# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
G.Campiani
; Dipartimento Farmaco Chimico Tecnologico
Universit\`a degli Studi di Siena
via Aldo Moro
I-53100 Siena
Italy
;
G.Giorgi
; Dipartimento di Chimica
Universit\`a degli Studi di Siena
Via Aldo Moro
I-53100 Siena
Italy
;
_publ_contact_author_address     
; Dipartimento di Chimica,
Universit\`a degli Studi di Siena
Via Aldo Moro
I-53100 Siena
Italy
;
_publ_contact_author_email       gianluca.giorgi@unisi.it
_publ_contact_author_fax         '+39 0577 234135'
_publ_contact_author_phone       '+39 0577 234137'

_publ_contact_author_name        'Gianluca Giorgi'

data_polymorph1
_database_code_depnum_ccdc_archive 'CCDC 612697'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
N-(7-Methoxy-5H-pyrrolo[1,2-a]quinoxalin-4-ylidene)-N'-quinolin-
4-ylmethylene-hydrazine hydrate
;
_chemical_formula_moiety         'C22 H17 N5 O, H2 O'
_chemical_formula_sum            'C22 H19 N5 O2'
_chemical_formula_weight         385.42

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   4.8025(2)
_cell_length_b                   11.5872(8)
_cell_length_c                   33.050(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1839.17(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2317
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.10

_exptl_crystal_description       Lath
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_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)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            28594
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         27.16
_reflns_number_total             4048
_reflns_number_gt                2768
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.5698P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    geom
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_number_reflns         4048
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0483(15) 0.0389(14) 0.0183(12) -0.0049(10) -0.0017(11) -0.0023(12)
C2 0.0427(18) 0.0371(17) 0.0262(15) -0.0011(12) -0.0006(13) 0.0022(14)
C3 0.0537(19) 0.0327(15) 0.0239(15) -0.0015(12) -0.0052(14) 0.0025(15)
C4 0.059(2) 0.0388(17) 0.0267(16) 0.0040(13) -0.0049(15) -0.0041(16)
C5 0.057(2) 0.0495(19) 0.0244(15) 0.0055(14) 0.0034(15) 0.0022(16)
C6 0.057(2) 0.0457(18) 0.0218(15) 0.0023(14) 0.0019(15) 0.0002(16)
N7 0.0521(15) 0.0361(13) 0.0215(12) -0.0020(11) -0.0009(12) -0.0005(12)
C8 0.0472(18) 0.0383(16) 0.0253(15) 0.0009(13) 0.0004(13) 0.0023(15)
C9 0.0530(19) 0.0401(17) 0.0252(16) -0.0046(13) -0.0030(14) 0.0059(16)
C10 0.0439(18) 0.0361(16) 0.0308(16) -0.0061(13) -0.0041(14) -0.0007(14)
C11 0.0360(17) 0.0436(17) 0.0305(16) -0.0042(14) 0.0014(13) -0.0004(14)
C12 0.0427(18) 0.0414(17) 0.0232(15) -0.0045(13) 0.0039(13) 0.0026(14)
C13 0.0392(17) 0.0376(17) 0.0253(15) -0.0059(12) -0.0027(13) 0.0029(14)
O14 0.0524(13) 0.0488(12) 0.0296(11) -0.0051(10) 0.0032(10) -0.0133(11)
N15 0.0535(16) 0.0387(14) 0.0230(12) -0.0008(10) -0.0015(11) -0.0038(13)
C15 0.057(2) 0.0550(19) 0.0386(18) -0.0059(16) 0.0069(18) -0.0196(18)
N16 0.0495(14) 0.0374(14) 0.0192(12) -0.0027(10) -0.0028(11) 0.0027(12)
C17 0.0497(18) 0.0350(16) 0.0278(15) 0.0058(13) -0.0005(14) -0.0026(15)
C18 0.0396(17) 0.0320(15) 0.0231(14) -0.0011(12) -0.0031(13) 0.0057(13)
C19 0.0351(16) 0.0323(16) 0.0292(15) -0.0007(12) -0.0009(12) 0.0063(13)
C20 0.0442(18) 0.0368(16) 0.0305(16) -0.0016(13) -0.0001(14) 0.0018(14)
C21 0.0405(17) 0.0345(16) 0.0376(17) -0.0015(14) 0.0038(14) 0.0003(14)
C22 0.0413(16) 0.0371(17) 0.0365(17) -0.0057(14) -0.0062(14) 0.0006(14)
C23 0.0435(18) 0.0380(16) 0.0274(16) -0.0039(13) -0.0025(14) 0.0066(14)
C24 0.0356(16) 0.0312(14) 0.0270(15) -0.0017(12) 0.0008(12) 0.0024(12)
N25 0.0366(14) 0.0370(13) 0.0287(13) -0.0030(11) 0.0003(11) 0.0027(11)
C26 0.0379(17) 0.0371(16) 0.0323(16) 0.0005(13) 0.0017(13) -0.0003(14)
C27 0.0414(17) 0.0317(16) 0.0277(15) -0.0024(12) -0.0051(13) -0.0004(13)
OW 0.0699(16) 0.0562(15) 0.0507(14) 0.0104(11) -0.0006(12) -0.0031(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048

data_polymorph2
_database_code_depnum_ccdc_archive 'CCDC 612698'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
N-(7-Methoxy-5H-pyrrolo[1,2-a]quinoxalin-4-ylidene)-N'-quinolin-4-ylmethylene-
-hydrazine hydrate with methanol
;

_chemical_formula_moiety         'C22 H17 N5 O, 0.208(O2), 0.584(O), 0.208(C2)'
_chemical_formula_sum            'C22.42 H17 N5 O2'
_chemical_formula_weight         388.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.252(3)
_cell_length_b                   9.3398(11)
_cell_length_c                   17.6282(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.784(5)
_cell_angle_gamma                90.00
_cell_volume                     3894.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3831

_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.10

_exptl_crystal_description       slab
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1620
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   'area detector absorption correction'
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            19860
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3420
_reflns_number_gt                2147
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^2^+11.4685P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    geom
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3420
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2440
_refine_ls_wR_factor_gt          0.2180
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28184(14) 0.5750(4) 0.04759(18) 0.0420(9) Uani 1 1 d . . .
H1 H 0.2664 0.6341 0.0757 0.060(15) Uiso 1 1 calc R . .
C2 C 0.33883(18) 0.5708(5) 0.0606(2) 0.0402(11) Uani 1 1 d . . .
C3 C 0.36368(18) 0.4759(5) 0.0135(2) 0.0436(11) Uani 1 1 d . . .
C4 C 0.4182(2) 0.4463(5) 0.0090(3) 0.0522(13) Uani 1 1 d . . .
H4 H 0.4513 0.4870 0.0408 0.043(12) Uiso 1 1 calc R . .
C5 C 0.4169(2) 0.3462(6) -0.0501(3) 0.0610(14) Uani 1 1 d . . .
H5 H 0.4488 0.3069 -0.0656 0.085(18) Uiso 1 1 calc R . .
C6 C 0.3614(2) 0.3147(6) -0.0817(3) 0.0548(13) Uani 1 1 d . . .
H6 H 0.3481 0.2494 -0.1230 0.056(13) Uiso 1 1 calc R . .
N7 N 0.32825(15) 0.3937(4) -0.04348(18) 0.0459(10) Uani 1 1 d . . .
C8 C 0.26925(19) 0.3966(5) -0.0537(2) 0.0412(11) Uani 1 1 d . . .
C9 C 0.2329(2) 0.3093(5) -0.1063(2) 0.0468(12) Uani 1 1 d . . .
H9 H 0.2482 0.2442 -0.1376 0.023(9) Uiso 1 1 calc R . .
C10 C 0.1758(2) 0.3154(5) -0.1139(2) 0.0472(12) Uani 1 1 d . . .
H10 H 0.1518 0.2530 -0.1491 0.054(13) Uiso 1 1 calc R . .
C11 C 0.15245(19) 0.4142(5) -0.0697(2) 0.0476(12) Uani 1 1 d . . .
C12 C 0.18791(18) 0.4990(5) -0.0160(2) 0.0446(11) Uani 1 1 d . . .
H12 H 0.1724 0.5632 0.0156 0.029(10) Uiso 1 1 calc R . .
C13 C 0.24609(18) 0.4914(5) -0.0076(2) 0.0411(11) Uani 1 1 d . . .
O14 O 0.09484(13) 0.4207(4) -0.08446(17) 0.0583(9) Uani 1 1 d . . .
C15 C 0.0704(2) 0.5190(7) -0.0385(3) 0.0670(16) Uani 1 1 d . . .
H15A H 0.0816 0.4917 0.0164 0.062(14) Uiso 1 1 calc R . .
H15B H 0.0291 0.5164 -0.0554 0.079(17) Uiso 1 1 calc R . .
H15C H 0.0840 0.6161 -0.0452 0.080(19) Uiso 1 1 calc R . .
N15 N 0.37274(15) 0.6497(4) 0.11368(19) 0.0455(10) Uani 1 1 d . . .
N16 N 0.34170(14) 0.7358(4) 0.15377(18) 0.0425(9) Uani 1 1 d . . .
C17 C 0.37095(18) 0.8252(5) 0.2006(2) 0.0451(11) Uani 1 1 d . . .
H17 H 0.4109 0.8277 0.2069 0.057(13) Uiso 1 1 calc R . .
C18 C 0.34344(17) 0.9239(5) 0.2447(2) 0.0407(11) Uani 1 1 d . . .
C19 C 0.37483(17) 1.0369(5) 0.2905(2) 0.0402(11) Uani 1 1 d . . .
C20 C 0.43299(18) 1.0599(5) 0.2972(2) 0.0486(12) Uani 1 1 d . . .
H20 H 0.4541 0.9964 0.2724 0.032(10) Uiso 1 1 calc R . .
C21 C 0.4595(2) 1.1741(6) 0.3395(3) 0.0600(14) Uani 1 1 d . . .
H21 H 0.4987 1.1897 0.3434 0.10(2) Uiso 1 1 calc R . .
C22 C 0.4289(2) 1.2677(6) 0.3769(3) 0.0613(14) Uani 1 1 d . . .
H22 H 0.4476 1.3461 0.4058 0.053(13) Uiso 1 1 calc R . .
C23 C 0.3727(2) 1.2478(6) 0.3723(3) 0.0559(13) Uani 1 1 d . . .
H23 H 0.3526 1.3121 0.3980 0.10(2) Uiso 1 1 calc R . .
C24 C 0.34423(17) 1.1316(5) 0.3293(2) 0.0427(11) Uani 1 1 d . . .
N25 N 0.28765(15) 1.1179(4) 0.32653(19) 0.0440(9) Uani 1 1 d . . .
C26 C 0.26074(18) 1.0138(5) 0.2824(2) 0.0416(11) Uani 1 1 d . . .
H26 H 0.2212 1.0050 0.2786 0.020(9) Uiso 1 1 calc R . .
C27 C 0.28621(17) 0.9160(5) 0.2408(2) 0.0374(10) Uani 1 1 d . . .
H27 H 0.2641 0.8443 0.2099 0.026(9) Uiso 1 1 calc R . .
CME C 0.0108(3) 0.0738(8) 0.2130(4) 0.096(3) Uani 0.416(9) 1 d P . 1
OME O 0.0108(3) 0.0738(8) 0.2130(4) 0.096(3) Uani 0.416(9) 1 d P . 1
OW O 0.4912(2) 0.6911(8) 0.1645(4) 0.075(3) Uani 0.584(9) 1 d P . 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.037(2) 0.057(2) 0.0340(19) -0.0051(18) 0.0127(16) -0.0016(18)
C2 0.041(3) 0.058(3) 0.025(2) 0.002(2) 0.0140(18) 0.001(2)
C3 0.042(3) 0.059(3) 0.031(2) 0.004(2) 0.0122(19) -0.005(2)
C4 0.042(3) 0.070(3) 0.049(3) -0.007(3) 0.021(2) -0.005(2)
C5 0.054(3) 0.084(4) 0.053(3) -0.013(3) 0.029(2) -0.002(3)
C6 0.062(3) 0.073(4) 0.037(2) -0.009(3) 0.025(2) -0.004(3)
N7 0.047(2) 0.065(3) 0.0299(18) -0.0014(18) 0.0172(16) -0.0005(19)
C8 0.051(3) 0.049(3) 0.025(2) 0.001(2) 0.0127(19) 0.001(2)
C9 0.064(3) 0.051(3) 0.029(2) 0.002(2) 0.016(2) 0.000(2)
C10 0.053(3) 0.056(3) 0.030(2) 0.000(2) 0.005(2) -0.011(2)
C11 0.044(3) 0.061(3) 0.036(2) 0.003(2) 0.006(2) -0.005(2)
C12 0.044(3) 0.058(3) 0.033(2) -0.001(2) 0.0103(19) -0.001(2)
C13 0.044(3) 0.052(3) 0.027(2) 0.006(2) 0.0074(18) -0.003(2)
O14 0.041(2) 0.082(3) 0.0495(19) -0.0046(18) 0.0055(15) -0.0101(17)
C15 0.041(3) 0.102(5) 0.056(3) -0.010(3) 0.006(2) -0.004(3)
N15 0.041(2) 0.064(3) 0.0347(19) -0.0058(19) 0.0160(16) -0.0016(19)
N16 0.039(2) 0.064(3) 0.0273(18) -0.0026(18) 0.0133(15) 0.0001(19)
C17 0.032(2) 0.070(3) 0.036(2) -0.005(2) 0.0131(18) 0.000(2)
C18 0.039(3) 0.063(3) 0.0217(19) 0.004(2) 0.0102(17) 0.003(2)
C19 0.038(2) 0.056(3) 0.027(2) 0.001(2) 0.0092(18) 0.000(2)
C20 0.039(3) 0.063(3) 0.046(3) -0.007(2) 0.015(2) 0.002(2)
C21 0.037(3) 0.080(4) 0.062(3) 0.001(3) 0.011(2) -0.006(3)
C22 0.050(3) 0.067(4) 0.068(3) -0.013(3) 0.015(3) -0.011(3)
C23 0.049(3) 0.064(3) 0.055(3) -0.013(3) 0.014(2) 0.001(3)
C24 0.036(3) 0.060(3) 0.033(2) 0.000(2) 0.0095(18) 0.000(2)
N25 0.038(2) 0.058(3) 0.0375(19) -0.0002(18) 0.0106(16) 0.0033(18)
C26 0.033(2) 0.059(3) 0.035(2) 0.004(2) 0.0123(18) 0.004(2)
C27 0.034(2) 0.051(3) 0.028(2) 0.000(2) 0.0077(17) -0.003(2)
CME 0.102(5) 0.116(7) 0.072(5) -0.006(4) 0.023(4) 0.020(4)
OME 0.102(5) 0.116(7) 0.072(5) -0.006(4) 0.023(4) 0.020(4)
OW 0.052(4) 0.115(6) 0.064(4) 0.002(4) 0.027(3) 0.008(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.350(5) . ?
N1 C13 1.391(5) . ?
N1 H1 0.8800 . ?
C2 N15 1.324(5) . ?
C2 C3 1.435(6) . ?
C3 C4 1.370(6) . ?
C3 N7 1.398(5) . ?
C4 C5 1.395(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(7) . ?
C5 H5 0.9500 . ?
C6 N7 1.372(6) . ?
C6 H6 0.9500 . ?
N7 C8 1.402(5) . ?
C8 C9 1.393(6) . ?
C8 C13 1.400(6) . ?
C9 C10 1.362(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(6) . ?
C10 H10 0.9500 . ?
C11 O14 1.365(5) . ?
C11 C12 1.380(6) . ?
C12 C13 1.388(6) . ?
C12 H12 0.9500 . ?
O14 C15 1.436(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N15 N16 1.395(5) . ?
N16 C17 1.275(5) . ?
C17 C18 1.458(6) . ?
C17 H17 0.9500 . ?
C18 C27 1.376(5) . ?
C18 C19 1.440(6) . ?
C19 C20 1.405(6) . ?
C19 C24 1.423(6) . ?
C20 C21 1.377(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.402(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.359(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.414(6) . ?
C23 H23 0.9500 . ?
C24 N25 1.368(5) . ?
N25 C26 1.324(5) . ?
C26 C27 1.398(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
CME OME 1.511(12) 2 ?
CME CME 1.511(12) 2 ?

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(4) . . ?
C2 N1 H1 118.0 . . ?
C13 N1 H1 118.0 . . ?
N15 C2 N1 123.8(4) . . ?
N15 C2 C3 118.5(4) . . ?
N1 C2 C3 117.7(4) . . ?
C4 C3 N7 107.2(4) . . ?
C4 C3 C2 133.8(4) . . ?
N7 C3 C2 119.0(4) . . ?
C3 C4 C5 108.4(4) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
C6 C5 C4 107.8(4) . . ?
C6 C5 H5 126.1 . . ?
C4 C5 H5 126.1 . . ?
C5 C6 N7 108.3(4) . . ?
C5 C6 H6 125.8 . . ?
N7 C6 H6 125.8 . . ?
C6 N7 C3 108.3(4) . . ?
C6 N7 C8 129.7(4) . . ?
C3 N7 C8 121.9(3) . . ?
C9 C8 C13 118.7(4) . . ?
C9 C8 N7 123.5(4) . . ?
C13 C8 N7 117.8(4) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
O14 C11 C12 124.1(4) . . ?
O14 C11 C10 116.4(4) . . ?
C12 C11 C10 119.4(4) . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 N1 120.5(4) . . ?
C12 C13 C8 120.0(4) . . ?
N1 C13 C8 119.5(4) . . ?
C11 O14 C15 117.0(4) . . ?
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 . . ?
C2 N15 N16 111.0(3) . . ?
C17 N16 N15 114.9(3) . . ?
N16 C17 C18 120.3(4) . . ?
N16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C27 C18 C19 118.0(4) . . ?
C27 C18 C17 121.0(4) . . ?
C19 C18 C17 120.9(4) . . ?
C20 C19 C24 119.0(4) . . ?
C20 C19 C18 123.7(4) . . ?
C24 C19 C18 117.2(4) . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.4(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.0(5) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
N25 C24 C23 117.2(4) . . ?
N25 C24 C19 123.4(4) . . ?
C23 C24 C19 119.4(4) . . ?
C26 N25 C24 116.7(4) . . ?
N25 C26 C27 124.8(4) . . ?
N25 C26 H26 117.6 . . ?
C27 C26 H26 117.6 . . ?
C18 C27 C26 119.8(4) . . ?
C18 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
OME CME CME 0.0(7) 2 2 ?

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 -179.4(4) . . . . ?
C13 N1 C2 C3 1.1(6) . . . . ?
N15 C2 C3 C4 -1.2(7) . . . . ?
N1 C2 C3 C4 178.3(5) . . . . ?
N15 C2 C3 N7 -179.0(4) . . . . ?
N1 C2 C3 N7 0.5(6) . . . . ?
N7 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 -178.2(5) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C4 C5 C6 N7 0.2(6) . . . . ?
C5 C6 N7 C3 -0.3(5) . . . . ?
C5 C6 N7 C8 -178.6(4) . . . . ?
C4 C3 N7 C6 0.3(5) . . . . ?
C2 C3 N7 C6 178.6(4) . . . . ?
C4 C3 N7 C8 178.8(4) . . . . ?
C2 C3 N7 C8 -2.8(6) . . . . ?
C6 N7 C8 C9 2.5(7) . . . . ?
C3 N7 C8 C9 -175.7(4) . . . . ?
C6 N7 C8 C13 -178.2(4) . . . . ?
C3 N7 C8 C13 3.6(6) . . . . ?
C13 C8 C9 C10 0.4(6) . . . . ?
N7 C8 C9 C10 179.7(4) . . . . ?
C8 C9 C10 C11 1.9(6) . . . . ?
C9 C10 C11 O14 175.6(4) . . . . ?
C9 C10 C11 C12 -3.4(6) . . . . ?
O14 C11 C12 C13 -176.4(4) . . . . ?
C10 C11 C12 C13 2.6(6) . . . . ?
C11 C12 C13 N1 -178.8(4) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
C2 N1 C13 C12 178.2(4) . . . . ?
C2 N1 C13 C8 -0.3(6) . . . . ?
C9 C8 C13 C12 -1.2(6) . . . . ?
N7 C8 C13 C12 179.5(4) . . . . ?
C9 C8 C13 N1 177.3(4) . . . . ?
N7 C8 C13 N1 -2.0(6) . . . . ?
C12 C11 O14 C15 -2.3(6) . . . . ?
C10 C11 O14 C15 178.7(4) . . . . ?
N1 C2 N15 N16 0.3(6) . . . . ?
C3 C2 N15 N16 179.8(3) . . . . ?
C2 N15 N16 C17 -173.4(4) . . . . ?
N15 N16 C17 C18 178.5(4) . . . . ?
N16 C17 C18 C27 4.6(6) . . . . ?
N16 C17 C18 C19 -172.3(4) . . . . ?
C27 C18 C19 C20 -177.8(4) . . . . ?
C17 C18 C19 C20 -0.8(6) . . . . ?
C27 C18 C19 C24 0.7(6) . . . . ?
C17 C18 C19 C24 177.7(4) . . . . ?
C24 C19 C20 C21 -1.3(6) . . . . ?
C18 C19 C20 C21 177.3(4) . . . . ?
C19 C20 C21 C22 0.6(7) . . . . ?
C20 C21 C22 C23 0.1(8) . . . . ?
C21 C22 C23 C24 -0.1(8) . . . . ?
C22 C23 C24 N25 -179.6(4) . . . . ?
C22 C23 C24 C19 -0.6(7) . . . . ?
C20 C19 C24 N25 -179.7(4) . . . . ?
C18 C19 C24 N25 1.6(6) . . . . ?
C20 C19 C24 C23 1.2(6) . . . . ?
C18 C19 C24 C23 -177.4(4) . . . . ?
C23 C24 N25 C26 176.1(4) . . . . ?
C19 C24 N25 C26 -2.9(6) . . . . ?
C24 N25 C26 C27 1.9(6) . . . . ?
C19 C18 C27 C26 -1.7(6) . . . . ?
C17 C18 C27 C26 -178.7(4) . . . . ?
N25 C26 C27 C18 0.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.065