#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:58:54 +0100 (mar 22 de mar de 2016) $
#$Revision: 178927 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/56/4115660.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_4115660
loop_
_publ_author_name
'Helfried Neumann'
'Axel Jacobi von Wangelin'
'Dirk Gördes'
'Anke Spannenberg'
'Matthias Beller'
_publ_section_title
;
 A New Multicomponent Coupling of Aldehydes, Amides, and Dienophiles:
 Atom-Efficient One-Pot Synthesis of Highly Substituted Cyclohexenes and
 Cyclohexadienes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8398
_journal_page_last               8399
_journal_paper_doi               10.1021/ja010503k
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 113.28(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.643(2)
_cell_length_b                   15.147(3)
_cell_length_c                   9.364(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     1126.1(5)
_computing_cell_refinement       STOE-CELL
_computing_data_collection       STOE-EXPOSE
_computing_data_reduction        STOE-INTEGRATE
_computing_molecular_graphics    XP
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       STOE-IPDS
_diffrn_measurement_method       'LASER SCANNED IMAGING PLATE'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.0929
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3311
_diffrn_reflns_theta_max         24.30
_diffrn_reflns_theta_min         2.57
_diffrn_standards_interval_time  360
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   NO
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.892
_refine_ls_goodness_of_fit_obs   1.104
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.892
_refine_ls_restrained_S_obs      1.104
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_obs          0.0562
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0890P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1614
_refine_ls_wR_factor_obs         0.1465
_reflns_number_observed          1032
_reflns_number_total             1803
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja010503k.cif
_cod_data_source_block           812
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1126.1(4)
_cod_database_code               4115660
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.045(2) 0.047(2) 0.032(2) -0.0048(13) 0.0168(13) -0.0015(14)
C2 0.045(2) 0.073(2) 0.048(2) -0.009(2) 0.0144(14) -0.013(2)
C3 0.043(2) 0.048(2) 0.0274(15) -0.0013(14) 0.0082(12) -0.0050(13)
C4 0.0371(15) 0.048(2) 0.036(2) 0.0033(13) 0.0066(12) 0.0038(14)
C5 0.034(2) 0.057(2) 0.043(2) 0.0036(14) 0.0089(13) 0.0041(14)
C6 0.038(2) 0.053(2) 0.050(2) 0.000(2) 0.0132(14) -0.0060(14)
C7 0.050(2) 0.043(2) 0.057(2) 0.001(2) 0.024(2) 0.0005(14)
C8 0.043(2) 0.053(2) 0.038(2) -0.0086(15) 0.0137(14) -0.0033(14)
C9 0.061(2) 0.055(2) 0.061(2) -0.012(2) 0.033(2) -0.006(2)
C10 0.066(2) 0.056(2) 0.070(2) 0.005(2) 0.025(2) 0.011(2)
C11 0.067(2) 0.062(2) 0.083(2) 0.018(2) 0.040(2) 0.001(2)
N1 0.0405(13) 0.0528(15) 0.0258(13) -0.0004(12) 0.0081(11) -0.0101(11)
N2 0.070(2) 0.080(2) 0.098(2) -0.011(2) 0.047(2) 0.002(2)
O 0.0743(15) 0.073(2) 0.0381(12) -0.0028(11) 0.0257(11) -0.0217(12)
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.1506(3) 0.2218(2) 0.7350(3) 0.0408(7) Uani 1 d .
C2 C -0.3083(4) 0.1958(2) 0.5971(3) 0.0564(9) Uani 1 d .
H2A H -0.3023(4) 0.2179(2) 0.5034(3) 0.085 Uiso 1 calc R
H2B H -0.4051(4) 0.2203(2) 0.6088(3) 0.085 Uiso 1 calc R
H2C H -0.3176(4) 0.1326(2) 0.5917(3) 0.085 Uiso 1 calc R
C3 C 0.1158(3) 0.3051(2) 0.8192(3) 0.0411(7) Uani 1 d .
H3 H 0.1261(34) 0.2756(17) 0.9095(36) 0.048(8) Uiso 1 d .
C4 C 0.2654(3) 0.2861(2) 0.7778(3) 0.0430(7) Uani 1 d .
C5 C 0.3498(4) 0.3509(2) 0.7454(3) 0.0465(8) Uani 1 d .
H5 H 0.4503(39) 0.3308(21) 0.7290(32) 0.060(9) Uiso 1 d .
C6 C 0.3075(4) 0.4471(2) 0.7357(4) 0.0482(8) Uani 1 d .
H6 H 0.3819(36) 0.4761(18) 0.8331(34) 0.050(8) Uiso 1 d .
C7 C 0.1269(4) 0.4594(2) 0.7211(4) 0.0490(8) Uani 1 d .
H7A H 0.1077(32) 0.5210(20) 0.7379(31) 0.048(8) Uiso 1 d .
H7B H 0.0505(38) 0.4372(21) 0.6161(37) 0.062(9) Uiso 1 d .
C8 C 0.0990(4) 0.4041(2) 0.8452(3) 0.0454(8) Uani 1 d .
H8 H 0.1800(33) 0.4202(16) 0.9442(31) 0.038(7) Uiso 1 d .
C9 C -0.0658(4) 0.4249(2) 0.8506(4) 0.0563(9) Uani 1 d .
C10 C 0.3126(4) 0.1904(2) 0.7834(4) 0.0646(10) Uani 1 d .
H10A H 0.2344(4) 0.1555(2) 0.8089(4) 0.097 Uiso 1 calc R
H10B H 0.4242(4) 0.1820(2) 0.8610(4) 0.097 Uiso 1 calc R
H10C H 0.3092(4) 0.1727(2) 0.6838(4) 0.097 Uiso 1 calc R
C11 C 0.3369(4) 0.4923(2) 0.6044(4) 0.0672(10) Uani 1 d .
H11A H 0.3085(4) 0.5537(2) 0.6020(4) 0.101 Uiso 1 calc R
H11B H 0.2677(4) 0.4652(2) 0.5074(4) 0.101 Uiso 1 calc R
H11C H 0.4533(4) 0.4866(2) 0.6205(4) 0.101 Uiso 1 calc R
N1 N -0.0395(3) 0.2694(2) 0.6996(3) 0.0413(6) Uani 1 d .
N2 N -0.1931(4) 0.4433(2) 0.8531(4) 0.0784(10) Uani 1 d .
HN H -0.0562(37) 0.2827(19) 0.6031(40) 0.051(9) Uiso 1 d .
O O -0.1280(3) 0.20126(14) 0.8685(2) 0.0608(7) Uani 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
O C1 N1 123.1(3)
O C1 C2 122.0(3)
N1 C1 C2 114.8(2)
N1 C3 C4 110.5(2)
N1 C3 C8 111.4(2)
C4 C3 C8 111.6(2)
C5 C4 C10 123.7(3)
C5 C4 C3 121.3(3)
C10 C4 C3 114.9(3)
C4 C5 C6 126.2(3)
C5 C6 C11 112.0(3)
C5 C6 C7 110.0(3)
C11 C6 C7 111.5(3)
C6 C7 C8 109.2(3)
C9 C8 C7 110.7(3)
C9 C8 C3 111.5(2)
C7 C8 C3 111.2(2)
N2 C9 C8 178.1(4)
C1 N1 C3 122.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O 1.227(3)
C1 N1 1.343(4)
C1 C2 1.513(4)
C3 N1 1.469(3)
C3 C4 1.516(4)
C3 C8 1.536(4)
C4 C5 1.327(4)
C4 C10 1.501(4)
C5 C6 1.497(4)
C6 C11 1.514(4)
C6 C7 1.523(4)
C7 C8 1.527(4)
C8 C9 1.479(4)
C9 N2 1.144(4)
