#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029212.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_4029212
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         'C27 H16 N4'
_chemical_formula_sum            'C27 H16 N4'
_chemical_formula_weight         396.44
_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                 105.625(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3440(6)
_cell_length_b                   9.3130(5)
_cell_length_c                   18.3365(9)
_cell_measurement_reflns_used    21757
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      29.68
_cell_measurement_theta_min      2.03
_cell_volume                     2030.06(18)
_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      253(2)
_diffrn_detector_area_resol_mean 32.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15034
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0399
_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)+(0.0518P)²+0.5600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                3256
_reflns_number_total             3579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4025978_si_003.cif
_cod_data_source_block           no_125
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029212.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029212
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
N1 N 0.26423(9) 0.49737(12) 0.05208(6) 0.0356(3) Uani 1 1 d .
N2 N 0.08957(9) 0.42653(12) 0.11838(7) 0.0382(3) Uani 1 1 d .
N3 N 0.18615(14) -0.55338(17) 0.36513(11) 0.0741(5) Uani 1 1 d .
N4 N 0.46418(9) 0.31490(13) 0.09651(7) 0.0382(3) Uani 1 1 d .
C1 C 0.26228(11) 0.37195(14) 0.08526(7) 0.0330(3) Uani 1 1 d .
C2 C 0.17220(11) 0.33612(15) 0.11844(8) 0.0353(3) Uani 1 1 d .
C3 C 0.09107(11) 0.55549(15) 0.08388(8) 0.0356(3) Uani 1 1 d .
C4 C 0.17838(11) 0.59080(14) 0.05038(7) 0.0347(3) Uani 1 1 d .
C5 C 0.17628(13) 0.72532(16) 0.01464(9) 0.0448(4) Uani 1 1 d .
H5A H 0.2332 0.7502 -0.0075 0.054 Uiso 1 1 calc R
C6 C 0.09024(14) 0.81899(17) 0.01260(9) 0.0514(4) Uani 1 1 d .
H6A H 0.0885 0.9070 -0.0117 0.062 Uiso 1 1 calc R
C7 C 0.00445(14) 0.78425(17) 0.04662(10) 0.0512(4) Uani 1 1 d .
H7A H -0.0528 0.8499 0.0452 0.061 Uiso 1 1 calc R
C8 C 0.00423(12) 0.65567(16) 0.08155(9) 0.0449(4) Uani 1 1 d .
H8A H -0.0530 0.6336 0.1039 0.054 Uiso 1 1 calc R
C9 C 0.16907(11) 0.19958(16) 0.15410(8) 0.0400(3) Uani 1 1 d .
C10 C 0.16848(12) 0.08589(16) 0.18454(8) 0.0406(3) Uani 1 1 d .
C11 C 0.17143(11) -0.05045(15) 0.22119(8) 0.0364(3) Uani 1 1 d .
C12 C 0.09899(12) -0.07902(16) 0.26595(9) 0.0430(3) Uani 1 1 d .
H12A H 0.0480 -0.0093 0.2717 0.052 Uiso 1 1 calc R
C13 C 0.10216(12) -0.20944(16) 0.30168(9) 0.0434(4) Uani 1 1 d .
H13A H 0.0540 -0.2274 0.3319 0.052 Uiso 1 1 calc R
C14 C 0.17741(11) -0.31412(15) 0.29249(8) 0.0383(3) Uani 1 1 d .
C15 C 0.24959(12) -0.28727(16) 0.24740(8) 0.0411(3) Uani 1 1 d .
H15A H 0.2994 -0.3579 0.2408 0.049 Uiso 1 1 calc R
C16 C 0.24721(11) -0.15602(16) 0.21253(8) 0.0401(3) Uani 1 1 d .
H16A H 0.2963 -0.1376 0.1831 0.048 Uiso 1 1 calc R
C17 C 0.18222(13) -0.44849(17) 0.33203(10) 0.0489(4) Uani 1 1 d .
C18 C 0.35382(11) 0.27043(15) 0.08778(8) 0.0363(3) Uani 1 1 d .
C19 C 0.34971(14) 0.12565(16) 0.07365(9) 0.0467(4) Uani 1 1 d .
H19A H 0.2861 0.0678 0.0654 0.056 Uiso 1 1 calc R
C20 C 0.45799(15) 0.07998(18) 0.07377(9) 0.0544(4) Uani 1 1 d .
H20A H 0.4792 -0.0132 0.0656 0.065 Uiso 1 1 calc R
C21 C 0.52608(14) 0.19686(18) 0.08810(9) 0.0494(4) Uani 1 1 d .
H21A H 0.6027 0.1969 0.0916 0.059 Uiso 1 1 calc R
C22 C 0.51247(11) 0.45155(15) 0.12254(8) 0.0369(3) Uani 1 1 d .
C23 C 0.48869(11) 0.51657(16) 0.18466(8) 0.0399(3) Uani 1 1 d .
H23A H 0.4413 0.4715 0.2093 0.048 Uiso 1 1 calc R
C24 C 0.53570(13) 0.64854(18) 0.20968(9) 0.0481(4) Uani 1 1 d .
H24A H 0.5191 0.6929 0.2508 0.058 Uiso 1 1 calc R
C25 C 0.60737(14) 0.71464(19) 0.17354(10) 0.0547(4) Uani 1 1 d .
H25A H 0.6382 0.8039 0.1899 0.066 Uiso 1 1 calc R
C26 C 0.63296(13) 0.6478(2) 0.11319(9) 0.0556(4) Uani 1 1 d .
H26A H 0.6823 0.6915 0.0896 0.067 Uiso 1 1 calc R
C27 C 0.58580(12) 0.51608(18) 0.08729(8) 0.0465(4) Uani 1 1 d .
H27A H 0.6033 0.4714 0.0465 0.056 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C4 117.65(11)
C2 N2 C3 117.10(11)
C21 N4 C18 107.85(13)
C21 N4 C22 123.76(12)
C18 N4 C22 127.58(11)
N1 C1 C2 120.71(12)
N1 C1 C18 118.43(11)
C2 C1 C18 120.86(12)
N2 C2 C9 116.68(12)
N2 C2 C1 122.29(12)
C9 C2 C1 121.02(12)
N2 C3 C8 119.47(12)
N2 C3 C4 120.96(12)
C8 C3 C4 119.57(13)
N1 C4 C5 119.58(12)
N1 C4 C3 121.27(12)
C5 C4 C3 119.15(13)
C6 C5 C4 119.75(14)
C6 C5 H5A 120.1
C4 C5 H5A 120.1
C5 C6 C7 120.95(14)
C5 C6 H6A 119.5
C7 C6 H6A 119.5
C8 C7 C6 120.67(14)
C8 C7 H7A 119.7
C6 C7 H7A 119.7
C7 C8 C3 119.90(14)
C7 C8 H8A 120.0
C3 C8 H8A 120.0
C10 C9 C2 178.81(16)
C9 C10 C11 178.23(15)
C12 C11 C16 119.28(13)
C12 C11 C10 120.44(13)
C16 C11 C10 120.28(12)
C13 C12 C11 120.60(13)
C13 C12 H12A 119.7
C11 C12 H12A 119.7
C12 C13 C14 119.76(13)
C12 C13 H13A 120.1
C14 C13 H13A 120.1
C13 C14 C15 120.17(13)
C13 C14 C17 119.18(13)
C15 C14 C17 120.61(13)
C16 C15 C14 119.91(13)
C16 C15 H15A 120.0
C14 C15 H15A 120.0
C15 C16 C11 120.27(12)
C15 C16 H16A 119.9
C11 C16 H16A 119.9
N3 C17 C14 178.23(19)
C19 C18 N4 107.44(12)
C19 C18 C1 129.78(13)
N4 C18 C1 122.32(12)
C18 C19 C20 108.13(14)
C18 C19 H19A 125.9
C20 C19 H19A 125.9
C21 C20 C19 107.31(14)
C21 C20 H20A 126.3
C19 C20 H20A 126.3
C20 C21 N4 109.27(14)
C20 C21 H21A 125.4
N4 C21 H21A 125.4
C27 C22 C23 120.20(14)
C27 C22 N4 119.76(13)
C23 C22 N4 120.00(12)
C24 C23 C22 119.78(13)
C24 C23 H23A 120.1
C22 C23 H23A 120.1
C23 C24 C25 120.09(15)
C23 C24 H24A 120.0
C25 C24 H24A 120.0
C26 C25 C24 119.85(16)
C26 C25 H25A 120.1
C24 C25 H25A 120.1
C25 C26 C27 120.59(15)
C25 C26 H26A 119.7
C27 C26 H26A 119.7
C22 C27 C26 119.45(14)
C22 C27 H27A 120.3
C26 C27 H27A 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3202(17)
N1 C4 1.3650(17)
N2 C2 1.3224(18)
N2 C3 1.3599(18)
N3 C17 1.144(2)
N4 C21 1.3710(18)
N4 C18 1.3913(18)
N4 C22 1.4315(19)
C1 C2 1.4430(18)
C1 C18 1.4645(18)
C2 C9 1.4352(19)
C3 C8 1.4130(19)
C3 C4 1.4155(19)
C4 C5 1.4109(19)
C5 C6 1.367(2)
C5 H5A 0.9300
C6 C7 1.404(2)
C6 H6A 0.9300
C7 C8 1.358(2)
C7 H7A 0.9300
C8 H8A 0.9300
C9 C10 1.198(2)
C10 C11 1.4325(19)
C11 C12 1.393(2)
C11 C16 1.395(2)
C12 C13 1.376(2)
C12 H12A 0.9300
C13 C14 1.388(2)
C13 H13A 0.9300
C14 C15 1.392(2)
C14 C17 1.439(2)
C15 C16 1.376(2)
C15 H15A 0.9300
C16 H16A 0.9300
C18 C19 1.371(2)
C19 C20 1.402(2)
C19 H19A 0.9300
C20 C21 1.357(2)
C20 H20A 0.9300
C21 H21A 0.9300
C22 C27 1.383(2)
C22 C23 1.389(2)
C23 C24 1.384(2)
C23 H23A 0.9300
C24 C25 1.384(2)
C24 H24A 0.9300
C25 C26 1.378(2)
C25 H25A 0.9300
C26 C27 1.386(2)
C26 H26A 0.9300
C27 H27A 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
C4 N1 C1 C2 -0.06(18)
C4 N1 C1 C18 -179.87(12)
C3 N2 C2 C9 -179.19(12)
C3 N2 C2 C1 1.45(19)
N1 C1 C2 N2 -1.1(2)
C18 C1 C2 N2 178.65(12)
N1 C1 C2 C9 179.53(12)
C18 C1 C2 C9 -0.7(2)
C2 N2 C3 C8 179.43(13)
C2 N2 C3 C4 -0.65(19)
C1 N1 C4 C5 -179.18(12)
C1 N1 C4 C3 0.84(19)
N2 C3 C4 N1 -0.5(2)
C8 C3 C4 N1 179.41(13)
N2 C3 C4 C5 179.51(13)
C8 C3 C4 C5 -0.6(2)
N1 C4 C5 C6 179.78(14)
C3 C4 C5 C6 -0.2(2)
C4 C5 C6 C7 1.0(2)
C5 C6 C7 C8 -0.9(3)
C6 C7 C8 C3 0.0(2)
N2 C3 C8 C7 -179.41(14)
C4 C3 C8 C7 0.7(2)
C16 C11 C12 C13 0.3(2)
C10 C11 C12 C13 -179.52(14)
C11 C12 C13 C14 -0.6(2)
C12 C13 C14 C15 0.1(2)
C12 C13 C14 C17 178.13(14)
C13 C14 C15 C16 0.7(2)
C17 C14 C15 C16 -177.26(14)
C14 C15 C16 C11 -1.0(2)
C12 C11 C16 C15 0.5(2)
C10 C11 C16 C15 -179.63(13)
C21 N4 C18 C19 -0.37(16)
C22 N4 C18 C19 -170.24(13)
C21 N4 C18 C1 -173.32(12)
C22 N4 C18 C1 16.8(2)
N1 C1 C18 C19 -135.57(16)
C2 C1 C18 C19 44.6(2)
N1 C1 C18 N4 35.67(18)
C2 C1 C18 N4 -144.13(13)
N4 C18 C19 C20 0.13(17)
C1 C18 C19 C20 172.37(14)
C18 C19 C20 C21 0.17(18)
C19 C20 C21 N4 -0.40(18)
C18 N4 C21 C20 0.48(17)
C22 N4 C21 C20 170.83(13)
C21 N4 C22 C27 52.96(19)
C18 N4 C22 C27 -138.66(15)
C21 N4 C22 C23 -124.82(15)
C18 N4 C22 C23 43.6(2)
C27 C22 C23 C24 2.1(2)
N4 C22 C23 C24 179.90(13)
C22 C23 C24 C25 -0.9(2)
C23 C24 C25 C26 -0.8(3)
C24 C25 C26 C27 1.3(3)
C23 C22 C27 C26 -1.7(2)
N4 C22 C27 C26 -179.47(13)
C25 C26 C27 C22 0.0(2)
