#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151927.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_7151927
loop_
_publ_author_name
'Gemma, Sandra'
'Colombo, Laura'
'Forloni, Gianluigi'
'Savini, Luisa'
'Fracasso, Claudia'
'Caccia, Silvio'
'Salmona, Mario'
'Brindisi, Margherita'
'Joshi, Bhupendra P.'
'Tripaldi, Pierangela'
'Giorgi, Gianluca'
'Taglialatela-Scafati, Orazio'
'Novellino, Ettore'
'Fiorini, Isabella'
'Campiani, Giuseppe'
'Butini, Stefania'
_publ_section_title
;
 Pyrroloquinoxaline hydrazones as fluorescent probes for amyloid
 fibrils.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5137
_journal_page_last               5148
_journal_paper_doi               10.1039/c1ob05288h
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C22 H17 N5 O, H2 O'
_chemical_formula_sum            'C22 H19 N5 O2'
_chemical_formula_weight         385.42
_chemical_name_systematic
;
N-(7-Methoxy-5H-pyrrolo[1,2-a]quinoxalin-4-ylidene)-N'-quinolin-
4-ylmethylene-hydrazine hydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8025(2)
_cell_length_b                   11.5872(8)
_cell_length_c                   33.050(2)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.91
_cell_volume                     1839.15(19)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            28594
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   'area detector absorption correction'
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lath
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    geom
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0573
_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)+(0.0305P)²+0.5698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2768
_reflns_number_total             4048
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05288h.txt
_cod_data_source_block           polymorph1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1839.17(19)
_cod_database_code               7151927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2590(5) 0.58730(19) -0.13252(7) 0.0352(6) Uani 1 1 d . . .
H1 H 0.2369 0.6012 -0.1065 0.026(7) Uiso 1 1 calc R . .
C2 C 0.4293(6) 0.6581(2) -0.15388(8) 0.0353(7) Uani 1 1 d . . .
C3 C 0.4824(6) 0.6262(2) -0.19518(8) 0.0368(7) Uani 1 1 d . . .
C4 C 0.6662(6) 0.6682(3) -0.22356(8) 0.0415(7) Uani 1 1 d . . .
H4 H 0.7926 0.7304 -0.2200 0.046(8) Uiso 1 1 calc R . .
C5 C 0.6323(6) 0.6019(3) -0.25872(9) 0.0436(8) Uani 1 1 d . . .
H5 H 0.7328 0.6111 -0.2833 0.039(8) Uiso 1 1 calc R . .
C6 C 0.4285(6) 0.5216(3) -0.25147(8) 0.0414(8) Uani 1 1 d . . .
H6 H 0.3623 0.4658 -0.2702 0.053(9) Uiso 1 1 calc R . .
N7 N 0.3377(5) 0.53605(19) -0.21278(7) 0.0366(6) Uani 1 1 d . . .
C8 C 0.1464(6) 0.4694(2) -0.19048(8) 0.0369(7) Uani 1 1 d . . .
C9 C -0.0090(6) 0.3813(2) -0.20788(9) 0.0394(7) Uani 1 1 d . . .
H9 H 0.0041 0.3677 -0.2362 0.034(7) Uiso 1 1 calc R . .
C10 C -0.1828(6) 0.3133(2) -0.18452(8) 0.0369(7) Uani 1 1 d . . .
H10 H -0.2886 0.2533 -0.1966 0.045(8) Uiso 1 1 calc R . .
C11 C -0.2011(6) 0.3335(3) -0.14319(8) 0.0367(7) Uani 1 1 d . . .
C12 C -0.0571(6) 0.4249(2) -0.12590(8) 0.0358(7) Uani 1 1 d . . .
H12 H -0.0771 0.4406 -0.0978 0.031(7) Uiso 1 1 calc R . .
C13 C 0.1154(6) 0.4931(2) -0.14940(8) 0.0341(7) Uani 1 1 d . . .
O14 O -0.3569(4) 0.26862(17) -0.11685(5) 0.0436(5) Uani 1 1 d . . .
N15 N 0.5513(5) 0.75310(19) -0.14020(6) 0.0384(6) Uani 1 1 d . . .
C15 C -0.5125(7) 0.1752(3) -0.13397(9) 0.0501(8) Uani 1 1 d . . .
H15A H -0.6540 0.2059 -0.1524 0.080(13) Uiso 1 1 calc R . .
H15B H -0.6034 0.1316 -0.1123 0.047(8) Uiso 1 1 calc R . .
H15C H -0.3865 0.1242 -0.1489 0.051(9) Uiso 1 1 calc R . .
N16 N 0.4968(5) 0.77293(19) -0.09944(6) 0.0354(6) Uani 1 1 d . . .
C17 C 0.6126(6) 0.8659(2) -0.08619(8) 0.0375(7) Uani 1 1 d . . .
H17 H 0.7111 0.9142 -0.1045 0.033(7) Uiso 1 1 calc R . .
C18 C 0.5949(6) 0.8984(2) -0.04353(8) 0.0316(6) Uani 1 1 d . . .
C19 C 0.7763(6) 0.9833(2) -0.02624(8) 0.0322(7) Uani 1 1 d . . .
C20 C 0.9662(6) 1.0516(2) -0.04879(9) 0.0372(7) Uani 1 1 d . . .
H20 H 0.9751 1.0431 -0.0774 0.032(7) Uiso 1 1 calc R . .
C21 C 1.1369(6) 1.1295(2) -0.02994(9) 0.0375(7) Uani 1 1 d . . .
H21 H 1.2620 1.1750 -0.0455 0.055(9) Uiso 1 1 calc R . .
C22 C 1.1275(6) 1.1423(2) 0.01221(9) 0.0383(7) Uani 1 1 d . . .
H22 H 1.2477 1.1961 0.0251 0.053(9) Uiso 1 1 calc R . .
C23 C 0.9484(6) 1.0785(2) 0.03487(9) 0.0363(7) Uani 1 1 d . . .
H23 H 0.9442 1.0882 0.0634 0.033(7) Uiso 1 1 calc R . .
C24 C 0.7679(6) 0.9978(2) 0.01628(8) 0.0313(6) Uani 1 1 d . . .
N25 N 0.5891(5) 0.93830(18) 0.04112(7) 0.0341(6) Uani 1 1 d . . .
C26 C 0.4107(6) 0.8693(2) 0.02342(8) 0.0357(7) Uani 1 1 d . . .
H26 H 0.2749 0.8324 0.0399 0.030(7) Uiso 1 1 calc R . .
C27 C 0.4074(6) 0.8464(2) -0.01823(8) 0.0336(7) Uani 1 1 d . . .
H27 H 0.2738 0.7943 -0.0290 0.036(8) Uiso 1 1 calc R . .
OW O 1.0040(5) 0.89553(19) -0.17418(6) 0.0589(6) Uani 1 1 d . . .
H1OW H 0.8937 0.8246 -0.1627 0.18(2) Uiso 1 1 d R . .
H2OW H 1.2249 0.8803 -0.1669 0.16(2) Uiso 1 1 d 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C13 124.0(2) . . ?
C2 N1 H1 118.0 . . ?
C13 N1 H1 118.0 . . ?
N15 C2 N1 126.2(2) . . ?
N15 C2 C3 117.3(2) . . ?
N1 C2 C3 116.4(3) . . ?
C4 C3 N7 107.6(2) . . ?
C4 C3 C2 132.1(3) . . ?
N7 C3 C2 120.3(3) . . ?
C3 C4 C5 107.3(3) . . ?
C3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
C6 C5 C4 108.0(3) . . ?
C6 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
N7 C6 C5 108.0(3) . . ?
N7 C6 H6 126.0 . . ?
C5 C6 H6 126.0 . . ?
C6 N7 C3 109.1(2) . . ?
C6 N7 C8 129.3(2) . . ?
C3 N7 C8 121.5(2) . . ?
C9 C8 C13 119.4(3) . . ?
C9 C8 N7 122.5(3) . . ?
C13 C8 N7 118.1(3) . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
O14 C11 C12 115.4(2) . . ?
O14 C11 C10 124.4(3) . . ?
C12 C11 C10 120.2(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.9(3) . . ?
C12 C13 N1 120.9(2) . . ?
C8 C13 N1 119.2(3) . . ?
C11 O14 C15 116.6(2) . . ?
C2 N15 N16 112.6(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 N16 N15 112.7(2) . . ?
N16 C17 C18 121.2(3) . . ?
N16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C27 C18 C19 117.3(2) . . ?
C27 C18 C17 120.9(3) . . ?
C19 C18 C17 121.8(2) . . ?
C24 C19 C20 118.3(3) . . ?
C24 C19 C18 117.4(2) . . ?
C20 C19 C18 124.3(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
N25 C24 C23 117.1(2) . . ?
N25 C24 C19 123.4(2) . . ?
C23 C24 C19 119.5(3) . . ?
C26 N25 C24 116.7(2) . . ?
N25 C26 C27 124.1(3) . . ?
N25 C26 H26 117.9 . . ?
C27 C26 H26 117.9 . . ?
C18 C27 C26 120.6(3) . . ?
C18 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
H1OW OW H2OW 106.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.357(3) . ?
N1 C13 1.406(3) . ?
N1 H1 0.8800 . ?
C2 N15 1.326(3) . ?
C2 C3 1.437(4) . ?
C3 C4 1.377(4) . ?
C3 N7 1.383(3) . ?
C4 C5 1.402(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9500 . ?
C6 N7 1.361(3) . ?
C6 H6 0.9500 . ?
N7 C8 1.408(3) . ?
C8 C9 1.389(4) . ?
C8 C13 1.393(3) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 O14 1.373(3) . ?
C11 C12 1.387(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
O14 C15 1.432(3) . ?
N15 N16 1.391(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N16 C17 1.289(3) . ?
C17 C18 1.462(3) . ?
C17 H17 0.9500 . ?
C18 C27 1.369(4) . ?
C18 C19 1.433(4) . ?
C19 C24 1.416(3) . ?
C19 C20 1.419(4) . ?
C20 C21 1.370(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.402(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.359(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.415(4) . ?
C23 H23 0.9500 . ?
C24 N25 1.374(3) . ?
N25 C26 1.310(3) . ?
C26 C27 1.402(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
OW H1OW 1.0492 . ?
OW H2OW 1.1022 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C2 N15 174.2(2) . . . . ?
C13 N1 C2 C3 -6.0(4) . . . . ?
N15 C2 C3 C4 8.9(5) . . . . ?
N1 C2 C3 C4 -170.8(3) . . . . ?
N15 C2 C3 N7 -172.6(2) . . . . ?
N1 C2 C3 N7 7.7(4) . . . . ?
N7 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 178.4(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 N7 -0.4(3) . . . . ?
C5 C6 N7 C3 0.3(3) . . . . ?
C5 C6 N7 C8 -174.8(3) . . . . ?
C4 C3 N7 C6 -0.1(3) . . . . ?
C2 C3 N7 C6 -178.9(3) . . . . ?
C4 C3 N7 C8 175.5(2) . . . . ?
C2 C3 N7 C8 -3.3(4) . . . . ?
C6 N7 C8 C9 -7.9(4) . . . . ?
C3 N7 C8 C9 177.5(3) . . . . ?
C6 N7 C8 C13 171.6(3) . . . . ?
C3 N7 C8 C13 -3.0(4) . . . . ?
C13 C8 C9 C10 -3.4(4) . . . . ?
N7 C8 C9 C10 176.2(3) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 O14 -177.1(3) . . . . ?
C9 C10 C11 C12 3.2(4) . . . . ?
O14 C11 C12 C13 177.4(2) . . . . ?
C10 C11 C12 C13 -3.0(4) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C11 C12 C13 N1 178.8(2) . . . . ?
C9 C8 C13 C12 3.6(4) . . . . ?
N7 C8 C13 C12 -175.9(2) . . . . ?
C9 C8 C13 N1 -175.7(2) . . . . ?
N7 C8 C13 N1 4.7(4) . . . . ?
C2 N1 C13 C12 -179.4(3) . . . . ?
C2 N1 C13 C8 -0.1(4) . . . . ?
C12 C11 O14 C15 178.7(3) . . . . ?
C10 C11 O14 C15 -1.0(4) . . . . ?
N1 C2 N15 N16 2.6(4) . . . . ?
C3 C2 N15 N16 -177.1(2) . . . . ?
C2 N15 N16 C17 -179.3(2) . . . . ?
N15 N16 C17 C18 -176.2(2) . . . . ?
N16 C17 C18 C27 -14.5(4) . . . . ?
N16 C17 C18 C19 163.9(3) . . . . ?
C27 C18 C19 C24 6.6(4) . . . . ?
C17 C18 C19 C24 -171.9(2) . . . . ?
C27 C18 C19 C20 -174.7(2) . . . . ?
C17 C18 C19 C20 6.8(4) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C18 C19 C20 C21 -178.7(3) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 N25 -178.8(2) . . . . ?
C22 C23 C24 C19 0.4(4) . . . . ?
C20 C19 C24 N25 178.7(2) . . . . ?
C18 C19 C24 N25 -2.5(4) . . . . ?
C20 C19 C24 C23 -0.4(4) . . . . ?
C18 C19 C24 C23 178.4(2) . . . . ?
C23 C24 N25 C26 175.8(2) . . . . ?
C19 C24 N25 C26 -3.4(4) . . . . ?
C24 N25 C26 C27 5.3(4) . . . . ?
C19 C18 C27 C26 -5.1(4) . . . . ?
C17 C18 C27 C26 173.4(3) . . . . ?
N25 C26 C27 C18 -1.1(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653511
