 
data_complex_6
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C13 H17 Br I N2 O4 Zn, H2 O'
_chemical_formula_sum
 'C13 H19 Br I N2 O5 Zn' 
_chemical_formula_weight          555.48

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'I'  'I'  -0.4742   1.8119
 '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'
 'Zn'  'Zn'   0.2839   1.4301
 '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'
 'N'  'N'   0.0061   0.0033
 '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'
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.599(3)
_cell_length_b                    21.956(7)
_cell_length_c                    7.911(2)
_cell_angle_alpha                 90
_cell_angle_beta                  99.741(4)
_cell_angle_gamma                 90
_cell_volume                      1814.4(9)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     5433
_cell_measurement_theta_min       2.69
_cell_measurement_theta_max       23.24
 
_exptl_crystal_description        needle
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     2.033          
_exptl_crystal_F_000              1076
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.22
_exptl_crystal_size_min           0.15
_exptl_absorpt_coefficient_mu     5.281
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.258
_exptl_absorpt_correction_T_max   0.453
_exptl_absorpt_process_details    'SADABS'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             22940
_diffrn_reflns_av_unetI/netI      0.0430
_diffrn_reflns_av_R_equivalents   0.0612
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -26
_diffrn_reflns_limit_k_max        27
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          1.855
_diffrn_reflns_theta_max          25.898
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3499
_reflns_number_gt                 2818
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material   'Wingx 2013.3 (Farrugia, 1999)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0805P)²+3.2914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3499
_refine_ls_number_parameters      215
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0613
_refine_ls_R_factor_gt            0.0460
_refine_ls_wR_factor_ref          0.1360
_refine_ls_wR_factor_gt           0.1261
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
I1 I 0.11267(5) 0.38874(2) 0.77915(6) 0.04383(18) Uani 1 1 d . . . . .
Br1 Br 0.86751(8) 0.20040(4) 0.97017(12) 0.0639(3) Uani 1 1 d . . . . .
Zn1 Zn 0.31615(7) 0.40311(3) 0.64042(9) 0.0313(2) Uani 1 1 d . . . . .
O6W O 0.5665(5) 0.5392(2) 0.8734(6) 0.0504(12) Uani 1 1 d G . . . .
H5A H 0.548900 0.548450 0.971167 0.076 Uiso 1 1 d G U . . .
H5B H 0.623599 0.563302 0.848961 0.076 Uiso 1 1 d G U . . .
O2 O 0.7059(4) 0.42579(19) 0.9739(6) 0.0435(11) Uani 1 1 d . . . . .
O1 O 0.4859(4) 0.40263(18) 0.7862(6) 0.0395(11) Uani 1 1 d . . . . .
N1 N 0.3408(5) 0.3154(2) 0.5516(6) 0.0339(11) Uani 1 1 d . . . . .
O7W O 0.5799(5) 0.1661(2) 0.7661(6) 0.0473(12) Uani 1 1 d . . . . .
C1 C 0.2392(7) 0.2907(3) 0.4233(9) 0.0466(17) Uani 1 1 d . . . . .
H1A H 0.162252 0.286265 0.473332 0.056 Uiso 1 1 calc R U . . .
H1B H 0.264040 0.250500 0.389879 0.056 Uiso 1 1 calc R U . . .
C2 C 0.1583(7) 0.3940(4) 0.2928(9) 0.0499(18) Uani 1 1 d . . . . .
H2A H 0.126727 0.412381 0.182287 0.060 Uiso 1 1 calc R U . . .
H2B H 0.086922 0.390439 0.354456 0.060 Uiso 1 1 calc R U . . .
N3 N 0.2572(6) 0.4341(3) 0.3905(6) 0.0417(13) Uani 1 1 d . . . . .
C1A C 0.4334(6) 0.2810(3) 0.6103(8) 0.0335(13) Uani 1 1 d . . . . .
H1AA H 0.430979 0.241511 0.567130 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5439(6) 0.2971(3) 0.7392(8) 0.0318(13) Uani 1 1 d . . . . .
C8 C 0.5665(6) 0.3566(3) 0.8111(8) 0.0309(13) Uani 1 1 d . . . . .
C9 C 0.6867(6) 0.3672(3) 0.9182(8) 0.0339(13) Uani 1 1 d . . . . .
C10 C 0.8280(7) 0.4396(3) 1.0751(10) 0.0497(18) Uani 1 1 d . . . . .
H10A H 0.840742 0.414911 1.176687 0.075 Uiso 1 1 calc R U . . .
H10B H 0.830572 0.481863 1.106854 0.075 Uiso 1 1 calc R U . . .
H10C H 0.894460 0.431352 1.009538 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7747(6) 0.3213(3) 0.9591(9) 0.0403(15) Uani 1 1 d . . . . .
H11 H 0.852521 0.329031 1.029712 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7464(6) 0.2633(3) 0.8940(9) 0.0392(15) Uani 1 1 d . . . . .
C13 C 0.6354(6) 0.2511(3) 0.7868(9) 0.0409(16) Uani 1 1 d . . . . .
H13 H 0.619485 0.211865 0.744285 0.049 Uiso 1 1 calc R U . . .
O3 O 0.3422(5) 0.5049(2) 0.6658(6) 0.0472(12) Uani 1 1 d . . . . .
H4 H 0.407(9) 0.529(4) 0.728(11) 0.071 Uiso 1 1 d . U . . .
C15 C 0.2083(8) 0.4977(3) 0.4006(10) 0.0529(19) Uani 1 1 d . . . . .
H15A H 0.186410 0.514960 0.286460 0.063 Uiso 1 1 calc R U . . .
H15B H 0.132129 0.497782 0.453543 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3118(8) 0.5345(3) 0.5058(10) 0.055(2) Uani 1 1 d . . . . .
H16A H 0.386401 0.536548 0.450007 0.066 Uiso 1 1 calc R U . . .
H16B H 0.282157 0.575673 0.520877 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2099(8) 0.3304(4) 0.2651(9) 0.056(2) Uani 1 1 d . . . . .
H17A H 0.147873 0.309462 0.180795 0.067 Uiso 1 1 calc R U . . .
H17B H 0.287685 0.334851 0.216736 0.067 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
I1 Zn1 2.5993(10) . ?
Br1 C12 1.911(6) . ?
Zn1 O1 1.966(4) . ?
Zn1 N1 2.082(5) . ?
Zn1 N3 2.084(5) . ?
Zn1 O3 2.257(5) . ?
O6W H5A 0.8500 . ?
O6W H5B 0.8499 . ?
O2 C9 1.363(7) . ?
O2 C10 1.435(8) . ?
O1 C8 1.317(7) . ?
N1 C1A 1.263(8) . ?
N1 C1 1.454(8) . ?
C1 C17 1.514(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N3 1.482(9) . ?
C2 C17 1.528(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C15 1.498(9) . ?
C1A C7 1.461(9) . ?
C1A H1AA 0.9300 . ?
C7 C13 1.407(8) . ?
C7 C8 1.428(8) . ?
C8 C9 1.425(9) . ?
C9 C11 1.375(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.388(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(9) . ?
C13 H13 0.9300 . ?
O3 C16 1.410(8) . ?
O3 H4 0.94(9) . ?
C15 C16 1.497(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 Zn1 N1 92.20(18) . . ?
O1 Zn1 N3 131.0(2) . . ?
N1 Zn1 N3 90.9(2) . . ?
O1 Zn1 O3 82.36(18) . . ?
N1 Zn1 O3 157.8(2) . . ?
N3 Zn1 O3 76.9(2) . . ?
O1 Zn1 I1 119.61(15) . . ?
N1 Zn1 I1 100.98(14) . . ?
N3 Zn1 I1 107.64(17) . . ?
O3 Zn1 I1 100.40(13) . . ?
H5A O6W H5B 109.5 . . ?
C9 O2 C10 116.8(5) . . ?
C8 O1 Zn1 126.7(4) . . ?
C1A N1 C1 118.1(5) . . ?
C1A N1 Zn1 124.3(4) . . ?
C1 N1 Zn1 117.4(4) . . ?
N1 C1 C17 112.7(6) . . ?
N1 C1 H1A 109.0 . . ?
C17 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C17 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N3 C2 C17 112.2(6) . . ?
N3 C2 H2A 109.2 . . ?
C17 C2 H2A 109.2 . . ?
N3 C2 H2B 109.2 . . ?
C17 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 N3 C15 111.2(6) . . ?
C2 N3 Zn1 111.9(4) . . ?
C15 N3 Zn1 107.8(4) . . ?
N1 C1A C7 126.4(6) . . ?
N1 C1A H1AA 116.8 . . ?
C7 C1A H1AA 116.8 . . ?
C13 C7 C8 119.2(6) . . ?
C13 C7 C1A 116.6(6) . . ?
C8 C7 C1A 124.1(5) . . ?
O1 C8 C9 117.1(5) . . ?
O1 C8 C7 125.6(6) . . ?
C9 C8 C7 117.3(5) . . ?
O2 C9 C11 123.9(6) . . ?
O2 C9 C8 114.6(5) . . ?
C11 C9 C8 121.5(6) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 119.4(6) . . ?
C9 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 121.5(6) . . ?
C13 C12 Br1 121.4(5) . . ?
C11 C12 Br1 117.0(5) . . ?
C12 C13 C7 120.8(6) . . ?
C12 C13 H13 119.6 . . ?
C7 C13 H13 119.6 . . ?
C16 O3 Zn1 111.8(4) . . ?
C16 O3 H4 104(5) . . ?
Zn1 O3 H4 132(5) . . ?
C16 C15 N3 107.8(6) . . ?
C16 C15 H15A 110.1 . . ?
N3 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
N3 C15 H15B 110.1 . . ?
H15A C15 H15B 108.5 . . ?
O3 C16 C15 106.6(6) . . ?
O3 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
O3 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C1 C17 C2 115.8(6) . . ?
C1 C17 H17A 108.3 . . ?
C2 C17 H17A 108.3 . . ?
C1 C17 H17B 108.3 . . ?
C2 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
 
_refine_diff_density_max    1.855
_refine_diff_density_min   -1.067
_refine_diff_density_rms    0.156



