#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240356.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240356
loop_
_publ_author_name
'Mohamed, Shaaban K.'
'Mague, Joel T.'
'Akkurt, Mehmet'
'El-Emary, Talaat I.'
'Albayati, Mustafa R.'
_publ_section_title
;
 Crystal structure of
 N-[(8E)-12-methyl-14-phenyl-10,13,14,16-tetraazatetracyclo[7.7.0.0^2,7^.0^11,15^]hexadeca-1(16),2,4,6,9,11(15),12-heptaen-8-ylidene]hydroxylamine
 1,4-dioxane hemisolvate
;
_journal_coeditor_code           HB7340
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o75
_journal_page_last               o76
_journal_paper_doi               10.1107/S2056989014027285
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C19 H13 N5 O, 0.5C4 H8 O2'
_chemical_formula_moiety         'C19 H13 N5 O, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C21 H17 N5 O2'
_chemical_formula_weight         371.40
_chemical_name_systematic
'N-[(8E)-12-Methyl-14-phenyl-10,13,14,16-tetraazatetracyclo[7.7.0.0^2,7^.0^11,15^]hexadeca-1(16),2,4,6,9,11(15),12-heptaen-8-ylidene]hydroxylamine 1,4-dioxane hemisolvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 102.093(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8019(4)
_cell_length_b                   5.56750(10)
_cell_length_c                   20.4756(5)
_cell_measurement_reflns_used    5735
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.034
_cell_measurement_theta_min      3.226
_cell_volume                     1761.41(7)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT  (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12942
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         67.132
_diffrn_reflns_theta_min         3.226
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+1.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                1934
_reflns_number_total             3122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7340sup1.cif
_cod_data_source_block           I
_cod_database_code               2240356
_cod_database_fobs_code          2240356
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.31941(17) 0.8942(5) 0.31844(14) 0.0526(9) Uani d 0.761(4) A 1
H H1 0.2653 0.8868 0.3133 0.063 Uiso d 0.761(4) A 1
N N5 0.3255(3) 0.7078(7) 0.27450(18) 0.0477(10) Uani d 0.761(4) A 1
O O1A 0.2787(7) 0.6744(19) 0.2677(5) 0.0526(9) Uani d 0.239(4) A 2
H H1A 0.2308 0.7294 0.2723 0.063 Uiso d 0.239(4) A 2
N N5A 0.3523(7) 0.811(3) 0.2922(7) 0.0477(10) Uani d 0.239(4) A 2
N N1 0.50054(14) 0.0011(5) 0.10956(11) 0.0441(6) Uani d 1 . .
N N2 0.42463(15) -0.1296(5) 0.08969(12) 0.0483(7) Uani d 1 . .
N N3 0.54532(15) 0.3519(5) 0.17927(11) 0.0436(6) Uani d 1 . .
N N4 0.36329(15) 0.3403(5) 0.18808(12) 0.0479(7) Uani d 1 . .
C C1 0.57561(18) -0.0748(6) 0.08673(14) 0.0434(7) Uani d 1 . .
C C2 0.65086(19) 0.0591(6) 0.10022(16) 0.0525(8) Uani d 1 . .
H H2 0.6541 0.2027 0.1257 0.063 Uiso calc 1 . .
C C3 0.7218(2) -0.0197(6) 0.07592(17) 0.0568(9) Uani d 1 . .
H H3 0.7737 0.0718 0.0849 0.068 Uiso calc 1 . .
C C4 0.7184(2) -0.2271(6) 0.03920(15) 0.0529(9) Uani d 1 . .
H H4 0.7674 -0.2792 0.0229 0.063 Uiso calc 1 . .
C C5 0.6431(2) -0.3581(6) 0.02643(16) 0.0558(9) Uani d 1 . .
H H5 0.6399 -0.5020 0.0011 0.067 Uiso calc 1 . .
C C6 0.5719(2) -0.2820(6) 0.05014(15) 0.0526(8) Uani d 1 . .
H H6 0.5201 -0.3738 0.0410 0.063 Uiso calc 1 . .
C C7 0.36423(19) -0.0231(6) 0.11490(14) 0.0478(8) Uani d 1 . .
C C8 0.27394(18) -0.1199(6) 0.10347(16) 0.0564(9) Uani d 1 . .
H H8A 0.2341 -0.0060 0.0763 0.085 Uiso calc 1 . .
H H8B 0.2573 -0.1429 0.1465 0.085 Uiso calc 1 . .
H H8C 0.2713 -0.2741 0.0801 0.085 Uiso calc 1 . .
C C9 0.39917(18) 0.1795(6) 0.15255(14) 0.0457(8) Uani d 1 . .
C C10 0.48730(18) 0.1895(6) 0.14854(14) 0.0435(7) Uani d 1 . .
C C11 0.50897(18) 0.5059(6) 0.21488(14) 0.0436(7) Uani d 1 . .
C C12 0.41977(18) 0.4993(6) 0.21947(14) 0.0467(8) Uani d 1 . .
C C13 0.40452(19) 0.6952(6) 0.26329(15) 0.0501(8) Uani d 1 . .
C C14 0.4877(2) 0.8210(6) 0.28446(14) 0.0492(8) Uani d 1 . .
C C15 0.55051(18) 0.7031(6) 0.25596(14) 0.0455(8) Uani d 1 . .
C C16 0.6360(2) 0.7815(6) 0.26910(16) 0.0531(8) Uani d 1 . .
H H16 0.6783 0.7027 0.2500 0.064 Uiso calc 1 . .
C C17 0.6576(2) 0.9791(6) 0.31112(16) 0.0573(9) Uani d 1 . .
H H17 0.7157 1.0349 0.3212 0.069 Uiso calc 1 . .
C C18 0.5955(2) 1.0949(6) 0.33833(16) 0.0595(9) Uani d 1 . .
H H18 0.6117 1.2305 0.3663 0.071 Uiso calc 1 . .
C C19 0.5100(2) 1.0176(6) 0.32565(16) 0.0560(9) Uani d 1 . .
H H19 0.4681 1.0978 0.3448 0.067 Uiso calc 1 . .
C C20 0.4575(3) 0.6668(10) 0.4576(3) 0.1110(18) Uani d 1 . .
H H20A 0.4427 0.8360 0.4454 0.133 Uiso calc 1 . .
H H20B 0.4296 0.5635 0.4198 0.133 Uiso calc 1 . .
O O6 0.42711(19) 0.6056(7) 0.51479(14) 0.1018(11) Uani d 1 . .
C C22 0.4493(3) 0.3649(12) 0.5297(3) 0.155(3) Uani d 1 . .
H H22A 0.4217 0.2617 0.4919 0.186 Uiso calc 1 . .
H H22B 0.4275 0.3149 0.5696 0.186 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N5 O1 H1 . . 95.1
C13 N5 O1 . . 110.4(4)
N5A O1A H1A . . 117.7
C13 N5A O1A . . 97.3(9)
C10 N1 N2 . . 110.3(2)
C10 N1 C1 . . 131.4(3)
N2 N1 C1 . . 118.4(2)
C7 N2 N1 . . 107.5(3)
C11 N3 C10 . . 111.0(2)
C12 N4 C9 . . 112.8(2)
C6 C1 C2 . . 120.0(3)
C6 C1 N1 . . 119.0(3)
C2 C1 N1 . . 120.9(3)
C1 C2 C3 . . 118.9(3)
C1 C2 H2 . . 120.6
C3 C2 H2 . . 120.6
C4 C3 C2 . . 121.4(3)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C3 C4 C5 . . 118.9(3)
C3 C4 H4 . . 120.6
C5 C4 H4 . . 120.6
C4 C5 C6 . . 120.5(3)
C4 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C1 C6 C5 . . 120.4(3)
C1 C6 H6 . . 119.8
C5 C6 H6 . . 119.8
N2 C7 C9 . . 109.9(3)
N2 C7 C8 . . 121.4(3)
C9 C7 C8 . . 128.6(3)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
N4 C9 C7 . . 131.5(3)
N4 C9 C10 . . 122.4(3)
C7 C9 C10 . . 106.1(3)
N3 C10 N1 . . 128.2(3)
N3 C10 C9 . . 125.6(3)
N1 C10 C9 . . 106.2(3)
N3 C11 C12 . . 124.3(3)
N3 C11 C15 . . 127.5(3)
C12 C11 C15 . . 108.2(3)
N4 C12 C11 . . 123.9(3)
N4 C12 C13 . . 127.9(3)
C11 C12 C13 . . 108.2(3)
N5A C13 C12 . . 149.3(6)
N5 C13 C12 . . 115.5(3)
N5A C13 C14 . . 104.2(6)
N5 C13 C14 . . 138.0(3)
C12 C13 C14 . . 106.5(2)
C19 C14 C15 . . 120.5(3)
C19 C14 C13 . . 130.9(3)
C15 C14 C13 . . 108.6(3)
C16 C15 C14 . . 120.8(3)
C16 C15 C11 . . 130.6(3)
C14 C15 C11 . . 108.6(3)
C15 C16 C17 . . 118.0(3)
C15 C16 H16 . . 121.0
C17 C16 H16 . . 121.0
C18 C17 C16 . . 120.8(3)
C18 C17 H17 . . 119.6
C16 C17 H17 . . 119.6
C17 C18 C19 . . 121.6(3)
C17 C18 H18 . . 119.2
C19 C18 H18 . . 119.2
C14 C19 C18 . . 118.3(3)
C14 C19 H19 . . 120.9
C18 C19 H19 . . 120.9
O6 C20 C22 . 3_666 109.5(4)
O6 C20 H20A . . 109.8
C22 C20 H20A 3_666 . 109.8
O6 C20 H20B . . 109.8
C22 C20 H20B 3_666 . 109.8
H20A C20 H20B . . 108.2
C20 O6 C22 . . 107.6(4)
O6 C22 C20 . 3_666 110.7(5)
O6 C22 H22A . . 109.5
C20 C22 H22A 3_666 . 109.5
O6 C22 H22B . . 109.5
C20 C22 H22B 3_666 . 109.5
H22A C22 H22B . . 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N5 . 1.390(4)
O1 H1 . 0.8400
N5 C13 . 1.318(5)
O1A N5A . 1.392(12)
O1A H1A . 0.8402
N5A C13 . 1.286(12)
N1 C10 . 1.360(4)
N1 N2 . 1.389(3)
N1 C1 . 1.427(3)
N2 C7 . 1.317(4)
N3 C11 . 1.331(4)
N3 C10 . 1.346(4)
N4 C12 . 1.324(4)
N4 C9 . 1.351(4)
C1 C6 . 1.370(4)
C1 C2 . 1.382(4)
C2 C3 . 1.389(4)
C2 H2 . 0.9500
C3 C4 . 1.373(5)
C3 H3 . 0.9500
C4 C5 . 1.374(4)
C4 H4 . 0.9500
C5 C6 . 1.382(4)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 C9 . 1.412(4)
C7 C8 . 1.497(4)
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 C10 . 1.413(4)
C11 C12 . 1.433(4)
C11 C15 . 1.453(4)
C12 C13 . 1.464(4)
C13 C14 . 1.472(4)
C14 C19 . 1.382(4)
C14 C15 . 1.414(4)
C15 C16 . 1.391(4)
C16 C17 . 1.394(5)
C16 H16 . 0.9500
C17 C18 . 1.385(4)
C17 H17 . 0.9500
C18 C19 . 1.389(5)
C18 H18 . 0.9500
C19 H19 . 0.9500
C20 O6 . 1.398(5)
C20 C22 3_666 1.452(6)
C20 H20A . 0.9900
C20 H20B . 0.9900
O6 C22 . 1.403(6)
C22 C20 3_666 1.452(6)
C22 H22A . 0.9900
C22 H22B . 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N4 2 0.84 2.04 2.878(3) 172 yes
O1a H1a N4 2 0.84 1.94 2.749(5) 162 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C10 N1 N2 C7 . . 0.9(3)
C1 N1 N2 C7 . . -178.2(2)
C10 N1 C1 C6 . . 176.7(3)
N2 N1 C1 C6 . . -4.5(4)
C10 N1 C1 C2 . . -4.3(5)
N2 N1 C1 C2 . . 174.6(3)
C6 C1 C2 C3 . . 0.2(5)
N1 C1 C2 C3 . . -178.8(3)
C1 C2 C3 C4 . . -0.2(5)
C2 C3 C4 C5 . . 0.1(5)
C3 C4 C5 C6 . . 0.1(5)
C2 C1 C6 C5 . . -0.1(5)
N1 C1 C6 C5 . . 179.0(3)
C4 C5 C6 C1 . . 0.0(5)
N1 N2 C7 C9 . . -0.5(3)
N1 N2 C7 C8 . . -179.4(3)
C12 N4 C9 C7 . . 176.7(3)
C12 N4 C9 C10 . . -1.9(4)
N2 C7 C9 N4 . . -178.8(3)
C8 C7 C9 N4 . . 0.0(5)
N2 C7 C9 C10 . . -0.1(3)
C8 C7 C9 C10 . . 178.8(3)
C11 N3 C10 N1 . . -178.0(3)
C11 N3 C10 C9 . . 0.1(4)
N2 N1 C10 N3 . . 177.4(3)
C1 N1 C10 N3 . . -3.6(5)
N2 N1 C10 C9 . . -1.0(3)
C1 N1 C10 C9 . . 178.0(3)
N4 C9 C10 N3 . . 1.1(5)
C7 C9 C10 N3 . . -177.8(3)
N4 C9 C10 N1 . . 179.5(3)
C7 C9 C10 N1 . . 0.6(3)
C10 N3 C11 C12 . . -0.2(4)
C10 N3 C11 C15 . . 178.7(3)
C9 N4 C12 C11 . . 1.8(4)
C9 N4 C12 C13 . . -178.7(3)
N3 C11 C12 N4 . . -0.8(5)
C15 C11 C12 N4 . . -179.8(3)
N3 C11 C12 C13 . . 179.6(3)
C15 C11 C12 C13 . . 0.5(3)
O1A N5A C13 C12 . . 0(2)
O1A N5A C13 C14 . . 179.8(8)
O1 N5 C13 C12 . . 177.9(3)
O1 N5 C13 C14 . . 0.6(6)
N4 C12 C13 N5A . . 0.6(15)
C11 C12 C13 N5A . . -179.8(14)
N4 C12 C13 N5 . . 2.7(5)
C11 C12 C13 N5 . . -177.7(3)
N4 C12 C13 C14 . . -179.2(3)
C11 C12 C13 C14 . . 0.4(3)
N5A C13 C14 C19 . . 0.2(8)
N5 C13 C14 C19 . . -2.6(7)
C12 C13 C14 C19 . . -180.0(3)
N5A C13 C14 C15 . . 178.9(7)
N5 C13 C14 C15 . . 176.2(4)
C12 C13 C14 C15 . . -1.2(3)
C19 C14 C15 C16 . . 0.4(4)
C13 C14 C15 C16 . . -178.5(3)
C19 C14 C15 C11 . . -179.5(3)
C13 C14 C15 C11 . . 1.6(3)
N3 C11 C15 C16 . . -0.3(5)
C12 C11 C15 C16 . . 178.8(3)
N3 C11 C15 C14 . . 179.6(3)
C12 C11 C15 C14 . . -1.3(3)
C14 C15 C16 C17 . . 0.0(4)
C11 C15 C16 C17 . . 179.9(3)
C15 C16 C17 C18 . . -0.7(5)
C16 C17 C18 C19 . . 0.8(5)
C15 C14 C19 C18 . . -0.2(4)
C13 C14 C19 C18 . . 178.4(3)
C17 C18 C19 C14 . . -0.4(5)
C22 C20 O6 C22 3_666 . -59.7(7)
C20 O6 C22 C20 . 3_666 60.4(7)
