# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liujj20190412c
_database_code_depnum_ccdc_archive 'CCDC 1911418'
loop_
_audit_author_name
_audit_author_address
'Jinjian liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H13 O11 Zn, C8 H11 N, H2 O'
_chemical_formula_sum            'C17 H26 N O12 Zn'
_chemical_formula_weight         501.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br Zn'
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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9320(2)
_cell_length_b                   11.7094(3)
_cell_length_c                   15.8407(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.4294(17)
_cell_angle_gamma                90
_cell_volume                     2027.09(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      71.8560
_cell_measurement_theta_min      3.7810
_shelx_estimated_absorpt_T_max   0.656
_shelx_estimated_absorpt_T_min   0.545
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.033
_diffrn_reflns_theta_min         4.697
_diffrn_ambient_temperature      273(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  64.00   1.00    1.00    --    0.00  77.00  30.00   67
  2  ω     -3.00  36.00   1.00    1.00    --    0.00 -99.00-120.00   39
  3  ω     79.00 114.00   1.00    5.00    --   54.94  57.00-180.00   35
  4  ω      4.00  76.00   1.00    5.00    --   54.94 -57.00 120.00   72
  5  ω     49.00 115.00   1.00    5.00    --   54.94  57.00-120.00   66
  6  ω    -17.00  78.00   1.00    5.00    --   54.94 -38.00   0.00   95
  7  ω     38.00 106.00   1.00    2.50    --  109.89-111.00  30.00   68
  8  ω     52.00  78.00   1.00    2.50    --  109.89-111.00 150.00   26
  9  ω    114.00 178.00   1.00    2.50    --  109.89 111.00  30.00   64
 10  ω     45.00  89.00   1.00    2.50    --  109.89-111.00-120.00   44
 11  ω     44.00 103.00   1.00    2.50    --  109.89-111.00 120.00   59
 12  ω     85.00 110.00   1.00    2.50    --  109.89-111.00 150.00   25
 13  ω     84.00 177.00   1.00    2.50    --  109.89  25.00-120.00   93
 14  ω     89.00 178.00   1.00    2.50    --  109.89  50.00 120.00   89
 15  ω     69.00 106.00   1.00    2.50    --  109.89 -25.00  60.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0161749000
_diffrn_orient_matrix_UB_12      -0.1219044000
_diffrn_orient_matrix_UB_13      -0.0345468000
_diffrn_orient_matrix_UB_21      0.1243780000
_diffrn_orient_matrix_UB_22      -0.0093215000
_diffrn_orient_matrix_UB_23      0.0474645000
_diffrn_orient_matrix_UB_31      -0.0644266000
_diffrn_orient_matrix_UB_32      -0.0486429000
_diffrn_orient_matrix_UB_33      0.0775283000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3505
_reflns_number_total             3911
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+2.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O12(H12A,H12B)
2.b Rotating group:
 O10(H10A,H10B), O7(H7A,H7B), O9(H9A,H9B), O11(H11A,H11B), O8(H8A,H8B)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C14(H14), C4(H4), C6(H6), C5(H5), C11(H11), C7(H7)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.56063(3) 0.45386(3) 0.15614(2) 0.02165(13) Uani 1 1 d . . . . .
O6 O 0.45603(18) 0.46157(14) 0.26612(11) 0.0279(4) Uani 1 1 d . . . . .
O5 O 0.38646(18) 0.64007(16) 0.25382(11) 0.0307(4) Uani 1 1 d . . . . .
O10 O 0.64370(18) 0.31179(16) 0.20762(11) 0.0302(4) Uani 1 1 d . . . . .
H10A H 0.6652 0.3246 0.2595 0.045 Uiso 1 1 d GR . . . .
H10B H 0.7080 0.2946 0.1798 0.045 Uiso 1 1 d GR . . . .
O4 O 0.26288(19) 0.84403(16) 0.51448(11) 0.0313(4) Uani 1 1 d . . . . .
O1 O 0.2945(2) 0.24234(17) 0.51301(13) 0.0466(6) Uani 1 1 d . . . . .
O7 O 0.46849(17) 0.59200(16) 0.09899(11) 0.0277(4) Uani 1 1 d . . . . .
H7A H 0.4161 0.6228 0.1335 0.042 Uiso 1 1 d GR . . . .
H7B H 0.4276 0.5701 0.0535 0.042 Uiso 1 1 d GR . . . .
O9 O 0.67381(17) 0.44637(14) 0.04883(11) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.7249 0.3893 0.0530 0.037 Uiso 1 1 d GR . . . .
H9B H 0.7162 0.5090 0.0443 0.037 Uiso 1 1 d GR . . . .
O2 O 0.3060(2) 0.32781(16) 0.63752(11) 0.0357(5) Uani 1 1 d . . . . .
O3 O 0.2885(2) 0.75776(18) 0.63775(11) 0.0466(6) Uani 1 1 d . . . . .
N1 N -0.0311(2) 0.4415(2) 0.28343(18) 0.0388(6) Uani 1 1 d . . . . .
C10 C 0.3702(2) 0.5470(2) 0.38681(15) 0.0220(5) Uani 1 1 d . . . . .
C15 C 0.3167(2) 0.6476(2) 0.51404(15) 0.0224(5) Uani 1 1 d . . . . .
O12 O 0.3443(3) 0.2433(2) 0.23570(18) 0.0595(7) Uani 1 1 d . . . . .
H12A H 0.2702 0.2245 0.2430 0.089 Uiso 1 1 d G . . . .
H12B H 0.3588 0.3069 0.2597 0.089 Uiso 1 1 d G . . . .
C17 C 0.3443(2) 0.6482(2) 0.42877(15) 0.0231(5) Uani 1 1 d . . . . .
H17 H 0.3455 0.7171 0.3995 0.028 Uiso 1 1 calc R . . . .
C9 C 0.4069(2) 0.5505(2) 0.29517(15) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.3306(2) 0.4414(2) 0.51443(16) 0.0221(5) Uani 1 1 d . . . . .
C14 C 0.3121(2) 0.5435(2) 0.55658(15) 0.0225(5) Uani 1 1 d . . . . .
H14 H 0.2965 0.5426 0.6140 0.027 Uiso 1 1 calc R . . . .
C13 C 0.3107(2) 0.3277(2) 0.55791(16) 0.0257(5) Uani 1 1 d . . . . .
C16 C 0.2880(2) 0.7583(2) 0.55846(15) 0.0250(5) Uani 1 1 d . . . . .
C8 C -0.0053(3) 0.4876(2) 0.4539(2) 0.0355(6) Uani 1 1 d . . . . .
C4 C -0.0371(3) 0.5497(3) 0.3109(2) 0.0444(8) Uani 1 1 d . . . . .
H4 H -0.0497 0.6087 0.2724 0.053 Uiso 1 1 calc R . . . .
C2 C 0.0211(6) 0.4870(5) 0.1341(3) 0.0881(16) Uani 1 1 d . . . . .
H2A H 0.0089 0.4564 0.0777 0.106 Uiso 1 1 calc R . . . .
H2B H -0.0147 0.5628 0.1342 0.106 Uiso 1 1 calc R . . . .
C6 C 0.0011(4) 0.3764(3) 0.4227(2) 0.0518(9) Uani 1 1 d . . . . .
H6 H 0.0148 0.3158 0.4597 0.062 Uiso 1 1 calc R . . . .
C5 C -0.0125(4) 0.3560(3) 0.3385(2) 0.0504(8) Uani 1 1 d . . . . .
H5 H -0.0089 0.2813 0.3188 0.061 Uiso 1 1 calc R . . . .
C1 C 0.1493(5) 0.4994(6) 0.1488(4) 0.108(2) Uani 1 1 d . . . . .
H1A H 0.1814 0.5526 0.1089 0.129 Uiso 1 1 calc GR . . . .
H1B H 0.1886 0.4267 0.1424 0.129 Uiso 1 1 calc GR . . . .
H1C H 0.1645 0.5274 0.2051 0.129 Uiso 1 1 calc GR . . . .
O11 O 0.43751(18) 0.33510(16) 0.09665(12) 0.0322(4) Uani 1 1 d . . . . .
H11A H 0.3852 0.3697 0.0618 0.048 Uiso 1 1 d GR . . . .
H11B H 0.3891 0.3036 0.1338 0.048 Uiso 1 1 d GR . . . .
C11 C 0.3621(2) 0.4433(2) 0.42972(16) 0.0237(5) Uani 1 1 d . . . . .
H11 H 0.3777 0.3753 0.4017 0.028 Uiso 1 1 calc R . . . .
C7 C -0.0247(3) 0.5737(3) 0.3953(2) 0.0424(7) Uani 1 1 d . . . . .
H7 H -0.0295 0.6490 0.4135 0.051 Uiso 1 1 calc R . . . .
C3 C -0.0498(3) 0.4156(3) 0.1919(2) 0.0492(8) Uani 1 1 d . . . . .
H3A H -0.0285 0.3362 0.1825 0.059 Uiso 1 1 calc R . . . .
H3B H -0.1361 0.4243 0.1775 0.059 Uiso 1 1 calc R . . . .
O8 O 0.68599(19) 0.56460(16) 0.21279(12) 0.0317(4) Uani 1 1 d . . . . .
H8A H 0.6584 0.5911 0.2601 0.048 Uiso 1 1 d GR . . . .
H8B H 0.6943 0.6258 0.1822 0.048 Uiso 1 1 d GR . . . .


_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
Zn1 O6 2.1095(17) . ?
Zn1 O10 2.0542(18) . ?
Zn1 O7 2.0988(18) . ?
Zn1 O9 2.1291(17) . ?
Zn1 O11 2.1378(19) . ?
Zn1 O8 2.0745(19) . ?
O6 C9 1.263(3) . ?
O5 C9 1.254(3) . ?
O4 C16 1.249(3) . ?
O1 C13 1.237(3) . ?
O2 C13 1.263(3) . ?
O3 C16 1.256(3) . ?
N1 C4 1.341(4) . ?
N1 C5 1.340(4) . ?
N1 C3 1.490(4) . ?
C10 C17 1.391(3) . ?
C10 C9 1.516(3) . ?
C10 C11 1.395(3) . ?
C15 C17 1.392(3) . ?
C15 C14 1.394(3) . ?
C15 C16 1.511(3) . ?
C12 C14 1.387(3) . ?
C12 C13 1.516(3) . ?
C12 C11 1.394(3) . ?
C8 C8 1.490(6) 3_566 ?
C8 C6 1.396(4) . ?
C8 C7 1.383(4) . ?
C4 C7 1.370(5) . ?
C2 C1 1.423(8) . ?
C2 C3 1.474(6) . ?
C6 C5 1.359(5) . ?

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
O6 Zn1 O9 177.30(7) . . ?
O6 Zn1 O11 92.50(8) . . ?
O10 Zn1 O6 87.15(7) . . ?
O10 Zn1 O7 176.34(8) . . ?
O10 Zn1 O9 91.35(7) . . ?
O10 Zn1 O11 85.15(8) . . ?
O10 Zn1 O8 93.08(8) . . ?
O7 Zn1 O6 93.38(7) . . ?
O7 Zn1 O9 88.25(7) . . ?
O7 Zn1 O11 91.21(8) . . ?
O9 Zn1 O11 89.61(7) . . ?
O8 Zn1 O6 88.96(8) . . ?
O8 Zn1 O7 90.55(8) . . ?
O8 Zn1 O9 88.87(7) . . ?
O8 Zn1 O11 177.64(8) . . ?
C9 O6 Zn1 125.47(15) . . ?
C4 N1 C3 120.1(3) . . ?
C5 N1 C4 120.2(3) . . ?
C5 N1 C3 119.7(3) . . ?
C17 C10 C9 119.8(2) . . ?
C17 C10 C11 119.5(2) . . ?
C11 C10 C9 120.8(2) . . ?
C17 C15 C14 119.0(2) . . ?
C17 C15 C16 120.0(2) . . ?
C14 C15 C16 121.0(2) . . ?
C10 C17 C15 120.7(2) . . ?
O6 C9 C10 116.9(2) . . ?
O5 C9 O6 124.8(2) . . ?
O5 C9 C10 118.3(2) . . ?
C14 C12 C13 120.9(2) . . ?
C14 C12 C11 119.4(2) . . ?
C11 C12 C13 119.6(2) . . ?
C12 C14 C15 120.9(2) . . ?
O1 C13 O2 124.4(2) . . ?
O1 C13 C12 117.9(2) . . ?
O2 C13 C12 117.6(2) . . ?
O4 C16 O3 123.9(2) . . ?
O4 C16 C15 118.4(2) . . ?
O3 C16 C15 117.7(2) . . ?
C6 C8 C8 121.7(4) . 3_566 ?
C7 C8 C8 121.5(3) . 3_566 ?
C7 C8 C6 116.7(3) . . ?
N1 C4 C7 120.4(3) . . ?
C1 C2 C3 119.2(6) . . ?
C5 C6 C8 120.4(3) . . ?
N1 C5 C6 121.3(3) . . ?
C12 C11 C10 120.3(2) . . ?
C4 C7 C8 121.1(3) . . ?
C2 C3 N1 115.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.095
_oxdiff_exptl_absorpt_empirical_full_min 0.759
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liujj0426a
_database_code_depnum_ccdc_archive 'CCDC 1912470'
loop_
_audit_author_name
_audit_author_address
'Jinjian liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H13 O11 Zn, C7 H9 N, H2 O'
_chemical_formula_sum            'C16 H24 N O12 Zn'
_chemical_formula_weight         487.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br Zn'
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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4847(3)
_cell_length_b                   11.7732(3)
_cell_length_c                   15.8026(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.078(2)
_cell_angle_gamma                90
_cell_volume                     1949.38(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2651
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      71.6920
_cell_measurement_theta_min      6.9240
_shelx_estimated_absorpt_T_max   0.536
_shelx_estimated_absorpt_T_min   0.536
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7374
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.157
_diffrn_reflns_theta_min         4.685
_diffrn_ambient_temperature      273(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  37.00   1.00    1.00    --    0.00 -99.00 120.00   26
  2  ω     -3.00  38.00   1.00    1.00    --    0.00 -99.00  60.00   41
  3  ω    -70.00 -36.00   1.00    1.00    --    0.00 178.00-120.00   34
  4  ω    -26.00   1.00   1.00    1.00    --    0.00 -55.00 -96.00   27
  5  ω     36.00 118.00   1.00    1.00    --   54.94  57.00-180.00   82
  6  ω     34.00 118.00   1.00    1.00    --   54.94  57.00 -60.00   84
  7  ω     47.00 110.00   1.00    1.00    --   54.94-125.00  90.00   63
  8  ω     27.00  79.00   1.00    1.00    --   54.94 -38.00 -60.00   52
  9  ω     38.00 144.00   1.00    2.50    --  109.89 -25.00 120.00  106
 10  ω     80.00 111.00   1.00    2.50    --  109.89-111.00-120.00   31
 11  ω     43.00  89.00   1.00    2.50    --  109.89-104.00 175.00   46
 12  ω    116.00 176.00   1.00    2.50    --  109.89 111.00  60.00   60
 13  ω     93.00 164.00   1.00    2.50    --  109.89  64.00 -60.00   71
 14  ω     53.00 131.00   1.00    2.50    --  109.89 -64.00 150.00   78
 15  ω     54.00 152.00   1.00    2.50    --  109.89  12.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0693245000
_diffrn_orient_matrix_UB_12      -0.0867889000
_diffrn_orient_matrix_UB_13      0.0583228000
_diffrn_orient_matrix_UB_21      -0.0984153000
_diffrn_orient_matrix_UB_22      -0.0914150000
_diffrn_orient_matrix_UB_23      -0.0270875000
_diffrn_orient_matrix_UB_31      0.0843377000
_diffrn_orient_matrix_UB_32      -0.0353336000
_diffrn_orient_matrix_UB_33      -0.0733416000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3055
_reflns_number_total             3771
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.4865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1272
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O12(H12A,H12B)
2.b Rotating group:
 O7(H7A,H7B), O8(H8A,H8B), O10(H10A,H10B), O9(H9A,H9B), O11(H11A,H11B)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C10(H10), C13(H13), C6(H6), C3(H3), C4(H4), C5(H5)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.56655(3) 0.45473(3) 0.65422(2) 0.02376(14) Uani 1 1 d . . . . .
O2 O 0.4578(2) 0.46261(16) 0.76476(13) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.3009(3) 0.24489(19) 1.01195(14) 0.0467(6) Uani 1 1 d . . . . .
O1 O 0.3805(2) 0.63814(18) 0.75005(13) 0.0340(5) Uani 1 1 d . . . . .
O6 O 0.2751(2) 0.84660(17) 1.01364(13) 0.0327(5) Uani 1 1 d . . . . .
O4 O 0.3153(2) 0.33010(18) 1.13682(13) 0.0372(5) Uani 1 1 d . . . . .
O7 O 0.6545(2) 0.31552(18) 0.70690(13) 0.0359(5) Uani 1 1 d . . . . .
H7A H 0.6833 0.3286 0.7598 0.054 Uiso 1 1 d GR . . . .
H7B H 0.7221 0.2935 0.6778 0.054 Uiso 1 1 d GR . . . .
O8 O 0.6952(2) 0.56566(18) 0.71240(13) 0.0337(5) Uani 1 1 d . . . . .
H8A H 0.7755 0.5325 0.7350 0.051 Uiso 1 1 d GR . . . .
H8B H 0.6622 0.6045 0.7612 0.051 Uiso 1 1 d GR . . . .
O5 O 0.2999(3) 0.7597(2) 1.13666(14) 0.0541(8) Uani 1 1 d . . . . .
C14 C 0.3210(3) 0.6488(2) 1.01272(17) 0.0232(5) Uani 1 1 d . . . . .
N1 N 0.4851(3) 0.0538(3) 0.2818(2) 0.0427(7) Uani 1 1 d . . . . .
C9 C 0.3681(3) 0.5476(2) 0.88415(17) 0.0231(5) Uani 1 1 d . . . . .
O12 O 0.6505(3) 0.7556(3) 0.2613(2) 0.0586(8) Uani 1 1 d . . . . .
H12A H 0.7270 0.7792 0.2596 0.088 Uiso 1 1 d G . . . .
H12B H 0.6421 0.6957 0.2316 0.088 Uiso 1 1 d G . . . .
C8 C 0.4046(3) 0.5502(2) 0.79285(17) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.3326(3) 0.4437(2) 1.01343(17) 0.0237(5) Uani 1 1 d . . . . .
C15 C 0.2976(3) 0.7599(2) 1.05762(17) 0.0272(6) Uani 1 1 d . . . . .
C16 C 0.3455(3) 0.6497(2) 0.92675(17) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.3469 0.7182 0.8975 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3161(3) 0.3308(2) 1.05714(18) 0.0268(6) Uani 1 1 d . . . . .
C7 C 0.4976(3) 0.0112(3) 0.4541(2) 0.0363(7) Uani 1 1 d . . . . .
C10 C 0.3611(3) 0.4457(2) 0.92787(17) 0.0240(5) Uani 1 1 d . . . . .
H10 H 0.3755 0.3777 0.8998 0.029 Uiso 1 1 calc R . . . .
C13 C 0.3167(3) 0.5460(2) 1.05590(16) 0.0236(5) Uani 1 1 d . . . . .
H13 H 0.3030 0.5456 1.1137 0.028 Uiso 1 1 calc R . . . .
C6 C 0.5053(4) 0.1219(3) 0.4220(3) 0.0511(9) Uani 1 1 d . . . . .
H6 H 0.5153 0.1829 0.4590 0.061 Uiso 1 1 calc R . . . .
C3 C 0.4981(4) 0.1403(3) 0.3369(3) 0.0515(9) Uani 1 1 d . . . . .
H3 H 0.5023 0.2143 0.3165 0.062 Uiso 1 1 calc R . . . .
C4 C 0.4763(4) -0.0529(3) 0.3106(3) 0.0469(9) Uani 1 1 d . . . . .
H4 H 0.4657 -0.1124 0.2723 0.056 Uiso 1 1 calc R . . . .
C2 C 0.4779(4) 0.0760(4) 0.1891(3) 0.0525(9) Uani 1 1 d . . . . .
H2A H 0.3977 0.0467 0.1655 0.063 Uiso 1 1 calc R . . . .
H2B H 0.4794 0.1573 0.1794 0.063 Uiso 1 1 calc R . . . .
C1 C 0.5842(7) 0.0227(6) 0.1456(4) 0.101(2) Uani 1 1 d . . . . .
H1A H 0.6637 0.0472 0.1715 0.151 Uiso 1 1 calc GR . . . .
H1B H 0.5807 0.0447 0.0870 0.151 Uiso 1 1 calc GR . . . .
H1C H 0.5775 -0.0584 0.1497 0.151 Uiso 1 1 calc GR . . . .
O10 O 0.4354(2) 0.33752(19) 0.59651(14) 0.0353(5) Uani 1 1 d . . . . .
H10A H 0.3661 0.3711 0.5579 0.053 Uiso 1 1 d GR . . . .
H10B H 0.3750 0.2941 0.6339 0.053 Uiso 1 1 d GR . . . .
C5 C 0.4826(4) -0.0755(3) 0.3954(3) 0.0440(8) Uani 1 1 d . . . . .
H5 H 0.4766 -0.1502 0.4140 0.053 Uiso 1 1 calc R . . . .
O9 O 0.6844(2) 0.44534(16) 0.54825(12) 0.0269(4) Uani 1 1 d . . . . .
H9A H 0.7188 0.5107 0.5392 0.040 Uiso 1 1 d GR . . . .
H9B H 0.6388 0.4326 0.5026 0.040 Uiso 1 1 d GR . . . .
O11 O 0.5299(2) 0.40749(17) 0.40297(13) 0.0296(4) Uani 1 1 d . . . . .
H11A H 0.5722 0.4294 0.4482 0.044 Uiso 1 1 d GR . . . .
H11B H 0.5887 0.3828 0.3705 0.044 Uiso 1 1 d GR . . . .


_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
Zn1 O2 2.1221(19) . ?
Zn1 O7 2.043(2) . ?
Zn1 O8 2.069(2) . ?
Zn1 O10 2.130(2) . ?
Zn1 O9 2.1199(19) . ?
Zn1 O11 2.099(2) 3_666 ?
O2 C8 1.261(3) . ?
O3 C12 1.245(4) . ?
O1 C8 1.258(3) . ?
O6 C15 1.252(4) . ?
O4 C12 1.260(3) . ?
O5 C15 1.248(4) . ?
C14 C15 1.512(4) . ?
C14 C16 1.392(4) . ?
C14 C13 1.391(4) . ?
N1 C3 1.344(5) . ?
N1 C4 1.340(4) . ?
N1 C2 1.486(5) . ?
C9 C8 1.506(3) . ?
C9 C16 1.402(4) . ?
C9 C10 1.388(4) . ?
C11 C12 1.511(4) . ?
C11 C10 1.395(4) . ?
C11 C13 1.392(4) . ?
C7 C7 1.475(7) 3_656 ?
C7 C6 1.401(5) . ?
C7 C5 1.384(5) . ?
C6 C3 1.362(6) . ?
C4 C5 1.366(6) . ?
C2 C1 1.471(7) . ?
O11 Zn1 2.099(2) 3_666 ?

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
O2 Zn1 O10 91.32(9) . . ?
O7 Zn1 O2 87.00(8) . . ?
O7 Zn1 O8 92.75(10) . . ?
O7 Zn1 O10 85.97(10) . . ?
O7 Zn1 O9 90.71(8) . . ?
O7 Zn1 O11 177.28(9) . 3_666 ?
O8 Zn1 O2 88.14(9) . . ?
O8 Zn1 O10 178.63(9) . . ?
O8 Zn1 O9 89.69(8) . . ?
O8 Zn1 O11 89.97(9) . 3_666 ?
O9 Zn1 O2 176.77(8) . . ?
O9 Zn1 O10 90.80(8) . . ?
O11 Zn1 O2 93.21(8) 3_666 . ?
O11 Zn1 O10 91.31(9) 3_666 . ?
O11 Zn1 O9 89.18(8) 3_666 . ?
C8 O2 Zn1 125.70(17) . . ?
C16 C14 C15 119.4(2) . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 C16 119.7(2) . . ?
C3 N1 C2 120.4(3) . . ?
C4 N1 C3 119.8(3) . . ?
C4 N1 C2 119.8(3) . . ?
C16 C9 C8 119.7(2) . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 C16 119.3(2) . . ?
O2 C8 C9 116.9(2) . . ?
O1 C8 O2 124.5(2) . . ?
O1 C8 C9 118.6(2) . . ?
C10 C11 C12 119.3(2) . . ?
C13 C11 C12 121.6(2) . . ?
C13 C11 C10 119.1(2) . . ?
O6 C15 C14 118.3(2) . . ?
O5 C15 O6 123.6(3) . . ?
O5 C15 C14 118.0(3) . . ?
C14 C16 C9 120.2(2) . . ?
O3 C12 O4 124.2(3) . . ?
O3 C12 C11 117.8(3) . . ?
O4 C12 C11 117.9(2) . . ?
C6 C7 C7 121.5(4) . 3_656 ?
C5 C7 C7 121.7(4) . 3_656 ?
C5 C7 C6 116.8(3) . . ?
C9 C10 C11 120.9(2) . . ?
C14 C13 C11 120.7(2) . . ?
C3 C6 C7 120.2(4) . . ?
N1 C3 C6 121.3(3) . . ?
N1 C4 C5 121.0(4) . . ?
C1 C2 N1 111.9(4) . . ?
C4 C5 C7 120.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liujj0426d
_database_code_depnum_ccdc_archive 'CCDC 1912472'
loop_
_audit_author_name
_audit_author_address
'Jinjian liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H13 O11 Zn, C6 H7 N, 2(H2 O)'
_chemical_formula_sum            'C15 H24 N O13 Zn'
_chemical_formula_weight         491.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br Zn'
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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5890(3)
_cell_length_b                   11.8282(3)
_cell_length_c                   15.8135(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.837(2)
_cell_angle_gamma                90
_cell_volume                     1979.61(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2969
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.4470
_cell_measurement_theta_min      3.7360
_shelx_estimated_absorpt_T_max   0.647
_shelx_estimated_absorpt_T_min   0.535
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7812
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.434
_diffrn_reflns_theta_min         4.669
_diffrn_ambient_temperature      273(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  59.00   1.00    1.00    --    0.00  57.00-120.00   25
  2  ω     -3.00  29.00   1.00    1.00    --    0.00 -99.00 120.00   32
  3  ω    -13.00  18.00   1.00    1.00    --    0.00  57.00-120.00   31
  4  ω    -77.00 -52.00   1.00    1.00    --    0.00 178.00-120.00   25
  5  ω     39.00 100.00   1.00    1.00    --   55.26  77.00  30.00   61
  6  ω     40.00 102.00   1.00    1.00    --   55.26  57.00 -90.00   62
  7  ω     55.00  81.00   1.00    1.00    --   55.26 -99.00-180.00   26
  8  ω     31.00 109.00   1.00    1.00    --   55.26-131.00-155.00   78
  9  ω     34.00 112.00   1.00    1.00    --   55.26  57.00-180.00   78
 10  ω     11.00  37.00   1.00    1.00    --   55.26 -77.00  90.00   26
 11  ω     51.00  88.00   1.00    2.00    --  110.51-131.00-155.00   37
 12  ω     39.00 106.00   1.00    2.00    --  110.51-111.00-120.00   67
 13  ω     84.00 133.00   1.00    2.00    --  110.51 -64.00-120.00   49
 14  ω     41.00 132.00   1.00    2.00    --  110.51 -50.00   0.00   91
 15  ω    102.00 166.00   1.00    2.00    --  110.51 111.00 -60.00   64
 16  ω    151.00 177.00   1.00    2.00    --  110.51 111.00 150.00   26
 17  ω     88.00 114.00   1.00    2.00    --  110.51-111.00 -30.00   26
 18  ω    111.00 178.00   1.00    2.00    --  110.51  64.00  30.00   67
 19  ω     44.00  71.00   1.00    2.00    --  110.51 -64.00-120.00   27
 20  ω     37.00  87.00   1.00    2.00    --  110.51 -12.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0250591000
_diffrn_orient_matrix_UB_12      0.1118101000
_diffrn_orient_matrix_UB_13      0.0476247000
_diffrn_orient_matrix_UB_21      -0.0137705000
_diffrn_orient_matrix_UB_22      -0.0617891000
_diffrn_orient_matrix_UB_23      0.0849893000
_diffrn_orient_matrix_UB_31      0.1426939000
_diffrn_orient_matrix_UB_32      -0.0255280000
_diffrn_orient_matrix_UB_33      0.0029965000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3245
_reflns_number_total             3822
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0936P)²+2.0058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1556
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13A,H13B), O12(H12A,H12B)
2.b Rotating group:
 O9(H9A,H9B), O10(H10A,H10B), O8(H8A,H8B), O11(H11A,H11B), O7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C13(H13), C6(H6), C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.56992(4) -0.05038(3) 0.15794(2) 0.02516(17) Uani 1 1 d . . . . .
O2 O 0.4759(2) -0.0337(2) 0.27092(14) 0.0321(5) Uani 1 1 d . . . . .
O9 O 0.6509(3) -0.1930(2) 0.20892(15) 0.0412(6) Uani 1 1 d . . . . .
H9A H 0.6028 -0.2587 0.1999 0.062 Uiso 1 1 d GR . . . .
H9B H 0.6646 -0.1906 0.2679 0.062 Uiso 1 1 d GR . . . .
O3 O 0.3033(3) -0.2470(2) 0.51569(16) 0.0479(7) Uani 1 1 d . . . . .
O4 O 0.2967(3) -0.1561(2) 0.63690(16) 0.0526(8) Uani 1 1 d . . . . .
O1 O 0.3939(3) 0.1379(2) 0.25020(15) 0.0473(7) Uani 1 1 d . . . . .
O6 O 0.2749(3) 0.3533(2) 0.50945(15) 0.0396(6) Uani 1 1 d . . . . .
O5 O 0.2989(4) 0.2685(3) 0.63268(16) 0.0696(12) Uani 1 1 d . . . . .
C11 C 0.3209(3) 0.1561(3) 0.51056(19) 0.0268(6) Uani 1 1 d . . . . .
C8 C 0.3759(3) 0.0535(3) 0.38533(19) 0.0257(6) Uani 1 1 d . . . . .
C7 C 0.4182(3) 0.0524(3) 0.2950(2) 0.0281(7) Uani 1 1 d . . . . .
C10 C 0.3507(3) 0.1548(3) 0.42585(19) 0.0283(6) Uani 1 1 d . . . . .
H10 H 0.3538 0.2223 0.3959 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3648(3) -0.0478(3) 0.4294(2) 0.0266(6) Uani 1 1 d . . . . .
H9 H 0.3806 -0.1159 0.4022 0.032 Uiso 1 1 calc R . . . .
C14 C 0.3305(3) -0.0482(3) 0.51358(19) 0.0250(6) Uani 1 1 d . . . . .
C12 C 0.2954(3) 0.2680(3) 0.5536(2) 0.0310(7) Uani 1 1 d . . . . .
C13 C 0.3125(3) 0.0545(3) 0.55432(19) 0.0260(6) Uani 1 1 d . . . . .
H13 H 0.2947 0.0552 0.6115 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3095(3) -0.1589(3) 0.5588(2) 0.0309(7) Uani 1 1 d . . . . .
N1 N 0.5034(5) 0.4379(4) 0.2174(5) 0.0853(17) Uani 1 1 d . . . . .
C5 C 0.4983(4) 0.4884(4) 0.0456(4) 0.0719(17) Uani 1 1 d . . . . .
C6 C 0.5050(6) 0.3761(4) 0.0747(5) 0.087(2) Uani 1 1 d . . . . .
H6 H 0.5060 0.3162 0.0366 0.105 Uiso 1 1 calc R . . . .
C2 C 0.5100(7) 0.3568(5) 0.1589(6) 0.097(2) Uani 1 1 d . . . . .
H2 H 0.5186 0.2824 0.1774 0.116 Uiso 1 1 calc R . . . .
C4 C 0.4935(7) 0.5708(5) 0.1061(6) 0.094(2) Uani 1 1 d . . . . .
H4 H 0.4904 0.6460 0.0891 0.113 Uiso 1 1 calc R . . . .
C3 C 0.4932(9) 0.5468(6) 0.1901(6) 0.105(3) Uani 1 1 d . . . . .
H3 H 0.4859 0.6050 0.2291 0.126 Uiso 1 1 calc R . . . .
O10 O 0.6781(2) -0.06239(18) 0.04718(14) 0.0285(5) Uani 1 1 d . . . . .
H10A H 0.7251 -0.0022 0.0413 0.043 Uiso 1 1 d GR . . . .
H10B H 0.6290 -0.0614 0.0016 0.043 Uiso 1 1 d GR . . . .
O8 O 0.4261(3) -0.1583(2) 0.10713(18) 0.0445(6) Uani 1 1 d . . . . .
H8A H 0.3769 -0.1229 0.0686 0.067 Uiso 1 1 d GR . . . .
H8B H 0.3711 -0.1776 0.1461 0.067 Uiso 1 1 d GR . . . .
O13 O 0.4246(7) 0.6660(8) 0.3789(6) 0.161(3) Uani 1 1 d . . . . .
H13A H 0.4041 0.7021 0.4228 0.241 Uiso 1 1 d G . . . .
H13B H 0.3548 0.6449 0.3562 0.241 Uiso 1 1 d G . . . .
O12 O 0.2977(7) -0.2206(6) 0.2409(3) 0.159(3) Uani 1 1 d . . . . .
H12A H 0.2456 -0.2627 0.2659 0.238 Uiso 1 1 d G . . . .
H12B H 0.3693 -0.2511 0.2512 0.238 Uiso 1 1 d G . . . .
O11 O 0.5181(2) -0.0918(2) -0.09938(14) 0.0341(5) Uani 1 1 d . . . . .
H11A H 0.5676 -0.0715 -0.0562 0.051 Uiso 1 1 d GR . . . .
H11B H 0.5710 -0.1245 -0.1336 0.051 Uiso 1 1 d GR . . . .
C1 C 0.5066(8) 0.4157(7) 0.3078(6) 0.108(3) Uani 1 1 d . . . . .
H1A H 0.4228 0.4224 0.3288 0.163 Uiso 1 1 calc GR . . . .
H1B H 0.5611 0.4695 0.3361 0.163 Uiso 1 1 calc GR . . . .
H1C H 0.5378 0.3407 0.3183 0.163 Uiso 1 1 calc GR . . . .
O7 O 0.7126(3) 0.0511(2) 0.21103(15) 0.0367(6) Uani 1 1 d . . . . .
H7A H 0.6886 0.0832 0.2580 0.055 Uiso 1 1 d GR . . . .
H7B H 0.7276 0.1093 0.1784 0.055 Uiso 1 1 d GR . . . .


_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
Zn1 O2 2.082(2) . ?
Zn1 O9 2.046(2) . ?
Zn1 O10 2.128(2) . ?
Zn1 O8 2.124(3) . ?
Zn1 O11 2.121(2) 3_655 ?
Zn1 O7 2.085(2) . ?
O2 C7 1.253(4) . ?
O3 C15 1.246(4) . ?
O4 C15 1.247(4) . ?
O1 C7 1.256(4) . ?
O6 C12 1.242(4) . ?
O5 C12 1.249(4) . ?
C11 C10 1.386(4) . ?
C11 C12 1.517(4) . ?
C11 C13 1.391(4) . ?
C8 C7 1.512(4) . ?
C8 C10 1.388(4) . ?
C8 C9 1.393(4) . ?
C9 C14 1.392(4) . ?
C14 C13 1.391(4) . ?
C14 C15 1.511(4) . ?
N1 C2 1.335(9) . ?
N1 C3 1.362(8) . ?
N1 C1 1.453(9) . ?
C5 C5 1.470(13) 3_665 ?
C5 C6 1.406(8) . ?
C5 C4 1.367(9) . ?
C6 C2 1.351(10) . ?
C4 C3 1.359(11) . ?
O11 Zn1 2.121(2) 3_655 ?

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
O2 Zn1 O10 175.74(10) . . ?
O2 Zn1 O8 91.43(11) . . ?
O2 Zn1 O11 94.83(9) . 3_655 ?
O2 Zn1 O7 87.71(10) . . ?
O9 Zn1 O2 86.88(10) . . ?
O9 Zn1 O10 92.27(9) . . ?
O9 Zn1 O8 86.54(11) . . ?
O9 Zn1 O11 176.77(10) . 3_655 ?
O9 Zn1 O7 91.56(11) . . ?
O8 Zn1 O10 92.68(10) . . ?
O11 Zn1 O10 86.22(9) 3_655 . ?
O11 Zn1 O8 90.67(10) 3_655 . ?
O7 Zn1 O10 88.14(10) . . ?
O7 Zn1 O8 177.96(10) . . ?
O7 Zn1 O11 91.25(10) . 3_655 ?
C7 O2 Zn1 126.0(2) . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 C13 119.4(3) . . ?
C13 C11 C12 121.0(3) . . ?
C10 C8 C7 120.8(3) . . ?
C10 C8 C9 119.4(3) . . ?
C9 C8 C7 119.8(3) . . ?
O2 C7 O1 125.2(3) . . ?
O2 C7 C8 117.2(3) . . ?
O1 C7 C8 117.6(3) . . ?
C11 C10 C8 120.6(3) . . ?
C14 C9 C8 120.6(3) . . ?
C9 C14 C15 120.1(3) . . ?
C13 C14 C9 119.0(3) . . ?
C13 C14 C15 120.9(3) . . ?
O6 C12 O5 123.9(3) . . ?
O6 C12 C11 119.1(3) . . ?
O5 C12 C11 117.0(3) . . ?
C14 C13 C11 120.8(3) . . ?
O3 C15 O4 123.9(3) . . ?
O3 C15 C14 118.2(3) . . ?
O4 C15 C14 117.9(3) . . ?
C2 N1 C3 117.7(8) . . ?
C2 N1 C1 123.5(7) . . ?
C3 N1 C1 118.8(7) . . ?
C6 C5 C5 119.6(7) . 3_665 ?
C4 C5 C5 123.8(7) . 3_665 ?
C4 C5 C6 116.6(7) . . ?
C2 C6 C5 118.8(6) . . ?
N1 C2 C6 124.1(7) . . ?
C3 C4 C5 122.4(6) . . ?
C4 C3 N1 120.3(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.778
