#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029214.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_4029214
loop_
_publ_author_name
'Gers, Charlotte F'
'Nordmann, Jan'
'Kumru, Ceyda'
'Frank, Walter'
'Müller, Thomas J J'
_publ_section_title
;
 Solvatochromic fluorescent 2-substituted 3-ethynyl quinoxalines:
 four-component synthesis, photophysical properties, and electronic
 structure.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3296
_journal_page_last               3310
_journal_paper_doi               10.1021/jo4025978
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C21 H14 N2 O S'
_chemical_formula_sum            'C21 H14 N2 O S'
_chemical_formula_weight         342.41
_chemical_name_systematic
; 
 ? 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.929(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0463(5)
_cell_length_b                   17.4093(6)
_cell_length_c                   9.5507(5)
_cell_measurement_reflns_used    21946
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      1.97
_cell_volume                     1715.50(14)
_computing_cell_refinement
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_data_collection
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_data_reduction
;
CrysAlis PRO, Ver.1.171.33.52 (Oxford Diffraction Ltd., 2009)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 16.2711
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_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  0.1244
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12707
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1646
_reflns_number_gt                2783
_reflns_number_total             3012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4025978_si_004.cif
_cod_data_source_block           no_181
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029214.cif.
;
_cod_original_cell_volume        1715.50(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029214
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
S1 S 0.18177(5) 0.59465(3) 0.19233(7) 0.0695(3) Uani 1 1 d .
O1 O 0.14426(19) 0.64529(12) 0.4304(2) 0.0909(6) Uani 1 1 d .
C1 C 0.33979(19) 0.58944(11) 0.0304(2) 0.0582(5) Uani 1 1 d .
N1 N 0.24318(16) 0.54609(10) -0.0563(2) 0.0628(5) Uani 1 1 d .
N2 N 0.46033(17) 0.57443(11) -0.1357(2) 0.0655(5) Uani 1 1 d .
C10 C 0.4009(2) 0.66209(15) 0.2836(3) 0.0732(6) Uani 1 1 d .
H10 H 0.4822 0.6800 0.2908 0.088 Uiso 1 1 calc R
C2 C 0.4493(2) 0.60483(12) -0.0151(2) 0.0593(5) Uani 1 1 d .
C16 C 0.72639(19) 0.76012(12) 0.2027(2) 0.0568(5) Uani 1 1 d .
C14 C 0.55060(19) 0.65674(13) 0.0676(3) 0.0632(5) Uani 1 1 d .
C3 C 0.3619(2) 0.52840(12) -0.2218(2) 0.0643(5) Uani 1 1 d .
C17 C 0.8539(2) 0.75621(16) 0.2089(3) 0.0782(7) Uani 1 1 d .
H17 H 0.8819 0.7155 0.1652 0.094 Uiso 1 1 calc R
C21 C 0.6882(2) 0.82087(14) 0.2708(3) 0.0685(6) Uani 1 1 d .
H21 H 0.6034 0.8234 0.2683 0.082 Uiso 1 1 calc R
C19 C 0.8991(3) 0.87448(17) 0.3470(3) 0.0856(8) Uani 1 1 d .
H19 H 0.9571 0.9133 0.3945 0.103 Uiso 1 1 calc R
C15 C 0.6333(2) 0.70220(12) 0.1276(3) 0.0617(5) Uani 1 1 d .
C9 C 0.32495(19) 0.61826(12) 0.1657(2) 0.0600(5) Uani 1 1 d .
C18 C 0.9388(2) 0.8148(2) 0.2824(4) 0.0920(9) Uani 1 1 d .
H18 H 1.0244 0.8130 0.2873 0.110 Uiso 1 1 calc R
C4 C 0.2519(2) 0.51548(12) -0.1825(2) 0.0625(5) Uani 1 1 d .
C12 C 0.2288(2) 0.64501(13) 0.3581(3) 0.0662(6) Uani 1 1 d .
C13 C 0.1818(4) 0.6888(2) 0.5656(4) 0.1017(10) Uani 1 1 d .
H13A H 0.1809 0.7425 0.5424 0.153 Uiso 1 1 calc R
H13B H 0.2675 0.6740 0.6293 0.153 Uiso 1 1 calc R
H13C H 0.1222 0.6792 0.6162 0.153 Uiso 1 1 calc R
C20 C 0.7750(3) 0.87756(16) 0.3422(3) 0.0829(7) Uani 1 1 d .
H20 H 0.7485 0.9182 0.3875 0.100 Uiso 1 1 calc R
C8 C 0.3692(3) 0.49486(16) -0.3527(3) 0.0791(7) Uani 1 1 d .
H8 H 0.4420 0.5024 -0.3785 0.095 Uiso 1 1 calc R
C7 C 0.2683(3) 0.45114(17) -0.4416(3) 0.0901(8) Uani 1 1 d .
H7 H 0.2723 0.4293 -0.5287 0.108 Uiso 1 1 calc R
C5 C 0.1496(2) 0.47028(16) -0.2778(3) 0.0811(7) Uani 1 1 d .
H5 H 0.0756 0.4621 -0.2546 0.097 Uiso 1 1 calc R
C6 C 0.1592(3) 0.43889(18) -0.4031(3) 0.0905(8) Uani 1 1 d .
H6 H 0.0919 0.4086 -0.4647 0.109 Uiso 1 1 calc R
C11 C 0.3464(2) 0.67780(15) 0.3926(3) 0.0741(6) Uani 1 1 d .
H11 H 0.3864 0.7072 0.4780 0.089 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'
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
C12 S1 C9 91.31(11)
C12 O1 C13 115.9(2)
N1 C1 C9 115.53(19)
N1 C1 C2 119.3(2)
C9 C1 C2 125.17(18)
C1 N1 C4 118.84(19)
C2 N2 C3 117.50(19)
C9 C10 C11 114.8(2)
C9 C10 H10 122.6
C11 C10 H10 122.6
N2 C2 C14 116.00(19)
N2 C2 C1 122.55(19)
C14 C2 C1 121.4(2)
C21 C16 C17 119.4(2)
C21 C16 C15 119.15(19)
C17 C16 C15 121.4(2)
C15 C14 C2 175.7(2)
N2 C3 C8 119.5(2)
N2 C3 C4 120.6(2)
C8 C3 C4 119.9(2)
C18 C17 C16 118.4(3)
C18 C17 H17 120.8
C16 C17 H17 120.8
C20 C21 C16 120.4(2)
C20 C21 H21 119.8
C16 C21 H21 119.8
C20 C19 C18 120.1(2)
C20 C19 H19 119.9
C18 C19 H19 119.9
C14 C15 C16 176.0(2)
C10 C9 C1 134.0(2)
C10 C9 S1 109.45(18)
C1 C9 S1 116.56(15)
C19 C18 C17 121.3(2)
C19 C18 H18 119.3
C17 C18 H18 119.3
N1 C4 C5 119.9(2)
N1 C4 C3 121.09(19)
C5 C4 C3 119.0(2)
O1 C12 C11 131.2(2)
O1 C12 S1 115.98(17)
C11 C12 S1 112.86(19)
O1 C13 H13A 109.5
O1 C13 H13B 109.5
H13A C13 H13B 109.5
O1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C19 C20 C21 120.4(3)
C19 C20 H20 119.8
C21 C20 H20 119.8
C7 C8 C3 119.3(3)
C7 C8 H8 120.4
C3 C8 H8 120.4
C8 C7 C6 120.8(3)
C8 C7 H7 119.6
C6 C7 H7 119.6
C6 C5 C4 119.8(3)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C7 121.3(3)
C5 C6 H6 119.4
C7 C6 H6 119.4
C12 C11 C10 111.6(2)
C12 C11 H11 124.2
C10 C11 H11 124.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.720(2)
S1 C9 1.738(2)
O1 C12 1.345(3)
O1 C13 1.425(3)
C1 N1 1.328(3)
C1 C9 1.449(3)
C1 C2 1.449(3)
N1 C4 1.352(3)
N2 C2 1.313(3)
N2 C3 1.365(3)
C10 C9 1.371(3)
C10 C11 1.403(4)
C10 H10 0.9300
C2 C14 1.436(3)
C16 C21 1.384(3)
C16 C17 1.390(3)
C16 C15 1.436(3)
C14 C15 1.190(3)
C3 C8 1.408(3)
C3 C4 1.412(3)
C17 C18 1.393(4)
C17 H17 0.9300
C21 C20 1.375(3)
C21 H21 0.9300
C19 C20 1.356(4)
C19 C18 1.359(4)
C19 H19 0.9300
C18 H18 0.9300
C4 C5 1.411(3)
C12 C11 1.348(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C20 H20 0.9300
C8 C7 1.366(4)
C8 H8 0.9300
C7 C6 1.395(5)
C7 H7 0.9300
C5 C6 1.354(4)
C5 H5 0.9300
C6 H6 0.9300
C11 H11 0.9300
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
C9 C1 N1 C4 -178.27(18)
C2 C1 N1 C4 2.1(3)
C3 N2 C2 C14 -176.23(19)
C3 N2 C2 C1 1.8(3)
N1 C1 C2 N2 -3.5(3)
C9 C1 C2 N2 176.93(19)
N1 C1 C2 C14 174.44(19)
C9 C1 C2 C14 -5.1(3)
C2 N2 C3 C8 179.7(2)
C2 N2 C3 C4 1.0(3)
C21 C16 C17 C18 -1.0(4)
C15 C16 C17 C18 179.4(2)
C17 C16 C21 C20 1.0(4)
C15 C16 C21 C20 -179.4(2)
C11 C10 C9 C1 179.1(2)
C11 C10 C9 S1 -0.8(3)
N1 C1 C9 C10 178.3(2)
C2 C1 C9 C10 -2.1(4)
N1 C1 C9 S1 -1.9(2)
C2 C1 C9 S1 177.70(16)
C12 S1 C9 C10 0.58(18)
C12 S1 C9 C1 -179.30(17)
C20 C19 C18 C17 0.7(4)
C16 C17 C18 C19 0.1(4)
C1 N1 C4 C5 -178.9(2)
C1 N1 C4 C3 0.6(3)
N2 C3 C4 N1 -2.3(3)
C8 C3 C4 N1 179.0(2)
N2 C3 C4 C5 177.2(2)
C8 C3 C4 C5 -1.4(3)
C13 O1 C12 C11 1.7(4)
C13 O1 C12 S1 -178.3(2)
C9 S1 C12 O1 179.74(19)
C9 S1 C12 C11 -0.2(2)
C18 C19 C20 C21 -0.7(4)
C16 C21 C20 C19 -0.1(4)
N2 C3 C8 C7 -177.6(2)
C4 C3 C8 C7 1.1(4)
C3 C8 C7 C6 -0.7(4)
N1 C4 C5 C6 -179.2(2)
C3 C4 C5 C6 1.3(4)
C4 C5 C6 C7 -0.9(4)
C8 C7 C6 C5 0.6(5)
O1 C12 C11 C10 179.9(3)
S1 C12 C11 C10 -0.2(3)
C9 C10 C11 C12 0.6(3)
