# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ascid-allyloxy_red
_database_code_depnum_ccdc_archive 'CCDC 1540826'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            3
_chemical_name_systematic        Zn(A-ip)(bipy)
_chemical_formula_moiety         'C21 H16 N2 O5 Zn'
_chemical_formula_sum            'C21 H16 N2 O5 Zn'
_chemical_formula_weight         441.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn C21 H17 N2 O5'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.3928(3)
_cell_length_b                   15.6359(5)
_cell_length_c                   16.3018(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.451(3)
_cell_angle_gamma                90
_cell_volume                     2885.56(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5050
_cell_measurement_temperature    102.9(3)
_cell_measurement_theta_max      74.0310
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.017
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.0611
_exptl_crystal_size_min          0.0437
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11282
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.111
_diffrn_reflns_theta_min         3.905
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      102.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -123.00  -79.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -99.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00  -45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302 -166.0000   15.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega -109.00  -52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2302  -57.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   50.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2302  166.0000   37.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega   48.00   77.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   59.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   31.00   69.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   66.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   45.00   77.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   87.00  151.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   61.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   62.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   32.00   66.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega   98.00  125.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  132.00  158.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   76.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -45.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  156.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562   61.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00   59.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      108.4562  -30.0000  120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0209295000
_diffrn_orient_matrix_UB_12      -0.0369917000
_diffrn_orient_matrix_UB_13      -0.0846903000
_diffrn_orient_matrix_UB_21      -0.1085637000
_diffrn_orient_matrix_UB_22      0.0490375000
_diffrn_orient_matrix_UB_23      -0.0405569000
_diffrn_orient_matrix_UB_31      0.0792978000
_diffrn_orient_matrix_UB_32      0.0770937000
_diffrn_orient_matrix_UB_33      -0.0148964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5121
_reflns_number_total             5691
_reflns_odcompleteness_completeness 99.93
_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.
 
 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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.916
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.110
_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)+(0.0944P)²+3.0083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1640
_refine_special_details          ', SQUEEZE'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C11A-C10 \\sim C11B-C10
 with sigma of 0.02
 C18B-C17 \\sim C17-C18A \\sim C21A-C17 \\sim C21B-C17
 with sigma of 0.02
 N2-C19A \\sim N2-C19B \\sim N2-C20B \\sim N2-C20A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21A) \\sim Ueq, Uanis(C21B) \\sim Ueq, Uanis(C20B) \\sim Ueq,
Uanis(C20A) \\sim Ueq, Uanis(C19B) \\sim Ueq, Uanis(C19A) \\sim Ueq,
Uanis(C18A) \\sim Ueq, Uanis(C18B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: C19B(0.5) H19B(0.5) C19A(0.5) H19A(0.5) C18A(0.5) H18A(0.5)
 C21B(0.5) H21B(0.5) C20B(0.5) H20B(0.5) C20A(0.5) H20A(0.5) C18B(0.5)
 H18B(0.5) C21A(0.5) H21A(0.5) H10A(0.5) H10(0.5) C11A(0.5) H11A(0.5) H11B(0.5)
 C11B(0.5) H11C(0.5) H11D(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C8(H8), C15(H15), C13(H13), C19B(H19B), C16(H16), C6(H6),
 C19A(H19A), C18A(H18A), C21B(H21B), C20B(H20B), C20A(H20A), C18B(H18B),
 C21A(H21A), C10(H10A), C10(H10)
5.c X=CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11B(H11C,H11D)
;
_atom_sites_solution_hydrogens   geom
_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 0.47711(3) 0.12601(2) 0.46145(2) 0.01718(14) Uani 1 1 d . . . . .
O4 O 0.48850(16) 0.23898(12) 0.95851(11) 0.0250(4) Uani 1 1 d . . . . .
O3 O 0.46594(18) 0.30053(12) 0.83664(12) 0.0279(4) Uani 1 1 d . . . . .
O1 O 0.49068(16) 0.12427(11) 0.58659(11) 0.0210(4) Uani 1 1 d . . . . .
O5 O 0.5696(3) -0.06714(15) 0.90841(14) 0.0541(8) Uani 1 1 d . . . . .
N1 N 0.2882(2) 0.12606(13) 0.45818(15) 0.0223(5) Uani 1 1 d . . . . .
N2 N -0.3348(2) 0.11672(14) 0.45953(14) 0.0228(5) Uani 1 1 d D . . . .
C2 C 0.5147(2) 0.06457(16) 0.72034(16) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.0416(2) 0.12164(17) 0.45766(19) 0.0257(6) Uani 1 1 d . . . . .
C4 C 0.4976(2) 0.14916(17) 0.84157(17) 0.0254(5) Uani 1 1 d . . . . .
C3 C 0.4936(2) 0.14268(17) 0.75642(17) 0.0227(5) Uani 1 1 d . . . . .
H3 H 0.4767 0.1907 0.7235 0.027 Uiso 1 1 calc R . . . .
C12 C 0.2354(2) 0.1502(2) 0.5239(2) 0.0329(6) Uani 1 1 d . . . . .
H12 H 0.2828 0.1686 0.5708 0.039 Uiso 1 1 calc R . . . .
C1 C 0.5157(2) 0.05730(16) 0.62851(16) 0.0191(5) Uani 1 1 d . . . . .
C17 C -0.0887(2) 0.11902(17) 0.45766(18) 0.0262(6) Uani 1 1 d D . . . .
C8 C 0.5401(3) -0.00754(17) 0.76961(18) 0.0301(6) Uani 1 1 d . . . . .
H8 H 0.5542 -0.0599 0.7455 0.036 Uiso 1 1 calc R . . . .
C15 C 0.0951(3) 0.0986(2) 0.3880(2) 0.0353(7) Uani 1 1 d . . . . .
H15 H 0.0494 0.0815 0.3400 0.042 Uiso 1 1 calc R . . . .
C13 C 0.1151(2) 0.1492(2) 0.5260(2) 0.0337(7) Uani 1 1 d . . . . .
H13 H 0.0831 0.1671 0.5732 0.040 Uiso 1 1 calc R . . . .
C5 C 0.4819(2) 0.23521(17) 0.88128(17) 0.0234(5) Uani 1 1 d . . . . .
C19B C -0.2869(5) 0.1163(6) 0.3871(4) 0.0285(14) Uani 0.5 1 d D U P A 2
H19B H -0.3371 0.1152 0.3380 0.034 Uiso 0.5 1 calc R . P A 2
C16 C 0.2172(2) 0.1014(2) 0.39127(19) 0.0335(6) Uani 1 1 d . . . . .
H16 H 0.2516 0.0853 0.3445 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5224(3) 0.07806(19) 0.89083(18) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.5246 0.0824 0.9479 0.041 Uiso 1 1 calc R . . . .
C7 C 0.5442(3) -0.00077(19) 0.85411(19) 0.0377(7) Uani 1 1 d . . . . .
C19A C -0.2794(6) 0.0730(5) 0.4062(5) 0.0347(15) Uani 0.5 1 d D U P A 1
H19A H -0.3249 0.0400 0.3672 0.042 Uiso 0.5 1 calc R . P A 1
C18A C -0.1605(6) 0.0727(5) 0.4044(5) 0.0360(15) Uani 0.5 1 d D U P A 1
H18A H -0.1282 0.0396 0.3651 0.043 Uiso 0.5 1 calc R . P A 1
C21B C -0.1369(5) 0.1128(4) 0.5298(3) 0.0254(11) Uani 0.5 1 d D U P A 2
H21B H -0.0886 0.1091 0.5796 0.030 Uiso 0.5 1 calc R . P A 2
C20B C -0.2586(5) 0.1120(5) 0.5288(3) 0.0281(12) Uani 0.5 1 d D U P A 2
H20B H -0.2896 0.1078 0.5790 0.034 Uiso 0.5 1 calc R . P A 2
C20A C -0.2675(6) 0.1697(6) 0.5121(5) 0.0466(18) Uani 0.5 1 d D U P A 1
H20A H -0.3037 0.2049 0.5477 0.056 Uiso 0.5 1 calc R . P A 1
C18B C -0.1649(6) 0.1173(6) 0.3834(4) 0.0324(14) Uani 0.5 1 d D U P A 2
H18B H -0.1346 0.1169 0.3328 0.039 Uiso 0.5 1 calc R . P A 2
O2 O 0.54485(16) -0.01240(11) 0.59975(11) 0.0224(4) Uani 1 1 d . . . . .
C21A C -0.1455(6) 0.1716(6) 0.5130(5) 0.0490(18) Uani 0.5 1 d D U P A 1
H21A H -0.1006 0.2073 0.5499 0.059 Uiso 0.5 1 calc R . P A 1
C9 C 0.6026(4) -0.1484(2) 0.8757(2) 0.0511(10) Uani 1 1 d . . . . .
H9A H 0.5493 -0.1615 0.8267 0.061 Uiso 1 1 calc R . . . .
H9B H 0.5938 -0.1927 0.9162 0.061 Uiso 1 1 calc R . . . .
C10 C 0.7285(5) -0.1493(3) 0.8539(3) 0.0659(12) Uani 1 1 d D . . . .
H10A H 0.7516 -0.2019 0.8344 0.079 Uiso 0.5 1 calc R . P B 2
H10 H 0.7823 -0.1157 0.8868 0.079 Uiso 0.5 1 calc R . P C 1
C11A C 0.8083(7) -0.0930(7) 0.8569(6) 0.065(2) Uani 0.5 1 d D . P D 2
H11A H 0.7937 -0.0382 0.8755 0.078 Uiso 0.5 1 calc R . P D 2
H11B H 0.8817 -0.1062 0.8404 0.078 Uiso 0.5 1 calc R . P D 2
C11B C 0.7659(9) -0.1866(7) 0.8016(6) 0.063(2) Uani 0.5 1 d D . P D 1
H11C H 0.7164 -0.2213 0.7666 0.076 Uiso 0.5 1 calc R . P D 1
H11D H 0.8454 -0.1819 0.7944 0.076 Uiso 0.5 1 calc R . P D 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.116(2) 4_565 ?
Zn1 O3 2.327(2) 4_565 ?
Zn1 O1 2.0287(19) . ?
Zn1 N1 2.147(2) . ?
Zn1 N2 2.152(2) 1_655 ?
Zn1 C5 2.537(3) 4_565 ?
Zn1 O2 2.0391(18) 3_656 ?
O4 Zn1 2.116(2) 4_566 ?
O4 C5 1.254(3) . ?
O3 Zn1 2.327(2) 4_566 ?
O3 C5 1.255(3) . ?
O1 C1 1.265(3) . ?
O5 C7 1.374(4) . ?
O5 C9 1.443(4) . ?
N1 C12 1.341(4) . ?
N1 C16 1.340(4) . ?
N2 Zn1 2.152(2) 1_455 ?
N2 C19B 1.355(6) . ?
N2 C19A 1.321(6) . ?
N2 C20B 1.346(6) . ?
N2 C20A 1.364(7) . ?
C2 C3 1.388(4) . ?
C2 C1 1.503(4) . ?
C2 C8 1.395(4) . ?
C14 C17 1.485(4) . ?
C14 C15 1.395(4) . ?
C14 C13 1.385(4) . ?
C4 C3 1.387(4) . ?
C4 C5 1.512(4) . ?
C4 C6 1.382(4) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C1 O2 1.246(3) . ?
C17 C18A 1.337(7) . ?
C17 C21B 1.356(6) . ?
C17 C18B 1.408(7) . ?
C17 C21A 1.429(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(4) . ?
C13 H13 0.9300 . ?
C5 Zn1 2.537(3) 4_566 ?
C19B H19B 0.9300 . ?
C19B C18B 1.398(9) . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.404(4) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.358(9) . ?
C18A H18A 0.9300 . ?
C21B H21B 0.9300 . ?
C21B C20B 1.384(8) . ?
C20B H20B 0.9300 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.388(10) . ?
C18B H18B 0.9300 . ?
O2 Zn1 2.0390(18) 3_656 ?
C21A H21A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.516(7) . ?
C10 H10A 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11A 1.263(10) . ?
C10 C11B 1.152(9) . ?
C11A H11A 0.9300 . ?
C11A H11B 0.9300 . ?
C11B H11C 0.9300 . ?
C11B H11D 0.9300 . ?

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
O4 Zn1 O3 59.02(7) 4_565 4_565 ?
O4 Zn1 N1 93.61(8) 4_565 . ?
O4 Zn1 N2 90.19(8) 4_565 1_655 ?
O4 Zn1 C5 29.54(8) 4_565 4_565 ?
O3 Zn1 C5 29.51(8) 4_565 4_565 ?
O1 Zn1 O4 92.19(7) . 4_565 ?
O1 Zn1 O3 151.19(7) . 4_565 ?
O1 Zn1 N1 89.31(8) . . ?
O1 Zn1 N2 92.88(8) . 1_655 ?
O1 Zn1 C5 121.73(8) . 4_565 ?
O1 Zn1 O2 118.14(7) . 3_656 ?
N1 Zn1 O3 91.25(8) . 4_565 ?
N1 Zn1 N2 175.54(8) . 1_655 ?
N1 Zn1 C5 93.80(8) . 4_565 ?
N2 Zn1 O3 88.70(8) 1_655 4_565 ?
N2 Zn1 C5 88.36(8) 1_655 4_565 ?
O2 Zn1 O4 149.61(7) 3_656 4_565 ?
O2 Zn1 O3 90.61(7) 3_656 4_565 ?
O2 Zn1 N1 85.45(8) 3_656 . ?
O2 Zn1 N2 90.10(8) 3_656 1_655 ?
O2 Zn1 C5 120.12(8) 3_656 4_565 ?
C5 O4 Zn1 94.17(16) . 4_566 ?
C5 O3 Zn1 84.53(16) . 4_566 ?
C1 O1 Zn1 122.77(16) . . ?
C7 O5 C9 118.1(3) . . ?
C12 N1 Zn1 121.3(2) . . ?
C16 N1 Zn1 122.16(19) . . ?
C16 N1 C12 116.6(2) . . ?
C19B N2 Zn1 120.8(3) . 1_455 ?
C19A N2 Zn1 126.5(3) . 1_455 ?
C19A N2 C20A 116.8(4) . . ?
C20B N2 Zn1 122.7(3) . 1_455 ?
C20B N2 C19B 116.5(4) . . ?
C20A N2 Zn1 116.1(3) . 1_455 ?
C3 C2 C1 120.6(2) . . ?
C3 C2 C8 120.1(2) . . ?
C8 C2 C1 119.2(2) . . ?
C15 C14 C17 121.4(3) . . ?
C13 C14 C17 121.5(3) . . ?
C13 C14 C15 117.0(3) . . ?
C3 C4 C5 120.1(2) . . ?
C6 C4 C3 120.3(3) . . ?
C6 C4 C5 119.6(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
N1 C12 H12 118.2 . . ?
N1 C12 C13 123.7(3) . . ?
C13 C12 H12 118.2 . . ?
O1 C1 C2 116.7(2) . . ?
O2 C1 O1 125.0(2) . . ?
O2 C1 C2 118.2(2) . . ?
C18A C17 C14 123.6(4) . . ?
C18A C17 C21A 115.8(4) . . ?
C21B C17 C14 120.3(3) . . ?
C21B C17 C18B 118.2(4) . . ?
C18B C17 C14 121.4(4) . . ?
C21A C17 C14 120.5(4) . . ?
C2 C8 H8 120.2 . . ?
C7 C8 C2 119.7(3) . . ?
C7 C8 H8 120.2 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
O4 C5 Zn1 56.29(14) . 4_566 ?
O4 C5 O3 122.1(2) . . ?
O4 C5 C4 118.3(2) . . ?
O3 C5 Zn1 65.96(14) . 4_566 ?
O3 C5 C4 119.5(2) . . ?
C4 C5 Zn1 172.7(2) . 4_566 ?
N2 C19B H19B 118.8 . . ?
N2 C19B C18B 122.4(5) . . ?
C18B C19B H19B 118.8 . . ?
N1 C16 C15 123.5(3) . . ?
N1 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C4 C6 H6 120.2 . . ?
C4 C6 C7 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
O5 C7 C8 124.6(3) . . ?
O5 C7 C6 115.0(3) . . ?
C8 C7 C6 120.4(3) . . ?
N2 C19A H19A 117.7 . . ?
N2 C19A C18A 124.5(6) . . ?
C18A C19A H19A 117.7 . . ?
C17 C18A C19A 121.5(5) . . ?
C17 C18A H18A 119.2 . . ?
C19A C18A H18A 119.2 . . ?
C17 C21B H21B 120.2 . . ?
C17 C21B C20B 119.5(5) . . ?
C20B C21B H21B 120.2 . . ?
N2 C20B C21B 124.0(5) . . ?
N2 C20B H20B 118.0 . . ?
C21B C20B H20B 118.0 . . ?
N2 C20A H20A 119.6 . . ?
N2 C20A C21A 120.8(6) . . ?
C21A C20A H20A 119.6 . . ?
C17 C18B H18B 120.5 . . ?
C19B C18B C17 118.9(5) . . ?
C19B C18B H18B 120.5 . . ?
C1 O2 Zn1 157.37(17) . 3_656 ?
C17 C21A H21A 119.9 . . ?
C20A C21A C17 120.3(6) . . ?
C20A C21A H21A 119.9 . . ?
O5 C9 H9A 109.0 . . ?
O5 C9 H9B 109.0 . . ?
O5 C9 C10 112.8(4) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 113.6 . . ?
C9 C10 H10 116.0 . . ?
C11A C10 C9 132.8(6) . . ?
C11A C10 H10A 113.6 . . ?
C11B C10 C9 128.0(7) . . ?
C11B C10 H10 116.0 . . ?
C10 C11A H11A 120.0 . . ?
C10 C11A H11B 120.0 . . ?
H11A C11A H11B 120.0 . . ?
C10 C11B H11C 120.0 . . ?
C10 C11B H11D 120.0 . . ?
H11C C11B H11D 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C5 O3 -3.8(3) 4_566 . . . ?
Zn1 O4 C5 C4 174.2(2) 4_566 . . . ?
Zn1 O3 C5 O4 3.5(2) 4_566 . . . ?
Zn1 O3 C5 C4 -174.5(2) 4_566 . . . ?
Zn1 O1 C1 C2 -176.05(16) . . . . ?
Zn1 O1 C1 O2 6.6(3) . . . . ?
Zn1 N1 C12 C13 -178.2(3) . . . . ?
Zn1 N1 C16 C15 178.2(3) . . . . ?
Zn1 N2 C19B C18B 174.7(6) 1_455 . . . ?
Zn1 N2 C19A C18A 176.1(7) 1_455 . . . ?
Zn1 N2 C20B C21B -174.6(5) 1_455 . . . ?
Zn1 N2 C20A C21A -177.0(8) 1_455 . . . ?
O1 C1 O2 Zn1 -75.1(5) . . . 3_656 ?
O5 C9 C10 C11A -1.9(9) . . . . ?
O5 C9 C10 C11B -147.4(7) . . . . ?
N1 C12 C13 C14 0.5(6) . . . . ?
N2 C19B C18B C17 -0.1(12) . . . . ?
N2 C19A C18A C17 -0.7(15) . . . . ?
N2 C20A C21A C17 1.1(15) . . . . ?
C2 C1 O2 Zn1 107.6(4) . . . 3_656 ?
C2 C8 C7 O5 -179.2(3) . . . . ?
C2 C8 C7 C6 0.3(5) . . . . ?
C14 C17 C18A C19A -179.4(7) . . . . ?
C14 C17 C21B C20B 178.9(5) . . . . ?
C14 C17 C18B C19B -179.0(6) . . . . ?
C14 C17 C21A C20A 179.2(7) . . . . ?
C14 C15 C16 N1 -0.6(6) . . . . ?
C4 C6 C7 O5 179.1(3) . . . . ?
C4 C6 C7 C8 -0.5(6) . . . . ?
C3 C2 C1 O1 -3.5(4) . . . . ?
C3 C2 C1 O2 174.1(2) . . . . ?
C3 C2 C8 C7 -0.1(5) . . . . ?
C3 C4 C5 O4 -178.5(2) . . . . ?
C3 C4 C5 O3 -0.5(4) . . . . ?
C3 C4 C6 C7 0.4(5) . . . . ?
C12 N1 C16 C15 -1.1(5) . . . . ?
C1 C2 C3 C4 -177.4(2) . . . . ?
C1 C2 C8 C7 177.3(3) . . . . ?
C17 C14 C15 C16 -179.5(3) . . . . ?
C17 C14 C13 C12 179.5(3) . . . . ?
C17 C21B C20B N2 0.2(11) . . . . ?
C8 C2 C3 C4 0.0(4) . . . . ?
C8 C2 C1 O1 179.1(2) . . . . ?
C8 C2 C1 O2 -3.3(4) . . . . ?
C15 C14 C17 C18A 20.5(7) . . . . ?
C15 C14 C17 C21B 157.5(4) . . . . ?
C15 C14 C17 C18B -18.4(6) . . . . ?
C15 C14 C17 C21A -155.4(6) . . . . ?
C15 C14 C13 C12 -2.2(5) . . . . ?
C13 C14 C17 C18A -161.2(6) . . . . ?
C13 C14 C17 C21B -24.2(5) . . . . ?
C13 C14 C17 C18B 159.9(5) . . . . ?
C13 C14 C17 C21A 22.8(6) . . . . ?
C13 C14 C15 C16 2.2(5) . . . . ?
C5 C4 C3 C2 176.3(2) . . . . ?
C5 C4 C6 C7 -176.1(3) . . . . ?
C19B N2 C20B C21B 4.7(10) . . . . ?
C16 N1 C12 C13 1.1(5) . . . . ?
C6 C4 C3 C2 -0.2(4) . . . . ?
C6 C4 C5 O4 -2.0(4) . . . . ?
C6 C4 C5 O3 176.0(3) . . . . ?
C7 O5 C9 C10 76.5(5) . . . . ?
C19A N2 C20A C21A -4.9(12) . . . . ?
C18A C17 C21A C20A 3.0(12) . . . . ?
C21B C17 C18B C19B 5.1(10) . . . . ?
C20B N2 C19B C18B -4.7(10) . . . . ?
C20A N2 C19A C18A 4.9(13) . . . . ?
C18B C17 C21B C20B -5.2(9) . . . . ?
C21A C17 C18A C19A -3.2(12) . . . . ?
C9 O5 C7 C8 4.6(6) . . . . ?
C9 O5 C7 C6 -175.0(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.644 -0.892 1211.7 387.2 DMF

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 9 -4 0.0256 -0.0112 9.0005 -3.9823 0.0041 0.6041 0.7523
0 -9 4 0.0256 0.0112 -9.0005 3.9823 -0.0041 -0.6041 -0.7523
-7 -1 -1 0.2000 -7.0004 -0.9932 -0.9943 -0.0256 0.7516 -0.6169
7 1 1 0.1820 7.0004 0.9932 0.9943 0.0256 -0.7516 0.6169
0 2 10 0.0262 0.0098 1.9756 10.0040 -0.9201 -0.3099 0.0041
0 -2 -10 0.0222 -0.0098 -1.9756 -10.0040 0.9201 0.3099 -0.0041
0 -7 -8 0.0131 -0.0038 -6.9754 -8.0139 0.9366 -0.0166 -0.4187
0 9 6 0.0295 0.0001 8.9780 6.0178 -0.8418 0.1962 0.6025

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Solvothermal Synthesis'
####################################################################### 
# 
# 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_as358b_red_till_run_12
_database_code_depnum_ccdc_archive 'CCDC 1540825'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            2
_chemical_name_systematic        Zn(P-ip)(bipy)
_chemical_formula_moiety         '0.25(C84 H72 N8 O20 Zn4)'
_chemical_formula_sum            'C21 H18 N2 O5 Zn'
_chemical_formula_weight         442.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn O5 N2 C21 H18'
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      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z'

_cell_length_a                   16.4960(7)
_cell_length_b                   15.8918(6)
_cell_length_c                   11.4039(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2989.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    240.00(14)
_cell_measurement_theta_max      74.5690
_cell_measurement_theta_min      3.8330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    0.984
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.2617
_exptl_crystal_size_mid          0.1137
_exptl_crystal_size_min          0.0781
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9046
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.264
_diffrn_reflns_theta_min         3.862
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -81.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8552  -57.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega  -97.00  -64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8552  125.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8552  -38.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
  4 omega   63.00  109.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   60.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00  104.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   76.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   40.00   65.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   77.00  139.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega   69.00  150.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
 11 omega -124.00  -99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4802  -99.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00  113.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4802  175.0000  -60.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0817840000
_diffrn_orient_matrix_UB_12      -0.0409798000
_diffrn_orient_matrix_UB_13      -0.0316762000
_diffrn_orient_matrix_UB_21      0.0418498000
_diffrn_orient_matrix_UB_22      0.0863565000
_diffrn_orient_matrix_UB_23      0.0099541000
_diffrn_orient_matrix_UB_31      0.0166195000
_diffrn_orient_matrix_UB_32      -0.0164316000
_diffrn_orient_matrix_UB_33      0.1309224000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2741
_reflns_number_total             3240
_reflns_odcompleteness_completeness 99.70
_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.
 
 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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.685
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     139
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.090
_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)+(0.1388P)²+1.8245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2113
_refine_ls_wR_factor_ref         0.2185
_refine_special_details          ', SQUEEZE'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O5B-C9B = O5A-C9A
 1.43 with sigma of 0.01
 C10A-C9A
 1.54 with sigma of 0.01
 C10A-C11A
 1.54 with sigma of 0.01
 C10B-C9B
 1.54 with sigma of 0.01
 C11B-C10B
 1.54 with sigma of 0.01
 C10B-C11C
 1.54 with sigma of 0.01
 C11A-C9A
 2.52 with sigma of 0.02
 C9B-C11B
 2.52 with sigma of 0.02
 C11C-C9B
 2.52 with sigma of 0.02
 O5A-C7A \\sim O5B-C7B
 with sigma of 0.02
 O5A-C9A \\sim O5B-C9B
 with sigma of 0.02
 C2-C8A \\sim C8B-C2 \\sim C6B-C4 \\sim C4-C6A
 with sigma of 0.02
 C7B-C8B \\sim C7A-C8A \\sim C7B-C6B \\sim C7A-C6A
 with sigma of 0.02
 N1-C12B \\sim N1-C12A \\sim N1-C16B \\sim N1-C16A
 with sigma of 0.02
 C16B-C15B \\sim C15A-C16A \\sim C13B-C12B \\sim C13A-C12A
 with sigma of 0.02
 C15A-C14 \\sim C15B-C14 \\sim C13A-C14 \\sim C13B-C14
 with sigma of 0.02
 C10A-C9A \\sim C10B-C9B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12B) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13B) \\sim Ueq,
Uanis(C16A) \\sim Ueq, Uanis(C16B) \\sim Ueq, Uanis(C13A) \\sim Ueq,
Uanis(C15B) \\sim Ueq, Uanis(C15A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8B) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C6B) \\sim Ueq, Uanis(C6A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C7A) \\sim Ueq, Uanis(C7B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O5B) \\sim Ueq, Uanis(O5A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(C9B)=Sof(C10B)=Sof(C8B)=Sof(H8B)=0.5*
 (1-FVAR(2))
 Sof(C11B)=Sof(C11C)=0.25*(1-FVAR(2))
 Sof(C6A)=Sof(H6A)=Sof(O5A)=Sof(C7A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(C8A)=
 Sof(H8A)=0.5*FVAR(2)
 Fixed Sof: C12A(0.5) H12A(0.5) C16A(0.5) H16A(0.5) C15A(0.5) H15A(0.5)
 C13A(0.5) H13A(0.5) C15B(0.5) H15B(0.5) C13B(0.5) H13B(0.5) C16B(0.5)
 H16B(0.5) C12B(0.5) H12B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C12A(H12A), C16A(H16A), C15A(H15A), C13A(H13A), C15B(H15B),
 C13B(H13B), C16B(H16B), C12B(H12B), C6A(H6A), C6B(H6B), C8A(H8A), C8B(H8B)
;
_atom_sites_solution_hydrogens   geom
_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 0.46271(3) 0.12334(4) 0.5000 0.0373(3) Uani 1 2 d S T P A .
O3 O 0.08664(19) 0.3733(2) 0.5000 0.0447(8) Uani 1 2 d S T P . .
O1 O 0.3338(2) 0.1940(2) 0.5000 0.0618(11) Uani 1 2 d S T P . .
O2 O 0.4538(2) 0.2543(2) 0.5000 0.0501(9) Uani 1 2 d S T P . .
N1 N 0.46058(17) 0.11713(19) 0.3109(3) 0.0478(7) Uani 1 1 d D . . . .
C2 C 0.3383(3) 0.3440(3) 0.5000 0.0456(11) Uani 1 2 d DS T P . .
C3 C 0.2529(3) 0.3504(3) 0.5000 0.0403(10) Uani 1 2 d S T P B .
H3 H 0.2207 0.3023 0.5000 0.048 Uiso 1 2 calc RS T P . .
C5 C 0.1274(2) 0.4396(3) 0.5000 0.0348(9) Uani 1 2 d S T P B .
C12A C 0.4069(8) 0.0714(7) 0.2496(11) 0.060(3) Uani 0.5 1 d D U . A 1
H12A H 0.3688 0.0401 0.2910 0.072 Uiso 0.5 1 calc R . . A 1
C4 C 0.2178(3) 0.4303(3) 0.5000 0.0403(10) Uani 1 2 d DS T P . .
C16A C 0.5161(7) 0.1587(7) 0.2506(9) 0.054(3) Uani 0.5 1 d D U . A 1
H16A H 0.5565 0.1872 0.2914 0.064 Uiso 0.5 1 calc R . . A 1
C14 C 0.4600(2) 0.1162(3) 0.0646(4) 0.0533(9) Uani 1 1 d D . . . .
C1 C 0.3759(3) 0.2587(3) 0.5000 0.0446(10) Uani 1 2 d S T P B .
C15A C 0.5167(7) 0.1615(7) 0.1305(9) 0.057(3) Uani 0.5 1 d D U . A 1
H15A H 0.5553 0.1940 0.0922 0.069 Uiso 0.5 1 calc R . . A 1
C13A C 0.4047(7) 0.0682(7) 0.1292(10) 0.057(3) Uani 0.5 1 d D U . A 1
H13A H 0.3670 0.0345 0.0911 0.069 Uiso 0.5 1 calc R . . A 1
O4 O 0.0981(2) 0.5112(2) 0.5000 0.0532(9) Uani 1 2 d S T P . .
C15B C 0.5311(6) 0.1269(8) 0.1265(11) 0.065(3) Uani 0.5 1 d D U . A 2
H15B H 0.5800 0.1352 0.0878 0.079 Uiso 0.5 1 calc R . . A 2
C13B C 0.3905(6) 0.1012(8) 0.1297(9) 0.061(3) Uani 0.5 1 d D U . A 2
H13B H 0.3417 0.0899 0.0920 0.073 Uiso 0.5 1 calc R . . A 2
C16B C 0.5278(7) 0.1249(9) 0.2462(11) 0.069(4) Uani 0.5 1 d D U . A 2
H16B H 0.5767 0.1295 0.2863 0.082 Uiso 0.5 1 calc R . . A 2
C12B C 0.3940(7) 0.1031(9) 0.2495(10) 0.062(3) Uani 0.5 1 d D U . A 2
H12B H 0.3461 0.0939 0.2907 0.075 Uiso 0.5 1 calc R . . A 2
C6A C 0.2624(12) 0.5066(11) 0.5000 0.024(5) Uani 0.31(2) 2 d DS TU P B 1
H6A H 0.2369 0.5588 0.5000 0.029 Uiso 0.31(2) 2 calc RS T P B 1
O5A O 0.4013(8) 0.5620(8) 0.5000 0.030(4) Uani 0.31(2) 2 d DS TU P B 1
C7A C 0.3461(13) 0.4989(13) 0.5000 0.036(8) Uani 0.31(2) 2 d DS TU P B 1
O5B O 0.4009(5) 0.5598(5) 0.4444(13) 0.056(3) Uani 0.347(12) 1 d D U . B 2
C6B C 0.2669(7) 0.5011(7) 0.4699(14) 0.039(3) Uani 0.347(12) 1 d D U . B 2
H6B H 0.2425 0.5529 0.4556 0.047 Uiso 0.347(12) 1 calc R . . B 2
C7B C 0.3507(6) 0.4937(6) 0.4616(15) 0.036(3) Uani 0.347(12) 1 d D U . B 2
C9B C 0.3699(7) 0.6388(6) 0.4012(12) 0.053(3) Uiso 0.347(12) 1 d D . . B 2
C9A C 0.3709(11) 0.6420(9) 0.4598(17) 0.033(5) Uiso 0.153(12) 1 d D . . B 1
C10B C 0.3441(13) 0.6374(13) 0.2716(14) 0.103(6) Uiso 0.347(12) 1 d D . . B 2
C10A C 0.3537(15) 0.6500(17) 0.3272(18) 0.056(7) Uiso 0.153(12) 1 d D . . B 1
C11A C 0.428(2) 0.623(3) 0.254(3) 0.102(14) Uiso 0.153(12) 1 d D . . B 1
C8A C 0.3827(16) 0.4201(11) 0.5000 0.032(7) Uani 0.31(2) 2 d DS TU P B 1
H8A H 0.4391 0.4173 0.5000 0.039 Uiso 0.31(2) 2 calc RS T P B 1
C8B C 0.3859(7) 0.4140(6) 0.4692(15) 0.037(3) Uani 0.347(12) 1 d D U . B 2
H8B H 0.4409 0.4072 0.4539 0.044 Uiso 0.347(12) 1 calc R . . B 2
C11B C 0.417(2) 0.623(4) 0.191(3) 0.15(2) Uiso 0.174(6) 1 d D . . B 2
C11C C 0.297(3) 0.715(2) 0.230(3) 0.128(16) Uiso 0.174(6) 1 d D . . B 2


_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 O3 2.045(3) 3_556 ?
Zn1 O1 2.404(4) . ?
Zn1 O2 2.086(4) . ?
Zn1 N1 2.159(4) 6_556 ?
Zn1 N1 2.159(4) . ?
Zn1 O4 2.045(3) 7_655 ?
O3 Zn1 2.045(3) 3_456 ?
O3 C5 1.249(5) . ?
O1 C1 1.240(6) 6_556 ?
O1 C1 1.240(6) . ?
O2 C1 1.287(6) . ?
O2 C1 1.287(6) 6_556 ?
N1 C12A 1.342(10) . ?
N1 C16A 1.322(9) . ?
N1 C16B 1.337(11) . ?
N1 C12B 1.321(10) . ?
C2 C3 1.412(6) . ?
C2 C1 1.491(6) 6_556 ?
C2 C1 1.491(6) . ?
C2 C8A 1.415(14) . ?
C2 C8B 1.407(10) . ?
C2 C8B 1.407(10) 6_556 ?
C3 H3 0.9300 . ?
C3 C4 1.395(6) . ?
C5 C4 1.500(6) . ?
C5 O4 1.236(5) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.374(12) . ?
C4 C6A 1.418(13) . ?
C4 C6B 1.429(10) 6_556 ?
C4 C6B 1.429(10) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.370(11) . ?
C14 C14 1.473(9) 6 ?
C14 C15A 1.400(9) . ?
C14 C13A 1.398(10) . ?
C14 C15B 1.380(10) . ?
C14 C13B 1.385(10) . ?
C1 C1 0.000(14) 6_556 ?
C15A H15A 0.9300 . ?
C13A H13A 0.9300 . ?
O4 Zn1 2.045(3) 7_665 ?
C15B H15B 0.9300 . ?
C15B C16B 1.366(12) . ?
C13B H13B 0.9300 . ?
C13B C12B 1.369(11) . ?
C16B H16B 0.9300 . ?
C12B H12B 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.387(15) . ?
O5A C7A 1.355(16) . ?
O5A C9A 1.441(9) . ?
O5A C9A 1.441(9) 6_556 ?
C7A C8A 1.390(15) . ?
O5B C7B 1.353(10) . ?
O5B C9B 1.443(8) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.390(10) . ?
C7B O5B 1.715(17) 6_556 ?
C7B C8B 1.397(10) . ?
C9B C10B 1.538(9) . ?
C9A C10A 1.545(9) . ?
C10B C11B 1.528(10) . ?
C10B C11C 1.524(10) . ?
C10A C11A 1.536(10) . ?
C8A H8A 0.9300 . ?
C8B H8B 0.9300 . ?

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
O3 Zn1 O1 150.68(12) 3_556 . ?
O3 Zn1 O2 92.56(13) 3_556 . ?
O3 Zn1 N1 91.00(8) 3_556 6_556 ?
O3 Zn1 N1 91.00(8) 3_556 . ?
O2 Zn1 O1 58.11(13) . . ?
O2 Zn1 N1 92.55(8) . . ?
O2 Zn1 N1 92.55(8) . 6_556 ?
N1 Zn1 O1 90.40(8) . . ?
N1 Zn1 O1 90.40(8) 6_556 . ?
N1 Zn1 N1 174.43(16) . 6_556 ?
O4 Zn1 O3 120.89(13) 7_655 3_556 ?
O4 Zn1 O1 88.43(13) 7_655 . ?
O4 Zn1 O2 146.55(14) 7_655 . ?
O4 Zn1 N1 87.26(8) 7_655 . ?
O4 Zn1 N1 87.25(8) 7_655 6_556 ?
C5 O3 Zn1 121.0(3) . 3_456 ?
C1 O1 Zn1 83.8(3) . . ?
C1 O1 Zn1 83.8(3) 6_556 . ?
C1 O1 C1 0.0(5) 6_556 . ?
C1 O2 Zn1 97.1(3) 6_556 . ?
C1 O2 Zn1 97.1(3) . . ?
C1 O2 C1 0.0(4) 6_556 . ?
C12A N1 Zn1 123.8(6) . . ?
C16A N1 Zn1 119.0(5) . . ?
C16A N1 C12A 117.2(8) . . ?
C16B N1 Zn1 122.2(6) . . ?
C12B N1 Zn1 123.4(6) . . ?
C12B N1 C16B 114.4(9) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 C1 118.7(4) . 6_556 ?
C3 C2 C8A 117.1(12) . . ?
C1 C2 C1 0.00(15) 6_556 . ?
C8A C2 C1 124.2(12) . 6_556 ?
C8A C2 C1 124.2(12) . . ?
C8B C2 C3 120.0(6) 6_556 . ?
C8B C2 C3 120.0(6) . . ?
C8B C2 C1 119.1(6) . 6_556 ?
C8B C2 C1 119.1(6) 6_556 6_556 ?
C8B C2 C1 119.1(6) 6_556 . ?
C8B C2 C1 119.1(6) . . ?
C8B C2 C8B 28.9(14) 6_556 . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
O3 C5 C4 116.9(4) . . ?
O4 C5 O3 124.5(4) . . ?
O4 C5 C4 118.6(4) . . ?
N1 C12A H12A 118.1 . . ?
N1 C12A C13A 123.9(11) . . ?
C13A C12A H12A 118.1 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 C6A 124.3(10) . . ?
C3 C4 C6B 118.9(6) . 6_556 ?
C3 C4 C6B 118.9(6) . . ?
C6A C4 C5 115.6(10) . . ?
C6B C4 C5 119.1(6) 6_556 . ?
C6B C4 C5 119.1(6) . . ?
C6B C4 C6B 27.8(13) 6_556 . ?
N1 C16A H16A 118.6 . . ?
N1 C16A C15A 122.7(10) . . ?
C15A C16A H16A 118.6 . . ?
C15A C14 C14 122.5(5) . 6 ?
C13A C14 C14 121.8(5) . 6 ?
C13A C14 C15A 115.7(8) . . ?
C15B C14 C14 120.8(5) . 6 ?
C15B C14 C13B 116.7(8) . . ?
C13B C14 C14 122.4(5) . 6 ?
O1 C1 O2 120.9(4) . . ?
O1 C1 C2 121.4(4) . . ?
O2 C1 C2 117.7(4) . . ?
C1 C1 O1 0(10) 6_556 . ?
C1 C1 O2 0(10) 6_556 . ?
C1 C1 C2 0(10) 6_556 . ?
C16A C15A C14 121.1(9) . . ?
C16A C15A H15A 119.5 . . ?
C14 C15A H15A 119.5 . . ?
C12A C13A C14 119.3(11) . . ?
C12A C13A H13A 120.3 . . ?
C14 C13A H13A 120.3 . . ?
C5 O4 Zn1 173.6(3) . 7_665 ?
C14 C15B H15B 120.8 . . ?
C16B C15B C14 118.3(11) . . ?
C16B C15B H15B 120.8 . . ?
C14 C13B H13B 120.1 . . ?
C12B C13B C14 119.8(10) . . ?
C12B C13B H13B 120.1 . . ?
N1 C16B C15B 125.9(12) . . ?
N1 C16B H16B 117.1 . . ?
C15B C16B H16B 117.1 . . ?
N1 C12B C13B 124.6(11) . . ?
N1 C12B H12B 117.7 . . ?
C13B C12B H12B 117.7 . . ?
C4 C6A H6A 121.9 . . ?
C7A C6A C4 116.1(16) . . ?
C7A C6A H6A 121.9 . . ?
C7A O5A C9A 114.8(15) . 6_556 ?
C7A O5A C9A 114.8(15) . . ?
C9A O5A C9A 37.1(16) 6_556 . ?
C6A C7A C8A 120.8(19) . . ?
O5A C7A C6A 127.2(17) . . ?
O5A C7A C8A 112.0(15) . . ?
C7B O5B C9B 120.5(9) . . ?
C4 C6B H6B 119.6 . . ?
C7B C6B C4 120.8(9) . . ?
C7B C6B H6B 119.6 . . ?
O5B C7B O5B 47.0(10) . 6_556 ?
O5B C7B C6B 123.6(9) . . ?
O5B C7B C8B 117.3(8) . . ?
C6B C7B O5B 112.7(10) . 6_556 ?
C6B C7B C8B 119.1(9) . . ?
C8B C7B O5B 108.4(10) . 6_556 ?
O5B C9B C10B 114.4(11) . . ?
O5A C9A C10A 116.6(14) . . ?
C11B C10B C9B 111.4(14) . . ?
C11C C10B C9B 115.1(14) . . ?
C11C C10B C11B 109(3) . . ?
C11A C10A C9A 111.1(14) . . ?
C2 C8A H8A 118.5 . . ?
C7A C8A C2 123.0(19) . . ?
C7A C8A H8A 118.5 . . ?
C2 C8B H8B 120.0 . . ?
C7B C8B C2 120.0(10) . . ?
C7B C8B H8B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 C5 C4 180.0 3_456 . . . ?
Zn1 O3 C5 O4 0.0 3_456 . . . ?
Zn1 O1 C1 O2 0.0 . . . . ?
Zn1 O1 C1 C2 180.0 . . . . ?
Zn1 O1 C1 C1 0.0 . . . 6_556 ?
Zn1 O2 C1 O1 0.0 . . . . ?
Zn1 O2 C1 C2 180.0 . . . . ?
Zn1 O2 C1 C1 0.0 . . . 6_556 ?
Zn1 N1 C12A C13A 179.1(9) . . . . ?
Zn1 N1 C16A C15A -176.7(9) . . . . ?
Zn1 N1 C16B C15B -175.8(11) . . . . ?
Zn1 N1 C12B C13B 178.1(10) . . . . ?
O3 C5 C4 C3 0.0 . . . . ?
O3 C5 C4 C6A 180.0 . . . . ?
O3 C5 C4 C6B -164.0(7) . . . 6_556 ?
O3 C5 C4 C6B 164.0(7) . . . . ?
N1 C12A C13A C14 -1.5(19) . . . . ?
N1 C16A C15A C14 -3.4(19) . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C2 C3 C4 C6A 0.0 . . . . ?
C2 C3 C4 C6B 15.9(7) . . . . ?
C2 C3 C4 C6B -15.9(7) . . . 6_556 ?
C3 C2 C1 O1 0.0 . . . . ?
C3 C2 C1 O2 180.0 . . . . ?
C3 C2 C1 C1 0.0 . . . 6_556 ?
C3 C2 C8A C7A 0.0 . . . . ?
C3 C2 C8B C7B 12.9(17) . . . . ?
C3 C4 C6A C7A 0.0 . . . . ?
C3 C4 C6B C7B -11.7(15) . . . . ?
C5 C4 C6A C7A 180.0 . . . . ?
C5 C4 C6B C7B -175.9(10) . . . . ?
C12A N1 C16A C15A 5.0(16) . . . . ?
C4 C6A C7A O5A 180.0 . . . . ?
C4 C6A C7A C8A 0.0 . . . . ?
C4 C6B C7B O5B -121.1(14) . . . 6_556 ?
C4 C6B C7B O5B -173.6(12) . . . . ?
C4 C6B C7B C8B 8(2) . . . . ?
C16A N1 C12A C13A -2.6(16) . . . . ?
C14 C14 C15A C16A -178.5(9) 6 . . . ?
C14 C14 C13A C12A -179.2(9) 6 . . . ?
C14 C14 C15B C16B -178.9(10) 6 . . . ?
C14 C14 C13B C12B -179.1(9) 6 . . . ?
C14 C15B C16B N1 -3(2) . . . . ?
C14 C13B C12B N1 -1(2) . . . . ?
C1 O1 C1 O2 0(100) 6_556 . . . ?
C1 O1 C1 C2 0.0 6_556 . . . ?
C1 O2 C1 O1 0.0 6_556 . . . ?
C1 O2 C1 C2 0(100) 6_556 . . . ?
C1 C2 C3 C4 180.0 6_556 . . . ?
C1 C2 C3 C4 180.0 . . . . ?
C1 C2 C1 O1 0.0 6_556 . . . ?
C1 C2 C1 O2 0(100) 6_556 . . . ?
C1 C2 C8A C7A 180.0 6_556 . . . ?
C1 C2 C8A C7A 180.0 . . . . ?
C1 C2 C8B C7B 176.1(10) 6_556 . . . ?
C1 C2 C8B C7B 176.1(10) . . . . ?
C15A C14 C13A C12A 3.0(14) . . . . ?
C13A C14 C15A C16A -0.8(15) . . . . ?
O4 C5 C4 C3 180.0 . . . . ?
O4 C5 C4 C6A 0.0 . . . . ?
O4 C5 C4 C6B 16.0(7) . . . 6_556 ?
O4 C5 C4 C6B -16.0(7) . . . . ?
C15B C14 C13B C12B 4.2(16) . . . . ?
C13B C14 C15B C16B -2.2(16) . . . . ?
C16B N1 C12B C13B -3.7(18) . . . . ?
C12B N1 C16B C15B 6.0(19) . . . . ?
C6A C7A C8A C2 0.0 . . . . ?
O5A C7A C8A C2 180.0 . . . . ?
O5A C9A C10A C11A -52(3) . . . . ?
C7A O5A C9A C10A -72.0(18) . . . . ?
O5B C7B C8B C2 172.9(12) . . . . ?
O5B C7B C8B C2 122.4(14) 6_556 . . . ?
O5B C9B C10B C11B -66(3) . . . . ?
O5B C9B C10B C11C 169(3) . . . . ?
C6B C4 C6B C7B 86.2(13) 6_556 . . . ?
C6B C7B C8B C2 -8(2) . . . . ?
C7B O5B C9B C10B -71.3(16) . . . . ?
C9B O5B C7B O5B -108.3(10) . . . 6_556 ?
C9B O5B C7B C6B -17(2) . . . . ?
C9B O5B C7B C8B 161.4(12) . . . . ?
C9A O5A C7A C6A 20.5(9) 6_556 . . . ?
C9A O5A C7A C6A -20.5(9) . . . . ?
C9A O5A C7A C8A -159.5(9) 6_556 . . . ?
C9A O5A C7A C8A 159.5(9) . . . . ?
C9A O5A C9A C10A -170.9(14) 6_556 . . . ?
C8A C2 C3 C4 0.0 . . . . ?
C8A C2 C1 O1 180.0 . . . . ?
C8A C2 C1 O2 0.0 . . . . ?
C8A C2 C1 C1 0.0 . . . 6_556 ?
C8B C2 C3 C4 -16.8(8) . . . . ?
C8B C2 C3 C4 16.8(8) 6_556 . . . ?
C8B C2 C1 O1 163.4(8) 6_556 . . . ?
C8B C2 C1 O1 -163.4(8) . . . . ?
C8B C2 C1 O2 16.6(8) . . . . ?
C8B C2 C1 O2 -16.6(8) 6_556 . . . ?
C8B C2 C1 C1 0.00(3) 6_556 . . 6_556 ?
C8B C2 C1 C1 0.00(3) . . . 6_556 ?
C8B C2 C8B C7B -85.7(13) 6_556 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.461 -0.254 0.000 849.3 226.1 DMF

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 7 0.1225 -0.3858 0.0711 7.3988 -0.2688 0.0636 0.9611
-8 7 1 0.0482 -8.2095 6.5760 0.5023 -0.9568 0.2293 -0.1787
1 0 -7 0.1374 0.6478 -0.2819 -7.3873 0.2985 -0.0708 -0.9518
8 -7 0 0.0446 8.1984 -6.5976 0.4428 0.9268 -0.2222 0.3026
2 -1 7 0.1220 2.4916 -0.9048 7.1711 0.0137 0.0975 0.9951
-6 -9 0 0.0411 -5.8406 -8.6452 0.1965 -0.1296 -0.9890 0.0707
-3 0 -7 0.1440 -3.0480 0.0463 -7.0972 -0.0264 -0.1942 -0.9806
6 9 0 0.0328 5.9076 8.6071 0.0180 0.1299 0.9907 -0.0409
10 -3 0 0.0501 10.0110 -2.9439 -0.0186 0.9400 0.1645 0.2123
-6 9 0 0.0569 -6.0322 8.9537 0.0010 -0.8603 0.5208 -0.2472
6 -9 0 0.0569 6.0322 -8.9537 -0.0010 0.8603 -0.5208 0.2472
-8 -6 0 0.0508 -7.9789 -6.0301 0.0267 -0.4063 -0.8544 -0.0300

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Solvothermal Synthesis'
####################################################################### 
# 
# 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_ascid-propoxy_red
_database_code_depnum_ccdc_archive 'CCDC 1540827'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-03-23
_audit_creation_method           ;
_shelx_SHELXL_version_number     2014/7


_chemical_name_common            2_CID
_chemical_name_systematic        Zn(P-ip)(bipy)_CID
_chemical_formula_moiety         'C21 H18 N2 O5 Zn'
_chemical_formula_sum            'C21 H18 N2 O5 Zn'
_chemical_formula_weight         443.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn N2 C20 H50 O5'
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       ;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9902(4)
_cell_length_b                   11.4259(4)
_cell_length_c                   12.1064(5)
_cell_angle_alpha                109.285(3)
_cell_angle_beta                 108.208(4)
_cell_angle_gamma                97.690(3)
_cell_volume                     1194.97(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4642
_cell_measurement_temperature    106.3(5)
_cell_measurement_theta_max      73.7170
_cell_measurement_theta_min      4.1650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.1166
_exptl_crystal_size_min          0.0627
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.189
_diffrn_reflns_theta_min         4.185
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106.3(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4372
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1626874000
_diffrn_orient_matrix_UB_12      0.0245535000
_diffrn_orient_matrix_UB_13      0.0800336000
_diffrn_orient_matrix_UB_21      0.0250075000
_diffrn_orient_matrix_UB_22      -0.0737457000
_diffrn_orient_matrix_UB_23      -0.1205207000
_diffrn_orient_matrix_UB_31      0.0352162000
_diffrn_orient_matrix_UB_32      0.1260824000
_diffrn_orient_matrix_UB_33      -0.0183635000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4323
_reflns_number_total             4677
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          ;


_reflns_Friedel_fraction         is
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01)'
_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    ;
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.086
_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)+(0.0499P)²+0.1933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0864
_refine_special_details          ', SQUEEZE'
_olex2_refinement_description    ;
_atom_sites_solution_hydrogens   geom
_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 0.22369(2) 0.57260(2) 0.12364(2) 0.01253(8) Uani 1 1 d . . . . .
O4 O 1.09783(12) 0.59918(10) 0.22700(11) 0.0150(2) Uani 1 1 d . . . . .
O3 O 0.88453(12) 0.49307(11) 0.06805(11) 0.0176(2) Uani 1 1 d . . . . .
O1 O 0.43332(12) 0.59494(11) 0.12214(11) 0.0184(2) Uani 1 1 d . . . . .
O2 O 0.43560(13) 0.66640(12) 0.31573(12) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.97286(13) 0.88130(12) 0.58069(11) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.22429(14) 0.76324(13) 0.12635(13) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.21687(15) 1.37960(13) 0.11521(13) 0.0164(3) Uani 1 1 d . . . . .
C3 C 0.73301(17) 0.61174(14) 0.21293(15) 0.0137(3) Uani 1 1 d . . . . .
H3 H 0.6778 0.5549 0.1298 0.016 Uiso 1 1 calc R . . . .
C4 C 0.88455(17) 0.63728(14) 0.26075(15) 0.0129(3) Uani 1 1 d . . . . .
C5 C 0.95961(17) 0.57133(14) 0.17770(15) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.66506(17) 0.67294(15) 0.29187(16) 0.0153(3) Uani 1 1 d . . . . .
C15 C 0.2640(2) 0.91717(16) 0.03725(16) 0.0207(3) Uani 1 1 d . . . . .
H15 H 0.2924 0.9374 -0.0219 0.025 Uiso 1 1 calc R . . . .
C1 C 0.50058(17) 0.64390(15) 0.24097(16) 0.0162(3) Uani 1 1 d . . . . .
C19 C 0.11909(19) 1.31675(16) 0.1438(2) 0.0262(4) Uani 1 1 d . . . . .
H19 H 0.0483 1.3556 0.1623 0.031 Uiso 1 1 calc R . . . .
C8 C 0.74711(18) 0.75974(15) 0.41508(16) 0.0170(3) Uani 1 1 d . . . . .
H8 H 0.7007 0.7986 0.4673 0.020 Uiso 1 1 calc R . . . .
C6 C 0.96847(17) 0.72526(15) 0.38400(15) 0.0153(3) Uani 1 1 d . . . . .
H6 H 1.0697 0.7415 0.4149 0.018 Uiso 1 1 calc R . . . .
C12 C 0.18659(18) 0.85064(16) 0.20860(16) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.1613 0.8288 0.2683 0.022 Uiso 1 1 calc R . . . .
C20 C 0.3156(2) 1.32017(17) 0.08645(19) 0.0263(4) Uani 1 1 d . . . . .
H20 H 0.3840 1.3617 0.0650 0.032 Uiso 1 1 calc R . . . .
C7 C 0.89991(18) 0.78889(15) 0.46097(15) 0.0160(3) Uani 1 1 d . . . . .
C16 C 0.2620(2) 0.79754(16) 0.04228(16) 0.0200(3) Uani 1 1 d . . . . .
H16 H 0.2880 0.7382 -0.0155 0.024 Uiso 1 1 calc R . . . .
C17 C 0.22065(18) 1.13563(15) 0.11908(15) 0.0163(3) Uani 1 1 d . . . . .
C18 C 0.11751(19) 1.19632(17) 0.1473(2) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.0475 1.1567 0.1685 0.031 Uiso 1 1 calc R . . . .
C9 C 1.12953(18) 0.92033(16) 0.62217(16) 0.0200(3) Uani 1 1 d . . . . .
H9A H 1.1559 0.9445 0.5606 0.024 Uiso 1 1 calc R . . . .
H9B H 1.1700 0.8495 0.6300 0.024 Uiso 1 1 calc R . . . .
C13 C 0.18357(19) 0.97138(15) 0.20891(16) 0.0191(3) Uani 1 1 d . . . . .
H13 H 0.1553 1.0283 0.2668 0.023 Uiso 1 1 calc R . . . .
C10 C 1.1908(2) 1.03325(17) 0.74864(16) 0.0220(3) Uani 1 1 d . . . . .
H10A H 1.1587 1.0110 0.8086 0.026 Uiso 1 1 calc R . . . .
H10B H 1.1557 1.1060 0.7396 0.026 Uiso 1 1 calc R . . . .
C11 C 1.3577(2) 1.06885(18) 0.79734(17) 0.0260(4) Uani 1 1 d . . . . .
H11A H 1.3883 1.0739 0.7310 0.039 Uiso 1 1 calc GR . . . .
H11B H 1.3929 1.0044 0.8236 0.039 Uiso 1 1 calc GR . . . .
H11C H 1.3966 1.1506 0.8679 0.039 Uiso 1 1 calc GR . . . .
C21 C 0.3210(2) 1.20002(18) 0.0871(2) 0.0278(4) Uani 1 1 d . . . . .
H21 H 0.3915 1.1625 0.0662 0.033 Uiso 1 1 calc R . . . .
C14 C 0.22326(17) 1.00695(15) 0.12178(16) 0.0162(3) Uani 1 1 d . . . . .


_geom_special_details            ;
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 O4 2.0182(11) 1_455 ?
Zn1 O3 2.0450(12) 2_665 ?
Zn1 O1 2.0821(11) . ?
Zn1 O2 2.3892(13) . ?
Zn1 N1 2.1668(13) . ?
Zn1 N2 2.1644(13) 1_545 ?
Zn1 C1 2.5515(16) . ?
O4 Zn1 2.0183(11) 1_655 ?
O4 C5 1.2674(19) . ?
O3 Zn1 2.0450(12) 2_665 ?
O3 C5 1.240(2) . ?
O1 C1 1.264(2) . ?
O2 C1 1.251(2) . ?
O5 C7 1.367(2) . ?
O5 C9 1.440(2) . ?
N1 C12 1.345(2) . ?
N1 C16 1.340(2) . ?
N2 Zn1 2.1644(13) 1_565 ?
N2 C19 1.333(2) . ?
N2 C20 1.339(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C3 C2 1.398(2) . ?
C4 C5 1.504(2) . ?
C4 C6 1.393(2) . ?
C2 C1 1.509(2) . ?
C2 C8 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C15 C14 1.395(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.401(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 C21 1.389(3) . ?
C17 C14 1.485(2) . ?
C18 H18 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.529(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C21 H21 0.9300 . ?

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
O4 Zn1 O3 115.87(5) 1_455 2_665 ?
O4 Zn1 O1 147.66(5) 1_455 . ?
O4 Zn1 O2 89.08(4) 1_455 . ?
O4 Zn1 N1 87.80(5) 1_455 . ?
O4 Zn1 N2 92.25(5) 1_455 1_545 ?
O4 Zn1 C1 118.17(5) 1_455 . ?
O3 Zn1 O1 96.24(5) 2_665 . ?
O3 Zn1 O2 154.33(4) 2_665 . ?
O3 Zn1 N1 86.23(5) 2_665 . ?
O3 Zn1 N2 92.07(5) 2_665 1_545 ?
O3 Zn1 C1 125.64(5) 2_665 . ?
O1 Zn1 O2 58.59(4) . . ?
O1 Zn1 N1 90.68(5) . . ?
O1 Zn1 N2 90.28(5) . 1_545 ?
O1 Zn1 C1 29.50(5) . . ?
O2 Zn1 C1 29.09(5) . . ?
N1 Zn1 O2 88.95(5) . . ?
N1 Zn1 C1 90.32(5) . . ?
N2 Zn1 O2 92.92(5) 1_545 . ?
N2 Zn1 N1 178.13(5) 1_545 . ?
N2 Zn1 C1 91.31(5) 1_545 . ?
C5 O4 Zn1 122.98(10) . 1_655 ?
C5 O3 Zn1 157.96(11) . 2_665 ?
C1 O1 Zn1 96.29(10) . . ?
C1 O2 Zn1 82.67(10) . . ?
C7 O5 C9 115.99(13) . . ?
C12 N1 Zn1 123.05(11) . . ?
C16 N1 Zn1 119.71(11) . . ?
C16 N1 C12 117.24(14) . . ?
C19 N2 Zn1 121.89(11) . 1_565 ?
C19 N2 C20 116.92(15) . . ?
C20 N2 Zn1 121.13(12) . 1_565 ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 118.93(14) . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.72(14) . . ?
C3 C4 C6 120.94(14) . . ?
C6 C4 C5 119.32(14) . . ?
O4 C5 C4 116.51(14) . . ?
O3 C5 O4 124.34(14) . . ?
O3 C5 C4 119.13(14) . . ?
C3 C2 C1 119.08(14) . . ?
C8 C2 C3 120.72(14) . . ?
C8 C2 C1 120.19(14) . . ?
C16 C15 H15 120.3 . . ?
C16 C15 C14 119.36(16) . . ?
C14 C15 H15 120.3 . . ?
O1 C1 Zn1 54.20(8) . . ?
O1 C1 C2 117.61(14) . . ?
O2 C1 Zn1 68.24(9) . . ?
O2 C1 O1 122.42(15) . . ?
O2 C1 C2 119.96(15) . . ?
C2 C1 Zn1 171.35(12) . . ?
N2 C19 H19 118.3 . . ?
N2 C19 C18 123.39(16) . . ?
C18 C19 H19 118.3 . . ?
C2 C8 H8 120.0 . . ?
C2 C8 C7 120.02(15) . . ?
C7 C8 H8 120.0 . . ?
C4 C6 H6 120.1 . . ?
C4 C6 C7 119.73(15) . . ?
C7 C6 H6 120.1 . . ?
N1 C12 H12 118.3 . . ?
N1 C12 C13 123.31(16) . . ?
C13 C12 H12 118.3 . . ?
N2 C20 H20 118.4 . . ?
N2 C20 C21 123.26(17) . . ?
C21 C20 H20 118.4 . . ?
O5 C7 C8 116.36(14) . . ?
O5 C7 C6 124.07(15) . . ?
C6 C7 C8 119.57(15) . . ?
N1 C16 C15 123.19(15) . . ?
N1 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C18 C17 C21 117.01(15) . . ?
C18 C17 C14 121.52(16) . . ?
C21 C17 C14 121.47(15) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 C19 119.65(17) . . ?
C17 C18 H18 120.2 . . ?
O5 C9 H9A 109.9 . . ?
O5 C9 H9B 109.9 . . ?
O5 C9 C10 109.10(14) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.34(15) . . ?
C14 C13 H13 120.3 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C9 C10 C11 109.22(15) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C20 C21 C17 119.75(16) . . ?
C20 C21 H21 120.1 . . ?
C17 C21 H21 120.1 . . ?
C15 C14 C17 121.68(15) . . ?
C13 C14 C15 117.54(15) . . ?
C13 C14 C17 120.77(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C5 O3 22.3(2) 1_655 . . . ?
Zn1 O4 C5 C4 -158.82(10) 1_655 . . . ?
Zn1 O3 C5 O4 -88.7(3) 2_665 . . . ?
Zn1 O3 C5 C4 92.5(3) 2_665 . . . ?
Zn1 O1 C1 O2 -2.11(17) . . . . ?
Zn1 O1 C1 C2 176.70(11) . . . . ?
Zn1 O2 C1 O1 1.84(15) . . . . ?
Zn1 O2 C1 C2 -176.94(13) . . . . ?
Zn1 N1 C12 C13 -178.48(13) . . . . ?
Zn1 N1 C16 C15 179.51(14) . . . . ?
Zn1 N2 C19 C18 -175.70(15) 1_565 . . . ?
Zn1 N2 C20 C21 176.10(16) 1_565 . . . ?
O5 C9 C10 C11 176.03(14) . . . . ?
N1 C12 C13 C14 -1.0(3) . . . . ?
N2 C19 C18 C17 -0.6(3) . . . . ?
N2 C20 C21 C17 -0.2(3) . . . . ?
C3 C4 C5 O4 179.80(13) . . . . ?
C3 C4 C5 O3 -1.3(2) . . . . ?
C3 C4 C6 C7 0.0(2) . . . . ?
C3 C2 C1 O1 -19.3(2) . . . . ?
C3 C2 C1 O2 159.56(15) . . . . ?
C3 C2 C8 C7 1.2(2) . . . . ?
C4 C3 C2 C1 -179.05(14) . . . . ?
C4 C3 C2 C8 1.3(2) . . . . ?
C4 C6 C7 O5 -176.61(15) . . . . ?
C4 C6 C7 C8 2.5(2) . . . . ?
C5 C4 C6 C7 178.72(14) . . . . ?
C2 C3 C4 C5 179.36(14) . . . . ?
C2 C3 C4 C6 -1.9(2) . . . . ?
C2 C8 C7 O5 176.04(15) . . . . ?
C2 C8 C7 C6 -3.2(2) . . . . ?
C1 C2 C8 C7 -178.39(14) . . . . ?
C19 N2 C20 C21 -0.9(3) . . . . ?
C8 C2 C1 O1 160.37(15) . . . . ?
C8 C2 C1 O2 -20.8(2) . . . . ?
C6 C4 C5 O4 1.1(2) . . . . ?
C6 C4 C5 O3 180.00(14) . . . . ?
C12 N1 C16 C15 0.2(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C17 179.73(15) . . . . ?
C20 N2 C19 C18 1.3(3) . . . . ?
C7 O5 C9 C10 173.11(14) . . . . ?
C16 N1 C12 C13 0.8(2) . . . . ?
C16 C15 C14 C17 -178.80(16) . . . . ?
C16 C15 C14 C13 0.7(3) . . . . ?
C18 C17 C21 C20 0.9(3) . . . . ?
C18 C17 C14 C15 145.49(19) . . . . ?
C18 C17 C14 C13 -34.0(3) . . . . ?
C9 O5 C7 C8 -173.72(14) . . . . ?
C9 O5 C7 C6 5.5(2) . . . . ?
C21 C17 C18 C19 -0.6(3) . . . . ?
C21 C17 C14 C15 -34.0(3) . . . . ?
C21 C17 C14 C13 146.54(18) . . . . ?
C14 C15 C16 N1 -1.0(3) . . . . ?
C14 C17 C18 C19 179.93(17) . . . . ?
C14 C17 C21 C20 -179.58(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.073 -0.969 0.500 347.9 97.2 DMF

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 7 -4 0.1379 0.5285 7.1742 -4.0586 -0.0627 -0.0267 0.9977
-6 1 1 0.0383 -6.3861 0.5682 1.4537 -0.9086 -0.3768 -0.1799
1 -7 4 0.1523 0.6883 -7.3064 3.7947 0.2363 0.0987 -0.9667
6 0 -2 0.0820 6.3778 -0.3558 -1.5672 0.9034 0.3746 0.2085
-1 0 7 0.0444 -0.5225 0.4851 6.8595 0.4759 -0.8756 -0.0832
0 -1 -7 0.0082 0.4526 -1.0102 -6.5774 -0.4776 0.8785 0.0094
6 -1 -2 0.0663 6.0019 -0.9985 -2.0059 0.7914 0.4655 0.1223
4 0 -7 0.0378 3.9976 0.0039 -7.0022 0.0900 0.9436 0.2699
3 -3 5 0.0923 3.0042 -3.0010 4.9944 0.8148 -0.3055 -0.3643
-3 0 7 0.0283 -2.9969 -0.0040 7.0012 0.0727 -0.9184 -0.2346
0 0 7 0.0413 0.0049 -0.0042 6.9982 0.5608 -0.8430 -0.1289

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Solvothermal Synthesis'
####################################################################### 
# 
# 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_as362_red
_database_code_depnum_ccdc_archive 'CCDC 1540824'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            1
_chemical_name_systematic        Zn(E-ip)(bipy)
_chemical_formula_moiety         'C20 H16 N2 O5 Zn'
_chemical_formula_sum            'C20 H16 N2 O5 Zn'
_chemical_formula_weight         429.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Zn N O C H'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0944(3)
_cell_length_b                   10.3898(2)
_cell_length_c                   10.4930(3)
_cell_angle_alpha                65.925(2)
_cell_angle_beta                 75.649(2)
_cell_angle_gamma                76.069(2)
_cell_volume                     961.20(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15955
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      75.9280
_cell_measurement_theta_min      4.5470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 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    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.1109
_exptl_crystal_size_mid          0.0734
_exptl_crystal_size_min          0.0619
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.287
_diffrn_reflns_theta_min         4.579
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2186
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1243144000
_diffrn_orient_matrix_UB_12      0.1038512000
_diffrn_orient_matrix_UB_13      -0.0647670000
_diffrn_orient_matrix_UB_21      -0.0942160000
_diffrn_orient_matrix_UB_22      -0.0516339000
_diffrn_orient_matrix_UB_23      0.1451679000
_diffrn_orient_matrix_UB_31      0.0334716000
_diffrn_orient_matrix_UB_32      0.1166057000
_diffrn_orient_matrix_UB_33      0.0367407000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3751
_reflns_number_total             3974
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'
_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         0.347
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+0.5828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0608
_refine_special_details          ', SQUEEZE'
_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
2. Restrained distances
 O5B-C9B = O5A-C9A
 1.43 with sigma of 0.01
 C8A-C2 = C8B-C2 = C8A-C7A = C8B-C7B = C7A-C6A = C6B-C7B = C6A-C4 = C6B-C4
 1.4 with sigma of 0.01
 C10B-C9B = C10A-C9A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C9B) \\sim Ueq, Uanis(C10B) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O5B) = Uanis(O5A)
Uanis(C8A) = Uanis(C8B)
Uanis(C7A) = Uanis(C7B)
Uanis(C6A) = Uanis(C6B)
4. Others
 Sof(O5B)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C7B)=Sof(C8B)=Sof(H8B)=Sof(C6B)=
 Sof(H6B)=Sof(C10B)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(O5A)=Sof(C8A)=Sof(H8A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C9B(H9BA,H9BB)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C17(H17), C3(H3), C14(H14), C20(H20), C8A(H8A), C6A(H6A),
 C8B(H8B), C6B(H6B)
5.c Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C10B(H10D,H10E,H10F)
;
_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 0.60657(2) 0.08684(2) 1.07431(2) 0.01667(6) Uani 1 1 d . . . . .
O4 O 1.40371(10) 0.16485(11) 1.14423(10) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.67932(10) 0.21291(12) 1.16980(11) 0.0253(2) Uani 1 1 d . . . . .
O3 O 1.33892(10) 0.04114(11) 1.04762(11) 0.0224(2) Uani 1 1 d . . . . .
O1 O 0.82491(10) 0.08186(12) 1.06026(11) 0.0245(2) Uani 1 1 d . . . . .
N1 N 0.59165(12) 0.26936(12) 0.88148(12) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.60018(12) 0.89990(13) 0.26124(12) 0.0205(2) Uani 1 1 d . . . . .
C18 C 0.51993(16) 0.90150(16) 0.38337(15) 0.0236(3) Uani 1 1 d . . . . .
H18 H 0.4657(19) 0.991(2) 0.3798(19) 0.028 Uiso 1 1 d R . . . .
C5 C 1.31322(13) 0.12966(14) 1.10589(13) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.80118(15) 0.16695(16) 1.12327(15) 0.0220(3) Uani 1 1 d . . . . .
C19 C 0.67832(16) 0.77548(17) 0.26184(16) 0.0291(4) Uani 1 1 d . . . . .
H19 H 0.735(2) 0.774(2) 0.179(2) 0.035 Uiso 1 1 d R . . . .
O5A O 0.96869(14) 0.51092(16) 1.22430(18) 0.0332(3) Uani 0.7879(17) 1 d D . P A
1
C13 C 0.59166(14) 0.52012(15) 0.63736(14) 0.0188(3) Uani 1 1 d . . . . .
C15 C 0.64887(16) 0.26614(16) 0.75308(16) 0.0238(3) Uani 1 1 d . . . . .
H15 H 0.6912(19) 0.176(2) 0.749(2) 0.029 Uiso 1 1 d R . . . .
C16 C 0.59527(14) 0.65259(15) 0.50831(14) 0.0195(3) Uani 1 1 d . . . . .
C12 C 0.52951(15) 0.52336(15) 0.77058(15) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.4863 0.6113 0.7809 0.027 Uiso 1 1 calc R . . . .
C4 C 1.16535(15) 0.20027(17) 1.13218(16) 0.0241(3) Uani 1 1 d D . . . .
C11 C 0.53140(15) 0.39688(15) 0.88786(15) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.4876 0.4009 0.9777 0.027 Uiso 1 1 calc R . . . .
C17 C 0.51435(16) 0.78232(16) 0.50790(15) 0.0233(3) Uani 1 1 d . . . . .
H17 H 0.4561 0.7888 0.5921 0.028 Uiso 1 1 calc R . . . .
C3 C 1.05751(14) 0.15213(16) 1.11254(15) 0.0215(3) Uani 1 1 d . . . . .
H3 H 1.0761 0.0753 1.0804 0.026 Uiso 1 1 calc R . . . .
C14 C 0.65092(16) 0.38685(16) 0.63057(15) 0.0240(3) Uani 1 1 d . . . . .
H14 H 0.6927 0.3790 0.5418 0.029 Uiso 1 1 calc R . . . .
C20 C 0.67882(16) 0.65180(17) 0.38102(16) 0.0274(3) Uani 1 1 d . . . . .
H20 H 0.7361 0.5662 0.3763 0.033 Uiso 1 1 calc R . . . .
C2 C 0.92114(15) 0.21836(18) 1.14073(17) 0.0269(3) Uani 1 1 d D . . . .
C8A C 0.89624(19) 0.3418(2) 1.1741(2) 0.0231(4) Uani 0.7879(17) 1 d D . P A 1
H8A H 0.8043 0.3904 1.1870 0.028 Uiso 0.7879(17) 1 calc R . P A 1
C6A C 1.14073(19) 0.3235(2) 1.1667(2) 0.0217(4) Uani 0.7879(17) 1 d D . P A 1
H6A H 1.2157 0.3584 1.1750 0.026 Uiso 0.7879(17) 1 calc R . P A 1
C7A C 1.00549(18) 0.3930(2) 1.1883(2) 0.0241(4) Uani 0.7879(17) 1 d D . P A 1
C9A C 1.0762(6) 0.5664(6) 1.2411(6) 0.0393(10) Uani 0.7879(17) 1 d D . P A 1
H9AA H 1.1466 0.5877 1.1538 0.047 Uiso 0.7879(17) 1 calc R . P A 1
H9AB H 1.1219 0.4952 1.3207 0.047 Uiso 0.7879(17) 1 calc R . P A 1
C10A C 1.0145(3) 0.7010(3) 1.2704(4) 0.0536(8) Uani 0.7879(17) 1 d D . P A 1
H10A H 0.9682 0.7704 1.1920 0.080 Uiso 0.7879(17) 1 calc GR . P A 1
H10B H 1.0883 0.7414 1.2799 0.080 Uiso 0.7879(17) 1 calc GR . P A 1
H10C H 0.9471 0.6787 1.3585 0.080 Uiso 0.7879(17) 1 calc GR . P A 1
O5B O 0.9558(5) 0.4068(6) 1.3484(7) 0.0332(3) Uani 0.2121(17) 1 d D . P A 2
C9B C 1.0525(7) 0.4892(8) 1.3505(10) 0.0277(16) Uani 0.2121(17) 1 d D U P A 2
H9BA H 1.1402 0.4269 1.3772 0.033 Uiso 0.2121(17) 1 calc R . P A 2
H9BB H 1.0124 0.5377 1.4186 0.033 Uiso 0.2121(17) 1 calc R . P A 2
C7B C 0.9950(6) 0.3226(8) 1.2683(9) 0.0241(4) Uani 0.2121(17) 1 d D . P A 2
C8B C 0.8879(7) 0.2856(9) 1.2360(8) 0.0231(4) Uani 0.2121(17) 1 d D . P A 2
H8B H 0.7946 0.3060 1.2783 0.028 Uiso 0.2121(17) 1 calc R . P A 2
C6B C 1.1323(7) 0.2720(9) 1.2244(8) 0.0217(4) Uani 0.2121(17) 1 d D . P A 2
H6B H 1.2041 0.2869 1.2582 0.026 Uiso 0.2121(17) 1 calc R . P A 2
C10B C 1.077(3) 0.598(2) 1.1995(15) 0.034(4) Uani 0.2121(17) 1 d D U P A 2
H10D H 1.1372 0.5502 1.1375 0.051 Uiso 0.2121(17) 1 calc GR . P A 2
H10E H 1.1216 0.6728 1.1979 0.051 Uiso 0.2121(17) 1 calc GR . P A 2
H10F H 0.9883 0.6407 1.1662 0.051 Uiso 0.2121(17) 1 calc GR . P A 2


_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 O4 2.0808(10) 1_455 ?
Zn1 O2 2.2711(11) . ?
Zn1 O3 2.0962(10) 2_757 ?
Zn1 O1 2.1615(10) . ?
Zn1 N1 2.1438(11) . ?
Zn1 N2 2.1244(12) 1_546 ?
Zn1 C1 2.5402(15) . ?
O4 Zn1 2.0808(9) 1_655 ?
O4 C5 1.2620(18) . ?
O2 C1 1.2607(18) . ?
O3 Zn1 2.0962(10) 2_757 ?
O3 C5 1.2460(18) . ?
O1 C1 1.2539(19) . ?
N1 C15 1.3385(19) . ?
N1 C11 1.3394(18) . ?
N2 Zn1 2.1244(12) 1_564 ?
N2 C18 1.3399(19) . ?
N2 C19 1.341(2) . ?
C18 H18 0.948(19) . ?
C18 C17 1.386(2) . ?
C5 C4 1.5087(18) . ?
C1 C2 1.512(2) . ?
C19 H19 0.92(2) . ?
C19 C20 1.380(2) . ?
O5A C7A 1.368(2) . ?
O5A C9A 1.421(6) . ?
C13 C16 1.4861(19) . ?
C13 C12 1.3936(19) . ?
C13 C14 1.393(2) . ?
C15 H15 0.948(19) . ?
C15 C14 1.382(2) . ?
C16 C17 1.397(2) . ?
C16 C20 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.386(2) . ?
C4 C3 1.391(2) . ?
C4 C6A 1.419(2) . ?
C4 C6B 1.382(7) . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.401(2) . ?
C14 H14 0.9500 . ?
C20 H20 0.9500 . ?
C2 C8A 1.414(2) . ?
C2 C8B 1.375(6) . ?
C8A H8A 0.9500 . ?
C8A C7A 1.396(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.393(2) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.508(6) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
O5B C9B 1.454(7) . ?
O5B C7B 1.377(8) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.526(9) . ?
C7B C8B 1.386(7) . ?
C7B C6B 1.392(7) . ?
C8B H8B 0.9500 . ?
C6B H6B 0.9500 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?

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
O4 Zn1 O2 88.32(4) 1_455 . ?
O4 Zn1 O3 124.20(4) 1_455 2_757 ?
O4 Zn1 O1 147.57(4) 1_455 . ?
O4 Zn1 N1 86.21(4) 1_455 . ?
O4 Zn1 N2 89.98(4) 1_455 1_546 ?
O4 Zn1 C1 118.02(4) 1_455 . ?
O2 Zn1 C1 29.71(4) . . ?
O3 Zn1 O2 147.26(4) 2_757 . ?
O3 Zn1 O1 88.16(4) 2_757 . ?
O3 Zn1 N1 87.92(4) 2_757 . ?
O3 Zn1 N2 89.50(4) 2_757 1_546 ?
O3 Zn1 C1 117.61(4) 2_757 . ?
O1 Zn1 O2 59.25(4) . . ?
O1 Zn1 C1 29.56(4) . . ?
N1 Zn1 O2 90.92(4) . . ?
N1 Zn1 O1 93.65(4) . . ?
N1 Zn1 C1 91.94(5) . . ?
N2 Zn1 O2 94.69(4) 1_546 . ?
N2 Zn1 O1 92.64(4) 1_546 . ?
N2 Zn1 N1 173.13(5) 1_546 . ?
N2 Zn1 C1 94.90(5) 1_546 . ?
C5 O4 Zn1 114.20(9) . 1_655 ?
C1 O2 Zn1 87.05(9) . . ?
C5 O3 Zn1 172.43(10) . 2_757 ?
C1 O1 Zn1 92.20(8) . . ?
C15 N1 Zn1 123.56(10) . . ?
C15 N1 C11 116.97(12) . . ?
C11 N1 Zn1 119.27(9) . . ?
C18 N2 Zn1 121.70(10) . 1_564 ?
C18 N2 C19 117.29(12) . . ?
C19 N2 Zn1 121.01(10) . 1_564 ?
N2 C18 H18 115.5(11) . . ?
N2 C18 C17 123.39(14) . . ?
C17 C18 H18 121.2(11) . . ?
O4 C5 C4 117.50(13) . . ?
O3 C5 O4 124.00(12) . . ?
O3 C5 C4 118.50(13) . . ?
O2 C1 Zn1 63.24(8) . . ?
O2 C1 C2 119.24(13) . . ?
O1 C1 Zn1 58.25(7) . . ?
O1 C1 O2 121.44(14) . . ?
O1 C1 C2 119.30(13) . . ?
C2 C1 Zn1 175.74(11) . . ?
N2 C19 H19 117.9(13) . . ?
N2 C19 C20 123.05(14) . . ?
C20 C19 H19 119.1(13) . . ?
C7A O5A C9A 117.6(3) . . ?
C12 C13 C16 121.67(13) . . ?
C14 C13 C16 121.38(13) . . ?
C14 C13 C12 116.95(13) . . ?
N1 C15 H15 116.7(11) . . ?
N1 C15 C14 123.22(14) . . ?
C14 C15 H15 120.0(11) . . ?
C17 C16 C13 121.99(13) . . ?
C20 C16 C13 121.01(13) . . ?
C20 C16 C17 117.00(13) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.30(13) . . ?
C11 C12 H12 120.4 . . ?
C3 C4 C5 120.73(13) . . ?
C3 C4 C6A 121.01(14) . . ?
C6A C4 C5 118.08(14) . . ?
C6B C4 C5 118.0(3) . . ?
C6B C4 C3 116.8(3) . . ?
N1 C11 C12 123.61(13) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C18 C17 C16 119.30(13) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.20(14) . . ?
C2 C3 H3 120.4 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.91(13) . . ?
C15 C14 H14 120.0 . . ?
C19 C20 C16 119.97(14) . . ?
C19 C20 H20 120.0 . . ?
C16 C20 H20 120.0 . . ?
C3 C2 C1 120.62(14) . . ?
C3 C2 C8A 119.67(15) . . ?
C8A C2 C1 119.50(14) . . ?
C8B C2 C1 114.6(3) . . ?
C8B C2 C3 119.6(3) . . ?
C2 C8A H8A 119.7 . . ?
C7A C8A C2 120.62(16) . . ?
C7A C8A H8A 119.7 . . ?
C4 C6A H6A 120.3 . . ?
C7A C6A C4 119.38(17) . . ?
C7A C6A H6A 120.3 . . ?
O5A C7A C8A 115.48(16) . . ?
O5A C7A C6A 124.72(17) . . ?
C6A C7A C8A 119.80(18) . . ?
O5A C9A H9AA 109.9 . . ?
O5A C9A H9AB 109.9 . . ?
O5A C9A C10A 108.9(4) . . ?
H9AA C9A H9AB 108.3 . . ?
C10A C9A H9AA 109.9 . . ?
C10A C9A H9AB 109.9 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C7B O5B C9B 120.2(5) . . ?
O5B C9B H9BA 110.8 . . ?
O5B C9B H9BB 110.8 . . ?
O5B C9B C10B 104.8(11) . . ?
H9BA C9B H9BB 108.9 . . ?
C10B C9B H9BA 110.8 . . ?
C10B C9B H9BB 110.8 . . ?
O5B C7B C8B 115.7(5) . . ?
O5B C7B C6B 123.8(6) . . ?
C8B C7B C6B 120.4(6) . . ?
C2 C8B C7B 117.8(6) . . ?
C2 C8B H8B 121.1 . . ?
C7B C8B H8B 121.1 . . ?
C4 C6B C7B 120.9(6) . . ?
C4 C6B H6B 119.6 . . ?
C7B C6B H6B 119.6 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C5 O3 9.12(17) 1_655 . . . ?
Zn1 O4 C5 C4 -170.61(9) 1_655 . . . ?
Zn1 O2 C1 O1 -2.42(14) . . . . ?
Zn1 O2 C1 C2 176.08(13) . . . . ?
Zn1 O1 C1 O2 2.54(15) . . . . ?
Zn1 O1 C1 C2 -175.95(12) . . . . ?
Zn1 N1 C15 C14 -173.23(12) . . . . ?
Zn1 N1 C11 C12 173.01(12) . . . . ?
Zn1 N2 C18 C17 -179.11(12) 1_564 . . . ?
Zn1 N2 C19 C20 179.22(13) 1_564 . . . ?
O4 C5 C4 C3 -170.36(13) . . . . ?
O4 C5 C4 C6A 14.4(2) . . . . ?
O4 C5 C4 C6B -14.9(5) . . . . ?
O2 C1 C2 C3 169.08(14) . . . . ?
O2 C1 C2 C8A -16.3(2) . . . . ?
O2 C1 C2 C8B 14.8(5) . . . . ?
O3 C5 C4 C3 9.9(2) . . . . ?
O3 C5 C4 C6A -165.30(15) . . . . ?
O3 C5 C4 C6B 165.4(4) . . . . ?
O1 C1 C2 C3 -12.4(2) . . . . ?
O1 C1 C2 C8A 162.22(16) . . . . ?
O1 C1 C2 C8B -166.7(4) . . . . ?
N1 C15 C14 C13 0.1(2) . . . . ?
N2 C18 C17 C16 -0.3(2) . . . . ?
N2 C19 C20 C16 0.1(3) . . . . ?
C18 N2 C19 C20 0.1(2) . . . . ?
C5 C4 C3 C2 178.71(13) . . . . ?
C5 C4 C6A C7A 178.51(17) . . . . ?
C5 C4 C6B C7B -171.2(6) . . . . ?
C1 C2 C8A C7A -178.84(17) . . . . ?
C1 C2 C8B C7B 173.6(6) . . . . ?
C19 N2 C18 C17 0.0(2) . . . . ?
C13 C16 C17 C18 -178.57(14) . . . . ?
C13 C16 C20 C19 178.67(15) . . . . ?
C13 C12 C11 N1 0.8(2) . . . . ?
C15 N1 C11 C12 -2.0(2) . . . . ?
C16 C13 C12 C11 -178.77(13) . . . . ?
C16 C13 C14 C15 178.35(14) . . . . ?
C12 C13 C16 C17 -13.0(2) . . . . ?
C12 C13 C16 C20 168.04(14) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
C4 C3 C2 C1 -178.81(14) . . . . ?
C4 C3 C2 C8A 6.6(2) . . . . ?
C4 C3 C2 C8B -25.7(5) . . . . ?
C4 C6A C7A O5A 178.82(19) . . . . ?
C4 C6A C7A C8A -0.8(3) . . . . ?
C11 N1 C15 C14 1.6(2) . . . . ?
C17 C16 C20 C19 -0.4(2) . . . . ?
C3 C4 C6A C7A 3.3(3) . . . . ?
C3 C4 C6B C7B -14.7(9) . . . . ?
C3 C2 C8A C7A -4.2(3) . . . . ?
C3 C2 C8B C7B 18.9(9) . . . . ?
C14 C13 C16 C17 167.30(14) . . . . ?
C14 C13 C16 C20 -11.7(2) . . . . ?
C14 C13 C12 C11 1.0(2) . . . . ?
C20 C16 C17 C18 0.5(2) . . . . ?
C2 C8A C7A O5A -178.39(18) . . . . ?
C2 C8A C7A C6A 1.3(3) . . . . ?
C6A C4 C3 C2 -6.2(2) . . . . ?
C7A O5A C9A C10A 176.1(3) . . . . ?
C9A O5A C7A C8A 179.5(3) . . . . ?
C9A O5A C7A C6A -0.1(4) . . . . ?
O5B C7B C8B C2 171.4(6) . . . . ?
O5B C7B C6B C4 -173.3(7) . . . . ?
C9B O5B C7B C8B -160.1(7) . . . . ?
C9B O5B C7B C6B 21.9(12) . . . . ?
C7B O5B C9B C10B 65.2(13) . . . . ?
C8B C7B C6B C4 8.8(13) . . . . ?
C6B C4 C3 C2 23.0(5) . . . . ?
C6B C7B C8B C2 -10.6(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 107.2 37.0 DMF

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 0 6 0.0529 1.7437 -0.1154 6.1309 -0.6258 0.7317 0.2702
-1 -5 2 0.0523 -0.8741 -5.0297 2.0508 -0.5465 0.6398 -0.5404
-3 -6 -5 0.0434 -3.2139 -5.8466 -5.1973 0.1290 -0.1498 -0.9803
-3 -4 -6 0.0459 -3.0654 -4.0784 -6.4661 0.3763 -0.4393 -0.8157
5 5 4 0.0271 5.2700 5.1073 3.5496 -0.3546 -0.2449 0.9024
6 0 0 0.0270 6.3320 0.0803 0.3405 -0.8009 -0.5513 0.2338
2 -5 -3 0.0338 2.4800 -5.1611 -3.2314 -0.6350 -0.4363 -0.6375
-5 -6 -4 0.0363 -4.7907 -5.5368 -3.8060 0.2671 0.1847 -0.9458
-6 2 1 0.0295 -5.5603 1.8506 0.9458 0.8221 0.5656 0.0644
6 2 -1 0.0396 5.9953 2.0033 -1.0051 -0.4722 -0.8142 0.3973
-5 0 4 0.0395 -4.9940 0.4977 3.5056 0.4455 0.9537 0.0197
4 -2 -4 0.0370 3.9946 -1.9986 -4.0053 -0.4447 -0.8546 -0.2465
-4 -5 1 0.0453 -3.9946 -5.0033 1.0025 -0.0879 0.7802 -0.6803
2 6 6 0.0295 2.0029 5.5022 5.5014 -0.0339 0.3258 0.9108
1 0 -6 0.0466 0.9925 0.0008 -6.0027 0.2655 -0.9650 -0.1872
-2 3 -4 0.0427 -2.0054 3.0003 -3.9986 0.8199 -0.5464 0.1358
-4 4 0 0.0290 -4.0004 3.9995 0.0046 0.9124 0.1711 0.3326
6 2 4 0.0328 6.0012 2.0030 3.9964 -0.7969 -0.0887 0.5813
-6 -1 1 0.0286 -5.9958 -1.0030 1.0054 0.5761 0.7626 -0.2807
5 -2 1 0.0413 5.0010 -2.4986 1.4953 -0.9780 -0.1251 -0.0690

_olex2_submission_special_instructions 'No special instructions were received'
