#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/76/1507611.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_1507611
loop_
_publ_author_name
'Grainger, Richard S.'
'Betou, Marie'
'Male, Louise'
'Pitak, Mateusz B.'
'Coles, Simon J.'
_publ_section_title
;
 Semipinacol Rearrangement of Cis-Fused β-Lactam Diols into Keto-Bridged
 Bicyclic Lactams.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2234
_journal_page_last               2237
_journal_paper_doi               10.1021/ol300605y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.657(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0675(3)
_cell_length_b                   6.0052(2)
_cell_length_c                   21.3783(8)
_cell_measurement_reflns_used    8194
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1150.83(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K,
& Puschmann, H., 2009)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12191
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut Plate'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0435
_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)+(0.0826P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                2144
_reflns_number_total             2628
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol300605y_si_002.cif
_cod_data_source_block           Compound_4b
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic 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_original_sg_symbol_H-M      'P 2(1)/n'
_cod_database_code               1507611
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
C1 C 0.19204(14) 0.3763(2) -0.12143(6) 0.0193(3) Uani 1 1 d .
C2 C 0.26232(14) 0.5519(2) -0.15723(6) 0.0199(3) Uani 1 1 d .
C3 C 0.34473(15) 0.5636(2) -0.20341(6) 0.0223(3) Uani 1 1 d .
H3 H 0.3301 0.4589 -0.2371 0.027 Uiso 1 1 calc R
C4 C 0.46111(15) 0.7420(2) -0.20261(7) 0.0241(3) Uani 1 1 d .
H4A H 0.4386 0.8318 -0.2417 0.029 Uiso 1 1 calc R
H4B H 0.5595 0.6707 -0.2027 0.029 Uiso 1 1 calc R
C5 C 0.47049(15) 0.8976(2) -0.14506(7) 0.0246(3) Uani 1 1 d .
H5A H 0.3964 1.0186 -0.1548 0.030 Uiso 1 1 calc R
H5B H 0.5708 0.9665 -0.1375 0.030 Uiso 1 1 calc R
C6 C 0.44182(16) 0.7780(2) -0.08430(7) 0.0248(3) Uani 1 1 d .
H6A H 0.5115 0.6515 -0.0745 0.030 Uiso 1 1 calc R
H6B H 0.4546 0.8819 -0.0479 0.030 Uiso 1 1 calc R
C7 C 0.28178(15) 0.6961(2) -0.09823(6) 0.0202(3) Uani 1 1 d .
H7 H 0.2085 0.8215 -0.1017 0.024 Uiso 1 1 calc R
C8 C 0.20296(14) 0.4673(2) -0.00355(6) 0.0173(3) Uani 1 1 d .
C9 C 0.14916(14) 0.2658(2) 0.01627(6) 0.0192(3) Uani 1 1 d .
H9 H 0.1286 0.1467 -0.0130 0.023 Uiso 1 1 calc R
C10 C 0.12540(14) 0.2381(2) 0.07876(6) 0.0188(3) Uani 1 1 d .
H10 H 0.0890 0.1004 0.0921 0.023 Uiso 1 1 calc R
C11 C 0.15517(14) 0.4132(2) 0.12154(6) 0.0189(3) Uani 1 1 d .
C12 C 0.20802(15) 0.6150(2) 0.10148(6) 0.0207(3) Uani 1 1 d .
H12 H 0.2275 0.7347 0.1306 0.025 Uiso 1 1 calc R
C13 C 0.23229(15) 0.6424(2) 0.03967(6) 0.0202(3) Uani 1 1 d .
H13 H 0.2689 0.7802 0.0265 0.024 Uiso 1 1 calc R
C14 C 0.10638(17) 0.1943(2) 0.20968(7) 0.0265(3) Uani 1 1 d .
H14A H 0.0144 0.1319 0.1863 0.040 Uiso 1 1 calc R
H14B H 0.0953 0.2119 0.2543 0.040 Uiso 1 1 calc R
H14C H 0.1899 0.0937 0.2062 0.040 Uiso 1 1 calc R
N1 N 0.22804(12) 0.49831(18) -0.06619(5) 0.0191(3) Uani 1 1 d .
O1 O 0.13238(11) 0.19576(15) -0.13166(5) 0.0237(3) Uani 1 1 d .
O2 O 0.13488(11) 0.40578(16) 0.18379(4) 0.0241(3) 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
O1 C1 N1 131.73(13)
O1 C1 C2 138.26(13)
N1 C1 C2 89.95(10)
C3 C2 C1 138.30(13)
C3 C2 C7 125.47(12)
C1 C2 C7 88.98(10)
C2 C3 C4 120.17(13)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 113.39(11)
C3 C4 H4A 108.9
C5 C4 H4A 108.9
C3 C4 H4B 108.9
C5 C4 H4B 108.9
H4A C4 H4B 107.7
C4 C5 C6 113.28(12)
C4 C5 H5A 108.9
C6 C5 H5A 108.9
C4 C5 H5B 108.9
C6 C5 H5B 108.9
H5A C5 H5B 107.7
C7 C6 C5 105.26(11)
C7 C6 H6A 110.7
C5 C6 H6A 110.7
C7 C6 H6B 110.7
C5 C6 H6B 110.7
H6A C6 H6B 108.8
N1 C7 C2 85.55(10)
N1 C7 C6 122.50(12)
C2 C7 C6 109.62(11)
N1 C7 H7 112.0
C2 C7 H7 112.0
C6 C7 H7 112.0
C9 C8 C13 119.48(12)
C9 C8 N1 121.28(11)
C13 C8 N1 119.24(11)
C8 C9 C10 120.41(12)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 119.76(12)
C11 C10 H10 120.1
C9 C10 H10 120.1
O2 C11 C10 124.88(12)
O2 C11 C12 115.41(12)
C10 C11 C12 119.71(12)
C13 C12 C11 120.62(12)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C8 120.02(12)
C12 C13 H13 120.0
C8 C13 H13 120.0
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C1 N1 C8 133.72(11)
C1 N1 C7 94.66(10)
C8 N1 C7 130.97(11)
C11 O2 C14 117.68(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2165(16)
C1 N1 1.3864(17)
C1 C2 1.5006(18)
C2 C3 1.3268(18)
C2 C7 1.5179(19)
C3 C4 1.5019(19)
C3 H3 0.9500
C4 C5 1.537(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5405(19)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.5187(19)
C6 H6A 0.9900
C6 H6B 0.9900
C7 N1 1.4890(16)
C7 H7 1.0000
C8 C9 1.3942(18)
C8 C13 1.3985(18)
C8 N1 1.4041(16)
C9 C10 1.3947(18)
C9 H9 0.9500
C10 C11 1.3928(19)
C10 H10 0.9500
C11 O2 1.3713(16)
C11 C12 1.3944(18)
C12 C13 1.3818(18)
C12 H12 0.9500
C13 H13 0.9500
C14 O2 1.4243(16)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
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 -35.8(3)
N1 C1 C2 C3 141.40(18)
O1 C1 C2 C7 175.68(16)
N1 C1 C2 C7 -7.08(10)
C1 C2 C3 C4 -145.14(16)
C7 C2 C3 C4 -5.1(2)
C2 C3 C4 C5 -0.05(19)
C3 C4 C5 C6 35.39(16)
C4 C5 C6 C7 -63.60(15)
C3 C2 C7 N1 -148.11(14)
C1 C2 C7 N1 6.61(9)
C3 C2 C7 C6 -25.13(19)
C1 C2 C7 C6 129.60(11)
C5 C6 C7 N1 153.30(12)
C5 C6 C7 C2 55.86(14)
C13 C8 C9 C10 -0.33(19)
N1 C8 C9 C10 179.81(11)
C8 C9 C10 C11 0.21(19)
C9 C10 C11 O2 179.40(12)
C9 C10 C11 C12 0.22(19)
O2 C11 C12 C13 -179.78(11)
C10 C11 C12 C13 -0.5(2)
C11 C12 C13 C8 0.4(2)
C9 C8 C13 C12 0.03(19)
N1 C8 C13 C12 179.89(12)
O1 C1 N1 C8 -4.1(2)
C2 C1 N1 C8 178.39(13)
O1 C1 N1 C7 -175.22(14)
C2 C1 N1 C7 7.24(10)
C9 C8 N1 C1 10.6(2)
C13 C8 N1 C1 -169.23(13)
C9 C8 N1 C7 178.91(12)
C13 C8 N1 C7 -1.0(2)
C2 C7 N1 C1 -7.18(10)
C6 C7 N1 C1 -117.65(13)
C2 C7 N1 C8 -178.71(13)
C6 C7 N1 C8 70.82(18)
C10 C11 O2 C14 11.49(19)
C12 C11 O2 C14 -169.29(11)
