# 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_sad_a
_database_code_depnum_ccdc_archive 'CCDC 1839909'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 Li N2 O4'
_chemical_formula_sum            'C23 H29 Li N2 O4'
_chemical_formula_weight         404.42

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'
Li Li -0.0003 0.0001 '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                   17.284(3)
_cell_length_b                   9.272(2)
_cell_length_c                   13.883(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.03(2)
_cell_angle_gamma                90
_cell_volume                     2208.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9207
_cell_measurement_theta_min      2.3745
_cell_measurement_theta_max      25.515

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.265
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8745
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'BRUKER Rotating Anode'
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24547
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         25.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4129
_reflns_number_gt                3481
_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0303P)²+0.8769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     279
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.63065(5) 0.23129(9) 0.16363(6) 0.0238(2) Uani 1 1 d . . . . .
Li1 Li 0.74344(13) 0.4913(2) 0.38359(15) 0.0250(5) Uani 1 1 d . . . . .
C1 C 0.61556(7) 0.26407(13) 0.32046(9) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.67372(6) 0.35873(11) 0.29962(7) 0.0206(2) Uani 1 1 d . . . . .
N2 N 0.80422(6) 0.55141(11) 0.27627(7) 0.0220(2) Uani 1 1 d . . . . .
O2 O 0.84484(5) 0.53891(10) 0.12631(6) 0.0259(2) Uani 1 1 d . . . . .
C2 C 0.58404(8) 0.23762(14) 0.40649(9) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.601267 0.289175 0.464287 0.030 Uiso 1 1 calc R U . . .
O4 O 0.68210(5) 0.63390(10) 0.44834(6) 0.0264(2) Uani 1 1 d . . . . .
C4 C 0.50060(8) 0.05626(15) 0.32013(10) 0.0297(3) Uani 1 1 d . . . . .
H4 H 0.460954 -0.014401 0.321595 0.036 Uiso 1 1 calc R U . . .
O3 O 0.81613(5) 0.41301(9) 0.49227(6) 0.0226(2) Uani 1 1 d . . . . .
C3 C 0.52634(8) 0.13273(14) 0.40431(10) 0.0284(3) Uani 1 1 d . . . . .
H3 H 0.503828 0.112646 0.461938 0.034 Uiso 1 1 calc R U . . .
C7 C 0.68204(7) 0.33525(13) 0.20697(9) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.58887(7) 0.18570(14) 0.23730(9) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.53199(8) 0.08148(14) 0.23343(10) 0.0276(3) Uani 1 1 d . . . . .
H5 H 0.515070 0.029860 0.175563 0.033 Uiso 1 1 calc R U . . .
C8 C 0.73441(8) 0.39583(14) 0.14965(9) 0.0238(3) Uani 1 1 d D . . . .
H8 H 0.7324(8) 0.3650(16) 0.0840(9) 0.035(4) Uiso 1 1 d D . . . .
C9 C 0.79116(7) 0.49318(14) 0.18796(9) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.89457(7) 0.63083(14) 0.18255(9) 0.0242(3) Uani 1 1 d . . . . .
C11 C 0.95829(8) 0.70323(15) 0.15638(10) 0.0294(3) Uani 1 1 d . . . . .
H11 H 0.974188 0.694008 0.093543 0.035 Uiso 1 1 calc R U . . .
C12 C 0.99818(8) 0.79103(15) 0.22758(11) 0.0313(3) Uani 1 1 d . . . . .
H12 H 1.042174 0.844482 0.212984 0.038 Uiso 1 1 calc R U . . .
C13 C 0.97448(8) 0.80154(15) 0.31990(10) 0.0301(3) Uani 1 1 d . . . . .
H13 H 1.002748 0.862273 0.366829 0.036 Uiso 1 1 calc R U . . .
C14 C 0.91034(8) 0.72517(14) 0.34505(10) 0.0270(3) Uani 1 1 d . . . . .
H14 H 0.894955 0.732098 0.408279 0.032 Uiso 1 1 calc R U . . .
C15 C 0.86974(7) 0.63858(14) 0.27430(9) 0.0228(3) Uani 1 1 d . . . . .
C16 C 0.64728(8) 0.75365(15) 0.39264(10) 0.0307(3) Uani 1 1 d . . . . .
H16A H 0.602638 0.790956 0.423540 0.037 Uiso 1 1 calc R U . . .
H16B H 0.627340 0.720398 0.326471 0.037 Uiso 1 1 calc R U . . .
C17 C 0.70523(9) 0.87191(15) 0.38623(11) 0.0351(3) Uani 1 1 d . . . . .
H17A H 0.680080 0.952436 0.348857 0.053 Uiso 1 1 calc R U . . .
H17B H 0.748701 0.835785 0.353925 0.053 Uiso 1 1 calc R U . . .
H17C H 0.724885 0.905021 0.451705 0.053 Uiso 1 1 calc R U . . .
C18 C 0.64509(8) 0.59937(15) 0.53276(9) 0.0268(3) Uani 1 1 d . . . . .
H18A H 0.662010 0.502101 0.556021 0.032 Uiso 1 1 calc R U . . .
H18B H 0.587929 0.596526 0.514391 0.032 Uiso 1 1 calc R U . . .
C19 C 0.66376(9) 0.70631(17) 0.61444(10) 0.0345(3) Uani 1 1 d . . . . .
H19A H 0.636712 0.678201 0.669596 0.052 Uiso 1 1 calc R U . . .
H19B H 0.646551 0.802719 0.592201 0.052 Uiso 1 1 calc R U . . .
H19C H 0.720128 0.707360 0.634502 0.052 Uiso 1 1 calc R U . . .
C20 C 0.84691(8) 0.51325(14) 0.56674(9) 0.0245(3) Uani 1 1 d . . . . .
H20A H 0.821637 0.608227 0.553611 0.029 Uiso 1 1 calc R U . . .
H20B H 0.903479 0.525600 0.563911 0.029 Uiso 1 1 calc R U . . .
C21 C 0.83433(8) 0.46452(15) 0.66800(9) 0.0283(3) Uani 1 1 d . . . . .
H21A H 0.850670 0.541266 0.714623 0.042 Uiso 1 1 calc R U . . .
H21B H 0.865217 0.377553 0.685059 0.042 Uiso 1 1 calc R U . . .
H21C H 0.778970 0.443269 0.669705 0.042 Uiso 1 1 calc R U . . .
C22 C 0.86591(8) 0.28999(15) 0.48766(9) 0.0270(3) Uani 1 1 d . . . . .
H22A H 0.870683 0.237557 0.550230 0.032 Uiso 1 1 calc R U . . .
H22B H 0.918581 0.322026 0.475913 0.032 Uiso 1 1 calc R U . . .
C23 C 0.83248(8) 0.19153(15) 0.40717(10) 0.0282(3) Uani 1 1 d . . . . .
H23A H 0.866288 0.107058 0.404869 0.042 Uiso 1 1 calc R U . . .
H23B H 0.829054 0.243076 0.345168 0.042 Uiso 1 1 calc R U . . .
H23C H 0.780311 0.160238 0.418979 0.042 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 C6 1.3882(15) . ?
O1 C7 1.3962(15) . ?
Li1 O4 1.978(2) . ?
Li1 O3 1.980(2) . ?
Li1 N1 1.995(2) . ?
Li1 N2 2.004(2) . ?
C1 N1 1.3913(16) . ?
C1 C2 1.3938(18) . ?
C1 C6 1.3941(17) . ?
N1 C7 1.3297(16) . ?
N2 C9 1.3334(16) . ?
N2 C15 1.3942(16) . ?
O2 C10 1.3822(16) . ?
O2 C9 1.4027(15) . ?
C2 C3 1.3906(19) . ?
C2 H2 0.9500 . ?
O4 C18 1.4383(15) . ?
O4 C16 1.4420(16) . ?
C4 C3 1.393(2) . ?
C4 C5 1.3991(19) . ?
C4 H4 0.9500 . ?
O3 C22 1.4349(15) . ?
O3 C20 1.4425(15) . ?
C3 H3 0.9500 . ?
C7 C8 1.3944(18) . ?
C6 C5 1.3749(18) . ?
C5 H5 0.9500 . ?
C8 C9 1.3900(19) . ?
C8 H8 0.951(12) . ?
C10 C11 1.3759(19) . ?
C10 C15 1.3950(18) . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3954(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3904(19) . ?
C14 H14 0.9500 . ?
C16 C17 1.495(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.5112(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5173(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.5026(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
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
C6 O1 C7 104.70(9) . . ?
O4 Li1 O3 102.96(10) . . ?
O4 Li1 N1 111.00(11) . . ?
O3 Li1 N1 120.06(12) . . ?
O4 Li1 N2 120.73(12) . . ?
O3 Li1 N2 109.09(11) . . ?
N1 Li1 N2 94.07(10) . . ?
N1 C1 C2 131.10(11) . . ?
N1 C1 C6 109.32(11) . . ?
C2 C1 C6 119.57(12) . . ?
C7 N1 C1 105.33(10) . . ?
C7 N1 Li1 122.48(10) . . ?
C1 N1 Li1 131.88(10) . . ?
C9 N2 C15 105.26(10) . . ?
C9 N2 Li1 121.73(11) . . ?
C15 N2 Li1 132.57(10) . . ?
C10 O2 C9 104.71(9) . . ?
C3 C2 C1 117.31(12) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C18 O4 C16 114.22(10) . . ?
C18 O4 Li1 122.56(10) . . ?
C16 O4 Li1 118.85(10) . . ?
C3 C4 C5 121.27(12) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C22 O3 C20 111.94(9) . . ?
C22 O3 Li1 125.86(10) . . ?
C20 O3 Li1 116.99(10) . . ?
C2 C3 C4 121.94(13) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1 C7 C8 129.85(12) . . ?
N1 C7 O1 113.04(11) . . ?
C8 C7 O1 117.08(11) . . ?
C5 C6 O1 128.27(12) . . ?
C5 C6 C1 124.14(12) . . ?
O1 C6 C1 107.58(11) . . ?
C6 C5 C4 115.76(12) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
C9 C8 C7 121.34(12) . . ?
C9 C8 H8 120.2(9) . . ?
C7 C8 H8 118.3(9) . . ?
N2 C9 C8 130.31(11) . . ?
N2 C9 O2 112.86(11) . . ?
C8 C9 O2 116.83(11) . . ?
C11 C10 O2 127.89(12) . . ?
C11 C10 C15 124.17(13) . . ?
O2 C10 C15 107.93(11) . . ?
C10 C11 C12 116.07(13) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C13 C12 C11 121.05(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 121.73(13) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 117.65(12) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 N2 131.44(12) . . ?
C14 C15 C10 119.32(12) . . ?
N2 C15 C10 109.24(11) . . ?
O4 C16 C17 110.97(11) . . ?
O4 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
O4 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 C19 112.95(11) . . ?
O4 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
O4 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
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 . . ?
O3 C20 C21 112.96(10) . . ?
O3 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
O3 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
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 C23 109.76(10) . . ?
O3 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O3 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_3l
_database_code_depnum_ccdc_archive 'CCDC 1839910'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 K N2 O3'
_chemical_formula_sum            'C19 H17 K N2 O3'
_chemical_formula_weight         360.44

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   11.200(2)
_cell_length_b                   19.897(3)
_cell_length_c                   7.745(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1725.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.7385
_cell_measurement_theta_max      26.111

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC Microsource'
_diffrn_measurement_device_type  'Bruker Smart APEX II Quazar'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26470
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         26.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3432
_reflns_number_gt                3325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.30C'
_computing_data_reduction        'SAINT V8.30C'
_computing_structure_solution    
'SHELXT(G.M.Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0350P)²+0.2658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3432
_refine_ls_number_parameters     249
_refine_ls_number_restraints     238
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      0.998
_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
O3 O 0.67815(12) 0.49293(6) 0.20346(19) 0.0220(3) Uani 0.745(13) 1 d D U P A 1
C16 C 0.73300(18) 0.42790(10) 0.2299(3) 0.0259(4) Uani 0.745(13) 1 d D U P A 1
H16A H 0.716204 0.397911 0.130845 0.031 Uiso 0.745(13) 1 calc R U P A 1
H16B H 0.701557 0.406649 0.336166 0.031 Uiso 0.745(13) 1 calc R U P A 1
C17 C 0.8677(4) 0.4403(3) 0.2465(8) 0.0328(12) Uani 0.745(13) 1 d D U P A 1
H17A H 0.904131 0.409179 0.331312 0.039 Uiso 0.745(13) 1 calc R U P A 1
H17B H 0.908351 0.434814 0.133872 0.039 Uiso 0.745(13) 1 calc R U P A 1
C18 C 0.8746(3) 0.5128(2) 0.3090(8) 0.0322(10) Uani 0.745(13) 1 d D U P A 1
H18A H 0.867246 0.515488 0.436163 0.039 Uiso 0.745(13) 1 calc R U P A 1
H18B H 0.950382 0.534272 0.272965 0.039 Uiso 0.745(13) 1 calc R U P A 1
C19 C 0.76841(18) 0.54486(10) 0.2202(3) 0.0266(4) Uani 0.745(13) 1 d D U P A 1
H19A H 0.737548 0.582808 0.289773 0.032 Uiso 0.745(13) 1 calc R U P A 1
H19B H 0.791618 0.562040 0.104998 0.032 Uiso 0.745(13) 1 calc R U P A 1
O3' O 0.67815(12) 0.49293(6) 0.20346(19) 0.0220(3) Uani 0.255(13) 1 d D U P A 2
C16' C 0.73300(18) 0.42790(10) 0.2299(3) 0.0259(4) Uani 0.255(13) 1 d D U P A 2
H16C H 0.741934 0.404056 0.118463 0.031 Uiso 0.255(13) 1 calc R U P A 2
H16D H 0.683274 0.400039 0.307658 0.031 Uiso 0.255(13) 1 calc R U P A 2
C17' C 0.8518(13) 0.4404(8) 0.309(2) 0.035(4) Uani 0.255(13) 1 d D U P A 2
H17C H 0.909479 0.404574 0.278679 0.042 Uiso 0.255(13) 1 calc R U P A 2
H17D H 0.846389 0.444493 0.435810 0.042 Uiso 0.255(13) 1 calc R U P A 2
C18' C 0.8847(9) 0.5069(6) 0.225(2) 0.033(3) Uani 0.255(13) 1 d D U P A 2
H18C H 0.945072 0.531208 0.294316 0.040 Uiso 0.255(13) 1 calc R U P A 2
H18D H 0.916423 0.499907 0.106859 0.040 Uiso 0.255(13) 1 calc R U P A 2
C19' C 0.76841(18) 0.54486(10) 0.2202(3) 0.0266(4) Uani 0.255(13) 1 d D U P A 2
H19C H 0.756779 0.570939 0.327729 0.032 Uiso 0.255(13) 1 calc R U P A 2
H19D H 0.765942 0.575998 0.120535 0.032 Uiso 0.255(13) 1 calc R U P A 2
K1 K 0.48971(3) 0.50265(2) 0.43119(9) 0.01730(10) Uani 1 1 d . . . . .
O1 O 0.71017(12) 0.33880(6) 0.79534(19) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.83990(11) 0.56391(6) 0.78081(17) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.57933(14) 0.40391(7) 0.6458(2) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.65596(14) 0.55347(7) 0.6584(2) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.53803(17) 0.33732(9) 0.6484(2) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.43652(17) 0.30785(10) 0.5759(3) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.380691 0.333665 0.511672 0.026 Uiso 1 1 calc R U . . .
C3 C 0.42037(18) 0.23939(10) 0.6014(3) 0.0257(4) Uani 1 1 d . . . . .
H3 H 0.351987 0.218102 0.553703 0.031 Uiso 1 1 calc R U . . .
C4 C 0.50207(19) 0.20101(10) 0.6954(3) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.487620 0.154345 0.710690 0.033 Uiso 1 1 calc R U . . .
C5 C 0.60444(19) 0.22957(10) 0.7673(3) 0.0261(4) Uani 1 1 d . . . . .
H5 H 0.660809 0.203876 0.830912 0.031 Uiso 1 1 calc R U . . .
C6 C 0.61827(17) 0.29791(9) 0.7397(2) 0.0193(4) Uani 1 1 d . . . . .
C7 C 0.68103(16) 0.40228(9) 0.7312(2) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.76290(16) 0.45333(9) 0.7713(2) 0.0185(4) Uani 1 1 d D . . . .
H8 H 0.8342(17) 0.4407(11) 0.832(3) 0.018(5) Uiso 1 1 d D . . . .
C9 C 0.74656(16) 0.52144(10) 0.7311(2) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.80125(17) 0.62763(9) 0.7348(2) 0.0189(4) Uani 1 1 d . . . . .
C11 C 0.85870(18) 0.68781(10) 0.7623(3) 0.0250(4) Uani 1 1 d . . . . .
H11 H 0.934616 0.690404 0.816581 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7978(2) 0.74471(10) 0.7050(3) 0.0282(5) Uani 1 1 d . . . . .
H12 H 0.833279 0.787662 0.720368 0.034 Uiso 1 1 calc R U . . .
C13 C 0.68621(19) 0.74036(10) 0.6258(3) 0.0265(5) Uani 1 1 d . . . . .
H13 H 0.647753 0.780300 0.588056 0.032 Uiso 1 1 calc R U . . .
C14 C 0.62997(18) 0.67865(10) 0.6008(3) 0.0227(4) Uani 1 1 d . . . . .
H14 H 0.554217 0.675702 0.546124 0.027 Uiso 1 1 calc R U . . .
C15 C 0.68944(16) 0.62129(8) 0.6593(2) 0.0179(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
O3 C16 1.447(2) . ?
O3 C19 1.451(2) . ?
O3 K1 2.7573(15) . ?
O3 K1 2.8265(16) 2_664 ?
C16 C17 1.534(5) . ?
C16 K1 3.474(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.524(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.515(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O3' C16' 1.447(2) . ?
O3' C19' 1.451(2) . ?
O3' K1 2.7573(15) . ?
O3' K1 2.8265(16) 2_664 ?
C16' C17' 1.484(14) . ?
C16' K1 3.474(2) . ?
C16' H16C 0.9900 . ?
C16' H16D 0.9900 . ?
C17' C18' 1.520(16) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' C19' 1.506(11) . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
K1 N2 2.7542(17) . ?
K1 N1 2.7621(16) . ?
K1 N2 2.8936(17) 2_664 ?
K1 N1 2.9901(17) 2_664 ?
K1 C7 3.1037(18) 2_664 ?
K1 C9 3.1038(19) 2_664 ?
K1 C8 3.2101(19) 2_664 ?
O1 C6 1.381(2) . ?
O1 C7 1.396(2) . ?
O2 C10 1.386(2) . ?
O2 C9 1.398(2) . ?
N1 C7 1.318(2) . ?
N1 C1 1.404(2) . ?
N2 C9 1.324(2) . ?
N2 C15 1.401(2) . ?
C1 C6 1.387(3) . ?
C1 C2 1.397(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.403(3) . ?
C8 C9 1.403(3) . ?
C8 H8 0.959(18) . ?
C10 C11 1.376(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(3) . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 C19 109.16(14) . . ?
C16 O3 K1 107.28(11) . . ?
C19 O3 K1 115.23(11) . . ?
C16 O3 K1 114.57(11) . 2_664 ?
C19 O3 K1 120.52(11) . 2_664 ?
K1 O3 K1 88.05(4) . 2_664 ?
O3 C16 C17 106.6(2) . . ?
O3 C16 K1 49.28(9) . . ?
C17 C16 K1 131.7(2) . . ?
O3 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
K1 C16 H16A 117.2 . . ?
O3 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
K1 C16 H16B 62.0 . . ?
H16A C16 H16B 108.6 . . ?
C18 C17 C16 103.2(3) . . ?
C18 C17 H17A 111.1 . . ?
C16 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C19 C18 C17 102.4(3) . . ?
C19 C18 H18A 111.3 . . ?
C17 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C17 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
O3 C19 C18 106.7(2) . . ?
O3 C19 H19A 110.4 . . ?
C18 C19 H19A 110.4 . . ?
O3 C19 H19B 110.4 . . ?
C18 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
C16' O3' C19' 109.16(14) . . ?
C16' O3' K1 107.28(11) . . ?
C19' O3' K1 115.23(11) . . ?
K1 O3' K1 88.05(4) . 2_664 ?
O3' C16' C17' 106.8(6) . . ?
O3' C16' K1 49.28(9) . . ?
C17' C16' K1 116.5(7) . . ?
O3' C16' H16C 110.4 . . ?
C17' C16' H16C 110.4 . . ?
K1 C16' H16C 132.5 . . ?
O3' C16' H16D 110.4 . . ?
C17' C16' H16D 110.4 . . ?
K1 C16' H16D 61.7 . . ?
H16C C16' H16D 108.6 . . ?
C16' C17' C18' 100.8(9) . . ?
C16' C17' H17C 111.6 . . ?
C18' C17' H17C 111.6 . . ?
C16' C17' H17D 111.6 . . ?
C18' C17' H17D 111.6 . . ?
H17C C17' H17D 109.4 . . ?
C19' C18' C17' 103.7(10) . . ?
C19' C18' H18C 111.0 . . ?
C17' C18' H18C 111.0 . . ?
C19' C18' H18D 111.0 . . ?
C17' C18' H18D 111.0 . . ?
H18C C18' H18D 109.0 . . ?
O3' C19' C18' 104.3(4) . . ?
O3' C19' H19C 110.9 . . ?
C18' C19' H19C 110.9 . . ?
O3' C19' H19D 110.9 . . ?
C18' C19' H19D 110.9 . . ?
H19C C19' H19D 108.9 . . ?
N2 K1 O3 85.23(5) . . ?
N2 K1 O3' 85.23(5) . . ?
N2 K1 N1 68.35(5) . . ?
O3 K1 N1 93.26(5) . . ?
O3' K1 N1 93.26(5) . . ?
N2 K1 O3 87.80(5) . 2_665 ?
O3 K1 O3 171.32(5) . 2_665 ?
N1 K1 O3 79.34(5) . 2_665 ?
N2 K1 N2 171.63(5) . 2_664 ?
O3 K1 N2 86.41(5) . 2_664 ?
N1 K1 N2 111.70(5) . 2_664 ?
O3 K1 N2 100.47(5) 2_665 2_664 ?
N2 K1 N1 114.77(4) . 2_664 ?
O3 K1 N1 76.62(4) . 2_664 ?
N1 K1 N1 168.82(5) . 2_664 ?
O3 K1 N1 111.11(4) 2_665 2_664 ?
N2 K1 N1 63.53(4) 2_664 2_664 ?
N2 K1 C7 120.77(5) . 2_664 ?
O3 K1 C7 101.25(5) . 2_664 ?
N1 K1 C7 163.26(5) . 2_664 ?
O3 K1 C7 86.76(5) 2_665 2_664 ?
N2 K1 C7 61.54(5) 2_664 2_664 ?
N1 K1 C7 24.89(5) 2_664 2_664 ?
N2 K1 C9 162.19(5) . 2_664 ?
O3 K1 C9 108.81(5) . 2_664 ?
O3' K1 C9 108.81(5) . 2_664 ?
N1 K1 C9 120.02(5) . 2_664 ?
O3 K1 C9 79.06(5) 2_665 2_664 ?
N2 K1 C9 25.19(5) 2_664 2_664 ?
N1 K1 C9 60.43(5) 2_664 2_664 ?
C7 K1 C9 47.14(5) 2_664 2_664 ?
N2 K1 C8 137.91(5) . 2_664 ?
O3 K1 C8 116.55(5) . 2_664 ?
N1 K1 C8 138.28(5) . 2_664 ?
O3 K1 C8 72.12(5) 2_665 2_664 ?
N2 K1 C8 47.68(5) 2_664 2_664 ?
N1 K1 C8 46.94(4) 2_664 2_664 ?
C7 K1 C8 25.61(5) 2_664 2_664 ?
C9 K1 C8 25.60(5) 2_664 2_664 ?
N2 K1 C16' 85.04(5) . . ?
O3' K1 C16' 23.44(4) . . ?
N1 K1 C16' 71.36(5) . . ?
N2 K1 C16' 87.10(5) 2_664 . ?
N1 K1 C16' 97.89(5) 2_664 . ?
C7 K1 C16' 121.35(6) 2_664 . ?
C9 K1 C16' 112.25(6) 2_664 . ?
C8 K1 C16' 129.43(6) 2_664 . ?
N2 K1 C16 85.04(5) . . ?
O3 K1 C16 23.44(4) . . ?
N1 K1 C16 71.36(5) . . ?
O3 K1 C16 150.44(5) 2_665 . ?
N2 K1 C16 87.10(5) 2_664 . ?
N1 K1 C16 97.89(5) 2_664 . ?
C7 K1 C16 121.35(6) 2_664 . ?
C9 K1 C16 112.25(6) 2_664 . ?
C8 K1 C16 129.43(6) 2_664 . ?
C6 O1 C7 104.35(14) . . ?
C10 O2 C9 104.38(14) . . ?
C7 N1 C1 104.73(15) . . ?
C7 N1 K1 129.33(12) . . ?
C1 N1 K1 124.09(12) . . ?
C7 N1 K1 82.39(10) . 2_665 ?
C1 N1 K1 119.40(11) . 2_665 ?
K1 N1 K1 84.76(4) . 2_665 ?
C9 N2 C15 104.85(15) . . ?
C9 N2 K1 127.83(12) . . ?
C15 N2 K1 122.54(12) . . ?
C9 N2 K1 86.31(11) . 2_665 ?
C15 N2 K1 121.27(12) . 2_665 ?
K1 N2 K1 86.77(4) . 2_665 ?
C6 C1 C2 119.68(17) . . ?
C6 C1 N1 109.12(16) . . ?
C2 C1 N1 131.19(17) . . ?
C3 C2 C1 117.43(18) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.69(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.59(18) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 115.46(19) . . ?
C6 C5 H5 122.3 . . ?
C4 C5 H5 122.3 . . ?
O1 C6 C5 127.85(18) . . ?
O1 C6 C1 108.00(15) . . ?
C5 C6 C1 124.14(18) . . ?
N1 C7 O1 113.77(16) . . ?
N1 C7 C8 131.17(17) . . ?
O1 C7 C8 115.05(16) . . ?
N1 C7 K1 72.73(10) . 2_665 ?
O1 C7 K1 121.20(11) . 2_665 ?
C8 C7 K1 81.44(10) . 2_665 ?
C9 C8 C7 124.40(17) . . ?
C9 C8 K1 72.96(10) . 2_665 ?
C7 C8 K1 72.96(10) . 2_665 ?
C9 C8 H8 118.0(13) . . ?
C7 C8 H8 117.6(13) . . ?
K1 C8 H8 128.1(13) 2_665 . ?
N2 C9 O2 113.54(16) . . ?
N2 C9 C8 131.26(17) . . ?
O2 C9 C8 115.17(15) . . ?
N2 C9 K1 68.49(10) . 2_665 ?
O2 C9 K1 126.40(12) . 2_665 ?
C8 C9 K1 81.44(10) . 2_665 ?
C11 C10 O2 127.58(18) . . ?
C11 C10 C15 124.50(17) . . ?
O2 C10 C15 107.88(15) . . ?
C10 C11 C12 115.37(19) . . ?
C10 C11 H11 122.3 . . ?
C12 C11 H11 122.3 . . ?
C11 C12 C13 121.86(19) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 121.39(19) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.34(18) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C10 C15 C14 119.51(17) . . ?
C10 C15 N2 109.35(16) . . ?
C14 C15 N2 131.14(18) . . ?

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
C19 O3 C16 C17 -5.7(3) . . . . ?
K1 O3 C16 C17 -131.2(3) . . . . ?
K1 O3 C16 C17 132.9(3) 2_664 . . . ?
C19 O3 C16 K1 125.50(16) . . . . ?
K1 O3 C16 K1 -95.91(9) 2_664 . . . ?
O3 C16 C17 C18 25.0(6) . . . . ?
K1 C16 C17 C18 -24.8(7) . . . . ?
C16 C17 C18 C19 -33.6(6) . . . . ?
C16 O3 C19 C18 -16.2(3) . . . . ?
K1 O3 C19 C18 104.5(3) . . . . ?
K1 O3 C19 C18 -151.9(3) 2_664 . . . ?
C17 C18 C19 O3 31.3(5) . . . . ?
C19' O3' C16' C17' 14.6(7) . . . . ?
K1 O3' C16' C17' -110.9(7) . . . . ?
K1 O3' C16' C17' 153.2(7) 2_664 . . . ?
C19' O3' C16' K1 125.50(16) . . . . ?
K1 O3' C16' K1 -95.91(9) 2_664 . . . ?
O3' C16' C17' C18' -32.8(15) . . . . ?
K1 C16' C17' C18' -85.1(14) . . . . ?
C16' C17' C18' C19' 38.6(18) . . . . ?
C16' O3' C19' C18' 10.4(8) . . . . ?
K1 O3' C19' C18' 131.1(7) . . . . ?
K1 O3' C19' C18' -125.4(7) 2_664 . . . ?
C17' C18' C19' O3' -30.7(15) . . . . ?
C7 N1 C1 C6 0.8(2) . . . . ?
K1 N1 C1 C6 166.56(12) . . . . ?
K1 N1 C1 C6 -88.69(16) 2_665 . . . ?
C7 N1 C1 C2 -178.4(2) . . . . ?
K1 N1 C1 C2 -12.6(3) . . . . ?
K1 N1 C1 C2 92.1(2) 2_665 . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
N1 C1 C2 C3 179.85(19) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C7 O1 C6 C5 179.37(19) . . . . ?
C7 O1 C6 C1 -0.81(19) . . . . ?
C4 C5 C6 O1 -179.94(19) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 O1 179.35(16) . . . . ?
N1 C1 C6 O1 0.0(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N1 C1 C6 C5 179.87(18) . . . . ?
C1 N1 C7 O1 -1.4(2) . . . . ?
K1 N1 C7 O1 -166.11(11) . . . . ?
K1 N1 C7 O1 117.12(14) 2_665 . . . ?
C1 N1 C7 C8 -179.9(2) . . . . ?
K1 N1 C7 C8 15.4(3) . . . . ?
K1 N1 C7 C8 -61.4(2) 2_665 . . . ?
C1 N1 C7 K1 -118.49(12) . . . 2_665 ?
K1 N1 C7 K1 76.78(11) . . . 2_665 ?
C6 O1 C7 N1 1.4(2) . . . . ?
C6 O1 C7 C8 -179.84(16) . . . . ?
C6 O1 C7 K1 84.94(15) . . . 2_665 ?
N1 C7 C8 C9 3.5(3) . . . . ?
O1 C7 C8 C9 -174.97(16) . . . . ?
K1 C7 C8 C9 -54.45(18) 2_665 . . . ?
N1 C7 C8 K1 57.96(19) . . . 2_665 ?
O1 C7 C8 K1 -120.52(15) . . . 2_665 ?
C15 N2 C9 O2 -0.2(2) . . . . ?
K1 N2 C9 O2 155.37(11) . . . . ?
K1 N2 C9 O2 -121.61(14) 2_665 . . . ?
C15 N2 C9 C8 177.45(19) . . . . ?
K1 N2 C9 C8 -27.0(3) . . . . ?
K1 N2 C9 C8 56.0(2) 2_665 . . . ?
C15 N2 C9 K1 121.40(13) . . . 2_665 ?
K1 N2 C9 K1 -83.02(11) . . . 2_665 ?
C10 O2 C9 N2 0.5(2) . . . . ?
C10 O2 C9 C8 -177.53(15) . . . . ?
C10 O2 C9 K1 -79.37(16) . . . 2_665 ?
C7 C8 C9 N2 3.2(3) . . . . ?
K1 C8 C9 N2 -51.3(2) 2_665 . . . ?
C7 C8 C9 O2 -179.23(17) . . . . ?
K1 C8 C9 O2 126.32(15) 2_665 . . . ?
C7 C8 C9 K1 54.45(18) . . . 2_665 ?
C9 O2 C10 C11 177.21(19) . . . . ?
C9 O2 C10 C15 -0.61(19) . . . . ?
O2 C10 C11 C12 -178.82(18) . . . . ?
C15 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C11 C10 C15 C14 2.1(3) . . . . ?
O2 C10 C15 C14 179.99(17) . . . . ?
C11 C10 C15 N2 -177.38(19) . . . . ?
O2 C10 C15 N2 0.5(2) . . . . ?
C13 C14 C15 C10 -1.5(3) . . . . ?
C13 C14 C15 N2 177.8(2) . . . . ?
C9 N2 C15 C10 -0.2(2) . . . . ?
K1 N2 C15 C10 -157.41(12) . . . . ?
K1 N2 C15 C10 94.58(16) 2_665 . . . ?
C9 N2 C15 C14 -179.6(2) . . . . ?
K1 N2 C15 C14 23.2(3) . . . . ?
K1 N2 C15 C14 -84.8(2) 2_665 . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_sad_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1839911'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-06-08 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         'C27 H33 K N2 O8'
_chemical_formula_sum            'C27 H33 K N2 O8'
_chemical_formula_weight         552.65

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.913(3)
_cell_length_b                   10.981(2)
_cell_length_c                   15.309(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8786
_cell_measurement_theta_min      2.2535
_cell_measurement_theta_max      25.4015

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6660
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'BRUKER Rotating Anode'
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33321
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         26.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5489
_reflns_number_gt                4843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 v2012.2'
_computing_cell_refinement       'SAINT V8.38A'
_computing_data_reduction        'SAINT V8.38A'
_computing_structure_solution    
'SHELXT(G.M.Sheldrick,Acta Cryst.(2015)A71,3-8)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_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)+(0.0352P)²+0.2234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5489
_refine_ls_number_parameters     361
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.071
_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
K1 K 0.37587(3) 0.68386(5) 0.46057(6) 0.02352(14) Uani 1 1 d . . . . .
C8 C 0.17250(18) 0.8324(2) 0.47900(19) 0.0229(6) Uani 1 1 d D . . . .
H8 H 0.1395(17) 0.879(3) 0.4411(19) 0.032(9) Uiso 1 1 d D . . . .
C7 C 0.21415(18) 0.8945(3) 0.54471(19) 0.0254(6) Uani 1 1 d D . . . .
N1 N 0.205(3) 1.0149(16) 0.5558(18) 0.023(4) Uani 0.61(3) 1 d D . P A 1
O1 O 0.259(3) 0.8410(15) 0.611(2) 0.0245(17) Uani 0.61(3) 1 d D . P A 1
C5 C 0.26476(19) 1.1534(2) 0.6717(2) 0.0272(7) Uani 1 1 d D . . . .
H5 H 0.242834 1.227258 0.648747 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3274(2) 0.9323(3) 0.7412(2) 0.0283(7) Uani 1 1 d D . . . .
H2 H 0.347491 0.857908 0.764980 0.034 Uiso 1 1 calc R U . . .
C1 C 0.28390(17) 0.9356(2) 0.6639(2) 0.0224(6) Uani 1 1 d D . . . .
C6 C 0.25258(18) 1.0434(2) 0.62913(19) 0.0220(6) Uani 1 1 d D . . . .
N1' N 0.261(6) 0.842(3) 0.607(5) 0.0245(17) Uani 0.39(3) 1 d D . P A 2
O1' O 0.215(3) 1.020(2) 0.550(2) 0.023(4) Uani 0.39(3) 1 d D . P A 2
O2 O 0.106(2) 0.6606(5) 0.413(2) 0.0234(7) Uani 0.82(3) 1 d D . P A 1
N2 N 0.2081(17) 0.6199(6) 0.5129(16) 0.022(2) Uani 0.82(3) 1 d D . P A 1
O3 O 0.38033(12) 0.42831(16) 0.47318(14) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.34067(19) 1.0436(3) 0.7832(2) 0.0263(7) Uani 1 1 d . . . . .
H3 H 0.371283 1.045378 0.836481 0.032 Uiso 1 1 calc R U . . .
O5 O 0.37551(13) 0.77151(19) 0.28552(14) 0.0299(5) Uani 1 1 d . . . . .
C4 C 0.31005(19) 1.1515(3) 0.7487(2) 0.0265(7) Uani 1 1 d . . . . .
H4 H 0.320414 1.225818 0.778619 0.032 Uiso 1 1 calc R U . . .
O4 O 0.37408(13) 0.51634(19) 0.30618(14) 0.0283(5) Uani 1 1 d . . . . .
O6 O 0.44576(13) 0.92340(18) 0.41482(15) 0.0286(5) Uani 1 1 d . . . . .
O7 O 0.45612(13) 0.82722(17) 0.58208(15) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.16566(17) 0.7059(2) 0.4718(2) 0.0223(6) Uani 1 1 d D . . . .
O8 O 0.45561(12) 0.57079(17) 0.60563(14) 0.0263(5) Uani 1 1 d . . . . .
C10 C 0.11093(17) 0.5353(2) 0.42337(19) 0.0200(6) Uani 1 1 d D . . . .
C11 C 0.06376(18) 0.4473(2) 0.3828(2) 0.0236(6) Uani 1 1 d D . . . .
H11 H 0.021999 0.467139 0.340775 0.028 Uiso 1 1 calc R U . . .
C12 C 0.08056(18) 0.3269(3) 0.4066(2) 0.0254(6) Uani 1 1 d . . . . .
H12 H 0.049447 0.262727 0.380455 0.030 Uiso 1 1 calc R U . . .
C13 C 0.14164(17) 0.2998(2) 0.4676(2) 0.0273(7) Uani 1 1 d . . . . .
H13 H 0.151973 0.217092 0.482199 0.033 Uiso 1 1 calc R U . . .
C14 C 0.18827(18) 0.3903(2) 0.5080(2) 0.0264(7) Uani 1 1 d D . . . .
H14 H 0.230193 0.371019 0.549945 0.032 Uiso 1 1 calc R U . . .
C15 C 0.17146(17) 0.5105(2) 0.48485(18) 0.0201(6) Uani 1 1 d D . . . .
N2' N 0.108(12) 0.662(2) 0.415(12) 0.0234(7) Uani 0.18(3) 1 d D . P A 2
O2' O 0.204(6) 0.617(2) 0.519(6) 0.022(2) Uani 0.18(3) 1 d D . P A 2
C16 C 0.3787(2) 0.3468(3) 0.4017(2) 0.0313(7) Uani 1 1 d . . . . .
H16A H 0.350138 0.270330 0.418734 0.038 Uiso 1 1 calc R U . . .
H16B H 0.436766 0.326850 0.383447 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3325(2) 0.4060(3) 0.3278(2) 0.0318(7) Uani 1 1 d . . . . .
H17A H 0.331504 0.351093 0.276535 0.038 Uiso 1 1 calc R U . . .
H17B H 0.273718 0.423072 0.345277 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3381(2) 0.5757(3) 0.2323(2) 0.0391(9) Uani 1 1 d . . . . .
H18A H 0.278567 0.596147 0.244145 0.047 Uiso 1 1 calc R U . . .
H18B H 0.340294 0.521461 0.180742 0.047 Uiso 1 1 calc R U . . .
C19 C 0.3873(2) 0.6895(3) 0.2152(2) 0.0374(8) Uani 1 1 d . . . . .
H19A H 0.447729 0.669545 0.209222 0.045 Uiso 1 1 calc R U . . .
H19B H 0.368153 0.727451 0.160023 0.045 Uiso 1 1 calc R U . . .
C20 C 0.4118(2) 0.8875(3) 0.2672(2) 0.0352(8) Uani 1 1 d . . . . .
H20A H 0.385288 0.923033 0.214537 0.042 Uiso 1 1 calc R U . . .
H20B H 0.472705 0.878188 0.255665 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3988(2) 0.9695(3) 0.3430(2) 0.0360(8) Uani 1 1 d . . . . .
H21A H 0.417948 1.052909 0.328453 0.043 Uiso 1 1 calc R U . . .
H21B H 0.338418 0.973029 0.358188 0.043 Uiso 1 1 calc R U . . .
C22 C 0.4396(2) 0.9989(3) 0.4902(2) 0.0343(8) Uani 1 1 d . . . . .
H22A H 0.380149 1.006300 0.508327 0.041 Uiso 1 1 calc R U . . .
H22B H 0.461152 1.081399 0.476720 0.041 Uiso 1 1 calc R U . . .
C23 C 0.4900(2) 0.9437(3) 0.5622(2) 0.0354(8) Uani 1 1 d . . . . .
H23A H 0.549448 0.935461 0.543924 0.042 Uiso 1 1 calc R U . . .
H23B H 0.487924 0.996526 0.614548 0.042 Uiso 1 1 calc R U . . .
C24 C 0.4997(2) 0.7678(3) 0.6511(2) 0.0359(8) Uani 1 1 d . . . . .
H24A H 0.504353 0.822973 0.702048 0.043 Uiso 1 1 calc R U . . .
H24B H 0.557152 0.745877 0.631900 0.043 Uiso 1 1 calc R U . . .
C25 C 0.4525(2) 0.6554(3) 0.6763(2) 0.0339(7) Uani 1 1 d . . . . .
H25A H 0.477893 0.618735 0.729110 0.041 Uiso 1 1 calc R U . . .
H25B H 0.393316 0.676241 0.689611 0.041 Uiso 1 1 calc R U . . .
C26 C 0.40662(19) 0.4648(3) 0.6229(2) 0.0282(7) Uani 1 1 d . . . . .
H26A H 0.346648 0.487341 0.628825 0.034 Uiso 1 1 calc R U . . .
H26B H 0.425147 0.426801 0.678284 0.034 Uiso 1 1 calc R U . . .
C27 C 0.4173(2) 0.3770(3) 0.5493(2) 0.0283(7) Uani 1 1 d . . . . .
H27A H 0.477725 0.361191 0.539176 0.034 Uiso 1 1 calc R U . . .
H27B H 0.389583 0.298784 0.563726 0.034 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
K1 O7 2.751(2) . ?
K1 O3 2.814(2) . ?
K1 O8 2.843(2) . ?
K1 O5 2.848(2) . ?
K1 N2 2.87(3) . ?
K1 O6 2.941(2) . ?
K1 O2' 2.97(12) . ?
K1 O4 2.995(2) . ?
K1 C9 3.358(3) . ?
K1 C12 3.362(3) 3_565 ?
K1 N1' 3.37(9) . ?
K1 O1 3.42(5) . ?
C8 H8 0.93(2) . ?
C8 C7 1.384(4) . ?
C8 C9 1.398(3) . ?
C7 N1' 1.33(2) . ?
C7 N1 1.342(18) . ?
C7 O1 1.371(13) . ?
C7 O1' 1.38(2) . ?
N1 C6 1.390(17) . ?
O1 C1 1.377(13) . ?
C5 C4 1.382(4) . ?
C5 C6 1.386(4) . ?
C2 C1 1.370(4) . ?
C2 C3 1.398(4) . ?
C1 C6 1.390(4) . ?
C1 N1' 1.40(2) . ?
C6 O1' 1.37(2) . ?
O2 C10 1.388(6) . ?
O2 C9 1.398(6) . ?
N2 C9 1.320(9) . ?
N2 C15 1.404(8) . ?
O3 C16 1.414(4) . ?
O3 C27 1.422(4) . ?
C3 C4 1.386(4) . ?
O5 C19 1.416(4) . ?
O5 C20 1.427(4) . ?
O4 C17 1.420(4) . ?
O4 C18 1.425(4) . ?
O6 C21 1.422(4) . ?
O6 C22 1.424(4) . ?
O7 C23 1.421(3) . ?
O7 C24 1.423(4) . ?
C9 N2' 1.35(3) . ?
C9 O2' 1.36(2) . ?
O8 C26 1.426(3) . ?
O8 C25 1.427(4) . ?
C10 C11 1.372(4) . ?
C10 C15 1.374(4) . ?
C10 N2' 1.40(2) . ?
C11 C12 1.397(4) . ?
C12 C13 1.380(5) . ?
C13 C14 1.386(4) . ?
C14 C15 1.392(4) . ?
C15 O2' 1.38(2) . ?
C16 C17 1.498(5) . ?
C18 C19 1.498(5) . ?
C20 C21 1.484(5) . ?
C22 C23 1.492(5) . ?
C24 C25 1.495(4) . ?
C26 C27 1.492(4) . ?

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
O7 K1 O3 120.84(6) . . ?
O7 K1 O8 60.96(6) . . ?
O3 K1 O8 59.98(6) . . ?
O7 K1 O5 116.35(6) . . ?
O3 K1 O5 113.69(6) . . ?
O8 K1 O5 152.08(6) . . ?
O7 K1 N2 112.5(4) . . ?
O3 K1 N2 76.2(2) . . ?
O8 K1 N2 95.2(2) . . ?
O5 K1 N2 110.1(3) . . ?
O7 K1 O6 58.24(6) . . ?
O3 K1 O6 154.02(6) . . ?
O8 K1 O6 114.07(6) . . ?
O5 K1 O6 58.28(6) . . ?
N2 K1 O6 129.5(2) . . ?
O7 K1 O2' 111.4(13) . . ?
O3 K1 O2' 75.8(7) . . ?
O8 K1 O2' 93.8(8) . . ?
O5 K1 O2' 111.5(10) . . ?
O6 K1 O2' 130.0(7) . . ?
O7 K1 O4 152.79(6) . . ?
O3 K1 O4 56.07(6) . . ?
O8 K1 O4 110.63(6) . . ?
O5 K1 O4 57.65(6) . . ?
N2 K1 O4 93.5(4) . . ?
O6 K1 O4 111.41(6) . . ?
O2' K1 O4 94.4(13) . . ?
O7 K1 C9 112.74(7) . . ?
O3 K1 C9 95.36(6) . . ?
O8 K1 C9 115.85(7) . . ?
O5 K1 C9 91.26(7) . . ?
N2 K1 C9 22.81(16) . . ?
O6 K1 C9 108.94(6) . . ?
O2' K1 C9 23.9(5) . . ?
O4 K1 C9 94.31(6) . . ?
O7 K1 C12 74.73(7) . 3_565 ?
O3 K1 C12 87.55(6) . 3_565 ?
O8 K1 C12 75.18(7) . 3_565 ?
O5 K1 C12 77.45(7) . 3_565 ?
N2 K1 C12 163.7(2) . 3_565 ?
O6 K1 C12 66.83(6) . 3_565 ?
O2' K1 C12 163.1(6) . 3_565 ?
O4 K1 C12 78.10(7) . 3_565 ?
C9 K1 C12 168.54(8) . 3_565 ?
O7 K1 N1' 60.6(12) . . ?
O3 K1 N1' 118.8(13) . . ?
O8 K1 N1' 87.1(5) . . ?
O5 K1 N1' 116.7(7) . . ?
O6 K1 N1' 84.4(14) . . ?
O2' K1 N1' 55.1(18) . . ?
O4 K1 N1' 146.6(11) . . ?
C9 K1 N1' 52.3(11) . . ?
C12 K1 N1' 135.0(13) 3_565 . ?
O7 K1 O1 60.6(6) . . ?
O3 K1 O1 118.1(7) . . ?
O8 K1 O1 86.4(2) . . ?
O5 K1 O1 117.4(3) . . ?
N2 K1 O1 55.4(8) . . ?
O6 K1 O1 85.1(7) . . ?
O4 K1 O1 146.6(6) . . ?
C9 K1 O1 52.3(6) . . ?
C12 K1 O1 135.1(6) 3_565 . ?
H8 C8 C7 117.0(19) . . ?
H8 C8 C9 116.6(19) . . ?
C7 C8 C9 125.7(3) . . ?
N1 C7 O1 112.7(6) . . ?
N1' C7 O1' 112.4(12) . . ?
N1' C7 C8 124.8(12) . . ?
N1 C7 C8 121.7(8) . . ?
O1 C7 C8 125.1(7) . . ?
O1' C7 C8 122.7(10) . . ?
C7 N1 C6 105.3(14) . . ?
C7 O1 C1 105.2(10) . . ?
C7 O1 K1 90(2) . . ?
C1 O1 K1 129(3) . . ?
C4 C5 C6 117.4(3) . . ?
C1 C2 C3 116.8(3) . . ?
C2 C1 O1 129.4(7) . . ?
C2 C1 C6 122.3(3) . . ?
O1 C1 C6 108.3(6) . . ?
C2 C1 N1' 130.8(11) . . ?
C6 C1 N1' 106.9(11) . . ?
O1' C6 C5 129.6(10) . . ?
C5 C6 N1 130.7(8) . . ?
O1' C6 C1 109.6(10) . . ?
C5 C6 C1 120.8(3) . . ?
N1 C6 C1 108.3(8) . . ?
C7 N1' C1 105.9(19) . . ?
C7 N1' K1 93(4) . . ?
C1 N1' K1 131(6) . . ?
C6 O1' C7 104.1(16) . . ?
C10 O2 C9 104.0(4) . . ?
C9 N2 C15 104.7(6) . . ?
C9 N2 K1 99.6(14) . . ?
C15 N2 K1 120.6(17) . . ?
C16 O3 C27 113.0(2) . . ?
C16 O3 K1 125.29(18) . . ?
C27 O3 K1 117.50(16) . . ?
C4 C3 C2 121.3(3) . . ?
C19 O5 C20 111.4(2) . . ?
C19 O5 K1 120.01(17) . . ?
C20 O5 K1 119.08(18) . . ?
C5 C4 C3 121.4(3) . . ?
C17 O4 C18 112.8(2) . . ?
C17 O4 K1 110.15(17) . . ?
C18 O4 K1 110.41(18) . . ?
C21 O6 C22 112.5(2) . . ?
C21 O6 K1 107.71(17) . . ?
C22 O6 K1 107.58(17) . . ?
C23 O7 C24 112.7(2) . . ?
C23 O7 K1 123.13(18) . . ?
C24 O7 K1 117.78(16) . . ?
N2' C9 O2' 113.1(12) . . ?
N2 C9 O2 113.6(4) . . ?
N2 C9 C8 129.3(4) . . ?
N2' C9 C8 117.1(13) . . ?
O2' C9 C8 129.6(11) . . ?
O2 C9 C8 117.2(3) . . ?
N2 C9 K1 57.5(13) . . ?
N2' C9 K1 128(10) . . ?
O2' C9 K1 62(5) . . ?
O2 C9 K1 128.0(18) . . ?
C8 C9 K1 89.89(17) . . ?
C26 O8 C25 111.8(2) . . ?
C26 O8 K1 104.91(17) . . ?
C25 O8 K1 106.98(17) . . ?
C11 C10 C15 123.6(3) . . ?
C11 C10 O2 128.1(3) . . ?
C15 C10 O2 108.3(3) . . ?
C11 C10 N2' 129.9(12) . . ?
C15 C10 N2' 106.4(12) . . ?
C10 C11 C12 116.3(3) . . ?
C10 C11 K1 126.75(19) . 3_465 ?
C12 C11 K1 71.79(16) . 3_465 ?
C13 C12 C11 121.0(3) . . ?
C13 C12 K1 120.6(2) . 3_465 ?
C11 C12 K1 84.96(17) . 3_465 ?
C12 C13 C14 121.6(3) . . ?
C13 C14 C15 117.6(3) . . ?
C10 C15 O2' 110.9(12) . . ?
C10 C15 C14 119.8(3) . . ?
O2' C15 C14 129.2(11) . . ?
C10 C15 N2 109.4(4) . . ?
C14 C15 N2 130.8(4) . . ?
C9 N2' C10 106(2) . . ?
C9 O2' C15 103.6(18) . . ?
C9 O2' K1 94(5) . . ?
C15 O2' K1 116(7) . . ?
O3 C16 C17 108.6(2) . . ?
O4 C17 C16 108.5(2) . . ?
O4 C18 C19 108.1(3) . . ?
O5 C19 C18 109.1(3) . . ?
O5 C20 C21 109.4(3) . . ?
O6 C21 C20 108.4(3) . . ?
O6 C22 C23 109.0(2) . . ?
O7 C23 C22 108.7(2) . . ?
O7 C24 C25 108.9(3) . . ?
O8 C25 C24 109.0(3) . . ?
O8 C25 K1 50.31(13) . . ?
C24 C25 K1 81.96(18) . . ?
O8 C26 C27 109.0(2) . . ?
O8 C26 K1 51.86(13) . . ?
C27 C26 K1 85.64(17) . . ?
O3 C27 C26 108.4(2) . . ?

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
H8 C8 C7 N1' 177(7) . . . . ?
C9 C8 C7 N1' 7(7) . . . . ?
H8 C8 C7 N1 3(3) . . . . ?
C9 C8 C7 N1 -168(2) . . . . ?
H8 C8 C7 O1 174(4) . . . . ?
C9 C8 C7 O1 4(3) . . . . ?
H8 C8 C7 O1' -7(4) . . . . ?
C9 C8 C7 O1' -177(3) . . . . ?
O1 C7 N1 C6 5(5) . . . . ?
C8 C7 N1 C6 177.5(14) . . . . ?
N1 C7 O1 C1 -4(5) . . . . ?
C8 C7 O1 C1 -175.6(16) . . . . ?
N1 C7 O1 K1 -134(2) . . . . ?
C8 C7 O1 K1 54(3) . . . . ?
C3 C2 C1 O1 -177(3) . . . . ?
C3 C2 C1 C6 -1.3(5) . . . . ?
C3 C2 C1 N1' 180(7) . . . . ?
C7 O1 C1 C2 176.9(13) . . . . ?
K1 O1 C1 C2 -80(3) . . . . ?
C7 O1 C1 C6 0(4) . . . . ?
K1 O1 C1 C6 103.3(8) . . . . ?
C4 C5 C6 O1' -175(3) . . . . ?
C4 C5 C6 N1 174(3) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C7 N1 C6 C5 -178.5(10) . . . . ?
C7 N1 C6 C1 -5(3) . . . . ?
C2 C1 C6 O1' 177(3) . . . . ?
N1' C1 C6 O1' -3(6) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
O1 C1 C6 C5 177(3) . . . . ?
N1' C1 C6 C5 180(5) . . . . ?
C2 C1 C6 N1 -174(2) . . . . ?
O1 C1 C6 N1 3(3) . . . . ?
O1' C7 N1' C1 9(9) . . . . ?
C8 C7 N1' C1 -174(3) . . . . ?
O1' C7 N1' K1 -125(3) . . . . ?
C8 C7 N1' K1 52(5) . . . . ?
C2 C1 N1' C7 176(3) . . . . ?
C6 C1 N1' C7 -3(9) . . . . ?
C2 C1 N1' K1 -76(7) . . . . ?
C6 C1 N1' K1 105.2(16) . . . . ?
C5 C6 O1' C7 -174.8(12) . . . . ?
C1 C6 O1' C7 9(4) . . . . ?
N1' C7 O1' C6 -11(7) . . . . ?
C8 C7 O1' C6 172.1(17) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C6 C5 C4 C3 -1.3(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C15 N2 C9 O2 -4(3) . . . . ?
K1 N2 C9 O2 121(2) . . . . ?
C15 N2 C9 C8 176.2(7) . . . . ?
K1 N2 C9 C8 -58.5(18) . . . . ?
C15 N2 C9 K1 -125(2) . . . . ?
C10 O2 C9 N2 3(4) . . . . ?
C10 O2 C9 C8 -177.1(15) . . . . ?
C10 O2 C9 K1 69(3) . . . . ?
H8 C8 C9 N2 175(3) . . . . ?
C7 C8 C9 N2 -14(2) . . . . ?
H8 C8 C9 N2' -5(13) . . . . ?
C7 C8 C9 N2' 166(13) . . . . ?
H8 C8 C9 O2' -178(8) . . . . ?
C7 C8 C9 O2' -8(7) . . . . ?
H8 C8 C9 O2 -4(3) . . . . ?
C7 C8 C9 O2 166(2) . . . . ?
H8 C8 C9 K1 130(2) . . . . ?
C7 C8 C9 K1 -60.2(3) . . . . ?
C9 O2 C10 C11 177.8(10) . . . . ?
C9 O2 C10 C15 -1(3) . . . . ?
C15 C10 C11 C12 -0.5(4) . . . . ?
O2 C10 C11 C12 -179(2) . . . . ?
N2' C10 C11 C12 -178(14) . . . . ?
C15 C10 C11 K1 85.7(3) . . . 3_465 ?
O2 C10 C11 K1 -93(3) . . . 3_465 ?
N2' C10 C11 K1 -92(14) . . . 3_465 ?
C10 C11 C12 C13 -0.2(4) . . . . ?
K1 C11 C12 C13 -122.9(3) 3_465 . . . ?
C10 C11 C12 K1 122.7(2) . . . 3_465 ?
C11 C12 C13 C14 0.5(5) . . . . ?
K1 C12 C13 C14 -103.2(3) 3_465 . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C11 C10 C15 O2' -176(6) . . . . ?
N2' C10 C15 O2' 3(13) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
O2 C10 C15 C14 180(2) . . . . ?
N2' C10 C15 C14 179(11) . . . . ?
C11 C10 C15 N2 179.7(15) . . . . ?
O2 C10 C15 N2 -2(3) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C13 C14 C15 O2' 175(7) . . . . ?
C13 C14 C15 N2 -179.1(19) . . . . ?
C9 N2 C15 C10 3(2) . . . . ?
K1 N2 C15 C10 -107.4(4) . . . . ?
C9 N2 C15 C14 -177.9(8) . . . . ?
K1 N2 C15 C14 71.2(17) . . . . ?
O2' C9 N2' C10 -2(20) . . . . ?
C8 C9 N2' C10 -177(9) . . . . ?
K1 C9 N2' C10 69(18) . . . . ?
C11 C10 N2' C9 178(6) . . . . ?
C15 C10 N2' C9 0(18) . . . . ?
N2' C9 O2' C15 4(16) . . . . ?
C8 C9 O2' C15 178(2) . . . . ?
K1 C9 O2' C15 -118(9) . . . . ?
N2' C9 O2' K1 122(12) . . . . ?
C8 C9 O2' K1 -63(6) . . . . ?
C10 C15 O2' C9 -4(9) . . . . ?
C14 C15 O2' C9 180(3) . . . . ?
C10 C15 O2' K1 -106.0(14) . . . . ?
C14 C15 O2' K1 78(6) . . . . ?
C27 O3 C16 C17 175.4(2) . . . . ?
K1 O3 C16 C17 -28.3(3) . . . . ?
C18 O4 C17 C16 176.0(3) . . . . ?
K1 O4 C17 C16 -60.1(3) . . . . ?
O3 C16 C17 O4 58.5(3) . . . . ?
C17 O4 C18 C19 -179.4(3) . . . . ?
K1 O4 C18 C19 56.9(3) . . . . ?
C20 O5 C19 C18 -172.2(3) . . . . ?
K1 O5 C19 C18 41.8(3) . . . . ?
O4 C18 C19 O5 -66.3(3) . . . . ?
C19 O5 C20 C21 -179.3(3) . . . . ?
K1 O5 C20 C21 -32.9(3) . . . . ?
C22 O6 C21 C20 177.9(2) . . . . ?
K1 O6 C21 C20 -63.7(3) . . . . ?
O5 C20 C21 O6 66.1(3) . . . . ?
C21 O6 C22 C23 179.7(2) . . . . ?
K1 O6 C22 C23 61.2(3) . . . . ?
C24 O7 C23 C22 -179.3(3) . . . . ?
K1 O7 C23 C22 29.4(3) . . . . ?
O6 C22 C23 O7 -61.4(3) . . . . ?
C23 O7 C24 C25 171.7(3) . . . . ?
K1 O7 C24 C25 -35.3(3) . . . . ?
C26 O8 C25 C24 -175.8(3) . . . . ?
K1 O8 C25 C24 -61.5(3) . . . . ?
C26 O8 C25 K1 -114.3(2) . . . . ?
O7 C24 C25 O8 66.8(3) . . . . ?
O7 C24 C25 K1 23.7(2) . . . . ?
C25 O8 C26 C27 -176.3(2) . . . . ?
K1 O8 C26 C27 68.1(2) . . . . ?
C25 O8 C26 K1 115.6(2) . . . . ?
C16 O3 C27 C26 -173.4(2) . . . . ?
K1 O3 C27 C26 28.2(3) . . . . ?
O8 C26 C27 O3 -66.9(3) . . . . ?
K1 C26 C27 O3 -19.8(2) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.040

