#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/10/2221012.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221012
loop_
_publ_author_name
'NizamMohideen, M.'
'SubbiahPandi, A.'
'Selvam, N. Panneer'
'Perumal, P. T.'
'Damodiran, M.'
_publ_section_title
'[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-ylidine]malonaldehyde'
_journal_coeditor_code           BT2875
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o582
_journal_paper_doi               10.1107/S1600536809006023
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H14 N2 O5'
_chemical_formula_moiety         'C21 H14 N2 O5'
_chemical_formula_sum            'C21 H14 N2 O5'
_chemical_formula_weight         374.34
_chemical_name_systematic
;
[1-(3-Nitrophenyl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazin-3-
ylidine]malonaldehyde
;
_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                 104.632(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9191(4)
_cell_length_b                   23.3876(11)
_cell_length_c                   9.6199(5)
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1723.91(15)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
;
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
'Bruker Kappa APEXII CCD diffractometer'
;
_diffrn_measurement_method       'ω and φ scan'
_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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16263
_diffrn_reflns_theta_full        24.94
_diffrn_reflns_theta_max         24.94
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0361
_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)+(0.0509P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2334
_reflns_number_total             3023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2875.cif
_cod_data_source_block           I
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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:

'_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221012
_cod_database_fobs_code          2221012
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.30114(13) 0.16841(5) 0.13932(12) 0.0486(3) Uani d . 1 . .
O O2 0.8553(2) -0.07387(6) 0.43720(18) 0.0878(5) Uani d . 1 . .
O O3 0.8486(3) -0.07086(8) 0.6565(2) 0.1195(7) Uani d . 1 . .
O O4 0.30819(17) 0.00916(5) -0.05620(14) 0.0638(4) Uani d . 1 . .
O O5 -0.14205(16) 0.09772(6) -0.06754(16) 0.0718(4) Uani d . 1 . .
N N1 0.47317(16) 0.09268(5) 0.11444(13) 0.0418(3) Uani d . 1 . .
H H1 0.4847 0.0619 0.0690 0.050 Uiso calc R 1 . .
N N2 0.8208(2) -0.04987(7) 0.53794(19) 0.0637(4) Uani d . 1 . .
C C1 0.3180(2) 0.11583(6) 0.08808(16) 0.0401(4) Uani d . 1 . .
C C2 0.62913(19) 0.11553(6) 0.21612(16) 0.0388(4) Uani d . 1 . .
H H2 0.7310 0.1063 0.1799 0.047 Uiso calc R 1 . .
C C3 0.61165(19) 0.17956(6) 0.21877(16) 0.0395(4) Uani d . 1 . .
C C4 0.45014(19) 0.20287(6) 0.18043(17) 0.0412(4) Uani d . 1 . .
C C5 0.4178(2) 0.26167(7) 0.17688(17) 0.0464(4) Uani d . 1 . .
H H5 0.3042 0.2757 0.1503 0.056 Uiso calc R 1 . .
C C6 0.5556(2) 0.29776(7) 0.21305(18) 0.0485(4) Uani d . 1 . .
H H6 0.5363 0.3370 0.2088 0.058 Uiso calc R 1 . .
C C7 0.7285(2) 0.27682(7) 0.25716(17) 0.0439(4) Uani d . 1 . .
C C8 0.8737(2) 0.31383(8) 0.29883(19) 0.0529(4) Uani d . 1 . .
H H8 0.8562 0.3532 0.2938 0.063 Uiso calc R 1 . .
C C9 1.0376(2) 0.29305(8) 0.3459(2) 0.0576(5) Uani d . 1 . .
H H9 1.1313 0.3181 0.3739 0.069 Uiso calc R 1 . .
C C10 1.0666(2) 0.23391(8) 0.35255(19) 0.0555(5) Uani d . 1 . .
H H10 1.1796 0.2199 0.3856 0.067 Uiso calc R 1 . .
C C11 0.9305(2) 0.19657(7) 0.31089(17) 0.0474(4) Uani d . 1 . .
H H11 0.9518 0.1574 0.3150 0.057 Uiso calc R 1 . .
C C12 0.7579(2) 0.21687(7) 0.26167(16) 0.0402(4) Uani d . 1 . .
C C13 0.65335(18) 0.08758(6) 0.36265(16) 0.0370(3) Uani d . 1 . .
C C14 0.6049(2) 0.11392(7) 0.47526(18) 0.0504(4) Uani d . 1 . .
H H14 0.5557 0.1503 0.4621 0.061 Uiso calc R 1 . .
C C15 0.6281(2) 0.08734(8) 0.60702(19) 0.0590(5) Uani d . 1 . .
H H15 0.5947 0.1060 0.6812 0.071 Uiso calc R 1 . .
C C16 0.6998(2) 0.03369(8) 0.62976(18) 0.0510(4) Uani d . 1 . .
H H16 0.7172 0.0157 0.7184 0.061 Uiso calc R 1 . .
C C17 0.7447(2) 0.00769(7) 0.51666(18) 0.0441(4) Uani d . 1 . .
C C18 0.72429(19) 0.03325(7) 0.38466(17) 0.0410(4) Uani d . 1 . .
H H18 0.7578 0.0142 0.3110 0.049 Uiso calc R 1 . .
C C19 0.1647(2) 0.08978(7) 0.00800(16) 0.0425(4) Uani d . 1 . .
C C20 -0.0008(2) 0.11766(8) -0.00797(18) 0.0525(4) Uani d . 1 . .
H H20 0.0004 0.1542 0.0307 0.063 Uiso calc R 1 . .
C C21 0.1741(2) 0.03622(8) -0.05856(18) 0.0529(4) Uani d . 1 . .
H H21 0.0691 0.0200 -0.1087 0.063 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C4 . . 118.37(12) ?
C1 N1 C2 . . 124.71(13) ?
C1 N1 H1 . . 117.6 ?
C2 N1 H1 . . 117.6 ?
O2 N2 O3 . . 122.89(17) ?
O2 N2 C17 . . 118.80(16) ?
O3 N2 C17 . . 118.31(17) ?
N1 C1 O1 . . 118.90(14) ?
N1 C1 C19 . . 124.59(14) ?
O1 C1 C19 . . 116.51(13) ?
N1 C2 C3 . . 107.93(12) ?
N1 C2 C13 . . 110.41(12) ?
C3 C2 C13 . . 113.73(12) ?
N1 C2 H2 . . 108.2 ?
C3 C2 H2 . . 108.2 ?
C13 C2 H2 . . 108.2 ?
C4 C3 C12 . . 118.39(14) ?
C4 C3 C2 . . 118.75(13) ?
C12 C3 C2 . . 122.86(13) ?
C3 C4 O1 . . 121.07(13) ?
C3 C4 C5 . . 123.91(15) ?
O1 C4 C5 . . 115.02(13) ?
C6 C5 C4 . . 118.41(15) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C7 . . 121.19(15) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C6 C7 C8 . . 121.97(15) ?
C6 C7 C12 . . 119.34(15) ?
C8 C7 C12 . . 118.69(15) ?
C9 C8 C7 . . 121.21(17) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C8 C9 C10 . . 120.15(16) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 120.65(17) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.58(16) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C7 . . 118.71(14) ?
C11 C12 C3 . . 122.58(14) ?
C7 C12 C3 . . 118.70(14) ?
C14 C13 C18 . . 118.15(15) ?
C14 C13 C2 . . 122.67(14) ?
C18 C13 C2 . . 119.18(13) ?
C13 C14 C15 . . 121.30(16) ?
C13 C14 H14 . . 119.3 ?
C15 C14 H14 . . 119.3 ?
C16 C15 C14 . . 120.76(16) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C17 C16 C15 . . 117.36(16) ?
C17 C16 H16 . . 121.3 ?
C15 C16 H16 . . 121.3 ?
C16 C17 C18 . . 123.15(15) ?
C16 C17 N2 . . 118.43(15) ?
C18 C17 N2 . . 118.41(15) ?
C17 C18 C13 . . 119.26(14) ?
C17 C18 H18 . . 120.4 ?
C13 C18 H18 . . 120.4 ?
C1 C19 C21 . . 119.67(15) ?
C1 C19 C20 . . 120.10(15) ?
C21 C19 C20 . . 120.22(15) ?
O5 C20 C19 . . 125.67(18) ?
O5 C20 H20 . . 117.2 ?
C19 C20 H20 . . 117.2 ?
O4 C21 C19 . . 126.11(16) ?
O4 C21 H21 . . 116.9 ?
C19 C21 H21 . . 116.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.3440(18) ?
O1 C4 . 1.4009(18) ?
O2 N2 . 1.209(2) ?
O3 N2 . 1.210(2) ?
O4 C21 . 1.232(2) ?
O5 C20 . 1.214(2) ?
N1 C1 . 1.3075(19) ?
N1 C2 . 1.4689(19) ?
N1 H1 . 0.8600 ?
N2 C17 . 1.468(2) ?
C1 C19 . 1.402(2) ?
C2 C3 . 1.505(2) ?
C2 C13 . 1.521(2) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.353(2) ?
C3 C12 . 1.425(2) ?
C4 C5 . 1.398(2) ?
C5 C6 . 1.354(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.414(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.414(2) ?
C7 C12 . 1.420(2) ?
C8 C9 . 1.352(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.401(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.366(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.411(2) ?
C11 H11 . 0.9300 ?
C13 C14 . 1.382(2) ?
C13 C18 . 1.384(2) ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.372(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.370(2) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.376(2) ?
C18 H18 . 0.9300 ?
C19 C21 . 1.417(2) ?
C19 C20 . 1.437(2) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C11 H11 O3 3_756 0.93 2.54 3.395(2) 152.9
C18 H18 O4 3_655 0.93 2.44 3.259(2) 147.6
N1 H1 O4 3_655 0.86 2.36 3.078(2) 141.4
N1 H1 O4 . 0.86 2.02 2.670(2) 132.0
C20 H20 O1 . 0.93 2.37 2.724(2) 102.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 10.5(2) ?
C2 N1 C1 C19 . . . . -169.97(14) ?
C4 O1 C1 N1 . . . . 18.7(2) ?
C4 O1 C1 C19 . . . . -160.81(13) ?
C1 N1 C2 C3 . . . . -31.1(2) ?
C1 N1 C2 C13 . . . . 93.82(17) ?
N1 C2 C3 C4 . . . . 24.17(19) ?
C13 C2 C3 C4 . . . . -98.69(16) ?
N1 C2 C3 C12 . . . . -156.62(13) ?
C13 C2 C3 C12 . . . . 80.52(17) ?
C12 C3 C4 O1 . . . . -179.04(13) ?
C2 C3 C4 O1 . . . . 0.2(2) ?
C12 C3 C4 C5 . . . . 1.6(2) ?
C2 C3 C4 C5 . . . . -179.12(15) ?
C1 O1 C4 C3 . . . . -24.0(2) ?
C1 O1 C4 C5 . . . . 155.39(14) ?
C3 C4 C5 C6 . . . . 0.4(2) ?
O1 C4 C5 C6 . . . . -178.97(14) ?
C4 C5 C6 C7 . . . . -1.7(2) ?
C5 C6 C7 C8 . . . . -178.35(16) ?
C5 C6 C7 C12 . . . . 0.9(2) ?
C6 C7 C8 C9 . . . . 177.48(16) ?
C12 C7 C8 C9 . . . . -1.8(2) ?
C7 C8 C9 C10 . . . . 0.8(3) ?
C8 C9 C10 C11 . . . . 0.4(3) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
C10 C11 C12 C7 . . . . -0.4(2) ?
C10 C11 C12 C3 . . . . -179.22(15) ?
C6 C7 C12 C11 . . . . -177.72(14) ?
C8 C7 C12 C11 . . . . 1.5(2) ?
C6 C7 C12 C3 . . . . 1.2(2) ?
C8 C7 C12 C3 . . . . -179.59(14) ?
C4 C3 C12 C11 . . . . 176.48(15) ?
C2 C3 C12 C11 . . . . -2.7(2) ?
C4 C3 C12 C7 . . . . -2.3(2) ?
C2 C3 C12 C7 . . . . 178.44(14) ?
N1 C2 C13 C14 . . . . -100.41(16) ?
C3 C2 C13 C14 . . . . 21.1(2) ?
N1 C2 C13 C18 . . . . 78.61(16) ?
C3 C2 C13 C18 . . . . -159.90(13) ?
C18 C13 C14 C15 . . . . 0.8(2) ?
C2 C13 C14 C15 . . . . 179.79(16) ?
C13 C14 C15 C16 . . . . -0.2(3) ?
C14 C15 C16 C17 . . . . -0.8(3) ?
C15 C16 C17 C18 . . . . 1.3(3) ?
C15 C16 C17 N2 . . . . -179.66(15) ?
O2 N2 C17 C16 . . . . 177.49(18) ?
O3 N2 C17 C16 . . . . -3.6(3) ?
O2 N2 C17 C18 . . . . -3.4(3) ?
O3 N2 C17 C18 . . . . 175.53(19) ?
C16 C17 C18 C13 . . . . -0.7(2) ?
N2 C17 C18 C13 . . . . -179.79(14) ?
C14 C13 C18 C17 . . . . -0.3(2) ?
C2 C13 C18 C17 . . . . -179.37(13) ?
N1 C1 C19 C21 . . . . -4.3(2) ?
O1 C1 C19 C21 . . . . 175.26(14) ?
N1 C1 C19 C20 . . . . 176.56(15) ?
O1 C1 C19 C20 . . . . -3.9(2) ?
C1 C19 C20 O5 . . . . -175.50(17) ?
C21 C19 C20 O5 . . . . 5.3(3) ?
C1 C19 C21 O4 . . . . -1.5(3) ?
C20 C19 C21 O4 . . . . 177.67(17) ?
