# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_Form-I
_database_code_depnum_ccdc_archive 'CCDC 2024365'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;

_chemical_name_systematic        
; ?
;
_chemical_name_common            'vinpocetine oxalate'
_chemical_formula_moiety         'C2 H O4, C22 H27 N2 O2'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48


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

# POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_symmetry_space_group_name_H-M   P21
_space_group_name_Hall           'p 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x, y+1/2, -z '
_cell_length_a                   18.5604(11)
_cell_length_b                   7.5949(4)
_cell_length_c                   8.0212(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.383(5)
_cell_angle_gamma                90
_cell_volume                     1123.70(12)

_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_theta_min      2
_cell_measurement_theta_max      80.19
_cell_measurement_reflns_used    20
_exptl_crystal_density_diffrn    1.3019(1)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_crystal_description       powder
_cell_special_details            
; ?
;



# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 'borosilicate capillary'
;
_pd_spec_mount_mode              transmission

_pd_spec_shape                   cylinder

_pd_char_particle_morphology     ?
_pd_char_colour                  white # use ICDD colour descriptions



_pd_prep_temperature             293


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

# EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_source_voltage           40
_diffrn_source_current           30
_diffrn_measurement_device_type  'Stoe StadiP'
_diffrn_detector                 'Single photon counting'
_diffrn_detector_type            'DECTRIS MYTHEN 1K'
_pd_meas_scan_method             cont


_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  'Ge 111'

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        5214
_pd_meas_2theta_range_min        2.000
_pd_meas_2theta_range_max        80.195
_pd_meas_2theta_range_inc        0.015




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

# REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.


# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'


_pd_proc_ls_prof_R_factor        0.055
_pd_proc_ls_prof_wR_factor       0.072
_pd_proc_ls_prof_wR_expected     0.023
_refine_ls_R_I_factor            0.037


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    undef
_refine_ls_number_parameters     52
_refine_ls_number_restraints     0
_refine_ls_number_constraints    56

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   3.078


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.

_pd_proc_2theta_range_min        2
_pd_proc_2theta_range_max        50
_pd_proc_2theta_range_inc        0.015
_pd_proc_wavelength              1.5406

#


# The following items are used to identify the programs used.

_computing_data_collection       'Stoe WinXPOW'
_computing_cell_refinement       EXPO2014
_computing_structure_solution    EXPO2014
_computing_structure_refinement  'TOPAS Academic v. 6'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N N 2 0.79834(17) 0.8509(7) 0.5228(7) 1 6.0(3)
C C 2 0.72865(18) 0.9038(8) 0.5460(8) 1 6.0(3)
C1 C 2 0.7146(3) 1.0617(9) 0.6479(9) 1 6.0(3)
N1 N 2 0.6425(4) 1.0459(13) 0.7059(12) 1 6.0(3)
C2 C 2 0.5892(3) 1.0038(15) 0.5618(14) 1 6.0(3)
C3 C 2 0.59914(17) 0.8244(15) 0.4772(13) 1 6.0(3)
C4 C 2 0.67851(18) 0.7949(10) 0.4683(10) 1 6.0(3)
C5 C 2 0.7182(3) 0.6586(9) 0.3919(9) 1 6.0(3)
C6 C 2 0.6964(5) 0.5122(10) 0.2924(10) 1 6.0(3)
C7 C 2 0.7492(6) 0.4040(9) 0.2395(10) 1 6.0(3)
C8 C 2 0.8224(6) 0.4390(8) 0.2828(10) 1 6.0(3)
C9 C 2 0.8456(4) 0.5840(8) 0.3781(9) 1 6.0(3)
C10 C 2 0.7927(3) 0.6953(7) 0.4298(8) 1 6.0(3)
C11 C 2 0.8576(2) 0.9503(8) 0.5971(8) 1 6.0(3)
C12 C 2 0.8478(3) 1.0644(8) 0.7197(8) 1 6.0(3)
C13 C 2 0.7765(4) 1.0923(8) 0.7909(8) 1 6.0(3)
C14 C 2 0.7710(5) 0.9555(9) 0.9311(8) 1 6.0(3)
C15 C 2 0.6955(5) 0.9549(12) 0.9884(10) 1 6.0(3)
C16 C 2 0.6394(4) 0.9170(13) 0.8416(12) 1 6.0(3)
C17 C 2 0.7700(6) 1.2833(9) 0.8541(10) 1 6.0(3)
C18 C 2 0.7846(19) 1.4296(8) 0.7339(19) 1 6.0(3)
C19 C 2 0.9256(2) 0.9468(11) 0.5151(10) 1 6.0(3)
O O 2 0.9846(2) 0.920(3) 0.5888(13) 1 6.0(3)
O1 O 2 0.9134(3) 0.971(3) 0.3503(11) 1 6.0(3)
C20 C 2 0.9777(5) 0.996(6) 0.2645(17) 1 6.0(3)
C21 C 2 0.971(2) 0.878(9) 0.116(4) 1 6.0(3)
H H 2 0.7120(4) 1.1650(9) 0.5703(10) 1 6.0(3)
H1 H 2 0.5408(3) 1.0126(18) 0.5972(16) 1 6.0(3)
H2 H 2 0.5935(3) 1.0957(15) 0.4780(14) 1 6.0(3)
H3 H 2 0.5724(2) 0.8267(17) 0.3608(14) 1 6.0(3)
H4 H 2 0.5801(2) 0.7207(16) 0.5425(14) 1 6.0(3)
H5 H 2 0.6437(5) 0.4899(13) 0.2569(12) 1 6.0(3)
H6 H 2 0.7377(7) 0.3067(10) 0.1722(11) 1 6.0(3)
H7 H 2 0.8594(6) 0.3590(9) 0.2503(11) 1 6.0(3)
H8 H 2 0.9004(4) 0.6035(10) 0.4044(10) 1 6.0(3)
H9 H 2 0.8891(4) 1.1425(10) 0.7575(9) 1 6.0(3)
H10 H 2 0.8092(6) 0.9724(10) 1.0330(7) 1 6.0(3)
H11 H 2 0.7858(4) 0.8346(9) 0.8903(7) 1 6.0(3)
H12 H 2 0.6843(6) 1.0636(13) 1.0367(11) 1 6.0(3)
H13 H 2 0.6892(6) 0.8579(13) 1.0711(10) 1 6.0(3)
H14 H 2 0.6476(4) 0.7907(13) 0.8019(12) 1 6.0(3)
H15 H 2 0.5867(5) 0.9184(16) 0.8649(15) 1 6.0(3)
H16 H 2 0.8036(11) 1.3011(13) 0.9509(19) 1 6.0(3)
H17 H 2 0.7222(7) 1.3032(14) 0.882(3) 1 6.0(3)
H18 H 2 0.7791(18) 1.5403(8) 0.7860(18) 1 6.0(3)
H19 H 2 0.833(2) 1.4191(12) 0.705(4) 1 6.0(3)
H20 H 2 0.751(3) 1.4212(11) 0.6354(11) 1 6.0(3)
H21 H 2 0.9804(19) 1.116(7) 0.231(4) 1 6.0(3)
H22 H 2 1.0197(4) 0.968(9) 0.338(2) 1 6.0(3)
H23 H 2 0.968(4) 0.759(8) 0.152(7) 1 6.0(3)
H24 H 2 0.9285(18) 0.908(11) 0.045(2) 1 6.0(3)
H25 H 2 1.012(2) 0.891(12) 0.057(4) 1 6.0(3)
H26 H 2 0.6297(5) 1.1508(14) 0.7457(13) 1 6.0(3)
C22 C 2 0.5714(5) 0.4124(7) 0.8234(14) 1 6.0(3)
O2 O 2 0.5936(18) 0.278(2) 0.904(2) 1 6.0(3)
O3 O 2 0.5863(9) 0.443(2) 0.6781(16) 1 6.0(3)
C23 C 2 0.524(2) 0.552(4) 0.896(3) 1 6.0(3)
O4 O 2 0.525(3) 0.532(6) 1.058(3) 1 6.0(3)
O5 O 2 0.487(4) 0.675(8) 0.799(5) 1 6.0(3)
H27 H 2 0.489(4) 0.596(8) 1.096(4) 1 6.0(3)
#==============================================================================

# BOND LENGTHS AND ANGLES

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance






























































O C19 1.201(9)
O1 C19 1.329(12)
O1 C20 1.458(14)
N C 1.387(5)
N C10 1.395(8)
N C11 1.411(7)
N1 C1 1.468(10)
N1 C2 1.471(13)
N1 C16 1.469(14)
C C1 1.490(9)
C C4 1.346(8)
C1 C13 1.548(9)
N1 H26 0.900(14)
O2 C22 1.253(19)
C2 C3 1.542(16)
O3 C22 1.250(17)
C3 C4 1.500(5)
C4 C5 1.445(9)
O4 C23 1.31(3)
C5 C10 1.410(8)
C5 C6 1.402(10)
O5 C23 1.34(6)
C6 C7 1.382(13)
C7 C8 1.392(15)
C8 C9 1.382(10)
C9 C10 1.392(9)
C11 C12 1.338(9)
C11 C19 1.485(7)
C18 H20 0.95(4)
C20 H21 0.95(7)
C20 H22 0.95(2)
C21 H25 0.95(5)
C12 C13 1.515(9)
C13 C17 1.545(9)
C13 C14 1.543(9)
C14 C15 1.523(13)
C15 C16 1.509(12)
C17 C18 1.515(16)
C20 C21 1.49(6)
C1 H 0.999(10)
C2 H2 0.978(16)
C2 H1 0.974(9)
C3 H3 1.007(14)
C3 H4 1.030(15)
O4 H27 0.91(8)
C6 H5 1.002(13)
C7 H6 0.926(11)
C8 H7 0.973(13)
C9 H8 1.026(11)
C12 H9 0.989(10)
C14 H10 1.029(11)
C14 H11 1.023(10)
C15 H13 1.007(13)
C15 H12 0.945(13)
C16 H15 1.018(12)
C16 H14 1.027(14)
C17 H17 0.950(18)
C17 H16 0.950(19)
C18 H19 0.96(5)
C18 H18 0.950(14)
C21 H23 0.96(9)
C21 H24 0.95(5)
C22 C23 1.54(3)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle

























































C19 O1 C20 115.5(7)
C N C10 107.6(4)
C N C11 118.9(5)
C10 N C11 133.5(4)
C1 N1 C2 108.9(7)
C1 N1 C16 113.6(7)
C2 N1 C16 111.1(8)
N C C1 122.1(5)
N C C4 111.5(5)
C1 C C4 126.4(4)
N1 C1 C 109.3(6)
N1 C1 C13 113.8(6)
C C1 C13 111.5(5)
C2 N1 H26 106.9(10)
C16 N1 H26 107.1(11)
C1 N1 H26 109.0(10)
N1 C2 C3 115.8(7)
C2 C3 C4 108.6(6)
C3 C4 C5 132.6(7)
C C4 C5 106.1(4)
C C4 C3 121.3(7)
C6 C5 C10 119.6(6)
C4 C5 C10 107.5(5)
C4 C5 C6 132.9(6)
C5 C6 C7 118.5(8)
C6 C7 C8 121.1(7)
C7 C8 C9 121.7(8)
C8 C9 C10 117.5(7)
H1 C2 H2 107.4(12)
C2 C3 H3 108.8(11)
C2 C3 H4 112.7(10)
C4 C3 H3 110.1(8)
C4 C3 H4 107.8(8)
H3 C3 H4 108.9(11)
C23 O4 H27 109(5)
C7 C6 H5 121.0(10)
C5 C6 H5 120.5(9)
C6 C7 H6 121.9(13)
C8 C7 H6 117.0(12)
C9 C8 H7 117.5(11)
C7 C8 H7 120.8(9)
C8 C9 H8 117.9(8)
C10 C9 H8 124.5(7)
C13 C12 H9 118.7(7)
C11 C12 H9 116.8(7)
C13 C14 H10 113.6(8)
C13 C14 H11 109.3(7)
C15 C14 H11 112.5(8)
H10 C14 H11 100.4(9)
C15 C14 H10 109.7(8)
C14 C15 H13 112.2(10)
C16 C15 H12 108.9(10)
C16 C15 H13 104.8(10)
H12 C15 H13 108.8(11)
C14 C15 H12 111.9(10)
N1 C16 H14 111.9(10)
O2 C22 O3 122.5(14)
O4 C23 C22 110(3)
####################################################################### 
# 
# 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_Form-II
_database_code_depnum_ccdc_archive 'CCDC 2024366'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-04-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a32 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C22 H27 N2 O2, C2 H O4'
_chemical_formula_sum            'C24 H28 N2 O6'
_chemical_formula_weight         440.48
_chemical_absolute_configuration ad


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

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.9007(2)
_cell_length_b                   6.30220(10)
_cell_length_c                   20.9554(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.3560(10)
_cell_angle_gamma                90
_cell_volume                     2279.66(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30841
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      72.4140
_cell_measurement_theta_min      4.3300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             936
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.563
_diffrn_reflns_theta_min         4.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_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  ω      1.00  30.00   1.00    1.03    --   38.00  89.00 -23.73   29
  2  ω      9.00  42.00   1.00    1.03    --   42.00  78.00-122.82   33
  3  ω   -123.00  -2.00   1.00    1.03    --  -42.62 -19.00  90.00  121
  4  ω   -117.00 -18.00   1.00    1.03    --  -42.62 -38.00   0.00   99
  5  ω    -87.00  -6.00   1.00    1.03    --  -42.62 125.00 150.00   81
  6  ω   -117.00 -18.00   1.00    1.03    --  -42.62 -38.00 150.00   99
  7  ω     27.00  99.00   1.00    1.03    --   42.62-125.00   0.00   72
  8  ω     13.00  42.00   1.00    1.03    --   46.00  78.00 150.72   29
  9  ω     13.00  42.00   1.00    1.03    --   46.00  78.00-117.21   29
 10  ω     13.00  42.00   1.00    1.03    --   46.00  78.00  75.07   29
 11  ω     26.00 133.00   1.00    1.03    --   58.00  74.00 -72.92  107
 12  ω     30.00 137.00   1.00    1.03    --   62.00  74.00-123.64  107
 13  ω     30.00 137.00   1.00    1.03    --   62.00  74.00  11.24  107
 14  ω     35.00 140.00   1.00    1.03    --   66.00  71.00-151.15  105
 15  ω     34.00 141.00   1.00    1.03    --   66.00  73.00 -49.90  107
 16  ω     34.00 141.00   1.00    1.03    --   66.00  74.00  82.25  107
 17  ω     40.00 143.00   1.00    1.03    --   70.00  64.00 171.26  103
 18  ω     39.00 144.00   1.00    1.03    --   70.00  71.00 -28.50  105
 19  ω     46.00 146.00   1.00    4.15    --   74.00  56.00  93.78  100
 20  ω     43.00 148.00   1.00    4.15    --   74.00  70.00 116.46  105
 21  ω     45.00 147.00   1.00    4.15    --   74.00  63.00 -88.06  102
 22  ω     47.00 152.00   1.00    4.15    --   78.00  71.00  32.07  105
 23  ω     63.00 162.00   1.00    4.15    --   90.00  50.00 -18.72   99
 24  ω     63.00 168.00   1.00    4.15    --   94.00  71.00-154.43  105
 25  ω     65.00 167.00   1.00    4.15    --   94.00  63.00 -80.82  102
 26  ω     97.00 178.00   1.00    4.15    --  104.49 125.00 -60.00   81
 27  ω     75.00 177.00   1.00    4.15    --  104.49  61.00  60.00  102
 28  ω     75.00 177.00   1.00    4.15    --  104.49  61.00-120.00  102
 29  ω     22.00 106.00   1.00    4.15    --  104.49 -94.00 -30.00   84
 30  ω     75.00 177.00   1.00    4.15    --  104.49  61.00-180.00  102
 31  ω     75.00 177.00   1.00    4.15    --  104.49  61.00 120.00  102
 32  ω     31.00 113.00   1.00    4.15    --  104.49-125.00 -60.00   82
 33  ω     22.00 106.00   1.00    4.15    --  104.49 -94.00 120.00   84
 34  ω     75.00 177.00   1.00    4.15    --  104.49  61.00   0.00  102
 35  ω     75.00 177.00   1.00    4.15    --  104.49  61.00 -30.00  102
 36  ω     22.00 106.00   1.00    4.15    --  104.49 -94.00-120.00   84
 37  ω     22.00 106.00   1.00    4.15    --  104.49 -94.00  30.00   84
 38  ω     75.00 177.00   1.00    4.15    --  104.49  61.00  30.00  102
 39  ω     75.00 177.00   1.00    4.15    --  104.49  61.00  90.00  102
 40  ω     97.00 178.00   1.00    4.15    --  104.49 125.00-180.00   81
 41  ω     73.00 178.00   1.00    4.15    --  104.49  72.00 -82.41  105
 42  ω     75.00 177.00   1.00    4.15    --  104.49  61.00 150.00  102
 43  ω     -4.00  22.00   1.00    1.03    --   34.00  93.00 129.18   26
 44  ω     -4.00  23.00   1.00    1.03    --   34.00  92.00   8.00   27
 45  ω     27.00  99.00   1.00    1.03    --   42.62-125.00-180.00   72
 46  ω    -46.00 131.00   1.00    1.03    --   42.62   0.00-180.00  177
 47  ω     10.00  42.00   1.00    1.03    --   42.62  79.00 -89.23   32
 48  ω     22.00 129.00   1.00    1.03    --   54.00  74.00  -7.94  107
 49  ω     22.00 129.00   1.00    1.03    --   54.00  74.00 124.92  107
 50  ω     27.00 132.00   1.00    1.03    --   58.00  72.00 141.74  105
 51  ω     31.00 136.00   1.00    1.03    --   62.00  72.00  47.03  105
 52  ω     34.00 141.00   1.00    1.03    --   66.00  74.00  60.23  107
 53  ω     35.00 139.00   1.00    1.03    --   66.00  69.00 151.62  104
 54  ω     34.00 141.00   1.00    1.03    --   66.00  74.00 121.82  107
 55  ω     42.00 143.00   1.00    1.03    --   70.00  57.00   9.67  101
 56  ω     45.00 146.00   1.00    4.15    --   74.00  62.00-117.34  101
 57  ω     53.00 154.00   1.00    4.15    --   82.00  60.00-103.58  101
 58  ω     79.00 178.00   1.00    4.15    --  104.49  45.00-180.00   99
 59  ω     79.00 143.00   1.00    4.15    --  104.49  45.00 -30.00   64
 60  ω    103.00 178.00   1.00    4.15    --  104.49  77.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0513388000
_diffrn_orient_matrix_UB_12      -0.0173803000
_diffrn_orient_matrix_UB_13      -0.0483087000
_diffrn_orient_matrix_UB_21      0.0567210000
_diffrn_orient_matrix_UB_22      0.1627697000
_diffrn_orient_matrix_UB_23      0.0415402000
_diffrn_orient_matrix_UB_31      0.0459393000
_diffrn_orient_matrix_UB_32      -0.1815160000
_diffrn_orient_matrix_UB_33      0.0418887000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4385
_reflns_number_total             4465
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S.; Flack, H. D.; Wagner, T. (2013). Acta Cryst. B69, 249-259).
 Hooft y determined according to Hooft et al. 
 (Hooft, R. W. W; Straver, L. H.; Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_abs_structure_Hooft   0.04(3)
_refine_ls_extinction_coef       0.00070(14)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.213
_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)+(0.0430P)²+0.9443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0745
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.003
Uanis(C16) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.006
3.a Ternary CH refined with riding coordinates:
 N1(H1), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C1(H1A,H1B), C19(H19A,H19B), C2(H2A,H2B), C21(H21A,H21B),
 C18(H18A,H18B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C7(H7), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C17(H17A,H17B,H17C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_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
O4 O 0.62579(7) 0.8142(2) 0.99815(6) 0.0246(3) Uani 1 1 d . . . . .
O3 O 0.59322(7) 0.9854(2) 0.90108(6) 0.0278(3) Uani 1 1 d . . . . .
O5 O 0.74298(7) 1.1412(2) 0.93593(6) 0.0254(3) Uani 1 1 d . . . . .
H5O H 0.783355 1.204670 0.952864 0.038 Uiso 1 1 calc R U . . .
O2 O 0.39086(7) 0.4261(3) 0.54642(6) 0.0340(4) Uani 1 1 d . . . . .
O6 O 0.73064(9) 1.1428(3) 1.03933(7) 0.0366(4) Uani 1 1 d . . . . .
O1 O 0.28364(7) 0.4008(3) 0.58226(6) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.38521(8) 0.3630(2) 0.71427(7) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.50875(8) 0.6402(2) 0.85848(7) 0.0171(3) Uani 1 1 d . . . . .
H1N H 0.534490 0.778243 0.868172 0.020 Uiso 1 1 calc R U . . .
C23 C 0.63613(10) 0.9495(3) 0.95788(8) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.41220(9) 0.4543(3) 0.77645(8) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.34472(9) 0.1665(3) 0.78931(8) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.34506(9) 0.1783(3) 0.72174(8) 0.0192(3) Uani 1 1 d . . . . .
C24 C 0.70862(10) 1.0893(3) 0.98201(8) 0.0208(3) Uani 1 1 d . . . . .
C14 C 0.40649(9) 0.4503(3) 0.65995(8) 0.0197(3) Uani 1 1 d . . . . .
C13 C 0.46679(9) 0.5842(3) 0.67041(8) 0.0196(3) Uani 1 1 d . . . . .
H13 H 0.478168 0.645869 0.633775 0.024 Uiso 1 1 calc R U . . .
C3 C 0.38830(9) 0.3449(3) 0.82261(8) 0.0192(3) Uani 1 1 d . . . . .
C20 C 0.57996(9) 0.4673(3) 0.75975(8) 0.0203(3) Uani 1 1 d . . . . .
H20A H 0.555452 0.328822 0.753263 0.024 Uiso 1 1 calc R U . . .
H20B H 0.615530 0.475416 0.732044 0.024 Uiso 1 1 calc R U . . .
C11 C 0.46459(9) 0.6422(3) 0.78637(7) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.432594 0.770555 0.777878 0.020 Uiso 1 1 calc R U . . .
C1 C 0.45338(10) 0.6211(3) 0.90159(8) 0.0224(4) Uani 1 1 d . . . . .
H1A H 0.415175 0.733622 0.890207 0.027 Uiso 1 1 calc R U . . .
H1B H 0.481949 0.640202 0.947501 0.027 Uiso 1 1 calc R U . . .
C12 C 0.51741(9) 0.6406(3) 0.73837(8) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.31340(10) 0.0170(3) 0.67718(9) 0.0233(4) Uani 1 1 d . . . . .
H8 H 0.314970 0.023317 0.633220 0.028 Uiso 1 1 calc R U . . .
C19 C 0.62509(9) 0.4912(3) 0.83193(9) 0.0224(4) Uani 1 1 d . . . . .
H19A H 0.664447 0.381712 0.843459 0.027 Uiso 1 1 calc R U . . .
H19B H 0.650777 0.628104 0.838516 0.027 Uiso 1 1 calc R U . . .
C7 C 0.27953(9) -0.1528(3) 0.70083(9) 0.0252(4) Uani 1 1 d . . . . .
H7 H 0.258641 -0.263231 0.672208 0.030 Uiso 1 1 calc R U . . .
C2 C 0.41172(10) 0.4075(3) 0.89413(8) 0.0230(4) Uani 1 1 d . . . . .
H2A H 0.445767 0.300508 0.919723 0.028 Uiso 1 1 calc R U . . .
H2B H 0.366184 0.417884 0.910777 0.028 Uiso 1 1 calc R U . . .
C21 C 0.55177(10) 0.8647(3) 0.73721(9) 0.0235(4) Uani 1 1 d . . . . .
H21A H 0.509798 0.961713 0.717899 0.028 Uiso 1 1 calc R U . . .
H21B H 0.574282 0.909574 0.782514 0.028 Uiso 1 1 calc R U . . .
C6 C 0.27590(10) -0.1627(3) 0.76678(10) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.251484 -0.277210 0.780748 0.030 Uiso 1 1 calc R U . . .
C18 C 0.57090(9) 0.4734(3) 0.87599(8) 0.0201(3) Uani 1 1 d . . . . .
H18A H 0.547236 0.333758 0.870967 0.024 Uiso 1 1 calc R U . . .
H18B H 0.600002 0.490069 0.921846 0.024 Uiso 1 1 calc R U . . .
C5 C 0.30817(9) -0.0045(3) 0.81139(9) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.305651 -0.011461 0.855102 0.027 Uiso 1 1 calc R U . . .
C15 C 0.35247(10) 0.4211(3) 0.59284(8) 0.0235(4) Uani 1 1 d . . . . .
C22 C 0.61346(12) 0.8854(4) 0.69916(11) 0.0364(5) Uani 1 1 d . . . . .
H22A H 0.593830 0.828271 0.655443 0.055 Uiso 1 1 calc R U . . .
H22B H 0.659012 0.808434 0.721938 0.055 Uiso 1 1 calc R U . . .
H22C H 0.626265 1.032308 0.696207 0.055 Uiso 1 1 calc R U . . .
C16 C 0.34383(13) 0.4219(5) 0.47791(9) 0.0415(6) Uani 1 1 d . U . A 1
H16A H 0.310639 0.545925 0.468459 0.050 Uiso 1 1 calc R U . A 1
H16B H 0.311546 0.295943 0.469800 0.050 Uiso 1 1 calc R U . A 1
C17 C 0.39859(17) 0.4207(8) 0.43590(12) 0.0798(11) Uani 1 1 d . U . A 1
H17A H 0.370230 0.432708 0.390249 0.120 Uiso 1 1 calc R U . A 1
H17B H 0.427373 0.290308 0.442505 0.120 Uiso 1 1 calc R U . A 1
H17C H 0.433677 0.538137 0.447726 0.120 Uiso 1 1 calc R U . 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
O4 C23 1.248(2) . ?
O3 C23 1.254(2) . ?
O5 H5O 0.8200 . ?
O5 C24 1.316(2) . ?
O2 C15 1.332(2) . ?
O2 C16 1.460(2) . ?
O6 C24 1.209(2) . ?
O1 C15 1.200(2) . ?
N2 C10 1.389(2) . ?
N2 C9 1.398(2) . ?
N2 C14 1.405(2) . ?
N1 H1N 0.9800 . ?
N1 C11 1.5086(19) . ?
N1 C1 1.512(2) . ?
N1 C18 1.504(2) . ?
C23 C24 1.539(2) . ?
C10 C3 1.347(2) . ?
C10 C11 1.490(2) . ?
C4 C9 1.420(2) . ?
C4 C3 1.439(3) . ?
C4 C5 1.401(3) . ?
C9 C8 1.395(3) . ?
C14 C13 1.341(3) . ?
C14 C15 1.492(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.514(2) . ?
C3 C2 1.499(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C12 1.543(2) . ?
C20 C19 1.522(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.552(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(3) . ?
C12 C21 1.543(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.510(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.402(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.529(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.385(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C5 H5 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.481(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C24 O5 H5O 109.5 . . ?
C15 O2 C16 116.30(14) . . ?
C10 N2 C9 107.53(13) . . ?
C10 N2 C14 119.77(15) . . ?
C9 N2 C14 132.40(14) . . ?
C11 N1 H1N 107.1 . . ?
C11 N1 C1 110.27(12) . . ?
C1 N1 H1N 107.1 . . ?
C18 N1 H1N 107.1 . . ?
C18 N1 C11 114.05(12) . . ?
C18 N1 C1 110.98(13) . . ?
O4 C23 O3 126.99(16) . . ?
O4 C23 C24 115.61(15) . . ?
O3 C23 C24 117.38(15) . . ?
N2 C10 C11 120.64(14) . . ?
C3 C10 N2 111.35(15) . . ?
C3 C10 C11 127.92(15) . . ?
C9 C4 C3 107.33(15) . . ?
C5 C4 C9 119.69(16) . . ?
C5 C4 C3 132.93(15) . . ?
N2 C9 C4 107.05(14) . . ?
C8 C9 N2 131.41(16) . . ?
C8 C9 C4 121.42(16) . . ?
O5 C24 C23 114.73(14) . . ?
O6 C24 O5 124.53(16) . . ?
O6 C24 C23 120.73(16) . . ?
N2 C14 C15 117.92(15) . . ?
C13 C14 N2 119.54(15) . . ?
C13 C14 C15 121.62(15) . . ?
C14 C13 H13 118.1 . . ?
C14 C13 C12 123.83(15) . . ?
C12 C13 H13 118.1 . . ?
C10 C3 C4 106.64(14) . . ?
C10 C3 C2 121.71(16) . . ?
C4 C3 C2 131.53(16) . . ?
H20A C20 H20B 107.9 . . ?
C12 C20 H20A 109.3 . . ?
C12 C20 H20B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C19 C20 C12 111.82(14) . . ?
N1 C11 H11 108.3 . . ?
N1 C11 C12 113.67(12) . . ?
C10 C11 N1 106.07(13) . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C12 111.93(13) . . ?
C12 C11 H11 108.3 . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 112.87(14) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C13 C12 C20 108.31(14) . . ?
C13 C12 C11 107.19(13) . . ?
C13 C12 C21 110.00(14) . . ?
C20 C12 C11 109.63(13) . . ?
C21 C12 C20 113.00(14) . . ?
C21 C12 C11 108.55(13) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 C9 117.55(16) . . ?
C7 C8 H8 121.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C18 C19 C20 110.02(13) . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C8 C7 H7 119.1 . . ?
C8 C7 C6 121.74(17) . . ?
C6 C7 H7 119.1 . . ?
C3 C2 C1 109.54(14) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C12 C21 H21A 108.4 . . ?
C12 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C22 C21 C12 115.59(16) . . ?
C22 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 120.90(18) . . ?
C5 C6 H6 119.6 . . ?
N1 C18 C19 110.62(13) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.62(16) . . ?
C6 C5 H5 120.7 . . ?
O2 C15 C14 110.76(14) . . ?
O1 C15 O2 124.82(16) . . ?
O1 C15 C14 124.40(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
O2 C16 C17 106.53(18) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O4 C23 C24 O5 144.54(16) . . . . ?
O4 C23 C24 O6 -35.1(2) . . . . ?
O3 C23 C24 O5 -36.8(2) . . . . ?
O3 C23 C24 O6 143.58(18) . . . . ?
N2 C10 C3 C4 1.79(19) . . . . ?
N2 C10 C3 C2 178.14(15) . . . . ?
N2 C10 C11 N1 -155.99(14) . . . . ?
N2 C10 C11 C12 -31.5(2) . . . . ?
N2 C9 C8 C7 177.15(17) . . . . ?
N2 C14 C13 C12 3.3(3) . . . . ?
N2 C14 C15 O2 -153.33(16) . . . . ?
N2 C14 C15 O1 28.3(3) . . . . ?
N1 C11 C12 C13 165.21(13) . . . . ?
N1 C11 C12 C20 47.86(18) . . . . ?
N1 C11 C12 C21 -76.01(17) . . . . ?
N1 C1 C2 C3 -41.29(19) . . . . ?
C10 N2 C9 C4 3.22(17) . . . . ?
C10 N2 C9 C8 -172.66(18) . . . . ?
C10 N2 C14 C13 16.7(2) . . . . ?
C10 N2 C14 C15 -152.53(16) . . . . ?
C10 C3 C2 C1 8.4(2) . . . . ?
C10 C11 C12 C13 45.06(18) . . . . ?
C10 C11 C12 C20 -72.29(17) . . . . ?
C10 C11 C12 C21 163.85(13) . . . . ?
C4 C9 C8 C7 1.8(2) . . . . ?
C4 C3 C2 C1 -176.32(17) . . . . ?
C9 N2 C10 C3 -3.19(18) . . . . ?
C9 N2 C10 C11 173.52(15) . . . . ?
C9 N2 C14 C13 -156.20(17) . . . . ?
C9 N2 C14 C15 34.6(3) . . . . ?
C9 C4 C3 C10 0.27(19) . . . . ?
C9 C4 C3 C2 -175.57(17) . . . . ?
C9 C4 C5 C6 2.6(2) . . . . ?
C9 C8 C7 C6 0.9(3) . . . . ?
C14 N2 C10 C3 -177.67(15) . . . . ?
C14 N2 C10 C11 -1.0(2) . . . . ?
C14 N2 C9 C4 176.72(16) . . . . ?
C14 N2 C9 C8 0.9(3) . . . . ?
C14 C13 C12 C20 84.0(2) . . . . ?
C14 C13 C12 C11 -34.2(2) . . . . ?
C14 C13 C12 C21 -152.01(17) . . . . ?
C13 C14 C15 O2 37.7(3) . . . . ?
C13 C14 C15 O1 -140.7(2) . . . . ?
C13 C12 C21 C22 -70.47(19) . . . . ?
C3 C10 C11 N1 20.1(2) . . . . ?
C3 C10 C11 C12 144.62(16) . . . . ?
C3 C4 C9 N2 -2.17(18) . . . . ?
C3 C4 C9 C8 174.20(15) . . . . ?
C3 C4 C5 C6 -174.48(18) . . . . ?
C20 C12 C21 C22 50.7(2) . . . . ?
C20 C19 C18 N1 -58.66(19) . . . . ?
C11 N1 C1 C2 66.67(17) . . . . ?
C11 N1 C18 C19 53.75(18) . . . . ?
C11 C10 C3 C4 -174.62(16) . . . . ?
C11 C10 C3 C2 1.7(3) . . . . ?
C11 C12 C21 C22 172.54(15) . . . . ?
C1 N1 C11 C10 -51.30(17) . . . . ?
C1 N1 C11 C12 -174.70(13) . . . . ?
C1 N1 C18 C19 179.03(14) . . . . ?
C12 C20 C19 C18 60.38(19) . . . . ?
C8 C7 C6 C5 -1.8(3) . . . . ?
C19 C20 C12 C13 -170.53(14) . . . . ?
C19 C20 C12 C11 -53.88(18) . . . . ?
C19 C20 C12 C21 67.34(18) . . . . ?
C7 C6 C5 C4 0.0(2) . . . . ?
C18 N1 C11 C10 74.35(16) . . . . ?
C18 N1 C11 C12 -49.06(19) . . . . ?
C18 N1 C1 C2 -60.70(18) . . . . ?
C5 C4 C9 N2 -179.92(14) . . . . ?
C5 C4 C9 C8 -3.6(2) . . . . ?
C5 C4 C3 C10 177.61(18) . . . . ?
C5 C4 C3 C2 1.8(3) . . . . ?
C15 O2 C16 C17 -178.0(3) . . . . ?
C15 C14 C13 C12 172.11(16) . . . . ?
C16 O2 C15 O1 4.7(3) . . . . ?
C16 O2 C15 C14 -173.72(18) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.744


####################################################################### 
# 
# 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_EtOAc-solvate
_database_code_depnum_ccdc_archive 'CCDC 2024367'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N2 O2, C2 H O4, 0.158(C4 H8 O2)'
_chemical_formula_sum            'C24.63 H29.26 N2 O6.32'
_chemical_formula_weight         454.41


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

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   17.8855(2)
_cell_length_b                   6.32180(10)
_cell_length_c                   21.0313(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.3460(10)
_cell_angle_gamma                90
_cell_volume                     2293.19(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110.00(10)
_cell_measurement_reflns_used    29449
_cell_measurement_theta_min      4.3220
_cell_measurement_theta_max      72.3610
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.050
_exptl_crystal_face_perp_dist    
;
  -3   -3   -9 0.1249
   5   -3    0 0.1842
   5    0   -1 0.0500
  -4   -3    5 0.1700
   4    3    4 0.1241
   0    0    1 0.0250
 -12    0    5 0.0489
   0    0   -1 0.0250
   4    0   -3 0.0528
;
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             966.20
_diffrn_ambient_temperature      110.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_number            37992
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.360
_diffrn_reflns_theta_max         72.636
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4462
_reflns_number_gt                4366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+1.2181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4462
_refine_ls_number_parameters     369
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.37410(8) 0.8277(2) 0.00160(7) 0.0210(3) Uani 1 1 d . . . . .
O5 O 0.25706(9) 1.1557(3) 0.06358(7) 0.0217(3) Uani 1 1 d . . . . .
H1 H 0.2089(18) 1.233(5) 0.0413(15) 0.037(8) Uiso 1 1 d . . . . .
O3 O 0.40738(9) 1.0006(2) 0.09796(7) 0.0246(3) Uani 1 1 d . . . . .
O6 O 0.26943(10) 1.1576(3) -0.03964(7) 0.0303(4) Uani 1 1 d . . . . .
O1 O 0.71495(9) 0.4191(3) 0.41634(8) 0.0344(4) Uani 1 1 d . . . . .
N006 N 0.61414(9) 0.3806(3) 0.28489(8) 0.0173(3) Uani 1 1 d . . . . .
N007 N 0.49111(9) 0.6552(3) 0.14051(8) 0.0162(3) Uani 1 1 d . . . . .
H007 H 0.465458 0.792825 0.130655 0.019 Uiso 1 1 calc R U . . .
C10 C 0.58741(11) 0.4703(3) 0.22269(9) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.65450(11) 0.1959(3) 0.27778(10) 0.0185(4) Uani 1 1 d . . . . .
C24 C 0.29151(12) 1.1033(3) 0.01760(10) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.61155(11) 0.3611(3) 0.17697(9) 0.0169(4) Uani 1 1 d . . . . .
C23 C 0.36398(11) 0.9640(3) 0.04150(10) 0.0177(4) Uani 1 1 d . . . . .
C20 C 0.41900(11) 0.4834(3) 0.23846(10) 0.0181(4) Uani 1 1 d . . . . .
H20A H 0.443459 0.345258 0.245139 0.022 Uiso 1 1 calc R U . . .
H20B H 0.383150 0.491892 0.265840 0.022 Uiso 1 1 calc R U . . .
C11 C 0.53488(10) 0.6571(3) 0.21260(9) 0.0152(4) Uani 1 1 d . . . . .
H11 H 0.566836 0.785230 0.221214 0.018 Uiso 1 1 calc R U . . .
C4 C 0.65497(11) 0.1833(3) 0.21034(9) 0.0177(4) Uani 1 1 d . . . . .
C12 C 0.48152(11) 0.6557(3) 0.25990(10) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.54680(12) 0.6354(4) 0.09813(10) 0.0203(4) Uani 1 1 d . . . . .
H1A H 0.585067 0.747423 0.109636 0.024 Uiso 1 1 calc R U . . .
H1AB H 0.518535 0.654416 0.052310 0.024 Uiso 1 1 calc R U . . .
C14 C 0.59233(12) 0.4676(4) 0.33866(10) 0.0219(4) Uani 1 1 d . . . . .
C19 C 0.37421(11) 0.5068(4) 0.16634(10) 0.0201(4) Uani 1 1 d . . . . .
H19A H 0.334913 0.397384 0.154721 0.024 Uiso 1 1 calc R U . . .
H19B H 0.348446 0.643097 0.159563 0.024 Uiso 1 1 calc R U . . .
C18 C 0.42889(11) 0.4888(3) 0.12296(9) 0.0178(4) Uani 1 1 d . . . . .
H18A H 0.452579 0.349685 0.128171 0.021 Uiso 1 1 calc R U . . .
H18B H 0.400074 0.505151 0.077168 0.021 Uiso 1 1 calc R U . . .
C7 C 0.72070(11) -0.1333(4) 0.29888(11) 0.0256(5) Uani 1 1 d . . . . .
H7 H 0.741806 -0.242887 0.327539 0.031 Uiso 1 1 calc R U . . .
C5 C 0.69161(11) 0.0124(4) 0.18854(11) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.693959 0.004480 0.144953 0.025 Uiso 1 1 calc R U . . .
C13 C 0.53168(12) 0.6008(4) 0.32783(10) 0.0221(5) Uani 1 1 d . . . . .
H13 H 0.519900 0.662598 0.364123 0.027 Uiso 1 1 calc R U . . .
C2 C 0.58852(12) 0.4223(3) 0.10572(9) 0.0205(4) Uani 1 1 d . . . . .
H2A H 0.554522 0.315452 0.080246 0.025 Uiso 1 1 calc R U . . .
H2AB H 0.634220 0.432440 0.089298 0.025 Uiso 1 1 calc R U . . .
C8 C 0.68660(12) 0.0364(4) 0.32224(11) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.685229 0.043366 0.366087 0.028 Uiso 1 1 calc R U . . .
C6 C 0.72413(12) -0.1439(4) 0.23316(12) 0.0249(5) Uani 1 1 d . . . . .
H6 H 0.748709 -0.257946 0.219380 0.030 Uiso 1 1 calc R U . . .
C21 C 0.44694(12) 0.8800(4) 0.26057(11) 0.0229(4) Uani 1 1 d . . . . .
H21A H 0.488747 0.976671 0.280375 0.028 Uiso 1 1 calc R U . . .
H21B H 0.425192 0.924906 0.215342 0.028 Uiso 1 1 calc R U . . .
C22 C 0.38445(14) 0.8998(5) 0.29735(13) 0.0352(6) Uani 1 1 d . . . . .
H22A H 0.372000 1.046294 0.300794 0.053 Uiso 1 1 calc R U . . .
H22B H 0.403094 0.840610 0.340707 0.053 Uiso 1 1 calc R U . . .
H22C H 0.338877 0.824786 0.273718 0.053 Uiso 1 1 calc R U . . .
C15 C 0.64624(13) 0.4422(5) 0.40576(11) 0.0322(6) Uani 1 1 d . . . . .
C16A C 0.6551(4) 0.4033(13) 0.5211(3) 0.0406(12) Uani 0.517(6) 1 d . U P A 1
H16A H 0.688832 0.525788 0.530833 0.049 Uiso 0.517(6) 1 calc R U P A 1
H16B H 0.686809 0.276573 0.528533 0.049 Uiso 0.517(6) 1 calc R U P A 1
C17A C 0.5996(5) 0.4021(17) 0.5637(4) 0.0522(19) Uani 0.517(6) 1 d . U P A 1
H17A H 0.627701 0.424646 0.608884 0.078 Uiso 0.517(6) 1 calc R U P A 1
H17B H 0.573537 0.268040 0.559719 0.078 Uiso 0.517(6) 1 calc R U P A 1
H17C H 0.562096 0.512851 0.549864 0.078 Uiso 0.517(6) 1 calc R U P A 1
O2A O 0.6066(3) 0.4109(9) 0.4522(2) 0.0283(7) Uani 0.517(6) 1 d . U P A 1
C16B C 0.6578(5) 0.5050(14) 0.5193(4) 0.0406(12) Uani 0.350(8) 1 d D U P A 2
H16C H 0.690524 0.629742 0.526933 0.049 Uiso 0.350(8) 1 calc R U P A 2
H16D H 0.690453 0.380340 0.529008 0.049 Uiso 0.350(8) 1 calc R U P A 2
C17B C 0.6003(7) 0.510(3) 0.5622(6) 0.0522(19) Uani 0.350(8) 1 d D U P A 2
H17D H 0.628385 0.523622 0.607751 0.078 Uiso 0.350(8) 1 calc R U P A 2
H17E H 0.570677 0.381776 0.556054 0.078 Uiso 0.350(8) 1 calc R U P A 2
H17F H 0.566017 0.628789 0.549661 0.078 Uiso 0.350(8) 1 calc R U P A 2
O2B O 0.6103(3) 0.4998(9) 0.4520(3) 0.0283(7) Uani 0.350(8) 1 d . U P A 2
C16C C 0.6578(5) 0.5050(14) 0.5193(4) 0.0406(12) Uani 0.132(7) 1 d D U P A 3
H16E H 0.708942 0.559833 0.521050 0.049 Uiso 0.132(7) 1 calc R U P A 3
H16F H 0.663323 0.363963 0.538136 0.049 Uiso 0.132(7) 1 calc R U P A 3
C17C C 0.6161(14) 0.651(5) 0.5573(10) 0.0522(19) Uani 0.132(7) 1 d D U P A 3
H17G H 0.644943 0.656198 0.602791 0.078 Uiso 0.132(7) 1 calc R U P A 3
H17H H 0.565064 0.596372 0.554131 0.078 Uiso 0.132(7) 1 calc R U P A 3
H17I H 0.612095 0.790212 0.538761 0.078 Uiso 0.132(7) 1 calc R U P A 3
O2C O 0.6103(3) 0.4998(9) 0.4520(3) 0.0283(7) Uani 0.132(7) 1 d . . P A 3
C25 C 0.4492(9) 0.984(3) 0.5355(8) 0.045(4) Uani 0.158(3) 1 d D U P B -1
C27 C 0.5743(10) 1.012(4) 0.5202(8) 0.050(5) Uani 0.158(3) 1 d D U P B -1
H27A H 0.601733 0.930220 0.558316 0.060 Uiso 0.158(3) 1 calc R U P B -1
H27B H 0.574832 1.159294 0.532935 0.060 Uiso 0.158(3) 1 calc R U P B -1
O8 O 0.4945(10) 0.9367(19) 0.4966(13) 0.051(3) Uani 0.158(3) 1 d D U P B -1
O7 O 0.4685(9) 1.069(3) 0.5879(7) 0.056(4) Uani 0.158(3) 1 d . U P B -1
C28 C 0.6124(10) 0.986(3) 0.4652(8) 0.035(4) Uani 0.158(3) 1 d D U P B -1
H28A H 0.667692 0.994274 0.482598 0.053 Uiso 0.158(3) 1 calc R U P B -1
H28B H 0.595205 1.095780 0.433249 0.053 Uiso 0.158(3) 1 calc R U P B -1
H28C H 0.598899 0.850503 0.444628 0.053 Uiso 0.158(3) 1 calc R U P B -1
C26 C 0.3683(11) 0.920(5) 0.5019(14) 0.075(8) Uani 0.158(3) 1 d D U P B -1
H26A H 0.334307 1.038744 0.499303 0.112 Uiso 0.158(3) 1 calc R U P B -1
H26B H 0.352551 0.808184 0.526416 0.112 Uiso 0.158(3) 1 calc R U P B -1
H26C H 0.366050 0.870781 0.458183 0.112 Uiso 0.158(3) 1 calc R U P B -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
O4 C23 1.249(3) . ?
O5 C24 1.319(3) . ?
O5 H1 0.99(3) . ?
O3 C23 1.256(2) . ?
O6 C24 1.213(3) . ?
O1 C15 1.198(3) . ?
N006 C10 1.389(2) . ?
N006 C9 1.401(3) . ?
N006 C14 1.403(3) . ?
N007 C18 1.504(2) . ?
N007 C1 1.507(3) . ?
N007 C11 1.511(2) . ?
N007 H007 0.9800 . ?
C10 C3 1.344(3) . ?
C10 C11 1.489(3) . ?
C9 C8 1.392(3) . ?
C9 C4 1.423(3) . ?
C24 C23 1.538(3) . ?
C3 C4 1.439(3) . ?
C3 C2 1.496(3) . ?
C20 C19 1.524(3) . ?
C20 C12 1.541(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C11 C12 1.550(3) . ?
C11 H11 0.9800 . ?
C4 C5 1.402(3) . ?
C12 C13 1.513(3) . ?
C12 C21 1.549(3) . ?
C1 C2 1.527(3) . ?
C1 H1A 0.9700 . ?
C1 H1AB 0.9700 . ?
C14 C13 1.344(3) . ?
C14 C15 1.492(3) . ?
C19 C18 1.508(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C7 C8 1.387(3) . ?
C7 C6 1.401(3) . ?
C7 H7 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C21 C22 1.523(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C15 O2C 1.350(6) . ?
C15 O2B 1.350(6) . ?
C15 O2A 1.364(6) . ?
C16A O2A 1.480(9) . ?
C16A C17A 1.503(9) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C16B O2B 1.446(9) . ?
C16B C17B 1.537(11) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C16C O2C 1.446(9) . ?
C16C C17C 1.536(12) . ?
C16C H16E 0.9700 . ?
C16C H16F 0.9700 . ?
C17C H17G 0.9600 . ?
C17C H17H 0.9600 . ?
C17C H17I 0.9600 . ?
C25 O7 1.19(2) . ?
C25 O8 1.330(3) . ?
C25 C26 1.490(3) . ?
C27 O8 1.460(3) . ?
C27 C28 1.499(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C24 O5 H1 107.0(17) . . ?
C10 N006 C9 107.35(16) . . ?
C10 N006 C14 119.95(18) . . ?
C9 N006 C14 132.37(18) . . ?
C18 N007 C1 111.01(15) . . ?
C18 N007 C11 113.90(15) . . ?
C1 N007 C11 110.24(14) . . ?
C18 N007 H007 107.1 . . ?
C1 N007 H007 107.1 . . ?
C11 N007 H007 107.1 . . ?
C3 C10 N006 111.61(18) . . ?
C3 C10 C11 127.97(18) . . ?
N006 C10 C11 120.32(17) . . ?
C8 C9 N006 131.7(2) . . ?
C8 C9 C4 121.2(2) . . ?
N006 C9 C4 107.00(17) . . ?
O6 C24 O5 124.33(19) . . ?
O6 C24 C23 120.77(18) . . ?
O5 C24 C23 114.91(17) . . ?
C10 C3 C4 106.64(17) . . ?
C10 C3 C2 121.89(18) . . ?
C4 C3 C2 131.34(18) . . ?
O4 C23 O3 126.79(19) . . ?
O4 C23 C24 115.79(17) . . ?
O3 C23 C24 117.40(18) . . ?
C19 C20 C12 111.86(17) . . ?
C19 C20 H20A 109.2 . . ?
C12 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C12 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C10 C11 N007 106.03(16) . . ?
C10 C11 C12 112.11(16) . . ?
N007 C11 C12 113.60(14) . . ?
C10 C11 H11 108.3 . . ?
N007 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C5 C4 C9 119.73(19) . . ?
C5 C4 C3 132.93(19) . . ?
C9 C4 C3 107.29(17) . . ?
C13 C12 C20 108.49(17) . . ?
C13 C12 C21 109.88(17) . . ?
C20 C12 C21 112.93(16) . . ?
C13 C12 C11 107.18(15) . . ?
C20 C12 C11 109.80(16) . . ?
C21 C12 C11 108.41(16) . . ?
N007 C1 C2 113.10(16) . . ?
N007 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N007 C1 H1AB 109.0 . . ?
C2 C1 H1AB 109.0 . . ?
H1A C1 H1AB 107.8 . . ?
C13 C14 N006 119.56(18) . . ?
C13 C14 C15 121.2(2) . . ?
N006 C14 C15 118.18(19) . . ?
C18 C19 C20 109.93(16) . . ?
C18 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
N007 C18 C19 110.80(16) . . ?
N007 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
N007 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C14 C13 C12 123.66(18) . . ?
C14 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
C3 C2 C1 109.28(17) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2AB 109.8 . . ?
C1 C2 H2AB 109.8 . . ?
H2A C2 H2AB 108.3 . . ?
C7 C8 C9 117.7(2) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C22 C21 C12 115.34(19) . . ?
C22 C21 H21A 108.4 . . ?
C12 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C12 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C15 O2C 124.1(3) . . ?
O1 C15 O2B 124.1(3) . . ?
O1 C15 O2A 123.4(3) . . ?
O1 C15 C14 124.3(2) . . ?
O2C C15 C14 109.9(3) . . ?
O2B C15 C14 109.9(3) . . ?
O2A C15 C14 111.4(3) . . ?
O2A C16A C17A 106.0(6) . . ?
O2A C16A H16A 110.5 . . ?
C17A C16A H16A 110.5 . . ?
O2A C16A H16B 110.5 . . ?
C17A C16A H16B 110.5 . . ?
H16A C16A H16B 108.7 . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C15 O2A C16A 115.2(5) . . ?
O2B C16B C17B 105.3(7) . . ?
O2B C16B H16C 110.7 . . ?
C17B C16B H16C 110.7 . . ?
O2B C16B H16D 110.7 . . ?
C17B C16B H16D 110.7 . . ?
H16C C16B H16D 108.8 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C15 O2B C16B 116.3(5) . . ?
O2C C16C C17C 106.4(9) . . ?
O2C C16C H16E 110.4 . . ?
C17C C16C H16E 110.4 . . ?
O2C C16C H16F 110.4 . . ?
C17C C16C H16F 110.4 . . ?
H16E C16C H16F 108.6 . . ?
C16C C17C H17G 109.5 . . ?
C16C C17C H17H 109.5 . . ?
H17G C17C H17H 109.5 . . ?
C16C C17C H17I 109.5 . . ?
H17G C17C H17I 109.5 . . ?
H17H C17C H17I 109.5 . . ?
C15 O2C C16C 116.3(5) . . ?
O7 C25 O8 126.7(19) . . ?
O7 C25 C26 125(2) . . ?
O8 C25 C26 108.6(17) . . ?
O8 C27 C28 107.8(14) . . ?
O8 C27 H27A 110.2 . . ?
C28 C27 H27A 110.2 . . ?
O8 C27 H27B 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C25 O8 C27 114.6(16) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N006 C10 C3 -3.3(2) . . . . ?
C14 N006 C10 C3 -177.44(18) . . . . ?
C9 N006 C10 C11 173.45(17) . . . . ?
C14 N006 C10 C11 -0.7(3) . . . . ?
C10 N006 C9 C8 -173.2(2) . . . . ?
C14 N006 C9 C8 0.0(4) . . . . ?
C10 N006 C9 C4 3.1(2) . . . . ?
C14 N006 C9 C4 176.3(2) . . . . ?
N006 C10 C3 C4 2.0(2) . . . . ?
C11 C10 C3 C4 -174.41(19) . . . . ?
N006 C10 C3 C2 178.19(17) . . . . ?
C11 C10 C3 C2 1.8(3) . . . . ?
O6 C24 C23 O4 -35.8(3) . . . . ?
O5 C24 C23 O4 144.09(18) . . . . ?
O6 C24 C23 O3 142.9(2) . . . . ?
O5 C24 C23 O3 -37.2(3) . . . . ?
C3 C10 C11 N007 19.8(3) . . . . ?
N006 C10 C11 N007 -156.30(17) . . . . ?
C3 C10 C11 C12 144.3(2) . . . . ?
N006 C10 C11 C12 -31.8(2) . . . . ?
C18 N007 C11 C10 74.58(19) . . . . ?
C1 N007 C11 C10 -51.0(2) . . . . ?
C18 N007 C11 C12 -49.0(2) . . . . ?
C1 N007 C11 C12 -174.53(16) . . . . ?
C8 C9 C4 C5 -3.1(3) . . . . ?
N006 C9 C4 C5 -179.87(17) . . . . ?
C8 C9 C4 C3 174.80(18) . . . . ?
N006 C9 C4 C3 -2.0(2) . . . . ?
C10 C3 C4 C5 177.5(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C10 C3 C4 C9 0.0(2) . . . . ?
C2 C3 C4 C9 -175.7(2) . . . . ?
C19 C20 C12 C13 -170.71(17) . . . . ?
C19 C20 C12 C21 67.2(2) . . . . ?
C19 C20 C12 C11 -53.9(2) . . . . ?
C10 C11 C12 C13 45.4(2) . . . . ?
N007 C11 C12 C13 165.54(17) . . . . ?
C10 C11 C12 C20 -72.3(2) . . . . ?
N007 C11 C12 C20 47.9(2) . . . . ?
C10 C11 C12 C21 163.92(16) . . . . ?
N007 C11 C12 C21 -75.9(2) . . . . ?
C18 N007 C1 C2 -60.5(2) . . . . ?
C11 N007 C1 C2 66.6(2) . . . . ?
C10 N006 C14 C13 16.5(3) . . . . ?
C9 N006 C14 C13 -155.9(2) . . . . ?
C10 N006 C14 C15 -151.9(2) . . . . ?
C9 N006 C14 C15 35.6(3) . . . . ?
C12 C20 C19 C18 60.2(2) . . . . ?
C1 N007 C18 C19 178.94(16) . . . . ?
C11 N007 C18 C19 53.8(2) . . . . ?
C20 C19 C18 N007 -58.6(2) . . . . ?
C9 C4 C5 C6 2.2(3) . . . . ?
C3 C4 C5 C6 -175.0(2) . . . . ?
N006 C14 C13 C12 3.4(3) . . . . ?
C15 C14 C13 C12 171.5(2) . . . . ?
C20 C12 C13 C14 84.3(3) . . . . ?
C21 C12 C13 C14 -151.8(2) . . . . ?
C11 C12 C13 C14 -34.2(3) . . . . ?
C10 C3 C2 C1 8.4(3) . . . . ?
C4 C3 C2 C1 -176.4(2) . . . . ?
N007 C1 C2 C3 -41.5(2) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
N006 C9 C8 C7 177.3(2) . . . . ?
C4 C9 C8 C7 1.4(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C8 C7 C6 C5 -1.8(3) . . . . ?
C13 C12 C21 C22 -71.1(2) . . . . ?
C20 C12 C21 C22 50.1(3) . . . . ?
C11 C12 C21 C22 172.03(18) . . . . ?
C13 C14 C15 O1 -142.1(3) . . . . ?
N006 C14 C15 O1 26.1(4) . . . . ?
C13 C14 C15 O2C 23.0(4) . . . . ?
N006 C14 C15 O2C -168.8(3) . . . . ?
C13 C14 C15 O2B 23.0(4) . . . . ?
N006 C14 C15 O2B -168.8(3) . . . . ?
C13 C14 C15 O2A 48.7(4) . . . . ?
N006 C14 C15 O2A -143.1(3) . . . . ?
O1 C15 O2A C16A 16.0(6) . . . . ?
C14 C15 O2A C16A -174.7(4) . . . . ?
C17A C16A O2A C15 171.4(5) . . . . ?
O1 C15 O2B C16B -8.6(7) . . . . ?
C14 C15 O2B C16B -173.7(5) . . . . ?
C17B C16B O2B C15 -164.1(7) . . . . ?
O1 C15 O2C C16C -8.6(7) . . . . ?
C14 C15 O2C C16C -173.7(5) . . . . ?
C17C C16C O2C C15 158.7(14) . . . . ?
O7 C25 O8 C27 -5(3) . . . . ?
C26 C25 O8 C27 174(2) . . . . ?
C28 C27 O8 C25 -168.5(18) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044

