##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3,5,7-triphenyl-1,2-diazacyclohepta-1(7),2-diene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H20 N2'
_chemical_formula_sum     'C23 H20 N2'
_chemical_formula_iupac     'C23 H20 N2'
_chemical_formula_weight     324.41
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.4245(14)
_cell_length_b     10.6605(16)
_cell_length_c     18.405(3)
_cell_angle_alpha     80.2989(19)
_cell_angle_beta     85.094(2)
_cell_angle_gamma     78.1155(19)
_cell_volume     1781.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5062
_cell_measurement_theta_min     1.98
_cell_measurement_theta_max     27.68
_cell_measurement_temperature     296
_exptl_crystal_description     block
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.210
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.071
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.967
_exptl_absorpt_correction_T_max     0.982
_exptl_special_details     ?
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15860
_diffrn_reflns_av_R_equivalents     0.0301
_diffrn_reflns_av_sigmaI/netI     0.0479
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     27.68
_diffrn_reflns_theta_full     27.68
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     8141
_reflns_number_gt     5062
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0875
_refine_ls_R_factor_gt     0.0490
_refine_ls_wR_factor_gt     0.1260
_refine_ls_wR_factor_ref     0.1492
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     8141
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0725P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.175
_refine_diff_density_min     -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and WinGX (Farrugia, 2012)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.45206(19) 0.35100(18) 0.06052(10) 0.0567(5) Uani d . 1 1 . .
    H H1 0.4049 0.4128 0.0240 0.068 Uiso calc R 1 1 . .
    C C2 0.5909(2) 0.2851(2) 0.04550(11) 0.0630(5) Uani d . 1 1 . .
    H H2 0.6366 0.3030 -0.0008 0.076 Uiso calc R 1 1 . .
    C C3 0.6618(2) 0.19324(19) 0.09872(12) 0.0650(5) Uani d . 1 1 . .
    H H3 0.7548 0.1481 0.0883 0.078 Uiso calc R 1 1 . .
    C C4 0.5946(2) 0.1683(2) 0.16752(13) 0.0693(6) Uani d . 1 1 . .
    H H4 0.6432 0.1071 0.2039 0.083 Uiso calc R 1 1 . .
    C C5 0.4549(2) 0.23370(17) 0.18309(11) 0.0589(5) Uani d . 1 1 . .
    H H5 0.4102 0.2154 0.2296 0.071 Uiso calc R 1 1 . .
    C C6 0.38163(17) 0.32626(15) 0.12960(9) 0.0459(4) Uani d . 1 1 . .
    C C7 0.23121(17) 0.39697(16) 0.14432(9) 0.0461(4) Uani d . 1 1 . .
    C C8 0.12814(18) 0.33644(16) 0.19997(9) 0.0478(4) Uani d . 1 1 . .
    H H8A 0.0805 0.3993 0.2311 0.057 Uiso calc R 1 1 . .
    H H8B 0.1826 0.2630 0.2312 0.057 Uiso calc R 1 1 . .
    C C9 0.01134(17) 0.29026(15) 0.16181(9) 0.0442(4) Uani d . 1 1 . .
    H H9 -0.0735 0.2906 0.1965 0.053 Uiso calc R 1 1 . .
    C C10 0.05610(17) 0.15394(15) 0.14295(9) 0.0444(4) Uani d . 1 1 . .
    C C11 0.1572(2) 0.12425(17) 0.08598(11) 0.0596(5) Uani d . 1 1 . .
    H H11 0.2032 0.1885 0.0597 0.071 Uiso calc R 1 1 . .
    C C12 0.1908(2) 0.00012(19) 0.06769(12) 0.0703(6) Uani d . 1 1 . .
    H H12 0.2587 -0.0179 0.0292 0.084 Uiso calc R 1 1 . .
    C C13 0.1246(2) -0.09664(18) 0.10582(12) 0.0658(5) Uani d . 1 1 . .
    H H13 0.1455 -0.1792 0.0926 0.079 Uiso calc R 1 1 . .
    C C14 0.0278(2) -0.06981(17) 0.16334(11) 0.0619(5) Uani d . 1 1 . .
    H H14 -0.0157 -0.1352 0.1902 0.074 Uiso calc R 1 1 . .
    C C15 -0.00653(18) 0.05436(17) 0.18225(10) 0.0517(4) Uani d . 1 1 . .
    H H15 -0.0723 0.0708 0.2218 0.062 Uiso calc R 1 1 . .
    C C16 -0.03654(18) 0.39067(15) 0.09335(9) 0.0474(4) Uani d . 1 1 . .
    H H16A 0.0364 0.3792 0.0533 0.057 Uiso calc R 1 1 . .
    H H16B -0.1269 0.3767 0.0776 0.057 Uiso calc R 1 1 . .
    C C17 -0.05721(18) 0.52700(15) 0.11026(9) 0.0463(4) Uani d . 1 1 . .
    C C18 -0.20589(18) 0.60540(16) 0.11874(9) 0.0475(4) Uani d . 1 1 . .
    C C19 -0.32386(19) 0.54717(19) 0.14197(11) 0.0592(5) Uani d . 1 1 . .
    H H19 -0.3103 0.4572 0.1529 0.071 Uiso calc R 1 1 . .
    C C20 -0.4617(2) 0.6214(2) 0.14902(12) 0.0688(5) Uani d . 1 1 . .
    H H20 -0.5402 0.5814 0.1649 0.083 Uiso calc R 1 1 . .
    C C21 -0.4828(2) 0.7542(2) 0.13257(11) 0.0690(6) Uani d . 1 1 . .
    H H21 -0.5757 0.8038 0.1372 0.083 Uiso calc R 1 1 . .
    C C22 -0.3676(2) 0.8138(2) 0.10936(11) 0.0650(5) Uani d . 1 1 . .
    H H22 -0.3827 0.9037 0.0980 0.078 Uiso calc R 1 1 . .
    C C23 -0.2289(2) 0.74058(17) 0.10276(10) 0.0553(4) Uani d . 1 1 . .
    H H23 -0.1509 0.7816 0.0877 0.066 Uiso calc R 1 1 . .
    C C24 0.64207(19) 0.85674(17) 0.43180(10) 0.0542(4) Uani d . 1 1 . .
    H H24 0.5895 0.8962 0.4698 0.065 Uiso calc R 1 1 . .
    C C25 0.7791(2) 0.78340(18) 0.44365(11) 0.0612(5) Uani d . 1 1 . .
    H H25 0.8178 0.7736 0.4895 0.073 Uiso calc R 1 1 . .
    C C26 0.8592(2) 0.72444(18) 0.38795(12) 0.0638(5) Uani d . 1 1 . .
    H H26 0.9515 0.6750 0.3962 0.077 Uiso calc R 1 1 . .
    C C27 0.8017(2) 0.73931(19) 0.32052(12) 0.0664(5) Uani d . 1 1 . .
    H H27 0.8558 0.7007 0.2826 0.080 Uiso calc R 1 1 . .
    C C28 0.6633(2) 0.81159(18) 0.30837(10) 0.0594(5) Uani d . 1 1 . .
    H H28 0.6247 0.8195 0.2626 0.071 Uiso calc R 1 1 . .
    C C29 0.58134(18) 0.87253(16) 0.36372(9) 0.0473(4) Uani d . 1 1 . .
    C C30 0.43378(18) 0.95174(16) 0.35081(9) 0.0472(4) Uani d . 1 1 . .
    C C31 0.33390(18) 0.91588(17) 0.30130(9) 0.0492(4) Uani d . 1 1 . .
    H H31A 0.3893 0.8541 0.2714 0.059 Uiso calc R 1 1 . .
    H H31B 0.2906 0.9927 0.2684 0.059 Uiso calc R 1 1 . .
    C C32 0.21158(18) 0.85520(15) 0.34815(9) 0.0455(4) Uani d . 1 1 . .
    H H32 0.1286 0.8720 0.3169 0.055 Uiso calc R 1 1 . .
    C C33 0.25497(17) 0.70859(15) 0.36832(9) 0.0458(4) Uani d . 1 1 . .
    C C34 0.2912(2) 0.64605(18) 0.43816(11) 0.0702(6) Uani d . 1 1 . .
    H H34 0.2901 0.6944 0.4759 0.084 Uiso calc R 1 1 . .
    C C35 0.3293(3) 0.5110(2) 0.45268(13) 0.0803(6) Uani d . 1 1 . .
    H H35 0.3527 0.4704 0.5001 0.096 Uiso calc R 1 1 . .
    C C36 0.3329(2) 0.43795(19) 0.39851(14) 0.0700(6) Uani d . 1 1 . .
    H H36 0.3590 0.3480 0.4085 0.084 Uiso calc R 1 1 . .
    C C37 0.2974(2) 0.4986(2) 0.32940(13) 0.0720(6) Uani d . 1 1 . .
    H H37 0.2996 0.4495 0.2919 0.086 Uiso calc R 1 1 . .
    C C38 0.2583(2) 0.63236(19) 0.31423(11) 0.0625(5) Uani d . 1 1 . .
    H H38 0.2337 0.6717 0.2667 0.075 Uiso calc R 1 1 . .
    C C39 0.16124(19) 0.92650(16) 0.41463(9) 0.0510(4) Uani d . 1 1 . .
    H H39A 0.0696 0.9055 0.4359 0.061 Uiso calc R 1 1 . .
    H H39B 0.2323 0.8984 0.4521 0.061 Uiso calc R 1 1 . .
    C C40 0.14324(19) 1.07091(16) 0.39051(9) 0.0478(4) Uani d . 1 1 . .
    C C41 -0.00265(18) 1.15585(16) 0.38144(9) 0.0465(4) Uani d . 1 1 . .
    C C42 -0.1257(2) 1.10590(18) 0.37626(10) 0.0570(5) Uani d . 1 1 . .
    H H42 -0.1177 1.0166 0.3806 0.068 Uiso calc R 1 1 . .
    C C43 -0.2598(2) 1.1862(2) 0.36478(12) 0.0700(6) Uani d . 1 1 . .
    H H43 -0.3410 1.1507 0.3617 0.084 Uiso calc R 1 1 . .
    C C44 -0.2728(2) 1.3181(2) 0.35797(12) 0.0739(6) Uani d . 1 1 . .
    H H44 -0.3623 1.3724 0.3491 0.089 Uiso calc R 1 1 . .
    C C45 -0.1526(2) 1.36985(19) 0.36436(11) 0.0679(5) Uani d . 1 1 . .
    H H45 -0.1619 1.4593 0.3605 0.082 Uiso calc R 1 1 . .
    C C46 -0.0187(2) 1.29029(17) 0.37643(10) 0.0543(4) Uani d . 1 1 . .
    H H46 0.0612 1.3263 0.3813 0.065 Uiso calc R 1 1 . .
    N N1 0.19129(15) 0.50891(14) 0.10536(8) 0.0554(4) Uani d . 1 1 . .
    N N2 0.05077(15) 0.57917(13) 0.11899(9) 0.0547(4) Uani d . 1 1 . .
    N N3 0.39270(16) 1.04815(14) 0.38622(8) 0.0543(4) Uani d . 1 1 . .
    N N4 0.25420(15) 1.12582(13) 0.37384(8) 0.0514(4) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.381(2) ?
    C1 C6 . 1.393(2) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.373(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.376(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.388(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.389(2) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.488(2) y
    C7 N1 . 1.286(2) y
    C7 C8 . 1.508(2) ?
    C8 C9 . 1.555(2) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.517(2) ?
    C9 C16 . 1.543(2) ?
    C9 H9 . 0.9800 ?
    C10 C15 . 1.387(2) ?
    C10 C11 . 1.387(2) ?
    C11 C12 . 1.387(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.375(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.365(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.392(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.508(2) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N2 . 1.289(2) y
    C17 C18 . 1.487(2) y
    C18 C19 . 1.385(2) ?
    C18 C23 . 1.396(2) ?
    C19 C20 . 1.384(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.372(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.370(3) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.385(2) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.379(2) ?
    C24 C29 . 1.392(2) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.380(3) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.368(3) ?
    C26 H26 . 0.9300 ?
    C27 C28 . 1.387(3) ?
    C27 H27 . 0.9300 ?
    C28 C29 . 1.392(2) ?
    C28 H28 . 0.9300 ?
    C29 C30 . 1.486(2) y
    C30 N3 . 1.284(2) y
    C30 C31 . 1.508(2) ?
    C31 C32 . 1.562(2) ?
    C31 H31A . 0.9700 ?
    C31 H31B . 0.9700 ?
    C32 C33 . 1.521(2) ?
    C32 C39 . 1.538(2) ?
    C32 H32 . 0.9800 ?
    C33 C34 . 1.380(2) ?
    C33 C38 . 1.382(2) ?
    C34 C35 . 1.395(3) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.359(3) ?
    C35 H35 . 0.9300 ?
    C36 C37 . 1.362(3) ?
    C36 H36 . 0.9300 ?
    C37 C38 . 1.384(3) ?
    C37 H37 . 0.9300 ?
    C38 H38 . 0.9300 ?
    C39 C40 . 1.507(2) ?
    C39 H39A . 0.9700 ?
    C39 H39B . 0.9700 ?
    C40 N4 . 1.291(2) y
    C40 C41 . 1.488(2) y
    C41 C42 . 1.388(2) ?
    C41 C46 . 1.398(2) ?
    C42 C43 . 1.384(3) ?
    C42 H42 . 0.9300 ?
    C43 C44 . 1.371(3) ?
    C43 H43 . 0.9300 ?
    C44 C45 . 1.380(3) ?
    C44 H44 . 0.9300 ?
    C45 C46 . 1.380(2) ?
    C45 H45 . 0.9300 ?
    C46 H46 . 0.9300 ?
    N1 N2 . 1.4056(19) y
    N3 N4 . 1.4083(19) y
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
    _geom_angle_publ_flag
    C2 C1 C6 . . 120.96(17) ?
    C2 C1 H1 . . 119.5 ?
    C6 C1 H1 . . 119.5 ?
    C3 C2 C1 . . 120.23(18) ?
    C3 C2 H2 . . 119.9 ?
    C1 C2 H2 . . 119.9 ?
    C2 C3 C4 . . 119.67(18) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 H3 . . 120.2 ?
    C3 C4 C5 . . 120.53(18) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 120.38(18) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C5 C6 C1 . . 118.22(16) ?
    C5 C6 C7 . . 121.65(15) ?
    C1 C6 C7 . . 120.12(15) ?
    N1 C7 C6 . . 117.17(14) y
    N1 C7 C8 . . 121.65(15) y
    C6 C7 C8 . . 121.11(14) y
    C7 C8 C9 . . 111.65(13) ?
    C7 C8 H8A . . 109.3 ?
    C9 C8 H8A . . 109.3 ?
    C7 C8 H8B . . 109.3 ?
    C9 C8 H8B . . 109.3 ?
    H8A C8 H8B . . 108.0 ?
    C10 C9 C16 . . 111.73(13) ?
    C10 C9 C8 . . 114.79(13) ?
    C16 C9 C8 . . 109.01(13) ?
    C10 C9 H9 . . 107.0 ?
    C16 C9 H9 . . 107.0 ?
    C8 C9 H9 . . 107.0 ?
    C15 C10 C11 . . 117.68(16) ?
    C15 C10 C9 . . 120.10(15) ?
    C11 C10 C9 . . 122.21(14) ?
    C12 C11 C10 . . 120.91(17) ?
    C12 C11 H11 . . 119.5 ?
    C10 C11 H11 . . 119.5 ?
    C13 C12 C11 . . 120.68(19) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 119.08(18) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C13 C14 C15 . . 120.72(17) ?
    C13 C14 H14 . . 119.6 ?
    C15 C14 H14 . . 119.6 ?
    C10 C15 C14 . . 120.88(17) ?
    C10 C15 H15 . . 119.6 ?
    C14 C15 H15 . . 119.6 ?
    C17 C16 C9 . . 110.90(13) ?
    C17 C16 H16A . . 109.5 ?
    C9 C16 H16A . . 109.5 ?
    C17 C16 H16B . . 109.5 ?
    C9 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 108.0 ?
    N2 C17 C18 . . 117.66(15) y
    N2 C17 C16 . . 122.19(15) y
    C18 C17 C16 . . 120.14(14) y
    C19 C18 C23 . . 118.65(16) ?
    C19 C18 C17 . . 121.36(15) ?
    C23 C18 C17 . . 119.99(15) ?
    C20 C19 C18 . . 120.67(18) ?
    C20 C19 H19 . . 119.7 ?
    C18 C19 H19 . . 119.7 ?
    C21 C20 C19 . . 120.03(19) ?
    C21 C20 H20 . . 120.0 ?
    C19 C20 H20 . . 120.0 ?
    C22 C21 C20 . . 120.26(18) ?
    C22 C21 H21 . . 119.9 ?
    C20 C21 H21 . . 119.9 ?
    C21 C22 C23 . . 120.28(19) ?
    C21 C22 H22 . . 119.9 ?
    C23 C22 H22 . . 119.9 ?
    C22 C23 C18 . . 120.11(18) ?
    C22 C23 H23 . . 119.9 ?
    C18 C23 H23 . . 119.9 ?
    C25 C24 C29 . . 120.87(17) ?
    C25 C24 H24 . . 119.6 ?
    C29 C24 H24 . . 119.6 ?
    C24 C25 C26 . . 120.53(18) ?
    C24 C25 H25 . . 119.7 ?
    C26 C25 H25 . . 119.7 ?
    C27 C26 C25 . . 119.50(18) ?
    C27 C26 H26 . . 120.2 ?
    C25 C26 H26 . . 120.2 ?
    C26 C27 C28 . . 120.37(19) ?
    C26 C27 H27 . . 119.8 ?
    C28 C27 H27 . . 119.8 ?
    C27 C28 C29 . . 120.92(18) ?
    C27 C28 H28 . . 119.5 ?
    C29 C28 H28 . . 119.5 ?
    C24 C29 C28 . . 117.80(16) ?
    C24 C29 C30 . . 120.94(15) ?
    C28 C29 C30 . . 121.26(16) ?
    N3 C30 C29 . . 117.17(15) y
    N3 C30 C31 . . 121.53(15) y
    C29 C30 C31 . . 121.22(15) y
    C30 C31 C32 . . 110.55(13) ?
    C30 C31 H31A . . 109.5 ?
    C32 C31 H31A . . 109.5 ?
    C30 C31 H31B . . 109.5 ?
    C32 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 108.1 ?
    C33 C32 C39 . . 114.17(13) ?
    C33 C32 C31 . . 112.31(13) ?
    C39 C32 C31 . . 109.82(13) ?
    C33 C32 H32 . . 106.7 ?
    C39 C32 H32 . . 106.7 ?
    C31 C32 H32 . . 106.7 ?
    C34 C33 C38 . . 117.41(17) ?
    C34 C33 C32 . . 123.80(16) ?
    C38 C33 C32 . . 118.78(16) ?
    C33 C34 C35 . . 120.62(19) ?
    C33 C34 H34 . . 119.7 ?
    C35 C34 H34 . . 119.7 ?
    C36 C35 C34 . . 121.0(2) ?
    C36 C35 H35 . . 119.5 ?
    C34 C35 H35 . . 119.5 ?
    C35 C36 C37 . . 118.90(19) ?
    C35 C36 H36 . . 120.6 ?
    C37 C36 H36 . . 120.6 ?
    C36 C37 C38 . . 120.83(19) ?
    C36 C37 H37 . . 119.6 ?
    C38 C37 H37 . . 119.6 ?
    C33 C38 C37 . . 121.25(19) ?
    C33 C38 H38 . . 119.4 ?
    C37 C38 H38 . . 119.4 ?
    C40 C39 C32 . . 109.97(13) ?
    C40 C39 H39A . . 109.7 ?
    C32 C39 H39A . . 109.7 ?
    C40 C39 H39B . . 109.7 ?
    C32 C39 H39B . . 109.7 ?
    H39A C39 H39B . . 108.2 ?
    N4 C40 C41 . . 116.91(14) y
    N4 C40 C39 . . 121.36(15) y
    C41 C40 C39 . . 121.68(14) y
    C42 C41 C46 . . 117.92(16) ?
    C42 C41 C40 . . 121.87(15) ?
    C46 C41 C40 . . 120.19(15) ?
    C43 C42 C41 . . 121.42(18) ?
    C43 C42 H42 . . 119.3 ?
    C41 C42 H42 . . 119.3 ?
    C44 C43 C42 . . 119.85(19) ?
    C44 C43 H43 . . 120.1 ?
    C42 C43 H43 . . 120.1 ?
    C43 C44 C45 . . 119.79(19) ?
    C43 C44 H44 . . 120.1 ?
    C45 C44 H44 . . 120.1 ?
    C44 C45 C46 . . 120.65(19) ?
    C44 C45 H45 . . 119.7 ?
    C46 C45 H45 . . 119.7 ?
    C45 C46 C41 . . 120.33(17) ?
    C45 C46 H46 . . 119.8 ?
    C41 C46 H46 . . 119.8 ?
    C7 N1 N2 . . 118.48(13) ?
    C17 N2 N1 . . 117.55(14) ?
    C30 N3 N4 . . 118.10(14) ?
    C40 N4 N3 . . 117.54(14) ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.2(3) ?
    C1 C2 C3 C4 . . . . -0.8(3) ?
    C2 C3 C4 C5 . . . . 1.0(3) ?
    C3 C4 C5 C6 . . . . -0.6(3) ?
    C4 C5 C6 C1 . . . . 0.0(3) ?
    C4 C5 C6 C7 . . . . 179.31(17) ?
    C2 C1 C6 C5 . . . . 0.2(3) ?
    C2 C1 C6 C7 . . . . -179.12(16) ?
    C5 C6 C7 N1 . . . . 155.10(17) ?
    C1 C6 C7 N1 . . . . -25.6(2) ?
    C5 C6 C7 C8 . . . . -27.9(2) ?
    C1 C6 C7 C8 . . . . 151.36(16) ?
    N1 C7 C8 C9 . . . . 71.8(2) ?
    C6 C7 C8 C9 . . . . -105.05(17) ?
    C7 C8 C9 C10 . . . . 87.21(17) ?
    C7 C8 C9 C16 . . . . -38.97(18) ?
    C16 C9 C10 C15 . . . . -126.52(16) ?
    C8 C9 C10 C15 . . . . 108.72(17) ?
    C16 C9 C10 C11 . . . . 52.3(2) ?
    C8 C9 C10 C11 . . . . -72.5(2) ?
    C15 C10 C11 C12 . . . . 2.0(3) ?
    C9 C10 C11 C12 . . . . -176.81(17) ?
    C10 C11 C12 C13 . . . . -0.2(3) ?
    C11 C12 C13 C14 . . . . -1.6(3) ?
    C12 C13 C14 C15 . . . . 1.6(3) ?
    C11 C10 C15 C14 . . . . -2.1(2) ?
    C9 C10 C15 C14 . . . . 176.75(15) ?
    C13 C14 C15 C10 . . . . 0.3(3) ?
    C10 C9 C16 C17 . . . . -170.82(13) ?
    C8 C9 C16 C17 . . . . -42.90(17) ?
    C9 C16 C17 N2 . . . . 72.4(2) ?
    C9 C16 C17 C18 . . . . -106.57(16) ?
    N2 C17 C18 C19 . . . . -151.71(17) ?
    C16 C17 C18 C19 . . . . 27.3(2) ?
    N2 C17 C18 C23 . . . . 28.7(2) ?
    C16 C17 C18 C23 . . . . -152.37(16) ?
    C23 C18 C19 C20 . . . . 0.2(3) ?
    C17 C18 C19 C20 . . . . -179.48(17) ?
    C18 C19 C20 C21 . . . . 0.3(3) ?
    C19 C20 C21 C22 . . . . -0.2(3) ?
    C20 C21 C22 C23 . . . . -0.4(3) ?
    C21 C22 C23 C18 . . . . 0.9(3) ?
    C19 C18 C23 C22 . . . . -0.8(3) ?
    C17 C18 C23 C22 . . . . 178.86(16) ?
    C29 C24 C25 C26 . . . . 0.3(3) ?
    C24 C25 C26 C27 . . . . 0.1(3) ?
    C25 C26 C27 C28 . . . . -0.9(3) ?
    C26 C27 C28 C29 . . . . 1.3(3) ?
    C25 C24 C29 C28 . . . . 0.2(2) ?
    C25 C24 C29 C30 . . . . -179.90(16) ?
    C27 C28 C29 C24 . . . . -1.0(3) ?
    C27 C28 C29 C30 . . . . 179.10(16) ?
    C24 C29 C30 N3 . . . . 31.3(2) ?
    C28 C29 C30 N3 . . . . -148.76(17) ?
    C24 C29 C30 C31 . . . . -145.51(16) ?
    C28 C29 C30 C31 . . . . 34.4(2) ?
    N3 C30 C31 C32 . . . . -71.6(2) ?
    C29 C30 C31 C32 . . . . 105.09(17) ?
    C30 C31 C32 C33 . . . . -89.81(17) ?
    C30 C31 C32 C39 . . . . 38.37(18) ?
    C39 C32 C33 C34 . . . . -19.5(2) ?
    C31 C32 C33 C34 . . . . 106.31(19) ?
    C39 C32 C33 C38 . . . . 160.18(16) ?
    C31 C32 C33 C38 . . . . -73.96(19) ?
    C38 C33 C34 C35 . . . . 0.0(3) ?
    C32 C33 C34 C35 . . . . 179.74(18) ?
    C33 C34 C35 C36 . . . . 0.5(3) ?
    C34 C35 C36 C37 . . . . -0.4(3) ?
    C35 C36 C37 C38 . . . . -0.1(3) ?
    C34 C33 C38 C37 . . . . -0.5(3) ?
    C32 C33 C38 C37 . . . . 179.76(16) ?
    C36 C37 C38 C33 . . . . 0.5(3) ?
    C33 C32 C39 C40 . . . . 171.24(14) ?
    C31 C32 C39 C40 . . . . 44.09(18) ?
    C32 C39 C40 N4 . . . . -72.9(2) ?
    C32 C39 C40 C41 . . . . 104.24(17) ?
    N4 C40 C41 C42 . . . . 160.69(16) ?
    C39 C40 C41 C42 . . . . -16.5(2) ?
    N4 C40 C41 C46 . . . . -18.1(2) ?
    C39 C40 C41 C46 . . . . 164.70(15) ?
    C46 C41 C42 C43 . . . . 1.5(3) ?
    C40 C41 C42 C43 . . . . -177.30(17) ?
    C41 C42 C43 C44 . . . . 0.3(3) ?
    C42 C43 C44 C45 . . . . -1.5(3) ?
    C43 C44 C45 C46 . . . . 1.0(3) ?
    C44 C45 C46 C41 . . . . 0.8(3) ?
    C42 C41 C46 C45 . . . . -2.0(3) ?
    C40 C41 C46 C45 . . . . 176.79(16) ?
    C6 C7 N1 N2 . . . . -178.77(14) ?
    C8 C7 N1 N2 . . . . 4.2(2) ?
    C18 C17 N2 N1 . . . . -175.19(14) ?
    C16 C17 N2 N1 . . . . 5.9(2) ?
    C7 N1 N2 C17 . . . . -60.5(2) y
    C29 C30 N3 N4 . . . . 178.94(13) ?
    C31 C30 N3 N4 . . . . -4.2(2) ?
    C41 C40 N4 N3 . . . . 176.38(14) ?
    C39 C40 N4 N3 . . . . -6.4(2) ?
    C30 N3 N4 C40 . . . . 61.8(2) y
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3,7-bis(2-hydroxyphenyl)-5-phenyl-1,2-diazacyclohepta-1(7),2-diene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H20 N2 O2'
_chemical_formula_sum     'Ctwo23 H20 N2 O2'
_chemical_formula_iupac     'C23 H20 N2 O2'
_chemical_formula_weight     356.41
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_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     23.9715(14)
_cell_length_b     9.5669(16)
_cell_length_c     18.2303(12)
_cell_angle_alpha     90.00
_cell_angle_beta     119.256(3)
_cell_angle_gamma     90.00
_cell_volume     3647.5(7)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1649
_cell_measurement_theta_min     1.95
_cell_measurement_theta_max     25.02
_cell_measurement_temperature     296
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.298
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1504
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.967
_exptl_absorpt_correction_T_max     0.972
_exptl_special_details     ?
_diffrn_ambient_temperature     296
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12998
_diffrn_reflns_av_R_equivalents     0.0706
_diffrn_reflns_av_sigmaI/netI     0.0683
_diffrn_reflns_theta_min     1.95
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     3224
_reflns_number_gt     1647
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1186
_refine_ls_R_factor_gt     0.0450
_refine_ls_wR_factor_gt     0.0862
_refine_ls_wR_factor_ref     0.1093
_refine_ls_goodness_of_fit_ref     0.963
_refine_ls_restrained_S_all     0.963
_refine_ls_number_reflns     3224
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0426P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.132
_refine_diff_density_min     -0.135
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0014(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and WinGX (Farrugia, 2012)
;
_computing_publication_material     'publCIF (Westrip, 2010)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.37760(14) 0.7121(3) 0.13321(16) 0.0607(7) Uani d . 1 1 . .
    C C2 0.42387(14) 0.8122(4) 0.14804(18) 0.0827(10) Uani d . 1 1 . .
    H H2 0.4647 0.7840 0.1606 0.099 Uiso calc R 1 1 . .
    C C3 0.41027(18) 0.9513(4) 0.14444(19) 0.0923(11) Uani d . 1 1 . .
    H H3 0.4421 1.0168 0.1552 0.111 Uiso calc R 1 1 . .
    C C4 0.34995(17) 0.9960(3) 0.12501(17) 0.0795(9) Uani d . 1 1 . .
    H H4 0.3406 1.0909 0.1217 0.095 Uiso calc R 1 1 . .
    C C5 0.30379(13) 0.8978(3) 0.11052(14) 0.0595(7) Uani d . 1 1 . .
    H H5 0.2631 0.9280 0.0973 0.071 Uiso calc R 1 1 . .
    C C6 0.31590(12) 0.7540(3) 0.11501(14) 0.0500(6) Uani d . 1 1 . .
    C C7 0.26667(11) 0.6507(3) 0.10285(13) 0.0450(6) Uani d . 1 1 . .
    C C8 0.20110(11) 0.6912(2) 0.08683(14) 0.0479(6) Uani d . 1 1 . .
    H H8A 0.1692 0.6360 0.0408 0.058 Uiso calc R 1 1 . .
    H H8B 0.1933 0.7890 0.0709 0.058 Uiso calc R 1 1 . .
    C C9 0.19542(10) 0.6666(2) 0.16681(14) 0.0420(6) Uani d . 1 1 . .
    H H9 0.2233 0.7356 0.2084 0.050 Uiso calc R 1 1 . .
    C C10 0.12857(11) 0.6920(2) 0.15289(15) 0.0415(6) Uani d . 1 1 . .
    C C11 0.12080(12) 0.7586(2) 0.21469(16) 0.0545(7) Uani d . 1 1 . .
    H H11 0.1567 0.7863 0.2641 0.065 Uiso calc R 1 1 . .
    C C12 0.06055(14) 0.7850(3) 0.20441(19) 0.0654(8) Uani d . 1 1 . .
    H H12 0.0564 0.8293 0.2469 0.079 Uiso calc R 1 1 . .
    C C13 0.00712(14) 0.7458(3) 0.1318(2) 0.0647(8) Uani d . 1 1 . .
    H H13 -0.0334 0.7644 0.1245 0.078 Uiso calc R 1 1 . .
    C C14 0.01365(13) 0.6789(3) 0.06980(17) 0.0626(7) Uani d . 1 1 . .
    H H14 -0.0226 0.6514 0.0207 0.075 Uiso calc R 1 1 . .
    C C15 0.07382(13) 0.6522(2) 0.07994(17) 0.0576(7) Uani d . 1 1 . .
    H H15 0.0776 0.6070 0.0374 0.069 Uiso calc R 1 1 . .
    C C16 0.22259(11) 0.5200(2) 0.20419(13) 0.0451(6) Uani d . 1 1 . .
    H H16A 0.2685 0.5272 0.2400 0.054 Uiso calc R 1 1 . .
    H H16B 0.2044 0.4902 0.2389 0.054 Uiso calc R 1 1 . .
    C C17 0.20836(11) 0.4110(2) 0.13753(14) 0.0435(6) Uani d . 1 1 . .
    C C18 0.16451(11) 0.2931(2) 0.12071(14) 0.0425(6) Uani d . 1 1 . .
    C C19 0.12935(11) 0.2789(2) 0.16312(15) 0.0523(7) Uani d . 1 1 . .
    H H19 0.1327 0.3478 0.2011 0.063 Uiso calc R 1 1 . .
    C C20 0.09007(12) 0.1661(3) 0.15024(16) 0.0640(7) Uani d . 1 1 . .
    H H20 0.0677 0.1584 0.1798 0.077 Uiso calc R 1 1 . .
    C C21 0.08399(13) 0.0638(3) 0.09293(17) 0.0646(8) Uani d . 1 1 . .
    H H21 0.0576 -0.0128 0.0841 0.077 Uiso calc R 1 1 . .
    C C22 0.11670(13) 0.0752(3) 0.04939(17) 0.0648(8) Uani d . 1 1 . .
    H H22 0.1119 0.0066 0.0106 0.078 Uiso calc R 1 1 . .
    C C23 0.15679(12) 0.1872(2) 0.06208(16) 0.0535(7) Uani d . 1 1 . .
    H H1O 0.3599(15) 0.519(3) 0.1286(18) 0.105(12) Uiso d . 1 1 . .
    H H2O 0.2146(13) 0.272(3) 0.0362(18) 0.098(10) Uiso d . 1 1 . .
    N N1 0.28238(9) 0.5199(2) 0.10805(12) 0.0511(5) Uani d . 1 1 . .
    N N2 0.23654(9) 0.41738(19) 0.09215(12) 0.0506(5) Uani d . 1 1 . .
    O O1 0.39492(9) 0.5766(3) 0.13736(12) 0.0776(6) Uani d . 1 1 . .
    O O2 0.18745(11) 0.1904(2) 0.01661(13) 0.0808(6) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.351(3) ?
    C1 C2 . 1.389(4) ?
    C1 C6 . 1.407(3) ?
    C2 C3 . 1.364(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.378(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.375(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.400(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.471(3) y
    C7 N1 . 1.297(3) y
    C7 C8 . 1.503(3) ?
    C8 C9 . 1.547(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.514(3) ?
    C9 C16 . 1.556(3) ?
    C9 H9 . 0.9800 ?
    C10 C11 . 1.384(3) ?
    C10 C15 . 1.389(3) ?
    C11 C12 . 1.386(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.370(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.372(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.386(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.509(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N2 . 1.300(3) y
    C17 C18 . 1.468(3) y
    C18 C19 . 1.401(3) ?
    C18 C23 . 1.418(3) ?
    C19 C20 . 1.375(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.386(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.366(3) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.381(3) ?
    C22 H22 . 0.9300 ?
    C23 O2 . 1.351(3) ?
    N1 N2 . 1.394(2) y
    O1 H1O . 0.95(3) ?
    O2 H2O . 0.97(3) ?
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
    _geom_angle_publ_flag
    O1 C1 C2 . . 117.2(3) ?
    O1 C1 C6 . . 123.1(2) ?
    C2 C1 C6 . . 119.8(3) ?
    C3 C2 C1 . . 121.0(3) ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C2 C3 C4 . . 120.7(3) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C5 C4 C3 . . 118.9(3) ?
    C5 C4 H4 . . 120.6 ?
    C3 C4 H4 . . 120.6 ?
    C4 C5 C6 . . 122.4(3) ?
    C4 C5 H5 . . 118.8 ?
    C6 C5 H5 . . 118.8 ?
    C5 C6 C1 . . 117.3(2) ?
    C5 C6 C7 . . 121.6(2) ?
    C1 C6 C7 . . 121.2(2) ?
    N1 C7 C6 . . 117.0(2) y
    N1 C7 C8 . . 120.1(2) y
    C6 C7 C8 . . 122.8(2) y
    C7 C8 C9 . . 110.07(18) ?
    C7 C8 H8A . . 109.6 ?
    C9 C8 H8A . . 109.6 ?
    C7 C8 H8B . . 109.6 ?
    C9 C8 H8B . . 109.6 ?
    H8A C8 H8B . . 108.2 ?
    C10 C9 C8 . . 113.01(18) ?
    C10 C9 C16 . . 113.57(17) ?
    C8 C9 C16 . . 109.80(17) ?
    C10 C9 H9 . . 106.7 ?
    C8 C9 H9 . . 106.7 ?
    C16 C9 H9 . . 106.7 ?
    C11 C10 C15 . . 117.7(2) ?
    C11 C10 C9 . . 119.3(2) ?
    C15 C10 C9 . . 122.9(2) ?
    C10 C11 C12 . . 121.3(2) ?
    C10 C11 H11 . . 119.3 ?
    C12 C11 H11 . . 119.3 ?
    C13 C12 C11 . . 120.1(3) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C13 C14 . . 119.6(3) ?
    C12 C13 H13 . . 120.2 ?
    C14 C13 H13 . . 120.2 ?
    C13 C14 C15 . . 120.4(3) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C14 C15 C10 . . 120.8(2) ?
    C14 C15 H15 . . 119.6 ?
    C10 C15 H15 . . 119.6 ?
    C17 C16 C9 . . 112.89(18) ?
    C17 C16 H16A . . 109.0 ?
    C9 C16 H16A . . 109.0 ?
    C17 C16 H16B . . 109.0 ?
    C9 C16 H16B . . 109.0 ?
    H16A C16 H16B . . 107.8 ?
    N2 C17 C18 . . 116.4(2) y
    N2 C17 C16 . . 119.8(2) y
    C18 C17 C16 . . 123.8(2) y
    C19 C18 C23 . . 117.0(2) ?
    C19 C18 C17 . . 121.4(2) ?
    C23 C18 C17 . . 121.5(2) ?
    C20 C19 C18 . . 121.9(2) ?
    C20 C19 H19 . . 119.1 ?
    C18 C19 H19 . . 119.1 ?
    C19 C20 C21 . . 119.6(2) ?
    C19 C20 H20 . . 120.2 ?
    C21 C20 H20 . . 120.2 ?
    C22 C21 C20 . . 120.2(2) ?
    C22 C21 H21 . . 119.9 ?
    C20 C21 H21 . . 119.9 ?
    C21 C22 C23 . . 121.0(2) ?
    C21 C22 H22 . . 119.5 ?
    C23 C22 H22 . . 119.5 ?
    O2 C23 C22 . . 117.2(2) ?
    O2 C23 C18 . . 122.5(2) ?
    C22 C23 C18 . . 120.3(2) ?
    C7 N1 N2 . . 119.52(19) ?
    C17 N2 N1 . . 120.17(19) ?
    C1 O1 H1O . . 108.9(18) ?
    C23 O2 H2O . . 105.1(16) ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . 179.5(3) ?
    C6 C1 C2 C3 . . . . -0.6(4) ?
    C1 C2 C3 C4 . . . . -0.8(5) ?
    C2 C3 C4 C5 . . . . 1.0(4) ?
    C3 C4 C5 C6 . . . . 0.2(4) ?
    C4 C5 C6 C1 . . . . -1.5(4) ?
    C4 C5 C6 C7 . . . . 177.4(2) ?
    O1 C1 C6 C5 . . . . -178.4(2) ?
    C2 C1 C6 C5 . . . . 1.7(4) ?
    O1 C1 C6 C7 . . . . 2.7(4) ?
    C2 C1 C6 C7 . . . . -177.1(2) ?
    C5 C6 C7 N1 . . . . 179.9(2) ?
    C1 C6 C7 N1 . . . . -1.3(3) ?
    C5 C6 C7 C8 . . . . -1.4(3) ?
    C1 C6 C7 C8 . . . . 177.4(2) ?
    N1 C7 C8 C9 . . . . 73.4(3) ?
    C6 C7 C8 C9 . . . . -105.2(2) ?
    C7 C8 C9 C10 . . . . -174.46(18) ?
    C7 C8 C9 C16 . . . . -46.5(2) ?
    C8 C9 C10 C11 . . . . -140.0(2) ?
    C16 C9 C10 C11 . . . . 94.1(2) ?
    C8 C9 C10 C15 . . . . 39.5(3) ?
    C16 C9 C10 C15 . . . . -86.4(3) ?
    C15 C10 C11 C12 . . . . 0.0(3) ?
    C9 C10 C11 C12 . . . . 179.5(2) ?
    C10 C11 C12 C13 . . . . -0.4(4) ?
    C11 C12 C13 C14 . . . . 0.8(4) ?
    C12 C13 C14 C15 . . . . -0.6(4) ?
    C13 C14 C15 C10 . . . . 0.2(4) ?
    C11 C10 C15 C14 . . . . 0.2(3) ?
    C9 C10 C15 C14 . . . . -179.4(2) ?
    C10 C9 C16 C17 . . . . 91.1(2) ?
    C8 C9 C16 C17 . . . . -36.5(3) ?
    C9 C16 C17 N2 . . . . 69.7(3) ?
    C9 C16 C17 C18 . . . . -111.5(2) ?
    N2 C17 C18 C19 . . . . -177.2(2) ?
    C16 C17 C18 C19 . . . . 4.0(3) ?
    N2 C17 C18 C23 . . . . 4.1(3) ?
    C16 C17 C18 C23 . . . . -174.7(2) ?
    C23 C18 C19 C20 . . . . 1.4(3) ?
    C17 C18 C19 C20 . . . . -177.4(2) ?
    C18 C19 C20 C21 . . . . -0.9(4) ?
    C19 C20 C21 C22 . . . . -0.2(4) ?
    C20 C21 C22 C23 . . . . 0.7(4) ?
    C21 C22 C23 O2 . . . . 179.9(2) ?
    C21 C22 C23 C18 . . . . -0.2(4) ?
    C19 C18 C23 O2 . . . . 179.1(2) ?
    C17 C18 C23 O2 . . . . -2.1(4) ?
    C19 C18 C23 C22 . . . . -0.8(3) ?
    C17 C18 C23 C22 . . . . 178.0(2) ?
    C6 C7 N1 N2 . . . . -176.21(19) ?
    C8 C7 N1 N2 . . . . 5.0(3) ?
    C18 C17 N2 N1 . . . . -175.34(19) ?
    C16 C17 N2 N1 . . . . 3.5(3) ?
    C7 N1 N2 C17 . . . . -59.8(3) y
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 H1O N1 . 0.95(3) 1.71(3) 2.539(3) 144(3) y
    O2 H2O N2 . 0.97(3) 1.65(3) 2.532(3) 150(2) y
    C21 H21 Cg2 1_545 0.93 2.74 3.495(3) 138 y
data_global
_journal_date_recd_electronic     2013-08-10
_journal_date_accepted     2013-08-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue     10
_journal_page_first     1177
_journal_page_last     1180
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113023792
_journal_coeditor_code     SK3507
_publ_contact_author_name     'Dr Yao-Cheng Shi'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering
Yangzhou University
180 SiWangTing Road
Yangzhou 225002
People's Republic of China
;
_publ_contact_author_email     ycshi@yzu.edu.cn
_publ_contact_author_fax     '86-0514-87857939'
_publ_contact_author_phone     '86-0514-87857939'
_publ_section_title
;
Two seven-membered heterocycles with 1,2-diaza ring N atoms:
3,5,7-triphenyl-1,2-diazacyclohepta-1(7),2-diene and
3,7-bis(2-hydroxyphenyl)-5-phenyl-1,2-diazacyclohepta-1(7),2-diene
;
loop_
    _publ_author_name
    _publ_author_address
    'Yao-Cheng Shi'
;
College of Chemistry and Chemical Engineering
Yangzhou University
180 SiWangTing Road
Yangzhou 225002
People's Republic of China
;
    'Hong-Yang Duan'
;
College of Chemistry and Chemical Engineering
Yangzhou University
180 SiWangTing Road
Yangzhou 225002
People's Republic of China
;
