#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150292.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_7150292
loop_
_publ_author_name
'Khlebnikov, Alexander F.'
'Novikov, Mikhail S.'
'Shinkevich, Ekaterina Yu'
'Vidovic, Denis'
_publ_section_title
;
 Selective transannular ring transformations in azirino-fused
 eight-membered O,N- or S,N-heterocycles.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4040
_journal_page_last               4042
_journal_paper_doi               10.1039/b512409c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C24 H22 N2 O'
_chemical_formula_weight         354.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.32(3)
_cell_angle_beta                 109.63(3)
_cell_angle_gamma                112.28(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4130(19)
_cell_length_b                   10.281(2)
_cell_length_c                   11.618(2)
_cell_measurement_temperature    133(2)
_cell_volume                     909.9(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9324
_diffrn_reflns_theta_full        24.87
_diffrn_reflns_theta_max         24.87
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0446
_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)+(0.0681P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                2368
_reflns_number_total             3128
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b512409c.txt
_cod_data_source_block           test
_cod_original_cell_volume        909.8(3)
_cod_database_code               7150292
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O5 O 0.05277(14) 0.46571(12) 0.73788(11) 0.0306(3) Uani 1 1 d . . .
N1 N -0.10673(18) 0.21741(15) 0.40426(13) 0.0318(3) Uani 1 1 d . . .
N10 N -0.23241(17) 0.33697(15) 0.49096(13) 0.0305(3) Uani 1 1 d . . .
C2 C 0.0409(2) 0.19538(19) 0.41170(18) 0.0362(4) Uani 1 1 d . . .
H2A H 0.1105 0.2696 0.3836 0.043 Uiso 1 1 calc R . .
H2B H -0.0022 0.0929 0.3492 0.043 Uiso 1 1 calc R . .
C3 C 0.1554(2) 0.21259(19) 0.54719(18) 0.0359(4) Uani 1 1 d . . .
H3A H 0.2675 0.2261 0.5522 0.043 Uiso 1 1 calc R . .
H3B H 0.1012 0.1199 0.5642 0.043 Uiso 1 1 calc R . .
C4 C 0.1839(2) 0.34808(18) 0.65039(17) 0.0326(4) Uani 1 1 d . . .
H4A H 0.2375 0.4409 0.6334 0.039 Uiso 1 1 calc R . .
H4B H 0.2626 0.3611 0.7387 0.039 Uiso 1 1 calc R . .
C4A C 0.0122(2) 0.32372(17) 0.64586(16) 0.0286(4) Uani 1 1 d . . .
C5A C -0.0888(2) 0.48158(17) 0.72844(16) 0.0287(4) Uani 1 1 d . . .
C6 C -0.0817(2) 0.57026(18) 0.83845(17) 0.0341(4) Uani 1 1 d . . .
H6A H 0.0169 0.6142 0.9213 0.041 Uiso 1 1 calc R . .
C7 C -0.2211(2) 0.59421(19) 0.82619(18) 0.0375(4) Uani 1 1 d . . .
H7A H -0.2176 0.6558 0.9007 0.045 Uiso 1 1 calc R . .
C8 C -0.3651(2) 0.52812(19) 0.70511(19) 0.0379(4) Uani 1 1 d . . .
H8A H -0.4606 0.5438 0.6971 0.045 Uiso 1 1 calc R . .
C9A C -0.2317(2) 0.41539(17) 0.60482(16) 0.0297(4) Uani 1 1 d . . .
C9 C -0.3702(2) 0.43926(18) 0.59581(18) 0.0349(4) Uani 1 1 d . . .
H9A H -0.4698 0.3940 0.5135 0.042 Uiso 1 1 calc R . .
C10A C -0.1141(2) 0.29662(17) 0.50859(16) 0.0285(4) Uani 1 1 d . . .
C11 C -0.2287(2) 0.18278(19) 0.26931(17) 0.0380(4) Uani 1 1 d . . .
H11A H -0.1640 0.2351 0.2259 0.046 Uiso 1 1 calc R . .
H11B H -0.3081 0.2229 0.2732 0.046 Uiso 1 1 calc R . .
C12 C -0.3327(2) 0.01554(18) 0.18743(16) 0.0325(4) Uani 1 1 d . . .
C13 C -0.3388(2) -0.0412(2) 0.06627(18) 0.0408(4) Uani 1 1 d . . .
H13A H -0.2714 0.0252 0.0364 0.049 Uiso 1 1 calc R . .
C14 C -0.4423(2) -0.1940(2) -0.01174(19) 0.0465(5) Uani 1 1 d . . .
H14A H -0.4450 -0.2313 -0.0944 0.056 Uiso 1 1 calc R . .
C15 C -0.5409(3) -0.2917(2) 0.0297(2) 0.0535(5) Uani 1 1 d . . .
H15A H -0.6123 -0.3961 -0.0240 0.064 Uiso 1 1 calc R . .
C17 C -0.4319(3) -0.0848(2) 0.22785(19) 0.0475(5) Uani 1 1 d . . .
H17A H -0.4287 -0.0485 0.3109 0.057 Uiso 1 1 calc R . .
C18 C -0.0687(2) 0.19545(17) 0.69044(15) 0.0283(4) Uani 1 1 d . . .
C19 C -0.2374(2) 0.07990(18) 0.61693(17) 0.0331(4) Uani 1 1 d . . .
H19A H -0.3066 0.0778 0.5346 0.040 Uiso 1 1 calc R . .
C20 C -0.3070(2) -0.03294(19) 0.66164(18) 0.0369(4) Uani 1 1 d . . .
H20A H -0.4227 -0.1115 0.6098 0.044 Uiso 1 1 calc R . .
C21 C -0.2085(2) -0.03080(19) 0.78072(18) 0.0393(4) Uani 1 1 d . . .
H21A H -0.2556 -0.1077 0.8116 0.047 Uiso 1 1 calc R . .
C22 C -0.0407(3) 0.0839(2) 0.85522(19) 0.0467(5) Uani 1 1 d . . .
H22A H 0.0277 0.0857 0.9377 0.056 Uiso 1 1 calc R . .
C23 C 0.0290(2) 0.1965(2) 0.81079(18) 0.0415(4) Uani 1 1 d . . .
H23A H 0.1446 0.2749 0.8632 0.050 Uiso 1 1 calc R . .
C16 C -0.5351(3) -0.2364(2) 0.1502(2) 0.0619(6) Uani 1 1 d . . .
H16A H -0.6026 -0.3031 0.1799 0.074 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A O5 C4A 114.14(13) . . ?
C10A N1 C2 124.63(14) . . ?
C10A N1 C11 119.99(14) . . ?
C2 N1 C11 113.45(14) . . ?
C10A N10 C9A 116.58(14) . . ?
N1 C2 C3 113.78(14) . . ?
C2 C3 C4 110.18(14) . . ?
C3 C4 C4A 109.34(14) . . ?
O5 C4A C4 104.35(13) . . ?
O5 C4A C10A 108.93(12) . . ?
C4 C4A C10A 110.77(13) . . ?
O5 C4A C18 108.67(12) . . ?
C4 C4A C18 113.59(13) . . ?
C10A C4A C18 110.28(13) . . ?
O5 C5A C6 119.32(15) . . ?
O5 C5A C9A 118.47(14) . . ?
C6 C5A C9A 122.06(15) . . ?
C5A C6 C7 119.02(17) . . ?
C8 C7 C6 119.99(16) . . ?
C9 C8 C7 120.24(16) . . ?
C9 C9A C5A 117.70(15) . . ?
C9 C9A N10 120.17(16) . . ?
C5A C9A N10 121.96(14) . . ?
C8 C9 C9A 120.98(17) . . ?
N10 C10A N1 120.81(15) . . ?
N10 C10A C4A 121.77(14) . . ?
N1 C10A C4A 117.21(14) . . ?
N1 C11 C12 113.05(14) . . ?
C17 C12 C13 117.94(17) . . ?
C17 C12 C11 120.93(16) . . ?
C13 C12 C11 121.05(16) . . ?
C12 C13 C14 120.70(18) . . ?
C15 C14 C13 120.46(19) . . ?
C14 C15 C16 119.25(19) . . ?
C16 C17 C12 121.39(19) . . ?
C19 C18 C23 118.20(15) . . ?
C19 C18 C4A 122.84(14) . . ?
C23 C18 C4A 118.95(15) . . ?
C18 C19 C20 121.15(16) . . ?
C21 C20 C19 119.99(17) . . ?
C20 C21 C22 119.51(16) . . ?
C21 C22 C23 120.60(18) . . ?
C22 C23 C18 120.55(18) . . ?
C17 C16 C15 120.3(2) . . ?
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
O5 C5A 1.3739(19) . ?
O5 C4A 1.4528(19) . ?
N1 C10A 1.360(2) . ?
N1 C2 1.469(2) . ?
N1 C11 1.471(2) . ?
N10 C10A 1.298(2) . ?
N10 C9A 1.404(2) . ?
C2 C3 1.509(3) . ?
C3 C4 1.515(2) . ?
C4 C4A 1.519(2) . ?
C4A C10A 1.528(2) . ?
C4A C18 1.536(2) . ?
C5A C6 1.381(2) . ?
C5A C9A 1.400(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.387(3) . ?
C8 C9 1.386(3) . ?
C9A C9 1.390(2) . ?
C11 C12 1.509(3) . ?
C12 C17 1.382(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.388(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.378(3) . ?
C17 C16 1.378(3) . ?
C18 C19 1.386(3) . ?
C18 C23 1.387(2) . ?
C19 C20 1.391(2) . ?
C20 C21 1.373(3) . ?
C21 C22 1.379(3) . ?
C22 C23 1.387(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9755946
