# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_compound_L1H
_database_code_depnum_ccdc_archive 'CCDC 2182070'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2020-11-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 N2 O'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   21.7702(6)
_cell_length_b                   21.9570(6)
_cell_length_c                   7.2513(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3466.18(17)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.86
_cell_measurement_theta_min      5.72
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.9021
_exptl_absorpt_correction_T_min  0.7393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.8195.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.693
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15105
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.855
_diffrn_reflns_theta_max         66.855
_diffrn_reflns_theta_min         5.724
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture (Cu)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                1429
_reflns_number_total             1510
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+2.8786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.28071(7) 0.81979(7) 0.2440(2) 0.0195(4) Uani 1 1 d . . . . .
H1 H 0.261493 0.800957 0.326733 0.029 Uiso 1 1 calc R U . . .
N1 N 0.31849(8) 0.72117(8) 0.4655(3) 0.0136(4) Uani 1 1 d . . . . .
N2 N 0.31003(9) 0.67424(9) 0.7518(3) 0.0189(5) Uani 1 1 d . . . . .
C1 C 0.36003(10) 0.74889(9) 0.3409(3) 0.0127(5) Uani 1 1 d . . . . .
C2 C 0.33856(10) 0.79669(9) 0.2293(3) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.37722(11) 0.82271(9) 0.0986(3) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.362335 0.854632 0.022295 0.020 Uiso 1 1 calc R U . . .
C4 C 0.43706(10) 0.80270(10) 0.0783(3) 0.0176(5) Uani 1 1 d . . . . .
H4 H 0.463073 0.821101 -0.010943 0.021 Uiso 1 1 calc R U . . .
C5 C 0.45914(10) 0.75592(10) 0.1877(4) 0.0165(5) Uani 1 1 d . . . . .
H5 H 0.500285 0.742214 0.174324 0.020 Uiso 1 1 calc R U . . .
C6 C 0.42063(10) 0.72917(10) 0.3173(3) 0.0150(5) Uani 1 1 d . . . . .
H6 H 0.435775 0.696804 0.391411 0.018 Uiso 1 1 calc R U . . .
C7 C 0.34089(10) 0.70489(10) 0.6226(3) 0.0142(5) Uani 1 1 d . . . . .
H7 H 0.382335 0.715471 0.648214 0.017 Uiso 1 1 calc R U . . .
C8 C 0.24839(11) 0.65209(12) 0.7182(4) 0.0240(6) Uani 1 1 d . . . . .
H8A H 0.250038 0.617141 0.634314 0.036 Uiso 1 1 calc R U . . .
H8B H 0.223696 0.684547 0.662470 0.036 Uiso 1 1 calc R U . . .
H8C H 0.229710 0.639584 0.835223 0.036 Uiso 1 1 calc R U . . .
C9 C 0.33965(12) 0.65563(12) 0.9220(4) 0.0244(6) Uani 1 1 d . . . . .
H9A H 0.378616 0.677519 0.935827 0.037 Uiso 1 1 calc R U . . .
H9B H 0.347553 0.611707 0.918590 0.037 Uiso 1 1 calc R U . . .
H9C H 0.312793 0.665109 1.026614 0.037 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
O1 H1 0.8400 . ?
O1 C2 1.362(3) . ?
N1 C1 1.416(3) . ?
N1 C7 1.290(3) . ?
N2 C7 1.335(3) . ?
N2 C8 1.448(3) . ?
N2 C9 1.452(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C7 N1 C1 116.17(18) . . ?
C7 N2 C8 121.2(2) . . ?
C7 N2 C9 121.0(2) . . ?
C8 N2 C9 117.4(2) . . ?
C2 C1 N1 118.43(18) . . ?
C6 C1 N1 123.19(19) . . ?
C6 C1 C2 118.3(2) . . ?
O1 C2 C1 122.7(2) . . ?
O1 C2 C3 117.41(19) . . ?
C3 C2 C1 119.88(19) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
N1 C7 N2 124.7(2) . . ?
N1 C7 H7 117.7 . . ?
N2 C7 H7 117.7 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 2.07 2.837(2) 151.9 14_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.5(2) . . . . ?
N1 C1 C2 O1 4.1(3) . . . . ?
N1 C1 C2 C3 -176.6(2) . . . . ?
N1 C1 C6 C5 177.1(2) . . . . ?
C1 N1 C7 N2 -174.9(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 O1 -178.8(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 N1 C1 C2 -143.1(2) . . . . ?
C7 N1 C1 C6 40.0(3) . . . . ?
C8 N2 C7 N1 5.0(3) . . . . ?
C9 N2 C7 N1 177.5(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_L3H
_database_code_depnum_ccdc_archive 'CCDC 2182071'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.7113(6)
_cell_length_b                   10.8251(4)
_cell_length_c                   15.6437(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2829.97(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8989
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0568 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.9385.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.191
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50670
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2378
_reflns_number_total             3246
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.056
_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)+(0.0374P)²+1.4267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C6'(H6'), C3'(H3'), C5(H5), C4(H4), C4'(H4'), C5'(H5')
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7'(H7'A,H7'B,H7'C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.80032(6) 0.61357(9) 0.63569(6) 0.0202(2) Uani 1 1 d . . . . .
H1 H 0.793434 0.669961 0.671834 0.030 Uiso 1 1 calc R U . . .
N1 N 0.66105(6) 0.67792(10) 0.72736(7) 0.0155(2) Uani 1 1 d . . . . .
N2 N 0.62633(7) 0.74385(11) 0.86212(7) 0.0191(3) Uani 1 1 d . . . . .
C7 C 0.63292(8) 0.65267(12) 0.80311(8) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.65795(8) 0.58662(12) 0.66216(8) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.72884(8) 0.55913(13) 0.61773(8) 0.0163(3) Uani 1 1 d . . . . .
C1' C 0.60617(8) 0.52581(13) 0.82929(8) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.58776(8) 0.52633(13) 0.63756(9) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.538973 0.546018 0.665596 0.023 Uiso 1 1 calc R U . . .
C2' C 0.52627(8) 0.50227(13) 0.85156(8) 0.0198(3) Uani 1 1 d . . . . .
C3 C 0.72872(9) 0.46999(13) 0.55380(9) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.777044 0.450715 0.524719 0.027 Uiso 1 1 calc R U . . .
C6' C 0.66150(9) 0.42933(13) 0.82607(9) 0.0205(3) Uani 1 1 d . . . . .
H6' H 0.715206 0.445749 0.809738 0.025 Uiso 1 1 calc R U . . .
C3' C 0.50471(9) 0.38058(14) 0.87088(9) 0.0237(3) Uani 1 1 d . . . . .
H3' H 0.450744 0.362462 0.885268 0.028 Uiso 1 1 calc R U . . .
C5 C 0.58770(9) 0.43840(14) 0.57316(9) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.539298 0.398536 0.557235 0.030 Uiso 1 1 calc R U . . .
C4 C 0.65873(9) 0.40901(14) 0.53213(9) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.659396 0.347031 0.489141 0.032 Uiso 1 1 calc R U . . .
C4' C 0.56030(9) 0.28632(14) 0.86945(9) 0.0263(3) Uani 1 1 d . . . . .
H4' H 0.544612 0.204753 0.884320 0.032 Uiso 1 1 calc R U . . .
C5' C 0.63882(9) 0.31005(14) 0.84644(9) 0.0252(3) Uani 1 1 d . . . . .
H5' H 0.676845 0.244861 0.844658 0.030 Uiso 1 1 calc R U . . .
C9 C 0.62603(9) 0.72028(14) 0.95392(9) 0.0250(3) Uani 1 1 d . . . . .
H9A H 0.615181 0.632590 0.964305 0.037 Uiso 1 1 calc R U . . .
H9B H 0.584387 0.770445 0.981133 0.037 Uiso 1 1 calc R U . . .
H9C H 0.678313 0.741978 0.977990 0.037 Uiso 1 1 calc R U . . .
C7' C 0.46329(9) 0.60182(15) 0.85358(10) 0.0286(4) Uani 1 1 d . . . . .
H7'A H 0.464053 0.642800 0.909434 0.043 Uiso 1 1 calc R U . . .
H7'B H 0.410515 0.564854 0.843974 0.043 Uiso 1 1 calc R U . . .
H7'C H 0.474324 0.662556 0.808648 0.043 Uiso 1 1 calc R U . . .
C8 C 0.64198(9) 0.87091(13) 0.83727(9) 0.0249(3) Uani 1 1 d . . . . .
H8A H 0.699647 0.882594 0.829255 0.037 Uiso 1 1 calc R U . . .
H8B H 0.622826 0.926739 0.882146 0.037 Uiso 1 1 calc R U . . .
H8C H 0.614023 0.889103 0.783665 0.037 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
O1 H1 0.8400 . ?
O1 C2 1.3613(16) . ?
N1 C7 1.3039(16) . ?
N1 C1 1.4212(16) . ?
N2 C7 1.3559(17) . ?
N2 C9 1.4585(17) . ?
N2 C8 1.4531(18) . ?
C7 C1' 1.5012(18) . ?
C1 C2 1.4054(18) . ?
C1 C6 1.3963(19) . ?
C2 C3 1.3897(19) . ?
C1' C2' 1.4034(19) . ?
C1' C6' 1.396(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(2) . ?
C2' C3' 1.399(2) . ?
C2' C7' 1.507(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C6' H6' 0.9500 . ?
C6' C5' 1.383(2) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.380(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4' H4' 0.9500 . ?
C4' C5' 1.385(2) . ?
C5' H5' 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C7 N1 C1 119.56(11) . . ?
C7 N2 C9 122.91(12) . . ?
C7 N2 C8 119.49(11) . . ?
C8 N2 C9 115.44(12) . . ?
N1 C7 N2 119.70(12) . . ?
N1 C7 C1' 123.17(12) . . ?
N2 C7 C1' 117.13(11) . . ?
C2 C1 N1 118.13(12) . . ?
C6 C1 N1 123.60(12) . . ?
C6 C1 C2 118.22(12) . . ?
O1 C2 C1 123.09(12) . . ?
O1 C2 C3 116.77(12) . . ?
C3 C2 C1 120.12(12) . . ?
C2' C1' C7 121.14(12) . . ?
C6' C1' C7 118.52(12) . . ?
C6' C1' C2' 120.22(13) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.46(13) . . ?
C5 C6 H6 119.3 . . ?
C1' C2' C7' 122.68(13) . . ?
C3' C2' C1' 118.02(13) . . ?
C3' C2' C7' 119.29(13) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.54(13) . . ?
C4 C3 H3 119.7 . . ?
C1' C6' H6' 119.7 . . ?
C5' C6' C1' 120.59(13) . . ?
C5' C6' H6' 119.7 . . ?
C2' C3' H3' 119.4 . . ?
C4' C3' C2' 121.30(13) . . ?
C4' C3' H3' 119.4 . . ?
C6 C5 H5 120.2 . . ?
C6 C5 C4 119.57(13) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 C5 120.02(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3' C4' H4' 119.8 . . ?
C3' C4' C5' 120.32(14) . . ?
C5' C4' H4' 119.8 . . ?
C6' C5' C4' 119.52(14) . . ?
C6' C5' H5' 120.2 . . ?
C4' C5' H5' 120.2 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2' C7' H7'A 109.5 . . ?
C2' C7' H7'B 109.5 . . ?
C2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 2.01 2.7509(14) 146.5 2_665 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.27(13) . . . . ?
N1 C7 C1' C2' -116.88(15) . . . . ?
N1 C7 C1' C6' 59.25(18) . . . . ?
N1 C1 C2 O1 1.66(19) . . . . ?
N1 C1 C2 C3 179.63(12) . . . . ?
N1 C1 C6 C5 179.57(13) . . . . ?
N2 C7 C1' C2' 62.65(17) . . . . ?
N2 C7 C1' C6' -121.21(13) . . . . ?
C7 N1 C1 C2 -128.40(13) . . . . ?
C7 N1 C1 C6 54.23(18) . . . . ?
C7 C1' C2' C3' 176.65(12) . . . . ?
C7 C1' C2' C7' -2.1(2) . . . . ?
C7 C1' C6' C5' -177.52(13) . . . . ?
C1 N1 C7 N2 -171.60(11) . . . . ?
C1 N1 C7 C1' 7.93(19) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C1 C6 C5 C4 0.2(2) . . . . ?
C2 C1 C6 C5 2.2(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C1' C2' C3' C4' 0.9(2) . . . . ?
C1' C6' C5' C4' 0.6(2) . . . . ?
C6 C1 C2 O1 179.17(12) . . . . ?
C6 C1 C2 C3 -2.86(19) . . . . ?
C6 C5 C4 C3 -1.9(2) . . . . ?
C2' C1' C6' C5' -1.4(2) . . . . ?
C2' C3' C4' C5' -1.7(2) . . . . ?
C6' C1' C2' C3' 0.58(19) . . . . ?
C6' C1' C2' C7' -178.12(13) . . . . ?
C3' C4' C5' C6' 0.9(2) . . . . ?
C9 N2 C7 N1 -155.50(13) . . . . ?
C9 N2 C7 C1' 24.95(18) . . . . ?
C7' C2' C3' C4' 179.70(13) . . . . ?
C8 N2 C7 N1 7.04(19) . . . . ?
C8 N2 C7 C1' -172.51(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_L5H
_database_code_depnum_ccdc_archive 'CCDC 2182073'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O'
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_formula_weight         316.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7993(2)
_cell_length_b                   9.5600(3)
_cell_length_c                   11.0330(4)
_cell_angle_alpha                92.371(2)
_cell_angle_beta                 100.401(2)
_cell_angle_gamma                114.782(2)
_cell_volume                     821.64(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6361
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0529 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.8878.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.869
_exptl_crystal_size_mid          0.623
_exptl_crystal_size_min          0.525
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20523
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         1.893
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3047
_reflns_number_total             3792
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0436
_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)+(0.0493P)²+0.4217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1193
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6'),
 C8'(H8'), C9'(H9'), C10'(H10')
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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 0.15487(14) 0.26186(12) 0.06138(10) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.200615 0.358616 0.061356 0.049 Uiso 1 1 calc R U . . .
N1 N 0.40138(14) 0.49755(13) 0.22910(11) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.59358(14) 0.74230(13) 0.21466(11) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.36117(16) 0.34442(15) 0.25474(13) 0.0233(3) Uani 1 1 d . . . . .
C1' C 0.70203(16) 0.54863(14) 0.22694(12) 0.0191(3) Uani 1 1 d . . . . .
C2 C 0.22846(17) 0.22557(16) 0.16853(13) 0.0246(3) Uani 1 1 d . . . . .
C2' C 0.84993(16) 0.60977(14) 0.32604(12) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.17036(18) 0.07163(17) 0.18859(15) 0.0302(3) Uani 1 1 d . . . . .
H3 H 0.082773 -0.007973 0.127787 0.036 Uiso 1 1 calc R U . . .
C3' C 0.86317(17) 0.70271(16) 0.43454(13) 0.0242(3) Uani 1 1 d . . . . .
H3' H 0.771873 0.728652 0.441900 0.029 Uiso 1 1 calc R U . . .
C4 C 0.2409(2) 0.03442(18) 0.29803(16) 0.0344(4) Uani 1 1 d . . . . .
H4 H 0.200075 -0.070871 0.313143 0.041 Uiso 1 1 calc R U . . .
C4' C 1.0063(2) 0.75531(17) 0.52868(14) 0.0317(3) Uani 1 1 d . . . . .
H4' H 1.012952 0.816816 0.601092 0.038 Uiso 1 1 calc R U . . .
C5 C 0.3703(2) 0.15009(19) 0.38509(16) 0.0342(4) Uani 1 1 d . . . . .
H5 H 0.418145 0.124124 0.460116 0.041 Uiso 1 1 calc R U . . .
C5' C 1.14384(19) 0.71929(18) 0.51945(15) 0.0327(3) Uani 1 1 d . . . . .
H5' H 1.242581 0.756543 0.585428 0.039 Uiso 1 1 calc R U . . .
C6 C 0.43125(18) 0.30467(17) 0.36355(14) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.521251 0.383468 0.423585 0.034 Uiso 1 1 calc R U . . .
C6' C 1.13542(17) 0.63124(17) 0.41616(14) 0.0279(3) Uani 1 1 d . . . . .
H6' H 1.229150 0.608231 0.410387 0.033 Uiso 1 1 calc R U . . .
C7 C 0.55719(16) 0.59303(15) 0.22602(12) 0.0205(3) Uani 1 1 d . . . . .
C7' C 0.98888(16) 0.57337(15) 0.31709(12) 0.0216(3) Uani 1 1 d . . . . .
C8 C 0.46346(18) 0.80150(16) 0.20934(14) 0.0269(3) Uani 1 1 d . . . . .
H8A H 0.421473 0.792372 0.287402 0.032 Uiso 1 1 calc R U . . .
H8B H 0.364929 0.744666 0.138720 0.032 Uiso 1 1 calc R U . . .
C8' C 0.97634(18) 0.47708(17) 0.21183(13) 0.0269(3) Uani 1 1 d . . . . .
H8' H 1.069813 0.454098 0.205097 0.032 Uiso 1 1 calc R U . . .
C9 C 0.75575(17) 0.86026(15) 0.19356(14) 0.0260(3) Uani 1 1 d . . . . .
H9A H 0.805857 0.814535 0.139224 0.031 Uiso 1 1 calc R U . . .
H9B H 0.840047 0.910180 0.273002 0.031 Uiso 1 1 calc R U . . .
C9' C 0.83191(19) 0.41678(17) 0.11987(13) 0.0283(3) Uani 1 1 d . . . . .
H9' H 0.824394 0.350467 0.050255 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5590(2) 0.97077(19) 0.19162(19) 0.0410(4) Uani 1 1 d . . . . .
H10A H 0.482234 1.005387 0.137490 0.049 Uiso 1 1 calc R U . . .
H10B H 0.606239 1.038360 0.272523 0.049 Uiso 1 1 calc R U . . .
C10' C 0.69281(17) 0.45217(15) 0.12722(13) 0.0232(3) Uani 1 1 d . . . . .
H10' H 0.592206 0.408929 0.062712 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7021(2) 0.9747(2) 0.13063(17) 0.0389(4) Uani 1 1 d . . . . .
H11A H 0.659965 0.941924 0.039916 0.047 Uiso 1 1 calc R U . . .
H11B H 0.798412 1.080092 0.145686 0.047 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
O1 H1 0.8400 . ?
O1 C2 1.3723(18) . ?
N1 C1 1.4087(17) . ?
N1 C7 1.2978(17) . ?
N2 C7 1.3419(17) . ?
N2 C8 1.4684(16) . ?
N2 C9 1.4680(17) . ?
C1 C2 1.399(2) . ?
C1 C6 1.390(2) . ?
C1' C2' 1.4235(18) . ?
C1' C7 1.5013(17) . ?
C1' C10' 1.3743(18) . ?
C2 C3 1.383(2) . ?
C2' C3' 1.4180(18) . ?
C2' C7' 1.4224(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.368(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(2) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.409(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.360(2) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C6' C7' 1.4165(19) . ?
C7' C8' 1.4101(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C10 1.519(2) . ?
C8' H8' 0.9500 . ?
C8' C9' 1.360(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C11 1.510(2) . ?
C9' H9' 0.9500 . ?
C9' C10' 1.4142(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(2) . ?
C10' H10' 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C2 O1 H1 109.5 . . ?
C7 N1 C1 120.92(11) . . ?
C7 N2 C8 121.89(11) . . ?
C7 N2 C9 125.92(11) . . ?
C9 N2 C8 111.90(11) . . ?
C2 C1 N1 116.43(12) . . ?
C6 C1 N1 124.95(13) . . ?
C6 C1 C2 118.30(13) . . ?
C2' C1' C7 121.17(11) . . ?
C10' C1' C2' 120.12(11) . . ?
C10' C1' C7 118.66(11) . . ?
O1 C2 C1 119.51(12) . . ?
O1 C2 C3 119.15(13) . . ?
C3 C2 C1 121.34(14) . . ?
C3' C2' C1' 122.79(11) . . ?
C3' C2' C7' 118.57(12) . . ?
C7' C2' C1' 118.63(11) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.49(14) . . ?
C4 C3 H3 120.3 . . ?
C2' C3' H3' 119.7 . . ?
C4' C3' C2' 120.58(13) . . ?
C4' C3' H3' 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.09(14) . . ?
C5 C4 H4 120.0 . . ?
C3' C4' H4' 119.6 . . ?
C3' C4' C5' 120.73(14) . . ?
C5' C4' H4' 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.34(15) . . ?
C6 C5 H5 119.8 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' C4' 120.08(13) . . ?
C6' C5' H5' 120.0 . . ?
C1 C6 C5 120.41(14) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5' C6' H6' 119.5 . . ?
C5' C6' C7' 120.93(13) . . ?
C7' C6' H6' 119.5 . . ?
N1 C7 N2 118.95(12) . . ?
N1 C7 C1' 125.09(12) . . ?
N2 C7 C1' 115.86(11) . . ?
C6' C7' C2' 119.12(13) . . ?
C8' C7' C2' 119.57(12) . . ?
C8' C7' C6' 121.29(12) . . ?
N2 C8 H8A 111.1 . . ?
N2 C8 H8B 111.1 . . ?
N2 C8 C10 103.47(11) . . ?
H8A C8 H8B 109.0 . . ?
C10 C8 H8A 111.1 . . ?
C10 C8 H8B 111.1 . . ?
C7' C8' H8' 119.6 . . ?
C9' C8' C7' 120.71(12) . . ?
C9' C8' H8' 119.6 . . ?
N2 C9 H9A 111.2 . . ?
N2 C9 H9B 111.2 . . ?
N2 C9 C11 102.83(11) . . ?
H9A C9 H9B 109.1 . . ?
C11 C9 H9A 111.2 . . ?
C11 C9 H9B 111.2 . . ?
C8' C9' H9' 119.8 . . ?
C8' C9' C10' 120.41(13) . . ?
C10' C9' H9' 119.8 . . ?
C8 C10 H10A 110.9 . . ?
C8 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 C8 104.44(12) . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C1' C10' C9' 120.52(12) . . ?
C1' C10' H10' 119.7 . . ?
C9' C10' H10' 119.7 . . ?
C9 C11 C10 103.21(13) . . ?
C9 C11 H11A 111.1 . . ?
C9 C11 H11B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 2.23 2.7045(15) 116.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -178.30(12) . . . . ?
N1 C1 C2 O1 4.93(18) . . . . ?
N1 C1 C2 C3 -175.52(12) . . . . ?
N1 C1 C6 C5 173.53(13) . . . . ?
N2 C8 C10 C11 25.23(17) . . . . ?
N2 C9 C11 C10 34.25(16) . . . . ?
C1 N1 C7 N2 -172.87(12) . . . . ?
C1 N1 C7 C1' 10.8(2) . . . . ?
C1 C2 C3 C4 2.1(2) . . . . ?
C1' C2' C3' C4' 178.25(13) . . . . ?
C1' C2' C7' C6' -178.86(12) . . . . ?
C1' C2' C7' C8' -0.66(18) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2' C1' C7 N1 -117.34(15) . . . . ?
C2' C1' C7 N2 66.23(17) . . . . ?
C2' C1' C10' C9' -2.1(2) . . . . ?
C2' C3' C4' C5' 0.5(2) . . . . ?
C2' C7' C8' C9' -1.0(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C3' C2' C7' C6' -0.20(18) . . . . ?
C3' C2' C7' C8' 178.00(12) . . . . ?
C3' C4' C5' C6' 0.0(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4' C5' C6' C7' -0.5(2) . . . . ?
C5' C6' C7' C2' 0.6(2) . . . . ?
C5' C6' C7' C8' -177.53(13) . . . . ?
C6 C1 C2 O1 178.82(12) . . . . ?
C6 C1 C2 C3 -1.63(19) . . . . ?
C6' C7' C8' C9' 177.11(13) . . . . ?
C7 N1 C1 C2 -126.45(14) . . . . ?
C7 N1 C1 C6 60.12(19) . . . . ?
C7 N2 C8 C10 -177.89(13) . . . . ?
C7 N2 C9 C11 154.58(14) . . . . ?
C7 C1' C2' C3' 6.34(19) . . . . ?
C7 C1' C2' C7' -175.05(11) . . . . ?
C7 C1' C10' C9' 175.23(12) . . . . ?
C7' C2' C3' C4' -0.4(2) . . . . ?
C7' C8' C9' C10' 1.2(2) . . . . ?
C8 N2 C7 N1 1.8(2) . . . . ?
C8 N2 C7 C1' 178.50(12) . . . . ?
C8 N2 C9 C11 -19.39(16) . . . . ?
C8 C10 C11 C9 -37.36(18) . . . . ?
C8' C9' C10' C1' 0.4(2) . . . . ?
C9 N2 C7 N1 -171.57(13) . . . . ?
C9 N2 C7 C1' 5.09(19) . . . . ?
C9 N2 C8 C10 -3.64(16) . . . . ?
C10' C1' C2' C3' -176.38(12) . . . . ?
C10' C1' C2' C7' 2.23(18) . . . . ?
C10' C1' C7 N1 65.34(18) . . . . ?
C10' C1' C7 N2 -111.09(14) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a glass fibre oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_L4H
_database_code_depnum_ccdc_archive 'CCDC 2182072'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.8302(12)
_cell_length_b                   8.1178(5)
_cell_length_c                   18.3922(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2960.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.8039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0904 after correction.
The Ratio of minimum to maximum transmission is 0.8389.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 3.00 -2.00 0.3030
-1.00 1.00 3.00 0.2020
0.00 0.00 1.00 0.2030
3.00 -2.00 4.00 0.3120
4.00 -3.00 -4.00 0.3380
0.00 0.00 -1.00 0.2280
3.00 1.00 0.00 0.2390
-3.00 0.00 -1.00 0.2220
-3.00 -1.00 0.00 0.2830
-2.00 1.00 -4.00 0.2670
2.00 -2.00 1.00 0.3100
-4.00 -4.00 -3.00 0.3080
-4.00 -2.00 -3.00 0.2740
-4.00 -1.00 -3.00 0.2450
-4.00 1.00 -4.00 0.2540
3.00 2.00 2.00 0.1990
4.00 1.00 3.00 0.2220
2.00 1.00 -1.00 0.1890
4.00 -1.00 2.00 0.2820
-1.00 -3.00 3.00 0.3470
-2.00 -1.00 1.00 0.2840
1.00 0.00 -1.00 0.2170
1.00 1.00 -4.00 0.2380
-4.00 1.00 1.00 0.2630
-1.00 0.00 1.00 0.2900

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.558
_exptl_crystal_size_min          0.475
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68139
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4631
_reflns_number_total             5224
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0868
_refine_ls_restrained_S_all      1.192
_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)+(0.1327P)²+3.4250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2210
_refine_ls_wR_factor_ref         0.2340
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(4)
 1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Others
 Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=FVAR(1)
 Sof(H9AE)=Sof(H9AF)=Sof(H11G)=Sof(H11H)=1-FVAR(2)
 Sof(H9AC)=Sof(H9AD)=Sof(H11E)=Sof(H11F)=FVAR(2)
 Fixed Sof: H9AA(0.8) H9AB(0.8) H9BC(0.2) H9BD(0.2) C10(0.8) H10A(0.8)
 H10B(0.8) C10*(0.2) H10C(0.2) H10D(0.2) C10A(0.77) H10E(0.77) H10F(0.77)
 C10B(0.23) H10G(0.23) H10H(0.23)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9AA,H9AB), C9(H9BC,H9BD), C10(H10A,H10B), C10*(H10C,H10D),
 C11(H11A,H11B), C11(H11C,H11D), C8A(H8AA,H8AB), C9A(H9AC,H9AD), C9A(H9AE,H9AF),
  C10A(H10E,H10F), C11A(H11E,H11F), C11A(H11G,H11H), C10B(H10G,H10H)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6'),
 C3'A(H3'A), C3A(H3A), C4'A(H4'A), C4A(H4A), C5'A(H5'A), C5A(H5A), C6'A(H6'A),
 C6A(H6A)
4.c Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C7'A(H7'D,H7'E,H7'F)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_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 0.5992(2) 0.6296(6) 0.3741(3) 0.0313(11) Uani 1 1 d . . . . .
H1 H 0.594682 0.616857 0.419161 0.047 Uiso 1 1 calc R U . . .
N1 N 0.6563(2) 0.7698(6) 0.4840(3) 0.0177(11) Uani 1 1 d . . . . .
N2 N 0.6344(3) 0.7908(7) 0.6043(3) 0.0254(12) Uani 1 1 d . . . . .
C1 C 0.6938(3) 0.7798(7) 0.4180(3) 0.0192(13) Uani 1 1 d . . . . .
C1' C 0.7466(3) 0.8650(7) 0.5681(3) 0.0194(13) Uani 1 1 d . . . . .
C2 C 0.6598(3) 0.7045(8) 0.3601(4) 0.0221(14) Uani 1 1 d . . . . .
C2' C 0.7998(3) 0.7495(7) 0.5749(4) 0.0180(13) Uani 1 1 d . . . . .
C3 C 0.6868(4) 0.7003(9) 0.2911(4) 0.0305(16) Uani 1 1 d . . . . .
H3 H 0.663324 0.646045 0.253040 0.037 Uiso 1 1 calc R U . . .
C3' C 0.8639(3) 0.8082(9) 0.5905(4) 0.0271(15) Uani 1 1 d . . . . .
H3' H 0.900060 0.732380 0.595623 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7475(4) 0.7743(8) 0.2775(4) 0.0291(16) Uani 1 1 d . . . . .
H4 H 0.766244 0.771895 0.229943 0.035 Uiso 1 1 calc R U . . .
C4' C 0.8763(4) 0.9764(9) 0.5988(4) 0.0318(16) Uani 1 1 d . . . . .
H4' H 0.920743 1.014294 0.608494 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7817(4) 0.8533(8) 0.3337(4) 0.0300(16) Uani 1 1 d . . . . .
H5 H 0.823603 0.905712 0.324233 0.036 Uiso 1 1 calc R U . . .
C5' C 0.8234(4) 1.0887(9) 0.5929(4) 0.0335(16) Uani 1 1 d . . . . .
H5' H 0.831679 1.203023 0.599389 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7550(3) 0.8562(8) 0.4038(4) 0.0217(13) Uani 1 1 d . . . . .
H6 H 0.778704 0.910395 0.441816 0.026 Uiso 1 1 calc R U . . .
C6' C 0.7587(3) 1.0337(8) 0.5776(4) 0.0263(14) Uani 1 1 d . . . . .
H6' H 0.722688 1.110340 0.573625 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6778(3) 0.8066(8) 0.5483(3) 0.0203(13) Uani 1 1 d . . . . .
C7' C 0.7849(3) 0.5703(8) 0.5697(4) 0.0259(14) Uani 1 1 d . . . . .
H7'A H 0.756160 0.537251 0.610554 0.039 Uiso 1 1 calc R U . . .
H7'B H 0.827144 0.507882 0.571240 0.039 Uiso 1 1 calc R U . . .
H7'C H 0.761443 0.547582 0.523849 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5667(3) 0.7335(9) 0.5948(4) 0.0272(16) Uani 1 1 d . . . . .
H8A H 0.566189 0.621882 0.573112 0.033 Uiso 1 1 calc R U . . .
H8B H 0.540866 0.809018 0.562998 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6507(4) 0.8217(11) 0.6811(4) 0.0369(18) Uani 1 1 d . . . . .
H9AA H 0.646612 0.940118 0.693100 0.044 Uiso 0.8 1 calc R U P A 1
H9AB H 0.696842 0.783759 0.692953 0.044 Uiso 0.8 1 calc R U P A 1
H9BC H 0.679238 0.732300 0.700921 0.044 Uiso 0.2 1 calc R U P B 2
H9BD H 0.674738 0.927768 0.686727 0.044 Uiso 0.2 1 calc R U P B 2
C10 C 0.5988(5) 0.7219(14) 0.7202(5) 0.034(2) Uani 0.8 1 d . . P C 1
H10A H 0.589277 0.769112 0.768767 0.041 Uiso 0.8 1 calc R U P C 1
H10B H 0.613967 0.606567 0.726150 0.041 Uiso 0.8 1 calc R U P C 1
C10* C 0.5888(19) 0.826(5) 0.716(2) 0.031(8) Uiso 0.2 1 d . . P C 2
H10C H 0.573917 0.941902 0.721611 0.037 Uiso 0.2 1 calc R U P C 2
H10D H 0.592969 0.777022 0.765035 0.037 Uiso 0.2 1 calc R U P C 2
C11 C 0.5369(4) 0.7308(11) 0.6719(4) 0.0328(17) Uani 1 1 d . . . . .
H11A H 0.510472 0.831912 0.681748 0.039 Uiso 0.95(12) 1 calc R U P C 1
H11B H 0.507508 0.633486 0.679074 0.039 Uiso 0.95(12) 1 calc R U P C 1
H11C H 0.492285 0.785654 0.673326 0.039 Uiso 0.05(12) 1 calc R U P C 2
H11D H 0.532101 0.616587 0.690075 0.039 Uiso 0.05(12) 1 calc R U P C 2
O1A O 0.6407(2) 0.3523(7) 0.6292(3) 0.0360(13) Uani 1 1 d . . . . .
H1A H 0.653252 0.331748 0.586525 0.054 Uiso 1 1 calc R U . . .
N1A N 0.5833(3) 0.2258(6) 0.5183(3) 0.0196(11) Uani 1 1 d . . . . .
N2A N 0.6042(2) 0.2110(7) 0.3966(3) 0.0222(12) Uani 1 1 d . . . . .
C1'A C 0.4902(3) 0.1437(8) 0.4329(3) 0.0217(14) Uani 1 1 d . . . . .
C1A C 0.5456(3) 0.2112(7) 0.5820(3) 0.0189(13) Uani 1 1 d . . . . .
C2'A C 0.4397(3) 0.2592(8) 0.4272(4) 0.0212(14) Uani 1 1 d . . . . .
C2A C 0.5802(3) 0.2787(8) 0.6418(4) 0.0236(14) Uani 1 1 d . . . . .
C3'A C 0.3744(3) 0.2033(9) 0.4136(4) 0.0282(15) Uani 1 1 d . . . . .
H3'A H 0.338196 0.279981 0.411745 0.034 Uiso 1 1 calc R U . . .
C3A C 0.5535(4) 0.2745(9) 0.7118(4) 0.0309(16) Uani 1 1 d . . . . .
H3A H 0.578742 0.317685 0.751360 0.037 Uiso 1 1 calc R U . . .
C4'A C 0.3615(4) 0.0361(9) 0.4027(4) 0.0329(16) Uani 1 1 d . . . . .
H4'A H 0.316940 0.000040 0.392342 0.040 Uiso 1 1 calc R U . . .
C4A C 0.4910(4) 0.2084(9) 0.7238(4) 0.0299(16) Uani 1 1 d . . . . .
H4A H 0.471948 0.211252 0.771171 0.036 Uiso 1 1 calc R U . . .
C5'A C 0.4130(4) -0.0763(9) 0.4068(4) 0.0328(16) Uani 1 1 d . . . . .
H5'A H 0.404215 -0.190043 0.399115 0.039 Uiso 1 1 calc R U . . .
C5A C 0.4554(4) 0.1372(9) 0.6669(4) 0.0289(15) Uani 1 1 d . . . . .
H5A H 0.412641 0.088234 0.675323 0.035 Uiso 1 1 calc R U . . .
C6'A C 0.4776(3) -0.0236(8) 0.4222(3) 0.0263(14) Uani 1 1 d . . . . .
H6'A H 0.513403 -0.101009 0.425368 0.032 Uiso 1 1 calc R U . . .
C6A C 0.4832(3) 0.1383(8) 0.5971(4) 0.0250(14) Uani 1 1 d . . . . .
H6A H 0.458882 0.087855 0.558596 0.030 Uiso 1 1 calc R U . . .
C7'A C 0.4540(4) 0.4398(9) 0.4338(5) 0.0345(17) Uani 1 1 d . . . . .
H7'D H 0.482494 0.475118 0.393115 0.052 Uiso 1 1 calc R U . . .
H7'E H 0.477498 0.461123 0.479739 0.052 Uiso 1 1 calc R U . . .
H7'F H 0.411508 0.501185 0.432876 0.052 Uiso 1 1 calc R U . . .
C7A C 0.5606(3) 0.1951(8) 0.4524(3) 0.0196(13) Uani 1 1 d . . . . .
C8A C 0.6746(3) 0.2582(8) 0.4066(4) 0.0205(14) Uani 1 1 d . . . . .
H8AA H 0.698767 0.176731 0.436972 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.678166 0.368080 0.429576 0.025 Uiso 1 1 calc R U . . .
C9A C 0.5861(3) 0.1992(10) 0.3187(4) 0.0323(16) Uani 1 1 d . . . . .
H9AC H 0.566288 0.303447 0.300845 0.039 Uiso 0.81(8) 1 calc R U P D 1
H9AD H 0.553962 0.108052 0.309954 0.039 Uiso 0.81(8) 1 calc R U P D 1
H9AE H 0.577702 0.083015 0.305067 0.039 Uiso 0.19(8) 1 calc R U P D 2
H9AF H 0.544947 0.264067 0.308532 0.039 Uiso 0.19(8) 1 calc R U P D 2
C10A C 0.6532(5) 0.1655(12) 0.2833(5) 0.027(2) Uani 0.77 1 d . . P E 1
H10E H 0.653561 0.204825 0.232403 0.033 Uiso 0.77 1 calc R U P E 1
H10F H 0.663638 0.046228 0.283991 0.033 Uiso 0.77 1 calc R U P E 1
C11A C 0.7028(3) 0.2610(8) 0.3293(4) 0.0244(15) Uani 1 1 d . . . . .
H11E H 0.706901 0.375673 0.311512 0.029 Uiso 0.81(8) 1 calc R U P D 1
H11F H 0.747869 0.208568 0.327726 0.029 Uiso 0.81(8) 1 calc R U P D 1
H11G H 0.730887 0.360316 0.321572 0.029 Uiso 0.19(8) 1 calc R U P D 2
H11H H 0.730778 0.162116 0.320126 0.029 Uiso 0.19(8) 1 calc R U P D 2
C10B C 0.6417(14) 0.263(4) 0.2791(18) 0.025(7) Uiso 0.23 1 d . . P E 2
H10G H 0.632098 0.377041 0.263041 0.030 Uiso 0.23 1 calc R U P E 2
H10H H 0.650438 0.194550 0.235604 0.030 Uiso 0.23 1 calc R U P E 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C2 1.372(8) . ?
N1 C1 1.426(8) . ?
N1 C7 1.293(9) . ?
N2 C7 1.348(8) . ?
N2 C8 1.433(9) . ?
N2 C9 1.469(9) . ?
C1 C2 1.401(9) . ?
C1 C6 1.388(9) . ?
C1' C2' 1.417(8) . ?
C1' C6' 1.402(9) . ?
C1' C7 1.489(9) . ?
C2 C3 1.377(10) . ?
C2' C3' 1.388(9) . ?
C2' C7' 1.488(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(11) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.396(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(11) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.394(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(9) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.387(10) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C11 1.537(10) . ?
C9 H9AA 0.9900 . ?
C9 H9AB 0.9900 . ?
C9 H9BC 0.9900 . ?
C9 H9BD 0.9900 . ?
C9 C10 1.494(12) . ?
C9 C10* 1.39(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.517(12) . ?
C10* H10C 0.9900 . ?
C10* H10D 0.9900 . ?
C10* C11 1.52(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
O1A H1A 0.8400 . ?
O1A C2A 1.360(8) . ?
N1A C1A 1.395(8) . ?
N1A C7A 1.316(8) . ?
N2A C7A 1.348(8) . ?
N2A C8A 1.459(8) . ?
N2A C9A 1.480(9) . ?
C1'A C2'A 1.376(9) . ?
C1'A C6'A 1.395(9) . ?
C1'A C7A 1.500(9) . ?
C1A C2A 1.407(9) . ?
C1A C6A 1.400(9) . ?
C2'A C3'A 1.396(9) . ?
C2'A C7'A 1.498(10) . ?
C2A C3A 1.393(11) . ?
C3'A H3'A 0.9500 . ?
C3'A C4'A 1.396(10) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.368(11) . ?
C4'A H4'A 0.9500 . ?
C4'A C5'A 1.372(10) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.389(10) . ?
C5'A H5'A 0.9500 . ?
C5'A C6'A 1.380(10) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.396(10) . ?
C6'A H6'A 0.9500 . ?
C6A H6A 0.9500 . ?
C7'A H7'D 0.9800 . ?
C7'A H7'E 0.9800 . ?
C7'A H7'F 0.9800 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C11A 1.527(10) . ?
C9A H9AC 0.9900 . ?
C9A H9AD 0.9900 . ?
C9A H9AE 0.9900 . ?
C9A H9AF 0.9900 . ?
C9A C10A 1.505(12) . ?
C9A C10B 1.42(3) . ?
C10A H10E 0.9900 . ?
C10A H10F 0.9900 . ?
C10A C11A 1.512(11) . ?
C11A H11E 0.9900 . ?
C11A H11F 0.9900 . ?
C11A H11G 0.9900 . ?
C11A H11H 0.9900 . ?
C11A C10B 1.52(3) . ?
C10B H10G 0.9900 . ?
C10B H10H 0.9900 . ?

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
C2 O1 H1 109.5 . . ?
C7 N1 C1 126.5(5) . . ?
C7 N2 C8 122.4(6) . . ?
C7 N2 C9 125.3(6) . . ?
C8 N2 C9 112.3(6) . . ?
C2 C1 N1 111.8(5) . . ?
C6 C1 N1 129.9(6) . . ?
C6 C1 C2 118.2(6) . . ?
C2' C1' C7 119.5(5) . . ?
C6' C1' C2' 120.5(6) . . ?
C6' C1' C7 120.0(5) . . ?
O1 C2 C1 118.2(6) . . ?
O1 C2 C3 120.2(6) . . ?
C3 C2 C1 121.6(6) . . ?
C1' C2' C7' 119.6(6) . . ?
C3' C2' C1' 118.2(6) . . ?
C3' C2' C7' 122.1(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(7) . . ?
C4 C3 H3 120.0 . . ?
C2' C3' H3' 119.3 . . ?
C2' C3' C4' 121.4(6) . . ?
C4' C3' H3' 119.3 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(7) . . ?
C5 C4 H4 120.2 . . ?
C3' C4' H4' 120.1 . . ?
C5' C4' C3' 119.9(7) . . ?
C5' C4' H4' 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(6) . . ?
C6 C5 H5 119.7 . . ?
C4' C5' H5' 119.9 . . ?
C6' C5' C4' 120.1(6) . . ?
C6' C5' H5' 119.9 . . ?
C1 C6 C5 119.9(6) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C1' C6' H6' 120.0 . . ?
C5' C6' C1' 119.9(6) . . ?
C5' C6' H6' 120.0 . . ?
N1 C7 N2 117.9(6) . . ?
N1 C7 C1' 126.8(6) . . ?
N2 C7 C1' 115.4(6) . . ?
C2' C7' H7'A 109.5 . . ?
C2' C7' H7'B 109.5 . . ?
C2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N2 C8 H8A 110.8 . . ?
N2 C8 H8B 110.8 . . ?
N2 C8 C11 104.6(6) . . ?
H8A C8 H8B 108.9 . . ?
C11 C8 H8A 110.8 . . ?
C11 C8 H8B 110.8 . . ?
N2 C9 H9AA 111.2 . . ?
N2 C9 H9AB 111.2 . . ?
N2 C9 H9BC 110.8 . . ?
N2 C9 H9BD 110.8 . . ?
N2 C9 C10 102.6(7) . . ?
H9AA C9 H9AB 109.2 . . ?
H9BC C9 H9BD 108.9 . . ?
C10 C9 H9AA 111.2 . . ?
C10 C9 H9AB 111.2 . . ?
C10* C9 N2 104.8(17) . . ?
C10* C9 H9BC 110.8 . . ?
C10* C9 H9BD 110.8 . . ?
C9 C10 H10A 110.9 . . ?
C9 C10 H10B 110.9 . . ?
C9 C10 C11 104.5(7) . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10* H10C 109.7 . . ?
C9 C10* H10D 109.7 . . ?
C9 C10* C11 110(3) . . ?
H10C C10* H10D 108.2 . . ?
C11 C10* H10C 109.7 . . ?
C11 C10* H10D 109.7 . . ?
C8 C11 H11A 111.1 . . ?
C8 C11 H11B 111.1 . . ?
C8 C11 H11C 111.2 . . ?
C8 C11 H11D 111.2 . . ?
C10 C11 C8 103.3(6) . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C10* C11 C8 102.9(16) . . ?
C10* C11 H11C 111.2 . . ?
C10* C11 H11D 111.2 . . ?
H11A C11 H11B 109.1 . . ?
H11C C11 H11D 109.1 . . ?
C2A O1A H1A 109.5 . . ?
C7A N1A C1A 125.1(5) . . ?
C7A N2A C8A 122.9(5) . . ?
C7A N2A C9A 125.1(5) . . ?
C8A N2A C9A 111.7(5) . . ?
C2'A C1'A C6'A 121.5(6) . . ?
C2'A C1'A C7A 120.4(6) . . ?
C6'A C1'A C7A 118.2(6) . . ?
N1A C1A C2A 111.2(5) . . ?
N1A C1A C6A 132.6(6) . . ?
C6A C1A C2A 116.2(6) . . ?
C1'A C2'A C3'A 117.9(6) . . ?
C1'A C2'A C7'A 121.5(6) . . ?
C3'A C2'A C7'A 120.6(6) . . ?
O1A C2A C1A 117.9(6) . . ?
O1A C2A C3A 120.2(6) . . ?
C3A C2A C1A 121.8(6) . . ?
C2'A C3'A H3'A 119.6 . . ?
C4'A C3'A C2'A 120.8(6) . . ?
C4'A C3'A H3'A 119.6 . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A C2A 120.2(6) . . ?
C4A C3A H3A 119.9 . . ?
C3'A C4'A H4'A 119.9 . . ?
C5'A C4'A C3'A 120.2(6) . . ?
C5'A C4'A H4'A 119.9 . . ?
C3A C4A H4A 119.9 . . ?
C3A C4A C5A 120.1(7) . . ?
C5A C4A H4A 119.9 . . ?
C4'A C5'A H5'A 120.1 . . ?
C4'A C5'A C6'A 119.7(6) . . ?
C6'A C5'A H5'A 120.1 . . ?
C4A C5A H5A 120.3 . . ?
C4A C5A C6A 119.3(6) . . ?
C6A C5A H5A 120.3 . . ?
C1'A C6'A H6'A 120.1 . . ?
C5'A C6'A C1'A 119.8(6) . . ?
C5'A C6'A H6'A 120.1 . . ?
C1A C6A H6A 118.9 . . ?
C5A C6A C1A 122.3(6) . . ?
C5A C6A H6A 118.9 . . ?
C2'A C7'A H7'D 109.5 . . ?
C2'A C7'A H7'E 109.5 . . ?
C2'A C7'A H7'F 109.5 . . ?
H7'D C7'A H7'E 109.5 . . ?
H7'D C7'A H7'F 109.5 . . ?
H7'E C7'A H7'F 109.5 . . ?
N1A C7A N2A 117.6(6) . . ?
N1A C7A C1'A 126.2(6) . . ?
N2A C7A C1'A 116.2(5) . . ?
N2A C8A H8AA 111.0 . . ?
N2A C8A H8AB 111.0 . . ?
N2A C8A C11A 103.8(5) . . ?
H8AA C8A H8AB 109.0 . . ?
C11A C8A H8AA 111.0 . . ?
C11A C8A H8AB 111.0 . . ?
N2A C9A H9AC 111.3 . . ?
N2A C9A H9AD 111.3 . . ?
N2A C9A H9AE 110.4 . . ?
N2A C9A H9AF 110.4 . . ?
N2A C9A C10A 102.5(6) . . ?
H9AC C9A H9AD 109.2 . . ?
H9AE C9A H9AF 108.6 . . ?
C10A C9A H9AC 111.3 . . ?
C10A C9A H9AD 111.3 . . ?
C10B C9A N2A 106.6(14) . . ?
C10B C9A H9AE 110.4 . . ?
C10B C9A H9AF 110.4 . . ?
C9A C10A H10E 111.0 . . ?
C9A C10A H10F 111.0 . . ?
C9A C10A C11A 103.9(7) . . ?
H10E C10A H10F 109.0 . . ?
C11A C10A H10E 111.0 . . ?
C11A C10A H10F 111.0 . . ?
C8A C11A H11E 110.6 . . ?
C8A C11A H11F 110.6 . . ?
C8A C11A H11G 110.6 . . ?
C8A C11A H11H 110.6 . . ?
C10A C11A C8A 105.9(6) . . ?
C10A C11A H11E 110.6 . . ?
C10A C11A H11F 110.6 . . ?
H11E C11A H11F 108.7 . . ?
H11G C11A H11H 108.7 . . ?
C10B C11A C8A 105.8(13) . . ?
C10B C11A H11G 110.6 . . ?
C10B C11A H11H 110.6 . . ?
C9A C10B C11A 108(2) . . ?
C9A C10B H10G 110.2 . . ?
C9A C10B H10H 110.2 . . ?
C11A C10B H10G 110.2 . . ?
C11A C10B H10H 110.2 . . ?
H10G C10B H10H 108.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 2.11 2.581(7) 115.0 . yes
O1A H1A N1A 0.84 2.06 2.552(8) 116.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.6(6) . . . . ?
N1 C1 C2 O1 -2.2(8) . . . . ?
N1 C1 C2 C3 179.8(6) . . . . ?
N1 C1 C6 C5 -178.5(6) . . . . ?
N2 C8 C11 C10 -22.0(8) . . . . ?
N2 C8 C11 C10* 12.3(19) . . . . ?
N2 C9 C10 C11 -33.6(9) . . . . ?
N2 C9 C10* C11 24(3) . . . . ?
C1 N1 C7 N2 179.2(6) . . . . ?
C1 N1 C7 C1' -1.0(10) . . . . ?
C1 C2 C3 C4 -1.6(10) . . . . ?
C1' C2' C3' C4' -0.4(11) . . . . ?
C2 C1 C6 C5 -1.4(9) . . . . ?
C2 C3 C4 C5 0.1(10) . . . . ?
C2' C1' C6' C5' 0.9(10) . . . . ?
C2' C1' C7 N1 -80.0(9) . . . . ?
C2' C1' C7 N2 99.8(7) . . . . ?
C2' C3' C4' C5' 1.3(11) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C3' C4' C5' C6' -1.1(11) . . . . ?
C4 C5 C6 C1 0.0(9) . . . . ?
C4' C5' C6' C1' 0.0(11) . . . . ?
C6 C1 C2 O1 -179.7(6) . . . . ?
C6 C1 C2 C3 2.2(9) . . . . ?
C6' C1' C2' C3' -0.7(10) . . . . ?
C6' C1' C2' C7' 175.7(6) . . . . ?
C6' C1' C7 N1 98.1(8) . . . . ?
C6' C1' C7 N2 -82.1(8) . . . . ?
C7 N1 C1 C2 169.7(6) . . . . ?
C7 N1 C1 C6 -13.1(10) . . . . ?
C7 N2 C8 C11 178.6(6) . . . . ?
C7 N2 C9 C10 -156.9(7) . . . . ?
C7 N2 C9 C10* 167(2) . . . . ?
C7 C1' C2' C3' 177.5(6) . . . . ?
C7 C1' C2' C7' -6.2(10) . . . . ?
C7 C1' C6' C5' -177.2(6) . . . . ?
C7' C2' C3' C4' -176.7(6) . . . . ?
C8 N2 C7 N1 0.8(9) . . . . ?
C8 N2 C7 C1' -179.0(6) . . . . ?
C8 N2 C9 C10 20.4(9) . . . . ?
C8 N2 C9 C10* -16(2) . . . . ?
C9 N2 C7 N1 177.9(6) . . . . ?
C9 N2 C7 C1' -1.9(9) . . . . ?
C9 N2 C8 C11 1.2(8) . . . . ?
C9 C10 C11 C8 34.7(9) . . . . ?
C9 C10* C11 C8 -23(3) . . . . ?
O1A C2A C3A C4A 176.4(6) . . . . ?
N1A C1A C2A O1A 3.2(8) . . . . ?
N1A C1A C2A C3A -178.2(6) . . . . ?
N1A C1A C6A C5A 179.1(6) . . . . ?
N2A C8A C11A C10A -17.1(7) . . . . ?
N2A C8A C11A C10B 15.9(15) . . . . ?
N2A C9A C10A C11A -34.2(8) . . . . ?
N2A C9A C10B C11A 19(2) . . . . ?
C1'A C2'A C3'A C4'A -3.1(11) . . . . ?
C1A N1A C7A N2A -178.2(5) . . . . ?
C1A N1A C7A C1'A 1.8(10) . . . . ?
C1A C2A C3A C4A -2.2(10) . . . . ?
C2'A C1'A C6'A C5'A -1.4(10) . . . . ?
C2'A C1'A C7A N1A 81.1(9) . . . . ?
C2'A C1'A C7A N2A -98.9(7) . . . . ?
C2'A C3'A C4'A C5'A 1.5(11) . . . . ?
C2A C1A C6A C5A 2.2(9) . . . . ?
C2A C3A C4A C5A 3.5(10) . . . . ?
C3'A C4'A C5'A C6'A 0.3(11) . . . . ?
C3A C4A C5A C6A -1.9(10) . . . . ?
C4'A C5'A C6'A C1'A -0.4(10) . . . . ?
C4A C5A C6A C1A -1.0(10) . . . . ?
C6'A C1'A C2'A C3'A 3.1(10) . . . . ?
C6'A C1'A C2'A C7'A -175.9(7) . . . . ?
C6'A C1'A C7A N1A -97.9(8) . . . . ?
C6'A C1'A C7A N2A 82.1(8) . . . . ?
C6A C1A C2A O1A -179.3(6) . . . . ?
C6A C1A C2A C3A -0.6(9) . . . . ?
C7'A C2'A C3'A C4'A 175.8(7) . . . . ?
C7A N1A C1A C2A -170.1(6) . . . . ?
C7A N1A C1A C6A 12.9(10) . . . . ?
C7A N2A C8A C11A -179.6(6) . . . . ?
C7A N2A C9A C10A -160.7(7) . . . . ?
C7A N2A C9A C10B 165.7(16) . . . . ?
C7A C1'A C2'A C3'A -175.9(6) . . . . ?
C7A C1'A C2'A C7'A 5.2(10) . . . . ?
C7A C1'A C6'A C5'A 177.6(6) . . . . ?
C8A N2A C7A N1A 0.8(9) . . . . ?
C8A N2A C7A C1'A -179.3(6) . . . . ?
C8A N2A C9A C10A 24.8(8) . . . . ?
C8A N2A C9A C10B -8.8(17) . . . . ?
C8A C11A C10B C9A -22(2) . . . . ?
C9A N2A C7A N1A -173.1(6) . . . . ?
C9A N2A C7A C1'A 6.9(9) . . . . ?
C9A N2A C8A C11A -5.0(7) . . . . ?
C9A C10A C11A C8A 32.3(8) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(4)
2 1(4)
####################################################################### 
# 
# 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_compound_1b
_database_code_depnum_ccdc_archive 'CCDC 2182075'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 Al N4 O2'
_chemical_formula_sum            'C19 H25 Al N4 O2'
_chemical_formula_weight         368.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.0344(13)
_cell_length_b                   13.1284(16)
_cell_length_c                   12.6875(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.976(4)
_cell_angle_gamma                90
_cell_volume                     1906.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9714
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0681 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.9196.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.627
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.219
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         2.563
_diffrn_ambient_temperature      120.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3550
_reflns_number_total             4390
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.038
_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)+(0.0395P)²+1.2720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3A(H3A), C4(H4), C4A(H4A), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C7(H7), C7A(H7A)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC),
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_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
Al1 Al 0.72419(4) 0.40282(3) 0.46314(3) 0.01353(11) Uani 1 1 d . . . . .
O1 O 0.84260(9) 0.33050(8) 0.44198(8) 0.0167(2) Uani 1 1 d . . . . .
O1A O 0.58036(9) 0.35140(8) 0.40539(8) 0.0177(2) Uani 1 1 d . . . . .
N1 N 0.76107(10) 0.31344(9) 0.60817(10) 0.0142(2) Uani 1 1 d . . . . .
N1A N 0.69209(10) 0.45539(10) 0.29501(10) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.65975(11) 0.37807(10) 0.72508(10) 0.0183(3) Uani 1 1 d . . . . .
N2A N 0.82552(11) 0.58242(10) 0.28172(10) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.84962(12) 0.24254(11) 0.60585(12) 0.0143(3) Uani 1 1 d . . . . .
C1A C 0.58946(12) 0.40395(11) 0.23066(12) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.89101(12) 0.25642(11) 0.51447(12) 0.0148(3) Uani 1 1 d . . . . .
C2A C 0.53086(13) 0.35290(11) 0.29508(12) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.97916(13) 0.19414(12) 0.50157(13) 0.0196(3) Uani 1 1 d . . . . .
H3 H 1.008324 0.204421 0.440821 0.024 Uiso 1 1 calc R U . . .
C3A C 0.42389(14) 0.30666(12) 0.24324(14) 0.0231(3) Uani 1 1 d . . . . .
H3A H 0.381094 0.275857 0.286393 0.028 Uiso 1 1 calc R U . . .
C4 C 1.02498(14) 0.11649(12) 0.57767(14) 0.0233(3) Uani 1 1 d . . . . .
H4 H 1.085551 0.074143 0.568938 0.028 Uiso 1 1 calc R U . . .
C4A C 0.37955(15) 0.30556(13) 0.12791(15) 0.0291(4) Uani 1 1 d . . . . .
H4A H 0.305564 0.275485 0.092717 0.035 Uiso 1 1 calc R U . . .
C5 C 0.98213(14) 0.10123(12) 0.66580(14) 0.0234(3) Uani 1 1 d . . . . .
H5 H 1.012969 0.047826 0.717008 0.028 Uiso 1 1 calc R U . . .
C5A C 0.44261(16) 0.34796(13) 0.06451(14) 0.0279(4) Uani 1 1 d . . . . .
H5A H 0.414077 0.343255 -0.013989 0.033 Uiso 1 1 calc R U . . .
C6 C 0.89401(13) 0.16354(11) 0.68021(13) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.864411 0.152128 0.740489 0.023 Uiso 1 1 calc R U . . .
C6A C 0.54798(14) 0.39763(12) 0.11536(12) 0.0213(3) Uani 1 1 d . . . . .
H6A H 0.591221 0.426961 0.071766 0.026 Uiso 1 1 calc R U . . .
C7 C 0.74698(13) 0.32869(11) 0.70567(12) 0.0159(3) Uani 1 1 d . . . . .
H7 H 0.805138 0.301563 0.768139 0.019 Uiso 1 1 calc R U . . .
C7A C 0.72544(12) 0.53171(12) 0.24596(12) 0.0170(3) Uani 1 1 d . . . . .
H7A H 0.672385 0.553240 0.177338 0.020 Uiso 1 1 calc R U . . .
C8 C 0.66326(15) 0.40130(13) 0.83895(13) 0.0244(3) Uani 1 1 d . . . . .
H8A H 0.600331 0.364558 0.856548 0.037 Uiso 1 1 calc R U . . .
H8B H 0.653020 0.474722 0.846360 0.037 Uiso 1 1 calc R U . . .
H8C H 0.738773 0.380154 0.890136 0.037 Uiso 1 1 calc R U . . .
C8A C 0.92183(13) 0.55284(13) 0.37789(13) 0.0208(3) Uani 1 1 d . . . . .
H8AA H 0.922732 0.596483 0.440812 0.031 Uiso 1 1 calc R U . . .
H8AB H 0.995684 0.560450 0.361233 0.031 Uiso 1 1 calc R U . . .
H8AC H 0.912065 0.481645 0.396495 0.031 Uiso 1 1 calc R U . . .
C9 C 0.55363(13) 0.40848(13) 0.63849(13) 0.0216(3) Uani 1 1 d . . . . .
H9A H 0.557330 0.481355 0.623184 0.032 Uiso 1 1 calc R U . . .
H9B H 0.485530 0.395010 0.663248 0.032 Uiso 1 1 calc R U . . .
H9C H 0.546778 0.369483 0.570910 0.032 Uiso 1 1 calc R U . . .
C9A C 0.84571(15) 0.67205(14) 0.22227(15) 0.0304(4) Uani 1 1 d . . . . .
H9AA H 0.779027 0.682078 0.155436 0.046 Uiso 1 1 calc R U . . .
H9AB H 0.916831 0.662243 0.201306 0.046 Uiso 1 1 calc R U . . .
H9AC H 0.854850 0.732078 0.270116 0.046 Uiso 1 1 calc R U . . .
C10 C 0.74591(13) 0.53804(11) 0.53581(13) 0.0189(3) Uani 1 1 d . . . . .
H10A H 0.827815 0.546256 0.580606 0.028 Uiso 1 1 calc R U . . .
H10B H 0.695885 0.543305 0.583610 0.028 Uiso 1 1 calc R U . . .
H10C H 0.724786 0.591481 0.479176 0.028 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
Al1 O1 1.8000(11) . ?
Al1 O1A 1.7905(11) . ?
Al1 N1 2.1109(13) . ?
Al1 N1A 2.1604(13) . ?
Al1 C10 1.9802(16) . ?
O1 C2 1.3418(17) . ?
O1A C2A 1.3414(18) . ?
N1 C1 1.4221(18) . ?
N1 C7 1.3147(19) . ?
N1A C1A 1.4233(18) . ?
N1A C7A 1.3062(19) . ?
N2 C7 1.3199(19) . ?
N2 C8 1.4644(19) . ?
N2 C9 1.4600(19) . ?
N2A C7A 1.3275(19) . ?
N2A C8A 1.4526(19) . ?
N2A C9A 1.458(2) . ?
C1 C2 1.408(2) . ?
C1 C6 1.393(2) . ?
C1A C2A 1.404(2) . ?
C1A C6A 1.395(2) . ?
C2 C3 1.388(2) . ?
C2A C3A 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.394(2) . ?
C6 H6 0.9500 . ?
C6A H6A 0.9500 . ?
C7 H7 0.9500 . ?
C7A H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Al1 N1 82.74(5) . . ?
O1 Al1 N1A 85.97(5) . . ?
O1 Al1 C10 123.06(6) . . ?
O1A Al1 O1 116.74(5) . . ?
O1A Al1 N1 93.66(5) . . ?
O1A Al1 N1A 81.99(5) . . ?
O1A Al1 C10 120.04(6) . . ?
N1 Al1 N1A 164.53(5) . . ?
C10 Al1 N1 97.49(6) . . ?
C10 Al1 N1A 97.53(6) . . ?
C2 O1 Al1 118.45(9) . . ?
C2A O1A Al1 118.90(9) . . ?
C1 N1 Al1 107.64(9) . . ?
C7 N1 Al1 133.01(10) . . ?
C7 N1 C1 115.74(12) . . ?
C1A N1A Al1 105.89(9) . . ?
C7A N1A Al1 136.70(10) . . ?
C7A N1A C1A 115.50(12) . . ?
C7 N2 C8 120.26(13) . . ?
C7 N2 C9 123.73(13) . . ?
C9 N2 C8 115.95(12) . . ?
C7A N2A C8A 123.89(13) . . ?
C7A N2A C9A 120.42(13) . . ?
C8A N2A C9A 115.66(12) . . ?
C2 C1 N1 112.96(12) . . ?
C6 C1 N1 127.34(13) . . ?
C6 C1 C2 119.67(13) . . ?
C2A C1A N1A 113.30(12) . . ?
C6A C1A N1A 126.59(14) . . ?
C6A C1A C2A 120.06(14) . . ?
O1 C2 C1 117.98(13) . . ?
O1 C2 C3 122.14(13) . . ?
C3 C2 C1 119.88(14) . . ?
O1A C2A C1A 118.26(13) . . ?
O1A C2A C3A 122.34(14) . . ?
C3A C2A C1A 119.40(14) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.13(15) . . ?
C4 C3 H3 119.9 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 119.95(16) . . ?
C4A C3A H3A 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.93(14) . . ?
C5 C4 H4 120.0 . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A C3A 120.37(15) . . ?
C5A C4A H4A 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.61(15) . . ?
C6 C5 H5 119.7 . . ?
C4A C5A H5A 119.9 . . ?
C4A C5A C6A 120.23(15) . . ?
C6A C5A H5A 119.9 . . ?
C1 C6 C5 119.74(14) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C1A C6A H6A 120.2 . . ?
C5A C6A C1A 119.54(16) . . ?
C5A C6A H6A 120.2 . . ?
N1 C7 N2 126.25(14) . . ?
N1 C7 H7 116.9 . . ?
N2 C7 H7 116.9 . . ?
N1A C7A N2A 126.98(14) . . ?
N1A C7A H7A 116.5 . . ?
N2A C7A H7A 116.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2A C8A H8AA 109.5 . . ?
N2A C8A H8AB 109.5 . . ?
N2A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2A C9A H9AA 109.5 . . ?
N2A C9A H9AB 109.5 . . ?
N2A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
Al1 C10 H10A 109.5 . . ?
Al1 C10 H10B 109.5 . . ?
Al1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Al1 O1 C2 C1 -2.74(17) . . . . ?
Al1 O1 C2 C3 177.11(11) . . . . ?
Al1 O1A C2A C1A -6.26(18) . . . . ?
Al1 O1A C2A C3A 174.31(12) . . . . ?
Al1 N1 C1 C2 3.82(14) . . . . ?
Al1 N1 C1 C6 -174.42(13) . . . . ?
Al1 N1 C7 N2 35.7(2) . . . . ?
Al1 N1A C1A C2A 11.06(14) . . . . ?
Al1 N1A C1A C6A -166.37(13) . . . . ?
Al1 N1A C7A N2A 28.4(2) . . . . ?
O1 Al1 O1A C2A -71.49(12) . . . . ?
O1 C2 C3 C4 -178.47(14) . . . . ?
O1A Al1 O1 C2 -86.60(11) . . . . ?
O1A C2A C3A C4A -176.38(15) . . . . ?
N1 Al1 O1 C2 3.85(10) . . . . ?
N1 Al1 O1A C2A -155.20(11) . . . . ?
N1 C1 C2 O1 -1.25(18) . . . . ?
N1 C1 C2 C3 178.90(13) . . . . ?
N1 C1 C6 C5 -179.51(14) . . . . ?
N1A Al1 O1 C2 -165.54(10) . . . . ?
N1A Al1 O1A C2A 9.87(11) . . . . ?
N1A C1A C2A O1A -4.89(19) . . . . ?
N1A C1A C2A C3A 174.56(13) . . . . ?
N1A C1A C6A C5A -177.09(14) . . . . ?
C1 N1 C7 N2 -168.84(14) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C1A N1A C7A N2A -170.05(14) . . . . ?
C1A C2A C3A C4A 4.2(2) . . . . ?
C2 C1 C6 C5 2.4(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2A C1A C6A C5A 5.6(2) . . . . ?
C2A C3A C4A C5A 1.6(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3A C4A C5A C6A -3.8(3) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4A C5A C6A C1A 0.2(2) . . . . ?
C6 C1 C2 O1 177.14(13) . . . . ?
C6 C1 C2 C3 -2.7(2) . . . . ?
C6A C1A C2A O1A 172.73(13) . . . . ?
C6A C1A C2A C3A -7.8(2) . . . . ?
C7 N1 C1 C2 -157.61(13) . . . . ?
C7 N1 C1 C6 24.1(2) . . . . ?
C7A N1A C1A C2A -155.91(13) . . . . ?
C7A N1A C1A C6A 26.7(2) . . . . ?
C8 N2 C7 N1 -171.65(15) . . . . ?
C8A N2A C7A N1A 7.3(2) . . . . ?
C9 N2 C7 N1 11.3(2) . . . . ?
C9A N2A C7A N1A -174.47(16) . . . . ?
C10 Al1 O1 C2 98.09(11) . . . . ?
C10 Al1 O1A C2A 103.97(11) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_1a
_database_code_depnum_ccdc_archive 'CCDC 2182074'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H34 Al2 N4 O2'
_chemical_formula_sum            'C22 H34 Al2 N4 O2'
_chemical_formula_weight         440.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.7561(7)
_cell_length_b                   10.6856(7)
_cell_length_c                   12.8516(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.758(3)
_cell_angle_gamma                90
_cell_volume                     1185.05(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.9215.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.175
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         3.034
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2337
_reflns_number_total             2733
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.063
_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)+(0.0390P)²+0.8205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_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
Al1 Al 0.42807(5) 0.36870(4) 0.47133(3) 0.01062(12) Uani 1 1 d . . . . .
O1 O 0.40303(11) 0.50950(9) 0.55062(8) 0.0129(2) Uani 1 1 d . . . . .
N2 N 0.09960(14) 0.14954(12) 0.43313(10) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.21810(13) 0.31865(11) 0.53081(9) 0.0116(2) Uani 1 1 d . . . . .
C7 C 0.09623(16) 0.25523(13) 0.48676(11) 0.0136(3) Uani 1 1 d . . . . .
H7 H -0.002590 0.287523 0.493791 0.016 Uiso 1 1 calc R U . . .
C2 C 0.29079(16) 0.51442(13) 0.61144(10) 0.0110(3) Uani 1 1 d . . . . .
C1 C 0.18902(16) 0.41237(13) 0.60338(10) 0.0116(3) Uani 1 1 d . . . . .
C5 C 0.06273(17) 0.50506(14) 0.73774(12) 0.0173(3) Uani 1 1 d . . . . .
H5 H -0.014106 0.501589 0.781732 0.021 Uiso 1 1 calc R U . . .
C4 C 0.16096(17) 0.60752(14) 0.74268(11) 0.0159(3) Uani 1 1 d . . . . .
H4 H 0.150343 0.674430 0.789609 0.019 Uiso 1 1 calc R U . . .
C3 C 0.27528(16) 0.61302(13) 0.67920(11) 0.0139(3) Uani 1 1 d . . . . .
H3 H 0.341878 0.683595 0.682327 0.017 Uiso 1 1 calc R U . . .
C6 C 0.07669(17) 0.40715(14) 0.66826(12) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.009634 0.336856 0.665118 0.018 Uiso 1 1 calc R U . . .
C10 C 0.32956(18) 0.36476(16) 0.32127(11) 0.0202(3) Uani 1 1 d . . . . .
H10A H 0.225058 0.329578 0.315195 0.030 Uiso 1 1 calc R U . . .
H10B H 0.391571 0.312736 0.281421 0.030 Uiso 1 1 calc R U . . .
H10C H 0.323154 0.450005 0.292737 0.030 Uiso 1 1 calc R U . . .
C11 C 0.57674(17) 0.24197(15) 0.53989(13) 0.0197(3) Uani 1 1 d . . . . .
H11A H 0.673542 0.283258 0.571356 0.030 Uiso 1 1 calc R U . . .
H11B H 0.597831 0.181044 0.487122 0.030 Uiso 1 1 calc R U . . .
H11C H 0.532468 0.198852 0.595163 0.030 Uiso 1 1 calc R U . . .
C9 C 0.24285(19) 0.08355(15) 0.42664(14) 0.0245(4) Uani 1 1 d . . . . .
H9A H 0.282550 0.110922 0.363508 0.037 Uiso 1 1 calc R U . . .
H9B H 0.222936 -0.006716 0.422479 0.037 Uiso 1 1 calc R U . . .
H9C H 0.319630 0.101948 0.489571 0.037 Uiso 1 1 calc R U . . .
C8 C -0.04214(19) 0.09703(16) 0.37282(14) 0.0252(4) Uani 1 1 d . . . . .
H8A H -0.131913 0.142867 0.389448 0.038 Uiso 1 1 calc R U . . .
H8B H -0.050486 0.008614 0.391337 0.038 Uiso 1 1 calc R U . . .
H8C H -0.039213 0.104336 0.297169 0.038 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
Al1 O1 1.8509(10) . ?
Al1 O1 2.0254(11) 3_666 ?
Al1 N1 2.1742(12) . ?
Al1 C10 1.9751(15) . ?
Al1 C11 1.9789(15) . ?
O1 C2 1.3565(16) . ?
N2 C7 1.3260(18) . ?
N2 C9 1.454(2) . ?
N2 C8 1.4594(19) . ?
N1 C7 1.3091(18) . ?
N1 C1 1.4205(17) . ?
C7 H7 0.9500 . ?
C2 C1 1.4009(19) . ?
C2 C3 1.3881(19) . ?
C1 C6 1.3942(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(2) . ?
C5 C6 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.396(2) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Al1 O1 73.25(5) . 3_666 ?
O1 Al1 N1 152.62(5) 3_666 . ?
O1 Al1 N1 79.64(4) . . ?
O1 Al1 C10 118.82(6) . . ?
O1 Al1 C11 116.20(6) . . ?
C10 Al1 O1 94.94(6) . 3_666 ?
C10 Al1 N1 94.74(6) . . ?
C10 Al1 C11 124.45(7) . . ?
C11 Al1 O1 93.50(5) . 3_666 ?
C11 Al1 N1 101.93(6) . . ?
Al1 O1 Al1 106.75(5) . 3_666 ?
C2 O1 Al1 132.28(9) . 3_666 ?
C2 O1 Al1 120.92(9) . . ?
C7 N2 C9 122.57(13) . . ?
C7 N2 C8 120.78(13) . . ?
C9 N2 C8 116.58(13) . . ?
C7 N1 Al1 130.63(10) . . ?
C7 N1 C1 115.16(12) . . ?
C1 N1 Al1 108.29(9) . . ?
N2 C7 H7 117.4 . . ?
N1 C7 N2 125.27(13) . . ?
N1 C7 H7 117.4 . . ?
O1 C2 C1 116.18(12) . . ?
O1 C2 C3 123.25(12) . . ?
C3 C2 C1 120.57(13) . . ?
C2 C1 N1 114.50(12) . . ?
C6 C1 N1 125.98(13) . . ?
C6 C1 C2 119.43(13) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.04(13) . . ?
C6 C5 H5 120.0 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.47(13) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 119.40(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C1 C6 C5 120.02(13) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
Al1 C10 H10A 109.5 . . ?
Al1 C10 H10B 109.5 . . ?
Al1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Al1 C11 H11A 109.5 . . ?
Al1 C11 H11B 109.5 . . ?
Al1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Al1 O1 C2 C1 -5.15(16) . . . . ?
Al1 O1 C2 C1 177.75(9) 3_666 . . . ?
Al1 O1 C2 C3 174.33(10) . . . . ?
Al1 O1 C2 C3 -2.8(2) 3_666 . . . ?
Al1 N1 C7 N2 44.2(2) . . . . ?
Al1 N1 C1 C2 4.93(14) . . . . ?
Al1 N1 C1 C6 -171.61(12) . . . . ?
O1 Al1 O1 Al1 -0.001(1) 3_666 . . 3_666 ?
O1 Al1 O1 C2 -177.76(13) 3_666 . . . ?
O1 C2 C1 N1 -0.72(17) . . . . ?
O1 C2 C1 C6 176.07(12) . . . . ?
O1 C2 C3 C4 -176.92(13) . . . . ?
N1 Al1 O1 Al1 -176.13(6) . . . 3_666 ?
N1 Al1 O1 C2 6.12(10) . . . . ?
N1 C1 C6 C5 178.65(13) . . . . ?
C7 N1 C1 C2 -150.99(12) . . . . ?
C7 N1 C1 C6 32.5(2) . . . . ?
C2 C1 C6 C5 2.3(2) . . . . ?
C1 N1 C7 N2 -166.45(13) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C5 C4 C3 C2 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C3 C2 C1 N1 179.78(12) . . . . ?
C3 C2 C1 C6 -3.4(2) . . . . ?
C6 C5 C4 C3 -0.7(2) . . . . ?
C10 Al1 O1 Al1 -86.39(7) . . . 3_666 ?
C10 Al1 O1 C2 95.85(11) . . . . ?
C11 Al1 O1 Al1 85.58(7) . . . 3_666 ?
C11 Al1 O1 C2 -92.18(11) . . . . ?
C9 N2 C7 N1 6.9(2) . . . . ?
C8 N2 C7 N1 -169.98(14) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_4d
_database_code_depnum_ccdc_archive 'CCDC 2182085'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C36 H38 N4 O2 Zn), 0.5(C6 H14), 1.5(C H2 Cl2)'
_chemical_formula_sum            'C76.50 H86 Cl3 N8 O4 Zn2'
_chemical_formula_weight         1418.62
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2841(6)
_cell_length_b                   10.5138(8)
_cell_length_c                   19.9849(15)
_cell_angle_alpha                89.305(3)
_cell_angle_beta                 80.720(4)
_cell_angle_gamma                82.276(4)
_cell_volume                     1702.2(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.79
_cell_measurement_theta_min      4.82
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.588
_exptl_absorpt_coefficient_mu    2.399
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1178 before and 0.0638 after correction.
 
For component 2:
 wR2(int) was 0.1014 before and 0.0772 after correction.
 The Ratio of minimum to maximum transmission is 0.80.

Final HKLF 4 output contains 44641 reflections, Rint = 0.0510
 (34520 with I > 3sig(I), Rint = 0.0474)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10719
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.897
_diffrn_reflns_theta_max         66.897
_diffrn_reflns_theta_min         4.781
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9531
_reflns_number_total             10719
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.895
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         10719
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.080
_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)+(0.0631P)²+3.7441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1636
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8060(9)
 0.1940(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.004 within 1.7A
Cl1 \\sim Cl2 \\sim C12: within 1.7A with sigma of 0.004 and sigma for terminal
atoms of 0.004 within 1.7A
4. Others
 Fixed Sof: Cl1(0.75) Cl2(0.75) C12(0.75) H12A(0.75) H12B(0.75) C18(0.25)
 H18A(0.25) H18B(0.25) H18C(0.25) C13(0.25) H13A(0.25) H13B(0.25) H13C(0.25)
 C14(0.25) H14A(0.25) H14B(0.25) C15(0.25) H15A(0.25) H15B(0.25) C16(0.25)
 H16A(0.25) H16B(0.25) C17(0.25) H17A(0.25) H17B(0.25)
5.a Free rotating group:
 C18(C13,C14,C15,C16,C17)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,H9B), C9A(H9AA,H9AB), C10(H10A,H10B),
 C10A(H10C,H10D), C11(H11A,H11B), C11A(H11C,H11D), C12(H12A,H12B), C14(H14A,
 H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C3'A(H3'A), C3A(H3A), C4(H4), C4'(H4'), C4'A(H4'A),
 C4A(H4A), C5(H5), C5'(H5'), C5'A(H5'A), C5A(H5A), C6(H6), C6'(H6'), C6'A(H6'A),
  C6A(H6A)
5.d Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C7'A(H7'D,H7'E,H7'F), C18(H18A,H18B,H18C), C13(H13A,H13B,
 H13C)
;
_atom_sites_solution_hydrogens   geom
_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
Zn1 Zn 0.48635(6) 0.38429(5) 0.28155(3) 0.01599(17) Uani 1 1 d . . . . .
O1 O 0.5242(4) 0.2591(3) 0.35020(15) 0.0236(7) Uani 1 1 d . . . . .
O1A O 0.6295(4) 0.3777(3) 0.19513(14) 0.0206(6) Uani 1 1 d . . . . .
N1 N 0.2594(4) 0.3245(3) 0.28609(16) 0.0152(7) Uani 1 1 d . . . . .
N1A N 0.5240(4) 0.5720(3) 0.28654(16) 0.0151(7) Uani 1 1 d . . . . .
N2 N 0.1794(4) 0.3968(3) 0.18586(16) 0.0156(7) Uani 1 1 d . . . . .
N2A N 0.4319(4) 0.6295(3) 0.39886(16) 0.0183(7) Uani 1 1 d . . . . .
C1 C 0.2410(5) 0.2421(4) 0.34304(19) 0.0170(8) Uani 1 1 d . . . . .
C1' C 0.1331(5) 0.1816(4) 0.21631(18) 0.0161(8) Uani 1 1 d . . . . .
C1'A C 0.6580(5) 0.7312(4) 0.34199(18) 0.0151(8) Uani 1 1 d . . . . .
C1A C 0.6043(5) 0.6018(4) 0.22015(19) 0.0160(8) Uani 1 1 d . . . . .
C2 C 0.3843(5) 0.2133(4) 0.3749(2) 0.0205(9) Uani 1 1 d . . . . .
C2' C 0.2509(5) 0.0747(4) 0.19852(19) 0.0181(8) Uani 1 1 d . . . . .
C2'A C 0.8238(5) 0.6788(4) 0.33728(19) 0.0192(8) Uani 1 1 d . . . . .
C2A C 0.6515(5) 0.4957(4) 0.1744(2) 0.0168(8) Uani 1 1 d . . . . .
C3 C 0.3716(6) 0.1375(4) 0.4330(2) 0.0246(9) Uani 1 1 d . . . . .
H3 H 0.466152 0.114399 0.454048 0.030 Uiso 1 1 calc R U . . .
C3' C 0.1945(6) -0.0371(4) 0.1801(2) 0.0259(10) Uani 1 1 d . . . . .
H3' H 0.271774 -0.111521 0.167642 0.031 Uiso 1 1 calc R U . . .
C3'A C 0.9399(6) 0.7624(4) 0.3384(2) 0.0248(9) Uani 1 1 d . . . . .
H3'A H 1.053053 0.728519 0.335568 0.030 Uiso 1 1 calc R U . . .
C3A C 0.7161(5) 0.5200(4) 0.1071(2) 0.0203(9) Uani 1 1 d . . . . .
H3A H 0.748962 0.450302 0.075967 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2232(6) 0.0953(4) 0.4604(2) 0.0289(10) Uani 1 1 d . . . . .
H4 H 0.217322 0.043753 0.499898 0.035 Uiso 1 1 calc R U . . .
C4' C 0.0281(6) -0.0422(4) 0.1796(2) 0.0269(10) Uani 1 1 d . . . . .
H4' H -0.007356 -0.119877 0.167576 0.032 Uiso 1 1 calc R U . . .
C4'A C 0.8945(6) 0.8924(5) 0.3434(2) 0.0300(11) Uani 1 1 d . . . . .
H4'A H 0.976873 0.947259 0.343228 0.036 Uiso 1 1 calc R U . . .
C4A C 0.7329(5) 0.6424(4) 0.0851(2) 0.0211(9) Uani 1 1 d . . . . .
H4A H 0.778814 0.656213 0.039346 0.025 Uiso 1 1 calc R U . . .
C5 C 0.0838(6) 0.1281(4) 0.4306(2) 0.0272(10) Uani 1 1 d . . . . .
H5 H -0.017939 0.100487 0.450059 0.033 Uiso 1 1 calc R U . . .
C5' C -0.0860(6) 0.0653(4) 0.1965(2) 0.0234(9) Uani 1 1 d . . . . .
H5' H -0.199752 0.062144 0.195676 0.028 Uiso 1 1 calc R U . . .
C5'A C 0.7313(7) 0.9451(4) 0.3487(2) 0.0306(11) Uani 1 1 d . . . . .
H5'A H 0.700753 1.035396 0.352417 0.037 Uiso 1 1 calc R U . . .
C5A C 0.6832(5) 0.7464(4) 0.1296(2) 0.0213(9) Uani 1 1 d . . . . .
H5A H 0.693995 0.831131 0.114252 0.026 Uiso 1 1 calc R U . . .
C6 C 0.0930(5) 0.2014(4) 0.3720(2) 0.0212(9) Uani 1 1 d . . . . .
H6 H -0.002857 0.223823 0.351651 0.025 Uiso 1 1 calc R U . . .
C6' C -0.0340(5) 0.1779(4) 0.2147(2) 0.0192(8) Uani 1 1 d . . . . .
H6' H -0.111903 0.252361 0.226156 0.023 Uiso 1 1 calc R U . . .
C6'A C 0.6109(6) 0.8632(4) 0.3485(2) 0.0217(9) Uani 1 1 d . . . . .
H6'A H 0.497616 0.897684 0.352780 0.026 Uiso 1 1 calc R U . . .
C6A C 0.6178(5) 0.7251(4) 0.1964(2) 0.0191(8) Uani 1 1 d . . . . .
H6A H 0.581560 0.796121 0.226517 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1919(5) 0.3053(4) 0.23198(18) 0.0140(8) Uani 1 1 d . . . . .
C7' C 0.4312(5) 0.0788(4) 0.1981(2) 0.0256(9) Uani 1 1 d . . . . .
H7'A H 0.462730 0.157431 0.175953 0.038 Uiso 1 1 calc R U . . .
H7'B H 0.495428 0.003922 0.173256 0.038 Uiso 1 1 calc R U . . .
H7'C H 0.453350 0.077574 0.244837 0.038 Uiso 1 1 calc R U . . .
C7'A C 0.8750(5) 0.5336(4) 0.3298(2) 0.0265(10) Uani 1 1 d . . . . .
H7'D H 0.792447 0.489001 0.358011 0.040 Uiso 1 1 calc R U . . .
H7'E H 0.982508 0.510600 0.344330 0.040 Uiso 1 1 calc R U . . .
H7'F H 0.882725 0.508189 0.282237 0.040 Uiso 1 1 calc R U . . .
C7A C 0.5325(5) 0.6415(4) 0.34050(19) 0.0144(8) Uani 1 1 d . . . . .
C8 C 0.2197(5) 0.5267(4) 0.1944(2) 0.0196(8) Uani 1 1 d . . . . .
H8A H 0.340566 0.527429 0.188052 0.023 Uiso 1 1 calc R U . . .
H8B H 0.169819 0.562505 0.239785 0.023 Uiso 1 1 calc R U . . .
C8A C 0.2983(5) 0.5486(4) 0.4079(2) 0.0227(9) Uani 1 1 d . . . . .
H8AA H 0.342640 0.456811 0.410695 0.027 Uiso 1 1 calc R U . . .
H8AB H 0.233861 0.560003 0.370096 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1349(5) 0.3792(4) 0.11805(19) 0.0196(9) Uani 1 1 d . . . . .
H9A H 0.016650 0.369572 0.121496 0.024 Uiso 1 1 calc R U . . .
H9B H 0.202374 0.303063 0.094445 0.024 Uiso 1 1 calc R U . . .
C9A C 0.4384(5) 0.6978(4) 0.4629(2) 0.0220(9) Uani 1 1 d . . . . .
H9AA H 0.402121 0.790991 0.459402 0.026 Uiso 1 1 calc R U . . .
H9AB H 0.551368 0.684970 0.474288 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1725(5) 0.5016(4) 0.0816(2) 0.0217(9) Uani 1 1 d . . . . .
H10A H 0.097383 0.525208 0.048334 0.026 Uiso 1 1 calc R U . . .
H10B H 0.288076 0.492546 0.057912 0.026 Uiso 1 1 calc R U . . .
C10A C 0.3187(5) 0.6358(5) 0.5156(2) 0.0247(9) Uani 1 1 d . . . . .
H10C H 0.376017 0.560066 0.536030 0.030 Uiso 1 1 calc R U . . .
H10D H 0.265041 0.697721 0.551975 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1439(6) 0.6008(4) 0.1388(2) 0.0221(9) Uani 1 1 d . . . . .
H11A H 0.200314 0.676428 0.124982 0.027 Uiso 1 1 calc R U . . .
H11B H 0.024730 0.629319 0.153418 0.027 Uiso 1 1 calc R U . . .
C11A C 0.1930(5) 0.5967(5) 0.4744(2) 0.0277(10) Uani 1 1 d . . . . .
H11C H 0.134641 0.527962 0.497346 0.033 Uiso 1 1 calc R U . . .
H11D H 0.110925 0.670901 0.467071 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.9395(3) 0.1911(2) 0.00751(10) 0.0514(5) Uani 0.75 1 d . . P A 1
Cl2 Cl 0.5833(3) 0.2184(3) 0.00862(12) 0.0647(6) Uani 0.75 1 d . . P A 1
C12 C 0.7497(11) 0.1684(9) 0.0508(5) 0.057(2) Uani 0.75 1 d . . P A 1
H12A H 0.731622 0.215170 0.094609 0.068 Uiso 0.75 1 calc R U P A 1
H12B H 0.750839 0.075909 0.060910 0.068 Uiso 0.75 1 calc R U P A 1
C18 C 1.3298(15) -0.0705(19) -0.0083(11) 0.054(5) Uiso 0.25 1 d G U P B -2
H18A H 1.370997 -0.114955 0.030228 0.081 Uiso 0.25 1 calc R U P B -2
H18B H 1.337609 0.021323 -0.005143 0.081 Uiso 0.25 1 calc R U P B -2
H18C H 1.396211 -0.105718 -0.050693 0.081 Uiso 0.25 1 calc R U P B -2
C13 C 0.5472(17) 0.124(3) 0.0179(15) 0.101(7) Uiso 0.25 1 d G U P B -2
H13A H 0.524440 0.046020 0.043479 0.151 Uiso 0.25 1 calc R U P B -2
H13B H 0.526822 0.114241 -0.028628 0.151 Uiso 0.25 1 calc R U P B -2
H13C H 0.474718 0.198060 0.039635 0.151 Uiso 0.25 1 calc R U P B -2
C14 C 0.7278(19) 0.1427(19) 0.0168(14) 0.092(6) Uiso 0.25 1 d G U P B -2
H14A H 0.738407 0.181942 0.060372 0.111 Uiso 0.25 1 calc R U P B -2
H14B H 0.759331 0.203342 -0.019758 0.111 Uiso 0.25 1 calc R U P B -2
C15 C 0.8478(15) 0.0175(15) 0.0055(10) 0.078(5) Uiso 0.25 1 d G U P B -2
H15A H 0.816087 -0.043124 0.041996 0.094 Uiso 0.25 1 calc R U P B -2
H15B H 0.836936 -0.021766 -0.038108 0.094 Uiso 0.25 1 calc R U P B -2
C16 C 1.0291(15) 0.0356(11) 0.0042(9) 0.062(5) Uiso 0.25 1 d G U P B -2
H16A H 1.039972 0.074826 0.047745 0.075 Uiso 0.25 1 calc R U P B -2
H16B H 1.060838 0.096136 -0.032365 0.075 Uiso 0.25 1 calc R U P B -2
C17 C 1.1490(16) -0.0897(12) -0.0071(11) 0.048(4) Uiso 0.25 1 d G U P B -2
H17A H 1.117495 -0.150306 0.029442 0.058 Uiso 0.25 1 calc R U P B -2
H17B H 1.138376 -0.128984 -0.050694 0.058 Uiso 0.25 1 calc R U P B -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.923(3) . ?
Zn1 O1A 1.927(3) . ?
Zn1 N1 2.049(3) . ?
Zn1 N1A 2.045(3) . ?
O1 C2 1.334(5) . ?
O1A C2A 1.329(5) . ?
N1 C1 1.423(5) . ?
N1 C7 1.324(5) . ?
N1A C1A 1.436(5) . ?
N1A C7A 1.326(5) . ?
N2 C7 1.330(5) . ?
N2 C8 1.467(5) . ?
N2 C9 1.480(5) . ?
N2A C7A 1.335(5) . ?
N2A C8A 1.472(5) . ?
N2A C9A 1.487(5) . ?
C1 C2 1.431(6) . ?
C1 C6 1.388(6) . ?
C1' C2' 1.395(6) . ?
C1' C6' 1.396(6) . ?
C1' C7 1.501(5) . ?
C1'A C2'A 1.398(6) . ?
C1'A C6'A 1.392(6) . ?
C1'A C7A 1.498(5) . ?
C1A C2A 1.424(5) . ?
C1A C6A 1.387(6) . ?
C2 C3 1.398(6) . ?
C2' C3' 1.396(6) . ?
C2' C7' 1.499(6) . ?
C2'A C3'A 1.390(6) . ?
C2'A C7'A 1.531(6) . ?
C2A C3A 1.398(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(7) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.388(6) . ?
C3'A H3'A 0.9500 . ?
C3'A C4'A 1.369(7) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.372(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(7) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.380(7) . ?
C4'A H4'A 0.9500 . ?
C4'A C5'A 1.379(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.393(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(6) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.384(6) . ?
C5'A H5'A 0.9500 . ?
C5'A C6'A 1.403(6) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.385(6) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C6'A H6'A 0.9500 . ?
C6A H6A 0.9500 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C7'A H7'D 0.9800 . ?
C7'A H7'E 0.9800 . ?
C7'A H7'F 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C11 1.519(6) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C11A 1.519(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(6) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.530(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(6) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
Cl1 C12 1.712(10) . ?
Cl2 C12 1.748(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C17 1.5341 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.5333 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5348 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5348 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5349 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
O1 Zn1 O1A 121.16(13) . . ?
O1 Zn1 N1 86.44(13) . . ?
O1 Zn1 N1A 124.54(12) . . ?
O1A Zn1 N1 118.27(12) . . ?
O1A Zn1 N1A 86.17(12) . . ?
N1A Zn1 N1 124.41(13) . . ?
C2 O1 Zn1 110.2(2) . . ?
C2A O1A Zn1 110.2(2) . . ?
C1 N1 Zn1 106.1(2) . . ?
C7 N1 Zn1 123.7(3) . . ?
C7 N1 C1 120.9(3) . . ?
C1A N1A Zn1 105.7(2) . . ?
C7A N1A Zn1 128.9(3) . . ?
C7A N1A C1A 121.5(3) . . ?
C7 N2 C8 123.6(3) . . ?
C7 N2 C9 124.9(3) . . ?
C8 N2 C9 111.3(3) . . ?
C7A N2A C8A 124.4(3) . . ?
C7A N2A C9A 124.4(3) . . ?
C8A N2A C9A 111.2(3) . . ?
N1 C1 C2 115.1(3) . . ?
C6 C1 N1 124.4(4) . . ?
C6 C1 C2 120.1(4) . . ?
C2' C1' C6' 121.5(4) . . ?
C2' C1' C7 118.2(3) . . ?
C6' C1' C7 120.1(4) . . ?
C2'A C1'A C7A 118.2(3) . . ?
C6'A C1'A C2'A 120.8(4) . . ?
C6'A C1'A C7A 121.0(4) . . ?
C2A C1A N1A 115.3(3) . . ?
C6A C1A N1A 124.7(4) . . ?
C6A C1A C2A 119.5(4) . . ?
O1 C2 C1 120.8(4) . . ?
O1 C2 C3 121.4(4) . . ?
C3 C2 C1 117.8(4) . . ?
C1' C2' C3' 117.3(4) . . ?
C1' C2' C7' 121.9(4) . . ?
C3' C2' C7' 120.8(4) . . ?
C1'A C2'A C7'A 120.6(4) . . ?
C3'A C2'A C1'A 118.1(4) . . ?
C3'A C2'A C7'A 121.4(4) . . ?
O1A C2A C1A 120.4(3) . . ?
O1A C2A C3A 121.5(4) . . ?
C3A C2A C1A 118.1(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2' C3' H3' 119.2 . . ?
C4' C3' C2' 121.6(4) . . ?
C4' C3' H3' 119.2 . . ?
C2'A C3'A H3'A 119.3 . . ?
C4'A C3'A C2'A 121.4(4) . . ?
C4'A C3'A H3'A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A C2A 121.5(4) . . ?
C4A C3A H3A 119.3 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3' C4' H4' 119.9 . . ?
C5' C4' C3' 120.1(4) . . ?
C5' C4' H4' 119.9 . . ?
C3'A C4'A H4'A 119.5 . . ?
C3'A C4'A C5'A 121.0(4) . . ?
C5'A C4'A H4'A 119.5 . . ?
C3A C4A H4A 119.8 . . ?
C3A C4A C5A 120.3(4) . . ?
C5A C4A H4A 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(4) . . ?
C6 C5 H5 120.1 . . ?
C4' C5' H5' 120.1 . . ?
C4' C5' C6' 119.7(4) . . ?
C6' C5' H5' 120.1 . . ?
C4'A C5'A H5'A 120.5 . . ?
C4'A C5'A C6'A 119.0(4) . . ?
C6'A C5'A H5'A 120.5 . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A C4A 119.4(4) . . ?
C6A C5A H5A 120.3 . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C1' C6' H6' 120.1 . . ?
C5' C6' C1' 119.8(4) . . ?
C5' C6' H6' 120.1 . . ?
C1'A C6'A C5'A 119.7(4) . . ?
C1'A C6'A H6'A 120.1 . . ?
C5'A C6'A H6'A 120.1 . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A C1A 121.2(4) . . ?
C5A C6A H6A 119.4 . . ?
N1 C7 N2 120.0(3) . . ?
N1 C7 C1' 124.1(3) . . ?
N2 C7 C1' 115.8(3) . . ?
C2' C7' H7'A 109.5 . . ?
C2' C7' H7'B 109.5 . . ?
C2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C2'A C7'A H7'D 109.5 . . ?
C2'A C7'A H7'E 109.5 . . ?
C2'A C7'A H7'F 109.5 . . ?
H7'D C7'A H7'E 109.5 . . ?
H7'D C7'A H7'F 109.5 . . ?
H7'E C7'A H7'F 109.5 . . ?
N1A C7A N2A 120.6(3) . . ?
N1A C7A C1'A 123.6(3) . . ?
N2A C7A C1'A 115.7(3) . . ?
N2 C8 H8A 111.2 . . ?
N2 C8 H8B 111.2 . . ?
N2 C8 C11 102.7(3) . . ?
H8A C8 H8B 109.1 . . ?
C11 C8 H8A 111.2 . . ?
C11 C8 H8B 111.2 . . ?
N2A C8A H8AA 111.0 . . ?
N2A C8A H8AB 111.0 . . ?
N2A C8A C11A 103.6(3) . . ?
H8AA C8A H8AB 109.0 . . ?
C11A C8A H8AA 111.0 . . ?
C11A C8A H8AB 111.0 . . ?
N2 C9 H9A 111.1 . . ?
N2 C9 H9B 111.1 . . ?
N2 C9 C10 103.4(3) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
N2A C9A H9AA 111.1 . . ?
N2A C9A H9AB 111.1 . . ?
N2A C9A C10A 103.4(3) . . ?
H9AA C9A H9AB 109.0 . . ?
C10A C9A H9AA 111.1 . . ?
C10A C9A H9AB 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C9 C10 C11 103.3(3) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9A C10A H10C 111.1 . . ?
C9A C10A H10D 111.1 . . ?
H10C C10A H10D 109.1 . . ?
C11A C10A C9A 103.3(3) . . ?
C11A C10A H10C 111.1 . . ?
C11A C10A H10D 111.1 . . ?
C8 C11 C10 102.4(3) . . ?
C8 C11 H11A 111.3 . . ?
C8 C11 H11B 111.3 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C8A C11A C10A 103.4(3) . . ?
C8A C11A H11C 111.1 . . ?
C8A C11A H11D 111.1 . . ?
C10A C11A H11C 111.1 . . ?
C10A C11A H11D 111.1 . . ?
H11C C11A H11D 109.1 . . ?
Cl1 C12 Cl2 115.2(6) . . ?
Cl1 C12 H12A 108.5 . . ?
Cl1 C12 H12B 108.5 . . ?
Cl2 C12 H12A 108.5 . . ?
Cl2 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.3 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.7 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C17 C16 113.3 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 C1 10.0(5) . . . . ?
Zn1 O1 C2 C3 -169.1(3) . . . . ?
Zn1 O1A C2A C1A 13.5(4) . . . . ?
Zn1 O1A C2A C3A -164.4(3) . . . . ?
Zn1 N1 C1 C2 -6.6(4) . . . . ?
Zn1 N1 C1 C6 166.6(3) . . . . ?
Zn1 N1 C7 N2 -52.3(5) . . . . ?
Zn1 N1 C7 C1' 124.6(3) . . . . ?
Zn1 N1A C1A C2A -7.2(4) . . . . ?
Zn1 N1A C1A C6A 164.1(3) . . . . ?
Zn1 N1A C7A N2A -39.2(5) . . . . ?
Zn1 N1A C7A C1'A 137.3(3) . . . . ?
O1 C2 C3 C4 176.8(4) . . . . ?
O1A C2A C3A C4A 177.5(4) . . . . ?
N1 C1 C2 O1 -1.9(5) . . . . ?
N1 C1 C2 C3 177.2(4) . . . . ?
N1 C1 C6 C5 -175.5(4) . . . . ?
N1A C1A C2A O1A -3.8(5) . . . . ?
N1A C1A C2A C3A 174.1(3) . . . . ?
N1A C1A C6A C5A -173.8(4) . . . . ?
N2 C8 C11 C10 -35.9(4) . . . . ?
N2 C9 C10 C11 -29.7(4) . . . . ?
N2A C8A C11A C10A -33.1(5) . . . . ?
N2A C9A C10A C11A -29.8(4) . . . . ?
C1 N1 C7 N2 165.6(3) . . . . ?
C1 N1 C7 C1' -17.5(6) . . . . ?
C1 C2 C3 C4 -2.3(6) . . . . ?
C1' C2' C3' C4' -0.1(6) . . . . ?
C1'A C2'A C3'A C4'A -0.5(6) . . . . ?
C1A N1A C7A N2A 166.5(4) . . . . ?
C1A N1A C7A C1'A -17.1(6) . . . . ?
C1A C2A C3A C4A -0.4(6) . . . . ?
C2 C1 C6 C5 -2.6(6) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C2' C1' C6' C5' 1.3(6) . . . . ?
C2' C1' C7 N1 -68.7(5) . . . . ?
C2' C1' C7 N2 108.3(4) . . . . ?
C2' C3' C4' C5' 1.0(7) . . . . ?
C2'A C1'A C6'A C5'A 1.6(6) . . . . ?
C2'A C1'A C7A N1A -66.9(5) . . . . ?
C2'A C1'A C7A N2A 109.7(4) . . . . ?
C2'A C3'A C4'A C5'A 1.1(6) . . . . ?
C2A C1A C6A C5A -2.8(6) . . . . ?
C2A C3A C4A C5A -1.0(6) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C3' C4' C5' C6' -0.7(7) . . . . ?
C3'A C4'A C5'A C6'A -0.4(6) . . . . ?
C3A C4A C5A C6A 0.6(6) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C4' C5' C6' C1' -0.4(6) . . . . ?
C4'A C5'A C6'A C1'A -0.9(6) . . . . ?
C4A C5A C6A C1A 1.4(6) . . . . ?
C6 C1 C2 O1 -175.5(4) . . . . ?
C6 C1 C2 C3 3.7(6) . . . . ?
C6' C1' C2' C3' -1.0(6) . . . . ?
C6' C1' C2' C7' 178.2(4) . . . . ?
C6' C1' C7 N1 116.1(4) . . . . ?
C6' C1' C7 N2 -66.9(5) . . . . ?
C6'A C1'A C2'A C3'A -0.8(6) . . . . ?
C6'A C1'A C2'A C7'A -179.7(4) . . . . ?
C6'A C1'A C7A N1A 113.6(4) . . . . ?
C6'A C1'A C7A N2A -69.7(5) . . . . ?
C6A C1A C2A O1A -175.6(4) . . . . ?
C6A C1A C2A C3A 2.3(6) . . . . ?
C7 N1 C1 C2 141.3(4) . . . . ?
C7 N1 C1 C6 -45.5(6) . . . . ?
C7 N2 C8 C11 -165.8(4) . . . . ?
C7 N2 C9 C10 -168.8(4) . . . . ?
C7 C1' C2' C3' -176.2(4) . . . . ?
C7 C1' C2' C7' 3.1(6) . . . . ?
C7 C1' C6' C5' 176.4(4) . . . . ?
C7' C2' C3' C4' -179.4(4) . . . . ?
C7'A C2'A C3'A C4'A 178.4(4) . . . . ?
C7A N1A C1A C2A 152.3(4) . . . . ?
C7A N1A C1A C6A -36.4(6) . . . . ?
C7A N2A C8A C11A -164.2(4) . . . . ?
C7A N2A C9A C10A -171.5(4) . . . . ?
C7A C1'A C2'A C3'A 179.7(3) . . . . ?
C7A C1'A C2'A C7'A 0.9(5) . . . . ?
C7A C1'A C6'A C5'A -179.0(4) . . . . ?
C8 N2 C7 N1 -7.2(6) . . . . ?
C8 N2 C7 C1' 175.6(3) . . . . ?
C8 N2 C9 C10 7.3(4) . . . . ?
C8A N2A C7A N1A -4.6(6) . . . . ?
C8A N2A C7A C1'A 178.7(4) . . . . ?
C8A N2A C9A C10A 9.5(5) . . . . ?
C9 N2 C7 N1 168.4(4) . . . . ?
C9 N2 C7 C1' -8.8(5) . . . . ?
C9 N2 C8 C11 18.1(4) . . . . ?
C9 C10 C11 C8 41.1(4) . . . . ?
C9A N2A C7A N1A 176.5(4) . . . . ?
C9A N2A C7A C1'A -0.2(6) . . . . ?
C9A N2A C8A C11A 14.7(5) . . . . ?
C9A C10A C11A C8A 39.2(5) . . . . ?
C13 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 180.0 . . . . ?
C15 C16 C17 C18 180.0 . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8060(9)
2 0.1940(9)
####################################################################### 
# 
# 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_compound_2d
_database_code_depnum_ccdc_archive 'CCDC 2182083'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 N4 O2 Zn, C5 H5 N'
_chemical_formula_sum            'C27 H31 N5 O2 Zn'
_chemical_formula_weight         522.94
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.7763(3)
_cell_length_b                   11.2517(3)
_cell_length_c                   12.6240(3)
_cell_angle_alpha                93.987(2)
_cell_angle_beta                 111.8620(10)
_cell_angle_gamma                115.4340(10)
_cell_volume                     1233.90(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  0.6202
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0401 before and 0.0347 after correction.
The Ratio of minimum to maximum transmission is 0.9273.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of cyclohexane and pyridine  by slow evaporation'
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.266
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32448
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5056
_reflns_number_total             5666
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0228P)²+0.8277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0593
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C9A(H9AA,H9AB), C11(H11A,H11B),
 C8A(H8AA,H8AB), C11A(H11C,H11D), C10A(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C7A(H7A), C7(H7), C4(H4), C5(H5), C3(H3), C5A(H5A),
 C6(H6), C14(H), C6A(H6A), C13(HA), C15(HB), C12(HC), C16(HD)
;
_atom_sites_solution_hydrogens   geom
_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
Zn1 Zn 0.76055(2) 0.25238(2) 0.50792(2) 0.01305(5) Uani 1 1 d . . . . .
O1 O 0.88347(11) 0.34436(10) 0.67627(8) 0.0172(2) Uani 1 1 d . . . . .
O1A O 0.78788(11) 0.10884(10) 0.44252(9) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.35988(12) 0.07588(12) 0.35547(10) 0.0138(2) Uani 1 1 d . . . . .
N2A N 0.81106(13) 0.55012(12) 0.42359(10) 0.0140(2) Uani 1 1 d . . . . .
N1A N 0.81438(12) 0.34528(11) 0.38926(10) 0.0126(2) Uani 1 1 d . . . . .
N1 N 0.57558(13) 0.18784(11) 0.53967(9) 0.0124(2) Uani 1 1 d . . . . .
C3A C 0.83390(16) 0.04198(14) 0.28440(13) 0.0174(3) Uani 1 1 d . . . . .
H3A H 0.822616 -0.040444 0.304968 0.021 Uiso 1 1 calc R U . . .
C4A C 0.86485(16) 0.06754(15) 0.18882(13) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.872777 0.002301 0.143705 0.023 Uiso 1 1 calc R U . . .
C1A C 0.83701(15) 0.25783(14) 0.31945(11) 0.0134(3) Uani 1 1 d . . . . .
C2A C 0.81883(15) 0.13491(14) 0.35148(11) 0.0139(3) Uani 1 1 d . . . . .
C2 C 0.79361(15) 0.31384(13) 0.73060(12) 0.0136(3) Uani 1 1 d . . . . .
C7A C 0.83637(14) 0.46385(14) 0.37019(11) 0.0132(3) Uani 1 1 d . . . . .
H7A H 0.873513 0.490028 0.313416 0.016 Uiso 1 1 calc R U . . .
C1 C 0.63193(15) 0.22832(13) 0.66568(11) 0.0121(2) Uani 1 1 d . . . . .
N3 N 0.48045(19) 0.41085(17) 0.17195(15) 0.0463(4) Uani 1 1 d . . . . .
C7 C 0.42728(15) 0.11179(13) 0.47263(12) 0.0131(3) Uani 1 1 d . . . . .
H7 H 0.363462 0.080120 0.511328 0.016 Uiso 1 1 calc R U . . .
C8 C 0.43817(16) 0.11588(15) 0.27996(12) 0.0182(3) Uani 1 1 d . . . . .
H8A H 0.515958 0.086063 0.296324 0.022 Uiso 1 1 calc R U . . .
H8B H 0.488806 0.216208 0.292133 0.022 Uiso 1 1 calc R U . . .
C9 C 0.19123(15) -0.00446(15) 0.28512(12) 0.0178(3) Uani 1 1 d . . . . .
H9A H 0.138840 0.025524 0.321583 0.021 Uiso 1 1 calc R U . . .
H9B H 0.153531 -0.103485 0.276608 0.021 Uiso 1 1 calc R U . . .
C4 C 0.76409(18) 0.32551(15) 0.91205(12) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.808813 0.360636 0.995680 0.024 Uiso 1 1 calc R U . . .
C10 C 0.16729(17) 0.02752(16) 0.16627(13) 0.0229(3) Uani 1 1 d . . . . .
H10A H 0.163156 0.113761 0.166743 0.027 Uiso 1 1 calc R U . . .
H10B H 0.071521 -0.047591 0.100891 0.027 Uiso 1 1 calc R U . . .
C5 C 0.60748(18) 0.23727(15) 0.84878(13) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.545266 0.209215 0.889081 0.025 Uiso 1 1 calc R U . . .
C3 C 0.85571(16) 0.36273(15) 0.85389(12) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.963055 0.422743 0.898582 0.022 Uiso 1 1 calc R U . . .
C5A C 0.88427(18) 0.18843(16) 0.15898(13) 0.0231(3) Uani 1 1 d . . . . .
H5A H 0.907003 0.206802 0.094127 0.028 Uiso 1 1 calc R U . . .
C6 C 0.54190(16) 0.19004(14) 0.72604(12) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.434210 0.130835 0.682611 0.020 Uiso 1 1 calc R U . . .
C9A C 0.82707(17) 0.67716(14) 0.39001(13) 0.0185(3) Uani 1 1 d . . . . .
H9AA H 0.783131 0.660779 0.302745 0.022 Uiso 1 1 calc R U . . .
H9AB H 0.936166 0.749549 0.426185 0.022 Uiso 1 1 calc R U . . .
C11 C 0.30785(17) 0.04120(17) 0.15427(13) 0.0249(3) Uani 1 1 d . . . . .
H11A H 0.327468 0.095084 0.097924 0.030 Uiso 1 1 calc R U . . .
H11B H 0.294894 -0.049787 0.126724 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2267(2) 0.31694(17) -0.04680(16) 0.0317(4) Uani 1 1 d . . . . .
H H 0.139990 0.284958 -0.121676 0.038 Uiso 1 1 calc R U . . .
C8A C 0.74565(18) 0.52494(15) 0.50808(13) 0.0201(3) Uani 1 1 d . . . . .
H8AA H 0.807928 0.504498 0.576646 0.024 Uiso 1 1 calc R U . . .
H8AB H 0.638843 0.447903 0.469683 0.024 Uiso 1 1 calc R U . . .
C6A C 0.87039(18) 0.28267(16) 0.22419(13) 0.0208(3) Uani 1 1 d . . . . .
H6A H 0.883910 0.365398 0.203394 0.025 Uiso 1 1 calc R U . . .
C11A C 0.75087(19) 0.65970(16) 0.54651(15) 0.0258(3) Uani 1 1 d . . . . .
H11C H 0.664716 0.643643 0.565520 0.031 Uiso 1 1 calc R U . . .
H11D H 0.848956 0.723329 0.616787 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2239(2) 0.36546(18) 0.05455(16) 0.0335(4) Uani 1 1 d . . . . .
HA H 0.135075 0.366788 0.051462 0.040 Uiso 1 1 calc R U . . .
C10A C 0.7366(2) 0.71593(17) 0.43928(15) 0.0271(3) Uani 1 1 d . . . . .
H10C H 0.780930 0.816489 0.462797 0.032 Uiso 1 1 calc R U . . .
H10D H 0.627814 0.673969 0.379986 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3569(2) 0.31521(19) -0.03854(18) 0.0374(4) Uani 1 1 d . . . . .
HB H 0.362006 0.282375 -0.107336 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3533(2) 0.41229(19) 0.16111(17) 0.0406(5) Uani 1 1 d . . . . .
HC H 0.351620 0.447634 0.230840 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4795(2) 0.3623(2) 0.0720(2) 0.0433(5) Uani 1 1 d . . . . .
HD H 0.568772 0.360039 0.077409 0.052 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 O1 1.9397(10) . ?
Zn1 O1A 1.9446(10) . ?
Zn1 N1A 2.0043(11) . ?
Zn1 N1 2.0133(11) . ?
O1 C2 1.3296(16) . ?
O1A C2A 1.3290(16) . ?
N2 C7 1.3203(17) . ?
N2 C8 1.4681(18) . ?
N2 C9 1.4778(17) . ?
N2A C7A 1.3207(17) . ?
N2A C9A 1.4763(17) . ?
N2A C8A 1.4647(18) . ?
N1A C1A 1.4319(17) . ?
N1A C7A 1.3074(17) . ?
N1 C1 1.4314(16) . ?
N1 C7 1.3114(17) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.384(2) . ?
C3A C2A 1.4007(19) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.386(2) . ?
C1A C2A 1.4209(19) . ?
C1A C6A 1.3914(19) . ?
C2 C1 1.4213(19) . ?
C2 C3 1.4007(18) . ?
C7A H7A 0.9500 . ?
C1 C6 1.3944(19) . ?
N3 C12 1.333(3) . ?
N3 C16 1.334(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C11 1.5289(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.521(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C4 C3 1.384(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3893(19) . ?
C3 H3 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.390(2) . ?
C6 H6 0.9500 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.518(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H 0.9500 . ?
C14 C13 1.372(3) . ?
C14 C15 1.376(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C11A 1.530(2) . ?
C6A H6A 0.9500 . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C10A 1.518(2) . ?
C13 HA 0.9500 . ?
C13 C12 1.380(3) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C15 HB 0.9500 . ?
C15 C16 1.377(3) . ?
C12 HC 0.9500 . ?
C16 HD 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
O1 Zn1 O1A 118.09(4) . . ?
O1 Zn1 N1A 120.15(4) . . ?
O1 Zn1 N1 86.81(4) . . ?
O1A Zn1 N1A 86.70(4) . . ?
O1A Zn1 N1 115.57(4) . . ?
N1A Zn1 N1 132.83(4) . . ?
C2 O1 Zn1 109.82(8) . . ?
C2A O1A Zn1 110.00(8) . . ?
C7 N2 C8 125.60(11) . . ?
C7 N2 C9 122.29(12) . . ?
C8 N2 C9 112.00(11) . . ?
C7A N2A C9A 121.73(12) . . ?
C7A N2A C8A 125.50(12) . . ?
C8A N2A C9A 112.26(11) . . ?
C1A N1A Zn1 107.37(8) . . ?
C7A N1A Zn1 133.22(9) . . ?
C7A N1A C1A 119.35(11) . . ?
C1 N1 Zn1 106.81(8) . . ?
C7 N1 Zn1 133.82(9) . . ?
C7 N1 C1 119.04(11) . . ?
C4A C3A H3A 119.3 . . ?
C4A C3A C2A 121.48(13) . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A H4A 120.0 . . ?
C3A C4A C5A 119.93(13) . . ?
C5A C4A H4A 120.0 . . ?
C2A C1A N1A 115.03(11) . . ?
C6A C1A N1A 125.51(12) . . ?
C6A C1A C2A 119.44(12) . . ?
O1A C2A C3A 120.99(12) . . ?
O1A C2A C1A 120.76(12) . . ?
C3A C2A C1A 118.25(12) . . ?
O1 C2 C1 121.03(12) . . ?
O1 C2 C3 121.01(12) . . ?
C3 C2 C1 117.95(12) . . ?
N2A C7A H7A 117.4 . . ?
N1A C7A N2A 125.20(12) . . ?
N1A C7A H7A 117.4 . . ?
C2 C1 N1 114.96(11) . . ?
C6 C1 N1 125.34(12) . . ?
C6 C1 C2 119.70(12) . . ?
C12 N3 C16 116.45(16) . . ?
N2 C7 H7 117.5 . . ?
N1 C7 N2 125.00(12) . . ?
N1 C7 H7 117.5 . . ?
N2 C8 H8A 111.1 . . ?
N2 C8 H8B 111.1 . . ?
N2 C8 C11 103.38(11) . . ?
H8A C8 H8B 109.1 . . ?
C11 C8 H8A 111.1 . . ?
C11 C8 H8B 111.1 . . ?
N2 C9 H9A 111.3 . . ?
N2 C9 H9B 111.3 . . ?
N2 C9 C10 102.44(11) . . ?
H9A C9 H9B 109.2 . . ?
C10 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.26(13) . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C9 C10 C11 103.15(12) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.61(13) . . ?
C6 C5 H5 120.2 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.45(13) . . ?
C4 C3 H3 119.3 . . ?
C4A C5A H5A 120.1 . . ?
C4A C5A C6A 119.82(14) . . ?
C6A C5A H5A 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.93(13) . . ?
C5 C6 H6 119.5 . . ?
N2A C9A H9AA 111.1 . . ?
N2A C9A H9AB 111.1 . . ?
N2A C9A C10A 103.28(12) . . ?
H9AA C9A H9AB 109.1 . . ?
C10A C9A H9AA 111.1 . . ?
C10A C9A H9AB 111.1 . . ?
C8 C11 H11A 111.0 . . ?
C8 C11 H11B 111.0 . . ?
C10 C11 C8 103.75(12) . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C13 C14 H 120.4 . . ?
C13 C14 C15 119.11(17) . . ?
C15 C14 H 120.4 . . ?
N2A C8A H8AA 111.1 . . ?
N2A C8A H8AB 111.1 . . ?
N2A C8A C11A 103.31(12) . . ?
H8AA C8A H8AB 109.1 . . ?
C11A C8A H8AA 111.1 . . ?
C11A C8A H8AB 111.1 . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A C1A 121.06(14) . . ?
C5A C6A H6A 119.5 . . ?
C8A C11A H11C 111.0 . . ?
C8A C11A H11D 111.0 . . ?
H11C C11A H11D 109.0 . . ?
C10A C11A C8A 103.85(12) . . ?
C10A C11A H11C 111.0 . . ?
C10A C11A H11D 111.0 . . ?
C14 C13 HA 120.8 . . ?
C14 C13 C12 118.35(18) . . ?
C12 C13 HA 120.8 . . ?
C9A C10A H10C 110.9 . . ?
C9A C10A H10D 110.9 . . ?
C11A C10A C9A 104.19(12) . . ?
C11A C10A H10C 110.9 . . ?
C11A C10A H10D 110.9 . . ?
H10C C10A H10D 108.9 . . ?
C14 C15 HB 120.8 . . ?
C14 C15 C16 118.31(19) . . ?
C16 C15 HB 120.8 . . ?
N3 C12 C13 123.85(19) . . ?
N3 C12 HC 118.1 . . ?
C13 C12 HC 118.1 . . ?
N3 C16 C15 123.90(19) . . ?
N3 C16 HD 118.0 . . ?
C15 C16 HD 118.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 C1 -1.60(15) . . . . ?
Zn1 O1 C2 C3 177.09(10) . . . . ?
Zn1 O1A C2A C3A -175.96(10) . . . . ?
Zn1 O1A C2A C1A 3.84(15) . . . . ?
Zn1 N1A C1A C2A -0.87(13) . . . . ?
Zn1 N1A C1A C6A 177.43(12) . . . . ?
Zn1 N1A C7A N2A -7.4(2) . . . . ?
Zn1 N1 C1 C2 7.45(13) . . . . ?
Zn1 N1 C1 C6 -172.20(11) . . . . ?
Zn1 N1 C7 N2 -12.7(2) . . . . ?
O1 C2 C1 N1 -4.32(18) . . . . ?
O1 C2 C1 C6 175.35(12) . . . . ?
O1 C2 C3 C4 -176.43(13) . . . . ?
N2 C8 C11 C10 27.86(15) . . . . ?
N2 C9 C10 C11 34.56(14) . . . . ?
N2A C9A C10A C11A 29.46(15) . . . . ?
N2A C8A C11A C10A 29.25(15) . . . . ?
N1A C1A C2A O1A -2.02(18) . . . . ?
N1A C1A C2A C3A 177.78(11) . . . . ?
N1A C1A C6A C5A -177.40(13) . . . . ?
N1 C1 C6 C5 -178.64(13) . . . . ?
C3A C4A C5A C6A -0.9(2) . . . . ?
C4A C3A C2A O1A 179.46(13) . . . . ?
C4A C3A C2A C1A -0.3(2) . . . . ?
C4A C5A C6A C1A -0.1(2) . . . . ?
C1A N1A C7A N2A 175.95(12) . . . . ?
C2A C3A C4A C5A 1.1(2) . . . . ?
C2A C1A C6A C5A 0.8(2) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C7A N2A C9A C10A 160.92(13) . . . . ?
C7A N2A C8A C11A 176.86(13) . . . . ?
C7A N1A C1A C2A 176.55(12) . . . . ?
C7A N1A C1A C6A -5.2(2) . . . . ?
C1 N1 C7 N2 174.86(12) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
C7 N2 C8 C11 177.39(13) . . . . ?
C7 N2 C9 C10 158.69(13) . . . . ?
C7 N1 C1 C2 -178.23(12) . . . . ?
C7 N1 C1 C6 2.1(2) . . . . ?
C8 N2 C7 N1 -0.8(2) . . . . ?
C8 N2 C9 C10 -17.84(15) . . . . ?
C9 N2 C7 N1 -176.89(12) . . . . ?
C9 N2 C8 C11 -6.21(15) . . . . ?
C9 C10 C11 C8 -39.17(15) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
C3 C2 C1 N1 176.95(12) . . . . ?
C3 C2 C1 C6 -3.38(19) . . . . ?
C3 C4 C5 C6 -2.3(2) . . . . ?
C9A N2A C7A N1A -175.02(12) . . . . ?
C9A N2A C8A C11A -11.21(15) . . . . ?
C14 C13 C12 N3 -1.3(3) . . . . ?
C14 C15 C16 N3 -0.6(3) . . . . ?
C8A N2A C7A N1A -3.8(2) . . . . ?
C8A N2A C9A C10A -11.35(15) . . . . ?
C8A C11A C10A C9A -36.80(16) . . . . ?
C6A C1A C2A O1A 179.57(12) . . . . ?
C6A C1A C2A C3A -0.63(19) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C15 C14 C13 C12 0.7(3) . . . . ?
C12 N3 C16 C15 0.1(3) . . . . ?
C16 N3 C12 C13 0.9(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_6d
_database_code_depnum_ccdc_archive 'CCDC 2182086'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N6 O2 Zn'
_chemical_formula_sum            'C24 H36 N6 O2 Zn'
_chemical_formula_weight         505.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6168(3)
_cell_length_b                   11.2860(4)
_cell_length_c                   11.5396(4)
_cell_angle_alpha                75.743(2)
_cell_angle_beta                 89.755(2)
_cell_angle_gamma                71.855(2)
_cell_volume                     1269.52(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    0.999
_exptl_absorpt_correction_T_max  0.8014
_exptl_absorpt_correction_T_min  0.6436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0663 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3.00 0.00 2.00 0.0230
-3.00 0.00 -2.00 0.0620
-1.00 -3.00 -1.00 0.1670
1.00 3.00 1.00 0.3910
1.00 0.00 -1.00 0.0300
-1.00 0.00 1.00 0.0640

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and cyclohexane  by slow evaporation'
_exptl_crystal_size_max          0.801
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            86013
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4799
_reflns_number_total             5840
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         5840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+0.7332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0655
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C10(H10A,H10B), C10A(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3A(H3A), C4(H4), C4A(H4A), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C7(H7), C7A(H7A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C11(H11A,H11B,H11C), C11A(H11D,H11E,
 H11F), C12(H12A,H12B,H12C), C12A(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_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
Zn1 Zn 0.49502(2) 0.25209(2) 0.50504(2) 0.01472(6) Uani 1 1 d . . . . .
O1 O 0.42031(11) 0.25941(10) 0.65723(10) 0.0175(2) Uani 1 1 d . . . . .
O1A O 0.68658(11) 0.17419(10) 0.52332(10) 0.0182(2) Uani 1 1 d . . . . .
N1 N 0.37217(12) 0.15327(12) 0.48211(11) 0.0142(3) Uani 1 1 d . . . . .
N1A N 0.52361(13) 0.40580(12) 0.39124(11) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.42452(13) 0.09109(12) 0.30404(11) 0.0158(3) Uani 1 1 d . . . . .
N2A N 0.31570(13) 0.56728(12) 0.34152(12) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.16676(14) 0.20226(14) 0.15414(12) 0.0217(3) Uani 1 1 d . . . . .
N3A N 0.34004(14) 0.65609(14) 0.07963(12) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.29668(15) 0.14385(14) 0.58524(13) 0.0149(3) Uani 1 1 d . . . . .
C1A C 0.66483(15) 0.37599(15) 0.38296(14) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.32652(15) 0.20314(14) 0.67222(13) 0.0153(3) Uani 1 1 d . . . . .
C2A C 0.74343(16) 0.25378(15) 0.45480(14) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.25647(16) 0.19808(16) 0.77552(14) 0.0208(3) Uani 1 1 d . . . . .
H3 H 0.274489 0.238066 0.834107 0.025 Uiso 1 1 calc R U . . .
C3A C 0.88164(16) 0.21997(17) 0.45364(15) 0.0227(4) Uani 1 1 d . . . . .
H3A H 0.935530 0.138266 0.501053 0.027 Uiso 1 1 calc R U . . .
C4 C 0.16142(17) 0.13594(17) 0.79402(15) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.115183 0.133400 0.864794 0.028 Uiso 1 1 calc R U . . .
C4A C 0.94181(17) 0.30318(18) 0.38474(17) 0.0276(4) Uani 1 1 d . . . . .
H4A H 1.036010 0.279305 0.386867 0.033 Uiso 1 1 calc R U . . .
C5 C 0.13397(16) 0.07757(17) 0.70919(16) 0.0239(4) Uani 1 1 d . . . . .
H5 H 0.069245 0.034468 0.721925 0.029 Uiso 1 1 calc R U . . .
C5A C 0.86423(18) 0.42119(17) 0.31279(17) 0.0264(4) Uani 1 1 d . . . . .
H5A H 0.905182 0.477864 0.264689 0.032 Uiso 1 1 calc R U . . .
C6 C 0.20116(16) 0.08209(16) 0.60540(15) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.181421 0.042292 0.547349 0.024 Uiso 1 1 calc R U . . .
C6A C 0.72668(17) 0.45657(16) 0.31101(15) 0.0214(3) Uani 1 1 d . . . . .
H6A H 0.673982 0.536741 0.260100 0.026 Uiso 1 1 calc R U . . .
C7 C 0.35825(15) 0.09359(14) 0.40184(13) 0.0149(3) Uani 1 1 d . . . . .
H7 H 0.295533 0.048158 0.414383 0.018 Uiso 1 1 calc R U . . .
C7A C 0.44745(15) 0.52433(15) 0.34381(13) 0.0156(3) Uani 1 1 d . . . . .
H7A H 0.490255 0.585140 0.307775 0.019 Uiso 1 1 calc R U . . .
C8 C 0.51745(16) 0.16261(17) 0.27074(15) 0.0216(3) Uani 1 1 d . . . . .
H8A H 0.468249 0.255054 0.243635 0.032 Uiso 1 1 calc R U . . .
H8B H 0.568102 0.134298 0.205800 0.032 Uiso 1 1 calc R U . . .
H8C H 0.578659 0.146705 0.340345 0.032 Uiso 1 1 calc R U . . .
C8A C 0.23728(17) 0.48321(17) 0.38879(17) 0.0257(4) Uani 1 1 d . . . . .
H8AA H 0.253158 0.415665 0.345849 0.038 Uiso 1 1 calc R U . . .
H8AB H 0.142678 0.534034 0.377909 0.038 Uiso 1 1 calc R U . . .
H8AC H 0.263291 0.443409 0.474394 0.038 Uiso 1 1 calc R U . . .
C9 C 0.38611(16) 0.03402(15) 0.21472(14) 0.0188(3) Uani 1 1 d . . . . .
H9A H 0.341846 -0.029007 0.254046 0.023 Uiso 1 1 calc R U . . .
H9B H 0.466933 -0.013081 0.181433 0.023 Uiso 1 1 calc R U . . .
C9A C 0.24627(16) 0.69774(15) 0.26837(14) 0.0204(3) Uani 1 1 d . . . . .
H9AA H 0.300836 0.753935 0.271629 0.024 Uiso 1 1 calc R U . . .
H9AB H 0.160999 0.732779 0.302346 0.024 Uiso 1 1 calc R U . . .
C10 C 0.29277(16) 0.13549(16) 0.11302(14) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.336510 0.199359 0.074763 0.023 Uiso 1 1 calc R U . . .
H10B H 0.275262 0.093542 0.051716 0.023 Uiso 1 1 calc R U . . .
C10A C 0.21868(17) 0.70083(17) 0.13810(15) 0.0236(4) Uani 1 1 d . . . . .
H10C H 0.162810 0.645798 0.134823 0.028 Uiso 1 1 calc R U . . .
H10D H 0.168019 0.790229 0.093617 0.028 Uiso 1 1 calc R U . . .
C11 C 0.09811(19) 0.32421(18) 0.06822(18) 0.0347(4) Uani 1 1 d . . . . .
H11A H 0.154905 0.379352 0.055581 0.052 Uiso 1 1 calc R U . . .
H11B H 0.015060 0.367499 0.099324 0.052 Uiso 1 1 calc R U . . .
H11C H 0.078148 0.307891 -0.008105 0.052 Uiso 1 1 calc R U . . .
C11A C 0.3107(2) 0.6294(2) -0.03319(17) 0.0375(5) Uani 1 1 d . . . . .
H11D H 0.263999 0.565272 -0.017687 0.056 Uiso 1 1 calc R U . . .
H11E H 0.393967 0.595792 -0.068936 0.056 Uiso 1 1 calc R U . . .
H11F H 0.254506 0.709173 -0.088550 0.056 Uiso 1 1 calc R U . . .
C12 C 0.08090(19) 0.1216(2) 0.17842(18) 0.0324(4) Uani 1 1 d . . . . .
H12A H 0.061585 0.099865 0.104743 0.049 Uiso 1 1 calc R U . . .
H12B H -0.002399 0.168536 0.206710 0.049 Uiso 1 1 calc R U . . .
H12C H 0.125837 0.042141 0.240114 0.049 Uiso 1 1 calc R U . . .
C12A C 0.4126(2) 0.7488(2) 0.05727(17) 0.0341(4) Uani 1 1 d . . . . .
H12D H 0.356623 0.830617 0.004508 0.051 Uiso 1 1 calc R U . . .
H12E H 0.493755 0.715071 0.018783 0.051 Uiso 1 1 calc R U . . .
H12F H 0.436238 0.763224 0.133491 0.051 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 O1 1.9337(11) . ?
Zn1 O1A 1.9370(11) . ?
Zn1 N1 2.0172(12) . ?
Zn1 N1A 2.0072(13) . ?
O1 C2 1.3278(18) . ?
O1A C2A 1.3342(18) . ?
N1 C1 1.4326(19) . ?
N1 C7 1.305(2) . ?
N1A C1A 1.4390(19) . ?
N1A C7A 1.309(2) . ?
N2 C7 1.3289(19) . ?
N2 C8 1.453(2) . ?
N2 C9 1.4621(19) . ?
N2A C7A 1.328(2) . ?
N2A C8A 1.457(2) . ?
N2A C9A 1.463(2) . ?
N3 C10 1.458(2) . ?
N3 C11 1.455(2) . ?
N3 C12 1.459(2) . ?
N3A C10A 1.458(2) . ?
N3A C11A 1.462(2) . ?
N3A C12A 1.457(2) . ?
C1 C2 1.422(2) . ?
C1 C6 1.388(2) . ?
C1A C2A 1.418(2) . ?
C1A C6A 1.394(2) . ?
C2 C3 1.401(2) . ?
C2A C3A 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.387(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.388(2) . ?
C6 H6 0.9500 . ?
C6A H6A 0.9500 . ?
C7 H7 0.9500 . ?
C7A H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(2) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.523(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1A 112.07(5) . . ?
O1 Zn1 N1 86.72(5) . . ?
O1 Zn1 N1A 122.65(5) . . ?
O1A Zn1 N1 122.19(5) . . ?
O1A Zn1 N1A 87.14(5) . . ?
N1A Zn1 N1 128.83(5) . . ?
C2 O1 Zn1 110.35(9) . . ?
C2A O1A Zn1 110.06(9) . . ?
C1 N1 Zn1 107.00(9) . . ?
C7 N1 Zn1 133.65(10) . . ?
C7 N1 C1 119.12(12) . . ?
C1A N1A Zn1 106.79(9) . . ?
C7A N1A Zn1 133.90(11) . . ?
C7A N1A C1A 118.21(13) . . ?
C7 N2 C8 122.78(13) . . ?
C7 N2 C9 119.00(13) . . ?
C8 N2 C9 117.29(12) . . ?
C7A N2A C8A 122.71(13) . . ?
C7A N2A C9A 117.89(13) . . ?
C8A N2A C9A 118.31(13) . . ?
C10 N3 C12 111.34(14) . . ?
C11 N3 C10 111.52(14) . . ?
C11 N3 C12 110.12(15) . . ?
C10A N3A C11A 110.97(14) . . ?
C12A N3A C10A 111.88(15) . . ?
C12A N3A C11A 109.57(15) . . ?
C2 C1 N1 114.97(13) . . ?
C6 C1 N1 125.51(14) . . ?
C6 C1 C2 119.52(14) . . ?
C2A C1A N1A 115.34(13) . . ?
C6A C1A N1A 125.17(15) . . ?
C6A C1A C2A 119.49(15) . . ?
O1 C2 C1 120.91(13) . . ?
O1 C2 C3 120.83(14) . . ?
C3 C2 C1 118.25(14) . . ?
O1A C2A C1A 120.66(14) . . ?
O1A C2A C3A 120.94(15) . . ?
C3A C2A C1A 118.39(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.37(15) . . ?
C4 C3 H3 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A C2A 121.39(16) . . ?
C4A C3A H3A 119.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(15) . . ?
C5 C4 H4 120.1 . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A C3A 119.85(16) . . ?
C5A C4A H4A 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.95(15) . . ?
C6 C5 H5 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 119.97(16) . . ?
C6A C5A H5A 120.0 . . ?
C1 C6 C5 121.02(15) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A C1A 120.85(16) . . ?
C5A C6A H6A 119.6 . . ?
N1 C7 N2 125.43(14) . . ?
N1 C7 H7 117.3 . . ?
N2 C7 H7 117.3 . . ?
N1A C7A N2A 125.87(14) . . ?
N1A C7A H7A 117.1 . . ?
N2A C7A H7A 117.1 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2A C8A H8AA 109.5 . . ?
N2A C8A H8AB 109.5 . . ?
N2A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
N2 C9 C10 111.96(13) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
N2A C9A H9AA 109.1 . . ?
N2A C9A H9AB 109.1 . . ?
N2A C9A C10A 112.35(13) . . ?
H9AA C9A H9AB 107.9 . . ?
C10A C9A H9AA 109.1 . . ?
C10A C9A H9AB 109.1 . . ?
N3 C10 C9 112.35(13) . . ?
N3 C10 H10A 109.1 . . ?
N3 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N3A C10A C9A 112.59(14) . . ?
N3A C10A H10C 109.1 . . ?
N3A C10A H10D 109.1 . . ?
C9A C10A H10C 109.1 . . ?
C9A C10A H10D 109.1 . . ?
H10C C10A H10D 107.8 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3A C11A H11D 109.5 . . ?
N3A C11A H11E 109.5 . . ?
N3A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3A C12A H12D 109.5 . . ?
N3A C12A H12E 109.5 . . ?
N3A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 C1 2.37(17) . . . . ?
Zn1 O1 C2 C3 -179.10(12) . . . . ?
Zn1 O1A C2A C1A 0.30(17) . . . . ?
Zn1 O1A C2A C3A 179.13(12) . . . . ?
Zn1 N1 C1 C2 -0.10(15) . . . . ?
Zn1 N1 C1 C6 -179.48(13) . . . . ?
Zn1 N1 C7 N2 -4.4(2) . . . . ?
Zn1 N1A C1A C2A -1.08(15) . . . . ?
Zn1 N1A C1A C6A 178.64(13) . . . . ?
Zn1 N1A C7A N2A -15.2(2) . . . . ?
O1 C2 C3 C4 -177.86(15) . . . . ?
O1A C2A C3A C4A -178.58(15) . . . . ?
N1 C1 C2 O1 -1.5(2) . . . . ?
N1 C1 C2 C3 179.88(14) . . . . ?
N1 C1 C6 C5 179.51(15) . . . . ?
N1A C1A C2A O1A 0.6(2) . . . . ?
N1A C1A C2A C3A -178.28(13) . . . . ?
N1A C1A C6A C5A 177.43(15) . . . . ?
N2 C9 C10 N3 -63.33(17) . . . . ?
N2A C9A C10A N3A -61.44(19) . . . . ?
C1 N1 C7 N2 -177.99(14) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C1A N1A C7A N2A 178.61(14) . . . . ?
C1A C2A C3A C4A 0.3(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2A C1A C6A C5A -2.9(2) . . . . ?
C2A C3A C4A C5A -1.7(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3A C4A C5A C6A 0.8(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4A C5A C6A C1A 1.4(3) . . . . ?
C6 C1 C2 O1 177.87(14) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C6A C1A C2A O1A -179.17(14) . . . . ?
C6A C1A C2A C3A 2.0(2) . . . . ?
C7 N1 C1 C2 175.07(13) . . . . ?
C7 N1 C1 C6 -4.3(2) . . . . ?
C7 N2 C9 C10 96.29(16) . . . . ?
C7A N1A C1A C2A 168.57(14) . . . . ?
C7A N1A C1A C6A -11.7(2) . . . . ?
C7A N2A C9A C10A 85.72(17) . . . . ?
C8 N2 C7 N1 -3.7(2) . . . . ?
C8 N2 C9 C10 -72.95(17) . . . . ?
C8A N2A C7A N1A -2.8(2) . . . . ?
C8A N2A C9A C10A -82.71(18) . . . . ?
C9 N2 C7 N1 -172.27(14) . . . . ?
C9A N2A C7A N1A -170.65(14) . . . . ?
C11 N3 C10 C9 160.91(14) . . . . ?
C11A N3A C10A C9A 165.69(15) . . . . ?
C12 N3 C10 C9 -75.65(17) . . . . ?
C12A N3A C10A C9A -71.59(18) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'


#======END

####################################################################### 
# 
# 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_compound_6c
_database_code_depnum_ccdc_archive 'CCDC 2182081'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H46 N6 O2 Zn2'
_chemical_formula_sum            'C28 H46 N6 O2 Zn2'
_chemical_formula_weight         629.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0934(6)
_cell_length_b                   14.4079(8)
_cell_length_c                   11.0432(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.793(2)
_cell_angle_gamma                90
_cell_volume                     1529.14(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.555
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  0.7142
_exptl_absorpt_correction_T_min  0.6160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0629 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.8625.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            81240
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.548
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3108
_reflns_number_total             3525
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0198
_refine_ls_restrained_S_all      1.054
_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)+(0.0222P)²+0.8573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0477
_refine_ls_wR_factor_ref         0.0500
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_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
Zn1 Zn -0.05083(2) 0.50551(2) 0.35642(2) 0.01015(5) Uani 1 1 d . . . . .
O1 O 0.05449(9) 0.41118(6) 0.49206(8) 0.01112(17) Uani 1 1 d . . . . .
N1 N 0.25511(11) 0.51607(7) 0.64784(10) 0.0105(2) Uani 1 1 d . . . . .
N2 N 0.32058(11) 0.66197(7) 0.73926(11) 0.0138(2) Uani 1 1 d . . . . .
N3 N 0.59806(12) 0.61477(8) 0.93455(11) 0.0167(2) Uani 1 1 d . . . . .
C14 C 0.18307(15) 0.57444(11) 0.27532(15) 0.0240(3) Uani 1 1 d . . . . .
H14A H 0.221040 0.586163 0.204995 0.036 Uiso 1 1 calc R U . . .
H14B H 0.241855 0.529233 0.333916 0.036 Uiso 1 1 calc R U . . .
H14C H 0.181000 0.632581 0.320771 0.036 Uiso 1 1 calc R U . . .
C1 C 0.29678(13) 0.43888(8) 0.58725(12) 0.0106(2) Uani 1 1 d . . . . .
C2 C 0.18702(13) 0.38766(8) 0.50310(11) 0.0104(2) Uani 1 1 d . . . . .
C3 C 0.21999(13) 0.31328(9) 0.43648(12) 0.0132(2) Uani 1 1 d . . . . .
H3 H 0.147582 0.280199 0.376667 0.016 Uiso 1 1 calc R U . . .
C4 C 0.35784(14) 0.28710(9) 0.45679(13) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.378802 0.236157 0.411173 0.019 Uiso 1 1 calc R U . . .
C5 C 0.46462(14) 0.33498(9) 0.54323(13) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.558446 0.316191 0.557932 0.020 Uiso 1 1 calc R U . . .
C6 C 0.43414(13) 0.41084(9) 0.60865(13) 0.0148(3) Uani 1 1 d . . . . .
H6 H 0.507395 0.443520 0.668072 0.018 Uiso 1 1 calc R U . . .
C7 C 0.34239(13) 0.58477(9) 0.68219(12) 0.0122(2) Uani 1 1 d . . . . .
H7 H 0.428746 0.579279 0.665059 0.015 Uiso 1 1 calc R U . . .
C8 C 0.19465(14) 0.67441(9) 0.77629(13) 0.0168(3) Uani 1 1 d . . . . .
H8A H 0.112683 0.664801 0.702121 0.025 Uiso 1 1 calc R U . . .
H8B H 0.192833 0.737457 0.809061 0.025 Uiso 1 1 calc R U . . .
H8C H 0.193928 0.629336 0.842543 0.025 Uiso 1 1 calc R U . . .
C9 C 0.43674(14) 0.72610(9) 0.79169(13) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.399856 0.789892 0.790361 0.020 Uiso 1 1 calc R U . . .
H9B H 0.498448 0.725219 0.737150 0.020 Uiso 1 1 calc R U . . .
C13 C 0.03516(13) 0.53594(10) 0.22264(13) 0.0166(3) Uani 1 1 d . . . . .
H13A H 0.037511 0.479247 0.172686 0.020 Uiso 1 1 calc R U . . .
H13B H -0.023631 0.582264 0.164194 0.020 Uiso 1 1 calc R U . . .
C10 C 0.52145(14) 0.70127(9) 0.92753(13) 0.0171(3) Uani 1 1 d . . . . .
H10A H 0.587928 0.752070 0.963336 0.021 Uiso 1 1 calc R U . . .
H10B H 0.458041 0.695703 0.980100 0.021 Uiso 1 1 calc R U . . .
C11 C 0.63685(16) 0.57724(11) 1.06310(14) 0.0254(3) Uani 1 1 d . . . . .
H11A H 0.694194 0.622578 1.122548 0.038 Uiso 1 1 calc R U . . .
H11B H 0.689800 0.519761 1.066625 0.038 Uiso 1 1 calc R U . . .
H11C H 0.552643 0.564143 1.086626 0.038 Uiso 1 1 calc R U . . .
C12 C 0.72318(16) 0.62859(12) 0.89738(16) 0.0305(4) Uani 1 1 d . . . . .
H12A H 0.697289 0.650286 0.809118 0.046 Uiso 1 1 calc R U . . .
H12B H 0.773865 0.569795 0.904876 0.046 Uiso 1 1 calc R U . . .
H12C H 0.782610 0.675008 0.953143 0.046 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 Zn1 3.0242(3) 3_566 ?
Zn1 O1 2.0689(9) 3_566 ?
Zn1 O1 2.0610(9) . ?
Zn1 N1 2.0714(10) 3_566 ?
Zn1 C13 1.9778(13) . ?
O1 C2 1.3489(15) . ?
N1 C1 1.4259(15) . ?
N1 C7 1.3022(16) . ?
N2 C7 1.3296(16) . ?
N2 C8 1.4603(16) . ?
N2 C9 1.4659(16) . ?
N3 C10 1.4563(17) . ?
N3 C11 1.4565(18) . ?
N3 C12 1.4559(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C13 1.5311(19) . ?
C1 C2 1.4165(17) . ?
C1 C6 1.3931(17) . ?
C2 C3 1.3964(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3920(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3857(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3954(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5250(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 Zn1 43.02(2) . 3_566 ?
O1 Zn1 Zn1 42.82(2) 3_566 3_566 ?
O1 Zn1 O1 85.84(3) . 3_566 ?
O1 Zn1 N1 101.91(4) . 3_566 ?
O1 Zn1 N1 80.90(4) 3_566 3_566 ?
N1 Zn1 Zn1 91.85(3) 3_566 3_566 ?
C13 Zn1 Zn1 135.17(4) . 3_566 ?
C13 Zn1 O1 126.58(5) . 3_566 ?
C13 Zn1 O1 116.26(5) . . ?
C13 Zn1 N1 132.63(5) . 3_566 ?
Zn1 O1 Zn1 94.16(3) . 3_566 ?
C2 O1 Zn1 120.56(7) . . ?
C2 O1 Zn1 109.57(7) . 3_566 ?
C1 N1 Zn1 107.86(8) . 3_566 ?
C7 N1 Zn1 134.49(9) . 3_566 ?
C7 N1 C1 117.33(10) . . ?
C7 N2 C8 121.33(11) . . ?
C7 N2 C9 119.09(11) . . ?
C8 N2 C9 118.13(10) . . ?
C10 N3 C11 110.47(11) . . ?
C12 N3 C10 111.11(11) . . ?
C12 N3 C11 109.12(12) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
C2 C1 N1 115.50(10) . . ?
C6 C1 N1 124.58(11) . . ?
C6 C1 C2 119.90(11) . . ?
O1 C2 C1 118.92(11) . . ?
O1 C2 C3 122.31(11) . . ?
C3 C2 C1 118.75(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.69(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.33(12) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.90(12) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.32(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 N2 125.36(12) . . ?
N1 C7 H7 117.3 . . ?
N2 C7 H7 117.3 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N2 C9 C10 112.39(11) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
Zn1 C13 H13A 108.9 . . ?
Zn1 C13 H13B 108.9 . . ?
C14 C13 Zn1 113.33(10) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N3 C10 C9 112.46(11) . . ?
N3 C10 H10A 109.1 . . ?
N3 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 C1 91.04(12) . . . . ?
Zn1 O1 C2 C1 -16.38(13) 3_566 . . . ?
Zn1 O1 C2 C3 162.24(10) 3_566 . . . ?
Zn1 O1 C2 C3 -90.35(12) . . . . ?
Zn1 N1 C1 C2 21.63(12) 3_566 . . . ?
Zn1 N1 C1 C6 -156.44(11) 3_566 . . . ?
Zn1 N1 C7 N2 7.2(2) 3_566 . . . ?
O1 C2 C3 C4 -175.58(11) . . . . ?
N1 C1 C2 O1 -3.80(16) . . . . ?
N1 C1 C2 C3 177.53(11) . . . . ?
N1 C1 C6 C5 -179.10(12) . . . . ?
N2 C9 C10 N3 68.27(14) . . . . ?
C1 N1 C7 N2 179.81(12) . . . . ?
C1 C2 C3 C4 3.03(18) . . . . ?
C2 C1 C6 C5 2.91(19) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 O1 174.36(11) . . . . ?
C6 C1 C2 C3 -4.30(18) . . . . ?
C7 N1 C1 C2 -152.84(11) . . . . ?
C7 N1 C1 C6 29.09(18) . . . . ?
C7 N2 C9 C10 -87.20(14) . . . . ?
C8 N2 C7 N1 3.7(2) . . . . ?
C8 N2 C9 C10 79.26(14) . . . . ?
C9 N2 C7 N1 169.69(12) . . . . ?
C11 N3 C10 C9 -160.32(12) . . . . ?
C12 N3 C10 C9 78.41(14) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_1bprime
_database_code_depnum_ccdc_archive 'CCDC 2182076'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 Al N4 O3'
_chemical_formula_sum            'C21 H29 Al N4 O3'
_chemical_formula_weight         412.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.6976(5)
_cell_length_b                   7.7241(4)
_cell_length_c                   25.9622(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.4237(15)
_cell_angle_gamma                90
_cell_volume                     2135.63(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5488
_cell_measurement_temperature    115.0(1)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.8319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0733 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8675.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3.00 1.00 1.00 0.1340
2.00 -1.00 -2.00 0.1040
-1.00 -2.00 -3.00 0.0580
4.00 0.00 -1.00 0.1080
-4.00 0.00 1.00 0.0450
-1.00 1.00 2.00 0.0790
0.00 0.00 1.00 0.0540
0.00 0.00 -1.00 0.0350
6.00 1.00 -6.00 0.0930
-1.00 0.00 -2.00 0.0390
0.00 1.00 -6.00 0.0490
0.00 -1.00 6.00 0.0650
-1.00 4.00 -5.00 0.0660

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and pentane  by slow evaporation'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.752
_diffrn_ambient_temperature      115.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius APEX-II CCD'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2304
_reflns_number_total             3760
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.013
_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)+(0.0543P)²+1.2718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C3A(H3A), C4(H4), C4A(H4A), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C7(H7), C7A(H7A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_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
Al1 Al 0.37211(8) 0.39781(12) 0.65320(3) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.50932(18) 0.3032(3) 0.68718(7) 0.0202(5) Uani 1 1 d . . . . .
O1A O 0.24114(18) 0.2723(3) 0.62673(7) 0.0203(5) Uani 1 1 d . . . . .
O2 O 0.36739(19) 0.6208(3) 0.64393(7) 0.0209(5) Uani 1 1 d . . . . .
N1 N 0.3103(2) 0.4111(3) 0.72558(9) 0.0178(6) Uani 1 1 d . . . . .
N1A N 0.4452(2) 0.3337(3) 0.58371(9) 0.0180(6) Uani 1 1 d . . . . .
N2 N 0.0899(2) 0.4117(4) 0.72379(9) 0.0199(6) Uani 1 1 d . . . . .
N2A N 0.6648(2) 0.3678(3) 0.59025(9) 0.0202(6) Uani 1 1 d . . . . .
C1 C 0.4209(3) 0.4064(4) 0.76055(11) 0.0176(7) Uani 1 1 d . . . . .
C1A C 0.3416(3) 0.2726(4) 0.54993(11) 0.0184(7) Uani 1 1 d . . . . .
C2 C 0.5267(3) 0.3456(4) 0.73755(11) 0.0195(7) Uani 1 1 d . . . . .
C2A C 0.2328(3) 0.2453(4) 0.57545(11) 0.0196(7) Uani 1 1 d . . . . .
C3 C 0.6420(3) 0.3387(4) 0.76670(12) 0.0229(8) Uani 1 1 d . . . . .
H3 H 0.713813 0.297065 0.751684 0.027 Uiso 1 1 calc R U . . .
C3A C 0.1229(3) 0.1936(4) 0.54695(12) 0.0231(8) Uani 1 1 d . . . . .
H3A H 0.048562 0.176859 0.563678 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6522(3) 0.3930(4) 0.81801(12) 0.0245(8) Uani 1 1 d . . . . .
H4 H 0.731364 0.388478 0.837927 0.029 Uiso 1 1 calc R U . . .
C4A C 0.1212(3) 0.1661(4) 0.49399(12) 0.0280(8) Uani 1 1 d . . . . .
H4A H 0.045810 0.130200 0.474682 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5484(3) 0.4532(4) 0.84026(12) 0.0230(8) Uani 1 1 d . . . . .
H5 H 0.556516 0.488521 0.875468 0.028 Uiso 1 1 calc R U . . .
C5A C 0.2292(3) 0.1907(5) 0.46913(12) 0.0286(8) Uani 1 1 d . . . . .
H5A H 0.228139 0.169145 0.433072 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4321(3) 0.4628(4) 0.81166(11) 0.0203(8) Uani 1 1 d . . . . .
H6 H 0.361254 0.507142 0.826791 0.024 Uiso 1 1 calc R U . . .
C6A C 0.3382(3) 0.2469(4) 0.49702(11) 0.0237(8) Uani 1 1 d . . . . .
H6A H 0.411229 0.267844 0.479773 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2043(3) 0.3818(4) 0.74589(11) 0.0182(7) Uani 1 1 d . . . . .
H7 H 0.210545 0.334529 0.779818 0.022 Uiso 1 1 calc R U . . .
C7A C 0.5575(3) 0.3013(4) 0.57006(11) 0.0193(7) Uani 1 1 d . . . . .
H7A H 0.562386 0.221070 0.542591 0.023 Uiso 1 1 calc R U . . .
C8 C 0.0642(3) 0.5043(4) 0.67503(11) 0.0238(8) Uani 1 1 d . . . . .
H8A H 0.138031 0.572670 0.668182 0.036 Uiso 1 1 calc R U . . .
H8B H -0.007760 0.581537 0.677207 0.036 Uiso 1 1 calc R U . . .
H8C H 0.045158 0.420971 0.646920 0.036 Uiso 1 1 calc R U . . .
C8A C 0.6767(3) 0.5064(4) 0.62867(12) 0.0227(8) Uani 1 1 d . . . . .
H8AA H 0.595626 0.564816 0.629557 0.034 Uiso 1 1 calc R U . . .
H8AB H 0.739765 0.589965 0.619430 0.034 Uiso 1 1 calc R U . . .
H8AC H 0.702708 0.457256 0.662816 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0198(3) 0.3505(5) 0.74837(13) 0.0268(8) Uani 1 1 d . . . . .
H9A H -0.067867 0.269468 0.725176 0.040 Uiso 1 1 calc R U . . .
H9B H -0.072961 0.449385 0.755474 0.040 Uiso 1 1 calc R U . . .
H9C H 0.008093 0.291800 0.780903 0.040 Uiso 1 1 calc R U . . .
C9A C 0.7835(3) 0.3043(5) 0.57439(13) 0.0341(9) Uani 1 1 d . . . . .
H9AA H 0.767367 0.210042 0.549380 0.051 Uiso 1 1 calc R U . . .
H9AB H 0.835843 0.261449 0.604741 0.051 Uiso 1 1 calc R U . . .
H9AC H 0.827269 0.398733 0.558374 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3661(3) 0.7167(4) 0.59747(12) 0.0256(8) Uani 1 1 d . . . . .
H10 H 0.410589 0.647642 0.572189 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4358(3) 0.8866(4) 0.60719(14) 0.0348(9) Uani 1 1 d . . . . .
H11A H 0.392599 0.957120 0.631411 0.052 Uiso 1 1 calc R U . . .
H11B H 0.437909 0.949195 0.574451 0.052 Uiso 1 1 calc R U . . .
H11C H 0.521819 0.863182 0.621991 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2322(3) 0.7468(5) 0.57449(12) 0.0328(9) Uani 1 1 d . . . . .
H12A H 0.191602 0.635119 0.566249 0.049 Uiso 1 1 calc R U . . .
H12B H 0.232672 0.815824 0.542841 0.049 Uiso 1 1 calc R U . . .
H12C H 0.185734 0.808824 0.599532 0.049 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
Al1 O1 1.795(2) . ?
Al1 O1A 1.787(2) . ?
Al1 O2 1.739(2) . ?
Al1 N1 2.053(2) . ?
Al1 N1A 2.092(2) . ?
O1 C2 1.344(3) . ?
O1A C2A 1.342(3) . ?
O2 C10 1.415(4) . ?
N1 C1 1.422(4) . ?
N1 C7 1.315(4) . ?
N1A C1A 1.427(4) . ?
N1A C7A 1.309(4) . ?
N2 C7 1.322(4) . ?
N2 C8 1.457(4) . ?
N2 C9 1.466(4) . ?
N2A C7A 1.320(4) . ?
N2A C8A 1.460(4) . ?
N2A C9A 1.457(4) . ?
C1 C2 1.409(4) . ?
C1 C6 1.391(4) . ?
C1A C2A 1.409(4) . ?
C1A C6A 1.385(4) . ?
C2 C3 1.386(4) . ?
C2A C3A 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.390(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.383(4) . ?
C6 H6 0.9500 . ?
C6A H6A 0.9500 . ?
C7 H7 0.9500 . ?
C7A H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.519(5) . ?
C10 C12 1.517(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Al1 N1 83.66(10) . . ?
O1 Al1 N1A 88.44(10) . . ?
O1A Al1 O1 122.92(11) . . ?
O1A Al1 N1 94.04(10) . . ?
O1A Al1 N1A 83.30(10) . . ?
O2 Al1 O1 118.86(11) . . ?
O2 Al1 O1A 118.20(11) . . ?
O2 Al1 N1 93.98(11) . . ?
O2 Al1 N1A 97.09(10) . . ?
N1 Al1 N1A 168.55(11) . . ?
C2 O1 Al1 114.24(18) . . ?
C2A O1A Al1 116.25(18) . . ?
C10 O2 Al1 129.38(19) . . ?
C1 N1 Al1 105.24(17) . . ?
C7 N1 Al1 136.3(2) . . ?
C7 N1 C1 115.9(2) . . ?
C1A N1A Al1 106.07(18) . . ?
C7A N1A Al1 134.9(2) . . ?
C7A N1A C1A 116.7(2) . . ?
C7 N2 C8 123.6(2) . . ?
C7 N2 C9 120.1(3) . . ?
C8 N2 C9 116.3(2) . . ?
C7A N2A C8A 125.0(3) . . ?
C7A N2A C9A 120.4(3) . . ?
C9A N2A C8A 114.7(2) . . ?
C2 C1 N1 113.0(3) . . ?
C6 C1 N1 126.4(3) . . ?
C6 C1 C2 120.5(3) . . ?
C2A C1A N1A 112.9(2) . . ?
C6A C1A N1A 127.1(3) . . ?
C6A C1A C2A 120.0(3) . . ?
O1 C2 C1 116.8(3) . . ?
O1 C2 C3 123.8(3) . . ?
C3 C2 C1 119.4(3) . . ?
O1A C2A C1A 117.5(3) . . ?
O1A C2A C3A 123.2(3) . . ?
C3A C2A C1A 119.3(3) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2A C3A H3A 119.9 . . ?
C2A C3A C4A 120.2(3) . . ?
C4A C3A H3A 119.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A C3A 120.4(3) . . ?
C5A C4A H4A 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.8(3) . . ?
C6A C5A H5A 120.1 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 H6 120.5 . . ?
C1A C6A H6A 119.8 . . ?
C5A C6A C1A 120.4(3) . . ?
C5A C6A H6A 119.8 . . ?
N1 C7 N2 126.4(3) . . ?
N1 C7 H7 116.8 . . ?
N2 C7 H7 116.8 . . ?
N1A C7A N2A 127.2(3) . . ?
N1A C7A H7A 116.4 . . ?
N2A C7A H7A 116.4 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2A C8A H8AA 109.5 . . ?
N2A C8A H8AB 109.5 . . ?
N2A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2A C9A H9AA 109.5 . . ?
N2A C9A H9AB 109.5 . . ?
N2A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O2 C10 H10 108.3 . . ?
O2 C10 C11 110.2(3) . . ?
O2 C10 C12 110.4(3) . . ?
C11 C10 H10 108.3 . . ?
C12 C10 H10 108.3 . . ?
C12 C10 C11 111.3(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Al1 O1 C2 C1 20.0(3) . . . . ?
Al1 O1 C2 C3 -157.5(3) . . . . ?
Al1 O1A C2A C1A 17.7(3) . . . . ?
Al1 O1A C2A C3A -161.9(3) . . . . ?
Al1 O2 C10 C11 -146.7(2) . . . . ?
Al1 O2 C10 C12 90.0(3) . . . . ?
Al1 N1 C1 C2 -17.2(3) . . . . ?
Al1 N1 C1 C6 159.3(3) . . . . ?
Al1 N1 C7 N2 -35.3(5) . . . . ?
Al1 N1A C1A C2A -10.6(3) . . . . ?
Al1 N1A C1A C6A 166.5(3) . . . . ?
Al1 N1A C7A N2A -31.8(5) . . . . ?
O1 Al1 O1A C2A -102.2(2) . . . . ?
O1 Al1 O2 C10 113.3(2) . . . . ?
O1 C2 C3 C4 176.9(3) . . . . ?
O1A Al1 O1 C2 -114.3(2) . . . . ?
O1A Al1 O2 C10 -65.0(3) . . . . ?
O1A C2A C3A C4A -179.3(3) . . . . ?
O2 Al1 O1 C2 67.5(2) . . . . ?
O2 Al1 O1A C2A 76.1(2) . . . . ?
N1 Al1 O1 C2 -23.5(2) . . . . ?
N1 Al1 O1A C2A 172.8(2) . . . . ?
N1 Al1 O2 C10 -161.8(2) . . . . ?
N1 C1 C2 O1 0.6(4) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
N1 C1 C6 C5 -178.3(3) . . . . ?
N1A Al1 O1 C2 164.8(2) . . . . ?
N1A Al1 O1A C2A -18.4(2) . . . . ?
N1A Al1 O2 C10 21.1(3) . . . . ?
N1A C1A C2A O1A -2.6(4) . . . . ?
N1A C1A C2A C3A 177.0(3) . . . . ?
N1A C1A C6A C5A -178.3(3) . . . . ?
C1 N1 C7 N2 166.1(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1A N1A C7A N2A 168.2(3) . . . . ?
C1A C2A C3A C4A 1.2(5) . . . . ?
C2 C1 C6 C5 -2.0(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2A C1A C6A C5A -1.4(5) . . . . ?
C2A C3A C4A C5A -0.2(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C3A C4A C5A C6A -1.5(5) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C4A C5A C6A C1A 2.3(5) . . . . ?
C6 C1 C2 O1 -176.2(3) . . . . ?
C6 C1 C2 C3 1.4(5) . . . . ?
C6A C1A C2A O1A -179.9(3) . . . . ?
C6A C1A C2A C3A -0.3(5) . . . . ?
C7 N1 C1 C2 147.7(3) . . . . ?
C7 N1 C1 C6 -35.8(4) . . . . ?
C7A N1A C1A C2A 154.8(3) . . . . ?
C7A N1A C1A C6A -28.1(5) . . . . ?
C8 N2 C7 N1 -8.4(5) . . . . ?
C8A N2A C7A N1A -7.0(5) . . . . ?
C9 N2 C7 N1 171.6(3) . . . . ?
C9A N2A C7A N1A 173.4(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound_3d
_database_code_depnum_ccdc_archive 'CCDC 2182084'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2022-06-27 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-06-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H34 N4 O2 Zn'
_chemical_formula_sum            'C32 H34 N4 O2 Zn'
_chemical_formula_weight         572.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.5932(7)
_cell_length_b                   12.3033(9)
_cell_length_c                   24.3137(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.317(2)
_cell_angle_gamma                90
_cell_volume                     2831.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    110.0(0)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_T_max  0.8878
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9186.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24097
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.715
_diffrn_ambient_temperature      110.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2621
_reflns_number_total             3244
_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       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.046
_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)+(0.0418P)²+3.1339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4(H4), C4'(H4'), C5(H5), C5'(H5'), C6(H6), C6'(H6')
2.b Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_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
Zn1 Zn 0.500000 0.67048(3) 0.750000 0.01885(12) Uani 1 2 d S T P . .
O1 O 0.63028(17) 0.74746(13) 0.71204(6) 0.0270(4) Uani 1 1 d . . . . .
N1 N 0.43059(18) 0.59700(14) 0.67527(7) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.21464(19) 0.52729(15) 0.68632(7) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.5299(2) 0.62657(17) 0.63975(8) 0.0185(4) Uani 1 1 d . . . . .
C1' C 0.2261(2) 0.61864(17) 0.59899(9) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.6327(2) 0.70419(18) 0.66189(9) 0.0232(5) Uani 1 1 d . . . . .
C2' C 0.1880(2) 0.72843(18) 0.59344(9) 0.0213(5) Uani 1 1 d . . . . .
C3 C 0.7384(2) 0.7309(2) 0.63071(10) 0.0307(5) Uani 1 1 d . . . . .
H3 H 0.807054 0.784111 0.644468 0.037 Uiso 1 1 calc R U . . .
C3' C 0.1140(2) 0.76296(19) 0.54235(9) 0.0243(5) Uani 1 1 d . . . . .
H3' H 0.084040 0.836518 0.538244 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7442(3) 0.6808(2) 0.57998(10) 0.0348(6) Uani 1 1 d . . . . .
H4 H 0.815475 0.701030 0.558980 0.042 Uiso 1 1 calc R U . . .
C4' C 0.0831(2) 0.69344(19) 0.49764(9) 0.0250(5) Uani 1 1 d . . . . .
H4' H 0.033635 0.719347 0.463115 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6467(2) 0.6015(2) 0.55982(10) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.652510 0.565890 0.525592 0.038 Uiso 1 1 calc R U . . .
C5' C 0.1244(2) 0.58586(19) 0.50320(9) 0.0249(5) Uani 1 1 d . . . . .
H5' H 0.105908 0.538066 0.472189 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5405(2) 0.57428(19) 0.58983(9) 0.0244(5) Uani 1 1 d . . . . .
H6 H 0.474313 0.519342 0.576176 0.029 Uiso 1 1 calc R U . . .
C6' C 0.1931(2) 0.54771(18) 0.55444(9) 0.0218(5) Uani 1 1 d . . . . .
H6' H 0.217488 0.473017 0.558864 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2968(2) 0.57905(16) 0.65515(8) 0.0194(4) Uani 1 1 d . . . . .
C7' C 0.2246(3) 0.80578(19) 0.64113(11) 0.0352(6) Uani 1 1 d . . . . .
H7'A H 0.196888 0.774252 0.674765 0.053 Uiso 1 1 calc R U . . .
H7'B H 0.174281 0.874494 0.632311 0.053 Uiso 1 1 calc R U . . .
H7'C H 0.326658 0.819221 0.647536 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2732(3) 0.48103(19) 0.74045(9) 0.0301(5) Uani 1 1 d . . . . .
H8A H 0.370995 0.458272 0.740122 0.045 Uiso 1 1 calc R U . . .
H8B H 0.216829 0.417972 0.747977 0.045 Uiso 1 1 calc R U . . .
H8C H 0.271206 0.535814 0.769568 0.045 Uiso 1 1 calc R U . . .
C9 C 0.0604(3) 0.5240(2) 0.67311(11) 0.0343(6) Uani 1 1 d . . . . .
H9A H 0.020031 0.568989 0.699822 0.051 Uiso 1 1 calc R U . . .
H9B H 0.027997 0.448807 0.675347 0.051 Uiso 1 1 calc R U . . .
H9C H 0.030001 0.551868 0.635326 0.051 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 O1 1.9195(15) . ?
Zn1 O1 1.9195(15) 2_656 ?
Zn1 N1 2.0422(17) 2_656 ?
Zn1 N1 2.0422(17) . ?
O1 C2 1.334(3) . ?
N1 C1 1.433(3) . ?
N1 C7 1.316(3) . ?
N2 C7 1.339(3) . ?
N2 C8 1.460(3) . ?
N2 C9 1.463(3) . ?
C1 C2 1.415(3) . ?
C1 C6 1.392(3) . ?
C1' C2' 1.400(3) . ?
C1' C6' 1.387(3) . ?
C1' C7 1.504(3) . ?
C2 C3 1.400(3) . ?
C2' C3' 1.394(3) . ?
C2' C7' 1.497(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C4' H4' 0.9500 . ?
C4' C5' 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.393(3) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 120.87(10) . 2_656 ?
O1 Zn1 N1 120.16(7) 2_656 . ?
O1 Zn1 N1 86.24(7) 2_656 2_656 ?
O1 Zn1 N1 86.24(7) . . ?
O1 Zn1 N1 120.16(7) . 2_656 ?
N1 Zn1 N1 127.45(10) . 2_656 ?
C2 O1 Zn1 110.58(13) . . ?
C1 N1 Zn1 105.72(13) . . ?
C7 N1 Zn1 124.25(14) . . ?
C7 N1 C1 121.50(17) . . ?
C7 N2 C8 121.29(18) . . ?
C7 N2 C9 123.77(18) . . ?
C8 N2 C9 114.52(18) . . ?
C2 C1 N1 115.64(18) . . ?
C6 C1 N1 123.9(2) . . ?
C6 C1 C2 119.9(2) . . ?
C2' C1' C7 118.18(19) . . ?
C6' C1' C2' 120.6(2) . . ?
C6' C1' C7 121.17(19) . . ?
O1 C2 C1 120.19(19) . . ?
O1 C2 C3 121.5(2) . . ?
C3 C2 C1 118.3(2) . . ?
C1' C2' C7' 120.91(19) . . ?
C3' C2' C1' 117.9(2) . . ?
C3' C2' C7' 121.2(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2' C3' H3' 119.1 . . ?
C4' C3' C2' 121.9(2) . . ?
C4' C3' H3' 119.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3' C4' H4' 120.1 . . ?
C3' C4' C5' 119.7(2) . . ?
C5' C4' H4' 120.1 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4' C5' H5' 120.1 . . ?
C4' C5' C6' 119.8(2) . . ?
C6' C5' H5' 120.1 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1' C6' C5' 120.1(2) . . ?
C1' C6' H6' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
N1 C7 N2 119.81(19) . . ?
N1 C7 C1' 123.53(18) . . ?
N2 C7 C1' 116.59(18) . . ?
C2' C7' H7'A 109.5 . . ?
C2' C7' H7'B 109.5 . . ?
C2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C2 C1 10.8(2) . . . . ?
Zn1 O1 C2 C3 -166.97(18) . . . . ?
Zn1 N1 C1 C2 -7.1(2) . . . . ?
Zn1 N1 C1 C6 164.54(17) . . . . ?
Zn1 N1 C7 N2 -52.6(3) . . . . ?
Zn1 N1 C7 C1' 124.24(18) . . . . ?
O1 C2 C3 C4 176.4(2) . . . . ?
N1 C1 C2 O1 -2.1(3) . . . . ?
N1 C1 C2 C3 175.78(19) . . . . ?
N1 C1 C6 C5 -174.74(19) . . . . ?
C1 N1 C7 N2 164.13(18) . . . . ?
C1 N1 C7 C1' -19.1(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1' C2' C3' C4' -2.4(3) . . . . ?
C2 C1 C6 C5 -3.5(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C2' C1' C6' C5' 1.5(3) . . . . ?
C2' C1' C7 N1 -77.2(3) . . . . ?
C2' C1' C7 N2 99.8(2) . . . . ?
C2' C3' C4' C5' 0.9(3) . . . . ?
C3 C4 C5 C6 1.7(4) . . . . ?
C3' C4' C5' C6' 1.9(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4' C5' C6' C1' -3.1(3) . . . . ?
C6 C1 C2 O1 -174.04(19) . . . . ?
C6 C1 C2 C3 3.8(3) . . . . ?
C6' C1' C2' C3' 1.3(3) . . . . ?
C6' C1' C2' C7' -179.3(2) . . . . ?
C6' C1' C7 N1 105.9(2) . . . . ?
C6' C1' C7 N2 -77.2(3) . . . . ?
C7 N1 C1 C2 142.0(2) . . . . ?
C7 N1 C1 C6 -46.3(3) . . . . ?
C7 C1' C2' C3' -175.73(18) . . . . ?
C7 C1' C2' C7' 3.7(3) . . . . ?
C7 C1' C6' C5' 178.35(19) . . . . ?
C7' C2' C3' C4' 178.1(2) . . . . ?
C8 N2 C7 N1 -5.8(3) . . . . ?
C8 N2 C7 C1' 177.17(19) . . . . ?
C9 N2 C7 N1 166.3(2) . . . . ?
C9 N2 C7 C1' -10.7(3) . . . . ?

