# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ML010
_database_code_depnum_ccdc_archive 'CCDC 1841078'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 Al N2 O2'
_chemical_formula_sum            'C23 H31 Al N2 O2'
_chemical_formula_weight         394.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.6122(12)
_cell_length_b                   21.655(3)
_cell_length_c                   12.1405(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.039(2)
_cell_angle_gamma                90
_cell_volume                     2264.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    8121
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.91

_exptl_crystal_description       'rectangular prism (cut)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25718
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.881
_diffrn_reflns_theta_max         27.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5078
_reflns_number_gt                4076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.1291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5078
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.65524(7) 0.49580(3) 0.26232(5) 0.02498(13) Uani 1 1 d . . . . .
N1 N 0.49465(17) 0.54370(7) 0.19505(12) 0.0244(4) Uani 1 1 d . . . . .
N2 N 0.51544(17) 0.43924(7) 0.33124(13) 0.0258(4) Uani 1 1 d . . . . .
O1 O 0.25295(14) 0.57330(6) 0.14765(11) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.29187(15) 0.38936(6) 0.36668(11) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.3430(2) 0.53119(8) 0.19943(14) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.2786(2) 0.47998(8) 0.25235(16) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.169940 0.473686 0.244915 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3621(2) 0.43715(9) 0.31564(15) 0.0258(4) Uani 1 1 d . . . . .
C4 C 0.5427(2) 0.59770(8) 0.13377(16) 0.0242(4) Uani 1 1 d . . . . .
C5 C 0.5788(2) 0.65211(9) 0.18773(16) 0.0293(5) Uani 1 1 d . . . . .
H5 H 0.570510 0.654391 0.265647 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6274(2) 0.70350(9) 0.12815(17) 0.0321(5) Uani 1 1 d . . . . .
H6 H 0.652690 0.740506 0.166166 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6396(2) 0.70166(9) 0.01382(16) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.6057(2) 0.64613(9) -0.03918(17) 0.0297(5) Uani 1 1 d . . . . .
H8 H 0.614956 0.643648 -0.117021 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5589(2) 0.59451(9) 0.01948(16) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.537825 0.556945 -0.018060 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6886(3) 0.75795(10) -0.05047(18) 0.0427(6) Uani 1 1 d . . . . .
H10A H 0.638808 0.794679 -0.019288 0.064 Uiso 1 1 calc R U . . .
H10B H 0.657289 0.753230 -0.127622 0.064 Uiso 1 1 calc R U . . .
H10C H 0.801697 0.762510 -0.046262 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5883(2) 0.39289(8) 0.40010(16) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.6357(2) 0.40813(9) 0.50625(16) 0.0322(5) Uani 1 1 d . . . . .
H12 H 0.616639 0.448395 0.534211 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7106(3) 0.36470(10) 0.57145(18) 0.0380(5) Uani 1 1 d . . . . .
H13 H 0.742070 0.375827 0.643785 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7407(2) 0.30525(10) 0.53346(17) 0.0344(5) Uani 1 1 d . . . . .
C15 C 0.6950(2) 0.29108(10) 0.42649(18) 0.0360(5) Uani 1 1 d . . . . .
H15 H 0.715138 0.251016 0.398028 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6205(2) 0.33417(9) 0.36052(17) 0.0324(5) Uani 1 1 d . . . . .
H16 H 0.591269 0.323387 0.287544 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8181(3) 0.25788(11) 0.6062(2) 0.0504(6) Uani 1 1 d . . . . .
H17A H 0.841514 0.276369 0.677987 0.076 Uiso 0.5 1 calc R U P . .
H17B H 0.748356 0.222568 0.616300 0.076 Uiso 0.5 1 calc R U P . .
H17C H 0.914664 0.243914 0.571570 0.076 Uiso 0.5 1 calc R U P . .
H17D H 0.828175 0.218865 0.565918 0.076 Uiso 0.5 1 calc R U P . .
H17E H 0.921334 0.272666 0.627604 0.076 Uiso 0.5 1 calc R U P . .
H17F H 0.755025 0.251320 0.672335 0.076 Uiso 0.5 1 calc R U P . .
C18 C 0.0857(2) 0.56579(9) 0.14540(18) 0.0330(5) Uani 1 1 d . . . . .
H18A H 0.045000 0.560566 0.221084 0.040 Uiso 1 1 calc R U . . .
H18B H 0.057050 0.528947 0.101589 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0195(2) 0.62309(10) 0.0938(2) 0.0433(6) Uani 1 1 d . . . . .
H19A H 0.049834 0.659220 0.137391 0.065 Uiso 1 1 calc R U . . .
H19B H -0.093963 0.620042 0.091638 0.065 Uiso 1 1 calc R U . . .
H19C H 0.059581 0.627390 0.018633 0.065 Uiso 1 1 calc R U . . .
C20 C 0.1234(2) 0.38340(9) 0.36816(18) 0.0336(5) Uani 1 1 d . . . . .
H20A H 0.075784 0.424888 0.362389 0.040 Uiso 1 1 calc R U . . .
H20B H 0.090578 0.364976 0.439050 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0667(3) 0.34366(10) 0.2748(2) 0.0443(6) Uani 1 1 d . . . . .
H21A H 0.094852 0.362833 0.204503 0.066 Uiso 1 1 calc R U . . .
H21B H -0.046482 0.339537 0.279250 0.066 Uiso 1 1 calc R U . . .
H21C H 0.114643 0.302725 0.279903 0.066 Uiso 1 1 calc R U . . .
C22 C 0.7778(2) 0.45349(9) 0.14839(17) 0.0314(5) Uani 1 1 d . . . . .
H22A H 0.881460 0.444133 0.177319 0.047 Uiso 1 1 calc R U . . .
H22B H 0.787314 0.480258 0.083660 0.047 Uiso 1 1 calc R U . . .
H22C H 0.725808 0.414988 0.127428 0.047 Uiso 1 1 calc R U . . .
C23 C 0.7728(2) 0.54462(10) 0.37075(17) 0.0340(5) Uani 1 1 d . . . . .
H23A H 0.701983 0.560047 0.427558 0.051 Uiso 1 1 calc R U . . .
H23B H 0.822741 0.579575 0.333678 0.051 Uiso 1 1 calc R U . . .
H23C H 0.852378 0.518542 0.404984 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
Al1 N2 1.9108(17) . ?
Al1 N1 1.9116(16) . ?
Al1 C22 1.967(2) . ?
Al1 C23 1.968(2) . ?
N1 C1 1.335(2) . ?
N1 C4 1.447(2) . ?
N2 C3 1.335(2) . ?
N2 C11 1.449(2) . ?
O1 C1 1.352(2) . ?
O1 C18 1.450(2) . ?
O2 C3 1.350(2) . ?
O2 C20 1.457(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.402(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.383(3) . ?
C4 C9 1.396(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C10 1.508(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.387(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 C17 1.508(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 C19 1.502(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.504(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
N2 Al1 N1 94.53(7) . . ?
N2 Al1 C22 110.36(8) . . ?
N1 Al1 C22 109.93(8) . . ?
N2 Al1 C23 112.06(8) . . ?
N1 Al1 C23 111.47(8) . . ?
C22 Al1 C23 116.37(9) . . ?
C1 N1 C4 117.70(15) . . ?
C1 N1 Al1 125.47(13) . . ?
C4 N1 Al1 116.83(11) . . ?
C3 N2 C11 119.12(16) . . ?
C3 N2 Al1 125.68(14) . . ?
C11 N2 Al1 115.07(12) . . ?
C1 O1 C18 120.19(15) . . ?
C3 O2 C20 121.34(15) . . ?
N1 C1 O1 113.93(16) . . ?
N1 C1 C2 124.65(17) . . ?
O1 C1 C2 121.43(17) . . ?
C1 C2 C3 124.99(17) . . ?
C1 C2 H2 117.5 . . ?
C3 C2 H2 117.5 . . ?
N2 C3 O2 113.86(17) . . ?
N2 C3 C2 124.21(18) . . ?
O2 C3 C2 121.94(17) . . ?
C5 C4 C9 119.35(17) . . ?
C5 C4 N1 120.61(17) . . ?
C9 C4 N1 119.99(17) . . ?
C4 C5 C6 120.16(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 121.19(18) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C8 117.95(18) . . ?
C6 C7 C10 120.93(18) . . ?
C8 C7 C10 121.12(18) . . ?
C9 C8 C7 121.29(19) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 120.01(18) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.67(18) . . ?
C16 C11 N2 121.44(18) . . ?
C12 C11 N2 119.78(17) . . ?
C13 C12 C11 120.23(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 117.41(19) . . ?
C15 C14 C17 121.4(2) . . ?
C13 C14 C17 121.2(2) . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O1 C18 C19 106.96(16) . . ?
O1 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 111.37(17) . . ?
O2 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
O2 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Al1 C22 H22A 109.5 . . ?
Al1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Al1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Al1 C23 H23A 109.5 . . ?
Al1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Al1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 N1 C1 O1 -2.3(2) . . . . ?
Al1 N1 C1 O1 178.18(11) . . . . ?
C4 N1 C1 C2 178.06(17) . . . . ?
Al1 N1 C1 C2 -1.5(3) . . . . ?
C18 O1 C1 N1 179.92(16) . . . . ?
C18 O1 C1 C2 -0.4(3) . . . . ?
N1 C1 C2 C3 5.3(3) . . . . ?
O1 C1 C2 C3 -174.30(17) . . . . ?
C11 N2 C3 O2 -1.2(2) . . . . ?
Al1 N2 C3 O2 174.44(12) . . . . ?
C11 N2 C3 C2 178.91(17) . . . . ?
Al1 N2 C3 C2 -5.5(3) . . . . ?
C20 O2 C3 N2 173.59(16) . . . . ?
C20 O2 C3 C2 -6.5(3) . . . . ?
C1 C2 C3 N2 -1.6(3) . . . . ?
C1 C2 C3 O2 178.49(17) . . . . ?
C1 N1 C4 C5 100.4(2) . . . . ?
Al1 N1 C4 C5 -80.06(19) . . . . ?
C1 N1 C4 C9 -82.2(2) . . . . ?
Al1 N1 C4 C9 97.38(18) . . . . ?
C9 C4 C5 C6 1.5(3) . . . . ?
N1 C4 C5 C6 178.95(17) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C5 C6 C7 C10 178.6(2) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C10 C7 C8 C9 -179.3(2) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C5 C4 C9 C8 -2.2(3) . . . . ?
N1 C4 C9 C8 -179.65(17) . . . . ?
C3 N2 C11 C16 79.5(2) . . . . ?
Al1 N2 C11 C16 -96.59(19) . . . . ?
C3 N2 C11 C12 -104.3(2) . . . . ?
Al1 N2 C11 C12 79.7(2) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
N2 C11 C12 C13 -177.69(19) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 C17 -178.2(2) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C17 C14 C15 C16 178.4(2) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
N2 C11 C16 C15 177.86(18) . . . . ?
C1 O1 C18 C19 173.70(16) . . . . ?
C3 O2 C20 C21 93.5(2) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_ML031
_database_code_depnum_ccdc_archive 'CCDC 1841085'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H50 N4 O4 Zn'
_chemical_formula_sum            'C42 H50 N4 O4 Zn'
_chemical_formula_weight         740.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4917(2)
_cell_length_b                   11.5000(2)
_cell_length_c                   17.1243(3)
_cell_angle_alpha                72.7160(10)
_cell_angle_beta                 77.5890(10)
_cell_angle_gamma                64.8750(10)
_cell_volume                     1946.07(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.47

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.677
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34049
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.252
_diffrn_reflns_theta_max         28.829
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9316
_reflns_number_gt                7430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.5454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9316
_refine_ls_number_parameters     467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.30551(2) 0.37448(2) 0.24273(2) 0.01876(7) Uani 1 1 d . . . . .
O1 O 0.66631(11) 0.21573(12) 0.11921(8) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.41324(11) 0.67550(12) 0.09414(8) 0.0233(3) Uani 1 1 d . . . . .
O3 O -0.04591(11) 0.35386(13) 0.25129(7) 0.0250(3) Uani 1 1 d . . . . .
O4 O 0.15737(12) 0.28635(14) 0.48592(8) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.47779(13) 0.25999(14) 0.20070(9) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.32320(13) 0.54507(14) 0.18873(9) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.15571(14) 0.35071(15) 0.22086(9) 0.0210(3) Uani 1 1 d . . . . .
N4 N 0.27096(14) 0.33352(15) 0.36456(9) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.55441(16) 0.30884(17) 0.14475(11) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.52852(16) 0.44303(17) 0.11073(11) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.589365 0.463445 0.067675 0.024 Uiso 1 1 calc R U . . .
C3 C 0.42240(16) 0.55062(17) 0.13336(11) 0.0195(4) Uani 1 1 d . . . . .
C4 C 0.52318(16) 0.11997(17) 0.23325(11) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.60630(18) 0.05921(19) 0.29398(12) 0.0283(4) Uani 1 1 d . . . . .
H5 H 0.634451 0.110600 0.314037 0.034 Uiso 1 1 calc R U . . .
C6 C 0.64889(19) -0.0760(2) 0.32586(13) 0.0326(5) Uani 1 1 d . . . . .
H6 H 0.706386 -0.116130 0.367352 0.039 Uiso 1 1 calc R U . . .
C7 C 0.60913(19) -0.15384(19) 0.29829(13) 0.0313(5) Uani 1 1 d . . . . .
C8 C 0.5228(2) -0.0915(2) 0.23950(13) 0.0339(5) Uani 1 1 d . . . . .
H8 H 0.492681 -0.142520 0.220606 0.041 Uiso 1 1 calc R U . . .
C9 C 0.47908(19) 0.04343(19) 0.20749(12) 0.0286(4) Uani 1 1 d . . . . .
H9 H 0.418683 0.083987 0.167724 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6610(2) -0.3020(2) 0.33135(15) 0.0455(6) Uani 1 1 d . . . . .
H10A H 0.609108 -0.338743 0.315425 0.068 Uiso 1 1 calc R U . . .
H10B H 0.656385 -0.322389 0.391437 0.068 Uiso 1 1 calc R U . . .
H10C H 0.751067 -0.340891 0.308591 0.068 Uiso 1 1 calc R U . . .
C11 C 0.23183(16) 0.66472(17) 0.21101(11) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.10079(17) 0.69939(18) 0.20969(11) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.072611 0.643673 0.194051 0.028 Uiso 1 1 calc R U . . .
C13 C 0.01041(18) 0.81501(19) 0.23106(12) 0.0285(4) Uani 1 1 d . . . . .
H13 H -0.078869 0.837907 0.229213 0.034 Uiso 1 1 calc R U . . .
C14 C 0.04890(19) 0.89762(19) 0.25512(12) 0.0283(4) Uani 1 1 d . . . . .
C15 C 0.17926(19) 0.85976(19) 0.25919(12) 0.0276(4) Uani 1 1 d . . . . .
H15 H 0.207096 0.913967 0.276700 0.033 Uiso 1 1 calc R U . . .
C16 C 0.27030(18) 0.74454(18) 0.23832(11) 0.0238(4) Uani 1 1 d . . . . .
H16 H 0.359149 0.719863 0.242629 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0494(2) 1.0257(2) 0.27615(15) 0.0417(6) Uani 1 1 d . . . . .
H17A H -0.136221 1.035983 0.269819 0.063 Uiso 0.5 1 calc R U P . .
H17B H -0.045152 1.023724 0.333106 0.063 Uiso 0.5 1 calc R U P . .
H17C H -0.030226 1.100109 0.239109 0.063 Uiso 0.5 1 calc R U P . .
H17D H -0.004844 1.070561 0.291537 0.063 Uiso 0.5 1 calc R U P . .
H17E H -0.095914 1.082820 0.228250 0.063 Uiso 0.5 1 calc R U P . .
H17F H -0.110840 1.006436 0.322248 0.063 Uiso 0.5 1 calc R U P . .
C18 C 0.76013(17) 0.25301(19) 0.05803(12) 0.0239(4) Uani 1 1 d . . . . .
H18A H 0.798908 0.297528 0.079888 0.029 Uiso 1 1 calc R U . . .
H18B H 0.718705 0.314128 0.008305 0.029 Uiso 1 1 calc R U . . .
C19 C 0.86214(18) 0.1274(2) 0.03758(13) 0.0328(5) Uani 1 1 d . . . . .
H19A H 0.905876 0.070227 0.086522 0.049 Uiso 1 1 calc R U . . .
H19B H 0.925336 0.148640 -0.006406 0.049 Uiso 1 1 calc R U . . .
H19C H 0.821583 0.081674 0.019314 0.049 Uiso 1 1 calc R U . . .
C20 C 0.52451(17) 0.69978(18) 0.04848(12) 0.0238(4) Uani 1 1 d . . . . .
H20A H 0.551603 0.663281 -0.001069 0.029 Uiso 1 1 calc R U . . .
H20B H 0.597434 0.657645 0.082794 0.029 Uiso 1 1 calc R U . . .
C21 C 0.48572(19) 0.84733(19) 0.02430(13) 0.0300(4) Uani 1 1 d . . . . .
H21A H 0.419133 0.886930 -0.013785 0.045 Uiso 1 1 calc R U . . .
H21B H 0.561300 0.867941 -0.002546 0.045 Uiso 1 1 calc R U . . .
H21C H 0.451480 0.883123 0.073514 0.045 Uiso 1 1 calc R U . . .
C22 C 0.06109(16) 0.34416(18) 0.27934(11) 0.0210(4) Uani 1 1 d . . . . .
C23 C 0.06204(17) 0.33053(19) 0.36343(11) 0.0232(4) Uani 1 1 d . . . . .
H23 H -0.015145 0.331393 0.397629 0.028 Uiso 1 1 calc R U . . .
C24 C 0.16520(17) 0.31569(18) 0.40262(11) 0.0224(4) Uani 1 1 d . . . . .
C25 C 0.15090(16) 0.33701(18) 0.14110(11) 0.0211(4) Uani 1 1 d . . . . .
C26 C 0.15490(16) 0.43652(19) 0.07172(11) 0.0231(4) Uani 1 1 d . . . . .
H26 H 0.156685 0.515414 0.077415 0.028 Uiso 1 1 calc R U . . .
C27 C 0.15627(17) 0.4208(2) -0.00569(12) 0.0266(4) Uani 1 1 d . . . . .
H27 H 0.157014 0.490430 -0.052340 0.032 Uiso 1 1 calc R U . . .
C28 C 0.15658(17) 0.3059(2) -0.01683(12) 0.0277(4) Uani 1 1 d . . . . .
C29 C 0.15409(18) 0.2071(2) 0.05258(13) 0.0291(4) Uani 1 1 d . . . . .
H29 H 0.154457 0.127342 0.046684 0.035 Uiso 1 1 calc R U . . .
C30 C 0.15108(17) 0.2219(2) 0.13062(12) 0.0270(4) Uani 1 1 d . . . . .
H30 H 0.149120 0.152614 0.177249 0.032 Uiso 1 1 calc R U . . .
C31 C 0.1631(2) 0.2885(2) -0.10179(13) 0.0383(5) Uani 1 1 d . . . . .
H31A H 0.253676 0.246538 -0.122778 0.057 Uiso 1 1 calc R U . . .
H31B H 0.123125 0.375011 -0.138502 0.057 Uiso 1 1 calc R U . . .
H31C H 0.116888 0.232676 -0.099303 0.057 Uiso 1 1 calc R U . . .
C32 C 0.37220(16) 0.31251(18) 0.41004(11) 0.0218(4) Uani 1 1 d . . . . .
C33 C 0.43805(19) 0.1912(2) 0.46064(13) 0.0297(4) Uani 1 1 d . . . . .
H33 H 0.411947 0.119894 0.469358 0.036 Uiso 1 1 calc R U . . .
C34 C 0.54136(19) 0.1738(2) 0.49837(13) 0.0339(5) Uani 1 1 d . . . . .
H34 H 0.584526 0.090530 0.533152 0.041 Uiso 1 1 calc R U . . .
C35 C 0.58331(18) 0.2752(2) 0.48654(12) 0.0306(5) Uani 1 1 d . . . . .
C36 C 0.51733(19) 0.3954(2) 0.43623(12) 0.0312(5) Uani 1 1 d . . . . .
H36 H 0.543522 0.466713 0.427515 0.037 Uiso 1 1 calc R U . . .
C37 C 0.41335(18) 0.4140(2) 0.39811(12) 0.0263(4) Uani 1 1 d . . . . .
H37 H 0.370078 0.497438 0.363488 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6946(2) 0.2556(3) 0.52902(15) 0.0451(6) Uani 1 1 d . . . . .
H38A H 0.720818 0.330716 0.505774 0.068 Uiso 1 1 calc R U . . .
H38B H 0.767491 0.174084 0.520961 0.068 Uiso 1 1 calc R U . . .
H38C H 0.667755 0.249342 0.587951 0.068 Uiso 1 1 calc R U . . .
C39 C -0.15934(16) 0.35172(19) 0.30648(11) 0.0217(4) Uani 1 1 d . . . . .
H39A H -0.189478 0.420919 0.337780 0.026 Uiso 1 1 calc R U . . .
H39B H -0.140528 0.264753 0.345858 0.026 Uiso 1 1 calc R U . . .
C40 C -0.26021(17) 0.3775(2) 0.25298(12) 0.0282(4) Uani 1 1 d . . . . .
H40A H -0.279674 0.465010 0.215629 0.042 Uiso 1 1 calc R U . . .
H40B H -0.339014 0.373963 0.287696 0.042 Uiso 1 1 calc R U . . .
H40C H -0.227496 0.310138 0.220856 0.042 Uiso 1 1 calc R U . . .
C41 C 0.05344(18) 0.2520(2) 0.53707(12) 0.0285(4) Uani 1 1 d . . . . .
H41A H 0.086347 0.187714 0.588356 0.034 Uiso 1 1 calc R U . . .
H41B H 0.023417 0.208984 0.507826 0.034 Uiso 1 1 calc R U . . .
C42 C -0.05910(19) 0.3713(2) 0.55850(13) 0.0336(5) Uani 1 1 d . . . . .
H42A H -0.028896 0.416847 0.584811 0.050 Uiso 1 1 calc R U . . .
H42B H -0.124356 0.343034 0.596332 0.050 Uiso 1 1 calc R U . . .
H42C H -0.097116 0.431372 0.508265 0.050 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 N1 1.9769(14) . ?
Zn1 N3 1.9788(14) . ?
Zn1 N2 1.9812(15) . ?
Zn1 N4 1.9877(15) . ?
O1 C1 1.363(2) . ?
O1 C18 1.444(2) . ?
O2 C3 1.361(2) . ?
O2 C20 1.438(2) . ?
O3 C22 1.364(2) . ?
O3 C39 1.441(2) . ?
O4 C24 1.357(2) . ?
O4 C41 1.448(2) . ?
N1 C1 1.322(2) . ?
N1 C4 1.433(2) . ?
N2 C3 1.328(2) . ?
N2 C11 1.433(2) . ?
N3 C22 1.322(2) . ?
N3 C25 1.436(2) . ?
N4 C24 1.317(2) . ?
N4 C32 1.434(2) . ?
C1 C2 1.400(2) . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.382(3) . ?
C4 C9 1.390(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 C10 1.513(3) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.388(2) . ?
C11 C16 1.395(2) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 C17 1.517(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 C19 1.506(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.506(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.404(2) . ?
C23 C24 1.410(2) . ?
C23 H23 0.9500 . ?
C25 C30 1.387(3) . ?
C25 C26 1.392(2) . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.384(3) . ?
C28 C31 1.508(3) . ?
C29 C30 1.388(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C37 1.383(3) . ?
C32 C33 1.391(3) . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.389(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 C38 1.508(3) . ?
C36 C37 1.391(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.508(2) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C42 1.509(3) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
N1 Zn1 N3 116.32(6) . . ?
N1 Zn1 N2 96.78(6) . . ?
N3 Zn1 N2 117.58(6) . . ?
N1 Zn1 N4 114.15(6) . . ?
N3 Zn1 N4 96.36(6) . . ?
N2 Zn1 N4 117.03(6) . . ?
C1 O1 C18 121.08(14) . . ?
C3 O2 C20 120.80(13) . . ?
C22 O3 C39 121.15(13) . . ?
C24 O4 C41 121.90(14) . . ?
C1 N1 C4 118.63(14) . . ?
C1 N1 Zn1 121.98(12) . . ?
C4 N1 Zn1 119.36(11) . . ?
C3 N2 C11 118.43(15) . . ?
C3 N2 Zn1 120.88(12) . . ?
C11 N2 Zn1 120.64(11) . . ?
C22 N3 C25 119.35(14) . . ?
C22 N3 Zn1 120.89(12) . . ?
C25 N3 Zn1 119.74(11) . . ?
C24 N4 C32 120.82(15) . . ?
C24 N4 Zn1 122.26(12) . . ?
C32 N4 Zn1 116.70(11) . . ?
N1 C1 O1 114.26(15) . . ?
N1 C1 C2 125.86(16) . . ?
O1 C1 C2 119.87(15) . . ?
C1 C2 C3 127.01(16) . . ?
C1 C2 H2 116.5 . . ?
C3 C2 H2 116.5 . . ?
N2 C3 O2 114.17(15) . . ?
N2 C3 C2 126.58(16) . . ?
O2 C3 C2 119.20(15) . . ?
C5 C4 C9 118.57(17) . . ?
C5 C4 N1 120.75(16) . . ?
C9 C4 N1 120.59(16) . . ?
C4 C5 C6 120.55(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 121.22(19) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.71(18) . . ?
C8 C7 C10 121.9(2) . . ?
C6 C7 C10 120.4(2) . . ?
C7 C8 C9 121.62(19) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 120.25(18) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.60(16) . . ?
C12 C11 N2 119.55(16) . . ?
C16 C11 N2 121.76(15) . . ?
C11 C12 C13 120.55(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.92(18) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 118.10(17) . . ?
C15 C14 C17 120.97(19) . . ?
C13 C14 C17 120.94(19) . . ?
C14 C15 C16 121.53(18) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C11 120.20(17) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O1 C18 C19 106.66(15) . . ?
O1 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
O1 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 106.87(14) . . ?
O2 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O2 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 O3 113.78(15) . . ?
N3 C22 C23 126.40(16) . . ?
O3 C22 C23 119.81(15) . . ?
C22 C23 C24 127.00(16) . . ?
C22 C23 H23 116.5 . . ?
C24 C23 H23 116.5 . . ?
N4 C24 O4 114.90(15) . . ?
N4 C24 C23 125.06(17) . . ?
O4 C24 C23 119.98(15) . . ?
C30 C25 C26 118.55(17) . . ?
C30 C25 N3 121.21(17) . . ?
C26 C25 N3 120.10(16) . . ?
C27 C26 C25 120.15(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 121.73(19) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C29 C28 C27 117.55(18) . . ?
C29 C28 C31 121.45(19) . . ?
C27 C28 C31 120.97(19) . . ?
C28 C29 C30 121.44(19) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C25 C30 C29 120.56(19) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C37 C32 C33 118.29(17) . . ?
C37 C32 N4 118.60(17) . . ?
C33 C32 N4 122.90(16) . . ?
C34 C33 C32 120.48(19) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 121.5(2) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C36 C35 C34 117.65(18) . . ?
C36 C35 C38 121.3(2) . . ?
C34 C35 C38 121.0(2) . . ?
C35 C36 C37 121.29(19) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C32 C37 C36 120.77(19) . . ?
C32 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O3 C39 C40 105.95(14) . . ?
O3 C39 H39A 110.5 . . ?
C40 C39 H39A 110.5 . . ?
O3 C39 H39B 110.5 . . ?
C40 C39 H39B 110.5 . . ?
H39A C39 H39B 108.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O4 C41 C42 112.07(17) . . ?
O4 C41 H41A 109.2 . . ?
C42 C41 H41A 109.2 . . ?
O4 C41 H41B 109.2 . . ?
C42 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C4 N1 C1 O1 5.4(2) . . . . ?
Zn1 N1 C1 O1 -176.35(10) . . . . ?
C4 N1 C1 C2 -175.65(16) . . . . ?
Zn1 N1 C1 C2 2.6(2) . . . . ?
C18 O1 C1 N1 179.74(15) . . . . ?
C18 O1 C1 C2 0.8(2) . . . . ?
N1 C1 C2 C3 5.1(3) . . . . ?
O1 C1 C2 C3 -176.01(16) . . . . ?
C11 N2 C3 O2 -10.3(2) . . . . ?
Zn1 N2 C3 O2 172.14(11) . . . . ?
C11 N2 C3 C2 172.32(16) . . . . ?
Zn1 N2 C3 C2 -5.2(2) . . . . ?
C20 O2 C3 N2 164.27(15) . . . . ?
C20 O2 C3 C2 -18.2(2) . . . . ?
C1 C2 C3 N2 -3.6(3) . . . . ?
C1 C2 C3 O2 179.20(16) . . . . ?
C1 N1 C4 C5 80.0(2) . . . . ?
Zn1 N1 C4 C5 -98.24(17) . . . . ?
C1 N1 C4 C9 -103.4(2) . . . . ?
Zn1 N1 C4 C9 78.32(19) . . . . ?
C9 C4 C5 C6 2.7(3) . . . . ?
N1 C4 C5 C6 179.35(17) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C5 C6 C7 C10 177.48(19) . . . . ?
C6 C7 C8 C9 1.4(3) . . . . ?
C10 C7 C8 C9 -177.77(19) . . . . ?
C7 C8 C9 C4 1.0(3) . . . . ?
C5 C4 C9 C8 -3.0(3) . . . . ?
N1 C4 C9 C8 -179.65(17) . . . . ?
C3 N2 C11 C12 129.46(18) . . . . ?
Zn1 N2 C11 C12 -53.0(2) . . . . ?
C3 N2 C11 C16 -54.0(2) . . . . ?
Zn1 N2 C11 C16 123.56(16) . . . . ?
C16 C11 C12 C13 3.3(3) . . . . ?
N2 C11 C12 C13 180.00(17) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C12 C13 C14 C17 178.28(19) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C17 C14 C15 C16 -178.49(19) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
C12 C11 C16 C15 -3.5(3) . . . . ?
N2 C11 C16 C15 179.87(17) . . . . ?
C1 O1 C18 C19 -173.35(15) . . . . ?
C3 O2 C20 C21 -171.69(15) . . . . ?
C25 N3 C22 O3 -13.8(2) . . . . ?
Zn1 N3 C22 O3 167.79(11) . . . . ?
C25 N3 C22 C23 167.10(17) . . . . ?
Zn1 N3 C22 C23 -11.3(3) . . . . ?
C39 O3 C22 N3 -178.53(15) . . . . ?
C39 O3 C22 C23 0.6(3) . . . . ?
N3 C22 C23 C24 -2.8(3) . . . . ?
O3 C22 C23 C24 178.12(17) . . . . ?
C32 N4 C24 O4 4.6(2) . . . . ?
Zn1 N4 C24 O4 178.97(11) . . . . ?
C32 N4 C24 C23 -178.33(17) . . . . ?
Zn1 N4 C24 C23 -3.9(3) . . . . ?
C41 O4 C24 N4 -174.24(16) . . . . ?
C41 O4 C24 C23 8.5(3) . . . . ?
C22 C23 C24 N4 11.6(3) . . . . ?
C22 C23 C24 O4 -171.38(18) . . . . ?
C22 N3 C25 C30 -61.7(2) . . . . ?
Zn1 N3 C25 C30 116.69(16) . . . . ?
C22 N3 C25 C26 122.67(18) . . . . ?
Zn1 N3 C25 C26 -58.89(19) . . . . ?
C30 C25 C26 C27 1.3(3) . . . . ?
N3 C25 C26 C27 177.02(15) . . . . ?
C25 C26 C27 C28 -1.4(3) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
C26 C27 C28 C31 -177.68(17) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C31 C28 C29 C30 178.49(17) . . . . ?
C26 C25 C30 C29 -0.5(3) . . . . ?
N3 C25 C30 C29 -176.18(16) . . . . ?
C28 C29 C30 C25 -0.2(3) . . . . ?
C24 N4 C32 C37 -124.87(19) . . . . ?
Zn1 N4 C32 C37 60.41(19) . . . . ?
C24 N4 C32 C33 60.5(2) . . . . ?
Zn1 N4 C32 C33 -114.26(17) . . . . ?
C37 C32 C33 C34 0.5(3) . . . . ?
N4 C32 C33 C34 175.20(17) . . . . ?
C32 C33 C34 C35 -0.7(3) . . . . ?
C33 C34 C35 C36 0.7(3) . . . . ?
C33 C34 C35 C38 179.03(19) . . . . ?
C34 C35 C36 C37 -0.6(3) . . . . ?
C38 C35 C36 C37 -178.94(19) . . . . ?
C33 C32 C37 C36 -0.4(3) . . . . ?
N4 C32 C37 C36 -175.36(16) . . . . ?
C35 C36 C37 C32 0.5(3) . . . . ?
C22 O3 C39 C40 174.75(15) . . . . ?
C24 O4 C41 C42 -91.6(2) . . . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_ML020
_database_code_depnum_ccdc_archive 'CCDC 1841081'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H28 N4'
_chemical_formula_sum            'C21 H28 N4'
_chemical_formula_weight         336.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   23.757(4)
_cell_length_b                   7.5454(11)
_cell_length_c                   21.366(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.621(2)
_cell_angle_gamma                90
_cell_volume                     3822.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.74

_exptl_crystal_description       'thin rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44914
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         28.925
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9521
_reflns_number_gt                6732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+1.2084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9521
_refine_ls_number_parameters     460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.28757(5) 1.00027(16) 0.62761(5) 0.0245(3) Uani 1 1 d . . . . .
N2 N 0.11061(5) 0.69950(16) 0.63275(5) 0.0248(3) Uani 1 1 d . . . . .
N3 N 0.19778(5) 1.10687(16) 0.61311(6) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.17331(5) 0.69394(17) 0.55681(5) 0.0270(3) Uani 1 1 d . . . . .
N5 N 0.36883(5) 0.54103(16) 0.44330(5) 0.0247(3) Uani 1 1 d . . . . .
N6 N 0.22691(5) 0.20386(16) 0.32199(5) 0.0232(3) Uani 1 1 d . . . . .
N7 N 0.29985(5) 0.65133(16) 0.37529(6) 0.0264(3) Uani 1 1 d . . . . .
N8 N 0.31847(5) 0.24387(16) 0.30000(6) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.23476(6) 0.97638(18) 0.63449(6) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.20859(6) 0.80911(18) 0.66018(6) 0.0211(3) Uani 1 1 d . . . . .
H2A H 0.193522 0.837098 0.701193 0.025 Uiso 1 1 calc R U . . .
H2B H 0.238548 0.718942 0.667532 0.025 Uiso 1 1 calc R U . . .
C3 C 0.16132(6) 0.72989(18) 0.61740(6) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.32968(6) 0.87708(18) 0.64736(7) 0.0227(3) Uani 1 1 d . . . . .
C5 C 0.34473(6) 0.8492(2) 0.71087(7) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.323496 0.903482 0.741851 0.031 Uiso 1 1 calc R U . . .
C6 C 0.39062(6) 0.7425(2) 0.72895(7) 0.0280(3) Uani 1 1 d . . . . .
H6 H 0.400529 0.726688 0.772365 0.034 Uiso 1 1 calc R U . . .
C7 C 0.42244(6) 0.6583(2) 0.68524(7) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.40728(6) 0.6879(2) 0.62204(7) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.428249 0.632129 0.591148 0.031 Uiso 1 1 calc R U . . .
C9 C 0.36246(6) 0.79647(19) 0.60313(7) 0.0253(3) Uani 1 1 d . . . . .
H9 H 0.353820 0.816577 0.559692 0.030 Uiso 1 1 calc R U . . .
C10 C 0.47168(7) 0.5403(2) 0.70467(8) 0.0369(4) Uani 1 1 d . . . . .
H10A H 0.488399 0.493971 0.667220 0.055 Uiso 0.5 1 calc R U P . .
H10B H 0.500018 0.608751 0.729685 0.055 Uiso 0.5 1 calc R U P . .
H10C H 0.458625 0.441430 0.729736 0.055 Uiso 0.5 1 calc R U P . .
H10D H 0.476295 0.535464 0.750541 0.055 Uiso 0.5 1 calc R U P . .
H10E H 0.464677 0.420684 0.688075 0.055 Uiso 0.5 1 calc R U P . .
H10F H 0.506069 0.588005 0.688025 0.055 Uiso 0.5 1 calc R U P . .
C11 C 0.09291(6) 0.72418(19) 0.69406(6) 0.0224(3) Uani 1 1 d . . . . .
C12 C 0.04528(6) 0.8296(2) 0.70179(7) 0.0258(3) Uani 1 1 d . . . . .
H12 H 0.028300 0.891271 0.666726 0.031 Uiso 1 1 calc R U . . .
C13 C 0.02251(6) 0.8454(2) 0.75964(7) 0.0262(3) Uani 1 1 d . . . . .
H13 H -0.009551 0.918851 0.763644 0.031 Uiso 1 1 calc R U . . .
C14 C 0.04581(6) 0.75562(19) 0.81207(7) 0.0237(3) Uani 1 1 d . . . . .
C15 C 0.09323(6) 0.65130(19) 0.80454(7) 0.0250(3) Uani 1 1 d . . . . .
H15 H 0.110055 0.589896 0.839746 0.030 Uiso 1 1 calc R U . . .
C16 C 0.11660(6) 0.63469(19) 0.74672(7) 0.0239(3) Uani 1 1 d . . . . .
H16 H 0.148881 0.562073 0.742969 0.029 Uiso 1 1 calc R U . . .
C17 C 0.01953(7) 0.7666(2) 0.87448(7) 0.0315(3) Uani 1 1 d . . . . .
H17A H 0.013496 0.646762 0.890397 0.047 Uiso 1 1 calc R U . . .
H17B H -0.016729 0.828519 0.869165 0.047 Uiso 1 1 calc R U . . .
H17C H 0.044749 0.831764 0.904381 0.047 Uiso 1 1 calc R U . . .
C18 C 0.22176(7) 1.2605(2) 0.58301(8) 0.0319(3) Uani 1 1 d . . . . .
H18A H 0.241671 1.334830 0.614849 0.048 Uiso 1 1 calc R U . . .
H18B H 0.191444 1.329281 0.561325 0.048 Uiso 1 1 calc R U . . .
H18C H 0.248274 1.220639 0.552622 0.048 Uiso 1 1 calc R U . . .
C19 C 0.14554(7) 1.1425(2) 0.64245(8) 0.0343(4) Uani 1 1 d . . . . .
H19A H 0.131842 1.033144 0.660986 0.051 Uiso 1 1 calc R U . . .
H19B H 0.117253 1.186559 0.610843 0.051 Uiso 1 1 calc R U . . .
H19C H 0.152214 1.232016 0.675324 0.051 Uiso 1 1 calc R U . . .
C20 C 0.22905(6) 0.6987(2) 0.53348(7) 0.0266(3) Uani 1 1 d . . . . .
H20A H 0.234915 0.813247 0.513243 0.040 Uiso 1 1 calc R U . . .
H20B H 0.232711 0.603230 0.502920 0.040 Uiso 1 1 calc R U . . .
H20C H 0.257341 0.683011 0.568440 0.040 Uiso 1 1 calc R U . . .
C21 C 0.12751(7) 0.6412(2) 0.51197(7) 0.0351(4) Uani 1 1 d . . . . .
H21A H 0.142514 0.620107 0.470941 0.053 Uiso 0.5 1 calc R U P . .
H21B H 0.110051 0.532256 0.526538 0.053 Uiso 0.5 1 calc R U P . .
H21C H 0.099196 0.735669 0.508320 0.053 Uiso 0.5 1 calc R U P . .
H21D H 0.091993 0.638582 0.532925 0.053 Uiso 0.5 1 calc R U P . .
H21E H 0.124456 0.726432 0.477328 0.053 Uiso 0.5 1 calc R U P . .
H21F H 0.135312 0.523019 0.495546 0.053 Uiso 0.5 1 calc R U P . .
C22 C 0.32279(6) 0.51258(18) 0.40976(6) 0.0213(3) Uani 1 1 d . . . . .
C23 C 0.29221(6) 0.33536(18) 0.40550(6) 0.0209(3) Uani 1 1 d . . . . .
H23A H 0.256934 0.347888 0.427420 0.025 Uiso 1 1 calc R U . . .
H23B H 0.315971 0.247522 0.429288 0.025 Uiso 1 1 calc R U . . .
C24 C 0.27676(6) 0.25722(18) 0.34088(6) 0.0204(3) Uani 1 1 d . . . . .
C25 C 0.39608(6) 0.40877(19) 0.48099(7) 0.0235(3) Uani 1 1 d . . . . .
C26 C 0.37256(6) 0.3392(2) 0.53385(7) 0.0272(3) Uani 1 1 d . . . . .
H26 H 0.334678 0.367289 0.541747 0.033 Uiso 1 1 calc R U . . .
C27 C 0.40363(7) 0.2295(2) 0.57508(7) 0.0295(3) Uani 1 1 d . . . . .
H27 H 0.386606 0.183781 0.610750 0.035 Uiso 1 1 calc R U . . .
C28 C 0.45916(7) 0.1852(2) 0.56528(7) 0.0296(3) Uani 1 1 d . . . . .
C29 C 0.48201(7) 0.2505(2) 0.51158(8) 0.0325(4) Uani 1 1 d . . . . .
H29 H 0.519473 0.219047 0.503025 0.039 Uiso 1 1 calc R U . . .
C30 C 0.45128(6) 0.3606(2) 0.47028(7) 0.0292(3) Uani 1 1 d . . . . .
H30 H 0.468104 0.403966 0.434115 0.035 Uiso 1 1 calc R U . . .
C31 C 0.49449(7) 0.0775(2) 0.61261(8) 0.0405(4) Uani 1 1 d . . . . .
H31A H 0.516975 -0.008711 0.590648 0.061 Uiso 1 1 calc R U . . .
H31B H 0.469747 0.014809 0.640194 0.061 Uiso 1 1 calc R U . . .
H31C H 0.519680 0.156506 0.637707 0.061 Uiso 1 1 calc R U . . .
C32 C 0.18091(6) 0.21210(18) 0.36057(6) 0.0214(3) Uani 1 1 d . . . . .
C33 C 0.13204(6) 0.30130(19) 0.33872(7) 0.0243(3) Uani 1 1 d . . . . .
H33 H 0.131216 0.361062 0.299538 0.029 Uiso 1 1 calc R U . . .
C34 C 0.08471(6) 0.30375(19) 0.37347(7) 0.0264(3) Uani 1 1 d . . . . .
H34 H 0.052017 0.365677 0.357658 0.032 Uiso 1 1 calc R U . . .
C35 C 0.08400(6) 0.2175(2) 0.43103(7) 0.0264(3) Uani 1 1 d . . . . .
C36 C 0.13230(6) 0.1256(2) 0.45230(7) 0.0265(3) Uani 1 1 d . . . . .
H36 H 0.132730 0.064052 0.491116 0.032 Uiso 1 1 calc R U . . .
C37 C 0.17994(6) 0.12233(19) 0.41766(6) 0.0239(3) Uani 1 1 d . . . . .
H37 H 0.212296 0.058070 0.433070 0.029 Uiso 1 1 calc R U . . .
C38 C 0.03250(7) 0.2265(2) 0.46888(8) 0.0380(4) Uani 1 1 d . . . . .
H38A H 0.032889 0.126777 0.498276 0.057 Uiso 1 1 calc R U . . .
H38B H -0.001573 0.220459 0.440602 0.057 Uiso 1 1 calc R U . . .
H38C H 0.032749 0.338199 0.492314 0.057 Uiso 1 1 calc R U . . .
C39 C 0.32660(7) 0.8240(2) 0.38399(8) 0.0318(3) Uani 1 1 d . . . . .
H39A H 0.317534 0.873188 0.424601 0.048 Uiso 1 1 calc R U . . .
H39B H 0.312683 0.904027 0.350353 0.048 Uiso 1 1 calc R U . . .
H39C H 0.367565 0.811022 0.382884 0.048 Uiso 1 1 calc R U . . .
C40 C 0.24110(6) 0.6556(2) 0.35101(7) 0.0301(3) Uani 1 1 d . . . . .
H40A H 0.233782 0.766266 0.327905 0.045 Uiso 0.5 1 calc R U P . .
H40B H 0.233634 0.554657 0.322838 0.045 Uiso 0.5 1 calc R U P . .
H40C H 0.216401 0.648735 0.385974 0.045 Uiso 0.5 1 calc R U P . .
H40D H 0.222096 0.546839 0.363239 0.045 Uiso 0.5 1 calc R U P . .
H40E H 0.222244 0.758448 0.368306 0.045 Uiso 0.5 1 calc R U P . .
H40F H 0.239477 0.664370 0.305171 0.045 Uiso 0.5 1 calc R U P . .
C41 C 0.30434(7) 0.1705(2) 0.23799(7) 0.0302(3) Uani 1 1 d . . . . .
H41A H 0.301906 0.041141 0.240841 0.045 Uiso 1 1 calc R U . . .
H41B H 0.333628 0.202875 0.209771 0.045 Uiso 1 1 calc R U . . .
H41C H 0.267957 0.218134 0.221605 0.045 Uiso 1 1 calc R U . . .
C42 C 0.37820(6) 0.2577(2) 0.31793(8) 0.0316(3) Uani 1 1 d . . . . .
H42A H 0.383378 0.283858 0.362850 0.047 Uiso 1 1 calc R U . . .
H42B H 0.394765 0.353118 0.293993 0.047 Uiso 1 1 calc R U . . .
H42C H 0.396839 0.145380 0.309065 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
N1 C1 1.2853(18) . ?
N1 C4 1.4105(18) . ?
N2 C3 1.2888(18) . ?
N2 C11 1.4132(18) . ?
N3 C1 1.3781(18) . ?
N3 C19 1.4505(19) . ?
N3 C18 1.4590(19) . ?
N4 C3 1.3700(18) . ?
N4 C20 1.4446(18) . ?
N4 C21 1.4591(18) . ?
N5 C22 1.2873(17) . ?
N5 C25 1.4134(18) . ?
N6 C24 1.2913(17) . ?
N6 C32 1.4110(17) . ?
N7 C22 1.3728(18) . ?
N7 C39 1.4563(19) . ?
N7 C40 1.4584(19) . ?
N8 C24 1.3654(17) . ?
N8 C42 1.4500(19) . ?
N8 C41 1.4555(19) . ?
C1 C2 1.5245(19) . ?
C2 C3 1.5246(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.397(2) . ?
C4 C9 1.401(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 C10 1.507(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C11 C16 1.3995(19) . ?
C11 C12 1.401(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(2) . ?
C14 C17 1.510(2) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C22 C23 1.5218(19) . ?
C23 C24 1.5246(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 C30 1.394(2) . ?
C25 C26 1.394(2) . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(2) . ?
C28 C31 1.510(2) . ?
C29 C30 1.386(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.3967(19) . ?
C32 C37 1.3969(19) . ?
C33 C34 1.386(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.393(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(2) . ?
C35 C38 1.510(2) . ?
C36 C37 1.391(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C40 H40D 0.9800 . ?
C40 H40E 0.9800 . ?
C40 H40F 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C1 N1 C4 123.53(12) . . ?
C3 N2 C11 123.38(12) . . ?
C1 N3 C19 122.30(12) . . ?
C1 N3 C18 117.09(12) . . ?
C19 N3 C18 114.31(12) . . ?
C3 N4 C20 124.82(12) . . ?
C3 N4 C21 118.91(12) . . ?
C20 N4 C21 116.24(12) . . ?
C22 N5 C25 122.82(12) . . ?
C24 N6 C32 122.17(12) . . ?
C22 N7 C39 117.30(12) . . ?
C22 N7 C40 123.10(12) . . ?
C39 N7 C40 115.19(12) . . ?
C24 N8 C42 124.29(12) . . ?
C24 N8 C41 118.38(12) . . ?
C42 N8 C41 115.69(12) . . ?
N1 C1 N3 117.93(13) . . ?
N1 C1 C2 125.50(13) . . ?
N3 C1 C2 116.42(12) . . ?
C1 C2 C3 114.23(11) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N2 C3 N4 117.31(12) . . ?
N2 C3 C2 125.59(12) . . ?
N4 C3 C2 117.06(12) . . ?
C5 C4 C9 118.09(13) . . ?
C5 C4 N1 121.53(13) . . ?
C9 C4 N1 119.88(13) . . ?
C6 C5 C4 120.34(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.85(14) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 117.31(14) . . ?
C6 C7 C10 122.00(14) . . ?
C8 C7 C10 120.69(14) . . ?
C9 C8 C7 121.68(14) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 120.70(13) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C16 C11 C12 117.76(13) . . ?
C16 C11 N2 123.61(13) . . ?
C12 C11 N2 118.28(12) . . ?
C13 C12 C11 121.19(13) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.17(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 117.73(13) . . ?
C15 C14 C17 121.07(13) . . ?
C13 C14 C17 121.17(13) . . ?
C16 C15 C14 121.66(13) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 120.49(13) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21D C21 H21E 109.5 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
N5 C22 N7 117.77(13) . . ?
N5 C22 C23 124.44(12) . . ?
N7 C22 C23 117.79(12) . . ?
C22 C23 C24 118.73(11) . . ?
C22 C23 H23A 107.6 . . ?
C24 C23 H23A 107.6 . . ?
C22 C23 H23B 107.6 . . ?
C24 C23 H23B 107.6 . . ?
H23A C23 H23B 107.1 . . ?
N6 C24 N8 117.74(12) . . ?
N6 C24 C23 124.55(12) . . ?
N8 C24 C23 117.71(12) . . ?
C30 C25 C26 117.68(13) . . ?
C30 C25 N5 119.49(13) . . ?
C26 C25 N5 122.34(13) . . ?
C27 C26 C25 120.99(14) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 121.34(14) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C29 117.59(14) . . ?
C27 C28 C31 121.42(15) . . ?
C29 C28 C31 120.92(15) . . ?
C30 C29 C28 121.37(15) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C25 120.99(14) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 117.79(13) . . ?
C33 C32 N6 118.96(12) . . ?
C37 C32 N6 123.03(13) . . ?
C34 C33 C32 120.85(13) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 121.49(14) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
C36 C35 C34 117.73(13) . . ?
C36 C35 C38 121.78(14) . . ?
C34 C35 C38 120.48(14) . . ?
C37 C36 C35 121.11(14) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C36 C37 C32 121.00(13) . . ?
C36 C37 H37 119.5 . . ?
C32 C37 H37 119.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N7 C39 H39A 109.5 . . ?
N7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N7 C40 H40A 109.5 . . ?
N7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
H40D C40 H40E 109.5 . . ?
H40D C40 H40F 109.5 . . ?
H40E C40 H40F 109.5 . . ?
N8 C41 H41A 109.5 . . ?
N8 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N8 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N8 C42 H42A 109.5 . . ?
N8 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N8 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C4 N1 C1 N3 -179.94(12) . . . . ?
C4 N1 C1 C2 -4.7(2) . . . . ?
C19 N3 C1 N1 -149.18(14) . . . . ?
C18 N3 C1 N1 1.32(19) . . . . ?
C19 N3 C1 C2 35.11(19) . . . . ?
C18 N3 C1 C2 -174.39(12) . . . . ?
N1 C1 C2 C3 -125.92(14) . . . . ?
N3 C1 C2 C3 49.43(16) . . . . ?
C11 N2 C3 N4 177.58(13) . . . . ?
C11 N2 C3 C2 -4.9(2) . . . . ?
C20 N4 C3 N2 -171.91(13) . . . . ?
C21 N4 C3 N2 6.1(2) . . . . ?
C20 N4 C3 C2 10.4(2) . . . . ?
C21 N4 C3 C2 -171.68(13) . . . . ?
C1 C2 C3 N2 -123.48(15) . . . . ?
C1 C2 C3 N4 54.04(17) . . . . ?
C1 N1 C4 C5 -71.18(18) . . . . ?
C1 N1 C4 C9 117.12(15) . . . . ?
C9 C4 C5 C6 -0.8(2) . . . . ?
N1 C4 C5 C6 -172.60(13) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C5 C6 C7 C10 -179.05(14) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C10 C7 C8 C9 -179.62(14) . . . . ?
C7 C8 C9 C4 -1.7(2) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
N1 C4 C9 C8 174.05(13) . . . . ?
C3 N2 C11 C16 -59.9(2) . . . . ?
C3 N2 C11 C12 127.04(15) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
N2 C11 C12 C13 173.77(13) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C12 C13 C14 C17 -177.34(14) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C17 C14 C15 C16 177.54(13) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -0.1(2) . . . . ?
N2 C11 C16 C15 -173.20(13) . . . . ?
C25 N5 C22 N7 179.57(12) . . . . ?
C25 N5 C22 C23 -0.7(2) . . . . ?
C39 N7 C22 N5 -5.62(19) . . . . ?
C40 N7 C22 N5 -160.89(13) . . . . ?
C39 N7 C22 C23 174.66(12) . . . . ?
C40 N7 C22 C23 19.39(19) . . . . ?
N5 C22 C23 C24 -127.90(14) . . . . ?
N7 C22 C23 C24 51.80(17) . . . . ?
C32 N6 C24 N8 -179.95(12) . . . . ?
C32 N6 C24 C23 -0.4(2) . . . . ?
C42 N8 C24 N6 -164.82(14) . . . . ?
C41 N8 C24 N6 -0.08(19) . . . . ?
C42 N8 C24 C23 15.6(2) . . . . ?
C41 N8 C24 C23 -179.65(12) . . . . ?
C22 C23 C24 N6 -128.04(14) . . . . ?
C22 C23 C24 N8 51.49(17) . . . . ?
C22 N5 C25 C30 120.71(16) . . . . ?
C22 N5 C25 C26 -67.50(19) . . . . ?
C30 C25 C26 C27 1.6(2) . . . . ?
N5 C25 C26 C27 -170.32(13) . . . . ?
C25 C26 C27 C28 0.0(2) . . . . ?
C26 C27 C28 C29 -1.9(2) . . . . ?
C26 C27 C28 C31 175.24(14) . . . . ?
C27 C28 C29 C30 2.1(2) . . . . ?
C31 C28 C29 C30 -175.04(15) . . . . ?
C28 C29 C30 C25 -0.5(2) . . . . ?
C26 C25 C30 C29 -1.4(2) . . . . ?
N5 C25 C30 C29 170.77(14) . . . . ?
C24 N6 C32 C33 124.85(15) . . . . ?
C24 N6 C32 C37 -60.77(19) . . . . ?
C37 C32 C33 C34 1.5(2) . . . . ?
N6 C32 C33 C34 176.19(13) . . . . ?
C32 C33 C34 C35 -0.2(2) . . . . ?
C33 C34 C35 C36 -1.1(2) . . . . ?
C33 C34 C35 C38 178.23(14) . . . . ?
C34 C35 C36 C37 1.0(2) . . . . ?
C38 C35 C36 C37 -178.31(14) . . . . ?
C35 C36 C37 C32 0.4(2) . . . . ?
C33 C32 C37 C36 -1.6(2) . . . . ?
N6 C32 C37 C36 -176.03(13) . . . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_ML015
_database_code_depnum_ccdc_archive 'CCDC 1841080'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O2'
_chemical_formula_sum            'C21 H26 N2 O2'
_chemical_formula_weight         338.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8526(14)
_cell_length_b                   10.4721(18)
_cell_length_c                   13.253(2)
_cell_angle_alpha                112.609(2)
_cell_angle_beta                 93.693(2)
_cell_angle_gamma                101.864(2)
_cell_volume                     972.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    5518
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.78

_exptl_crystal_description       'irregular lump'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11909
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         28.940
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4707
_reflns_number_gt                3547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.2136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4707
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.45889(10) 0.66375(9) 0.62479(6) 0.02483(19) Uani 1 1 d . . . . .
O2 O 0.13991(10) 0.74570(9) 0.53748(6) 0.02410(19) Uani 1 1 d . . . . .
N1 N 0.55858(13) 0.75052(11) 0.50005(8) 0.0249(2) Uani 1 1 d . . . . .
N2 N 0.01389(13) 0.59728(11) 0.36007(8) 0.0276(2) Uani 1 1 d . . . . .
C1 C 0.44402(15) 0.66684(12) 0.52370(9) 0.0218(2) Uani 1 1 d . . . . .
C2 C 0.27853(15) 0.56169(12) 0.45026(9) 0.0233(2) Uani 1 1 d . . . . .
H2A H 0.237479 0.489446 0.480163 0.028 Uiso 1 1 calc R U . . .
H2B H 0.305769 0.511432 0.375359 0.028 Uiso 1 1 calc R U . . .
C3 C 0.13260(14) 0.63288(12) 0.44152(9) 0.0219(2) Uani 1 1 d . . . . .
C4 C 0.53680(15) 0.74777(13) 0.39144(9) 0.0240(2) Uani 1 1 d . . . . .
C5 C 0.61456(16) 0.66177(14) 0.30936(10) 0.0296(3) Uani 1 1 d . . . . .
H5 H 0.677868 0.601383 0.324606 0.035 Uiso 1 1 calc R U . . .
C6 C 0.60014(17) 0.66372(15) 0.20507(10) 0.0337(3) Uani 1 1 d . . . . .
H6 H 0.652885 0.603395 0.149477 0.040 Uiso 1 1 calc R U . . .
C7 C 0.51035(17) 0.75183(15) 0.18005(11) 0.0331(3) Uani 1 1 d . . . . .
C8 C 0.43514(18) 0.83868(14) 0.26373(11) 0.0326(3) Uani 1 1 d . . . . .
H8 H 0.373632 0.900264 0.248781 0.039 Uiso 1 1 calc R U . . .
C9 C 0.44740(16) 0.83791(13) 0.36838(10) 0.0282(3) Uani 1 1 d . . . . .
H9 H 0.395114 0.898539 0.424081 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4928(2) 0.7523(2) 0.06589(12) 0.0508(4) Uani 1 1 d . . . . .
H10A H 0.570343 0.698118 0.022410 0.076 Uiso 1 1 calc R U . . .
H10B H 0.526317 0.850928 0.072414 0.076 Uiso 1 1 calc R U . . .
H10C H 0.370415 0.708113 0.028877 0.076 Uiso 1 1 calc R U . . .
C11 C 0.01177(15) 0.48303(13) 0.25747(9) 0.0253(3) Uani 1 1 d . . . . .
C12 C 0.08986(19) 0.51196(15) 0.17508(11) 0.0380(3) Uani 1 1 d . . . . .
H12 H 0.151204 0.606944 0.189563 0.046 Uiso 1 1 calc R U . . .
C13 C 0.07918(19) 0.40353(15) 0.07184(11) 0.0385(3) Uani 1 1 d . . . . .
H13 H 0.134491 0.425413 0.016761 0.046 Uiso 1 1 calc R U . . .
C14 C -0.01024(16) 0.26414(14) 0.04721(10) 0.0302(3) Uani 1 1 d . . . . .
C15 C -0.08896(18) 0.23676(14) 0.12995(11) 0.0342(3) Uani 1 1 d . . . . .
H15 H -0.151377 0.141918 0.115106 0.041 Uiso 1 1 calc R U . . .
C16 C -0.07903(18) 0.34443(14) 0.23413(10) 0.0319(3) Uani 1 1 d . . . . .
H16 H -0.134620 0.322699 0.289182 0.038 Uiso 1 1 calc R U . . .
C17 C -0.0212(2) 0.14730(16) -0.06598(11) 0.0420(3) Uani 1 1 d . . . . .
H17A H -0.089125 0.056198 -0.068417 0.063 Uiso 0.5 1 calc R U P . .
H17B H -0.079588 0.170090 -0.122233 0.063 Uiso 0.5 1 calc R U P . .
H17C H 0.097840 0.139855 -0.080700 0.063 Uiso 0.5 1 calc R U P . .
H17D H 0.041876 0.187897 -0.112483 0.063 Uiso 0.5 1 calc R U P . .
H17E H 0.032340 0.074005 -0.058667 0.063 Uiso 0.5 1 calc R U P . .
H17F H -0.145089 0.104241 -0.100200 0.063 Uiso 0.5 1 calc R U P . .
C18 C 0.60432(17) 0.76903(13) 0.70609(9) 0.0289(3) Uani 1 1 d . . . . .
H18A H 0.598724 0.866406 0.715286 0.035 Uiso 1 1 calc R U . . .
H18B H 0.717920 0.753197 0.682233 0.035 Uiso 1 1 calc R U . . .
C19 C 0.58890(19) 0.75272(17) 0.81316(10) 0.0388(3) Uani 1 1 d . . . . .
H19A H 0.476045 0.768668 0.835868 0.058 Uiso 1 1 calc R U . . .
H19B H 0.685702 0.822768 0.870433 0.058 Uiso 1 1 calc R U . . .
H19C H 0.594895 0.656069 0.803014 0.058 Uiso 1 1 calc R U . . .
C20 C 0.01232(16) 0.82860(14) 0.53849(10) 0.0284(3) Uani 1 1 d . . . . .
H20A H -0.108754 0.769453 0.527678 0.034 Uiso 1 1 calc R U . . .
H20B H 0.021236 0.862195 0.478217 0.034 Uiso 1 1 calc R U . . .
C21 C 0.05301(18) 0.95369(14) 0.64901(11) 0.0333(3) Uani 1 1 d . . . . .
H21A H 0.047321 0.919097 0.708014 0.050 Uiso 1 1 calc R U . . .
H21B H -0.033299 1.010482 0.653479 0.050 Uiso 1 1 calc R U . . .
H21C H 0.171574 1.013123 0.657659 0.050 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 C1 1.3507(13) . ?
O1 C18 1.4461(14) . ?
O2 C3 1.3506(13) . ?
O2 C20 1.4519(14) . ?
N1 C1 1.2643(15) . ?
N1 C4 1.4271(14) . ?
N2 C3 1.2614(15) . ?
N2 C11 1.4208(15) . ?
C1 C2 1.5078(16) . ?
C2 C3 1.5110(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.3877(17) . ?
C4 C9 1.3943(17) . ?
C5 C6 1.3879(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3896(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3913(19) . ?
C7 C10 1.5123(18) . ?
C8 C9 1.3873(17) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.3826(18) . ?
C11 C12 1.3873(18) . ?
C12 C13 1.3856(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3832(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3867(18) . ?
C14 C17 1.5112(17) . ?
C15 C16 1.3917(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 C19 1.5026(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5020(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 O1 C18 116.17(9) . . ?
C3 O2 C20 116.33(9) . . ?
C1 N1 C4 118.81(10) . . ?
C3 N2 C11 121.06(10) . . ?
N1 C1 O1 121.36(10) . . ?
N1 C1 C2 127.70(10) . . ?
O1 C1 C2 110.94(10) . . ?
C1 C2 C3 112.43(9) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 O2 121.22(10) . . ?
N2 C3 C2 128.12(10) . . ?
O2 C3 C2 110.65(9) . . ?
C5 C4 C9 119.17(11) . . ?
C5 C4 N1 120.11(11) . . ?
C9 C4 N1 120.58(11) . . ?
C4 C5 C6 120.21(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 121.55(12) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 117.48(12) . . ?
C6 C7 C10 121.42(13) . . ?
C8 C7 C10 121.10(13) . . ?
C9 C8 C7 121.88(12) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 119.70(12) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.76(11) . . ?
C16 C11 N2 121.45(11) . . ?
C12 C11 N2 119.57(12) . . ?
C13 C12 C11 120.58(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 121.45(13) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.44(12) . . ?
C13 C14 C17 120.75(12) . . ?
C15 C14 C17 121.81(13) . . ?
C14 C15 C16 121.79(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 119.97(12) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O1 C18 C19 107.22(10) . . ?
O1 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 107.29(10) . . ?
O2 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O2 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 N1 C1 O1 179.28(10) . . . . ?
C4 N1 C1 C2 -1.23(18) . . . . ?
C18 O1 C1 N1 4.91(15) . . . . ?
C18 O1 C1 C2 -174.66(9) . . . . ?
N1 C1 C2 C3 -78.21(15) . . . . ?
O1 C1 C2 C3 101.33(11) . . . . ?
C11 N2 C3 O2 176.81(10) . . . . ?
C11 N2 C3 C2 -4.52(19) . . . . ?
C20 O2 C3 N2 -4.27(16) . . . . ?
C20 O2 C3 C2 176.84(9) . . . . ?
C1 C2 C3 N2 147.68(12) . . . . ?
C1 C2 C3 O2 -33.53(13) . . . . ?
C1 N1 C4 C5 -92.88(14) . . . . ?
C1 N1 C4 C9 91.35(14) . . . . ?
C9 C4 C5 C6 -1.29(18) . . . . ?
N1 C4 C5 C6 -177.13(11) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C8 0.08(19) . . . . ?
C5 C6 C7 C10 -179.19(13) . . . . ?
C6 C7 C8 C9 -0.35(19) . . . . ?
C10 C7 C8 C9 178.91(12) . . . . ?
C7 C8 C9 C4 -0.19(19) . . . . ?
C5 C4 C9 C8 1.01(18) . . . . ?
N1 C4 C9 C8 176.83(11) . . . . ?
C3 N2 C11 C16 91.02(15) . . . . ?
C3 N2 C11 C12 -94.40(15) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
N2 C11 C12 C13 -175.66(12) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C12 C13 C14 C17 179.73(14) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C17 C14 C15 C16 -179.90(12) . . . . ?
C12 C11 C16 C15 0.76(19) . . . . ?
N2 C11 C16 C15 175.39(11) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C1 O1 C18 C19 176.38(10) . . . . ?
C3 O2 C20 C21 -175.71(10) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_ML014
_database_code_depnum_ccdc_archive 'CCDC 1841079'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 N2 O4 Rh'
_chemical_formula_sum            'C23 H25 N2 O4 Rh'
_chemical_formula_weight         496.36

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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7606(9)
_cell_length_b                   10.5377(10)
_cell_length_c                   11.5641(11)
_cell_angle_alpha                96.6850(10)
_cell_angle_beta                 103.8860(10)
_cell_angle_gamma                98.2180(10)
_cell_volume                     1128.65(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.79

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.787
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13739
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         28.918
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5422
_reflns_number_gt                5028
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+0.5790P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5422
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0513
_refine_ls_wR_factor_gt          0.0497
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Rh1 Rh 0.76535(2) 0.51528(2) 0.22603(2) 0.02043(4) Uani 1 1 d . . . . .
O1 O 0.34392(11) 0.29895(11) 0.11877(10) 0.0257(2) Uani 1 1 d . . . . .
O2 O 0.51108(11) 0.64935(11) 0.44621(10) 0.0247(2) Uani 1 1 d . . . . .
O3 O 0.88571(14) 0.41515(14) 0.02506(13) 0.0437(3) Uani 1 1 d . . . . .
O4 O 1.04084(13) 0.70684(13) 0.30554(13) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.57741(13) 0.38494(12) 0.15621(11) 0.0206(2) Uani 1 1 d . . . . .
N2 N 0.68234(13) 0.59453(12) 0.35935(11) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.45554(16) 0.39015(14) 0.18643(14) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.43680(15) 0.47862(15) 0.27863(14) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.342301 0.474697 0.288025 0.026 Uiso 1 1 calc R U . . .
C3 C 0.54402(16) 0.57225(15) 0.35823(13) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.57663(15) 0.28486(14) 0.05923(13) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.52756(18) 0.30070(16) -0.06034(15) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.481588 0.371959 -0.079674 0.034 Uiso 1 1 calc R U . . .
C6 C 0.54594(19) 0.21202(17) -0.15150(15) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.513306 0.224365 -0.232977 0.036 Uiso 1 1 calc R U . . .
C7 C 0.61077(18) 0.10572(16) -0.12672(14) 0.0273(3) Uani 1 1 d . . . . .
C8 C 0.65365(19) 0.08826(16) -0.00681(15) 0.0296(3) Uani 1 1 d . . . . .
H8 H 0.694619 0.014336 0.012361 0.036 Uiso 1 1 calc R U . . .
C9 C 0.63749(18) 0.17731(16) 0.08544(14) 0.0256(3) Uani 1 1 d . . . . .
H9 H 0.668378 0.164252 0.166874 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6358(2) 0.01318(19) -0.22638(17) 0.0424(5) Uani 1 1 d . . . . .
H10A H 0.575505 0.024553 -0.304133 0.064 Uiso 1 1 calc R U . . .
H10B H 0.611251 -0.076301 -0.212648 0.064 Uiso 1 1 calc R U . . .
H10C H 0.736910 0.031250 -0.227045 0.064 Uiso 1 1 calc R U . . .
C11 C 0.77722(16) 0.69176(15) 0.45431(13) 0.0216(3) Uani 1 1 d . . . . .
C12 C 0.88913(16) 0.65518(15) 0.53571(14) 0.0233(3) Uani 1 1 d . . . . .
H12 H 0.899403 0.566545 0.530478 0.028 Uiso 1 1 calc R U . . .
C13 C 0.98607(17) 0.74757(16) 0.62470(14) 0.0255(3) Uani 1 1 d . . . . .
H13 H 1.061960 0.720983 0.679365 0.031 Uiso 1 1 calc R U . . .
C14 C 0.97391(17) 0.87817(16) 0.63510(14) 0.0265(3) Uani 1 1 d . . . . .
C15 C 0.86223(18) 0.91368(16) 0.55228(15) 0.0274(3) Uani 1 1 d . . . . .
H15 H 0.852368 1.002387 0.556872 0.033 Uiso 1 1 calc R U . . .
C16 C 0.76525(17) 0.82223(16) 0.46336(15) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.689990 0.848963 0.408149 0.031 Uiso 1 1 calc R U . . .
C17 C 1.0777(2) 0.97888(18) 0.73218(16) 0.0389(4) Uani 1 1 d . . . . .
H17A H 1.085944 0.949857 0.810666 0.058 Uiso 1 1 calc R U . . .
H17B H 1.042493 1.061462 0.733663 0.058 Uiso 1 1 calc R U . . .
H17C H 1.171952 0.990657 0.715183 0.058 Uiso 1 1 calc R U . . .
C18 C 0.20259(16) 0.29644(17) 0.13691(16) 0.0290(3) Uani 1 1 d . . . . .
H18A H 0.173862 0.382383 0.131465 0.035 Uiso 1 1 calc R U . . .
H18B H 0.200640 0.273880 0.217318 0.035 Uiso 1 1 calc R U . . .
C19 C 0.10251(19) 0.19464(19) 0.03862(18) 0.0381(4) Uani 1 1 d . . . . .
H19A H 0.110282 0.215282 -0.040283 0.057 Uiso 1 1 calc R U . . .
H19B H 0.003691 0.193233 0.044151 0.057 Uiso 1 1 calc R U . . .
H19C H 0.128620 0.109335 0.048216 0.057 Uiso 1 1 calc R U . . .
C20 C 0.36310(16) 0.65110(16) 0.44429(14) 0.0250(3) Uani 1 1 d . . . . .
H20A H 0.318200 0.567596 0.461682 0.030 Uiso 1 1 calc R U . . .
H20B H 0.308955 0.665073 0.364075 0.030 Uiso 1 1 calc R U . . .
C21 C 0.36233(19) 0.76093(18) 0.53985(16) 0.0335(4) Uani 1 1 d . . . . .
H21A H 0.415814 0.745630 0.618731 0.050 Uiso 1 1 calc R U . . .
H21B H 0.263201 0.765776 0.541231 0.050 Uiso 1 1 calc R U . . .
H21C H 0.407474 0.842824 0.521741 0.050 Uiso 1 1 calc R U . . .
C22 C 0.83914(17) 0.45049(16) 0.10160(16) 0.0292(3) Uani 1 1 d . . . . .
C23 C 0.93548(17) 0.63438(16) 0.27939(15) 0.0269(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rh1 C23 1.8562(17) . ?
Rh1 C22 1.8614(17) . ?
Rh1 N1 2.0528(13) . ?
Rh1 N2 2.0553(13) . ?
O1 C1 1.3562(18) . ?
O1 C18 1.4413(18) . ?
O2 C3 1.3557(18) . ?
O2 C20 1.4421(17) . ?
O3 C22 1.137(2) . ?
O4 C23 1.142(2) . ?
N1 C1 1.3243(19) . ?
N1 C4 1.4451(19) . ?
N2 C3 1.3335(19) . ?
N2 C11 1.4464(19) . ?
C1 C2 1.397(2) . ?
C2 C3 1.395(2) . ?
C2 H2 0.9500 . ?
C4 C9 1.384(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 C10 1.510(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.390(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(2) . ?
C14 C17 1.511(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.510(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.506(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C23 Rh1 C22 86.52(7) . . ?
C23 Rh1 N1 176.43(6) . . ?
C22 Rh1 N1 90.71(6) . . ?
C23 Rh1 N2 92.68(6) . . ?
C22 Rh1 N2 177.22(6) . . ?
N1 Rh1 N2 89.98(5) . . ?
C1 O1 C18 120.34(12) . . ?
C3 O2 C20 119.96(12) . . ?
C1 N1 C4 117.70(12) . . ?
C1 N1 Rh1 125.78(10) . . ?
C4 N1 Rh1 116.34(9) . . ?
C3 N2 C11 117.35(12) . . ?
C3 N2 Rh1 124.50(10) . . ?
C11 N2 Rh1 117.81(9) . . ?
N1 C1 O1 113.87(13) . . ?
N1 C1 C2 125.59(14) . . ?
O1 C1 C2 120.54(13) . . ?
C3 C2 C1 126.04(14) . . ?
C3 C2 H2 117.0 . . ?
C1 C2 H2 117.0 . . ?
N2 C3 O2 113.95(13) . . ?
N2 C3 C2 126.35(14) . . ?
O2 C3 C2 119.69(13) . . ?
C9 C4 C5 119.32(14) . . ?
C9 C4 N1 119.63(13) . . ?
C5 C4 N1 120.79(14) . . ?
C6 C5 C4 119.74(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.71(15) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 117.77(15) . . ?
C6 C7 C10 121.14(16) . . ?
C8 C7 C10 121.08(16) . . ?
C9 C8 C7 121.02(15) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C4 C9 C8 120.34(15) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.62(14) . . ?
C16 C11 N2 122.14(13) . . ?
C12 C11 N2 119.15(14) . . ?
C13 C12 C11 120.46(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 121.25(15) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 117.71(15) . . ?
C13 C14 C17 121.61(15) . . ?
C15 C14 C17 120.69(16) . . ?
C16 C15 C14 121.39(15) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 120.57(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 C19 106.49(13) . . ?
O1 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
O1 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 106.86(13) . . ?
O2 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O2 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 Rh1 177.65(15) . . ?
O4 C23 Rh1 176.04(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 -0.81(19) . . . . ?
Rh1 N1 C1 O1 174.17(9) . . . . ?
C4 N1 C1 C2 179.00(14) . . . . ?
Rh1 N1 C1 C2 -6.0(2) . . . . ?
C18 O1 C1 N1 -176.89(13) . . . . ?
C18 O1 C1 C2 3.3(2) . . . . ?
N1 C1 C2 C3 -3.3(3) . . . . ?
O1 C1 C2 C3 176.50(14) . . . . ?
C11 N2 C3 O2 2.23(19) . . . . ?
Rh1 N2 C3 O2 -170.79(9) . . . . ?
C11 N2 C3 C2 -176.56(14) . . . . ?
Rh1 N2 C3 C2 10.4(2) . . . . ?
C20 O2 C3 N2 169.91(13) . . . . ?
C20 O2 C3 C2 -11.2(2) . . . . ?
C1 C2 C3 N2 0.8(3) . . . . ?
C1 C2 C3 O2 -177.93(14) . . . . ?
C1 N1 C4 C9 -104.72(17) . . . . ?
Rh1 N1 C4 C9 79.83(16) . . . . ?
C1 N1 C4 C5 81.25(19) . . . . ?
Rh1 N1 C4 C5 -94.21(15) . . . . ?
C9 C4 C5 C6 -2.9(2) . . . . ?
N1 C4 C5 C6 171.15(15) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 1.8(3) . . . . ?
C5 C6 C7 C10 -177.35(17) . . . . ?
C6 C7 C8 C9 -2.6(3) . . . . ?
C10 C7 C8 C9 176.54(17) . . . . ?
C5 C4 C9 C8 2.1(2) . . . . ?
N1 C4 C9 C8 -172.01(15) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
C3 N2 C11 C16 -65.1(2) . . . . ?
Rh1 N2 C11 C16 108.37(15) . . . . ?
C3 N2 C11 C12 118.40(16) . . . . ?
Rh1 N2 C11 C12 -68.10(16) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
N2 C11 C12 C13 177.09(14) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C12 C13 C14 C17 179.36(16) . . . . ?
C13 C14 C15 C16 0.8(2) . . . . ?
C17 C14 C15 C16 -179.37(16) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
N2 C11 C16 C15 -177.00(14) . . . . ?
C1 O1 C18 C19 173.57(14) . . . . ?
C3 O2 C20 C21 -170.64(14) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_ML023
_database_code_depnum_ccdc_archive 'CCDC 1841083'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H54 N8 Zn'
_chemical_formula_sum            'C42 H54 N8 Zn'
_chemical_formula_weight         736.30

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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                   17.462(2)
_cell_length_b                   10.8487(14)
_cell_length_c                   21.572(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.3770(10)
_cell_angle_gamma                90
_cell_volume                     3940.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.59

_exptl_crystal_description       irregular
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.663
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23441
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.934
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4936
_reflns_number_gt                4067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+4.2331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4936
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.20347(2) 0.250000 0.01474(8) Uani 1 2 d S T P . .
N1 N 0.39768(8) 0.10801(12) 0.22222(6) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.46709(8) 0.29261(12) 0.31984(6) 0.0162(3) Uani 1 1 d . . . . .
N3 N 0.31384(8) -0.03145(13) 0.25753(7) 0.0200(3) Uani 1 1 d . . . . .
N4 N 0.42386(9) 0.26824(14) 0.41377(7) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.36637(9) 0.06633(15) 0.26937(8) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.38707(10) 0.11592(15) 0.33189(7) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.373173 0.067220 0.363868 0.021 Uiso 1 1 calc R U . . .
C3 C 0.42570(9) 0.22832(15) 0.35345(7) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.35298(9) 0.10095(14) 0.15706(7) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.27041(10) 0.11349(16) 0.13799(8) 0.0205(3) Uani 1 1 d . . . . .
H5 H 0.242510 0.128487 0.169525 0.025 Uiso 1 1 calc R U . . .
C6 C 0.22844(10) 0.10443(17) 0.07383(8) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.172202 0.111415 0.062426 0.028 Uiso 1 1 calc R U . . .
C7 C 0.26698(11) 0.08531(16) 0.02573(8) 0.0223(4) Uani 1 1 d . . . . .
C8 C 0.34931(10) 0.07933(15) 0.04444(8) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.377266 0.069943 0.012479 0.025 Uiso 1 1 calc R U . . .
C9 C 0.39210(10) 0.08670(15) 0.10876(8) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.448427 0.081998 0.119918 0.021 Uiso 1 1 calc R U . . .
C10 C 0.22011(12) 0.0719(2) -0.04364(8) 0.0314(4) Uani 1 1 d . . . . .
H10A H 0.208612 0.153719 -0.063129 0.047 Uiso 1 1 calc R U . . .
H10B H 0.170151 0.028846 -0.045722 0.047 Uiso 1 1 calc R U . . .
H10C H 0.251154 0.024397 -0.067079 0.047 Uiso 1 1 calc R U . . .
C11 C 0.47797(9) 0.42142(15) 0.32971(7) 0.0169(3) Uani 1 1 d . . . . .
C12 C 0.54981(10) 0.47574(16) 0.32809(8) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.591398 0.425662 0.321162 0.023 Uiso 1 1 calc R U . . .
C13 C 0.56140(10) 0.60139(16) 0.33644(8) 0.0223(4) Uani 1 1 d . . . . .
H13 H 0.610920 0.636046 0.335157 0.027 Uiso 1 1 calc R U . . .
C14 C 0.50204(10) 0.67823(15) 0.34667(8) 0.0216(3) Uani 1 1 d . . . . .
C15 C 0.42985(10) 0.62413(16) 0.34644(8) 0.0221(4) Uani 1 1 d . . . . .
H15 H 0.387885 0.674687 0.352274 0.027 Uiso 1 1 calc R U . . .
C16 C 0.41744(10) 0.49850(15) 0.33794(8) 0.0201(3) Uani 1 1 d . . . . .
H16 H 0.367240 0.464455 0.337704 0.024 Uiso 1 1 calc R U . . .
C17 C 0.51398(12) 0.81503(17) 0.35732(11) 0.0327(4) Uani 1 1 d . . . . .
H17A H 0.568193 0.830836 0.383441 0.049 Uiso 1 1 calc R U . . .
H17B H 0.475946 0.846478 0.379689 0.049 Uiso 1 1 calc R U . . .
H17C H 0.505552 0.856682 0.315736 0.049 Uiso 1 1 calc R U . . .
C18 C 0.32084(11) -0.13172(16) 0.21480(8) 0.0248(4) Uani 1 1 d . . . . .
H18A H 0.366037 -0.116260 0.196954 0.037 Uiso 1 1 calc R U . . .
H18B H 0.272031 -0.137221 0.179727 0.037 Uiso 1 1 calc R U . . .
H18C H 0.329175 -0.209371 0.238872 0.037 Uiso 1 1 calc R U . . .
C19 C 0.26408(11) -0.05982(18) 0.30010(9) 0.0269(4) Uani 1 1 d . . . . .
H19A H 0.294340 -0.109469 0.336301 0.040 Uiso 1 1 calc R U . . .
H19B H 0.217291 -0.106126 0.276356 0.040 Uiso 1 1 calc R U . . .
H19C H 0.247100 0.017028 0.316314 0.040 Uiso 1 1 calc R U . . .
C20 C 0.36015(13) 0.23539(19) 0.44228(10) 0.0344(5) Uani 1 1 d . . . . .
H20A H 0.312850 0.212575 0.408269 0.052 Uiso 1 1 calc R U . . .
H20B H 0.347797 0.305941 0.466316 0.052 Uiso 1 1 calc R U . . .
H20C H 0.376767 0.165460 0.471520 0.052 Uiso 1 1 calc R U . . .
C21 C 0.49134(13) 0.32872(19) 0.45728(8) 0.0324(4) Uani 1 1 d . . . . .
H21A H 0.537677 0.322749 0.439896 0.049 Uiso 1 1 calc R U . . .
H21B H 0.503169 0.288482 0.499430 0.049 Uiso 1 1 calc R U . . .
H21C H 0.478667 0.415685 0.461837 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
Zn1 N2 1.9986(13) 2_655 ?
Zn1 N2 1.9987(13) . ?
Zn1 N1 2.0140(13) . ?
Zn1 N1 2.0141(13) 2_655 ?
N1 C1 1.354(2) . ?
N1 C4 1.4175(19) . ?
N2 C3 1.346(2) . ?
N2 C11 1.419(2) . ?
N3 C1 1.381(2) . ?
N3 C18 1.452(2) . ?
N3 C19 1.455(2) . ?
N4 C3 1.380(2) . ?
N4 C20 1.451(2) . ?
N4 C21 1.454(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.411(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.397(2) . ?
C4 C9 1.398(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C10 1.510(2) . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.395(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 C17 1.508(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
N2 Zn1 N2 122.12(8) 2_655 . ?
N2 Zn1 N1 115.74(5) 2_655 . ?
N2 Zn1 N1 93.63(5) . . ?
N2 Zn1 N1 93.63(5) 2_655 2_655 ?
N2 Zn1 N1 115.74(5) . 2_655 ?
N1 Zn1 N1 118.12(8) . 2_655 ?
C1 N1 C4 120.07(13) . . ?
C1 N1 Zn1 116.83(10) . . ?
C4 N1 Zn1 122.32(10) . . ?
C3 N2 C11 119.95(13) . . ?
C3 N2 Zn1 117.26(11) . . ?
C11 N2 Zn1 122.40(10) . . ?
C1 N3 C18 121.96(14) . . ?
C1 N3 C19 121.62(14) . . ?
C18 N3 C19 114.03(14) . . ?
C3 N4 C20 122.33(15) . . ?
C3 N4 C21 122.20(15) . . ?
C20 N4 C21 114.74(15) . . ?
N1 C1 N3 119.89(14) . . ?
N1 C1 C2 122.69(14) . . ?
N3 C1 C2 117.39(14) . . ?
C1 C2 C3 128.67(15) . . ?
C1 C2 H2 115.7 . . ?
C3 C2 H2 115.7 . . ?
N2 C3 N4 119.69(14) . . ?
N2 C3 C2 123.25(14) . . ?
N4 C3 C2 116.95(14) . . ?
C5 C4 C9 117.49(14) . . ?
C5 C4 N1 122.72(14) . . ?
C9 C4 N1 119.72(14) . . ?
C6 C5 C4 121.19(15) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.44(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 117.25(15) . . ?
C8 C7 C10 122.08(16) . . ?
C6 C7 C10 120.67(16) . . ?
C7 C8 C9 121.85(15) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 120.65(15) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.82(15) . . ?
C12 C11 N2 119.86(14) . . ?
C16 C11 N2 122.24(14) . . ?
C13 C12 C11 120.98(16) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.42(16) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.35(16) . . ?
C15 C14 C17 120.33(16) . . ?
C13 C14 C17 122.32(16) . . ?
C16 C15 C14 121.76(16) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 120.63(15) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 N1 C1 N3 31.7(2) . . . . ?
Zn1 N1 C1 N3 -158.19(11) . . . . ?
C4 N1 C1 C2 -150.58(15) . . . . ?
Zn1 N1 C1 C2 19.6(2) . . . . ?
C18 N3 C1 N1 34.1(2) . . . . ?
C19 N3 C1 N1 -164.52(15) . . . . ?
C18 N3 C1 C2 -143.80(16) . . . . ?
C19 N3 C1 C2 17.6(2) . . . . ?
N1 C1 C2 C3 16.0(3) . . . . ?
N3 C1 C2 C3 -166.15(16) . . . . ?
C11 N2 C3 N4 -28.4(2) . . . . ?
Zn1 N2 C3 N4 158.63(12) . . . . ?
C11 N2 C3 C2 155.63(15) . . . . ?
Zn1 N2 C3 C2 -17.4(2) . . . . ?
C20 N4 C3 N2 156.27(17) . . . . ?
C21 N4 C3 N2 -34.0(2) . . . . ?
C20 N4 C3 C2 -27.5(2) . . . . ?
C21 N4 C3 C2 142.19(17) . . . . ?
C1 C2 C3 N2 -17.6(3) . . . . ?
C1 C2 C3 N4 166.34(16) . . . . ?
C1 N1 C4 C5 33.4(2) . . . . ?
Zn1 N1 C4 C5 -136.23(14) . . . . ?
C1 N1 C4 C9 -149.75(15) . . . . ?
Zn1 N1 C4 C9 40.65(19) . . . . ?
C9 C4 C5 C6 3.9(2) . . . . ?
N1 C4 C5 C6 -179.13(15) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C5 C6 C7 C10 178.16(17) . . . . ?
C6 C7 C8 C9 2.7(3) . . . . ?
C10 C7 C8 C9 -177.32(17) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C5 C4 C9 C8 -3.1(2) . . . . ?
N1 C4 C9 C8 179.88(14) . . . . ?
C3 N2 C11 C12 142.81(15) . . . . ?
Zn1 N2 C11 C12 -44.57(19) . . . . ?
C3 N2 C11 C16 -40.5(2) . . . . ?
Zn1 N2 C11 C16 132.11(14) . . . . ?
C16 C11 C12 C13 2.0(2) . . . . ?
N2 C11 C12 C13 178.84(15) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -1.7(3) . . . . ?
C12 C13 C14 C17 178.64(17) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
C17 C14 C15 C16 -178.84(17) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 C15 -2.2(2) . . . . ?
N2 C11 C16 C15 -178.96(15) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_ML021
_database_code_depnum_ccdc_archive 'CCDC 1841082'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#============================================================================== 
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N4 O2 Rh'
_chemical_formula_sum            'C23 H27 N4 O2 Rh'
_chemical_formula_weight         494.39

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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, 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                   15.376(5)
_cell_length_b                   14.622(5)
_cell_length_c                   20.208(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4543(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.63

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.777
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52413
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.170
_diffrn_reflns_theta_max         28.915
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5799
_reflns_number_gt                4587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+3.0541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5799
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
Rh1 Rh 0.56081(2) 0.38210(2) 0.40489(2) 0.01617(5) Uani 1 1 d . . . . .
O1 O 0.52953(10) 0.37194(11) 0.55102(7) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.37474(9) 0.43756(11) 0.38691(8) 0.0338(4) Uani 1 1 d . . . . .
N1 N 0.68889(10) 0.33859(10) 0.41322(7) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.58643(10) 0.37383(10) 0.30455(7) 0.0177(3) Uani 1 1 d . . . . .
N3 N 0.77985(10) 0.21108(10) 0.40154(7) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.59754(10) 0.26643(10) 0.21936(7) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.71134(11) 0.26149(12) 0.37953(9) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.66454(11) 0.23191(12) 0.32347(9) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.665197 0.168702 0.312599 0.021 Uiso 1 1 calc R U . . .
C3 C 0.61703(11) 0.29186(12) 0.28304(9) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.75433(12) 0.40229(12) 0.43188(9) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.82443(13) 0.42136(13) 0.38973(9) 0.0217(4) Uani 1 1 d . . . . .
H5 H 0.830979 0.387761 0.349805 0.026 Uiso 1 1 calc R U . . .
C6 C 0.88442(13) 0.48888(14) 0.40573(10) 0.0254(4) Uani 1 1 d . . . . .
H6 H 0.931575 0.500371 0.376517 0.031 Uiso 1 1 calc R U . . .
C7 C 0.87711(13) 0.54009(13) 0.46352(10) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.80817(13) 0.52015(13) 0.50562(10) 0.0240(4) Uani 1 1 d . . . . .
H8 H 0.801981 0.553482 0.545693 0.029 Uiso 1 1 calc R U . . .
C9 C 0.74804(13) 0.45227(13) 0.49017(9) 0.0221(4) Uani 1 1 d . . . . .
H9 H 0.701828 0.439864 0.520051 0.027 Uiso 1 1 calc R U . . .
C10 C 0.94094(15) 0.61548(14) 0.47934(12) 0.0347(5) Uani 1 1 d . . . . .
H10A H 1.000406 0.592688 0.473648 0.052 Uiso 1 1 calc R U . . .
H10B H 0.932673 0.635443 0.525207 0.052 Uiso 1 1 calc R U . . .
H10C H 0.931162 0.667231 0.449435 0.052 Uiso 1 1 calc R U . . .
C11 C 0.59421(12) 0.45092(12) 0.26214(9) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.53061(13) 0.51862(13) 0.26033(9) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.480404 0.512871 0.287416 0.027 Uiso 1 1 calc R U . . .
C13 C 0.53949(13) 0.59445(13) 0.21949(10) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.495061 0.639594 0.219195 0.030 Uiso 1 1 calc R U . . .
C14 C 0.61184(13) 0.60592(12) 0.17900(10) 0.0229(4) Uani 1 1 d . . . . .
C15 C 0.67549(13) 0.53837(13) 0.18098(9) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.725484 0.544198 0.153674 0.026 Uiso 1 1 calc R U . . .
C16 C 0.66757(12) 0.46249(12) 0.22203(9) 0.0197(4) Uani 1 1 d . . . . .
H16 H 0.712540 0.417943 0.222857 0.024 Uiso 1 1 calc R U . . .
C17 C 0.62109(15) 0.68961(15) 0.13574(12) 0.0350(5) Uani 1 1 d . . . . .
H17A H 0.652435 0.737337 0.160038 0.052 Uiso 1 1 calc R U . . .
H17B H 0.563266 0.712152 0.123486 0.052 Uiso 1 1 calc R U . . .
H17C H 0.653554 0.673636 0.095644 0.052 Uiso 1 1 calc R U . . .
C18 C 0.81276(13) 0.21973(13) 0.46890(9) 0.0229(4) Uani 1 1 d . . . . .
H18A H 0.864184 0.259328 0.469004 0.034 Uiso 1 1 calc R U . . .
H18B H 0.828553 0.159152 0.485815 0.034 Uiso 1 1 calc R U . . .
H18C H 0.767673 0.246526 0.497165 0.034 Uiso 1 1 calc R U . . .
C19 C 0.81815(12) 0.13791(13) 0.36188(10) 0.0230(4) Uani 1 1 d . . . . .
H19A H 0.784392 0.081666 0.367872 0.034 Uiso 1 1 calc R U . . .
H19B H 0.878282 0.127510 0.376084 0.034 Uiso 1 1 calc R U . . .
H19C H 0.817471 0.155460 0.315079 0.034 Uiso 1 1 calc R U . . .
C20 C 0.64924(13) 0.20018(14) 0.18304(10) 0.0275(4) Uani 1 1 d . . . . .
H20A H 0.706399 0.194034 0.204029 0.041 Uiso 1 1 calc R U . . .
H20B H 0.656606 0.220968 0.137272 0.041 Uiso 1 1 calc R U . . .
H20C H 0.619615 0.140844 0.183297 0.041 Uiso 1 1 calc R U . . .
C21 C 0.52243(13) 0.30228(14) 0.18393(10) 0.0262(4) Uani 1 1 d . . . . .
H21A H 0.480585 0.327360 0.215686 0.039 Uiso 1 1 calc R U . . .
H21B H 0.494924 0.252927 0.158660 0.039 Uiso 1 1 calc R U . . .
H21C H 0.541251 0.350683 0.153589 0.039 Uiso 1 1 calc R U . . .
C22 C 0.54226(12) 0.37814(13) 0.49545(10) 0.0217(4) Uani 1 1 d . . . . .
C23 C 0.44611(13) 0.41789(14) 0.39332(9) 0.0222(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rh1 C22 1.853(2) . ?
Rh1 C23 1.854(2) . ?
Rh1 N2 2.0690(16) . ?
Rh1 N1 2.0764(16) . ?
O1 C22 1.143(2) . ?
O2 C23 1.142(2) . ?
N1 C1 1.362(2) . ?
N1 C4 1.422(2) . ?
N2 C3 1.359(2) . ?
N2 C11 1.421(2) . ?
N3 C1 1.360(2) . ?
N3 C18 1.458(2) . ?
N3 C19 1.461(2) . ?
N4 C3 1.373(2) . ?
N4 C20 1.452(2) . ?
N4 C21 1.456(2) . ?
C1 C2 1.410(2) . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C4 C9 1.389(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 C10 1.510(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.392(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 C17 1.511(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C22 Rh1 C23 89.25(8) . . ?
C22 Rh1 N2 174.43(7) . . ?
C23 Rh1 N2 94.25(7) . . ?
C22 Rh1 N1 93.23(7) . . ?
C23 Rh1 N1 177.07(7) . . ?
N2 Rh1 N1 83.16(6) . . ?
C1 N1 C4 119.71(15) . . ?
C1 N1 Rh1 116.98(12) . . ?
C4 N1 Rh1 119.47(11) . . ?
C3 N2 C11 118.52(15) . . ?
C3 N2 Rh1 115.53(11) . . ?
C11 N2 Rh1 124.11(11) . . ?
C1 N3 C18 121.81(15) . . ?
C1 N3 C19 121.98(15) . . ?
C18 N3 C19 115.84(15) . . ?
C3 N4 C20 122.34(16) . . ?
C3 N4 C21 122.45(15) . . ?
C20 N4 C21 115.19(15) . . ?
N3 C1 N1 118.79(16) . . ?
N3 C1 C2 119.45(16) . . ?
N1 C1 C2 121.75(16) . . ?
C3 C2 C1 122.81(16) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
N2 C3 N4 117.60(16) . . ?
N2 C3 C2 123.01(16) . . ?
N4 C3 C2 119.35(16) . . ?
C9 C4 C5 117.64(17) . . ?
C9 C4 N1 121.34(17) . . ?
C5 C4 N1 120.88(16) . . ?
C6 C5 C4 120.70(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.60(18) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.53(18) . . ?
C8 C7 C10 121.28(19) . . ?
C6 C7 C10 121.19(19) . . ?
C7 C8 C9 121.26(18) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 121.26(18) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.73(17) . . ?
C12 C11 N2 121.38(17) . . ?
C16 C11 N2 120.87(16) . . ?
C13 C12 C11 120.94(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.63(18) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 117.40(17) . . ?
C13 C14 C17 120.88(18) . . ?
C15 C14 C17 121.71(19) . . ?
C16 C15 C14 121.47(18) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 120.83(17) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 Rh1 177.06(18) . . ?
O2 C23 Rh1 178.03(19) . . ?

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
C18 N3 C1 N1 18.9(2) . . . . ?
C19 N3 C1 N1 -168.32(16) . . . . ?
C18 N3 C1 C2 -159.88(17) . . . . ?
C19 N3 C1 C2 12.9(3) . . . . ?
C4 N1 C1 N3 47.1(2) . . . . ?
Rh1 N1 C1 N3 -155.10(13) . . . . ?
C4 N1 C1 C2 -134.13(18) . . . . ?
Rh1 N1 C1 C2 23.7(2) . . . . ?
N3 C1 C2 C3 -155.39(17) . . . . ?
N1 C1 C2 C3 25.8(3) . . . . ?
C11 N2 C3 N4 -44.7(2) . . . . ?
Rh1 N2 C3 N4 150.11(13) . . . . ?
C11 N2 C3 C2 137.43(18) . . . . ?
Rh1 N2 C3 C2 -27.7(2) . . . . ?
C20 N4 C3 N2 157.47(17) . . . . ?
C21 N4 C3 N2 -24.0(2) . . . . ?
C20 N4 C3 C2 -24.6(3) . . . . ?
C21 N4 C3 C2 153.94(17) . . . . ?
C1 C2 C3 N2 -23.6(3) . . . . ?
C1 C2 C3 N4 158.61(17) . . . . ?
C1 N1 C4 C9 -146.58(17) . . . . ?
Rh1 N1 C4 C9 56.2(2) . . . . ?
C1 N1 C4 C5 37.9(2) . . . . ?
Rh1 N1 C4 C5 -119.39(16) . . . . ?
C9 C4 C5 C6 -0.9(3) . . . . ?
N1 C4 C5 C6 174.82(17) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C10 -177.92(19) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C10 C7 C8 C9 178.30(18) . . . . ?
C5 C4 C9 C8 1.3(3) . . . . ?
N1 C4 C9 C8 -174.42(17) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C3 N2 C11 C12 144.85(18) . . . . ?
Rh1 N2 C11 C12 -51.3(2) . . . . ?
C3 N2 C11 C16 -36.9(2) . . . . ?
Rh1 N2 C11 C16 126.86(16) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
N2 C11 C12 C13 178.95(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 C17 -178.98(19) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C17 C14 C15 C16 178.50(19) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
N2 C11 C16 C15 -179.42(16) . . . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_ML026
_database_code_depnum_ccdc_archive 'CCDC 1841084'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H33 Al N4'
_chemical_formula_sum            'C23 H33 Al N4'
_chemical_formula_weight         392.51

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'

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

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

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

_cell_length_a                   17.128(2)
_cell_length_b                   8.9959(10)
_cell_length_c                   17.166(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.633(2)
_cell_angle_gamma                90
_cell_volume                     2321.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2131
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.97

_exptl_crystal_description       'wedge (cut)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27970
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         29.157
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             5164
_reflns_number_gt                4345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.8782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5164
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.25720(2) 0.67170(5) 0.45465(2) 0.01699(11) Uani 1 1 d . . . . .
N1 N 0.35338(7) 0.69487(13) 0.57252(7) 0.0189(2) Uani 1 1 d . . . . .
N2 N 0.25931(7) 0.45887(13) 0.45538(7) 0.0192(2) Uani 1 1 d . . . . .
N3 N 0.50740(8) 0.64819(14) 0.65856(7) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.34902(8) 0.25066(14) 0.47005(8) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.42538(8) 0.60649(16) 0.59293(8) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.41906(9) 0.47446(16) 0.54600(8) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.473215 0.435016 0.552257 0.026 Uiso 1 1 calc R U . . .
C3 C 0.34086(9) 0.39462(16) 0.49071(8) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.34777(8) 0.77632(15) 0.64109(8) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.37891(9) 0.71690(17) 0.72633(8) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.404289 0.620193 0.739172 0.027 Uiso 1 1 calc R U . . .
C6 C 0.37307(10) 0.79788(17) 0.79224(9) 0.0251(3) Uani 1 1 d . . . . .
H6 H 0.396087 0.756294 0.849953 0.030 Uiso 1 1 calc R U . . .
C7 C 0.33439(9) 0.93835(17) 0.77592(9) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.30120(9) 0.99475(17) 0.69013(8) 0.0233(3) Uani 1 1 d . . . . .
H8 H 0.273084 1.089323 0.676525 0.028 Uiso 1 1 calc R U . . .
C9 C 0.30826(9) 0.91582(16) 0.62384(8) 0.0215(3) Uani 1 1 d . . . . .
H9 H 0.285818 0.957919 0.566308 0.026 Uiso 1 1 calc R U . . .
C10 C 0.33009(11) 1.0267(2) 0.84862(10) 0.0335(4) Uani 1 1 d . . . . .
H10A H 0.312403 1.129197 0.828520 0.050 Uiso 1 1 calc R U . . .
H10B H 0.388693 1.026708 0.901641 0.050 Uiso 1 1 calc R U . . .
H10C H 0.286375 0.981588 0.862850 0.050 Uiso 1 1 calc R U . . .
C11 C 0.18312(9) 0.36959(15) 0.43629(8) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.10462(9) 0.38898(17) 0.35728(9) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.102338 0.459608 0.315090 0.030 Uiso 1 1 calc R U . . .
C13 C 0.02906(10) 0.30569(18) 0.33928(10) 0.0282(3) Uani 1 1 d . . . . .
H13 H -0.024390 0.321836 0.285432 0.034 Uiso 1 1 calc R U . . .
C14 C 0.03079(10) 0.19946(17) 0.39892(10) 0.0262(3) Uani 1 1 d . . . . .
C15 C 0.11017(10) 0.18012(17) 0.47761(9) 0.0256(3) Uani 1 1 d . . . . .
H15 H 0.113113 0.107363 0.519043 0.031 Uiso 1 1 calc R U . . .
C16 C 0.18488(9) 0.26459(16) 0.49677(8) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.237695 0.250797 0.551540 0.027 Uiso 1 1 calc R U . . .
C17 C -0.05000(11) 0.1076(2) 0.38027(12) 0.0371(4) Uani 1 1 d . . . . .
H17A H -0.072115 0.136503 0.421235 0.056 Uiso 1 1 calc R U . . .
H17B H -0.033891 0.002092 0.388432 0.056 Uiso 1 1 calc R U . . .
H17C H -0.096501 0.124690 0.319036 0.056 Uiso 1 1 calc R U . . .
C18 C 0.53053(10) 0.80278(17) 0.68392(10) 0.0279(3) Uani 1 1 d . . . . .
H18A H 0.489756 0.867515 0.635552 0.042 Uiso 1 1 calc R U . . .
H18B H 0.591665 0.821054 0.695815 0.042 Uiso 1 1 calc R U . . .
H18C H 0.525740 0.823952 0.737477 0.042 Uiso 1 1 calc R U . . .
C19 C 0.57970(10) 0.5421(2) 0.70308(10) 0.0363(4) Uani 1 1 d . . . . .
H19A H 0.555092 0.444088 0.703732 0.054 Uiso 1 1 calc R U . . .
H19B H 0.618426 0.574978 0.764177 0.054 Uiso 1 1 calc R U . . .
H19C H 0.614248 0.535990 0.671290 0.054 Uiso 1 1 calc R U . . .
C20 C 0.42879(11) 0.16397(18) 0.52373(11) 0.0328(4) Uani 1 1 d . . . . .
H20A H 0.472702 0.182224 0.503631 0.049 Uiso 1 1 calc R U . . .
H20B H 0.413657 0.058030 0.517606 0.049 Uiso 1 1 calc R U . . .
H20C H 0.453745 0.193278 0.586122 0.049 Uiso 1 1 calc R U . . .
C21 C 0.28489(10) 0.18113(18) 0.38695(10) 0.0290(3) Uani 1 1 d . . . . .
H21A H 0.244989 0.116771 0.397876 0.044 Uiso 1 1 calc R U . . .
H21B H 0.316599 0.121613 0.363182 0.044 Uiso 1 1 calc R U . . .
H21C H 0.250039 0.258332 0.344003 0.044 Uiso 1 1 calc R U . . .
C22 C 0.14497(9) 0.74875(17) 0.44417(9) 0.0243(3) Uani 1 1 d . . . . .
H22A H 0.141834 0.725459 0.498369 0.036 Uiso 1 1 calc R U . . .
H22B H 0.094678 0.702399 0.393117 0.036 Uiso 1 1 calc R U . . .
H22C H 0.142550 0.856738 0.435798 0.036 Uiso 1 1 calc R U . . .
C23 C 0.29590(10) 0.74374(16) 0.36954(9) 0.0236(3) Uani 1 1 d . . . . .
H23A H 0.286686 0.851403 0.361864 0.035 Uiso 1 1 calc R U . . .
H23B H 0.261038 0.694165 0.312226 0.035 Uiso 1 1 calc R U . . .
H23C H 0.359137 0.721302 0.392421 0.035 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 N1 1.9122(11) . ?
Al1 N2 1.9148(13) . ?
Al1 C22 1.9688(15) . ?
Al1 C23 1.9804(14) . ?
N1 C1 1.3645(17) . ?
N1 C4 1.4283(16) . ?
N2 C3 1.3569(17) . ?
N2 C11 1.4302(17) . ?
N3 C1 1.3662(17) . ?
N3 C18 1.454(2) . ?
N3 C19 1.4563(18) . ?
N4 C3 1.3676(19) . ?
N4 C20 1.4552(18) . ?
N4 C21 1.4597(18) . ?
C1 C2 1.410(2) . ?
C2 C3 1.4114(19) . ?
C2 H2 0.9500 . ?
C4 C9 1.3887(19) . ?
C4 C5 1.4010(17) . ?
C5 C6 1.3890(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3953(18) . ?
C7 C10 1.5109(19) . ?
C8 C9 1.3948(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3893(18) . ?
C11 C16 1.3931(19) . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(2) . ?
C14 C17 1.508(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
N1 Al1 N2 95.63(5) . . ?
N1 Al1 C22 111.51(5) . . ?
N2 Al1 C22 111.54(6) . . ?
N1 Al1 C23 108.76(6) . . ?
N2 Al1 C23 108.67(6) . . ?
C22 Al1 C23 118.34(6) . . ?
C1 N1 C4 119.79(10) . . ?
C1 N1 Al1 115.00(8) . . ?
C4 N1 Al1 124.32(9) . . ?
C3 N2 C11 119.61(12) . . ?
C3 N2 Al1 116.16(9) . . ?
C11 N2 Al1 123.21(9) . . ?
C1 N3 C18 122.30(12) . . ?
C1 N3 C19 122.18(13) . . ?
C18 N3 C19 115.35(12) . . ?
C3 N4 C20 121.66(12) . . ?
C3 N4 C21 122.46(12) . . ?
C20 N4 C21 115.32(12) . . ?
N1 C1 N3 119.83(12) . . ?
N1 C1 C2 122.11(11) . . ?
N3 C1 C2 118.01(12) . . ?
C1 C2 C3 126.96(12) . . ?
C1 C2 H2 116.5 . . ?
C3 C2 H2 116.5 . . ?
N2 C3 N4 119.91(12) . . ?
N2 C3 C2 121.72(13) . . ?
N4 C3 C2 118.32(12) . . ?
C9 C4 C5 118.06(12) . . ?
C9 C4 N1 120.40(11) . . ?
C5 C4 N1 121.51(12) . . ?
C6 C5 C4 120.70(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.70(12) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 117.16(12) . . ?
C6 C7 C10 121.23(12) . . ?
C8 C7 C10 121.60(14) . . ?
C9 C8 C7 121.68(13) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C4 C9 C8 120.65(12) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.54(13) . . ?
C12 C11 N2 120.21(12) . . ?
C16 C11 N2 121.23(12) . . ?
C11 C12 C13 120.64(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 121.03(13) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.78(13) . . ?
C13 C14 C17 121.76(14) . . ?
C15 C14 C17 120.46(14) . . ?
C16 C15 C14 121.51(13) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 120.48(13) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Al1 C22 H22A 109.5 . . ?
Al1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Al1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Al1 C23 H23A 109.5 . . ?
Al1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Al1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 N1 C1 N3 -34.72(18) . . . . ?
Al1 N1 C1 N3 155.65(10) . . . . ?
C4 N1 C1 C2 147.77(13) . . . . ?
Al1 N1 C1 C2 -21.86(16) . . . . ?
C18 N3 C1 N1 -25.27(19) . . . . ?
C19 N3 C1 N1 159.62(13) . . . . ?
C18 N3 C1 C2 152.33(13) . . . . ?
C19 N3 C1 C2 -22.77(19) . . . . ?
N1 C1 C2 C3 -17.5(2) . . . . ?
N3 C1 C2 C3 164.95(13) . . . . ?
C11 N2 C3 N4 31.54(17) . . . . ?
Al1 N2 C3 N4 -159.61(10) . . . . ?
C11 N2 C3 C2 -151.14(12) . . . . ?
Al1 N2 C3 C2 17.70(15) . . . . ?
C20 N4 C3 N2 -162.25(13) . . . . ?
C21 N4 C3 N2 26.71(19) . . . . ?
C20 N4 C3 C2 20.34(19) . . . . ?
C21 N4 C3 C2 -150.69(13) . . . . ?
C1 C2 C3 N2 20.0(2) . . . . ?
C1 C2 C3 N4 -162.64(13) . . . . ?
C1 N1 C4 C9 145.66(13) . . . . ?
Al1 N1 C4 C9 -45.73(17) . . . . ?
C1 N1 C4 C5 -36.46(19) . . . . ?
Al1 N1 C4 C5 132.15(12) . . . . ?
C9 C4 C5 C6 -2.2(2) . . . . ?
N1 C4 C5 C6 179.86(13) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C5 C6 C7 C10 -178.74(14) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C10 C7 C8 C9 177.43(14) . . . . ?
C5 C4 C9 C8 0.9(2) . . . . ?
N1 C4 C9 C8 178.88(12) . . . . ?
C7 C8 C9 C4 1.0(2) . . . . ?
C3 N2 C11 C12 -136.91(13) . . . . ?
Al1 N2 C11 C12 55.07(16) . . . . ?
C3 N2 C11 C16 44.75(17) . . . . ?
Al1 N2 C11 C16 -123.27(12) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
N2 C11 C12 C13 -177.95(13) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C13 C14 C17 -179.53(14) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C17 C14 C15 C16 -179.08(14) . . . . ?
C14 C15 C16 C11 -1.5(2) . . . . ?
C12 C11 C16 C15 0.9(2) . . . . ?
N2 C11 C16 C15 179.31(12) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.052

