#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154112.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_7154112
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_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_chemical_melting_point          453
_chemical_name_systematic
'N-[2-(4-nitrophenyl)-3-(phenylamino)allylidene]aniline '
_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                 109.782(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.649(7)
_cell_length_b                   21.553(15)
_cell_length_c                   9.886(8)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.4
_cell_volume                     1734(2)
_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_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  'Varimax mirror'
_diffrn_radiation_source         RA
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6840
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0889
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0296P)²+0.7328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                2330
_reflns_number_total             3031
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ob01507j2.cif
_cod_data_source_block           2011acc0752
_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_sg_symbol_H-M      P21/c
_cod_database_code               7154112
#BEGIN Tags that were not found in dictionaries:
_shelx_title                     ' 2011acc0752 in P2(1)/c'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            113.48
_shelx_f_squared_multiplier      1.000
#END Tags that were not found in dictionaries
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
O1 O -0.3695(3) 1.02755(11) 0.7303(3) 0.0469(7) Uani 1 1 d .
O2 O -0.3275(3) 1.06743(11) 0.5443(3) 0.0516(8) Uani 1 1 d .
N1 N -0.3190(3) 1.02376(14) 0.6282(3) 0.0359(8) Uani 1 1 d .
N2 N -0.0587(3) 0.68242(12) 0.5445(3) 0.0269(7) Uani 1 1 d .
N3 N 0.1379(3) 0.73973(14) 0.4287(3) 0.0282(7) Uani 1 1 d .
H93 H 0.094(4) 0.7032(16) 0.459(4) 0.056(12) Uiso 1 1 d .
C1 C -0.2460(4) 0.96546(15) 0.6039(4) 0.0289(8) Uani 1 1 d .
C2 C -0.2323(4) 0.91618(15) 0.6984(3) 0.0278(8) Uani 1 1 d .
H2 H -0.2694 0.9201 0.7781 0.033 Uiso 1 1 calc R
C3 C -0.1633(4) 0.86135(15) 0.6734(3) 0.0288(8) Uani 1 1 d .
H3 H -0.1514 0.8278 0.7383 0.035 Uiso 1 1 calc R
C4 C -0.1099(4) 0.85379(15) 0.5541(3) 0.0258(8) Uani 1 1 d .
C5 C -0.1243(4) 0.90564(15) 0.4639(3) 0.0309(8) Uani 1 1 d .
H5 H -0.0871 0.9024 0.3841 0.037 Uiso 1 1 calc R
C6 C -0.1908(4) 0.96103(16) 0.4877(4) 0.0345(9) Uani 1 1 d .
H6 H -0.1986 0.9955 0.4258 0.041 Uiso 1 1 calc R
C7 C -0.0455(4) 0.79369(15) 0.5243(3) 0.0254(8) Uani 1 1 d .
C8 C -0.1064(4) 0.73785(15) 0.5652(3) 0.0263(8) Uani 1 1 d .
H8 H -0.1870 0.7413 0.6104 0.032 Uiso 1 1 calc R
C9 C -0.1396(4) 0.62901(15) 0.5748(3) 0.0266(8) Uani 1 1 d .
C10 C -0.3035(4) 0.62957(15) 0.5700(3) 0.0268(8) Uani 1 1 d .
H10 H -0.3651 0.6670 0.5488 0.032 Uiso 1 1 calc R
C11 C -0.3758(4) 0.57525(15) 0.5964(3) 0.0300(8) Uani 1 1 d .
H11 H -0.4861 0.5760 0.5953 0.036 Uiso 1 1 calc R
C12 C -0.2878(4) 0.51989(16) 0.6243(3) 0.0331(9) Uani 1 1 d .
H12 H -0.3380 0.4829 0.6411 0.040 Uiso 1 1 calc R
C13 C -0.1267(4) 0.51909(16) 0.6273(3) 0.0312(8) Uani 1 1 d .
H13 H -0.0665 0.4813 0.6461 0.037 Uiso 1 1 calc R
C14 C -0.0526(4) 0.57293(15) 0.6031(3) 0.0303(8) Uani 1 1 d .
H14 H 0.0582 0.5718 0.6058 0.036 Uiso 1 1 calc R
C15 C 0.0728(4) 0.79211(16) 0.4586(3) 0.0284(8) Uani 1 1 d .
H15 H 0.1098 0.8305 0.4333 0.034 Uiso 1 1 calc R
C16 C 0.2614(4) 0.73427(16) 0.3651(3) 0.0285(8) Uani 1 1 d .
C17 C 0.2883(4) 0.67550(17) 0.3181(3) 0.0319(8) Uani 1 1 d .
H17 H 0.2282 0.6408 0.3328 0.038 Uiso 1 1 calc R
C18 C 0.4037(4) 0.66816(19) 0.2497(4) 0.0388(9) Uani 1 1 d .
H18 H 0.4216 0.6282 0.2170 0.047 Uiso 1 1 calc R
C19 C 0.4920(4) 0.71813(18) 0.2289(4) 0.0408(10) Uani 1 1 d .
H19 H 0.5690 0.7129 0.1804 0.049 Uiso 1 1 calc R
C20 C 0.4680(4) 0.77619(18) 0.2790(4) 0.0398(10) Uani 1 1 d .
H20 H 0.5315 0.8104 0.2673 0.048 Uiso 1 1 calc R
C21 C 0.3524(4) 0.78486(17) 0.3461(4) 0.0350(9) Uani 1 1 d .
H21 H 0.3353 0.8249 0.3788 0.042 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
O1 N1 O2 122.8(3)
O1 N1 C1 119.0(3)
O2 N1 C1 118.2(3)
C8 N2 C9 120.1(3)
C15 N3 C16 127.3(3)
C6 C1 C2 121.8(3)
C6 C1 N1 118.9(3)
C2 C1 N1 119.2(3)
C3 C2 C1 118.4(3)
C2 C3 C4 122.0(3)
C5 C4 C3 116.9(3)
C5 C4 C7 121.9(3)
C3 C4 C7 121.2(3)
C6 C5 C4 122.1(3)
C5 C6 C1 118.7(3)
C15 C7 C8 120.9(3)
C15 C7 C4 120.1(3)
C8 C7 C4 118.9(3)
N2 C8 C7 124.3(3)
C14 C9 C10 118.9(3)
C14 C9 N2 117.9(3)
C10 C9 N2 123.1(3)
C11 C10 C9 120.0(3)
C10 C11 C12 120.5(3)
C13 C12 C11 119.6(3)
C12 C13 C14 120.5(3)
C13 C14 C9 120.6(3)
N3 C15 C7 123.9(3)
C21 C16 C17 120.0(3)
C21 C16 N3 122.7(3)
C17 C16 N3 117.3(3)
C18 C17 C16 119.5(3)
C19 C18 C17 120.6(4)
C18 C19 C20 119.7(3)
C19 C20 C21 120.8(3)
C20 C21 C16 119.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.231(3)
O2 N1 1.240(3)
N1 C1 1.462(4)
N2 C8 1.302(4)
N2 C9 1.431(4)
N3 C15 1.339(4)
N3 C16 1.416(4)
C1 C6 1.388(4)
C1 C2 1.393(4)
C2 C3 1.384(4)
C3 C4 1.414(4)
C4 C5 1.408(4)
C4 C7 1.478(4)
C5 C6 1.379(4)
C7 C15 1.385(4)
C7 C8 1.426(4)
C9 C14 1.401(4)
C9 C10 1.402(4)
C10 C11 1.393(4)
C11 C12 1.392(4)
C12 C13 1.383(5)
C13 C14 1.385(4)
C16 C21 1.394(4)
C16 C17 1.395(4)
C17 C18 1.392(4)
C18 C19 1.376(5)
C19 C20 1.387(5)
C20 C21 1.387(4)
