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

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

data_exp_1177_a
_database_code_depnum_ccdc_archive 'CCDC 2080966'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
nicolas.zigon@univ-angers.fr
_chemical_name_common            ?
_chemical_name_systematic        'Zn salen phenyl bis[4]helicene'
_chemical_formula_moiety         'C44 H28 N2 O3 Zn, C4 H8 O'
_chemical_formula_sum            'C48 H36 N2 O4 Zn'
_chemical_formula_weight         770.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C52N2O2Zn1C26
_chemical_oxdiff_usercomment     'Crystallized from CHCl3/MeOH'
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                   8.1499(14)
_cell_length_b                   30.4057(15)
_cell_length_c                   17.238(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.19(2)
_cell_angle_gamma                90
_cell_volume                     3654.2(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1139
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.6830
_cell_measurement_theta_min      5.3330
_cell_oxdiff_angle_alpha         90.046(7)
_cell_oxdiff_angle_beta          121.168(14)
_cell_oxdiff_angle_gamma         89.971(9)
_cell_oxdiff_length_a            8.1514(13)
_cell_oxdiff_length_b            30.401(2)
_cell_oxdiff_length_c            17.234(2)
_cell_oxdiff_measurement_reflns_used 1140
_cell_oxdiff_volume              3654.2(7)
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 -1 0.0382
0 -5 1 0.0502
2 -2 -7 0.0705
0 4 -5 0.0452
0 -3 5 0.0477
0 -1 0 0.0565
-1 -5 3 0.0589
0 1 0 0.0472
1 -5 -2 0.0706
-2 -5 4 0.0788
-2 -5 -3 0.0541
0 5 3 0.0561
1 5 3 0.0654
0 -5 -3 0.0480
-1 5 4 0.0559
-1 3 -4 0.0384
1 -2 -6 0.0499
2 18 -3 0.0517

_exptl_crystal_preparation       'vapor diffusion of MeOH in THF'
_exptl_crystal_recrystallization_method 'vapor diffusion of MeOH in THF'
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.088
loop_
_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
-0.0022 5.0027 -1.0057 0.0522 0.2505 -0.0992
0.0022 -5.0027 1.0057 -0.0522 -0.2505 0.0992
1.9996 -2.0062 -6.9961 0.1298 0.2972 0.5481
-0.0022 4.0038 -5.0132 0.3666 0.4031 0.1368
0.0017 -3.0033 5.0125 -0.3717 -0.3626 -0.1670
0.0004 -1.0005 0.0007 0.0050 -0.0405 0.0301
-0.9973 -4.9994 3.0015 0.0040 -0.3672 -0.0675
-0.0004 1.0005 -0.0007 -0.0050 0.0405 -0.0301
1.0016 -5.0055 -1.9920 -0.0310 -0.0856 0.3174
-1.9970 -4.9958 3.9951 0.1376 -0.4357 -0.1828
-1.9977 -4.9931 -3.0192 0.6792 -0.0979 0.1776
-0.0018 5.0011 3.0025 -0.2573 0.0576 -0.3051
0.9979 4.9971 3.0108 -0.4682 0.0777 -0.2413
0.0018 -5.0011 -3.0025 0.2573 -0.0576 0.3051
-1.0015 5.0047 3.9961 -0.1237 -0.0109 -0.4203
-1.0014 3.0069 -4.0188 0.5053 0.2942 0.0517
1.0000 -2.0026 -6.0024 0.2633 0.2287 0.4329
1.9916 18.0014 -3.0027 -0.2805 0.9134 -0.2604

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.1345
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13239
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.887
_diffrn_reflns_theta_min         3.331
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3980
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  26.00   0.50    7.28    --   41.11 -19.00  90.00  128
  2  ω    -15.00  82.00   0.50    7.28    --   41.11 -99.00   0.00  194
  3  ω     21.00 106.00   0.50   24.98    --  103.45 -94.00  30.00  170
  4  ω     42.00  71.00   0.50   24.98    --  103.45 -61.00  90.00   58
  5  ω     82.00 158.00   0.50   24.98    --  103.45 125.00  30.00  152
  6  ω     78.00 106.00   0.50   24.98    --  103.45  45.00-180.00   56
  7  ω     82.00 158.00   0.50   24.98    --  103.45  77.00  90.00  152
  8  ω    115.00 149.00   0.50   24.98    --  103.45  45.00-180.00   68
  9  ω     82.00 147.00   0.50   24.98    --  103.45  77.00-150.00  130
 10  ω     90.00 150.00   0.50   24.98    --  103.45  45.00 150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2103579000
_diffrn_orient_matrix_UB_12      -0.0051853000
_diffrn_orient_matrix_UB_13      -0.0771870000
_diffrn_orient_matrix_UB_21      0.0207544000
_diffrn_orient_matrix_UB_22      0.0404148000
_diffrn_orient_matrix_UB_23      -0.0481338000
_diffrn_orient_matrix_UB_31      0.0640870000
_diffrn_orient_matrix_UB_32      -0.0301297000
_diffrn_orient_matrix_UB_33      -0.0513877000
_diffrn_oxdiff_digest_frames     
;
019b3d0cf3c67e568d9f6d5c6ad6853bee01280435b
;
_diffrn_oxdiff_digest_hkl        
;
01da44ffbcda5557eb953f1dce434a51a0b40c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3232
_reflns_number_total             6896
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         6896
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.0933
_refine_ls_restrained_S_all      1.026
_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)+(0.0961P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2204
_refine_ls_wR_factor_ref         0.2875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O4-H4A = O4-H4B
 0.96 with sigma of 0.02
 H4A-H4B
 1.63 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim O1 \\sim C2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4C,H4D)
4.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C30(H30), C19(H19), C22(H22), C36(H36), C33(H33), C48(H48),
 C25(H25), C11(H11), C16(H16), C28(H28), C37(H37), C38(H38), C45(H45), C15(H15),
  C5(H5), C12(H12), C42(H42), C46(H46), C47(H47), C26(H26), C41(H41), C27(H27),
 C8(H8), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.65656(16) 0.46938(3) 0.44949(7) 0.0631(3) Uani 1 1 d . . . . .
N1 N 0.6585(10) 0.41038(19) 0.3889(4) 0.0650(16) Uani 1 1 d . . . . .
O2 O 0.6728(9) 0.43701(15) 0.5528(3) 0.0693(14) Uani 1 1 d . . . . .
C1 C 0.773(3) 0.5257(8) 0.0086(16) 0.221(9) Uani 1 1 d . U . . .
H1A H 0.639119 0.518670 -0.033236 0.265 Uiso 1 1 calc R U . . .
H1B H 0.849696 0.499989 0.014971 0.265 Uiso 1 1 calc R U . . .
O1 O 0.802(3) 0.5381(6) 0.0938(12) 0.239(7) Uani 1 1 d . U . . .
C2 C 0.830(4) 0.5623(8) -0.0243(18) 0.237(11) Uani 1 1 d . U . . .
H2A H 0.732723 0.568886 -0.086584 0.285 Uiso 1 1 calc R U . . .
H2B H 0.949687 0.555925 -0.021641 0.285 Uiso 1 1 calc R U . . .
C3 C 0.856(3) 0.6014(9) 0.0383(18) 0.251(13) Uani 1 1 d . U . . .
H3A H 0.737452 0.617285 0.018571 0.301 Uiso 1 1 calc R U . . .
H3B H 0.955958 0.621587 0.046434 0.301 Uiso 1 1 calc R U . . .
C4 C 0.919(3) 0.5712(10) 0.1266(17) 0.273(13) Uani 1 1 d . U . . .
H4C H 1.051480 0.561625 0.153756 0.328 Uiso 1 1 calc R U . . .
H4D H 0.904885 0.587007 0.171562 0.328 Uiso 1 1 calc R U . . .
O3 O 0.7794(8) 0.52093(14) 0.5304(3) 0.0635(12) Uani 1 1 d . . . . .
O4 O 0.3774(9) 0.49121(15) 0.3720(4) 0.0697(14) Uani 1 1 d D . . . .
H4A H 0.326(13) 0.471(2) 0.396(6) 0.10(3) Uiso 1 1 d D . . . .
H4B H 0.390(11) 0.5207(10) 0.393(5) 0.07(2) Uiso 1 1 d D . . . .
N2 N 0.7684(10) 0.49074(19) 0.3695(4) 0.0662(16) Uani 1 1 d . . . . .
C18 C 0.6657(11) 0.3352(2) 0.6626(5) 0.0607(17) Uani 1 1 d . . . . .
C35 C 0.8411(12) 0.6389(2) 0.5315(5) 0.0668(19) Uani 1 1 d . . . . .
C14 C 0.6701(11) 0.3199(2) 0.7436(5) 0.0629(18) Uani 1 1 d . . . . .
C24 C 0.6785(13) 0.4168(2) 0.3136(5) 0.0653(19) Uani 1 1 d . . . . .
C40 C 0.8257(12) 0.6784(2) 0.5748(6) 0.070(2) Uani 1 1 d . . . . .
C34 C 0.8754(12) 0.6436(2) 0.4583(5) 0.0648(19) Uani 1 1 d . . . . .
C13 C 0.7138(12) 0.2750(2) 0.7665(6) 0.0665(19) Uani 1 1 d . . . . .
C23 C 0.6589(12) 0.3719(2) 0.4204(5) 0.0639(18) Uani 1 1 d . . . . .
H23 H 0.662942 0.347889 0.387973 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6398(12) 0.3475(2) 0.8038(5) 0.0655(18) Uani 1 1 d . . . . .
C17 C 0.6643(12) 0.3038(2) 0.6006(6) 0.0653(19) Uani 1 1 d . . . . .
C29 C 0.7411(12) 0.4593(2) 0.3050(5) 0.0643(18) Uani 1 1 d . . . . .
C30 C 0.8453(12) 0.5285(2) 0.3757(5) 0.0629(18) Uani 1 1 d . . . . .
H30 H 0.898502 0.533552 0.340119 0.076 Uiso 1 1 calc R U . . .
C21 C 0.6655(12) 0.3941(2) 0.5627(5) 0.0621(18) Uani 1 1 d . . . . .
C19 C 0.6560(12) 0.3179(2) 0.5222(5) 0.0650(19) Uani 1 1 d . . . . .
H19 H 0.651903 0.296837 0.482069 0.078 Uiso 1 1 calc R U . . .
C44 C 0.8232(13) 0.6787(2) 0.6594(6) 0.070(2) Uani 1 1 d . . . . .
C22 C 0.6741(12) 0.3795(2) 0.6428(5) 0.0625(18) Uani 1 1 d . . . . .
H22 H 0.686051 0.400485 0.684588 0.075 Uiso 1 1 calc R U . . .
C20 C 0.6535(12) 0.3626(2) 0.5005(5) 0.0627(18) Uani 1 1 d . . . . .
C32 C 0.8087(12) 0.5585(2) 0.5051(5) 0.0647(18) Uani 1 1 d . . . . .
C9 C 0.6877(13) 0.3312(3) 0.8894(6) 0.071(2) Uani 1 1 d . . . . .
C36 C 0.8086(12) 0.5968(2) 0.5511(5) 0.0648(19) Uani 1 1 d . . . . .
H36 H 0.784984 0.593503 0.598077 0.078 Uiso 1 1 calc R U . . .
C33 C 0.8863(11) 0.6060(2) 0.4146(5) 0.0663(19) Uani 1 1 d . . . . .
H33 H 0.916328 0.609473 0.369715 0.080 Uiso 1 1 calc R U . . .
C31 C 0.8545(12) 0.5636(2) 0.4346(5) 0.0631(18) Uani 1 1 d . . . . .
C48 C 0.8826(13) 0.6434(2) 0.7205(5) 0.074(2) Uani 1 1 d . . . . .
H48 H 0.934559 0.618600 0.709788 0.088 Uiso 1 1 calc R U . . .
C43 C 0.7610(13) 0.7178(2) 0.6824(6) 0.074(2) Uani 1 1 d . . . . .
C25 C 0.6328(12) 0.3855(2) 0.2472(5) 0.0682(19) Uani 1 1 d . . . . .
H25 H 0.583953 0.358428 0.250809 0.082 Uiso 1 1 calc R U . . .
C11 C 0.7518(14) 0.2867(3) 0.9130(6) 0.078(2) Uani 1 1 d . . . . .
H11 H 0.792697 0.276429 0.971107 0.094 Uiso 1 1 calc R U . . .
C16 C 0.6867(13) 0.2581(2) 0.6234(6) 0.073(2) Uani 1 1 d . . . . .
H16 H 0.679409 0.237294 0.582152 0.087 Uiso 1 1 calc R U . . .
C28 C 0.7687(12) 0.4666(3) 0.2324(5) 0.069(2) Uani 1 1 d . . . . .
H28 H 0.815094 0.493719 0.227107 0.083 Uiso 1 1 calc R U . . .
C37 C 0.8752(13) 0.6864(2) 0.4240(6) 0.071(2) Uani 1 1 d . . . . .
H37 H 0.902292 0.689613 0.378088 0.085 Uiso 1 1 calc R U . . .
C38 C 0.8361(13) 0.7222(2) 0.4577(6) 0.077(2) Uani 1 1 d . . . . .
H38 H 0.826733 0.749492 0.431189 0.092 Uiso 1 1 calc R U . . .
C45 C 0.7407(14) 0.7170(3) 0.7591(6) 0.082(2) Uani 1 1 d . . . . .
H45 H 0.691754 0.741671 0.772284 0.098 Uiso 1 1 calc R U . . .
C15 C 0.7181(14) 0.2454(2) 0.7040(6) 0.075(2) Uani 1 1 d . . . . .
H15 H 0.743924 0.215900 0.719966 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5454(13) 0.3891(2) 0.7779(6) 0.070(2) Uani 1 1 d . . . . .
H5 H 0.497939 0.399452 0.719312 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7530(13) 0.2598(3) 0.8522(6) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.780372 0.230213 0.866486 0.092 Uiso 1 1 calc R U . . .
C42 C 0.7292(14) 0.7569(3) 0.6327(7) 0.082(2) Uani 1 1 d . . . . .
H42 H 0.686322 0.781911 0.647993 0.099 Uiso 1 1 calc R U . . .
C46 C 0.7909(16) 0.6811(3) 0.8144(7) 0.089(3) Uani 1 1 d . . . . .
H46 H 0.774806 0.681113 0.863969 0.107 Uiso 1 1 calc R U . . .
C39 C 0.8089(13) 0.7196(2) 0.5324(6) 0.073(2) Uani 1 1 d . . . . .
C47 C 0.8661(16) 0.6447(3) 0.7957(6) 0.085(3) Uani 1 1 d . . . . .
H47 H 0.906014 0.620636 0.834666 0.102 Uiso 1 1 calc R U . . .
C26 C 0.6592(15) 0.3940(3) 0.1754(6) 0.083(3) Uani 1 1 d . . . . .
H26 H 0.630454 0.372417 0.131855 0.100 Uiso 1 1 calc R U . . .
C41 C 0.7603(15) 0.7583(3) 0.5634(6) 0.084(3) Uani 1 1 d . . . . .
H41 H 0.750006 0.785022 0.534941 0.101 Uiso 1 1 calc R U . . .
C27 C 0.7280(16) 0.4343(3) 0.1683(6) 0.085(3) Uani 1 1 d . . . . .
H27 H 0.746985 0.439839 0.120458 0.102 Uiso 1 1 calc R U . . .
C8 C 0.6666(15) 0.3577(3) 0.9496(6) 0.083(2) Uani 1 1 d . . . . .
H8 H 0.707579 0.347194 1.007481 0.100 Uiso 1 1 calc R U . . .
C6 C 0.5237(15) 0.4139(3) 0.8380(6) 0.085(3) Uani 1 1 d . . . . .
H6 H 0.465528 0.441345 0.820092 0.102 Uiso 1 1 calc R U . . .
C7 C 0.5871(17) 0.3990(3) 0.9259(7) 0.093(3) Uani 1 1 d . . . . .
H7 H 0.575588 0.416461 0.967091 0.112 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.979(5) . ?
Zn1 O3 1.990(5) . ?
Zn1 O4 2.062(6) . ?
Zn1 N1 2.080(6) . ?
Zn1 N2 2.112(6) . ?
N1 C23 1.289(9) . ?
N1 C24 1.403(9) . ?
O2 C21 1.322(8) . ?
C1 O1 1.41(2) . ?
C1 C2 1.43(3) . ?
O1 C4 1.30(2) . ?
C2 C3 1.55(3) . ?
C3 C4 1.62(3) . ?
O3 C32 1.289(9) . ?
N2 C30 1.284(9) . ?
N2 C29 1.394(9) . ?
C18 C22 1.398(10) . ?
C18 C17 1.428(10) . ?
C18 C14 1.454(10) . ?
C35 C36 1.385(10) . ?
C35 C34 1.434(11) . ?
C35 C40 1.454(11) . ?
C14 C13 1.415(10) . ?
C14 C10 1.453(11) . ?
C24 C25 1.385(10) . ?
C24 C29 1.423(10) . ?
C40 C39 1.418(11) . ?
C40 C44 1.470(12) . ?
C34 C33 1.397(11) . ?
C34 C37 1.429(10) . ?
C13 C15 1.418(11) . ?
C13 C12 1.419(11) . ?
C23 C20 1.433(11) . ?
C10 C9 1.407(11) . ?
C10 C5 1.426(11) . ?
C17 C19 1.386(11) . ?
C17 C16 1.430(10) . ?
C29 C28 1.400(10) . ?
C30 C31 1.450(10) . ?
C21 C20 1.402(10) . ?
C21 C22 1.417(10) . ?
C19 C20 1.407(10) . ?
C44 C48 1.401(11) . ?
C44 C43 1.428(11) . ?
C32 C36 1.408(10) . ?
C32 C31 1.452(10) . ?
C9 C8 1.393(12) . ?
C9 C11 1.433(12) . ?
C33 C31 1.393(10) . ?
C48 C47 1.371(12) . ?
C43 C42 1.407(12) . ?
C43 C45 1.416(12) . ?
C25 C26 1.386(11) . ?
C11 C12 1.332(12) . ?
C16 C15 1.333(11) . ?
C28 C27 1.384(11) . ?
C37 C38 1.347(11) . ?
C38 C39 1.417(12) . ?
C45 C46 1.366(12) . ?
C5 C6 1.364(11) . ?
C42 C41 1.345(13) . ?
C46 C47 1.382(12) . ?
C39 C41 1.431(12) . ?
C26 C27 1.381(13) . ?
C8 C7 1.373(13) . ?
C6 C7 1.400(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O3 89.2(2) . . ?
O2 Zn1 O4 106.3(2) . . ?
O3 Zn1 O4 100.7(2) . . ?
O2 Zn1 N1 90.5(2) . . ?
O3 Zn1 N1 154.1(3) . . ?
O4 Zn1 N1 104.2(2) . . ?
O2 Zn1 N2 153.0(3) . . ?
O3 Zn1 N2 89.1(2) . . ?
O4 Zn1 N2 100.5(2) . . ?
N1 Zn1 N2 79.6(2) . . ?
C23 N1 C24 122.7(6) . . ?
C23 N1 Zn1 124.8(5) . . ?
C24 N1 Zn1 112.3(4) . . ?
C21 O2 Zn1 128.4(5) . . ?
O1 C1 C2 107(2) . . ?
C4 O1 C1 110(2) . . ?
C1 C2 C3 106(2) . . ?
C2 C3 C4 95(2) . . ?
O1 C4 C3 103.1(18) . . ?
C32 O3 Zn1 125.1(5) . . ?
C30 N2 C29 123.4(6) . . ?
C30 N2 Zn1 125.2(5) . . ?
C29 N2 Zn1 111.4(5) . . ?
C22 C18 C17 116.3(7) . . ?
C22 C18 C14 124.1(7) . . ?
C17 C18 C14 119.5(6) . . ?
C36 C35 C34 117.2(7) . . ?
C36 C35 C40 124.2(7) . . ?
C34 C35 C40 118.4(7) . . ?
C13 C14 C10 118.0(7) . . ?
C13 C14 C18 117.0(7) . . ?
C10 C14 C18 125.0(6) . . ?
C25 C24 N1 124.0(7) . . ?
C25 C24 C29 119.7(7) . . ?
N1 C24 C29 116.3(6) . . ?
C39 C40 C35 118.4(7) . . ?
C39 C40 C44 117.4(7) . . ?
C35 C40 C44 124.2(7) . . ?
C33 C34 C37 120.6(7) . . ?
C33 C34 C35 119.2(7) . . ?
C37 C34 C35 119.8(7) . . ?
C14 C13 C15 120.2(7) . . ?
C14 C13 C12 119.6(7) . . ?
C15 C13 C12 120.2(7) . . ?
N1 C23 C20 126.1(7) . . ?
C9 C10 C5 116.9(7) . . ?
C9 C10 C14 119.3(7) . . ?
C5 C10 C14 123.5(7) . . ?
C19 C17 C18 120.1(6) . . ?
C19 C17 C16 120.2(7) . . ?
C18 C17 C16 119.6(7) . . ?
N2 C29 C28 124.7(7) . . ?
N2 C29 C24 117.2(7) . . ?
C28 C29 C24 118.1(7) . . ?
N2 C30 C31 124.3(7) . . ?
O2 C21 C20 124.4(7) . . ?
O2 C21 C22 116.9(6) . . ?
C20 C21 C22 118.6(6) . . ?
C17 C19 C20 122.9(7) . . ?
C48 C44 C43 117.6(8) . . ?
C48 C44 C40 124.4(7) . . ?
C43 C44 C40 117.9(7) . . ?
C18 C22 C21 123.8(7) . . ?
C21 C20 C19 118.1(7) . . ?
C21 C20 C23 125.3(6) . . ?
C19 C20 C23 116.3(6) . . ?
O3 C32 C36 119.1(7) . . ?
O3 C32 C31 123.5(7) . . ?
C36 C32 C31 117.3(7) . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 C11 120.2(8) . . ?
C10 C9 C11 119.6(7) . . ?
C35 C36 C32 124.8(7) . . ?
C31 C33 C34 123.5(7) . . ?
C33 C31 C30 117.2(7) . . ?
C33 C31 C32 117.9(7) . . ?
C30 C31 C32 124.3(6) . . ?
C47 C48 C44 121.6(8) . . ?
C42 C43 C45 120.6(8) . . ?
C42 C43 C44 121.0(8) . . ?
C45 C43 C44 118.3(8) . . ?
C24 C25 C26 120.7(7) . . ?
C12 C11 C9 120.4(8) . . ?
C15 C16 C17 119.7(7) . . ?
C27 C28 C29 121.1(8) . . ?
C38 C37 C34 120.5(8) . . ?
C37 C38 C39 121.9(7) . . ?
C46 C45 C43 121.8(8) . . ?
C16 C15 C13 122.7(7) . . ?
C6 C5 C10 120.9(8) . . ?
C11 C12 C13 122.1(7) . . ?
C41 C42 C43 120.5(8) . . ?
C45 C46 C47 119.2(9) . . ?
C38 C39 C40 120.0(8) . . ?
C38 C39 C41 119.7(7) . . ?
C40 C39 C41 120.3(8) . . ?
C48 C47 C46 121.0(8) . . ?
C27 C26 C25 120.1(8) . . ?
C42 C41 C39 121.4(8) . . ?
C26 C27 C28 120.1(8) . . ?
C7 C8 C9 121.9(8) . . ?
C5 C6 C7 121.5(8) . . ?
C8 C7 C6 118.1(8) . . ?



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

data_exp_1156_a
_database_code_depnum_ccdc_archive 'CCDC 2080968'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-27
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
nicolas.zigon@univ-angers.fr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 O2'
_chemical_formula_sum            'C19 H12 O2'
_chemical_formula_weight         272.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H12O2
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.1657(14)
_cell_length_b                   4.0638(4)
_cell_length_c                   20.4368(16)
_cell_angle_alpha                90
_cell_angle_beta                 109.294(9)
_cell_angle_gamma                90
_cell_volume                     1267.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    150
_cell_measurement_theta_min      4.2780
_cell_measurement_theta_max      75.6500
_cell_oxdiff_angle_alpha         90.029(6)
_cell_oxdiff_angle_beta          109.334(7)
_cell_oxdiff_angle_gamma         89.990(7)
_cell_oxdiff_length_a            16.1730(13)
_cell_oxdiff_length_b            4.0606(4)
_cell_oxdiff_length_c            20.4424(13)
_cell_oxdiff_measurement_reflns_used 2630
_cell_oxdiff_volume              1266.78(18)
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_min  0.83994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -2 0 0.0995
1 2 0 0.1129
1 0 5 0.0481
-1 0 -5 0.0444
1 0 -1 0.0495
-1 0 1 0.0460

_exptl_crystal_preparation       'evaporation from chloroform'
_exptl_crystal_recrystallization_method 'evaporation from chloroform'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
loop_
_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
-0.9963 -2.0003 -0.0064 0.1093 -0.7533 0.0814
0.9963 2.0003 0.0064 -0.1093 0.7533 -0.0814
0.9838 -0.0007 4.9985 -0.0489 0.0709 0.4337
-0.9838 0.0007 -4.9985 0.0489 -0.0709 -0.4337
1.0019 0.0009 -0.9996 0.1020 0.0231 -0.0178
-1.0019 -0.0009 0.9996 -0.1020 -0.0231 0.0178

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5363
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.606
_diffrn_reflns_theta_min         3.042
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -45.00   1.00    4.31    --  -41.11 125.00  60.00   44
  2  ω    -56.00  14.00   1.00    4.31    --  -41.11  57.00 -30.00   70
  3  ω      2.00  42.00   1.00    4.31    --   41.11 -38.00 -30.00   40
  4  ω    -33.00  43.00   1.00    4.31    --   41.11 -38.00 120.00   76
  5  ω    125.00 158.00   1.00   20.02    --  112.00  25.00  66.00   33
  6  ω     39.00 105.00   1.00   20.02    --  112.00 -77.00 120.00   66
  7  ω     84.00 157.00   1.00   20.02    --  112.00 111.00 120.00   73
  8  ω     40.00  65.00   1.00   20.02    --  112.00 -61.00-180.00   25
  9  ω     83.00 149.00   1.00   20.02    --  112.00  61.00-180.00   66
 10  ω     80.00 107.00   1.00   20.02    --  112.00  25.00  66.00   27
 11  ω     84.00 109.00   1.00   20.02    --  112.00-111.00 120.00   25
 12  ω     91.00 139.00   1.00   20.02    --  112.00  61.00 -90.00   48
 13  ω     36.00  63.00   1.00   20.02    --  112.00-111.00 120.00   27
 14  ω     47.00 109.00   1.00   20.02    --  112.00-111.00  60.00   62
 15  ω     88.00 158.00   1.00   20.02    --  112.00  45.00 120.00   70
 16  ω     38.00 101.00   1.00   20.02    --  112.00 -77.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0769920000
_diffrn_orient_matrix_UB_12      -0.0928906000
_diffrn_orient_matrix_UB_13      -0.0249567000
_diffrn_orient_matrix_UB_21      0.0308802000
_diffrn_orient_matrix_UB_22      0.3612061000
_diffrn_orient_matrix_UB_23      0.0081517000
_diffrn_orient_matrix_UB_31      0.0575259000
_diffrn_orient_matrix_UB_32      -0.0695833000
_diffrn_orient_matrix_UB_33      0.0754266000
_diffrn_oxdiff_digest_frames     
;
019ed3087f45f48a9985bbed9a23bc25f6008513080
;
_diffrn_oxdiff_digest_hkl        
;
0109819a36e6e4fb8c09b6b82b77961f0558f9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2261
_reflns_number_total             2583
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.036
_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)+(0.0663P)²+0.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.78998(7) 0.6394(3) 0.53318(6) 0.0384(3) Uani 1 1 d . . . . .
O1 O 0.93661(8) 0.3157(4) 0.53994(6) 0.0427(3) Uani 1 1 d . . . . .
C14 C 0.63271(9) 0.4760(4) 0.36012(7) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.52138(9) 0.4906(4) 0.24441(7) 0.0275(3) Uani 1 1 d . . . . .
C10 C 0.54392(9) 0.5560(4) 0.31599(7) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.47709(9) 0.7039(4) 0.34003(7) 0.0263(3) Uani 1 1 d . . . . .
C5 C 0.40077(9) 0.8407(4) 0.29007(8) 0.0285(3) Uani 1 1 d . . . . .
C13 C 0.68679(9) 0.2869(4) 0.33118(7) 0.0263(3) Uani 1 1 d . . . . .
C17 C 0.75637(9) 0.5141(4) 0.46805(7) 0.0283(3) Uani 1 1 d . . . . .
C16 C 0.80838(9) 0.3144(4) 0.44027(7) 0.0287(3) Uani 1 1 d . . . . .
C18 C 0.67147(9) 0.5935(4) 0.42871(7) 0.0274(3) Uani 1 1 d . . . . .
C11 C 0.57733(10) 0.2993(4) 0.21786(7) 0.0304(3) Uani 1 1 d . . . . .
C1 C 0.47848(10) 0.6993(4) 0.40950(8) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.65576(10) 0.1909(4) 0.26011(8) 0.0295(3) Uani 1 1 d . . . . .
C15 C 0.77270(10) 0.2073(4) 0.37249(8) 0.0296(3) Uani 1 1 d . . . . .
C7 C 0.38659(9) 0.8021(4) 0.21782(8) 0.0315(3) Uani 1 1 d . . . . .
C8 C 0.44180(10) 0.6168(4) 0.19620(7) 0.0310(3) Uani 1 1 d . . . . .
C2 C 0.41236(10) 0.8394(4) 0.42880(8) 0.0333(3) Uani 1 1 d . . . . .
C4 C 0.33624(10) 0.9949(4) 0.31181(8) 0.0335(4) Uani 1 1 d . . . . .
C3 C 0.34133(10) 0.9958(4) 0.38007(9) 0.0359(4) Uani 1 1 d . . . . .
C19 C 0.89851(10) 0.2287(5) 0.47997(8) 0.0363(4) Uani 1 1 d . . . . .
H11 H 0.5573(12) 0.249(5) 0.1676(10) 0.028(4) Uiso 1 1 d . . . . .
H18 H 0.6412(13) 0.751(5) 0.4483(10) 0.037(5) Uiso 1 1 d . . . . .
H8 H 0.4315(13) 0.566(5) 0.1475(10) 0.035(5) Uiso 1 1 d . . . . .
H2A H 0.4151(13) 0.827(5) 0.4790(10) 0.035(5) Uiso 1 1 d . . . . .
H19 H 0.9294(14) 0.087(6) 0.4537(11) 0.040(5) Uiso 1 1 d . . . . .
H1 H 0.5240(13) 0.578(5) 0.4450(10) 0.035(5) Uiso 1 1 d . . . . .
H12 H 0.6931(13) 0.051(5) 0.2425(9) 0.034(5) Uiso 1 1 d . . . . .
H15 H 0.8096(13) 0.074(5) 0.3527(10) 0.034(5) Uiso 1 1 d . . . . .
H7 H 0.3326(13) 0.901(5) 0.1842(10) 0.033(5) Uiso 1 1 d . . . . .
H4 H 0.2855(14) 1.098(6) 0.2749(10) 0.041(5) Uiso 1 1 d . . . . .
H3 H 0.2973(15) 1.101(6) 0.3954(11) 0.046(6) Uiso 1 1 d . . . . .
H2 H 0.8449(18) 0.559(7) 0.5521(13) 0.067(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C17 1.3595(18) . ?
O2 H2 0.90(3) . ?
O1 C19 1.228(2) . ?
C14 C18 1.4161(19) . ?
C14 C13 1.430(2) . ?
C14 C10 1.4573(19) . ?
C9 C10 1.411(2) . ?
C9 C11 1.428(2) . ?
C9 C8 1.432(2) . ?
C10 C6 1.456(2) . ?
C6 C1 1.413(2) . ?
C6 C5 1.429(2) . ?
C5 C4 1.409(2) . ?
C5 C7 1.426(2) . ?
C13 C15 1.404(2) . ?
C13 C12 1.426(2) . ?
C17 C18 1.380(2) . ?
C17 C16 1.415(2) . ?
C16 C15 1.383(2) . ?
C16 C19 1.456(2) . ?
C18 H18 0.97(2) . ?
C11 C12 1.351(2) . ?
C11 H11 0.991(19) . ?
C1 C2 1.379(2) . ?
C1 H1 0.98(2) . ?
C12 H12 0.98(2) . ?
C15 H15 0.99(2) . ?
C7 C8 1.349(2) . ?
C7 H7 1.00(2) . ?
C8 H8 0.97(2) . ?
C2 C3 1.399(2) . ?
C2 H2A 1.01(2) . ?
C4 C3 1.370(2) . ?
C4 H4 1.00(2) . ?
C3 H3 0.97(2) . ?
C19 H19 1.02(2) . ?

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
C17 O2 H2 107.5(17) . . ?
C18 C14 C13 117.35(12) . . ?
C18 C14 C10 124.09(13) . . ?
C13 C14 C10 118.39(12) . . ?
C10 C9 C11 121.14(13) . . ?
C10 C9 C8 120.75(14) . . ?
C11 C9 C8 118.11(13) . . ?
C9 C10 C6 117.47(13) . . ?
C9 C10 C14 117.62(13) . . ?
C6 C10 C14 124.90(12) . . ?
C1 C6 C5 116.53(14) . . ?
C1 C6 C10 124.49(13) . . ?
C5 C6 C10 118.77(13) . . ?
C4 C5 C7 119.54(13) . . ?
C4 C5 C6 120.15(14) . . ?
C7 C5 C6 120.16(14) . . ?
C15 C13 C12 119.65(13) . . ?
C15 C13 C14 119.57(13) . . ?
C12 C13 C14 120.72(13) . . ?
O2 C17 C18 118.79(13) . . ?
O2 C17 C16 120.62(13) . . ?
C18 C17 C16 120.57(13) . . ?
C15 C16 C17 118.40(13) . . ?
C15 C16 C19 119.48(14) . . ?
C17 C16 C19 122.08(14) . . ?
C17 C18 C14 121.83(13) . . ?
C17 C18 H18 117.0(12) . . ?
C14 C18 H18 120.9(12) . . ?
C12 C11 C9 120.88(13) . . ?
C12 C11 H11 120.8(11) . . ?
C9 C11 H11 118.3(11) . . ?
C2 C1 C6 121.70(14) . . ?
C2 C1 H1 117.4(12) . . ?
C6 C1 H1 120.7(12) . . ?
C11 C12 C13 120.13(14) . . ?
C11 C12 H12 121.1(11) . . ?
C13 C12 H12 118.7(11) . . ?
C16 C15 C13 122.14(14) . . ?
C16 C15 H15 118.4(11) . . ?
C13 C15 H15 119.5(11) . . ?
C8 C7 C5 120.21(13) . . ?
C8 C7 H7 121.4(11) . . ?
C5 C7 H7 118.2(11) . . ?
C7 C8 C9 121.05(14) . . ?
C7 C8 H8 123.0(12) . . ?
C9 C8 H8 115.9(12) . . ?
C1 C2 C3 121.03(15) . . ?
C1 C2 H2A 119.3(11) . . ?
C3 C2 H2A 119.7(11) . . ?
C3 C4 C5 121.39(14) . . ?
C3 C4 H4 121.5(12) . . ?
C5 C4 H4 117.1(12) . . ?
C4 C3 C2 118.84(15) . . ?
C4 C3 H3 121.9(13) . . ?
C2 C3 H3 119.3(13) . . ?
O1 C19 C16 124.52(16) . . ?
O1 C19 H19 121.0(11) . . ?
C16 C19 H19 114.5(11) . . ?



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

data_exp_1123_a
_database_code_depnum_ccdc_archive 'CCDC 2080967'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           SHELXL2018/3
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
nicolas.zigon@univ-angers.fr
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 N O, C H4 O'
_chemical_formula_sum            'C20 H15 N O2'
_chemical_formula_weight         301.33
_chemical_oxdiff_formula         'C19 O1 N1 H11'

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   10.7403(2)
_cell_length_b                   10.84250(16)
_cell_length_c                   13.7128(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 109.066(2)
_cell_angle_gamma                90.0
_cell_volume                     1509.27(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      76.1990
_cell_measurement_theta_min      4.3190
_cell_oxdiff_angle_alpha         90.033(3)
_cell_oxdiff_angle_beta          109.074(3)
_cell_oxdiff_angle_gamma         89.987(3)
_cell_oxdiff_length_a            10.7415(4)
_cell_oxdiff_length_b            10.8420(4)
_cell_oxdiff_length_c            13.7125(5)
_cell_oxdiff_measurement_reflns_used 6556
_cell_oxdiff_volume              1509.27(9)
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_preparation       'diffusion of MeOH in CHCl3'
_exptl_crystal_recrystallization_method 'diffusion of MeOH in CHCl3'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9899
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.461
_diffrn_reflns_theta_min         4.572
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  32.00   1.00    1.00    --  -43.24  19.00  90.00   94
  2  ω      5.00  34.00   1.00    1.00    --   43.24-125.00-150.00   29
  3  ω     31.00 108.00   1.00    2.97    --  111.00 -94.00 -90.00   77
  4  ω     89.00 116.00   1.00    2.97    --  111.00 -61.00 -90.00   27
  5  ω     76.00 125.00   1.00    2.97    --  111.00 -30.00 -90.00   49
  6  ω    122.00 156.00   1.00    2.97    --  111.00  45.00   0.00   34
  7  ω    127.00 156.00   1.00    2.97    --  111.00  77.00   0.00   29
  8  ω    131.00 156.00   1.00    2.97    --  111.00  77.00  60.00   25
  9  ω    120.00 155.00   1.00    2.97    --  111.00  30.00  90.00   35
 10  ω     95.00 158.00   1.00    2.97    --  111.00  61.00 -30.00   63
 11  ω    126.00 153.00   1.00    2.97    --  111.00  45.00 -60.00   27
 12  ω    120.00 151.00   1.00    2.97    --  111.00  45.00-150.00   31
 13  ω     99.00 134.00   1.00    2.97    --  111.00  45.00-180.00   35
 14  ω     90.00 115.00   1.00    2.97    --  111.00  45.00-150.00   25
 15  ω     99.00 124.00   1.00    2.97    --  111.00  45.00 -90.00   25
 16  ω     99.00 152.00   1.00    2.97    --  111.00  77.00 -60.00   53
 17  ω     92.00 117.00   1.00    2.97    --  111.00  45.00 -60.00   25
 18  ω     97.00 129.00   1.00    2.97    --  111.00 125.00-120.00   32
 19  ω     86.00 145.00   1.00    2.97    --  111.00  77.00  90.00   59
 20  ω     90.00 126.00   1.00    2.97    --  111.00  45.00 150.00   36
 21  ω     66.00 108.00   1.00    2.97    --  111.00 -94.00 -30.00   42
 22  ω     47.00  72.00   1.00    2.97    --  111.00 -61.00 -90.00   25
 23  ω     37.00  74.00   1.00    2.97    --  111.00 -94.00-120.00   37
 24  ω     40.00  66.00   1.00    2.97    --  111.00-125.00-180.00   26
 25  ω   -113.00 -21.00   1.00    1.00    --  -43.24 -38.00 -90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1247159000
_diffrn_orient_matrix_UB_12      -0.0808611000
_diffrn_orient_matrix_UB_13      -0.0349622000
_diffrn_orient_matrix_UB_21      -0.0681872000
_diffrn_orient_matrix_UB_22      0.0879040000
_diffrn_orient_matrix_UB_23      0.0549949000
_diffrn_orient_matrix_UB_31      -0.0531554000
_diffrn_orient_matrix_UB_32      0.0769718000
_diffrn_orient_matrix_UB_33      -0.0994187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2939
_reflns_number_total             3167
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.055
_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)+(0.0585P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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
O1 O 0.36611(7) 0.36959(8) 0.70916(6) 0.0349(2) Uani 1 1 d . . . . .
H1 H 0.3487(17) 0.3256(17) 0.6487(15) 0.054(4) Uiso 1 1 d . . . . .
O2 O 0.31087(9) 0.23786(8) 0.53671(6) 0.0395(2) Uani 1 1 d . . . . .
H2A H 0.2635(19) 0.1798(18) 0.5424(14) 0.057(5) Uiso 1 1 d . . . . .
N1 N 0.34697(10) 0.56167(10) 0.90713(8) 0.0394(2) Uani 1 1 d . . . . .
C10 C 0.80433(9) 0.42773(9) 0.67168(8) 0.0251(2) Uani 1 1 d . . . . .
C14 C 0.70685(10) 0.44680(8) 0.72339(7) 0.0243(2) Uani 1 1 d . . . . .
C6 C 0.77525(10) 0.37919(9) 0.56776(8) 0.0251(2) Uani 1 1 d . . . . .
C18 C 0.58049(10) 0.39182(9) 0.69162(7) 0.0250(2) Uani 1 1 d . . . . .
H18 H 0.5545(13) 0.3310(12) 0.6371(10) 0.028(3) Uiso 1 1 d . . . . .
C1 C 0.64702(10) 0.36753(10) 0.49475(8) 0.0281(2) Uani 1 1 d . . . . .
H1A H 0.5711(13) 0.3993(13) 0.5111(11) 0.032(3) Uiso 1 1 d . . . . .
C13 C 0.74223(10) 0.51995(9) 0.81520(8) 0.0282(2) Uani 1 1 d . . . . .
C16 C 0.52145(10) 0.49996(10) 0.82424(8) 0.0291(2) Uani 1 1 d . . . . .
C17 C 0.48838(10) 0.41826(10) 0.73910(8) 0.0272(2) Uani 1 1 d . . . . .
C5 C 0.88239(10) 0.34893(10) 0.53166(9) 0.0300(2) Uani 1 1 d . . . . .
C9 C 0.93566(10) 0.46232(10) 0.72579(9) 0.0306(2) Uani 1 1 d . . . . .
C15 C 0.64759(11) 0.54697(10) 0.86252(8) 0.0303(2) Uani 1 1 d . . . . .
H15 H 0.6750(14) 0.5970(14) 0.9236(12) 0.037(3) Uiso 1 1 d . . . . .
C19 C 0.42379(11) 0.53295(10) 0.87024(8) 0.0328(2) Uani 1 1 d . . . . .
C4 C 0.85749(12) 0.29747(11) 0.43261(10) 0.0367(3) Uani 1 1 d . . . . .
C2 C 0.62596(12) 0.31868(11) 0.39810(9) 0.0341(2) Uani 1 1 d . . . . .
H2 H 0.5349(16) 0.3126(14) 0.3501(12) 0.043(4) Uiso 1 1 d . . . . .
C7 C 1.01432(11) 0.37679(11) 0.59366(10) 0.0367(3) Uani 1 1 d . . . . .
H7 H 1.0854(17) 0.3579(16) 0.5684(13) 0.052(4) Uiso 1 1 d . . . . .
C11 C 0.96883(11) 0.52704(11) 0.82168(10) 0.0375(3) Uani 1 1 d . . . . .
H11 H 1.0633(16) 0.5502(14) 0.8559(12) 0.046(4) Uiso 1 1 d . . . . .
C8 C 1.03906(11) 0.43530(11) 0.68472(10) 0.0367(3) Uani 1 1 d . . . . .
H8 H 1.1281(16) 0.4608(15) 0.7251(13) 0.047(4) Uiso 1 1 d . . . . .
C3 C 0.73215(13) 0.28038(11) 0.36715(9) 0.0386(3) Uani 1 1 d . . . . .
H3 H 0.7166(15) 0.2451(15) 0.3003(12) 0.042(4) Uiso 1 1 d . . . . .
C12 C 0.87532(11) 0.55987(10) 0.86259(9) 0.0351(3) Uani 1 1 d . . . . .
H12 H 0.8973(15) 0.6085(15) 0.9262(13) 0.045(4) Uiso 1 1 d . . . . .
C20 C 0.27805(17) 0.27891(13) 0.43492(10) 0.0480(3) Uani 1 1 d . . . . .
H20A H 0.316(3) 0.221(3) 0.396(2) 0.130(11) Uiso 1 1 d . . . . .
H20B H 0.190(3) 0.286(3) 0.403(2) 0.113(9) Uiso 1 1 d . . . . .
H20C H 0.3237(18) 0.3528(19) 0.4306(14) 0.060(5) Uiso 1 1 d . . . . .
H4 H 0.9364(16) 0.2765(15) 0.4122(13) 0.048(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.3489(13) . ?
O1 H1 0.921(19) . ?
O2 C20 1.3961(15) . ?
O2 H2A 0.83(2) . ?
N1 C19 1.1430(15) . ?
C10 C9 1.4131(14) . ?
C10 C6 1.4542(14) . ?
C10 C14 1.4583(13) . ?
C14 C18 1.4145(14) . ?
C14 C13 1.4303(14) . ?
C6 C1 1.4193(15) . ?
C6 C5 1.4315(14) . ?
C18 C17 1.3805(14) . ?
C18 H18 0.967(14) . ?
C1 C2 1.3756(15) . ?
C1 H1A 0.976(14) . ?
C13 C15 1.4039(15) . ?
C13 C12 1.4304(15) . ?
C16 C15 1.3806(16) . ?
C16 C17 1.4152(15) . ?
C16 C19 1.4348(14) . ?
C5 C4 1.4108(16) . ?
C5 C7 1.4265(16) . ?
C9 C11 1.4291(17) . ?
C9 C8 1.4299(15) . ?
C15 H15 0.961(16) . ?
C4 C3 1.3648(19) . ?
C4 H4 1.002(16) . ?
C2 C3 1.4034(17) . ?
C2 H2 0.986(16) . ?
C7 C8 1.3475(19) . ?
C7 H7 0.958(17) . ?
C11 C12 1.3485(17) . ?
C11 H11 1.000(16) . ?
C8 H8 0.976(17) . ?
C3 H3 0.957(16) . ?
C12 H12 0.980(17) . ?
C20 H20A 0.99(3) . ?
C20 H20B 0.91(3) . ?
C20 H20C 0.95(2) . ?

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
C17 O1 H1 111.6(11) . . ?
C20 O2 H2A 112.0(13) . . ?
C9 C10 C6 117.94(9) . . ?
C9 C10 C14 117.33(9) . . ?
C6 C10 C14 124.70(9) . . ?
C18 C14 C13 117.20(9) . . ?
C18 C14 C10 124.02(9) . . ?
C13 C14 C10 118.69(9) . . ?
C1 C6 C5 116.11(9) . . ?
C1 C6 C10 124.88(9) . . ?
C5 C6 C10 118.83(9) . . ?
C17 C18 C14 122.04(9) . . ?
C17 C18 H18 115.9(8) . . ?
C14 C18 H18 122.1(8) . . ?
C2 C1 C6 122.02(10) . . ?
C2 C1 H1A 118.1(8) . . ?
C6 C1 H1A 119.8(8) . . ?
C15 C13 C14 119.89(9) . . ?
C15 C13 C12 119.59(10) . . ?
C14 C13 C12 120.42(10) . . ?
C15 C16 C17 119.70(9) . . ?
C15 C16 C19 120.55(10) . . ?
C17 C16 C19 119.75(10) . . ?
O1 C17 C18 123.48(9) . . ?
O1 C17 C16 116.94(9) . . ?
C18 C17 C16 119.58(9) . . ?
C4 C5 C7 119.77(10) . . ?
C4 C5 C6 120.17(10) . . ?
C7 C5 C6 119.97(10) . . ?
C10 C9 C11 121.29(10) . . ?
C10 C9 C8 120.62(10) . . ?
C11 C9 C8 118.08(10) . . ?
C16 C15 C13 121.05(9) . . ?
C16 C15 H15 121.6(8) . . ?
C13 C15 H15 117.3(8) . . ?
N1 C19 C16 178.58(13) . . ?
C3 C4 C5 121.53(10) . . ?
C3 C4 H4 121.9(10) . . ?
C5 C4 H4 116.6(10) . . ?
C1 C2 C3 120.74(11) . . ?
C1 C2 H2 118.9(9) . . ?
C3 C2 H2 120.3(9) . . ?
C8 C7 C5 120.58(10) . . ?
C8 C7 H7 119.8(10) . . ?
C5 C7 H7 119.5(10) . . ?
C12 C11 C9 121.11(10) . . ?
C12 C11 H11 121.1(9) . . ?
C9 C11 H11 117.7(9) . . ?
C7 C8 C9 121.20(10) . . ?
C7 C8 H8 121.3(9) . . ?
C9 C8 H8 117.5(9) . . ?
C4 C3 C2 119.04(11) . . ?
C4 C3 H3 120.7(9) . . ?
C2 C3 H3 120.3(9) . . ?
C11 C12 C13 120.05(10) . . ?
C11 C12 H12 121.1(9) . . ?
C13 C12 H12 118.8(9) . . ?
O2 C20 H20A 109.1(18) . . ?
O2 C20 H20B 113.0(18) . . ?
H20A C20 H20B 110(3) . . ?
O2 C20 H20C 111.3(11) . . ?
H20A C20 H20C 101(2) . . ?
H20B C20 H20C 112(2) . . ?



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

data_exp_1368_a
_database_code_depnum_ccdc_archive 'CCDC 2080969'
loop_
_audit_author_name
_audit_author_address
'Narcis Avarvari'
;CNRS University of Angers
France
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2021-04-27
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
nicolas.zigon@univ-angers.fr
_chemical_name_common            ?
_chemical_name_systematic        'Zn salen cyclohexyldiamine (R,R) [4]helicene'
_chemical_formula_moiety         '2(C44 H34 N2 O3 Zn)'
_chemical_formula_sum            'C88 H68 N4 O6 Zn2'
_chemical_formula_weight         1408.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C44H32O2N2Zn
_chemical_oxdiff_usercomment     'yellow needle'
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           3
_space_group_name_H-M_alt        'P 1 2 1'
_space_group_name_Hall           'P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'

_cell_length_a                   19.960(3)
_cell_length_b                   8.349(2)
_cell_length_c                   20.342(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.642(13)
_cell_angle_gamma                90
_cell_volume                     3389.7(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    560
_cell_measurement_temperature    150(10)
_cell_measurement_theta_max      30.0110
_cell_measurement_theta_min      3.1220
_cell_oxdiff_angle_alpha         90.085(15)
_cell_oxdiff_angle_beta          90.684(11)
_cell_oxdiff_angle_gamma         90.048(11)
_cell_oxdiff_length_a            19.951(2)
_cell_oxdiff_length_b            8.3547(15)
_cell_oxdiff_length_c            20.337(4)
_cell_oxdiff_measurement_reflns_used 560
_cell_oxdiff_volume              3389.7(9)
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1464
_exptl_crystal_preparation       'vapor diffusion of MeOH in THF'
_exptl_crystal_recrystallization_method 'vapor diffusion of MeOh in THF'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1775
_diffrn_reflns_av_unetI/netI     0.2632
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        50.419
_diffrn_reflns_theta_max         50.419
_diffrn_reflns_theta_min         3.085
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  33.00   1.00   34.97    --    0.00 -77.00-120.00   73
  2  ω    -33.00  42.00   1.00   34.97    --    0.00  77.00  90.00   75
  3  ω      9.00  71.00   1.00   42.34    --   81.13 -61.00 120.00   62
  4  ω     -2.00 107.00   1.00   42.34    --   81.13 -94.00-150.00  109
  5  ω      8.00  51.00   1.00   42.34    --   81.13 -45.00 -30.00   43
  6  ω     19.00  61.00   1.00   42.34    --   81.13 -61.00-120.00   42
  7  ω      5.00  35.00   1.00   42.34    --   81.13 -30.00-180.00   30
  8  ω     36.00 112.00   1.00   42.34    --   81.13-125.00 120.00   76
  9  ω      9.00  47.00   1.00   42.34    --   81.13 -61.00  30.00   38
 10  ω      5.00  30.00   1.00   42.34    --   81.13 -30.00-150.00   25
 11  ω     14.00 105.00   1.00   42.34    --   81.13 -77.00 -60.00   91
 12  ω      3.00 154.00   1.00   42.34    --   81.13   0.00-150.00  151
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047557000
_diffrn_orient_matrix_UB_12      -0.1404370000
_diffrn_orient_matrix_UB_13      -0.0488925000
_diffrn_orient_matrix_UB_21      -0.0043935000
_diffrn_orient_matrix_UB_22      -0.1194772000
_diffrn_orient_matrix_UB_23      0.0574176000
_diffrn_orient_matrix_UB_31      -0.0769493000
_diffrn_orient_matrix_UB_32      -0.0020172000
_diffrn_orient_matrix_UB_33      -0.0072078000
_diffrn_oxdiff_digest_frames     
;
0103aec69cfca905f3ea9999b45fbecd7700027a2ae
;
_diffrn_oxdiff_digest_hkl        
;
015e24549f2222fd21821f33afdadba950d11e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                1981
_reflns_number_total             7046
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_coef       0.00051(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     868
_refine_ls_number_reflns         7046
_refine_ls_number_restraints     698
_refine_ls_R_factor_all          0.2592
_refine_ls_R_factor_gt           0.0853
_refine_ls_restrained_S_all      1.236
_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)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.2361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H6A,H6B} of O6, All C(H,H) groups
 At 1.5 times of:
  {H3A,H3B} of O3
2. Restrained distances
 O6-H6B = O6-H6A
 0.84 with sigma of 0.005
 O3-H3A = O3-H3B
 0.84 with sigma of 0.005
 H6B-H6A
 1.33 with sigma of 0.005
 H3A-H3B
 1.33 with sigma of 0.01
 Zn2-H6B \\sim Zn2-H6A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C45 \\sim C47 \\sim C48 \\sim C51 \\sim C50 \\sim C49 \\sim C53 \\sim C52 \\sim
C54 \\sim C55 \\sim C58 \\sim C57 \\sim C56 \\sim C59 \\sim C61 \\sim C60 \\sim
C62 \\sim C63 \\sim C65 \\sim C64 \\sim C66 \\sim C69 \\sim C68 \\sim C67 \\sim
C70 \\sim C71 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim C72 \\sim C46 \\sim
C77 \\sim C78 \\sim C80 \\sim C79 \\sim C81 \\sim C82 \\sim C83 \\sim C84 \\sim
C88 \\sim C87 \\sim C86 \\sim C85 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5
\\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21
\\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C29 \\sim C30
\\sim C31 \\sim C32 \\sim C28 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37
\\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C44 \\sim N4
\\sim N2 \\sim N1 \\sim N3: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C6) \\sim
Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Rigid body (RIGU) restrains
 C1, C5, C10, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Rotating group:
 O3(H3A,H3B)
5.b Ternary CH refined with riding coordinates:
 C64(H64), C69(H69), C20(H20), C25(H25)
5.c Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C66(H66A,H66B), C68(H68A,H68B), C67(H67A,H67B), C21(H21A,
 H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
5.d Aromatic/amide H refined with riding coordinates:
 C45(H45), C47(H47), C48(H48), C51(H51), C52(H52), C55(H55), C56(H56),
 C59(H59), C62(H62), C63(H63), C70(H70), C73(H73), C76(H76), C46(H46), C77(H77),
  C78(H78), C81(H81), C82(H82), C88(H88), C87(H87), C86(H86), C85(H85), C1(H1),
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C11(H11), C12(H12), C15(H15), C18(H18),
  C19(H19), C26(H26), C29(H29), C32(H32), C33(H33), C34(H34), C37(H37),
 C38(H38), C41(H41), C42(H42), C43(H43), C44(H44)
5.e Fitted hexagon refined as free rotating group:
 C71(C73,C74,C75,C76,C72)
5.f Naphthalene refined as free rotating group:
 C80(C79,C81,C82,C83,C84,C88,C87,C86,C85)
;


# start Validation Reply Form
_vrf_THETM01_exp_1368_a          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Many crystals were looked at and despite long exposure times,
 the crystal did not exhibit observable intensity to a resolution higher
 than 1.0 Ang. Data were trimmed to 1.00 angstrom resolution.
;
_vrf_PLAT026_exp_1368_a          
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        28% Check
RESPONSE: This low ratio is caused by weak diffraction data at high angle.
;
_vrf_PLAT410_exp_1368_a          
;
PROBLEM: Short Intra H...H Contact 
RESPONSE: This short distance is due to large thermal ellipsoids of riding C 
atoms, in addition to the constrained, curved structure of the [4]helicene
moiety placing H atoms in close proximity.
;
# end Validation Reply Form



_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn2 Zn 0.4950(2) -0.0104(8) 0.1192(2) 0.145(2) Uani 1 1 d D . . . .
C45 C 0.6527(18) 0.641(5) 0.2369(17) 0.141(13) Uani 1 1 d . U . . .
H45 H 0.651135 0.527032 0.238729 0.169 Uiso 1 1 calc R U . . .
O5 O 0.5742(10) -0.044(4) 0.0613(10) 0.153(10) Uani 1 1 d . . . . .
N4 N 0.4790(17) -0.272(4) 0.1248(16) 0.143(11) Uani 1 1 d . U . . .
O2 O 0.1538(12) 0.733(3) 0.4754(11) 0.140(10) Uani 1 1 d . . . . .
C47 C 0.7015(17) 0.879(6) 0.1989(19) 0.136(14) Uani 1 1 d . U . . .
H47 H 0.733059 0.936513 0.173588 0.163 Uiso 1 1 calc R U . . .
N2 N 0.2016(12) 0.974(4) 0.5659(12) 0.104(8) Uani 1 1 d . U . . .
N1 N 0.1099(14) 1.193(4) 0.5296(16) 0.125(10) Uani 1 1 d . U . . .
C48 C 0.6567(15) 0.949(6) 0.2305(17) 0.131(12) Uani 1 1 d . U . . .
H48 H 0.653717 1.060423 0.222171 0.157 Uiso 1 1 calc R U . . .
O1 O 0.0618(10) 0.977(4) 0.4272(10) 0.135(9) Uani 1 1 d . . . . .
C51 C 0.5710(14) 0.984(5) 0.3217(16) 0.117(10) Uani 1 1 d . U . . .
H51 H 0.574473 1.097674 0.324823 0.141 Uiso 1 1 calc R U . . .
C50 C 0.6036(17) 0.714(6) 0.2691(18) 0.125(11) Uani 1 1 d . U . . .
O3 O 0.0509(8) 0.835(3) 0.5702(9) 0.128(8) Uani 1 1 d D . . . .
H3A H 0.014129 0.748983 0.551632 0.192 Uiso 1 1 d DR U . . .
H3B H 0.010796 0.905101 0.595374 0.192 Uiso 1 1 d DR U . . .
C49 C 0.6102(17) 0.892(6) 0.2760(17) 0.118(12) Uani 1 1 d . U . . .
O6 O 0.4326(12) 0.104(3) 0.0511(10) 0.136(8) Uiso 1 1 d D . . . .
H6A H 0.432(11) 0.059(13) 0.014(3) 0.163 Uiso 1 1 d D U . . .
H6B H 0.444(10) 0.199(8) 0.043(7) 0.163 Uiso 1 1 d D U . . .
C53 C 0.5147(17) 0.726(5) 0.353(2) 0.113(11) Uani 1 1 d . U . . .
C52 C 0.5280(14) 0.897(5) 0.3604(18) 0.115(12) Uani 1 1 d . U . . .
H52 H 0.505416 0.951958 0.394369 0.138 Uiso 1 1 calc R U . . .
C54 C 0.5486(18) 0.649(5) 0.3060(17) 0.113(10) Uani 1 1 d . U . . .
C55 C 0.4636(18) 0.662(5) 0.3936(18) 0.128(12) Uani 1 1 d . U . . .
H55 H 0.442920 0.725431 0.426513 0.154 Uiso 1 1 calc R U . . .
C58 C 0.5234(15) 0.484(6) 0.2903(16) 0.108(10) Uani 1 1 d . U . . .
C57 C 0.4670(17) 0.413(5) 0.3286(16) 0.103(10) Uani 1 1 d . U . . .
C56 C 0.4445(15) 0.501(5) 0.3830(18) 0.118(11) Uani 1 1 d . U . . .
H56 H 0.415720 0.450349 0.413620 0.142 Uiso 1 1 calc R U . . .
C59 C 0.4385(14) 0.272(5) 0.3091(16) 0.105(10) Uani 1 1 d . U . . .
H59 H 0.404875 0.230580 0.336897 0.125 Uiso 1 1 calc R U . . .
C61 C 0.5081(18) 0.251(5) 0.2152(17) 0.106(11) Uani 1 1 d . U . . .
C60 C 0.4523(18) 0.185(5) 0.2550(16) 0.113(10) Uani 1 1 d . U . . .
C62 C 0.5395(15) 0.397(5) 0.2360(17) 0.125(12) Uani 1 1 d . U . . .
H62 H 0.574758 0.436429 0.209563 0.150 Uiso 1 1 calc R U . . .
C63 C 0.4127(19) 0.053(4) 0.2383(18) 0.121(12) Uani 1 1 d . U . . .
H63 H 0.377106 0.025852 0.266807 0.145 Uiso 1 1 calc R U . . .
C65 C 0.3247(15) -0.218(5) 0.2239(16) 0.138(10) Uani 1 1 d . U . . .
H65A H 0.344541 -0.245488 0.267269 0.166 Uiso 1 1 calc R U . . .
H65B H 0.294646 -0.125087 0.229511 0.166 Uiso 1 1 calc R U . . .
C64 C 0.3794(17) -0.177(5) 0.1762(15) 0.122(9) Uani 1 1 d . U . . .
H64 H 0.356689 -0.159818 0.132682 0.146 Uiso 1 1 calc R U . . .
C66 C 0.2853(16) -0.359(5) 0.1977(16) 0.146(10) Uani 1 1 d . U . . .
H66A H 0.262671 -0.329302 0.155841 0.176 Uiso 1 1 calc R U . . .
H66B H 0.250572 -0.390345 0.229575 0.176 Uiso 1 1 calc R U . . .
C69 C 0.426(2) -0.314(5) 0.1669(19) 0.144(11) Uani 1 1 d . U . . .
H69 H 0.445689 -0.340766 0.210837 0.173 Uiso 1 1 calc R U . . .
C68 C 0.3882(17) -0.460(5) 0.1425(17) 0.155(12) Uani 1 1 d . U . . .
H68A H 0.369634 -0.438486 0.098026 0.186 Uiso 1 1 calc R U . . .
H68B H 0.419767 -0.551303 0.139017 0.186 Uiso 1 1 calc R U . . .
C67 C 0.3345(16) -0.503(6) 0.1859(17) 0.163(11) Uani 1 1 d . U . . .
H67A H 0.353674 -0.537984 0.228663 0.196 Uiso 1 1 calc R U . . .
H67B H 0.309188 -0.593938 0.166848 0.196 Uiso 1 1 calc R U . . .
C70 C 0.5250(18) -0.353(6) 0.0984(18) 0.156(14) Uani 1 1 d . U . . .
H70 H 0.514455 -0.463577 0.098568 0.187 Uiso 1 1 calc R U . . .
C71 C 0.5862(11) -0.326(5) 0.0695(11) 0.182(16) Uani 1 1 d G U . . .
C73 C 0.6271(18) -0.457(4) 0.0577(12) 0.206(17) Uani 1 1 d G U . . .
H73 H 0.612495 -0.561901 0.068964 0.248 Uiso 1 1 calc R U . . .
C74 C 0.6895(15) -0.436(4) 0.0293(13) 0.223(18) Uani 1 1 d G U . . .
C75 C 0.7109(11) -0.282(5) 0.0127(10) 0.212(17) Uani 1 1 d G U . . .
C76 C 0.6700(18) -0.151(4) 0.0246(12) 0.167(15) Uani 1 1 d G U . . .
H76 H 0.684585 -0.046563 0.013239 0.200 Uiso 1 1 calc R U . . .
C72 C 0.6076(16) -0.173(4) 0.0529(13) 0.164(16) Uani 1 1 d G U . . .
C46 C 0.7032(19) 0.698(6) 0.203(2) 0.143(14) Uani 1 1 d . U . . .
H46 H 0.736597 0.633658 0.183172 0.171 Uiso 1 1 calc R U . . .
Zn1 Zn 0.11905(18) 0.9440(8) 0.5063(2) 0.126(2) Uani 1 1 d . . . . .
O4 O 0.5297(11) 0.191(3) 0.1621(13) 0.146(10) Uani 1 1 d . . . . .
N3 N 0.4206(12) -0.029(4) 0.1894(13) 0.117(9) Uani 1 1 d . U . . .
C77 C 0.734(2) -0.579(8) 0.027(2) 0.25(2) Uani 1 1 d . U . . .
H77 H 0.720476 -0.683041 0.039022 0.300 Uiso 1 1 calc R U . . .
C78 C 0.798(2) -0.546(10) 0.004(2) 0.26(2) Uani 1 1 d . U . . .
H78 H 0.827665 -0.633499 0.001606 0.314 Uiso 1 1 calc R U . . .
C80 C 0.7812(11) -0.263(4) -0.0279(10) 0.232(18) Uani 1 1 d G U . . .
C79 C 0.8229(16) -0.393(3) -0.0153(11) 0.26(2) Uani 1 1 d G U . . .
C81 C 0.8901(15) -0.386(4) -0.0323(11) 0.26(2) Uani 1 1 d G U . . .
H81 H 0.918653 -0.474958 -0.023702 0.308 Uiso 1 1 calc R U . . .
C82 C 0.9155(10) -0.249(4) -0.0620(11) 0.25(2) Uani 1 1 d G U . . .
H82 H 0.961408 -0.244721 -0.073668 0.300 Uiso 1 1 calc R U . . .
C83 C 0.8737(7) -0.120(3) -0.0746(7) 0.229(19) Uani 1 1 d G U . . .
C84 C 0.8065(7) -0.126(3) -0.0575(7) 0.222(18) Uani 1 1 d G U . . .
C88 C 0.7648(8) 0.003(4) -0.0702(11) 0.24(2) Uani 1 1 d G U . . .
H88 H 0.718860 -0.001270 -0.058493 0.292 Uiso 1 1 calc R U . . .
C87 C 0.7902(13) 0.140(3) -0.0998(12) 0.25(2) Uani 1 1 d G U . . .
H87 H 0.761613 0.228971 -0.108459 0.304 Uiso 1 1 calc R U . . .
C86 C 0.8573(14) 0.147(3) -0.1169(11) 0.25(2) Uani 1 1 d G U . . .
H86 H 0.874696 0.240571 -0.137194 0.305 Uiso 1 1 calc R U . . .
C85 C 0.8991(10) 0.017(4) -0.1043(10) 0.24(2) Uani 1 1 d G U . . .
H85 H 0.945027 0.021933 -0.115963 0.291 Uiso 1 1 calc R U . . .
C1 C -0.0814(16) 0.981(6) 0.2356(19) 0.147(11) Uani 1 1 d . U . . .
H1 H -0.079107 0.985946 0.282207 0.176 Uiso 1 1 calc R U . . .
C2 C -0.1101(19) 0.838(6) 0.208(2) 0.170(14) Uani 1 1 d . U . . .
H2 H -0.120105 0.745873 0.232805 0.204 Uiso 1 1 calc R U . . .
C3 C -0.122(2) 0.848(7) 0.140(2) 0.197(17) Uani 1 1 d . U . . .
H3 H -0.139529 0.759928 0.116329 0.237 Uiso 1 1 calc R U . . .
C4 C -0.105(2) 1.003(7) 0.107(2) 0.176(16) Uani 1 1 d . U . . .
H4 H -0.121763 1.014740 0.063069 0.211 Uiso 1 1 calc R U . . .
C5 C -0.069(2) 1.130(8) 0.131(3) 0.172(13) Uani 1 1 d . U . . .
C6 C -0.0564(18) 1.115(6) 0.202(2) 0.138(12) Uani 1 1 d . U . . .
C7 C -0.054(2) 1.254(7) 0.098(2) 0.179(18) Uani 1 1 d . U . . .
H7 H -0.054200 1.246068 0.051664 0.215 Uiso 1 1 calc R U . . .
C8 C -0.038(2) 1.395(7) 0.125(2) 0.181(18) Uani 1 1 d . U . . .
H8 H -0.041443 1.493470 0.101868 0.217 Uiso 1 1 calc R U . . .
C9 C -0.013(2) 1.383(8) 0.198(3) 0.166(15) Uani 1 1 d . U . . .
C10 C -0.021(2) 1.226(7) 0.228(2) 0.159(12) Uani 1 1 d . U . . .
C11 C 0.009(2) 1.536(7) 0.219(3) 0.187(17) Uani 1 1 d . U . . .
H11 H 0.011091 1.622501 0.188462 0.224 Uiso 1 1 calc R U . . .
C12 C 0.0291(18) 1.557(7) 0.286(2) 0.178(16) Uani 1 1 d . U . . .
H12 H 0.040333 1.656349 0.306015 0.213 Uiso 1 1 calc R U . . .
C13 C 0.029(2) 1.401(7) 0.319(3) 0.162(15) Uani 1 1 d . U . . .
C14 C 0.0136(18) 1.259(7) 0.299(2) 0.139(13) Uani 1 1 d . U . . .
C15 C 0.0553(14) 1.421(6) 0.3886(18) 0.148(13) Uani 1 1 d . U . . .
H15 H 0.064709 1.521074 0.409095 0.178 Uiso 1 1 calc R U . . .
C16 C 0.0638(15) 1.269(7) 0.419(2) 0.125(12) Uani 1 1 d . U . . .
C17 C 0.0519(17) 1.113(7) 0.399(2) 0.115(12) Uani 1 1 d . U . . .
C18 C 0.0263(15) 1.102(6) 0.3344(18) 0.139(13) Uani 1 1 d . U . . .
H18 H 0.017490 1.002156 0.313983 0.167 Uiso 1 1 calc R U . . .
C19 C 0.0886(16) 1.297(5) 0.486(2) 0.133(12) Uani 1 1 d . U . . .
H19 H 0.089270 1.405985 0.499907 0.160 Uiso 1 1 calc R U . . .
C20 C 0.1403(16) 1.209(4) 0.5970(16) 0.110(10) Uani 1 1 d . U . . .
H20 H 0.112896 1.146347 0.628778 0.132 Uiso 1 1 calc R U . . .
C21 C 0.1410(14) 1.392(4) 0.6191(15) 0.120(11) Uani 1 1 d . U . . .
H21A H 0.167941 1.455894 0.588176 0.144 Uiso 1 1 calc R U . . .
H21B H 0.094835 1.434707 0.619188 0.144 Uiso 1 1 calc R U . . .
C22 C 0.1713(15) 1.401(4) 0.6874(15) 0.128(11) Uani 1 1 d . U . . .
H22A H 0.141207 1.348523 0.719291 0.154 Uiso 1 1 calc R U . . .
H22B H 0.176999 1.514237 0.700569 0.154 Uiso 1 1 calc R U . . .
C23 C 0.2415(16) 1.314(4) 0.6877(15) 0.125(11) Uani 1 1 d . U . . .
H23A H 0.272943 1.375977 0.660377 0.150 Uiso 1 1 calc R U . . .
H23B H 0.259645 1.312177 0.733212 0.150 Uiso 1 1 calc R U . . .
C24 C 0.2379(15) 1.142(4) 0.6618(16) 0.119(10) Uani 1 1 d . U . . .
H24A H 0.211304 1.075864 0.692218 0.142 Uiso 1 1 calc R U . . .
H24B H 0.283708 1.096718 0.660141 0.142 Uiso 1 1 calc R U . . .
C25 C 0.2055(15) 1.136(4) 0.5920(16) 0.102(10) Uani 1 1 d . U . . .
H25 H 0.233298 1.202298 0.561727 0.122 Uiso 1 1 calc R U . . .
C26 C 0.2502(15) 0.880(5) 0.5699(16) 0.107(11) Uani 1 1 d . U . . .
H26 H 0.286414 0.915301 0.596863 0.129 Uiso 1 1 calc R U . . .
C27 C 0.2592(16) 0.723(4) 0.5386(15) 0.094(9) Uani 1 1 d . U . . .
C29 C 0.3179(15) 0.637(4) 0.5576(13) 0.089(9) Uani 1 1 d . U . . .
H29 H 0.348742 0.678806 0.589061 0.107 Uiso 1 1 calc R U . . .
C30 C 0.3284(14) 0.487(5) 0.5280(14) 0.098(9) Uani 1 1 d . U . . .
C31 C 0.2824(15) 0.442(5) 0.4747(14) 0.098(9) Uani 1 1 d . U . . .
C32 C 0.2236(14) 0.528(5) 0.4610(14) 0.104(11) Uani 1 1 d . U . . .
H32 H 0.193433 0.488490 0.428372 0.124 Uiso 1 1 calc R U . . .
C28 C 0.208(2) 0.668(5) 0.4938(19) 0.121(12) Uani 1 1 d . U . . .
C33 C 0.3856(16) 0.396(5) 0.5508(17) 0.120(12) Uani 1 1 d . U . . .
H33 H 0.418513 0.441733 0.579294 0.144 Uiso 1 1 calc R U . . .
C34 C 0.3901(15) 0.239(5) 0.5288(15) 0.114(11) Uani 1 1 d . U . . .
H34 H 0.421694 0.168728 0.548843 0.137 Uiso 1 1 calc R U . . .
C35 C 0.3489(18) 0.182(5) 0.4778(16) 0.112(10) Uani 1 1 d . U . . .
C36 C 0.2984(15) 0.285(5) 0.4455(17) 0.101(10) Uani 1 1 d . U . . .
C37 C 0.3553(16) 0.006(5) 0.4592(18) 0.125(12) Uani 1 1 d . U . . .
H37 H 0.390248 -0.057868 0.477134 0.150 Uiso 1 1 calc R U . . .
C38 C 0.3123(18) -0.053(6) 0.4185(19) 0.137(12) Uani 1 1 d . U . . .
H38 H 0.311444 -0.165803 0.414160 0.165 Uiso 1 1 calc R U . . .
C39 C 0.2675(19) 0.032(6) 0.381(2) 0.135(13) Uani 1 1 d . U . . .
C40 C 0.2611(19) 0.199(6) 0.393(2) 0.131(12) Uani 1 1 d . U . . .
C41 C 0.2262(17) -0.027(6) 0.328(2) 0.160(13) Uani 1 1 d . U . . .
H41 H 0.227879 -0.138240 0.318572 0.192 Uiso 1 1 calc R U . . .
C42 C 0.1869(18) 0.061(6) 0.292(2) 0.162(16) Uani 1 1 d . U . . .
H42 H 0.154281 0.009212 0.264560 0.194 Uiso 1 1 calc R U . . .
C43 C 0.1907(19) 0.234(6) 0.291(2) 0.160(15) Uani 1 1 d . U . . .
H43 H 0.170615 0.298039 0.257440 0.192 Uiso 1 1 calc R U . . .
C44 C 0.2286(17) 0.301(6) 0.347(2) 0.154(13) Uani 1 1 d . U . . .
H44 H 0.231488 0.413788 0.351884 0.185 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn2 O5 2.00(2) . ?
Zn2 O4 2.01(3) . ?
Zn2 N3 2.08(2) . ?
Zn2 O6 2.08(2) . ?
Zn2 N4 2.21(4) . ?
C45 C46 1.32(4) . ?
C45 C50 1.33(4) . ?
C45 H45 0.9500 . ?
O5 C72 1.28(3) . ?
N4 C70 1.26(4) . ?
N4 C69 1.42(4) . ?
O2 C28 1.27(4) . ?
O2 Zn1 2.00(3) . ?
C47 C48 1.25(4) . ?
C47 C46 1.51(5) . ?
C47 H47 0.9500 . ?
N2 C26 1.25(3) . ?
N2 C25 1.46(4) . ?
N2 Zn1 2.05(2) . ?
N1 C19 1.31(4) . ?
N1 C20 1.50(4) . ?
N1 Zn1 2.14(3) . ?
C48 C49 1.40(4) . ?
C48 H48 0.9500 . ?
O1 C17 1.28(5) . ?
O1 Zn1 1.982(19) . ?
C51 C52 1.38(4) . ?
C51 C49 1.45(4) . ?
C51 H51 0.9500 . ?
C50 C54 1.44(4) . ?
C50 C49 1.50(5) . ?
O3 Zn1 2.098(18) . ?
O3 H3A 1.0925 . ?
O3 H3B 1.1200 . ?
O6 H6A 0.840(8) . ?
O6 H6B 0.841(8) . ?
C53 C54 1.35(4) . ?
C53 C55 1.42(4) . ?
C53 C52 1.45(4) . ?
C52 H52 0.9500 . ?
C54 C58 1.50(5) . ?
C55 C56 1.42(4) . ?
C55 H55 0.9500 . ?
C58 C62 1.36(4) . ?
C58 C57 1.50(4) . ?
C57 C59 1.36(4) . ?
C57 C56 1.41(4) . ?
C56 H56 0.9500 . ?
C59 C60 1.35(4) . ?
C59 H59 0.9500 . ?
C61 O4 1.27(3) . ?
C61 C62 1.43(4) . ?
C61 C60 1.49(5) . ?
C60 C63 1.40(4) . ?
C62 H62 0.9500 . ?
C63 N3 1.22(4) . ?
C63 H63 0.9500 . ?
C65 C66 1.51(4) . ?
C65 C64 1.51(4) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C64 C69 1.48(4) . ?
C64 N3 1.51(4) . ?
C64 H64 1.0000 . ?
C66 C67 1.57(5) . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C69 C68 1.51(5) . ?
C69 H69 1.0000 . ?
C68 C67 1.44(4) . ?
C68 H68A 0.9900 . ?
C68 H68B 0.9900 . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C70 C71 1.38(4) . ?
C70 H70 0.9500 . ?
C71 C73 1.3900 . ?
C71 C72 1.3900 . ?
C73 C74 1.3900 . ?
C73 H73 0.9500 . ?
C74 C75 1.3900 . ?
C74 C77 1.50(6) . ?
C75 C76 1.3900 . ?
C75 C80 1.64(3) . ?
C76 C72 1.3900 . ?
C76 H76 0.9500 . ?
C46 H46 0.9500 . ?
C77 C78 1.37(6) . ?
C77 H77 0.9500 . ?
C78 C79 1.43(8) . ?
C78 H78 0.9500 . ?
C80 C79 1.3900 . ?
C80 C84 1.3900 . ?
C79 C81 1.3900 . ?
C81 C82 1.3900 . ?
C81 H81 0.9500 . ?
C82 C83 1.3900 . ?
C82 H82 0.9500 . ?
C83 C84 1.3900 . ?
C83 C85 1.3900 . ?
C84 C88 1.3900 . ?
C88 C87 1.3900 . ?
C88 H88 0.9500 . ?
C87 C86 1.3900 . ?
C87 H87 0.9500 . ?
C86 C85 1.3900 . ?
C86 H86 0.9500 . ?
C85 H85 0.9500 . ?
C1 C6 1.41(5) . ?
C1 C2 1.44(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.39(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.50(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.37(6) . ?
C4 H4 0.9500 . ?
C5 C7 1.28(6) . ?
C5 C6 1.45(6) . ?
C6 C10 1.28(6) . ?
C7 C8 1.33(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.55(6) . ?
C8 H8 0.9500 . ?
C9 C11 1.41(6) . ?
C9 C10 1.46(6) . ?
C10 C14 1.62(6) . ?
C11 C12 1.44(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.47(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.29(5) . ?
C13 C15 1.51(6) . ?
C14 C18 1.52(5) . ?
C15 C16 1.43(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.39(5) . ?
C16 C19 1.46(5) . ?
C17 C18 1.41(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.44(4) . ?
C20 C21 1.59(4) . ?
C20 H20 1.0000 . ?
C21 C22 1.51(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.58(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.53(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.55(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25 1.0000 . ?
C26 C27 1.47(4) . ?
C26 H26 0.9500 . ?
C27 C29 1.43(4) . ?
C27 C28 1.43(4) . ?
C29 C30 1.40(4) . ?
C29 H29 0.9500 . ?
C30 C33 1.44(4) . ?
C30 C31 1.46(4) . ?
C31 C32 1.40(4) . ?
C31 C36 1.48(4) . ?
C32 C28 1.38(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.39(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.40(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.47(4) . ?
C35 C37 1.52(5) . ?
C36 C40 1.47(5) . ?
C37 C38 1.28(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.37(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.42(5) . ?
C39 C41 1.44(5) . ?
C40 C44 1.42(5) . ?
C41 C42 1.30(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.45(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.47(5) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?

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
O5 Zn2 O4 95.7(11) . . ?
O5 Zn2 N3 165.8(13) . . ?
O4 Zn2 N3 90.6(13) . . ?
O5 Zn2 O6 98.1(9) . . ?
O4 Zn2 O6 96.2(10) . . ?
N3 Zn2 O6 93.7(9) . . ?
O5 Zn2 N4 90.5(14) . . ?
O4 Zn2 N4 148.4(11) . . ?
N3 Zn2 N4 77.6(14) . . ?
O6 Zn2 N4 113.6(10) . . ?
C46 C45 C50 131(5) . . ?
C46 C45 H45 114.3 . . ?
C50 C45 H45 114.3 . . ?
C72 O5 Zn2 128(3) . . ?
C70 N4 C69 133(4) . . ?
C70 N4 Zn2 114(3) . . ?
C69 N4 Zn2 113(2) . . ?
C28 O2 Zn1 126(3) . . ?
C48 C47 C46 117(5) . . ?
C48 C47 H47 121.5 . . ?
C46 C47 H47 121.5 . . ?
C26 N2 C25 121(3) . . ?
C26 N2 Zn1 126(3) . . ?
C25 N2 Zn1 111(2) . . ?
C19 N1 C20 133(4) . . ?
C19 N1 Zn1 122(3) . . ?
C20 N1 Zn1 105(2) . . ?
C47 C48 C49 132(5) . . ?
C47 C48 H48 114.2 . . ?
C49 C48 H48 114.2 . . ?
C17 O1 Zn1 125(3) . . ?
C52 C51 C49 115(4) . . ?
C52 C51 H51 122.4 . . ?
C49 C51 H51 122.4 . . ?
C45 C50 C54 131(5) . . ?
C45 C50 C49 116(4) . . ?
C54 C50 C49 113(4) . . ?
Zn1 O3 H3A 120.6 . . ?
Zn1 O3 H3B 122.0 . . ?
H3A O3 H3B 91.1 . . ?
C48 C49 C51 128(5) . . ?
C48 C49 C50 109(4) . . ?
C51 C49 C50 123(4) . . ?
Zn2 O6 H6A 113(10) . . ?
Zn2 O6 H6B 113(10) . . ?
H6A O6 H6B 104.7(13) . . ?
C54 C53 C55 127(5) . . ?
C54 C53 C52 116(4) . . ?
C55 C53 C52 116(4) . . ?
C51 C52 C53 125(4) . . ?
C51 C52 H52 117.3 . . ?
C53 C52 H52 117.3 . . ?
C53 C54 C50 126(5) . . ?
C53 C54 C58 115(4) . . ?
C50 C54 C58 119(4) . . ?
C56 C55 C53 118(4) . . ?
C56 C55 H55 121.1 . . ?
C53 C55 H55 121.1 . . ?
C62 C58 C57 113(4) . . ?
C62 C58 C54 125(4) . . ?
C57 C58 C54 120(3) . . ?
C59 C57 C56 123(4) . . ?
C59 C57 C58 120(3) . . ?
C56 C57 C58 117(4) . . ?
C57 C56 C55 122(4) . . ?
C57 C56 H56 119.1 . . ?
C55 C56 H56 119.1 . . ?
C60 C59 C57 128(4) . . ?
C60 C59 H59 116.0 . . ?
C57 C59 H59 116.0 . . ?
O4 C61 C62 116(4) . . ?
O4 C61 C60 125(4) . . ?
C62 C61 C60 119(4) . . ?
C59 C60 C63 120(4) . . ?
C59 C60 C61 114(4) . . ?
C63 C60 C61 126(4) . . ?
C58 C62 C61 126(4) . . ?
C58 C62 H62 117.1 . . ?
C61 C62 H62 117.1 . . ?
N3 C63 C60 124(4) . . ?
N3 C63 H63 117.8 . . ?
C60 C63 H63 117.8 . . ?
C66 C65 C64 109(3) . . ?
C66 C65 H65A 109.9 . . ?
C64 C65 H65A 109.9 . . ?
C66 C65 H65B 109.9 . . ?
C64 C65 H65B 109.9 . . ?
H65A C65 H65B 108.3 . . ?
C69 C64 N3 108(3) . . ?
C69 C64 C65 111(4) . . ?
N3 C64 C65 118(3) . . ?
C69 C64 H64 106.1 . . ?
N3 C64 H64 106.1 . . ?
C65 C64 H64 106.1 . . ?
C65 C66 C67 109(3) . . ?
C65 C66 H66A 109.9 . . ?
C67 C66 H66A 109.9 . . ?
C65 C66 H66B 109.9 . . ?
C67 C66 H66B 109.9 . . ?
H66A C66 H66B 108.3 . . ?
N4 C69 C64 111(4) . . ?
N4 C69 C68 112(3) . . ?
C64 C69 C68 111(4) . . ?
N4 C69 H69 107.6 . . ?
C64 C69 H69 107.6 . . ?
C68 C69 H69 107.6 . . ?
C67 C68 C69 111(4) . . ?
C67 C68 H68A 109.3 . . ?
C69 C68 H68A 109.3 . . ?
C67 C68 H68B 109.3 . . ?
C69 C68 H68B 109.3 . . ?
H68A C68 H68B 108.0 . . ?
C68 C67 C66 112(4) . . ?
C68 C67 H67A 109.2 . . ?
C66 C67 H67A 109.2 . . ?
C68 C67 H67B 109.2 . . ?
C66 C67 H67B 109.2 . . ?
H67A C67 H67B 107.9 . . ?
N4 C70 C71 138(5) . . ?
N4 C70 H70 110.9 . . ?
C71 C70 H70 110.9 . . ?
C70 C71 C73 118(4) . . ?
C70 C71 C72 122(4) . . ?
C73 C71 C72 120.0 . . ?
C71 C73 C74 120.0 . . ?
C71 C73 H73 120.0 . . ?
C74 C73 H73 120.0 . . ?
C75 C74 C73 120.0 . . ?
C75 C74 C77 123(4) . . ?
C73 C74 C77 117(4) . . ?
C76 C75 C74 120.0 . . ?
C76 C75 C80 121(3) . . ?
C74 C75 C80 119(3) . . ?
C75 C76 C72 120.0 . . ?
C75 C76 H76 120.0 . . ?
C72 C76 H76 120.0 . . ?
O5 C72 C76 115(3) . . ?
O5 C72 C71 125(3) . . ?
C76 C72 C71 120.0 . . ?
C45 C46 C47 112(4) . . ?
C45 C46 H46 124.0 . . ?
C47 C46 H46 124.0 . . ?
O1 Zn1 O2 93.8(11) . . ?
O1 Zn1 N2 156.3(11) . . ?
O2 Zn1 N2 90.7(11) . . ?
O1 Zn1 O3 101.0(9) . . ?
O2 Zn1 O3 92.5(10) . . ?
N2 Zn1 O3 102.0(9) . . ?
O1 Zn1 N1 89.7(13) . . ?
O2 Zn1 N1 163.1(11) . . ?
N2 Zn1 N1 79.7(13) . . ?
O3 Zn1 N1 103.1(11) . . ?
C61 O4 Zn2 125(3) . . ?
C63 N3 C64 122(3) . . ?
C63 N3 Zn2 128(3) . . ?
C64 N3 Zn2 109(2) . . ?
C78 C77 C74 114(6) . . ?
C78 C77 H77 123.1 . . ?
C74 C77 H77 123.1 . . ?
C77 C78 C79 127(6) . . ?
C77 C78 H78 116.5 . . ?
C79 C78 H78 116.5 . . ?
C79 C80 C84 120.0 . . ?
C79 C80 C75 110(2) . . ?
C84 C80 C75 128(2) . . ?
C81 C79 C80 120.0 . . ?
C81 C79 C78 117(3) . . ?
C80 C79 C78 122(3) . . ?
C79 C81 C82 120.0 . . ?
C79 C81 H81 120.0 . . ?
C82 C81 H81 120.0 . . ?
C83 C82 C81 120.0 . . ?
C83 C82 H82 120.0 . . ?
C81 C82 H82 120.0 . . ?
C82 C83 C84 120.0 . . ?
C82 C83 C85 120.0 . . ?
C84 C83 C85 120.0 . . ?
C88 C84 C83 120.0 . . ?
C88 C84 C80 120.0 . . ?
C83 C84 C80 120.0 . . ?
C87 C88 C84 120.0 . . ?
C87 C88 H88 120.0 . . ?
C84 C88 H88 120.0 . . ?
C86 C87 C88 120.0 . . ?
C86 C87 H87 120.0 . . ?
C88 C87 H87 120.0 . . ?
C87 C86 C85 120.0 . . ?
C87 C86 H86 120.0 . . ?
C85 C86 H86 120.0 . . ?
C86 C85 C83 120.0 . . ?
C86 C85 H85 120.0 . . ?
C83 C85 H85 120.0 . . ?
C6 C1 C2 127(4) . . ?
C6 C1 H1 116.4 . . ?
C2 C1 H1 116.4 . . ?
C3 C2 C1 114(5) . . ?
C3 C2 H2 123.1 . . ?
C1 C2 H2 123.1 . . ?
C2 C3 C4 118(6) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 128(5) . . ?
C5 C4 H4 116.0 . . ?
C3 C4 H4 116.0 . . ?
C7 C5 C4 124(6) . . ?
C7 C5 C6 124(6) . . ?
C4 C5 C6 112(6) . . ?
C10 C6 C1 125(6) . . ?
C10 C6 C5 116(6) . . ?
C1 C6 C5 120(5) . . ?
C5 C7 C8 124(6) . . ?
C5 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 114(5) . . ?
C7 C8 H8 123.1 . . ?
C9 C8 H8 123.1 . . ?
C11 C9 C10 136(6) . . ?
C11 C9 C8 109(6) . . ?
C10 C9 C8 115(5) . . ?
C6 C10 C9 123(6) . . ?
C6 C10 C14 136(6) . . ?
C9 C10 C14 100(5) . . ?
C9 C11 C12 119(5) . . ?
C9 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 109(5) . . ?
C11 C12 H12 125.3 . . ?
C13 C12 H12 125.3 . . ?
C14 C13 C12 132(6) . . ?
C14 C13 C15 119(6) . . ?
C12 C13 C15 109(5) . . ?
C13 C14 C18 127(5) . . ?
C13 C14 C10 123(6) . . ?
C18 C14 C10 110(4) . . ?
C16 C15 C13 110(5) . . ?
C16 C15 H15 124.9 . . ?
C13 C15 H15 124.9 . . ?
C17 C16 C15 134(5) . . ?
C17 C16 C19 119(5) . . ?
C15 C16 C19 107(5) . . ?
O1 C17 C16 132(5) . . ?
O1 C17 C18 115(5) . . ?
C16 C17 C18 113(5) . . ?
C17 C18 C14 117(5) . . ?
C17 C18 H18 121.6 . . ?
C14 C18 H18 121.6 . . ?
N1 C19 C16 129(5) . . ?
N1 C19 H19 115.7 . . ?
C16 C19 H19 115.7 . . ?
C25 C20 N1 105(3) . . ?
C25 C20 C21 115(3) . . ?
N1 C20 C21 110(3) . . ?
C25 C20 H20 108.9 . . ?
N1 C20 H20 108.9 . . ?
C21 C20 H20 108.9 . . ?
C22 C21 C20 108(3) . . ?
C22 C21 H21A 110.1 . . ?
C20 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
C20 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 C23 109(2) . . ?
C21 C22 H22A 109.9 . . ?
C23 C22 H22A 109.9 . . ?
C21 C22 H22B 109.9 . . ?
C23 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C22 113(3) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 111(3) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C20 C25 N2 112(3) . . ?
C20 C25 C24 107(3) . . ?
N2 C25 C24 112(3) . . ?
C20 C25 H25 108.5 . . ?
N2 C25 H25 108.5 . . ?
C24 C25 H25 108.5 . . ?
N2 C26 C27 129(3) . . ?
N2 C26 H26 115.5 . . ?
C27 C26 H26 115.5 . . ?
C29 C27 C28 126(4) . . ?
C29 C27 C26 116(3) . . ?
C28 C27 C26 118(4) . . ?
C30 C29 C27 117(3) . . ?
C30 C29 H29 121.3 . . ?
C27 C29 H29 121.3 . . ?
C29 C30 C33 117(3) . . ?
C29 C30 C31 117(3) . . ?
C33 C30 C31 126(4) . . ?
C32 C31 C30 122(3) . . ?
C32 C31 C36 124(3) . . ?
C30 C31 C36 113(3) . . ?
C28 C32 C31 122(4) . . ?
C28 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
O2 C28 C32 114(4) . . ?
O2 C28 C27 130(4) . . ?
C32 C28 C27 115(4) . . ?
C34 C33 C30 117(4) . . ?
C34 C33 H33 121.7 . . ?
C30 C33 H33 121.7 . . ?
C33 C34 C35 121(4) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C34 C35 C36 122(4) . . ?
C34 C35 C37 117(4) . . ?
C36 C35 C37 121(3) . . ?
C35 C36 C40 112(4) . . ?
C35 C36 C31 119(3) . . ?
C40 C36 C31 128(4) . . ?
C38 C37 C35 118(4) . . ?
C38 C37 H37 120.9 . . ?
C35 C37 H37 120.9 . . ?
C37 C38 C39 126(5) . . ?
C37 C38 H38 116.9 . . ?
C39 C38 H38 116.9 . . ?
C38 C39 C40 118(5) . . ?
C38 C39 C41 127(5) . . ?
C40 C39 C41 115(5) . . ?
C39 C40 C44 121(5) . . ?
C39 C40 C36 124(5) . . ?
C44 C40 C36 114(5) . . ?
C42 C41 C39 125(5) . . ?
C42 C41 H41 117.5 . . ?
C39 C41 H41 117.5 . . ?
C41 C42 C43 123(5) . . ?
C41 C42 H42 118.7 . . ?
C43 C42 H42 118.7 . . ?
C42 C43 C44 113(5) . . ?
C42 C43 H43 123.3 . . ?
C44 C43 H43 123.3 . . ?
C40 C44 C43 121(5) . . ?
C40 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?




