##############################################################################
#                                                                            #
# 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_Sm
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;
(Z)-3-[(3-Acetyl-2-hydroxyphenyl)amino]-2-bromoprop-2-enal
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 Br N O3'
_chemical_formula_sum     'C11 H10 Br N O3'
_chemical_formula_iupac     'C11 H10 Br N O3'
_chemical_formula_weight     284.11
_chemical_melting_point     403.35
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.8671(7)
_cell_length_b     10.6765(8)
_cell_length_c     11.8719(8)
_cell_angle_alpha     85.770(2)
_cell_angle_beta     86.907(2)
_cell_angle_gamma     63.586(2)
_cell_volume     1116.73(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8447
_cell_measurement_theta_min     3.01
_cell_measurement_theta_max     25.97
_cell_measurement_temperature     273(2)
_cell_special_details     ?
_exptl_crystal_description     irregular
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.248
_exptl_crystal_size_mid     0.151
_exptl_crystal_size_min     0.081
_exptl_crystal_density_diffrn     1.690
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     3.671
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.5334
_exptl_absorpt_correction_T_max     0.7456
_exptl_special_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1097 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.7154.
The λ/2 correction factor is Not present.
;
_diffrn_ambient_temperature     273(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     16.0233
_diffrn_reflns_number     19863
_diffrn_reflns_av_R_equivalents     0.0314
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_theta_min     3.443
_diffrn_reflns_theta_max     25.094
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_refine_special_details     ?
_reflns_number_total     3956
_reflns_number_gt     3058
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0471
_refine_ls_R_factor_gt     0.0310
_refine_ls_wR_factor_gt     0.0674
_refine_ls_wR_factor_ref     0.0737
_refine_ls_goodness_of_fit_ref     0.998
_refine_ls_restrained_S_all     0.998
_refine_ls_number_reflns     3956
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0313P)²+0.7701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.376
_refine_diff_density_min     -0.412
_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'
    'Br' 'Br' -0.2901 2.4595
                         '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, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015) and OLEX2 (Dolomanov et
al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics     ?
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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 0.16665(4) 0.62157(4) 0.72653(3) 0.05801(12) Uani d 1 . .
    O O1 0.2875(3) 0.7949(3) 0.56457(19) 0.0763(7) Uani d 1 . .
    N N1 0.1587(3) 0.7602(3) 0.95138(18) 0.0461(6) Uani d 1 . .
    H H1 0.1350 0.6933 0.9422 0.055 Uiso calc 1 . .
    C C1 0.2849(4) 0.8174(3) 0.6639(3) 0.0566(8) Uani d 1 . .
    H H1A 0.3217 0.8801 0.6811 0.068 Uiso calc 1 . .
    Br Br2 0.48752(5) 0.93823(4) 0.37672(3) 0.06600(13) Uani d 1 . .
    O O2 0.0242(3) 0.6586(2) 1.10169(18) 0.0607(6) Uani d 1 . .
    H H2 -0.0131 0.6292 1.1542 0.091 Uiso calc 1 . .
    N N2 0.4378(3) 0.6752(2) 0.32647(19) 0.0431(6) Uani d 1 . .
    H H2A 0.4159 0.7196 0.3875 0.052 Uiso calc 1 . .
    C C2 0.2315(3) 0.7577(3) 0.7562(2) 0.0434(7) Uani d 1 . .
    O O3 -0.0753(3) 0.6459(3) 1.3025(2) 0.0751(7) Uani d 1 . .
    C C3 0.2167(3) 0.8032(3) 0.8615(2) 0.0452(7) Uani d 1 . .
    H H3 0.2500 0.8703 0.8720 0.054 Uiso calc 1 . .
    O O4 0.6521(3) 0.9619(3) 0.1490(2) 0.0838(8) Uani d 1 . .
    C C4 0.1322(3) 0.8127(3) 1.0598(2) 0.0412(7) Uani d 1 . .
    O O5 0.4446(3) 0.5331(2) 0.13048(15) 0.0507(5) Uani d 1 . .
    H H5A 0.4402 0.4848 0.0815 0.076 Uiso calc 1 . .
    C C5 0.1711(3) 0.9136(3) 1.0911(2) 0.0466(7) Uani d 1 . .
    H H5 0.2171 0.9525 1.0387 0.056 Uiso calc 1 . .
    O O6 0.3822(3) 0.3576(3) 0.04444(18) 0.0802(8) Uani d 1 . .
    C C6 0.1419(3) 0.9575(3) 1.2007(3) 0.0516(8) Uani d 1 . .
    H H6 0.1683 1.0261 1.2211 0.062 Uiso calc 1 . .
    C C7 0.0749(3) 0.9010(3) 1.2792(3) 0.0496(7) Uani d 1 . .
    H H7 0.0576 0.9304 1.3526 0.060 Uiso calc 1 . .
    C C8 0.0609(3) 0.7567(3) 1.1384(2) 0.0432(7) Uani d 1 . .
    C C9 0.0321(3) 0.7993(3) 1.2495(2) 0.0446(7) Uani d 1 . .
    C C10 -0.0394(4) 0.7359(4) 1.3315(3) 0.0583(8) Uani d 1 . .
    C C11 -0.0681(5) 0.7794(5) 1.4509(3) 0.0827(12) Uani d 1 . .
    H H11A -0.1480 0.8730 1.4530 0.124 Uiso calc 1 . .
    H H11B 0.0224 0.7765 1.4798 0.124 Uiso calc 1 . .
    H H11C -0.0969 0.7167 1.4964 0.124 Uiso calc 1 . .
    C C12 0.6158(4) 0.8655(4) 0.1585(3) 0.0644(10) Uani d 1 . .
    H H12 0.6413 0.8089 0.0973 0.077 Uiso calc 1 . .
    C C13 0.5411(3) 0.8294(3) 0.2491(2) 0.0460(7) Uani d 1 . .
    C C14 0.5073(3) 0.7195(3) 0.2459(2) 0.0435(7) Uani d 1 . .
    H H14 0.5358 0.6702 0.1804 0.052 Uiso calc 1 . .
    C C15 0.3946(3) 0.5659(3) 0.3264(2) 0.0369(6) Uani d 1 . .
    C C16 0.3950(3) 0.4978(3) 0.2302(2) 0.0371(6) Uani d 1 . .
    C C17 0.3440(3) 0.5285(3) 0.4280(2) 0.0470(7) Uani d 1 . .
    H H17 0.3435 0.5736 0.4922 0.056 Uiso calc 1 . .
    C C18 0.2940(4) 0.4262(3) 0.4371(2) 0.0551(8) Uani d 1 . .
    H H18 0.2620 0.4019 0.5068 0.066 Uiso calc 1 . .
    C C19 0.2918(4) 0.3609(3) 0.3427(2) 0.0520(8) Uani d 1 . .
    H H19 0.2573 0.2926 0.3484 0.062 Uiso calc 1 . .
    C C20 0.3410(3) 0.3957(3) 0.2379(2) 0.0408(6) Uani d 1 . .
    C C21 0.3321(4) 0.3320(3) 0.1352(3) 0.0540(8) Uani d 1 . .
    C C22 0.2604(5) 0.2335(4) 0.1402(3) 0.0760(11) Uani d 1 . .
    H H22A 0.2267 0.2238 0.2163 0.114 Uiso calc 1 . .
    H H22B 0.1755 0.2703 0.0912 0.114 Uiso calc 1 . .
    H H22C 0.3333 0.1437 0.1164 0.114 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C2 . 1.890(3) ?
    O1 C1 . 1.217(4) ?
    N1 C3 . 1.331(3) ?
    N1 C4 . 1.407(3) ?
    N1 H1 . 0.8600 ?
    C1 C2 . 1.421(4) ?
    C1 H1A . 0.9300 ?
    Br2 C13 . 1.885(3) ?
    O2 C8 . 1.356(3) ?
    O2 H2 . 0.8200 ?
    N2 C14 . 1.327(3) ?
    N2 C15 . 1.409(3) ?
    N2 H2A . 0.8600 ?
    C2 C3 . 1.351(4) ?
    O3 C10 . 1.238(4) ?
    C3 H3 . 0.9300 ?
    O4 C12 . 1.228(4) ?
    C4 C5 . 1.374(4) ?
    C4 C8 . 1.395(4) ?
    O5 C16 . 1.349(3) ?
    O5 H5A . 0.8200 ?
    C5 C6 . 1.387(4) ?
    C5 H5 . 0.9300 ?
    O6 C21 . 1.224(3) ?
    C6 C7 . 1.369(4) ?
    C6 H6 . 0.9300 ?
    C7 C9 . 1.401(4) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.399(4) ?
    C9 C10 . 1.469(4) ?
    C10 C11 . 1.497(5) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.398(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.359(4) ?
    C14 H14 . 0.9300 ?
    C15 C17 . 1.380(4) ?
    C15 C16 . 1.397(4) ?
    C16 C20 . 1.406(4) ?
    C17 C18 . 1.380(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.369(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.396(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.465(4) ?
    C21 C22 . 1.502(4) ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
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
    C3 N1 C4 . . 126.9(2) ?
    C3 N1 H1 . . 116.6 ?
    C4 N1 H1 . . 116.6 ?
    O1 C1 C2 . . 126.6(3) ?
    O1 C1 H1A . . 116.7 ?
    C2 C1 H1A . . 116.7 ?
    C8 O2 H2 . . 109.5 ?
    C14 N2 C15 . . 129.3(2) ?
    C14 N2 H2A . . 115.3 ?
    C15 N2 H2A . . 115.3 ?
    C3 C2 C1 . . 121.4(3) ?
    C3 C2 Br1 . . 120.1(2) ?
    C1 C2 Br1 . . 118.3(2) ?
    N1 C3 C2 . . 125.7(3) ?
    N1 C3 H3 . . 117.1 ?
    C2 C3 H3 . . 117.1 ?
    C5 C4 C8 . . 119.5(3) ?
    C5 C4 N1 . . 124.4(3) ?
    C8 C4 N1 . . 116.2(2) ?
    C16 O5 H5A . . 109.5 ?
    C4 C5 C6 . . 120.2(3) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C7 C6 C5 . . 120.8(3) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C7 C9 . . 120.4(3) ?
    C6 C7 H7 . . 119.8 ?
    C9 C7 H7 . . 119.8 ?
    O2 C8 C4 . . 116.5(3) ?
    O2 C8 C9 . . 122.7(3) ?
    C4 C8 C9 . . 120.8(3) ?
    C8 C9 C7 . . 118.3(3) ?
    C8 C9 C10 . . 119.7(3) ?
    C7 C9 C10 . . 121.9(3) ?
    O3 C10 C9 . . 120.3(3) ?
    O3 C10 C11 . . 119.8(3) ?
    C9 C10 C11 . . 120.0(3) ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O4 C12 C13 . . 128.6(3) ?
    O4 C12 H12 . . 115.7 ?
    C13 C12 H12 . . 115.7 ?
    C14 C13 C12 . . 121.4(3) ?
    C14 C13 Br2 . . 120.5(2) ?
    C12 C13 Br2 . . 118.1(2) ?
    N2 C14 C13 . . 126.7(3) ?
    N2 C14 H14 . . 116.6 ?
    C13 C14 H14 . . 116.6 ?
    C17 C15 C16 . . 118.7(2) ?
    C17 C15 N2 . . 117.0(2) ?
    C16 C15 N2 . . 124.3(2) ?
    O5 C16 C15 . . 119.3(2) ?
    O5 C16 C20 . . 120.9(2) ?
    C15 C16 C20 . . 119.8(2) ?
    C18 C17 C15 . . 122.0(3) ?
    C18 C17 H17 . . 119.0 ?
    C15 C17 H17 . . 119.0 ?
    C19 C18 C17 . . 119.4(3) ?
    C19 C18 H18 . . 120.3 ?
    C17 C18 H18 . . 120.3 ?
    C18 C19 C20 . . 120.7(3) ?
    C18 C19 H19 . . 119.6 ?
    C20 C19 H19 . . 119.6 ?
    C19 C20 C16 . . 119.3(3) ?
    C19 C20 C21 . . 121.3(3) ?
    C16 C20 C21 . . 119.3(2) ?
    O6 C21 C20 . . 121.2(3) ?
    O6 C21 C22 . . 118.9(3) ?
    C20 C21 C22 . . 119.9(3) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
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
    O1 C1 C2 C3 . . . . -171.7(3) ?
    O1 C1 C2 Br1 . . . . 3.6(5) ?
    C4 N1 C3 C2 . . . . -175.1(3) ?
    C1 C2 C3 N1 . . . . 175.4(3) ?
    Br1 C2 C3 N1 . . . . 0.1(4) ?
    C3 N1 C4 C5 . . . . -3.9(5) ?
    C3 N1 C4 C8 . . . . 175.9(3) ?
    C8 C4 C5 C6 . . . . 1.1(4) ?
    N1 C4 C5 C6 . . . . -179.2(3) ?
    C4 C5 C6 C7 . . . . 0.3(5) ?
    C5 C6 C7 C9 . . . . -1.1(5) ?
    C5 C4 C8 O2 . . . . 179.4(3) ?
    N1 C4 C8 O2 . . . . -0.3(4) ?
    C5 C4 C8 C9 . . . . -1.7(4) ?
    N1 C4 C8 C9 . . . . 178.6(3) ?
    O2 C8 C9 C7 . . . . 179.8(3) ?
    C4 C8 C9 C7 . . . . 0.9(4) ?
    O2 C8 C9 C10 . . . . 0.5(4) ?
    C4 C8 C9 C10 . . . . -178.3(3) ?
    C6 C7 C9 C8 . . . . 0.5(4) ?
    C6 C7 C9 C10 . . . . 179.7(3) ?
    C8 C9 C10 O3 . . . . -0.6(5) ?
    C7 C9 C10 O3 . . . . -179.8(3) ?
    C8 C9 C10 C11 . . . . 179.0(3) ?
    C7 C9 C10 C11 . . . . -0.2(5) ?
    O4 C12 C13 C14 . . . . 179.2(4) ?
    O4 C12 C13 Br2 . . . . -0.6(6) ?
    C15 N2 C14 C13 . . . . 177.3(3) ?
    C12 C13 C14 N2 . . . . 179.7(3) ?
    Br2 C13 C14 N2 . . . . -0.5(4) ?
    C14 N2 C15 C17 . . . . 170.5(3) ?
    C14 N2 C15 C16 . . . . -11.8(5) ?
    C17 C15 C16 O5 . . . . -179.8(3) ?
    N2 C15 C16 O5 . . . . 2.5(4) ?
    C17 C15 C16 C20 . . . . 1.5(4) ?
    N2 C15 C16 C20 . . . . -176.1(3) ?
    C16 C15 C17 C18 . . . . 0.0(4) ?
    N2 C15 C17 C18 . . . . 177.8(3) ?
    C15 C17 C18 C19 . . . . -1.1(5) ?
    C17 C18 C19 C20 . . . . 0.6(5) ?
    C18 C19 C20 C16 . . . . 0.9(5) ?
    C18 C19 C20 C21 . . . . -176.8(3) ?
    O5 C16 C20 C19 . . . . 179.5(3) ?
    C15 C16 C20 C19 . . . . -2.0(4) ?
    O5 C16 C20 C21 . . . . -2.8(4) ?
    C15 C16 C20 C21 . . . . 175.8(3) ?
    C19 C20 C21 O6 . . . . -176.3(3) ?
    C16 C20 C21 O6 . . . . 6.0(5) ?
    C19 C20 C21 C22 . . . . 3.7(5) ?
    C16 C20 C21 C22 . . . . -174.0(3) ?
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
    N1 H1 Br1 . 0.86 2.69 3.127(2) 113.0 yes
    O2 H2 O3 . 0.82 1.83 2.547(3) 145.6 yes
    N2 H2A O1 . 0.86 2.39 3.196(3) 155.8 yes
    N2 H2A Br2 . 0.86 2.72 3.160(2) 113.6 yes
    C3 H3 O4 2_676 0.93 2.38 3.288(4) 166.0 yes
    O5 H5A O6 . 0.82 1.78 2.513(3) 147.6 yes
    C12 H12 O6 2_665 0.93 2.63 3.503(4) 157.5 yes
    C14 H14 O5 . 0.93 2.16 2.794(3) 124.6 yes
    C17 H17 O1 . 0.93 2.39 3.194(4) 144.6 yes
_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     0.463
_shelx_estimated_absorpt_T_max     0.755
_shelxl_version_number        2.014
data_px2
_audit_creation_method     SHELXL-2014
_chemical_name_systematic
;\
Di-μ-acetato-1:2κ⁴O:O'-(μ-2-acetyl-6-{[(Z)-2-\
bromo-3-oxoprop-1-en-1-yl]azanidyl}phenolato-\
1κ²O¹,O²:2κ³O¹,N,O⁶)\
(N,N-dimethyl-acetamide-1κO)dizinc(II)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H23 Br N2 O8 Zn2'
_chemical_formula_sum     'C19 H23 Br N2 O8 Zn2'
_chemical_formula_iupac     '[Zn2 (C11 H8 Br N O3) (C2 H3 O2)2 (C4 H9 N O)]'
_chemical_formula_weight     618.04
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.0300(5)
_cell_length_b     10.1184(10)
_cell_length_c     14.4723(14)
_cell_angle_alpha     87.217(8)
_cell_angle_beta     89.232(7)
_cell_angle_gamma     83.518(7)
_cell_volume     1166.95(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2035
_cell_measurement_theta_min     3.7380
_cell_measurement_theta_max     25.2190
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     ORANGE
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.759
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     620
_exptl_absorpt_coefficient_mu     3.814
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_absorpt_correction_T_min     0.557
_exptl_absorpt_correction_T_max     0.796
_exptl_special_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     293(2)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
         'Rigaku OD SuperNova Single source diffractometer with an Eos detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0233
_diffrn_reflns_number     7311
_diffrn_reflns_av_R_equivalents     0.0265
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_theta_min     3.336
_diffrn_reflns_theta_max     25.099
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     4142
_reflns_number_gt     3027
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0632
_refine_ls_R_factor_gt     0.0387
_refine_ls_wR_factor_gt     0.0790
_refine_ls_wR_factor_ref     0.0939
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     4142
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0366P)²+0.1413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.317
_refine_diff_density_min     -0.490
_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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
    'Zn' 'Zn' 0.2839 1.4301
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015) and OLEX2 (Dolomanov et
al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics     ?
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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
    Zn Zn1 0.68765(6) 0.69170(5) 0.67187(3) 0.04309(16) Uani d 1 . .
    Br Br1 0.64484(7) 0.13167(5) 1.11694(4) 0.06499(18) Uani d 1 . .
    O O1 0.5393(4) 0.2610(3) 0.8539(2) 0.0616(9) Uani d 1 . .
    N N1 0.7054(4) 0.4572(3) 0.9468(2) 0.0400(8) Uani d 1 . .
    C C1 0.5575(5) 0.2019(5) 0.9320(3) 0.0517(12) Uani d 1 . .
    H H1 0.5142 0.1206 0.9399 0.062 Uiso calc 1 . .
    Zn Zn2 0.62359(6) 0.43658(5) 0.81579(3) 0.04353(16) Uani d 1 . .
    O O2 0.7241(4) 0.6165(3) 0.8007(2) 0.0523(8) Uani d 1 . .
    N N2 0.6575(5) 0.8954(5) 0.4111(3) 0.0649(12) Uani d 1 . .
    C C2 0.6357(5) 0.2458(4) 1.0078(3) 0.0443(11) Uani d 1 . .
    O O3 0.7827(4) 0.8552(3) 0.7231(2) 0.0573(9) Uani d 1 . .
    C C3 0.7025(5) 0.3669(4) 1.0129(3) 0.0416(10) Uani d 1 . .
    H H3 0.7492 0.3840 1.0689 0.050 Uiso calc 1 . .
    O O4 0.7673(4) 0.3595(3) 0.7134(2) 0.0593(9) Uani d 1 . .
    C C4 0.7707(5) 0.5788(4) 0.9595(3) 0.0390(10) Uani d 1 . .
    O O5 0.8095(4) 0.5304(3) 0.6163(2) 0.0563(8) Uani d 1 . .
    C C5 0.8246(5) 0.6219(5) 1.0417(3) 0.0528(12) Uani d 1 . .
    H H5 0.8222 0.5673 1.0952 0.063 Uiso calc 1 . .
    O O6 0.3989(3) 0.5142(3) 0.7658(2) 0.0545(8) Uani d 1 . .
    C C6 0.8824(6) 0.7453(5) 1.0456(3) 0.0633(14) Uani d 1 . .
    H H6 0.9191 0.7722 1.1017 0.076 Uiso calc 1 . .
    O O7 0.4412(3) 0.6849(3) 0.6677(2) 0.0547(8) Uani d 1 . .
    C C7 0.8862(5) 0.8277(5) 0.9688(3) 0.0557(13) Uani d 1 . .
    H H7 0.9254 0.9102 0.9732 0.067 Uiso calc 1 . .
    O O8 0.6958(4) 0.8040(3) 0.5514(2) 0.0571(8) Uani d 1 . .
    C C8 0.7751(5) 0.6631(4) 0.8778(3) 0.0389(10) Uani d 1 . .
    C C9 0.8311(5) 0.7899(4) 0.8816(3) 0.0416(10) Uani d 1 . .
    C C10 0.8308(5) 0.8810(4) 0.8014(3) 0.0466(11) Uani d 1 . .
    C C11 0.8921(6) 1.0151(5) 0.8074(4) 0.0654(14) Uani d 1 . .
    H H11A 1.0075 1.0039 0.8256 0.098 Uiso calc 1 . .
    H H11B 0.8263 1.0652 0.8524 0.098 Uiso calc 1 . .
    H H11C 0.8815 1.0620 0.7481 0.098 Uiso calc 1 . .
    C C12 0.9477(7) 0.3202(6) 0.5861(4) 0.097(2) Uani d 1 . .
    H H12A 1.0255 0.2662 0.6258 0.145 Uiso calc 1 . .
    H H12B 1.0081 0.3723 0.5429 0.145 Uiso calc 1 . .
    H H12C 0.8834 0.2639 0.5529 0.145 Uiso calc 1 . .
    C C13 0.8313(5) 0.4117(5) 0.6437(4) 0.0528(12) Uani d 1 . .
    C C14 0.3511(5) 0.6114(5) 0.7124(3) 0.0471(11) Uani d 1 . .
    C C15 0.1634(5) 0.6422(6) 0.7005(4) 0.0778(17) Uani d 1 . .
    H H15A 0.1067 0.5994 0.7503 0.117 Uiso calc 1 . .
    H H15B 0.1314 0.6100 0.6427 0.117 Uiso calc 1 . .
    H H15C 0.1331 0.7367 0.7007 0.117 Uiso calc 1 . .
    C C16 0.5588(7) 0.6796(6) 0.4448(4) 0.0852(18) Uani d 1 . .
    H H16A 0.6136 0.6004 0.4754 0.128 Uiso calc 1 . .
    H H16B 0.5678 0.6718 0.3790 0.128 Uiso calc 1 . .
    H H16C 0.4427 0.6906 0.4627 0.128 Uiso calc 1 . .
    C C17 0.6408(5) 0.7983(5) 0.4720(3) 0.0521(12) Uani d 1 . .
    C C18 0.5994(9) 0.8999(8) 0.3153(4) 0.126(3) Uani d 1 . .
    H H18A 0.6782 0.8453 0.2789 0.189 Uiso calc 1 . .
    H H18B 0.5902 0.9900 0.2903 0.189 Uiso calc 1 . .
    H H18C 0.4919 0.8672 0.3138 0.189 Uiso calc 1 . .
    C C19 0.7426(7) 1.0085(5) 0.4376(4) 0.0897(19) Uani d 1 . .
    H H19A 0.7562 1.0045 0.5036 0.135 Uiso calc 1 . .
    H H19B 0.6766 1.0902 0.4188 0.135 Uiso calc 1 . .
    H H19C 0.8506 1.0047 0.4080 0.135 Uiso calc 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Zn1 O7 . 1.989(3) y
    Zn1 O2 . 1.992(3) y
    Zn1 O5 . 2.003(3) y
    Zn1 O8 . 2.039(3) y
    Zn1 O3 . 2.072(3) y
    Br1 C2 . 1.908(4) ?
    O1 C1 . 1.255(5) ?
    O1 Zn2 . 2.022(3) y
    N1 C3 . 1.292(5) ?
    N1 C4 . 1.412(5) ?
    N1 Zn2 . 2.043(3) y
    C1 C2 . 1.388(6) ?
    C1 H1 . 0.9300 ?
    Zn2 O4 . 2.000(3) y
    Zn2 O6 . 2.014(3) y
    Zn2 O2 . 2.074(3) y
    O2 C8 . 1.319(5) ?
    N2 C17 . 1.305(6) ?
    N2 C18 . 1.466(6) ?
    N2 C19 . 1.466(7) ?
    C2 C3 . 1.397(6) ?
    O3 C10 . 1.250(5) ?
    C3 H3 . 0.9300 ?
    O4 C13 . 1.247(6) ?
    C4 C5 . 1.378(6) ?
    C4 C8 . 1.427(6) ?
    O5 C13 . 1.241(5) ?
    C5 C6 . 1.384(6) ?
    C5 H5 . 0.9300 ?
    O6 C14 . 1.249(5) ?
    C6 C7 . 1.359(6) ?
    C6 H6 . 0.9300 ?
    O7 C14 . 1.248(5) ?
    C7 C9 . 1.427(6) ?
    C7 H7 . 0.9300 ?
    O8 C17 . 1.244(5) ?
    C8 C9 . 1.411(6) ?
    C9 C10 . 1.446(6) ?
    C10 C11 . 1.501(6) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.512(6) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C14 C15 . 1.515(6) ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C16 C17 . 1.505(7) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
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
    O7 Zn1 O2 . . 97.62(12) y
    O7 Zn1 O5 . . 110.42(13) y
    O2 Zn1 O5 . . 92.97(12) y
    O7 Zn1 O8 . . 94.36(13) y
    O2 Zn1 O8 . . 163.92(12) y
    O5 Zn1 O8 . . 92.86(13) y
    O7 Zn1 O3 . . 120.19(13) y
    O2 Zn1 O3 . . 83.31(12) y
    O5 Zn1 O3 . . 129.32(13) y
    O8 Zn1 O3 . . 81.39(13) y
    C1 O1 Zn2 . . 125.6(3) ?
    C3 N1 C4 . . 121.8(4) ?
    C3 N1 Zn2 . . 123.9(3) ?
    C4 N1 Zn2 . . 114.2(3) ?
    O1 C1 C2 . . 126.5(4) ?
    O1 C1 H1 . . 116.7 ?
    C2 C1 H1 . . 116.7 ?
    O4 Zn2 O6 . . 109.83(13) y
    O4 Zn2 O1 . . 93.61(14) y
    O6 Zn2 O1 . . 92.73(13) y
    O4 Zn2 N1 . . 124.52(13) y
    O6 Zn2 N1 . . 125.10(13) y
    O1 Zn2 N1 . . 91.22(14) y
    O4 Zn2 O2 . . 91.95(13) y
    O6 Zn2 O2 . . 93.35(12) y
    O1 Zn2 O2 . . 169.87(12) y
    N1 Zn2 O2 . . 78.65(13) y
    C8 O2 Zn1 . . 134.3(3) ?
    C8 O2 Zn2 . . 115.5(3) ?
    Zn1 O2 Zn2 . . 109.40(13) y
    C17 N2 C18 . . 124.7(5) ?
    C17 N2 C19 . . 119.1(4) ?
    C18 N2 C19 . . 116.2(5) ?
    C1 C2 C3 . . 126.4(4) ?
    C1 C2 Br1 . . 116.3(3) ?
    C3 C2 Br1 . . 117.2(3) ?
    C10 O3 Zn1 . . 133.3(3) ?
    N1 C3 C2 . . 125.9(4) ?
    N1 C3 H3 . . 117.0 ?
    C2 C3 H3 . . 117.0 ?
    C13 O4 Zn2 . . 132.1(3) ?
    C5 C4 N1 . . 126.3(4) ?
    C5 C4 C8 . . 119.2(4) ?
    N1 C4 C8 . . 114.5(3) ?
    C13 O5 Zn1 . . 132.0(3) ?
    C4 C5 C6 . . 120.8(5) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C14 O6 Zn2 . . 134.0(3) ?
    C7 C6 C5 . . 121.0(5) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C14 O7 Zn1 . . 130.1(3) ?
    C6 C7 C9 . . 121.2(4) ?
    C6 C7 H7 . . 119.4 ?
    C9 C7 H7 . . 119.4 ?
    C17 O8 Zn1 . . 135.4(3) ?
    O2 C8 C9 . . 122.9(4) ?
    O2 C8 C4 . . 116.8(4) ?
    C9 C8 C4 . . 120.3(4) ?
    C8 C9 C7 . . 117.5(4) ?
    C8 C9 C10 . . 122.2(4) ?
    C7 C9 C10 . . 120.3(4) ?
    O3 C10 C9 . . 123.8(4) ?
    O3 C10 C11 . . 115.2(4) ?
    C9 C10 C11 . . 121.0(4) ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C13 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    O5 C13 O4 . . 127.2(5) ?
    O5 C13 C12 . . 116.4(5) ?
    O4 C13 C12 . . 116.5(5) ?
    O7 C14 O6 . . 127.0(4) ?
    O7 C14 C15 . . 116.8(4) ?
    O6 C14 C15 . . 116.2(5) ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C17 C16 H16A . . 109.5 ?
    C17 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C17 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O8 C17 N2 . . 119.5(5) ?
    O8 C17 C16 . . 120.8(5) ?
    N2 C17 C16 . . 119.7(5) ?
    N2 C18 H18A . . 109.5 ?
    N2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    N2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    N2 C19 H19A . . 109.5 ?
    N2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    N2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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
    Zn2 O1 C1 C2 . . . . 1.2(7) ?
    O1 C1 C2 C3 . . . . 3.1(7) ?
    O1 C1 C2 Br1 . . . . -179.4(4) ?
    C4 N1 C3 C2 . . . . 177.8(4) ?
    Zn2 N1 C3 C2 . . . . -3.9(6) ?
    C1 C2 C3 N1 . . . . -1.5(7) ?
    Br1 C2 C3 N1 . . . . -179.0(3) ?
    C3 N1 C4 C5 . . . . -5.8(6) ?
    Zn2 N1 C4 C5 . . . . 175.7(3) ?
    C3 N1 C4 C8 . . . . 175.8(3) ?
    Zn2 N1 C4 C8 . . . . -2.7(4) ?
    N1 C4 C5 C6 . . . . -178.3(4) ?
    C8 C4 C5 C6 . . . . 0.1(7) ?
    C4 C5 C6 C7 . . . . 0.5(7) ?
    C5 C6 C7 C9 . . . . -0.1(7) ?
    Zn1 O2 C8 C9 . . . . -4.9(6) ?
    Zn2 O2 C8 C9 . . . . -173.5(3) ?
    Zn1 O2 C8 C4 . . . . 174.7(3) ?
    Zn2 O2 C8 C4 . . . . 6.1(4) ?
    C5 C4 C8 O2 . . . . 179.2(4) ?
    N1 C4 C8 O2 . . . . -2.2(5) ?
    C5 C4 C8 C9 . . . . -1.2(6) ?
    N1 C4 C8 C9 . . . . 177.4(3) ?
    O2 C8 C9 C7 . . . . -178.8(4) ?
    C4 C8 C9 C7 . . . . 1.6(6) ?
    O2 C8 C9 C10 . . . . 2.4(6) ?
    C4 C8 C9 C10 . . . . -177.2(4) ?
    C6 C7 C9 C8 . . . . -1.0(6) ?
    C6 C7 C9 C10 . . . . 177.9(4) ?
    Zn1 O3 C10 C9 . . . . 0.7(6) ?
    Zn1 O3 C10 C11 . . . . 179.9(3) ?
    C8 C9 C10 O3 . . . . -0.4(6) ?
    C7 C9 C10 O3 . . . . -179.2(4) ?
    C8 C9 C10 C11 . . . . -179.7(4) ?
    C7 C9 C10 C11 . . . . 1.5(6) ?
    Zn1 O5 C13 O4 . . . . 6.6(8) ?
    Zn1 O5 C13 C12 . . . . -173.7(3) ?
    Zn2 O4 C13 O5 . . . . -6.0(8) ?
    Zn2 O4 C13 C12 . . . . 174.3(3) ?
    Zn1 O7 C14 O6 . . . . -7.1(7) ?
    Zn1 O7 C14 C15 . . . . 173.3(3) ?
    Zn2 O6 C14 O7 . . . . 6.3(8) ?
    Zn2 O6 C14 C15 . . . . -174.2(3) ?
    Zn1 O8 C17 N2 . . . . 174.3(3) ?
    Zn1 O8 C17 C16 . . . . -7.0(7) ?
    C18 N2 C17 O8 . . . . 179.5(5) ?
    C19 N2 C17 O8 . . . . 0.7(7) ?
    C18 N2 C17 C16 . . . . 0.7(7) ?
    C19 N2 C17 C16 . . . . -178.0(5) ?
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
    C1 H1 Br1 2_657 0.93 3.13 4.005(5) 157.6 yes
    C11 H11A Br1 2_767 0.96 3.07 3.992(5) 160.4 yes
    C16 H16A O5 . 0.96 2.61 3.401(6) 139.6 yes
    C18 H18B Br1 1_564 0.96 2.88 3.658(7) 138.7 yes
    C19 H19B O7 2_676 0.96 2.63 3.563(6) 164.5 yes
_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     0.501
_shelx_estimated_absorpt_T_max     0.803
_shelxl_version_number        2.014
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2021-10-22
_journal_date_accepted     2022-01-26
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2022
_journal_volume     78
_journal_issue      2
_journal_page_first     123
_journal_page_last     130
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229622000924
_journal_coeditor_code     LF3125
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Wei-Zhou Li'
;\
Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured \
Materials
School of Resources
Environment and Materials
Guangxi University
Nanning
Guangxi 530004
People's Republic of China
;
 wz-li@hotmail.com
    'Jin-Ying Pang'
;
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics
College of Chemistry and Materials Science
Nanning Normal University
Nanning
Guangxi 530000
People's Republic of China
College of Materials Science and Engineering
Guilin University of Technology
Guilin
Guangxi 541004
People's Republic of China
;
 pangjinying@126.com
    'Shu-Hua Zhang'
;
College of Chemistry
Guangdong University of Petrochemical Technology
Maoming
Guangdong 525000
People's Republic of China
;
 zsh720108@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Syntheses, crystal structures and Hirshfeld surface analysis of
(Z)-3-[(3-acetyl-2-hydroxyphenyl)amino]-2-bromoprop-2-enal and a novel
ZnII complex
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tan-Lin Jiang' .
;\
Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured \
Materials
School of Resources
Environment and Materials
Guangxi University
Nanning
Guangxi 530004
People's Republic of China
;
    'Wei-Zhou Li' .
;\
Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured \
Materials
School of Resources
Environment and Materials
Guangxi University
Nanning
Guangxi 530004
People's Republic of China
;
    'Qi-Feng Gao' .
;\
Guangxi Key Laboratory of Processing for Non-ferrous Metals and Featured \
Materials
School of Resources
Environment and Materials
Guangxi University
Nanning
Guangxi 530004
People's Republic of China
;
    'Deng-Feng Tan' .
;
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics
College of Chemistry and Materials Science
Nanning Normal University
Nanning
Guangxi 530000
People's Republic of China
;
    'Jin-Ying Pang' .
;
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics
College of Chemistry and Materials Science
Nanning Normal University
Nanning
Guangxi 530000
People's Republic of China
College of Materials Science and Engineering
Guilin University of Technology
Guilin
Guangxi 541004
People's Republic of China
;
    'Shu-Hua Zhang' .
;
College of Chemistry
Guangdong University of Petrochemical Technology
Maoming
Guangdong 525000
People's Republic of China
;
_publ_section_synopsis
;
A novel zero-dimensional dinuclear zinc complex of
(Z)-3-[(3-acetyl-2-hydroxyphenyl)amino]-2-bromoprop-2-enal
(H₂L) was synthesized from 1-(3-amino-2-hydroxyphenyl)ethanone and
2-bromomalonaldehyde. Theoretical calculations of the bond order and excited
state of H₂L confirmed that there is a large range of electron
delocalization in the molecules. The main frame of the complex remains stable
to about 190 °C and it possesses high purity and acid and alkali resistance.
;
