# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_cu_dm16061_0m
_database_code_depnum_ccdc_archive 'CCDC 1462825'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_audit_creation_date             2016-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '21-deoxymacropodumine D'
_chemical_formula_moiety         'C23 H31 N O4, C H4 O'
_chemical_formula_sum            'C24 H35 N O5'
_chemical_formula_weight         417.53
_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 0.0181 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           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                   10.7411(2)
_cell_length_b                   9.0530(2)
_cell_length_c                   11.5845(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4430(10)
_cell_angle_gamma                90
_cell_volume                     1124.43(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.06
_cell_measurement_theta_min      4.12
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.7461.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8067
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.726
_diffrn_reflns_theta_min         3.822
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                3610
_reflns_number_total             3732
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 1442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(11)
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.073
_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)+(0.1233P)²+0.0639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1582
_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(H2A), C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B),
 C17(H17A,H17B), C19(H19A,H19B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5013(2) 0.3153(3) 0.8812(2) 0.0574(7) Uani 1 1 d . . . . .
O2 O 0.49181(19) 0.5007(3) 0.51806(16) 0.0424(5) Uani 1 1 d . . . . .
H2 H 0.5396 0.5032 0.4655 0.064 Uiso 1 1 calc GR . . . .
O3 O 0.8568(4) 0.1932(5) 0.5473(4) 0.0956(12) Uani 1 1 d . . . . .
O4 O 0.8609(3) -0.0241(3) 0.6358(3) 0.0663(8) Uani 1 1 d . . . . .
N1 N 0.4414(2) 0.7228(3) 0.7773(2) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.5091(3) 0.3922(3) 0.7961(2) 0.0382(6) Uani 1 1 d . . . . .
C2 C 0.3935(3) 0.4697(4) 0.7431(3) 0.0411(7) Uani 1 1 d . . . . .
H2A H 0.3489 0.4032 0.6881 0.049 Uiso 1 1 calc R . . . .
C3 C 0.4230(2) 0.6139(4) 0.6822(2) 0.0385(6) Uani 1 1 d . . . . .
H3 H 0.3490 0.6432 0.6340 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5320(2) 0.6032(3) 0.6052(2) 0.0362(6) Uani 1 1 d . . . . .
H4 H 0.5454 0.6996 0.5696 0.043 Uiso 1 1 calc R . . . .
C5 C 0.6513(2) 0.5581(3) 0.6783(2) 0.0344(6) Uani 1 1 d . . . . .
C6 C 0.6694(3) 0.6868(3) 0.7667(2) 0.0405(6) Uani 1 1 d . . . . .
H6 H 0.6661 0.7765 0.7193 0.049 Uiso 1 1 calc R . . . .
C7 C 0.5612(3) 0.7025(4) 0.8451(2) 0.0449(7) Uani 1 1 d . . . . .
H7A H 0.5565 0.6149 0.8929 0.054 Uiso 1 1 calc R . . . .
H7B H 0.5761 0.7867 0.8959 0.054 Uiso 1 1 calc R . . . .
C8 C 0.6322(2) 0.4041(3) 0.7349(2) 0.0327(6) Uani 1 1 d . . . . .
C9 C 0.7374(2) 0.3560(4) 0.8192(2) 0.0385(6) Uani 1 1 d . . . . .
C10 C 0.8174(3) 0.4231(4) 0.8937(3) 0.0442(7) Uani 1 1 d . . . . .
C11 C 0.8215(3) 0.5809(4) 0.9318(3) 0.0531(8) Uani 1 1 d . . . . .
H11A H 0.9034 0.6004 0.9686 0.064 Uiso 1 1 calc R . . . .
H11B H 0.7611 0.5941 0.9900 0.064 Uiso 1 1 calc R . . . .
C12 C 0.7954(3) 0.6961(4) 0.8371(3) 0.0511(7) Uani 1 1 d . . . . .
H12A H 0.8612 0.6893 0.7834 0.061 Uiso 1 1 calc R . . . .
H12B H 0.8015 0.7931 0.8726 0.061 Uiso 1 1 calc R . . . .
C13 C 0.6262(3) 0.2714(3) 0.6455(2) 0.0412(6) Uani 1 1 d . . . . .
H13A H 0.5408 0.2371 0.6335 0.049 Uiso 1 1 calc R . . . .
H13B H 0.6541 0.3045 0.5718 0.049 Uiso 1 1 calc R . . . .
C14 C 0.7099(3) 0.1440(3) 0.6926(3) 0.0401(6) Uani 1 1 d . . . . .
H14 H 0.6588 0.0549 0.6982 0.048 Uiso 1 1 calc R . . . .
C15 C 0.7564(3) 0.1925(4) 0.8161(3) 0.0422(7) Uani 1 1 d . . . . .
H15 H 0.7021 0.1472 0.8712 0.051 Uiso 1 1 calc R . . . .
C16 C 0.8923(3) 0.1760(5) 0.8645(4) 0.0596(9) Uani 1 1 d . . . . .
H16A H 0.9049 0.0833 0.9055 0.072 Uiso 1 1 calc R . . . .
H16B H 0.9501 0.1819 0.8034 0.072 Uiso 1 1 calc R . . . .
C17 C 0.9074(3) 0.3084(5) 0.9471(3) 0.0519(8) Uani 1 1 d . . . . .
H17A H 0.8853 0.2818 1.0244 0.062 Uiso 1 1 calc R . . . .
H17B H 0.9925 0.3450 0.9509 0.062 Uiso 1 1 calc R . . . .
C18 C 0.3032(3) 0.5229(5) 0.8346(3) 0.0579(9) Uani 1 1 d . . . . .
H18 H 0.3214 0.4711 0.9079 0.069 Uiso 1 1 calc R . . . .
C19 C 0.3339(3) 0.6884(5) 0.8487(3) 0.0542(8) Uani 1 1 d . . . . .
H19A H 0.2621 0.7475 0.8232 0.065 Uiso 1 1 calc R . . . .
H19B H 0.3553 0.7108 0.9293 0.065 Uiso 1 1 calc R . . . .
C20 C 0.1671(4) 0.4978(7) 0.7926(6) 0.0938(17) Uani 1 1 d . . . . .
H20A H 0.1482 0.5551 0.7240 0.141 Uiso 1 1 calc GR . . . .
H20B H 0.1135 0.5276 0.8518 0.141 Uiso 1 1 calc GR . . . .
H20C H 0.1541 0.3950 0.7756 0.141 Uiso 1 1 calc GR . . . .
C21 C 0.7622(3) 0.5575(4) 0.6001(3) 0.0457(7) Uani 1 1 d . . . . .
H21A H 0.7400 0.5035 0.5306 0.069 Uiso 1 1 calc GR . . . .
H21B H 0.8328 0.5115 0.6401 0.069 Uiso 1 1 calc GR . . . .
H21C H 0.7829 0.6573 0.5807 0.069 Uiso 1 1 calc GR . . . .
C22 C 0.8169(3) 0.1107(4) 0.6169(3) 0.0489(7) Uani 1 1 d . . . . .
C23 C 0.9653(5) -0.0684(7) 0.5717(6) 0.0953(18) Uani 1 1 d . . . . .
H23A H 0.9392 -0.0778 0.4913 0.143 Uiso 1 1 calc GR . . . .
H23B H 0.9966 -0.1616 0.6004 0.143 Uiso 1 1 calc GR . . . .
H23C H 1.0299 0.0048 0.5807 0.143 Uiso 1 1 calc GR . . . .
O5 O 0.3845(4) 0.9911(5) 0.6812(3) 0.0849(11) Uani 1 1 d . . . . .
C24 C 0.2978(5) 1.0640(6) 0.7401(5) 0.0865(15) Uani 1 1 d . . . . .
H24A H 0.2488 1.1260 0.6877 0.130 Uiso 1 1 calc GR . . . .
H24B H 0.3388 1.1238 0.7993 0.130 Uiso 1 1 calc GR . . . .
H24C H 0.2444 0.9939 0.7748 0.130 Uiso 1 1 calc GR . . . .
H5 H 0.410(5) 0.900(9) 0.710(5) 0.089(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.214(4) . ?
O2 H2 0.8200 . ?
O2 C4 1.420(4) . ?
O3 C22 1.197(5) . ?
O4 C22 1.323(5) . ?
O4 C23 1.439(5) . ?
N1 C3 1.483(4) . ?
N1 C7 1.479(4) . ?
N1 C19 1.494(4) . ?
C1 C2 1.524(4) . ?
C1 C8 1.541(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.526(4) . ?
C2 C18 1.555(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.517(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.547(3) . ?
C5 C6 1.556(4) . ?
C5 C8 1.559(4) . ?
C5 C21 1.539(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.524(4) . ?
C6 C12 1.539(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.512(3) . ?
C8 C13 1.585(4) . ?
C9 C10 1.328(4) . ?
C9 C15 1.495(5) . ?
C10 C11 1.495(5) . ?
C10 C17 1.525(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.528(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.541(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.551(4) . ?
C14 C22 1.517(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.539(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.537(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9800 . ?
C18 C19 1.541(6) . ?
C18 C20 1.529(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O5 C24 1.359(6) . ?
O5 H5 0.93(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C4 O2 H2 109.5 . . ?
C22 O4 C23 117.0(4) . . ?
C3 N1 C19 101.5(2) . . ?
C7 N1 C3 112.7(2) . . ?
C7 N1 C19 110.9(2) . . ?
O1 C1 C2 119.8(3) . . ?
O1 C1 C8 121.1(3) . . ?
C2 C1 C8 118.9(2) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 C3 113.2(2) . . ?
C1 C2 C18 113.2(3) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 C18 101.9(3) . . ?
C18 C2 H2A 109.4 . . ?
N1 C3 C2 104.3(2) . . ?
N1 C3 H3 108.1 . . ?
N1 C3 C4 113.9(2) . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 114.0(2) . . ?
C4 C3 H3 108.1 . . ?
O2 C4 C3 104.3(2) . . ?
O2 C4 H4 109.2 . . ?
O2 C4 C5 115.0(2) . . ?
C3 C4 H4 109.2 . . ?
C3 C4 C5 109.8(2) . . ?
C5 C4 H4 109.2 . . ?
C4 C5 C6 103.2(2) . . ?
C4 C5 C8 109.9(2) . . ?
C6 C5 C8 114.0(2) . . ?
C21 C5 C4 108.9(2) . . ?
C21 C5 C6 108.6(2) . . ?
C21 C5 C8 111.8(2) . . ?
C5 C6 H6 104.7 . . ?
C7 C6 C5 113.1(2) . . ?
C7 C6 H6 104.7 . . ?
C7 C6 C12 110.9(2) . . ?
C12 C6 C5 117.4(3) . . ?
C12 C6 H6 104.7 . . ?
N1 C7 C6 111.4(2) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C1 C8 C5 113.2(2) . . ?
C1 C8 C13 104.2(2) . . ?
C5 C8 C13 113.8(2) . . ?
C9 C8 C1 108.2(2) . . ?
C9 C8 C5 114.6(2) . . ?
C9 C8 C13 101.7(2) . . ?
C10 C9 C8 135.8(3) . . ?
C10 C9 C15 112.6(3) . . ?
C15 C9 C8 111.6(2) . . ?
C9 C10 C11 129.5(3) . . ?
C9 C10 C17 108.8(3) . . ?
C11 C10 C17 121.6(3) . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C10 C11 C12 116.0(3) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C6 C12 H12A 107.9 . . ?
C6 C12 H12B 107.9 . . ?
C11 C12 C6 117.4(3) . . ?
C11 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C8 C13 H13A 109.7 . . ?
C8 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 C8 109.6(2) . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C13 C14 H14 108.8 . . ?
C13 C14 C15 105.3(2) . . ?
C15 C14 H14 108.8 . . ?
C22 C14 C13 113.0(2) . . ?
C22 C14 H14 108.8 . . ?
C22 C14 C15 112.1(2) . . ?
C9 C15 C14 105.4(2) . . ?
C9 C15 H15 108.1 . . ?
C9 C15 C16 102.4(3) . . ?
C14 C15 H15 108.1 . . ?
C16 C15 C14 123.7(3) . . ?
C16 C15 H15 108.1 . . ?
C15 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C17 C16 C15 102.3(3) . . ?
C17 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
C10 C17 C16 103.8(2) . . ?
C10 C17 H17A 111.0 . . ?
C10 C17 H17B 111.0 . . ?
C16 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C2 C18 H18 110.0 . . ?
C19 C18 C2 103.6(3) . . ?
C19 C18 H18 110.0 . . ?
C20 C18 C2 111.1(4) . . ?
C20 C18 H18 110.0 . . ?
C20 C18 C19 111.9(4) . . ?
N1 C19 C18 108.2(3) . . ?
N1 C19 H19A 110.1 . . ?
N1 C19 H19B 110.1 . . ?
C18 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 O4 123.2(3) . . ?
O3 C22 C14 125.4(3) . . ?
O4 C22 C14 111.3(3) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 O5 H5 117(4) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.82 1.93 2.733(3) 165.5 2_646

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 150.8(3) . . . . ?
O1 C1 C2 C18 35.5(4) . . . . ?
O1 C1 C8 C5 -148.0(3) . . . . ?
O1 C1 C8 C9 -19.9(4) . . . . ?
O1 C1 C8 C13 87.8(3) . . . . ?
O2 C4 C5 C6 -178.4(2) . . . . ?
O2 C4 C5 C8 -56.4(3) . . . . ?
O2 C4 C5 C21 66.3(3) . . . . ?
N1 C3 C4 O2 -176.8(2) . . . . ?
N1 C3 C4 C5 59.4(3) . . . . ?
C1 C2 C3 N1 -79.7(3) . . . . ?
C1 C2 C3 C4 45.2(3) . . . . ?
C1 C2 C18 C19 99.6(3) . . . . ?
C1 C2 C18 C20 -140.2(4) . . . . ?
C1 C8 C9 C10 -94.2(4) . . . . ?
C1 C8 C9 C15 86.7(3) . . . . ?
C1 C8 C13 C14 -102.7(2) . . . . ?
C2 C1 C8 C5 36.4(3) . . . . ?
C2 C1 C8 C9 164.6(3) . . . . ?
C2 C1 C8 C13 -87.8(3) . . . . ?
C2 C3 C4 O2 63.6(3) . . . . ?
C2 C3 C4 C5 -60.1(3) . . . . ?
C2 C18 C19 N1 -4.4(4) . . . . ?
C3 N1 C7 C6 48.1(3) . . . . ?
C3 N1 C19 C18 30.0(3) . . . . ?
C3 C2 C18 C19 -22.3(3) . . . . ?
C3 C2 C18 C20 98.0(4) . . . . ?
C3 C4 C5 C6 -61.2(3) . . . . ?
C3 C4 C5 C8 60.8(3) . . . . ?
C3 C4 C5 C21 -176.4(2) . . . . ?
C4 C5 C6 C7 61.7(3) . . . . ?
C4 C5 C6 C12 -167.1(2) . . . . ?
C4 C5 C8 C1 -48.8(3) . . . . ?
C4 C5 C8 C9 -173.5(2) . . . . ?
C4 C5 C8 C13 69.9(3) . . . . ?
C5 C6 C7 N1 -56.6(3) . . . . ?
C5 C6 C12 C11 -72.3(4) . . . . ?
C5 C8 C9 C10 33.1(4) . . . . ?
C5 C8 C9 C15 -145.9(2) . . . . ?
C5 C8 C13 C14 133.5(2) . . . . ?
C6 C5 C8 C1 66.6(3) . . . . ?
C6 C5 C8 C9 -58.1(3) . . . . ?
C6 C5 C8 C13 -174.7(2) . . . . ?
C7 N1 C3 C2 73.8(3) . . . . ?
C7 N1 C3 C4 -51.0(3) . . . . ?
C7 N1 C19 C18 -89.9(3) . . . . ?
C7 C6 C12 C11 59.9(4) . . . . ?
C8 C1 C2 C3 -33.5(4) . . . . ?
C8 C1 C2 C18 -148.9(3) . . . . ?
C8 C5 C6 C7 -57.5(3) . . . . ?
C8 C5 C6 C12 73.7(3) . . . . ?
C8 C9 C10 C11 8.2(6) . . . . ?
C8 C9 C10 C17 -176.1(3) . . . . ?
C8 C9 C15 C14 27.0(3) . . . . ?
C8 C9 C15 C16 157.6(3) . . . . ?
C8 C13 C14 C15 5.6(3) . . . . ?
C8 C13 C14 C22 -117.0(3) . . . . ?
C9 C8 C13 C14 9.6(3) . . . . ?
C9 C10 C11 C12 -41.7(5) . . . . ?
C9 C10 C17 C16 17.2(3) . . . . ?
C9 C15 C16 C17 30.3(3) . . . . ?
C10 C9 C15 C14 -152.3(2) . . . . ?
C10 C9 C15 C16 -21.7(3) . . . . ?
C10 C11 C12 C6 58.2(4) . . . . ?
C11 C10 C17 C16 -166.7(3) . . . . ?
C12 C6 C7 N1 169.0(3) . . . . ?
C13 C8 C9 C10 156.4(3) . . . . ?
C13 C8 C9 C15 -22.6(3) . . . . ?
C13 C14 C15 C9 -18.9(3) . . . . ?
C13 C14 C15 C16 -135.8(3) . . . . ?
C13 C14 C22 O3 19.7(5) . . . . ?
C13 C14 C22 O4 -159.2(3) . . . . ?
C14 C15 C16 C17 148.6(3) . . . . ?
C15 C9 C10 C11 -172.8(3) . . . . ?
C15 C9 C10 C17 3.0(3) . . . . ?
C15 C14 C22 O3 -99.0(5) . . . . ?
C15 C14 C22 O4 82.0(4) . . . . ?
C15 C16 C17 C10 -29.1(3) . . . . ?
C17 C10 C11 C12 143.0(3) . . . . ?
C18 C2 C3 N1 42.2(3) . . . . ?
C18 C2 C3 C4 167.1(3) . . . . ?
C19 N1 C3 C2 -44.9(3) . . . . ?
C19 N1 C3 C4 -169.7(2) . . . . ?
C19 N1 C7 C6 161.2(3) . . . . ?
C20 C18 C19 N1 -124.1(4) . . . . ?
C21 C5 C6 C7 177.1(2) . . . . ?
C21 C5 C6 C12 -51.7(3) . . . . ?
C21 C5 C8 C1 -169.8(2) . . . . ?
C21 C5 C8 C9 65.5(3) . . . . ?
C21 C5 C8 C13 -51.1(3) . . . . ?
C22 C14 C15 C9 104.2(3) . . . . ?
C22 C14 C15 C16 -12.6(4) . . . . ?
C23 O4 C22 O3 2.8(7) . . . . ?
C23 O4 C22 C14 -178.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method methanol
_chemical_compound_source        'Daphniphyllum himalense'
