# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_21699_sq
_database_code_depnum_ccdc_archive 'CCDC 2071927'
loop_
_audit_author_name
_audit_author_address
'Mao-Long Chen'
;Changsha University of Science and Technology
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-09-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_exp_21699_sq        
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The theta_max is 60
;
# Added during the CSD deposition process: Monday 22 March 2021 04:54 AM
# end Validation Reply Form

_audit_creation_date             2020-07-16
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        Zn-MOF
_chemical_formula_moiety         'C14 H13 N O6 Zn, C2 H8 N'
_chemical_formula_sum            'C16 H21 N2 O6 Zn'
_chemical_formula_weight         402.72
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   18.3597(8)
_cell_length_b                   30.8839(13)
_cell_length_c                   11.3262(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6422.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    193
_cell_measurement_theta_max      60.4570
_cell_measurement_theta_min      4.1500
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (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    0.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11235
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        60.698
_diffrn_reflns_theta_max         60.698
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      193.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  32.00   1.00    2.50    --    0.78   0.00 -30.00   52
  2  ω     52.00  86.00   1.00    2.50    --    0.78   0.00 -30.00   34
  3  ω   -113.00 -32.00   1.00   15.00    --  -46.29 126.00-120.00   81
  4  ω     51.00 122.00   1.00   15.00    --   47.85  57.00-180.00   71
  5  ω     80.00 110.00   1.00   15.00    --   47.85 126.00-120.00   30
  6  ω   -166.00 -64.00   1.00   35.00    --  -93.36 -50.00  90.00  102
  7  ω   -154.00-126.00   1.00   35.00    --  -93.36-112.00 -90.00   28
  8  ω   -107.00 -22.00   1.00   35.00    --  -93.36  64.00 -30.00   85
  9  ω   -132.00-107.00   1.00   35.00    --  -93.36-112.00-180.00   25
 10  ω     64.00  90.00   1.00   35.00    --   94.92-112.00-180.00   26
 11  ω     22.00  48.00   1.00   35.00    --   94.92-112.00-180.00   26
 12  ω     58.00  85.00   1.00   35.00    --   94.92-112.00 -30.00   27
 13  ω     16.00  41.00   1.00   35.00    --   94.92-112.00 -30.00   25
 14  ω     52.00  89.00   1.00   35.00    --   94.92-112.00 120.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0617905000
_diffrn_orient_matrix_UB_12      0.0251834000
_diffrn_orient_matrix_UB_13      -0.0614432000
_diffrn_orient_matrix_UB_21      -0.0546868000
_diffrn_orient_matrix_UB_22      -0.0174468000
_diffrn_orient_matrix_UB_23      0.0915827000
_diffrn_orient_matrix_UB_31      0.0151527000
_diffrn_orient_matrix_UB_32      0.0393870000
_diffrn_orient_matrix_UB_33      0.0795679000
_diffrn_radiation_monochromator  mirror
_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 Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4169
_reflns_number_total             4910
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.079
_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)+(0.0749P)²+14.9771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1901
_refine_special_details          SQUEEZE
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.25200(3) 0.42569(2) 0.18144(5) 0.0382(2) Uani 1 1 d . . . . .
O4 O 0.19216(16) 0.47024(11) -0.0343(3) 0.0481(8) Uani 1 1 d . . . . .
O5 O 0.33126(17) 0.50208(11) 0.1741(3) 0.0465(8) Uani 1 1 d . . . . .
O2 O 0.34178(16) 0.43690(10) 0.0920(3) 0.0446(7) Uani 1 1 d . . . . .
O1 O 0.15727(16) 0.45215(10) 0.1485(3) 0.0429(7) Uani 1 1 d . . . . .
N1 N 0.2691(2) 0.44070(13) 0.3568(3) 0.0453(9) Uani 1 1 d . . . . .
H1 H 0.281940 0.472098 0.362086 0.054 Uiso 1 1 calc R . . . .
C3 C 0.0215(2) 0.49092(16) 0.1149(4) 0.0445(11) Uani 1 1 d . . . . .
H3 H 0.035681 0.484586 0.193722 0.053 Uiso 1 1 calc R . . . .
N2 N 0.2817(3) 0.41639(14) -0.1639(4) 0.0572(11) Uani 1 1 d . . . . .
H2A H 0.256685 0.427737 -0.101799 0.069 Uiso 1 1 calc R . . . .
H2B H 0.313705 0.396544 -0.134998 0.069 Uiso 1 1 calc R . . . .
C6 C 0.4353(2) 0.48792(15) 0.0533(4) 0.0403(10) Uani 1 1 d . . . . .
C8 C 0.4741(2) 0.45834(16) -0.0124(4) 0.0438(11) Uani 1 1 d . . . . .
H8 H 0.456634 0.429562 -0.021028 0.053 Uiso 1 1 calc R . . . .
C1 C 0.1457(2) 0.46820(14) 0.0459(4) 0.0399(10) Uani 1 1 d . . . . .
C7 C 0.4610(2) 0.52923(16) 0.0661(4) 0.0436(11) Uani 1 1 d . . . . .
H7 H 0.434422 0.549571 0.111923 0.052 Uiso 1 1 calc R . . . .
O6 O 0.2197(3) 0.36323(13) 0.0132(4) 0.0761(12) Uani 1 1 d . . . . .
C10 C 0.2309(3) 0.29533(16) 0.1074(4) 0.0490(11) Uani 1 1 d . . . . .
C4 C 0.0487(2) 0.49312(16) -0.0924(4) 0.0441(11) Uani 1 1 d . . . . .
H4 H 0.081267 0.488356 -0.156252 0.053 Uiso 1 1 calc R . . . .
O3 O 0.2426(2) 0.36221(11) 0.2043(3) 0.0577(9) Uani 1 1 d . . . . .
C15 C 0.3221(3) 0.45101(19) -0.2232(5) 0.0599(14) Uani 1 1 d . . . . .
H15A H 0.355857 0.438334 -0.280695 0.090 Uiso 1 1 calc GR . . . .
H15B H 0.349702 0.467635 -0.164586 0.090 Uiso 1 1 calc GR . . . .
H15C H 0.287927 0.470224 -0.264020 0.090 Uiso 1 1 calc GR . . . .
C11 C 0.2214(3) 0.27270(18) 0.0040(5) 0.0627(14) Uani 1 1 d . . . . .
H11 H 0.214773 0.287949 -0.068007 0.075 Uiso 1 1 calc R . . . .
C5 C 0.3636(2) 0.47502(16) 0.1115(4) 0.0395(10) Uani 1 1 d . . . . .
C9 C 0.2309(3) 0.34351(17) 0.1063(5) 0.0519(12) Uani 1 1 d . . . . .
C14 C 0.2011(3) 0.4334(2) 0.4274(5) 0.0652(15) Uani 1 1 d . . . . .
H14A H 0.159877 0.447413 0.388095 0.098 Uiso 1 1 calc GR . . . .
H14B H 0.207289 0.445645 0.506562 0.098 Uiso 1 1 calc GR . . . .
H14C H 0.191786 0.402197 0.433785 0.098 Uiso 1 1 calc GR . . . .
C2 C 0.0711(2) 0.48421(15) 0.0224(4) 0.0406(10) Uani 1 1 d . . . . .
C13 C 0.3293(3) 0.4155(2) 0.4074(5) 0.0681(16) Uani 1 1 d . . . . .
H13A H 0.317228 0.384654 0.404919 0.102 Uiso 1 1 calc GR . . . .
H13B H 0.337180 0.424437 0.489482 0.102 Uiso 1 1 calc GR . . . .
H13C H 0.373734 0.420770 0.361603 0.102 Uiso 1 1 calc GR . . . .
C16 C 0.2301(4) 0.3946(2) -0.2444(6) 0.089(2) Uani 1 1 d . . . . .
H16A H 0.256747 0.382764 -0.312088 0.133 Uiso 1 1 calc GR . . . .
H16B H 0.193870 0.415536 -0.272210 0.133 Uiso 1 1 calc GR . . . .
H16C H 0.205536 0.371042 -0.202309 0.133 Uiso 1 1 calc GR . . . .
C12 C 0.2422(4) 0.27217(19) 0.2101(5) 0.0698(17) Uani 1 1 d . . . . .
H12 H 0.250112 0.287274 0.282025 0.084 Uiso 1 1 calc R . . . .


_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 1.965(3) . ?
Zn1 O1 1.958(3) . ?
Zn1 N1 2.063(4) . ?
Zn1 O3 1.985(3) . ?
O4 C1 1.248(5) . ?
O5 C5 1.247(5) . ?
O2 C5 1.263(6) . ?
O1 C1 1.281(5) . ?
N1 C14 1.499(6) . ?
N1 C13 1.468(7) . ?
C3 C4 1.404(6) 5_565 ?
C3 C2 1.403(6) . ?
N2 C15 1.465(7) . ?
N2 C16 1.477(8) . ?
C6 C8 1.377(6) . ?
C6 C7 1.368(7) . ?
C6 C5 1.524(6) . ?
C8 C7 1.391(6) 5_665 ?
C1 C2 1.480(6) . ?
O6 C9 1.235(6) . ?
C10 C11 1.374(7) . ?
C10 C9 1.488(7) . ?
C10 C12 1.382(8) . ?
C4 C2 1.392(6) . ?
O3 C9 1.269(6) . ?
C11 C11 1.402(11) 8_565 ?
C12 C12 1.369(11) 8_565 ?

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 N1 109.21(14) . . ?
O2 Zn1 O3 108.32(14) . . ?
O1 Zn1 O2 124.97(13) . . ?
O1 Zn1 N1 102.99(14) . . ?
O1 Zn1 O3 111.08(14) . . ?
O3 Zn1 N1 96.30(16) . . ?
C5 O2 Zn1 109.9(3) . . ?
C1 O1 Zn1 118.8(3) . . ?
C14 N1 Zn1 110.7(3) . . ?
C13 N1 Zn1 111.8(3) . . ?
C13 N1 C14 109.8(4) . . ?
C2 C3 C4 120.8(4) . 5_565 ?
C15 N2 C16 112.0(4) . . ?
C8 C6 C5 120.4(4) . . ?
C7 C6 C8 119.8(4) . . ?
C7 C6 C5 119.7(4) . . ?
C6 C8 C7 119.8(4) . 5_665 ?
O4 C1 O1 124.5(4) . . ?
O4 C1 C2 119.0(4) . . ?
O1 C1 C2 116.4(4) . . ?
C6 C7 C8 120.4(4) . 5_665 ?
C11 C10 C9 120.1(5) . . ?
C11 C10 C12 118.2(5) . . ?
C12 C10 C9 121.6(5) . . ?
C2 C4 C3 120.7(4) . 5_565 ?
C9 O3 Zn1 110.5(3) . . ?
C10 C11 C11 120.6(3) . 8_565 ?
O5 C5 O2 124.9(4) . . ?
O5 C5 C6 118.8(4) . . ?
O2 C5 C6 116.3(4) . . ?
O6 C9 C10 120.0(5) . . ?
O6 C9 O3 123.4(5) . . ?
O3 C9 C10 116.6(5) . . ?
C3 C2 C1 121.0(4) . . ?
C4 C2 C3 118.5(4) . . ?
C4 C2 C1 120.5(4) . . ?
C12 C12 C10 121.2(3) 8_565 . ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C7(H7), C4(H4), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C16(H16A,H16B,
 H16C)
;
_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 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.739
_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.906 0.250 -0.093 1640 491 ' '
2 0.089 0.750 0.030 1640 491 ' '

_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.790
_shelx_SHELXL_version_number     2018/3
_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.
;
_exptl_crystal_preparation       Luminescent
