.0468(4) Uani 1 1 d .
C3 C 0.8375(3) 0.1902(3) 0.53079(18) 0.0615(5) Uani 1 1 d .
H3A H 0.8596 0.0924 0.5187 0.074 Uiso 1 1 calc R
H3B H 0.9618 0.2820 0.5421 0.074 Uiso 1 1 calc R
C4 C 0.7018(3) 0.1998(3) 0.43567(17) 0.0633(6) Uani 1 1 d .
H4A H 0.5769 0.1087 0.4241 0.076 Uiso 1 1 calc R
H4B H 0.7549 0.1962 0.3734 0.076 Uiso 1 1 calc R
C5 C 0.6760(3) 0.3562(3) 0.45383(16) 0.0584(5) Uani 1 1 d .
H5A H 0.5789 0.3589 0.3955 0.070 Uiso 1 1 calc R
H5B H 0.7978 0.4466 0.4559 0.070 Uiso 1 1 calc R
C6 C 0.6124(3) 0.3730(2) 0.55738(14) 0.0461(4) Uani 1 1 d .
H6 H 0.6322 0.4860 0.5756 0.055 Uiso 1 1 calc R
C7 C 0.4060(3) 0.2685(2) 0.55772(17) 0.0555(5) Uani 1 1 d .
H7 H 0.3019 0.2452 0.5006 0.067 Uiso 1 1 calc R
C8 C 0.3886(3) 0.2135(2) 0.64753(17) 0.0564(5) Uani 1 1 d .
H8 H 0.2709 0.1462 0.6615 0.068 Uiso 1 1 calc R
C9 C 0.5810(3) 0.2719(2) 0.72530(15) 0.0511(5) Uani 1 1 d .
H9 H 0.5955 0.1823 0.7586 0.061 Uiso 1 1 calc R
C11 C 1.0352(4) 0.4355(4) 0.7715(2) 0.0861(8) Uani 1 1 d .
H11A H 1.1494 0.5340 0.7961 0.129 Uiso 1 1 calc R
H11B H 1.0706 0.3543 0.7407 0.129 Uiso 1 1 calc R
H11C H 0.9776 0.3993 0.8299 0.129 Uiso 1 1 calc R
C10 C 0.6045(3) 0.4082(3) 0.80878(16) 0.0596(5) Uani 1 1 d .
H12A H 0.7365 0.4536 0.8514 0.072 Uiso 1 1 calc R
H12B H 0.5820 0.4930 0.7746 0.072 Uiso 1 1 calc R
C14 C 0.5253(3) 0.2855(3) 0.95834(16) 0.0571(5) Uani 1 1 d .
C15 C 0.3783(3) 0.2314(2) 1.02438(15) 0.0499(5) Uani 1 1 d .
C16 C 0.2014(3) 0.2444(2) 0.99878(15) 0.0527(5) Uani 1 1 d .
H16 H 0.1702 0.2845 0.9374 0.063 Uiso 1 1 calc R
C17 C 0.0709(3) 0.1984(2) 1.06316(15) 0.0525(5) Uani 1 1 d .
H17 H -0.0491 0.2054 1.0456 0.063 Uiso 1 1 calc R
C18 C 0.1222(3) 0.1419(2) 1.15377(15) 0.0489(5) Uani 1 1 d .
C19 C 0.2957(3) 0.1248(3) 1.18118(16) 0.0566(5) Uani 1 1 d .
H19 H 0.3259 0.0845 1.2426 0.068 Uiso 1 1 calc R
C20 C 0.4227(3) 0.1692(3) 1.11503(16) 0.0590(5) Uani 1 1 d .
H20 H 0.5400 0.1573 1.1313 0.071 Uiso 1 1 calc R
N21 N -0.0130(3) 0.0979(2) 1.22499(14) 0.0603(5) Uani 1 1 d .
O2 O 0.7586(2) 0.18959(16) 0.62318(11) 0.0533(4) Uani 1 1 d .
O10 O 0.8989(2) 0.46365(17) 0.69399(11) 0.0593(4) Uani 1 1 d .
O13 O 0.4677(2) 0.34911(18) 0.87647(10) 0.0586(4) Uani 1 1 d .
O15 O 0.6793(2) 0.2751(3) 0.97763(14) 0.0865(6) Uani 1 1 d .
O22 O -0.1810(2) 0.0772(2) 1.19090(14) 0.0838(5) Uani 1 1 d .
O23 O 0.0488(3) 0.0847(3) 1.31509(14) 0.0929(6) 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
O2 C1 O10 111.43(15)
O2 C1 C6 113.02(15)
O10 C1 C6 107.53(15)
O2 C1 C9 103.76(14)
O10 C1 C9 115.93(15)
C6 C1 C9 105.15(15)
O2 C3 C4 110.83(17)
C3 C4 C5 108.82(18)
C4 C5 C6 111.09(16)
C7 C6 C5 116.27(17)
C7 C6 C1 101.48(15)
C5 C6 C1 114.49(16)
C8 C7 C6 112.34(18)
C7 C8 C9 112.04(18)
C8 C9 C10 111.54(17)
C8 C9 C1 100.91(15)
C10 C9 C1 112.78(16)
O13 C10 C9 110.48(17)
O15 C14 O13 123.8(2)
O15 C14 C15 123.73(19)
O13 C14 C15 112.45(17)
C16 C15 C20 119.46(19)
C16 C15 C14 121.90(18)
C20 C15 C14 118.64(18)
C17 C16 C15 120.65(18)
C18 C17 C16 118.25(18)
C17 C18 C19 122.84(19)
C17 C18 N21 118.70(17)
C19 C18 N21 118.46(18)
C20 C19 C18 117.97(18)
C19 C20 C15 120.79(19)
O23 N21 O22 123.28(19)
O23 N21 C18 118.40(18)
O22 N21 C18 118.32(18)
C1 O2 C3 115.25(15)
C1 O10 C11 115.22(17)
C14 O13 C10 116.12(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.411(2)
C1 O10 1.412(2)
C1 C6 1.530(3)
C1 C9 1.545(3)
C3 O2 1.435(2)
C3 C4 1.495(3)
C4 C5 1.511(3)
C5 C6 1.525(3)
C6 C7 1.495(3)
C7 C8 1.310(3)
C8 C9 1.501(3)
C9 C10 1.517(3)
C11 O10 1.423(3)
C10 O13 1.454(2)
C14 O15 1.197(2)
C14 O13 1.331(2)
C14 C15 1.488(3)
C15 C16 1.382(3)
C15 C20 1.386(3)
C16 C17 1.376(3)
C17 C18 1.370(3)
C18 C19 1.377(3)
C18 N21 1.469(3)
C19 C20 1.373(3)
N21 O23 1.214(2)
N21 O22 1.214(2)
