#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:23:55 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178948 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/77/4117750.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_4117750
loop_
_publ_author_name
'Francis Beaumier'
'Marianne Dupuis'
'Claude Spino'
'Claude Y. Legault'
_publ_section_title
;
 Formal Intramolecular (4 + 1)-Cycloaddition of Dialkoxycarbenes: Control
 of the Stereoselectivity and a Mechanistic Portrait
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5938
_journal_page_last               5953
_journal_paper_doi               10.1021/ja211927b
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C9 H13 N O4'
_chemical_formula_weight         199.2
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2008-04-14T08:50:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.31(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6278(17)
_cell_length_b                   8.754(2)
_cell_length_c                   16.144(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     936.4(5)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1746
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       Prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.96
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.96
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.053
_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)+(0.0422P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1007
_reflns_number_total             1746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211927b_si_005.cif
_cod_data_source_block           fb3120
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Psi-Scan' changed to
'psi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               4117750
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
H3 H 0.579(4) 0.593(3) 0.9460(14) 0.032(7) Uiso 1 1 d .
H1 H 0.067(4) 0.516(3) 0.8140(14) 0.023(7) Uiso 1 1 d .
H4 H 0.394(3) 0.829(3) 0.8780(13) 0.014(6) Uiso 1 1 d .
H2 H 0.413(3) 0.413(3) 0.8448(13) 0.021(6) Uiso 1 1 d .
C1 C 0.1798(4) 0.5752(3) 0.81873(16) 0.0249(6) Uani 1 1 d .
C2 C 0.3671(4) 0.5118(3) 0.85843(15) 0.0248(6) Uani 1 1 d .
C3 C 0.4529(4) 0.6101(3) 0.90895(15) 0.0231(6) Uani 1 1 d .
C4 C 0.3393(4) 0.7582(3) 0.91291(15) 0.0217(6) Uani 1 1 d .
C5 C 0.3273(4) 0.8326(3) 0.99826(16) 0.0317(7) Uani 1 1 d .
H5A H 0.4601 0.8319 1.0248 0.038 Uiso 1 1 calc R
H5B H 0.2854 0.9382 0.9918 0.038 Uiso 1 1 calc R
C6 C 0.1799(4) 0.7503(3) 1.05319(16) 0.0318(7) Uani 1 1 d .
H6A H 0.2312 0.6496 1.0672 0.038 Uiso 1 1 calc R
H6B H 0.163 0.8071 1.1042 0.038 Uiso 1 1 calc R
C7 C -0.0193(4) 0.7367(3) 1.00727(16) 0.0319(7) Uani 1 1 d .
H7A H -0.1158 0.6863 1.0424 0.038 Uiso 1 1 calc R
H7B H -0.0705 0.838 0.9944 0.038 Uiso 1 1 calc R
C8 C 0.1329(4) 0.7145(3) 0.87459(14) 0.0217(6) Uani 1 1 d .
C9 C -0.1577(4) 0.8326(4) 0.80933(17) 0.0399(8) Uani 1 1 d .
H9A H -0.1817 0.7382 0.7804 0.06 Uiso 1 1 calc R
H9B H -0.1927 0.9167 0.7736 0.06 Uiso 1 1 calc R
H9C H -0.2389 0.836 0.8578 0.06 Uiso 1 1 calc R
N1 N 0.2181(4) 0.6315(2) 0.73154(13) 0.0303(6) Uani 1 1 d .
O1 O 0.0828(3) 0.6123(2) 0.67916(11) 0.0423(6) Uani 1 1 d .
O2 O 0.3761(3) 0.6975(2) 0.71883(11) 0.0387(5) Uani 1 1 d .
O3 O 0.0516(2) 0.84273(18) 0.83342(10) 0.0255(5) Uani 1 1 d .
O4 O -0.0002(2) 0.65111(19) 0.93152(10) 0.0251(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
C1 0.0264(16) 0.0240(14) 0.0243(14) 0.0026(12) -0.0029(12) -0.0050(13)
C2 0.0297(16) 0.0200(15) 0.0249(14) 0.0026(12) 0.0082(12) 0.0066(13)
C3 0.0220(15) 0.0240(14) 0.0233(13) 0.0061(12) 0.0009(11) 0.0001(12)
C4 0.0233(15) 0.0166(13) 0.0253(15) 0.0028(12) 0.0039(11) -0.0001(12)
C5 0.0310(16) 0.0274(15) 0.0365(16) -0.0075(13) -0.0019(13) -0.0010(13)
C6 0.0332(17) 0.0350(17) 0.0272(15) -0.0062(13) 0.0013(13) 0.0017(14)
C7 0.0323(17) 0.0339(16) 0.0302(15) 0.0037(13) 0.0133(13) 0.0056(14)
C8 0.0201(14) 0.0194(14) 0.0258(14) 0.0050(11) 0.0012(12) -0.0003(12)
C9 0.0238(15) 0.051(2) 0.0447(17) 0.0138(15) -0.0008(13) 0.0057(15)
N1 0.0419(15) 0.0244(13) 0.0246(13) -0.0001(10) 0.0018(11) 0.0067(12)
O1 0.0577(14) 0.0402(12) 0.0283(10) -0.0008(9) -0.0165(10) 0.0034(11)
O2 0.0434(13) 0.0397(12) 0.0336(11) 0.0060(10) 0.0126(9) -0.0039(10)
O3 0.0205(10) 0.0236(10) 0.0323(10) 0.0092(8) -0.0003(8) 0.0027(8)
O4 0.0238(10) 0.0267(10) 0.0253(9) 0.0021(8) 0.0067(8) -0.0052(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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
C2 C1 N1 111.3(2)
C2 C1 C8 102.6(2)
N1 C1 C8 108.9(2)
C3 C2 C1 111.7(3)
C2 C3 C4 112.6(2)
C3 C4 C5 116.3(2)
C3 C4 C8 102.2(2)
C5 C4 C8 113.9(2)
C6 C5 C4 111.9(2)
C7 C6 C5 108.6(2)
O4 C7 C6 111.5(2)
O4 C8 O3 112.68(19)
O4 C8 C4 113.70(19)
O3 C8 C4 108.66(19)
O4 C8 C1 101.9(2)
O3 C8 C1 115.61(18)
C4 C8 C1 104.0(2)
O2 N1 O1 124.4(2)
O2 N1 C1 118.2(2)
O1 N1 C1 117.3(2)
C8 O3 C9 115.9(2)
C8 O4 C7 114.75(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.491(4)
C1 N1 1.518(3)
C1 C8 1.553(3)
C2 C3 1.307(3)
C3 C4 1.501(3)
C4 C5 1.528(3)
C4 C8 1.537(3)
C5 C6 1.516(4)
C6 C7 1.504(3)
C7 O4 1.442(3)
C8 O4 1.403(3)
C8 O3 1.406(3)
C9 O3 1.435(3)
N1 O2 1.218(3)
N1 O1 1.230(2)
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
N1 C1 C2 C3 100.0(3)
C8 C1 C2 C3 -16.3(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 140.9(2)
C2 C3 C4 C8 16.3(3)
C3 C4 C5 C6 -74.6(3)
C8 C4 C5 C6 43.8(3)
C4 C5 C6 C7 -52.6(3)
C5 C6 C7 O4 60.4(3)
C3 C4 C8 O4 85.2(2)
C5 C4 C8 O4 -41.0(3)
C3 C4 C8 O3 -148.5(2)
C5 C4 C8 O3 85.3(3)
C3 C4 C8 C1 -24.8(2)
C5 C4 C8 C1 -151.0(2)
C2 C1 C8 O4 -93.4(2)
N1 C1 C8 O4 148.58(19)
C2 C1 C8 O3 144.1(2)
N1 C1 C8 O3 26.0(3)
C2 C1 C8 C4 25.1(2)
N1 C1 C8 C4 -93.0(2)
C2 C1 N1 O2 -39.4(3)
C8 C1 N1 O2 73.0(3)
C2 C1 N1 O1 143.4(2)
C8 C1 N1 O1 -104.2(2)
O4 C8 O3 C9 -40.2(3)
C4 C8 O3 C9 -167.2(2)
C1 C8 O3 C9 76.5(3)
O3 C8 O4 C7 -75.1(2)
C4 C8 O4 C7 49.1(3)
C1 C8 O4 C7 160.35(18)
C6 C7 O4 C8 -60.2(3)
