#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154113.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_7154113
loop_
_publ_author_name
'Romero-Fernández, María P'
'Avalos, Martín'
'Babiano, Reyes'
'Cintas, Pedro'
'Jiménez, José L'
'Light, Mark E.'
'Palacios, Juan C.'
_publ_section_title
;
 Pseudo-cyclic structures of mono- and di-azaderivatives of
 malondialdehydes. Synthesis and conformational disentanglement by
 computational analyses.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8997
_journal_page_last               9010
_journal_paper_doi               10.1039/c4ob01507j
_journal_volume                  12
_journal_year                    2014
_chemical_compound_source        'Pedro Cintas'
_chemical_formula_sum            'C16 H14 N2 O3'
_chemical_formula_weight         282.29
_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                 93.169(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.1847(19)
_cell_length_b                   13.013(6)
_cell_length_c                   24.919(11)
_cell_measurement_reflns_used    3424
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.9
_cell_volume                     1354.9(11)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6477
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.1248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2016
_reflns_number_total             2360
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ob01507j2.cif
_cod_data_source_block           2011acc0768
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7154112--7154113.cif.
;
_cod_original_cell_volume        1354.9(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7154113
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
O1 O 0.0826(3) 0.90450(9) 0.03202(5) 0.0211(3) Uani 1 1 d .
O2 O -0.6036(4) 0.46598(10) 0.23832(6) 0.0355(4) Uani 1 1 d .
O3 O -0.7782(4) 0.58428(11) 0.29014(6) 0.0376(4) Uani 1 1 d .
N1 N -0.3207(4) 1.03866(11) 0.07523(6) 0.0176(4) Uani 1 1 d .
H901 H -0.176(5) 1.0263(16) 0.0478(9) 0.038(7) Uiso 1 1 d .
N2 N -0.6436(4) 0.55695(13) 0.24971(6) 0.0252(4) Uani 1 1 d .
C1 C -0.3623(5) 1.29531(14) 0.03221(8) 0.0217(5) Uani 1 1 d .
H1 H -0.4765 1.2758 -0.0002 0.026 Uiso 1 1 calc R
C2 C -0.2081(5) 1.38976(14) 0.03531(8) 0.0262(5) Uani 1 1 d .
H2 H -0.2196 1.4349 0.0053 0.031 Uiso 1 1 calc R
C3 C -0.0375(5) 1.41805(15) 0.08215(8) 0.0269(5) Uani 1 1 d .
H3 H 0.0716 1.4821 0.0841 0.032 Uiso 1 1 calc R
C4 C -0.0263(5) 1.35298(15) 0.12596(8) 0.0267(5) Uani 1 1 d .
H4 H 0.0889 1.3726 0.1583 0.032 Uiso 1 1 calc R
C5 C -0.1823(5) 1.25939(14) 0.12289(8) 0.0228(5) Uani 1 1 d .
H5 H -0.1740 1.2151 0.1532 0.027 Uiso 1 1 calc R
C6 C -0.3515(4) 1.22933(13) 0.07581(7) 0.0178(4) Uani 1 1 d .
C7 C -0.5295(5) 1.12858(13) 0.07282(8) 0.0197(4) Uani 1 1 d .
H7A H -0.6741 1.1252 0.1029 0.024 Uiso 1 1 calc R
H7B H -0.6639 1.1264 0.0389 0.024 Uiso 1 1 calc R
C8 C -0.3649(4) 0.96143(13) 0.10777(7) 0.0184(4) Uani 1 1 d .
H8 H -0.5139 0.9720 0.1346 0.022 Uiso 1 1 calc R
C9 C -0.2164(4) 0.86512(13) 0.10722(7) 0.0174(4) Uani 1 1 d .
C10 C 0.0018(4) 0.84347(14) 0.06707(7) 0.0184(4) Uani 1 1 d .
H10 H 0.0936 0.7767 0.0670 0.022 Uiso 1 1 calc R
C11 C -0.3133(4) 0.78562(14) 0.14500(7) 0.0176(4) Uani 1 1 d .
C12 C -0.4427(5) 0.81147(14) 0.19408(7) 0.0210(5) Uani 1 1 d .
H12 H -0.4528 0.8817 0.2042 0.025 Uiso 1 1 calc R
C13 C -0.5549(5) 0.73792(14) 0.22771(8) 0.0215(5) Uani 1 1 d .
H13 H -0.6509 0.7573 0.2599 0.026 Uiso 1 1 calc R
C14 C -0.5265(5) 0.63516(14) 0.21428(7) 0.0200(4) Uani 1 1 d .
C15 C -0.3937(5) 0.60558(14) 0.16725(8) 0.0219(5) Uani 1 1 d .
H15 H -0.3726 0.5348 0.1587 0.026 Uiso 1 1 calc R
C16 C -0.2919(5) 0.68024(14) 0.13280(8) 0.0207(5) Uani 1 1 d .
H16 H -0.2051 0.6601 0.1000 0.025 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
C8 N1 C7 122.38(17)
O2 N2 O3 122.65(17)
O2 N2 C14 118.68(17)
O3 N2 C14 118.68(16)
C6 C1 C2 120.71(18)
C3 C2 C1 119.94(19)
C4 C3 C2 119.82(19)
C3 C4 C5 120.11(19)
C4 C5 C6 120.72(18)
C1 C6 C5 118.71(17)
C1 C6 C7 120.41(17)
C5 C6 C7 120.84(17)
N1 C7 C6 113.69(16)
N1 C8 C9 127.08(19)
C8 C9 C10 119.20(17)
C8 C9 C11 119.04(18)
C10 C9 C11 121.50(17)
O1 C10 C9 125.44(18)
C12 C11 C16 116.94(17)
C12 C11 C9 121.45(17)
C16 C11 C9 121.56(17)
C13 C12 C11 121.73(18)
C12 C13 C14 119.29(18)
C15 C14 C13 121.24(18)
C15 C14 N2 119.14(17)
C13 C14 N2 119.61(18)
C14 C15 C16 119.02(17)
C15 C16 C11 121.71(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.241(2)
O2 N2 1.231(2)
O3 N2 1.234(2)
N1 C8 1.311(2)
N1 C7 1.460(2)
N2 C14 1.450(2)
C1 C6 1.384(3)
C1 C2 1.388(3)
C2 C3 1.384(3)
C3 C4 1.380(3)
C4 C5 1.382(3)
C5 C6 1.393(3)
C6 C7 1.508(3)
C8 C9 1.399(3)
C9 C10 1.419(3)
C9 C11 1.471(3)
C11 C12 1.405(3)
C11 C16 1.409(3)
C12 C13 1.372(3)
C13 C14 1.385(3)
C14 C15 1.379(3)
C15 C16 1.380(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H901 O1 0.95(2) 1.97(2) 2.694(2) 131.1(18) .
N1 H901 O1 0.95(2) 2.24(2) 2.996(2) 136.1(18) 3_575
