# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1471950'
_audit_update_record             
;
2016-06-15 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            'C28 H41.70 N12.40 O18.45 Zn4'
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C28 H41.70 N12.40 O18.45 Zn4'
_chemical_formula_sum            'C28 H41.70 N12.40 O18.45 Zn4'
_chemical_formula_weight         1108.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           81
_space_group_name_H-M_alt        'P -4'
_space_group_name_Hall           'P -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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   14.952(2)
_cell_length_b                   14.952(2)
_cell_length_c                   9.0826(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2030.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8054
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    2.426
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            21606
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.046
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4655
_reflns_number_gt                4278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+2.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4655
_refine_ls_number_parameters     316
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.021
_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
Zn1 Zn 0.29197(5) 0.00616(7) 1.01181(8) 0.01962(17) Uani 1 1 d . . . . .
Zn2 Zn 0.50719(11) 0.33627(7) -0.00282(18) 0.0501(3) Uani 1 1 d . . . . .
O2WA O 0.4711(9) 0.2046(7) -0.0571(16) 0.055(4) Uani 0.80(2) 1 d . . P A 1
O2WB O 0.513(4) 0.206(3) 0.024(6) 0.055(4) Uani 0.20(2) 1 d . . P A 2
O11 O 0.4362(7) 0.3219(8) 0.1853(11) 0.068(3) Uani 1 1 d . . . . .
O12 O 0.3147(6) 0.4008(7) 0.1647(11) 0.064(3) Uani 1 1 d . . . . .
N11 N 0.0881(5) 0.2006(5) 1.0520(7) 0.0243(15) Uani 1 1 d . . . . .
N12 N 0.0696(7) 0.1400(7) 1.1555(13) 0.047(3) Uani 1 1 d . . . . .
N13 N 0.1367(8) 0.0837(7) 1.1690(12) 0.050(3) Uani 1 1 d . . . . .
N14 N 0.1988(5) 0.1039(5) 1.0647(8) 0.0269(17) Uani 1 1 d . . . . .
N15 N 0.2314(8) 0.2598(8) 0.6219(10) 0.055(3) Uani 1 1 d D . . . .
H15C H 0.2229(19) 0.3143(14) 0.651(3) 0.066 Uiso 1 1 d D U . . .
C11 C 0.1701(6) 0.1743(6) 0.9976(15) 0.0365(17) Uani 1 1 d . . . . .
C12 C 0.2253(8) 0.2282(9) 0.8895(11) 0.046(2) Uani 1 1 d . . . . .
H12A H 0.2163 0.2919 0.9035 0.056 Uiso 1 1 calc R U . . .
H12B H 0.2885 0.2146 0.8990 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1909(9) 0.1990(10) 0.7488(14) 0.058(3) Uani 1 1 d D . . . .
H13A H 0.1261 0.2035 0.7483 0.070 Uiso 1 1 calc R U . . .
H13B H 0.2070 0.1370 0.7321 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3308(8) 0.2423(11) 0.6058(15) 0.053(4) Uani 1 1 d D . . . .
H14A H 0.3609 0.2575 0.6970 0.064 Uiso 1 1 calc R U . . .
H14B H 0.3406 0.1792 0.5867 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3695(8) 0.2964(13) 0.4823(18) 0.080(5) Uani 1 1 d . . . . .
H15A H 0.3740 0.3583 0.5135 0.096 Uiso 1 1 calc R U . . .
H15B H 0.4296 0.2752 0.4620 0.096 Uiso 1 1 calc R U . . .
C16 C 0.3188(9) 0.2925(10) 0.3506(16) 0.062(4) Uani 1 1 d . . . . .
H16A H 0.3235 0.2296 0.3211 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3586(7) 0.3426(8) 0.2203(12) 0.041(2) Uani 1 1 d . . . . .
C18 C 0.2228(10) 0.3072(16) 0.3591(17) 0.084(7) Uani 1 1 d . . . . .
H18A H 0.1953 0.2949 0.2645 0.101 Uiso 1 1 calc R U . . .
H18B H 0.2105 0.3689 0.3851 0.101 Uiso 1 1 calc R U . . .
C19 C 0.1821(10) 0.2394(12) 0.486(2) 0.092(6) Uani 1 1 d D . . . .
H19A H 0.1186 0.2498 0.4993 0.110 Uiso 1 1 calc R U . . .
H19B H 0.1909 0.1775 0.4575 0.110 Uiso 1 1 calc R U . . .
O21 O 0.4170(5) -0.0687(5) 0.8775(7) 0.0340(17) Uani 1 1 d . . . . .
O22 O 0.3403(5) 0.0520(4) 0.8170(7) 0.0301(14) Uani 1 1 d . . . . .
O23 O 0.3405(5) -0.0326(4) 0.2102(7) 0.0309(15) Uani 1 1 d . . . . .
O24 O 0.4242(7) 0.0822(6) 0.1641(8) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.4013(6) -0.0047(8) 0.7920(7) 0.0213(17) Uani 1 1 d . . . . .
C22 C 0.4532(6) 0.0005(7) 0.6511(7) 0.0183(17) Uani 1 1 d . . . . .
C23 C 0.4068(4) 0.0072(6) 0.5155(8) 0.0219(14) Uani 1 1 d . . . . .
H23A H 0.3449 0.0129 0.5151 0.026 Uiso 1 1 calc R U . . .
C24 C 0.4528(6) 0.0055(7) 0.3843(8) 0.0213(19) Uani 1 1 d . . . . .
C25 C 0.4029(6) 0.0204(6) 0.2401(8) 0.023(2) Uani 1 1 d . . . . .
OH O 0.411(2) 0.401(3) -0.112(3) 0.044(4) Uani 0.6 1 d . U P A 1
H1A H 0.4392 0.4199 -0.1837 0.066 Uiso 0.6 1 d R U P A 1
O3W O -0.0218(14) 0.162(2) 0.511(4) 0.130(10) Uani 0.5 1 d . . P B 1
N31 N 0.427(6) 0.412(7) -0.126(7) 0.065(9) Uani 0.4 1 d D U P A 2
N32 N 0.452(2) 0.443(2) -0.239(3) 0.066(6) Uani 0.4 1 d D U P A 2
N33 N 0.5000 0.5000 -0.327(3) 0.116(6) Uani 0.8 2 d DS TU P A 2
O5W O 0.0000 0.0000 0.585(6) 0.12(2) Uani 0.25 2 d S TU P C 2
O4W O 0.5615(8) 0.2100(8) 0.3064(16) 0.093(4) Uani 1 1 d . . . . .


_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 O23 2.027(6) 1_556 ?
Zn1 O22 2.030(6) . ?
Zn1 N11 2.047(7) 3_557 ?
Zn1 N14 2.076(7) . ?
Zn1 C21 2.585(8) . ?
Zn2 O2WB 1.97(4) . ?
Zn2 N31 1.99(9) . ?
Zn2 OH 2.00(4) . ?
Zn2 O11 2.023(9) . ?
Zn2 O12 2.039(8) 4_655 ?
Zn2 OH 2.06(4) 4_655 ?
Zn2 O2WA 2.100(11) . ?
Zn2 N31 2.16(11) 4_655 ?
O11 C17 1.242(14) . ?
O12 C17 1.201(15) . ?
O12 Zn2 2.039(8) 3_565 ?
N11 N12 1.334(12) . ?
N11 C11 1.380(12) . ?
N11 Zn1 2.047(7) 4_557 ?
N12 N13 1.316(12) . ?
N13 N14 1.360(12) . ?
N14 C11 1.290(13) . ?
N15 C19 1.47(2) . ?
N15 C14 1.516(17) . ?
N15 C13 1.588(16) . ?
N15 H15C 0.866(15) . ?
C11 C12 1.513(13) . ?
C12 C13 1.445(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.500(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.42(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.453(19) . ?
C16 C17 1.521(14) . ?
C16 H16A 0.9800 . ?
C18 C19 1.65(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O21 C21 1.255(12) . ?
O22 C21 1.265(13) . ?
O23 C25 1.254(12) . ?
O23 Zn1 2.027(6) 1_554 ?
O24 C25 1.197(12) . ?
C21 C22 1.499(10) . ?
C22 C22 1.399(17) 2_655 ?
C22 C23 1.418(10) . ?
C23 C24 1.376(12) . ?
C23 H23A 0.9300 . ?
C24 C24 1.420(18) 2_655 ?
C24 C25 1.523(11) . ?
OH Zn2 2.06(4) 3_565 ?
OH H1A 0.8216 . ?
N31 N32 1.19(2) . ?
N31 Zn2 2.16(11) 3_565 ?
N32 N33 1.379(18) . ?
N33 N32 1.379(18) 2_665 ?
O5W O5W 1.54(12) 3_556 ?

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
O23 Zn1 O22 138.0(2) 1_556 . ?
O23 Zn1 N11 107.1(3) 1_556 3_557 ?
O22 Zn1 N11 102.9(3) . 3_557 ?
O23 Zn1 N14 103.6(3) 1_556 . ?
O22 Zn1 N14 101.7(3) . . ?
N11 Zn1 N14 95.9(3) 3_557 . ?
O23 Zn1 C21 116.2(3) 1_556 . ?
O22 Zn1 C21 28.7(3) . . ?
N11 Zn1 C21 99.2(3) 3_557 . ?
N14 Zn1 C21 130.3(3) . . ?
O2WB Zn2 N31 131(3) . . ?
O2WB Zn2 O11 79.1(12) . . ?
N31 Zn2 O11 102.5(19) . . ?
OH Zn2 O11 95.5(7) . . ?
O2WB Zn2 O12 84.5(12) . 4_655 ?
N31 Zn2 O12 95(2) . 4_655 ?
OH Zn2 O12 101.7(8) . 4_655 ?
O11 Zn2 O12 161.1(4) . 4_655 ?
OH Zn2 OH 118.0(18) . 4_655 ?
O11 Zn2 OH 88.8(8) . 4_655 ?
O12 Zn2 OH 90.1(7) 4_655 4_655 ?
OH Zn2 O2WA 98.8(11) . . ?
O11 Zn2 O2WA 87.9(5) . . ?
O12 Zn2 O2WA 81.7(4) 4_655 . ?
OH Zn2 O2WA 143.3(10) 4_655 . ?
O2WB Zn2 N31 122(3) . 4_655 ?
N31 Zn2 N31 107(5) . 4_655 ?
O11 Zn2 N31 84.5(17) . 4_655 ?
O12 Zn2 N31 96.3(15) 4_655 4_655 ?
C17 O11 Zn2 132.9(8) . . ?
C17 O12 Zn2 134.9(8) . 3_565 ?
N12 N11 C11 104.1(8) . . ?
N12 N11 Zn1 120.7(6) . 4_557 ?
C11 N11 Zn1 134.5(6) . 4_557 ?
N13 N12 N11 110.0(9) . . ?
N12 N13 N14 108.3(9) . . ?
C11 N14 N13 106.5(8) . . ?
C11 N14 Zn1 133.5(7) . . ?
N13 N14 Zn1 117.5(6) . . ?
C19 N15 C14 112.0(11) . . ?
C19 N15 C13 107.5(10) . . ?
C14 N15 C13 110.2(10) . . ?
C19 N15 H15C 112(2) . . ?
C14 N15 H15C 110(2) . . ?
C13 N15 H15C 105(2) . . ?
N14 C11 N11 111.0(8) . . ?
N14 C11 C12 124.0(10) . . ?
N11 C11 C12 124.5(10) . . ?
C13 C12 C11 102.7(9) . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C12 C13 N15 109.5(9) . . ?
C12 C13 H13A 109.8 . . ?
N15 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
N15 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 N15 111.0(10) . . ?
C15 C14 H14A 109.4 . . ?
N15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
N15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 113.7(12) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C18 118.5(13) . . ?
C15 C16 C17 115.2(12) . . ?
C18 C16 C17 110.7(11) . . ?
C15 C16 H16A 103.4 . . ?
C18 C16 H16A 103.4 . . ?
C17 C16 H16A 103.4 . . ?
O12 C17 O11 125.6(10) . . ?
O12 C17 C16 118.0(10) . . ?
O11 C17 C16 116.3(10) . . ?
C16 C18 C19 108.0(12) . . ?
C16 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
C16 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
N15 C19 C18 105.9(13) . . ?
N15 C19 H19A 110.6 . . ?
C18 C19 H19A 110.6 . . ?
N15 C19 H19B 110.6 . . ?
C18 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
C21 O22 Zn1 100.8(5) . . ?
C25 O23 Zn1 106.2(6) . 1_554 ?
O21 C21 O22 122.3(7) . . ?
O21 C21 C22 118.1(9) . . ?
O22 C21 C22 119.5(9) . . ?
O21 C21 Zn1 71.8(5) . . ?
O22 C21 Zn1 50.5(4) . . ?
C22 C21 Zn1 169.6(7) . . ?
C22 C22 C23 119.4(4) 2_655 . ?
C22 C22 C21 121.2(4) 2_655 . ?
C23 C22 C21 119.5(7) . . ?
C24 C23 C22 120.4(6) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C24 119.9(4) . 2_655 ?
C23 C24 C25 119.8(8) . . ?
C24 C24 C25 120.2(5) 2_655 . ?
O24 C25 O23 124.1(9) . . ?
O24 C25 C24 118.6(9) . . ?
O23 C25 C24 117.3(8) . . ?
Zn2 OH Zn2 117.4(15) . 3_565 ?
Zn2 OH H1A 101.1 . . ?
Zn2 OH H1A 116.7 3_565 . ?
N32 N31 Zn2 121(7) . . ?
N32 N31 Zn2 117(7) . 3_565 ?
Zn2 N31 Zn2 113(3) . 3_565 ?
N31 N32 N33 156(5) . . ?
N32 N33 N32 109(3) 2_665 . ?

_refine_diff_density_max         0.707
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.114

_shelxl_version_number           2014/6

