#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/87/1508745.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_1508745
loop_
_publ_author_name
'Lam, Jonathan K.'
'Schmidt, Yvonne'
'Vanderwal, Christopher D.'
_publ_section_title
;
 Complex polycyclic scaffolds by metathesis rearrangement of Himbert
 arene/allene cycloadducts.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5566
_journal_page_last               5569
_journal_paper_doi               10.1021/ol302680m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_weight         244.25
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 116.9766(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5663(7)
_cell_length_b                   10.9334(7)
_cell_length_c                   11.1163(8)
_cell_measurement_reflns_used    8506
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.77
_cell_volume                     1144.48(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12984
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2479
_reflns_number_total             2725
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302680m_si_002.cif
_cod_data_source_block           cdv16
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1508745
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
O1 O 0.22977(9) 0.00146(8) 1.23160(8) 0.0243(2) Uani 1 1 d
O2 O 0.32499(10) 0.53449(8) 0.93473(10) 0.0310(2) Uani 1 1 d
O3 O 0.35003(11) 0.41431(10) 0.79202(10) 0.0340(2) Uani 1 1 d
N1 N 0.17208(9) 0.19813(8) 1.14960(9) 0.01554(19) Uani 1 1 d
N2 N 0.29707(10) 0.44094(9) 0.86682(10) 0.0217(2) Uani 1 1 d
C1 C 0.18764(11) 0.07325(10) 1.13727(11) 0.0172(2) Uani 1 1 d
C2 C 0.14221(11) 0.04753(10) 0.99277(11) 0.0175(2) Uani 1 1 d
C3 C 0.08285(11) 0.14739(9) 0.92092(10) 0.0153(2) Uani 1 1 d
C4 C 0.02628(12) 0.17696(10) 0.77540(10) 0.0170(2) Uani 1 1 d
C5 C 0.12594(11) 0.26935(10) 0.75408(10) 0.0172(2) Uani 1 1 d
C6 C 0.19636(11) 0.35179(9) 0.87544(11) 0.0167(2) Uani 1 1 d
C7 C 0.18430(11) 0.35058(9) 0.98928(11) 0.0159(2) Uani 1 1 d
C8 C 0.09715(11) 0.25272(9) 1.01406(10) 0.0150(2) Uani 1 1 d
C9 C -0.03464(11) 0.30655(10) 1.01493(11) 0.0189(2) Uani 1 1 d
C10 C -0.02537(12) 0.30039(11) 1.13778(12) 0.0219(2) Uani 1 1 d
C11 C 0.11071(12) 0.24138(11) 1.23771(11) 0.0198(2) Uani 1 1 d
C12 C 0.04019(13) 0.34216(11) 0.62716(12) 0.0224(2) Uani 1 1 d
C13 C 0.05202(18) 0.33128(13) 0.51488(13) 0.0352(3) Uani 1 1 d
H2 H 0.1512(15) -0.0300(14) 0.9603(14) 0.023(3) Uiso 1 1 d
H4A H -0.0691(16) 0.2155(13) 0.7440(14) 0.020(3) Uiso 1 1 d
H4B H 0.0186(15) 0.1055(14) 0.7215(14) 0.021(3) Uiso 1 1 d
H5 H 0.2012(15) 0.2244(14) 0.7423(14) 0.022(3) Uiso 1 1 d
H7 H 0.2316(15) 0.4090(14) 1.0572(14) 0.021(3) Uiso 1 1 d
H9 H -0.1086(16) 0.3455(14) 0.9361(15) 0.025(4) Uiso 1 1 d
H10 H -0.0955(16) 0.3318(15) 1.1633(15) 0.028(4) Uiso 1 1 d
H11A H 0.1717(15) 0.3009(14) 1.3033(14) 0.021(3) Uiso 1 1 d
H11B H 0.0993(15) 0.1698(14) 1.2870(14) 0.024(4) Uiso 1 1 d
H12 H -0.0292(17) 0.3975(16) 0.6315(15) 0.032(4) Uiso 1 1 d
H13A H 0.120(2) 0.2751(18) 0.5065(19) 0.049(5) Uiso 1 1 d
H13B H -0.006(2) 0.3749(18) 0.4371(19) 0.047(5) Uiso 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
C1 N1 C8 109.27(8)
C1 N1 C11 119.17(9)
C8 N1 C11 110.78(8)
O2 N2 O3 123.93(10)
O2 N2 C6 119.34(10)
O3 N2 C6 116.72(10)
O1 C1 N1 124.09(10)
O1 C1 C2 128.50(10)
N1 C1 C2 107.41(9)
C3 C2 C1 109.16(9)
C3 C2 H2 127.6(9)
C1 C2 H2 123.1(9)
C2 C3 C4 132.89(10)
C2 C3 C8 109.95(9)
C4 C3 C8 116.55(9)
C3 C4 C5 110.02(9)
C3 C4 H4A 108.5(8)
C5 C4 H4A 108.6(8)
C3 C4 H4B 112.3(8)
C5 C4 H4B 107.7(8)
H4A C4 H4B 109.7(12)
C6 C5 C12 111.32(9)
C6 C5 C4 110.23(8)
C12 C5 C4 108.91(9)
C6 C5 H5 108.3(8)
C12 C5 H5 108.3(8)
C4 C5 H5 109.7(9)
C7 C6 N2 116.83(10)
C7 C6 C5 128.65(10)
N2 C6 C5 114.44(9)
C6 C7 C8 120.58(10)
C6 C7 H7 120.8(9)
C8 C7 H7 118.6(8)
N1 C8 C3 103.44(8)
N1 C8 C9 102.69(8)
C3 C8 C9 119.61(9)
N1 C8 C7 112.51(8)
C3 C8 C7 107.09(8)
C9 C8 C7 111.26(9)
C10 C9 C8 110.37(10)
C10 C9 H9 127.3(9)
C8 C9 H9 122.1(9)
C9 C10 C11 112.41(10)
C9 C10 H10 125.1(9)
C11 C10 H10 122.5(9)
N1 C11 C10 101.98(8)
N1 C11 H11A 111.8(8)
C10 C11 H11A 110.7(9)
N1 C11 H11B 108.2(9)
C10 C11 H11B 115.5(9)
H11A C11 H11B 108.6(12)
C13 C12 C5 124.29(12)
C13 C12 H12 120.3(9)
C5 C12 H12 115.4(9)
C12 C13 H13A 122.4(11)
C12 C13 H13B 121.7(12)
H13A C13 H13B 115.9(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2207(13)
O2 N2 1.2251(14)
O3 N2 1.2295(13)
N1 C1 1.3894(14)
N1 C8 1.4735(13)
N1 C11 1.4764(13)
N2 C6 1.4779(14)
C1 C2 1.4800(15)
C2 C3 1.3300(15)
C2 H2 0.942(15)
C3 C4 1.4836(14)
C3 C8 1.5096(14)
C4 C5 1.5530(15)
C4 H4A 0.998(15)
C4 H4B 0.966(15)
C5 C6 1.5084(15)
C5 C12 1.5118(15)
C5 H5 0.993(15)
C6 C7 1.3282(15)
C7 C8 1.5161(14)
C7 H7 0.941(15)
C8 C9 1.5159(15)
C9 C10 1.3258(16)
C9 H9 0.968(15)
C10 C11 1.5062(16)
C10 H10 0.969(16)
C11 H11A 0.972(15)
C11 H11B 0.994(15)
C12 C13 1.3150(18)
C12 H12 0.969(17)
C13 H13A 0.98(2)
C13 H13B 0.93(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
C8 N1 C1 O1 -170.60(10)
C11 N1 C1 O1 -41.88(15)
C8 N1 C1 C2 8.48(11)
C11 N1 C1 C2 137.20(9)
O1 C1 C2 C3 170.07(11)
N1 C1 C2 C3 -8.95(12)
C1 C2 C3 C4 176.15(11)
C1 C2 C3 C8 5.66(12)
C2 C3 C4 C5 -109.07(13)
C8 C3 C4 C5 60.92(12)
C3 C4 C5 C6 -31.14(12)
C3 C4 C5 C12 -153.54(9)
O2 N2 C6 C7 -25.93(15)
O3 N2 C6 C7 152.80(11)
O2 N2 C6 C5 156.98(10)
O3 N2 C6 C5 -24.29(14)
C12 C5 C6 C7 122.55(12)
C4 C5 C6 C7 1.57(15)
C12 C5 C6 N2 -60.79(12)
C4 C5 C6 N2 178.24(9)
N2 C6 C7 C8 -172.76(9)
C5 C6 C7 C8 3.84(17)
C1 N1 C8 C3 -5.11(11)
C11 N1 C8 C3 -138.34(9)
C1 N1 C8 C9 119.96(9)
C11 N1 C8 C9 -13.27(11)
C1 N1 C8 C7 -120.33(9)
C11 N1 C8 C7 106.44(10)
C2 C3 C8 N1 -0.55(11)
C4 C3 C8 N1 -172.77(8)
C2 C3 C8 C9 -113.86(11)
C4 C3 C8 C9 73.92(12)
C2 C3 C8 C7 118.48(10)
C4 C3 C8 C7 -53.74(11)
C6 C7 C8 N1 133.19(10)
C6 C7 C8 C3 20.19(13)
C6 C7 C8 C9 -112.21(11)
N1 C8 C9 C10 8.41(12)
C3 C8 C9 C10 122.12(11)
C7 C8 C9 C10 -112.17(11)
C8 C9 C10 C11 -0.60(14)
C1 N1 C11 C10 -115.16(10)
C8 N1 C11 C10 12.86(11)
C9 C10 C11 N1 -7.44(13)
C6 C5 C12 C13 128.33(13)
C4 C5 C12 C13 -109.93(14)
