#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150390.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_7150390
loop_
_publ_author_name
'Zhang, Min'
'An, Hui-Ying'
'Zhao, Bao-Guo'
'Xu, Jian-Hua'
_publ_section_title
;
 Aromatic annulation strategy for naphthalenes fused at 1,2- and
 3,4-positions with two heterocycles.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              33
_journal_page_last               35
_journal_paper_doi               10.1039/b514496e
_journal_volume                  4
_journal_year                    2006
_chemical_formula_moiety         'C19 H11 N O3'
_chemical_formula_sum            'C19 H11 N O3'
_chemical_formula_weight         301.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5260(19)
_cell_length_b                   18.319(4)
_cell_length_c                   7.9420(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.15
_cell_volume                     1377.7(5)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2629
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo,1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0551
_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)+(0.0445P)²+1.75P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                1361
_reflns_number_total             2439
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b514496e.txt
_cod_data_source_block           5b
_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 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7150390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O3 O 0.8887(3) -0.00696(13) 0.2387(3) 0.0421(7) Uani 1 1 d . . .
O2 O 0.5007(3) 0.11644(15) 0.7028(3) 0.0571(8) Uani 1 1 d . . .
O1 O 0.7119(3) 0.14345(14) 0.2186(3) 0.0537(8) Uani 1 1 d . . .
C4 C 0.6616(4) 0.03542(19) 0.5720(4) 0.0373(9) Uani 1 1 d . . .
N N 0.5898(3) 0.14674(16) 0.4538(4) 0.0424(8) Uani 1 1 d . . .
C12 C 0.9462(4) -0.11209(19) 0.3894(4) 0.0373(9) Uani 1 1 d . . .
C3 C 0.7243(4) 0.04527(19) 0.4241(4) 0.0374(9) Uani 1 1 d . . .
C7 C 0.9683(4) -0.0708(2) 0.2469(4) 0.0390(9) Uani 1 1 d . . .
C19 C 0.6881(4) -0.0259(2) 0.6795(4) 0.0379(9) Uani 1 1 d . . .
C6 C 0.8171(4) -0.00897(19) 0.3796(4) 0.0372(9) Uani 1 1 d . . .
C10 C 1.1092(4) -0.1993(2) 0.2980(5) 0.0507(11) Uani 1 1 d . . .
H13A H 1.1573 -0.2433 0.3130 0.061 Uiso 1 1 calc R . .
C11 C 1.0190(4) -0.1781(2) 0.4119(5) 0.0447(10) Uani 1 1 d . . .
H12A H 1.0063 -0.2077 0.5042 0.054 Uiso 1 1 calc R . .
C13 C 0.8471(4) -0.07076(19) 0.4765(4) 0.0366(9) Uani 1 1 d . . .
C14 C 0.7844(4) -0.08043(19) 0.6324(4) 0.0374(9) Uani 1 1 d . . .
C5 C 0.5741(4) 0.1011(2) 0.5928(5) 0.0423(9) Uani 1 1 d . . .
C2 C 0.6791(4) 0.1160(2) 0.3463(5) 0.0409(9) Uani 1 1 d . . .
C1 C 0.5267(4) 0.2184(2) 0.4293(5) 0.0556(11) Uani 1 1 d . . .
H7A H 0.5520 0.2391 0.3257 0.083 Uiso 1 1 calc R . .
H7B H 0.5605 0.2494 0.5225 0.083 Uiso 1 1 calc R . .
H7C H 0.4259 0.2143 0.4236 0.083 Uiso 1 1 calc R . .
C15 C 0.8155(4) -0.1405(2) 0.7402(5) 0.0486(10) Uani 1 1 d . . .
H6A H 0.8779 -0.1761 0.7111 0.058 Uiso 1 1 calc R . .
C16 C 0.7542(4) -0.1469(2) 0.8885(5) 0.0563(11) Uani 1 1 d . . .
H5A H 0.7761 -0.1866 0.9593 0.068 Uiso 1 1 calc R . .
C17 C 0.6594(4) -0.0942(2) 0.9335(5) 0.0578(12) Uani 1 1 d . . .
H4A H 0.6176 -0.0996 1.0332 0.069 Uiso 1 1 calc R . .
C18 C 0.6274(4) -0.0351(2) 0.8330(5) 0.0497(10) Uani 1 1 d . . .
H3A H 0.5648 -0.0002 0.8657 0.060 Uiso 1 1 calc R . .
C8 C 1.0593(4) -0.0897(2) 0.1288(5) 0.0450(10) Uani 1 1 d . . .
H2A H 1.0719 -0.0604 0.0360 0.054 Uiso 1 1 calc R . .
C9 C 1.1295(4) -0.1547(2) 0.1585(5) 0.0494(10) Uani 1 1 d . . .
H1A H 1.1925 -0.1698 0.0839 0.059 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
C6 O3 C7 104.8(3) . . ?
C3 C4 C19 123.3(3) . . ?
C3 C4 C5 106.7(3) . . ?
C19 C4 C5 129.9(3) . . ?
C2 N C5 111.5(3) . . ?
C2 N C1 123.9(3) . . ?
C5 N C1 124.5(3) . . ?
C11 C12 C7 117.1(3) . . ?
C11 C12 C13 137.3(3) . . ?
C7 C12 C13 105.6(3) . . ?
C4 C3 C6 117.6(3) . . ?
C4 C3 C2 109.6(3) . . ?
C6 C3 C2 132.8(3) . . ?
C8 C7 O3 123.7(3) . . ?
C8 C7 C12 125.0(3) . . ?
O3 C7 C12 111.3(3) . . ?
C18 C19 C4 123.4(3) . . ?
C18 C19 C14 118.4(3) . . ?
C4 C19 C14 118.2(3) . . ?
O3 C6 C13 112.6(3) . . ?
O3 C6 C3 124.7(3) . . ?
C13 C6 C3 122.6(3) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H13A 119.8 . . ?
C9 C10 H13A 119.8 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H12A 120.0 . . ?
C12 C11 H12A 120.0 . . ?
C6 C13 C14 119.9(3) . . ?
C6 C13 C12 105.6(3) . . ?
C14 C13 C12 134.4(3) . . ?
C15 C14 C19 119.0(3) . . ?
C15 C14 C13 122.7(3) . . ?
C19 C14 C13 118.4(3) . . ?
O2 C5 N 123.3(4) . . ?
O2 C5 C4 130.1(4) . . ?
N C5 C4 106.6(3) . . ?
O1 C2 N 125.5(3) . . ?
O1 C2 C3 128.9(3) . . ?
N C2 C3 105.6(3) . . ?
N C1 H7A 109.5 . . ?
N C1 H7B 109.5 . . ?
H7A C1 H7B 109.5 . . ?
N C1 H7C 109.5 . . ?
H7A C1 H7C 109.5 . . ?
H7B C1 H7C 109.5 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H6A 119.7 . . ?
C14 C15 H6A 119.7 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H5A 119.8 . . ?
C17 C16 H5A 119.8 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H4A 119.6 . . ?
C16 C17 H4A 119.6 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H3A 119.6 . . ?
C19 C18 H3A 119.6 . . ?
C9 C8 C7 115.3(4) . . ?
C9 C8 H2A 122.3 . . ?
C7 C8 H2A 122.3 . . ?
C8 C9 C10 122.2(4) . . ?
C8 C9 H1A 118.9 . . ?
C10 C9 H1A 118.9 . . ?
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
O3 C6 1.373(4) . ?
O3 C7 1.391(4) . ?
O2 C5 1.210(4) . ?
O1 C2 1.203(4) . ?
C4 C3 1.387(5) . ?
C4 C19 1.417(5) . ?
C4 C5 1.484(5) . ?
N C2 1.389(4) . ?
N C5 1.405(4) . ?
N C1 1.448(5) . ?
C12 C11 1.396(5) . ?
C12 C7 1.396(5) . ?
C12 C13 1.443(5) . ?
C3 C6 1.400(5) . ?
C3 C2 1.479(5) . ?
C7 C8 1.389(5) . ?
C19 C18 1.415(5) . ?
C19 C14 1.433(5) . ?
C6 C13 1.381(5) . ?
C10 C11 1.369(5) . ?
C10 C9 1.406(5) . ?
C10 H13A 0.9300 . ?
C11 H12A 0.9300 . ?
C13 C14 1.443(5) . ?
C14 C15 1.405(5) . ?
C1 H7A 0.9600 . ?
C1 H7B 0.9600 . ?
C1 H7C 0.9600 . ?
C15 C16 1.375(5) . ?
C15 H6A 0.9300 . ?
C16 C17 1.394(6) . ?
C16 H5A 0.9300 . ?
C17 C18 1.360(5) . ?
C17 H4A 0.9300 . ?
C18 H3A 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H2A 0.9300 . ?
C9 H1A 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9827100
