# 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 
# 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_lzwa913
_database_code_depnum_ccdc_archive 'CCDC 1444994'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '3-oxo-7R-coronaridine hydroxyindolenine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 N3 O4'
_chemical_formula_weight         409.48

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.07340(18)
_cell_length_b                   9.87893(13)
_cell_length_c                   11.00555(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.6571(19)
_cell_angle_gamma                90.00
_cell_volume                     1043.61(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.0(2)
_cell_measurement_reflns_used    11209
_cell_measurement_theta_min      4.4470
_cell_measurement_theta_max      62.8940

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Agilent Gemini S ultra'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16047
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.22
_diffrn_reflns_theta_max         62.73
_reflns_number_total             3290
_reflns_number_gt                3274
_reflns_threshold_expression     >2sigma(I)

_chemical_absolute_configuration rm

_computing_data_collection       'CrysAlis PRO '
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.1815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.051(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     274
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14845(9) 0.21159(9) 0.58833(8) 0.0228(2) Uani 1 1 d . . .
H1A H 0.0865 0.2686 0.5741 0.033(5) Uiso 1 1 calc R . .
O2 O 0.05789(10) -0.09477(10) 0.48383(9) 0.0295(2) Uani 1 1 d . . .
O3 O 0.10325(11) 0.32250(12) 0.09203(10) 0.0393(3) Uani 1 1 d . . .
O4 O 0.32970(10) 0.31331(10) 0.20076(9) 0.0299(2) Uani 1 1 d . . .
N1 N 0.23890(11) 0.44223(11) 0.40424(10) 0.0242(3) Uani 1 1 d . . .
C2 C 0.22814(13) 0.31423(13) 0.41784(12) 0.0204(3) Uani 1 1 d . . .
C3 C 0.09860(14) -0.02562(13) 0.40783(12) 0.0229(3) Uani 1 1 d . . .
N4 N 0.23115(11) 0.01353(11) 0.42823(10) 0.0206(2) Uani 1 1 d . . .
C5 C 0.33278(13) 0.01614(13) 0.55503(12) 0.0219(3) Uani 1 1 d . . .
H5A H 0.4121 -0.0397 0.5553 0.026 Uiso 1 1 calc R . .
H5B H 0.2911 -0.0216 0.6162 0.026 Uiso 1 1 calc R . .
C6 C 0.38259(13) 0.16066(13) 0.59507(12) 0.0215(3) Uani 1 1 d . . .
H6A H 0.4260 0.1627 0.6867 0.026 Uiso 1 1 calc R . .
H6B H 0.4529 0.1852 0.5552 0.026 Uiso 1 1 calc R . .
C7 C 0.26573(13) 0.26607(13) 0.55916(12) 0.0197(3) Uani 1 1 d . . .
C8 C 0.30892(13) 0.40076(14) 0.62335(12) 0.0216(3) Uani 1 1 d . . .
C9 C 0.35694(14) 0.43470(15) 0.75144(13) 0.0254(3) Uani 1 1 d . . .
H9A H 0.3733 0.3682 0.8141 0.031 Uiso 1 1 calc R . .
C10 C 0.38008(15) 0.57057(15) 0.78409(14) 0.0292(3) Uani 1 1 d . . .
H10A H 0.4135 0.5955 0.8695 0.035 Uiso 1 1 calc R . .
C11 C 0.35361(15) 0.66889(15) 0.69023(14) 0.0314(3) Uani 1 1 d . . .
H11A H 0.3677 0.7594 0.7139 0.038 Uiso 1 1 calc R . .
C12 C 0.30621(16) 0.63570(15) 0.56077(14) 0.0296(3) Uani 1 1 d . . .
H12A H 0.2887 0.7021 0.4980 0.035 Uiso 1 1 calc R . .
C13 C 0.28645(14) 0.49994(14) 0.53008(13) 0.0232(3) Uani 1 1 d . . .
C14 C 0.00536(14) 0.02762(15) 0.28120(13) 0.0262(3) Uani 1 1 d . . .
H14A H -0.0918 0.0022 0.2693 0.031 Uiso 1 1 calc R . .
C15 C 0.05412(14) -0.02799(15) 0.17206(13) 0.0299(3) Uani 1 1 d . . .
H15A H 0.0048 0.0172 0.0930 0.036 Uiso 1 1 calc R . .
H15B H 0.0343 -0.1241 0.1617 0.036 Uiso 1 1 calc R . .
C16 C 0.17616(14) 0.22142(13) 0.30350(12) 0.0215(3) Uani 1 1 d . . .
C17 C 0.02071(14) 0.18281(14) 0.28372(13) 0.0242(3) Uani 1 1 d . . .
H17A H -0.0095 0.2200 0.3525 0.029 Uiso 1 1 calc R . .
H17B H -0.0375 0.2207 0.2040 0.029 Uiso 1 1 calc R . .
C18 C 0.2799(2) -0.21159(18) 0.09893(17) 0.0443(4) Uani 1 1 d . . .
H18A H 0.3327 -0.2940 0.1171 0.066 Uiso 1 1 calc R . .
H18B H 0.3147 -0.1558 0.0440 0.066 Uiso 1 1 calc R . .
H18C H 0.1836 -0.2324 0.0575 0.066 Uiso 1 1 calc R . .
C19 C 0.29352(16) -0.13672(14) 0.22248(14) 0.0292(3) Uani 1 1 d . . .
H19A H 0.3912 -0.1179 0.2646 0.035 Uiso 1 1 calc R . .
H19B H 0.2604 -0.1947 0.2783 0.035 Uiso 1 1 calc R . .
C20 C 0.21231(14) -0.00368(14) 0.20299(12) 0.0243(3) Uani 1 1 d . . .
H20A H 0.2294 0.0453 0.1317 0.029 Uiso 1 1 calc R . .
C21 C 0.25950(13) 0.08573(13) 0.32302(12) 0.0203(3) Uani 1 1 d . . .
H21A H 0.3594 0.1046 0.3441 0.024 Uiso 1 1 calc R . .
C22 C 0.19565(14) 0.29308(14) 0.18652(13) 0.0245(3) Uani 1 1 d . . .
C23 C 0.36211(19) 0.38066(18) 0.09674(16) 0.0418(4) Uani 1 1 d . . .
H23A H 0.4613 0.3900 0.1166 0.063 Uiso 1 1 calc R . .
H23B H 0.3196 0.4686 0.0841 0.063 Uiso 1 1 calc R . .
H23C H 0.3270 0.3281 0.0203 0.063 Uiso 1 1 calc R . .
N5 N 0.34526(19) 0.0861(2) 0.89668(15) 0.0576(4) Uani 1 1 d . . .
C24 C 0.2276(2) 0.07273(17) 0.85515(16) 0.0402(4) Uani 1 1 d . . .
C25 C 0.0782(2) 0.0546(2) 0.8028(2) 0.0578(5) Uani 1 1 d . . .
H25A H 0.0473 -0.0104 0.8532 0.087 Uiso 1 1 calc R . .
H25B H 0.0563 0.0228 0.7166 0.087 Uiso 1 1 calc R . .
H25C H 0.0323 0.1395 0.8041 0.087 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.4208(15) . ?
O2 C3 1.2419(16) . ?
O3 C22 1.2021(18) . ?
O4 C22 1.3265(17) . ?
O4 C23 1.4444(18) . ?
N1 C2 1.2818(18) . ?
N1 C13 1.4387(17) . ?
C2 C16 1.5161(19) . ?
C2 C7 1.5593(17) . ?
C3 N4 1.3421(17) . ?
C3 C14 1.5189(19) . ?
N4 C5 1.4593(16) . ?
N4 C21 1.4600(16) . ?
C5 C6 1.5330(19) . ?
C6 C7 1.5309(18) . ?
C7 C8 1.5075(19) . ?
C8 C9 1.3857(19) . ?
C8 C13 1.3871(19) . ?
C9 C10 1.391(2) . ?
C10 C11 1.384(2) . ?
C11 C12 1.397(2) . ?
C12 C13 1.383(2) . ?
C14 C15 1.5309(19) . ?
C14 C17 1.5403(19) . ?
C15 C20 1.5439(19) . ?
C16 C22 1.5330(18) . ?
C16 C17 1.5615(18) . ?
C16 C21 1.5616(18) . ?
C18 C19 1.517(2) . ?
C19 C20 1.5284(19) . ?
C20 C21 1.5396(18) . ?
N5 C24 1.141(2) . ?
C24 C25 1.450(3) . ?

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
C22 O4 C23 116.26(11) . . ?
C2 N1 C13 107.08(11) . . ?
N1 C2 C16 121.32(12) . . ?
N1 C2 C7 114.45(12) . . ?
C16 C2 C7 124.17(11) . . ?
O2 C3 N4 124.12(12) . . ?
O2 C3 C14 124.74(12) . . ?
N4 C3 C14 111.14(11) . . ?
C3 N4 C5 122.60(10) . . ?
C3 N4 C21 115.60(10) . . ?
C5 N4 C21 120.04(10) . . ?
N4 C5 C6 111.40(10) . . ?
C7 C6 C5 113.59(10) . . ?
O1 C7 C8 111.71(10) . . ?
O1 C7 C6 108.12(10) . . ?
C8 C7 C6 112.92(10) . . ?
O1 C7 C2 111.96(10) . . ?
C8 C7 C2 98.42(10) . . ?
C6 C7 C2 113.59(10) . . ?
C9 C8 C13 120.68(13) . . ?
C9 C8 C7 130.73(12) . . ?
C13 C8 C7 108.51(11) . . ?
C8 C9 C10 118.41(13) . . ?
C11 C10 C9 120.36(13) . . ?
C10 C11 C12 121.69(14) . . ?
C13 C12 C11 117.13(13) . . ?
C12 C13 C8 121.69(13) . . ?
C12 C13 N1 126.92(12) . . ?
C8 C13 N1 111.37(12) . . ?
C3 C14 C15 109.84(11) . . ?
C3 C14 C17 107.30(11) . . ?
C15 C14 C17 108.48(12) . . ?
C14 C15 C20 109.06(10) . . ?
C2 C16 C22 108.53(11) . . ?
C2 C16 C17 110.04(10) . . ?
C22 C16 C17 111.97(10) . . ?
C2 C16 C21 111.65(10) . . ?
C22 C16 C21 108.15(10) . . ?
C17 C16 C21 106.50(10) . . ?
C14 C17 C16 109.67(11) . . ?
C18 C19 C20 113.22(12) . . ?
C19 C20 C21 111.10(11) . . ?
C19 C20 C15 111.71(12) . . ?
C21 C20 C15 107.93(11) . . ?
N4 C21 C20 108.45(10) . . ?
N4 C21 C16 107.59(10) . . ?
C20 C21 C16 111.18(10) . . ?
O3 C22 O4 123.99(13) . . ?
O3 C22 C16 125.12(13) . . ?
O4 C22 C16 110.82(11) . . ?
N5 C24 C25 179.5(2) . . ?

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
C13 N1 C2 C16 178.23(11) . . . . ?
C13 N1 C2 C7 0.97(15) . . . . ?
O2 C3 N4 C5 -19.5(2) . . . . ?
C14 C3 N4 C5 159.55(12) . . . . ?
O2 C3 N4 C21 175.59(12) . . . . ?
C14 C3 N4 C21 -5.34(16) . . . . ?
C3 N4 C5 C6 -115.87(13) . . . . ?
C21 N4 C5 C6 48.38(15) . . . . ?
N4 C5 C6 C7 41.17(14) . . . . ?
C5 C6 C7 O1 43.25(13) . . . . ?
C5 C6 C7 C8 167.37(10) . . . . ?
C5 C6 C7 C2 -81.65(14) . . . . ?
N1 C2 C7 O1 114.56(13) . . . . ?
C16 C2 C7 O1 -62.61(16) . . . . ?
N1 C2 C7 C8 -3.02(14) . . . . ?
C16 C2 C7 C8 179.81(12) . . . . ?
N1 C2 C7 C6 -122.63(13) . . . . ?
C16 C2 C7 C6 60.20(16) . . . . ?
O1 C7 C8 C9 62.79(17) . . . . ?
C6 C7 C8 C9 -59.34(18) . . . . ?
C2 C7 C8 C9 -179.45(13) . . . . ?
O1 C7 C8 C13 -113.91(11) . . . . ?
C6 C7 C8 C13 123.96(11) . . . . ?
C2 C7 C8 C13 3.85(12) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
C7 C8 C9 C10 -175.45(13) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C8 1.7(2) . . . . ?
C11 C12 C13 N1 -179.89(12) . . . . ?
C9 C8 C13 C12 -2.3(2) . . . . ?
C7 C8 C13 C12 174.83(13) . . . . ?
C9 C8 C13 N1 179.10(11) . . . . ?
C7 C8 C13 N1 -3.80(14) . . . . ?
C2 N1 C13 C12 -176.75(14) . . . . ?
C2 N1 C13 C8 1.79(15) . . . . ?
O2 C3 C14 C15 -120.10(15) . . . . ?
N4 C3 C14 C15 60.84(14) . . . . ?
O2 C3 C14 C17 122.17(14) . . . . ?
N4 C3 C14 C17 -56.89(14) . . . . ?
C3 C14 C15 C20 -50.22(15) . . . . ?
C17 C14 C15 C20 66.77(14) . . . . ?
N1 C2 C16 C22 21.10(17) . . . . ?
C7 C2 C16 C22 -161.92(11) . . . . ?
N1 C2 C16 C17 -101.75(14) . . . . ?
C7 C2 C16 C17 75.24(15) . . . . ?
N1 C2 C16 C21 140.21(12) . . . . ?
C7 C2 C16 C21 -42.80(16) . . . . ?
C3 C14 C17 C16 59.35(14) . . . . ?
C15 C14 C17 C16 -59.26(14) . . . . ?
C2 C16 C17 C14 -125.12(12) . . . . ?
C22 C16 C17 C14 114.08(12) . . . . ?
C21 C16 C17 C14 -3.95(14) . . . . ?
C18 C19 C20 C21 -164.78(13) . . . . ?
C18 C19 C20 C15 74.64(16) . . . . ?
C14 C15 C20 C19 114.42(13) . . . . ?
C14 C15 C20 C21 -8.00(15) . . . . ?
C3 N4 C21 C20 -56.01(14) . . . . ?
C5 N4 C21 C20 138.68(12) . . . . ?
C3 N4 C21 C16 64.34(13) . . . . ?
C5 N4 C21 C16 -100.97(12) . . . . ?
C19 C20 C21 N4 -61.65(14) . . . . ?
C15 C20 C21 N4 61.14(13) . . . . ?
C19 C20 C21 C16 -179.74(11) . . . . ?
C15 C20 C21 C16 -56.95(14) . . . . ?
C2 C16 C21 N4 65.10(13) . . . . ?
C22 C16 C21 N4 -175.56(10) . . . . ?
C17 C16 C21 N4 -55.04(12) . . . . ?
C2 C16 C21 C20 -176.29(11) . . . . ?
C22 C16 C21 C20 -56.95(13) . . . . ?
C17 C16 C21 C20 63.57(13) . . . . ?
C23 O4 C22 O3 2.9(2) . . . . ?
C23 O4 C22 C16 -179.83(12) . . . . ?
C2 C16 C22 O3 -118.57(15) . . . . ?
C17 C16 C22 O3 3.10(19) . . . . ?
C21 C16 C22 O3 120.14(15) . . . . ?
C2 C16 C22 O4 64.25(14) . . . . ?
C17 C16 C22 O4 -174.08(11) . . . . ?
C21 C16 C22 O4 -57.05(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        62.73
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_lzwa9
_database_code_depnum_ccdc_archive 'CCDC 1444995'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3S-(24S-hydroxyethyl)-coronaridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H30 N2 O3'
_chemical_formula_weight         382.45

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   9.7015(8)
_cell_length_b                   10.7426(8)
_cell_length_c                   10.0282(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.663(10)
_cell_angle_gamma                90.00
_cell_volume                     995.86(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.0(3)
_cell_measurement_reflns_used    1742
_cell_measurement_theta_min      4.5970
_cell_measurement_theta_max      62.7220

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             418
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_min  0.81742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini S ultra'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4010
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.63
_diffrn_reflns_theta_max         62.72
_reflns_number_total             2310
_reflns_number_gt                2101
_reflns_threshold_expression     >2sigma(I)

_chemical_absolute_configuration rm

_computing_cell_refinement       'CrysAlis PRO '
_computing_data_collection       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4294(3) -0.5495(3) -0.2288(3) 0.0403(6) Uani 1 1 d . . .
H1A H 0.3639 -0.5711 -0.2981 0.058(14) Uiso 1 1 calc R . .
O2 O -0.1943(3) -0.7078(2) -0.0437(2) 0.0386(6) Uani 1 1 d . . .
O3 O -0.2802(2) -0.6993(2) -0.2769(2) 0.0308(5) Uani 1 1 d . . .
N1 N -0.3056(3) -0.4311(2) -0.2449(3) 0.0279(6) Uani 1 1 d . . .
H1B H -0.3581 -0.4815 -0.2145 0.033 Uiso 1 1 calc R . .
C2 C -0.1631(3) -0.4516(3) -0.2398(3) 0.0255(6) Uani 1 1 d . . .
C3 C 0.2385(3) -0.5316(3) -0.1165(3) 0.0283(7) Uani 1 1 d . . .
H3A H 0.2445 -0.4423 -0.0957 0.034 Uiso 1 1 calc R . .
N4 N 0.1370(3) -0.5496(3) -0.2584(3) 0.0266(5) Uani 1 1 d . . .
C5 C 0.1086(3) -0.4389(3) -0.3483(3) 0.0278(6) Uani 1 1 d . . .
H5A H 0.0474 -0.4638 -0.4402 0.033 Uiso 1 1 calc R . .
H5B H 0.1999 -0.4113 -0.3589 0.033 Uiso 1 1 calc R . .
C6 C 0.0374(3) -0.3270(3) -0.3009(3) 0.0288(7) Uani 1 1 d . . .
H6A H 0.0972 -0.3017 -0.2087 0.035 Uiso 1 1 calc R . .
H6B H 0.0345 -0.2582 -0.3644 0.035 Uiso 1 1 calc R . .
C7 C -0.1136(3) -0.3510(3) -0.2954(3) 0.0259(6) Uani 1 1 d . . .
C8 C -0.2318(3) -0.2645(3) -0.3398(3) 0.0280(6) Uani 1 1 d . . .
C9 C -0.2494(4) -0.1472(3) -0.4063(3) 0.0333(7) Uani 1 1 d . . .
H9A H -0.1735 -0.1104 -0.4304 0.040 Uiso 1 1 calc R . .
C10 C -0.3817(4) -0.0881(3) -0.4350(4) 0.0389(8) Uani 1 1 d . . .
H10A H -0.3945 -0.0112 -0.4798 0.047 Uiso 1 1 calc R . .
C11 C -0.4966(4) -0.1410(4) -0.3982(4) 0.0408(8) Uani 1 1 d . . .
H11A H -0.5836 -0.0980 -0.4175 0.049 Uiso 1 1 calc R . .
C12 C -0.4832(4) -0.2567(3) -0.3334(4) 0.0359(8) Uani 1 1 d . . .
H12A H -0.5595 -0.2923 -0.3090 0.043 Uiso 1 1 calc R . .
C13 C -0.3500(3) -0.3172(3) -0.3065(3) 0.0290(7) Uani 1 1 d . . .
C14 C 0.1755(3) -0.5970(3) -0.0116(3) 0.0269(7) Uani 1 1 d . . .
H14A H 0.2408 -0.5859 0.0836 0.032 Uiso 1 1 calc R . .
C15 C 0.1537(3) -0.7372(3) -0.0452(3) 0.0291(7) Uani 1 1 d . . .
H15A H 0.1036 -0.7754 0.0147 0.035 Uiso 1 1 calc R . .
H15B H 0.2469 -0.7776 -0.0276 0.035 Uiso 1 1 calc R . .
C16 C -0.0816(3) -0.5666(3) -0.1696(3) 0.0246(6) Uani 1 1 d . . .
C17 C 0.0296(3) -0.5363(3) -0.0242(3) 0.0277(6) Uani 1 1 d . . .
H17A H 0.0417 -0.4469 -0.0136 0.033 Uiso 1 1 calc R . .
H17B H -0.0068 -0.5668 0.0498 0.033 Uiso 1 1 calc R . .
C18 C 0.1511(4) -0.9621(4) -0.2661(4) 0.0429(8) Uani 1 1 d . . .
H18A H 0.2013 -1.0004 -0.3244 0.064 Uiso 1 1 calc R . .
H18B H 0.0546 -0.9948 -0.2892 0.064 Uiso 1 1 calc R . .
H18C H 0.2015 -0.9793 -0.1697 0.064 Uiso 1 1 calc R . .
C19 C 0.1445(4) -0.8213(3) -0.2901(3) 0.0325(7) Uani 1 1 d . . .
H19A H 0.0965 -0.8044 -0.3883 0.039 Uiso 1 1 calc R . .
H19B H 0.2422 -0.7887 -0.2671 0.039 Uiso 1 1 calc R . .
C20 C 0.0635(3) -0.7542(3) -0.2015(3) 0.0274(6) Uani 1 1 d . . .
H20A H -0.0218 -0.8043 -0.2041 0.033 Uiso 1 1 calc R . .
C21 C 0.0103(3) -0.6248(3) -0.2604(3) 0.0246(6) Uani 1 1 d . . .
H21A H -0.0517 -0.6337 -0.3574 0.029 Uiso 1 1 calc R . .
C22 C 0.3910(3) -0.5783(4) -0.1060(4) 0.0371(8) Uani 1 1 d . . .
H22A H 0.3924 -0.6690 -0.0953 0.044 Uiso 1 1 calc R . .
C23 C 0.5055(4) -0.5243(6) 0.0160(4) 0.0584(12) Uani 1 1 d . . .
H23A H 0.5982 -0.5569 0.0178 0.088 Uiso 1 1 calc R . .
H23B H 0.4857 -0.5461 0.1012 0.088 Uiso 1 1 calc R . .
H23C H 0.5061 -0.4354 0.0071 0.088 Uiso 1 1 calc R . .
C24 C -0.1896(3) -0.6655(3) -0.1527(3) 0.0270(7) Uani 1 1 d . . .
C25 C -0.3827(4) -0.7959(3) -0.2718(4) 0.0377(8) Uani 1 1 d . . .
H25A H -0.4428 -0.8143 -0.3650 0.057 Uiso 1 1 calc R . .
H25B H -0.4419 -0.7679 -0.2165 0.057 Uiso 1 1 calc R . .
H25C H -0.3312 -0.8696 -0.2305 0.057 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C22 1.424(4) . ?
O2 C24 1.197(4) . ?
O3 C24 1.338(4) . ?
O3 C25 1.449(4) . ?
N1 C13 1.379(4) . ?
N1 C2 1.385(4) . ?
C2 C7 1.369(5) . ?
C2 C16 1.519(5) . ?
C3 N4 1.477(4) . ?
C3 C22 1.535(5) . ?
C3 C14 1.537(4) . ?
N4 C21 1.466(4) . ?
N4 C5 1.467(4) . ?
C5 C6 1.532(5) . ?
C6 C7 1.504(4) . ?
C7 C8 1.437(5) . ?
C8 C13 1.408(5) . ?
C8 C9 1.412(5) . ?
C9 C10 1.382(5) . ?
C10 C11 1.397(6) . ?
C11 C12 1.391(6) . ?
C12 C13 1.397(5) . ?
C14 C17 1.529(4) . ?
C14 C15 1.544(5) . ?
C15 C20 1.557(5) . ?
C16 C24 1.538(4) . ?
C16 C17 1.562(4) . ?
C16 C21 1.584(4) . ?
C18 C19 1.529(5) . ?
C19 C20 1.533(5) . ?
C20 C21 1.538(4) . ?
C22 C23 1.497(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O3 C25 115.1(3) . . ?
C13 N1 C2 109.3(3) . . ?
C7 C2 N1 109.2(3) . . ?
C7 C2 C16 129.2(3) . . ?
N1 C2 C16 121.3(3) . . ?
N4 C3 C22 111.7(3) . . ?
N4 C3 C14 108.2(2) . . ?
C22 C3 C14 112.3(3) . . ?
C21 N4 C5 116.0(2) . . ?
C21 N4 C3 113.4(2) . . ?
C5 N4 C3 115.6(3) . . ?
N4 C5 C6 117.6(3) . . ?
C7 C6 C5 114.4(3) . . ?
C2 C7 C8 106.9(3) . . ?
C2 C7 C6 128.1(3) . . ?
C8 C7 C6 124.9(3) . . ?
C13 C8 C9 118.7(3) . . ?
C13 C8 C7 107.3(3) . . ?
C9 C8 C7 133.9(3) . . ?
C10 C9 C8 118.7(3) . . ?
C9 C10 C11 121.6(3) . . ?
C12 C11 C10 121.2(3) . . ?
C11 C12 C13 117.2(3) . . ?
N1 C13 C12 130.1(3) . . ?
N1 C13 C8 107.2(3) . . ?
C12 C13 C8 122.6(3) . . ?
C17 C14 C3 107.4(2) . . ?
C17 C14 C15 109.6(3) . . ?
C3 C14 C15 110.7(3) . . ?
C14 C15 C20 109.4(3) . . ?
C2 C16 C24 109.7(2) . . ?
C2 C16 C17 112.2(3) . . ?
C24 C16 C17 110.0(2) . . ?
C2 C16 C21 111.1(2) . . ?
C24 C16 C21 108.2(2) . . ?
C17 C16 C21 105.6(2) . . ?
C14 C17 C16 110.4(2) . . ?
C18 C19 C20 112.2(3) . . ?
C19 C20 C21 111.9(3) . . ?
C19 C20 C15 114.1(3) . . ?
C21 C20 C15 107.5(3) . . ?
N4 C21 C20 108.1(2) . . ?
N4 C21 C16 113.0(2) . . ?
C20 C21 C16 108.5(2) . . ?
O1 C22 C23 107.4(3) . . ?
O1 C22 C3 111.7(3) . . ?
C23 C22 C3 113.0(3) . . ?
O2 C24 O3 123.4(3) . . ?
O2 C24 C16 125.4(3) . . ?
O3 C24 C16 111.2(3) . . ?

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
C13 N1 C2 C7 1.0(3) . . . . ?
C13 N1 C2 C16 176.4(3) . . . . ?
C22 C3 N4 C21 122.7(3) . . . . ?
C14 C3 N4 C21 -1.4(3) . . . . ?
C22 C3 N4 C5 -99.9(3) . . . . ?
C14 C3 N4 C5 136.0(3) . . . . ?
C21 N4 C5 C6 73.9(3) . . . . ?
C3 N4 C5 C6 -62.4(3) . . . . ?
N4 C5 C6 C7 -64.4(4) . . . . ?
N1 C2 C7 C8 -1.1(3) . . . . ?
C16 C2 C7 C8 -176.0(3) . . . . ?
N1 C2 C7 C6 174.5(3) . . . . ?
C16 C2 C7 C6 -0.4(5) . . . . ?
C5 C6 C7 C2 45.8(4) . . . . ?
C5 C6 C7 C8 -139.4(3) . . . . ?
C2 C7 C8 C13 0.8(3) . . . . ?
C6 C7 C8 C13 -174.9(3) . . . . ?
C2 C7 C8 C9 -178.4(3) . . . . ?
C6 C7 C8 C9 5.8(5) . . . . ?
C13 C8 C9 C10 0.6(4) . . . . ?
C7 C8 C9 C10 179.8(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C12 -1.2(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C2 N1 C13 C12 -179.6(3) . . . . ?
C2 N1 C13 C8 -0.5(3) . . . . ?
C11 C12 C13 N1 -179.8(3) . . . . ?
C11 C12 C13 C8 1.2(5) . . . . ?
C9 C8 C13 N1 179.1(3) . . . . ?
C7 C8 C13 N1 -0.2(3) . . . . ?
C9 C8 C13 C12 -1.6(4) . . . . ?
C7 C8 C13 C12 179.0(3) . . . . ?
N4 C3 C14 C17 -60.4(3) . . . . ?
C22 C3 C14 C17 175.8(3) . . . . ?
N4 C3 C14 C15 59.2(3) . . . . ?
C22 C3 C14 C15 -64.5(3) . . . . ?
C17 C14 C15 C20 65.5(3) . . . . ?
C3 C14 C15 C20 -52.8(3) . . . . ?
C7 C2 C16 C24 -168.0(3) . . . . ?
N1 C2 C16 C24 17.6(4) . . . . ?
C7 C2 C16 C17 69.4(4) . . . . ?
N1 C2 C16 C17 -104.9(3) . . . . ?
C7 C2 C16 C21 -48.6(4) . . . . ?
N1 C2 C16 C21 137.1(3) . . . . ?
C3 C14 C17 C16 67.5(3) . . . . ?
C15 C14 C17 C16 -52.8(3) . . . . ?
C2 C16 C17 C14 -133.0(3) . . . . ?
C24 C16 C17 C14 104.6(3) . . . . ?
C21 C16 C17 C14 -11.9(3) . . . . ?
C18 C19 C20 C21 -159.9(3) . . . . ?
C18 C19 C20 C15 77.7(4) . . . . ?
C14 C15 C20 C19 116.8(3) . . . . ?
C14 C15 C20 C21 -7.9(3) . . . . ?
C5 N4 C21 C20 161.8(2) . . . . ?
C3 N4 C21 C20 -61.0(3) . . . . ?
C5 N4 C21 C16 -78.1(3) . . . . ?
C3 N4 C21 C16 59.2(3) . . . . ?
C19 C20 C21 N4 -61.2(3) . . . . ?
C15 C20 C21 N4 64.8(3) . . . . ?
C19 C20 C21 C16 175.9(2) . . . . ?
C15 C20 C21 C16 -58.0(3) . . . . ?
C2 C16 C21 N4 72.0(3) . . . . ?
C24 C16 C21 N4 -167.6(2) . . . . ?
C17 C16 C21 N4 -49.9(3) . . . . ?
C2 C16 C21 C20 -168.1(2) . . . . ?
C24 C16 C21 C20 -47.7(3) . . . . ?
C17 C16 C21 C20 70.0(3) . . . . ?
N4 C3 C22 O1 39.2(4) . . . . ?
C14 C3 C22 O1 161.0(3) . . . . ?
N4 C3 C22 C23 160.4(4) . . . . ?
C14 C3 C22 C23 -77.8(4) . . . . ?
C25 O3 C24 O2 -2.4(4) . . . . ?
C25 O3 C24 C16 177.8(3) . . . . ?
C2 C16 C24 O2 -119.5(3) . . . . ?
C17 C16 C24 O2 4.4(4) . . . . ?
C21 C16 C24 O2 119.3(3) . . . . ?
C2 C16 C24 O3 60.3(3) . . . . ?
C17 C16 C24 O3 -175.8(2) . . . . ?
C21 C16 C24 O3 -60.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        62.72
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_LIUZHIWEN_EH-A9-43
_database_code_depnum_ccdc_archive 'CCDC 1444996'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        5-oxo-6S-hydroxycoronaridine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 N2 O4'
_chemical_formula_weight         368.42

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.44984(14)
_cell_length_b                   11.4893(2)
_cell_length_c                   21.3736(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1829.44(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9664
_cell_measurement_theta_min      3.8270
_cell_measurement_theta_max      62.8400

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            14469
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.369
_diffrn_reflns_theta_max         62.697
_diffrn_reflns_theta_full        62.698
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2906
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.3854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ref
_refine_ls_number_reflns         2906
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1458(2) 0.73651(12) 0.82374(7) 0.0310(3) Uani 1 1 d . . . . .
O2 O 0.3567(2) 0.71177(12) 0.76449(7) 0.0340(4) Uani 1 1 d . . . . .
H2 H 0.3923 0.6611 0.7405 0.051 Uiso 1 1 calc R U . . .
N3 N 0.3206(2) 0.94010(13) 0.82657(7) 0.0204(3) Uani 1 1 d . . . . .
N4 N -0.1265(2) 0.91932(14) 0.70658(7) 0.0229(4) Uani 1 1 d . . . . .
H4 H -0.2279 0.9471 0.7186 0.027 Uiso 1 1 calc R U . . .
O5 O 0.52632(18) 0.98737(12) 0.75326(7) 0.0278(3) Uani 1 1 d . . . . .
O6 O -0.27305(19) 0.88583(14) 0.87460(7) 0.0355(4) Uani 1 1 d . . . . .
C7 C 0.0957(3) 0.85013(16) 0.64589(9) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.1564(3) 0.85074(16) 0.70989(8) 0.0208(4) Uani 1 1 d . . . . .
C9 C 0.1330(3) 1.07784(17) 0.88071(9) 0.0260(4) Uani 1 1 d . . . . .
H9 H 0.1204 1.1595 0.8933 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0007(3) 0.91631(16) 0.81440(9) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.4076(2) 0.92030(17) 0.77281(9) 0.0212(4) Uani 1 1 d . . . . .
C12 C -0.0815(3) 0.89354(16) 0.64576(9) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.3211(3) 1.05753(18) 0.85414(10) 0.0283(5) Uani 1 1 d . . . . .
H13A H 0.3487 1.1153 0.8225 0.034 Uiso 1 1 calc R U . . .
H13B H 0.4102 1.0627 0.8871 0.034 Uiso 1 1 calc R U . . .
C14 C -0.0075(3) 1.04867(17) 0.83064(9) 0.0262(4) Uani 1 1 d . . . . .
H14A H 0.0152 1.0943 0.7933 0.031 Uiso 1 1 calc R U . . .
H14B H -0.1263 1.0682 0.8460 0.031 Uiso 1 1 calc R U . . .
C15 C 0.0154(3) 0.89399(16) 0.74502(9) 0.0202(4) Uani 1 1 d . . . . .
C16 C -0.1592(3) 0.84828(18) 0.84074(8) 0.0241(4) Uani 1 1 d . . . . .
C17 C -0.1010(3) 0.87300(19) 0.53577(9) 0.0318(5) Uani 1 1 d . . . . .
H17 H -0.1641 0.8808 0.4985 0.038 Uiso 1 1 calc R U . . .
C18 C 0.1732(3) 0.81731(17) 0.58869(9) 0.0269(4) Uani 1 1 d . . . . .
H18 H 0.2897 0.7884 0.5873 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1072(3) 0.99941(18) 0.93750(9) 0.0269(5) Uani 1 1 d . . . . .
H19A H -0.0158 1.0045 0.9522 0.032 Uiso 1 1 calc R U . . .
H19B H 0.1859 1.0242 0.9711 0.032 Uiso 1 1 calc R U . . .
C20 C 0.1692(3) 0.86693(16) 0.84691(8) 0.0193(4) Uani 1 1 d . . . . .
H20 H 0.1889 0.7862 0.8337 0.023 Uiso 1 1 calc R U . . .
C21 C 0.3243(3) 0.6893(2) 0.94633(11) 0.0392(5) Uani 1 1 d . . . . .
H21A H 0.3210 0.6671 0.9031 0.059 Uiso 1 1 calc R U . . .
H21B H 0.2237 0.6558 0.9678 0.059 Uiso 1 1 calc R U . . .
H21C H 0.4337 0.6618 0.9649 0.059 Uiso 1 1 calc R U . . .
C22 C -0.1819(3) 0.90545(17) 0.59118(9) 0.0283(4) Uani 1 1 d . . . . .
H22 H -0.2986 0.9341 0.5920 0.034 Uiso 1 1 calc R U . . .
C23 C 0.3429(3) 0.82021(17) 0.73161(9) 0.0229(4) Uani 1 1 d . . . . .
H23 H 0.4210 0.8163 0.6948 0.027 Uiso 1 1 calc R U . . .
C24 C -0.2720(3) 0.6570(2) 0.85204(11) 0.0412(6) Uani 1 1 d . . . . .
H24A H -0.3912 0.6754 0.8381 0.062 Uiso 1 1 calc R U . . .
H24B H -0.2660 0.6640 0.8967 0.062 Uiso 1 1 calc R U . . .
H24C H -0.2428 0.5787 0.8401 0.062 Uiso 1 1 calc R U . . .
C25 C 0.1512(3) 0.87274(17) 0.91875(8) 0.0219(4) Uani 1 1 d . . . . .
H25 H 0.0477 0.8247 0.9304 0.026 Uiso 1 1 calc R U . . .
C26 C 0.0736(3) 0.82866(18) 0.53453(9) 0.0315(5) Uani 1 1 d . . . . .
H26 H 0.1237 0.8064 0.4965 0.038 Uiso 1 1 calc R U . . .
C27 C 0.3159(3) 0.82138(19) 0.95147(9) 0.0286(5) Uani 1 1 d . . . . .
H27A H 0.4235 0.8544 0.9331 0.034 Uiso 1 1 calc R U . . .
H27B H 0.3134 0.8431 0.9953 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.338(3) . ?
O1 C24 1.444(3) . ?
O2 C23 1.434(2) . ?
O2 H2 0.8200 . ?
N3 C11 1.339(2) . ?
N3 C13 1.472(3) . ?
N3 C20 1.472(2) . ?
N4 C15 1.370(3) . ?
N4 C12 1.375(2) . ?
N4 H4 0.8600 . ?
O5 C11 1.245(2) . ?
O6 C16 1.196(2) . ?
C7 C18 1.403(3) . ?
C7 C12 1.411(3) . ?
C7 C8 1.441(3) . ?
C8 C15 1.384(3) . ?
C8 C23 1.507(3) . ?
C9 C19 1.524(3) . ?
C9 C13 1.530(3) . ?
C9 C14 1.534(3) . ?
C9 H9 0.9800 . ?
C10 C15 1.509(3) . ?
C10 C16 1.532(3) . ?
C10 C20 1.543(3) . ?
C10 C14 1.561(3) . ?
C11 C23 1.526(3) . ?
C12 C22 1.392(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 C22 1.380(3) . ?
C17 C26 1.397(3) . ?
C17 H17 0.9300 . ?
C18 C26 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C25 1.545(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.543(2) . ?
C20 H20 0.9800 . ?
C21 C27 1.522(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C27 1.531(3) . ?
C25 H25 0.9800 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 C24 116.42(17) . . ?
C23 O2 H2 109.5 . . ?
C11 N3 C13 119.88(16) . . ?
C11 N3 C20 121.83(15) . . ?
C13 N3 C20 114.00(15) . . ?
C15 N4 C12 109.49(16) . . ?
C15 N4 H4 125.3 . . ?
C12 N4 H4 125.3 . . ?
C18 C7 C12 118.56(18) . . ?
C18 C7 C8 134.37(19) . . ?
C12 C7 C8 107.07(16) . . ?
C15 C8 C7 106.19(17) . . ?
C15 C8 C23 128.08(17) . . ?
C7 C8 C23 125.51(17) . . ?
C19 C9 C13 108.70(17) . . ?
C19 C9 C14 109.91(16) . . ?
C13 C9 C14 109.44(15) . . ?
C19 C9 H9 109.6 . . ?
C13 C9 H9 109.6 . . ?
C14 C9 H9 109.6 . . ?
C15 C10 C16 109.30(16) . . ?
C15 C10 C20 108.76(16) . . ?
C16 C10 C20 106.22(15) . . ?
C15 C10 C14 112.77(15) . . ?
C16 C10 C14 112.61(16) . . ?
C20 C10 C14 106.87(16) . . ?
O5 C11 N3 121.78(18) . . ?
O5 C11 C23 119.79(17) . . ?
N3 C11 C23 118.05(16) . . ?
N4 C12 C22 129.83(19) . . ?
N4 C12 C7 107.59(17) . . ?
C22 C12 C7 122.58(18) . . ?
N3 C13 C9 106.63(16) . . ?
N3 C13 H13A 110.4 . . ?
C9 C13 H13A 110.4 . . ?
N3 C13 H13B 110.4 . . ?
C9 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C9 C14 C10 109.94(16) . . ?
C9 C14 H14A 109.7 . . ?
C10 C14 H14A 109.7 . . ?
C9 C14 H14B 109.7 . . ?
C10 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N4 C15 C8 109.66(16) . . ?
N4 C15 C10 119.85(17) . . ?
C8 C15 C10 130.48(19) . . ?
O6 C16 O1 124.30(19) . . ?
O6 C16 C10 126.16(19) . . ?
O1 C16 C10 109.38(16) . . ?
C22 C17 C26 121.40(19) . . ?
C22 C17 H17 119.3 . . ?
C26 C17 H17 119.3 . . ?
C26 C18 C7 118.9(2) . . ?
C26 C18 H18 120.5 . . ?
C7 C18 H18 120.5 . . ?
C9 C19 C25 108.89(15) . . ?
C9 C19 H19A 109.9 . . ?
C25 C19 H19A 109.9 . . ?
C9 C19 H19B 109.9 . . ?
C25 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
N3 C20 C10 106.26(14) . . ?
N3 C20 C25 109.63(15) . . ?
C10 C20 C25 111.20(16) . . ?
N3 C20 H20 109.9 . . ?
C10 C20 H20 109.9 . . ?
C25 C20 H20 109.9 . . ?
C27 C21 H21A 109.5 . . ?
C27 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C27 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 C12 117.3(2) . . ?
C17 C22 H22 121.4 . . ?
C12 C22 H22 121.4 . . ?
O2 C23 C8 114.80(16) . . ?
O2 C23 C11 110.44(15) . . ?
C8 C23 C11 107.08(15) . . ?
O2 C23 H23 108.1 . . ?
C8 C23 H23 108.1 . . ?
C11 C23 H23 108.1 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C20 111.60(16) . . ?
C27 C25 C19 114.49(17) . . ?
C20 C25 C19 108.51(15) . . ?
C27 C25 H25 107.3 . . ?
C20 C25 H25 107.3 . . ?
C19 C25 H25 107.3 . . ?
C18 C26 C17 121.24(19) . . ?
C18 C26 H26 119.4 . . ?
C17 C26 H26 119.4 . . ?
C21 C27 C25 112.60(18) . . ?
C21 C27 H27A 109.1 . . ?
C25 C27 H27A 109.1 . . ?
C21 C27 H27B 109.1 . . ?
C25 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 C7 C8 C15 179.9(2) . . . . ?
C12 C7 C8 C15 -0.1(2) . . . . ?
C18 C7 C8 C23 5.0(3) . . . . ?
C12 C7 C8 C23 -175.04(17) . . . . ?
C13 N3 C11 O5 19.0(3) . . . . ?
C20 N3 C11 O5 174.36(17) . . . . ?
C13 N3 C11 C23 -154.00(18) . . . . ?
C20 N3 C11 C23 1.3(3) . . . . ?
C15 N4 C12 C22 -179.6(2) . . . . ?
C15 N4 C12 C7 0.0(2) . . . . ?
C18 C7 C12 N4 -179.98(17) . . . . ?
C8 C7 C12 N4 0.0(2) . . . . ?
C18 C7 C12 C22 -0.3(3) . . . . ?
C8 C7 C12 C22 179.73(18) . . . . ?
C11 N3 C13 C9 140.97(17) . . . . ?
C20 N3 C13 C9 -16.2(2) . . . . ?
C19 C9 C13 N3 69.69(19) . . . . ?
C14 C9 C13 N3 -50.4(2) . . . . ?
C19 C9 C14 C10 -54.8(2) . . . . ?
C13 C9 C14 C10 64.6(2) . . . . ?
C15 C10 C14 C9 -128.66(18) . . . . ?
C16 C10 C14 C9 107.06(18) . . . . ?
C20 C10 C14 C9 -9.2(2) . . . . ?
C12 N4 C15 C8 -0.1(2) . . . . ?
C12 N4 C15 C10 179.13(17) . . . . ?
C7 C8 C15 N4 0.1(2) . . . . ?
C23 C8 C15 N4 174.90(17) . . . . ?
C7 C8 C15 C10 -179.00(19) . . . . ?
C23 C8 C15 C10 -4.2(3) . . . . ?
C16 C10 C15 N4 57.8(2) . . . . ?
C20 C10 C15 N4 173.42(16) . . . . ?
C14 C10 C15 N4 -68.2(2) . . . . ?
C16 C10 C15 C8 -123.1(2) . . . . ?
C20 C10 C15 C8 -7.5(3) . . . . ?
C14 C10 C15 C8 110.8(2) . . . . ?
C24 O1 C16 O6 -4.1(3) . . . . ?
C24 O1 C16 C10 171.50(16) . . . . ?
C15 C10 C16 O6 -132.2(2) . . . . ?
C20 C10 C16 O6 110.6(2) . . . . ?
C14 C10 C16 O6 -6.1(3) . . . . ?
C15 C10 C16 O1 52.3(2) . . . . ?
C20 C10 C16 O1 -64.93(19) . . . . ?
C14 C10 C16 O1 178.42(16) . . . . ?
C12 C7 C18 C26 0.0(3) . . . . ?
C8 C7 C18 C26 -180.0(2) . . . . ?
C13 C9 C19 C25 -53.1(2) . . . . ?
C14 C9 C19 C25 66.7(2) . . . . ?
C11 N3 C20 C10 -84.5(2) . . . . ?
C13 N3 C20 C10 72.16(18) . . . . ?
C11 N3 C20 C25 155.22(17) . . . . ?
C13 N3 C20 C25 -48.1(2) . . . . ?
C15 C10 C20 N3 68.13(18) . . . . ?
C16 C10 C20 N3 -174.33(14) . . . . ?
C14 C10 C20 N3 -53.88(18) . . . . ?
C15 C10 C20 C25 -172.63(15) . . . . ?
C16 C10 C20 C25 -55.08(19) . . . . ?
C14 C10 C20 C25 65.36(19) . . . . ?
C26 C17 C22 C12 0.8(3) . . . . ?
N4 C12 C22 C17 179.51(19) . . . . ?
C7 C12 C22 C17 -0.1(3) . . . . ?
C15 C8 C23 O2 77.2(2) . . . . ?
C7 C8 C23 O2 -108.9(2) . . . . ?
C15 C8 C23 C11 -45.8(3) . . . . ?
C7 C8 C23 C11 128.07(19) . . . . ?
O5 C11 C23 O2 125.95(18) . . . . ?
N3 C11 C23 O2 -60.9(2) . . . . ?
O5 C11 C23 C8 -108.40(19) . . . . ?
N3 C11 C23 C8 64.8(2) . . . . ?
N3 C20 C25 C27 -64.1(2) . . . . ?
C10 C20 C25 C27 178.71(15) . . . . ?
N3 C20 C25 C19 63.0(2) . . . . ?
C10 C20 C25 C19 -54.2(2) . . . . ?
C9 C19 C25 C27 114.47(18) . . . . ?
C9 C19 C25 C20 -10.9(2) . . . . ?
C7 C18 C26 C17 0.6(3) . . . . ?
C22 C17 C26 C18 -1.0(3) . . . . ?
C20 C25 C27 C21 -72.4(2) . . . . ?
C19 C25 C27 C21 163.88(17) . . . . ?

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
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455
O2 H2 O5 0.82 2.09 2.7478(19) 137.0 4_646
N4 H4 O5 0.86 2.03 2.881(2) 170.9 1_455
C20 H20 O2 0.98 2.12 2.869(2) 132.2 .
C24 H24A O2 0.96 2.49 3.398(3) 158.8 1_455

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lzw42
_database_code_depnum_ccdc_archive 'CCDC 1444997'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '3-oxo-7S-coronaridine hydroxyindolenine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 N2 O4'
_chemical_formula_weight         368.42

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.78022(19)
_cell_length_b                   13.8217(4)
_cell_length_c                   15.0748(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1829.43(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.00(10)
_cell_measurement_reflns_used    7321
_cell_measurement_theta_min      4.3330
_cell_measurement_theta_max      62.9440

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Agilent Gemini S ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_reflns_number            14636
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.340
_diffrn_reflns_theta_max         62.832
_diffrn_reflns_theta_full        62.832
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2930
_reflns_number_gt                2827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.996
_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_data_collection       'CrysAlis PRO '
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79162(17) 0.41068(10) 0.40693(10) 0.0254(3) Uani 1 1 d . . . . .
H1A H 0.7847 0.4349 0.4564 0.038 Uiso 1 1 calc R U . . .
O2 O 0.74248(17) 0.50075(11) 0.06898(10) 0.0305(4) Uani 1 1 d . . . . .
O3 O 0.94040(18) 0.63081(11) 0.44202(10) 0.0314(4) Uani 1 1 d . . . . .
O4 O 0.8671(2) 0.76983(12) 0.38036(13) 0.0484(5) Uani 1 1 d . . . . .
N1 N 0.57071(19) 0.60715(12) 0.37010(12) 0.0245(4) Uani 1 1 d . . . . .
N4 N 0.87646(18) 0.49042(12) 0.19795(11) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.6867(2) 0.56045(14) 0.34117(14) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.8170(2) 0.53933(15) 0.12909(14) 0.0236(5) Uani 1 1 d . . . . .
C5 C 0.8308(2) 0.39141(14) 0.21722(15) 0.0243(5) Uani 1 1 d . . . . .
H5A H 0.9073 0.3607 0.2541 0.029 Uiso 1 1 calc R U . . .
H5B H 0.8231 0.3551 0.1623 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6782(2) 0.39015(14) 0.26476(14) 0.0244(5) Uani 1 1 d . . . . .
H6A H 0.6513 0.3235 0.2776 0.029 Uiso 1 1 calc R U . . .
H6B H 0.6012 0.4159 0.2251 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6744(2) 0.44799(15) 0.35152(14) 0.0214(4) Uani 1 1 d . . . . .
C8 C 0.5156(2) 0.44344(14) 0.39104(14) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.4225(3) 0.36587(16) 0.41062(15) 0.0282(5) Uani 1 1 d . . . . .
H9A H 0.4569 0.3027 0.4036 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2755(3) 0.38482(16) 0.44126(15) 0.0297(5) Uani 1 1 d . . . . .
H10A H 0.2110 0.3335 0.4546 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2242(3) 0.47860(16) 0.45213(15) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.1261 0.4895 0.4731 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3175(2) 0.55680(16) 0.43208(16) 0.0287(5) Uani 1 1 d . . . . .
H12A H 0.2838 0.6201 0.4396 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4620(2) 0.53744(14) 0.40057(14) 0.0235(5) Uani 1 1 d . . . . .
C14 C 0.8467(2) 0.64624(15) 0.13784(15) 0.0261(5) Uani 1 1 d . . . . .
H14A H 0.8068 0.6809 0.0861 0.031 Uiso 1 1 calc R U . . .
C15 C 1.0191(3) 0.66332(16) 0.14699(16) 0.0284(5) Uani 1 1 d . . . . .
H15A H 1.0390 0.7318 0.1548 0.034 Uiso 1 1 calc R U . . .
H15B H 1.0707 0.6420 0.0936 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8199(2) 0.61839(15) 0.30275(13) 0.0212(5) Uani 1 1 d . . . . .
C17 C 0.7670(2) 0.68088(15) 0.22286(16) 0.0269(5) Uani 1 1 d . . . . .
H17A H 0.6575 0.6755 0.2159 0.032 Uiso 1 1 calc R U . . .
H17B H 0.7915 0.7483 0.2336 0.032 Uiso 1 1 calc R U . . .
C18 C 1.3534(3) 0.5956(2) 0.17589(17) 0.0375(6) Uani 1 1 d . . . . .
H18A H 1.3289 0.6395 0.1287 0.056 Uiso 1 1 calc R U . . .
H18B H 1.4310 0.5515 0.1564 0.056 Uiso 1 1 calc R U . . .
H18C H 1.3898 0.6315 0.2261 0.056 Uiso 1 1 calc R U . . .
C19 C 1.2114(3) 0.53888(17) 0.20210(16) 0.0307(5) Uani 1 1 d . . . . .
H19B H 1.2353 0.4970 0.2519 0.037 Uiso 1 1 calc R U . . .
H19A H 1.1802 0.4983 0.1529 0.037 Uiso 1 1 calc R U . . .
C20 C 1.0797(2) 0.60639(15) 0.22772(15) 0.0245(5) Uani 1 1 d . . . . .
H20A H 1.1168 0.6527 0.2719 0.029 Uiso 1 1 calc R U . . .
C21 C 0.9466(2) 0.54988(15) 0.26796(14) 0.0212(4) Uani 1 1 d . . . . .
H21A H 0.9832 0.5084 0.3162 0.025 Uiso 1 1 calc R U . . .
C22 C 0.8773(2) 0.68323(16) 0.37779(15) 0.0255(5) Uani 1 1 d . . . . .
C23 C 0.9870(3) 0.68382(19) 0.52079(17) 0.0398(6) Uani 1 1 d . . . . .
H23C H 1.0497 0.7376 0.5038 0.060 Uiso 1 1 calc R U . . .
H23A H 1.0437 0.6417 0.5592 0.060 Uiso 1 1 calc R U . . .
H23B H 0.8984 0.7071 0.5514 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.422(2) . ?
O2 C3 1.238(3) . ?
O3 C22 1.330(3) . ?
O3 C23 1.454(3) . ?
O4 C22 1.201(3) . ?
N1 C2 1.282(3) . ?
N1 C13 1.432(3) . ?
N4 C3 1.344(3) . ?
N4 C5 1.455(3) . ?
N4 C21 1.473(3) . ?
C2 C16 1.531(3) . ?
C2 C7 1.566(3) . ?
C3 C14 1.506(3) . ?
C5 C6 1.520(3) . ?
C6 C7 1.533(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.389(3) . ?
C9 C10 1.396(3) . ?
C10 C11 1.382(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.381(3) . ?
C14 C15 1.538(3) . ?
C14 C17 1.537(3) . ?
C15 C20 1.544(3) . ?
C16 C22 1.529(3) . ?
C16 C21 1.552(3) . ?
C16 C17 1.553(3) . ?
C18 C19 1.525(3) . ?
C19 C20 1.536(3) . ?
C20 C21 1.531(3) . ?

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
C22 O3 C23 115.92(17) . . ?
C2 N1 C13 107.44(17) . . ?
C3 N4 C5 121.34(17) . . ?
C3 N4 C21 115.80(17) . . ?
C5 N4 C21 119.79(17) . . ?
N1 C2 C16 118.17(17) . . ?
N1 C2 C7 114.26(17) . . ?
C16 C2 C7 127.56(17) . . ?
O2 C3 N4 123.62(19) . . ?
O2 C3 C14 125.3(2) . . ?
N4 C3 C14 111.01(19) . . ?
N4 C5 C6 110.35(16) . . ?
C5 C6 C7 114.56(17) . . ?
O1 C7 C8 114.80(17) . . ?
O1 C7 C6 107.22(16) . . ?
C8 C7 C6 109.48(16) . . ?
O1 C7 C2 111.60(16) . . ?
C8 C7 C2 98.27(15) . . ?
C6 C7 C2 115.53(18) . . ?
C9 C8 C13 120.28(19) . . ?
C9 C8 C7 131.3(2) . . ?
C13 C8 C7 108.23(17) . . ?
C8 C9 C10 118.2(2) . . ?
C11 C10 C9 121.1(2) . . ?
C10 C11 C12 120.8(2) . . ?
C13 C12 C11 117.8(2) . . ?
C12 C13 C8 121.86(19) . . ?
C12 C13 N1 126.31(19) . . ?
C8 C13 N1 111.76(18) . . ?
C3 C14 C15 109.21(18) . . ?
C3 C14 C17 107.44(18) . . ?
C15 C14 C17 109.01(19) . . ?
C14 C15 C20 109.38(18) . . ?
C22 C16 C2 106.16(17) . . ?
C22 C16 C21 111.82(16) . . ?
C2 C16 C21 110.86(16) . . ?
C22 C16 C17 110.27(17) . . ?
C2 C16 C17 110.81(16) . . ?
C21 C16 C17 106.98(16) . . ?
C14 C17 C16 109.68(16) . . ?
C18 C19 C20 111.64(18) . . ?
C21 C20 C19 111.38(17) . . ?
C21 C20 C15 108.01(17) . . ?
C19 C20 C15 111.79(18) . . ?
N4 C21 C20 108.66(16) . . ?
N4 C21 C16 106.44(15) . . ?
C20 C21 C16 111.69(16) . . ?
O4 C22 O3 123.4(2) . . ?
O4 C22 C16 125.7(2) . . ?
O3 C22 C16 110.89(17) . . ?

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
C13 N1 C2 C16 178.90(17) . . . . ?
C13 N1 C2 C7 -2.1(2) . . . . ?
C5 N4 C3 O2 -13.3(3) . . . . ?
C21 N4 C3 O2 -173.38(18) . . . . ?
C5 N4 C3 C14 163.96(17) . . . . ?
C21 N4 C3 C14 3.8(2) . . . . ?
C3 N4 C5 C6 -79.0(2) . . . . ?
C21 N4 C5 C6 80.4(2) . . . . ?
N4 C5 C6 C7 -57.5(2) . . . . ?
C5 C6 C7 O1 -56.4(2) . . . . ?
C5 C6 C7 C8 178.43(17) . . . . ?
C5 C6 C7 C2 68.7(2) . . . . ?
N1 C2 C7 O1 -118.6(2) . . . . ?
C16 C2 C7 O1 60.3(3) . . . . ?
N1 C2 C7 C8 2.2(2) . . . . ?
C16 C2 C7 C8 -178.85(19) . . . . ?
N1 C2 C7 C6 118.5(2) . . . . ?
C16 C2 C7 C6 -62.6(3) . . . . ?
O1 C7 C8 C9 -68.0(3) . . . . ?
C6 C7 C8 C9 52.6(3) . . . . ?
C2 C7 C8 C9 173.5(2) . . . . ?
O1 C7 C8 C13 117.04(19) . . . . ?
C6 C7 C8 C13 -122.34(19) . . . . ?
C2 C7 C8 C13 -1.4(2) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C7 C8 C9 C10 -175.4(2) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C8 -1.7(3) . . . . ?
C11 C12 C13 N1 175.0(2) . . . . ?
C9 C8 C13 C12 2.0(3) . . . . ?
C7 C8 C13 C12 177.6(2) . . . . ?
C9 C8 C13 N1 -175.2(2) . . . . ?
C7 C8 C13 N1 0.5(2) . . . . ?
C2 N1 C13 C12 -176.0(2) . . . . ?
C2 N1 C13 C8 1.0(2) . . . . ?
O2 C3 C14 C15 -126.8(2) . . . . ?
N4 C3 C14 C15 56.1(2) . . . . ?
O2 C3 C14 C17 115.1(2) . . . . ?
N4 C3 C14 C17 -62.0(2) . . . . ?
C3 C14 C15 C20 -57.4(2) . . . . ?
C17 C14 C15 C20 59.7(2) . . . . ?
N1 C2 C16 C22 60.5(2) . . . . ?
C7 C2 C16 C22 -118.3(2) . . . . ?
N1 C2 C16 C21 -177.83(18) . . . . ?
C7 C2 C16 C21 3.3(3) . . . . ?
N1 C2 C16 C17 -59.2(2) . . . . ?
C7 C2 C16 C17 121.9(2) . . . . ?
C3 C14 C17 C16 54.1(2) . . . . ?
C15 C14 C17 C16 -64.1(2) . . . . ?
C22 C16 C17 C14 127.12(18) . . . . ?
C2 C16 C17 C14 -115.64(18) . . . . ?
C21 C16 C17 C14 5.3(2) . . . . ?
C18 C19 C20 C21 -170.91(19) . . . . ?
C18 C19 C20 C15 68.2(2) . . . . ?
C14 C15 C20 C21 2.1(2) . . . . ?
C14 C15 C20 C19 125.0(2) . . . . ?
C3 N4 C21 C20 -61.6(2) . . . . ?
C5 N4 C21 C20 137.91(17) . . . . ?
C3 N4 C21 C16 58.8(2) . . . . ?
C5 N4 C21 C16 -101.67(19) . . . . ?
C19 C20 C21 N4 -68.7(2) . . . . ?
C15 C20 C21 N4 54.5(2) . . . . ?
C19 C20 C21 C16 174.22(17) . . . . ?
C15 C20 C21 C16 -62.7(2) . . . . ?
C22 C16 C21 N4 178.79(16) . . . . ?
C2 C16 C21 N4 60.5(2) . . . . ?
C17 C16 C21 N4 -60.39(19) . . . . ?
C22 C16 C21 C20 -62.8(2) . . . . ?
C2 C16 C21 C20 178.98(17) . . . . ?
C17 C16 C21 C20 58.1(2) . . . . ?
C23 O3 C22 O4 4.8(3) . . . . ?
C23 O3 C22 C16 -174.67(18) . . . . ?
C2 C16 C22 O4 -111.8(2) . . . . ?
C21 C16 C22 O4 127.2(2) . . . . ?
C17 C16 C22 O4 8.3(3) . . . . ?
C2 C16 C22 O3 67.7(2) . . . . ?
C21 C16 C22 O3 -53.4(2) . . . . ?
C17 C16 C22 O3 -172.26(16) . . . . ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

