#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023454.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_4023454
loop_
_publ_author_name
'Cynthia B. Gilley'
'Yoshihisa Kobayashi'
_publ_section_title
;
 2-Nitrophenyl Isocyanide as a Versatile Convertible Isocyanide:
 Rapid Access to a Fused γ-Lactam β-Lactone Bicycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4198
_journal_page_last               4204
_journal_paper_doi               10.1021/jo800486k
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H27 N3 O7'
_chemical_formula_weight         469.49
_chemical_name_common            KOB12
_chemical_name_systematic
;
 ?
;
_space_group.centring_type       C
_space_group_IT_number           5
_space_group.IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 105.377(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5404(13)
_cell_length_b                   7.9786(5)
_cell_length_c                   14.1152(10)
_cell_measurement_reflns_used    3120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.04
_cell_measurement_theta_min      4.47
_cell_volume                     2230.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_refln_scan_rate          30
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10250
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         4.46
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0490
_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)+(0.0406P)²+1.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                3055
_reflns_number_total             3817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800486k-File003.cif
_cod_data_source_block           kob12
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_space_group.centring_type' value 'C-centered' was replaced with the
value 'C' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4023454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79144(19) 0.7936(4) 0.5776(3) 0.0241(7) Uani 1 1 d . . .
C2 C 0.73454(18) 0.7962(4) 0.6283(3) 0.0229(7) Uani 1 1 d . . .
H2 H 0.6926 0.7523 0.5814 0.027 Uiso 1 1 calc R . .
C3 C 0.76128(16) 0.6626(4) 0.7070(2) 0.0199(6) Uani 1 1 d . . .
H3 H 0.7497 0.5512 0.6745 0.024 Uiso 1 1 calc R . .
C4 C 0.83845(16) 0.6793(4) 0.7325(2) 0.0205(6) Uani 1 1 d . . .
C5 C 0.90971(17) 0.6930(4) 0.6074(3) 0.0246(7) Uani 1 1 d . . .
H5A H 0.9436 0.7622 0.6541 0.030 Uiso 1 1 calc R . .
H5B H 0.9038 0.7405 0.5408 0.030 Uiso 1 1 calc R . .
C6 C 0.93626(17) 0.5148(4) 0.6090(2) 0.0229(7) Uani 1 1 d . . .
C7 C 1.00491(17) 0.4864(4) 0.6285(2) 0.0242(7) Uani 1 1 d . . .
H7 H 1.0349 0.5794 0.6417 0.029 Uiso 1 1 calc R . .
C8 C 1.03143(17) 0.3262(4) 0.6296(3) 0.0246(7) Uani 1 1 d . . .
H8 H 1.0786 0.3096 0.6406 0.029 Uiso 1 1 calc R . .
C9 C 0.98751(17) 0.1909(4) 0.6142(2) 0.0222(7) Uani 1 1 d . . .
C10 C 0.91819(17) 0.2157(4) 0.5949(2) 0.0224(7) Uani 1 1 d . . .
H10 H 0.8883 0.1226 0.5849 0.027 Uiso 1 1 calc R . .
C11 C 0.89312(18) 0.3771(4) 0.5904(2) 0.0221(7) Uani 1 1 d . . .
H11 H 0.8457 0.3943 0.5745 0.027 Uiso 1 1 calc R . .
C12 C 1.07812(17) -0.0055(4) 0.6289(3) 0.0282(7) Uani 1 1 d . . .
H12A H 1.0914 0.0366 0.5715 0.042 Uiso 1 1 calc R . .
H12B H 1.0866 -0.1263 0.6354 0.042 Uiso 1 1 calc R . .
H12C H 1.1045 0.0518 0.6881 0.042 Uiso 1 1 calc R . .
C13 C 0.71957(18) 0.9702(4) 0.6624(3) 0.0293(8) Uani 1 1 d . . .
H13A H 0.7603 1.0152 0.7083 0.044 Uiso 1 1 calc R . .
H13B H 0.6832 0.9624 0.6952 0.044 Uiso 1 1 calc R . .
H13C H 0.7056 1.0447 0.6054 0.044 Uiso 1 1 calc R . .
C14 C 0.76326(17) 0.5174(4) 0.8509(3) 0.0245(7) Uani 1 1 d . . .
C15 C 0.7511(2) 0.5533(5) 0.9501(3) 0.0350(9) Uani 1 1 d . . .
H15A H 0.7707 0.4631 0.9960 0.053 Uiso 1 1 calc R . .
H15B H 0.7024 0.5597 0.9432 0.053 Uiso 1 1 calc R . .
H15C H 0.7723 0.6601 0.9753 0.053 Uiso 1 1 calc R . .
C16 C 0.72944(18) 0.3541(4) 0.8070(3) 0.0279(8) Uani 1 1 d . . .
H16A H 0.7355 0.3388 0.7409 0.042 Uiso 1 1 calc R . .
H16B H 0.6811 0.3590 0.8031 0.042 Uiso 1 1 calc R . .
H16C H 0.7500 0.2598 0.8487 0.042 Uiso 1 1 calc R . .
C17 C 0.86362(16) 0.5135(4) 0.7861(2) 0.0211(6) Uani 1 1 d . . .
H17A H 0.8481 0.4166 0.7421 0.025 Uiso 1 1 calc R . .
H17B H 0.9136 0.5117 0.8082 0.025 Uiso 1 1 calc R . .
C18 C 0.86841(17) 0.8384(4) 0.7941(2) 0.0202(7) Uani 1 1 d . . .
C19 C 0.90529(17) 0.9471(4) 0.9650(2) 0.0208(7) Uani 1 1 d . . .
C20 C 0.89787(17) 1.1167(4) 0.9429(3) 0.0226(7) Uani 1 1 d . . .
H20 H 0.8784 1.1509 0.8770 0.027 Uiso 1 1 calc R . .
C21 C 0.91841(19) 1.2370(4) 1.0155(3) 0.0267(8) Uani 1 1 d . . .
H21 H 0.9125 1.3523 0.9986 0.032 Uiso 1 1 calc R . .
C22 C 0.94748(18) 1.1920(5) 1.1124(3) 0.0283(8) Uani 1 1 d . . .
H22 H 0.9614 1.2758 1.1615 0.034 Uiso 1 1 calc R . .
C23 C 0.95594(16) 1.0258(4) 1.1368(2) 0.0230(7) Uani 1 1 d . . .
H23 H 0.9759 0.9934 1.2029 0.028 Uiso 1 1 calc R . .
C24 C 0.93519(18) 0.9055(4) 1.0645(3) 0.0233(7) Uani 1 1 d . . .
N1 N 0.84559(14) 0.7027(3) 0.6332(2) 0.0203(6) Uani 1 1 d . . .
N2 N 0.88214(15) 0.8210(3) 0.8942(2) 0.0241(6) Uani 1 1 d . . .
H2A H 0.8758 0.7209 0.9165 0.029 Uiso 1 1 calc R . .
N3 N 0.9467(2) 0.7329(4) 1.0971(3) 0.0446(10) Uani 1 1 d . . .
O1 O 1.00795(11) 0.0260(3) 0.61654(18) 0.0263(5) Uani 1 1 d . . .
O2 O 0.78930(14) 0.8586(3) 0.49814(19) 0.0310(6) Uani 1 1 d . . .
O3 O 0.73685(12) 0.6619(3) 0.79129(18) 0.0234(5) Uani 1 1 d . . .
O4 O 0.83520(12) 0.5074(3) 0.86914(17) 0.0225(5) Uani 1 1 d . . .
O5 O 0.87883(13) 0.9642(3) 0.75300(18) 0.0276(6) Uani 1 1 d . . .
O6 O 0.9837(10) 0.705(3) 1.1737(19) 0.044(3) Uani 0.487(5) 1 d P . .
O6A O 0.9612(10) 0.685(3) 1.1768(19) 0.044(3) Uani 0.487(5) 1 d P . .
O7 O 0.8977(3) 0.6277(6) 1.0611(4) 0.0310(13) Uani 0.513(5) 1 d P . .
O7A O 0.9714(3) 0.6369(6) 1.0297(4) 0.0332(13) Uani 0.513(5) 1 d P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 N1 124.7(3) . . ?
O2 C1 C2 125.3(3) . . ?
N1 C1 C2 110.0(3) . . ?
C1 C2 C13 113.8(3) . . ?
C1 C2 C3 99.2(3) . . ?
C13 C2 C3 117.9(3) . . ?
C1 C2 H2 108.5 . . ?
C13 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
O3 C3 C2 118.4(3) . . ?
O3 C3 C4 112.3(3) . . ?
C2 C3 C4 105.0(3) . . ?
O3 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C4 C3 H3 106.8 . . ?
N1 C4 C3 98.4(3) . . ?
N1 C4 C17 118.3(3) . . ?
C3 C4 C17 103.4(3) . . ?
N1 C4 C18 107.7(3) . . ?
C3 C4 C18 115.4(3) . . ?
C17 C4 C18 113.0(3) . . ?
N1 C5 C6 112.9(3) . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C11 118.3(3) . . ?
C7 C6 C5 119.9(3) . . ?
C11 C6 C5 121.8(3) . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
O1 C9 C8 123.9(3) . . ?
O1 C9 C10 115.4(3) . . ?
C8 C9 C10 120.6(3) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C6 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 O3 111.0(3) . . ?
O4 C14 C15 105.1(3) . . ?
O3 C14 C15 105.0(3) . . ?
O4 C14 C16 111.2(3) . . ?
O3 C14 C16 112.6(3) . . ?
C15 C14 C16 111.5(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C4 105.8(3) . . ?
O4 C17 H17A 110.6 . . ?
C4 C17 H17A 110.6 . . ?
O4 C17 H17B 110.6 . . ?
C4 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
O5 C18 N2 124.4(3) . . ?
O5 C18 C4 120.0(3) . . ?
N2 C18 C4 115.6(3) . . ?
C20 C19 N2 122.7(3) . . ?
C20 C19 C24 116.4(3) . . ?
N2 C19 C24 120.8(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C19 122.5(3) . . ?
C23 C24 N3 115.6(3) . . ?
C19 C24 N3 121.9(3) . . ?
C1 N1 C5 121.9(3) . . ?
C1 N1 C4 109.9(3) . . ?
C5 N1 C4 124.1(3) . . ?
C18 N2 C19 126.6(3) . . ?
C18 N2 H2A 116.7 . . ?
C19 N2 H2A 116.7 . . ?
O6A N3 O6 24.9(12) . . ?
O6A N3 O7 98.1(9) . . ?
O6 N3 O7 118.9(9) . . ?
O6A N3 O7A 115.6(13) . . ?
O6 N3 O7A 104.9(12) . . ?
O7 N3 O7A 76.6(4) . . ?
O6A N3 C24 127.0(13) . . ?
O6 N3 C24 119.1(11) . . ?
O7 N3 C24 116.2(3) . . ?
O7A N3 C24 110.9(4) . . ?
C9 O1 C12 117.5(3) . . ?
C3 O3 C14 109.4(2) . . ?
C14 O4 C17 118.2(2) . . ?
N3 O7A O7A 142.1(4) . 2_757 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.226(4) . ?
C1 N1 1.384(4) . ?
C1 C2 1.524(5) . ?
C2 C13 1.527(5) . ?
C2 C3 1.532(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.408(4) . ?
C3 C4 1.535(4) . ?
C3 H3 1.0000 . ?
C4 N1 1.460(4) . ?
C4 C17 1.543(4) . ?
C4 C18 1.569(4) . ?
C5 N1 1.459(4) . ?
C5 C6 1.521(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.382(5) . ?
C6 C11 1.392(5) . ?
C7 C8 1.388(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9500 . ?
C9 O1 1.379(4) . ?
C9 C10 1.391(5) . ?
C10 C11 1.381(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 O1 1.428(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O4 1.433(4) . ?
C14 O3 1.445(4) . ?
C14 C15 1.514(5) . ?
C14 C16 1.528(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O4 1.442(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O5 1.206(4) . ?
C18 N2 1.374(4) . ?
C19 C20 1.388(5) . ?
C19 N2 1.409(4) . ?
C19 C24 1.414(5) . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.369(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(5) . ?
C23 H23 0.9500 . ?
C24 N3 1.452(4) . ?
N2 H2A 0.8800 . ?
N3 O6A 1.15(2) . ?
N3 O6 1.17(3) . ?
N3 O7 1.305(6) . ?
N3 O7A 1.416(7) . ?
O7A O7A 1.613(11) 2_757 ?
