# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mj19025_0m
_database_code_depnum_ccdc_archive 'CCDC 2160133'
loop_
_audit_author_name
_audit_author_address
'avicenine A'
;State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Scie
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'avicenine A'
_chemical_formula_moiety         'C15 H15 N O4, C H4 O'
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   8.5101(3)
_cell_length_b                   9.0807(3)
_cell_length_c                   9.5903(3)
_cell_angle_alpha                77.6570(10)
_cell_angle_beta                 83.0550(10)
_cell_angle_gamma                88.4020(10)
_cell_volume                     718.67(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.002
_cell_measurement_theta_min      4.136
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1491 before and 0.0788 after correction. The Ratio of minimum to maximum transmission is 0.7697. 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    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15698
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.059
_diffrn_reflns_theta_min         4.134
_diffrn_ambient_temperature      170.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2512
_reflns_number_total             2729
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.046
_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)+(0.0557P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1055
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2'(H2'A,H2'B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3'(H3'A,H3'B,H3'C), C1S(H1SA,H1SB,H1SC)
2.e 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
O1 O 0.27875(10) 0.47588(9) 0.77348(10) 0.0242(2) Uani 1 1 d . . . . .
O2 O 0.47297(11) 0.15835(10) 0.74559(9) 0.0258(2) Uani 1 1 d . . . . .
O3 O 0.77572(11) 0.29505(10) 0.91509(11) 0.0311(2) Uani 1 1 d . . . . .
O4 O 0.14472(11) 0.11296(10) 0.73744(11) 0.0312(2) Uani 1 1 d . . . . .
H4 H 0.188824 0.043587 0.701416 0.047 Uiso 1 1 calc GR . . . .
N9 N 0.47184(12) 0.64905(11) 0.76323(11) 0.0220(2) Uani 1 1 d . . . . .
C2 C 0.25615(15) 0.31336(13) 0.81050(13) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.168638 0.284161 0.890550 0.027 Uiso 1 1 calc R . . . .
C3 C 0.41508(15) 0.24217(13) 0.85305(13) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.402017 0.176203 0.951552 0.027 Uiso 1 1 calc R . . . .
C4 C 0.66902(15) 0.39955(14) 0.86805(13) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.88587(16) 0.58315(15) 0.85146(13) 0.0257(3) Uani 1 1 d . . . . .
H5 H 0.955273 0.502754 0.884065 0.031 Uiso 1 1 calc R . . . .
C6 C 0.93945(16) 0.72885(16) 0.82075(14) 0.0284(3) Uani 1 1 d . . . . .
H6 H 1.045351 0.748999 0.832796 0.034 Uiso 1 1 calc R . . . .
C7 C 0.83852(17) 0.84787(15) 0.77171(14) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.876439 0.948543 0.750912 0.033 Uiso 1 1 calc R . . . .
C9A C 0.42741(15) 0.50859(13) 0.79406(12) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.68481(16) 0.82078(14) 0.75324(13) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.617608 0.902621 0.719442 0.030 Uiso 1 1 calc R . . . .
C10 C 0.72657(19) 0.14194(15) 0.97254(17) 0.0348(3) Uani 1 1 d . . . . .
H10A H 0.681806 0.102137 0.898649 0.052 Uiso 1 1 calc GR . . . .
H10B H 0.646297 0.138472 1.055548 0.052 Uiso 1 1 calc GR . . . .
H10C H 0.818060 0.080692 1.002639 0.052 Uiso 1 1 calc GR . . . .
C1' C 0.22794(15) 0.25080(13) 0.67880(13) 0.0231(3) Uani 1 1 d . . . . .
C2' C 0.39699(15) 0.22057(14) 0.62046(13) 0.0243(3) Uani 1 1 d . . . . .
H2'A H 0.399476 0.148173 0.556313 0.029 Uiso 1 1 calc R . . . .
H2'B H 0.449384 0.315093 0.566285 0.029 Uiso 1 1 calc R . . . .
C3A C 0.51550(15) 0.37778(13) 0.84669(12) 0.0210(3) Uani 1 1 d . . . . .
C4A C 0.72842(15) 0.55154(14) 0.83506(12) 0.0217(3) Uani 1 1 d . . . . .
C3' C 0.13504(18) 0.35356(16) 0.57198(16) 0.0330(3) Uani 1 1 d . . . . .
H3'A H 0.123471 0.305391 0.491589 0.050 Uiso 1 1 calc GR . . . .
H3'B H 0.191422 0.449306 0.535848 0.050 Uiso 1 1 calc GR . . . .
H3'C H 0.030093 0.372524 0.619342 0.050 Uiso 1 1 calc GR . . . .
C8A C 0.62670(15) 0.67168(14) 0.78439(12) 0.0213(3) Uani 1 1 d . . . . .
O5 O 0.28560(12) -0.11838(11) 0.62185(12) 0.0351(3) Uani 1 1 d . . . . .
H5A H 0.344(2) -0.187(2) 0.667(2) 0.050(5) Uiso 1 1 d . . . . .
C1S C 0.20358(17) -0.17850(16) 0.52648(15) 0.0319(3) Uani 1 1 d . . . . .
H1SA H 0.273705 -0.179204 0.437692 0.048 Uiso 1 1 calc GR . . . .
H1SB H 0.110396 -0.116126 0.503957 0.048 Uiso 1 1 calc GR . . . .
H1SC H 0.169956 -0.281729 0.571869 0.048 Uiso 1 1 calc GR . . . .


_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 C2 1.4548(14) . ?
O1 C9A 1.3542(15) . ?
O2 C3 1.4407(15) . ?
O2 C2' 1.4335(15) . ?
O3 C4 1.3404(15) . ?
O3 C10 1.4355(16) . ?
O4 H4 0.8400 . ?
O4 C1' 1.4271(15) . ?
N9 C9A 1.3023(16) . ?
N9 C8A 1.3848(17) . ?
C2 H2 1.0000 . ?
C2 C3 1.5446(18) . ?
C2 C1' 1.5372(17) . ?
C3 H3 1.0000 . ?
C3 C3A 1.5048(17) . ?
C4 C3A 1.3727(18) . ?
C4 C4A 1.4402(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3711(19) . ?
C5 C4A 1.4122(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3768(19) . ?
C9A C3A 1.4188(17) . ?
C8 H8 0.9500 . ?
C8 C8A 1.4127(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1' C2' 1.5189(18) . ?
C1' C3' 1.5137(18) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C4A C8A 1.4135(18) . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
O5 H5A 0.87(2) . ?
O5 C1S 1.4181(18) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A O1 C2 109.43(9) . . ?
C2' O2 C3 106.58(9) . . ?
C4 O3 C10 119.78(11) . . ?
C1' O4 H4 109.5 . . ?
C9A N9 C8A 114.71(10) . . ?
O1 C2 H2 111.2 . . ?
O1 C2 C3 107.01(9) . . ?
O1 C2 C1' 111.61(10) . . ?
C3 C2 H2 111.2 . . ?
C1' C2 H2 111.2 . . ?
C1' C2 C3 104.22(10) . . ?
O2 C3 C2 106.50(10) . . ?
O2 C3 H3 111.6 . . ?
O2 C3 C3A 112.40(10) . . ?
C2 C3 H3 111.6 . . ?
C3A C3 C2 102.78(9) . . ?
C3A C3 H3 111.6 . . ?
O3 C4 C3A 128.00(12) . . ?
O3 C4 C4A 113.89(11) . . ?
C3A C4 C4A 118.10(11) . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4A 120.57(12) . . ?
C4A C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.14(13) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.73(12) . . ?
C8 C7 H7 119.6 . . ?
O1 C9A C3A 112.54(11) . . ?
N9 C9A O1 118.65(11) . . ?
N9 C9A C3A 128.80(12) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C8A 120.21(12) . . ?
C8A C8 H8 119.9 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C1' C2 104.57(10) . . ?
O4 C1' C2' 110.87(10) . . ?
O4 C1' C3' 110.45(11) . . ?
C2' C1' C2 100.73(10) . . ?
C3' C1' C2 114.98(10) . . ?
C3' C1' C2' 114.49(11) . . ?
O2 C2' C1' 104.59(10) . . ?
O2 C2' H2'A 110.8 . . ?
O2 C2' H2'B 110.8 . . ?
C1' C2' H2'A 110.8 . . ?
C1' C2' H2'B 110.8 . . ?
H2'A C2' H2'B 108.9 . . ?
C4 C3A C3 134.97(11) . . ?
C4 C3A C9A 116.74(11) . . ?
C9A C3A C3 108.02(11) . . ?
C5 C4A C4 121.57(11) . . ?
C5 C4A C8A 119.33(12) . . ?
C8A C4A C4 119.10(12) . . ?
C1' C3' H3'A 109.5 . . ?
C1' C3' H3'B 109.5 . . ?
C1' C3' H3'C 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
N9 C8A C8 118.45(11) . . ?
N9 C8A C4A 122.54(11) . . ?
C8 C8A C4A 119.01(12) . . ?
C1S O5 H5A 110.3(13) . . ?
O5 C1S H1SA 109.5 . . ?
O5 C1S H1SB 109.5 . . ?
O5 C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

_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_mj19352_0m
_database_code_depnum_ccdc_archive 'CCDC 2160134'
loop_
_audit_author_name
_audit_author_address
'-avicenine A'
;State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Scie
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        '(-)-avicenine A'
_chemical_formula_moiety         'C15 H15 N O4, H2 O'
_chemical_formula_sum            'C15 H17 N O5'
_chemical_formula_weight         291.29
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   9.7252(4)
_cell_length_b                   7.2357(3)
_cell_length_c                   10.0005(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.737(2)
_cell_angle_gamma                90
_cell_volume                     695.56(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7908
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.968
_cell_measurement_theta_min      5.997
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1312 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.7479. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9299
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.068
_diffrn_reflns_theta_min         5.996
_diffrn_ambient_temperature      170.04
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2342
_reflns_number_total             2585
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.051
_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)+(0.0258P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0869
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2'(H2'A,H2'B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C3'(H3'A,H3'B,H3'C)
2.e 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
O1 O 0.48894(16) 0.4407(3) 0.86525(16) 0.0321(5) Uani 1 1 d . . . . .
O2 O 0.70274(17) 0.2634(3) 0.68724(17) 0.0302(4) Uani 1 1 d . . . . .
O3 O 0.43778(17) 0.3660(3) 0.38876(16) 0.0298(4) Uani 1 1 d . . . . .
O4 O 0.86836(16) 0.4561(3) 0.90632(18) 0.0310(4) Uani 1 1 d . . . . .
H4 H 0.867757 0.562880 0.939257 0.047 Uiso 1 1 calc GR . . . .
N9 N 0.2723(2) 0.3744(3) 0.7526(2) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.6254(2) 0.4891(4) 0.8337(2) 0.0258(6) Uani 1 1 d . . . . .
H2 H 0.645894 0.623544 0.848763 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6257(2) 0.4335(4) 0.6853(2) 0.0242(6) Uani 1 1 d . . . . .
H3 H 0.667374 0.532323 0.634135 0.029 Uiso 1 1 calc R . . . .
C4 C 0.3943(2) 0.3785(4) 0.5105(2) 0.0239(5) Uani 1 1 d . . . . .
C5 C 0.1582(3) 0.3185(4) 0.3812(3) 0.0300(6) Uani 1 1 d . . . . .
H5 H 0.194216 0.323228 0.298108 0.036 Uiso 1 1 calc R . . . .
C6 C 0.0205(3) 0.2826(4) 0.3808(3) 0.0379(7) Uani 1 1 d . . . . .
H6 H -0.038957 0.261875 0.297633 0.046 Uiso 1 1 calc R . . . .
C7 C -0.0337(3) 0.2763(4) 0.5031(3) 0.0371(7) Uani 1 1 d . . . . .
H7 H -0.129539 0.249527 0.501941 0.045 Uiso 1 1 calc R . . . .
C8 C 0.0489(3) 0.3078(4) 0.6229(3) 0.0333(6) Uani 1 1 d . . . . .
H8 H 0.009980 0.305252 0.704462 0.040 Uiso 1 1 calc R . . . .
C10 C 0.5827(3) 0.3877(4) 0.3800(3) 0.0337(6) Uani 1 1 d . . . . .
H10A H 0.598922 0.358550 0.287969 0.051 Uiso 1 1 calc GR . . . .
H10B H 0.637479 0.303810 0.444217 0.051 Uiso 1 1 calc GR . . . .
H10C H 0.610850 0.515572 0.401844 0.051 Uiso 1 1 calc GR . . . .
C1' C 0.7380(2) 0.3678(4) 0.9130(2) 0.0277(6) Uani 1 1 d . . . . .
C2' C 0.7316(3) 0.1977(4) 0.8243(3) 0.0317(6) Uani 1 1 d . . . . .
H2'A H 0.821265 0.130457 0.839788 0.038 Uiso 1 1 calc R . . . .
H2'B H 0.657029 0.113336 0.844032 0.038 Uiso 1 1 calc R . . . .
C3' C 0.7202(3) 0.3284(5) 1.0585(3) 0.0411(7) Uani 1 1 d . . . . .
H3'A H 0.790591 0.238835 1.097702 0.062 Uiso 1 1 calc GR . . . .
H3'B H 0.627215 0.277582 1.060839 0.062 Uiso 1 1 calc GR . . . .
H3'C H 0.731392 0.443318 1.110891 0.062 Uiso 1 1 calc GR . . . .
C3A C 0.4737(2) 0.4080(4) 0.6338(2) 0.0237(5) Uani 1 1 d . . . . .
C4A C 0.2477(2) 0.3486(4) 0.5044(2) 0.0260(5) Uani 1 1 d . . . . .
C8A C 0.1919(2) 0.3444(4) 0.6278(3) 0.0271(6) Uani 1 1 d . . . . .
C9A C 0.4024(2) 0.4061(4) 0.7479(2) 0.0259(6) Uani 1 1 d . . . . .
O1S O 0.8627(2) 0.8038(3) 1.0109(2) 0.0365(5) Uani 1 1 d . . . . .
H1SA H 0.942(4) 0.845(6) 1.042(4) 0.066(12) Uiso 1 1 d . . . . .
H1SB H 0.822(4) 0.829(7) 1.084(4) 0.081(13) 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 C2 1.453(3) . ?
O1 C9A 1.360(3) . ?
O2 C3 1.440(3) . ?
O2 C2' 1.438(3) . ?
O3 C4 1.351(3) . ?
O3 C10 1.434(3) . ?
O4 H4 0.8400 . ?
O4 C1' 1.430(3) . ?
N9 C8A 1.386(3) . ?
N9 C9A 1.293(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.538(3) . ?
C2 C1' 1.528(4) . ?
C3 H3 1.0000 . ?
C3 C3A 1.500(3) . ?
C4 C3A 1.369(3) . ?
C4 C4A 1.434(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(3) . ?
C5 C4A 1.413(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.404(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.357(4) . ?
C8 H8 0.9500 . ?
C8 C8A 1.409(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1' C2' 1.513(4) . ?
C1' C3' 1.518(3) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C3A C9A 1.422(3) . ?
C4A C8A 1.422(3) . ?
O1S H1SA 0.84(4) . ?
O1S H1SB 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A O1 C2 108.85(16) . . ?
C2' O2 C3 108.76(17) . . ?
C4 O3 C10 119.51(18) . . ?
C1' O4 H4 109.5 . . ?
C9A N9 C8A 114.60(19) . . ?
O1 C2 H2 111.7 . . ?
O1 C2 C3 106.38(17) . . ?
O1 C2 C1' 110.8(2) . . ?
C3 C2 H2 111.7 . . ?
C1' C2 H2 111.7 . . ?
C1' C2 C3 104.2(2) . . ?
O2 C3 C2 106.70(19) . . ?
O2 C3 H3 111.5 . . ?
O2 C3 C3A 112.5(2) . . ?
C2 C3 H3 111.5 . . ?
C3A C3 C2 102.55(17) . . ?
C3A C3 H3 111.5 . . ?
O3 C4 C3A 127.7(2) . . ?
O3 C4 C4A 113.4(2) . . ?
C3A C4 C4A 118.9(2) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4A 120.4(2) . . ?
C4A C5 H5 119.8 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C8A 120.7(2) . . ?
C8A C8 H8 119.6 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C1' C2 106.8(2) . . ?
O4 C1' C2' 107.10(19) . . ?
O4 C1' C3' 111.1(2) . . ?
C2' C1' C2 101.6(2) . . ?
C2' C1' C3' 114.1(2) . . ?
C3' C1' C2 115.4(2) . . ?
O2 C2' C1' 105.9(2) . . ?
O2 C2' H2'A 110.5 . . ?
O2 C2' H2'B 110.5 . . ?
C1' C2' H2'A 110.5 . . ?
C1' C2' H2'B 110.5 . . ?
H2'A C2' H2'B 108.7 . . ?
C1' C3' H3'A 109.5 . . ?
C1' C3' H3'B 109.5 . . ?
C1' C3' H3'C 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C4 C3A C3 136.0(2) . . ?
C4 C3A C9A 116.3(2) . . ?
C9A C3A C3 107.5(2) . . ?
C5 C4A C4 122.5(2) . . ?
C5 C4A C8A 119.2(2) . . ?
C8A C4A C4 118.3(2) . . ?
N9 C8A C8 118.7(2) . . ?
N9 C8A C4A 122.7(2) . . ?
C8 C8A C4A 118.6(2) . . ?
O1 C9A C3A 112.1(2) . . ?
N9 C9A O1 118.79(19) . . ?
N9 C9A C3A 129.1(2) . . ?
H1SA O1S H1SB 97(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_mj19351_0m
_database_code_depnum_ccdc_archive 'CCDC 2160135'
loop_
_audit_author_name
_audit_author_address
myrtopsine
;State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Scie
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        (+)-Myrtopsine
_chemical_formula_moiety         'C15 H17 N O4'
_chemical_formula_sum            'C15 H17 N O4'
_chemical_formula_weight         275.29
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   8.5948(3)
_cell_length_b                   8.5216(3)
_cell_length_c                   18.7212(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.0350(10)
_cell_angle_gamma                90
_cell_volume                     1350.19(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.964
_cell_measurement_theta_min      4.546
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1050 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.8330. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14913
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.944
_diffrn_reflns_theta_min         4.545
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4762
_reflns_number_total             5038
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 2045 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0331
_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)+(0.0427P)²+0.1309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3), C2B(H2BA), C3B(H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C2'(H2'A,H2'B,H2'C), C3'(H3'A,H3'B,H3'C), C2'B(H2'D,H2'E,
 H2'F), C3'B(H3'D,H3'E,H3'F), C10B(H10D,H10E,H10F)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O2B(H2B), O4B(H4B)
;
_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
O1 O 0.0885(2) 0.72742(19) 0.26699(9) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.43087(18) 0.56494(19) 0.25208(9) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.459567 0.493823 0.282602 0.038 Uiso 1 1 calc GR . . . .
O3 O 0.3410(2) 0.6466(2) 0.06410(9) 0.0300(4) Uani 1 1 d . . . . .
O4 O -0.0448(2) 0.4216(2) 0.21250(9) 0.0315(4) Uani 1 1 d . . . . .
H4 H -0.102192 0.341508 0.211345 0.047 Uiso 1 1 calc GR . . . .
N9 N 0.0762(2) 0.9247(2) 0.18354(11) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.1615(3) 0.5729(3) 0.28116(12) 0.0232(5) Uani 1 1 d . . . . .
H2A H 0.232482 0.577603 0.329484 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2664(3) 0.5469(3) 0.22318(12) 0.0220(5) Uani 1 1 d . . . . .
H3 H 0.244309 0.443169 0.198522 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2564(3) 0.7253(3) 0.10632(12) 0.0218(5) Uani 1 1 d . . . . .
C5 C 0.2317(3) 0.9294(3) 0.01013(13) 0.0308(6) Uani 1 1 d . . . . .
H5 H 0.287064 0.863933 -0.017966 0.037 Uiso 1 1 calc R . . . .
C6 C 0.1807(3) 1.0741(4) -0.01570(15) 0.0372(6) Uani 1 1 d . . . . .
H6 H 0.199404 1.108076 -0.061782 0.045 Uiso 1 1 calc R . . . .
C7 C 0.1013(3) 1.1714(3) 0.02567(15) 0.0372(6) Uani 1 1 d . . . . .
H7 H 0.068261 1.272669 0.007958 0.045 Uiso 1 1 calc R . . . .
C8 C 0.0701(3) 1.1233(3) 0.09156(15) 0.0339(6) Uani 1 1 d . . . . .
H8 H 0.016173 1.191481 0.119147 0.041 Uiso 1 1 calc R . . . .
C10 C 0.3946(4) 0.4911(3) 0.08354(16) 0.0388(7) Uani 1 1 d . . . . .
H10A H 0.455627 0.451415 0.047766 0.058 Uiso 1 1 calc GR . . . .
H10B H 0.303422 0.422663 0.084595 0.058 Uiso 1 1 calc GR . . . .
H10C H 0.461592 0.492642 0.131596 0.058 Uiso 1 1 calc GR . . . .
C1' C 0.0368(3) 0.4470(3) 0.28546(12) 0.0251(5) Uani 1 1 d . . . . .
C2' C 0.1196(3) 0.2970(3) 0.31591(15) 0.0347(6) Uani 1 1 d . . . . .
H2'A H 0.040465 0.217651 0.322070 0.052 Uiso 1 1 calc GR . . . .
H2'B H 0.185704 0.319248 0.362973 0.052 Uiso 1 1 calc GR . . . .
H2'C H 0.186023 0.257551 0.282261 0.052 Uiso 1 1 calc GR . . . .
C3' C -0.0813(3) 0.4999(3) 0.33248(15) 0.0367(6) Uani 1 1 d . . . . .
H3'A H -0.135462 0.594942 0.311692 0.055 Uiso 1 1 calc GR . . . .
H3'B H -0.025410 0.522325 0.381648 0.055 Uiso 1 1 calc GR . . . .
H3'C H -0.159100 0.416602 0.334364 0.055 Uiso 1 1 calc GR . . . .
C3A C 0.2193(3) 0.6802(3) 0.17169(11) 0.0208(5) Uani 1 1 d . . . . .
C4A C 0.2028(3) 0.8764(3) 0.07810(12) 0.0230(5) Uani 1 1 d . . . . .
C8A C 0.1175(3) 0.9728(3) 0.11875(13) 0.0244(5) Uani 1 1 d . . . . .
C9A C 0.1259(3) 0.7853(3) 0.20485(12) 0.0228(5) Uani 1 1 d . . . . .
O1B O 0.50397(19) 0.1702(2) 0.25435(8) 0.0260(4) Uani 1 1 d . . . . .
O2B O 0.5231(2) -0.1720(2) 0.33318(10) 0.0350(4) Uani 1 1 d . . . . .
H2B H 0.505577 -0.246928 0.303728 0.053 Uiso 1 1 calc GR . . . .
O3B O 0.8027(2) -0.0064(2) 0.47698(10) 0.0344(4) Uani 1 1 d . . . . .
O4B O 0.81280(19) 0.09576(19) 0.21813(9) 0.0275(4) Uani 1 1 d . . . . .
H4B H 0.889121 0.040458 0.210483 0.041 Uiso 1 1 calc GR . . . .
N9B N 0.5396(2) 0.3388(2) 0.35004(10) 0.0222(4) Uani 1 1 d . . . . .
C1'B C 0.6676(3) 0.0284(3) 0.18136(12) 0.0257(5) Uani 1 1 d . . . . .
C2'B C 0.6937(3) -0.1343(3) 0.15177(15) 0.0333(6) Uani 1 1 d . . . . .
H2'D H 0.764229 -0.126341 0.116050 0.050 Uiso 1 1 calc GR . . . .
H2'E H 0.592084 -0.178319 0.128570 0.050 Uiso 1 1 calc GR . . . .
H2'F H 0.741614 -0.202704 0.191665 0.050 Uiso 1 1 calc GR . . . .
C3'B C 0.5989(3) 0.1382(3) 0.11990(13) 0.0366(6) Uani 1 1 d . . . . .
H3'D H 0.596622 0.245457 0.138568 0.055 Uiso 1 1 calc GR . . . .
H3'E H 0.491235 0.104879 0.099432 0.055 Uiso 1 1 calc GR . . . .
H3'F H 0.664620 0.135027 0.082075 0.055 Uiso 1 1 calc GR . . . .
C3AB C 0.6501(3) 0.0727(3) 0.36026(12) 0.0229(5) Uani 1 1 d . . . . .
C4AB C 0.6955(3) 0.2456(3) 0.46402(13) 0.0237(5) Uani 1 1 d . . . . .
C8AB C 0.6052(3) 0.3625(3) 0.42216(12) 0.0223(5) Uani 1 1 d . . . . .
C9AB C 0.5662(3) 0.2011(3) 0.32473(12) 0.0219(5) Uani 1 1 d . . . . .
C2B C 0.5560(3) 0.0139(3) 0.23629(12) 0.0237(5) Uani 1 1 d . . . . .
H2BA H 0.461361 -0.048139 0.213810 0.028 Uiso 1 1 calc R . . . .
C3B C 0.6289(3) -0.0637(3) 0.30882(13) 0.0248(5) Uani 1 1 d . . . . .
H3B H 0.732452 -0.114464 0.305688 0.030 Uiso 1 1 calc R . . . .
C4B C 0.7174(3) 0.0968(3) 0.43151(13) 0.0245(5) Uani 1 1 d . . . . .
C5B C 0.7587(3) 0.2784(3) 0.53735(13) 0.0285(5) Uani 1 1 d . . . . .
H5B H 0.819255 0.200723 0.566185 0.034 Uiso 1 1 calc R . . . .
C6B C 0.7338(3) 0.4206(3) 0.56733(13) 0.0325(6) Uani 1 1 d . . . . .
H6B H 0.776735 0.440813 0.616744 0.039 Uiso 1 1 calc R . . . .
C7B C 0.6458(3) 0.5360(3) 0.52568(13) 0.0299(5) Uani 1 1 d . . . . .
H7B H 0.629832 0.634822 0.546751 0.036 Uiso 1 1 calc R . . . .
C8B C 0.5816(3) 0.5077(3) 0.45410(13) 0.0263(5) Uani 1 1 d . . . . .
H8B H 0.521083 0.586771 0.426235 0.032 Uiso 1 1 calc R . . . .
C10B C 0.8461(3) -0.1528(3) 0.44873(16) 0.0382(6) Uani 1 1 d . . . . .
H10D H 0.911959 -0.133477 0.411857 0.057 Uiso 1 1 calc GR . . . .
H10E H 0.750559 -0.209776 0.426824 0.057 Uiso 1 1 calc GR . . . .
H10F H 0.905498 -0.215658 0.488147 0.057 Uiso 1 1 calc GR . . . .


_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 C2 1.462(3) . ?
O1 C9A 1.353(3) . ?
O2 H2 0.8400 . ?
O2 C3 1.431(3) . ?
O3 C4 1.343(3) . ?
O3 C10 1.429(3) . ?
O4 H4 0.8400 . ?
O4 C1' 1.439(3) . ?
N9 C8A 1.384(3) . ?
N9 C9A 1.301(3) . ?
C2 H2A 1.0000 . ?
C2 C3 1.543(3) . ?
C2 C1' 1.529(3) . ?
C3 H3 1.0000 . ?
C3 C3A 1.499(3) . ?
C4 C3A 1.372(3) . ?
C4 C4A 1.437(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(4) . ?
C5 C4A 1.412(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.370(4) . ?
C8 H8 0.9500 . ?
C8 C8A 1.413(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1' C2' 1.525(3) . ?
C1' C3' 1.523(4) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C3A C9A 1.417(3) . ?
C4A C8A 1.409(3) . ?
O1B C9AB 1.359(3) . ?
O1B C2B 1.463(3) . ?
O2B H2B 0.8400 . ?
O2B C3B 1.425(3) . ?
O3B C4B 1.348(3) . ?
O3B C10B 1.430(3) . ?
O4B H4B 0.8400 . ?
O4B C1'B 1.436(3) . ?
N9B C8AB 1.384(3) . ?
N9B C9AB 1.301(3) . ?
C1'B C2'B 1.524(3) . ?
C1'B C3'B 1.520(3) . ?
C1'B C2B 1.528(3) . ?
C2'B H2'D 0.9800 . ?
C2'B H2'E 0.9800 . ?
C2'B H2'F 0.9800 . ?
C3'B H3'D 0.9800 . ?
C3'B H3'E 0.9800 . ?
C3'B H3'F 0.9800 . ?
C3AB C9AB 1.411(3) . ?
C3AB C3B 1.500(3) . ?
C3AB C4B 1.374(3) . ?
C4AB C8AB 1.413(3) . ?
C4AB C4B 1.433(3) . ?
C4AB C5B 1.413(3) . ?
C8AB C8B 1.404(3) . ?
C2B H2BA 1.0000 . ?
C2B C3B 1.542(3) . ?
C3B H3B 1.0000 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.368(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.393(4) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.379(3) . ?
C8B H8B 0.9500 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A O1 C2 109.01(17) . . ?
C3 O2 H2 109.5 . . ?
C4 O3 C10 119.79(19) . . ?
C1' O4 H4 109.5 . . ?
C9A N9 C8A 114.7(2) . . ?
O1 C2 H2A 107.6 . . ?
O1 C2 C3 106.64(17) . . ?
O1 C2 C1' 111.05(19) . . ?
C3 C2 H2A 107.6 . . ?
C1' C2 H2A 107.6 . . ?
C1' C2 C3 115.91(19) . . ?
O2 C3 C2 112.23(18) . . ?
O2 C3 H3 111.4 . . ?
O2 C3 C3A 107.44(17) . . ?
C2 C3 H3 111.4 . . ?
C3A C3 C2 102.61(18) . . ?
C3A C3 H3 111.4 . . ?
O3 C4 C3A 128.2(2) . . ?
O3 C4 C4A 113.74(19) . . ?
C3A C4 C4A 118.0(2) . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4A 120.7(3) . . ?
C4A C5 H5 119.6 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C8A 120.4(3) . . ?
C8A C8 H8 119.8 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C1' C2 106.59(18) . . ?
O4 C1' C2' 110.3(2) . . ?
O4 C1' C3' 109.3(2) . . ?
C2' C1' C2 108.79(19) . . ?
C3' C1' C2 111.5(2) . . ?
C3' C1' C2' 110.3(2) . . ?
C1' C2' H2'A 109.5 . . ?
C1' C2' H2'B 109.5 . . ?
C1' C2' H2'C 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C1' C3' H3'A 109.5 . . ?
C1' C3' H3'B 109.5 . . ?
C1' C3' H3'C 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C4 C3A C3 135.0(2) . . ?
C4 C3A C9A 116.8(2) . . ?
C9A C3A C3 107.90(19) . . ?
C5 C4A C4 121.5(2) . . ?
C8A C4A C4 119.2(2) . . ?
C8A C4A C5 119.3(2) . . ?
N9 C8A C8 118.8(2) . . ?
N9 C8A C4A 122.5(2) . . ?
C4A C8A C8 118.6(2) . . ?
O1 C9A C3A 112.6(2) . . ?
N9 C9A O1 118.8(2) . . ?
N9 C9A C3A 128.6(2) . . ?
C9AB O1B C2B 108.41(17) . . ?
C3B O2B H2B 109.5 . . ?
C4B O3B C10B 118.9(2) . . ?
C1'B O4B H4B 109.5 . . ?
C9AB N9B C8AB 114.77(19) . . ?
O4B C1'B C2'B 111.5(2) . . ?
O4B C1'B C3'B 107.9(2) . . ?
O4B C1'B C2B 107.73(18) . . ?
C2'B C1'B C2B 108.7(2) . . ?
C3'B C1'B C2'B 110.3(2) . . ?
C3'B C1'B C2B 110.6(2) . . ?
C1'B C2'B H2'D 109.5 . . ?
C1'B C2'B H2'E 109.5 . . ?
C1'B C2'B H2'F 109.5 . . ?
H2'D C2'B H2'E 109.5 . . ?
H2'D C2'B H2'F 109.5 . . ?
H2'E C2'B H2'F 109.5 . . ?
C1'B C3'B H3'D 109.5 . . ?
C1'B C3'B H3'E 109.5 . . ?
C1'B C3'B H3'F 109.5 . . ?
H3'D C3'B H3'E 109.5 . . ?
H3'D C3'B H3'F 109.5 . . ?
H3'E C3'B H3'F 109.5 . . ?
C9AB C3AB C3B 107.65(19) . . ?
C4B C3AB C9AB 115.9(2) . . ?
C4B C3AB C3B 136.3(2) . . ?
C8AB C4AB C4B 119.2(2) . . ?
C8AB C4AB C5B 118.7(2) . . ?
C5B C4AB C4B 122.1(2) . . ?
N9B C8AB C4AB 122.0(2) . . ?
N9B C8AB C8B 118.6(2) . . ?
C8B C8AB C4AB 119.4(2) . . ?
O1B C9AB C3AB 112.9(2) . . ?
N9B C9AB O1B 117.60(19) . . ?
N9B C9AB C3AB 129.5(2) . . ?
O1B C2B C1'B 109.59(18) . . ?
O1B C2B H2BA 108.6 . . ?
O1B C2B C3B 106.31(18) . . ?
C1'B C2B H2BA 108.6 . . ?
C1'B C2B C3B 114.89(19) . . ?
C3B C2B H2BA 108.6 . . ?
O2B C3B C3AB 107.99(18) . . ?
O2B C3B C2B 112.05(19) . . ?
O2B C3B H3B 111.3 . . ?
C3AB C3B C2B 102.58(18) . . ?
C3AB C3B H3B 111.3 . . ?
C2B C3B H3B 111.3 . . ?
O3B C4B C3AB 127.3(2) . . ?
O3B C4B C4AB 113.9(2) . . ?
C3AB C4B C4AB 118.7(2) . . ?
C4AB C5B H5B 119.6 . . ?
C6B C5B C4AB 120.8(2) . . ?
C6B C5B H5B 119.6 . . ?
C5B C6B H6B 119.9 . . ?
C5B C6B C7B 120.3(2) . . ?
C7B C6B H6B 119.9 . . ?
C6B C7B H7B 119.8 . . ?
C8B C7B C6B 120.4(2) . . ?
C8B C7B H7B 119.8 . . ?
C8AB C8B H8B 119.8 . . ?
C7B C8B C8AB 120.3(2) . . ?
C7B C8B H8B 119.8 . . ?
O3B C10B H10D 109.5 . . ?
O3B C10B H10E 109.5 . . ?
O3B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
