#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:41:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180444 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/13/7211303.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_7211303
loop_
_publ_author_name
'Matos, Catiúcia R M O'
'Miranda, Fabio S.'
'Carneiro, José W de M'
'Pinheiro, Carlos B.'
'Ronconi, Célia M'
_publ_section_title
;
 The effect of the molecular structures of dicyanomethylene compounds on
 their supramolecular assembly, photophysical and electrochemical
 properties.
;
_journal_issue                   31
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              13013
_journal_page_last               13023
_journal_paper_doi               10.1039/c3cp51957k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C25 H20 N4 O2'
_chemical_formula_sum            'C25 H20 N4 O2'
_chemical_formula_weight         408.45
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_audit_creation_date             2012-10-25T18:53:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.267(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.4458(9)
_cell_length_b                   4.38430(10)
_cell_length_c                   19.1157(7)
_cell_measurement_reflns_used    13038
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      62.226
_cell_measurement_theta_min      1.7144
_cell_volume                     2157.80(12)
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.017881
_diffrn_orient_matrix_UB_12      -0.0658776
_diffrn_orient_matrix_UB_13      0.0665079
_diffrn_orient_matrix_UB_21      -0.0554294
_diffrn_orient_matrix_UB_22      -0.0623477
_diffrn_orient_matrix_UB_23      -0.0543025
_diffrn_orient_matrix_UB_31      0.0137173
_diffrn_orient_matrix_UB_32      -0.3394736
_diffrn_orient_matrix_UB_33      -0.0029206
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15224
_diffrn_reflns_theta_full        62.38
_diffrn_reflns_theta_max         62.38
_diffrn_reflns_theta_min         6.45
_exptl_absorpt_coefficient_mu    0.66
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.66888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       primatic
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.6398
_exptl_crystal_size_mid          0.2095
_exptl_crystal_size_min          0.0987
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.5034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                2540
_reflns_number_total             3272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cp51957k.txt
_cod_data_source_block           dcyme11
_cod_original_cell_volume        2157.79(12)
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               7211303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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 0.39771(10) 0.0812(5) 0.62820(13) 0.0653(7) Uani 1 1 d .
C26 C 0 0.5884(9) 0.25 0.0529(11) Uani 1 2 d S
H26A H 0.0006 0.4581 0.2093 0.063 Uiso 0.5 1 calc PR
H26B H -0.0006 0.4582 0.2907 0.063 Uiso 0.5 1 calc PR
O2 O 0.10202(9) 0.4639(6) 0.23306(13) 0.0610(6) Uani 1 1 d .
C25 C 0.5 -0.0382(10) 0.75 0.0557(12) Uani 1 2 d S
H25A H 0.5002 0.0923 0.7911 0.067 Uiso 0.5 1 calc PR
H25B H 0.4998 0.0923 0.7089 0.067 Uiso 0.5 1 calc PR
C17 C 0.14651(12) 0.1867(8) 0.1699(2) 0.0591(9) Uani 1 1 d .
C10 C 0.35573(12) 0.2483(7) 0.58941(19) 0.0535(8) Uani 1 1 d .
C6 C 0.31331(15) 0.5369(9) 0.4782(2) 0.0723(11) Uani 1 1 d .
H6 H 0.3128 0.6127 0.4326 0.087 Uiso 1 1 calc R
C12 C 0.45082(13) -0.2286(7) 0.72590(19) 0.0622(9) Uani 1 1 d .
H12A H 0.4516 -0.3653 0.6864 0.075 Uiso 1 1 calc R
H12B H 0.4506 -0.353 0.7677 0.075 Uiso 1 1 calc R
C23 C 0.09916(13) 0.6023(7) 0.2993(2) 0.0590(9) Uani 1 1 d .
H22A H 0.1285 0.7373 0.3213 0.071 Uiso 1 1 calc R
H23B H 0.0992 0.4477 0.3357 0.071 Uiso 1 1 calc R
C13 C 0.12711(16) 0.0124(12) 0.0030(3) 0.0871(14) Uani 1 1 d .
C5 C 0.35524(13) 0.3649(8) 0.52035(19) 0.0591(9) Uani 1 1 d .
C11 C 0.40174(14) -0.0490(8) 0.6989(2) 0.0612(9) Uani 1 1 d .
H11A H 0.3722 -0.1803 0.6934 0.073 Uiso 1 1 calc R
H11B H 0.4024 0.111 0.7343 0.073 Uiso 1 1 calc R
C21 C 0.18737(13) 0.2604(8) 0.3038(2) 0.0648(10) Uani 1 1 d .
H21 H 0.1865 0.3403 0.3485 0.078 Uiso 1 1 calc R
C18 C 0.19066(14) 0.0229(10) 0.1721(2) 0.0737(11) Uani 1 1 d .
H18 H 0.1924 -0.059 0.1282 0.088 Uiso 1 1 calc R
C22 C 0.14543(12) 0.3051(7) 0.23788(19) 0.0532(8) Uani 1 1 d .
C20 C 0.22946(15) 0.1000(10) 0.3028(3) 0.0783(12) Uani 1 1 d .
H20 H 0.2573 0.0708 0.3469 0.094 Uiso 1 1 calc R
C16 C 0.10183(14) 0.2388(9) 0.1037(2) 0.0731(11) Uani 1 1 d .
H16 H 0.0744 0.3385 0.112 0.088 Uiso 1 1 calc R
C2 C 0.40897(15) 0.3578(11) 0.4365(2) 0.0844(13) Uani 1 1 d .
N3 N 0.15324(17) -0.1051(14) -0.0233(3) 0.137(2) Uani 1 1 d .
C1 C 0.37476(17) 0.5119(14) 0.3729(3) 0.0987(17) Uani 1 1 d .
C9 C 0.31515(13) 0.3120(8) 0.6137(2) 0.0660(10) Uani 1 1 d .
H9 H 0.3154 0.2389 0.6594 0.079 Uiso 1 1 calc R
C15 C 0.09318(14) 0.1674(10) 0.0319(2) 0.0785(12) Uani 1 1 d .
C7 C 0.27209(16) 0.6005(10) 0.5013(3) 0.0786(12) Uani 1 1 d .
H7 H 0.2441 0.7164 0.472 0.094 Uiso 1 1 calc R
C4 C 0.39928(15) 0.2912(10) 0.4988(2) 0.0765(12) Uani 1 1 d .
H4 H 0.4252 0.1793 0.5339 0.092 Uiso 1 1 calc R
C19 C 0.23137(14) -0.0199(11) 0.2372(3) 0.0813(13) Uani 1 1 d .
H19 H 0.2603 -0.1299 0.2371 0.098 Uiso 1 1 calc R
N1 N 0.35003(17) 0.6386(15) 0.3212(3) 0.153(2) Uani 1 1 d .
C3 C 0.4562(2) 0.2655(15) 0.4290(3) 0.118(2) Uani 1 1 d .
C14 C 0.04349(18) 0.2364(14) -0.0253(3) 0.116(2) Uani 1 1 d .
N2 N 0.4939(2) 0.1894(15) 0.4222(3) 0.176(3) Uani 1 1 d .
C24 C 0.04876(12) 0.7803(6) 0.2755(2) 0.0599(9) Uani 1 1 d .
H24A H 0.0482 0.906 0.3169 0.072 Uiso 1 1 calc R
H24B H 0.0482 0.9161 0.2351 0.072 Uiso 1 1 calc R
C8 C 0.27373(15) 0.4871(10) 0.5690(3) 0.0751(12) Uani 1 1 d .
H8 H 0.2463 0.5285 0.5855 0.09 Uiso 1 1 calc R
N4 N 0.00530(18) 0.2939(15) -0.0703(3) 0.160(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.1034
0 -1 0 0.3302
0 1 0 0.3092
0 0 -1 0.0493
0 0 1 0.0493
1 0 0 0.1092
-37 -1 4 0.0936
27 -4 -3 0.2603
-1 0 1 0.0446
1 0 -1 0.0569
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
C10 O1 C11 120.4(3) . .
C24 C26 C24 112.4(3) 2 .
C24 C26 H26A 109.1 2 .
C24 C26 H26A 109.1 . .
C24 C26 H26B 109.1 2 .
C24 C26 H26B 109.1 . .
H26A C26 H26B 107.9 . .
C22 O2 C23 118.3(3) . .
C12 C25 C12 113.2(4) . 2_656
C12 C25 H25A 108.9 . .
C12 C25 H25A 108.9 2_656 .
C12 C25 H25B 108.9 . .
C12 C25 H25B 108.9 2_656 .
H25A C25 H25B 107.7 . .
C18 C17 C22 117.2(3) . .
C18 C17 C16 124.9(4) . .
C22 C17 C16 117.9(3) . .
O1 C10 C9 124.2(3) . .
O1 C10 C5 116.1(3) . .
C9 C10 C5 119.7(3) . .
C7 C6 C5 122.4(4) . .
C7 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
C11 C12 C25 114.7(3) . .
C11 C12 H12A 108.6 . .
C25 C12 H12A 108.6 . .
C11 C12 H12B 108.6 . .
C25 C12 H12B 108.6 . .
H12A C12 H12B 107.6 . .
O2 C23 C24 106.0(3) . .
O2 C23 H22A 110.5 . .
C24 C23 H22A 110.5 . .
O2 C23 H23B 110.5 . .
C24 C23 H23B 110.5 . .
H22A C23 H23B 108.7 . .
N3 C13 C15 176.7(5) . .
C6 C5 C10 118.7(3) . .
C6 C5 C4 124.7(3) . .
C10 C5 C4 116.6(3) . .
O1 C11 C12 107.6(3) . .
O1 C11 H11A 110.2 . .
C12 C11 H11A 110.2 . .
O1 C11 H11B 110.2 . .
C12 C11 H11B 110.2 . .
H11A C11 H11B 108.5 . .
C20 C21 C22 119.9(4) . .
C20 C21 H21 120 . .
C22 C21 H21 120 . .
C19 C18 C17 121.7(4) . .
C19 C18 H18 119.2 . .
C17 C18 H18 119.2 . .
O2 C22 C21 124.3(3) . .
O2 C22 C17 115.2(3) . .
C21 C22 C17 120.5(3) . .
C21 C20 C19 120.8(4) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C15 C16 C17 130.8(3) . .
C15 C16 H16 114.6 . .
C17 C16 H16 114.6 . .
C4 C2 C3 120.0(4) . .
C4 C2 C1 126.0(4) . .
C3 C2 C1 114.1(4) . .
N1 C1 C2 175.9(5) . .
C10 C9 C8 119.3(4) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
C16 C15 C13 127.1(4) . .
C16 C15 C14 120.4(4) . .
C13 C15 C14 112.4(4) . .
C8 C7 C6 117.8(4) . .
C8 C7 H7 121.1 . .
C6 C7 H7 121.1 . .
C2 C4 C5 130.5(3) . .
C2 C4 H4 114.8 . .
C5 C4 H4 114.8 . .
C18 C19 C20 119.9(4) . .
C18 C19 H19 120 . .
C20 C19 H19 120 . .
N2 C3 C2 179.2(7) . .
N4 C14 C15 178.8(7) . .
C26 C24 C23 115.1(2) . .
C26 C24 H24A 108.5 . .
C23 C24 H24A 108.5 . .
C26 C24 H24B 108.5 . .
C23 C24 H24B 108.5 . .
H24A C24 H24B 107.5 . .
C7 C8 C9 122.1(4) . .
C7 C8 H8 119 . .
C9 C8 H8 119 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.350(4) .
O1 C11 1.436(4) .
C26 C24 1.511(4) 2
C26 C24 1.511(4) .
C26 H26A 0.97 .
C26 H26B 0.97 .
O2 C22 1.355(4) .
O2 C23 1.431(4) .
C25 C12 1.517(4) .
C25 C12 1.517(4) 2_656
C25 H25A 0.97 .
C25 H25B 0.97 .
C17 C18 1.397(5) .
C17 C22 1.409(5) .
C17 C16 1.444(5) .
C10 C9 1.375(4) .
C10 C5 1.411(5) .
C6 C7 1.378(6) .
C6 C5 1.378(5) .
C6 H6 0.93 .
C12 C11 1.490(5) .
C12 H12A 0.97 .
C12 H12B 0.97 .
C23 C24 1.514(4) .
C23 H22A 0.97 .
C23 H23B 0.97 .
C13 N3 1.132(5) .
C13 C15 1.411(6) .
C5 C4 1.442(5) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C21 C20 1.358(5) .
C21 C22 1.396(5) .
C21 H21 0.93 .
C18 C19 1.367(6) .
C18 H18 0.93 .
C20 C19 1.378(6) .
C20 H20 0.93 .
C16 C15 1.347(6) .
C16 H16 0.93 .
C2 C4 1.341(6) .
C2 C3 1.411(6) .
C2 C1 1.422(6) .
C1 N1 1.133(6) .
C9 C8 1.392(6) .
C9 H9 0.93 .
C15 C14 1.454(6) .
C7 C8 1.372(6) .
C7 H7 0.93 .
C4 H4 0.93 .
C19 H19 0.93 .
C3 N2 1.138(6) .
C14 N4 1.130(5) .
C24 H24A 0.97 .
C24 H24B 0.97 .
C8 H8 0.93 .
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
C4 H4 N2 0.93 2.64 3.500(6) 154.3 3_656
C16 H16 N4 0.93 2.61 3.457(5) 151.6 3_565
C19 H19 N1 0.93 2.63 3.436(6) 144.9 1_545
