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#$Date: 2016-03-21 02:57:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178413 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/34/4023474.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_4023474
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_sum            'C17 H15 N3 O2'
_chemical_formula_weight         293.32
_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                 101.39(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3390(15)
_cell_length_b                   13.311(3)
_cell_length_c                   14.787(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.1
_cell_volume                     1416.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_method       /w
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3346
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0.3
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0455
_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)+(0.0905P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                1459
_reflns_number_total             3090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8003698-File006.cif
_cod_data_source_block           u
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023474
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1209(3) 0.15535(13) 0.45801(12) 0.0601(5) Uani 1 1 d . . .
N1 N 0.2388(3) 0.48300(13) 0.60933(12) 0.0363(5) Uani 1 1 d . . .
N2 N 0.1545(3) 0.18599(13) 0.68377(12) 0.0386(5) Uani 1 1 d . . .
N3 N 0.2004(4) 0.2013(2) 0.34929(17) 0.0737(8) Uani 1 1 d . . .
C1 C 0.2504(3) 0.50776(16) 0.52036(14) 0.0340(5) Uani 1 1 d . . .
C2 C 0.2910(4) 0.60781(17) 0.50068(17) 0.0441(6) Uani 1 1 d . . .
H2A H 0.3036 0.6561 0.5469 0.053 Uiso 1 1 calc R . .
C3 C 0.3119(3) 0.63422(19) 0.41475(17) 0.0488(7) Uani 1 1 d . . .
H3A H 0.3401 0.7004 0.4027 0.059 Uiso 1 1 calc R . .
C4 C 0.2914(4) 0.56320(19) 0.34436(17) 0.0487(7) Uani 1 1 d . . .
H4A H 0.3058 0.5824 0.2857 0.058 Uiso 1 1 calc R . .
C5 C 0.2506(3) 0.46571(18) 0.36058(15) 0.0413(6) Uani 1 1 d . . .
H5A H 0.2377 0.4188 0.3131 0.050 Uiso 1 1 calc R . .
C6 C 0.2280(3) 0.43595(16) 0.44922(14) 0.0330(5) Uani 1 1 d . . .
C7 C 0.1871(3) 0.33543(15) 0.47227(14) 0.0327(5) Uani 1 1 d . . .
C8 C 0.1658(3) 0.31141(15) 0.56096(14) 0.0310(5) Uani 1 1 d . . .
C9 C 0.1055(3) 0.21525(16) 0.58539(13) 0.0369(5) Uani 1 1 d . . .
C10 C -0.0317(4) 0.15085(17) 0.53917(17) 0.0456(6) Uani 1 1 d . . .
C11 C -0.0635(4) 0.0757(2) 0.60890(19) 0.0557(7) Uani 1 1 d . . .
H11A H -0.1444 0.0214 0.5967 0.067 Uiso 1 1 calc R . .
C12 C 0.0384(4) 0.09659(18) 0.68967(18) 0.0507(7) Uani 1 1 d . . .
H12A H 0.0378 0.0602 0.7433 0.061 Uiso 1 1 calc R . .
C13 C 0.1032(4) 0.27010(17) 0.74325(15) 0.0447(6) Uani 1 1 d . . .
H13A H -0.0302 0.2806 0.7286 0.054 Uiso 1 1 calc R . .
H13B H 0.1370 0.2510 0.8077 0.054 Uiso 1 1 calc R . .
C14 C 0.2010(4) 0.36662(17) 0.72799(14) 0.0433(6) Uani 1 1 d . . .
H14A H 0.1417 0.4217 0.7540 0.052 Uiso 1 1 calc R . .
H14B H 0.3287 0.3628 0.7613 0.052 Uiso 1 1 calc R . .
C15 C 0.2015(3) 0.38991(16) 0.62875(13) 0.0330(5) Uani 1 1 d . . .
C16 C 0.1880(4) 0.25815(18) 0.40479(15) 0.0440(6) Uani 1 1 d . . .
C17 C 0.3539(4) 0.15738(19) 0.71286(18) 0.0511(7) Uani 1 1 d . . .
H17A H 0.3823 0.1041 0.6742 0.077 Uiso 1 1 calc R . .
H17B H 0.3769 0.1352 0.7759 0.077 Uiso 1 1 calc R . .
H17C H 0.4308 0.2145 0.7073 0.077 Uiso 1 1 calc R . .
O1W O -0.4443(4) 0.0397(2) 0.41692(18) 0.1016(9) Uani 1 1 d D . .
H1W H -0.336(6) 0.087(3) 0.436(3) 0.150 Uiso 1 1 d D . .
H2W H -0.496(7) 0.043(3) 0.486(3) 0.150 Uiso 1 1 d 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
C15 N1 C1 119.37(18) . . ?
C12 N2 C9 103.85(18) . . ?
C12 N2 C17 108.78(18) . . ?
C9 N2 C17 112.61(19) . . ?
C12 N2 C13 110.41(18) . . ?
C9 N2 C13 109.63(16) . . ?
C17 N2 C13 111.30(19) . . ?
N1 C1 C6 122.2(2) . . ?
N1 C1 C2 118.7(2) . . ?
C6 C1 C2 119.1(2) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 C4 120.6(2) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 120.1(2) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 117.22(18) . . ?
C5 C6 C7 123.7(2) . . ?
C8 C7 C6 120.65(18) . . ?
C8 C7 C16 120.60(19) . . ?
C6 C7 C16 118.43(19) . . ?
C7 C8 C9 123.04(18) . . ?
C7 C8 C15 116.92(19) . . ?
C9 C8 C15 120.01(18) . . ?
C10 C9 C8 131.2(2) . . ?
C10 C9 N2 109.36(19) . . ?
C8 C9 N2 117.30(18) . . ?
O1 C10 C9 129.2(2) . . ?
O1 C10 C11 125.0(2) . . ?
C9 C10 C11 105.7(2) . . ?
C12 C11 C10 110.5(2) . . ?
C11 C12 N2 110.5(2) . . ?
C14 C13 N2 111.19(18) . . ?
C15 C14 C13 114.52(18) . . ?
N1 C15 C8 123.46(19) . . ?
N1 C15 C14 116.73(18) . . ?
C8 C15 C14 119.80(19) . . ?
N3 C16 C7 174.3(3) . . ?
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 C10 1.250(3) . ?
N1 C15 1.313(3) . ?
N1 C1 1.375(3) . ?
N2 C12 1.476(3) . ?
N2 C9 1.480(3) . ?
N2 C17 1.491(3) . ?
N2 C13 1.516(3) . ?
N3 C16 1.133(3) . ?
C1 C6 1.407(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.356(3) . ?
C3 C4 1.392(4) . ?
C4 C5 1.364(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.427(3) . ?
C7 C8 1.388(3) . ?
C7 C16 1.434(3) . ?
C8 C9 1.424(3) . ?
C8 C15 1.436(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.488(4) . ?
C11 C12 1.308(4) . ?
C13 C14 1.510(3) . ?
C14 C15 1.501(3) . ?
