# 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_test
_database_code_depnum_ccdc_archive 'CCDC 2249045'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2023-07-01 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9709(6)
_cell_length_b                   11.5289(5)
_cell_length_c                   14.3295(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.951(2)
_cell_angle_gamma                90
_cell_volume                     1821.08(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8722
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1331 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.7758.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36211
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.106
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                4014
_reflns_number_total             6359
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         6359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.031
_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)+(0.0849P)²+0.2493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
2.d 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 0.78733(11) 0.72749(11) 0.62673(11) 0.0786(4) Uani 1 1 d . . . . .
H1 H 0.713316 0.720691 0.604446 0.118 Uiso 1 1 calc R U . . .
O2 O 0.67585(9) 0.49355(9) 0.67318(10) 0.0667(3) Uani 1 1 d . . . . .
O3 O 0.51357(11) 0.16998(9) 0.66669(12) 0.0815(4) Uani 1 1 d . . . . .
O4 O 0.33610(9) 0.26108(9) 0.61762(9) 0.0613(3) Uani 1 1 d . . . . .
N1 N 0.55887(10) 0.78535(9) 0.60199(9) 0.0491(3) Uani 1 1 d . . . . .
N2 N 0.45600(10) 0.57292(9) 0.59082(9) 0.0492(3) Uani 1 1 d . . . . .
H2 H 0.532444 0.587241 0.612451 0.059 Uiso 1 1 calc R U . . .
C1 C 0.81995(13) 0.82657(14) 0.67976(13) 0.0596(4) Uani 1 1 d . . . . .
C2 C 0.94176(15) 0.85756(18) 0.71845(16) 0.0773(5) Uani 1 1 d . . . . .
H2A H 0.997689 0.810959 0.705766 0.093 Uiso 1 1 calc R U . . .
C3 C 0.98017(16) 0.95685(18) 0.77546(16) 0.0813(6) Uani 1 1 d . . . . .
H3 H 1.061926 0.976700 0.800938 0.098 Uiso 1 1 calc R U . . .
C4 C 0.89915(17) 1.02687(16) 0.79510(15) 0.0776(5) Uani 1 1 d . . . . .
H4 H 0.926051 1.093263 0.834363 0.093 Uiso 1 1 calc R U . . .
C5 C 0.77799(15) 0.99836(14) 0.75645(13) 0.0648(4) Uani 1 1 d . . . . .
H5 H 0.723270 1.045971 0.769809 0.078 Uiso 1 1 calc R U . . .
C6 C 0.73592(12) 0.89880(12) 0.69734(11) 0.0521(3) Uani 1 1 d . . . . .
C7 C 0.60668(12) 0.87585(11) 0.65463(11) 0.0497(3) Uani 1 1 d . . . . .
H7 H 0.555497 0.929681 0.665996 0.060 Uiso 1 1 calc R U . . .
C8 C 0.43086(12) 0.77709(11) 0.55788(10) 0.0462(3) Uani 1 1 d . . . . .
C9 C 0.35605(13) 0.87227(12) 0.51768(12) 0.0554(3) Uani 1 1 d . . . . .
H9 H 0.390497 0.945061 0.519941 0.066 Uiso 1 1 calc R U . . .
C10 C 0.23176(14) 0.86036(14) 0.47459(12) 0.0613(4) Uani 1 1 d . . . . .
H10 H 0.182749 0.924898 0.448878 0.074 Uiso 1 1 calc R U . . .
C11 C 0.18034(13) 0.75241(14) 0.46973(12) 0.0610(4) Uani 1 1 d . . . . .
H11 H 0.096394 0.744463 0.441234 0.073 Uiso 1 1 calc R U . . .
C12 C 0.25257(13) 0.65579(13) 0.50689(12) 0.0560(3) Uani 1 1 d . . . . .
H12 H 0.217190 0.583074 0.502303 0.067 Uiso 1 1 calc R U . . .
C13 C 0.37807(11) 0.66732(11) 0.55110(10) 0.0462(3) Uani 1 1 d . . . . .
C14 C 0.42521(12) 0.46425(11) 0.59879(10) 0.0480(3) Uani 1 1 d . . . . .
H14 H 0.342945 0.446444 0.573259 0.058 Uiso 1 1 calc R U . . .
C15 C 0.50634(12) 0.37513(11) 0.64228(10) 0.0469(3) Uani 1 1 d . . . . .
C16 C 0.63605(12) 0.39748(11) 0.68476(11) 0.0503(3) Uani 1 1 d . . . . .
C17 C 0.72514(14) 0.30856(15) 0.74577(14) 0.0642(4) Uani 1 1 d . . . . .
H17A H 0.736624 0.251862 0.701250 0.096 Uiso 1 1 calc R U . . .
H17B H 0.694954 0.271181 0.791114 0.096 Uiso 1 1 calc R U . . .
H17C H 0.801185 0.345423 0.784216 0.096 Uiso 1 1 calc R U . . .
C18 C 0.45677(13) 0.25921(12) 0.64481(11) 0.0519(3) Uani 1 1 d . . . . .
C19 C 0.27640(17) 0.15121(16) 0.60902(19) 0.0812(6) Uani 1 1 d . . . . .
H19A H 0.310119 0.110002 0.673021 0.097 Uiso 1 1 calc R U . . .
H19B H 0.288471 0.104214 0.557575 0.097 Uiso 1 1 calc R U . . .
C20 C 0.14523(18) 0.1720(2) 0.5811(2) 0.0944(7) Uani 1 1 d . . . . .
H20A H 0.112070 0.210937 0.516839 0.142 Uiso 1 1 calc R U . . .
H20B H 0.134069 0.219325 0.631880 0.142 Uiso 1 1 calc R U . . .
H20C H 0.104515 0.099148 0.576392 0.142 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 0.8200 . ?
O1 C1 1.343(2) . ?
O2 C16 1.2422(17) . ?
O3 C18 1.2052(16) . ?
O4 C18 1.3417(17) . ?
O4 C19 1.4358(19) . ?
N1 C7 1.2839(18) . ?
N1 C8 1.4148(16) . ?
N2 H2 0.8600 . ?
N2 C13 1.4015(15) . ?
N2 C14 1.3234(17) . ?
C1 C2 1.390(2) . ?
C1 C6 1.402(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(2) . ?
C6 C7 1.4490(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.3912(17) . ?
C8 C13 1.4009(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.3906(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3839(17) . ?
C15 C16 1.4529(19) . ?
C15 C18 1.4685(18) . ?
C16 C17 1.492(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.481(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
C18 O4 C19 117.01(12) . . ?
C7 N1 C8 118.30(11) . . ?
C13 N2 H2 116.3 . . ?
C14 N2 H2 116.3 . . ?
C14 N2 C13 127.34(12) . . ?
O1 C1 C2 118.22(15) . . ?
O1 C1 C6 122.42(14) . . ?
C2 C1 C6 119.36(16) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.41(18) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.75(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.69(18) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.94(17) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.57(14) . . ?
C5 C6 C1 118.82(14) . . ?
C5 C6 C7 118.60(13) . . ?
N1 C7 C6 123.67(12) . . ?
N1 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
C9 C8 N1 122.83(12) . . ?
C9 C8 C13 118.93(12) . . ?
C13 C8 N1 118.20(11) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.02(14) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.72(13) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(13) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.04(14) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 N2 117.55(11) . . ?
C12 C13 N2 122.72(12) . . ?
C12 C13 C8 119.73(11) . . ?
N2 C14 H14 117.6 . . ?
N2 C14 C15 124.86(13) . . ?
C15 C14 H14 117.6 . . ?
C14 C15 C16 120.31(12) . . ?
C14 C15 C18 117.87(12) . . ?
C16 C15 C18 121.82(11) . . ?
O2 C16 C15 120.34(12) . . ?
O2 C16 C17 117.85(13) . . ?
C15 C16 C17 121.78(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 121.57(13) . . ?
O3 C18 C15 126.21(13) . . ?
O4 C18 C15 112.20(11) . . ?
O4 C19 H19A 110.0 . . ?
O4 C19 H19B 110.0 . . ?
O4 C19 C20 108.68(16) . . ?
H19A C19 H19B 108.3 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 H1 N1 0.82 1.98 2.7007(15) 146.1 .
N2 H2 O2 0.86 1.93 2.5951(14) 133.7 .
C3 H3 O2 0.93 3.02 3.913(2) 161.5 2_756
C5 H5 O3 0.93 2.76 3.523(2) 139.6 1_565
C7 H7 O3 0.93 2.82 3.5947(17) 142.0 1_565
C14 H14 O1 0.93 3.34 3.9231(19) 122.5 3_666
C19 H19A O2 0.97 2.53 3.461(3) 161.0 2_646
C20 H20A O1 0.96 2.85 3.569(3) 132.5 3_666
C20 H20B O1 0.96 3.21 3.994(3) 139.8 2_646

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 C1 C2 C3 -178.39(18) . . . . ?
O1 C1 C6 C5 177.71(15) . . . . ?
O1 C1 C6 C7 -3.8(2) . . . . ?
N1 C8 C9 C10 179.43(13) . . . . ?
N1 C8 C13 N2 1.44(18) . . . . ?
N1 C8 C13 C12 -179.10(12) . . . . ?
N2 C14 C15 C16 0.8(2) . . . . ?
N2 C14 C15 C18 -179.90(13) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 N1 3.7(2) . . . . ?
C2 C1 C6 C5 -2.1(2) . . . . ?
C2 C1 C6 C7 176.35(15) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C4 C5 C6 C7 -177.16(15) . . . . ?
C5 C6 C7 N1 -177.77(14) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C7 N1 C8 C9 37.46(19) . . . . ?
C7 N1 C8 C13 -145.11(13) . . . . ?
C8 N1 C7 C6 -175.23(12) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
C9 C8 C13 N2 178.97(13) . . . . ?
C9 C8 C13 C12 -1.6(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C11 C12 C13 N2 179.49(14) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C13 N2 C14 C15 -177.43(13) . . . . ?
C13 C8 C9 C10 2.0(2) . . . . ?
C14 N2 C13 C8 174.79(13) . . . . ?
C14 N2 C13 C12 -4.7(2) . . . . ?
C14 C15 C16 O2 -7.5(2) . . . . ?
C14 C15 C16 C17 170.63(14) . . . . ?
C14 C15 C18 O3 169.07(16) . . . . ?
C14 C15 C18 O4 -9.86(18) . . . . ?
C16 C15 C18 O3 -11.6(2) . . . . ?
C16 C15 C18 O4 169.43(12) . . . . ?
C18 O4 C19 C20 178.59(16) . . . . ?
C18 C15 C16 O2 173.23(14) . . . . ?
C18 C15 C16 C17 -8.6(2) . . . . ?
C19 O4 C18 O3 -4.1(2) . . . . ?
C19 O4 C18 C15 174.86(15) . . . . ?

_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_test_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2249048'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2023-07-01 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 Ni O5'
_chemical_formula_sum            'C21 H20 N2 Ni O5'
_chemical_formula_weight         439.10
_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'
Ni Ni 0.3393 1.1124 '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                   8.142(5)
_cell_length_b                   10.284(5)
_cell_length_c                   11.733(6)
_cell_angle_alpha                90.098(16)
_cell_angle_beta                 93.951(16)
_cell_angle_gamma                100.460(12)
_cell_volume                     963.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8995
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.7144.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            33528
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.951
_diffrn_reflns_theta_min         2.681
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                4508
_reflns_number_total             6042
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.090
_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)+(0.0605P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1347
_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:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
Ni1 Ni 0.61611(3) 0.38311(3) 0.52747(2) 0.04133(10) Uani 1 1 d . . . . .
O1 O 0.6126(2) 0.44112(17) 0.67518(14) 0.0507(4) Uani 1 1 d . . . . .
O2 O 0.4504(2) 0.24602(17) 0.56969(14) 0.0489(4) Uani 1 1 d . . . . .
O3 O 0.1991(3) -0.0791(2) 0.3689(2) 0.0831(7) Uani 1 1 d . . . . .
O4 O 0.3997(3) -0.0299(2) 0.24582(18) 0.0696(5) Uani 1 1 d . . . . .
O5 O 0.9709(3) 0.8796(2) 0.90593(17) 0.0811(7) Uani 1 1 d . . . . .
N1 N 0.7786(2) 0.52261(17) 0.48429(14) 0.0378(3) Uani 1 1 d . . . . .
N2 N 0.6161(2) 0.31803(18) 0.37998(15) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.7022(3) 0.5479(2) 0.72264(18) 0.0437(4) Uani 1 1 d . . . . .
C2 C 0.6752(3) 0.5773(3) 0.8383(2) 0.0541(6) Uani 1 1 d . . . . .
H2 H 0.595066 0.520834 0.876292 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7652(4) 0.6869(3) 0.8936(2) 0.0580(6) Uani 1 1 d . . . . .
H3 H 0.745442 0.703799 0.968890 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8878(4) 0.7750(3) 0.8389(2) 0.0558(6) Uani 1 1 d . . . . .
C5 C 0.9176(3) 0.7516(3) 0.72708(19) 0.0485(5) Uani 1 1 d . . . . .
H5 H 0.998172 0.809832 0.690976 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8247(3) 0.6380(2) 0.66665(18) 0.0412(4) Uani 1 1 d . . . . .
C7 C 0.8554(3) 0.6193(2) 0.55030(17) 0.0398(4) Uani 1 1 d . . . . .
H7 H 0.937055 0.681453 0.519051 0.048 Uiso 1 1 calc R U . . .
C8 C 0.8105(3) 0.5169(2) 0.36558(17) 0.0397(4) Uani 1 1 d . . . . .
C9 C 0.9167(3) 0.6114(2) 0.3066(2) 0.0499(5) Uani 1 1 d . . . . .
H9 H 0.975659 0.687232 0.343974 0.060 Uiso 1 1 calc R U . . .
C10 C 0.9331(4) 0.5904(3) 0.1906(2) 0.0578(6) Uani 1 1 d . . . . .
H10 H 1.004067 0.652446 0.150649 0.069 Uiso 1 1 calc R U . . .
C11 C 0.8446(3) 0.4783(3) 0.1346(2) 0.0567(6) Uani 1 1 d . . . . .
H11 H 0.856852 0.465433 0.057404 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7376(3) 0.3846(3) 0.1928(2) 0.0510(5) Uani 1 1 d . . . . .
H12 H 0.677645 0.309763 0.154520 0.061 Uiso 1 1 calc R U . . .
C13 C 0.7206(3) 0.4036(2) 0.30929(18) 0.0411(4) Uani 1 1 d . . . . .
C14 C 0.5280(3) 0.2051(2) 0.3409(2) 0.0457(5) Uani 1 1 d . . . . .
H14 H 0.544398 0.180875 0.266707 0.055 Uiso 1 1 calc R U . . .
C15 C 0.4101(3) 0.1160(2) 0.4004(2) 0.0471(5) Uani 1 1 d . . . . .
C16 C 0.3740(3) 0.1452(2) 0.5127(2) 0.0472(5) Uani 1 1 d . . . . .
C17 C 0.2396(4) 0.0603(3) 0.5777(3) 0.0654(7) Uani 1 1 d . . . . .
H17A H 0.252962 0.086878 0.656807 0.098 Uiso 1 1 calc R U . . .
H17B H 0.249910 -0.030913 0.571236 0.098 Uiso 1 1 calc R U . . .
H17C H 0.131035 0.071240 0.546261 0.098 Uiso 1 1 calc R U . . .
C18 C 0.3228(3) -0.0056(3) 0.3397(2) 0.0557(6) Uani 1 1 d . . . . .
C19 C 0.3256(5) -0.1498(3) 0.1806(3) 0.0830(10) Uani 1 1 d . . . . .
H19A H 0.226297 -0.135758 0.135313 0.100 Uiso 1 1 calc R U . . .
H19B H 0.293554 -0.222235 0.232097 0.100 Uiso 1 1 calc R U . . .
C20 C 0.4504(7) -0.1822(4) 0.1053(4) 0.1226(19) Uani 1 1 d . . . . .
H20A H 0.400662 -0.256532 0.057237 0.184 Uiso 1 1 calc R U . . .
H20B H 0.544031 -0.203671 0.150940 0.184 Uiso 1 1 calc R U . . .
H20C H 0.487885 -0.107471 0.058747 0.184 Uiso 1 1 calc R U . . .
C21 C 1.0947(5) 0.9720(4) 0.8553(3) 0.0821(10) Uani 1 1 d . . . . .
H21A H 1.044598 1.010522 0.790287 0.123 Uiso 1 1 calc R U . . .
H21B H 1.180918 0.927791 0.831243 0.123 Uiso 1 1 calc R U . . .
H21C H 1.142533 1.040304 0.909985 0.123 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
Ni1 O1 1.8357(18) . ?
Ni1 O2 1.8594(18) . ?
Ni1 N1 1.8631(19) . ?
Ni1 N2 1.854(2) . ?
O1 C1 1.304(3) . ?
O2 C16 1.271(3) . ?
O3 C18 1.214(3) . ?
O4 C18 1.349(4) . ?
O4 C19 1.460(3) . ?
O5 C4 1.376(3) . ?
O5 C21 1.418(4) . ?
N1 C7 1.298(3) . ?
N1 C8 1.437(3) . ?
N2 C13 1.420(3) . ?
N2 C14 1.313(3) . ?
C1 C2 1.430(3) . ?
C1 C6 1.429(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(4) . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.429(3) . ?
C6 C7 1.424(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(3) . ?
C8 C13 1.397(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.423(3) . ?
C15 C16 1.412(4) . ?
C15 C18 1.477(3) . ?
C16 C17 1.522(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.472(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 Ni1 O2 83.93(8) . . ?
O1 Ni1 N1 96.02(8) . . ?
O1 Ni1 N2 177.80(8) . . ?
O2 Ni1 N1 178.76(7) . . ?
N2 Ni1 O2 94.02(8) . . ?
N2 Ni1 N1 86.05(8) . . ?
C1 O1 Ni1 126.87(15) . . ?
C16 O2 Ni1 129.85(16) . . ?
C18 O4 C19 116.3(2) . . ?
C4 O5 C21 117.4(2) . . ?
C7 N1 Ni1 125.67(15) . . ?
C7 N1 C8 121.19(19) . . ?
C8 N1 Ni1 113.11(14) . . ?
C13 N2 Ni1 113.56(15) . . ?
C14 N2 Ni1 124.95(16) . . ?
C14 N2 C13 121.5(2) . . ?
O1 C1 C2 117.7(2) . . ?
O1 C1 C6 124.4(2) . . ?
C6 C1 C2 117.8(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
O5 C4 C3 114.8(2) . . ?
O5 C4 C5 125.2(2) . . ?
C5 C4 C3 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.9(2) . . ?
C7 C6 C1 121.7(2) . . ?
C7 C6 C5 118.4(2) . . ?
N1 C7 C6 125.3(2) . . ?
N1 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
C9 C8 N1 126.5(2) . . ?
C13 C8 N1 112.99(19) . . ?
C13 C8 C9 120.5(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C8 C13 N2 114.04(19) . . ?
C8 C13 C12 119.6(2) . . ?
C12 C13 N2 126.3(2) . . ?
N2 C14 H14 116.7 . . ?
N2 C14 C15 126.7(2) . . ?
C15 C14 H14 116.7 . . ?
C14 C15 C18 117.9(2) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 C18 121.2(2) . . ?
O2 C16 C15 123.3(2) . . ?
O2 C16 C17 112.9(2) . . ?
C15 C16 C17 123.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 122.1(3) . . ?
O3 C18 C15 126.2(3) . . ?
O4 C18 C15 111.7(2) . . ?
O4 C19 H19A 110.0 . . ?
O4 C19 H19B 110.0 . . ?
O4 C19 C20 108.4(3) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C9 H9 O3 0.93 2.74 3.613(4) 156.8 1_665
C17 H17C O3 0.96 2.94 3.707(4) 137.3 2_556
C19 H19B O1 0.97 2.71 3.541(4) 143.8 2_656
C20 H20B O2 0.96 3.31 3.924(6) 124.0 2_656
C21 H21A O3 0.96 2.81 3.735(5) 160.9 2_666
C21 H21C O5 0.96 2.60 3.309(4) 131.3 2_777

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
Ni1 O1 C1 C2 177.70(16) . . . . ?
Ni1 O1 C1 C6 -1.8(3) . . . . ?
Ni1 O2 C16 C15 2.7(3) . . . . ?
Ni1 O2 C16 C17 -176.95(16) . . . . ?
Ni1 N1 C7 C6 -2.2(3) . . . . ?
Ni1 N1 C8 C9 175.52(19) . . . . ?
Ni1 N1 C8 C13 -3.8(2) . . . . ?
Ni1 N2 C13 C8 3.3(2) . . . . ?
Ni1 N2 C13 C12 -175.82(19) . . . . ?
Ni1 N2 C14 C15 4.0(3) . . . . ?
O1 Ni1 O2 C16 -177.6(2) . . . . ?
O1 Ni1 N1 C7 1.88(19) . . . . ?
O1 Ni1 N1 C8 -176.23(14) . . . . ?
O1 C1 C2 C3 179.6(2) . . . . ?
O1 C1 C6 C5 -179.3(2) . . . . ?
O1 C1 C6 C7 1.9(3) . . . . ?
O2 Ni1 O1 C1 -178.7(2) . . . . ?
O2 Ni1 N2 C13 174.39(14) . . . . ?
O2 Ni1 N2 C14 -4.73(19) . . . . ?
O5 C4 C5 C6 179.0(3) . . . . ?
N1 Ni1 O1 C1 0.1(2) . . . . ?
N1 Ni1 N2 C13 -4.37(14) . . . . ?
N1 Ni1 N2 C14 176.51(19) . . . . ?
N1 C8 C9 C10 -179.9(2) . . . . ?
N1 C8 C13 N2 0.3(3) . . . . ?
N1 C8 C13 C12 179.52(19) . . . . ?
N2 Ni1 O2 C16 1.6(2) . . . . ?
N2 Ni1 N1 C7 -177.34(18) . . . . ?
N2 Ni1 N1 C8 4.54(14) . . . . ?
N2 C14 C15 C16 1.3(4) . . . . ?
N2 C14 C15 C18 179.3(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C6 C7 N1 0.2(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 -177.6(2) . . . . ?
C2 C3 C4 O5 -178.8(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C6 C7 N1 -178.6(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 N1 C8 C9 -2.7(3) . . . . ?
C7 N1 C8 C13 177.99(19) . . . . ?
C8 N1 C7 C6 175.79(19) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C8 C13 N2 -179.03(19) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 N2 179.5(2) . . . . ?
C11 C12 C13 C8 0.4(4) . . . . ?
C13 N2 C14 C15 -175.0(2) . . . . ?
C13 C8 C9 C10 -0.6(4) . . . . ?
C14 N2 C13 C8 -177.55(19) . . . . ?
C14 N2 C13 C12 3.3(3) . . . . ?
C14 C15 C16 O2 -4.8(4) . . . . ?
C14 C15 C16 C17 174.9(2) . . . . ?
C14 C15 C18 O3 -165.7(3) . . . . ?
C14 C15 C18 O4 15.8(3) . . . . ?
C16 C15 C18 O3 12.3(4) . . . . ?
C16 C15 C18 O4 -166.2(2) . . . . ?
C18 O4 C19 C20 -162.6(3) . . . . ?
C18 C15 C16 O2 177.2(2) . . . . ?
C18 C15 C16 C17 -3.1(4) . . . . ?
C19 O4 C18 O3 0.1(4) . . . . ?
C19 O4 C18 C15 178.7(3) . . . . ?
C21 O5 C4 C3 -179.6(3) . . . . ?
C21 O5 C4 C5 1.2(5) . . . . ?

_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_dv_dv3_ni
_database_code_depnum_ccdc_archive 'CCDC 2249047'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2023-07-01 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 Ni O4'
_chemical_formula_sum            'C20 H18 N2 Ni O4'
_chemical_formula_weight         409.07
_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'
Ni Ni 0.3393 1.1124 '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                   11.2066(7)
_cell_length_b                   11.7649(9)
_cell_length_c                   13.5458(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.150(3)
_cell_angle_gamma                90
_cell_volume                     1745.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1127 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8194.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.049
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36870
_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         33.246
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                4657
_reflns_number_total             6680
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         6680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.014
_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)+(0.0482P)²+0.4107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1156
_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:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_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
Ni1 Ni 0.60530(2) 0.20912(2) 0.64197(2) 0.03406(8) Uani 1 1 d . . . . .
O1 O 0.76491(12) 0.15836(11) 0.66850(11) 0.0466(3) Uani 1 1 d . . . . .
O2 O 0.67231(12) 0.35396(10) 0.65204(10) 0.0420(3) Uani 1 1 d . . . . .
O3 O 0.48676(15) 0.67018(12) 0.63076(13) 0.0589(4) Uani 1 1 d . . . . .
O4 O 0.31412(14) 0.57098(11) 0.58523(12) 0.0525(4) Uani 1 1 d . . . . .
N1 N 0.53583(13) 0.06558(11) 0.63241(11) 0.0337(3) Uani 1 1 d . . . . .
N2 N 0.44728(14) 0.26362(12) 0.61452(11) 0.0346(3) Uani 1 1 d . . . . .
C1 C 0.80214(17) 0.05382(15) 0.68240(15) 0.0410(4) Uani 1 1 d . . . . .
C2 C 0.92911(19) 0.03087(19) 0.70591(18) 0.0551(5) Uani 1 1 d . . . . .
H2 H 0.983839 0.090977 0.710066 0.066 Uiso 1 1 calc R U . . .
C3 C 0.9733(2) -0.0775(2) 0.7227(2) 0.0605(6) Uani 1 1 d . . . . .
H3 H 1.057225 -0.089460 0.738327 0.073 Uiso 1 1 calc R U . . .
C4 C 0.8948(2) -0.1698(2) 0.7167(2) 0.0641(6) Uani 1 1 d . . . . .
H4 H 0.925720 -0.243066 0.728452 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7716(2) -0.15188(17) 0.69324(19) 0.0549(5) Uani 1 1 d . . . . .
H5 H 0.718823 -0.213543 0.689119 0.066 Uiso 1 1 calc R U . . .
C6 C 0.72305(17) -0.04128(15) 0.67518(14) 0.0391(4) Uani 1 1 d . . . . .
C7 C 0.59502(17) -0.03036(15) 0.64948(14) 0.0393(4) Uani 1 1 d . . . . .
H7 H 0.549088 -0.096763 0.644273 0.047 Uiso 1 1 calc R U . . .
C8 C 0.40665(16) 0.06717(14) 0.60747(13) 0.0353(3) Uani 1 1 d . . . . .
C9 C 0.33059(19) -0.02786(16) 0.59325(16) 0.0460(4) Uani 1 1 d . . . . .
H9 H 0.363393 -0.100743 0.600694 0.055 Uiso 1 1 calc R U . . .
C10 C 0.20661(19) -0.01212(18) 0.56812(18) 0.0533(5) Uani 1 1 d . . . . .
H10 H 0.155163 -0.074995 0.558479 0.064 Uiso 1 1 calc R U . . .
C11 C 0.15689(19) 0.09630(19) 0.55690(18) 0.0529(5) Uani 1 1 d . . . . .
H11 H 0.072623 0.105357 0.539516 0.063 Uiso 1 1 calc R U . . .
C12 C 0.23163(18) 0.19099(17) 0.57135(17) 0.0472(5) Uani 1 1 d . . . . .
H12 H 0.198027 0.263561 0.563801 0.057 Uiso 1 1 calc R U . . .
C13 C 0.35752(16) 0.17666(15) 0.59727(13) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.41497(17) 0.37080(14) 0.61173(13) 0.0372(4) Uani 1 1 d . . . . .
H14 H 0.331699 0.385805 0.600004 0.045 Uiso 1 1 calc R U . . .
C15 C 0.49344(18) 0.46557(14) 0.62468(13) 0.0373(4) Uani 1 1 d . . . . .
C16 C 0.62137(18) 0.45075(15) 0.64265(13) 0.0382(4) Uani 1 1 d . . . . .
C17 C 0.7090(2) 0.54909(16) 0.65089(17) 0.0487(5) Uani 1 1 d . . . . .
H17A H 0.720706 0.581511 0.717276 0.073 Uiso 1 1 calc R U . . .
H17B H 0.676193 0.605686 0.601558 0.073 Uiso 1 1 calc R U . . .
H17C H 0.785834 0.522738 0.639098 0.073 Uiso 1 1 calc R U . . .
C18 C 0.43570(19) 0.57903(15) 0.61513(14) 0.0404(4) Uani 1 1 d . . . . .
C19 C 0.2436(2) 0.67546(17) 0.57339(18) 0.0529(5) Uani 1 1 d . . . . .
H19A H 0.271119 0.725606 0.525893 0.063 Uiso 1 1 calc R U . . .
H19B H 0.253142 0.714426 0.637686 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1132(3) 0.6438(3) 0.5350(3) 0.0839(9) Uani 1 1 d . . . . .
H20A H 0.103935 0.609792 0.469416 0.126 Uiso 1 1 calc R U . . .
H20B H 0.063186 0.710661 0.530382 0.126 Uiso 1 1 calc R U . . .
H20C H 0.088417 0.590549 0.580542 0.126 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
Ni1 O1 1.8479(13) . ?
Ni1 O2 1.8556(12) . ?
Ni1 N1 1.8526(13) . ?
Ni1 N2 1.8461(15) . ?
O1 C1 1.300(2) . ?
O2 C16 1.268(2) . ?
O3 C18 1.213(2) . ?
O4 C18 1.341(3) . ?
O4 C19 1.452(2) . ?
N1 C7 1.305(2) . ?
N1 C8 1.416(2) . ?
N2 C13 1.419(2) . ?
N2 C14 1.310(2) . ?
C1 C2 1.417(3) . ?
C1 C6 1.418(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.412(3) . ?
C6 C7 1.409(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(2) . ?
C8 C13 1.396(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.408(2) . ?
C15 C16 1.414(3) . ?
C15 C18 1.477(2) . ?
C16 C17 1.506(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.492(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 Ni1 O2 85.54(6) . . ?
O1 Ni1 N1 95.41(6) . . ?
N1 Ni1 O2 178.97(6) . . ?
N2 Ni1 O1 178.44(6) . . ?
N2 Ni1 O2 92.98(6) . . ?
N2 Ni1 N1 86.07(6) . . ?
C1 O1 Ni1 127.02(12) . . ?
C16 O2 Ni1 130.58(12) . . ?
C18 O4 C19 117.95(16) . . ?
C7 N1 Ni1 125.85(13) . . ?
C7 N1 C8 120.65(14) . . ?
C8 N1 Ni1 113.46(11) . . ?
C13 N2 Ni1 113.54(11) . . ?
C14 N2 Ni1 125.99(13) . . ?
C14 N2 C13 120.46(16) . . ?
O1 C1 C2 119.30(17) . . ?
O1 C1 C6 124.04(17) . . ?
C2 C1 C6 116.66(18) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.20(18) . . ?
C7 C6 C1 122.29(16) . . ?
C7 C6 C5 117.51(17) . . ?
N1 C7 C6 125.15(16) . . ?
N1 C7 H7 117.4 . . ?
C6 C7 H7 117.4 . . ?
C9 C8 N1 125.94(16) . . ?
C9 C8 C13 120.61(17) . . ?
C13 C8 N1 113.45(15) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 118.94(18) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.92(19) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.52(19) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.35(18) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 N2 113.43(16) . . ?
C12 C13 N2 126.90(17) . . ?
C12 C13 C8 119.66(16) . . ?
N2 C14 H14 116.7 . . ?
N2 C14 C15 126.65(17) . . ?
C15 C14 H14 116.7 . . ?
C14 C15 C16 120.53(16) . . ?
C14 C15 C18 117.01(17) . . ?
C16 C15 C18 122.43(16) . . ?
O2 C16 C15 123.15(16) . . ?
O2 C16 C17 114.18(17) . . ?
C15 C16 C17 122.66(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 121.82(18) . . ?
O3 C18 C15 127.00(19) . . ?
O4 C18 C15 111.17(16) . . ?
O4 C19 H19A 110.2 . . ?
O4 C19 H19B 110.2 . . ?
O4 C19 C20 107.33(19) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C5 H5 O3 0.93 2.90 3.762(3) 155.1 1_545
C7 H7 O3 0.93 2.83 3.717(2) 161.0 1_545
C9 H9 O3 0.93 3.02 3.946(3) 176.0 1_545
C19 H19A O1 0.97 2.92 3.799(3) 151.7 3_666
C19 H19A O2 0.97 2.78 3.398(3) 122.2 3_666
C19 H19B O1 0.97 2.76 3.523(3) 136.5 2_656

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
Ni1 O1 C1 C2 -177.59(15) . . . . ?
Ni1 O1 C1 C6 2.7(3) . . . . ?
Ni1 O2 C16 C15 2.4(3) . . . . ?
Ni1 O2 C16 C17 -176.79(13) . . . . ?
Ni1 N1 C7 C6 -2.1(3) . . . . ?
Ni1 N1 C8 C9 178.57(16) . . . . ?
Ni1 N1 C8 C13 -1.3(2) . . . . ?
Ni1 N2 C13 C8 1.8(2) . . . . ?
Ni1 N2 C13 C12 -177.45(16) . . . . ?
Ni1 N2 C14 C15 2.9(3) . . . . ?
O1 Ni1 O2 C16 179.68(16) . . . . ?
O1 Ni1 N1 C7 4.64(16) . . . . ?
O1 Ni1 N1 C8 -177.64(12) . . . . ?
O1 C1 C2 C3 179.1(2) . . . . ?
O1 C1 C6 C5 -178.89(19) . . . . ?
O1 C1 C6 C7 1.6(3) . . . . ?
O2 Ni1 O1 C1 174.67(17) . . . . ?
O2 Ni1 N2 C13 178.35(12) . . . . ?
O2 Ni1 N2 C14 -2.73(15) . . . . ?
N1 Ni1 O1 C1 -4.94(17) . . . . ?
N1 Ni1 N2 C13 -2.04(12) . . . . ?
N1 Ni1 N2 C14 176.88(15) . . . . ?
N1 C8 C9 C10 -179.28(18) . . . . ?
N1 C8 C13 N2 -0.3(2) . . . . ?
N1 C8 C13 C12 179.01(16) . . . . ?
N2 Ni1 O2 C16 0.17(16) . . . . ?
N2 Ni1 N1 C7 -175.84(16) . . . . ?
N2 Ni1 N1 C8 1.88(12) . . . . ?
N2 C14 C15 C16 0.1(3) . . . . ?
N2 C14 C15 C18 178.11(17) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 N1 -1.8(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C6 C7 -178.17(18) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C5 C6 C7 N1 178.62(19) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C7 N1 C8 C9 -3.6(3) . . . . ?
C7 N1 C8 C13 176.52(16) . . . . ?
C8 N1 C7 C6 -179.71(16) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C8 C13 N2 179.80(17) . . . . ?
C9 C8 C13 C12 -0.9(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 N2 179.76(19) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C13 N2 C14 C15 -178.22(17) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
C14 N2 C13 C8 -177.19(16) . . . . ?
C14 N2 C13 C12 3.6(3) . . . . ?
C14 C15 C16 O2 -2.9(3) . . . . ?
C14 C15 C16 C17 176.28(17) . . . . ?
C14 C15 C18 O3 174.21(19) . . . . ?
C14 C15 C18 O4 -6.1(2) . . . . ?
C16 C15 C18 O3 -7.8(3) . . . . ?
C16 C15 C18 O4 171.84(16) . . . . ?
C18 O4 C19 C20 177.2(2) . . . . ?
C18 C15 C16 O2 179.27(16) . . . . ?
C18 C15 C16 C17 -1.6(3) . . . . ?
C19 O4 C18 O3 -1.0(3) . . . . ?
C19 O4 C18 C15 179.28(16) . . . . ?

_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_dv4
_database_code_depnum_ccdc_archive 'CCDC 2249046'
loop_
_audit_author_name
_audit_author_address
'David Villaman'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2023-07-01 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   22.8904(11)
_cell_length_b                   14.1561(6)
_cell_length_c                   24.2635(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7862.3(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.55
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1348 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.8140.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51082
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_min         2.288
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                5111
_reflns_number_total             9795
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9795
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.003
_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)+(0.0676P)²+2.3023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C19A-C20 \\sim C19A-C20A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C19A, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19A, C20A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C19A(H19A,H19B), C19A(H19C,H19D), C19B(H19E,H19F)
5.b Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C2A(H2AA), C3A(H3A), C5A(H5A), C7A(H7A), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C14A(H14A), N2B(H2B), C2B(H2BA), C3B(H3B), C5B(H5B),
 C7B(H7B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C14B(H14B)
5.c Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C21A(H21A,H21B,H21C), C20(H20A,H20B,H20C), C20A(H20D,
 H20E,H20F), C17B(H17D,H17E,H17F), C20B(H20G,H20H,H20I), C21B(H21D,H21E,H21F)
5.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_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
O1A O 0.57973(9) 0.51876(13) 0.39680(8) 0.0949(6) Uani 1 1 d . . . . .
H1A H 0.582844 0.534431 0.364402 0.142 Uiso 1 1 calc R U . . .
O2A O 0.70673(8) 0.58708(14) 0.32929(8) 0.0897(5) Uani 1 1 d . . . . .
O3A O 0.85048(8) 0.63754(17) 0.22792(12) 0.1255(8) Uani 1 1 d . . . . .
O4A O 0.79053(8) 0.63083(16) 0.15716(10) 0.1053(7) Uani 1 1 d . . . . .
O5A O 0.45910(10) 0.78174(15) 0.51869(7) 0.1057(6) Uani 1 1 d . . . . .
N1A N 0.54635(7) 0.61125(12) 0.30584(7) 0.0580(4) Uani 1 1 d . . . . .
N2A N 0.64355(7) 0.61521(12) 0.24110(7) 0.0592(4) Uani 1 1 d . . . . .
H2A H 0.643293 0.602536 0.275767 0.071 Uiso 1 1 calc R U . . .
C1A C 0.54827(10) 0.58493(17) 0.42448(10) 0.0696(6) Uani 1 1 d . . . . .
C2A C 0.54797(12) 0.5823(2) 0.48149(11) 0.0870(8) Uani 1 1 d . . . . .
H2AA H 0.568525 0.535219 0.499860 0.104 Uiso 1 1 calc R U . . .
C3A C 0.51788(12) 0.6481(2) 0.51091(11) 0.0890(8) Uani 1 1 d . . . . .
H3A H 0.518238 0.645461 0.549210 0.107 Uiso 1 1 calc R U . . .
C4A C 0.48680(11) 0.71870(18) 0.48476(10) 0.0748(6) Uani 1 1 d . . . . .
C5A C 0.48560(9) 0.72183(16) 0.42845(9) 0.0654(5) Uani 1 1 d . . . . .
H5A H 0.464201 0.768629 0.410664 0.078 Uiso 1 1 calc R U . . .
C6A C 0.51658(8) 0.65459(15) 0.39724(9) 0.0584(5) Uani 1 1 d . . . . .
C7A C 0.51461(9) 0.66168(15) 0.33807(9) 0.0591(5) Uani 1 1 d . . . . .
H7A H 0.489015 0.705035 0.322382 0.071 Uiso 1 1 calc R U . . .
C8A C 0.53892(8) 0.62225(13) 0.24810(8) 0.0539(5) Uani 1 1 d . . . . .
C9A C 0.48426(9) 0.62923(16) 0.22355(10) 0.0662(6) Uani 1 1 d . . . . .
H9A H 0.450793 0.627476 0.245256 0.079 Uiso 1 1 calc R U . . .
C10A C 0.47935(10) 0.63873(18) 0.16727(10) 0.0770(7) Uani 1 1 d . . . . .
H10A H 0.442692 0.644370 0.151062 0.092 Uiso 1 1 calc R U . . .
C11A C 0.52866(11) 0.63984(19) 0.13517(10) 0.0811(7) Uani 1 1 d . . . . .
H11A H 0.525207 0.646541 0.097176 0.097 Uiso 1 1 calc R U . . .
C12A C 0.58288(10) 0.63120(18) 0.15839(9) 0.0729(6) Uani 1 1 d . . . . .
H12A H 0.615899 0.630945 0.136057 0.088 Uiso 1 1 calc R U . . .
C13A C 0.58885(8) 0.62281(14) 0.21513(8) 0.0555(5) Uani 1 1 d . . . . .
C14A C 0.69555(9) 0.62557(15) 0.21768(10) 0.0632(5) Uani 1 1 d . . . . .
H14A H 0.696209 0.640657 0.180383 0.076 Uiso 1 1 calc R U . . .
C15A C 0.74871(9) 0.61590(15) 0.24389(11) 0.0685(6) Uani 1 1 d . . . . .
C16A C 0.75198(11) 0.59323(17) 0.30132(12) 0.0775(7) Uani 1 1 d . . . . .
C17A C 0.80915(12) 0.5751(3) 0.33018(14) 0.1147(11) Uani 1 1 d . . . . .
H17A H 0.833038 0.534660 0.307790 0.172 Uiso 1 1 calc R U . . .
H17B H 0.801859 0.545093 0.364993 0.172 Uiso 1 1 calc R U . . .
H17C H 0.829000 0.633944 0.336155 0.172 Uiso 1 1 calc R U . . .
C18A C 0.80151(11) 0.62910(18) 0.21052(15) 0.0857(8) Uani 1 1 d . . . . .
C19A C 0.84171(15) 0.6395(3) 0.12149(18) 0.1271(13) Uani 1 1 d D . . . .
H19A H 0.866008 0.691949 0.133218 0.152 Uiso 0.48(4) 1 calc R U P A 1
H19B H 0.864811 0.582123 0.122565 0.152 Uiso 0.48(4) 1 calc R U P A 1
H19C H 0.854394 0.704837 0.119661 0.152 Uiso 0.52(4) 1 calc R U P A 2
H19D H 0.873637 0.601584 0.135656 0.152 Uiso 0.52(4) 1 calc R U P A 2
C21A C 0.43150(18) 0.8600(2) 0.49361(14) 0.1241(12) Uani 1 1 d . . . . .
H21A H 0.459322 0.893592 0.471400 0.186 Uiso 1 1 calc R U . . .
H21B H 0.416477 0.901357 0.521601 0.186 Uiso 1 1 calc R U . . .
H21C H 0.399972 0.838343 0.470804 0.186 Uiso 1 1 calc R U . . .
C20 C 0.8197(10) 0.656(3) 0.0672(7) 0.177(11) Uani 0.48(4) 1 d D . P A 1
H20A H 0.792687 0.606422 0.057729 0.266 Uiso 0.48(4) 1 calc R U P A 1
H20B H 0.851556 0.655684 0.041477 0.266 Uiso 0.48(4) 1 calc R U P A 1
H20C H 0.800172 0.715573 0.066047 0.266 Uiso 0.48(4) 1 calc R U P A 1
C20A C 0.8247(8) 0.607(2) 0.0679(5) 0.161(8) Uani 0.52(4) 1 d D . P A 2
H20D H 0.816294 0.540453 0.069540 0.242 Uiso 0.52(4) 1 calc R U P A 2
H20E H 0.855844 0.617836 0.042263 0.242 Uiso 0.52(4) 1 calc R U P A 2
H20F H 0.790418 0.640372 0.056116 0.242 Uiso 0.52(4) 1 calc R U P A 2
O1B O 0.57587(10) 0.94871(15) 0.41507(8) 0.1045(6) Uani 1 1 d . . . . .
H1B H 0.569773 0.938177 0.382342 0.157 Uiso 1 1 calc R U . . .
O2B O 0.43559(8) 0.89320(14) 0.34658(8) 0.0890(5) Uani 1 1 d . . . . .
O3B O 0.29052(8) 0.86396(17) 0.24381(11) 0.1242(8) Uani 1 1 d . . . . .
O4B O 0.35203(7) 0.85119(15) 0.17411(9) 0.0966(6) Uani 1 1 d . . . . .
O5B O 0.70753(12) 0.67005(19) 0.51303(9) 0.1215(8) Uani 1 1 d . . . . .
N1B N 0.59807(7) 0.86866(13) 0.31736(8) 0.0626(4) Uani 1 1 d . . . . .
N2B N 0.49767(7) 0.88404(11) 0.25619(8) 0.0603(4) Uani 1 1 d . . . . .
H2B H 0.498801 0.892335 0.291284 0.072 Uiso 1 1 calc R U . . .
C1B C 0.60985(12) 0.87917(19) 0.43629(11) 0.0795(7) Uani 1 1 d . . . . .
C2B C 0.61858(15) 0.8768(2) 0.49294(13) 0.1054(10) Uani 1 1 d . . . . .
H2BA H 0.602088 0.923163 0.515178 0.127 Uiso 1 1 calc R U . . .
C3B C 0.65130(16) 0.8065(3) 0.51606(12) 0.1075(10) Uani 1 1 d . . . . .
H3B H 0.656676 0.805700 0.554045 0.129 Uiso 1 1 calc R U . . .
C4B C 0.67638(12) 0.7373(2) 0.48452(11) 0.0860(7) Uani 1 1 d . . . . .
C5B C 0.66929(10) 0.73958(18) 0.42870(10) 0.0721(6) Uani 1 1 d . . . . .
H5B H 0.686760 0.693352 0.407010 0.086 Uiso 1 1 calc R U . . .
C6B C 0.63593(9) 0.81086(16) 0.40361(9) 0.0638(5) Uani 1 1 d . . . . .
C7B C 0.63133(9) 0.81163(16) 0.34422(9) 0.0632(5) Uani 1 1 d . . . . .
H7B H 0.653617 0.768562 0.324323 0.076 Uiso 1 1 calc R U . . .
C8B C 0.60235(8) 0.87103(14) 0.25901(9) 0.0586(5) Uani 1 1 d . . . . .
C9B C 0.65553(9) 0.86655(17) 0.23194(10) 0.0707(6) Uani 1 1 d . . . . .
H9B H 0.689728 0.859260 0.252182 0.085 Uiso 1 1 calc R U . . .
C10B C 0.65833(11) 0.87278(19) 0.17514(11) 0.0808(7) Uani 1 1 d . . . . .
H10B H 0.694164 0.868645 0.157239 0.097 Uiso 1 1 calc R U . . .
C11B C 0.60801(11) 0.88508(19) 0.14533(11) 0.0813(7) Uani 1 1 d . . . . .
H11B H 0.609855 0.889437 0.107122 0.098 Uiso 1 1 calc R U . . .
C12B C 0.55512(10) 0.89098(17) 0.17136(10) 0.0727(6) Uani 1 1 d . . . . .
H12B H 0.521387 0.900567 0.150736 0.087 Uiso 1 1 calc R U . . .
C13B C 0.55132(8) 0.88282(14) 0.22820(9) 0.0581(5) Uani 1 1 d . . . . .
C14B C 0.44530(9) 0.87356(14) 0.23341(10) 0.0619(5) Uani 1 1 d . . . . .
H14B H 0.444239 0.863406 0.195553 0.074 Uiso 1 1 calc R U . . .
C15B C 0.39248(9) 0.87629(15) 0.26040(11) 0.0671(6) Uani 1 1 d . . . . .
C16B C 0.38987(11) 0.88976(17) 0.31918(12) 0.0770(7) Uani 1 1 d . . . . .
C17B C 0.33259(12) 0.9015(2) 0.34922(14) 0.1086(10) Uani 1 1 d . . . . .
H17D H 0.311155 0.843262 0.347912 0.163 Uiso 1 1 calc R U . . .
H17E H 0.310154 0.950552 0.331933 0.163 Uiso 1 1 calc R U . . .
H17F H 0.340020 0.918188 0.386925 0.163 Uiso 1 1 calc R U . . .
C18B C 0.33967(10) 0.86380(18) 0.22713(13) 0.0801(7) Uani 1 1 d . . . . .
C19B C 0.30255(13) 0.8437(3) 0.13696(16) 0.1151(12) Uani 1 1 d . . . . .
H19E H 0.279788 0.901466 0.137542 0.138 Uiso 1 1 calc R U . . .
H19F H 0.277497 0.791642 0.147825 0.138 Uiso 1 1 calc R U . . .
C20B C 0.32650(18) 0.8272(3) 0.08167(17) 0.1543(17) Uani 1 1 d . . . . .
H20G H 0.348802 0.769724 0.081672 0.231 Uiso 1 1 calc R U . . .
H20H H 0.351300 0.879016 0.071523 0.231 Uiso 1 1 calc R U . . .
H20I H 0.295075 0.821940 0.055646 0.231 Uiso 1 1 calc R U . . .
C21B C 0.73395(19) 0.5982(3) 0.48190(16) 0.1342(14) Uani 1 1 d . . . . .
H21D H 0.754731 0.556291 0.506030 0.201 Uiso 1 1 calc R U . . .
H21E H 0.760739 0.625750 0.456029 0.201 Uiso 1 1 calc R U . . .
H21F H 0.704467 0.563565 0.462350 0.201 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
O1A H1A 0.8200 . ?
O1A C1A 1.359(3) . ?
O2A C16A 1.241(3) . ?
O3A C18A 1.204(3) . ?
O4A C18A 1.319(4) . ?
O4A C19A 1.462(3) . ?
O5A C4A 1.370(3) . ?
O5A C21A 1.413(4) . ?
N1A C7A 1.284(3) . ?
N1A C8A 1.420(3) . ?
N2A H2A 0.8600 . ?
N2A C13A 1.406(2) . ?
N2A C14A 1.327(2) . ?
C1A C2A 1.384(3) . ?
C1A C6A 1.391(3) . ?
C2A H2AA 0.9300 . ?
C2A C3A 1.360(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.381(3) . ?
C4A C5A 1.367(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.408(3) . ?
C6A C7A 1.440(3) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.389(3) . ?
C8A C13A 1.395(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.377(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.371(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.369(3) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.389(3) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.380(3) . ?
C15A C16A 1.432(4) . ?
C15A C18A 1.466(3) . ?
C16A C17A 1.506(3) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C20 1.427(13) . ?
C19A C20A 1.434(12) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
O1B H1B 0.8200 . ?
O1B C1B 1.356(3) . ?
O2B C16B 1.241(3) . ?
O3B C18B 1.196(3) . ?
O4B C18B 1.329(3) . ?
O4B C19B 1.451(3) . ?
O5B C4B 1.376(3) . ?
O5B C21B 1.403(4) . ?
N1B C7B 1.287(3) . ?
N1B C8B 1.419(3) . ?
N2B H2B 0.8600 . ?
N2B C13B 1.403(3) . ?
N2B C14B 1.328(2) . ?
C1B C2B 1.389(4) . ?
C1B C6B 1.386(3) . ?
C2B H2BA 0.9300 . ?
C2B C3B 1.365(4) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.369(4) . ?
C4B C5B 1.365(3) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.404(3) . ?
C6B C7B 1.445(3) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.385(3) . ?
C8B C13B 1.397(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.382(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.371(3) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.368(3) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.387(3) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.376(3) . ?
C15B C16B 1.440(4) . ?
C15B C18B 1.464(3) . ?
C16B C17B 1.510(3) . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C19B H19E 0.9700 . ?
C19B H19F 0.9700 . ?
C19B C20B 1.468(5) . ?
C20B H20G 0.9600 . ?
C20B H20H 0.9600 . ?
C20B H20I 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?

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
C1A O1A H1A 109.5 . . ?
C18A O4A C19A 115.5(3) . . ?
C4A O5A C21A 117.3(2) . . ?
C7A N1A C8A 118.18(17) . . ?
C13A N2A H2A 116.6 . . ?
C14A N2A H2A 116.6 . . ?
C14A N2A C13A 126.75(19) . . ?
O1A C1A C2A 118.6(2) . . ?
O1A C1A C6A 122.0(2) . . ?
C2A C1A C6A 119.4(2) . . ?
C1A C2A H2AA 119.7 . . ?
C3A C2A C1A 120.6(2) . . ?
C3A C2A H2AA 119.7 . . ?
C2A C3A H3A 119.5 . . ?
C2A C3A C4A 121.0(2) . . ?
C4A C3A H3A 119.5 . . ?
O5A C4A C3A 115.7(2) . . ?
C5A C4A O5A 124.8(2) . . ?
C5A C4A C3A 119.5(2) . . ?
C4A C5A H5A 119.8 . . ?
C4A C5A C6A 120.4(2) . . ?
C6A C5A H5A 119.8 . . ?
C1A C6A C5A 119.1(2) . . ?
C1A C6A C7A 122.6(2) . . ?
C5A C6A C7A 118.25(19) . . ?
N1A C7A C6A 123.4(2) . . ?
N1A C7A H7A 118.3 . . ?
C6A C7A H7A 118.3 . . ?
C9A C8A N1A 122.60(18) . . ?
C9A C8A C13A 119.43(19) . . ?
C13A C8A N1A 117.93(17) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A C8A 120.4(2) . . ?
C10A C9A H9A 119.8 . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A C9A 119.8(2) . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A H11A 119.6 . . ?
C12A C11A C10A 120.8(2) . . ?
C12A C11A H11A 119.6 . . ?
C11A C12A H12A 119.8 . . ?
C11A C12A C13A 120.3(2) . . ?
C13A C12A H12A 119.8 . . ?
C8A C13A N2A 118.17(18) . . ?
C12A C13A N2A 122.58(18) . . ?
C12A C13A C8A 119.24(18) . . ?
N2A C14A H14A 117.2 . . ?
N2A C14A C15A 125.6(2) . . ?
C15A C14A H14A 117.2 . . ?
C14A C15A C16A 121.1(2) . . ?
C14A C15A C18A 117.4(3) . . ?
C16A C15A C18A 121.5(2) . . ?
O2A C16A C15A 120.3(2) . . ?
O2A C16A C17A 117.3(3) . . ?
C15A C16A C17A 122.4(3) . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O3A C18A O4A 121.3(3) . . ?
O3A C18A C15A 125.9(3) . . ?
O4A C18A C15A 112.8(2) . . ?
O4A C19A H19A 110.5 . . ?
O4A C19A H19B 110.5 . . ?
O4A C19A H19C 110.3 . . ?
O4A C19A H19D 110.3 . . ?
H19A C19A H19B 108.7 . . ?
H19C C19A H19D 108.6 . . ?
C20 C19A O4A 106.1(10) . . ?
C20 C19A H19A 110.5 . . ?
C20 C19A H19B 110.5 . . ?
C20A C19A O4A 106.9(8) . . ?
C20A C19A H19C 110.3 . . ?
C20A C19A H19D 110.3 . . ?
O5A C21A H21A 109.5 . . ?
O5A C21A H21B 109.5 . . ?
O5A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C19A C20 H20A 109.5 . . ?
C19A C20 H20B 109.5 . . ?
C19A C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C1B O1B H1B 109.5 . . ?
C18B O4B C19B 116.4(2) . . ?
C4B O5B C21B 117.0(3) . . ?
C7B N1B C8B 118.62(18) . . ?
C13B N2B H2B 117.0 . . ?
C14B N2B H2B 117.0 . . ?
C14B N2B C13B 125.9(2) . . ?
O1B C1B C2B 118.4(2) . . ?
O1B C1B C6B 122.4(2) . . ?
C6B C1B C2B 119.1(3) . . ?
C1B C2B H2BA 119.9 . . ?
C3B C2B C1B 120.2(3) . . ?
C3B C2B H2BA 119.9 . . ?
C2B C3B H3B 119.3 . . ?
C2B C3B C4B 121.4(3) . . ?
C4B C3B H3B 119.3 . . ?
C3B C4B O5B 115.6(3) . . ?
C5B C4B O5B 125.2(3) . . ?
C5B C4B C3B 119.2(3) . . ?
C4B C5B H5B 119.6 . . ?
C4B C5B C6B 120.8(2) . . ?
C6B C5B H5B 119.6 . . ?
C1B C6B C5B 119.2(2) . . ?
C1B C6B C7B 122.3(2) . . ?
C5B C6B C7B 118.5(2) . . ?
N1B C7B C6B 123.6(2) . . ?
N1B C7B H7B 118.2 . . ?
C6B C7B H7B 118.2 . . ?
C9B C8B N1B 122.20(18) . . ?
C9B C8B C13B 119.1(2) . . ?
C13B C8B N1B 118.61(18) . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B C8B 120.7(2) . . ?
C10B C9B H9B 119.6 . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B C9B 119.7(2) . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B H11B 119.7 . . ?
C12B C11B C10B 120.5(2) . . ?
C12B C11B H11B 119.7 . . ?
C11B C12B H12B 119.7 . . ?
C11B C12B C13B 120.6(2) . . ?
C13B C12B H12B 119.7 . . ?
C8B C13B N2B 118.31(19) . . ?
C12B C13B N2B 122.34(18) . . ?
C12B C13B C8B 119.33(19) . . ?
N2B C14B H14B 116.9 . . ?
N2B C14B C15B 126.3(2) . . ?
C15B C14B H14B 116.9 . . ?
C14B C15B C16B 120.8(2) . . ?
C14B C15B C18B 117.4(2) . . ?
C16B C15B C18B 121.9(2) . . ?
O2B C16B C15B 120.1(2) . . ?
O2B C16B C17B 118.0(3) . . ?
C15B C16B C17B 121.9(3) . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
O3B C18B O4B 121.9(3) . . ?
O3B C18B C15B 126.2(3) . . ?
O4B C18B C15B 112.0(2) . . ?
O4B C19B H19E 110.4 . . ?
O4B C19B H19F 110.4 . . ?
O4B C19B C20B 106.7(3) . . ?
H19E C19B H19F 108.6 . . ?
C20B C19B H19E 110.4 . . ?
C20B C19B H19F 110.4 . . ?
C19B C20B H20G 109.5 . . ?
C19B C20B H20H 109.5 . . ?
C19B C20B H20I 109.5 . . ?
H20G C20B H20H 109.5 . . ?
H20G C20B H20I 109.5 . . ?
H20H C20B H20I 109.5 . . ?
O5B C21B H21D 109.5 . . ?
O5B C21B H21E 109.5 . . ?
O5B C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 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
O1A H1A N1A 0.82 1.97 2.678(2) 143.3 .
N2A H2A O2A 0.86 1.96 2.613(2) 131.8 .
C5A H5A O2B 0.93 2.44 3.338(3) 162.1 .
C7A H7A O2B 0.93 2.99 3.749(3) 139.9 .
C7A H7A N2B 0.93 3.01 3.743(3) 137.2 .
C9A H9A O3A 0.93 2.39 3.283(3) 160.7 6_556
C11A H11A O5A 0.93 2.64 3.428(3) 143.5 7_575
C17A H17A N1B 0.96 2.84 3.626(3) 139.8 8_755
C21A H21B O1B 0.96 2.63 3.502(4) 151.9 5_676
C20 H20C O5B 0.96 2.96 3.80(3) 146.1 7_575
O1B H1B N1B 0.82 1.97 2.676(3) 144.2 .
N2B H2B O2B 0.86 1.97 2.617(3) 130.7 .
C5B H5B O2A 0.93 2.46 3.348(3) 161.0 .
C7B H7B O2A 0.93 2.84 3.635(3) 143.6 .
C7B H7B N2A 0.93 2.97 3.751(3) 142.0 .
C9B H9B O3B 0.93 2.31 3.146(3) 149.3 6_656
C12B H12B O1A 0.93 3.08 3.941(3) 154.8 3_655
C14B H14B O1A 0.93 3.19 3.812(3) 126.3 3_655
C17B H17D O4A 0.96 3.05 3.954(4) 158.2 6_556
C17B H17E N2A 0.96 3.11 3.775(3) 127.4 3_655
C19B H19E O2A 0.97 2.77 3.548(4) 138.2 3_655
C20B H20G O5A 0.96 3.04 3.731(5) 130.1 7_575
C20B H20H O1A 0.96 2.65 3.498(4) 148.2 3_655

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
O1A C1A C2A C3A 178.9(3) . . . . ?
O1A C1A C6A C5A -179.1(2) . . . . ?
O1A C1A C6A C7A 0.2(3) . . . . ?
O5A C4A C5A C6A 178.7(2) . . . . ?
N1A C8A C9A C10A -179.2(2) . . . . ?
N1A C8A C13A N2A -1.8(3) . . . . ?
N1A C8A C13A C12A 178.49(19) . . . . ?
N2A C14A C15A C16A -0.3(3) . . . . ?
N2A C14A C15A C18A 179.3(2) . . . . ?
C1A C2A C3A C4A 0.2(4) . . . . ?
C1A C6A C7A N1A -7.5(3) . . . . ?
C2A C1A C6A C5A 1.0(3) . . . . ?
C2A C1A C6A C7A -179.8(2) . . . . ?
C2A C3A C4A O5A -178.9(3) . . . . ?
C2A C3A C4A C5A 0.9(4) . . . . ?
C3A C4A C5A C6A -1.1(4) . . . . ?
C4A C5A C6A C1A 0.1(3) . . . . ?
C4A C5A C6A C7A -179.1(2) . . . . ?
C5A C6A C7A N1A 171.74(19) . . . . ?
C6A C1A C2A C3A -1.1(4) . . . . ?
C7A N1A C8A C9A -43.1(3) . . . . ?
C7A N1A C8A C13A 139.07(19) . . . . ?
C8A N1A C7A C6A 177.72(18) . . . . ?
C8A C9A C10A C11A 1.0(4) . . . . ?
C9A C8A C13A N2A -179.72(18) . . . . ?
C9A C8A C13A C12A 0.6(3) . . . . ?
C9A C10A C11A C12A 0.3(4) . . . . ?
C10A C11A C12A C13A -1.1(4) . . . . ?
C11A C12A C13A N2A -179.0(2) . . . . ?
C11A C12A C13A C8A 0.7(3) . . . . ?
C13A N2A C14A C15A -178.6(2) . . . . ?
C13A C8A C9A C10A -1.4(3) . . . . ?
C14A N2A C13A C8A -171.44(19) . . . . ?
C14A N2A C13A C12A 8.3(3) . . . . ?
C14A C15A C16A O2A -4.1(3) . . . . ?
C14A C15A C16A C17A 175.4(2) . . . . ?
C14A C15A C18A O3A 167.9(3) . . . . ?
C14A C15A C18A O4A -12.2(3) . . . . ?
C16A C15A C18A O3A -12.5(4) . . . . ?
C16A C15A C18A O4A 167.3(2) . . . . ?
C18A O4A C19A C20 -170.7(18) . . . . ?
C18A O4A C19A C20A 159.8(14) . . . . ?
C18A C15A C16A O2A 176.4(2) . . . . ?
C18A C15A C16A C17A -4.2(4) . . . . ?
C19A O4A C18A O3A 2.5(4) . . . . ?
C19A O4A C18A C15A -177.4(2) . . . . ?
C21A O5A C4A C3A 174.1(3) . . . . ?
C21A O5A C4A C5A -5.6(4) . . . . ?
O1B C1B C2B C3B 178.4(3) . . . . ?
O1B C1B C6B C5B -178.3(2) . . . . ?
O1B C1B C6B C7B 3.3(4) . . . . ?
O5B C4B C5B C6B 179.2(2) . . . . ?
N1B C8B C9B C10B -177.4(2) . . . . ?
N1B C8B C13B N2B -5.1(3) . . . . ?
N1B C8B C13B C12B 176.15(19) . . . . ?
N2B C14B C15B C16B -1.3(3) . . . . ?
N2B C14B C15B C18B 179.5(2) . . . . ?
C1B C2B C3B C4B 0.2(5) . . . . ?
C1B C6B C7B N1B -7.7(3) . . . . ?
C2B C1B C6B C5B 1.6(4) . . . . ?
C2B C1B C6B C7B -176.7(2) . . . . ?
C2B C3B C4B O5B -179.1(3) . . . . ?
C2B C3B C4B C5B 1.1(5) . . . . ?
C3B C4B C5B C6B -1.1(4) . . . . ?
C4B C5B C6B C1B -0.3(3) . . . . ?
C4B C5B C6B C7B 178.1(2) . . . . ?
C5B C6B C7B N1B 173.9(2) . . . . ?
C6B C1B C2B C3B -1.6(5) . . . . ?
C7B N1B C8B C9B -40.6(3) . . . . ?
C7B N1B C8B C13B 142.5(2) . . . . ?
C8B N1B C7B C6B 172.36(19) . . . . ?
C8B C9B C10B C11B 1.1(4) . . . . ?
C9B C8B C13B N2B 177.91(19) . . . . ?
C9B C8B C13B C12B -0.8(3) . . . . ?
C9B C10B C11B C12B -0.2(4) . . . . ?
C10B C11B C12B C13B -1.3(4) . . . . ?
C11B C12B C13B N2B -176.9(2) . . . . ?
C11B C12B C13B C8B 1.7(3) . . . . ?
C13B N2B C14B C15B -178.8(2) . . . . ?
C13B C8B C9B C10B -0.6(3) . . . . ?
C14B N2B C13B C8B -164.14(19) . . . . ?
C14B N2B C13B C12B 14.6(3) . . . . ?
C14B C15B C16B O2B -4.5(3) . . . . ?
C14B C15B C16B C17B 174.6(2) . . . . ?
C14B C15B C18B O3B 179.8(3) . . . . ?
C14B C15B C18B O4B 0.1(3) . . . . ?
C16B C15B C18B O3B 0.6(4) . . . . ?
C16B C15B C18B O4B -179.1(2) . . . . ?
C18B O4B C19B C20B -178.2(3) . . . . ?
C18B C15B C16B O2B 174.7(2) . . . . ?
C18B C15B C16B C17B -6.2(3) . . . . ?
C19B O4B C18B O3B 3.8(4) . . . . ?
C19B O4B C18B C15B -176.5(2) . . . . ?
C21B O5B C4B C3B -179.8(3) . . . . ?
C21B O5B C4B C5B 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
