# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_LK61_0m
_database_code_depnum_ccdc_archive 'CCDC 2009784'
loop_
_audit_author_name
_audit_author_address
'Maryana Kraft'
;University Augsburg
Germany
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_STRVA01_mo_LK61_0m          
;

PROBLEM: Flack test results are ambiguous.
RESPONSE: the Flack parameter is not relevant for this structure, 
		since the measurement has been done with Mo-radiation 
		and the structure contains only C, H and N atoms.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 N6'
_chemical_formula_weight         358.44

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   9.0638(3)
_cell_length_b                   9.0638(3)
_cell_length_c                   22.3036(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1586.81(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6739
_cell_measurement_theta_min      2.595
_cell_measurement_theta_max      25.037

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_F_000             570
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6241
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17089
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_full        25.037
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1877
_reflns_number_gt                1613
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     1.000
_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       'Bruker Instrument Service v3.0.25'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, Diamond'
_computing_publication_material  Word
_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)+(0.0372P)²+0.7735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1877
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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
N2 N 0.2543(4) 0.5022(4) 0.33858(13) 0.0188(7) Uani 1 1 d . . . . .
N3 N 0.3647(4) 0.4459(4) 0.32871(12) 0.0166(7) Uani 1 1 d . . . . .
N1 N 0.1122(4) 0.4012(4) 0.30986(12) 0.0187(7) Uani 1 1 d . . . . .
C7 C 0.000000 -0.0803(5) 0.166667 0.0171(11) Uani 1 2 d S T P . .
C2 C 0.2954(4) 0.3076(4) 0.29242(14) 0.0136(7) Uani 1 1 d . . . . .
C3 C 0.3594(5) 0.2088(4) 0.26700(15) 0.0164(8) Uani 1 1 d . . . . .
C6 C 0.0228(5) 0.1504(5) 0.24048(15) 0.0169(8) Uani 1 1 d . . . . .
C1 C 0.1320(4) 0.2789(4) 0.28008(14) 0.0150(8) Uani 1 1 d . . . . .
C5 C 0.0872(4) 0.0561(4) 0.21439(14) 0.0158(8) Uani 1 1 d . . . . .
C4 C 0.2524(5) 0.0850(4) 0.22771(13) 0.0152(8) Uani 1 1 d . . . . .
C9 C 0.2885(4) -0.0367(4) 0.19230(15) 0.0195(8) Uani 1 1 d . . . . .
C10 C 0.2615(6) -0.1855(5) 0.23276(18) 0.0246(9) Uani 1 1 d . . . . .
C11 C 0.4684(5) 0.0503(6) 0.16661(19) 0.0285(9) Uani 1 1 d . . . . .
C8 C 0.1515(5) -0.0968(5) 0.14219(15) 0.0193(8) Uani 1 1 d . . . . .
H1 H 0.473(6) 0.507(5) 0.3444(18) 0.036(12) Uiso 1 1 d . . . . .
H2 H 0.473(5) 0.232(4) 0.2768(14) 0.011(8) Uiso 1 1 d . . . . .
H3 H -0.087(5) 0.135(4) 0.2317(14) 0.015(9) Uiso 1 1 d . . . . .
H4 H 0.203(4) -0.022(4) 0.1073(15) 0.017(9) Uiso 1 1 d . . . . .
H5 H 0.115(4) -0.215(5) 0.1285(15) 0.018(9) Uiso 1 1 d . . . . .
H6 H 0.345(5) -0.147(5) 0.2661(16) 0.026(10) Uiso 1 1 d . . . . .
H7 H 0.274(5) -0.267(5) 0.2076(17) 0.031(11) Uiso 1 1 d . . . . .
H8 H 0.142(6) -0.248(5) 0.2511(18) 0.042(12) Uiso 1 1 d . . . . .
H9 H 0.555(4) 0.087(5) 0.2009(16) 0.021(10) Uiso 1 1 d . . . . .
H10 H 0.489(5) 0.148(5) 0.1416(17) 0.027(11) Uiso 1 1 d . . . . .
H11 H 0.485(5) -0.034(5) 0.1433(17) 0.038(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 N1 1.315(4) . ?
N2 N3 1.350(4) . ?
N3 C2 1.354(4) . ?
N1 C1 1.379(4) . ?
C7 C5 1.519(4) . ?
C7 C5 1.519(4) 6 ?
C7 C8 1.553(4) . ?
C7 C8 1.553(5) 6 ?
C2 C1 1.397(4) . ?
C2 C3 1.407(5) . ?
C3 C4 1.371(5) . ?
C6 C5 1.382(5) . ?
C6 C1 1.401(5) . ?
C5 C4 1.416(5) . ?
C4 C9 1.520(5) . ?
C9 C11 1.524(5) . ?
C9 C10 1.537(5) . ?
C9 C8 1.553(5) . ?

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 N2 N3 108.1(3) . . ?
N2 N3 C2 111.0(3) . . ?
N2 N1 C1 108.6(3) . . ?
C5 C7 C5 112.8(4) . 6 ?
C5 C7 C8 101.48(18) . . ?
C5 C7 C8 113.38(18) 6 . ?
C5 C7 C8 113.38(18) . 6 ?
C5 C7 C8 101.47(18) 6 6 ?
C8 C7 C8 114.8(4) . 6 ?
N3 C2 C1 104.4(3) . . ?
N3 C2 C3 133.0(3) . . ?
C1 C2 C3 122.5(3) . . ?
C4 C3 C2 115.5(3) . . ?
C5 C6 C1 116.0(3) . . ?
N1 C1 C2 107.9(3) . . ?
N1 C1 C6 130.6(3) . . ?
C2 C1 C6 121.4(3) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 C7 126.1(3) . . ?
C4 C5 C7 111.7(3) . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 C9 127.3(3) . . ?
C5 C4 C9 110.4(3) . . ?
C4 C9 C11 112.5(3) . . ?
C4 C9 C10 109.5(3) . . ?
C11 C9 C10 109.6(3) . . ?
C4 C9 C8 101.7(3) . . ?
C11 C9 C8 111.8(3) . . ?
C10 C9 C8 111.5(3) . . ?
C7 C8 C9 107.7(2) . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_mo_bb_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2009786'
loop_
_audit_author_name
_audit_author_address
'Maryana Kraft'
;University Augsburg
Germany
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cl2 N2 O6'
_chemical_formula_weight         483.33

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7580(3)
_cell_length_b                   10.9296(3)
_cell_length_c                   11.4620(4)
_cell_angle_alpha                67.7990(10)
_cell_angle_beta                 72.2600(10)
_cell_angle_gamma                65.8980(10)
_cell_volume                     1120.83(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      26.11

_exptl_crystal_description       'block crystal'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31212
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         26.11
_reflns_number_total             4463
_reflns_number_gt                3491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX 2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury, Diamond'
_computing_publication_material  Word

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0306P)²+0.7066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.74241(5) 0.84400(6) 0.14731(5) 0.02919(14) Uani 1 1 d . . .
Cl2 Cl 0.97102(6) 0.87108(6) -0.06676(5) 0.03132(14) Uani 1 1 d . . .
O1 O 0.65678(14) 0.91800(14) -0.30266(12) 0.0236(3) Uani 1 1 d . . .
O2 O 0.86267(15) 0.77060(16) -0.32352(14) 0.0346(4) Uani 1 1 d . . .
N1 N 0.74557(16) 0.80839(17) -0.25998(15) 0.0180(4) Uani 1 1 d . . .
N2 N 0.95892(16) 0.16217(18) 0.59424(15) 0.0191(4) Uani 1 1 d . . .
C1 C 0.81046(19) 0.5897(2) -0.08282(18) 0.0178(4) Uani 1 1 d . . .
C2 C 0.71273(19) 0.72014(19) -0.13189(17) 0.0148(4) Uani 1 1 d . . .
O3 O 1.02271(14) 0.21729(16) 0.62231(13) 0.0268(3) Uani 1 1 d . . .
C3 C 0.58139(18) 0.76887(19) -0.06045(17) 0.0146(4) Uani 1 1 d . . .
H3 H 0.5170 0.8574 -0.0948 0.017 Uiso 1 1 calc R . .
O4 O 0.97298(14) 0.03773(15) 0.63980(13) 0.0262(3) Uani 1 1 d . . .
C4 C 0.54766(18) 0.68570(19) 0.06058(17) 0.0128(4) Uani 1 1 d . . .
O5 O 0.93775(14) 0.53727(16) -0.14709(14) 0.0309(4) Uani 1 1 d . . .
H5 H 0.9510 0.5964 -0.2180 0.046 Uiso 1 1 calc R . .
C5 C 0.64340(18) 0.55550(19) 0.10937(16) 0.0124(4) Uani 1 1 d . . .
O6 O 0.92866(15) 0.45534(15) 0.45769(14) 0.0245(3) Uani 1 1 d . . .
H6 H 0.9784 0.3994 0.5128 0.037 Uiso 1 1 calc R . .
C6 C 0.77311(19) 0.5078(2) 0.03934(17) 0.0163(4) Uani 1 1 d . . .
H6A H 0.8368 0.4192 0.0746 0.020 Uiso 1 1 calc R . .
C7 C 0.41372(18) 0.7168(2) 0.15611(17) 0.0152(4) Uani 1 1 d . . .
C8 C 0.45532(18) 0.59936(19) 0.28093(17) 0.0146(4) Uani 1 1 d . . .
H8A H 0.4773 0.6371 0.3354 0.017 Uiso 1 1 calc R . .
H8B H 0.3779 0.5633 0.3300 0.017 Uiso 1 1 calc R . .
C9 C 0.58424(18) 0.47970(19) 0.24203(17) 0.0130(4) Uani 1 1 d . . .
C10 C 0.3706(2) 0.8621(2) 0.17079(18) 0.0211(4) Uani 1 1 d . . .
H10A H 0.4449 0.8692 0.1978 0.032 Uiso 1 1 calc R . .
H10B H 0.2863 0.8776 0.2354 0.032 Uiso 1 1 calc R . .
H10C H 0.3530 0.9330 0.0886 0.032 Uiso 1 1 calc R . .
C11 C 0.29767(19) 0.7041(2) 0.11462(19) 0.0238(5) Uani 1 1 d . . .
H11A H 0.2771 0.7768 0.0340 0.036 Uiso 1 1 calc R . .
H11B H 0.2145 0.7159 0.1809 0.036 Uiso 1 1 calc R . .
H11C H 0.3273 0.6115 0.1025 0.036 Uiso 1 1 calc R . .
C12 C 0.55448(19) 0.35165(19) 0.24170(17) 0.0160(4) Uani 1 1 d . . .
H12A H 0.4558 0.3783 0.2380 0.019 Uiso 1 1 calc R . .
H12B H 0.6115 0.3200 0.1659 0.019 Uiso 1 1 calc R . .
C13 C 0.59032(19) 0.23215(19) 0.36623(17) 0.0158(4) Uani 1 1 d . . .
C14 C 0.69184(18) 0.27134(19) 0.40077(16) 0.0131(4) Uani 1 1 d . . .
C15 C 0.68502(18) 0.41023(19) 0.33500(16) 0.0129(4) Uani 1 1 d . . .
C16 C 0.4625(2) 0.2359(2) 0.47330(18) 0.0201(4) Uani 1 1 d . . .
H16A H 0.4901 0.1652 0.5528 0.030 Uiso 1 1 calc R . .
H16B H 0.3946 0.2160 0.4490 0.030 Uiso 1 1 calc R . .
H16C H 0.4214 0.3289 0.4865 0.030 Uiso 1 1 calc R . .
C17 C 0.6547(2) 0.0888(2) 0.3434(2) 0.0227(4) Uani 1 1 d . . .
H17A H 0.7376 0.0867 0.2769 0.034 Uiso 1 1 calc R . .
H17B H 0.5878 0.0707 0.3157 0.034 Uiso 1 1 calc R . .
H17C H 0.6800 0.0167 0.4230 0.034 Uiso 1 1 calc R . .
C18 C 0.78216(18) 0.1903(2) 0.48547(17) 0.0154(4) Uani 1 1 d . . .
H18 H 0.7896 0.0951 0.5291 0.018 Uiso 1 1 calc R . .
C19 C 0.86258(18) 0.25043(19) 0.50612(16) 0.0145(4) Uani 1 1 d . . .
C20 C 0.85357(18) 0.39162(19) 0.44263(17) 0.0143(4) Uani 1 1 d . . .
C21 C 0.76396(18) 0.47039(19) 0.35542(17) 0.0143(4) Uani 1 1 d . . .
H21 H 0.7571 0.5652 0.3101 0.017 Uiso 1 1 calc R . .
C22 C 0.9223(2) 0.8154(2) 0.10194(19) 0.0270(5) Uani 1 1 d . . .
H22A H 0.9736 0.7143 0.1348 0.032 Uiso 1 1 calc R . .
H22B H 0.9473 0.8673 0.1406 0.032 Uiso 1 1 calc R . .


_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
Cl1 C22 1.768(2) . ?
Cl2 C22 1.771(2) . ?
O1 N1 1.222(2) . ?
O2 N1 1.237(2) . ?
N1 C2 1.450(2) . ?
N2 O4 1.220(2) . ?
N2 O3 1.247(2) . ?
N2 C19 1.453(2) . ?
C1 O5 1.345(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.409(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.376(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C4 C7 1.520(2) . ?
O5 H5 0.8400 . ?
C5 C6 1.379(3) . ?
C5 C9 1.514(2) . ?
O6 C20 1.343(2) . ?
O6 H6 0.8400 . ?
C6 H6A 0.9500 . ?
C7 C10 1.523(3) . ?
C7 C11 1.535(3) . ?
C7 C8 1.558(2) . ?
C8 C9 1.554(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C15 1.519(2) . ?
C9 C12 1.559(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.552(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(3) . ?
C13 C17 1.521(3) . ?
C13 C16 1.537(3) . ?
C14 C18 1.376(3) . ?
C14 C15 1.398(2) . ?
C15 C21 1.379(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.394(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.412(3) . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 121.64(15) . . ?
O1 N1 C2 119.19(15) . . ?
O2 N1 C2 119.16(16) . . ?
O4 N2 O3 122.33(16) . . ?
O4 N2 C19 119.14(16) . . ?
O3 N2 C19 118.53(16) . . ?
O5 C1 C6 117.25(17) . . ?
O5 C1 C2 124.49(17) . . ?
C6 C1 C2 118.26(16) . . ?
C3 C2 C1 121.85(16) . . ?
C3 C2 N1 117.72(16) . . ?
C1 C2 N1 120.44(16) . . ?
C4 C3 C2 118.55(17) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.96(16) . . ?
C3 C4 C7 128.09(17) . . ?
C5 C4 C7 111.95(15) . . ?
C1 O5 H5 109.5 . . ?
C6 C5 C4 121.51(16) . . ?
C6 C5 C9 127.10(16) . . ?
C4 C5 C9 111.39(15) . . ?
C20 O6 H6 109.5 . . ?
C5 C6 C1 119.87(17) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C4 C7 C10 111.35(15) . . ?
C4 C7 C11 110.41(15) . . ?
C10 C7 C11 109.90(16) . . ?
C4 C7 C8 101.62(14) . . ?
C10 C7 C8 111.60(15) . . ?
C11 C7 C8 111.75(15) . . ?
C9 C8 C7 108.00(14) . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C5 C9 C15 113.46(14) . . ?
C5 C9 C8 102.00(14) . . ?
C15 C9 C8 112.86(14) . . ?
C5 C9 C12 111.86(14) . . ?
C15 C9 C12 101.61(14) . . ?
C8 C9 C12 115.57(15) . . ?
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 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 108.23(14) . . ?
C13 C12 H12A 110.1 . . ?
C9 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C9 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C14 C13 C17 112.28(15) . . ?
C14 C13 C16 109.34(15) . . ?
C17 C13 C16 110.20(15) . . ?
C14 C13 C12 101.47(14) . . ?
C17 C13 C12 111.85(15) . . ?
C16 C13 C12 111.42(15) . . ?
C18 C14 C15 119.75(16) . . ?
C18 C14 C13 128.67(17) . . ?
C15 C14 C13 111.58(15) . . ?
C21 C15 C14 121.67(16) . . ?
C21 C15 C9 126.61(16) . . ?
C14 C15 C9 111.71(15) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 118.79(17) . . ?
C14 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C20 121.76(16) . . ?
C18 C19 N2 117.81(17) . . ?
C20 C19 N2 120.42(16) . . ?
O6 C20 C21 116.96(16) . . ?
O6 C20 C19 124.64(16) . . ?
C21 C20 C19 118.37(16) . . ?
C15 C21 C20 119.61(17) . . ?
C15 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
Cl1 C22 Cl2 111.14(11) . . ?
Cl1 C22 H22A 109.4 . . ?
Cl2 C22 H22A 109.4 . . ?
Cl1 C22 H22B 109.4 . . ?
Cl2 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.11
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_181215_tts1_26_29_0m_P3121
_database_code_depnum_ccdc_archive 'CCDC 2009788'
loop_
_audit_author_name
_audit_author_address
'Maryana Kraft'
;University Augsburg
Germany
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT201_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         15 		Report 
             N4      C1      C2      C3      C4 C5                  etc.

RESPONSE: The crystals were of poor quality, small and weakly scattering. 
	Several crystals of the same structure have been measured and all
	of them have shown the similar behavior. All measured crystals 
	showed merohedral twinning caused by 180\% rotation around [001] 
	and thus simulating hexagonal symmetry. The position of atoms of 
	cyclopentan and methylgroups of linker could be found only after 
	applying the twin matrix. Isotropic non-H Atoms in the structure 
	could be explained by steric strains of the coordinated linker in
	the crystal packing arrangement (see Fig. 10 of the publication).
;


_vrf_PLAT241_181215_tts1_26_29_0m_P3121 
;

PROBLEM: High   ?MainMol? Ueq as Compared to Neighbors of        C14 		Check 

RESPONSE: The differences in Ueq in the coordinated DMF arise from 
	possible disorder of DMF, which could not be refined because of 
	poor quality of the measured crystal.
;


_vrf_PLAT242_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Low    ?MainMol? Ueq as Compared to Neighbors of         O1 		Check 

RESPONSE: The differences in Ueq in the coordinated DMF arise from 
	possible disorder of DMF, which could not be refined because of 
	poor quality of the measured crystal.
;



_vrf_PLAT410_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Short Intra H...H Contact  H8B ..H8B . 1.50 Ang. y,x,-z =      4_555 		Check 

RESPONSE: The crystals were of poor quality, small and weakly scattering. 
	Several crystals of the same structure have been measured and all
	of them have shown the similar behavior. All measured crystals 
	showed merohedral twinning caused by 180\% rotation around [001] 
	and thus simulating hexagonal symmetry. The position of atoms of 
	cyclopentan and methylgroups of linker could be found only after 
	applying the twin matrix. It was not possible to determine the 
	positions of hydrogen atoms. Missing H-atoms were added by AFIX 
	constrains. Short H...H-contacts could be explained by steric 
	strains of the coordinated linker in
	the crystal packing arrangement (see Fig. 10 of the publication).
;


_vrf_PLAT413_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Short Inter XH3 .. XHn H11B ..H11C . 1.34 Ang.

RESPONSE: The crystals were of poor quality, small and weakly scattering. 
	Several crystals of the same structure have been measured and all
	of them have shown the similar behavior. All measured crystals 
	showed merohedral twinning caused by 180\% rotation around [001] 
	and thus simulating hexagonal symmetry. The position of atoms of 
	cyclopentan and methylgroups of linker could be found only after 
	applying the twin matrix. It was not possible to determine the 
	positions of hydrogen atoms. Missing H-atoms were added by AFIX 
	constrains. Short H...H-contacts could be explained by steric 
	strains of the coordinated linker in
	the crystal packing arrangement (see Fig. 10 of the publication).
;


_vrf_THETM01_181215_tts1_26_29_0m_P3121 
;

PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575

RESPONSE: The crystals were of poor quality, small and weakly scattering. 
;


_vrf_PLAT220_181215_tts1_26_29_0m_P3121 
;

PROBLEM: NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 7.2 Ratio

RESPONSE: High C Ueq(max)/Ueq(min) ratio results from high Ueq of 
	coordinated DMF molecules. The ppossible disorder of DMF 
	molecules could not be refined because of poor quality of 
	the measured crystal.
;


_vrf_PLAT230_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Hirshfeld Test Diff for N2 --N3 . 7.5 s.u.

RESPONSE: Hirshfeld test violations for atoms N2 and N3 are caused by
	steric strains of the coordinated linker in the crystal packing 
	arrangement (see Fig. 10 of the publication).
;


_vrf_PLAT341_181215_tts1_26_29_0m_P3121 
;

PROBLEM: Low Bond Precision on C-C Bonds ............... 0.055 Ang.

RESPONSE: Because of very small and weakly scattering crystals the 
	structure could not be solved with higher precision.
;



# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H34 Cl2 Mn2 N8 O2'
_chemical_formula_weight         683.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1800 0.2070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3710 0.9340 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0040 '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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   17.344(3)
_cell_length_b                   17.344(3)
_cell_length_c                   8.8070(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2294.5(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1969
_cell_measurement_theta_min      5.356
_cell_measurement_theta_max      34.62

_exptl_crystal_description       needle-shaped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.495
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   
'SADABS-2016/2 - Burker AXS area detector scaling and adsorption correction'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.8104
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Dectris EIGER X 1M'
_diffrn_measurement_method       \/Yw
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22416
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.1139
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        27.481
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2365
_reflns_number_gt                1223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     1.000
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'SPring-8 BL40XU Data Collection Software'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc. 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc. 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, Diamond'
_computing_publication_material  Word
_refine_special_details          
;
 Refined as a 2-component twin.
 The crystal showd merohedral twinning caused by rotation around [001].
 The position of atoms of cyclopentan and methylgroups of linker 
 could be found only after applying the twin matrix -1 0 0  0 -1 0  0 0 1
 FLAT and DFIX restrain were used for the refinement of DMF molecules
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1858P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2365
_refine_ls_number_parameters     115
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0999
_refine_ls_wR_factor_ref         0.3084
_refine_ls_wR_factor_gt          0.2540
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
Mn1 Mn 0.3761(4) 0.6243(4) 0.2496(8) 0.1280(14) Uani 1 1 d . . . . .
Cl1 Cl 0.2573(9) 0.5081(3) 0.0798(15) 0.160(2) Uani 1 1 d . . . . .
O1 O 0.453(3) 0.557(3) 0.236(5) 0.202(10) Uani 1 1 d D . . . .
C2 C 0.5262(17) 0.720(2) -0.024(3) 0.138(9) Uiso 1 1 d D . . . .
N1 N 0.4401(18) 0.688(2) 0.018(4) 0.166(13) Uani 1 1 d D . . . .
N2 N 0.3985(12) 0.6997(19) -0.092(3) 0.131(9) Uani 1 1 d D . . . .
N3 N 0.4441(12) 0.7440(16) -0.201(2) 0.110(7) Uani 1 1 d D . . . .
C1 C 0.5298(16) 0.7578(19) -0.179(3) 0.125(7) Uiso 1 1 d D . . . .
C3 C 0.5995(17) 0.7212(18) 0.044(3) 0.127(7) Uiso 1 1 d . . . . .
H3 H 0.597785 0.699477 0.143857 0.152 Uiso 1 1 calc R U . . .
C6 C 0.607(3) 0.784(2) -0.260(5) 0.166(10) Uiso 1 1 d . . . . .
H6 H 0.610767 0.799185 -0.364928 0.200 Uiso 1 1 calc R U . . .
C4 C 0.675(2) 0.757(2) -0.046(3) 0.140(8) Uiso 1 1 d . . . . .
C5 C 0.679(2) 0.789(2) -0.184(4) 0.149(9) Uiso 1 1 d . . . . .
C7 C 0.773(2) 0.823(2) -0.256(4) 0.165(10) Uiso 1 1 d D . . . .
C8 C 0.827(3) 0.809(3) -0.118(5) 0.201(14) Uiso 1 1 d . . . . .
H8A H 0.852117 0.771410 -0.152708 0.242 Uiso 1 1 calc R U . . .
H8B H 0.876752 0.866838 -0.083731 0.242 Uiso 1 1 calc R U . . .
C9 C 0.767(3) 0.767(3) 0.000000 0.151(13) Uiso 1 2 d S . P . .
C10 C 0.819(3) 0.914(3) -0.333(6) 0.23(2) Uiso 1 1 d . . . . .
H10A H 0.876825 0.926617 -0.372124 0.341 Uiso 1 1 calc R U . . .
H10B H 0.781784 0.913845 -0.417513 0.341 Uiso 1 1 calc R U . . .
H10C H 0.827045 0.959984 -0.259663 0.341 Uiso 1 1 calc R U . . .
C11 C 0.737(4) 0.745(3) -0.378(6) 0.28(3) Uiso 1 1 d D . . . .
H11A H 0.707546 0.687139 -0.325487 0.418 Uiso 1 1 calc R U . . .
H11B H 0.693652 0.748771 -0.444721 0.418 Uiso 1 1 calc R U . . .
H11C H 0.786505 0.750066 -0.438410 0.418 Uiso 1 1 calc R U . . .
N4 N 0.454(3) 0.426(4) 0.229(6) 0.28(2) Uiso 1 1 d D . . . .
C12 C 0.411(4) 0.329(3) 0.229(10) 0.33(4) Uiso 1 1 d D . . . .
H12A H 0.456128 0.310774 0.235151 0.498 Uiso 1 1 calc R U . . .
H12B H 0.370709 0.304749 0.316237 0.498 Uiso 1 1 calc R U . . .
H12C H 0.376659 0.305445 0.134865 0.498 Uiso 1 1 calc R U . . .
C13 C 0.552(4) 0.484(7) 0.24(2) 0.44(6) Uiso 1 1 d D . . . .
H13A H 0.580219 0.446946 0.243822 0.659 Uiso 1 1 calc R U . . .
H13B H 0.573690 0.522039 0.148525 0.659 Uiso 1 1 calc R U . . .
H13C H 0.567467 0.521082 0.329876 0.659 Uiso 1 1 calc R U . . .
C14 C 0.413(7) 0.474(4) 0.22(3) 0.9(2) Uiso 1 1 d D . . . .
H14 H 0.350071 0.443176 0.205578 1.026 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
Mn1 O1 2.174(19) . ?
Mn1 N2 2.259(18) 2_665 ?
Mn1 N3 2.283(19) 3_565 ?
Mn1 N1 2.32(2) . ?
Mn1 Cl1 2.528(14) . ?
Mn1 Cl1 2.541(13) 2_665 ?
O1 C14 1.26(3) . ?
C2 N1 1.36(3) . ?
C2 C3 1.40(3) . ?
C2 C1 1.51(4) . ?
N1 N2 1.28(2) . ?
N2 N3 1.24(2) . ?
N3 C1 1.40(3) . ?
C1 C6 1.38(4) . ?
C3 C4 1.39(4) . ?
C3 H3 0.9500 . ?
C6 C5 1.38(5) . ?
C6 H6 0.9500 . ?
C4 C5 1.33(4) . ?
C4 C9 1.56(4) . ?
C5 C7 1.56(5) . ?
C7 C10 1.53(6) . ?
C7 C11 1.60(3) . ?
C7 C8 1.63(6) . ?
C8 C9 1.40(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N4 C14 1.35(3) . ?
N4 C12 1.46(3) . ?
N4 C13 1.48(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
O1 Mn1 N2 174.7(11) . 2_665 ?
O1 Mn1 N3 96.8(12) . 3_565 ?
N2 Mn1 N3 88.4(10) 2_665 3_565 ?
O1 Mn1 N1 86.1(13) . . ?
N2 Mn1 N1 88.7(12) 2_665 . ?
N3 Mn1 N1 174.4(11) 3_565 . ?
O1 Mn1 Cl1 90.8(12) . . ?
N2 Mn1 Cl1 87.9(8) 2_665 . ?
N3 Mn1 Cl1 92.9(6) 3_565 . ?
N1 Mn1 Cl1 82.3(10) . . ?
O1 Mn1 Cl1 93.0(12) . 2_665 ?
N2 Mn1 Cl1 88.2(8) 2_665 2_665 ?
N3 Mn1 Cl1 88.6(6) 3_565 2_665 ?
N1 Mn1 Cl1 96.0(10) . 2_665 ?
Cl1 Mn1 Cl1 175.7(2) . 2_665 ?
Mn1 Cl1 Mn1 93.01(19) . 3_564 ?
C14 O1 Mn1 119(4) . . ?
N1 C2 C3 134(3) . . ?
N1 C2 C1 102.9(17) . . ?
C3 C2 C1 123(2) . . ?
N2 N1 C2 108.8(17) . . ?
N2 N1 Mn1 124(2) . . ?
C2 N1 Mn1 127(2) . . ?
N3 N2 N1 116.7(18) . . ?
N3 N2 Mn1 125.3(15) . 3_564 ?
N1 N2 Mn1 118(2) . 3_564 ?
N2 N3 C1 107.1(16) . . ?
N2 N3 Mn1 119.7(15) . 2_664 ?
C1 N3 Mn1 130.2(14) . 2_664 ?
C6 C1 N3 139(3) . . ?
C6 C1 C2 116(2) . . ?
N3 C1 C2 104.0(15) . . ?
C4 C3 C2 115(3) . . ?
C4 C3 H3 122.7 . . ?
C2 C3 H3 122.7 . . ?
C1 C6 C5 118(3) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C5 C4 C3 123(3) . . ?
C5 C4 C9 111(3) . . ?
C3 C4 C9 126(3) . . ?
C4 C5 C6 125(4) . . ?
C4 C5 C7 110(3) . . ?
C6 C5 C7 125(3) . . ?
C10 C7 C5 119(3) . . ?
C10 C7 C11 111(4) . . ?
C5 C7 C11 93(3) . . ?
C10 C7 C8 117(3) . . ?
C5 C7 C8 102(3) . . ?
C11 C7 C8 113(4) . . ?
C9 C8 C7 107(3) . . ?
C9 C8 H8A 110.3 . . ?
C7 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 C8 101(5) 4 . ?
C8 C9 C4 109(2) 4 4 ?
C8 C9 C4 113(2) . 4 ?
C8 C9 C4 113(2) 4 . ?
C8 C9 C4 109(2) . . ?
C4 C9 C4 111(4) 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 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 N4 C12 126(4) . . ?
C14 N4 C13 112(8) . . ?
C12 N4 C13 123(7) . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 N4 123(8) . . ?
O1 C14 H14 118.7 . . ?
N4 C14 H14 118.7 . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_LL__a_IPa
_database_code_depnum_ccdc_archive 'CCDC 2009789'
loop_
_audit_author_name
_audit_author_address
'Maryana Kraft'
;University Augsburg
Germany
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2020-10-29 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         ?
_chemical_formula_sum            'C43 H60 O6'
_chemical_formula_weight         672.91

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.6730(5)
_cell_length_b                   10.5884(5)
_cell_length_c                   39.5971(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4055.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9714
_cell_measurement_theta_min      2.344
_cell_measurement_theta_max      20.796

_exptl_crystal_description       'block crystal'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.137
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7220
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            238667
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0782
_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       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         28.785
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10542
_reflns_number_gt                6941
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_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       'Bruker Instrument Service v3.0.25'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, Diamond'
_computing_publication_material  Word
_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+0.6377P] 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 2213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(17)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         10542
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.4927(2) 0.56020(19) 0.36052(5) 0.0552(5) Uani 1 1 d . . . . .
O2 O 0.3313(2) -0.0185(2) 0.42492(5) 0.0606(6) Uani 1 1 d . . . . .
O3 O 0.2336(2) 0.0111(2) 0.47259(4) 0.0638(6) Uani 1 1 d . . . . .
O4 O 0.6934(2) 0.6096(2) 0.37785(5) 0.0658(6) Uani 1 1 d . . . . .
O5 O 0.1231(3) 0.0735(3) 0.42645(5) 0.0833(8) Uani 1 1 d . . . . .
C1 C 0.2975(3) 0.3096(2) 0.31798(6) 0.0367(6) Uani 1 1 d . . . . .
C2 C 0.3326(3) 0.0792(2) 0.33559(6) 0.0380(6) Uani 1 1 d . . . . .
O6 O 0.6739(2) 0.5113(3) 0.32820(7) 0.0982(10) Uani 1 1 d . . . . .
C3 C 0.1831(3) 0.3772(3) 0.30763(6) 0.0428(6) Uani 1 1 d . . . . .
C4 C 0.4104(3) -0.0178(2) 0.32219(6) 0.0422(6) Uani 1 1 d . . . . .
C5 C 0.3483(3) -0.0143(3) 0.38987(6) 0.0441(6) Uani 1 1 d . . . . .
C6 C 0.3019(3) 0.0834(2) 0.36981(6) 0.0422(6) Uani 1 1 d . . . . .
C7 C 0.6272(3) 0.5551(3) 0.35295(8) 0.0508(7) Uani 1 1 d . . . . .
C8 C 0.2853(3) 0.1713(2) 0.30883(6) 0.0398(6) Uani 1 1 d . . . . .
C9 C 0.3967(3) 0.4972(3) 0.34003(7) 0.0442(6) Uani 1 1 d . . . . .
C10 C 0.2194(3) 0.0283(3) 0.44010(7) 0.0458(6) Uani 1 1 d . . . . .
C11 C 0.4052(3) 0.3685(3) 0.33464(7) 0.0419(6) Uani 1 1 d . . . . .
C12 C 0.0897(3) -0.0307(3) 0.52108(7) 0.0518(7) Uani 1 1 d . . . . .
C13 C 0.0736(3) 0.2913(3) 0.29241(7) 0.0504(7) Uani 1 1 d . . . . .
C14 C 0.4562(3) -0.1141(3) 0.34263(8) 0.0515(7) Uani 1 1 d . . . . .
C15 C 0.1277(3) 0.0659(3) 0.49454(7) 0.0532(8) Uani 1 1 d . . . . .
C16 C 0.4243(3) -0.1123(3) 0.37666(8) 0.0522(7) Uani 1 1 d . . . . .
C17 C 0.4303(3) -0.0019(3) 0.28441(7) 0.0516(7) Uani 1 1 d . . . . .
C18 C 0.1291(3) 0.1606(3) 0.30130(8) 0.0534(8) Uani 1 1 d . . . . .
C19 C 0.2875(3) 0.5664(3) 0.32828(8) 0.0524(7) Uani 1 1 d . . . . .
C20 C 0.3820(4) 0.1344(3) 0.27901(7) 0.0501(7) Uani 1 1 d . . . . .
C21 C 0.1795(3) 0.5067(3) 0.31210(8) 0.0539(7) Uani 1 1 d . . . . .
C22 C 0.8451(3) 0.6090(3) 0.37718(8) 0.0538(8) Uani 1 1 d . . . . .
C23 C 0.8917(3) 0.7386(3) 0.38832(8) 0.0555(8) Uani 1 1 d . . . . .
C24 C 0.8931(4) 0.5047(4) 0.40016(10) 0.0688(9) Uani 1 1 d . . . . .
C25 C -0.0121(4) 0.0323(4) 0.54564(9) 0.0699(10) Uani 1 1 d . . . . .
C26 C 0.0428(5) 0.1532(5) 0.56048(10) 0.0812(12) Uani 1 1 d . . . . .
C27 C 0.0391(4) -0.1565(4) 0.50673(9) 0.0678(9) Uani 1 1 d . . . . .
C28 C 0.3383(5) -0.0976(3) 0.26524(8) 0.0780(11) Uani 1 1 d . . . . .
H28A H 0.369839 -0.181857 0.269811 0.117 Uiso 1 1 calc R U . . .
H28B H 0.343800 -0.081448 0.241420 0.117 Uiso 1 1 calc R U . . .
H28C H 0.244216 -0.088894 0.272591 0.117 Uiso 1 1 calc R U . . .
C29 C 0.0859(5) 0.2480(4) 0.53394(12) 0.0818(11) Uani 1 1 d . . . . .
C30 C 1.0476(4) 0.7366(4) 0.39318(12) 0.0734(10) Uani 1 1 d . . . . .
C31 C -0.0684(4) 0.3156(4) 0.30751(11) 0.0826(11) Uani 1 1 d . . . . .
H31A H -0.132721 0.254383 0.298968 0.124 Uiso 1 1 calc R U . . .
H31B H -0.098713 0.398846 0.301445 0.124 Uiso 1 1 calc R U . . .
H31C H -0.063319 0.308780 0.331654 0.124 Uiso 1 1 calc R U . . .
C32 C 0.1852(4) 0.1850(4) 0.50932(11) 0.0701(10) Uani 1 1 d . . . . .
C33 C 0.8395(4) 0.8448(4) 0.36500(10) 0.0742(10) Uani 1 1 d . . . . .
C34 C 1.0496(4) 0.5040(4) 0.40523(11) 0.0779(10) Uani 1 1 d . . . . .
C35 C 0.5802(4) -0.0215(4) 0.27328(9) 0.0795(11) Uani 1 1 d . . . . .
H35A H 0.639344 0.034505 0.285703 0.119 Uiso 1 1 calc R U . . .
H35B H 0.588311 -0.004114 0.249574 0.119 Uiso 1 1 calc R U . . .
H35C H 0.606940 -0.107349 0.277585 0.119 Uiso 1 1 calc R U . . .
C36 C 0.0666(4) 0.3126(4) 0.25396(8) 0.0788(11) Uani 1 1 d . . . . .
H36A H 0.156421 0.299505 0.244277 0.118 Uiso 1 1 calc R U . . .
H36B H 0.036784 0.397469 0.249477 0.118 Uiso 1 1 calc R U . . .
H36C H 0.002127 0.254207 0.244170 0.118 Uiso 1 1 calc R U . . .
C37 C 1.0965(5) 0.6332(5) 0.41646(14) 0.0907(13) Uani 1 1 d . . . . .
C38 C -0.0954(4) -0.1465(5) 0.48708(11) 0.0965(13) Uani 1 1 d . . . . .
H38A H -0.168065 -0.119475 0.501950 0.145 Uiso 1 1 calc R U . . .
H38B H -0.118408 -0.227416 0.477719 0.145 Uiso 1 1 calc R U . . .
H38C H -0.084833 -0.086145 0.469169 0.145 Uiso 1 1 calc R U . . .
C39 C 0.0271(5) -0.2561(4) 0.53417(12) 0.1051(15) Uani 1 1 d . . . . .
H39A H 0.105515 -0.250545 0.548940 0.158 Uiso 1 1 calc R U . . .
H39B H 0.024139 -0.338374 0.524027 0.158 Uiso 1 1 calc R U . . .
H39C H -0.056077 -0.242223 0.546882 0.158 Uiso 1 1 calc R U . . .
C40 C 0.8463(7) 0.9726(4) 0.38107(14) 0.1240(19) Uani 1 1 d . . . . .
H40A H 0.941118 0.997974 0.383257 0.186 Uiso 1 1 calc R U . . .
H40B H 0.804233 0.969300 0.403017 0.186 Uiso 1 1 calc R U . . .
H40C H 0.797788 1.032486 0.367247 0.186 Uiso 1 1 calc R U . . .
C41 C 0.1502(6) 0.3652(5) 0.54952(17) 0.140(2) Uani 1 1 d . . . . .
H41A H 0.233050 0.342279 0.561390 0.210 Uiso 1 1 calc R U . . .
H41B H 0.085928 0.402892 0.565004 0.210 Uiso 1 1 calc R U . . .
H41C H 0.172349 0.424630 0.532020 0.210 Uiso 1 1 calc R U . . .
C42 C 0.9120(8) 0.8468(6) 0.33142(11) 0.149(3) Uani 1 1 d . . . . .
H42A H 0.871309 0.910486 0.317310 0.223 Uiso 1 1 calc R U . . .
H42B H 0.902774 0.765818 0.320749 0.223 Uiso 1 1 calc R U . . .
H42C H 1.008161 0.865365 0.334751 0.223 Uiso 1 1 calc R U . . .
C43 C 1.0928(6) 0.3992(5) 0.42897(15) 0.133(2) Uani 1 1 d . . . . .
H43A H 1.191744 0.391696 0.428836 0.199 Uiso 1 1 calc R U . . .
H43B H 1.052343 0.321044 0.421706 0.199 Uiso 1 1 calc R U . . .
H43C H 1.061901 0.418502 0.451418 0.199 Uiso 1 1 calc R U . . .
H1 H 0.482(3) 0.324(2) 0.3419(6) 0.037(7) Uiso 1 1 d . . . . .
H2 H 0.457(3) -0.179(3) 0.3899(8) 0.059(9) Uiso 1 1 d . . . . .
H3 H 0.852(4) 0.516(4) 0.4204(11) 0.099(14) Uiso 1 1 d . . . . .
H4 H 0.872(3) 0.592(3) 0.3538(7) 0.045(7) Uiso 1 1 d . . . . .
H5 H 0.512(3) -0.186(3) 0.3340(8) 0.067(9) Uiso 1 1 d . . . . .
H6 H 0.123(4) 0.133(4) 0.5738(10) 0.089(13) Uiso 1 1 d . . . . .
H7 H 0.250(3) 0.151(3) 0.3790(6) 0.041(7) Uiso 1 1 d . . . . .
H8 H 0.847(3) 0.749(3) 0.4124(7) 0.051(8) Uiso 1 1 d . . . . .
H9 H 0.859(4) 0.418(4) 0.3905(8) 0.076(10) Uiso 1 1 d . . . . .
H10 H 0.271(4) 0.166(3) 0.5229(8) 0.069(10) Uiso 1 1 d . . . . .
H11 H 0.176(3) -0.050(3) 0.5338(7) 0.057(8) Uiso 1 1 d . . . . .
H12 H -0.026(4) 0.196(4) 0.5763(10) 0.092(12) Uiso 1 1 d . . . . .
H13 H 0.046(3) 0.083(3) 0.4803(7) 0.048(7) Uiso 1 1 d . . . . .
H14 H 0.468(3) 0.190(3) 0.2795(7) 0.054(8) Uiso 1 1 d . . . . .
H15 H 0.114(3) 0.098(3) 0.2842(8) 0.061(9) Uiso 1 1 d . . . . .
H16 H -0.038(4) -0.035(4) 0.5633(10) 0.088(12) Uiso 1 1 d . . . . .
H17 H 0.003(5) 0.269(4) 0.5210(10) 0.090(13) Uiso 1 1 d . . . . .
H18 H 0.290(3) 0.657(3) 0.3321(7) 0.057(8) Uiso 1 1 d . . . . .
H19 H 1.094(4) 0.486(3) 0.3835(9) 0.072(10) Uiso 1 1 d . . . . .
H20 H 0.328(3) 0.147(3) 0.2565(8) 0.066(9) Uiso 1 1 d . . . . .
H21 H 0.077(3) 0.128(3) 0.3233(8) 0.053(8) Uiso 1 1 d . . . . .
H22 H 1.089(4) 0.724(3) 0.3722(9) 0.066(11) Uiso 1 1 d . . . . .
H23 H 1.074(4) 0.820(4) 0.3999(9) 0.081(11) Uiso 1 1 d . . . . .
H24 H 0.113(4) -0.185(3) 0.4914(9) 0.083(11) Uiso 1 1 d . . . . .
H25 H 0.104(4) 0.554(3) 0.3052(8) 0.068(10) Uiso 1 1 d . . . . .
H26 H 1.061(5) 0.657(4) 0.4390(11) 0.101(15) Uiso 1 1 d . . . . .
H27 H 1.203(6) 0.642(4) 0.4192(12) 0.131(16) Uiso 1 1 d . . . . .
H28 H -0.101(4) 0.053(3) 0.5328(8) 0.070(10) Uiso 1 1 d . . . . .
H29 H 0.735(5) 0.827(4) 0.3626(10) 0.098(13) Uiso 1 1 d . . . . .
H30 H 0.204(4) 0.238(4) 0.4931(10) 0.082(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.336(3) . ?
O1 C9 1.402(3) . ?
O2 C10 1.333(3) . ?
O2 C5 1.398(3) . ?
O3 C10 1.307(3) . ?
O3 C15 1.463(3) . ?
O4 C7 1.310(4) . ?
O4 C22 1.467(4) . ?
O5 C10 1.178(3) . ?
C1 C3 1.380(4) . ?
C1 C11 1.382(4) . ?
C1 C8 1.513(4) . ?
C2 C4 1.380(4) . ?
C2 C6 1.388(3) . ?
C2 C8 1.510(4) . ?
O6 C7 1.174(3) . ?
C3 C21 1.383(4) . ?
C3 C13 1.520(4) . ?
C4 C14 1.375(4) . ?
C4 C17 1.518(4) . ?
C5 C16 1.375(4) . ?
C5 C6 1.380(4) . ?
C8 C18 1.544(4) . ?
C8 C20 1.557(4) . ?
C9 C19 1.368(4) . ?
C9 C11 1.382(4) . ?
C12 C15 1.512(4) . ?
C12 C27 1.529(5) . ?
C12 C25 1.536(4) . ?
C13 C31 1.520(5) . ?
C13 C18 1.525(4) . ?
C13 C36 1.541(4) . ?
C14 C16 1.383(4) . ?
C15 C32 1.498(5) . ?
C17 C35 1.529(4) . ?
C17 C20 1.531(4) . ?
C17 C28 1.548(4) . ?
C19 C21 1.379(4) . ?
C22 C24 1.505(5) . ?
C22 C23 1.510(4) . ?
C23 C30 1.521(5) . ?
C23 C33 1.540(5) . ?
C24 C34 1.527(5) . ?
C25 C26 1.506(6) . ?
C26 C29 1.511(6) . ?
C27 C39 1.518(5) . ?
C27 C38 1.520(5) . ?
C29 C41 1.520(6) . ?
C29 C32 1.522(6) . ?
C30 C37 1.508(6) . ?
C33 C40 1.497(6) . ?
C33 C42 1.504(6) . ?
C34 C37 1.508(6) . ?
C34 C43 1.513(6) . ?

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
C7 O1 C9 119.7(2) . . ?
C10 O2 C5 122.1(2) . . ?
C10 O3 C15 117.1(2) . . ?
C7 O4 C22 118.2(2) . . ?
C3 C1 C11 120.8(2) . . ?
C3 C1 C8 111.6(2) . . ?
C11 C1 C8 127.6(2) . . ?
C4 C2 C6 121.0(2) . . ?
C4 C2 C8 112.1(2) . . ?
C6 C2 C8 126.8(2) . . ?
C1 C3 C21 119.8(3) . . ?
C1 C3 C13 111.4(2) . . ?
C21 C3 C13 128.8(3) . . ?
C14 C4 C2 120.1(2) . . ?
C14 C4 C17 128.4(2) . . ?
C2 C4 C17 111.4(2) . . ?
C16 C5 C6 121.4(2) . . ?
C16 C5 O2 114.7(2) . . ?
C6 C5 O2 123.8(2) . . ?
C5 C6 C2 117.9(3) . . ?
O6 C7 O4 127.9(3) . . ?
O6 C7 O1 125.3(3) . . ?
O4 C7 O1 106.8(2) . . ?
C2 C8 C1 115.6(2) . . ?
C2 C8 C18 112.7(2) . . ?
C1 C8 C18 101.1(2) . . ?
C2 C8 C20 100.8(2) . . ?
C1 C8 C20 112.2(2) . . ?
C18 C8 C20 115.1(2) . . ?
C19 C9 C11 121.5(3) . . ?
C19 C9 O1 116.9(2) . . ?
C11 C9 O1 121.3(2) . . ?
O5 C10 O3 126.2(3) . . ?
O5 C10 O2 125.9(3) . . ?
O3 C10 O2 107.9(2) . . ?
C9 C11 C1 118.3(3) . . ?
C15 C12 C27 114.1(2) . . ?
C15 C12 C25 107.6(3) . . ?
C27 C12 C25 114.1(3) . . ?
C31 C13 C3 111.8(3) . . ?
C31 C13 C18 112.4(3) . . ?
C3 C13 C18 101.9(2) . . ?
C31 C13 C36 108.9(3) . . ?
C3 C13 C36 109.6(3) . . ?
C18 C13 C36 112.1(3) . . ?
C4 C14 C16 119.4(3) . . ?
O3 C15 C32 107.8(3) . . ?
O3 C15 C12 108.4(3) . . ?
C32 C15 C12 112.8(3) . . ?
C5 C16 C14 120.0(3) . . ?
C4 C17 C35 112.9(3) . . ?
C4 C17 C20 101.8(2) . . ?
C35 C17 C20 112.1(3) . . ?
C4 C17 C28 109.8(3) . . ?
C35 C17 C28 108.3(3) . . ?
C20 C17 C28 111.9(3) . . ?
C13 C18 C8 108.8(2) . . ?
C9 C19 C21 119.8(3) . . ?
C17 C20 C8 108.3(2) . . ?
C19 C21 C3 119.7(3) . . ?
O4 C22 C24 107.5(3) . . ?
O4 C22 C23 106.8(3) . . ?
C24 C22 C23 113.5(3) . . ?
C22 C23 C30 108.7(3) . . ?
C22 C23 C33 113.0(3) . . ?
C30 C23 C33 114.3(3) . . ?
C22 C24 C34 112.9(3) . . ?
C26 C25 C12 112.9(3) . . ?
C25 C26 C29 113.0(3) . . ?
C39 C27 C38 110.5(3) . . ?
C39 C27 C12 111.3(3) . . ?
C38 C27 C12 113.8(3) . . ?
C26 C29 C41 111.9(4) . . ?
C26 C29 C32 109.2(3) . . ?
C41 C29 C32 111.1(4) . . ?
C37 C30 C23 113.5(4) . . ?
C15 C32 C29 112.6(3) . . ?
C40 C33 C42 110.0(4) . . ?
C40 C33 C23 113.0(3) . . ?
C42 C33 C23 112.8(4) . . ?
C37 C34 C43 113.5(4) . . ?
C37 C34 C24 109.4(4) . . ?
C43 C34 C24 111.1(4) . . ?
C30 C37 C34 112.6(3) . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.168
_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_cu_BB2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2009785'
loop_
_audit_author_name
_audit_author_address
'Maryana Kraft'
;University Augsburg
Germany
;
_audit_update_record             
;
2020-10-05 deposited with the CCDC.	2020-10-29 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         ?
_chemical_formula_sum            'C21 H22 N2 O6'
_chemical_formula_weight         398.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7978(3)
_cell_length_b                   12.4501(4)
_cell_length_c                   7.9839(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     973.90(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4300
_cell_measurement_theta_min      4.513
_cell_measurement_theta_max      68.042

_exptl_crystal_description       'block crystal'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.836
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5274
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.541
_diffrn_reflns_theta_max         68.036
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1751
_reflns_number_gt                1679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.968

_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 Instrument Service v3.0.25'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, Diamond'
_computing_publication_material  Word
_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)+(0.0433P)²+0.2011P] 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_abs_structure_details 
;
 Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1751
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.30734(19) 0.04873(13) 0.1290(2) 0.0340(4) Uani 1 1 d . . . . .
O2 O 0.42489(18) 0.09889(13) -0.0855(2) 0.0330(4) Uani 1 1 d . . . . .
O3 O 0.60709(16) 0.24852(13) -0.0484(2) 0.0294(4) Uani 1 1 d . . . . .
H3 H 0.575665 0.193037 -0.094159 0.035 Uiso 1 1 calc R U . . .
N1 N 0.38253(19) 0.11309(15) 0.0594(2) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.5295(2) 0.27427(18) 0.0855(3) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.4213(2) 0.21070(16) 0.1460(3) 0.0219(4) Uani 1 1 d . . . . .
C3 C 0.3461(2) 0.24021(17) 0.2872(3) 0.0209(4) Uani 1 1 d . . . . .
H3A H 0.275233 0.195106 0.327880 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3757(2) 0.33535(17) 0.3665(3) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.4828(2) 0.39902(17) 0.3065(3) 0.0196(4) Uani 1 1 d . . . . .
C6 C 0.5593(2) 0.36929(17) 0.1690(3) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.632122 0.413637 0.131578 0.026 Uiso 1 1 calc R U . . .
C7 C 0.500000 0.500000 0.4103(4) 0.0210(6) Uani 1 2 d S T P . .
C8 C 0.3653(2) 0.50113(18) 0.5140(2) 0.0217(4) Uani 1 1 d . . . . .
H8A H 0.383684 0.526543 0.629317 0.033 Uiso 1 1 calc R U . . .
H8B H 0.298294 0.550275 0.461655 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3074(2) 0.38470(17) 0.5184(3) 0.0226(5) Uani 1 1 d . . . . .
C10 C 0.1523(2) 0.38486(19) 0.5045(3) 0.0288(5) Uani 1 1 d . . . . .
H10A H 0.125063 0.420883 0.400588 0.043 Uiso 1 1 calc R U . . .
H10B H 0.113210 0.423109 0.600474 0.043 Uiso 1 1 calc R U . . .
H10C H 0.118770 0.310694 0.503512 0.043 Uiso 1 1 calc R U . . .
C11 C 0.3515(3) 0.32514(19) 0.6777(3) 0.0291(5) Uani 1 1 d . . . . .
H11A H 0.322361 0.249965 0.670933 0.044 Uiso 1 1 calc R U . . .
H11B H 0.309245 0.359111 0.775577 0.044 Uiso 1 1 calc R U . . .
H11C H 0.451056 0.328313 0.688482 0.044 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 N1 1.222(3) . ?
O2 N1 1.242(2) . ?
O3 C1 1.350(3) . ?
O3 H3 0.8400 . ?
N1 C2 1.449(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.409(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.374(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(3) . ?
C4 C9 1.515(3) . ?
C5 C6 1.380(3) . ?
C5 C7 1.515(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.558(2) 2_665 ?
C7 C8 1.558(2) . ?
C8 C9 1.557(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(3) . ?
C9 C11 1.535(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 O3 H3 109.5 . . ?
O1 N1 O2 122.13(19) . . ?
O1 N1 C2 119.39(18) . . ?
O2 N1 C2 118.46(18) . . ?
O3 C1 C6 117.64(18) . . ?
O3 C1 C2 124.2(2) . . ?
C6 C1 C2 118.16(19) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 N1 117.87(19) . . ?
C1 C2 N1 120.31(19) . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 C9 128.7(2) . . ?
C5 C4 C9 112.06(18) . . ?
C6 C5 C4 121.86(19) . . ?
C6 C5 C7 126.66(18) . . ?
C4 C5 C7 111.47(17) . . ?
C5 C6 C1 119.73(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C5 C7 C5 113.7(2) . 2_665 ?
C5 C7 C8 112.17(11) . 2_665 ?
C5 C7 C8 101.77(11) 2_665 2_665 ?
C5 C7 C8 101.76(11) . . ?
C5 C7 C8 112.18(11) 2_665 . ?
C8 C7 C8 115.8(2) 2_665 . ?
C9 C8 C7 108.19(15) . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C4 C9 C10 112.53(18) . . ?
C4 C9 C11 110.06(17) . . ?
C10 C9 C11 109.98(19) . . ?
C4 C9 C8 101.46(16) . . ?
C10 C9 C8 111.14(18) . . ?
C11 C9 C8 111.44(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036

