# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_a167
_database_code_depnum_ccdc_archive 'CCDC 2119858'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O2'
_chemical_formula_sum            'C17 H21 N3 O2'
_chemical_formula_weight         299.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.684
_cell_length_b                   7.971
_cell_length_c                   10.899
_cell_angle_alpha                90
_cell_angle_beta                 108.39
_cell_angle_gamma                90
_cell_volume                     798.4
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_temperature    290
_cell_measurement_theta_max      19.25
_cell_measurement_theta_min      6.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3905
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.975
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         2
_diffrn_standards_interval_time  120
_diffrn_standards_interval_count 400
_diffrn_standards_decay_%        2
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                2245
_reflns_number_total             3698
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1419
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,
 H14B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C7(H7), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7745(3) 0.3826(4) 0.8089(2) 0.0545(8) Uani 1 1 d . . . . .
N1 N 0.5779(3) 0.2251(4) 0.6848(3) 0.0442(8) Uani 1 1 d . . . . .
N3 N 0.9307(3) 0.5803(4) 0.7234(3) 0.0417(8) Uani 1 1 d . . . . .
O11 O 0.8859(3) 0.3129(5) 0.4520(3) 0.0678(10) Uani 1 1 d . . . . .
N2 N 0.5273(4) 0.1520(4) 0.5617(3) 0.0471(9) Uani 1 1 d . . . . .
C2 C 0.7420(4) 0.2863(5) 0.5883(4) 0.0406(9) Uani 1 1 d . . . . .
C3 C 0.6254(4) 0.1891(5) 0.5065(4) 0.0458(10) Uani 1 1 d . . . . .
C1 C 0.7081(4) 0.3067(5) 0.7040(4) 0.0421(9) Uani 1 1 d . . . . .
C11 C 0.8648(4) 0.3466(5) 0.5557(4) 0.0463(10) Uani 1 1 d . . . . .
C13 C 1.0564(4) 0.6659(6) 0.8195(4) 0.0544(12) Uani 1 1 d . . . . .
H13A H 1.112153 0.727129 0.774215 0.065 Uiso 1 1 calc R U . . .
H13B H 1.119772 0.582482 0.873956 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4917(4) 0.2079(6) 0.7673(4) 0.0455(10) Uani 1 1 d . . . . .
C12 C 0.9819(5) 0.4556(6) 0.6463(4) 0.0539(11) Uani 1 1 d . . . . .
H12A H 1.052340 0.382882 0.705463 0.065 Uiso 1 1 calc R U . . .
H12B H 1.032036 0.515201 0.595264 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3727(5) 0.1041(7) 0.7311(5) 0.0613(13) Uani 1 1 d . . . . .
H6 H 0.351718 0.042739 0.654825 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7714(5) 0.8218(6) 0.7238(5) 0.0619(12) Uani 1 1 d . . . . .
H16A H 0.716515 0.757899 0.768275 0.074 Uiso 1 1 calc R U . . .
H16B H 0.706672 0.904090 0.669294 0.074 Uiso 1 1 calc R U . . .
C15 C 0.8966(6) 0.9110(7) 0.8222(5) 0.0742(15) Uani 1 1 d . . . . .
H15A H 0.945098 0.984577 0.777894 0.089 Uiso 1 1 calc R U . . .
H15B H 0.859336 0.979096 0.878456 0.089 Uiso 1 1 calc R U . . .
C14 C 1.0040(6) 0.7847(7) 0.9018(4) 0.0710(15) Uani 1 1 d . . . . .
H14A H 1.086699 0.843668 0.959588 0.085 Uiso 1 1 calc R U . . .
H14B H 0.958279 0.721170 0.954450 0.085 Uiso 1 1 calc R U . . .
C4 C 0.6047(5) 0.1263(7) 0.3728(4) 0.0639(13) Uani 1 1 d . . . . .
H4A H 0.683149 0.052098 0.373827 0.096 Uiso 1 1 calc R U . . .
H4B H 0.603664 0.219492 0.316765 0.096 Uiso 1 1 calc R U . . .
H4C H 0.514057 0.066957 0.342001 0.096 Uiso 1 1 calc R U . . .
C17 C 0.8276(4) 0.7055(6) 0.6409(4) 0.0468(10) Uani 1 1 d . . . . .
H17A H 0.746596 0.647354 0.580104 0.056 Uiso 1 1 calc R U . . .
H17B H 0.876939 0.770233 0.591867 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5216(6) 0.2971(7) 0.8819(5) 0.0734(15) Uani 1 1 d . . . . .
H10 H 0.601618 0.368307 0.907790 0.088 Uiso 1 1 calc R U . . .
C7 C 0.2841(6) 0.0907(9) 0.8079(6) 0.0834(17) Uani 1 1 d . . . . .
H7 H 0.202562 0.021753 0.781798 0.100 Uiso 1 1 calc R U . . .
C9 C 0.4319(6) 0.2795(8) 0.9571(5) 0.0854(18) Uani 1 1 d . . . . .
H9 H 0.452652 0.339332 1.034014 0.102 Uiso 1 1 calc R U . . .
C8 C 0.3137(6) 0.1767(8) 0.9216(6) 0.0849(18) Uani 1 1 d . . . . .
H8 H 0.254490 0.165372 0.973678 0.102 Uiso 1 1 calc R U . . .
H3 H 0.877(4) 0.522(5) 0.776(4) 0.043(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
O1 C1 1.274(4) . ?
N1 N2 1.402(4) . ?
N1 C1 1.375(5) . ?
N1 C5 1.414(5) . ?
N3 C13 1.496(5) . ?
N3 C12 1.484(5) . ?
N3 C17 1.495(5) . ?
N3 H3 1.00(4) . ?
O11 C11 1.240(5) . ?
N2 C3 1.308(5) . ?
C2 C3 1.426(5) . ?
C2 C1 1.410(5) . ?
C2 C11 1.427(5) . ?
C3 C4 1.493(5) . ?
C11 C12 1.520(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.500(7) . ?
C5 C6 1.372(6) . ?
C5 C10 1.386(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.379(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.518(6) . ?
C16 C17 1.511(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.510(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C9 1.376(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.361(7) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 118.1(3) . . ?
C1 N1 N2 111.7(3) . . ?
C1 N1 C5 130.2(3) . . ?
C13 N3 H3 106(2) . . ?
C12 N3 C13 111.0(3) . . ?
C12 N3 C17 112.6(3) . . ?
C12 N3 H3 110(2) . . ?
C17 N3 C13 111.0(3) . . ?
C17 N3 H3 107(2) . . ?
C3 N2 N1 105.1(3) . . ?
C3 C2 C11 125.8(4) . . ?
C1 C2 C3 105.1(3) . . ?
C1 C2 C11 129.1(4) . . ?
N2 C3 C2 112.4(3) . . ?
N2 C3 C4 118.6(4) . . ?
C2 C3 C4 128.9(4) . . ?
O1 C1 N1 122.8(3) . . ?
O1 C1 C2 131.6(4) . . ?
N1 C1 C2 105.7(3) . . ?
O11 C11 C2 122.9(4) . . ?
O11 C11 C12 114.3(4) . . ?
C2 C11 C12 122.7(4) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 C14 110.6(3) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C6 C5 N1 119.1(4) . . ?
C6 C5 C10 119.1(4) . . ?
C10 C5 N1 121.8(4) . . ?
N3 C12 C11 115.9(3) . . ?
N3 C12 H12A 108.3 . . ?
N3 C12 H12B 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
H16A C16 H16B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 C15 110.6(4) . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 C16 110.2(4) . . ?
C14 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C13 C14 C15 112.3(4) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C17 C16 110.3(3) . . ?
N3 C17 H17A 109.6 . . ?
N3 C17 H17B 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.5(5) . . ?
C9 C10 H10 120.2 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 H7 119.4 . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.6(5) . . ?
C8 C9 H9 119.2 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.5(5) . . ?
C9 C8 H8 120.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13A O11 0.97 2.56 3.389(5) 142.9 2_756 yes
C12 H12B O11 0.97 2.60 3.429(6) 143.0 2_756 yes
C16 H16B N2 0.97 2.65 3.606(6) 169.3 1_565 yes
C14 H14A O1 0.97 2.48 3.299(5) 142.5 2_757 yes
C17 H17A N2 0.97 2.62 3.476(5) 148.0 2_656 yes
C17 H17B O11 0.97 2.51 3.351(5) 144.6 2_756 yes
C10 H10 O1 0.93 2.26 2.886(5) 123.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C3 C2 -0.2(4) . . . . ?
N1 N2 C3 C4 179.1(4) . . . . ?
N1 C5 C6 C7 -177.5(5) . . . . ?
N1 C5 C10 C9 178.2(5) . . . . ?
N3 C13 C14 C15 -55.3(5) . . . . ?
O11 C11 C12 N3 143.9(4) . . . . ?
N2 N1 C1 O1 179.9(4) . . . . ?
N2 N1 C1 C2 0.4(4) . . . . ?
N2 N1 C5 C6 8.1(6) . . . . ?
N2 N1 C5 C10 -169.9(4) . . . . ?
C2 C11 C12 N3 -36.9(6) . . . . ?
C3 C2 C1 O1 -179.9(4) . . . . ?
C3 C2 C1 N1 -0.5(4) . . . . ?
C3 C2 C11 O11 -3.4(6) . . . . ?
C3 C2 C11 C12 177.5(4) . . . . ?
C1 N1 N2 C3 -0.1(4) . . . . ?
C1 N1 C5 C6 -173.0(4) . . . . ?
C1 N1 C5 C10 9.1(7) . . . . ?
C1 C2 C3 N2 0.5(5) . . . . ?
C1 C2 C3 C4 -178.7(4) . . . . ?
C1 C2 C11 O11 176.3(4) . . . . ?
C1 C2 C11 C12 -2.8(7) . . . . ?
C11 C2 C3 N2 -179.7(4) . . . . ?
C11 C2 C3 C4 1.1(7) . . . . ?
C11 C2 C1 O1 0.3(8) . . . . ?
C11 C2 C1 N1 179.7(4) . . . . ?
C13 N3 C12 C11 173.4(4) . . . . ?
C13 N3 C17 C16 -58.6(4) . . . . ?
C5 N1 N2 C3 179.0(4) . . . . ?
C5 N1 C1 O1 0.9(7) . . . . ?
C5 N1 C1 C2 -178.6(4) . . . . ?
C5 C6 C7 C8 -1.3(9) . . . . ?
C5 C10 C9 C8 -0.2(9) . . . . ?
C12 N3 C13 C14 -176.9(4) . . . . ?
C12 N3 C17 C16 176.2(3) . . . . ?
C6 C5 C10 C9 0.2(8) . . . . ?
C6 C7 C8 C9 1.2(9) . . . . ?
C16 C15 C14 C13 54.5(6) . . . . ?
C15 C16 C17 N3 57.8(5) . . . . ?
C17 N3 C13 C14 57.0(4) . . . . ?
C17 N3 C12 C11 -61.4(5) . . . . ?
C17 C16 C15 C14 -55.3(6) . . . . ?
C10 C5 C6 C7 0.5(7) . . . . ?
C10 C9 C8 C7 -0.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0168_0m
_database_code_depnum_ccdc_archive 'CCDC 2119870'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N3 O2'
_chemical_formula_sum            'C18 H23 N3 O2'
_chemical_formula_weight         313.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7130(5)
_cell_length_b                   18.2866(15)
_cell_length_c                   13.4679(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.780(3)
_cell_angle_gamma                90
_cell_volume                     1651.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    290
_cell_measurement_theta_max      32.483
_cell_measurement_theta_min      2.693
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0979 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.9147.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51749
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.694
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2781
_reflns_number_total             3619
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0906P)²+0.9456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1973
_refine_ls_wR_factor_ref         0.2115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H14C)=Sof(H14D)=Sof(H17C)=Sof(H17D)=Sof(C15B)=Sof(H15C)=Sof(H15D)=
 Sof(C16B)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(H17A)=Sof(H17B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C18(H18A,H18B), C14(H14C,H14D), C14(H14A,
 H14B), C17(H17A,H17B), C17(H17C,H17D), C15A(H15A,H15B), C16A(H16A,H16B),
 C15B(H15C,H15D), C16B(H16C,H16D)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C6(H6), C8(H8), C7(H7)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8123(3) 0.32465(10) 0.60353(13) 0.0592(5) Uani 1 1 d . . . . .
N1 N 0.5115(3) 0.27954(11) 0.53813(14) 0.0475(5) Uani 1 1 d . . . . .
N3 N 1.0084(3) 0.27870(12) 0.75999(15) 0.0524(5) Uani 1 1 d . . . . .
N2 N 0.3952(3) 0.21645(12) 0.54085(16) 0.0546(5) Uani 1 1 d . . . . .
O11 O 0.8269(4) 0.09969(11) 0.71620(19) 0.0837(7) Uani 1 1 d . . . . .
C2 C 0.6868(4) 0.20083(13) 0.63146(17) 0.0490(6) Uani 1 1 d . . . . .
C1 C 0.6878(3) 0.27269(13) 0.59274(16) 0.0456(5) Uani 1 1 d . . . . .
C5 C 0.4341(3) 0.34271(13) 0.48836(16) 0.0450(5) Uani 1 1 d . . . . .
C10 C 0.5601(4) 0.38678(14) 0.43654(18) 0.0551(6) Uani 1 1 d . . . . .
H10 H 0.694000 0.374647 0.432584 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5018(4) 0.17009(14) 0.59594(18) 0.0532(6) Uani 1 1 d . . . . .
C11 C 0.8386(4) 0.16379(15) 0.69189(19) 0.0558(6) Uani 1 1 d . . . . .
C9 C 0.4845(5) 0.44905(17) 0.3907(2) 0.0702(8) Uani 1 1 d . . . . .
H9 H 0.568395 0.479097 0.355884 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2350(4) 0.36033(15) 0.49284(19) 0.0559(6) Uani 1 1 d . . . . .
H6 H 0.150174 0.330230 0.527077 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0315(4) 0.20308(16) 0.7235(2) 0.0607(7) Uani 1 1 d . . . . .
H12A H 1.099937 0.174638 0.775466 0.073 Uiso 1 1 calc R U . . .
H12B H 1.116315 0.204211 0.667209 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2869(5) 0.46711(18) 0.3960(2) 0.0765(9) Uani 1 1 d . . . . .
H8 H 0.237452 0.509422 0.365480 0.092 Uiso 1 1 calc R U . . .
C13 C 0.8826(5) 0.28042(17) 0.8496(2) 0.0705(8) Uani 1 1 d . . . . .
H13A H 0.782988 0.242070 0.843094 0.085 Uiso 1 1 calc R U . . .
H13B H 0.966893 0.269976 0.908446 0.085 Uiso 1 1 calc R U . . .
C4 C 0.4245(5) 0.09477(16) 0.6131(3) 0.0753(9) Uani 1 1 d . . . . .
H4A H 0.289621 0.091187 0.586344 0.113 Uiso 1 1 calc R U . . .
H4B H 0.427933 0.084883 0.683145 0.113 Uiso 1 1 calc R U . . .
H4C H 0.506122 0.059820 0.580749 0.113 Uiso 1 1 calc R U . . .
C18 C 1.2062(4) 0.3146(2) 0.7773(2) 0.0779(9) Uani 1 1 d . . . . .
H18A H 1.287774 0.303959 0.721595 0.094 Uiso 1 1 calc R U . . .
H18B H 1.272098 0.293767 0.836421 0.094 Uiso 1 1 calc R U . . .
C7 C 0.1624(5) 0.42224(18) 0.4467(2) 0.0727(8) Uani 1 1 d . . . . .
H7 H 0.028048 0.434048 0.449749 0.087 Uiso 1 1 calc R U . . .
C14 C 0.7809(6) 0.3511(3) 0.8636(3) 0.1004(13) Uani 1 1 d . . . . .
H14C H 0.660706 0.343955 0.899620 0.120 Uiso 0.427(17) 1 calc R U P A 2
H14D H 0.744281 0.372997 0.799714 0.120 Uiso 0.427(17) 1 calc R U P A 2
H14A H 0.678004 0.354315 0.810667 0.120 Uiso 0.573(17) 1 calc R U P A 1
H14B H 0.712127 0.346589 0.925021 0.120 Uiso 0.573(17) 1 calc R U P A 1
C17 C 1.1943(9) 0.3963(3) 0.7899(4) 0.1251(18) Uani 1 1 d . . . . .
H17A H 1.328936 0.414978 0.786143 0.150 Uiso 0.573(17) 1 calc R U P A 1
H17B H 1.118523 0.415038 0.732313 0.150 Uiso 0.573(17) 1 calc R U P A 1
H17C H 1.293584 0.408623 0.841967 0.150 Uiso 0.427(17) 1 calc R U P A 2
H17D H 1.240964 0.417169 0.729082 0.150 Uiso 0.427(17) 1 calc R U P A 2
C15A C 0.8724(18) 0.4175(4) 0.8673(11) 0.106(3) Uani 0.573(17) 1 d . . P A 1
H15A H 0.817658 0.443472 0.922615 0.127 Uiso 0.573(17) 1 calc R U P A 1
H15B H 0.826306 0.443299 0.807604 0.127 Uiso 0.573(17) 1 calc R U P A 1
C16A C 1.111(2) 0.4297(6) 0.8775(8) 0.123(4) Uani 0.573(17) 1 d . . P A 1
H16A H 1.141620 0.481507 0.880124 0.148 Uiso 0.573(17) 1 calc R U P A 1
H16B H 1.165786 0.406822 0.937725 0.148 Uiso 0.573(17) 1 calc R U P A 1
C15B C 0.942(2) 0.4054(9) 0.9287(13) 0.108(5) Uani 0.427(17) 1 d . . P A 2
H15C H 1.036619 0.379206 0.972042 0.129 Uiso 0.427(17) 1 calc R U P A 2
H15D H 0.878717 0.444867 0.963626 0.129 Uiso 0.427(17) 1 calc R U P A 2
C16B C 1.038(2) 0.4320(6) 0.809(2) 0.138(9) Uani 0.427(17) 1 d . . P A 2
H16C H 0.936287 0.423733 0.757127 0.166 Uiso 0.427(17) 1 calc R U P A 2
H16D H 1.068972 0.483825 0.810755 0.166 Uiso 0.427(17) 1 calc R U P A 2
H3 H 0.935(5) 0.3043(17) 0.705(3) 0.080(9) 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 C1 1.269(3) . ?
N1 N2 1.395(3) . ?
N1 C1 1.368(3) . ?
N1 C5 1.421(3) . ?
N3 C12 1.478(4) . ?
N3 C13 1.507(3) . ?
N3 C18 1.490(3) . ?
N3 H3 0.99(3) . ?
N2 C3 1.315(3) . ?
O11 C11 1.221(3) . ?
C2 C1 1.414(3) . ?
C2 C3 1.425(3) . ?
C2 C11 1.442(3) . ?
C5 C10 1.382(3) . ?
C5 C6 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.380(4) . ?
C3 C4 1.494(4) . ?
C11 C12 1.523(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.372(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C7 1.377(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.478(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.505(6) . ?
C7 H7 0.9300 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15A 1.361(10) . ?
C14 C15B 1.681(14) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C17 C16A 1.464(12) . ?
C17 C16B 1.273(16) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A C16A 1.61(2) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C16B 1.83(3) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 119.48(19) . . ?
C1 N1 N2 112.39(19) . . ?
C1 N1 C5 127.9(2) . . ?
C12 N3 C13 111.0(2) . . ?
C12 N3 C18 110.9(2) . . ?
C12 N3 H3 104.3(19) . . ?
C13 N3 H3 108.4(19) . . ?
C18 N3 C13 113.3(2) . . ?
C18 N3 H3 108.4(19) . . ?
C3 N2 N1 104.9(2) . . ?
C1 C2 C3 105.2(2) . . ?
C1 C2 C11 129.0(2) . . ?
C3 C2 C11 125.8(2) . . ?
O1 C1 N1 122.7(2) . . ?
O1 C1 C2 131.9(2) . . ?
N1 C1 C2 105.31(19) . . ?
C10 C5 N1 119.6(2) . . ?
C6 C5 N1 120.2(2) . . ?
C6 C5 C10 120.3(2) . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.1(3) . . ?
C9 C10 H10 120.4 . . ?
N2 C3 C2 112.1(2) . . ?
N2 C3 C4 119.9(2) . . ?
C2 C3 C4 128.0(3) . . ?
O11 C11 C2 123.3(3) . . ?
O11 C11 C12 116.3(2) . . ?
C2 C11 C12 120.3(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
N3 C12 C11 115.6(2) . . ?
N3 C12 H12A 108.4 . . ?
N3 C12 H12B 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C9 C8 H8 120.2 . . ?
C9 C8 C7 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
N3 C13 H13A 108.8 . . ?
N3 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 N3 113.6(3) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C18 H18A 108.8 . . ?
N3 C18 H18B 108.8 . . ?
N3 C18 C17 113.8(3) . . ?
H18A C18 H18B 107.7 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C13 C14 H14C 110.3 . . ?
C13 C14 H14D 110.3 . . ?
C13 C14 H14A 106.1 . . ?
C13 C14 H14B 106.1 . . ?
C13 C14 C15B 107.1(7) . . ?
H14C C14 H14D 108.6 . . ?
H14A C14 H14B 106.3 . . ?
C15A C14 C13 125.1(5) . . ?
C15A C14 H14A 106.1 . . ?
C15A C14 H14B 106.1 . . ?
C15B C14 H14C 110.3 . . ?
C15B C14 H14D 110.3 . . ?
C18 C17 H17A 106.8 . . ?
C18 C17 H17B 106.8 . . ?
C18 C17 H17C 105.9 . . ?
C18 C17 H17D 105.9 . . ?
H17A C17 H17B 106.7 . . ?
H17C C17 H17D 106.3 . . ?
C16A C17 C18 122.0(6) . . ?
C16A C17 H17A 106.8 . . ?
C16A C17 H17B 106.8 . . ?
C16B C17 C18 125.5(6) . . ?
C16B C17 H17C 105.9 . . ?
C16B C17 H17D 105.9 . . ?
C14 C15A H15A 106.1 . . ?
C14 C15A H15B 106.1 . . ?
C14 C15A C16A 124.7(8) . . ?
H15A C15A H15B 106.3 . . ?
C16A C15A H15A 106.1 . . ?
C16A C15A H15B 106.1 . . ?
C17 C16A C15A 106.9(9) . . ?
C17 C16A H16A 110.3 . . ?
C17 C16A H16B 110.3 . . ?
C15A C16A H16A 110.3 . . ?
C15A C16A H16B 110.3 . . ?
H16A C16A H16B 108.6 . . ?
C14 C15B H15C 114.2 . . ?
C14 C15B H15D 114.2 . . ?
C14 C15B C16B 86.9(11) . . ?
H15C C15B H15D 111.3 . . ?
C16B C15B H15C 114.2 . . ?
C16B C15B H15D 114.2 . . ?
C17 C16B C15B 112.1(15) . . ?
C17 C16B H16C 109.2 . . ?
C17 C16B H16D 109.2 . . ?
C15B C16B H16C 109.2 . . ?
C15B C16B H16D 109.2 . . ?
H16C C16B H16D 107.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O1 0.93 2.54 3.333(3) 143.6 1_455 yes
C12 H12B N2 0.97 2.60 3.557(4) 169.1 1_655 yes
N3 H3 O1 0.99(3) 1.60(4) 2.571(3) 165(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C3 C2 0.7(3) . . . . ?
N1 N2 C3 C4 -178.4(2) . . . . ?
N1 C5 C10 C9 -178.3(2) . . . . ?
N1 C5 C6 C7 178.4(2) . . . . ?
N3 C13 C14 C15A -53.0(9) . . . . ?
N3 C13 C14 C15B -86.2(7) . . . . ?
N3 C18 C17 C16A 69.1(10) . . . . ?
N3 C18 C17 C16B 17.0(17) . . . . ?
N2 N1 C1 O1 -177.1(2) . . . . ?
N2 N1 C1 C2 1.0(2) . . . . ?
N2 N1 C5 C10 -143.7(2) . . . . ?
N2 N1 C5 C6 37.1(3) . . . . ?
O11 C11 C12 N3 -138.8(3) . . . . ?
C2 C11 C12 N3 44.8(3) . . . . ?
C1 N1 N2 C3 -1.1(3) . . . . ?
C1 N1 C5 C10 41.6(3) . . . . ?
C1 N1 C5 C6 -137.6(2) . . . . ?
C1 C2 C3 N2 -0.1(3) . . . . ?
C1 C2 C3 C4 178.9(3) . . . . ?
C1 C2 C11 O11 -175.3(3) . . . . ?
C1 C2 C11 C12 0.8(4) . . . . ?
C5 N1 N2 C3 -176.6(2) . . . . ?
C5 N1 C1 O1 -2.1(4) . . . . ?
C5 N1 C1 C2 176.1(2) . . . . ?
C5 C10 C9 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C10 C5 C6 C7 -0.8(4) . . . . ?
C10 C9 C8 C7 -0.6(5) . . . . ?
C3 C2 C1 O1 177.4(2) . . . . ?
C3 C2 C1 N1 -0.6(2) . . . . ?
C3 C2 C11 O11 3.0(4) . . . . ?
C3 C2 C11 C12 179.1(2) . . . . ?
C11 C2 C1 O1 -4.1(4) . . . . ?
C11 C2 C1 N1 178.0(2) . . . . ?
C11 C2 C3 N2 -178.7(2) . . . . ?
C11 C2 C3 C4 0.3(4) . . . . ?
C9 C8 C7 C6 0.8(5) . . . . ?
C6 C5 C10 C9 0.9(4) . . . . ?
C12 N3 C13 C14 -154.7(3) . . . . ?
C12 N3 C18 C17 165.7(3) . . . . ?
C13 N3 C12 C11 59.8(3) . . . . ?
C13 N3 C18 C17 -68.7(4) . . . . ?
C13 C14 C15A C16A -11.9(17) . . . . ?
C13 C14 C15B C16B 87.1(9) . . . . ?
C18 N3 C12 C11 -173.3(2) . . . . ?
C18 N3 C13 C14 79.7(4) . . . . ?
C18 C17 C16A C15A -72.6(13) . . . . ?
C18 C17 C16B C15B 61(2) . . . . ?
C14 C15A C16A C17 61.2(17) . . . . ?
C14 C15B C16B C17 -97.7(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0147_0m
_database_code_depnum_ccdc_archive 'CCDC 2119864'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 Cs N3 O5'
_chemical_formula_sum            'C20 H26 Cs N3 O5'
_chemical_formula_weight         521.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1311(3)
_cell_length_b                   18.2830(6)
_cell_length_c                   14.9298(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.0150(10)
_cell_angle_gamma                90
_cell_volume                     2178.59(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.619
_cell_measurement_theta_min      2.626
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.624
_exptl_absorpt_coefficient_mu    1.735
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8765.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            68060
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.648
_diffrn_reflns_theta_min         2.228
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4456
_reflns_number_total             5020
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+3.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B), C13(H13A,H13B), C14(H14A,H14B), C18(H18A,
 H18B), C19(H19A,H19B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs -0.05496(3) 0.60777(2) 0.51530(2) 0.05787(9) Uani 1 1 d . . . . .
O11 O 0.1896(3) 0.53239(14) 0.41808(19) 0.0667(7) Uani 1 1 d . . . . .
O2 O -0.0053(3) 0.74570(15) 0.41111(19) 0.0686(7) Uani 1 1 d . . . . .
O1 O 0.6641(4) 0.61342(18) 0.3586(2) 0.0759(8) Uani 1 1 d . . . . .
O3 O -0.1463(4) 0.76463(16) 0.5712(2) 0.0789(8) Uani 1 1 d . . . . .
N3 N 0.3066(3) 0.67340(15) 0.49640(19) 0.0513(6) Uani 1 1 d . . . . .
O4 O 0.1566(4) 0.69805(17) 0.66278(18) 0.0790(8) Uani 1 1 d . . . . .
N2 N 0.4628(4) 0.47761(17) 0.2135(2) 0.0621(8) Uani 1 1 d . . . . .
N1 N 0.5920(4) 0.52664(17) 0.2447(2) 0.0586(7) Uani 1 1 d . . . . .
C2 C 0.4136(4) 0.53613(17) 0.3406(2) 0.0478(7) Uani 1 1 d . . . . .
C11 C 0.3292(4) 0.55741(17) 0.4116(2) 0.0497(7) Uani 1 1 d . . . . .
C3 C 0.3609(5) 0.48304(18) 0.2712(2) 0.0549(8) Uani 1 1 d . . . . .
C1 C 0.5681(4) 0.5650(2) 0.3221(2) 0.0542(8) Uani 1 1 d . . . . .
C12 C 0.4128(4) 0.6104(2) 0.4840(3) 0.0613(9) Uani 1 1 d . . . . .
H12A H 0.442801 0.584512 0.541531 0.074 Uiso 1 1 calc R U . . .
H12B H 0.515494 0.628105 0.467528 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7117(5) 0.5400(2) 0.1893(3) 0.0597(9) Uani 1 1 d . . . . .
C20 C 0.3828(5) 0.7147(3) 0.5771(3) 0.0799(13) Uani 1 1 d . . . . .
H20A H 0.352295 0.765799 0.567780 0.096 Uiso 1 1 calc R U . . .
H20B H 0.503723 0.711247 0.584629 0.096 Uiso 1 1 calc R U . . .
C13 C 0.2768(6) 0.7197(2) 0.4127(3) 0.0722(11) Uani 1 1 d . . . . .
H13A H 0.381754 0.742826 0.407098 0.087 Uiso 1 1 calc R U . . .
H13B H 0.244092 0.688088 0.360151 0.087 Uiso 1 1 calc R U . . .
C6 C 0.6756(6) 0.5191(2) 0.0992(3) 0.0690(10) Uani 1 1 d . . . . .
H6 H 0.576647 0.494121 0.076580 0.083 Uiso 1 1 calc R U . . .
C8 C 0.9328(6) 0.5705(3) 0.0749(4) 0.0854(14) Uani 1 1 d . . . . .
H8 H 1.006418 0.581676 0.036247 0.103 Uiso 1 1 calc R U . . .
C7 C 0.7868(7) 0.5352(2) 0.0418(3) 0.0820(13) Uani 1 1 d . . . . .
H7 H 0.761191 0.521745 -0.019400 0.098 Uiso 1 1 calc R U . . .
C14 C 0.1474(6) 0.7776(2) 0.4095(3) 0.0824(13) Uani 1 1 d . . . . .
H14A H 0.177899 0.810077 0.461433 0.099 Uiso 1 1 calc R U . . .
H14B H 0.140542 0.806360 0.354270 0.099 Uiso 1 1 calc R U . . .
C18 C 0.1133(8) 0.7678(3) 0.6849(4) 0.1016(17) Uani 1 1 d . . . . .
H18A H 0.162925 0.803251 0.649620 0.122 Uiso 1 1 calc R U . . .
H18B H 0.156691 0.777012 0.749092 0.122 Uiso 1 1 calc R U . . .
C10 C 0.8615(5) 0.5740(3) 0.2232(3) 0.0804(12) Uani 1 1 d . . . . .
H10 H 0.889066 0.586640 0.284627 0.096 Uiso 1 1 calc R U . . .
C19 C 0.3322(7) 0.6891(3) 0.6602(3) 0.0968(16) Uani 1 1 d . . . . .
H19A H 0.360112 0.637614 0.668016 0.116 Uiso 1 1 calc R U . . .
H19B H 0.397370 0.715097 0.711623 0.116 Uiso 1 1 calc R U . . .
C9 C 0.9713(6) 0.5895(3) 0.1650(4) 0.0912(15) Uani 1 1 d . . . . .
H9 H 1.072098 0.613039 0.187515 0.109 Uiso 1 1 calc R U . . .
C17 C -0.0672(7) 0.7763(3) 0.6663(4) 0.0992(18) Uani 1 1 d . . . . .
H17A H -0.094148 0.825254 0.683974 0.119 Uiso 1 1 calc R U . . .
H17B H -0.114591 0.742035 0.703952 0.119 Uiso 1 1 calc R U . . .
C16 C -0.1306(8) 0.8231(3) 0.5140(5) 0.114(2) Uani 1 1 d . . . . .
H16A H -0.025782 0.848362 0.536091 0.137 Uiso 1 1 calc R U . . .
H16B H -0.221479 0.857441 0.514357 0.137 Uiso 1 1 calc R U . . .
C15 C -0.1346(9) 0.7977(3) 0.4228(4) 0.1107(19) Uani 1 1 d . . . . .
H15A H -0.126060 0.839756 0.384349 0.133 Uiso 1 1 calc R U . . .
H15B H -0.242845 0.775200 0.400768 0.133 Uiso 1 1 calc R U . . .
C4 C 0.2121(6) 0.4337(2) 0.2587(3) 0.0770(12) Uani 1 1 d . . . . .
H4A H 0.196066 0.411624 0.199300 0.116 Uiso 1 1 calc R U . . .
H4B H 0.114395 0.461466 0.264245 0.116 Uiso 1 1 calc R U . . .
H4C H 0.230120 0.396126 0.304500 0.116 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
Cs1 Cs1 4.0857(4) 3_566 ?
Cs1 O11 3.011(2) . ?
Cs1 O11 3.028(2) 3_566 ?
Cs1 O2 3.030(3) . ?
Cs1 O1 2.943(3) 1_455 ?
Cs1 O3 3.116(3) . ?
Cs1 N3 3.237(3) . ?
Cs1 O4 3.014(3) . ?
Cs1 C1 3.867(4) 1_455 ?
Cs1 H12B 3.449(4) 1_455 ?
Cs1 C4 3.904(4) 3_566 ?
O11 C11 1.245(4) . ?
O2 C14 1.377(5) . ?
O2 C15 1.452(6) . ?
O1 C1 1.236(4) . ?
O3 C17 1.458(6) . ?
O3 C16 1.389(6) . ?
N3 C12 1.473(4) . ?
N3 C20 1.455(5) . ?
N3 C13 1.490(5) . ?
O4 C18 1.381(6) . ?
O4 C19 1.445(6) . ?
N2 N1 1.392(4) . ?
N2 C3 1.308(4) . ?
N1 C1 1.396(4) . ?
N1 C5 1.414(4) . ?
C2 C11 1.422(4) . ?
C2 C3 1.424(5) . ?
C2 C1 1.437(5) . ?
C11 C12 1.512(5) . ?
C3 C4 1.493(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C6 1.376(6) . ?
C5 C10 1.376(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.457(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.487(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.358(7) . ?
C8 C9 1.367(8) . ?
C7 H7 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.449(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.389(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C9 H9 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.434(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cs1 Cs1 H12B 108.38(7) 3_566 1_455 ?
O11 Cs1 Cs1 47.61(5) . 3_566 ?
O11 Cs1 Cs1 47.25(4) 3_566 3_566 ?
O11 Cs1 O11 94.86(6) . 3_566 ?
O11 Cs1 O2 88.19(7) . . ?
O11 Cs1 O2 164.75(8) 3_566 . ?
O11 Cs1 O3 139.78(7) . . ?
O11 Cs1 O3 124.83(7) 3_566 . ?
O11 Cs1 N3 137.20(8) 3_566 . ?
O11 Cs1 N3 55.46(7) . . ?
O11 Cs1 O4 105.39(8) . . ?
O11 Cs1 C1 92.88(7) . 1_455 ?
O11 Cs1 C1 77.82(8) 3_566 1_455 ?
O11 Cs1 H12B 75.15(9) 3_566 1_455 ?
O11 Cs1 H12B 133.30(8) . 1_455 ?
O11 Cs1 C4 133.11(9) . 3_566 ?
O11 Cs1 C4 49.71(7) 3_566 3_566 ?
O2 Cs1 Cs1 133.78(6) . 3_566 ?
O2 Cs1 O3 55.49(8) . . ?
O2 Cs1 N3 55.56(7) . . ?
O2 Cs1 C1 87.12(7) . 1_455 ?
O2 Cs1 H12B 91.90(9) . 1_455 ?
O2 Cs1 C4 134.66(8) . 3_566 ?
O1 Cs1 Cs1 95.64(6) 1_455 3_566 ?
O1 Cs1 O11 90.93(8) 1_455 3_566 ?
O1 Cs1 O11 96.71(8) 1_455 . ?
O1 Cs1 O2 73.86(8) 1_455 . ?
O1 Cs1 O3 89.54(9) 1_455 . ?
O1 Cs1 N3 119.85(7) 1_455 . ?
O1 Cs1 O4 144.05(9) 1_455 . ?
O1 Cs1 C1 13.99(8) 1_455 1_455 ?
O1 Cs1 H12B 39.65(8) 1_455 1_455 ?
O1 Cs1 C4 111.18(9) 1_455 3_566 ?
O3 Cs1 Cs1 170.43(6) . 3_566 ?
O3 Cs1 N3 87.08(7) . . ?
O3 Cs1 C1 100.98(8) . 1_455 ?
O3 Cs1 H12B 70.88(8) . 1_455 ?
O3 Cs1 C4 79.23(9) . 3_566 ?
N3 Cs1 Cs1 97.24(5) . 3_566 ?
N3 Cs1 C1 127.85(7) . 1_455 ?
N3 Cs1 H12B 147.43(9) . 1_455 ?
N3 Cs1 C4 126.86(8) . 3_566 ?
O4 Cs1 Cs1 120.22(6) . 3_566 ?
O4 Cs1 O11 114.53(8) . 3_566 ?
O4 Cs1 O2 78.80(8) . . ?
O4 Cs1 O3 55.42(9) . . ?
O4 Cs1 N3 57.28(8) . . ?
O4 Cs1 C1 156.39(8) . 1_455 ?
O4 Cs1 H12B 120.41(9) . 1_455 ?
O4 Cs1 C4 73.16(8) . 3_566 ?
C1 Cs1 Cs1 83.14(5) 1_455 3_566 ?
C1 Cs1 H12B 40.57(8) 1_455 1_455 ?
C1 Cs1 C4 105.19(9) 1_455 3_566 ?
C4 Cs1 Cs1 91.39(6) 3_566 3_566 ?
C4 Cs1 H12B 73.37(10) 3_566 1_455 ?
Cs1 O11 Cs1 85.14(6) . 3_566 ?
C11 O11 Cs1 136.8(2) . 3_566 ?
C11 O11 Cs1 124.5(2) . . ?
C14 O2 Cs1 124.8(2) . . ?
C14 O2 C15 113.6(4) . . ?
C15 O2 Cs1 108.2(3) . . ?
C1 O1 Cs1 130.9(3) . 1_655 ?
C17 O3 Cs1 108.2(3) . . ?
C16 O3 Cs1 119.3(3) . . ?
C16 O3 C17 114.2(4) . . ?
C12 N3 Cs1 106.6(2) . . ?
C12 N3 C13 110.1(3) . . ?
C20 N3 Cs1 111.7(2) . . ?
C20 N3 C12 110.0(3) . . ?
C20 N3 C13 112.0(3) . . ?
C13 N3 Cs1 106.2(2) . . ?
C18 O4 Cs1 123.0(3) . . ?
C18 O4 C19 114.2(4) . . ?
C19 O4 Cs1 110.3(2) . . ?
C3 N2 N1 105.2(3) . . ?
N2 N1 C1 112.7(3) . . ?
N2 N1 C5 118.4(3) . . ?
C1 N1 C5 128.1(3) . . ?
C11 C2 C3 127.4(3) . . ?
C11 C2 C1 127.4(3) . . ?
C3 C2 C1 105.2(3) . . ?
O11 C11 C2 122.3(3) . . ?
O11 C11 C12 118.1(3) . . ?
C2 C11 C12 119.5(3) . . ?
N2 C3 C2 113.0(3) . . ?
N2 C3 C4 118.1(3) . . ?
C2 C3 C4 128.8(3) . . ?
O1 C1 Cs1 35.12(19) . 1_655 ?
O1 C1 N1 123.3(3) . . ?
O1 C1 C2 132.8(3) . . ?
N1 C1 Cs1 120.2(2) . 1_655 ?
N1 C1 C2 103.9(3) . . ?
C2 C1 Cs1 121.9(2) . 1_655 ?
N3 C12 C11 113.4(3) . . ?
N3 C12 H12A 108.9 . . ?
N3 C12 H12B 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C6 C5 N1 118.8(4) . . ?
C10 C5 N1 121.6(4) . . ?
C10 C5 C6 119.6(4) . . ?
N3 C20 H20A 108.9 . . ?
N3 C20 H20B 108.9 . . ?
N3 C20 C19 113.2(4) . . ?
H20A C20 H20B 107.8 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
N3 C13 H13A 108.4 . . ?
N3 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 N3 115.6(3) . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.1(4) . . ?
C7 C6 H6 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
O2 C14 C13 109.4(3) . . ?
O2 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
O4 C18 H18A 109.6 . . ?
O4 C18 H18B 109.6 . . ?
O4 C18 C17 110.4(5) . . ?
H18A C18 H18B 108.1 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C5 C10 H10 120.3 . . ?
C5 C10 C9 119.4(5) . . ?
C9 C10 H10 120.3 . . ?
O4 C19 C20 115.3(4) . . ?
O4 C19 H19A 108.4 . . ?
O4 C19 H19B 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O3 C17 H17A 108.6 . . ?
O3 C17 H17B 108.6 . . ?
C18 C17 O3 114.5(4) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O3 C16 H16A 109.6 . . ?
O3 C16 H16B 109.6 . . ?
O3 C16 C15 110.2(5) . . ?
H16A C16 H16B 108.1 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
O2 C15 H15A 108.3 . . ?
O2 C15 H15B 108.2 . . ?
C16 C15 O2 116.1(5) . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
Cs1 C4 H4A 135.1 3_566 . ?
Cs1 C4 H4B 67.4 3_566 . ?
Cs1 C4 H4C 43.6 3_566 . ?
C3 C4 Cs1 113.6(3) . 3_566 ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12B O1 0.97 2.22 3.023(5) 139.5 . yes
C18 H18B O1 0.97 2.58 3.347(5) 136.1 4_576 yes
C10 H10 O1 0.93 2.36 2.902(5) 116.7 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cs1 O11 C11 C2 -156.5(2) . . . . ?
Cs1 O11 C11 C2 78.0(4) 3_566 . . . ?
Cs1 O11 C11 C12 -100.0(3) 3_566 . . . ?
Cs1 O11 C11 C12 25.5(4) . . . . ?
Cs1 O2 C14 C13 34.7(5) . . . . ?
Cs1 O2 C15 C16 63.9(6) . . . . ?
Cs1 O1 C1 N1 -96.4(4) 1_655 . . . ?
Cs1 O1 C1 C2 86.3(5) 1_655 . . . ?
Cs1 O3 C17 C18 57.8(5) . . . . ?
Cs1 O3 C16 C15 21.9(7) . . . . ?
Cs1 N3 C12 C11 48.8(3) . . . . ?
Cs1 N3 C20 C19 28.9(5) . . . . ?
Cs1 N3 C13 C14 54.5(4) . . . . ?
Cs1 O4 C18 C17 29.0(6) . . . . ?
Cs1 O4 C19 C20 63.3(5) . . . . ?
O11 C11 C12 N3 -54.1(4) . . . . ?
O3 C16 C15 O2 -59.4(8) . . . . ?
N3 C20 C19 O4 -64.8(6) . . . . ?
N3 C13 C14 O2 -62.2(5) . . . . ?
O4 C18 C17 O3 -59.9(7) . . . . ?
N2 N1 C1 Cs1 141.8(2) . . . 1_655 ?
N2 N1 C1 O1 -176.8(3) . . . . ?
N2 N1 C1 C2 1.1(4) . . . . ?
N2 N1 C5 C6 15.7(5) . . . . ?
N2 N1 C5 C10 -165.2(4) . . . . ?
N2 C3 C4 Cs1 152.8(3) . . . 3_566 ?
N1 N2 C3 C2 1.6(4) . . . . ?
N1 N2 C3 C4 -176.9(3) . . . . ?
N1 C5 C6 C7 176.4(4) . . . . ?
N1 C5 C10 C9 -176.5(4) . . . . ?
C2 C11 C12 N3 127.9(3) . . . . ?
C2 C3 C4 Cs1 -25.4(5) . . . 3_566 ?
C11 C2 C3 N2 177.6(3) . . . . ?
C11 C2 C3 C4 -4.1(6) . . . . ?
C11 C2 C1 Cs1 41.5(4) . . . 1_655 ?
C11 C2 C1 O1 -1.0(6) . . . . ?
C11 C2 C1 N1 -178.7(3) . . . . ?
C3 N2 N1 C1 -1.7(4) . . . . ?
C3 N2 N1 C5 -172.1(3) . . . . ?
C3 C2 C11 O11 -3.2(5) . . . . ?
C3 C2 C11 C12 174.7(3) . . . . ?
C3 C2 C1 Cs1 -139.9(2) . . . 1_655 ?
C3 C2 C1 O1 177.6(4) . . . . ?
C3 C2 C1 N1 -0.1(3) . . . . ?
C1 N1 C5 C6 -152.9(4) . . . . ?
C1 N1 C5 C10 26.2(6) . . . . ?
C1 C2 C11 O11 175.0(3) . . . . ?
C1 C2 C11 C12 -7.1(5) . . . . ?
C1 C2 C3 N2 -1.0(4) . . . . ?
C1 C2 C3 C4 177.3(4) . . . . ?
C12 N3 C20 C19 -89.3(4) . . . . ?
C12 N3 C13 C14 169.5(4) . . . . ?
C5 N1 C1 Cs1 -49.1(4) . . . 1_655 ?
C5 N1 C1 O1 -7.6(6) . . . . ?
C5 N1 C1 C2 170.3(3) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C5 C10 C9 C8 -0.7(7) . . . . ?
C20 N3 C12 C11 170.1(3) . . . . ?
C20 N3 C13 C14 -67.7(5) . . . . ?
C13 N3 C12 C11 -66.0(4) . . . . ?
C13 N3 C20 C19 147.9(4) . . . . ?
C6 C5 C10 C9 2.6(7) . . . . ?
C7 C8 C9 C10 -0.9(8) . . . . ?
C14 O2 C15 C16 -79.2(7) . . . . ?
C18 O4 C19 C20 -80.1(5) . . . . ?
C10 C5 C6 C7 -2.8(6) . . . . ?
C19 O4 C18 C17 167.3(4) . . . . ?
C9 C8 C7 C6 0.7(7) . . . . ?
C17 O3 C16 C15 152.1(5) . . . . ?
C16 O3 C17 C18 -77.6(6) . . . . ?
C15 O2 C14 C13 170.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0130_0m
_database_code_depnum_ccdc_archive 'CCDC 2119859'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.3849(4)
_cell_length_b                   9.9562(4)
_cell_length_c                   13.2945(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.3400(10)
_cell_angle_gamma                90
_cell_volume                     1477.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.112
_cell_measurement_theta_min      2.741
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.8292.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25571
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.167
_diffrn_reflns_theta_min         2.741
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2508
_reflns_number_total             2916
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0582P)²+0.5756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1294
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C6(H6), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58676(9) 0.25126(10) 0.63262(9) 0.0381(3) Uani 1 1 d . . . . .
O11 O 0.64334(10) 0.67644(12) 0.70536(12) 0.0533(4) Uani 1 1 d . . . . .
N1 N 0.39005(11) 0.32911(12) 0.59411(10) 0.0345(3) Uani 1 1 d . . . . .
N2 N 0.32637(11) 0.44855(12) 0.59613(11) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.85740(11) 0.56181(13) 0.71311(10) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.52586(12) 0.48618(15) 0.64714(11) 0.0314(3) Uani 1 1 d . . . . .
C1 C 0.51252(12) 0.34617(15) 0.62547(11) 0.0301(3) Uani 1 1 d . . . . .
C5 C 0.32530(13) 0.20843(15) 0.57136(11) 0.0332(3) Uani 1 1 d . . . . .
C3 C 0.40781(13) 0.53993(15) 0.62658(12) 0.0334(3) Uani 1 1 d . . . . .
C11 C 0.63531(13) 0.55661(15) 0.68223(12) 0.0355(3) Uani 1 1 d . . . . .
C10 C 0.36229(15) 0.11094(16) 0.51046(12) 0.0402(4) Uani 1 1 d . . . . .
H10 H 0.431790 0.123323 0.484711 0.048 Uiso 1 1 calc R U . . .
C12 C 0.74969(13) 0.47457(16) 0.69291(14) 0.0405(4) Uani 1 1 d . . . . .
H12A H 0.753594 0.411046 0.748789 0.049 Uiso 1 1 calc R U . . .
H12B H 0.748455 0.423974 0.630356 0.049 Uiso 1 1 calc R U . . .
C13 C 0.97136(14) 0.48148(17) 0.74403(16) 0.0480(4) Uani 1 1 d . . . . .
H13A H 1.009165 0.501200 0.814415 0.058 Uiso 1 1 calc R U . . .
H13B H 0.954382 0.386021 0.738123 0.058 Uiso 1 1 calc R U . . .
C9 C 0.29558(18) -0.00509(18) 0.48794(15) 0.0513(5) Uani 1 1 d . . . . .
H9 H 0.321002 -0.071416 0.447833 0.062 Uiso 1 1 calc R U . . .
C6 C 0.22105(16) 0.19010(18) 0.60887(15) 0.0487(4) Uani 1 1 d . . . . .
H6 H 0.195859 0.255395 0.649960 0.058 Uiso 1 1 calc R U . . .
C4 C 0.37069(15) 0.68301(16) 0.63121(16) 0.0485(4) Uani 1 1 d . . . . .
H4A H 0.402344 0.734423 0.581531 0.073 Uiso 1 1 calc R U . . .
H4B H 0.400991 0.718081 0.698579 0.073 Uiso 1 1 calc R U . . .
H4C H 0.284842 0.688684 0.616497 0.073 Uiso 1 1 calc R U . . .
C16 C 0.87275(16) 0.6469(2) 0.62335(14) 0.0495(4) Uani 1 1 d . . . . .
H16A H 0.835248 0.605000 0.559176 0.059 Uiso 1 1 calc R U . . .
H16B H 0.838079 0.735267 0.627307 0.059 Uiso 1 1 calc R U . . .
C8 C 0.19174(19) -0.02286(19) 0.52460(19) 0.0636(6) Uani 1 1 d . . . . .
H8 H 0.146642 -0.100592 0.508591 0.076 Uiso 1 1 calc R U . . .
C7 C 0.15480(18) 0.0739(2) 0.5847(2) 0.0670(6) Uani 1 1 d . . . . .
H7 H 0.084643 0.061488 0.609426 0.080 Uiso 1 1 calc R U . . .
C15 C 1.0059(2) 0.6560(3) 0.6320(2) 0.0718(6) Uani 1 1 d . . . . .
H15A H 1.026249 0.672203 0.565489 0.086 Uiso 1 1 calc R U . . .
H15B H 1.039534 0.727355 0.678563 0.086 Uiso 1 1 calc R U . . .
C14 C 1.0502(2) 0.5217(3) 0.6732(2) 0.0886(9) Uani 1 1 d . . . . .
H14A H 1.045361 0.457028 0.617936 0.106 Uiso 1 1 calc R U . . .
H14B H 1.132799 0.527599 0.709350 0.106 Uiso 1 1 calc R U . . .
H3 H 0.8546(18) 0.623(2) 0.7620(16) 0.055(6) 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 C1 1.2589(17) . ?
O11 C11 1.2310(19) . ?
N1 N2 1.3957(17) . ?
N1 C1 1.3850(18) . ?
N1 C5 1.4110(19) . ?
N2 C3 1.3053(19) . ?
N3 C12 1.4835(19) . ?
N3 C13 1.5107(19) . ?
N3 C16 1.501(2) . ?
N3 H3 0.90(2) . ?
C2 C1 1.426(2) . ?
C2 C3 1.422(2) . ?
C2 C11 1.426(2) . ?
C5 C10 1.382(2) . ?
C5 C6 1.387(2) . ?
C3 C4 1.491(2) . ?
C11 C12 1.520(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.383(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.479(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.501(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(3) . ?
C7 H7 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.495(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 118.57(11) . . ?
C1 N1 N2 112.69(12) . . ?
C1 N1 C5 128.42(12) . . ?
C3 N2 N1 105.06(12) . . ?
C12 N3 C13 111.99(12) . . ?
C12 N3 C16 114.06(13) . . ?
C12 N3 H3 112.6(13) . . ?
C13 N3 H3 108.3(13) . . ?
C16 N3 C13 106.68(13) . . ?
C16 N3 H3 102.5(13) . . ?
C1 C2 C11 126.76(13) . . ?
C3 C2 C1 105.67(12) . . ?
C3 C2 C11 127.58(14) . . ?
O1 C1 N1 123.50(13) . . ?
O1 C1 C2 132.49(13) . . ?
N1 C1 C2 103.98(12) . . ?
C10 C5 N1 121.15(14) . . ?
C10 C5 C6 119.95(15) . . ?
C6 C5 N1 118.87(14) . . ?
N2 C3 C2 112.59(13) . . ?
N2 C3 C4 119.28(14) . . ?
C2 C3 C4 128.06(14) . . ?
O11 C11 C2 125.14(14) . . ?
O11 C11 C12 118.51(13) . . ?
C2 C11 C12 116.35(13) . . ?
C5 C10 H10 120.1 . . ?
C5 C10 C9 119.74(16) . . ?
C9 C10 H10 120.1 . . ?
N3 C12 C11 111.40(12) . . ?
N3 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N3 C13 H13A 110.5 . . ?
N3 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 N3 106.25(16) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.29(18) . . ?
C8 C9 H9 119.9 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.50(18) . . ?
C7 C6 H6 120.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C16 H16A 110.9 . . ?
N3 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 N3 104.32(15) . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.99(17) . . ?
C7 C8 H8 120.0 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.52(19) . . ?
C8 C7 H7 119.7 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C14 C15 C16 103.68(19) . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C13 C14 C15 105.81(18) . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12A O11 0.97 2.63 3.3875(19) 135.0 2_646 yes
C13 H13B O11 0.97 2.55 3.424(2) 150.5 2_646 yes
C16 H16A N2 0.97 2.54 3.458(2) 158.3 3_666 yes
N3 H3 O1 0.90(2) 1.91(2) 2.7669(17) 158.0(19) 2_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C11 C12 N3 -10.3(2) . . . . ?
N1 N2 C3 C2 -0.93(17) . . . . ?
N1 N2 C3 C4 176.26(14) . . . . ?
N1 C5 C10 C9 -178.74(14) . . . . ?
N1 C5 C6 C7 178.14(17) . . . . ?
N2 N1 C1 O1 177.75(13) . . . . ?
N2 N1 C1 C2 -0.80(16) . . . . ?
N2 N1 C5 C10 140.71(15) . . . . ?
N2 N1 C5 C6 -37.5(2) . . . . ?
N3 C13 C14 C15 21.5(3) . . . . ?
N3 C16 C15 C14 35.0(2) . . . . ?
C2 C11 C12 N3 170.65(13) . . . . ?
C1 N1 N2 C3 1.09(17) . . . . ?
C1 N1 C5 C10 -46.2(2) . . . . ?
C1 N1 C5 C6 135.57(17) . . . . ?
C1 C2 C3 N2 0.47(17) . . . . ?
C1 C2 C3 C4 -176.42(16) . . . . ?
C1 C2 C11 O11 -176.01(16) . . . . ?
C1 C2 C11 C12 3.0(2) . . . . ?
C5 N1 N2 C3 175.19(13) . . . . ?
C5 N1 C1 O1 4.4(2) . . . . ?
C5 N1 C1 C2 -174.18(14) . . . . ?
C5 C10 C9 C8 1.0(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C3 C2 C1 O1 -178.14(16) . . . . ?
C3 C2 C1 N1 0.21(15) . . . . ?
C3 C2 C11 O11 3.9(3) . . . . ?
C3 C2 C11 C12 -177.11(15) . . . . ?
C11 C2 C1 O1 1.8(3) . . . . ?
C11 C2 C1 N1 -179.85(14) . . . . ?
C11 C2 C3 N2 -179.47(15) . . . . ?
C11 C2 C3 C4 3.6(3) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C10 C9 C8 C7 -0.8(3) . . . . ?
C12 N3 C13 C14 125.92(19) . . . . ?
C12 N3 C16 C15 -146.21(16) . . . . ?
C13 N3 C12 C11 168.99(14) . . . . ?
C13 N3 C16 C15 -22.0(2) . . . . ?
C9 C8 C7 C6 0.1(4) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C16 N3 C12 C11 -69.72(18) . . . . ?
C16 N3 C13 C14 0.5(2) . . . . ?
C16 C15 C14 C13 -35.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0170_0m
_database_code_depnum_ccdc_archive 'CCDC 2119865'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H32 Cs N3 O7'
_chemical_formula_sum            'C22 H32 Cs N3 O7'
_chemical_formula_weight         583.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.8674(8)
_cell_length_b                   12.8807(8)
_cell_length_c                   16.3307(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.978(2)
_cell_angle_gamma                90
_cell_volume                     2492.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.049
_cell_measurement_theta_min      2.957
_shelx_estimated_absorpt_T_max   0.657
_shelx_estimated_absorpt_T_min   0.580
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1226 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.7873.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            76373
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4711
_reflns_number_total             5427
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5427
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+1.5109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1106
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1WB) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Sof(H15C)=Sof(H15D)=Sof(H14C)=Sof(H14D)=Sof(O2B)=Sof(Cs1B)=Sof(O1WB)=
 Sof(H1WC)=Sof(H1WD)=1-FVAR(1)
 Sof(Cs1A)=Sof(O1WA)=Sof(H1WA)=Sof(H1WB)=Sof(H15A)=Sof(H15B)=Sof(H14A)=
 Sof(H14B)=Sof(O2A)=FVAR(1)
4.a Rotating group:
 O1WA(H1WA,H1WB), O1WB(H1WC,H1WD)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B), C21(H21A,H21B), C20(H20A,
 H20B), C19(H19A,H19B), C18(H18A,H18B), C17(H17A,H17B), C15(H15C,H15D),
 C15(H15A,H15B), C16(H16A,H16B), C14(H14C,H14D), C14(H14A,H14B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C7(H7), C8(H8), C9(H9)
4.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1A Cs 0.55454(10) 0.34199(10) 0.52978(9) 0.0653(2) Uani 0.662(8) 1 d . . P A
1
O1 O 0.2576(2) 0.42931(19) 0.72178(13) 0.0751(6) Uani 1 1 d . . . . .
O11 O 0.4228(2) 0.16954(18) 0.85116(14) 0.0726(6) Uani 1 1 d . . . . .
N1 N 0.1448(2) 0.4132(2) 0.83334(14) 0.0595(5) Uani 1 1 d . . . . .
O5 O 0.5755(2) 0.1123(2) 0.54631(15) 0.0877(7) Uani 1 1 d . . . . .
N3 N 0.5336(2) 0.21438(19) 0.70537(15) 0.0585(5) Uani 1 1 d . . . . .
O4 O 0.7524(2) 0.2187(2) 0.4678(2) 0.1018(9) Uani 1 1 d . . . . .
N2 N 0.1363(3) 0.3510(2) 0.90270(16) 0.0679(7) Uani 1 1 d . . . . .
C2 C 0.2860(2) 0.2997(2) 0.83061(16) 0.0564(6) Uani 1 1 d . . . . .
C5 C 0.0696(2) 0.4986(2) 0.82349(17) 0.0573(6) Uani 1 1 d . . . . .
O3 O 0.8124(3) 0.4108(3) 0.5418(2) 0.1116(10) Uani 1 1 d . . . . .
C3 C 0.2193(3) 0.2853(2) 0.90013(18) 0.0629(7) Uani 1 1 d . . . . .
C1 C 0.2342(2) 0.3847(2) 0.78670(16) 0.0566(6) Uani 1 1 d . . . . .
C6 C -0.0052(3) 0.5176(3) 0.88364(19) 0.0686(7) Uani 1 1 d . . . . .
H6 H -0.006752 0.473351 0.928559 0.082 Uiso 1 1 calc R U . . .
C12 C 0.4367(3) 0.2735(2) 0.73002(18) 0.0609(7) Uani 1 1 d . . . . .
H12A H 0.379107 0.270029 0.685724 0.073 Uiso 1 1 calc R U . . .
H12B H 0.459475 0.345623 0.735456 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3825(3) 0.2419(2) 0.80887(17) 0.0581(6) Uani 1 1 d . . . . .
C10 C 0.0702(3) 0.5642(3) 0.7560(2) 0.0703(8) Uani 1 1 d . . . . .
H10 H 0.119738 0.552648 0.714608 0.084 Uiso 1 1 calc R U . . .
C7 C -0.0779(3) 0.6015(3) 0.8781(2) 0.0796(9) Uani 1 1 d . . . . .
H7 H -0.126851 0.614033 0.919647 0.096 Uiso 1 1 calc R U . . .
C8 C -0.0779(3) 0.6663(3) 0.8115(3) 0.0832(10) Uani 1 1 d . . . . .
H8 H -0.127212 0.722371 0.807261 0.100 Uiso 1 1 calc R U . . .
C13 C 0.6342(3) 0.2251(3) 0.7621(2) 0.0746(9) Uani 1 1 d . . . . .
H13A H 0.609587 0.243769 0.815849 0.090 Uiso 1 1 calc R U . . .
H13B H 0.671368 0.158117 0.767094 0.090 Uiso 1 1 calc R U . . .
C22 C 0.5073(3) 0.1083(3) 0.6810(2) 0.0713(8) Uani 1 1 d . . . . .
H22A H 0.432036 0.106471 0.654886 0.086 Uiso 1 1 calc R U . . .
H22B H 0.507062 0.065204 0.729678 0.086 Uiso 1 1 calc R U . . .
C21 C 0.5888(3) 0.0632(3) 0.6232(2) 0.0822(9) Uani 1 1 d . . . . .
H21A H 0.665488 0.072879 0.645493 0.099 Uiso 1 1 calc R U . . .
H21B H 0.575322 -0.010698 0.616991 0.099 Uiso 1 1 calc R U . . .
C4 C 0.2346(4) 0.2069(4) 0.9669(3) 0.0956(13) Uani 1 1 d . . . . .
H4A H 0.165808 0.200541 0.995002 0.143 Uiso 1 1 calc R U . . .
H4B H 0.294300 0.228705 1.005003 0.143 Uiso 1 1 calc R U . . .
H4C H 0.253456 0.140996 0.943874 0.143 Uiso 1 1 calc R U . . .
C9 C -0.0045(3) 0.6475(3) 0.7513(3) 0.0835(10) Uani 1 1 d . . . . .
H9 H -0.004584 0.691534 0.706144 0.100 Uiso 1 1 calc R U . . .
O1WA O 0.4174(4) 0.5072(3) 0.6135(2) 0.0650(11) Uani 0.662(8) 1 d . . P A 1
H1WA H 0.348177 0.504693 0.624839 0.098 Uiso 0.662(8) 1 d R U P A 1
H1WB H 0.451077 0.531382 0.656759 0.098 Uiso 0.662(8) 1 d R U P A 1
C20 C 0.6442(6) 0.0708(4) 0.4865(4) 0.151(3) Uani 1 1 d . . . . .
H20A H 0.651819 -0.003085 0.496804 0.181 Uiso 1 1 calc R U . . .
H20B H 0.604088 0.078652 0.433570 0.181 Uiso 1 1 calc R U . . .
C19 C 0.7466(6) 0.1095(4) 0.4804(6) 0.159(3) Uani 1 1 d . . . . .
H19A H 0.781421 0.075135 0.435325 0.190 Uiso 1 1 calc R U . . .
H19B H 0.791036 0.092574 0.530196 0.190 Uiso 1 1 calc R U . . .
C18 C 0.8649(4) 0.2519(5) 0.4769(5) 0.132(2) Uani 1 1 d . . . . .
H18A H 0.907559 0.224301 0.432780 0.159 Uiso 1 1 calc R U . . .
H18B H 0.898801 0.226796 0.528508 0.159 Uiso 1 1 calc R U . . .
C17 C 0.8676(5) 0.3638(6) 0.4754(5) 0.132(2) Uani 1 1 d . . . . .
H17A H 0.945667 0.386481 0.477143 0.158 Uiso 1 1 calc R U . . .
H17B H 0.831877 0.387685 0.424029 0.158 Uiso 1 1 calc R U . . .
C15 C 0.7964(7) 0.4407(5) 0.6845(4) 0.161(3) Uani 1 1 d . . . . .
H15C H 0.738797 0.491349 0.668748 0.193 Uiso 0.338(8) 1 calc R U P A 2
H15D H 0.835619 0.459805 0.735895 0.193 Uiso 0.338(8) 1 calc R U P A 2
H15A H 0.770633 0.511343 0.674845 0.193 Uiso 0.662(8) 1 calc R U P A 1
H15B H 0.842629 0.441755 0.735256 0.193 Uiso 0.662(8) 1 calc R U P A 1
C16 C 0.8726(6) 0.4155(6) 0.6184(4) 0.151(3) Uani 1 1 d . . . . .
H16A H 0.931021 0.468078 0.616586 0.182 Uiso 1 1 calc R U . . .
H16B H 0.908888 0.349243 0.629873 0.182 Uiso 1 1 calc R U . . .
C14 C 0.7136(6) 0.2993(8) 0.7382(5) 0.212(5) Uani 1 1 d . . . . .
H14C H 0.684095 0.362452 0.761358 0.255 Uiso 0.338(8) 1 calc R U P A 2
H14D H 0.778800 0.281916 0.773862 0.255 Uiso 0.338(8) 1 calc R U P A 2
H14A H 0.754120 0.321299 0.788349 0.255 Uiso 0.662(8) 1 calc R U P A 1
H14B H 0.767506 0.261520 0.706939 0.255 Uiso 0.662(8) 1 calc R U P A 1
O2B O 0.7550(7) 0.3302(7) 0.6821(4) 0.063(2) Uani 0.338(8) 1 d . . P A 2
Cs1B Cs 0.5703(4) 0.3625(5) 0.5464(3) 0.0936(9) Uani 0.338(8) 1 d . . P A 2
O1WB O 0.3435(11) 0.4831(7) 0.5839(6) 0.088(3) Uani 0.338(8) 1 d . U P A 2
H1WC H 0.373632 0.472010 0.634965 0.132 Uiso 0.338(8) 1 d R U P A 2
H1WD H 0.282768 0.441103 0.578703 0.132 Uiso 0.338(8) 1 d R U P A 2
O2A O 0.6926(5) 0.3765(4) 0.7006(4) 0.0971(19) Uani 0.662(8) 1 d . . P A 1


_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
Cs1A Cs1A 4.366(2) 3_666 ?
Cs1A O11 3.240(3) 4_565 ?
Cs1A O5 2.981(3) . ?
Cs1A N3 3.326(3) . ?
Cs1A O4 3.050(3) . ?
Cs1A O3 3.183(4) . ?
Cs1A O1WA 3.072(3) 3_666 ?
Cs1A H1WB 3.4674 . ?
Cs1A O2A 3.192(5) . ?
O1 C1 1.250(3) . ?
O11 C11 1.241(3) . ?
O11 Cs1B 3.580(7) 4_566 ?
N1 N2 1.395(3) . ?
N1 C5 1.420(4) . ?
N1 C1 1.387(4) . ?
O5 C21 1.407(5) . ?
O5 C20 1.409(5) . ?
O5 Cs1B 3.224(6) . ?
N3 C12 1.454(4) . ?
N3 C13 1.479(4) . ?
N3 C22 1.453(4) . ?
N3 Cs1B 3.269(4) . ?
O4 C19 1.424(7) . ?
O4 C18 1.403(6) . ?
O4 Cs1B 3.168(5) . ?
N2 C3 1.302(4) . ?
C2 C3 1.429(4) . ?
C2 C1 1.430(4) . ?
C2 C11 1.427(4) . ?
C5 C6 1.380(4) . ?
C5 C10 1.390(4) . ?
O3 C17 1.431(8) . ?
O3 C16 1.409(6) . ?
O3 Cs1B 2.946(6) . ?
C3 C4 1.490(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.524(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.392(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.411(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.503(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C9 H9 0.9300 . ?
O1WA H1WA 0.8524 . ?
O1WA H1WB 0.8523 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.322(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.441(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.480(10) . ?
C15 O2B 1.506(9) . ?
C15 O2A 1.519(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 O2B 1.134(9) . ?
C14 O2A 1.188(8) . ?
O2B Cs1B 3.063(8) . ?
Cs1B Cs1B 4.166(6) 3_666 ?
Cs1B O1WB 3.124(8) 3_666 ?
Cs1B H1WC 3.1429 . ?
O1WB H1WC 0.9012 . ?
O1WB H1WD 0.9012 . ?

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
Cs1A Cs1A H1WB 50.7 3_666 . ?
O11 Cs1A Cs1A 73.66(6) 4_565 3_666 ?
O11 Cs1A N3 134.38(8) 4_565 . ?
O11 Cs1A H1WB 113.7 4_565 . ?
O5 Cs1A Cs1A 165.52(9) . 3_666 ?
O5 Cs1A O11 94.02(8) . 4_565 ?
O5 Cs1A N3 56.00(7) . . ?
O5 Cs1A O4 56.70(8) . . ?
O5 Cs1A O3 101.27(9) . . ?
O5 Cs1A O1WA 133.22(9) . 3_666 ?
O5 Cs1A H1WB 132.4 . . ?
O5 Cs1A O2A 91.28(11) . . ?
N3 Cs1A Cs1A 128.20(7) . 3_666 ?
N3 Cs1A H1WB 77.7 . . ?
O4 Cs1A Cs1A 129.49(8) . 3_666 ?
O4 Cs1A O11 91.21(9) . 4_565 ?
O4 Cs1A N3 97.00(8) . . ?
O4 Cs1A O3 53.93(10) . . ?
O4 Cs1A O1WA 87.76(11) . 3_666 ?
O4 Cs1A H1WB 150.1 . . ?
O4 Cs1A O2A 89.62(15) . . ?
O3 Cs1A Cs1A 91.55(8) . 3_666 ?
O3 Cs1A O11 119.05(9) . 4_565 ?
O3 Cs1A N3 101.49(8) . . ?
O3 Cs1A H1WB 97.8 . . ?
O3 Cs1A O2A 57.25(14) . . ?
O1WA Cs1A Cs1A 44.23(7) 3_666 3_666 ?
O1WA Cs1A O11 53.82(10) 3_666 4_565 ?
O1WA Cs1A N3 170.07(9) 3_666 . ?
O1WA Cs1A O3 74.27(12) 3_666 . ?
O1WA Cs1A H1WB 93.8 3_666 . ?
O1WA Cs1A O2A 120.43(12) 3_666 . ?
O2A Cs1A Cs1A 101.41(13) . 3_666 ?
O2A Cs1A O11 174.15(10) . 4_565 ?
O2A Cs1A N3 51.18(10) . . ?
O2A Cs1A H1WB 64.0 . . ?
Cs1A O11 Cs1B 4.04(9) 4_566 4_566 ?
C11 O11 Cs1A 133.6(2) . 4_566 ?
C11 O11 Cs1B 137.6(2) . 4_566 ?
N2 N1 C5 117.7(2) . . ?
C1 N1 N2 112.5(2) . . ?
C1 N1 C5 129.6(2) . . ?
C21 O5 Cs1A 122.1(2) . . ?
C21 O5 C20 114.0(4) . . ?
C21 O5 Cs1B 116.7(2) . . ?
C20 O5 Cs1A 111.2(3) . . ?
C20 O5 Cs1B 113.0(3) . . ?
C12 N3 Cs1A 94.32(15) . . ?
C12 N3 C13 113.7(3) . . ?
C12 N3 Cs1B 93.09(16) . . ?
C13 N3 Cs1A 113.59(17) . . ?
C13 N3 Cs1B 107.9(2) . . ?
C22 N3 Cs1A 104.66(17) . . ?
C22 N3 C12 114.0(2) . . ?
C22 N3 C13 114.5(3) . . ?
C22 N3 Cs1B 111.5(2) . . ?
C19 O4 Cs1A 115.0(2) . . ?
C19 O4 Cs1B 118.7(3) . . ?
C18 O4 Cs1A 123.4(3) . . ?
C18 O4 C19 109.8(4) . . ?
C18 O4 Cs1B 116.4(4) . . ?
C3 N2 N1 105.1(2) . . ?
C3 C2 C1 104.9(2) . . ?
C11 C2 C3 127.9(3) . . ?
C11 C2 C1 127.2(3) . . ?
C6 C5 N1 118.7(3) . . ?
C6 C5 C10 119.1(3) . . ?
C10 C5 N1 122.1(3) . . ?
C17 O3 Cs1A 108.2(3) . . ?
C17 O3 Cs1B 114.6(3) . . ?
C16 O3 Cs1A 120.5(4) . . ?
C16 O3 C17 117.4(5) . . ?
C16 O3 Cs1B 115.9(4) . . ?
N2 C3 C2 113.1(3) . . ?
N2 C3 C4 118.7(3) . . ?
C2 C3 C4 128.2(3) . . ?
O1 C1 N1 123.6(3) . . ?
O1 C1 C2 132.0(3) . . ?
N1 C1 C2 104.4(2) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
N3 C12 H12A 107.8 . . ?
N3 C12 H12B 107.8 . . ?
N3 C12 C11 117.9(2) . . ?
H12A C12 H12B 107.2 . . ?
C11 C12 H12A 107.8 . . ?
C11 C12 H12B 107.8 . . ?
O11 C11 C2 123.0(3) . . ?
O11 C11 C12 120.2(3) . . ?
C2 C11 C12 116.8(2) . . ?
C5 C10 H10 120.6 . . ?
C5 C10 C9 118.9(3) . . ?
C9 C10 H10 120.6 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
N3 C13 H13A 108.6 . . ?
N3 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 N3 114.7(3) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
N3 C22 H22A 108.9 . . ?
N3 C22 H22B 108.9 . . ?
N3 C22 C21 113.5(3) . . ?
H22A C22 H22B 107.7 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
O5 C21 C22 109.9(3) . . ?
O5 C21 H21A 109.7 . . ?
O5 C21 H21B 109.7 . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9 119.2 . . ?
Cs1A O1WA H1WA 109.5 3_666 . ?
Cs1A O1WA H1WB 109.6 3_666 . ?
H1WA O1WA H1WB 104.4 . . ?
O5 C20 H20A 107.7 . . ?
O5 C20 H20B 107.7 . . ?
H20A C20 H20B 107.1 . . ?
C19 C20 O5 118.4(5) . . ?
C19 C20 H20A 107.7 . . ?
C19 C20 H20B 107.7 . . ?
O4 C19 H19A 108.4 . . ?
O4 C19 H19B 108.4 . . ?
C20 C19 O4 115.7(6) . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.4 . . ?
O4 C18 H18A 109.9 . . ?
O4 C18 H18B 109.9 . . ?
O4 C18 C17 109.0(5) . . ?
H18A C18 H18B 108.3 . . ?
C17 C18 H18A 109.9 . . ?
C17 C18 H18B 109.9 . . ?
O3 C17 C18 113.5(5) . . ?
O3 C17 H17A 108.9 . . ?
O3 C17 H17B 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
H15C C15 H15D 111.0 . . ?
H15A C15 H15B 106.6 . . ?
C16 C15 H15C 113.8 . . ?
C16 C15 H15D 113.8 . . ?
C16 C15 H15A 106.7 . . ?
C16 C15 H15B 106.7 . . ?
C16 C15 O2B 89.1(6) . . ?
C16 C15 O2A 122.6(6) . . ?
O2B C15 H15C 113.8 . . ?
O2B C15 H15D 113.8 . . ?
O2A C15 H15A 106.7 . . ?
O2A C15 H15B 106.7 . . ?
O3 C16 C15 110.9(6) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C13 C14 H14C 101.6 . . ?
C13 C14 H14D 101.6 . . ?
C13 C14 H14A 105.9 . . ?
C13 C14 H14B 105.9 . . ?
H14C C14 H14D 104.6 . . ?
H14A C14 H14B 106.2 . . ?
O2B C14 C13 141.6(9) . . ?
O2B C14 H14C 101.6 . . ?
O2B C14 H14D 101.6 . . ?
O2A C14 C13 125.8(6) . . ?
O2A C14 H14A 105.9 . . ?
O2A C14 H14B 105.9 . . ?
C15 O2B Cs1B 96.4(5) . . ?
C14 O2B C15 117.7(9) . . ?
C14 O2B Cs1B 108.0(5) . . ?
O11 Cs1B Cs1B 66.82(16) 4_565 3_666 ?
O11 Cs1B H1WC 97.0 4_565 . ?
O5 Cs1B O11 83.9(2) . 4_565 ?
O5 Cs1B N3 54.56(9) . . ?
O5 Cs1B Cs1B 149.0(3) . 3_666 ?
O5 Cs1B H1WC 117.6 . . ?
N3 Cs1B O11 124.1(2) . 4_565 ?
N3 Cs1B Cs1B 135.86(16) . 3_666 ?
N3 Cs1B H1WC 76.3 . . ?
O4 Cs1B O11 83.34(17) . 4_565 ?
O4 Cs1B O5 53.24(11) . . ?
O4 Cs1B N3 95.86(11) . . ?
O4 Cs1B Cs1B 128.20(15) . 3_666 ?
O4 Cs1B H1WC 170.8 . . ?
O3 Cs1B O11 115.72(14) . 4_565 ?
O3 Cs1B O5 101.09(12) . . ?
O3 Cs1B N3 108.29(15) . . ?
O3 Cs1B O4 54.98(11) . . ?
O3 Cs1B O2B 52.03(15) . . ?
O3 Cs1B Cs1B 100.6(2) . 3_666 ?
O3 Cs1B O1WB 59.6(2) . 3_666 ?
O3 Cs1B H1WC 131.7 . . ?
O2B Cs1B O5 81.44(18) . . ?
O2B Cs1B N3 57.71(14) . . ?
O2B Cs1B O4 74.69(17) . . ?
O2B Cs1B O1WB 109.4(2) . 3_666 ?
O2B Cs1B H1WC 104.4 . . ?
Cs1B Cs1B H1WC 59.5 3_666 . ?
O1WB Cs1B O5 129.00(19) 3_666 . ?
O1WB Cs1B N3 167.0(2) 3_666 . ?
O1WB Cs1B O4 80.90(17) 3_666 . ?
O1WB Cs1B H1WC 107.8 3_666 . ?
Cs1B O1WB H1WC 127.0 3_666 . ?
Cs1B O1WB H1WD 127.3 3_666 . ?
H1WC O1WB H1WD 105.7 . . ?
C15 O2A Cs1A 108.0(4) . . ?
C14 O2A Cs1A 114.8(5) . . ?
C14 O2A C15 113.3(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O1 0.93 2.28 2.899(4) 123.6 . yes
C13 H13A O11 0.97 2.51 3.050(4) 115.1 . yes
C22 H22B O11 0.97 2.64 3.105(4) 110.1 . yes
O1WA H1WA O1 0.85 2.19 2.843(4) 133.6 . yes
O1WA H1WB O11 0.85 2.33 2.861(5) 120.5 2_656 yes
O1WB H1WC O1 0.90 2.10 2.613(7) 115.0 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cs1A O11 C11 C2 -68.9(4) 4_566 . . . ?
Cs1A O11 C11 C12 110.7(3) 4_566 . . . ?
Cs1A O5 C21 C22 45.2(4) . . . . ?
Cs1A O5 C20 C19 54.1(8) . . . . ?
Cs1A N3 C12 C11 176.0(2) . . . . ?
Cs1A N3 C13 C14 9.3(7) . . . . ?
Cs1A N3 C22 C21 53.2(3) . . . . ?
Cs1A O4 C19 C20 25.2(8) . . . . ?
Cs1A O4 C18 C17 -31.2(7) . . . . ?
Cs1A O3 C17 C18 -60.9(5) . . . . ?
Cs1A O3 C16 C15 -30.0(7) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
N1 N2 C3 C4 179.7(3) . . . . ?
N1 C5 C6 C7 178.1(3) . . . . ?
N1 C5 C10 C9 -178.8(3) . . . . ?
O5 C20 C19 O4 -55.7(10) . . . . ?
N3 C12 C11 O11 1.9(4) . . . . ?
N3 C12 C11 C2 -178.6(3) . . . . ?
N3 C13 C14 O2B -39.9(18) . . . . ?
N3 C13 C14 O2A 31.0(15) . . . . ?
N3 C22 C21 O5 -69.6(4) . . . . ?
O4 C18 C17 O3 63.2(7) . . . . ?
N2 N1 C5 C6 1.9(4) . . . . ?
N2 N1 C5 C10 -179.0(3) . . . . ?
N2 N1 C1 O1 179.7(3) . . . . ?
N2 N1 C1 C2 -0.9(3) . . . . ?
C5 N1 N2 C3 -174.9(3) . . . . ?
C5 N1 C1 O1 -5.4(5) . . . . ?
C5 N1 C1 C2 174.0(3) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C5 C10 C9 C8 0.2(6) . . . . ?
C3 C2 C1 O1 -179.9(3) . . . . ?
C3 C2 C1 N1 0.8(3) . . . . ?
C3 C2 C11 O11 -1.3(5) . . . . ?
C3 C2 C11 C12 179.2(3) . . . . ?
C1 N1 N2 C3 0.6(3) . . . . ?
C1 N1 C5 C6 -172.7(3) . . . . ?
C1 N1 C5 C10 6.4(5) . . . . ?
C1 C2 C3 N2 -0.5(4) . . . . ?
C1 C2 C3 C4 179.8(4) . . . . ?
C1 C2 C11 O11 179.3(3) . . . . ?
C1 C2 C11 C12 -0.3(4) . . . . ?
C6 C5 C10 C9 0.3(5) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C12 N3 C13 C14 -97.1(7) . . . . ?
C12 N3 C22 C21 154.9(3) . . . . ?
C11 C2 C3 N2 180.0(3) . . . . ?
C11 C2 C3 C4 0.3(6) . . . . ?
C11 C2 C1 O1 -0.4(5) . . . . ?
C11 C2 C1 N1 -179.7(3) . . . . ?
C10 C5 C6 C7 -1.0(5) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C13 N3 C12 C11 -65.9(3) . . . . ?
C13 N3 C22 C21 -71.7(4) . . . . ?
C13 C14 O2B C15 153.2(12) . . . . ?
C13 C14 O2B Cs1B 45.6(18) . . . . ?
C13 C14 O2A Cs1A -55.4(14) . . . . ?
C13 C14 O2A C15 179.9(9) . . . . ?
C22 N3 C12 C11 67.9(3) . . . . ?
C22 N3 C13 C14 129.4(6) . . . . ?
C21 O5 C20 C19 -88.7(7) . . . . ?
C20 O5 C21 C22 -176.5(4) . . . . ?
C19 O4 C18 C17 -172.1(6) . . . . ?
C18 O4 C19 C20 169.7(7) . . . . ?
C17 O3 C16 C15 -165.5(5) . . . . ?
C16 O3 C17 C18 79.7(6) . . . . ?
C16 C15 O2B C14 159.0(9) . . . . ?
C16 C15 O2B Cs1B -86.8(4) . . . . ?
C16 C15 O2A Cs1A -48.7(8) . . . . ?
C16 C15 O2A C14 79.7(10) . . . . ?
O2B C15 C16 O3 77.1(6) . . . . ?
Cs1B O11 C11 C2 -69.1(4) 4_566 . . . ?
Cs1B O11 C11 C12 110.4(3) 4_566 . . . ?
Cs1B O5 C21 C22 48.8(4) . . . . ?
Cs1B O5 C20 C19 47.7(8) . . . . ?
Cs1B N3 C12 C11 -176.9(3) . . . . ?
Cs1B N3 C13 C14 4.7(7) . . . . ?
Cs1B N3 C22 C21 51.1(3) . . . . ?
Cs1B O4 C19 C20 32.3(9) . . . . ?
Cs1B O4 C18 C17 -33.6(7) . . . . ?
Cs1B O3 C17 C18 -61.3(6) . . . . ?
Cs1B O3 C16 C15 -25.0(6) . . . . ?
O2A C15 C16 O3 56.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0124_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2119868'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H19 N3 O2), C2 H3 N'
_chemical_formula_sum            'C34 H41 N7 O4'
_chemical_formula_weight         611.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.9053(5)
_cell_length_b                   11.6377(6)
_cell_length_c                   15.0249(6)
_cell_angle_alpha                86.844(4)
_cell_angle_beta                 89.823(4)
_cell_angle_gamma                69.381(5)
_cell_volume                     1618.34(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6093
_cell_measurement_temperature    290
_cell_measurement_theta_max      30.7950
_cell_measurement_theta_min      2.3190
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11782
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.873
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     -9.39 350.61   0.40   10.00  83.13  -7.74  28.85    --   900
  2  ω   -101.52  19.68   0.40   10.00    --   -7.74 -59.25  92.08  303
  3  ω   -101.52  19.68   0.40   10.00    --   -7.74 -59.25 -51.92  303
  4  ω   -101.52  19.68   0.40   20.00    --   -7.74 -59.25 164.08  303
  5  ω   -101.52  19.68   0.40   20.00    --   -7.74 -59.25  20.08  303
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350329000
_diffrn_orient_matrix_UB_12      0.0132691000
_diffrn_orient_matrix_UB_13      0.0414221000
_diffrn_orient_matrix_UB_21      -0.0328093000
_diffrn_orient_matrix_UB_22      -0.0442269000
_diffrn_orient_matrix_UB_23      -0.0063682000
_diffrn_orient_matrix_UB_31      0.0595952000
_diffrn_orient_matrix_UB_32      -0.0460721000
_diffrn_orient_matrix_UB_33      0.0219026000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5754
_reflns_number_total             11782
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         11782
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      0.930
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1047P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1781
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4899(13)
 0.5101(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C132(H13A,H13B), C122(H12A,H12B), C162(H16A,H16B), C121(H12C,H12D), C152(H15A,
 H15B), C142(H14A,H14B), C131(H13C,H13D), C161(H16C,H16D), C151(H15C,H15D),
 C141(H14C,H14D)
3.b Aromatic/amide H refined with riding coordinates:
 C62(H62), C102(H102), C101(H101), C92(H92), C82(H82), C61(H61), C72(H72),
 C91(H91), C81(H81), C71(H71)
3.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O12 O 0.8121(2) 0.84250(19) 0.56670(12) 0.0541(6) Uani 1 1 d . . . . .
O11 O 0.3911(2) 0.65324(19) 0.84124(12) 0.0526(5) Uani 1 1 d . . . . .
N32 N 1.1250(3) 0.8097(2) 0.77319(14) 0.0424(6) Uani 1 1 d . . . . .
O111 O 0.7375(2) 0.7911(2) 0.78303(13) 0.0651(6) Uani 1 1 d . . . . .
O112 O 1.2684(2) 0.7601(2) 0.61927(13) 0.0747(7) Uani 1 1 d . . . . .
N12 N 0.8925(2) 0.8454(2) 0.42159(14) 0.0481(6) Uani 1 1 d . . . . .
N11 N 0.4333(3) 0.7062(2) 0.98329(15) 0.0535(7) Uani 1 1 d . . . . .
N31 N 0.6902(3) 0.6804(3) 0.64277(16) 0.0523(7) Uani 1 1 d . . . . .
N22 N 1.0214(3) 0.8280(3) 0.37603(15) 0.0611(8) Uani 1 1 d . . . . .
C12 C 0.9116(3) 0.8336(3) 0.51299(17) 0.0434(7) Uani 1 1 d . . . . .
N21 N 0.5136(3) 0.7669(3) 1.02331(16) 0.0694(8) Uani 1 1 d . . . . .
C22 C 1.0625(3) 0.8081(3) 0.52558(17) 0.0471(8) Uani 1 1 d . . . . .
C52 C 0.7654(3) 0.8689(3) 0.37173(18) 0.0434(7) Uani 1 1 d . . . . .
C11 C 0.4585(3) 0.6977(3) 0.89246(18) 0.0458(7) Uani 1 1 d . . . . .
C132 C 1.0433(3) 0.7986(3) 0.85687(17) 0.0502(8) Uani 1 1 d . . . . .
H13A H 0.953401 0.787929 0.841877 0.060 Uiso 1 1 calc R U . . .
H13B H 1.100635 0.729057 0.895474 0.060 Uiso 1 1 calc R U . . .
C62 C 0.7706(3) 0.8181(3) 0.28914(19) 0.0554(8) Uani 1 1 d . . . . .
H62 H 0.857714 0.764871 0.268763 0.066 Uiso 1 1 calc R U . . .
C21 C 0.5651(3) 0.7512(3) 0.87605(18) 0.0493(8) Uani 1 1 d . . . . .
C111 C 0.6368(3) 0.7539(3) 0.79455(18) 0.0504(8) Uani 1 1 d . . . . .
C122 C 1.0445(3) 0.8034(3) 0.69167(16) 0.0519(8) Uani 1 1 d . . . . .
H12A H 0.960299 0.877838 0.683598 0.062 Uiso 1 1 calc R U . . .
H12B H 1.011422 0.734359 0.699021 0.062 Uiso 1 1 calc R U . . .
C102 C 0.6336(3) 0.9450(3) 0.40135(19) 0.0550(8) Uani 1 1 d . . . . .
H102 H 0.627958 0.979292 0.456308 0.066 Uiso 1 1 calc R U . . .
C112 C 1.1368(3) 0.7890(3) 0.60935(19) 0.0502(8) Uani 1 1 d . . . . .
C51 C 0.3302(3) 0.6739(3) 1.03417(19) 0.0534(8) Uani 1 1 d . . . . .
C162 C 1.1570(4) 0.9263(3) 0.7770(2) 0.0599(9) Uani 1 1 d . . . . .
H16A H 1.255970 0.912711 0.760468 0.072 Uiso 1 1 calc R U . . .
H16B H 1.093108 0.990382 0.736882 0.072 Uiso 1 1 calc R U . . .
C32 C 1.1195(3) 0.8071(3) 0.43863(19) 0.0567(9) Uani 1 1 d . . . . .
C121 C 0.5833(3) 0.7069(3) 0.71439(18) 0.0607(9) Uani 1 1 d . . . . .
H12C H 0.564642 0.632604 0.732442 0.073 Uiso 1 1 calc R U . . .
H12D H 0.493346 0.768078 0.692162 0.073 Uiso 1 1 calc R U . . .
C101 C 0.2882(4) 0.5782(3) 1.0113(2) 0.0639(9) Uani 1 1 d . . . . .
H101 H 0.331139 0.531005 0.964010 0.077 Uiso 1 1 calc R U . . .
C92 C 0.5105(3) 0.9702(3) 0.3499(2) 0.0652(9) Uani 1 1 d . . . . .
H92 H 0.421942 1.020359 0.370624 0.078 Uiso 1 1 calc R U . . .
C82 C 0.5184(4) 0.9214(3) 0.2680(2) 0.0683(10) Uani 1 1 d . . . . .
H82 H 0.435473 0.939363 0.232958 0.082 Uiso 1 1 calc R U . . .
C61 C 0.2691(4) 0.7412(3) 1.1067(2) 0.0691(10) Uani 1 1 d . . . . .
H61 H 0.298761 0.804784 1.122726 0.083 Uiso 1 1 calc R U . . .
C31 C 0.5918(4) 0.7915(3) 0.9593(2) 0.0660(10) Uani 1 1 d . . . . .
C72 C 0.6476(4) 0.8466(3) 0.2381(2) 0.0657(9) Uani 1 1 d . . . . .
H72 H 0.652500 0.814541 0.182394 0.079 Uiso 1 1 calc R U . . .
C91 C 0.1809(4) 0.5530(4) 1.0598(3) 0.0800(11) Uani 1 1 d . . . . .
H91 H 0.151161 0.489252 1.044271 0.096 Uiso 1 1 calc R U . . .
C152 C 1.1332(4) 0.9615(3) 0.8706(2) 0.0770(11) Uani 1 1 d . . . . .
H15A H 1.102892 1.049947 0.873965 0.092 Uiso 1 1 calc R U . . .
H15B H 1.220255 0.922755 0.906543 0.092 Uiso 1 1 calc R U . . .
C81 C 0.1183(4) 0.6222(4) 1.1307(3) 0.0852(13) Uani 1 1 d . . . . .
H81 H 0.044887 0.606371 1.161898 0.102 Uiso 1 1 calc R U . . .
C71 C 0.1643(4) 0.7142(4) 1.1550(2) 0.0860(12) Uani 1 1 d . . . . .
H71 H 0.124904 0.758520 1.204236 0.103 Uiso 1 1 calc R U . . .
C142 C 1.0152(4) 0.9151(4) 0.9010(3) 0.0880(13) Uani 1 1 d . . . . .
H14A H 1.018568 0.900967 0.965284 0.106 Uiso 1 1 calc R U . . .
H14B H 0.921157 0.974103 0.883279 0.106 Uiso 1 1 calc R U . . .
C2 C 0.2680(5) 0.4691(4) 0.7503(3) 0.0899(13) Uani 1 1 d . . . . .
C42 C 1.2717(4) 0.7896(5) 0.4143(2) 0.0955(15) Uani 1 1 d . . . . .
H42A H 1.277789 0.799886 0.350793 0.143 Uiso 1 1 calc R U . . .
H42B H 1.333596 0.708321 0.434302 0.143 Uiso 1 1 calc R U . . .
H42C H 1.301391 0.849210 0.442294 0.143 Uiso 1 1 calc R U . . .
C41 C 0.6917(5) 0.8583(5) 0.9792(2) 0.1095(17) Uani 1 1 d . . . . .
H41A H 0.666518 0.896331 1.034950 0.164 Uiso 1 1 calc R U . . .
H41B H 0.683512 0.920253 0.932542 0.164 Uiso 1 1 calc R U . . .
H41C H 0.789157 0.801089 0.982880 0.164 Uiso 1 1 calc R U . . .
N2 N 0.1478(4) 0.5054(4) 0.7609(4) 0.1403(18) Uani 1 1 d . . . . .
C1 C 0.4195(5) 0.4241(4) 0.7392(3) 0.1226(18) Uani 1 1 d . . . . .
H1A H 0.446105 0.354227 0.703150 0.184 Uiso 1 1 calc R U . . .
H1B H 0.466852 0.400295 0.796466 0.184 Uiso 1 1 calc R U . . .
H1C H 0.448232 0.487436 0.710465 0.184 Uiso 1 1 calc R U . . .
H31 H 0.721(3) 0.745(3) 0.6364(18) 0.056(10) Uiso 1 1 d . . . . .
C131 C 0.6289(4) 0.6664(4) 0.55463(19) 0.0703(10) Uani 1 1 d . . . . .
H13C H 0.544432 0.643358 0.562862 0.084 Uiso 1 1 calc R U . . .
H13D H 0.602085 0.742497 0.517921 0.084 Uiso 1 1 calc R U . . .
C161 C 0.8152(4) 0.5658(4) 0.6612(3) 0.0819(11) Uani 1 1 d . . . . .
H16C H 0.891413 0.583474 0.691481 0.098 Uiso 1 1 calc R U . . .
H16D H 0.786915 0.508272 0.699117 0.098 Uiso 1 1 calc R U . . .
C151 C 0.8621(8) 0.5171(6) 0.5829(4) 0.229(4) Uani 1 1 d . . . . .
H15C H 0.889607 0.428409 0.589277 0.275 Uiso 1 1 calc R U . . .
H15D H 0.946373 0.536237 0.565016 0.275 Uiso 1 1 calc R U . . .
C141 C 0.7455(7) 0.5682(5) 0.5132(3) 0.150(2) Uani 1 1 d . . . . .
H14C H 0.781147 0.601149 0.461319 0.180 Uiso 1 1 calc R U . . .
H14D H 0.711007 0.504614 0.494911 0.180 Uiso 1 1 calc R U . . .
H32 H 1.213(3) 0.754(3) 0.7763(19) 0.066(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
O12 C12 1.251(3) . ?
O11 C11 1.264(3) . ?
N32 C132 1.517(3) . ?
N32 C122 1.483(3) . ?
N32 C162 1.503(4) . ?
N32 H32 0.89(3) . ?
O111 C111 1.228(3) . ?
O112 C112 1.233(3) . ?
N12 N22 1.403(3) . ?
N12 C12 1.380(3) . ?
N12 C52 1.400(3) . ?
N11 N21 1.391(3) . ?
N11 C11 1.389(3) . ?
N11 C51 1.416(4) . ?
N31 C121 1.475(3) . ?
N31 H31 0.91(3) . ?
N31 C131 1.499(4) . ?
N31 C161 1.479(4) . ?
N22 C32 1.305(4) . ?
C12 C22 1.428(4) . ?
N21 C31 1.315(4) . ?
C22 C112 1.426(4) . ?
C22 C32 1.421(4) . ?
C52 C62 1.397(4) . ?
C52 C102 1.383(4) . ?
C11 C21 1.416(4) . ?
C132 H13A 0.9700 . ?
C132 H13B 0.9700 . ?
C132 C142 1.479(4) . ?
C62 H62 0.9300 . ?
C62 C72 1.369(4) . ?
C21 C111 1.418(4) . ?
C21 C31 1.418(4) . ?
C111 C121 1.520(4) . ?
C122 H12A 0.9700 . ?
C122 H12B 0.9700 . ?
C122 C112 1.517(4) . ?
C102 H102 0.9300 . ?
C102 C92 1.378(4) . ?
C51 C101 1.378(4) . ?
C51 C61 1.386(4) . ?
C162 H16A 0.9700 . ?
C162 H16B 0.9700 . ?
C162 C152 1.480(4) . ?
C32 C42 1.495(4) . ?
C121 H12C 0.9700 . ?
C121 H12D 0.9700 . ?
C101 H101 0.9300 . ?
C101 C91 1.392(4) . ?
C92 H92 0.9300 . ?
C92 C82 1.375(4) . ?
C82 H82 0.9300 . ?
C82 C72 1.360(5) . ?
C61 H61 0.9300 . ?
C61 C71 1.380(5) . ?
C31 C41 1.497(5) . ?
C72 H72 0.9300 . ?
C91 H91 0.9300 . ?
C91 C81 1.381(5) . ?
C152 H15A 0.9700 . ?
C152 H15B 0.9700 . ?
C152 C142 1.510(4) . ?
C81 H81 0.9300 . ?
C81 C71 1.369(5) . ?
C71 H71 0.9300 . ?
C142 H14A 0.9700 . ?
C142 H14B 0.9700 . ?
C2 N2 1.129(5) . ?
C2 C1 1.418(6) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C131 H13C 0.9700 . ?
C131 H13D 0.9700 . ?
C131 C141 1.473(6) . ?
C161 H16C 0.9700 . ?
C161 H16D 0.9700 . ?
C161 C151 1.343(6) . ?
C151 H15C 0.9700 . ?
C151 H15D 0.9700 . ?
C151 C141 1.497(7) . ?
C141 H14C 0.9700 . ?
C141 H14D 0.9700 . ?

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
C132 N32 H32 110.0(19) . . ?
C122 N32 C132 111.5(2) . . ?
C122 N32 C162 114.0(2) . . ?
C122 N32 H32 112.6(19) . . ?
C162 N32 C132 107.0(2) . . ?
C162 N32 H32 101(2) . . ?
C12 N12 N22 112.8(2) . . ?
C12 N12 C52 128.6(2) . . ?
C52 N12 N22 118.6(2) . . ?
N21 N11 C51 119.2(2) . . ?
C11 N11 N21 111.8(2) . . ?
C11 N11 C51 128.7(3) . . ?
C121 N31 H31 107.2(18) . . ?
C121 N31 C131 113.1(2) . . ?
C121 N31 C161 113.3(3) . . ?
C131 N31 H31 107.8(18) . . ?
C161 N31 H31 109.7(19) . . ?
C161 N31 C131 105.6(3) . . ?
C32 N22 N12 104.8(2) . . ?
O12 C12 N12 123.8(3) . . ?
O12 C12 C22 132.3(2) . . ?
N12 C12 C22 103.9(2) . . ?
C31 N21 N11 105.3(2) . . ?
C112 C22 C12 125.8(2) . . ?
C32 C22 C12 105.8(2) . . ?
C32 C22 C112 128.4(3) . . ?
C62 C52 N12 120.1(3) . . ?
C102 C52 N12 121.3(3) . . ?
C102 C52 C62 118.6(3) . . ?
O11 C11 N11 123.1(3) . . ?
O11 C11 C21 132.0(3) . . ?
N11 C11 C21 104.9(3) . . ?
N32 C132 H13A 110.7 . . ?
N32 C132 H13B 110.7 . . ?
H13A C132 H13B 108.8 . . ?
C142 C132 N32 105.4(2) . . ?
C142 C132 H13A 110.7 . . ?
C142 C132 H13B 110.7 . . ?
C52 C62 H62 120.0 . . ?
C72 C62 C52 120.1(3) . . ?
C72 C62 H62 120.0 . . ?
C11 C21 C111 126.4(3) . . ?
C11 C21 C31 105.5(2) . . ?
C31 C21 C111 127.9(3) . . ?
O111 C111 C21 125.9(3) . . ?
O111 C111 C121 117.3(2) . . ?
C21 C111 C121 116.8(2) . . ?
N32 C122 H12A 109.2 . . ?
N32 C122 H12B 109.2 . . ?
N32 C122 C112 111.9(2) . . ?
H12A C122 H12B 107.9 . . ?
C112 C122 H12A 109.2 . . ?
C112 C122 H12B 109.2 . . ?
C52 C102 H102 119.8 . . ?
C92 C102 C52 120.4(3) . . ?
C92 C102 H102 119.8 . . ?
O112 C112 C22 125.1(3) . . ?
O112 C112 C122 118.6(2) . . ?
C22 C112 C122 116.3(2) . . ?
C101 C51 N11 120.7(3) . . ?
C101 C51 C61 120.0(3) . . ?
C61 C51 N11 119.3(3) . . ?
N32 C162 H16A 110.6 . . ?
N32 C162 H16B 110.6 . . ?
H16A C162 H16B 108.7 . . ?
C152 C162 N32 105.7(2) . . ?
C152 C162 H16A 110.6 . . ?
C152 C162 H16B 110.6 . . ?
N22 C32 C22 112.7(3) . . ?
N22 C32 C42 119.8(3) . . ?
C22 C32 C42 127.5(3) . . ?
N31 C121 C111 111.1(2) . . ?
N31 C121 H12C 109.4 . . ?
N31 C121 H12D 109.4 . . ?
C111 C121 H12C 109.4 . . ?
C111 C121 H12D 109.4 . . ?
H12C C121 H12D 108.0 . . ?
C51 C101 H101 120.3 . . ?
C51 C101 C91 119.3(3) . . ?
C91 C101 H101 120.3 . . ?
C102 C92 H92 119.9 . . ?
C82 C92 C102 120.1(3) . . ?
C82 C92 H92 119.9 . . ?
C92 C82 H82 120.0 . . ?
C72 C82 C92 120.0(3) . . ?
C72 C82 H82 120.0 . . ?
C51 C61 H61 119.9 . . ?
C71 C61 C51 120.1(4) . . ?
C71 C61 H61 119.9 . . ?
N21 C31 C21 112.4(3) . . ?
N21 C31 C41 119.7(3) . . ?
C21 C31 C41 127.9(3) . . ?
C62 C72 H72 119.6 . . ?
C82 C72 C62 120.8(3) . . ?
C82 C72 H72 119.6 . . ?
C101 C91 H91 119.8 . . ?
C81 C91 C101 120.4(4) . . ?
C81 C91 H91 119.8 . . ?
C162 C152 H15A 111.0 . . ?
C162 C152 H15B 111.0 . . ?
C162 C152 C142 103.9(3) . . ?
H15A C152 H15B 109.0 . . ?
C142 C152 H15A 111.0 . . ?
C142 C152 H15B 111.0 . . ?
C91 C81 H81 120.0 . . ?
C71 C81 C91 119.9(4) . . ?
C71 C81 H81 120.0 . . ?
C61 C71 H71 119.9 . . ?
C81 C71 C61 120.2(4) . . ?
C81 C71 H71 119.9 . . ?
C132 C142 C152 105.5(3) . . ?
C132 C142 H14A 110.6 . . ?
C132 C142 H14B 110.6 . . ?
C152 C142 H14A 110.6 . . ?
C152 C142 H14B 110.6 . . ?
H14A C142 H14B 108.8 . . ?
N2 C2 C1 178.6(6) . . ?
C32 C42 H42A 109.5 . . ?
C32 C42 H42B 109.5 . . ?
C32 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C31 C41 H41A 109.5 . . ?
C31 C41 H41B 109.5 . . ?
C31 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N31 C131 H13C 110.7 . . ?
N31 C131 H13D 110.7 . . ?
H13C C131 H13D 108.8 . . ?
C141 C131 N31 105.0(3) . . ?
C141 C131 H13C 110.7 . . ?
C141 C131 H13D 110.7 . . ?
N31 C161 H16C 110.1 . . ?
N31 C161 H16D 110.1 . . ?
H16C C161 H16D 108.4 . . ?
C151 C161 N31 108.0(4) . . ?
C151 C161 H16C 110.1 . . ?
C151 C161 H16D 110.1 . . ?
C161 C151 H15C 109.7 . . ?
C161 C151 H15D 109.7 . . ?
C161 C151 C141 109.9(5) . . ?
H15C C151 H15D 108.2 . . ?
C141 C151 H15C 109.7 . . ?
C141 C151 H15D 109.7 . . ?
C131 C141 C151 106.1(4) . . ?
C131 C141 H14C 110.5 . . ?
C131 C141 H14D 110.5 . . ?
C151 C141 H14C 110.5 . . ?
C151 C141 H14D 110.5 . . ?
H14C C141 H14D 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C132 H13A O111 0.97 2.30 3.261(3) 168.5 . yes
C122 H12B N2 0.97 2.64 3.357(5) 130.6 1_655 yes
C102 H102 O12 0.93 2.51 2.989(3) 112.4 . yes
C162 H16B N22 0.97 2.56 3.511(4) 166.3 2_776 yes
C121 H12C O11 0.97 2.33 2.886(3) 115.8 . yes
C121 H12D O112 0.97 2.52 3.275(4) 134.7 1_455 yes
C101 H101 O11 0.93 2.47 2.949(4) 112.5 . yes
N31 H31 O12 0.91(3) 1.94(3) 2.771(3) 151(2) . yes
C161 H16C N2 0.97 2.58 3.446(6) 148.9 1_655 yes
N32 H32 O11 0.89(3) 1.96(3) 2.782(3) 153(3) 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 C12 C22 C112 -1.9(5) . . . . ?
O12 C12 C22 C32 178.5(3) . . . . ?
O11 C11 C21 C111 -8.5(6) . . . . ?
O11 C11 C21 C31 176.0(3) . . . . ?
N32 C132 C142 C152 -26.0(4) . . . . ?
N32 C122 C112 O112 14.0(4) . . . . ?
N32 C122 C112 C22 -167.1(3) . . . . ?
N32 C162 C152 C142 -31.4(4) . . . . ?
O111 C111 C121 N31 16.9(4) . . . . ?
N12 N22 C32 C22 0.7(4) . . . . ?
N12 N22 C32 C42 -177.3(3) . . . . ?
N12 C12 C22 C112 179.6(3) . . . . ?
N12 C12 C22 C32 0.0(3) . . . . ?
N12 C52 C62 C72 -176.3(3) . . . . ?
N12 C52 C102 C92 177.8(3) . . . . ?
N11 N21 C31 C21 1.1(4) . . . . ?
N11 N21 C31 C41 179.6(3) . . . . ?
N11 C11 C21 C111 173.6(3) . . . . ?
N11 C11 C21 C31 -1.9(3) . . . . ?
N11 C51 C101 C91 -176.5(3) . . . . ?
N11 C51 C61 C71 177.5(3) . . . . ?
N31 C131 C141 C151 7.5(6) . . . . ?
N31 C161 C151 C141 -19.9(8) . . . . ?
N22 N12 C12 O12 -178.2(3) . . . . ?
N22 N12 C12 C22 0.5(3) . . . . ?
N22 N12 C52 C62 31.8(4) . . . . ?
N22 N12 C52 C102 -146.3(3) . . . . ?
C12 N12 N22 C32 -0.7(4) . . . . ?
C12 N12 C52 C62 -146.7(3) . . . . ?
C12 N12 C52 C102 35.2(5) . . . . ?
C12 C22 C112 O112 175.6(3) . . . . ?
C12 C22 C112 C122 -3.1(5) . . . . ?
C12 C22 C32 N22 -0.5(4) . . . . ?
C12 C22 C32 C42 177.4(4) . . . . ?
N21 N11 C11 O11 -175.4(3) . . . . ?
N21 N11 C11 C21 2.7(3) . . . . ?
N21 N11 C51 C101 -155.7(3) . . . . ?
N21 N11 C51 C61 25.6(4) . . . . ?
C52 N12 N22 C32 -179.4(3) . . . . ?
C52 N12 C12 O12 0.3(5) . . . . ?
C52 N12 C12 C22 179.0(3) . . . . ?
C52 C62 C72 C82 -2.0(5) . . . . ?
C52 C102 C92 C82 -1.0(5) . . . . ?
C11 N11 N21 C31 -2.4(4) . . . . ?
C11 N11 C51 C101 31.9(5) . . . . ?
C11 N11 C51 C61 -146.8(3) . . . . ?
C11 C21 C111 O111 -173.4(3) . . . . ?
C11 C21 C111 C121 6.9(5) . . . . ?
C11 C21 C31 N21 0.5(4) . . . . ?
C11 C21 C31 C41 -177.8(4) . . . . ?
C132 N32 C122 C112 -168.7(2) . . . . ?
C132 N32 C162 C152 15.7(3) . . . . ?
C62 C52 C102 C92 -0.3(5) . . . . ?
C21 C111 C121 N31 -163.3(3) . . . . ?
C111 C21 C31 N21 -174.9(3) . . . . ?
C111 C21 C31 C41 6.8(6) . . . . ?
C122 N32 C132 C142 -118.7(3) . . . . ?
C122 N32 C162 C152 139.4(3) . . . . ?
C102 C52 C62 C72 1.8(5) . . . . ?
C102 C92 C82 C72 0.9(5) . . . . ?
C112 C22 C32 N22 180.0(3) . . . . ?
C112 C22 C32 C42 -2.1(6) . . . . ?
C51 N11 N21 C31 -176.0(3) . . . . ?
C51 N11 C11 O11 -2.6(5) . . . . ?
C51 N11 C11 C21 175.5(3) . . . . ?
C51 C101 C91 C81 -0.8(5) . . . . ?
C51 C61 C71 C81 -1.2(6) . . . . ?
C162 N32 C132 C142 6.6(3) . . . . ?
C162 N32 C122 C112 70.0(3) . . . . ?
C162 C152 C142 C132 36.0(4) . . . . ?
C32 C22 C112 O112 -4.9(6) . . . . ?
C32 C22 C112 C122 176.3(3) . . . . ?
C121 N31 C131 C141 -143.1(4) . . . . ?
C121 N31 C161 C151 148.6(5) . . . . ?
C101 C51 C61 C71 -1.2(5) . . . . ?
C101 C91 C81 C71 -1.6(6) . . . . ?
C92 C82 C72 C62 0.7(5) . . . . ?
C61 C51 C101 C91 2.2(5) . . . . ?
C31 C21 C111 O111 1.1(6) . . . . ?
C31 C21 C111 C121 -178.6(3) . . . . ?
C91 C81 C71 C61 2.6(6) . . . . ?
C131 N31 C121 C111 -164.7(3) . . . . ?
C131 N31 C161 C151 24.2(5) . . . . ?
C161 N31 C121 C111 75.1(4) . . . . ?
C161 N31 C131 C141 -18.7(4) . . . . ?
C161 C151 C141 C131 7.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.723
_oxdiff_exptl_absorpt_empirical_full_min 0.372
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4899(13) 19936 20028 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5101(13) 19867 20028 nmt 1.0011 -0.0018 -0.0013 0.8252 -1.0014 -0.0010
0.0074 0.0009 -1.0003

_twin_special_details            
;
Component 2 rotated by 179.9640° 
around [0.92 0.38 0.00] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
####################################################################### 
# 
# 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_b_0144
_database_code_depnum_ccdc_archive 'CCDC 2119866'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl Cs N2 O5'
_chemical_formula_sum            'C13 H10 Cl Cs N2 O5'
_chemical_formula_weight         442.59
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   48.4669(10)
_cell_length_b                   32.2650(5)
_cell_length_c                   4.40930(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6895.2(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    15288
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.8460
_cell_measurement_theta_min      2.1020
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            33825
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_min         1.516
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -130.61  53.59   0.60   10.00  14.61  -8.96 -28.85    --   307
  2  ω   -104.62  19.58   0.60   10.00    --   -8.96 -59.25 -51.92  207
  3  ω   -104.62  19.58   0.60   10.00    --   -8.96 -59.25  92.08  207
  4  ω   -104.62  19.58   0.60   10.00    --   -8.96 -59.25 164.08  207
  5  ω   -104.62  19.58   0.60   10.00    --   -8.96 -59.25-123.92  207
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3270
_reflns_number_total             3406
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+34.1559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.36717(2) 0.29665(2) -0.05280(7) 0.06142(14) Uani 1 1 d . . . . .
Cl1 Cl 0.34500(5) 0.45130(6) -0.0760(7) 0.0853(6) Uani 1 1 d . . . . .
O1 O 0.39347(8) 0.35129(12) 0.4364(15) 0.0550(10) Uani 1 1 d . . . . .
O11 O 0.39510(10) 0.48220(13) 0.1943(17) 0.0667(12) Uani 1 1 d . . . . .
N2 N 0.45385(11) 0.40489(17) 0.6352(16) 0.0581(15) Uani 1 1 d . . . . .
N1 N 0.43682(11) 0.36991(16) 0.6171(13) 0.0516(14) Uani 1 1 d . . . . .
C1 C 0.41215(11) 0.37751(17) 0.4697(17) 0.0446(12) Uani 1 1 d . . . . .
C3 C 0.43984(14) 0.4343(2) 0.5067(17) 0.0559(18) Uani 1 1 d . . . . .
C5 C 0.44679(12) 0.3321(2) 0.7411(17) 0.0506(15) Uani 1 1 d . . . . .
C2 C 0.41374(13) 0.42085(18) 0.3941(15) 0.0464(14) Uani 1 1 d . . . . .
C6 C 0.46715(14) 0.3338(2) 0.961(2) 0.0661(17) Uani 1 1 d . . . . .
H6 H 0.473732 0.359293 1.027518 0.079 Uiso 1 1 calc R U . . .
C7 C 0.47752(18) 0.2982(3) 1.079(2) 0.081(3) Uani 1 1 d . . . . .
H7 H 0.490926 0.299768 1.229478 0.097 Uiso 1 1 calc R U . . .
C11 C 0.39356(14) 0.44398(18) 0.2364(17) 0.0509(15) Uani 1 1 d . . . . .
C8 C 0.46872(16) 0.2597(2) 0.982(2) 0.070(2) Uani 1 1 d . . . . .
H8 H 0.476596 0.235587 1.058241 0.084 Uiso 1 1 calc R U . . .
C10 C 0.43708(15) 0.2941(2) 0.6445(18) 0.0586(17) Uani 1 1 d . . . . .
H10 H 0.423387 0.292735 0.497124 0.070 Uiso 1 1 calc R U . . .
C9 C 0.44779(17) 0.2581(2) 0.7677(18) 0.065(2) Uani 1 1 d . . . . .
H9 H 0.440888 0.232537 0.706238 0.078 Uiso 1 1 calc R U . . .
C50 C 0.2943(3) 0.3431(4) 0.367(4) 0.121(5) Uani 1 1 d . . . . .
O502 O 0.31631(19) 0.3285(3) 0.325(5) 0.236(11) Uani 1 1 d . . . . .
C4 C 0.45178(18) 0.4769(2) 0.483(3) 0.095(3) Uani 1 1 d . . . . .
H4A H 0.470374 0.476687 0.557814 0.142 Uiso 1 1 calc R U . . .
H4B H 0.440897 0.495799 0.601032 0.142 Uiso 1 1 calc R U . . .
H4C H 0.451732 0.485533 0.274566 0.142 Uiso 1 1 calc R U . . .
O503 O 0.2674(3) 0.3179(5) 0.300(5) 0.258(11) Uani 1 1 d . . . . .
C12 C 0.36947(15) 0.4196(2) 0.1086(17) 0.0591(17) Uani 1 1 d . . . . .
H12A H 0.360444 0.404742 0.272322 0.071 Uiso 1 1 calc R U . . .
H12B H 0.376400 0.399202 -0.034249 0.071 Uiso 1 1 calc R U . . .
O501 O 0.2896(3) 0.3840(5) 0.506(6) 0.298(11) 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
Cs1 Cs1 4.40931(11) 1_554 ?
Cs1 Cs1 4.40929(9) 1_556 ?
Cs1 Cl1 3.718(2) 16_545 ?
Cs1 O1 3.064(5) . ?
Cs1 O1 3.131(5) 1_554 ?
Cs1 O11 3.098(6) 16_544 ?
Cs1 O11 3.079(6) 16_545 ?
Cs1 C10 3.643(7) 1_554 ?
Cs1 O502 3.148(12) . ?
Cl1 C12 1.766(7) . ?
O1 C1 1.248(7) . ?
O11 C11 1.249(7) . ?
N2 N1 1.401(7) . ?
N2 C3 1.298(9) . ?
N1 C1 1.383(8) . ?
N1 C5 1.420(8) . ?
C1 C2 1.439(8) . ?
C3 C2 1.427(9) . ?
C3 C4 1.494(9) . ?
C5 C6 1.384(11) . ?
C5 C10 1.381(10) . ?
C2 C11 1.413(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.358(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(13) . ?
C11 C12 1.517(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(12) . ?
C10 H10 0.9300 . ?
C10 C9 1.384(10) . ?
C9 H9 0.9300 . ?
C50 O502 1.178(13) . ?
C50 O503 1.568(18) . ?
C50 O501 1.47(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
Cs1 Cs1 Cs1 180.0 1_556 1_554 ?
Cl1 Cs1 Cs1 105.60(4) 16_545 1_554 ?
Cl1 Cs1 Cs1 74.39(4) 16_545 1_556 ?
O1 Cs1 Cs1 134.76(10) . 1_554 ?
O1 Cs1 Cs1 44.01(9) 1_554 1_554 ?
O1 Cs1 Cs1 45.24(10) . 1_556 ?
O1 Cs1 Cs1 135.99(9) 1_554 1_556 ?
O1 Cs1 Cl1 94.68(9) . 16_545 ?
O1 Cs1 Cl1 117.29(9) 1_554 16_545 ?
O1 Cs1 O1 90.75(10) . 1_554 ?
O1 Cs1 O11 165.99(12) . 16_544 ?
O1 Cs1 O11 88.16(16) . 16_545 ?
O1 Cs1 C10 50.98(13) 1_554 1_554 ?
O1 Cs1 C10 83.33(16) . 1_554 ?
O1 Cs1 O502 121.0(3) 1_554 . ?
O1 Cs1 O502 76.4(3) . . ?
O11 Cs1 Cs1 44.62(12) 16_545 1_556 ?
O11 Cs1 Cs1 44.29(10) 16_544 1_554 ?
O11 Cs1 Cs1 135.38(12) 16_545 1_554 ?
O11 Cs1 Cs1 135.71(10) 16_544 1_556 ?
O11 Cs1 Cl1 74.44(11) 16_544 16_545 ?
O11 Cs1 Cl1 49.09(10) 16_545 16_545 ?
O11 Cs1 O1 166.12(12) 16_545 1_554 ?
O11 Cs1 O1 86.63(15) 16_544 1_554 ?
O11 Cs1 O11 91.09(11) 16_545 16_544 ?
O11 Cs1 C10 115.18(14) 16_545 1_554 ?
O11 Cs1 C10 84.34(15) 16_544 1_554 ?
O11 Cs1 O502 116.6(3) 16_544 . ?
O11 Cs1 O502 72.1(3) 16_545 . ?
C10 Cs1 Cs1 111.49(13) 1_554 1_556 ?
C10 Cs1 Cs1 68.51(13) 1_554 1_554 ?
C10 Cs1 Cl1 67.75(11) 1_554 16_545 ?
O502 Cs1 Cs1 122.0(3) . 1_554 ?
O502 Cs1 Cs1 58.0(3) . 1_556 ?
O502 Cs1 Cl1 120.9(3) . 16_545 ?
O502 Cs1 C10 158.4(3) . 1_554 ?
C12 Cl1 Cs1 105.8(3) . 12_554 ?
Cs1 O1 Cs1 90.75(10) . 1_556 ?
C1 O1 Cs1 140.8(5) . . ?
C1 O1 Cs1 126.3(5) . 1_556 ?
Cs1 O11 Cs1 91.09(11) 12_554 12 ?
C11 O11 Cs1 139.5(5) . 12_554 ?
C11 O11 Cs1 123.0(5) . 12 ?
C3 N2 N1 104.9(5) . . ?
N2 N1 C5 118.0(5) . . ?
C1 N1 N2 113.1(5) . . ?
C1 N1 C5 128.9(5) . . ?
O1 C1 N1 124.2(5) . . ?
O1 C1 C2 132.1(6) . . ?
N1 C1 C2 103.6(5) . . ?
N2 C3 C2 113.1(6) . . ?
N2 C3 C4 120.0(7) . . ?
C2 C3 C4 126.8(7) . . ?
C6 C5 N1 118.6(6) . . ?
C10 C5 N1 121.8(6) . . ?
C10 C5 C6 119.6(7) . . ?
C3 C2 C1 105.2(5) . . ?
C11 C2 C1 126.1(6) . . ?
C11 C2 C3 128.6(6) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(8) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.8(9) . . ?
C8 C7 H7 119.1 . . ?
O11 C11 C2 123.6(6) . . ?
O11 C11 C12 120.2(6) . . ?
C2 C11 C12 116.2(5) . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.1(7) . . ?
C9 C8 H8 120.9 . . ?
Cs1 C10 H10 66.0 1_556 . ?
C5 C10 Cs1 100.6(4) . 1_556 ?
C5 C10 H10 120.1 . . ?
C5 C10 C9 119.8(7) . . ?
C9 C10 Cs1 102.9(5) . 1_556 ?
C9 C10 H10 120.1 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(8) . . ?
C10 C9 H9 119.7 . . ?
O502 C50 O503 121.1(14) . . ?
O502 C50 O501 124.4(15) . . ?
O501 C50 O503 114.4(13) . . ?
C50 O502 Cs1 157.1(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Cl1 C12 H12A 109.0 . . ?
Cl1 C12 H12B 109.0 . . ?
C11 C12 Cl1 112.8(5) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?

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
Cs1 Cl1 C12 C11 23.3(6) 12_554 . . . ?
Cs1 O1 C1 N1 -107.0(8) . . . . ?
Cs1 O1 C1 N1 51.0(9) 1_556 . . . ?
Cs1 O1 C1 C2 -124.4(7) 1_556 . . . ?
Cs1 O1 C1 C2 77.5(10) . . . . ?
Cs1 O11 C11 C2 -76.3(8) 12 . . . ?
Cs1 O11 C11 C2 140.9(6) 12_554 . . . ?
Cs1 O11 C11 C12 -37.4(11) 12_554 . . . ?
Cs1 O11 C11 C12 105.4(7) 12 . . . ?
Cs1 C10 C9 C8 -112.1(7) 1_556 . . . ?
O1 C1 C2 C3 176.4(8) . . . . ?
O1 C1 C2 C11 -4.7(13) . . . . ?
O11 C11 C12 Cl1 -3.0(10) . . . . ?
N2 N1 C1 O1 -177.5(7) . . . . ?
N2 N1 C1 C2 -0.9(7) . . . . ?
N2 N1 C5 C6 22.6(10) . . . . ?
N2 N1 C5 C10 -156.2(6) . . . . ?
N2 C3 C2 C1 0.6(8) . . . . ?
N2 C3 C2 C11 -178.3(7) . . . . ?
N1 N2 C3 C2 -1.1(8) . . . . ?
N1 N2 C3 C4 -179.8(8) . . . . ?
N1 C1 C2 C3 0.2(7) . . . . ?
N1 C1 C2 C11 179.2(6) . . . . ?
N1 C5 C6 C7 -178.6(7) . . . . ?
N1 C5 C10 Cs1 -69.6(7) . . . 1_556 ?
N1 C5 C10 C9 178.7(6) . . . . ?
C1 N1 C5 C6 -159.0(7) . . . . ?
C1 N1 C5 C10 22.2(11) . . . . ?
C1 C2 C11 O11 175.0(7) . . . . ?
C1 C2 C11 C12 -6.6(11) . . . . ?
C3 N2 N1 C1 1.3(8) . . . . ?
C3 N2 N1 C5 180.0(6) . . . . ?
C3 C2 C11 O11 -6.3(12) . . . . ?
C3 C2 C11 C12 172.1(7) . . . . ?
C5 N1 C1 O1 4.1(12) . . . . ?
C5 N1 C1 C2 -179.4(6) . . . . ?
C5 C6 C7 C8 1.3(14) . . . . ?
C5 C10 C9 C8 -1.7(11) . . . . ?
C2 C11 C12 Cl1 178.6(5) . . . . ?
C6 C5 C10 Cs1 111.6(6) . . . 1_556 ?
C6 C5 C10 C9 -0.1(11) . . . . ?
C6 C7 C8 C9 -3.0(13) . . . . ?
C7 C8 C9 C10 3.1(12) . . . . ?
C10 C5 C6 C7 0.3(12) . . . . ?
C4 C3 C2 C1 179.1(9) . . . . ?
C4 C3 C2 C11 0.2(13) . . . . ?
O503 C50 O502 Cs1 74(3) . . . . ?
O501 C50 O502 Cs1 -111(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_b_0145_0ma
_database_code_depnum_ccdc_archive 'CCDC 2119861'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N4 O2'
_chemical_formula_sum            'C22 H24 N4 O2'
_chemical_formula_weight         376.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.0544(6)
_cell_length_b                   13.0083(6)
_cell_length_c                   11.7110(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.3530(10)
_cell_angle_gamma                90
_cell_volume                     1926.64(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7122
_cell_measurement_temperature    290
_cell_measurement_theta_max      31.449
_cell_measurement_theta_min      2.382
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0848 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37820
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2949
_reflns_number_total             4394
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.6588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C10(H10), C18(H18), C20(H20), C6(H6), C19(H19), C21(H21), C8(H8),
 C7(H7), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47331(9) 0.33300(10) 0.79048(10) 0.0429(3) Uani 1 1 d . . . . .
O11 O 0.37684(11) 0.36862(12) 0.41196(11) 0.0556(4) Uani 1 1 d . . . . .
N3 N 0.57253(12) 0.28696(11) 0.47184(13) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.29658(11) 0.37973(12) 0.76953(12) 0.0377(4) Uani 1 1 d . . . . .
N2 N 0.20609(11) 0.39792(12) 0.67924(13) 0.0411(4) Uani 1 1 d . . . . .
N4 N 0.76021(11) 0.28437(12) 0.38204(13) 0.0392(4) Uani 1 1 d . . . . .
C1 C 0.38277(13) 0.35547(13) 0.72659(14) 0.0336(4) Uani 1 1 d . . . . .
C2 C 0.34572(13) 0.36401(13) 0.60210(15) 0.0346(4) Uani 1 1 d . . . . .
C11 C 0.40670(14) 0.35046(14) 0.51856(15) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.23658(14) 0.38973(14) 0.58145(16) 0.0382(4) Uani 1 1 d . . . . .
C15 C 0.67421(14) 0.35727(14) 0.33798(16) 0.0403(4) Uani 1 1 d . . . . .
H15A H 0.625297 0.328270 0.269396 0.048 Uiso 1 1 calc R U . . .
H15B H 0.702963 0.420032 0.313736 0.048 Uiso 1 1 calc R U . . .
C16 C 0.61565(15) 0.38228(14) 0.42986(16) 0.0408(4) Uani 1 1 d . . . . .
H16A H 0.663083 0.416255 0.496005 0.049 Uiso 1 1 calc R U . . .
H16B H 0.558052 0.429078 0.396946 0.049 Uiso 1 1 calc R U . . .
C5 C 0.29055(15) 0.39016(14) 0.88773(16) 0.0398(4) Uani 1 1 d . . . . .
C12 C 0.51802(14) 0.30859(15) 0.56667(15) 0.0400(4) Uani 1 1 d . . . . .
H12A H 0.559161 0.358128 0.621152 0.048 Uiso 1 1 calc R U . . .
H12B H 0.514276 0.245767 0.610072 0.048 Uiso 1 1 calc R U . . .
C17 C 0.83181(13) 0.27161(15) 0.30951(16) 0.0398(4) Uani 1 1 d . . . . .
C14 C 0.71977(15) 0.19045(14) 0.42185(17) 0.0419(4) Uani 1 1 d . . . . .
H14A H 0.778055 0.144105 0.453722 0.050 Uiso 1 1 calc R U . . .
H14B H 0.672456 0.156685 0.355453 0.050 Uiso 1 1 calc R U . . .
C13 C 0.66144(14) 0.21322(15) 0.51482(16) 0.0422(4) Uani 1 1 d . . . . .
H13A H 0.633677 0.149642 0.538356 0.051 Uiso 1 1 calc R U . . .
H13B H 0.710365 0.241917 0.583598 0.051 Uiso 1 1 calc R U . . .
C22 C 0.87411(15) 0.35712(16) 0.26753(18) 0.0491(5) Uani 1 1 d . . . . .
H22 H 0.855829 0.422533 0.287706 0.059 Uiso 1 1 calc R U . . .
C10 C 0.37795(16) 0.41734(16) 0.97549(17) 0.0507(5) Uani 1 1 d . . . . .
H10 H 0.442243 0.429742 0.957260 0.061 Uiso 1 1 calc R U . . .
C18 C 0.86300(15) 0.17488(16) 0.27944(18) 0.0498(5) Uani 1 1 d . . . . .
H18 H 0.836292 0.116108 0.306890 0.060 Uiso 1 1 calc R U . . .
C4 C 0.15866(16) 0.40587(18) 0.46615(18) 0.0577(6) Uani 1 1 d . . . . .
H4A H 0.090013 0.418399 0.479279 0.087 Uiso 1 1 calc R U . . .
H4B H 0.156039 0.345670 0.418096 0.087 Uiso 1 1 calc R U . . .
H4C H 0.179736 0.463944 0.426796 0.087 Uiso 1 1 calc R U . . .
C20 C 0.97241(18) 0.2507(2) 0.1660(2) 0.0638(6) Uani 1 1 d . . . . .
H20 H 1.018174 0.243997 0.116894 0.077 Uiso 1 1 calc R U . . .
C6 C 0.19477(18) 0.37593(18) 0.91585(19) 0.0578(6) Uani 1 1 d . . . . .
H6 H 0.134737 0.359392 0.857240 0.069 Uiso 1 1 calc R U . . .
C19 C 0.93343(17) 0.16573(19) 0.2090(2) 0.0604(6) Uani 1 1 d . . . . .
H19 H 0.954493 0.100746 0.190778 0.072 Uiso 1 1 calc R U . . .
C21 C 0.94310(16) 0.34628(18) 0.1961(2) 0.0586(6) Uani 1 1 d . . . . .
H21 H 0.970099 0.404552 0.167939 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2757(2) 0.40985(19) 1.1192(2) 0.0699(7) Uani 1 1 d . . . . .
H8 H 0.271031 0.414674 1.196942 0.084 Uiso 1 1 calc R U . . .
C7 C 0.1885(2) 0.3863(2) 1.0312(2) 0.0732(7) Uani 1 1 d . . . . .
H7 H 0.123758 0.377165 1.049468 0.088 Uiso 1 1 calc R U . . .
C9 C 0.3699(2) 0.42615(19) 1.0908(2) 0.0662(7) Uani 1 1 d . . . . .
H9 H 0.429400 0.443398 1.149737 0.079 Uiso 1 1 calc R U . . .
H3 H 0.5236(17) 0.2550(16) 0.4044(18) 0.056(6) 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 C1 1.2664(19) . ?
O11 C11 1.235(2) . ?
N3 C16 1.494(2) . ?
N3 C12 1.487(2) . ?
N3 C13 1.494(2) . ?
N3 H3 0.98(2) . ?
N1 N2 1.3966(19) . ?
N1 C1 1.378(2) . ?
N1 C5 1.412(2) . ?
N2 C3 1.307(2) . ?
N4 C15 1.463(2) . ?
N4 C17 1.420(2) . ?
N4 C14 1.453(2) . ?
C1 C2 1.422(2) . ?
C2 C11 1.417(2) . ?
C2 C3 1.425(2) . ?
C11 C12 1.523(2) . ?
C3 C4 1.490(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.502(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C5 C10 1.379(3) . ?
C5 C6 1.382(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 C22 1.385(3) . ?
C17 C18 1.394(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.505(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C21 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.365(3) . ?
C20 C21 1.372(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.367(4) . ?
C8 C9 1.368(4) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?

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 N3 H3 108.1(12) . . ?
C12 N3 C16 112.20(14) . . ?
C12 N3 C13 110.22(13) . . ?
C12 N3 H3 110.3(12) . . ?
C13 N3 C16 108.60(14) . . ?
C13 N3 H3 107.3(12) . . ?
N2 N1 C5 118.92(14) . . ?
C1 N1 N2 112.11(13) . . ?
C1 N1 C5 128.95(15) . . ?
C3 N2 N1 105.40(13) . . ?
C17 N4 C15 115.24(14) . . ?
C17 N4 C14 116.05(15) . . ?
C14 N4 C15 110.50(14) . . ?
O1 C1 N1 124.34(15) . . ?
O1 C1 C2 130.86(16) . . ?
N1 C1 C2 104.79(14) . . ?
C1 C2 C3 105.31(15) . . ?
C11 C2 C1 126.27(16) . . ?
C11 C2 C3 128.42(16) . . ?
O11 C11 C2 125.69(17) . . ?
O11 C11 C12 118.40(16) . . ?
C2 C11 C12 115.91(15) . . ?
N2 C3 C2 112.30(15) . . ?
N2 C3 C4 119.66(16) . . ?
C2 C3 C4 128.03(17) . . ?
N4 C15 H15A 109.3 . . ?
N4 C15 H15B 109.3 . . ?
N4 C15 C16 111.73(15) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N3 C16 C15 110.86(14) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C10 C5 N1 121.21(17) . . ?
C10 C5 C6 119.14(18) . . ?
C6 C5 N1 119.62(18) . . ?
N3 C12 C11 112.38(14) . . ?
N3 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C22 C17 N4 119.86(17) . . ?
C22 C17 C18 117.91(17) . . ?
C18 C17 N4 122.23(17) . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 C13 110.85(15) . . ?
H14A C14 H14B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
N3 C13 C14 111.90(14) . . ?
N3 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.71(19) . . ?
C21 C22 H22 119.6 . . ?
C5 C10 H10 120.0 . . ?
C5 C10 C9 119.9(2) . . ?
C9 C10 H10 120.0 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.1(2) . . ?
C21 C20 H20 120.5 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C22 C21 H21 119.5 . . ?
C20 C21 C22 120.9(2) . . ?
C20 C21 H21 119.5 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15B N2 0.97 2.64 3.575(2) 161.6 3_666 yes
C16 H16B O11 0.97 2.54 3.077(2) 114.9 . yes
C14 H14B O1 0.97 2.52 3.218(2) 128.4 4_565 yes
C22 H22 N2 0.93 2.53 3.459(3) 174.0 3_666 yes
C10 H10 O1 0.93 2.44 2.964(2) 115.6 . yes
N3 H3 O1 0.98(2) 1.76(2) 2.6944(19) 159.6(18) 4_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -1.5(3) . . . . ?
O1 C1 C2 C3 179.09(18) . . . . ?
O11 C11 C12 N3 -5.0(2) . . . . ?
N1 N2 C3 C2 1.3(2) . . . . ?
N1 N2 C3 C4 -179.39(17) . . . . ?
N1 C1 C2 C11 177.29(16) . . . . ?
N1 C1 C2 C3 -2.09(18) . . . . ?
N1 C5 C10 C9 -179.45(18) . . . . ?
N1 C5 C6 C7 -179.83(19) . . . . ?
N2 N1 C1 O1 -178.04(16) . . . . ?
N2 N1 C1 C2 3.05(19) . . . . ?
N2 N1 C5 C10 -151.61(18) . . . . ?
N2 N1 C5 C6 26.5(2) . . . . ?
N4 C15 C16 N3 -57.4(2) . . . . ?
N4 C17 C22 C21 -179.42(18) . . . . ?
N4 C17 C18 C19 -179.65(18) . . . . ?
N4 C14 C13 N3 57.4(2) . . . . ?
C1 N1 N2 C3 -2.78(19) . . . . ?
C1 N1 C5 C10 26.6(3) . . . . ?
C1 N1 C5 C6 -155.31(19) . . . . ?
C1 C2 C11 O11 -171.81(18) . . . . ?
C1 C2 C11 C12 8.9(3) . . . . ?
C1 C2 C3 N2 0.5(2) . . . . ?
C1 C2 C3 C4 -178.73(19) . . . . ?
C2 C11 C12 N3 174.31(15) . . . . ?
C11 C2 C3 N2 -178.87(17) . . . . ?
C11 C2 C3 C4 1.9(3) . . . . ?
C3 C2 C11 O11 7.4(3) . . . . ?
C3 C2 C11 C12 -171.83(17) . . . . ?
C15 N4 C17 C22 48.5(2) . . . . ?
C15 N4 C17 C18 -132.34(18) . . . . ?
C15 N4 C14 C13 -56.82(19) . . . . ?
C16 N3 C12 C11 79.26(19) . . . . ?
C16 N3 C13 C14 -55.89(19) . . . . ?
C5 N1 N2 C3 175.74(15) . . . . ?
C5 N1 C1 O1 3.6(3) . . . . ?
C5 N1 C1 C2 -175.28(16) . . . . ?
C5 C10 C9 C8 -1.1(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C12 N3 C16 C15 177.53(15) . . . . ?
C12 N3 C13 C14 -179.17(15) . . . . ?
C17 N4 C15 C16 -168.50(15) . . . . ?
C17 N4 C14 C13 169.59(15) . . . . ?
C17 C22 C21 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C14 N4 C15 C16 57.50(19) . . . . ?
C14 N4 C17 C22 179.93(17) . . . . ?
C14 N4 C17 C18 -0.9(2) . . . . ?
C13 N3 C16 C15 55.45(19) . . . . ?
C13 N3 C12 C11 -159.58(15) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C10 C5 C6 C7 -1.7(3) . . . . ?
C18 C17 C22 C21 1.4(3) . . . . ?
C6 C5 C10 C9 2.5(3) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C21 C20 C19 C18 1.8(4) . . . . ?
C7 C8 C9 C10 -1.1(4) . . . . ?
C9 C8 C7 C6 1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0161_0m
_database_code_depnum_ccdc_archive 'CCDC 2119867'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N3 O2'
_chemical_formula_sum            'C19 H25 N3 O2'
_chemical_formula_weight         327.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7988(8)
_cell_length_b                   18.792(2)
_cell_length_c                   13.5975(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.066(4)
_cell_angle_gamma                90
_cell_volume                     1732.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.246
_cell_measurement_theta_min      2.637
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0770 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50776
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             3786
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.067(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+1.0650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H18C)=Sof(H18D)=Sof(H14C)=Sof(H14D)=Sof(H16C)=Sof(H16D)=Sof(C15B)=
 Sof(H15C)=Sof(H15D)=Sof(C17B)=Sof(H17C)=Sof(H17D)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(H14A)=Sof(H14B)=Sof(H16A)=Sof(H16B)=Sof(C15A)=
 Sof(H15A)=Sof(H15B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C13(H13A,H13B), C18(H18A,H18B), C18(H18C,
 H18D), C14(H14A,H14B), C14(H14C,H14D), C16(H16A,H16B), C16(H16C,H16D),
 C15A(H15A,H15B), C17A(H17A,H17B), C15B(H15C,H15D), C17B(H17C,H17D)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C7(H7), C9(H9), C8(H8)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8107(2) 0.67965(7) 0.60660(11) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.5056(2) 0.72095(8) 0.54181(12) 0.0422(4) Uani 1 1 d . . . . .
N3 N 1.0144(2) 0.72585(9) 0.76263(13) 0.0446(4) Uani 1 1 d . . . . .
N2 N 0.3881(2) 0.78171(9) 0.54440(13) 0.0468(4) Uani 1 1 d . . . . .
O11 O 0.8144(3) 0.89704(8) 0.72213(15) 0.0731(6) Uani 1 1 d . . . . .
C2 C 0.6782(3) 0.79883(10) 0.63514(14) 0.0419(4) Uani 1 1 d . . . . .
C1 C 0.6823(3) 0.72876(10) 0.59633(13) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.4301(3) 0.65902(10) 0.49261(13) 0.0406(4) Uani 1 1 d . . . . .
C11 C 0.8297(3) 0.83558(10) 0.69422(15) 0.0474(5) Uani 1 1 d . . . . .
C3 C 0.4929(3) 0.82728(10) 0.59940(15) 0.0450(5) Uani 1 1 d . . . . .
C6 C 0.2326(3) 0.64179(12) 0.49583(16) 0.0516(5) Uani 1 1 d . . . . .
H6 H 0.149207 0.671078 0.529058 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5536(3) 0.61610(12) 0.44227(15) 0.0521(5) Uani 1 1 d . . . . .
H10 H 0.685802 0.627960 0.439147 0.062 Uiso 1 1 calc R U . . .
C12 C 1.0274(3) 0.79922(11) 0.72134(16) 0.0499(5) Uani 1 1 d . . . . .
H12A H 1.100827 0.796988 0.662802 0.060 Uiso 1 1 calc R U . . .
H12B H 1.102048 0.828656 0.769230 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4137(4) 0.90035(12) 0.6157(2) 0.0626(6) Uani 1 1 d . . . . .
H4A H 0.495838 0.934909 0.586657 0.094 Uiso 1 1 calc R U . . .
H4B H 0.412563 0.909226 0.685229 0.094 Uiso 1 1 calc R U . . .
H4C H 0.281810 0.903771 0.585817 0.094 Uiso 1 1 calc R U . . .
C19 C 0.9039(4) 0.72577(13) 0.85406(17) 0.0658(7) Uani 1 1 d . . . . .
H19A H 0.998842 0.728831 0.910606 0.079 Uiso 1 1 calc R U . . .
H19B H 0.823187 0.768343 0.853783 0.079 Uiso 1 1 calc R U . . .
C13 C 1.2182(3) 0.69474(14) 0.7761(2) 0.0692(7) Uani 1 1 d . . . . .
H13A H 1.296804 0.714768 0.726130 0.083 Uiso 1 1 calc R U . . .
H13B H 1.277000 0.709945 0.839757 0.083 Uiso 1 1 calc R U . . .
C7 C 0.1605(4) 0.58104(14) 0.4495(2) 0.0678(7) Uani 1 1 d . . . . .
H7 H 0.027728 0.569546 0.451305 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4779(4) 0.55502(14) 0.39636(19) 0.0685(7) Uani 1 1 d . . . . .
H9 H 0.560150 0.525822 0.362273 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2828(4) 0.53729(14) 0.4008(2) 0.0746(8) Uani 1 1 d . . . . .
H8 H 0.233650 0.495805 0.370944 0.090 Uiso 1 1 calc R U . . .
C18 C 0.7749(4) 0.66338(18) 0.8678(2) 0.0827(9) Uani 1 1 d . . . . .
H18A H 0.722576 0.646801 0.803631 0.099 Uiso 0.610(6) 1 calc R U P A 1
H18B H 0.664406 0.678240 0.904241 0.099 Uiso 0.610(6) 1 calc R U P A 1
H18C H 0.759405 0.660685 0.938067 0.099 Uiso 0.390(6) 1 calc R U P A 2
H18D H 0.646593 0.676162 0.837163 0.099 Uiso 0.390(6) 1 calc R U P A 2
C14 C 1.2322(5) 0.61643(18) 0.7709(3) 0.0998(11) Uani 1 1 d . . . . .
H14A H 1.144756 0.601319 0.715394 0.120 Uiso 0.610(6) 1 calc R U P A 1
H14B H 1.365284 0.605276 0.754457 0.120 Uiso 0.610(6) 1 calc R U P A 1
H14C H 1.300262 0.606533 0.712088 0.120 Uiso 0.390(6) 1 calc R U P A 2
H14D H 1.322295 0.602725 0.826200 0.120 Uiso 0.390(6) 1 calc R U P A 2
C16 C 0.9804(8) 0.5473(2) 0.8621(4) 0.1291(16) Uani 1 1 d . . . . .
H16A H 0.911780 0.543640 0.797278 0.155 Uiso 0.610(6) 1 calc R U P A 1
H16B H 0.979453 0.500901 0.893352 0.155 Uiso 0.610(6) 1 calc R U P A 1
H16C H 0.946566 0.497148 0.862444 0.155 Uiso 0.390(6) 1 calc R U P A 2
H16D H 1.053475 0.560379 0.923283 0.155 Uiso 0.390(6) 1 calc R U P A 2
C15A C 1.1907(9) 0.5719(3) 0.8532(5) 0.105(2) Uani 0.610(6) 1 d . . P A 1
H15A H 1.232231 0.597380 0.913137 0.127 Uiso 0.610(6) 1 calc R U P A 1
H15B H 1.273035 0.529844 0.851006 0.127 Uiso 0.610(6) 1 calc R U P A 1
C17A C 0.8813(12) 0.6009(3) 0.9231(5) 0.103(2) Uani 0.610(6) 1 d . . P A 1
H17A H 0.979862 0.620674 0.970491 0.124 Uiso 0.610(6) 1 calc R U P A 1
H17B H 0.785585 0.576088 0.960133 0.124 Uiso 0.610(6) 1 calc R U P A 1
C15B C 1.0846(9) 0.5697(3) 0.7698(5) 0.0587(18) Uani 0.390(6) 1 d . . P A 2
H15C H 1.133347 0.526233 0.741660 0.070 Uiso 0.390(6) 1 calc R U P A 2
H15D H 0.982417 0.587675 0.722932 0.070 Uiso 0.390(6) 1 calc R U P A 2
C17B C 0.8096(13) 0.5936(4) 0.8377(11) 0.100(4) Uani 0.390(6) 1 d . . P A 2
H17C H 0.797134 0.595279 0.766216 0.120 Uiso 0.390(6) 1 calc R U P A 2
H17D H 0.696828 0.566632 0.856905 0.120 Uiso 0.390(6) 1 calc R U P A 2
H3 H 0.946(4) 0.7024(13) 0.7110(18) 0.056(6) 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 C1 1.271(2) . ?
N1 N2 1.396(2) . ?
N1 C1 1.374(2) . ?
N1 C5 1.420(2) . ?
N3 C12 1.494(3) . ?
N3 C19 1.498(3) . ?
N3 C13 1.503(3) . ?
N3 H3 0.93(3) . ?
N2 C3 1.313(3) . ?
O11 C11 1.223(2) . ?
C2 C1 1.420(3) . ?
C2 C11 1.437(3) . ?
C2 C3 1.422(3) . ?
C5 C6 1.385(3) . ?
C5 C10 1.380(3) . ?
C11 C12 1.530(3) . ?
C3 C4 1.497(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.388(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.484(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.477(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(4) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C18 C17A 1.546(7) . ?
C18 C17B 1.399(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C15A 1.441(7) . ?
C14 C15B 1.333(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C16 C15A 1.515(7) . ?
C16 C17A 1.496(7) . ?
C16 C15B 1.542(8) . ?
C16 C17B 1.470(10) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 119.59(15) . . ?
C1 N1 N2 112.29(15) . . ?
C1 N1 C5 127.94(15) . . ?
C12 N3 C19 111.06(16) . . ?
C12 N3 C13 109.06(16) . . ?
C12 N3 H3 101.2(15) . . ?
C19 N3 C13 114.3(2) . . ?
C19 N3 H3 111.9(15) . . ?
C13 N3 H3 108.5(15) . . ?
C3 N2 N1 105.03(15) . . ?
C1 C2 C11 128.41(17) . . ?
C1 C2 C3 105.19(16) . . ?
C3 C2 C11 126.35(18) . . ?
O1 C1 N1 123.29(17) . . ?
O1 C1 C2 131.61(17) . . ?
N1 C1 C2 105.08(15) . . ?
C6 C5 N1 119.71(18) . . ?
C10 C5 N1 120.02(18) . . ?
C10 C5 C6 120.27(19) . . ?
O11 C11 C2 123.6(2) . . ?
O11 C11 C12 116.10(19) . . ?
C2 C11 C12 120.19(17) . . ?
N2 C3 C2 112.40(17) . . ?
N2 C3 C4 119.75(19) . . ?
C2 C3 C4 127.83(19) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C10 H10 120.4 . . ?
C5 C10 C9 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
N3 C12 C11 115.39(16) . . ?
N3 C12 H12A 108.4 . . ?
N3 C12 H12B 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C19 H19A 108.2 . . ?
N3 C19 H19B 108.2 . . ?
H19A C19 H19B 107.4 . . ?
C18 C19 N3 116.2(2) . . ?
C18 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
N3 C13 H13A 108.2 . . ?
N3 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 N3 116.4(2) . . ?
C14 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C19 C18 H18C 105.8 . . ?
C19 C18 H18D 105.8 . . ?
C19 C18 C17A 113.6(4) . . ?
H18A C18 H18B 107.7 . . ?
H18C C18 H18D 106.2 . . ?
C17A C18 H18A 108.8 . . ?
C17A C18 H18B 108.8 . . ?
C17B C18 C19 126.2(4) . . ?
C17B C18 H18C 105.8 . . ?
C17B C18 H18D 105.8 . . ?
C13 C14 H14A 106.9 . . ?
C13 C14 H14B 106.9 . . ?
C13 C14 H14C 105.5 . . ?
C13 C14 H14D 105.5 . . ?
H14A C14 H14B 106.7 . . ?
H14C C14 H14D 106.1 . . ?
C15A C14 C13 121.7(4) . . ?
C15A C14 H14A 106.9 . . ?
C15A C14 H14B 106.9 . . ?
C15B C14 C13 127.3(3) . . ?
C15B C14 H14C 105.5 . . ?
C15B C14 H14D 105.5 . . ?
H16A C16 H16B 108.5 . . ?
H16C C16 H16D 110.5 . . ?
C15A C16 H16A 110.2 . . ?
C15A C16 H16B 110.2 . . ?
C17A C16 H16A 110.2 . . ?
C17A C16 H16B 110.2 . . ?
C17A C16 C15A 107.7(5) . . ?
C15B C16 H16C 113.1 . . ?
C15B C16 H16D 113.1 . . ?
C17B C16 H16C 113.1 . . ?
C17B C16 H16D 113.1 . . ?
C17B C16 C15B 93.2(6) . . ?
C14 C15A C16 118.5(5) . . ?
C14 C15A H15A 107.7 . . ?
C14 C15A H15B 107.7 . . ?
C16 C15A H15A 107.7 . . ?
C16 C15A H15B 107.7 . . ?
H15A C15A H15B 107.1 . . ?
C18 C17A H17A 108.0 . . ?
C18 C17A H17B 108.0 . . ?
C16 C17A C18 117.1(5) . . ?
C16 C17A H17A 108.0 . . ?
C16 C17A H17B 108.0 . . ?
H17A C17A H17B 107.3 . . ?
C14 C15B C16 124.0(5) . . ?
C14 C15B H15C 106.3 . . ?
C14 C15B H15D 106.3 . . ?
C16 C15B H15C 106.3 . . ?
C16 C15B H15D 106.3 . . ?
H15C C15B H15D 106.4 . . ?
C18 C17B C16 129.5(9) . . ?
C18 C17B H17C 104.9 . . ?
C18 C17B H17D 104.9 . . ?
C16 C17B H17C 104.9 . . ?
C16 C17B H17D 104.9 . . ?
H17C C17B H17D 105.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 O1 0.93 2.60 3.408(3) 145.1 1_455 yes
C12 H12A N2 0.97 2.63 3.570(3) 162.5 1_655 yes
N3 H3 O1 0.93(3) 1.69(3) 2.600(2) 166(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C3 C2 -0.6(2) . . . . ?
N1 N2 C3 C4 178.04(18) . . . . ?
N1 C5 C6 C7 -178.85(19) . . . . ?
N1 C5 C10 C9 178.68(19) . . . . ?
N3 C19 C18 C17A 88.8(4) . . . . ?
N3 C19 C18 C17B 33.0(8) . . . . ?
N3 C13 C14 C15A -79.3(5) . . . . ?
N3 C13 C14 C15B -10.5(7) . . . . ?
N2 N1 C1 O1 178.18(17) . . . . ?
N2 N1 C1 C2 -0.6(2) . . . . ?
N2 N1 C5 C6 -35.8(3) . . . . ?
N2 N1 C5 C10 144.52(19) . . . . ?
O11 C11 C12 N3 133.5(2) . . . . ?
C2 C11 C12 N3 -49.4(3) . . . . ?
C1 N1 N2 C3 0.8(2) . . . . ?
C1 N1 C5 C6 138.8(2) . . . . ?
C1 N1 C5 C10 -40.8(3) . . . . ?
C1 C2 C11 O11 177.9(2) . . . . ?
C1 C2 C11 C12 1.0(3) . . . . ?
C1 C2 C3 N2 0.2(2) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C5 N1 N2 C3 176.19(16) . . . . ?
C5 N1 C1 O1 3.2(3) . . . . ?
C5 N1 C1 C2 -175.59(17) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C5 C10 C9 C8 0.0(4) . . . . ?
C11 C2 C1 O1 4.1(3) . . . . ?
C11 C2 C1 N1 -177.19(19) . . . . ?
C11 C2 C3 N2 177.73(19) . . . . ?
C11 C2 C3 C4 -0.7(3) . . . . ?
C3 C2 C1 O1 -178.4(2) . . . . ?
C3 C2 C1 N1 0.3(2) . . . . ?
C3 C2 C11 O11 1.0(3) . . . . ?
C3 C2 C11 C12 -175.92(18) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
C6 C7 C8 C9 -1.4(4) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C10 C9 C8 C7 1.2(4) . . . . ?
C12 N3 C19 C18 143.1(2) . . . . ?
C12 N3 C13 C14 -152.5(3) . . . . ?
C19 N3 C12 C11 -58.7(2) . . . . ?
C19 N3 C13 C14 82.6(3) . . . . ?
C19 C18 C17A C16 -89.0(7) . . . . ?
C19 C18 C17B C16 56.5(15) . . . . ?
C13 N3 C12 C11 174.50(19) . . . . ?
C13 N3 C19 C18 -93.1(3) . . . . ?
C13 C14 C15A C16 88.9(6) . . . . ?
C13 C14 C15B C16 -77.6(7) . . . . ?
C15A C16 C17A C18 90.2(7) . . . . ?
C17A C16 C15A C14 -91.1(7) . . . . ?
C15B C16 C17B C18 -93.2(11) . . . . ?
C17B C16 C15B C14 101.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0178_0m
_database_code_depnum_ccdc_archive 'CCDC 2119871'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 Cs N3 O7 S, H2 O'
_chemical_formula_sum            'C17 H26 Cs N3 O8 S'
_chemical_formula_weight         565.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6127(10)
_cell_length_b                   11.6570(11)
_cell_length_c                   15.4167(19)
_cell_angle_alpha                101.296(4)
_cell_angle_beta                 103.003(3)
_cell_angle_gamma                105.412(4)
_cell_volume                     1236.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    1.624
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.8069.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            62002
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.049
_diffrn_reflns_theta_min         2.642
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4551
_reflns_number_total             4829
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4829
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.0844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 Cs1-H3WA \\sim Cs1-H3WB
 with sigma of 0.02
3.a Free rotating group:
 O3W(H3WA,H3WB)
3.b Rotating group:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
3.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C9(H9), C7(H7), C8(H8)
3.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.72106(2) 0.05076(2) 0.43522(2) 0.05028(7) Uani 1 1 d D . . . .
S1 S 0.8912(2) 0.22980(17) 0.92509(7) 0.1203(5) Uani 1 1 d . . . . .
O1 O 0.4665(3) 0.19698(15) 0.36995(12) 0.0471(4) Uani 1 1 d . . . . .
O11 O 0.5446(3) 0.19577(16) 0.56339(12) 0.0496(4) Uani 1 1 d . . . . .
O3W O 1.1276(3) 0.23764(19) 0.57090(15) 0.0590(5) Uani 1 1 d G . . . .
H3WA H 1.129537 0.308664 0.564531 0.089 Uiso 1 1 d DG U . . .
H3WB H 1.202916 0.217962 0.542189 0.089 Uiso 1 1 d DG U . . .
N1 N 0.6094(3) 0.39896(18) 0.36871(13) 0.0393(4) Uani 1 1 d . . . . .
O2W O 1.1520(3) 0.0770(2) 0.40854(15) 0.0656(5) Uani 1 1 d . . . . .
H2WA H 1.250047 0.114670 0.393750 0.098 Uiso 1 1 d R U . . .
H2WB H 1.081012 0.021146 0.358326 0.098 Uiso 1 1 d R U . . .
O1W O 0.6663(3) -0.1996(2) 0.26788(15) 0.0658(5) Uani 1 1 d . . . . .
H1WA H 0.549013 -0.246037 0.248965 0.099 Uiso 1 1 d R U . . .
H1WB H 0.727203 -0.244567 0.290415 0.099 Uiso 1 1 d R U . . .
N2 N 0.7281(3) 0.51101(19) 0.43129(14) 0.0434(4) Uani 1 1 d . . . . .
N3 N 0.7277(3) 0.3114(2) 0.74824(13) 0.0448(5) Uani 1 1 d . . . . .
O5 O 0.8444(4) 0.0207(3) 0.24654(17) 0.0806(7) Uani 1 1 d . . . . .
C1 C 0.5650(3) 0.3069(2) 0.41250(16) 0.0369(5) Uani 1 1 d . . . . .
C2 C 0.6589(3) 0.3666(2) 0.50863(15) 0.0364(4) Uani 1 1 d . . . . .
C11 C 0.6402(3) 0.3054(2) 0.57991(15) 0.0381(5) Uani 1 1 d . . . . .
C3 C 0.7558(3) 0.4910(2) 0.51326(16) 0.0404(5) Uani 1 1 d . . . . .
C5 C 0.5559(3) 0.3904(2) 0.27328(16) 0.0402(5) Uani 1 1 d . . . . .
C12 C 0.7422(4) 0.3810(2) 0.67958(17) 0.0479(6) Uani 1 1 d . . . . .
H12A H 0.875916 0.418014 0.685438 0.058 Uiso 1 1 calc R U . . .
H12B H 0.690534 0.447701 0.693509 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6618(4) 0.4779(3) 0.23946(19) 0.0517(6) Uani 1 1 d . . . . .
H6 H 0.767583 0.542070 0.279543 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3969(4) 0.2961(3) 0.21288(18) 0.0538(6) Uani 1 1 d . . . . .
H10 H 0.324110 0.237287 0.234844 0.065 Uiso 1 1 calc R U . . .
C13 C 0.8406(5) 0.2276(3) 0.7432(2) 0.0601(7) Uani 1 1 d . . . . .
H13A H 0.974638 0.275699 0.760926 0.072 Uiso 1 1 calc R U . . .
H13B H 0.805418 0.177346 0.679974 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8788(4) 0.5982(2) 0.59465(19) 0.0552(7) Uani 1 1 d . . . . .
H4A H 0.922534 0.669933 0.573681 0.083 Uiso 1 1 calc R U . . .
H4B H 0.986448 0.578612 0.626072 0.083 Uiso 1 1 calc R U . . .
H4C H 0.806325 0.614543 0.636331 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3477(5) 0.2902(3) 0.1195(2) 0.0656(8) Uani 1 1 d . . . . .
H9 H 0.240589 0.227362 0.079064 0.079 Uiso 1 1 calc R U . . .
C7 C 0.6097(5) 0.4694(3) 0.1462(2) 0.0650(8) Uani 1 1 d . . . . .
H7 H 0.681093 0.528326 0.123767 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7942(5) 0.4008(3) 0.84026(19) 0.0658(8) Uani 1 1 d . . . . .
H16A H 0.726270 0.460400 0.839654 0.079 Uiso 1 1 calc R U . . .
H16B H 0.928862 0.445350 0.854358 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4543(5) 0.3755(3) 0.0860(2) 0.0678(8) Uani 1 1 d . . . . .
H8 H 0.421553 0.369705 0.023012 0.081 Uiso 1 1 calc R U . . .
C15 C 0.7626(6) 0.3370(5) 0.9143(2) 0.0868(12) Uani 1 1 d . . . . .
H15A H 0.627539 0.293316 0.900187 0.104 Uiso 1 1 calc R U . . .
H15B H 0.801436 0.399006 0.973172 0.104 Uiso 1 1 calc R U . . .
C14 C 0.8097(7) 0.1448(4) 0.8056(3) 0.0888(12) Uani 1 1 d . . . . .
H14A H 0.876887 0.085574 0.796154 0.107 Uiso 1 1 calc R U . . .
H14B H 0.674942 0.098992 0.789205 0.107 Uiso 1 1 calc R U . . .
C17 C 0.7846(11) 0.0548(5) 0.1655(3) 0.134(3) Uani 1 1 d . . . . .
O3 O 0.8142(12) 0.1812(6) 0.1787(4) 0.220(3) Uani 1 1 d . . . . .
O4 O 0.750(2) -0.0262(7) 0.0832(4) 0.316(7) Uani 1 1 d . . . . .
H4 H 0.732186 -0.096110 0.089835 0.474 Uiso 1 1 calc R U . . .
H5 H 0.786(7) -0.047(5) 0.240(3) 0.107(18) 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
Cs1 Cs1 4.3071(5) 2_656 ?
Cs1 Cs1 4.8173(6) 2_756 ?
Cs1 O1 3.0370(19) . ?
Cs1 O11 3.1079(19) . ?
Cs1 O11 3.0502(17) 2_656 ?
Cs1 O2W 3.175(2) 2_756 ?
Cs1 H2WB 3.2921 . ?
Cs1 O5 3.236(3) . ?
Cs1 H5 3.20(5) . ?
S1 C15 1.791(5) . ?
S1 C14 1.790(4) . ?
O1 C1 1.254(3) . ?
O11 C11 1.234(3) . ?
O3W H3WA 0.8493 . ?
O3W H3WB 0.8498 . ?
N1 N2 1.393(3) . ?
N1 C1 1.384(3) . ?
N1 C5 1.411(3) . ?
O2W H2WA 0.8620 . ?
O2W H2WB 0.8619 . ?
O1W H1WA 0.8596 . ?
O1W H1WB 0.8595 . ?
N2 C3 1.310(3) . ?
N3 C12 1.460(3) . ?
N3 C13 1.465(4) . ?
N3 C16 1.474(3) . ?
O5 C17 1.400(5) . ?
O5 H5 0.77(5) . ?
C1 C2 1.430(3) . ?
C2 C11 1.435(3) . ?
C2 C3 1.422(3) . ?
C11 C12 1.520(3) . ?
C3 C4 1.499(3) . ?
C5 C6 1.386(4) . ?
C5 C10 1.388(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.386(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.502(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.370(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.509(5) . ?
C8 H8 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 O3 1.395(7) . ?
C17 O4 1.349(7) . ?
O4 H4 0.8200 . ?

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
Cs1 Cs1 Cs1 112.971(10) 2_656 2_756 ?
Cs1 Cs1 H2WB 155.5 2_656 . ?
Cs1 Cs1 H2WB 47.6 2_756 . ?
Cs1 Cs1 H5 85.3(9) 2_756 . ?
Cs1 Cs1 H5 136.2(9) 2_656 . ?
O1 Cs1 Cs1 78.45(3) . 2_656 ?
O1 Cs1 Cs1 161.30(3) . 2_756 ?
O1 Cs1 O11 56.52(5) . . ?
O1 Cs1 O11 106.21(5) . 2_656 ?
O1 Cs1 O2W 144.70(5) . 2_756 ?
O1 Cs1 H2WB 124.7 . . ?
O1 Cs1 O5 91.46(6) . . ?
O1 Cs1 H5 96.5(9) . . ?
O11 Cs1 Cs1 46.17(4) 2_656 2_656 ?
O11 Cs1 Cs1 92.03(4) 2_656 2_756 ?
O11 Cs1 Cs1 45.07(3) . 2_656 ?
O11 Cs1 Cs1 120.41(3) . 2_756 ?
O11 Cs1 O11 91.24(5) 2_656 . ?
O11 Cs1 O2W 89.68(5) . 2_756 ?
O11 Cs1 O2W 60.49(5) 2_656 2_756 ?
O11 Cs1 H2WB 151.7 . . ?
O11 Cs1 H2WB 112.8 2_656 . ?
O11 Cs1 O5 110.09(6) 2_656 . ?
O11 Cs1 O5 146.09(6) . . ?
O11 Cs1 H5 96.4(9) 2_656 . ?
O11 Cs1 H5 153.0(9) . . ?
O2W Cs1 Cs1 69.34(4) 2_756 2_656 ?
O2W Cs1 Cs1 43.64(4) 2_756 2_756 ?
O2W Cs1 H2WB 89.6 2_756 . ?
O2W Cs1 O5 123.54(7) 2_756 . ?
O2W Cs1 H5 116.6(9) 2_756 . ?
H2WB Cs1 H5 43.0 . . ?
O5 Cs1 Cs1 85.93(5) . 2_756 ?
O5 Cs1 Cs1 147.36(5) . 2_656 ?
O5 Cs1 H2WB 39.2 . . ?
O5 Cs1 H5 13.7(9) . . ?
C14 S1 C15 96.96(17) . . ?
C1 O1 Cs1 103.36(14) . . ?
Cs1 O11 Cs1 88.76(5) 2_656 . ?
C11 O11 Cs1 104.96(15) . . ?
C11 O11 Cs1 165.63(16) . 2_656 ?
H3WA O3W H3WB 104.6 . . ?
N2 N1 C5 119.55(19) . . ?
C1 N1 N2 111.76(18) . . ?
C1 N1 C5 128.7(2) . . ?
Cs1 O2W H2WA 109.8 2_756 . ?
Cs1 O2W H2WB 109.7 2_756 . ?
H2WA O2W H2WB 104.1 . . ?
H1WA O1W H1WB 104.3 . . ?
C3 N2 N1 106.10(19) . . ?
C12 N3 C13 110.7(2) . . ?
C12 N3 C16 108.0(2) . . ?
C13 N3 C16 111.1(2) . . ?
Cs1 O5 H5 80(4) . . ?
C17 O5 Cs1 132.0(3) . . ?
C17 O5 H5 109(4) . . ?
O1 C1 N1 123.3(2) . . ?
O1 C1 C2 132.0(2) . . ?
N1 C1 C2 104.71(19) . . ?
C1 C2 C11 123.1(2) . . ?
C3 C2 C1 105.45(19) . . ?
C3 C2 C11 131.4(2) . . ?
O11 C11 C2 122.8(2) . . ?
O11 C11 C12 119.5(2) . . ?
C2 C11 C12 117.7(2) . . ?
N2 C3 C2 112.0(2) . . ?
N2 C3 C4 117.4(2) . . ?
C2 C3 C4 130.7(2) . . ?
C6 C5 N1 119.8(2) . . ?
C6 C5 C10 119.5(2) . . ?
C10 C5 N1 120.7(2) . . ?
N3 C12 C11 114.9(2) . . ?
N3 C12 H12A 108.5 . . ?
N3 C12 H12B 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C10 H10 120.3 . . ?
C9 C10 C5 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
N3 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
N3 C13 C14 111.5(3) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C9 H9 119.5 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
N3 C16 H16A 109.3 . . ?
N3 C16 H16B 109.4 . . ?
N3 C16 C15 111.4(3) . . ?
H16A C16 H16B 108.0 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
S1 C15 H15A 109.0 . . ?
S1 C15 H15B 109.0 . . ?
C16 C15 S1 113.0(3) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
S1 C14 H14A 109.2 . . ?
S1 C14 H14B 109.2 . . ?
C13 C14 S1 112.2(3) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O3 C17 O5 114.5(4) . . ?
O4 C17 O5 118.7(5) . . ?
O4 C17 O3 124.6(5) . . ?
C17 O4 H4 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2W H2WA O1 0.86 1.83 2.688(3) 176.4 1_655 yes
O2W H2WB O5 0.86 2.19 2.839(3) 131.6 . yes
O1W H1WA N3 0.86 2.05 2.866(3) 157.2 2_656 yes
O1W H1WB O3W 0.86 2.15 2.808(3) 133.1 2_756 yes
C10 H10 O1 0.93 2.32 2.885(3) 118.9 . yes
C13 H13B O11 0.97 2.45 3.040(3) 119.1 . yes
C4 H4A O3W 0.96 2.66 3.477(3) 143.8 2_766 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cs1 O1 C1 N1 124.5(2) . . . . ?
Cs1 O1 C1 C2 -53.3(3) . . . . ?
Cs1 O11 C11 C2 58.4(2) . . . . ?
Cs1 O11 C11 C2 -139.3(5) 2_656 . . . ?
Cs1 O11 C11 C12 -122.2(2) . . . . ?
Cs1 O11 C11 C12 40.1(8) 2_656 . . . ?
Cs1 O5 C17 O3 59.7(8) . . . . ?
Cs1 O5 C17 O4 -136.2(9) . . . . ?
O1 C1 C2 C11 -5.8(4) . . . . ?
O1 C1 C2 C3 177.1(2) . . . . ?
O11 C11 C12 N3 4.4(3) . . . . ?
N1 N2 C3 C2 0.3(3) . . . . ?
N1 N2 C3 C4 -179.5(2) . . . . ?
N1 C1 C2 C11 176.0(2) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
N1 C5 C10 C9 179.9(3) . . . . ?
N2 N1 C1 O1 -177.0(2) . . . . ?
N2 N1 C1 C2 1.3(3) . . . . ?
N2 N1 C5 C6 19.2(3) . . . . ?
N2 N1 C5 C10 -160.1(2) . . . . ?
N3 C13 C14 S1 -64.2(4) . . . . ?
N3 C16 C15 S1 61.8(3) . . . . ?
C1 N1 N2 C3 -1.0(3) . . . . ?
C1 N1 C5 C6 -158.3(2) . . . . ?
C1 N1 C5 C10 22.4(4) . . . . ?
C1 C2 C11 O11 1.5(4) . . . . ?
C1 C2 C11 C12 -177.9(2) . . . . ?
C1 C2 C3 N2 0.5(3) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C2 C11 C12 N3 -176.2(2) . . . . ?
C11 C2 C3 N2 -176.3(2) . . . . ?
C11 C2 C3 C4 3.4(4) . . . . ?
C3 C2 C11 O11 177.8(2) . . . . ?
C3 C2 C11 C12 -1.6(4) . . . . ?
C5 N1 N2 C3 -179.0(2) . . . . ?
C5 N1 C1 O1 0.7(4) . . . . ?
C5 N1 C1 C2 179.0(2) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C10 C9 C8 0.5(5) . . . . ?
C12 N3 C13 C14 -173.4(3) . . . . ?
C12 N3 C16 C15 173.4(3) . . . . ?
C6 C5 C10 C9 0.6(4) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C10 C5 C6 C7 -0.8(4) . . . . ?
C10 C9 C8 C7 -1.4(5) . . . . ?
C13 N3 C12 C11 70.8(3) . . . . ?
C13 N3 C16 C15 -65.0(3) . . . . ?
C16 N3 C12 C11 -167.3(2) . . . . ?
C16 N3 C13 C14 66.6(4) . . . . ?
C15 S1 C14 C13 52.8(3) . . . . ?
C14 S1 C15 C16 -52.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_373
_database_code_depnum_ccdc_archive 'CCDC 2119860'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O3'
_chemical_formula_sum            'C16 H19 N3 O3'
_chemical_formula_weight         301.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c26 N3 O2 H24'
_chemical_oxdiff_usercomment     'V Kurteva 322'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4773(2)
_cell_length_b                   7.8846(2)
_cell_length_c                   20.2726(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.646(2)
_cell_angle_gamma                90
_cell_volume                     1507.50(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8143
_cell_measurement_temperature    290
_cell_measurement_theta_max      38.3420
_cell_measurement_theta_min      3.8040
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32182
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         43.692
_diffrn_reflns_theta_min         2.774
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00   85.00   1.0000   17.5000
omega____ theta____ kappa____ phi______ frames
    -       -0.3125 -178.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00  122.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8132   19.0000   60.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   66.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8132  -37.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -26.00   70.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       43.8132  -57.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00  -12.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.4382  -80.0000  117.7349 34

#__ type_ start__ end____ width___ exp.time_
  6 omega -130.00  -80.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -44.4382  178.0000  150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0309643000
_diffrn_orient_matrix_UB_12      -0.0415152000
_diffrn_orient_matrix_UB_13      -0.0260714000
_diffrn_orient_matrix_UB_21      -0.0524152000
_diffrn_orient_matrix_UB_22      0.0357439000
_diffrn_orient_matrix_UB_23      -0.0233170000
_diffrn_orient_matrix_UB_31      0.0441925000
_diffrn_orient_matrix_UB_32      0.0713545000
_diffrn_orient_matrix_UB_33      -0.0034893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6242
_reflns_number_total             11468
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         11468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.2070
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.57143(8) 0.41961(9) 0.12864(4) 0.02988(14) Uani 1 1 d . . . . .
C2 C 0.44412(9) 0.71072(11) 0.20131(4) 0.02928(15) Uani 1 1 d . . . . .
N1 N 0.22769(8) 0.77368(10) 0.15522(4) 0.03160(15) Uani 1 1 d . . . . .
N2 N 0.23897(9) 0.84507(11) 0.21841(4) 0.03501(16) Uani 1 1 d . . . . .
O1 O 0.36286(8) 0.60993(10) 0.08910(3) 0.03833(16) Uani 1 1 d . . . . .
C5 C 0.09902(10) 0.79507(12) 0.11446(5) 0.03289(17) Uani 1 1 d . . . . .
C1 C 0.34929(9) 0.68936(11) 0.14284(4) 0.02888(15) Uani 1 1 d . . . . .
C3 C 0.36648(10) 0.80781(12) 0.24502(5) 0.03287(17) Uani 1 1 d . . . . .
C11 C 0.58757(9) 0.65429(12) 0.21558(5) 0.03244(17) Uani 1 1 d . . . . .
C16 C 0.51537(11) 0.28637(13) 0.17130(5) 0.03466(17) Uani 1 1 d . . . . .
O11 O 0.66159(9) 0.69381(13) 0.26667(5) 0.0506(2) Uani 1 1 d . . . . .
C12 C 0.66199(10) 0.54527(14) 0.16738(6) 0.0387(2) Uani 1 1 d . . . . .
C13 C 0.64982(12) 0.33866(14) 0.07675(6) 0.0390(2) Uani 1 1 d . . . . .
O2 O 0.50466(12) 0.08719(10) 0.08012(5) 0.0533(2) Uani 1 1 d . . . . .
C15 C 0.42581(14) 0.16391(15) 0.12793(6) 0.0451(2) Uani 1 1 d . . . . .
C14 C 0.55517(15) 0.21174(16) 0.03829(6) 0.0470(3) Uani 1 1 d . . . . .
C6 C -0.00785(13) 0.89159(15) 0.13838(6) 0.0454(2) Uani 1 1 d . . . . .
C10 C 0.07562(14) 0.7203(2) 0.05257(7) 0.0553(3) Uani 1 1 d . . . . .
C7 C -0.13598(14) 0.91439(18) 0.09975(8) 0.0557(3) Uani 1 1 d . . . . .
C4 C 0.41309(15) 0.8666(2) 0.31359(6) 0.0501(3) Uani 1 1 d . . . . .
C8 C -0.15754(15) 0.8456(2) 0.03752(8) 0.0597(4) Uani 1 1 d . . . . .
C9 C -0.05230(17) 0.7474(3) 0.01454(8) 0.0684(4) Uani 1 1 d . . . . .
H16A H 0.4617(15) 0.3425(17) 0.2011(7) 0.038(3) Uiso 1 1 d . . . . .
H13A H 0.6761(17) 0.4253(19) 0.0495(7) 0.047(4) Uiso 1 1 d . . . . .
H16B H 0.6021(18) 0.232(2) 0.1972(8) 0.054(4) Uiso 1 1 d . . . . .
H14A H 0.6094(19) 0.154(2) 0.0058(8) 0.061(5) Uiso 1 1 d . . . . .
H6 H 0.0080(18) 0.945(2) 0.1828(8) 0.062(5) Uiso 1 1 d . . . . .
H15A H 0.3931(17) 0.074(2) 0.1543(8) 0.054(4) Uiso 1 1 d . . . . .
H14B H 0.4776(18) 0.272(2) 0.0137(8) 0.049(4) Uiso 1 1 d . . . . .
H13B H 0.7334(17) 0.2849(18) 0.0985(7) 0.044(4) Uiso 1 1 d . . . . .
H15B H 0.3438(18) 0.225(2) 0.1057(8) 0.052(4) Uiso 1 1 d . . . . .
H7 H -0.213(2) 0.986(2) 0.1196(9) 0.076(5) Uiso 1 1 d . . . . .
H10 H 0.152(2) 0.650(2) 0.0367(10) 0.076(6) Uiso 1 1 d . . . . .
H9 H -0.066(2) 0.700(3) -0.0302(12) 0.099(7) Uiso 1 1 d . . . . .
H8 H -0.251(2) 0.860(3) 0.0109(10) 0.080(6) Uiso 1 1 d . . . . .
H4A H 0.3332(19) 0.915(2) 0.3330(8) 0.061(5) Uiso 1 1 d . . . . .
H4B H 0.487(2) 0.952(3) 0.3114(9) 0.079(6) Uiso 1 1 d . . . . .
H4C H 0.449(2) 0.774(3) 0.3430(10) 0.078(6) Uiso 1 1 d . . . . .
H12A H 0.698(2) 0.624(2) 0.1360(9) 0.066(5) Uiso 1 1 d . . . . .
H12B H 0.7430(18) 0.489(2) 0.1941(8) 0.060(4) Uiso 1 1 d . . . . .
H3 H 0.4872(17) 0.489(2) 0.1062(8) 0.058(4) 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
N3 C16 1.4914(12) . ?
N3 C12 1.4840(12) . ?
N3 C13 1.4898(12) . ?
N3 H3 1.036(16) . ?
C2 C1 1.4252(12) . ?
C2 C3 1.4287(12) . ?
C2 C11 1.4327(13) . ?
N1 N2 1.3938(11) . ?
N1 C5 1.4142(12) . ?
N1 C1 1.3748(11) . ?
N2 C3 1.3074(13) . ?
O1 C1 1.2742(11) . ?
C5 C6 1.3917(14) . ?
C5 C10 1.3843(16) . ?
C3 C4 1.4906(14) . ?
C11 O11 1.2324(12) . ?
C11 C12 1.5254(14) . ?
C16 C15 1.5095(15) . ?
C16 H16A 0.938(14) . ?
C16 H16B 1.024(17) . ?
C12 H12A 0.975(19) . ?
C12 H12B 1.000(17) . ?
C13 C14 1.5088(17) . ?
C13 H13A 0.929(15) . ?
C13 H13B 0.965(15) . ?
O2 C15 1.4165(16) . ?
O2 C14 1.4116(16) . ?
C15 H15A 0.956(17) . ?
C15 H15B 0.984(17) . ?
C14 H14A 0.987(18) . ?
C14 H14B 0.971(16) . ?
C6 C7 1.3903(17) . ?
C6 H6 0.991(17) . ?
C10 C9 1.3878(18) . ?
C10 H10 0.99(2) . ?
C7 C8 1.370(2) . ?
C7 H7 1.032(19) . ?
C4 H4A 0.965(18) . ?
C4 H4B 0.98(2) . ?
C4 H4C 0.98(2) . ?
C8 C9 1.379(2) . ?
C8 H8 1.00(2) . ?
C9 H9 0.98(2) . ?

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 N3 H3 108.9(9) . . ?
C12 N3 C16 112.58(8) . . ?
C12 N3 C13 110.92(7) . . ?
C12 N3 H3 105.0(9) . . ?
C13 N3 C16 109.79(8) . . ?
C13 N3 H3 109.5(9) . . ?
C1 C2 C3 104.95(8) . . ?
C1 C2 C11 129.76(8) . . ?
C3 C2 C11 125.28(8) . . ?
N2 N1 C5 118.21(7) . . ?
C1 N1 N2 111.91(7) . . ?
C1 N1 C5 129.88(8) . . ?
C3 N2 N1 105.83(7) . . ?
C6 C5 N1 118.48(9) . . ?
C10 C5 N1 122.06(9) . . ?
C10 C5 C6 119.45(10) . . ?
N1 C1 C2 105.22(7) . . ?
O1 C1 C2 131.36(8) . . ?
O1 C1 N1 123.41(8) . . ?
C2 C3 C4 128.44(9) . . ?
N2 C3 C2 112.09(8) . . ?
N2 C3 C4 119.47(9) . . ?
C2 C11 C12 122.34(8) . . ?
O11 C11 C2 122.79(9) . . ?
O11 C11 C12 114.83(9) . . ?
N3 C16 C15 108.96(8) . . ?
N3 C16 H16A 106.7(8) . . ?
N3 C16 H16B 106.0(9) . . ?
C15 C16 H16A 111.6(8) . . ?
C15 C16 H16B 114.2(9) . . ?
H16A C16 H16B 108.9(12) . . ?
N3 C12 C11 115.82(7) . . ?
N3 C12 H12A 107.6(11) . . ?
N3 C12 H12B 111.3(10) . . ?
C11 C12 H12A 105.7(11) . . ?
C11 C12 H12B 106.4(10) . . ?
H12A C12 H12B 109.8(15) . . ?
N3 C13 C14 109.67(9) . . ?
N3 C13 H13A 106.7(9) . . ?
N3 C13 H13B 108.0(9) . . ?
C14 C13 H13A 111.2(9) . . ?
C14 C13 H13B 111.3(9) . . ?
H13A C13 H13B 109.8(13) . . ?
C14 O2 C15 110.30(9) . . ?
C16 C15 H15A 109.9(10) . . ?
C16 C15 H15B 109.2(9) . . ?
O2 C15 C16 111.55(10) . . ?
O2 C15 H15A 106.9(10) . . ?
O2 C15 H15B 110.0(10) . . ?
H15A C15 H15B 109.3(14) . . ?
C13 C14 H14A 109.3(10) . . ?
C13 C14 H14B 108.8(9) . . ?
O2 C14 C13 111.74(10) . . ?
O2 C14 H14A 108.0(10) . . ?
O2 C14 H14B 111.4(9) . . ?
H14A C14 H14B 107.5(13) . . ?
C5 C6 H6 119.8(10) . . ?
C7 C6 C5 119.97(11) . . ?
C7 C6 H6 120.2(10) . . ?
C5 C10 C9 119.41(13) . . ?
C5 C10 H10 118.4(12) . . ?
C9 C10 H10 122.2(12) . . ?
C6 C7 H7 117.6(11) . . ?
C8 C7 C6 120.69(12) . . ?
C8 C7 H7 121.7(10) . . ?
C3 C4 H4A 109.3(10) . . ?
C3 C4 H4B 108.7(11) . . ?
C3 C4 H4C 112.9(12) . . ?
H4A C4 H4B 110.2(16) . . ?
H4A C4 H4C 106.5(16) . . ?
H4B C4 H4C 109.3(16) . . ?
C7 C8 C9 119.07(12) . . ?
C7 C8 H8 120.0(12) . . ?
C9 C8 H8 120.8(12) . . ?
C10 C9 H9 118.8(14) . . ?
C8 C9 C10 121.33(14) . . ?
C8 C9 H9 119.8(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16A N2 0.938(14) 2.625(14) 3.4762(13) 151.1(11) 2_545 yes
C16 H16B O11 1.024(17) 2.307(17) 3.2756(13) 157.4(13) 2_645 yes
C10 H10 O1 0.99(2) 2.19(2) 2.8843(14) 125.8(15) . yes
C12 H12B O11 1.000(17) 2.592(17) 3.4384(15) 142.3(13) 2_645 yes
N3 H3 O1 1.036(16) 1.528(17) 2.5475(10) 166.8(15) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C16 C15 O2 58.67(12) . . . . ?
N3 C13 C14 O2 -57.26(13) . . . . ?
C2 C11 C12 N3 -35.34(14) . . . . ?
N1 N2 C3 C2 -0.25(11) . . . . ?
N1 N2 C3 C4 179.94(11) . . . . ?
N1 C5 C6 C7 -179.64(11) . . . . ?
N1 C5 C10 C9 -179.32(14) . . . . ?
N2 N1 C5 C6 2.42(14) . . . . ?
N2 N1 C5 C10 -176.17(11) . . . . ?
N2 N1 C1 C2 -0.90(10) . . . . ?
N2 N1 C1 O1 178.01(9) . . . . ?
C5 N1 N2 C3 -179.73(8) . . . . ?
C5 N1 C1 C2 179.63(9) . . . . ?
C5 N1 C1 O1 -1.45(15) . . . . ?
C5 C6 C7 C8 -1.4(2) . . . . ?
C5 C10 C9 C8 -0.9(3) . . . . ?
C1 C2 C3 N2 -0.29(11) . . . . ?
C1 C2 C3 C4 179.50(12) . . . . ?
C1 C2 C11 O11 173.89(10) . . . . ?
C1 C2 C11 C12 -3.97(15) . . . . ?
C1 N1 N2 C3 0.73(11) . . . . ?
C1 N1 C5 C6 -178.14(10) . . . . ?
C1 N1 C5 C10 3.26(17) . . . . ?
C3 C2 C1 N1 0.70(9) . . . . ?
C3 C2 C1 O1 -178.09(10) . . . . ?
C3 C2 C11 O11 -4.45(16) . . . . ?
C3 C2 C11 C12 177.69(9) . . . . ?
C11 C2 C1 N1 -177.90(9) . . . . ?
C11 C2 C1 O1 3.31(17) . . . . ?
C11 C2 C3 N2 178.39(9) . . . . ?
C11 C2 C3 C4 -1.82(17) . . . . ?
C16 N3 C12 C11 -64.70(11) . . . . ?
C16 N3 C13 C14 54.93(11) . . . . ?
O11 C11 C12 N3 146.64(10) . . . . ?
C12 N3 C16 C15 -179.57(9) . . . . ?
C12 N3 C13 C14 179.98(9) . . . . ?
C13 N3 C16 C15 -55.48(11) . . . . ?
C13 N3 C12 C11 171.84(9) . . . . ?
C15 O2 C14 C13 59.78(14) . . . . ?
C14 O2 C15 C16 -60.69(14) . . . . ?
C6 C5 C10 C9 2.1(2) . . . . ?
C6 C7 C8 C9 2.6(3) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?

_olex2_date_sample_data_collection 2016-10-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0126_0m
_database_code_depnum_ccdc_archive 'CCDC 2119863'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O2 S'
_chemical_formula_sum            'C16 H19 N3 O2 S'
_chemical_formula_weight         317.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6424(5)
_cell_length_b                   8.0087(3)
_cell_length_c                   10.9078(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.047(2)
_cell_angle_gamma                90
_cell_volume                     796.22(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    290
_cell_measurement_theta_max      34.094
_cell_measurement_theta_min      2.235
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0860 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9367.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44584
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_min         1.975
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4264
_reflns_number_total             4862
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1568 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4862
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1197
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C16(H16A,H16B), C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09508(11) 0.08056(11) 0.16451(10) 0.0586(3) Uani 1 1 d . . . . .
O1 O 0.2293(2) 0.6254(3) 0.19208(17) 0.0365(5) Uani 1 1 d . . . . .
N3 N 0.0652(2) 0.4409(3) 0.2767(2) 0.0288(4) Uani 1 1 d . . . . .
O11 O 0.1167(3) 0.7146(3) 0.5459(2) 0.0541(6) Uani 1 1 d . . . . .
N1 N 0.4236(2) 0.7930(3) 0.3124(2) 0.0319(5) Uani 1 1 d . . . . .
N2 N 0.4740(2) 0.8689(3) 0.4348(2) 0.0369(5) Uani 1 1 d . . . . .
C1 C 0.2943(3) 0.7077(3) 0.2948(2) 0.0276(5) Uani 1 1 d . . . . .
C11 C 0.1372(3) 0.6755(3) 0.4446(3) 0.0325(5) Uani 1 1 d . . . . .
C3 C 0.3771(3) 0.8328(3) 0.4906(3) 0.0336(6) Uani 1 1 d . . . . .
C2 C 0.2601(3) 0.7328(3) 0.4099(2) 0.0286(5) Uani 1 1 d . . . . .
C13 C 0.1664(3) 0.3144(4) 0.3608(3) 0.0340(6) Uani 1 1 d . . . . .
H13A H 0.112952 0.246833 0.404082 0.041 Uiso 1 1 calc R U . . .
H13B H 0.244764 0.371213 0.426769 0.041 Uiso 1 1 calc R U . . .
C12 C 0.0169(3) 0.5664(4) 0.3543(3) 0.0382(6) Uani 1 1 d . . . . .
H12A H -0.032477 0.508166 0.406228 0.046 Uiso 1 1 calc R U . . .
H12B H -0.054699 0.638879 0.295030 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0643(3) 0.3627(4) 0.1783(3) 0.0380(6) Uani 1 1 d . . . . .
H16A H -0.129169 0.449555 0.129516 0.046 Uiso 1 1 calc R U . . .
H16B H -0.118207 0.296524 0.222083 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5103(3) 0.8051(4) 0.2302(3) 0.0357(6) Uani 1 1 d . . . . .
C6 C 0.6304(3) 0.9105(5) 0.2665(4) 0.0496(8) Uani 1 1 d . . . . .
H6 H 0.650182 0.974444 0.341474 0.060 Uiso 1 1 calc R U . . .
C15 C -0.0182(4) 0.2531(5) 0.0865(3) 0.0501(8) Uani 1 1 d . . . . .
H15A H 0.034988 0.320297 0.042718 0.060 Uiso 1 1 calc R U . . .
H15B H -0.105276 0.210228 0.021131 0.060 Uiso 1 1 calc R U . . .
C14 C 0.2312(3) 0.2032(4) 0.2824(3) 0.0444(7) Uani 1 1 d . . . . .
H14A H 0.302075 0.128899 0.340598 0.053 Uiso 1 1 calc R U . . .
H14B H 0.283015 0.271642 0.238075 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4827(4) 0.7095(5) 0.1191(3) 0.0530(8) Uani 1 1 d . . . . .
H10 H 0.403127 0.636879 0.094766 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3975(4) 0.8987(5) 0.6235(3) 0.0526(8) Uani 1 1 d . . . . .
H4A H 0.490492 0.954550 0.655910 0.079 Uiso 1 1 calc R U . . .
H4B H 0.394965 0.807854 0.680151 0.079 Uiso 1 1 calc R U . . .
H4C H 0.320263 0.976115 0.619910 0.079 Uiso 1 1 calc R U . . .
C7 C 0.7211(4) 0.9209(6) 0.1916(5) 0.0683(12) Uani 1 1 d . . . . .
H7 H 0.802249 0.991261 0.216792 0.082 Uiso 1 1 calc R U . . .
C8 C 0.6926(5) 0.8286(7) 0.0806(5) 0.0741(13) Uani 1 1 d . . . . .
H8 H 0.753185 0.837478 0.029819 0.089 Uiso 1 1 calc R U . . .
C9 C 0.5736(5) 0.7223(7) 0.0443(4) 0.0717(12) Uani 1 1 d . . . . .
H9 H 0.554485 0.658877 -0.030851 0.086 Uiso 1 1 calc R U . . .
H3 H 0.112(4) 0.498(4) 0.237(3) 0.035(8) 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
S1 C15 1.794(4) . ?
S1 C14 1.800(3) . ?
O1 C1 1.274(3) . ?
N3 C13 1.495(3) . ?
N3 C12 1.483(4) . ?
N3 C16 1.493(3) . ?
N3 H3 0.86(4) . ?
O11 C11 1.225(3) . ?
N1 N2 1.402(3) . ?
N1 C1 1.379(3) . ?
N1 C5 1.415(3) . ?
N2 C3 1.303(4) . ?
C1 C2 1.412(4) . ?
C11 C2 1.433(4) . ?
C11 C12 1.527(4) . ?
C3 C2 1.428(3) . ?
C3 C4 1.495(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.503(5) . ?
C5 C6 1.383(4) . ?
C5 C10 1.384(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C9 1.383(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.368(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(6) . ?
C9 H9 0.9300 . ?

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
C15 S1 C14 96.17(15) . . ?
C13 N3 H3 109(2) . . ?
C12 N3 C13 111.9(2) . . ?
C12 N3 C16 110.5(2) . . ?
C12 N3 H3 104(2) . . ?
C16 N3 C13 112.5(2) . . ?
C16 N3 H3 109(2) . . ?
N2 N1 C5 118.7(2) . . ?
C1 N1 N2 111.4(2) . . ?
C1 N1 C5 129.8(2) . . ?
C3 N2 N1 105.7(2) . . ?
O1 C1 N1 122.8(2) . . ?
O1 C1 C2 131.6(2) . . ?
N1 C1 C2 105.6(2) . . ?
O11 C11 C2 123.2(3) . . ?
O11 C11 C12 114.6(2) . . ?
C2 C11 C12 122.2(2) . . ?
N2 C3 C2 112.3(2) . . ?
N2 C3 C4 119.1(3) . . ?
C2 C3 C4 128.6(3) . . ?
C1 C2 C11 130.0(2) . . ?
C1 C2 C3 105.1(2) . . ?
C3 C2 C11 124.9(2) . . ?
N3 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
N3 C13 C14 111.2(2) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
N3 C12 C11 116.3(2) . . ?
N3 C12 H12A 108.2 . . ?
N3 C12 H12B 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
N3 C16 H16A 109.4 . . ?
N3 C16 H16B 109.4 . . ?
N3 C16 C15 111.3(2) . . ?
H16A C16 H16B 108.0 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C6 C5 N1 118.3(3) . . ?
C6 C5 C10 119.5(3) . . ?
C10 C5 N1 122.2(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
S1 C15 H15A 108.8 . . ?
S1 C15 H15B 108.8 . . ?
C16 C15 S1 113.6(2) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
S1 C14 H14A 109.0 . . ?
S1 C14 H14B 109.0 . . ?
C13 C14 S1 112.8(2) . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13A O11 0.97 2.46 3.307(3) 145.7 2_546 yes
C13 H13B N2 0.97 2.64 3.484(3) 145.8 2_646 yes
C12 H12A O11 0.97 2.60 3.420(4) 143.0 2_546 yes
C16 H16B O11 0.97 2.61 3.421(4) 141.3 2_546 yes
C15 H15A S1 0.97 3.03 3.688(4) 126.3 2 yes
C15 H15B O1 0.97 2.34 3.223(4) 150.7 2_545 yes
C14 H14A N2 0.97 2.65 3.588(4) 162.4 1_545 yes
C10 H10 O1 0.93 2.26 2.886(4) 124.1 . yes
N3 H3 O1 0.86(4) 1.70(4) 2.548(3) 167(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -1.9(5) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
N3 C13 C14 S1 -63.3(3) . . . . ?
N3 C16 C15 S1 62.0(3) . . . . ?
O11 C11 C2 C1 -175.8(3) . . . . ?
O11 C11 C2 C3 3.9(4) . . . . ?
O11 C11 C12 N3 -146.1(3) . . . . ?
N1 N2 C3 C2 0.1(3) . . . . ?
N1 N2 C3 C4 -178.9(3) . . . . ?
N1 C1 C2 C11 178.9(3) . . . . ?
N1 C1 C2 C3 -0.8(3) . . . . ?
N1 C5 C6 C7 177.5(3) . . . . ?
N1 C5 C10 C9 -177.9(4) . . . . ?
N2 N1 C1 O1 -178.3(2) . . . . ?
N2 N1 C1 C2 1.0(3) . . . . ?
N2 N1 C5 C6 -8.9(4) . . . . ?
N2 N1 C5 C10 168.0(3) . . . . ?
N2 C3 C2 C1 0.4(3) . . . . ?
N2 C3 C2 C11 -179.3(3) . . . . ?
C1 N1 N2 C3 -0.7(3) . . . . ?
C1 N1 C5 C6 175.0(3) . . . . ?
C1 N1 C5 C10 -8.2(5) . . . . ?
C2 C11 C12 N3 36.5(4) . . . . ?
C13 N3 C12 C11 62.9(3) . . . . ?
C13 N3 C16 C15 -62.1(3) . . . . ?
C12 N3 C13 C14 -171.9(2) . . . . ?
C12 N3 C16 C15 172.0(3) . . . . ?
C12 C11 C2 C1 1.4(4) . . . . ?
C12 C11 C2 C3 -179.0(3) . . . . ?
C16 N3 C13 C14 63.1(3) . . . . ?
C16 N3 C12 C11 -170.9(2) . . . . ?
C5 N1 N2 C3 -177.5(2) . . . . ?
C5 N1 C1 O1 -1.9(4) . . . . ?
C5 N1 C1 C2 177.4(3) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C5 C10 C9 C8 0.6(7) . . . . ?
C6 C5 C10 C9 -1.1(5) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C15 S1 C14 C13 54.7(3) . . . . ?
C14 S1 C15 C16 -54.3(3) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C4 C3 C2 C1 179.4(3) . . . . ?
C4 C3 C2 C11 -0.3(5) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0146_0m
_database_code_depnum_ccdc_archive 'CCDC 2119862'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H29 Cs N6 O2'
_chemical_formula_sum            'C26 H29 Cs N6 O2'
_chemical_formula_weight         590.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5466(8)
_cell_length_b                   11.0591(11)
_cell_length_c                   14.5749(14)
_cell_angle_alpha                72.225(3)
_cell_angle_beta                 80.490(2)
_cell_angle_gamma                70.549(2)
_cell_volume                     1378.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9676
_cell_measurement_temperature    290
_cell_measurement_theta_max      29.556
_cell_measurement_theta_min      2.268
_shelx_estimated_absorpt_T_max   0.770
_shelx_estimated_absorpt_T_min   0.683
_exptl_absorpt_coefficient_mu    1.376
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.7354.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            78956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5980
_reflns_number_total             6899
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         6899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+0.7913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0701
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C13(H13a,H13b), C15(H15a,H15b), C16(H16a,H16b), C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C22(H22), C21(H21), C7(H7), C18(H18), C19(H19), C9(H9),
 C20(H20), C8(H8)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C52(H52a,H52b,H52c), C50(H50a,H50b,H50c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.11104(2) 0.54436(2) 0.60489(2) 0.05645(6) Uani 1 1 d . . . . .
O11 O 0.83136(15) 0.47622(16) 0.60385(10) 0.0525(3) Uani 1 1 d . . . . .
O1 O 0.37279(16) 0.49239(16) 0.70647(11) 0.0549(4) Uani 1 1 d . . . . .
N3 N 0.64234(18) 0.69023(17) 0.48453(11) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.49723(18) 0.32382(17) 0.83222(11) 0.0460(4) Uani 1 1 d . . . . .
N4 N 0.6530(2) 0.93515(17) 0.34722(12) 0.0471(4) Uani 1 1 d . . . . .
N2 N 0.6436(2) 0.25241(19) 0.85565(13) 0.0541(4) Uani 1 1 d . . . . .
C11 C 0.6972(2) 0.4938(2) 0.62927(13) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.4907(2) 0.42117(19) 0.74478(13) 0.0410(4) Uani 1 1 d . . . . .
C2 C 0.6437(2) 0.41153(19) 0.71389(13) 0.0413(4) Uani 1 1 d . . . . .
C14 C 0.6023(3) 0.8393(2) 0.32332(15) 0.0532(5) Uani 1 1 d . . . . .
H14A H 0.685790 0.778632 0.296393 0.064 Uiso 1 1 calc R U . . .
H14B H 0.529716 0.885374 0.275083 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5330(2) 0.7618(2) 0.41228(15) 0.0535(5) Uani 1 1 d . . . . .
H13A H 0.448296 0.822251 0.438568 0.064 Uiso 1 1 calc R U . . .
H13B H 0.497779 0.699092 0.395467 0.064 Uiso 1 1 calc R U . . .
C5 C 0.3796(2) 0.2903(2) 0.89593(13) 0.0457(4) Uani 1 1 d . . . . .
C3 C 0.7275(2) 0.3050(2) 0.78565(14) 0.0475(4) Uani 1 1 d . . . . .
C17 C 0.6976(2) 1.0306(2) 0.26936(15) 0.0502(5) Uani 1 1 d . . . . .
C15 C 0.7566(2) 0.8688(2) 0.42410(15) 0.0511(5) Uani 1 1 d . . . . .
H15A H 0.782968 0.935133 0.442605 0.061 Uiso 1 1 calc R U . . .
H15B H 0.847003 0.811256 0.400276 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6875(2) 0.7873(2) 0.51123(14) 0.0486(4) Uani 1 1 d . . . . .
H16A H 0.758996 0.741735 0.560194 0.058 Uiso 1 1 calc R U . . .
H16B H 0.601537 0.845647 0.538219 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5806(2) 0.6065(2) 0.56832(16) 0.0537(5) Uani 1 1 d . . . . .
H12A H 0.518380 0.568736 0.546181 0.064 Uiso 1 1 calc R U . . .
H12B H 0.517366 0.661847 0.608643 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2343(3) 0.3720(3) 0.88825(17) 0.0605(6) Uani 1 1 d . . . . .
H10 H 0.211642 0.451562 0.839728 0.073 Uiso 1 1 calc R U . . .
C4 C 0.8933(3) 0.2526(3) 0.7899(2) 0.0721(7) Uani 1 1 d . . . . .
H4A H 0.917961 0.180874 0.847405 0.108 Uiso 1 1 calc R U . . .
H4B H 0.931008 0.322530 0.790761 0.108 Uiso 1 1 calc R U . . .
H4C H 0.937147 0.220654 0.734257 0.108 Uiso 1 1 calc R U . . .
C6 C 0.4107(3) 0.1738(2) 0.96926(18) 0.0657(6) Uani 1 1 d . . . . .
H6 H 0.508233 0.118369 0.975751 0.079 Uiso 1 1 calc R U . . .
C22 C 0.7262(3) 1.1363(2) 0.2875(2) 0.0704(7) Uani 1 1 d . . . . .
H22 H 0.720160 1.140889 0.350773 0.085 Uiso 1 1 calc R U . . .
C21 C 0.7633(4) 1.2347(3) 0.2123(3) 0.0930(10) Uani 1 1 d . . . . .
H21 H 0.782016 1.304795 0.225581 0.112 Uiso 1 1 calc R U . . .
C7 C 0.2974(4) 0.1390(3) 1.0332(2) 0.0854(9) Uani 1 1 d . . . . .
H7 H 0.319730 0.060191 1.082425 0.102 Uiso 1 1 calc R U . . .
C18 C 0.7098(3) 1.0262(3) 0.17411(17) 0.0704(7) Uani 1 1 d . . . . .
H18 H 0.693375 0.955721 0.159921 0.084 Uiso 1 1 calc R U . . .
C19 C 0.7466(4) 1.1268(4) 0.1000(2) 0.0902(10) Uani 1 1 d . . . . .
H19 H 0.753416 1.123509 0.036317 0.108 Uiso 1 1 calc R U . . .
C9 C 0.1223(3) 0.3351(3) 0.9531(2) 0.0759(7) Uani 1 1 d . . . . .
H9 H 0.024603 0.390325 0.947676 0.091 Uiso 1 1 calc R U . . .
N51 N 0.1213(4) 0.8405(4) 0.4788(3) 0.1115(10) Uani 1 1 d . . . . .
C20 C 0.7729(3) 1.2304(4) 0.1190(3) 0.0943(11) Uani 1 1 d . . . . .
H20 H 0.797047 1.297437 0.068810 0.113 Uiso 1 1 calc R U . . .
C8 C 0.1541(3) 0.2180(3) 1.0252(2) 0.0828(8) Uani 1 1 d . . . . .
H8 H 0.078436 0.193234 1.068071 0.099 Uiso 1 1 calc R U . . .
C53 C -0.2396(4) 0.6247(4) 0.8142(3) 0.0895(9) Uani 1 1 d . . . . .
N53 N -0.1413(5) 0.6424(4) 0.7649(3) 0.1277(13) Uani 1 1 d . . . . .
C51 C 0.1321(4) 0.9156(4) 0.4100(3) 0.0925(10) Uani 1 1 d . . . . .
C52 C -0.3651(5) 0.6007(6) 0.8778(3) 0.1254(16) Uani 1 1 d . . . . .
H52A H -0.378413 0.519671 0.875055 0.188 Uiso 1 1 calc R U . . .
H52B H -0.452930 0.673497 0.858328 0.188 Uiso 1 1 calc R U . . .
H52C H -0.347736 0.593009 0.942704 0.188 Uiso 1 1 calc R U . . .
C50 C 0.1479(6) 1.0122(5) 0.3201(4) 0.146(2) Uani 1 1 d . . . . .
H50A H 0.056761 1.046099 0.288386 0.219 Uiso 1 1 calc R U . . .
H50B H 0.227436 0.970812 0.279453 0.219 Uiso 1 1 calc R U . . .
H50C H 0.170209 1.084040 0.332417 0.219 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
Cs1 Cs1 4.4905(4) 2_566 ?
Cs1 O11 3.0653(15) 2_666 ?
Cs1 O11 3.0095(14) 1_455 ?
Cs1 O1 2.9177(14) . ?
Cs1 N3 3.3099(18) 2_666 ?
Cs1 C11 3.6710(19) 2_666 ?
Cs1 H14A 3.429(2) 2_666 ?
Cs1 N51 3.254(4) . ?
Cs1 N53 3.220(4) . ?
O11 C11 1.239(2) . ?
O1 C1 1.244(2) . ?
N3 C13 1.459(3) . ?
N3 C16 1.452(3) . ?
N3 C12 1.460(2) . ?
N1 N2 1.397(2) . ?
N1 C1 1.390(2) . ?
N1 C5 1.408(2) . ?
N4 C14 1.450(3) . ?
N4 C17 1.411(3) . ?
N4 C15 1.467(3) . ?
N2 C3 1.303(3) . ?
C11 C2 1.424(3) . ?
C11 C12 1.520(3) . ?
C1 C2 1.434(3) . ?
C2 C3 1.421(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.506(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C5 C10 1.382(3) . ?
C5 C6 1.378(3) . ?
C3 C4 1.498(3) . ?
C17 C22 1.392(4) . ?
C17 C18 1.388(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C9 1.387(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.382(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.362(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.358(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(4) . ?
N51 C51 1.104(5) . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C53 N53 1.117(5) . ?
C53 C52 1.435(6) . ?
C51 C50 1.438(6) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cs1 Cs1 H14A 96.33(4) 2_566 2_666 ?
O11 Cs1 Cs1 41.86(3) 2_666 2_566 ?
O11 Cs1 Cs1 42.82(3) 1_455 2_566 ?
O11 Cs1 O11 84.68(4) 1_455 2_666 ?
O11 Cs1 N3 50.93(4) 2_666 2_666 ?
O11 Cs1 N3 99.91(4) 1_455 2_666 ?
O11 Cs1 C11 102.08(4) 1_455 2_666 ?
O11 Cs1 C11 18.55(4) 2_666 2_666 ?
O11 Cs1 H14A 94.30(5) 1_455 2_666 ?
O11 Cs1 H14A 95.05(5) 2_666 2_666 ?
O11 Cs1 N51 76.30(8) 2_666 . ?
O11 Cs1 N51 116.82(7) 1_455 . ?
O11 Cs1 N53 67.84(8) 1_455 . ?
O11 Cs1 N53 144.48(9) 2_666 . ?
O1 Cs1 Cs1 150.11(3) . 2_566 ?
O1 Cs1 O11 147.12(4) . 1_455 ?
O1 Cs1 O11 116.46(4) . 2_666 ?
O1 Cs1 N3 78.48(4) . 2_666 ?
O1 Cs1 C11 98.01(4) . 2_666 ?
O1 Cs1 H14A 60.76(5) . 2_666 ?
O1 Cs1 N51 93.54(7) . . ?
O1 Cs1 N53 98.39(9) . . ?
N3 Cs1 Cs1 71.65(3) 2_666 2_566 ?
N3 Cs1 C11 41.58(4) 2_666 2_666 ?
N3 Cs1 H14A 45.85(5) 2_666 2_666 ?
C11 Cs1 Cs1 59.54(3) 2_666 2_566 ?
C11 Cs1 H14A 87.38(5) 2_666 2_666 ?
N51 Cs1 Cs1 98.09(7) . 2_566 ?
N51 Cs1 N3 111.63(8) . 2_666 ?
N51 Cs1 C11 74.14(8) . 2_666 ?
N51 Cs1 H14A 146.22(7) . 2_666 ?
N53 Cs1 Cs1 107.63(8) . 2_566 ?
N53 Cs1 N3 152.42(8) . 2_666 ?
N53 Cs1 C11 161.27(9) . 2_666 ?
N53 Cs1 H14A 108.57(9) . 2_666 ?
N53 Cs1 N51 95.86(11) . . ?
Cs1 O11 Cs1 95.32(4) 1_655 2_666 ?
C11 O11 Cs1 109.56(12) . 2_666 ?
C11 O11 Cs1 148.16(14) . 1_655 ?
C1 O1 Cs1 154.37(14) . . ?
C13 N3 Cs1 105.41(13) . 2_666 ?
C13 N3 C12 110.67(15) . . ?
C16 N3 Cs1 121.11(12) . 2_666 ?
C16 N3 C13 108.23(16) . . ?
C16 N3 C12 111.54(16) . . ?
C12 N3 Cs1 99.41(13) . 2_666 ?
N2 N1 C5 118.80(16) . . ?
C1 N1 N2 112.21(15) . . ?
C1 N1 C5 128.99(17) . . ?
C14 N4 C15 110.73(16) . . ?
C17 N4 C14 116.99(17) . . ?
C17 N4 C15 114.96(16) . . ?
C3 N2 N1 105.54(16) . . ?
O11 C11 Cs1 51.89(10) . 2_666 ?
O11 C11 C2 123.27(18) . . ?
O11 C11 C12 120.08(17) . . ?
C2 C11 Cs1 136.54(13) . 2_666 ?
C2 C11 C12 116.65(16) . . ?
C12 C11 Cs1 84.25(12) . 2_666 ?
O1 C1 N1 123.86(17) . . ?
O1 C1 C2 132.04(17) . . ?
N1 C1 C2 104.06(15) . . ?
C11 C2 C1 126.32(17) . . ?
C3 C2 C11 128.23(17) . . ?
C3 C2 C1 105.45(16) . . ?
N4 C14 H14A 109.6 . . ?
N4 C14 H14B 109.6 . . ?
N4 C14 C13 110.21(17) . . ?
H14A C14 H14B 108.1 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
N3 C13 C14 109.94(17) . . ?
N3 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C10 C5 N1 121.91(19) . . ?
C6 C5 N1 119.1(2) . . ?
C6 C5 C10 119.0(2) . . ?
N2 C3 C2 112.71(17) . . ?
N2 C3 C4 119.17(19) . . ?
C2 C3 C4 128.10(19) . . ?
C22 C17 N4 119.2(2) . . ?
C18 C17 N4 122.7(2) . . ?
C18 C17 C22 118.1(2) . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 C16 110.90(17) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
N3 C16 C15 110.44(16) . . ?
N3 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
Cs1 C12 H12A 86.0 2_666 . ?
Cs1 C12 H12B 164.5 2_666 . ?
N3 C12 Cs1 58.49(11) . 2_666 ?
N3 C12 C11 114.08(16) . . ?
N3 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C11 C12 Cs1 72.49(11) . 2_666 ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C5 C10 H10 120.1 . . ?
C5 C10 C9 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.9(3) . . ?
C20 C21 H21 119.6 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C51 N51 Cs1 152.8(4) . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N53 C53 C52 179.5(6) . . ?
C53 N53 Cs1 146.2(3) . . ?
N51 C51 C50 179.3(5) . . ?
C53 C52 H52A 109.5 . . ?
C53 C52 H52B 109.5 . . ?
C53 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
C51 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O1 0.93 2.30 2.898(3) 121.8 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cs1 O11 C11 Cs1 139.4(3) 1_655 . . 2_666 ?
Cs1 O11 C11 C2 -94.6(3) 1_655 . . . ?
Cs1 O11 C11 C2 126.07(17) 2_666 . . . ?
Cs1 O11 C11 C12 86.3(3) 1_655 . . . ?
Cs1 O11 C11 C12 -53.0(2) 2_666 . . . ?
Cs1 O1 C1 N1 -71.9(4) . . . . ?
Cs1 O1 C1 C2 105.2(3) . . . . ?
Cs1 N3 C13 C14 -69.04(19) 2_666 . . . ?
Cs1 N3 C16 C15 61.41(19) 2_666 . . . ?
Cs1 N3 C12 C11 48.7(2) 2_666 . . . ?
Cs1 C11 C2 C1 -108.6(2) 2_666 . . . ?
Cs1 C11 C2 C3 72.2(3) 2_666 . . . ?
Cs1 C11 C12 N3 -42.17(18) 2_666 . . . ?
O11 C11 C2 C1 -176.22(19) . . . . ?
O11 C11 C2 C3 4.6(3) . . . . ?
O11 C11 C12 Cs1 39.18(17) . . . 2_666 ?
O11 C11 C12 N3 -3.0(3) . . . . ?
O1 C1 C2 C11 4.9(4) . . . . ?
O1 C1 C2 C3 -175.8(2) . . . . ?
N1 N2 C3 C2 0.1(2) . . . . ?
N1 N2 C3 C4 178.6(2) . . . . ?
N1 C1 C2 C11 -177.56(18) . . . . ?
N1 C1 C2 C3 1.8(2) . . . . ?
N1 C5 C10 C9 -179.6(2) . . . . ?
N1 C5 C6 C7 179.6(3) . . . . ?
N4 C14 C13 N3 -60.3(3) . . . . ?
N4 C17 C22 C21 -177.0(3) . . . . ?
N4 C17 C18 C19 176.6(2) . . . . ?
N4 C15 C16 N3 57.1(2) . . . . ?
N2 N1 C1 O1 175.98(19) . . . . ?
N2 N1 C1 C2 -1.9(2) . . . . ?
N2 N1 C5 C10 166.7(2) . . . . ?
N2 N1 C5 C6 -12.1(3) . . . . ?
C11 C2 C3 N2 178.1(2) . . . . ?
C11 C2 C3 C4 -0.2(4) . . . . ?
C1 N1 N2 C3 1.1(2) . . . . ?
C1 N1 C5 C10 -13.9(3) . . . . ?
C1 N1 C5 C6 167.4(2) . . . . ?
C1 C2 C3 N2 -1.2(2) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?
C2 C11 C12 Cs1 -139.97(17) . . . 2_666 ?
C2 C11 C12 N3 177.86(17) . . . . ?
C14 N4 C17 C22 170.6(2) . . . . ?
C14 N4 C17 C18 -7.3(3) . . . . ?
C14 N4 C15 C16 -54.6(2) . . . . ?
C13 N3 C16 C15 -60.3(2) . . . . ?
C13 N3 C12 Cs1 110.51(17) . . . 2_666 ?
C13 N3 C12 C11 159.2(2) . . . . ?
C5 N1 N2 C3 -179.28(18) . . . . ?
C5 N1 C1 O1 -3.5(3) . . . . ?
C5 N1 C1 C2 178.63(19) . . . . ?
C5 C10 C9 C8 0.1(5) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C17 N4 C14 C13 -169.61(18) . . . . ?
C17 N4 C15 C16 170.06(18) . . . . ?
C17 C22 C21 C20 0.0(5) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C15 N4 C14 C13 56.0(2) . . . . ?
C15 N4 C17 C22 -57.0(3) . . . . ?
C15 N4 C17 C18 125.2(2) . . . . ?
C16 N3 C13 C14 61.9(2) . . . . ?
C16 N3 C12 Cs1 -128.94(16) . . . 2_666 ?
C16 N3 C12 C11 -80.3(2) . . . . ?
C12 N3 C13 C14 -175.61(19) . . . . ?
C12 N3 C16 C15 177.74(17) . . . . ?
C12 C11 C2 C1 2.9(3) . . . . ?
C12 C11 C2 C3 -176.3(2) . . . . ?
C10 C5 C6 C7 0.8(4) . . . . ?
C10 C9 C8 C7 0.8(5) . . . . ?
C6 C5 C10 C9 -0.9(4) . . . . ?
C6 C7 C8 C9 -0.9(5) . . . . ?
C22 C17 C18 C19 -1.3(4) . . . . ?
C22 C21 C20 C19 -0.6(5) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_b_0175_0ma
_database_code_depnum_ccdc_archive 'CCDC 2119869'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;INSTITUTE OF MINERALOGY AND CRYSTALLOGRAPHY BAS
Bulgaria
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N3 O5, H2 O'
_chemical_formula_sum            'C20 H29 N3 O6'
_chemical_formula_weight         407.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.097(3)
_cell_length_b                   14.929(3)
_cell_length_c                   11.827(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.816(8)
_cell_angle_gamma                90
_cell_volume                     2033.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      2.265
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8590.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48896
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.268
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      290
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3220
_reflns_number_total             3601
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.050(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.5095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B), C19(H19A,
 H19B), C16(H16A,H16B), C14(H14A,H14B), C18(H18A,H18B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C7(H7), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.55172(8) 0.25738(6) 0.79326(8) 0.0475(3) Uani 1 1 d . . . . .
O1 O 0.71996(8) 0.43565(7) 0.60580(8) 0.0480(3) Uani 1 1 d . . . . .
O3 O 0.24477(9) 0.15826(7) 0.62133(9) 0.0530(3) Uani 1 1 d . . . . .
O2 O 0.46816(9) 0.11281(7) 0.60482(10) 0.0592(3) Uani 1 1 d . . . . .
O4 O 0.25070(9) 0.32354(7) 0.73279(9) 0.0569(3) Uani 1 1 d . . . . .
N3 N 0.40071(9) 0.30374(7) 0.58560(10) 0.0390(3) Uani 1 1 d . . . . .
N1 N 0.87981(9) 0.39653(7) 0.76597(9) 0.0411(3) Uani 1 1 d . . . . .
N2 N 0.90413(10) 0.34506(8) 0.86992(10) 0.0447(3) Uani 1 1 d . . . . .
O1W O 0.56981(14) 0.43417(9) 0.36938(13) 0.0817(4) Uani 1 1 d . . . . .
C2 C 0.71299(11) 0.33301(8) 0.76535(11) 0.0377(3) Uani 1 1 d . . . . .
C1 C 0.76303(11) 0.39270(8) 0.69965(11) 0.0372(3) Uani 1 1 d . . . . .
C3 C 0.80601(11) 0.30772(8) 0.86755(11) 0.0394(3) Uani 1 1 d . . . . .
C11 C 0.59459(11) 0.30963(8) 0.73672(11) 0.0392(3) Uani 1 1 d . . . . .
C5 C 0.96206(11) 0.46092(9) 0.75739(11) 0.0393(3) Uani 1 1 d . . . . .
C20 C 0.29601(12) 0.36343(9) 0.55408(12) 0.0463(3) Uani 1 1 d . . . . .
H20A H 0.229984 0.330923 0.503274 0.056 Uiso 1 1 calc R U . . .
H20B H 0.310008 0.414696 0.509939 0.056 Uiso 1 1 calc R U . . .
C10 C 0.95164(12) 0.50487(10) 0.65116(12) 0.0493(3) Uani 1 1 d . . . . .
H10 H 0.893242 0.488903 0.582454 0.059 Uiso 1 1 calc R U . . .
C4 C 0.80161(13) 0.24671(10) 0.96587(13) 0.0498(4) Uani 1 1 d . . . . .
H4A H 0.781905 0.187327 0.935178 0.075 Uiso 1 1 calc R U . . .
H4B H 0.743990 0.267745 1.000140 0.075 Uiso 1 1 calc R U . . .
H4C H 0.876091 0.245779 1.025596 0.075 Uiso 1 1 calc R U . . .
C6 C 1.05281(12) 0.48287(10) 0.85735(12) 0.0475(3) Uani 1 1 d . . . . .
H6 H 1.062399 0.452283 0.928220 0.057 Uiso 1 1 calc R U . . .
C12 C 0.51118(12) 0.35531(10) 0.62915(14) 0.0523(4) Uani 1 1 d . . . . .
H12A H 0.494698 0.415479 0.650474 0.063 Uiso 1 1 calc R U . . .
H12B H 0.546971 0.359813 0.566328 0.063 Uiso 1 1 calc R U . . .
C13 C 0.39897(13) 0.24469(10) 0.48297(12) 0.0501(4) Uani 1 1 d . . . . .
H13A H 0.414958 0.280577 0.421395 0.060 Uiso 1 1 calc R U . . .
H13B H 0.322012 0.219167 0.450403 0.060 Uiso 1 1 calc R U . . .
C7 C 1.12896(13) 0.55017(10) 0.85161(14) 0.0548(4) Uani 1 1 d . . . . .
H7 H 1.189547 0.564654 0.919239 0.066 Uiso 1 1 calc R U . . .
C9 C 1.02861(14) 0.57244(11) 0.64830(14) 0.0575(4) Uani 1 1 d . . . . .
H9 H 1.020497 0.602576 0.577390 0.069 Uiso 1 1 calc R U . . .
C8 C 1.11722(14) 0.59616(11) 0.74833(15) 0.0576(4) Uani 1 1 d . . . . .
H8 H 1.167962 0.642377 0.745808 0.069 Uiso 1 1 calc R U . . .
C17 C 0.17024(14) 0.17710(12) 0.69023(15) 0.0607(4) Uani 1 1 d . . . . .
H17A H 0.207104 0.159264 0.771996 0.073 Uiso 1 1 calc R U . . .
H17B H 0.098524 0.143599 0.659899 0.073 Uiso 1 1 calc R U . . .
C19 C 0.26783(14) 0.39559(10) 0.66242(14) 0.0563(4) Uani 1 1 d . . . . .
H19A H 0.330797 0.432896 0.709493 0.068 Uiso 1 1 calc R U . . .
H19B H 0.198087 0.431965 0.638089 0.068 Uiso 1 1 calc R U . . .
C16 C 0.29086(15) 0.07023(10) 0.64027(14) 0.0580(4) Uani 1 1 d . . . . .
H16A H 0.228257 0.026793 0.619077 0.070 Uiso 1 1 calc R U . . .
H16B H 0.334100 0.062074 0.723430 0.070 Uiso 1 1 calc R U . . .
C14 C 0.48668(15) 0.16994(11) 0.51758(15) 0.0597(4) Uani 1 1 d . . . . .
H14A H 0.483384 0.134934 0.447527 0.072 Uiso 1 1 calc R U . . .
H14B H 0.563843 0.195602 0.547257 0.072 Uiso 1 1 calc R U . . .
C18 C 0.14482(14) 0.27480(12) 0.68457(17) 0.0647(4) Uani 1 1 d . . . . .
H18A H 0.108168 0.292595 0.602749 0.078 Uiso 1 1 calc R U . . .
H18B H 0.091816 0.288126 0.729462 0.078 Uiso 1 1 calc R U . . .
C15 C 0.36855(15) 0.05651(11) 0.56593(16) 0.0636(4) Uani 1 1 d . . . . .
H15A H 0.392891 -0.005646 0.570655 0.076 Uiso 1 1 calc R U . . .
H15B H 0.326618 0.069832 0.483693 0.076 Uiso 1 1 calc R U . . .
H1WA H 0.626(2) 0.4252(18) 0.445(3) 0.121(9) Uiso 1 1 d . . . . .
H1WB H 0.567(2) 0.3860(19) 0.321(2) 0.110(8) Uiso 1 1 d . . . . .
H3 H 0.3963(13) 0.2693(10) 0.6423(14) 0.045(4) 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
O11 C11 1.2397(16) . ?
O1 C1 1.2494(15) . ?
O3 C17 1.4163(19) . ?
O3 C16 1.4183(19) . ?
O2 C14 1.4083(19) . ?
O2 C15 1.425(2) . ?
O4 C19 1.4136(19) . ?
O4 C18 1.431(2) . ?
N3 C20 1.4994(17) . ?
N3 C12 1.4909(17) . ?
N3 C13 1.4951(18) . ?
N3 H3 0.859(16) . ?
N1 N2 1.4024(15) . ?
N1 C1 1.3915(16) . ?
N1 C5 1.4093(17) . ?
N2 C3 1.3040(18) . ?
O1W H1WA 0.95(3) . ?
O1W H1WB 0.91(3) . ?
C2 C1 1.4325(18) . ?
C2 C3 1.4274(17) . ?
C2 C11 1.4111(18) . ?
C3 C4 1.4908(19) . ?
C11 C12 1.5219(18) . ?
C5 C10 1.3885(19) . ?
C5 C6 1.3842(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.502(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.380(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.379(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.508(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.370(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.378(2) . ?
C8 H8 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.488(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.485(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C17 O3 C16 112.45(12) . . ?
C14 O2 C15 115.41(13) . . ?
C19 O4 C18 115.26(12) . . ?
C20 N3 H3 107.5(10) . . ?
C12 N3 C20 112.25(11) . . ?
C12 N3 C13 111.92(11) . . ?
C12 N3 H3 107.6(10) . . ?
C13 N3 C20 110.34(10) . . ?
C13 N3 H3 107.0(10) . . ?
N2 N1 C5 118.26(10) . . ?
C1 N1 N2 112.09(10) . . ?
C1 N1 C5 127.22(11) . . ?
C3 N2 N1 105.66(10) . . ?
H1WA O1W H1WB 111(2) . . ?
C3 C2 C1 105.62(11) . . ?
C11 C2 C1 126.17(11) . . ?
C11 C2 C3 128.11(12) . . ?
O1 C1 N1 123.73(12) . . ?
O1 C1 C2 132.11(12) . . ?
N1 C1 C2 104.15(10) . . ?
N2 C3 C2 112.45(11) . . ?
N2 C3 C4 119.60(11) . . ?
C2 C3 C4 127.95(12) . . ?
O11 C11 C2 125.99(12) . . ?
O11 C11 C12 116.94(12) . . ?
C2 C11 C12 117.03(11) . . ?
C10 C5 N1 121.12(12) . . ?
C6 C5 N1 119.53(12) . . ?
C6 C5 C10 119.32(13) . . ?
N3 C20 H20A 109.2 . . ?
N3 C20 H20B 109.2 . . ?
N3 C20 C19 111.89(11) . . ?
H20A C20 H20B 107.9 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C5 C10 H10 120.3 . . ?
C9 C10 C5 119.50(13) . . ?
C9 C10 H10 120.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.85(13) . . ?
C7 C6 H6 120.1 . . ?
N3 C12 C11 110.63(11) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N3 C13 H13A 109.1 . . ?
N3 C13 H13B 109.1 . . ?
N3 C13 C14 112.47(12) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.36(14) . . ?
C8 C7 H7 119.3 . . ?
C10 C9 H9 119.3 . . ?
C8 C9 C10 121.35(14) . . ?
C8 C9 H9 119.3 . . ?
C7 C8 C9 118.55(14) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
O3 C17 H17A 109.9 . . ?
O3 C17 H17B 109.9 . . ?
O3 C17 C18 109.14(13) . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
O4 C19 C20 111.81(12) . . ?
O4 C19 H19A 109.3 . . ?
O4 C19 H19B 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
O3 C16 H16A 109.9 . . ?
O3 C16 H16B 109.9 . . ?
O3 C16 C15 108.90(13) . . ?
H16A C16 H16B 108.3 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
O2 C14 C13 113.00(12) . . ?
O2 C14 H14A 109.0 . . ?
O2 C14 H14B 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O4 C18 C17 109.45(13) . . ?
O4 C18 H18A 109.8 . . ?
O4 C18 H18B 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
O2 C15 C16 110.70(13) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20B O1 0.97 2.59 3.5193(17) 161.2 3_666 yes
C10 H10 O1 0.93 2.34 2.8794(18) 117.0 . yes
C12 H12A O1W 0.97 2.36 3.294(2) 160.2 3_666 yes
C12 H12B O1 0.97 2.30 2.8845(18) 118.1 . yes
C13 H13A O11 0.97 2.62 3.3145(18) 128.3 4_565 yes
C13 H13B O3 0.97 2.63 3.1129(18) 110.7 . yes
C13 H13B O4 0.97 2.53 3.1244(19) 119.3 4_565 yes
C19 H19A O1W 0.97 2.63 3.303(2) 126.3 3_666 yes
O1W H1WA O1 0.95(3) 1.90(3) 2.8302(18) 165(2) . yes
O1W H1WB O11 0.91(3) 2.17(3) 2.9858(17) 150(2) 4_565 yes
O1W H1WB O2 0.91(3) 2.47(3) 3.0723(19) 124(2) 4_565 yes
N3 H3 O11 0.859(16) 2.168(15) 2.6650(15) 116.6(12) . yes
N3 H3 O3 0.859(16) 2.428(15) 2.9904(15) 123.6(12) . yes
N3 H3 O4 0.859(16) 2.461(15) 2.8885(16) 111.5(12) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C11 C12 N3 -21.38(18) . . . . ?
O3 C17 C18 O4 -61.24(18) . . . . ?
O3 C16 C15 O2 66.20(17) . . . . ?
N3 C20 C19 O4 -56.75(16) . . . . ?
N3 C13 C14 O2 60.33(18) . . . . ?
N1 N2 C3 C2 -1.00(15) . . . . ?
N1 N2 C3 C4 179.22(11) . . . . ?
N1 C5 C10 C9 174.98(13) . . . . ?
N1 C5 C6 C7 -175.52(13) . . . . ?
N2 N1 C1 O1 177.30(11) . . . . ?
N2 N1 C1 C2 -1.70(14) . . . . ?
N2 N1 C5 C10 170.61(12) . . . . ?
N2 N1 C5 C6 -11.44(18) . . . . ?
C2 C11 C12 N3 160.80(12) . . . . ?
C1 N1 N2 C3 1.72(14) . . . . ?
C1 N1 C5 C10 -28.59(19) . . . . ?
C1 N1 C5 C6 149.36(13) . . . . ?
C1 C2 C3 N2 -0.01(15) . . . . ?
C1 C2 C3 C4 179.75(13) . . . . ?
C1 C2 C11 O11 179.38(12) . . . . ?
C1 C2 C11 C12 -3.02(19) . . . . ?
C3 C2 C1 O1 -177.86(13) . . . . ?
C3 C2 C1 N1 1.02(13) . . . . ?
C3 C2 C11 O11 -4.9(2) . . . . ?
C3 C2 C11 C12 172.67(13) . . . . ?
C11 C2 C1 O1 -1.4(2) . . . . ?
C11 C2 C1 N1 177.50(12) . . . . ?
C11 C2 C3 N2 -176.40(12) . . . . ?
C11 C2 C3 C4 3.4(2) . . . . ?
C5 N1 N2 C3 165.30(11) . . . . ?
C5 N1 C1 O1 15.5(2) . . . . ?
C5 N1 C1 C2 -163.48(12) . . . . ?
C5 C10 C9 C8 1.3(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C20 N3 C12 C11 137.08(12) . . . . ?
C20 N3 C13 C14 -167.32(12) . . . . ?
C10 C5 C6 C7 2.5(2) . . . . ?
C10 C9 C8 C7 1.0(3) . . . . ?
C6 C5 C10 C9 -3.0(2) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C12 N3 C20 C19 -77.39(15) . . . . ?
C12 N3 C13 C14 66.91(15) . . . . ?
C13 N3 C20 C19 157.02(12) . . . . ?
C13 N3 C12 C11 -98.20(14) . . . . ?
C17 O3 C16 C15 -179.43(13) . . . . ?
C19 O4 C18 C17 131.48(14) . . . . ?
C16 O3 C17 C18 168.64(13) . . . . ?
C14 O2 C15 C16 -123.80(14) . . . . ?
C18 O4 C19 C20 -72.54(16) . . . . ?
C15 O2 C14 C13 70.76(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
