#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:48:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180519 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/88/7218873.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_7218873
loop_
_publ_author_name
'Marco, A. Belén'
'Mayorga Burrezo, Paula'
'Mosteo, Laura'
'Franco, Santiago'
'Garin, Javier'
'Orduna, Jesús'
'Diosdado, Beatriz'
'Villacampa, Belén'
'López Navarrete, Juan T.'
'Casado, Juan'
'Andreu, Raquel'
_publ_section_title
;
 Polarization, second-order nonlinear optical properties and
 electrochromism in 4H-pyranylidene chromophores with a quinoid/aromatic
 thiophene ring bridge
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12791A
_journal_year                    2014
_chemical_formula_moiety         'C22 H24 N2 O S'
_chemical_formula_sum            'C22 H24 N2 O S'
_chemical_formula_weight         364.49
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-06-12 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.222(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1986(13)
_cell_length_b                   6.8265(10)
_cell_length_c                   17.101(3)
_cell_measurement_reflns_used    660
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      18.7210
_cell_measurement_theta_min      3.7560
_cell_volume                     1036.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Diamond 3.2h'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip
                    Version: 03/16/09 15:32
Palatinus, L. & Chapuis, G.(2007): J. Appl. Cryst. 40, 786-790
;
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1603
_diffrn_reflns_av_sigmaI/netI    0.1485
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11105
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.1046
_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)+(0.0985P)²+0.4679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2475
_reflns_number_gt                1088
_reflns_number_total             1945
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ra12791a2.cif
_cod_data_source_block           compound
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               7218873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
S1 S 0.9466(2) 0.2500 0.49163(12) 0.0338(6) Uani 1 2 d S
C1 C 1.1379(9) 0.2500 0.5391(5) 0.0349(19) Uani 1 2 d S
C2 C 1.2200(9) 0.2500 0.4816(5) 0.039(2) Uani 1 2 d S
H2 H 1.3270 0.2500 0.4953 0.046 Uiso 1 2 calc SR
C3 C 1.1312(10) 0.2500 0.4022(5) 0.043(2) Uani 1 2 d S
H3 H 1.1714 0.2500 0.3564 0.052 Uiso 1 2 calc SR
C4 C 0.9761(10) 0.2500 0.3964(5) 0.040(2) Uani 1 2 d S
C5 C 0.8649(11) 0.2500 0.3216(5) 0.048(2) Uani 1 2 d S
H5 H 0.9035 0.2500 0.2753 0.058 Uiso 1 2 calc SR
C6 C 0.7144(11) 0.2500 0.3050(5) 0.049(2) Uani 1 2 d S
C7 C 0.6251(10) 0.2500 0.2210(6) 0.046(2) Uani 1 2 d S
N1 N 0.5477(8) 0.2500 0.1580(4) 0.054(2) Uani 1 2 d S
C8 C 0.6343(10) 0.2500 0.3655(5) 0.053(2) Uani 1 2 d S
N2 N 0.5627(10) 0.2500 0.4137(5) 0.088(3) Uani 1 2 d S
C9 C 1.2015(8) 0.2500 0.6246(4) 0.0301(18) Uani 1 2 d S
H9 H 1.3085 0.2500 0.6407 0.036 Uiso 1 2 calc SR
C10 C 1.1362(8) 0.2500 0.6872(4) 0.0317(18) Uani 1 2 d S
C11 C 0.9794(9) 0.2500 0.6812(5) 0.0343(19) Uani 1 2 d S
H11 H 0.9103 0.2500 0.6290 0.041 Uiso 1 2 calc SR
C12 C 0.9262(9) 0.2500 0.7462(5) 0.040(2) Uani 1 2 d S
O1 O 1.0205(6) 0.2500 0.8235(3) 0.0428(14) Uani 1 2 d S
C13 C 1.1741(9) 0.2500 0.8336(4) 0.0339(18) Uani 1 2 d S
C14 C 1.2296(8) 0.2500 0.7704(4) 0.0329(19) Uani 1 2 d S
H14 H 1.3360 0.2500 0.7793 0.040 Uiso 1 2 calc SR
C15 C 0.7633(10) 0.2500 0.7490(5) 0.053(2) Uani 1 2 d S
C16 C 0.6595(10) 0.2500 0.6631(7) 0.095(4) Uani 1 2 d S
H16A H 0.5543 0.2500 0.6656 0.142 Uiso 1 2 calc SR
H16B H 0.6789 0.1328 0.6343 0.142 Uiso 0.50 1 calc PR
H16C H 0.6789 0.3672 0.6343 0.142 Uiso 0.50 1 calc PR
C17 C 0.7317(8) 0.4328(10) 0.7933(5) 0.083(2) Uani 1 1 d .
H17A H 0.6257 0.4336 0.7943 0.125 Uiso 1 1 calc R
H17B H 0.7530 0.5499 0.7650 0.125 Uiso 1 1 calc R
H17C H 0.7962 0.4324 0.8489 0.125 Uiso 1 1 calc R
C18 C 1.2544(9) 0.2500 0.9228(5) 0.047(2) Uani 1 2 d S
C19 C 1.2083(8) 0.4339(10) 0.9621(4) 0.072(2) Uani 1 1 d .
H19A H 1.2606 0.4358 1.0199 0.108 Uiso 1 1 calc R
H19B H 1.0992 0.4324 0.9555 0.108 Uiso 1 1 calc R
H19C H 1.2356 0.5509 0.9359 0.108 Uiso 1 1 calc R
C20 C 1.4227(9) 0.2500 0.9334(5) 0.048(2) Uani 1 2 d S
H20A H 1.4746 0.2500 0.9914 0.072 Uiso 1 2 calc SR
H20B H 1.4513 0.3672 0.9079 0.072 Uiso 0.50 1 calc PR
H20C H 1.4513 0.1328 0.9079 0.072 Uiso 0.50 1 calc PR
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'
S S 0.1246 0.1234 '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
C4 S1 C1 92.9(4) . .
C2 C1 C9 125.0(7) . .
C2 C1 S1 110.0(6) . .
C9 C1 S1 125.0(6) . .
C3 C2 C1 113.7(8) . .
C3 C2 H2 123.1 . .
C1 C2 H2 123.1 . .
C2 C3 C4 113.3(7) . .
C2 C3 H3 123.4 . .
C4 C3 H3 123.4 . .
C3 C4 C5 123.0(8) . .
C3 C4 S1 110.1(6) . .
C5 C4 S1 126.9(7) . .
C6 C5 C4 131.0(9) . .
C6 C5 H5 114.5 . .
C4 C5 H5 114.5 . .
C5 C6 C8 123.4(9) . .
C5 C6 C7 119.7(8) . .
C8 C6 C7 116.9(8) . .
N1 C7 C6 175.3(10) . .
N2 C8 C6 177.6(10) . .
C10 C9 C1 131.4(7) . .
C10 C9 H9 114.3 . .
C1 C9 H9 114.3 . .
C9 C10 C11 126.5(7) . .
C9 C10 C14 120.0(7) . .
C11 C10 C14 113.4(6) . .
C12 C11 C10 122.1(8) . .
C12 C11 H11 119.0 . .
C10 C11 H11 119.0 . .
C11 C12 O1 121.8(7) . .
C11 C12 C15 127.8(8) . .
O1 C12 C15 110.4(7) . .
C13 O1 C12 119.1(6) . .
C14 C13 O1 120.3(7) . .
C14 C13 C18 129.8(7) . .
O1 C13 C18 109.9(6) . .
C13 C14 C10 123.3(7) . .
C13 C14 H14 118.4 . .
C10 C14 H14 118.4 . .
C12 C15 C17 109.6(5) . .
C12 C15 C17 109.6(5) . 4_565
C17 C15 C17 109.7(8) . 4_565
C12 C15 C16 110.1(7) . .
C17 C15 C16 108.9(5) . .
C17 C15 C16 108.9(5) 4_565 .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C13 C18 C20 109.6(6) . .
C13 C18 C19 108.9(5) . .
C20 C18 C19 109.9(5) . .
C13 C18 C19 108.9(5) . 4_565
C20 C18 C19 109.9(5) . 4_565
C19 C18 C19 109.7(7) . 4_565
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.719(8) .
S1 C1 1.733(8) .
C1 C2 1.389(10) .
C1 C9 1.426(10) .
C2 C3 1.388(10) .
C2 H2 0.9500 .
C3 C4 1.404(11) .
C3 H3 0.9500 .
C4 C5 1.413(11) .
C5 C6 1.337(11) .
C5 H5 0.9500 .
C6 C8 1.420(12) .
C6 C7 1.455(12) .
C7 N1 1.125(9) .
C8 N2 1.182(11) .
C9 C10 1.357(9) .
C9 H9 0.9500 .
C10 C11 1.419(10) .
C10 C14 1.457(10) .
C11 C12 1.327(10) .
C11 H11 0.9500 .
C12 O1 1.379(9) .
C12 C15 1.511(11) .
O1 C13 1.378(9) .
C13 C14 1.312(9) .
C13 C18 1.510(10) .
C14 H14 0.9500 .
C15 C17 1.527(7) .
C15 C17 1.527(7) 4_565
C15 C16 1.528(13) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C20 1.511(10) .
C18 C19 1.535(7) .
C18 C19 1.535(7) 4_565
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
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
C11 H11 S1 0.95 2.46 3.176(8) 132.3
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
_geom_torsion_site_symmetry_4
C4 S1 C1 C2 0.000(2) .
C4 S1 C1 C9 180.000(2) .
C9 C1 C2 C3 180.000(3) .
S1 C1 C2 C3 0.000(3) .
C1 C2 C3 C4 0.000(2) .
C2 C3 C4 C5 180.000(3) .
C2 C3 C4 S1 0.000(2) .
C1 S1 C4 C3 0.000(2) .
C1 S1 C4 C5 180.000(2) .
C3 C4 C5 C6 180.000(2) .
S1 C4 C5 C6 0.000(3) .
C4 C5 C6 C8 0.000(3) .
C4 C5 C6 C7 180.000(2) .
C2 C1 C9 C10 180.000(4) .
S1 C1 C9 C10 0.000(4) .
C1 C9 C10 C11 0.000(4) .
C1 C9 C10 C14 180.000(4) .
C9 C10 C11 C12 180.000(4) .
C14 C10 C11 C12 0.000(4) .
C10 C11 C12 O1 0.000(4) .
C10 C11 C12 C15 180.000(4) .
C11 C12 O1 C13 0.000(4) .
C15 C12 O1 C13 180.000(4) .
C12 O1 C13 C14 0.000(5) .
C12 O1 C13 C18 180.000(4) .
O1 C13 C14 C10 0.000(5) .
C18 C13 C14 C10 180.000(4) .
C9 C10 C14 C13 180.000(4) .
C11 C10 C14 C13 0.000(4) .
C11 C12 C15 C17 -119.8(5) .
O1 C12 C15 C17 60.2(5) .
C11 C12 C15 C17 119.8(5) 4_565
O1 C12 C15 C17 -60.2(5) 4_565
C11 C12 C15 C16 0.000(5) .
O1 C12 C15 C16 180.000(4) .
C14 C13 C18 C20 0.000(5) .
O1 C13 C18 C20 180.000(4) .
C14 C13 C18 C19 120.2(5) .
O1 C13 C18 C19 -59.8(5) .
C14 C13 C18 C19 -120.2(5) 4_565
O1 C13 C18 C19 59.8(5) 4_565
