##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                        #
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##############################################################################
data_global
_audit_creation_method     'APEX2 v2014.9-0'
_journal_date_recd_electronic     2015-04-09
_journal_date_accepted     2015-04-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      5
_journal_page_first     o349
_journal_page_last     o350
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015007471
_journal_coeditor_code     BG2553
_publ_contact_author_name
;
Mustafa R. Albayati
;
_publ_contact_author_address
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
_publ_contact_author_email     'shaabankamel@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structure of
4-bromo-2-[(E)-N-(2,2,6,6-tetramethylpiperidin-4-yl)\
carboximidoyl]phenol dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Joel T. Mague'
;
Department of Chemistry,
Tulane University,
New Orleans,
LA 70118,
USA
;
    'Mohamed, Shaaban K.'
;
Chemistry and Environmental Division,
Manchester Metropolitan University,
Manchester M1 5GD,
England
Chemistry Department,
Faculty of Science,
Minia University,
61519 El-Minia,
Egypt
;
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Antar A. Abdelhamid'
;
Department of Chemistry,
Faculty of Science,
Sohag University,
82524 Sohag,
Egypt
;
    'Mustafa R. Albayati'
;
Kirkuk University,
College of Science,
Department of Chemistry,
Kirkuk,
Iraq
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1059897'
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;\
4-Bromo-2-[(E)-N-(2,2,6,6-tetramethylpiperidin-\
4-yl)carboximidoyl]phenol dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H23 Br N2 O, 2(H2 O)'
_chemical_formula_sum     'C16 H27 Br N2 O3'
_chemical_formula_iupac     'C16 H23 Br N2 O, 2H2 O'
_chemical_formula_weight     375.30
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 2/c'
_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_operation_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     39.6126(7)
_cell_length_b     6.04970(10)
_cell_length_c     14.8673(3)
_cell_angle_alpha     90
_cell_angle_beta     98.8890(10)
_cell_angle_gamma     90
_cell_volume     3520.07(11)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9702
_cell_measurement_theta_min     6.0253
_cell_measurement_theta_max     72.0869
_cell_measurement_temperature     150.(2)
_exptl_crystal_description     column
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.335
_exptl_crystal_size_mid     0.094
_exptl_crystal_size_min     0.082
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1568
_exptl_absorpt_coefficient_mu     3.299
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.405
_shelx_estimated_absorpt_T_max     0.774
_exptl_absorpt_correction_T_min     0.54
_exptl_absorpt_correction_T_max     0.77
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     12901
_diffrn_reflns_av_R_equivalents     0.0254
_diffrn_reflns_theta_min     6.025
_diffrn_reflns_theta_max     72.150
_diffrn_reflns_theta_full     70.000
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -48
_diffrn_reflns_limit_h_max     45
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     15
_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. H-atoms attached to carbon were placed in calculated positions
(C---H = 0.95 - 0.98 Å) while those attached to nitrogen and oxygen were
placed in locations derived from a difference map and their parameters
adjusted to give N---H = 0.91 Å and O---H = 0.84 Å. All were included as
riding contributions with isotropic displacement parameters 1.2 - 1.5 times
those of the attached atoms. Each lattice water molecule is disordered over
two sites with the oxygen and one hydrogen in common. Based on peak heights
for the disordered H atoms, the two sites for these atoms were judged to be
equally occupied.
;
_reflns_number_total     3428
_reflns_number_gt     3113
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0346
_refine_ls_R_factor_gt     0.0309
_refine_ls_wR_factor_gt     0.0744
_refine_ls_wR_factor_ref     0.0769
_refine_ls_goodness_of_fit_ref     1.095
_refine_ls_restrained_S_all     1.095
_refine_ls_number_reflns     3428
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0323P)²+4.9527P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.556
_refine_diff_density_min     -0.667
_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' 0.0181 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'
    'Br' 'Br' -0.6763 1.2805
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT  (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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
    Br Br1 0.82893(2) 0.47282(5) 0.33146(2) 0.04137(10) Uani d 1 . .
    O O1 0.69904(4) 0.0570(2) 0.41569(10) 0.0300(3) Uani d 1 . .
    H H1A 0.6835 0.1527 0.4080 0.056(9) Uiso d 1 . .
    N N1 0.66823(4) 0.4316(3) 0.36510(11) 0.0236(3) Uani d 1 . .
    N N2 0.56827(4) 0.6877(2) 0.37146(10) 0.0191(3) Uani d 1 . .
    H H2A 0.5586 0.5638 0.3912 0.023 Uiso d 1 . .
    C C1 0.72738(5) 0.3664(3) 0.35750(12) 0.0224(4) Uani d 1 . .
    C C2 0.72757(5) 0.1514(3) 0.39411(12) 0.0251(4) Uani d 1 . .
    C C3 0.75833(6) 0.0340(3) 0.40982(13) 0.0301(4) Uani d 1 . .
    H H3 0.7587 -0.1111 0.4344 0.036 Uiso calc 1 . .
    C C4 0.78818(5) 0.1262(4) 0.39007(13) 0.0335(5) Uani d 1 . .
    H H4 0.8089 0.0450 0.4008 0.040 Uiso calc 1 . .
    C C5 0.78768(5) 0.3385(4) 0.35440(13) 0.0288(4) Uani d 1 . .
    C C6 0.75773(5) 0.4580(3) 0.33731(12) 0.0249(4) Uani d 1 . .
    H H6 0.7577 0.6021 0.3119 0.030 Uiso calc 1 . .
    C C7 0.69657(5) 0.5031(3) 0.34611(12) 0.0215(4) Uani d 1 . .
    H H7 0.6977 0.6497 0.3239 0.026 Uiso calc 1 . .
    C C8 0.63930(4) 0.5860(3) 0.35583(12) 0.0210(4) Uani d 1 . .
    H H8 0.6465 0.7326 0.3343 0.025 Uiso calc 1 . .
    C C9 0.62799(5) 0.6125(3) 0.44904(12) 0.0215(4) Uani d 1 . .
    H H9A 0.6469 0.6795 0.4917 0.026 Uiso calc 1 . .
    H H9B 0.6233 0.4646 0.4728 0.026 Uiso calc 1 . .
    C C10 0.59592(4) 0.7571(3) 0.44580(12) 0.0200(4) Uani d 1 . .
    C C11 0.57716(4) 0.6334(3) 0.28012(11) 0.0196(3) Uani d 1 . .
    C C12 0.60997(5) 0.4941(3) 0.28757(12) 0.0213(4) Uani d 1 . .
    H H12A 0.6049 0.3418 0.3058 0.026 Uiso calc 1 . .
    H H12B 0.6173 0.4862 0.2269 0.026 Uiso calc 1 . .
    C C13 0.60480(5) 1.0012(3) 0.43633(14) 0.0249(4) Uani d 1 . .
    H H13A 0.6170 1.0200 0.3844 0.037 Uiso calc 1 . .
    H H13B 0.6193 1.0512 0.4920 0.037 Uiso calc 1 . .
    H H13C 0.5837 1.0889 0.4265 0.037 Uiso calc 1 . .
    C C14 0.58145(5) 0.7278(3) 0.53433(12) 0.0269(4) Uani d 1 . .
    H H14A 0.5617 0.8258 0.5342 0.040 Uiso calc 1 . .
    H H14B 0.5990 0.7650 0.5860 0.040 Uiso calc 1 . .
    H H14C 0.5743 0.5740 0.5397 0.040 Uiso calc 1 . .
    C C15 0.58037(5) 0.8434(3) 0.22423(12) 0.0247(4) Uani d 1 . .
    H H15A 0.5606 0.9394 0.2272 0.037 Uiso calc 1 . .
    H H15B 0.5811 0.8031 0.1607 0.037 Uiso calc 1 . .
    H H15C 0.6014 0.9218 0.2491 0.037 Uiso calc 1 . .
    C C16 0.54701(5) 0.4976(3) 0.23218(13) 0.0252(4) Uani d 1 . .
    H H16A 0.5435 0.3684 0.2694 0.038 Uiso calc 1 . .
    H H16B 0.5519 0.4485 0.1727 0.038 Uiso calc 1 . .
    H H16C 0.5263 0.5889 0.2237 0.038 Uiso calc 1 . .
    O O2 0.51008(4) 0.9736(2) 0.35246(11) 0.0331(3) Uani d 0.5 A 1
    H H2B 0.5278 0.8954 0.3562 0.040 Uiso d 0.5 A 1
    H H2C 0.5038 1.0005 0.2970 0.040 Uiso d 0.5 A 1
    O O3 0.51664(4) 0.2904(3) 0.49776(11) 0.0399(4) Uani d 0.5 B 1
    H H3A 0.5127 0.2158 0.5427 0.048 Uiso d 0.5 B 1
    H H3B 0.5124 0.2081 0.4519 0.048 Uiso d 0.5 B 1
    O O2A 0.51008(4) 0.9736(2) 0.35246(11) 0.0331(3) Uani d 0.5 C 2
    H H2BA 0.5278 0.8954 0.3562 0.040 Uiso d 0.5 C 2
    H H2D 0.5105 1.0762 0.3907 0.040 Uiso d 0.5 C 2
    O O3A 0.51664(4) 0.2904(3) 0.49776(11) 0.0399(4) Uani d 0.5 D 2
    H H3AA 0.5127 0.2158 0.5427 0.048 Uiso d 0.5 D 2
    H H3C 0.5069 0.4131 0.5000 0.048 Uiso d 0.5 D 2
_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
    Br1 C5 . 1.902(2) ?
    O1 C2 . 1.348(2) ?
    O1 H1A . 0.8400 ?
    N1 C7 . 1.275(2) ?
    N1 C8 . 1.468(2) ?
    N2 C10 . 1.491(2) ?
    N2 C11 . 1.491(2) ?
    N2 H2A . 0.9099 ?
    C1 C6 . 1.398(3) ?
    C1 C2 . 1.409(3) ?
    C1 C7 . 1.463(2) ?
    C2 C3 . 1.399(3) ?
    C3 C4 . 1.379(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.388(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.379(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C12 . 1.525(3) ?
    C8 C9 . 1.529(2) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.537(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C14 . 1.525(2) ?
    C10 C13 . 1.530(2) ?
    C11 C16 . 1.532(2) ?
    C11 C15 . 1.534(2) ?
    C11 C12 . 1.538(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    O2 H2B . 0.8400 ?
    O2 H2C . 0.8400 ?
    O3 H3A . 0.8399 ?
    O3 H3B . 0.8400 ?
    O2A H2BA . 0.8400 ?
    O2A H2D . 0.8400 ?
    O3A H3AA . 0.8399 ?
    O3A H3C . 0.8401 ?
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 O1 H1A . . 107.4 ?
    C7 N1 C8 . . 117.69(15) ?
    C10 N2 C11 . . 119.17(13) ?
    C10 N2 H2A . . 106.8 ?
    C11 N2 H2A . . 106.4 ?
    C6 C1 C2 . . 119.71(17) ?
    C6 C1 C7 . . 118.73(17) ?
    C2 C1 C7 . . 121.42(17) ?
    O1 C2 C3 . . 119.07(18) ?
    O1 C2 C1 . . 121.87(17) ?
    C3 C2 C1 . . 119.06(19) ?
    C4 C3 C2 . . 120.81(19) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 119.57(18) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    C6 C5 C4 . . 121.09(19) ?
    C6 C5 Br1 . . 118.76(17) ?
    C4 C5 Br1 . . 120.12(15) ?
    C5 C6 C1 . . 119.75(19) ?
    C5 C6 H6 . . 120.1 ?
    C1 C6 H6 . . 120.1 ?
    N1 C7 C1 . . 122.01(17) ?
    N1 C7 H7 . . 119.0 ?
    C1 C7 H7 . . 119.0 ?
    N1 C8 C12 . . 109.52(15) ?
    N1 C8 C9 . . 108.38(14) ?
    C12 C8 C9 . . 109.97(14) ?
    N1 C8 H8 . . 109.6 ?
    C12 C8 H8 . . 109.6 ?
    C9 C8 H8 . . 109.6 ?
    C8 C9 C10 . . 112.81(14) ?
    C8 C9 H9A . . 109.0 ?
    C10 C9 H9A . . 109.0 ?
    C8 C9 H9B . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    N2 C10 C14 . . 106.03(14) ?
    N2 C10 C13 . . 110.90(14) ?
    C14 C10 C13 . . 108.29(15) ?
    N2 C10 C9 . . 111.84(14) ?
    C14 C10 C9 . . 109.03(15) ?
    C13 C10 C9 . . 110.57(15) ?
    N2 C11 C16 . . 105.38(14) ?
    N2 C11 C15 . . 111.20(14) ?
    C16 C11 C15 . . 108.43(15) ?
    N2 C11 C12 . . 111.77(14) ?
    C16 C11 C12 . . 109.21(15) ?
    C15 C11 C12 . . 110.66(14) ?
    C8 C12 C11 . . 113.38(14) ?
    C8 C12 H12A . . 108.9 ?
    C11 C12 H12A . . 108.9 ?
    C8 C12 H12B . . 108.9 ?
    C11 C12 H12B . . 108.9 ?
    H12A C12 H12B . . 107.7 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C10 C14 H14A . . 109.5 ?
    C10 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C10 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C11 C15 H15A . . 109.5 ?
    C11 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C11 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C11 C16 H16A . . 109.5 ?
    C11 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C11 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    H2B O2 H2C . . 106.9 ?
    H3A O3 H3B . . 106.7 ?
    H2BA O2A H2D . . 116.2 ?
    H3AA O3A H3C . . 107.5 ?
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 O1 . . . . 179.19(17) ?
    C7 C1 C2 O1 . . . . 3.7(3) ?
    C6 C1 C2 C3 . . . . 0.2(3) ?
    C7 C1 C2 C3 . . . . -175.29(17) ?
    O1 C2 C3 C4 . . . . -178.91(17) ?
    C1 C2 C3 C4 . . . . 0.1(3) ?
    C2 C3 C4 C5 . . . . 0.2(3) ?
    C3 C4 C5 C6 . . . . -0.8(3) ?
    C3 C4 C5 Br1 . . . . 177.42(15) ?
    C4 C5 C6 C1 . . . . 1.1(3) ?
    Br1 C5 C6 C1 . . . . -177.13(13) ?
    C2 C1 C6 C5 . . . . -0.8(3) ?
    C7 C1 C6 C5 . . . . 174.83(16) ?
    C8 N1 C7 C1 . . . . 176.84(16) ?
    C6 C1 C7 N1 . . . . -178.48(17) ?
    C2 C1 C7 N1 . . . . -2.9(3) ?
    C7 N1 C8 C12 . . . . 120.82(18) ?
    C7 N1 C8 C9 . . . . -119.20(18) ?
    N1 C8 C9 C10 . . . . -175.48(14) ?
    C12 C8 C9 C10 . . . . -55.78(19) ?
    C11 N2 C10 C14 . . . . -162.17(15) ?
    C11 N2 C10 C13 . . . . 80.49(19) ?
    C11 N2 C10 C9 . . . . -43.4(2) ?
    C8 C9 C10 N2 . . . . 49.0(2) ?
    C8 C9 C10 C14 . . . . 165.96(15) ?
    C8 C9 C10 C13 . . . . -75.08(19) ?
    C10 N2 C11 C16 . . . . 161.25(15) ?
    C10 N2 C11 C15 . . . . -81.47(18) ?
    C10 N2 C11 C12 . . . . 42.7(2) ?
    N1 C8 C12 C11 . . . . 174.37(14) ?
    C9 C8 C12 C11 . . . . 55.37(19) ?
    N2 C11 C12 C8 . . . . -48.0(2) ?
    C16 C11 C12 C8 . . . . -164.17(15) ?
    C15 C11 C12 C8 . . . . 76.55(18) ?
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 H1A N1 . 0.84 1.87 2.628(2) 149 yes
    O2 H2B N2 . 0.84 2.02 2.861(2) 175 yes
    O3 H3A O2 5_666 0.84 2.24 3.059(2) 167 yes
    O3 H3B O2 1_545 0.84 2.04 2.869(2) 168 yes
    O2A H2BA N2 . 0.84 2.02 2.861(2) 175 yes
    O2A H2D O3A 1_565 0.84 2.04 2.869(2) 170 yes
    O3A H3AA O2A 5_666 0.84 2.24 3.059(2) 167 yes
_shelxl_version_number     2014/6
