#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023472.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_4023472
loop_
_publ_author_name
'Leonid G. Voskressensky'
'Ilya V. Vorobiev'
'Tatyana N. Borisova'
'Alexey V. Varlamov'
_publ_section_title
;
 Synthesis and Reactivity of a Novel Class of Long-Lived Ammonium
 Ylides: Derivatives of Benzo[b]pyrrolo[2,1-f][1.6]naphthyridine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4596
_journal_page_last               4601
_journal_paper_doi               10.1021/jo8003698
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C20 H15 N3 O4'
_chemical_formula_sum            'C20 H15 N3 O4'
_chemical_formula_weight         361.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3267(9)
_cell_length_b                   7.3356(6)
_cell_length_c                   36.777(3)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.32
_cell_measurement_theta_min      2.21
_cell_volume                     3325.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24367
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0878
_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)+(0.0500P)²+15.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                2503
_reflns_number_total             2915
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8003698-File002.cif
_cod_data_source_block           UDN-5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
;
_cod_database_code               4023472
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
O1 O -0.0506(2) -0.0460(4) 0.31646(7) 0.0263(7) Uani 1 1 d . . .
O2 O -0.0039(3) 0.1379(7) 0.27030(10) 0.0766(15) Uani 1 1 d . . .
O3 O 0.3778(2) 0.0609(5) 0.38779(8) 0.0368(8) Uani 1 1 d . . .
O4 O 0.3726(2) 0.0262(4) 0.32739(8) 0.0342(8) Uani 1 1 d . . .
C1 C 0.0392(3) 0.0015(5) 0.33686(11) 0.0243(9) Uani 1 1 d . . .
C2 C 0.1464(3) 0.0107(6) 0.32599(11) 0.0266(9) Uani 1 1 d . . .
H2A H 0.1726 0.0018 0.3018 0.032 Uiso 1 1 calc R . .
C3 C 0.2088(3) 0.0353(6) 0.35695(11) 0.0264(9) Uani 1 1 d . . .
N4 N 0.1395(3) 0.0419(5) 0.38614(8) 0.0229(7) Uani 1 1 d . . .
C5 C 0.1627(3) 0.0621(6) 0.42507(10) 0.0262(9) Uani 1 1 d . . .
H5A H 0.1451 0.1875 0.4331 0.031 Uiso 1 1 calc R . .
H5B H 0.2408 0.0401 0.4297 0.031 Uiso 1 1 calc R . .
C6 C 0.0950(3) -0.0741(6) 0.44606(11) 0.0265(9) Uani 1 1 d . . .
H6A H 0.1202 -0.1990 0.4404 0.032 Uiso 1 1 calc R . .
H6B H 0.1051 -0.0536 0.4724 0.032 Uiso 1 1 calc R . .
C7 C -0.0236(3) -0.0582(5) 0.43692(10) 0.0210(8) Uani 1 1 d . . .
N8 N -0.0939(3) -0.1004(4) 0.46252(8) 0.0213(7) Uani 1 1 d . . .
C9 C -0.2023(3) -0.0850(5) 0.45483(10) 0.0221(8) Uani 1 1 d . . .
C10 C -0.2773(3) -0.1394(5) 0.48131(10) 0.0234(9) Uani 1 1 d . . .
H10A H -0.2521 -0.1902 0.5035 0.028 Uiso 1 1 calc R . .
C11 C -0.3865(3) -0.1203(6) 0.47570(11) 0.0256(9) Uani 1 1 d . . .
H11A H -0.4365 -0.1571 0.4939 0.031 Uiso 1 1 calc R . .
C12 C -0.4244(3) -0.0459(6) 0.44282(11) 0.0259(9) Uani 1 1 d . . .
H12A H -0.5002 -0.0329 0.4390 0.031 Uiso 1 1 calc R . .
C13 C -0.3534(3) 0.0079(5) 0.41625(10) 0.0247(9) Uani 1 1 d . . .
H13A H -0.3801 0.0587 0.3942 0.030 Uiso 1 1 calc R . .
C14 C -0.2405(3) -0.0122(5) 0.42156(10) 0.0218(8) Uani 1 1 d . . .
C15 C -0.1619(3) 0.0346(5) 0.39467(10) 0.0220(8) Uani 1 1 d . . .
C16 C -0.0531(3) 0.0015(5) 0.40127(10) 0.0216(8) Uani 1 1 d . . .
C17 C 0.0346(3) 0.0204(5) 0.37436(10) 0.0231(9) Uani 1 1 d . . .
C18 C -0.0643(4) 0.0282(7) 0.28281(11) 0.0374(11) Uani 1 1 d . . .
C19 C -0.1643(3) -0.0445(7) 0.26532(11) 0.0328(10) Uani 1 1 d . . .
H19A H -0.1728 0.0101 0.2412 0.049 Uiso 1 1 calc R . .
H19B H -0.2275 -0.0144 0.2803 0.049 Uiso 1 1 calc R . .
H19C H -0.1585 -0.1772 0.2629 0.049 Uiso 1 1 calc R . .
C20 C 0.3267(3) 0.0440(6) 0.36001(11) 0.0272(9) Uani 1 1 d . . .
C21 C 0.4908(3) 0.0160(7) 0.32671(13) 0.0392(12) Uani 1 1 d . . .
H21A H 0.5157 0.0028 0.3015 0.059 Uiso 1 1 calc R . .
H21B H 0.5149 -0.0894 0.3410 0.059 Uiso 1 1 calc R . .
H21C H 0.5213 0.1276 0.3372 0.059 Uiso 1 1 calc R . .
C22 C -0.1983(3) 0.1275(5) 0.36252(11) 0.0227(9) Uani 1 1 d . . .
N22 N -0.2304(3) 0.2114(5) 0.33855(9) 0.0304(8) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C1 119.4(3) . . ?
C20 O4 C21 116.4(3) . . ?
C2 C1 O1 128.4(4) . . ?
C2 C1 C17 108.8(3) . . ?
O1 C1 C17 122.1(4) . . ?
C1 C2 C3 107.4(3) . . ?
N4 C3 C2 107.6(3) . . ?
N4 C3 C20 123.9(4) . . ?
C2 C3 C20 128.4(4) . . ?
C17 N4 C3 109.6(3) . . ?
C17 N4 C5 120.2(3) . . ?
C3 N4 C5 130.2(3) . . ?
N4 C5 C6 108.9(3) . . ?
C7 C6 C5 111.8(3) . . ?
N8 C7 C16 124.1(4) . . ?
N8 C7 C6 117.5(3) . . ?
C16 C7 C6 118.4(3) . . ?
C7 N8 C9 118.3(3) . . ?
N8 C9 C10 118.5(3) . . ?
N8 C9 C14 122.2(4) . . ?
C10 C9 C14 119.3(4) . . ?
C11 C10 C9 121.0(4) . . ?
C10 C11 C12 119.7(4) . . ?
C13 C12 C11 120.9(4) . . ?
C12 C13 C14 120.0(4) . . ?
C13 C14 C9 119.1(4) . . ?
C13 C14 C15 123.2(3) . . ?
C9 C14 C15 117.7(4) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 C22 122.0(4) . . ?
C14 C15 C22 118.2(3) . . ?
C15 C16 C7 117.5(4) . . ?
C15 C16 C17 125.2(3) . . ?
C7 C16 C17 117.3(3) . . ?
N4 C17 C1 106.6(3) . . ?
N4 C17 C16 119.4(3) . . ?
C1 C17 C16 133.6(4) . . ?
O2 C18 O1 123.0(4) . . ?
O2 C18 C19 126.4(4) . . ?
O1 C18 C19 110.6(4) . . ?
O3 C20 O4 123.4(4) . . ?
O3 C20 C3 126.1(4) . . ?
O4 C20 C3 110.4(3) . . ?
N22 C22 C15 174.9(4) . . ?
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
O1 C18 1.362(5) . ?
O1 C1 1.382(5) . ?
O2 C18 1.189(5) . ?
O3 C20 1.206(5) . ?
O4 C20 1.333(5) . ?
O4 C21 1.460(5) . ?
C1 C2 1.382(6) . ?
C1 C17 1.387(5) . ?
C2 C3 1.386(6) . ?
C3 N4 1.373(5) . ?
C3 C20 1.459(6) . ?
N4 C17 1.373(5) . ?
N4 C5 1.468(5) . ?
C5 C6 1.514(6) . ?
C6 C7 1.505(5) . ?
C7 N8 1.317(5) . ?
C7 C16 1.429(5) . ?
N8 C9 1.370(5) . ?
C9 C10 1.401(5) . ?
C9 C14 1.415(5) . ?
C10 C11 1.368(6) . ?
C11 C12 1.406(6) . ?
C12 C13 1.369(6) . ?
C13 C14 1.414(6) . ?
C14 C15 1.426(5) . ?
C15 C16 1.384(6) . ?
C15 C22 1.437(5) . ?
C16 C17 1.472(5) . ?
C18 C19 1.490(6) . ?
C22 N22 1.146(5) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 -46.5(6) . . . . ?
C18 O1 C1 C17 144.0(4) . . . . ?
O1 C1 C2 C3 -170.5(4) . . . . ?
C17 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 N4 -0.4(5) . . . . ?
C1 C2 C3 C20 176.7(4) . . . . ?
C2 C3 N4 C17 0.6(5) . . . . ?
C20 C3 N4 C17 -176.6(4) . . . . ?
C2 C3 N4 C5 178.7(4) . . . . ?
C20 C3 N4 C5 1.5(7) . . . . ?
C17 N4 C5 C6 43.1(5) . . . . ?
C3 N4 C5 C6 -134.9(4) . . . . ?
N4 C5 C6 C7 -53.8(4) . . . . ?
C5 C6 C7 N8 -149.8(3) . . . . ?
C5 C6 C7 C16 30.2(5) . . . . ?
C16 C7 N8 C9 -0.6(6) . . . . ?
C6 C7 N8 C9 179.4(3) . . . . ?
C7 N8 C9 C10 176.6(3) . . . . ?
C7 N8 C9 C14 -5.1(6) . . . . ?
N8 C9 C10 C11 177.4(4) . . . . ?
C14 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C12 C13 C14 C9 -1.2(6) . . . . ?
C12 C13 C14 C15 177.7(4) . . . . ?
N8 C9 C14 C13 -176.9(4) . . . . ?
C10 C9 C14 C13 1.5(6) . . . . ?
N8 C9 C14 C15 4.2(6) . . . . ?
C10 C9 C14 C15 -177.5(3) . . . . ?
C13 C14 C15 C16 -176.5(4) . . . . ?
C9 C14 C15 C16 2.4(5) . . . . ?
C13 C14 C15 C22 8.0(6) . . . . ?
C9 C14 C15 C22 -173.1(3) . . . . ?
C14 C15 C16 C7 -7.5(5) . . . . ?
C22 C15 C16 C7 167.8(3) . . . . ?
C14 C15 C16 C17 171.6(3) . . . . ?
C22 C15 C16 C17 -13.1(6) . . . . ?
N8 C7 C16 C15 6.9(6) . . . . ?
C6 C7 C16 C15 -173.0(3) . . . . ?
N8 C7 C16 C17 -172.2(4) . . . . ?
C6 C7 C16 C17 7.8(5) . . . . ?
C3 N4 C17 C1 -0.5(4) . . . . ?
C5 N4 C17 C1 -178.9(3) . . . . ?
C3 N4 C17 C16 173.0(3) . . . . ?
C5 N4 C17 C16 -5.4(5) . . . . ?
C2 C1 C17 N4 0.3(5) . . . . ?
O1 C1 C17 N4 171.6(3) . . . . ?
C2 C1 C17 C16 -171.9(4) . . . . ?
O1 C1 C17 C16 -0.6(7) . . . . ?
C15 C16 C17 N4 159.0(4) . . . . ?
C7 C16 C17 N4 -21.9(5) . . . . ?
C15 C16 C17 C1 -29.6(7) . . . . ?
C7 C16 C17 C1 149.5(4) . . . . ?
C1 O1 C18 O2 -2.5(7) . . . . ?
C1 O1 C18 C19 178.7(4) . . . . ?
C21 O4 C20 O3 3.8(6) . . . . ?
C21 O4 C20 C3 -174.7(4) . . . . ?
N4 C3 C20 O3 -1.3(7) . . . . ?
C2 C3 C20 O3 -177.9(4) . . . . ?
N4 C3 C20 O4 177.2(4) . . . . ?
C2 C3 C20 O4 0.6(6) . . . . ?
C16 C15 C22 N22 -118(5) . . . . ?
C14 C15 C22 N22 57(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658682
