# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1554993'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CHEMW03_compound_1          
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: The SQUEEZE/PLATON procedure was employed to treat diffuse solvent
that could not model in terms of atomic sites. Its contribution 
was nevertheless taken into account in the chemical formula that constitutes
the crystal.
;
_vrf_PLAT340_compound_1          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............
RESPONSE: Crystals diffracted weakly especially at high resolution (cf Alert C)
and this likely impacted the model refinement in terms of bond length
accuracy for instance.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(1R,2R,4aS,12bS)-1-chloro-2-hydroxy-2,5,5,7-tetramethyl-1,2,3,4,4a,5,7,12b-octahydro-12H-isochromeno[3,4-b]quinolin-12-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Cl N O3, 0.57(C H4 O)'
_chemical_formula_sum            'C20.57 H26.27 Cl N O3.57'
_chemical_formula_weight         380.07

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.4603(3)
_cell_length_b                   16.6736(3)
_cell_length_c                   13.8087(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.239(7)
_cell_angle_gamma                90
_cell_volume                     4137.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11742
_cell_measurement_theta_min      6.5
_cell_measurement_theta_max      71.2

_exptl_crystal_description       'square flat cobbledstone'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             1618
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.811
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_process_details   'Reqab (Higashi, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku mm007HF Rotating Anode'
_diffrn_radiation_monochromator  'PSMIC CMF Confocal optics'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer Chi partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007 Rapid 2 conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            22873
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.523
_diffrn_reflns_theta_max         65.486
_diffrn_reflns_theta_full        65.486
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6991
_reflns_number_gt                3457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.964

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT(Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ', SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1605P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6982
_refine_ls_number_parameters     462
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2755
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_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
Cl1B Cl 0.72825(14) 0.34493(19) 0.9307(2) 0.0974(9) Uani 1 1 d . . . . .
Cl1 Cl 0.72559(19) 0.6304(2) 0.9612(2) 0.1150(11) Uani 1 1 d . . . . .
O3B' O 0.8835(3) 0.4197(4) 0.7918(5) 0.0887(19) Uani 1 1 d . . . . .
H3B' H 0.855941 0.455727 0.764901 0.133 Uiso 1 1 calc R U . . .
O1 O 0.8306(4) 0.5722(4) 0.7664(6) 0.091(2) Uani 1 1 d . . . . .
O2 O 0.7767(5) 0.8465(5) 0.7967(5) 0.099(2) Uani 1 1 d . . . . .
O1B O 0.6430(4) 0.4269(5) 0.6768(5) 0.095(2) Uani 1 1 d D . . . .
O2B' O 0.6988(4) 0.1490(4) 0.6977(6) 0.098(2) Uani 1 1 d . . . . .
N1 N 0.8956(6) 0.8024(6) 0.8390(6) 0.091(3) Uani 1 1 d . . . . .
O3' O 0.5910(4) 0.5757(5) 0.6974(9) 0.127(3) Uani 1 1 d . . . . .
H3' H 0.603203 0.528937 0.691626 0.190 Uiso 1 1 calc R U . . .
C3B' C 0.7576(4) 0.3096(5) 0.7485(7) 0.068(2) Uani 1 1 d . . . . .
H3BA H 0.779222 0.331725 0.695667 0.082 Uiso 1 1 calc R U . . .
C2B' C 0.7707(4) 0.3720(5) 0.8341(7) 0.068(2) Uani 1 1 d . . . . .
H2B' H 0.748414 0.422701 0.806184 0.082 Uiso 1 1 calc R U . . .
C8A C 0.9487(7) 0.7440(7) 0.8538(7) 0.090(3) Uani 1 1 d . . . . .
N1B N 0.5807(5) 0.1907(6) 0.6515(6) 0.098(3) Uani 1 1 d . . . . .
C4A C 0.9288(5) 0.6630(6) 0.8329(7) 0.079(3) Uani 1 1 d . . . . .
C3B C 0.6768(5) 0.2917(6) 0.7029(7) 0.080(3) Uani 1 1 d . . . . .
C3 C 0.7966(5) 0.7023(6) 0.7938(7) 0.080(3) Uani 1 1 d . . . . .
C4 C 0.8501(6) 0.6415(7) 0.7953(8) 0.083(3) Uani 1 1 d . . . . .
C2B C 0.6532(6) 0.2138(8) 0.6856(7) 0.089(3) Uani 1 1 d . . . . .
C3' C 0.7137(5) 0.6838(6) 0.7723(9) 0.083(3) Uani 1 1 d . . . . .
H3'A H 0.698207 0.669103 0.701838 0.099 Uiso 1 1 calc R U . . .
C4' C 0.6691(6) 0.7617(7) 0.7877(10) 0.099(3) Uani 1 1 d . . . . .
H4' H 0.678442 0.771171 0.859536 0.118 Uiso 1 1 calc R U . . .
C4AB C 0.5454(5) 0.3293(8) 0.6417(7) 0.088(3) Uani 1 1 d . . . . .
C4B C 0.6240(5) 0.3525(6) 0.6739(7) 0.083(3) Uani 1 1 d D . . . .
C8 C 1.0268(7) 0.7635(9) 0.8885(8) 0.105(4) Uani 1 1 d . . . . .
H8 H 1.042276 0.816298 0.901199 0.125 Uiso 1 1 calc R U . . .
C4B' C 0.7991(5) 0.2321(6) 0.7838(8) 0.083(3) Uani 1 1 d . . . . .
H4B' H 0.781890 0.214641 0.842503 0.099 Uiso 1 1 calc R U . . .
C8AB C 0.5245(6) 0.2492(8) 0.6327(8) 0.091(3) Uani 1 1 d . . . . .
C2 C 0.8213(7) 0.7833(6) 0.8098(8) 0.088(3) Uani 1 1 d . . . . .
C8B' C 0.7792(6) 0.1652(6) 0.7074(9) 0.088(3) Uani 1 1 d . . . . .
C2' C 0.6931(6) 0.6158(6) 0.8309(8) 0.091(3) Uani 1 1 d . . . . .
H2' H 0.718125 0.567859 0.813387 0.110 Uiso 1 1 calc R U . . .
C5 C 0.9831(6) 0.6045(7) 0.8473(8) 0.095(3) Uani 1 1 d . . . . .
H5 H 0.969342 0.551488 0.832341 0.114 Uiso 1 1 calc R U . . .
C6B' C 0.8984(6) 0.3081(7) 0.9016(8) 0.095(3) Uani 1 1 d . . . . .
H6BA H 0.951292 0.319803 0.918986 0.114 Uiso 1 1 calc R U . . .
H6BB H 0.885066 0.285379 0.959799 0.114 Uiso 1 1 calc R U . . .
C7 C 1.0764(7) 0.7028(10) 0.9018(9) 0.112(4) Uani 1 1 d . . . . .
H7 H 1.126462 0.715503 0.924661 0.134 Uiso 1 1 calc R U . . .
C1B' C 0.8552(5) 0.3866(6) 0.8736(7) 0.077(2) Uani 1 1 d . . . . .
C5B C 0.4891(6) 0.3864(9) 0.6215(8) 0.105(4) Uani 1 1 d . . . . .
H5B H 0.502598 0.440217 0.626923 0.125 Uiso 1 1 calc R U . . .
C8' C 0.6978(7) 0.8332(7) 0.7429(10) 0.104(3) Uani 1 1 d . . . . .
C6B C 0.4160(8) 0.3684(13) 0.5944(10) 0.122(5) Uani 1 1 d . . . . .
H6B H 0.379703 0.408110 0.583073 0.146 Uiso 1 1 calc R U . . .
C6 C 1.0580(6) 0.6228(9) 0.8838(8) 0.107(4) Uani 1 1 d . . . . .
H6 H 1.094164 0.582934 0.895620 0.128 Uiso 1 1 calc R U . . .
C1' C 0.6073(7) 0.5977(7) 0.8045(12) 0.114(4) Uani 1 1 d . . . . .
C5B' C 0.8832(6) 0.2475(7) 0.8191(10) 0.101(4) Uani 1 1 d . . . . .
H5BA H 0.908325 0.197688 0.842336 0.121 Uiso 1 1 calc R U . . .
H5BB H 0.902564 0.266924 0.763857 0.121 Uiso 1 1 calc R U . . .
C9B' C 0.7896(7) 0.1866(8) 0.6047(9) 0.111(4) Uani 1 1 d . . . . .
H9BA H 0.768420 0.145285 0.558407 0.167 Uiso 1 1 calc R U . . .
H9BB H 0.841767 0.191485 0.606675 0.167 Uiso 1 1 calc R U . . .
H9BC H 0.765257 0.236658 0.583877 0.167 Uiso 1 1 calc R U . . .
C7B' C 0.8720(7) 0.4469(8) 0.9610(9) 0.108(4) Uani 1 1 d . . . . .
H7BA H 0.923437 0.462261 0.974174 0.162 Uiso 1 1 calc R U . . .
H7BB H 0.861634 0.422316 1.019237 0.162 Uiso 1 1 calc R U . . .
H7BC H 0.841278 0.493590 0.943864 0.162 Uiso 1 1 calc R U . . .
C8B C 0.4496(7) 0.2279(10) 0.6050(8) 0.115(4) Uani 1 1 d . . . . .
H8B H 0.434869 0.174490 0.600424 0.138 Uiso 1 1 calc R U . . .
C9' C 0.6986(7) 0.8277(9) 0.6335(9) 0.119(4) Uani 1 1 d . . . . .
H9'A H 0.713540 0.878305 0.611339 0.178 Uiso 1 1 calc R U . . .
H9'B H 0.649620 0.814403 0.595752 0.178 Uiso 1 1 calc R U . . .
H9'C H 0.732994 0.786833 0.624264 0.178 Uiso 1 1 calc R U . . .
C5' C 0.5867(7) 0.7440(8) 0.7519(13) 0.127(5) Uani 1 1 d . . . . .
H5'A H 0.575902 0.729433 0.682090 0.153 Uiso 1 1 calc R U . . .
H5'B H 0.558187 0.791653 0.758905 0.153 Uiso 1 1 calc R U . . .
C7B C 0.3981(8) 0.2895(16) 0.5846(9) 0.138(7) Uani 1 1 d . . . . .
H7B H 0.348203 0.275957 0.562728 0.166 Uiso 1 1 calc R U . . .
C6' C 0.5635(8) 0.6739(8) 0.8137(14) 0.137(5) Uani 1 1 d . . . . .
H6'A H 0.572395 0.689512 0.883091 0.165 Uiso 1 1 calc R U . . .
H6'B H 0.510700 0.663374 0.790176 0.165 Uiso 1 1 calc R U . . .
C7' C 0.5859(8) 0.5301(9) 0.8636(15) 0.147(6) Uani 1 1 d . . . . .
H7'A H 0.534982 0.515657 0.836461 0.221 Uiso 1 1 calc R U . . .
H7'B H 0.591727 0.546588 0.931557 0.221 Uiso 1 1 calc R U . . .
H7'C H 0.617361 0.484721 0.860694 0.221 Uiso 1 1 calc R U . . .
C1B" C 0.5637(8) 0.1041(8) 0.6314(11) 0.127(5) Uani 1 1 d . . . . .
H1BA H 0.574880 0.089485 0.569123 0.190 Uiso 1 1 calc R U . . .
H1BB H 0.511974 0.094578 0.628283 0.190 Uiso 1 1 calc R U . . .
H1BC H 0.593433 0.072411 0.683802 0.190 Uiso 1 1 calc R U . . .
C1" C 0.9142(9) 0.8886(7) 0.8530(10) 0.127(5) Uani 1 1 d . . . . .
H1"A H 0.959155 0.894663 0.903529 0.190 Uiso 1 1 calc R U . . .
H1"B H 0.874301 0.916163 0.872934 0.190 Uiso 1 1 calc R U . . .
H1"C H 0.921058 0.910840 0.791619 0.190 Uiso 1 1 calc R U . . .
C10B C 0.8139(8) 0.0849(8) 0.7442(13) 0.131(5) Uani 1 1 d . . . . .
H10A H 0.807582 0.075197 0.810330 0.196 Uiso 1 1 calc R U . . .
H10B H 0.865999 0.085826 0.744879 0.196 Uiso 1 1 calc R U . . .
H10C H 0.789990 0.043033 0.700751 0.196 Uiso 1 1 calc R U . . .
C10' C 0.6619(9) 0.9108(7) 0.7644(12) 0.141(5) Uani 1 1 d . . . . .
H10D H 0.662664 0.913743 0.834032 0.212 Uiso 1 1 calc R U . . .
H10E H 0.611347 0.912534 0.726523 0.212 Uiso 1 1 calc R U . . .
H10F H 0.688926 0.955409 0.746210 0.212 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
Cl1B C2B' 1.754(9) . ?
Cl1 C2' 1.779(11) . ?
O3B' C1B' 1.457(11) . ?
O3B' H3B' 0.8200 . ?
O1 C4 1.249(11) . ?
O2 C2 1.324(13) . ?
O2 C8' 1.492(14) . ?
O1B C4B 1.287(10) . ?
O2B' C2B 1.356(13) . ?
O2B' C8B' 1.484(12) . ?
N1 C8A 1.363(14) . ?
N1 C2 1.376(15) . ?
N1 C1" 1.479(14) . ?
O3' C1' 1.487(17) . ?
O3' H3' 0.8200 . ?
C3B' C3B 1.510(12) . ?
C3B' C4B' 1.525(12) . ?
C3B' C2B' 1.551(12) . ?
C3B' H3BA 0.9800 . ?
C2B' C1B' 1.550(12) . ?
C2B' H2B' 0.9800 . ?
C8A C4A 1.411(15) . ?
C8A C8 1.449(16) . ?
N1B C2B 1.369(12) . ?
N1B C8AB 1.406(15) . ?
N1B C1B" 1.490(16) . ?
C4A C5 1.381(15) . ?
C4A C4 1.471(13) . ?
C3B C2B 1.374(14) . ?
C3B C4B 1.400(14) . ?
C3 C4 1.412(14) . ?
C3 C2 1.426(14) . ?
C3 C3' 1.522(13) . ?
C3' C2' 1.492(14) . ?
C3' C4' 1.579(14) . ?
C3' H3'A 0.9800 . ?
C4' C8' 1.496(16) . ?
C4' C5' 1.516(17) . ?
C4' H4' 0.9800 . ?
C4AB C8AB 1.387(17) . ?
C4AB C5B 1.391(16) . ?
C4AB C4B 1.468(13) . ?
C8 C7 1.350(19) . ?
C8 H8 0.9300 . ?
C4B' C8B' 1.522(14) . ?
C4B' C5B' 1.538(14) . ?
C4B' H4B' 0.9800 . ?
C8AB C8B 1.392(15) . ?
C8B' C9B' 1.517(16) . ?
C8B' C10B 1.520(17) . ?
C2' C1' 1.572(16) . ?
C2' H2' 0.9800 . ?
C5 C6 1.392(14) . ?
C5 H5 0.9300 . ?
C6B' C5B' 1.500(16) . ?
C6B' C1B' 1.535(14) . ?
C6B' H6BA 0.9700 . ?
C6B' H6BB 0.9700 . ?
C7 C6 1.384(19) . ?
C7 H7 0.9300 . ?
C1B' C7B' 1.546(15) . ?
C5B C6B 1.348(17) . ?
C5B H5B 0.9300 . ?
C8' C10' 1.514(16) . ?
C8' C9' 1.516(16) . ?
C6B C7B 1.35(2) . ?
C6B H6B 0.9300 . ?
C6 H6 0.9300 . ?
C1' C7' 1.496(19) . ?
C1' C6' 1.527(16) . ?
C5B' H5BA 0.9700 . ?
C5B' H5BB 0.9700 . ?
C9B' H9BA 0.9600 . ?
C9B' H9BB 0.9600 . ?
C9B' H9BC 0.9600 . ?
C7B' H7BA 0.9600 . ?
C7B' H7BB 0.9600 . ?
C7B' H7BC 0.9600 . ?
C8B C7B 1.38(2) . ?
C8B H8B 0.9300 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C5' C6' 1.56(2) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C7B H7B 0.9300 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C1B" H1BA 0.9600 . ?
C1B" H1BB 0.9600 . ?
C1B" H1BC 0.9600 . ?
C1" H1"A 0.9600 . ?
C1" H1"B 0.9600 . ?
C1" H1"C 0.9600 . ?
C10B H10A 0.9600 . ?
C10B H10B 0.9600 . ?
C10B H10C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 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
C1B' O3B' H3B' 109.5 . . ?
C2 O2 C8' 117.1(9) . . ?
C2B O2B' C8B' 116.5(8) . . ?
C8A N1 C2 120.8(9) . . ?
C8A N1 C1" 122.6(10) . . ?
C2 N1 C1" 116.6(12) . . ?
C1' O3' H3' 109.5 . . ?
C3B C3B' C4B' 110.0(7) . . ?
C3B C3B' C2B' 114.6(7) . . ?
C4B' C3B' C2B' 110.2(7) . . ?
C3B C3B' H3BA 107.2 . . ?
C4B' C3B' H3BA 107.2 . . ?
C2B' C3B' H3BA 107.2 . . ?
C1B' C2B' C3B' 110.1(7) . . ?
C1B' C2B' Cl1B 111.2(6) . . ?
C3B' C2B' Cl1B 112.9(6) . . ?
C1B' C2B' H2B' 107.5 . . ?
C3B' C2B' H2B' 107.5 . . ?
Cl1B C2B' H2B' 107.5 . . ?
N1 C8A C4A 120.6(10) . . ?
N1 C8A C8 121.0(11) . . ?
C4A C8A C8 118.3(13) . . ?
C2B N1B C8AB 119.4(10) . . ?
C2B N1B C1B" 119.0(12) . . ?
C8AB N1B C1B" 121.6(10) . . ?
C5 C4A C8A 120.0(9) . . ?
C5 C4A C4 120.3(10) . . ?
C8A C4A C4 119.7(10) . . ?
C2B C3B C4B 117.6(9) . . ?
C2B C3B C3B' 120.2(9) . . ?
C4B C3B C3B' 122.2(9) . . ?
C4 C3 C2 118.7(9) . . ?
C4 C3 C3' 121.7(9) . . ?
C2 C3 C3' 119.6(10) . . ?
O1 C4 C3 120.7(9) . . ?
O1 C4 C4A 121.8(10) . . ?
C3 C4 C4A 117.5(9) . . ?
O2B' C2B N1B 110.4(10) . . ?
O2B' C2B C3B 124.7(9) . . ?
N1B C2B C3B 124.9(12) . . ?
C2' C3' C3 114.7(9) . . ?
C2' C3' C4' 110.3(8) . . ?
C3 C3' C4' 109.8(9) . . ?
C2' C3' H3'A 107.2 . . ?
C3 C3' H3'A 107.2 . . ?
C4' C3' H3'A 107.2 . . ?
C8' C4' C5' 116.4(11) . . ?
C8' C4' C3' 110.8(9) . . ?
C5' C4' C3' 108.2(9) . . ?
C8' C4' H4' 107.0 . . ?
C5' C4' H4' 107.0 . . ?
C3' C4' H4' 107.0 . . ?
C8AB C4AB C5B 117.4(10) . . ?
C8AB C4AB C4B 121.2(10) . . ?
C5B C4AB C4B 121.4(12) . . ?
O1B C4B C3B 121.5(9) . . ?
O1B C4B C4AB 120.5(10) . . ?
C3B C4B C4AB 118.0(10) . . ?
C7 C8 C8A 118.0(12) . . ?
C7 C8 H8 121.0 . . ?
C8A C8 H8 121.0 . . ?
C8B' C4B' C3B' 112.1(8) . . ?
C8B' C4B' C5B' 114.1(9) . . ?
C3B' C4B' C5B' 110.9(8) . . ?
C8B' C4B' H4B' 106.4 . . ?
C3B' C4B' H4B' 106.4 . . ?
C5B' C4B' H4B' 106.4 . . ?
C4AB C8AB C8B 120.6(13) . . ?
C4AB C8AB N1B 118.2(9) . . ?
C8B C8AB N1B 121.2(12) . . ?
O2 C2 N1 113.8(10) . . ?
O2 C2 C3 124.4(11) . . ?
N1 C2 C3 121.8(11) . . ?
O2B' C8B' C9B' 107.2(9) . . ?
O2B' C8B' C10B 101.9(9) . . ?
C9B' C8B' C10B 112.7(11) . . ?
O2B' C8B' C4B' 105.9(8) . . ?
C9B' C8B' C4B' 114.4(9) . . ?
C10B C8B' C4B' 113.4(10) . . ?
C3' C2' C1' 112.9(10) . . ?
C3' C2' Cl1 112.1(7) . . ?
C1' C2' Cl1 110.4(9) . . ?
C3' C2' H2' 107.0 . . ?
C1' C2' H2' 107.0 . . ?
Cl1 C2' H2' 107.0 . . ?
C4A C5 C6 121.7(12) . . ?
C4A C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5B' C6B' C1B' 112.8(8) . . ?
C5B' C6B' H6BA 109.0 . . ?
C1B' C6B' H6BA 109.0 . . ?
C5B' C6B' H6BB 109.0 . . ?
C1B' C6B' H6BB 109.0 . . ?
H6BA C6B' H6BB 107.8 . . ?
C8 C7 C6 124.5(12) . . ?
C8 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
O3B' C1B' C6B' 105.1(8) . . ?
O3B' C1B' C7B' 108.5(9) . . ?
C6B' C1B' C7B' 111.0(8) . . ?
O3B' C1B' C2B' 107.3(7) . . ?
C6B' C1B' C2B' 112.1(8) . . ?
C7B' C1B' C2B' 112.5(8) . . ?
C6B C5B C4AB 123.9(15) . . ?
C6B C5B H5B 118.0 . . ?
C4AB C5B H5B 118.0 . . ?
O2 C8' C4' 108.1(10) . . ?
O2 C8' C10' 101.3(11) . . ?
C4' C8' C10' 112.8(10) . . ?
O2 C8' C9' 106.0(9) . . ?
C4' C8' C9' 116.6(11) . . ?
C10' C8' C9' 110.6(11) . . ?
C5B C6B C7B 116.7(16) . . ?
C5B C6B H6B 121.7 . . ?
C7B C6B H6B 121.7 . . ?
C7 C6 C5 117.3(13) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
O3' C1' C7' 109.8(11) . . ?
O3' C1' C6' 107.3(13) . . ?
C7' C1' C6' 111.7(12) . . ?
O3' C1' C2' 104.0(10) . . ?
C7' C1' C2' 113.3(12) . . ?
C6' C1' C2' 110.2(10) . . ?
C6B' C5B' C4B' 110.7(9) . . ?
C6B' C5B' H5BA 109.5 . . ?
C4B' C5B' H5BA 109.5 . . ?
C6B' C5B' H5BB 109.5 . . ?
C4B' C5B' H5BB 109.5 . . ?
H5BA C5B' H5BB 108.1 . . ?
C8B' C9B' H9BA 109.5 . . ?
C8B' C9B' H9BB 109.5 . . ?
H9BA C9B' H9BB 109.5 . . ?
C8B' C9B' H9BC 109.5 . . ?
H9BA C9B' H9BC 109.5 . . ?
H9BB C9B' H9BC 109.5 . . ?
C1B' C7B' H7BA 109.5 . . ?
C1B' C7B' H7BB 109.5 . . ?
H7BA C7B' H7BB 109.5 . . ?
C1B' C7B' H7BC 109.5 . . ?
H7BA C7B' H7BC 109.5 . . ?
H7BB C7B' H7BC 109.5 . . ?
C7B C8B C8AB 117.3(15) . . ?
C7B C8B H8B 121.3 . . ?
C8AB C8B H8B 121.3 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C4' C5' C6' 110.3(12) . . ?
C4' C5' H5'A 109.6 . . ?
C6' C5' H5'A 109.6 . . ?
C4' C5' H5'B 109.6 . . ?
C6' C5' H5'B 109.6 . . ?
H5'A C5' H5'B 108.1 . . ?
C6B C7B C8B 124.0(14) . . ?
C6B C7B H7B 118.0 . . ?
C8B C7B H7B 118.0 . . ?
C1' C6' C5' 111.1(11) . . ?
C1' C6' H6'A 109.4 . . ?
C5' C6' H6'A 109.4 . . ?
C1' C6' H6'B 109.4 . . ?
C5' C6' H6'B 109.4 . . ?
H6'A C6' H6'B 108.0 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N1B C1B" H1BA 109.5 . . ?
N1B C1B" H1BB 109.5 . . ?
H1BA C1B" H1BB 109.5 . . ?
N1B C1B" H1BC 109.5 . . ?
H1BA C1B" H1BC 109.5 . . ?
H1BB C1B" H1BC 109.5 . . ?
N1 C1" H1"A 109.5 . . ?
N1 C1" H1"B 109.5 . . ?
H1"A C1" H1"B 109.5 . . ?
N1 C1" H1"C 109.5 . . ?
H1"A C1" H1"C 109.5 . . ?
H1"B C1" H1"C 109.5 . . ?
C8B' C10B H10A 109.5 . . ?
C8B' C10B H10B 109.5 . . ?
H10A C10B H10B 109.5 . . ?
C8B' C10B H10C 109.5 . . ?
H10A C10B H10C 109.5 . . ?
H10B C10B H10C 109.5 . . ?
C8' C10' H10D 109.5 . . ?
C8' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C8' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.101






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/H2O'
####################################################################### 
# 
# 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_compound_16_FO5-99_hklf5
_database_code_depnum_ccdc_archive 'CCDC 1589038'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Cl N O3'
_chemical_formula_sum            'C20 H24 Cl N O3'
_chemical_formula_weight         361.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4568(5)
_cell_length_b                   11.4834(3)
_cell_length_c                   14.2866(7)
_cell_angle_alpha                94.508(3)
_cell_angle_beta                 106.183(4)
_cell_angle_gamma                90.764(2)
_cell_volume                     1798.31(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13461
_cell_measurement_theta_min      3.9960
_cell_measurement_theta_max      30.6470

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.53972
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Rigaku four-circle diffractometer'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku(Mo) X-ray Source'
_diffrn_radiation_monochromator  'Confocal MaxFlux double bounce optic'
_diffrn_measurement_device_type  'XtaLABPRO AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_reflns_number            45746
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.601
_diffrn_reflns_theta_max         30.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             9861
_reflns_number_gt                8036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+1.6071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9814
_refine_ls_number_parameters     467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1833
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.20023(16) -0.01098(16) 0.05923(16) 0.0401(4) Uani 1 1 d . . . . .
N1 N 0.40590(18) 0.00758(17) 0.12742(15) 0.0305(4) Uani 1 1 d . . . . .
C2 C 0.2982(2) 0.04129(19) 0.06496(17) 0.0279(4) Uani 1 1 d . . . . .
C3 C 0.3037(2) 0.13832(18) 0.00637(16) 0.0250(4) Uani 1 1 d . . . . .
C4 C 0.4124(2) 0.18992(19) 0.01063(17) 0.0269(4) Uani 1 1 d . . . . .
C4A C 0.5247(2) 0.1539(2) 0.07664(17) 0.0286(4) Uani 1 1 d . . . . .
C5 C 0.6376(2) 0.2091(3) 0.0854(2) 0.0398(6) Uani 1 1 d . . . . .
H5 H 0.642006 0.270066 0.047177 0.048 Uiso 1 1 calc R U . . .
C6 C 0.7424(2) 0.1741(3) 0.1501(2) 0.0458(7) Uani 1 1 d . . . . .
H6 H 0.816980 0.211195 0.155415 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7354(2) 0.0832(3) 0.2069(2) 0.0414(6) Uani 1 1 d . . . . .
H7 H 0.805823 0.059628 0.250526 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6258(2) 0.0273(2) 0.19997(19) 0.0354(5) Uani 1 1 d . . . . .
H8 H 0.622974 -0.033687 0.238573 0.042 Uiso 1 1 calc R U . . .
C8A C 0.5182(2) 0.0619(2) 0.13470(17) 0.0278(4) Uani 1 1 d . . . . .
C9 C 0.4006(3) -0.0927(3) 0.1840(2) 0.0463(7) Uani 1 1 d . . . . .
H9AA H 0.436718 -0.070392 0.252278 0.070 Uiso 1 1 calc R U . . .
H9AB H 0.444223 -0.155722 0.163105 0.070 Uiso 1 1 calc R U . . .
H9AC H 0.317266 -0.117622 0.173591 0.070 Uiso 1 1 calc R U . . .
Cl1' Cl 0.15300(6) 0.31476(7) 0.09505(5) 0.04496(18) Uani 1 1 d . . . . .
O1' O -0.07670(17) 0.16529(17) -0.15198(15) 0.0385(4) Uani 1 1 d . . . . .
H1' H -0.115(4) 0.121(3) -0.132(3) 0.058 Uiso 1 1 d . U . . .
C1' C -0.0229(2) 0.26025(19) -0.08223(18) 0.0278(4) Uani 1 1 d . . . . .
O2' O 0.42923(16) 0.27541(17) -0.04464(15) 0.0388(4) Uani 1 1 d . . . . .
C2' C 0.0904(2) 0.21205(19) -0.01180(16) 0.0256(4) Uani 1 1 d . . . . .
H2' H 0.062631 0.142088 0.012140 0.031 Uiso 1 1 calc R U . . .
C3' C 0.18670(19) 0.17246(18) -0.06318(16) 0.0239(4) Uani 1 1 d . . . . .
H3' H 0.152188 0.099197 -0.101352 0.029 Uiso 1 1 calc R U . . .
C4' C 0.2136(2) 0.25023(19) -0.13939(16) 0.0268(4) Uani 1 1 d . . . . .
H4' H 0.235520 0.194752 -0.186872 0.032 Uiso 1 1 calc R U . . .
C5' C 0.0979(2) 0.3061(2) -0.19947(19) 0.0362(5) Uani 1 1 d . . . . .
H5'A H 0.121923 0.369628 -0.231900 0.043 Uiso 1 1 calc R U . . .
H5'B H 0.052104 0.248165 -0.249831 0.043 Uiso 1 1 calc R U . . .
C6' C 0.0149(2) 0.3534(2) -0.1393(2) 0.0352(5) Uani 1 1 d . . . . .
H6'A H 0.056854 0.417919 -0.094001 0.042 Uiso 1 1 calc R U . . .
H6'B H -0.057276 0.383225 -0.182786 0.042 Uiso 1 1 calc R U . . .
C7' C -0.1145(3) 0.3058(3) -0.0300(2) 0.0454(6) Uani 1 1 d . . . . .
H7'A H -0.078655 0.371418 0.015318 0.068 Uiso 1 1 calc R U . . .
H7'B H -0.136865 0.245051 0.004902 0.068 Uiso 1 1 calc R U . . .
H7'C H -0.185549 0.329650 -0.077136 0.068 Uiso 1 1 calc R U . . .
C8' C 0.3253(2) 0.3361(2) -0.10250(19) 0.0316(5) Uani 1 1 d . . . . .
C10' C 0.3704(3) 0.3700(3) -0.1885(2) 0.0509(8) Uani 1 1 d . . . . .
H10A H 0.311628 0.417351 -0.228697 0.076 Uiso 1 1 calc R U . . .
H10B H 0.381242 0.300559 -0.226743 0.076 Uiso 1 1 calc R U . . .
H10C H 0.446527 0.413312 -0.163989 0.076 Uiso 1 1 calc R U . . .
C9' C 0.3127(3) 0.4454(3) -0.0399(3) 0.0522(8) Uani 1 1 d . . . . .
H9A H 0.246633 0.489333 -0.075475 0.078 Uiso 1 1 calc R U . . .
H9B H 0.386750 0.492317 -0.023743 0.078 Uiso 1 1 calc R U . . .
H9C H 0.296837 0.423860 0.019040 0.078 Uiso 1 1 calc R U . . .
O1B O 0.53457(17) 0.17980(16) 0.56658(17) 0.0449(5) Uani 1 1 d . . . . .
N1B N 0.55273(18) 0.36771(18) 0.63478(16) 0.0324(4) Uani 1 1 d . . . . .
Cl1B Cl 0.20923(7) 0.12199(6) 0.59266(5) 0.04314(17) Uani 1 1 d . . . . .
C2B C 0.4881(2) 0.27662(19) 0.57202(18) 0.0301(5) Uani 1 1 d . . . . .
C3B C 0.3662(2) 0.29701(18) 0.51252(17) 0.0260(4) Uani 1 1 d . . . . .
C4B C 0.3201(2) 0.40490(19) 0.51648(17) 0.0279(4) Uani 1 1 d . . . . .
C4AB C 0.3893(2) 0.5002(2) 0.58217(17) 0.0296(4) Uani 1 1 d . . . . .
C5B C 0.3429(3) 0.6120(2) 0.5885(2) 0.0412(6) Uani 1 1 d . . . . .
H5B H 0.266167 0.626956 0.548864 0.049 Uiso 1 1 calc R U . . .
C6B C 0.4101(3) 0.6999(3) 0.6529(3) 0.0505(7) Uani 1 1 d . . . . .
H6B H 0.379124 0.774143 0.656032 0.061 Uiso 1 1 calc R U . . .
C7B C 0.5241(3) 0.6777(3) 0.7130(2) 0.0458(7) Uani 1 1 d . . . . .
H7B H 0.568421 0.736800 0.757480 0.055 Uiso 1 1 calc R U . . .
C8B C 0.5723(3) 0.5690(2) 0.7075(2) 0.0387(6) Uani 1 1 d . . . . .
H8B H 0.649175 0.555397 0.747631 0.046 Uiso 1 1 calc R U . . .
C8AB C 0.5056(2) 0.4784(2) 0.64142(17) 0.0293(4) Uani 1 1 d . . . . .
C9B C 0.6763(3) 0.3466(3) 0.6937(3) 0.0523(8) Uani 1 1 d . . . . .
H9BA H 0.683361 0.367667 0.761481 0.078 Uiso 1 1 calc R U . . .
H9BB H 0.733648 0.393073 0.673407 0.078 Uiso 1 1 calc R U . . .
H9BC H 0.692717 0.265399 0.684793 0.078 Uiso 1 1 calc R U . . .
C1'B C 0.1995(2) -0.00661(19) 0.41725(19) 0.0302(5) Uani 1 1 d . . . . .
O1'B O 0.27149(17) -0.03749(16) 0.35269(15) 0.0373(4) Uani 1 1 d . . . . .
H1'B H 0.330(3) -0.078(3) 0.382(2) 0.034(8) Uiso 1 1 d . . . . .
C2'B C 0.2751(2) 0.08884(19) 0.49147(17) 0.0277(4) Uani 1 1 d . . . . .
H2'B H 0.354795 0.056508 0.519567 0.033 Uiso 1 1 calc R U . . .
O2'B O 0.21083(17) 0.43539(15) 0.46061(15) 0.0393(4) Uani 1 1 d . . . . .
C3'B C 0.29829(19) 0.19845(18) 0.44212(16) 0.0248(4) Uani 1 1 d . . . . .
H3'B H 0.355117 0.172981 0.405180 0.030 Uiso 1 1 calc R U . . .
C4'B C 0.1898(2) 0.24495(19) 0.36420(16) 0.0258(4) Uani 1 1 d . . . . .
H4'B H 0.227861 0.280436 0.319277 0.031 Uiso 1 1 calc R U . . .
C5'B C 0.1078(2) 0.1446(2) 0.30022(18) 0.0334(5) Uani 1 1 d . . . . .
H5'C H 0.030753 0.176175 0.266580 0.040 Uiso 1 1 calc R U . . .
H5'D H 0.145630 0.114625 0.250821 0.040 Uiso 1 1 calc R U . . .
C6'B C 0.0823(2) 0.0425(2) 0.3553(2) 0.0335(5) Uani 1 1 d . . . . .
H6'C H 0.032824 0.068810 0.397502 0.040 Uiso 1 1 calc R U . . .
H6'D H 0.036487 -0.019042 0.308652 0.040 Uiso 1 1 calc R U . . .
C7'B C 0.1718(3) -0.1141(2) 0.4652(3) 0.0464(7) Uani 1 1 d . . . . .
H7'D H 0.117528 -0.093937 0.503879 0.070 Uiso 1 1 calc R U . . .
H7'E H 0.246131 -0.140898 0.506403 0.070 Uiso 1 1 calc R U . . .
H7'F H 0.134514 -0.175000 0.415447 0.070 Uiso 1 1 calc R U . . .
C8'B C 0.1216(2) 0.34621(19) 0.40101(18) 0.0290(4) Uani 1 1 d . . . . .
C9'B C 0.0359(3) 0.3174(3) 0.4605(3) 0.0512(8) Uani 1 1 d . . . . .
H9'D H -0.023843 0.259323 0.423797 0.077 Uiso 1 1 calc R U . . .
H9'E H -0.003991 0.386808 0.474844 0.077 Uiso 1 1 calc R U . . .
H9'F H 0.081232 0.287989 0.520516 0.077 Uiso 1 1 calc R U . . .
C10B C 0.0540(3) 0.4137(2) 0.3150(2) 0.0442(7) Uani 1 1 d . . . . .
H10D H -0.011523 0.365195 0.272685 0.066 Uiso 1 1 calc R U . . .
H10E H 0.109228 0.435212 0.279023 0.066 Uiso 1 1 calc R U . . .
H10F H 0.021998 0.482857 0.339226 0.066 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 C2 1.245(3) . ?
N1 C2 1.387(3) . ?
N1 C8A 1.396(3) . ?
N1 C9 1.468(3) . ?
C2 C3 1.456(3) . ?
C3 C4 1.356(3) . ?
C3 C3' 1.507(3) . ?
C4 O2' 1.351(3) . ?
C4 C4A 1.454(3) . ?
C4A C5 1.403(3) . ?
C4A C8A 1.407(3) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.407(3) . ?
C8 H8 0.9300 . ?
C9 H9AA 0.9600 . ?
C9 H9AB 0.9600 . ?
C9 H9AC 0.9600 . ?
Cl1' C2' 1.822(2) . ?
O1' C1' 1.425(3) . ?
O1' H1' 0.78(4) . ?
C1' C7' 1.523(3) . ?
C1' C6' 1.523(3) . ?
C1' C2' 1.544(3) . ?
O2' C8' 1.467(3) . ?
C2' C3' 1.541(3) . ?
C2' H2' 0.9800 . ?
C3' C4' 1.553(3) . ?
C3' H3' 0.9800 . ?
C4' C5' 1.543(3) . ?
C4' C8' 1.548(3) . ?
C4' H4' 0.9800 . ?
C5' C6' 1.528(4) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' C9' 1.515(4) . ?
C8' C10' 1.534(4) . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C9' H9A 0.9600 . ?
C9' H9B 0.9600 . ?
C9' H9C 0.9600 . ?
O1B C2B 1.246(3) . ?
N1B C2B 1.382(3) . ?
N1B C8AB 1.395(3) . ?
N1B C9B 1.465(3) . ?
Cl1B C2'B 1.826(2) . ?
C2B C3B 1.451(3) . ?
C3B C4B 1.357(3) . ?
C3B C3'B 1.503(3) . ?
C4B O2'B 1.351(3) . ?
C4B C4AB 1.451(3) . ?
C4AB C5B 1.402(3) . ?
C4AB C8AB 1.403(3) . ?
C5B C6B 1.377(4) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.389(5) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.377(4) . ?
C7B H7B 0.9300 . ?
C8B C8AB 1.407(3) . ?
C8B H8B 0.9300 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C1'B O1'B 1.427(3) . ?
C1'B C7'B 1.529(3) . ?
C1'B C6'B 1.530(3) . ?
C1'B C2'B 1.535(3) . ?
O1'B H1'B 0.85(3) . ?
C2'B C3'B 1.545(3) . ?
C2'B H2'B 0.9800 . ?
O2'B C8'B 1.473(3) . ?
C3'B C4'B 1.552(3) . ?
C3'B H3'B 0.9800 . ?
C4'B C5'B 1.541(3) . ?
C4'B C8'B 1.548(3) . ?
C4'B H4'B 0.9800 . ?
C5'B C6'B 1.531(4) . ?
C5'B H5'C 0.9700 . ?
C5'B H5'D 0.9700 . ?
C6'B H6'C 0.9700 . ?
C6'B H6'D 0.9700 . ?
C7'B H7'D 0.9600 . ?
C7'B H7'E 0.9600 . ?
C7'B H7'F 0.9600 . ?
C8'B C9'B 1.515(4) . ?
C8'B C10B 1.532(3) . ?
C9'B H9'D 0.9600 . ?
C9'B H9'E 0.9600 . ?
C9'B H9'F 0.9600 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 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
C2 N1 C8A 122.47(19) . . ?
C2 N1 C9 117.9(2) . . ?
C8A N1 C9 119.6(2) . . ?
O1 C2 N1 120.4(2) . . ?
O1 C2 C3 121.5(2) . . ?
N1 C2 C3 118.0(2) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 C3' 121.97(19) . . ?
C2 C3 C3' 117.70(19) . . ?
O2' C4 C3 125.3(2) . . ?
O2' C4 C4A 113.56(19) . . ?
C3 C4 C4A 121.1(2) . . ?
C5 C4A C8A 119.5(2) . . ?
C5 C4A C4 122.2(2) . . ?
C8A C4A C4 118.3(2) . . ?
C6 C5 C4A 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4A C5 H5 119.6 . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
N1 C8A C8 121.3(2) . . ?
N1 C8A C4A 119.8(2) . . ?
C8 C8A C4A 118.9(2) . . ?
N1 C9 H9AA 109.5 . . ?
N1 C9 H9AB 109.5 . . ?
H9AA C9 H9AB 109.5 . . ?
N1 C9 H9AC 109.5 . . ?
H9AA C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C1' O1' H1' 113(3) . . ?
O1' C1' C7' 109.9(2) . . ?
O1' C1' C6' 106.4(2) . . ?
C7' C1' C6' 111.5(2) . . ?
O1' C1' C2' 106.05(18) . . ?
C7' C1' C2' 112.5(2) . . ?
C6' C1' C2' 110.21(18) . . ?
C4 O2' C8' 120.69(18) . . ?
C3' C2' C1' 112.80(18) . . ?
C3' C2' Cl1' 112.57(15) . . ?
C1' C2' Cl1' 111.24(15) . . ?
C3' C2' H2' 106.6 . . ?
C1' C2' H2' 106.6 . . ?
Cl1' C2' H2' 106.6 . . ?
C3 C3' C2' 113.44(18) . . ?
C3 C3' C4' 110.37(17) . . ?
C2' C3' C4' 118.25(17) . . ?
C3 C3' H3' 104.4 . . ?
C2' C3' H3' 104.4 . . ?
C4' C3' H3' 104.4 . . ?
C5' C4' C8' 113.91(19) . . ?
C5' C4' C3' 112.04(18) . . ?
C8' C4' C3' 116.51(19) . . ?
C5' C4' H4' 104.2 . . ?
C8' C4' H4' 104.2 . . ?
C3' C4' H4' 104.2 . . ?
C6' C5' C4' 114.4(2) . . ?
C6' C5' H5'A 108.7 . . ?
C4' C5' H5'A 108.7 . . ?
C6' C5' H5'B 108.7 . . ?
C4' C5' H5'B 108.7 . . ?
H5'A C5' H5'B 107.6 . . ?
C1' C6' C5' 112.2(2) . . ?
C1' C6' H6'A 109.2 . . ?
C5' C6' H6'A 109.2 . . ?
C1' C6' H6'B 109.2 . . ?
C5' C6' H6'B 109.2 . . ?
H6'A C6' H6'B 107.9 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
O2' C8' C9' 106.3(2) . . ?
O2' C8' C10' 102.2(2) . . ?
C9' C8' C10' 109.5(2) . . ?
O2' C8' C4' 109.62(18) . . ?
C9' C8' C4' 117.6(2) . . ?
C10' C8' C4' 110.3(2) . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C8' C9' H9A 109.5 . . ?
C8' C9' H9B 109.5 . . ?
H9A C9' H9B 109.5 . . ?
C8' C9' H9C 109.5 . . ?
H9A C9' H9C 109.5 . . ?
H9B C9' H9C 109.5 . . ?
C2B N1B C8AB 122.2(2) . . ?
C2B N1B C9B 118.1(2) . . ?
C8AB N1B C9B 119.7(2) . . ?
O1B C2B N1B 120.2(2) . . ?
O1B C2B C3B 121.2(2) . . ?
N1B C2B C3B 118.5(2) . . ?
C4B C3B C2B 119.9(2) . . ?
C4B C3B C3'B 121.9(2) . . ?
C2B C3B C3'B 118.04(19) . . ?
O2'B C4B C3B 125.0(2) . . ?
O2'B C4B C4AB 113.95(19) . . ?
C3B C4B C4AB 121.0(2) . . ?
C5B C4AB C8AB 119.5(2) . . ?
C5B C4AB C4B 122.1(2) . . ?
C8AB C4AB C4B 118.4(2) . . ?
C6B C5B C4AB 120.6(3) . . ?
C6B C5B H5B 119.7 . . ?
C4AB C5B H5B 119.7 . . ?
C5B C6B C7B 119.9(3) . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C8B C7B C6B 120.7(3) . . ?
C8B C7B H7B 119.7 . . ?
C6B C7B H7B 119.7 . . ?
C7B C8B C8AB 120.2(3) . . ?
C7B C8B H8B 119.9 . . ?
C8AB C8B H8B 119.9 . . ?
N1B C8AB C4AB 119.8(2) . . ?
N1B C8AB C8B 121.1(2) . . ?
C4AB C8AB C8B 119.1(2) . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O1'B C1'B C7'B 110.2(2) . . ?
O1'B C1'B C6'B 106.8(2) . . ?
C7'B C1'B C6'B 110.9(2) . . ?
O1'B C1'B C2'B 105.13(19) . . ?
C7'B C1'B C2'B 112.8(2) . . ?
C6'B C1'B C2'B 110.70(18) . . ?
C1'B O1'B H1'B 109(2) . . ?
C1'B C2'B C3'B 112.08(19) . . ?
C1'B C2'B Cl1B 111.35(16) . . ?
C3'B C2'B Cl1B 113.09(15) . . ?
C1'B C2'B H2'B 106.6 . . ?
C3'B C2'B H2'B 106.6 . . ?
Cl1B C2'B H2'B 106.6 . . ?
C4B O2'B C8'B 120.95(17) . . ?
C3B C3'B C2'B 114.06(18) . . ?
C3B C3'B C4'B 110.65(17) . . ?
C2'B C3'B C4'B 117.95(18) . . ?
C3B C3'B H3'B 104.1 . . ?
C2'B C3'B H3'B 104.1 . . ?
C4'B C3'B H3'B 104.1 . . ?
C5'B C4'B C8'B 115.16(19) . . ?
C5'B C4'B C3'B 111.78(17) . . ?
C8'B C4'B C3'B 115.94(18) . . ?
C5'B C4'B H4'B 104.1 . . ?
C8'B C4'B H4'B 104.1 . . ?
C3'B C4'B H4'B 104.1 . . ?
C6'B C5'B C4'B 115.2(2) . . ?
C6'B C5'B H5'C 108.5 . . ?
C4'B C5'B H5'C 108.5 . . ?
C6'B C5'B H5'D 108.5 . . ?
C4'B C5'B H5'D 108.5 . . ?
H5'C C5'B H5'D 107.5 . . ?
C1'B C6'B C5'B 112.01(19) . . ?
C1'B C6'B H6'C 109.2 . . ?
C5'B C6'B H6'C 109.2 . . ?
C1'B C6'B H6'D 109.2 . . ?
C5'B C6'B H6'D 109.2 . . ?
H6'C C6'B H6'D 107.9 . . ?
C1'B C7'B H7'D 109.5 . . ?
C1'B C7'B H7'E 109.5 . . ?
H7'D C7'B H7'E 109.5 . . ?
C1'B C7'B H7'F 109.5 . . ?
H7'D C7'B H7'F 109.5 . . ?
H7'E C7'B H7'F 109.5 . . ?
O2'B C8'B C9'B 107.1(2) . . ?
O2'B C8'B C10B 101.87(19) . . ?
C9'B C8'B C10B 109.4(2) . . ?
O2'B C8'B C4'B 109.21(18) . . ?
C9'B C8'B C4'B 118.2(2) . . ?
C10B C8'B C4'B 109.9(2) . . ?
C8'B C9'B H9'D 109.5 . . ?
C8'B C9'B H9'E 109.5 . . ?
H9'D C9'B H9'E 109.5 . . ?
C8'B C9'B H9'F 109.5 . . ?
H9'D C9'B H9'F 109.5 . . ?
H9'E C9'B H9'F 109.5 . . ?
C8'B C10B H10D 109.5 . . ?
C8'B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C8'B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A N1 C2 O1 178.6(2) . . . . ?
C9 N1 C2 O1 1.5(4) . . . . ?
C8A N1 C2 C3 -1.0(3) . . . . ?
C9 N1 C2 C3 -178.0(2) . . . . ?
O1 C2 C3 C4 -176.8(2) . . . . ?
N1 C2 C3 C4 2.7(3) . . . . ?
O1 C2 C3 C3' -1.0(3) . . . . ?
N1 C2 C3 C3' 178.5(2) . . . . ?
C2 C3 C4 O2' 175.7(2) . . . . ?
C3' C3 C4 O2' 0.1(4) . . . . ?
C2 C3 C4 C4A -3.0(3) . . . . ?
C3' C3 C4 C4A -178.6(2) . . . . ?
O2' C4 C4A C5 3.9(3) . . . . ?
C3 C4 C4A C5 -177.3(2) . . . . ?
O2' C4 C4A C8A -177.4(2) . . . . ?
C3 C4 C4A C8A 1.4(3) . . . . ?
C8A C4A C5 C6 0.2(4) . . . . ?
C4 C4A C5 C6 178.9(3) . . . . ?
C4A C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C8A -0.2(4) . . . . ?
C2 N1 C8A C8 178.9(2) . . . . ?
C9 N1 C8A C8 -4.1(4) . . . . ?
C2 N1 C8A C4A -0.5(3) . . . . ?
C9 N1 C8A C4A 176.5(2) . . . . ?
C7 C8 C8A N1 -179.1(2) . . . . ?
C7 C8 C8A C4A 0.3(4) . . . . ?
C5 C4A C8A N1 179.1(2) . . . . ?
C4 C4A C8A N1 0.3(3) . . . . ?
C5 C4A C8A C8 -0.3(4) . . . . ?
C4 C4A C8A C8 -179.1(2) . . . . ?
C3 C4 O2' C8' 11.9(4) . . . . ?
C4A C4 O2' C8' -169.3(2) . . . . ?
O1' C1' C2' C3' 63.2(2) . . . . ?
C7' C1' C2' C3' -176.6(2) . . . . ?
C6' C1' C2' C3' -51.5(3) . . . . ?
O1' C1' C2' Cl1' -169.20(15) . . . . ?
C7' C1' C2' Cl1' -49.0(2) . . . . ?
C6' C1' C2' Cl1' 76.1(2) . . . . ?
C4 C3 C3' C2' -123.2(2) . . . . ?
C2 C3 C3' C2' 61.1(3) . . . . ?
C4 C3 C3' C4' 12.1(3) . . . . ?
C2 C3 C3' C4' -163.59(19) . . . . ?
C1' C2' C3' C3 173.30(17) . . . . ?
Cl1' C2' C3' C3 46.4(2) . . . . ?
C1' C2' C3' C4' 41.7(3) . . . . ?
Cl1' C2' C3' C4' -85.2(2) . . . . ?
C3 C3' C4' C5' -169.24(19) . . . . ?
C2' C3' C4' C5' -36.3(3) . . . . ?
C3 C3' C4' C8' -35.6(3) . . . . ?
C2' C3' C4' C8' 97.4(2) . . . . ?
C8' C4' C5' C6' -92.5(2) . . . . ?
C3' C4' C5' C6' 42.4(3) . . . . ?
O1' C1' C6' C5' -55.2(3) . . . . ?
C7' C1' C6' C5' -174.9(2) . . . . ?
C2' C1' C6' C5' 59.3(3) . . . . ?
C4' C5' C6' C1' -55.9(3) . . . . ?
C4 O2' C8' C9' 94.5(3) . . . . ?
C4 O2' C8' C10' -150.7(2) . . . . ?
C4 O2' C8' C4' -33.6(3) . . . . ?
C5' C4' C8' O2' 178.7(2) . . . . ?
C3' C4' C8' O2' 45.9(3) . . . . ?
C5' C4' C8' C9' 57.2(3) . . . . ?
C3' C4' C8' C9' -75.6(3) . . . . ?
C5' C4' C8' C10' -69.4(3) . . . . ?
C3' C4' C8' C10' 157.8(2) . . . . ?
C8AB N1B C2B O1B 178.3(2) . . . . ?
C9B N1B C2B O1B 0.1(4) . . . . ?
C8AB N1B C2B C3B -1.1(4) . . . . ?
C9B N1B C2B C3B -179.3(3) . . . . ?
O1B C2B C3B C4B -176.8(2) . . . . ?
N1B C2B C3B C4B 2.6(3) . . . . ?
O1B C2B C3B C3'B -1.3(4) . . . . ?
N1B C2B C3B C3'B 178.0(2) . . . . ?
C2B C3B C4B O2'B 176.2(2) . . . . ?
C3'B C3B C4B O2'B 0.9(4) . . . . ?
C2B C3B C4B C4AB -2.2(3) . . . . ?
C3'B C3B C4B C4AB -177.5(2) . . . . ?
O2'B C4B C4AB C5B 2.3(4) . . . . ?
C3B C4B C4AB C5B -179.1(2) . . . . ?
O2'B C4B C4AB C8AB -178.2(2) . . . . ?
C3B C4B C4AB C8AB 0.3(3) . . . . ?
C8AB C4AB C5B C6B -0.6(4) . . . . ?
C4B C4AB C5B C6B 178.9(3) . . . . ?
C4AB C5B C6B C7B -0.8(5) . . . . ?
C5B C6B C7B C8B 1.5(5) . . . . ?
C6B C7B C8B C8AB -0.8(5) . . . . ?
C2B N1B C8AB C4AB -0.8(4) . . . . ?
C9B N1B C8AB C4AB 177.4(3) . . . . ?
C2B N1B C8AB C8B 178.6(2) . . . . ?
C9B N1B C8AB C8B -3.3(4) . . . . ?
C5B C4AB C8AB N1B -179.3(2) . . . . ?
C4B C4AB C8AB N1B 1.2(3) . . . . ?
C5B C4AB C8AB C8B 1.3(4) . . . . ?
C4B C4AB C8AB C8B -178.2(2) . . . . ?
C7B C8B C8AB N1B -180.0(3) . . . . ?
C7B C8B C8AB C4AB -0.6(4) . . . . ?
O1'B C1'B C2'B C3'B 61.9(2) . . . . ?
C7'B C1'B C2'B C3'B -178.0(2) . . . . ?
C6'B C1'B C2'B C3'B -53.0(3) . . . . ?
O1'B C1'B C2'B Cl1B -170.28(15) . . . . ?
C7'B C1'B C2'B Cl1B -50.2(2) . . . . ?
C6'B C1'B C2'B Cl1B 74.8(2) . . . . ?
C3B C4B O2'B C8'B 10.8(4) . . . . ?
C4AB C4B O2'B C8'B -170.7(2) . . . . ?
C4B C3B C3'B C2'B -123.1(2) . . . . ?
C2B C3B C3'B C2'B 61.5(3) . . . . ?
C4B C3B C3'B C4'B 12.7(3) . . . . ?
C2B C3B C3'B C4'B -162.68(19) . . . . ?
C1'B C2'B C3'B C3B 176.84(18) . . . . ?
Cl1B C2'B C3'B C3B 50.0(2) . . . . ?
C1'B C2'B C3'B C4'B 44.5(3) . . . . ?
Cl1B C2'B C3'B C4'B -82.4(2) . . . . ?
C3B C3'B C4'B C5'B -171.81(19) . . . . ?
C2'B C3'B C4'B C5'B -37.9(3) . . . . ?
C3B C3'B C4'B C8'B -37.1(3) . . . . ?
C2'B C3'B C4'B C8'B 96.8(2) . . . . ?
C8'B C4'B C5'B C6'B -93.2(2) . . . . ?
C3'B C4'B C5'B C6'B 41.9(3) . . . . ?
O1'B C1'B C6'B C5'B -55.6(2) . . . . ?
C7'B C1'B C6'B C5'B -175.6(2) . . . . ?
C2'B C1'B C6'B C5'B 58.3(3) . . . . ?
C4'B C5'B C6'B C1'B -53.7(3) . . . . ?
C4B O2'B C8'B C9'B 95.5(3) . . . . ?
C4B O2'B C8'B C10B -149.8(2) . . . . ?
C4B O2'B C8'B C4'B -33.6(3) . . . . ?
C5'B C4'B C8'B O2'B -179.87(19) . . . . ?
C3'B C4'B C8'B O2'B 47.0(3) . . . . ?
C5'B C4'B C8'B C9'B 57.5(3) . . . . ?
C3'B C4'B C8'B C9'B -75.7(3) . . . . ?
C5'B C4'B C8'B C10B -68.9(3) . . . . ?
C3'B C4'B C8'B C10B 157.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 Cl1B 0.93 2.90 3.612(3) 134.8 2_656 yes
O1' H1' O1 0.78(4) 2.10(4) 2.872(3) 171(4) 2 yes
C2' H2' O1 0.98 2.39 2.993(3) 119.4 . yes
C9' H9C Cl1' 0.96 2.57 3.416(3) 146.6 . yes
O1'B H1'B O1B 0.85(3) 1.96(3) 2.811(3) 173(3) 2_656 yes
C2'B H2'B O1B 0.98 2.39 3.007(3) 120.6 . yes
C9'B H9'F Cl1B 0.96 2.53 3.353(3) 144.1 . yes

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.069






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ether/methanol'
####################################################################### 
# 
# 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_compound_15_FO5-94-10
_database_code_depnum_ccdc_archive 'CCDC 1589037'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H25 N O4'
_chemical_formula_sum            'C20 H25 N O4'
_chemical_formula_weight         343.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   17.0841(12)
_cell_length_b                   18.7193(11)
_cell_length_c                   11.1858(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.620(7)
_cell_angle_gamma                90
_cell_volume                     3516.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3296
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      68.0

_exptl_crystal_description       'elongated plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.729
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_process_details   'Reqab, Rigaku, 1998'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF Confocal mirror'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid 2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            18272
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.632
_diffrn_reflns_theta_max         65.825
_diffrn_reflns_theta_full        65.825
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             5900
_reflns_number_gt                4457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0566P)²+0.5346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5866
_refine_ls_number_parameters     471
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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 0.89785(6) 0.30540(6) 0.80424(12) 0.0423(3) Uani 1 1 d . . . . .
C1' C 0.64607(10) 0.14689(9) 0.78075(17) 0.0382(4) Uani 1 1 d . . . . .
O1 O 0.62652(7) 0.37149(7) 0.73368(14) 0.0533(4) Uani 1 1 d . . . . .
C3 C 0.75761(10) 0.32845(9) 0.75766(16) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.71590(8) 0.44411(7) 0.66662(14) 0.0404(4) Uani 1 1 d . . . . .
O1'B O 0.16386(6) 0.20192(6) 0.63262(12) 0.0418(3) Uani 1 1 d . . . . .
O3' O 0.68909(8) 0.20525(7) 0.60823(13) 0.0509(4) Uani 1 1 d . U . . .
H3'O H 0.6540(14) 0.1776(12) 0.574(2) 0.076 Uiso 1 1 d . U . . .
C2' C 0.66676(10) 0.21769(9) 0.72336(17) 0.0371(4) Uani 1 1 d . U . . .
H2' H 0.619721 0.248674 0.711295 0.045 Uiso 1 1 calc R U . . .
C2 C 0.69579(10) 0.38089(9) 0.71924(17) 0.0384(4) Uani 1 1 d . . . . .
O2' O 0.59573(8) 0.10742(7) 0.68502(13) 0.0492(4) Uani 1 1 d . . . . .
H2'O H 0.5457(13) 0.1180(12) 0.688(2) 0.074 Uiso 1 1 d . U . . .
C3' C 0.73608(9) 0.25686(9) 0.80526(17) 0.0351(4) Uani 1 1 d . . . . .
H3' H 0.720663 0.264928 0.884335 0.042 Uiso 1 1 calc R U . . .
C4 C 0.83427(10) 0.34687(9) 0.75826(16) 0.0361(4) Uani 1 1 d . . . . .
C4' C 0.80902(9) 0.20714(9) 0.82564(17) 0.0358(4) Uani 1 1 d . . . . .
H4' H 0.816669 0.191137 0.745172 0.043 Uiso 1 1 calc R U . . .
C5 C 0.93412(11) 0.43021(11) 0.7001(2) 0.0515(5) Uani 1 1 d . . . . .
H4 H 0.974938 0.399302 0.733524 0.062 Uiso 1 1 calc R U . . .
C6 C 0.95197(13) 0.49176(12) 0.6452(2) 0.0661(7) Uani 1 1 d . . . . .
H5 H 1.004481 0.502480 0.640563 0.079 Uiso 1 1 calc R U . . .
C5' C 0.78967(10) 0.14091(9) 0.89407(18) 0.0430(5) Uani 1 1 d . . . . .
H5'A H 0.835963 0.109969 0.910390 0.052 Uiso 1 1 calc R U . . .
H5'B H 0.776346 0.154942 0.971358 0.052 Uiso 1 1 calc R U . . .
O2'B O 0.46598(8) 0.39818(7) 0.65583(14) 0.0563(4) Uani 1 1 d . . . . .
H2'W H 0.5173(14) 0.3826(13) 0.673(2) 0.085 Uiso 1 1 d . U . . .
C6' C 0.72008(10) 0.10066(10) 0.81943(19) 0.0449(5) Uani 1 1 d . . . . .
H6'A H 0.706524 0.060648 0.866830 0.054 Uiso 1 1 calc R U . . .
H6'B H 0.736434 0.081537 0.747264 0.054 Uiso 1 1 calc R U . . .
C7 C 0.89118(14) 0.53801(12) 0.5965(2) 0.0679(7) Uani 1 1 d . . . . .
H6 H 0.903372 0.579784 0.558814 0.081 Uiso 1 1 calc R U . . .
C7' C 0.60212(11) 0.15993(10) 0.88511(19) 0.0489(5) Uani 1 1 d . . . . .
H7'A H 0.584079 0.115173 0.912025 0.073 Uiso 1 1 calc R U . . .
H7'B H 0.557160 0.190422 0.858073 0.073 Uiso 1 1 calc R U . . .
H7'C H 0.637342 0.182422 0.951173 0.073 Uiso 1 1 calc R U . . .
C8 C 0.81343(12) 0.52349(10) 0.6027(2) 0.0537(5) Uani 1 1 d . . . . .
H7 H 0.773496 0.555449 0.570027 0.064 Uiso 1 1 calc R U . . .
O3'B O 0.37055(8) 0.29958(8) 0.53274(13) 0.0576(4) Uani 1 1 d . . . . .
H3'W H 0.4100(14) 0.3360(12) 0.518(2) 0.086 Uiso 1 1 d . U . . .
C10' C 0.88261(12) 0.27632(11) 1.00867(18) 0.0533(5) Uani 1 1 d . . . . .
H10A H 0.881479 0.238009 1.065379 0.080 Uiso 1 1 calc R U . . .
H10B H 0.835700 0.305137 1.004542 0.080 Uiso 1 1 calc R U . . .
H10C H 0.929018 0.305192 1.035074 0.080 Uiso 1 1 calc R U . . .
N1B N 0.34096(8) 0.06131(7) 0.58391(14) 0.0412(4) Uani 1 1 d . . . . .
O1B O 0.43528(7) 0.13474(7) 0.68816(14) 0.0567(4) Uani 1 1 d . . . . .
C9 C 0.65199(11) 0.49550(10) 0.6225(2) 0.0536(5) Uani 1 1 d . . . . .
H8A H 0.665029 0.540955 0.660796 0.080 Uiso 1 1 calc R U . . .
H8AB H 0.602843 0.478495 0.642071 0.080 Uiso 1 1 calc R U . . .
H8AC H 0.646363 0.500601 0.535977 0.080 Uiso 1 1 calc R U . . .
C9' C 0.95880(11) 0.20010(11) 0.8865(2) 0.0547(6) Uani 1 1 d . . . . .
H9'A H 0.958284 0.161145 0.942195 0.082 Uiso 1 1 calc R U . . .
H9'B H 1.005550 0.228619 0.912408 0.082 Uiso 1 1 calc R U . . .
H9'C H 0.959162 0.181635 0.806560 0.082 Uiso 1 1 calc R U . . .
C4'B C 0.25487(9) 0.29963(9) 0.69477(17) 0.0364(4) Uani 1 1 d . . . . .
H4'B H 0.243016 0.314402 0.609288 0.044 Uiso 1 1 calc R U . . .
C4AB C 0.20185(10) 0.09295(9) 0.55742(17) 0.0395(4) Uani 1 1 d . . . . .
C3'B C 0.32758(9) 0.24970(9) 0.70914(17) 0.0361(4) Uani 1 1 d . . . . .
H3'B H 0.345884 0.241786 0.796422 0.043 Uiso 1 1 calc R U . . .
C8'B C 0.18136(10) 0.26046(9) 0.72060(17) 0.0392(4) Uani 1 1 d . . . . .
C1'B C 0.41756(10) 0.35934(9) 0.72599(19) 0.0423(5) Uani 1 1 d . . . . .
C8AB C 0.26128(11) 0.04484(9) 0.53956(17) 0.0406(4) Uani 1 1 d . . . . .
C2'B C 0.39516(10) 0.28813(10) 0.66062(18) 0.0416(5) Uani 1 1 d . . . . .
H2'B H 0.442189 0.257128 0.673570 0.050 Uiso 1 1 calc R U . . .
C5'B C 0.27686(10) 0.36699(10) 0.77002(19) 0.0467(5) Uani 1 1 d . . . . .
H5'C H 0.230794 0.398054 0.763010 0.056 Uiso 1 1 calc R U . . .
H5'D H 0.293512 0.354359 0.855012 0.056 Uiso 1 1 calc R U . . .
C6'B C 0.34422(11) 0.40590(10) 0.7250(2) 0.0491(5) Uani 1 1 d . . . . .
H6'C H 0.359325 0.447437 0.775849 0.059 Uiso 1 1 calc R U . . .
H6'D H 0.325068 0.422609 0.642699 0.059 Uiso 1 1 calc R U . . .
C7'B C 0.46359(11) 0.34686(10) 0.85451(19) 0.0512(5) Uani 1 1 d . . . . .
H7'D H 0.431037 0.320432 0.900315 0.077 Uiso 1 1 calc R U . . .
H7'E H 0.477592 0.392019 0.893279 0.077 Uiso 1 1 calc R U . . .
H7'F H 0.511149 0.320267 0.850898 0.077 Uiso 1 1 calc R U . . .
C8' C 0.88517(10) 0.24575(9) 0.88401(17) 0.0390(4) Uani 1 1 d . . . . .
C9'B C 0.19142(11) 0.22851(11) 0.84681(18) 0.0507(5) Uani 1 1 d . . . . .
H9'D H 0.199584 0.266080 0.906226 0.076 Uiso 1 1 calc R U . . .
H9'E H 0.236628 0.197114 0.859828 0.076 Uiso 1 1 calc R U . . .
H9'F H 0.144440 0.202075 0.854418 0.076 Uiso 1 1 calc R U . . .
C10" C 0.10721(10) 0.30667(11) 0.6935(2) 0.0532(5) Uani 1 1 d . . . . .
H10D H 0.109979 0.343117 0.754537 0.080 Uiso 1 1 calc R U . . .
H10E H 0.060967 0.277586 0.693817 0.080 Uiso 1 1 calc R U . . .
H10F H 0.103794 0.328533 0.615102 0.080 Uiso 1 1 calc R U . . .
C4A C 0.85541(10) 0.41300(9) 0.70677(17) 0.0386(4) Uani 1 1 d . . . . .
C2B C 0.36432(10) 0.12504(9) 0.64320(17) 0.0391(4) Uani 1 1 d . . . . .
C8A C 0.79414(10) 0.46041(9) 0.65823(17) 0.0394(4) Uani 1 1 d . . . . .
C8B C 0.23944(13) -0.01925(10) 0.4787(2) 0.0539(5) Uani 1 1 d . . . . .
H8B H 0.278270 -0.052244 0.468021 0.065 Uiso 1 1 calc R U . . .
C9B C 0.40311(12) 0.00860(10) 0.5728(2) 0.0552(6) Uani 1 1 d . . . . .
H9BA H 0.454141 0.026972 0.610627 0.083 Uiso 1 1 calc R U . . .
H9BB H 0.403084 -0.000538 0.488330 0.083 Uiso 1 1 calc R U . . .
H9BC H 0.392638 -0.035022 0.612140 0.083 Uiso 1 1 calc R U . . .
C7B C 0.16056(14) -0.03354(11) 0.4345(2) 0.0639(6) Uani 1 1 d . . . . .
H7B H 0.146698 -0.075797 0.392150 0.077 Uiso 1 1 calc R U . . .
C6B C 0.10146(13) 0.01351(12) 0.4517(2) 0.0617(6) Uani 1 1 d . . . . .
H6B H 0.048294 0.002885 0.421681 0.074 Uiso 1 1 calc R U . . .
C5B C 0.12181(11) 0.07606(11) 0.51329(19) 0.0515(5) Uani 1 1 d . . . . .
H5B H 0.082097 0.107627 0.525947 0.062 Uiso 1 1 calc R U . . .
C4B C 0.22586(10) 0.15975(9) 0.61744(16) 0.0368(4) Uani 1 1 d . . . . .
C3B C 0.30362(10) 0.17799(9) 0.65196(16) 0.0360(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' C4 1.3569(19) . ?
O1' C8' 1.470(2) . ?
C1' O2' 1.447(2) . ?
C1' C7' 1.520(3) . ?
C1' C6' 1.528(2) . ?
C1' C2' 1.542(2) . ?
O1 C2 1.2361(19) . ?
C3 C4 1.353(2) . ?
C3 C2 1.448(2) . ?
C3 C3' 1.512(2) . ?
N1 C8A 1.391(2) . ?
N1 C2 1.393(2) . ?
N1 C9 1.470(2) . ?
O1'B C4B 1.3565(19) . ?
O1'B C8'B 1.466(2) . ?
O3' C2' 1.428(2) . ?
O3' H3'O 0.83(2) . ?
C2' C3' 1.543(2) . ?
C2' H2' 0.9800 . ?
O2' H2'O 0.88(2) . ?
C3' C4' 1.538(2) . ?
C3' H3' 0.9800 . ?
C4 C4A 1.439(2) . ?
C4' C5' 1.525(2) . ?
C4' C8' 1.526(2) . ?
C4' H4' 0.9800 . ?
C5 C6 1.366(3) . ?
C5 C4A 1.398(2) . ?
C5 H4 0.9300 . ?
C6 C7 1.384(3) . ?
C6 H5 0.9300 . ?
C5' C6' 1.521(2) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
O2'B C1'B 1.438(2) . ?
O2'B H2'W 0.91(2) . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7 C8 1.370(3) . ?
C7 H6 0.9300 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8 C8A 1.402(3) . ?
C8 H7 0.9300 . ?
O3'B C2'B 1.431(2) . ?
O3'B H3'W 0.99(2) . ?
C10' C8' 1.515(3) . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
N1B C2B 1.387(2) . ?
N1B C8AB 1.395(2) . ?
N1B C9B 1.471(2) . ?
O1B C2B 1.237(2) . ?
C9 H8A 0.9600 . ?
C9 H8AB 0.9600 . ?
C9 H8AC 0.9600 . ?
C9' C8' 1.517(2) . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C4'B C5'B 1.524(2) . ?
C4'B C8'B 1.527(2) . ?
C4'B C3'B 1.539(2) . ?
C4'B H4'B 0.9800 . ?
C4AB C8AB 1.399(2) . ?
C4AB C5B 1.402(2) . ?
C4AB C4B 1.443(2) . ?
C3'B C3B 1.511(2) . ?
C3'B C2'B 1.542(2) . ?
C3'B H3'B 0.9800 . ?
C8'B C9'B 1.514(3) . ?
C8'B C10" 1.518(2) . ?
C1'B C7'B 1.524(3) . ?
C1'B C6'B 1.524(2) . ?
C1'B C2'B 1.535(2) . ?
C8AB C8B 1.396(2) . ?
C2'B H2'B 0.9800 . ?
C5'B C6'B 1.524(3) . ?
C5'B H5'C 0.9700 . ?
C5'B H5'D 0.9700 . ?
C6'B H6'C 0.9700 . ?
C6'B H6'D 0.9700 . ?
C7'B H7'D 0.9600 . ?
C7'B H7'E 0.9600 . ?
C7'B H7'F 0.9600 . ?
C9'B H9'D 0.9600 . ?
C9'B H9'E 0.9600 . ?
C9'B H9'F 0.9600 . ?
C10" H10D 0.9600 . ?
C10" H10E 0.9600 . ?
C10" H10F 0.9600 . ?
C4A C8A 1.403(2) . ?
C2B C3B 1.451(2) . ?
C8B C7B 1.373(3) . ?
C8B H8B 0.9300 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C7B C6B 1.380(3) . ?
C7B H7B 0.9300 . ?
C6B C5B 1.371(3) . ?
C6B H6B 0.9300 . ?
C5B H5B 0.9300 . ?
C4B C3B 1.357(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1' C8' 117.86(13) . . ?
O2' C1' C7' 109.89(14) . . ?
O2' C1' C6' 105.57(14) . . ?
C7' C1' C6' 111.95(16) . . ?
O2' C1' C2' 106.35(14) . . ?
C7' C1' C2' 111.44(14) . . ?
C6' C1' C2' 111.32(14) . . ?
C4 C3 C2 118.76(16) . . ?
C4 C3 C3' 121.47(15) . . ?
C2 C3 C3' 119.59(14) . . ?
C8A N1 C2 122.00(14) . . ?
C8A N1 C9 119.83(15) . . ?
C2 N1 C9 118.15(14) . . ?
C4B O1'B C8'B 116.84(12) . . ?
C2' O3' H3'O 103.0(17) . . ?
O3' C2' C1' 110.80(14) . . ?
O3' C2' C3' 108.04(14) . . ?
C1' C2' C3' 111.79(14) . . ?
O3' C2' H2' 108.7 . . ?
C1' C2' H2' 108.7 . . ?
C3' C2' H2' 108.7 . . ?
O1 C2 N1 119.53(16) . . ?
O1 C2 C3 121.89(16) . . ?
N1 C2 C3 118.57(15) . . ?
C1' O2' H2'O 107.7(15) . . ?
C3 C3' C4' 110.21(13) . . ?
C3 C3' C2' 114.96(14) . . ?
C4' C3' C2' 108.22(13) . . ?
C3 C3' H3' 107.7 . . ?
C4' C3' H3' 107.7 . . ?
C2' C3' H3' 107.7 . . ?
C3 C4 O1' 124.24(15) . . ?
C3 C4 C4A 122.09(15) . . ?
O1' C4 C4A 113.66(14) . . ?
C5' C4' C8' 114.64(14) . . ?
C5' C4' C3' 108.77(14) . . ?
C8' C4' C3' 112.36(14) . . ?
C5' C4' H4' 106.9 . . ?
C8' C4' H4' 106.9 . . ?
C3' C4' H4' 106.9 . . ?
C6 C5 C4A 121.00(19) . . ?
C6 C5 H4 119.5 . . ?
C4A C5 H4 119.5 . . ?
C5 C6 C7 119.40(19) . . ?
C5 C6 H5 120.3 . . ?
C7 C6 H5 120.3 . . ?
C6' C5' C4' 110.31(15) . . ?
C6' C5' H5'A 109.6 . . ?
C4' C5' H5'A 109.6 . . ?
C6' C5' H5'B 109.6 . . ?
C4' C5' H5'B 109.6 . . ?
H5'A C5' H5'B 108.1 . . ?
C1'B O2'B H2'W 110.6(16) . . ?
C5' C6' C1' 113.42(15) . . ?
C5' C6' H6'A 108.9 . . ?
C1' C6' H6'A 108.9 . . ?
C5' C6' H6'B 108.9 . . ?
C1' C6' H6'B 108.9 . . ?
H6'A C6' H6'B 107.7 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H6 119.3 . . ?
C6 C7 H6 119.3 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C7 C8 C8A 119.93(19) . . ?
C7 C8 H7 120.0 . . ?
C8A C8 H7 120.0 . . ?
C2'B O3'B H3'W 100.8(14) . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C2B N1B C8AB 122.42(14) . . ?
C2B N1B C9B 117.94(15) . . ?
C8AB N1B C9B 119.59(15) . . ?
N1 C9 H8A 109.5 . . ?
N1 C9 H8AB 109.5 . . ?
H8A C9 H8AB 109.5 . . ?
N1 C9 H8AC 109.5 . . ?
H8A C9 H8AC 109.5 . . ?
H8AB C9 H8AC 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C5'B C4'B C8'B 114.85(15) . . ?
C5'B C4'B C3'B 109.42(13) . . ?
C8'B C4'B C3'B 111.40(14) . . ?
C5'B C4'B H4'B 106.9 . . ?
C8'B C4'B H4'B 106.9 . . ?
C3'B C4'B H4'B 106.9 . . ?
C8AB C4AB C5B 119.41(17) . . ?
C8AB C4AB C4B 118.23(15) . . ?
C5B C4AB C4B 122.32(17) . . ?
C3B C3'B C4'B 110.17(13) . . ?
C3B C3'B C2'B 115.32(15) . . ?
C4'B C3'B C2'B 108.81(14) . . ?
C3B C3'B H3'B 107.4 . . ?
C4'B C3'B H3'B 107.4 . . ?
C2'B C3'B H3'B 107.4 . . ?
O1'B C8'B C9'B 107.74(15) . . ?
O1'B C8'B C10" 103.45(14) . . ?
C9'B C8'B C10" 111.01(16) . . ?
O1'B C8'B C4'B 107.76(14) . . ?
C9'B C8'B C4'B 114.22(15) . . ?
C10" C8'B C4'B 111.96(15) . . ?
O2'B C1'B C7'B 110.09(14) . . ?
O2'B C1'B C6'B 105.16(15) . . ?
C7'B C1'B C6'B 112.04(17) . . ?
O2'B C1'B C2'B 107.28(15) . . ?
C7'B C1'B C2'B 110.88(15) . . ?
C6'B C1'B C2'B 111.14(14) . . ?
N1B C8AB C8B 121.28(17) . . ?
N1B C8AB C4AB 119.56(16) . . ?
C8B C8AB C4AB 119.16(17) . . ?
O3'B C2'B C1'B 110.36(15) . . ?
O3'B C2'B C3'B 108.71(14) . . ?
C1'B C2'B C3'B 112.01(15) . . ?
O3'B C2'B H2'B 108.6 . . ?
C1'B C2'B H2'B 108.6 . . ?
C3'B C2'B H2'B 108.6 . . ?
C6'B C5'B C4'B 109.70(16) . . ?
C6'B C5'B H5'C 109.7 . . ?
C4'B C5'B H5'C 109.7 . . ?
C6'B C5'B H5'D 109.7 . . ?
C4'B C5'B H5'D 109.7 . . ?
H5'C C5'B H5'D 108.2 . . ?
C5'B C6'B C1'B 113.20(15) . . ?
C5'B C6'B H6'C 108.9 . . ?
C1'B C6'B H6'C 108.9 . . ?
C5'B C6'B H6'D 108.9 . . ?
C1'B C6'B H6'D 108.9 . . ?
H6'C C6'B H6'D 107.8 . . ?
C1'B C7'B H7'D 109.5 . . ?
C1'B C7'B H7'E 109.5 . . ?
H7'D C7'B H7'E 109.5 . . ?
C1'B C7'B H7'F 109.5 . . ?
H7'D C7'B H7'F 109.5 . . ?
H7'E C7'B H7'F 109.5 . . ?
O1' C8' C10' 107.71(15) . . ?
O1' C8' C9' 102.99(14) . . ?
C10' C8' C9' 111.12(16) . . ?
O1' C8' C4' 108.03(13) . . ?
C10' C8' C4' 113.93(15) . . ?
C9' C8' C4' 112.33(15) . . ?
C8'B C9'B H9'D 109.5 . . ?
C8'B C9'B H9'E 109.5 . . ?
H9'D C9'B H9'E 109.5 . . ?
C8'B C9'B H9'F 109.5 . . ?
H9'D C9'B H9'F 109.5 . . ?
H9'E C9'B H9'F 109.5 . . ?
C8'B C10" H10D 109.5 . . ?
C8'B C10" H10E 109.5 . . ?
H10D C10" H10E 109.5 . . ?
C8'B C10" H10F 109.5 . . ?
H10D C10" H10F 109.5 . . ?
H10E C10" H10F 109.5 . . ?
C5 C4A C8A 119.33(17) . . ?
C5 C4A C4 122.31(16) . . ?
C8A C4A C4 118.33(15) . . ?
O1B C2B N1B 119.63(16) . . ?
O1B C2B C3B 122.10(17) . . ?
N1B C2B C3B 118.26(15) . . ?
N1 C8A C8 121.47(16) . . ?
N1 C8A C4A 119.53(16) . . ?
C8 C8A C4A 119.00(17) . . ?
C7B C8B C8AB 119.95(19) . . ?
C7B C8B H8B 120.0 . . ?
C8AB C8B H8B 120.0 . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8B C7B C6B 121.4(2) . . ?
C8B C7B H7B 119.3 . . ?
C6B C7B H7B 119.3 . . ?
C5B C6B C7B 119.41(19) . . ?
C5B C6B H6B 120.3 . . ?
C7B C6B H6B 120.3 . . ?
C6B C5B C4AB 120.69(19) . . ?
C6B C5B H5B 119.7 . . ?
C4AB C5B H5B 119.7 . . ?
O1'B C4B C3B 124.35(16) . . ?
O1'B C4B C4AB 113.64(14) . . ?
C3B C4B C4AB 122.00(16) . . ?
C4B C3B C2B 118.91(16) . . ?
C4B C3B C3'B 121.24(15) . . ?
C2B C3B C3'B 119.63(14) . . ?

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
O2' C1' C2' O3' -45.42(17) . . . . ?
C7' C1' C2' O3' -165.16(14) . . . . ?
C6' C1' C2' O3' 69.09(18) . . . . ?
O2' C1' C2' C3' -165.98(14) . . . . ?
C7' C1' C2' C3' 74.27(18) . . . . ?
C6' C1' C2' C3' -51.5(2) . . . . ?
C8A N1 C2 O1 174.03(17) . . . . ?
C9 N1 C2 O1 -4.0(3) . . . . ?
C8A N1 C2 C3 -4.8(3) . . . . ?
C9 N1 C2 C3 177.10(16) . . . . ?
C4 C3 C2 O1 -168.94(18) . . . . ?
C3' C3 C2 O1 6.3(3) . . . . ?
C4 C3 C2 N1 9.9(3) . . . . ?
C3' C3 C2 N1 -174.88(16) . . . . ?
C4 C3 C3' C4' -11.7(2) . . . . ?
C2 C3 C3' C4' 173.19(15) . . . . ?
C4 C3 C3' C2' -134.32(17) . . . . ?
C2 C3 C3' C2' 50.6(2) . . . . ?
O3' C2' C3' C3 60.35(18) . . . . ?
C1' C2' C3' C3 -177.48(14) . . . . ?
O3' C2' C3' C4' -63.31(17) . . . . ?
C1' C2' C3' C4' 58.85(18) . . . . ?
C2 C3 C4 O1' 172.70(16) . . . . ?
C3' C3 C4 O1' -2.4(3) . . . . ?
C2 C3 C4 C4A -8.6(3) . . . . ?
C3' C3 C4 C4A 176.26(16) . . . . ?
C8' O1' C4 C3 -15.5(2) . . . . ?
C8' O1' C4 C4A 165.68(15) . . . . ?
C3 C3' C4' C5' 170.11(15) . . . . ?
C2' C3' C4' C5' -63.40(18) . . . . ?
C3 C3' C4' C8' 42.1(2) . . . . ?
C2' C3' C4' C8' 168.58(15) . . . . ?
C4A C5 C6 C7 0.6(4) . . . . ?
C8' C4' C5' C6' -171.75(15) . . . . ?
C3' C4' C5' C6' 61.53(19) . . . . ?
C4' C5' C6' C1' -54.8(2) . . . . ?
O2' C1' C6' C5' 164.25(16) . . . . ?
C7' C1' C6' C5' -76.2(2) . . . . ?
C2' C1' C6' C5' 49.3(2) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C8A -0.6(4) . . . . ?
C5'B C4'B C3'B C3B 170.96(15) . . . . ?
C8'B C4'B C3'B C3B 42.9(2) . . . . ?
C5'B C4'B C3'B C2'B -61.70(19) . . . . ?
C8'B C4'B C3'B C2'B 170.21(15) . . . . ?
C4B O1'B C8'B C9'B -75.85(18) . . . . ?
C4B O1'B C8'B C10" 166.54(15) . . . . ?
C4B O1'B C8'B C4'B 47.84(19) . . . . ?
C5'B C4'B C8'B O1'B 174.20(14) . . . . ?
C3'B C4'B C8'B O1'B -60.69(19) . . . . ?
C5'B C4'B C8'B C9'B -66.1(2) . . . . ?
C3'B C4'B C8'B C9'B 59.0(2) . . . . ?
C5'B C4'B C8'B C10" 61.1(2) . . . . ?
C3'B C4'B C8'B C10" -173.79(15) . . . . ?
C2B N1B C8AB C8B 179.07(18) . . . . ?
C9B N1B C8AB C8B -3.6(3) . . . . ?
C2B N1B C8AB C4AB -1.7(3) . . . . ?
C9B N1B C8AB C4AB 175.72(17) . . . . ?
C5B C4AB C8AB N1B -179.67(17) . . . . ?
C4B C4AB C8AB N1B 2.5(3) . . . . ?
C5B C4AB C8AB C8B -0.4(3) . . . . ?
C4B C4AB C8AB C8B -178.24(17) . . . . ?
O2'B C1'B C2'B O3'B -45.09(18) . . . . ?
C7'B C1'B C2'B O3'B -165.33(15) . . . . ?
C6'B C1'B C2'B O3'B 69.4(2) . . . . ?
O2'B C1'B C2'B C3'B -166.35(14) . . . . ?
C7'B C1'B C2'B C3'B 73.41(19) . . . . ?
C6'B C1'B C2'B C3'B -51.9(2) . . . . ?
C3B C3'B C2'B O3'B 59.54(19) . . . . ?
C4'B C3'B C2'B O3'B -64.81(18) . . . . ?
C3B C3'B C2'B C1'B -178.26(14) . . . . ?
C4'B C3'B C2'B C1'B 57.40(19) . . . . ?
C8'B C4'B C5'B C6'B -172.95(15) . . . . ?
C3'B C4'B C5'B C6'B 60.9(2) . . . . ?
C4'B C5'B C6'B C1'B -56.1(2) . . . . ?
O2'B C1'B C6'B C5'B 167.00(16) . . . . ?
C7'B C1'B C6'B C5'B -73.4(2) . . . . ?
C2'B C1'B C6'B C5'B 51.2(2) . . . . ?
C4 O1' C8' C10' -78.61(18) . . . . ?
C4 O1' C8' C9' 163.89(15) . . . . ?
C4 O1' C8' C4' 44.87(19) . . . . ?
C5' C4' C8' O1' 176.79(14) . . . . ?
C3' C4' C8' O1' -58.36(18) . . . . ?
C5' C4' C8' C10' -63.6(2) . . . . ?
C3' C4' C8' C10' 61.3(2) . . . . ?
C5' C4' C8' C9' 63.9(2) . . . . ?
C3' C4' C8' C9' -171.27(16) . . . . ?
C6 C5 C4A C8A -1.2(3) . . . . ?
C6 C5 C4A C4 176.7(2) . . . . ?
C3 C4 C4A C5 -175.77(18) . . . . ?
O1' C4 C4A C5 3.1(3) . . . . ?
C3 C4 C4A C8A 2.1(3) . . . . ?
O1' C4 C4A C8A -179.07(15) . . . . ?
C8AB N1B C2B O1B 174.95(17) . . . . ?
C9B N1B C2B O1B -2.5(3) . . . . ?
C8AB N1B C2B C3B -4.0(3) . . . . ?
C9B N1B C2B C3B 178.54(17) . . . . ?
C2 N1 C8A C8 178.58(18) . . . . ?
C9 N1 C8A C8 -3.4(3) . . . . ?
C2 N1 C8A C4A -1.7(3) . . . . ?
C9 N1 C8A C4A 176.36(17) . . . . ?
C7 C8 C8A N1 179.7(2) . . . . ?
C7 C8 C8A C4A 0.0(3) . . . . ?
C5 C4A C8A N1 -178.85(17) . . . . ?
C4 C4A C8A N1 3.2(3) . . . . ?
C5 C4A C8A C8 0.9(3) . . . . ?
C4 C4A C8A C8 -177.05(17) . . . . ?
N1B C8AB C8B C7B -179.08(19) . . . . ?
C4AB C8AB C8B C7B 1.6(3) . . . . ?
C8AB C8B C7B C6B -1.7(3) . . . . ?
C8B C7B C6B C5B 0.5(4) . . . . ?
C7B C6B C5B C4AB 0.8(3) . . . . ?
C8AB C4AB C5B C6B -0.9(3) . . . . ?
C4B C4AB C5B C6B 176.90(19) . . . . ?
C8'B O1'B C4B C3B -17.8(3) . . . . ?
C8'B O1'B C4B C4AB 163.66(15) . . . . ?
C8AB C4AB C4B O1'B -178.69(16) . . . . ?
C5B C4AB C4B O1'B 3.5(3) . . . . ?
C8AB C4AB C4B C3B 2.7(3) . . . . ?
C5B C4AB C4B C3B -175.06(18) . . . . ?
O1'B C4B C3B C2B 173.13(17) . . . . ?
C4AB C4B C3B C2B -8.4(3) . . . . ?
O1'B C4B C3B C3'B -1.5(3) . . . . ?
C4AB C4B C3B C3'B 176.96(16) . . . . ?
O1B C2B C3B C4B -169.96(18) . . . . ?
N1B C2B C3B C4B 9.0(3) . . . . ?
O1B C2B C3B C3'B 4.7(3) . . . . ?
N1B C2B C3B C3'B -176.30(15) . . . . ?
C4'B C3'B C3B C4B -12.0(2) . . . . ?
C2'B C3'B C3B C4B -135.68(18) . . . . ?
C4'B C3'B C3B C2B 173.39(16) . . . . ?
C2'B C3'B C3B C2B 49.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3' H3'O O2' 0.83(2) 2.17(2) 2.6722(19) 119(2) . yes
C2' H2' O1 0.98 2.31 2.967(2) 123.3 . yes
O2' H2'O O1B 0.88(2) 1.91(2) 2.7951(18) 176(2) . yes
O2'B H2'W O1 0.91(2) 1.88(2) 2.7658(18) 165(2) . yes
O3'B H3'W O2'B 0.99(2) 2.03(2) 2.671(2) 120.3(19) . yes
C2'B H2'B O1B 0.98 2.30 2.955(2) 123.3 . yes
C9B H9BC O1 0.96 2.52 3.455(3) 164.4 2_646 yes

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046








_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ether/methanol'
####################################################################### 
# 
# 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_compound_17
_database_code_depnum_ccdc_archive 'CCDC 1589039'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Cl N O5'
_chemical_formula_sum            'C20 H24 Cl N O5'
_chemical_formula_weight         393.85

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3027(5)
_cell_length_b                   7.2512(2)
_cell_length_c                   23.1020(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.784(7)
_cell_angle_gamma                90
_cell_volume                     1871.19(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      68.1

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    2.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_process_details   'Reqab (Higashi,Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'OSMIC CMF Confocal'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            9812
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.872
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3350
_reflns_number_gt                2563
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0621P)²+0.2619P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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_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
N1 N 0.66926(15) 0.5990(2) 0.64851(8) 0.0366(5) Uani 1 1 d . . . . .
O1 O 0.57952(13) 0.6258(2) 0.55384(7) 0.0460(4) Uani 1 1 d . . . . .
Cl1 Cl 0.45313(4) 0.87822(7) 0.65581(2) 0.03760(18) Uani 1 1 d . . . . .
C2 C 0.57318(18) 0.6208(3) 0.60623(9) 0.0331(5) Uani 1 1 d . . . . .
O2 O 0.47077(13) 0.3269(2) 0.65751(7) 0.0393(4) Uani 1 1 d . . . . .
H2O H 0.437(2) 0.323(4) 0.6244(11) 0.059 Uiso 1 1 d . U . . .
C3 C 0.45227(17) 0.6448(3) 0.62794(9) 0.0287(5) Uani 1 1 d . . . . .
C4 C 0.44790(16) 0.5055(3) 0.67830(9) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.5385(2) 0.5478(3) 0.78502(9) 0.0410(6) Uani 1 1 d . . . . .
H5 H 0.465010 0.520442 0.796418 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6364(2) 0.5876(3) 0.82694(11) 0.0514(7) Uani 1 1 d . . . . .
H6 H 0.628459 0.588673 0.866411 0.062 Uiso 1 1 calc R U . . .
C7 C 0.7458(2) 0.6256(3) 0.81006(12) 0.0538(7) Uani 1 1 d . . . . .
H7 H 0.811848 0.649407 0.838309 0.065 Uiso 1 1 calc R U . . .
C8 C 0.7576(2) 0.6285(3) 0.75162(10) 0.0441(6) Uani 1 1 d . . . . .
H8 H 0.831559 0.654643 0.740542 0.053 Uiso 1 1 calc R U . . .
C9 C 0.78816(19) 0.5848(3) 0.63033(11) 0.0491(7) Uani 1 1 d . . . . .
H9A H 0.832819 0.487814 0.651918 0.074 Uiso 1 1 calc R U . . .
H9AB H 0.830074 0.699509 0.638003 0.074 Uiso 1 1 calc R U . . .
H9AC H 0.779168 0.557964 0.589198 0.074 Uiso 1 1 calc R U . . .
C1' C 0.2220(2) 0.8634(3) 0.50864(10) 0.0425(6) Uani 1 1 d . . . . .
O1' O 0.27485(15) 0.7219(2) 0.47604(6) 0.0516(5) Uani 1 1 d . . . . .
C2' C 0.33530(19) 0.7741(3) 0.53324(9) 0.0381(5) Uani 1 1 d . . . . .
H2' H 0.407636 0.849064 0.533908 0.046 Uiso 1 1 calc R U . . .
O2' O 0.34765(13) 0.4441(2) 0.55468(6) 0.0376(4) Uani 1 1 d . . . . .
H2'O H 0.379(2) 0.445(4) 0.5262(11) 0.056 Uiso 1 1 d . U . . .
C3' C 0.34143(17) 0.6229(3) 0.58010(9) 0.0306(5) Uani 1 1 d . . . . .
O3' O 0.34070(11) 0.5144(2) 0.70125(5) 0.0366(4) Uani 1 1 d . . . . .
C4' C 0.22831(17) 0.6324(3) 0.60999(9) 0.0346(5) Uani 1 1 d . . . . .
H4' H 0.227901 0.756585 0.626665 0.041 Uiso 1 1 calc R U . . .
C5' C 0.11786(19) 0.6230(3) 0.56228(10) 0.0437(6) Uani 1 1 d . . . . .
H5'A H 0.125840 0.521251 0.535901 0.052 Uiso 1 1 calc R U . . .
H5'B H 0.046470 0.602990 0.580011 0.052 Uiso 1 1 calc R U . . .
C6' C 0.1074(2) 0.8038(4) 0.52852(11) 0.0551(7) Uani 1 1 d . . . . .
H6'A H 0.046058 0.790993 0.494486 0.066 Uiso 1 1 calc R U . . .
H6'B H 0.081736 0.899599 0.553167 0.066 Uiso 1 1 calc R U . . .
C7' C 0.2257(3) 1.0544(4) 0.48435(11) 0.0601(7) Uani 1 1 d . . . . .
H7'A H 0.224093 1.142587 0.515199 0.090 Uiso 1 1 calc R U . . .
H7'B H 0.157609 1.073010 0.454603 0.090 Uiso 1 1 calc R U . . .
H7'C H 0.297838 1.069917 0.467669 0.090 Uiso 1 1 calc R U . . .
C8' C 0.22657(17) 0.4990(4) 0.66172(9) 0.0393(6) Uani 1 1 d . . . . .
C9' C 0.1979(2) 0.2994(4) 0.64502(10) 0.0526(7) Uani 1 1 d . . . . .
H9'A H 0.116382 0.290291 0.626112 0.079 Uiso 1 1 calc R U . . .
H9'B H 0.208931 0.224261 0.679641 0.079 Uiso 1 1 calc R U . . .
H9'C H 0.250372 0.257532 0.618750 0.079 Uiso 1 1 calc R U . . .
C10' C 0.1384(2) 0.5687(5) 0.70072(10) 0.0613(8) Uani 1 1 d . . . . .
H10A H 0.058998 0.569298 0.678898 0.092 Uiso 1 1 calc R U . . .
H10B H 0.160046 0.691643 0.713707 0.092 Uiso 1 1 calc R U . . .
H10C H 0.140781 0.489072 0.734070 0.092 Uiso 1 1 calc R U . . .
C4A C 0.54971(17) 0.5487(3) 0.72636(9) 0.0329(5) Uani 1 1 d . . . . .
C8A C 0.66004(18) 0.5927(3) 0.70945(10) 0.0361(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.354(3) . ?
N1 C8A 1.428(3) . ?
N1 C9 1.472(2) . ?
O1 C2 1.224(2) . ?
Cl1 C3 1.810(2) . ?
C2 C3 1.536(3) . ?
O2 C4 1.418(3) . ?
O2 H2O 0.80(2) . ?
C3 C3' 1.547(3) . ?
C3 C4 1.547(3) . ?
C4 O3' 1.396(2) . ?
C4 C4A 1.505(3) . ?
C5 C4A 1.380(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C8A 1.380(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9AB 0.9600 . ?
C9 H9AC 0.9600 . ?
C1' O1' 1.454(3) . ?
C1' C2' 1.470(3) . ?
C1' C7' 1.497(3) . ?
C1' C6' 1.502(3) . ?
O1' C2' 1.442(2) . ?
C2' C3' 1.535(3) . ?
C2' H2' 0.9800 . ?
O2' C3' 1.429(2) . ?
O2' H2'O 0.79(2) . ?
C3' C4' 1.545(3) . ?
O3' C8' 1.466(2) . ?
C4' C5' 1.535(3) . ?
C4' C8' 1.540(3) . ?
C4' H4' 0.9800 . ?
C5' C6' 1.521(3) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' C9' 1.520(4) . ?
C8' C10' 1.528(3) . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C4A C8A 1.399(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
C2 N1 C8A 122.92(17) . . ?
C2 N1 C9 117.96(18) . . ?
C8A N1 C9 119.11(18) . . ?
O1 C2 N1 123.72(19) . . ?
O1 C2 C3 120.60(19) . . ?
N1 C2 C3 115.66(17) . . ?
C4 O2 H2O 106(2) . . ?
C2 C3 C3' 114.76(16) . . ?
C2 C3 C4 107.67(16) . . ?
C3' C3 C4 110.77(16) . . ?
C2 C3 Cl1 105.40(13) . . ?
C3' C3 Cl1 108.06(14) . . ?
C4 C3 Cl1 110.01(14) . . ?
O3' C4 O2 112.62(16) . . ?
O3' C4 C4A 108.68(16) . . ?
O2 C4 C4A 106.35(16) . . ?
O3' C4 C3 112.59(16) . . ?
O2 C4 C3 108.26(16) . . ?
C4A C4 C3 108.07(16) . . ?
C4A C5 C6 120.1(2) . . ?
C4A C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
N1 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
O1' C1' C2' 59.12(13) . . ?
O1' C1' C7' 114.9(2) . . ?
C2' C1' C7' 118.7(2) . . ?
O1' C1' C6' 113.4(2) . . ?
C2' C1' C6' 119.8(2) . . ?
C7' C1' C6' 117.1(2) . . ?
C2' O1' C1' 60.98(13) . . ?
O1' C2' C1' 59.89(13) . . ?
O1' C2' C3' 115.02(18) . . ?
C1' C2' C3' 122.02(19) . . ?
O1' C2' H2' 115.9 . . ?
C1' C2' H2' 115.9 . . ?
C3' C2' H2' 115.9 . . ?
C3' O2' H2'O 113(2) . . ?
O2' C3' C2' 110.97(16) . . ?
O2' C3' C4' 108.66(16) . . ?
C2' C3' C4' 109.40(16) . . ?
O2' C3' C3 107.55(16) . . ?
C2' C3' C3 112.01(17) . . ?
C4' C3' C3 108.13(16) . . ?
C4 O3' C8' 119.46(14) . . ?
C5' C4' C8' 115.10(17) . . ?
C5' C4' C3' 108.36(17) . . ?
C8' C4' C3' 115.38(17) . . ?
C5' C4' H4' 105.7 . . ?
C8' C4' H4' 105.7 . . ?
C3' C4' H4' 105.7 . . ?
C6' C5' C4' 108.73(19) . . ?
C6' C5' H5'A 109.9 . . ?
C4' C5' H5'A 109.9 . . ?
C6' C5' H5'B 109.9 . . ?
C4' C5' H5'B 109.9 . . ?
H5'A C5' H5'B 108.3 . . ?
C1' C6' C5' 113.7(2) . . ?
C1' C6' H6'A 108.8 . . ?
C5' C6' H6'A 108.8 . . ?
C1' C6' H6'B 108.8 . . ?
C5' C6' H6'B 108.8 . . ?
H6'A C6' H6'B 107.7 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
O3' C8' C9' 111.32(19) . . ?
O3' C8' C10' 101.45(17) . . ?
C9' C8' C10' 109.4(2) . . ?
O3' C8' C4' 108.74(16) . . ?
C9' C8' C4' 115.36(18) . . ?
C10' C8' C4' 109.7(2) . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C5 C4A C8A 119.65(19) . . ?
C5 C4A C4 123.28(19) . . ?
C8A C4A C4 117.07(18) . . ?
C8 C8A C4A 119.7(2) . . ?
C8 C8A N1 121.3(2) . . ?
C4A C8A N1 118.99(18) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.058






_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ether/methanol'
####################################################################### 
# 
# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1554994'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(6aS,9R,10R,10aS)-10-chloro-9-hydroxy-6,6,9,12-tetramethyl-6,6a,7,8,9,10,10a,12-octahydro-11H-isochromeno[4,3-c]quinolin-11-one)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Cl N O3'
_chemical_formula_sum            'C20 H24 Cl N O3'
_chemical_formula_weight         361.85

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'
Cl Cl 0.3639 0.7018 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5080(2)
_cell_length_b                   11.2397(3)
_cell_length_c                   21.9828(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1855.08(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5010
_cell_measurement_theta_min      3.9
_cell_measurement_theta_max      71.7

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.971
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_process_details   'Reqab (Higashi, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode'
_diffrn_measurement_device_type  
'Rigaku rotating anode diffractometer mm007HF Rapid2'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10037
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.022
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3348
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.981

_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_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)+(0.0150P)²+2.0034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
Cl1' Cl 0.1917(3) 0.51856(17) 0.36830(8) 0.0663(6) Uani 1 1 d . . . . .
O2' O 0.6521(7) 0.6593(3) 0.47755(18) 0.0492(12) Uani 1 1 d . . . . .
O1 O 0.5788(7) 0.3253(4) 0.3473(2) 0.0604(15) Uani 1 1 d . . . . .
O1' O 0.4853(7) 0.6239(5) 0.2283(2) 0.0636(15) Uani 1 1 d . . . . .
H1' H 0.475257 0.672523 0.200675 0.095 Uiso 1 1 calc R U . . .
N1 N 0.6221(8) 0.2980(4) 0.4491(2) 0.0513(16) Uani 1 1 d . . . . .
C3 C 0.5875(9) 0.4992(5) 0.4090(3) 0.0439(16) Uani 1 1 d . . . . .
C4 C 0.6313(9) 0.5411(5) 0.4647(3) 0.0426(16) Uani 1 1 d . . . . .
C4A C 0.6511(9) 0.4653(5) 0.5169(3) 0.0434(16) Uani 1 1 d . . . . .
C8A C 0.6421(10) 0.3424(5) 0.5075(3) 0.0450(16) Uani 1 1 d . . . . .
C8' C 0.6618(10) 0.7406(5) 0.4256(3) 0.0455(17) Uani 1 1 d . . . . .
C2 C 0.5946(10) 0.3707(5) 0.3990(3) 0.0451(17) Uani 1 1 d . . . . .
C3' C 0.5420(9) 0.5817(5) 0.3569(3) 0.0450(17) Uani 1 1 d . . . . .
H3' H 0.645308 0.583746 0.329667 0.054 Uiso 1 1 calc R U . . .
C1' C 0.3338(11) 0.6328(6) 0.2684(3) 0.0547(19) Uani 1 1 d . . . . .
C4' C 0.5158(9) 0.7073(5) 0.3816(3) 0.0425(16) Uani 1 1 d . . . . .
H4' H 0.405039 0.705769 0.405201 0.051 Uiso 1 1 calc R U . . .
C2' C 0.3801(9) 0.5419(6) 0.3187(3) 0.0497(18) Uani 1 1 d . . . . .
H2' H 0.409346 0.465963 0.299191 0.060 Uiso 1 1 calc R U . . .
C5 C 0.6754(9) 0.5107(6) 0.5758(3) 0.0519(17) Uani 1 1 d . . . . .
H5 H 0.683316 0.592366 0.581848 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6555(11) 0.2660(6) 0.5582(3) 0.0567(19) Uani 1 1 d . . . . .
H8 H 0.648144 0.184031 0.553018 0.068 Uiso 1 1 calc R U . . .
C7 C 0.6793(11) 0.3130(6) 0.6153(3) 0.060(2) Uani 1 1 d . . . . .
H7 H 0.690150 0.262043 0.648428 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6874(10) 0.4343(6) 0.6246(3) 0.0572(19) Uani 1 1 d . . . . .
H6 H 0.701073 0.464408 0.663718 0.069 Uiso 1 1 calc R U . . .
C6' C 0.3202(11) 0.7583(6) 0.2937(3) 0.057(2) Uani 1 1 d . . . . .
H6'A H 0.216827 0.763443 0.320013 0.069 Uiso 1 1 calc R U . . .
H6'B H 0.302821 0.813580 0.260294 0.069 Uiso 1 1 calc R U . . .
C5' C 0.4854(10) 0.7950(6) 0.3295(3) 0.0536(19) Uani 1 1 d . . . . .
H5'A H 0.469573 0.874597 0.345638 0.064 Uiso 1 1 calc R U . . .
H5'B H 0.588389 0.795574 0.302822 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6350(11) 0.1687(5) 0.4381(3) 0.062(2) Uani 1 1 d . . . . .
H9A H 0.747312 0.139921 0.452905 0.093 Uiso 1 1 calc R U . . .
H9B H 0.626139 0.153343 0.395236 0.093 Uiso 1 1 calc R U . . .
H9C H 0.539943 0.128712 0.458957 0.093 Uiso 1 1 calc R U . . .
C10' C 0.6372(12) 0.8629(5) 0.4546(3) 0.063(2) Uani 1 1 d . . . . .
H10A H 0.519064 0.869030 0.470966 0.094 Uiso 1 1 calc R U . . .
H10B H 0.654404 0.923469 0.424338 0.094 Uiso 1 1 calc R U . . .
H10C H 0.722679 0.873122 0.486621 0.094 Uiso 1 1 calc R U . . .
C9' C 0.8495(10) 0.7306(6) 0.3986(3) 0.063(2) Uani 1 1 d . . . . .
H9'A H 0.935660 0.753195 0.428762 0.095 Uiso 1 1 calc R U . . .
H9'B H 0.859519 0.782250 0.364042 0.095 Uiso 1 1 calc R U . . .
H9'C H 0.870916 0.649920 0.386236 0.095 Uiso 1 1 calc R U . . .
C7' C 0.1655(11) 0.5978(7) 0.2339(3) 0.075(3) Uani 1 1 d . . . . .
H7'A H 0.147602 0.651696 0.200526 0.112 Uiso 1 1 calc R U . . .
H7'B H 0.064953 0.601526 0.260782 0.112 Uiso 1 1 calc R U . . .
H7'C H 0.178045 0.518294 0.218560 0.112 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
Cl1' C2' 1.805(7) . ?
O2' C4 1.367(6) . ?
O2' C8' 1.465(7) . ?
O1 C2 1.251(7) . ?
O1' C1' 1.443(8) . ?
O1' H1' 0.8200 . ?
N1 C8A 1.384(7) . ?
N1 C2 1.387(7) . ?
N1 C9 1.477(7) . ?
C3 C4 1.353(8) . ?
C3 C2 1.462(8) . ?
C3 C3' 1.514(8) . ?
C4 C4A 1.436(7) . ?
C4A C8A 1.399(8) . ?
C4A C5 1.403(8) . ?
C8A C8 1.411(8) . ?
C8' C4' 1.509(9) . ?
C8' C10' 1.526(8) . ?
C8' C9' 1.533(10) . ?
C3' C4' 1.525(8) . ?
C3' C2' 1.544(9) . ?
C3' H3' 0.9800 . ?
C1' C6' 1.519(8) . ?
C1' C7' 1.526(10) . ?
C1' C2' 1.545(8) . ?
C4' C5' 1.529(8) . ?
C4' H4' 0.9800 . ?
C2' H2' 0.9800 . ?
C5 C6 1.377(8) . ?
C5 H5 0.9300 . ?
C8 C7 1.374(8) . ?
C8 H8 0.9300 . ?
C7 C6 1.379(9) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C6' C5' 1.526(10) . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 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' C8' 116.8(5) . . ?
C1' O1' H1' 109.5 . . ?
C8A N1 C2 122.7(5) . . ?
C8A N1 C9 119.9(5) . . ?
C2 N1 C9 117.3(5) . . ?
C4 C3 C2 118.2(6) . . ?
C4 C3 C3' 121.8(5) . . ?
C2 C3 C3' 119.9(5) . . ?
C3 C4 O2' 123.6(5) . . ?
C3 C4 C4A 122.8(6) . . ?
O2' C4 C4A 113.6(5) . . ?
C8A C4A C5 120.1(5) . . ?
C8A C4A C4 117.6(6) . . ?
C5 C4A C4 122.3(6) . . ?
N1 C8A C4A 119.9(5) . . ?
N1 C8A C8 121.4(6) . . ?
C4A C8A C8 118.7(6) . . ?
O2' C8' C4' 108.0(5) . . ?
O2' C8' C10' 103.3(5) . . ?
C4' C8' C10' 113.8(6) . . ?
O2' C8' C9' 107.5(6) . . ?
C4' C8' C9' 113.7(5) . . ?
C10' C8' C9' 109.8(6) . . ?
O1 C2 N1 119.7(6) . . ?
O1 C2 C3 122.4(6) . . ?
N1 C2 C3 117.8(6) . . ?
C3 C3' C4' 109.1(5) . . ?
C3 C3' C2' 114.3(5) . . ?
C4' C3' C2' 111.1(5) . . ?
C3 C3' H3' 107.3 . . ?
C4' C3' H3' 107.3 . . ?
C2' C3' H3' 107.3 . . ?
O1' C1' C6' 109.9(6) . . ?
O1' C1' C7' 109.3(5) . . ?
C6' C1' C7' 111.5(7) . . ?
O1' C1' C2' 102.4(6) . . ?
C6' C1' C2' 111.6(5) . . ?
C7' C1' C2' 111.8(6) . . ?
C8' C4' C3' 111.3(5) . . ?
C8' C4' C5' 115.4(5) . . ?
C3' C4' C5' 110.4(5) . . ?
C8' C4' H4' 106.4 . . ?
C3' C4' H4' 106.4 . . ?
C5' C4' H4' 106.4 . . ?
C3' C2' C1' 112.0(6) . . ?
C3' C2' Cl1' 109.3(4) . . ?
C1' C2' Cl1' 110.6(5) . . ?
C3' C2' H2' 108.3 . . ?
C1' C2' H2' 108.3 . . ?
Cl1' C2' H2' 108.3 . . ?
C6 C5 C4A 120.1(6) . . ?
C6 C5 H5 120.0 . . ?
C4A C5 H5 120.0 . . ?
C7 C8 C8A 119.8(6) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C8 C7 C6 121.4(6) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C5 C6 C7 119.9(6) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C1' C6' C5' 112.6(6) . . ?
C1' C6' H6'A 109.1 . . ?
C5' C6' H6'A 109.1 . . ?
C1' C6' H6'B 109.1 . . ?
C5' C6' H6'B 109.1 . . ?
H6'A C6' H6'B 107.8 . . ?
C6' C5' C4' 109.5(6) . . ?
C6' C5' H5'A 109.8 . . ?
C4' C5' H5'A 109.8 . . ?
C6' C5' H5'B 109.8 . . ?
C4' C5' H5'B 109.8 . . ?
H5'A C5' H5'B 108.2 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.071




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_compound_18_FO5-102-1
_database_code_depnum_ccdc_archive 'CCDC 1589040'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 Cl N O4'
_chemical_formula_sum            'C20 H22 Cl N O4'
_chemical_formula_weight         375.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.278(2)
_cell_length_b                   12.6989(10)
_cell_length_c                   17.255(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.191(13)
_cell_angle_gamma                90
_cell_volume                     3700.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4169
_cell_measurement_theta_max      28.3880
_cell_measurement_theta_min      4.0080

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Rigaku four-circle diffractometer'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku(Mo) X-ray Source'
_diffrn_radiation_monochromator  'Confocal MaxFlux double bounce optic'
_diffrn_measurement_device_type  'XtaLABPRO AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_reflns_number            33386
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.549
_diffrn_reflns_theta_max         30.661
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10185
_reflns_number_gt                6215
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0546P)²+1.0648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10185
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
N1 N 0.30202(11) 0.89163(12) 0.47390(10) 0.0391(4) Uani 1 1 d . . . . .
O1 O 0.39483(10) 0.83628(14) 0.40731(11) 0.0596(5) Uani 1 1 d . . . . .
C2 C 0.32530(13) 0.83318(15) 0.41408(12) 0.0372(5) Uani 1 1 d . . . . .
C3 C 0.26370(12) 0.77225(13) 0.36097(11) 0.0321(4) Uani 1 1 d . . . . .
C4 C 0.18779(12) 0.77595(14) 0.37097(13) 0.0365(4) Uani 1 1 d . . . . .
C4A C 0.16547(13) 0.83445(15) 0.43478(13) 0.0394(5) Uani 1 1 d . . . . .
C5 C 0.08674(15) 0.83572(18) 0.44556(16) 0.0509(6) Uani 1 1 d . . . . .
H5 H 0.047875 0.796901 0.412001 0.061 Uiso 1 1 calc R U . . .
C6 C 0.06758(19) 0.8946(2) 0.50589(18) 0.0655(8) Uani 1 1 d . . . . .
H6 H 0.015751 0.895618 0.513120 0.079 Uiso 1 1 calc R U . . .
C7 C 0.1256(2) 0.9523(2) 0.55579(18) 0.0691(8) Uani 1 1 d . . . . .
H7 H 0.111930 0.992206 0.596065 0.083 Uiso 1 1 calc R U . . .
C8 C 0.20285(18) 0.95207(18) 0.54727(14) 0.0566(7) Uani 1 1 d . . . . .
H8 H 0.240799 0.990924 0.581895 0.068 Uiso 1 1 calc R U . . .
C8A C 0.22481(14) 0.89268(15) 0.48575(12) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.36350(17) 0.95546(19) 0.52512(15) 0.0600(7) Uani 1 1 d . . . . .
H9A H 0.347596 1.028034 0.522040 0.090 Uiso 1 1 calc R U . . .
H9AB H 0.412507 0.948405 0.507769 0.090 Uiso 1 1 calc R U . . .
H9AC H 0.370466 0.931528 0.578925 0.090 Uiso 1 1 calc R U . . .
C1' C 0.37379(14) 0.64499(16) 0.21880(13) 0.0431(5) Uani 1 1 d . . . . .
Cl1' Cl 0.36174(5) 0.52975(5) 0.35275(5) 0.0736(2) Uani 1 1 d . . . . .
O1' O 0.35997(11) 0.75463(12) 0.19421(10) 0.0556(4) Uani 1 1 d . . . . .
O2' O 0.30493(9) 0.80083(10) 0.24051(9) 0.0427(4) Uani 1 1 d . . . . .
C2' C 0.36122(13) 0.65343(15) 0.30356(12) 0.0390(5) Uani 1 1 d . . . . .
H2' H 0.403495 0.697316 0.334185 0.047 Uiso 1 1 calc R U . . .
C3' C 0.28350(12) 0.71620(13) 0.28980(11) 0.0323(4) Uani 1 1 d . . . . .
O3' O 0.12558(9) 0.72755(13) 0.32230(11) 0.0525(4) Uani 1 1 d . . . . .
C4' C 0.21031(13) 0.66016(16) 0.23789(13) 0.0423(5) Uani 1 1 d . . . . .
H4' H 0.187319 0.712075 0.197534 0.051 Uiso 1 1 calc R U . . .
C5' C 0.23265(16) 0.56568(19) 0.19092(16) 0.0584(7) Uani 1 1 d . . . . .
H5'A H 0.234070 0.502863 0.223176 0.070 Uiso 1 1 calc R U . . .
H5'B H 0.191287 0.555966 0.143835 0.070 Uiso 1 1 calc R U . . .
C6' C 0.31150(17) 0.5757(2) 0.16571(17) 0.0619(7) Uani 1 1 d . . . . .
H6'A H 0.301648 0.603986 0.112317 0.074 Uiso 1 1 calc R U . . .
H6'B H 0.333528 0.505691 0.163848 0.074 Uiso 1 1 calc R U . . .
C7' C 0.45752(16) 0.6189(2) 0.21122(17) 0.0622(7) Uani 1 1 d . . . . .
H7'A H 0.471860 0.550558 0.233513 0.093 Uiso 1 1 calc R U . . .
H7'B H 0.493372 0.670638 0.239111 0.093 Uiso 1 1 calc R U . . .
H7'C H 0.460323 0.618877 0.156247 0.093 Uiso 1 1 calc R U . . .
C8' C 0.14359(14) 0.63330(17) 0.28074(14) 0.0458(5) Uani 1 1 d . . . . .
C10' C 0.06644(17) 0.6103(3) 0.2201(2) 0.0838(10) Uani 1 1 d . . . . .
H10A H 0.069031 0.541024 0.198484 0.126 Uiso 1 1 calc R U . . .
H10B H 0.059762 0.661292 0.178146 0.126 Uiso 1 1 calc R U . . .
H10C H 0.022384 0.614163 0.245827 0.126 Uiso 1 1 calc R U . . .
C9' C 0.15981(19) 0.54509(19) 0.34263(17) 0.0662(8) Uani 1 1 d . . . . .
H9'A H 0.167078 0.479795 0.317039 0.099 Uiso 1 1 calc R U . . .
H9'B H 0.115719 0.538881 0.368121 0.099 Uiso 1 1 calc R U . . .
H9'C H 0.206803 0.561315 0.381505 0.099 Uiso 1 1 calc R U . . .
Cl1B Cl 0.33307(4) 0.46452(4) 0.72022(4) 0.05398(17) Uani 1 1 d . . . . .
O1B O 0.39552(9) 0.72132(14) 0.85690(10) 0.0549(4) Uani 1 1 d . . . . .
N1B N 0.30620(10) 0.76229(13) 0.93166(10) 0.0395(4) Uani 1 1 d . . . . .
C2B C 0.32550(12) 0.72562(15) 0.86172(12) 0.0365(4) Uani 1 1 d . . . . .
C3B C 0.25927(11) 0.69579(13) 0.79667(11) 0.0310(4) Uani 1 1 d . . . . .
C4B C 0.18367(11) 0.70056(14) 0.80825(11) 0.0316(4) Uani 1 1 d . . . . .
C5B C 0.08846(13) 0.72834(18) 0.89663(14) 0.0444(5) Uani 1 1 d . . . . .
H5B H 0.047186 0.705150 0.856569 0.053 Uiso 1 1 calc R U . . .
C6B C 0.07298(16) 0.7600(2) 0.96828(15) 0.0566(6) Uani 1 1 d . . . . .
H6B H 0.021613 0.757896 0.976779 0.068 Uiso 1 1 calc R U . . .
C7B C 0.13482(17) 0.7950(2) 1.02755(15) 0.0582(7) Uani 1 1 d . . . . .
H7B H 0.124064 0.817901 1.075372 0.070 Uiso 1 1 calc R U . . .
C8B C 0.21213(16) 0.79667(19) 1.01731(14) 0.0526(6) Uani 1 1 d . . . . .
H8B H 0.252818 0.819384 1.058156 0.063 Uiso 1 1 calc R U . . .
C9B C 0.37253(15) 0.7969(2) 0.99536(15) 0.0609(7) Uani 1 1 d . . . . .
H9BA H 0.361640 0.866001 1.012887 0.091 Uiso 1 1 calc R U . . .
H9BB H 0.420438 0.798508 0.975568 0.091 Uiso 1 1 calc R U . . .
H9BC H 0.378622 0.748569 1.039036 0.091 Uiso 1 1 calc R U . . .
C10B C 0.13823(15) 0.49695(17) 0.72218(15) 0.0526(6) Uani 1 1 d . . . . .
H10D H 0.186242 0.493359 0.762006 0.079 Uiso 1 1 calc R U . . .
H10E H 0.140434 0.446653 0.681165 0.079 Uiso 1 1 calc R U . . .
H10F H 0.093915 0.481319 0.745698 0.079 Uiso 1 1 calc R U . . .
C9'B C 0.04983(15) 0.6191(2) 0.62666(16) 0.0611(7) Uani 1 1 d . . . . .
H9'D H 0.045473 0.688892 0.604804 0.092 Uiso 1 1 calc R U . . .
H9'E H 0.006929 0.606627 0.652920 0.092 Uiso 1 1 calc R U . . .
H9'F H 0.047654 0.568643 0.584821 0.092 Uiso 1 1 calc R U . . .
C5'B C 0.21184(15) 0.5822(2) 0.58228(14) 0.0507(6) Uani 1 1 d . . . . .
H5'C H 0.207971 0.508651 0.596044 0.061 Uiso 1 1 calc R U . . .
H5'D H 0.170136 0.596471 0.536257 0.061 Uiso 1 1 calc R U . . .
O3'B O 0.11849(8) 0.67883(12) 0.75140(9) 0.0413(3) Uani 1 1 d . . . . .
C1'B C 0.35909(15) 0.63478(19) 0.62765(15) 0.0507(6) Uani 1 1 d . . . . .
O1'B O 0.35730(14) 0.74860(14) 0.63578(13) 0.0755(6) Uani 1 1 d . . . . .
O2'B O 0.30610(9) 0.77432(10) 0.69215(10) 0.0458(4) Uani 1 1 d . . . . .
C6'B C 0.29195(17) 0.6004(2) 0.55984(15) 0.0618(7) Uani 1 1 d . . . . .
H6'C H 0.307619 0.535693 0.537523 0.074 Uiso 1 1 calc R U . . .
H6'D H 0.285246 0.653663 0.518663 0.074 Uiso 1 1 calc R U . . .
C4AB C 0.16589(12) 0.73079(14) 0.88358(12) 0.0337(4) Uani 1 1 d . . . . .
C7'B C 0.44094(18) 0.6069(3) 0.6135(2) 0.0807(9) Uani 1 1 d . . . . .
H7'D H 0.445582 0.531786 0.609910 0.121 Uiso 1 1 calc R U . . .
H7'E H 0.480830 0.632739 0.656660 0.121 Uiso 1 1 calc R U . . .
H7'F H 0.447868 0.638573 0.564864 0.121 Uiso 1 1 calc R U . . .
C3'B C 0.27483(12) 0.67414(13) 0.71514(12) 0.0326(4) Uani 1 1 d . . . . .
C8AB C 0.22881(13) 0.76364(15) 0.94440(12) 0.0376(5) Uani 1 1 d . . . . .
C8'B C 0.12881(12) 0.60809(16) 0.68648(12) 0.0378(5) Uani 1 1 d . . . . .
C4'B C 0.19746(12) 0.65088(15) 0.65236(12) 0.0362(4) Uani 1 1 d . . . . .
H4'B H 0.179466 0.719312 0.629078 0.043 Uiso 1 1 calc R U . . .
C2'B C 0.34603(13) 0.60307(15) 0.70951(13) 0.0381(5) Uani 1 1 d . . . . .
H2'B H 0.391928 0.625929 0.749621 0.046 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
N1 C8A 1.392(3) . ?
N1 C2 1.398(3) . ?
N1 C9 1.473(3) . ?
O1 C2 1.232(3) . ?
C2 C3 1.469(3) . ?
C3 C4 1.359(3) . ?
C3 C3' 1.520(3) . ?
C4 O3' 1.363(3) . ?
C4 C4A 1.447(3) . ?
C4A C8A 1.411(3) . ?
C4A C5 1.411(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.418(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9AB 0.9600 . ?
C9 H9AC 0.9600 . ?
C1' O1' 1.460(3) . ?
C1' C7' 1.516(3) . ?
C1' C2' 1.527(3) . ?
C1' C6' 1.535(3) . ?
Cl1' C2' 1.784(2) . ?
O1' O2' 1.486(2) . ?
O2' C3' 1.466(2) . ?
C2' C3' 1.536(3) . ?
C2' H2' 0.9800 . ?
C3' C4' 1.559(3) . ?
O3' C8' 1.462(3) . ?
C4' C8' 1.534(3) . ?
C4' C5' 1.542(3) . ?
C4' H4' 0.9800 . ?
C5' C6' 1.520(4) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' C9' 1.532(4) . ?
C8' C10' 1.539(3) . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
Cl1B C2'B 1.788(2) . ?
O1B C2B 1.231(3) . ?
N1B C2B 1.398(3) . ?
N1B C8AB 1.400(3) . ?
N1B C9B 1.477(3) . ?
C2B C3B 1.473(3) . ?
C3B C4B 1.364(3) . ?
C3B C3'B 1.512(3) . ?
C4B O3'B 1.357(2) . ?
C4B C4AB 1.449(3) . ?
C5B C6B 1.379(3) . ?
C5B C4AB 1.403(3) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.387(4) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.384(4) . ?
C7B H7B 0.9300 . ?
C8B C8AB 1.412(3) . ?
C8B H8B 0.9300 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10B C8'B 1.535(3) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C9'B C8'B 1.534(3) . ?
C9'B H9'D 0.9600 . ?
C9'B H9'E 0.9600 . ?
C9'B H9'F 0.9600 . ?
C5'B C6'B 1.531(4) . ?
C5'B C4'B 1.552(3) . ?
C5'B H5'C 0.9700 . ?
C5'B H5'D 0.9700 . ?
O3'B C8'B 1.476(2) . ?
C1'B O1'B 1.453(3) . ?
C1'B C7'B 1.527(4) . ?
C1'B C6'B 1.527(4) . ?
C1'B C2'B 1.530(3) . ?
O1'B O2'B 1.483(2) . ?
O2'B C3'B 1.469(2) . ?
C6'B H6'C 0.9700 . ?
C6'B H6'D 0.9700 . ?
C4AB C8AB 1.405(3) . ?
C7'B H7'D 0.9600 . ?
C7'B H7'E 0.9600 . ?
C7'B H7'F 0.9600 . ?
C3'B C2'B 1.545(3) . ?
C3'B C4'B 1.561(3) . ?
C8'B C4'B 1.531(3) . ?
C4'B H4'B 0.9800 . ?
C2'B H2'B 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
C8A N1 C2 123.22(17) . . ?
C8A N1 C9 119.92(18) . . ?
C2 N1 C9 116.9(2) . . ?
O1 C2 N1 119.44(19) . . ?
O1 C2 C3 123.37(19) . . ?
N1 C2 C3 117.17(19) . . ?
C4 C3 C2 119.60(18) . . ?
C4 C3 C3' 120.44(18) . . ?
C2 C3 C3' 119.58(18) . . ?
C3 C4 O3' 124.26(18) . . ?
C3 C4 C4A 122.27(19) . . ?
O3' C4 C4A 113.46(19) . . ?
C8A C4A C5 120.4(2) . . ?
C8A C4A C4 117.9(2) . . ?
C5 C4A C4 121.7(2) . . ?
C6 C5 C4A 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4A C5 H5 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C8A 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
N1 C8A C4A 119.77(18) . . ?
N1 C8A C8 122.1(2) . . ?
C4A C8A C8 118.1(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
N1 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
O1' C1' C7' 106.49(19) . . ?
O1' C1' C2' 99.43(16) . . ?
C7' C1' C2' 115.4(2) . . ?
O1' C1' C6' 108.8(2) . . ?
C7' C1' C6' 112.6(2) . . ?
C2' C1' C6' 112.8(2) . . ?
C1' O1' O2' 107.71(14) . . ?
C3' O2' O1' 106.94(13) . . ?
C1' C2' C3' 100.66(17) . . ?
C1' C2' Cl1' 113.98(14) . . ?
C3' C2' Cl1' 116.53(15) . . ?
C1' C2' H2' 108.4 . . ?
C3' C2' H2' 108.4 . . ?
Cl1' C2' H2' 108.4 . . ?
O2' C3' C3 104.66(14) . . ?
O2' C3' C2' 98.65(15) . . ?
C3 C3' C2' 117.18(17) . . ?
O2' C3' C4' 105.96(15) . . ?
C3 C3' C4' 112.61(17) . . ?
C2' C3' C4' 115.37(16) . . ?
C4 O3' C8' 116.71(16) . . ?
C8' C4' C5' 112.18(18) . . ?
C8' C4' C3' 115.19(17) . . ?
C5' C4' C3' 113.24(19) . . ?
C8' C4' H4' 105.0 . . ?
C5' C4' H4' 105.0 . . ?
C3' C4' H4' 105.0 . . ?
C6' C5' C4' 115.11(19) . . ?
C6' C5' H5'A 108.5 . . ?
C4' C5' H5'A 108.5 . . ?
C6' C5' H5'B 108.5 . . ?
C4' C5' H5'B 108.5 . . ?
H5'A C5' H5'B 107.5 . . ?
C5' C6' C1' 115.78(19) . . ?
C5' C6' H6'A 108.3 . . ?
C1' C6' H6'A 108.3 . . ?
C5' C6' H6'B 108.3 . . ?
C1' C6' H6'B 108.3 . . ?
H6'A C6' H6'B 107.4 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
O3' C8' C9' 106.45(19) . . ?
O3' C8' C4' 108.30(16) . . ?
C9' C8' C4' 116.9(2) . . ?
O3' C8' C10' 104.2(2) . . ?
C9' C8' C10' 109.9(2) . . ?
C4' C8' C10' 110.2(2) . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C2B N1B C8AB 123.32(17) . . ?
C2B N1B C9B 116.90(19) . . ?
C8AB N1B C9B 119.74(19) . . ?
O1B C2B N1B 119.33(19) . . ?
O1B C2B C3B 123.6(2) . . ?
N1B C2B C3B 117.06(18) . . ?
C4B C3B C2B 119.39(18) . . ?
C4B C3B C3'B 120.55(17) . . ?
C2B C3B C3'B 119.57(17) . . ?
O3'B C4B C3B 124.02(18) . . ?
O3'B C4B C4AB 113.68(17) . . ?
C3B C4B C4AB 122.30(17) . . ?
C6B C5B C4AB 120.6(2) . . ?
C6B C5B H5B 119.7 . . ?
C4AB C5B H5B 119.7 . . ?
C5B C6B C7B 119.3(2) . . ?
C5B C6B H6B 120.3 . . ?
C7B C6B H6B 120.3 . . ?
C8B C7B C6B 121.7(2) . . ?
C8B C7B H7B 119.2 . . ?
C6B C7B H7B 119.2 . . ?
C7B C8B C8AB 119.5(2) . . ?
C7B C8B H8B 120.2 . . ?
C8AB C8B H8B 120.2 . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8'B C10B H10D 109.5 . . ?
C8'B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C8'B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C8'B C9'B H9'D 109.5 . . ?
C8'B C9'B H9'E 109.5 . . ?
H9'D C9'B H9'E 109.5 . . ?
C8'B C9'B H9'F 109.5 . . ?
H9'D C9'B H9'F 109.5 . . ?
H9'E C9'B H9'F 109.5 . . ?
C6'B C5'B C4'B 114.5(2) . . ?
C6'B C5'B H5'C 108.6 . . ?
C4'B C5'B H5'C 108.6 . . ?
C6'B C5'B H5'D 108.6 . . ?
C4'B C5'B H5'D 108.6 . . ?
H5'C C5'B H5'D 107.6 . . ?
C4B O3'B C8'B 117.24(15) . . ?
O1'B C1'B C7'B 106.6(2) . . ?
O1'B C1'B C6'B 109.3(2) . . ?
C7'B C1'B C6'B 113.0(2) . . ?
O1'B C1'B C2'B 99.35(18) . . ?
C7'B C1'B C2'B 114.1(2) . . ?
C6'B C1'B C2'B 113.3(2) . . ?
C1'B O1'B O2'B 108.07(15) . . ?
C3'B O2'B O1'B 106.91(14) . . ?
C1'B C6'B C5'B 115.5(2) . . ?
C1'B C6'B H6'C 108.4 . . ?
C5'B C6'B H6'C 108.4 . . ?
C1'B C6'B H6'D 108.4 . . ?
C5'B C6'B H6'D 108.4 . . ?
H6'C C6'B H6'D 107.5 . . ?
C5B C4AB C8AB 120.01(19) . . ?
C5B C4AB C4B 121.87(19) . . ?
C8AB C4AB C4B 118.12(19) . . ?
C1'B C7'B H7'D 109.5 . . ?
C1'B C7'B H7'E 109.5 . . ?
H7'D C7'B H7'E 109.5 . . ?
C1'B C7'B H7'F 109.5 . . ?
H7'D C7'B H7'F 109.5 . . ?
H7'E C7'B H7'F 109.5 . . ?
O2'B C3'B C3B 103.98(14) . . ?
O2'B C3'B C2'B 98.37(15) . . ?
C3B C3'B C2'B 117.71(16) . . ?
O2'B C3'B C4'B 106.64(15) . . ?
C3B C3'B C4'B 112.69(17) . . ?
C2'B C3'B C4'B 114.98(16) . . ?
N1B C8AB C4AB 119.53(18) . . ?
N1B C8AB C8B 121.6(2) . . ?
C4AB C8AB C8B 118.8(2) . . ?
O3'B C8'B C4'B 107.67(15) . . ?
O3'B C8'B C9'B 102.85(17) . . ?
C4'B C8'B C9'B 111.12(19) . . ?
O3'B C8'B C10B 105.94(18) . . ?
C4'B C8'B C10B 117.11(18) . . ?
C9'B C8'B C10B 110.96(19) . . ?
C8'B C4'B C5'B 111.39(17) . . ?
C8'B C4'B C3'B 114.81(16) . . ?
C5'B C4'B C3'B 113.11(18) . . ?
C8'B C4'B H4'B 105.5 . . ?
C5'B C4'B H4'B 105.5 . . ?
C3'B C4'B H4'B 105.5 . . ?
C1'B C2'B C3'B 100.30(16) . . ?
C1'B C2'B Cl1B 113.60(15) . . ?
C3'B C2'B Cl1B 116.70(14) . . ?
C1'B C2'B H2'B 108.6 . . ?
C3'B C2'B H2'B 108.6 . . ?
Cl1B C2'B H2'B 108.6 . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.045





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ether/methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# 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_compound_19
_database_code_depnum_ccdc_archive 'CCDC 1824664'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 Cl N O3, H2 O'
_chemical_formula_sum            'C20 H26 Cl N O4'
_chemical_formula_weight         379.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.1270(8)
_cell_length_b                   7.2090(4)
_cell_length_c                   16.3705(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.080(5)
_cell_angle_gamma                90
_cell_volume                     1902.90(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6241
_cell_measurement_theta_min      3.5700
_cell_measurement_theta_max      29.6930

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.62130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'HPAD DECTRIS PILATUS3R 200K'
_diffrn_reflns_number            20009
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.514
_diffrn_reflns_theta_max         29.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4819
_reflns_number_gt                3578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_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)+(0.0915P)²+0.9367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4818
_refine_ls_number_parameters     246
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1929
_refine_ls_wR_factor_gt          0.1793
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_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
Cl1' Cl 0.93803(4) 0.52884(11) 0.38547(4) 0.0560(2) Uani 1 1 d . . . . .
O1 O 0.67975(10) 0.5838(2) 0.33229(9) 0.0387(4) Uani 1 1 d . . . . .
O2' O 0.70442(11) 0.5849(2) 0.62103(9) 0.0434(4) Uani 1 1 d . . . . .
O1' O 0.78576(11) 0.9532(3) 0.42984(12) 0.0505(5) Uani 1 1 d . . . . .
H1' H 0.783504 1.039042 0.397031 0.076 Uiso 1 1 calc R U . . .
N1 N 0.57433(11) 0.6963(3) 0.40742(11) 0.0346(4) Uani 1 1 d . . . . .
C2 C 0.65410(13) 0.6280(3) 0.40117(12) 0.0320(4) Uani 1 1 d . . . . .
C8A C 0.53767(13) 0.7275(3) 0.48299(14) 0.0348(5) Uani 1 1 d . . . . .
C4 C 0.66722(14) 0.6244(3) 0.54831(13) 0.0339(5) Uani 1 1 d . . . . .
C4A C 0.58295(14) 0.6895(3) 0.55440(13) 0.0355(5) Uani 1 1 d . . . . .
C3' C 0.79484(13) 0.5545(3) 0.46886(12) 0.0331(4) Uani 1 1 d . . . . .
H3' H 0.796649 0.422457 0.454687 0.040 Uiso 1 1 calc R U . . .
C3 C 0.70435(13) 0.6083(3) 0.47455(12) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.54608(17) 0.7192(3) 0.63079(16) 0.0458(6) Uani 1 1 d . . . . .
H5 H 0.576327 0.697046 0.678737 0.055 Uiso 1 1 calc R U . . .
C7' C 0.91813(16) 0.9518(4) 0.36003(16) 0.0478(6) Uani 1 1 d . . . . .
H7'A H 0.923440 1.082026 0.371173 0.072 Uiso 1 1 calc R U . . .
H7'B H 0.892875 0.934528 0.307004 0.072 Uiso 1 1 calc R U . . .
H7'C H 0.972048 0.895291 0.361301 0.072 Uiso 1 1 calc R U . . .
C2' C 0.84359(13) 0.6603(3) 0.40311(13) 0.0352(5) Uani 1 1 d . . . . .
H2' H 0.810301 0.659718 0.352410 0.042 Uiso 1 1 calc R U . . .
C4' C 0.83728(14) 0.5762(3) 0.55376(13) 0.0378(5) Uani 1 1 d . . . . .
H4' H 0.890203 0.509461 0.552768 0.045 Uiso 1 1 calc R U . . .
C9 C 0.52681(17) 0.7276(4) 0.33097(16) 0.0476(6) Uani 1 1 d . . . . .
H9A H 0.478401 0.650095 0.330098 0.071 Uiso 1 1 calc R U . . .
H9B H 0.560736 0.697792 0.285231 0.071 Uiso 1 1 calc R U . . .
H9C H 0.510313 0.855397 0.327732 0.071 Uiso 1 1 calc R U . . .
C1' C 0.86432(14) 0.8623(3) 0.42438(14) 0.0400(5) Uani 1 1 d . . . . .
C8 C 0.45578(15) 0.7900(3) 0.48821(18) 0.0476(6) Uani 1 1 d . . . . .
H8 H 0.424731 0.813186 0.440855 0.057 Uiso 1 1 calc R U . . .
C6 C 0.46546(18) 0.7808(4) 0.63451(19) 0.0533(7) Uani 1 1 d . . . . .
H6 H 0.440851 0.797860 0.684881 0.064 Uiso 1 1 calc R U . . .
C6' C 0.90638(17) 0.8721(4) 0.50833(15) 0.0476(6) Uani 1 1 d . . . . .
H6'A H 0.960249 0.812666 0.505982 0.057 Uiso 1 1 calc R U . . .
H6'B H 0.915137 1.001073 0.522964 0.057 Uiso 1 1 calc R U . . .
C8' C 0.78332(17) 0.4849(4) 0.61874(14) 0.0439(6) Uani 1 1 d . . . . .
C5' C 0.85582(17) 0.7792(4) 0.57358(14) 0.0470(6) Uani 1 1 d . . . . .
H5'A H 0.803950 0.845635 0.579346 0.056 Uiso 1 1 calc R U . . .
H5'B H 0.885856 0.786195 0.625389 0.056 Uiso 1 1 calc R U . . .
C7 C 0.42130(17) 0.8172(4) 0.5635(2) 0.0561(8) Uani 1 1 d . . . . .
H7 H 0.367194 0.860945 0.566462 0.067 Uiso 1 1 calc R U . . .
C10' C 0.7656(2) 0.2804(4) 0.60034(18) 0.0588(7) Uani 1 1 d . . . . .
H10A H 0.738407 0.269771 0.547873 0.088 Uiso 1 1 calc R U . . .
H10B H 0.730427 0.230469 0.641581 0.088 Uiso 1 1 calc R U . . .
H10C H 0.816848 0.212683 0.600017 0.088 Uiso 1 1 calc R U . . .
C9' C 0.8197(2) 0.5050(5) 0.70499(15) 0.0596(8) Uani 1 1 d . . . . .
H9'A H 0.785334 0.440061 0.742764 0.089 Uiso 1 1 calc R U . . .
H9'B H 0.821999 0.633984 0.719496 0.089 Uiso 1 1 calc R U . . .
H9'C H 0.874616 0.453703 0.706990 0.089 Uiso 1 1 calc R U . . .
OW1 O 0.75482(16) 0.7162(3) 0.19052(12) 0.0661(6) Uani 1 1 d D . . . .
HW1 H 0.726(3) 0.706(6) 0.2320(19) 0.099 Uiso 1 1 d D U . . .
HW2 H 0.768(3) 0.825(3) 0.190(3) 0.099 Uiso 1 1 d D 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
Cl1' C2' 1.821(2) . ?
O1 C2 1.250(2) . ?
O2' C4 1.353(3) . ?
O2' C8' 1.463(3) . ?
O1' C1' 1.431(3) . ?
O1' H1' 0.8200 . ?
N1 C2 1.383(3) . ?
N1 C8A 1.399(3) . ?
N1 C9 1.473(3) . ?
C2 C3 1.443(3) . ?
C8A C4A 1.394(3) . ?
C8A C8 1.400(3) . ?
C4 C3 1.363(3) . ?
C4 C4A 1.443(3) . ?
C4A C5 1.411(3) . ?
C3' C3 1.515(3) . ?
C3' C4' 1.546(3) . ?
C3' C2' 1.546(3) . ?
C3' H3' 0.9800 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C7' C1' 1.521(3) . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C2' C1' 1.533(3) . ?
C2' H2' 0.9800 . ?
C4' C5' 1.528(3) . ?
C4' C8' 1.535(3) . ?
C4' H4' 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1' C6' 1.523(3) . ?
C8 C7 1.375(4) . ?
C8 H8 0.9300 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9300 . ?
C6' C5' 1.512(3) . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C8' C9' 1.526(4) . ?
C8' C10' 1.531(4) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C7 H7 0.9300 . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C9' H9'A 0.9600 . ?
C9' H9'B 0.9600 . ?
C9' H9'C 0.9600 . ?
OW1 HW1 0.830(19) . ?
OW1 HW2 0.816(19) . ?

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' C8' 116.88(16) . . ?
C1' O1' H1' 109.5 . . ?
C2 N1 C8A 122.12(19) . . ?
C2 N1 C9 117.49(18) . . ?
C8A N1 C9 120.32(19) . . ?
O1 C2 N1 118.80(19) . . ?
O1 C2 C3 122.39(19) . . ?
N1 C2 C3 118.81(18) . . ?
C4A C8A N1 119.11(19) . . ?
C4A C8A C8 119.5(2) . . ?
N1 C8A C8 121.4(2) . . ?
O2' C4 C3 124.5(2) . . ?
O2' C4 C4A 114.21(18) . . ?
C3 C4 C4A 121.3(2) . . ?
C8A C4A C5 119.4(2) . . ?
C8A C4A C4 119.03(18) . . ?
C5 C4A C4 121.6(2) . . ?
C3 C3' C4' 109.24(17) . . ?
C3 C3' C2' 114.81(18) . . ?
C4' C3' C2' 110.71(18) . . ?
C3 C3' H3' 107.2 . . ?
C4' C3' H3' 107.2 . . ?
C2' C3' H3' 107.2 . . ?
C4 C3 C2 118.68(19) . . ?
C4 C3 C3' 121.08(19) . . ?
C2 C3 C3' 120.03(17) . . ?
C6 C5 C4A 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4A C5 H5 119.9 . . ?
C1' C7' H7'A 109.5 . . ?
C1' C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C1' C7' H7'C 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C1' C2' C3' 114.98(17) . . ?
C1' C2' Cl1' 110.54(15) . . ?
C3' C2' Cl1' 106.94(15) . . ?
C1' C2' H2' 108.1 . . ?
C3' C2' H2' 108.1 . . ?
Cl1' C2' H2' 108.1 . . ?
C5' C4' C8' 112.00(19) . . ?
C5' C4' C3' 111.69(18) . . ?
C8' C4' C3' 109.42(19) . . ?
C5' C4' H4' 107.9 . . ?
C8' C4' H4' 107.9 . . ?
C3' C4' H4' 107.9 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1' C1' C7' 111.5(2) . . ?
O1' C1' C6' 107.6(2) . . ?
C7' C1' C6' 110.8(2) . . ?
O1' C1' C2' 105.05(18) . . ?
C7' C1' C2' 111.8(2) . . ?
C6' C1' C2' 109.9(2) . . ?
C7 C8 C8A 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C5' C6' C1' 112.3(2) . . ?
C5' C6' H6'A 109.1 . . ?
C1' C6' H6'A 109.1 . . ?
C5' C6' H6'B 109.1 . . ?
C1' C6' H6'B 109.1 . . ?
H6'A C6' H6'B 107.9 . . ?
O2' C8' C9' 104.4(2) . . ?
O2' C8' C10' 108.7(2) . . ?
C9' C8' C10' 109.9(2) . . ?
O2' C8' C4' 108.14(18) . . ?
C9' C8' C4' 112.8(2) . . ?
C10' C8' C4' 112.5(2) . . ?
C6' C5' C4' 112.3(2) . . ?
C6' C5' H5'A 109.1 . . ?
C4' C5' H5'A 109.1 . . ?
C6' C5' H5'B 109.1 . . ?
C4' C5' H5'B 109.1 . . ?
H5'A C5' H5'B 107.9 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C8' C10' H10A 109.5 . . ?
C8' C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
C8' C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
HW1 OW1 HW2 104(4) . . ?

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
C8A N1 C2 O1 172.11(19) . . . . ?
C9 N1 C2 O1 -5.1(3) . . . . ?
C8A N1 C2 C3 -7.2(3) . . . . ?
C9 N1 C2 C3 175.62(19) . . . . ?
C2 N1 C8A C4A 0.3(3) . . . . ?
C9 N1 C8A C4A 177.4(2) . . . . ?
C2 N1 C8A C8 -177.6(2) . . . . ?
C9 N1 C8A C8 -0.5(3) . . . . ?
C8' O2' C4 C3 -12.4(3) . . . . ?
C8' O2' C4 C4A 168.43(19) . . . . ?
N1 C8A C4A C5 -179.47(19) . . . . ?
C8 C8A C4A C5 -1.6(3) . . . . ?
N1 C8A C4A C4 1.9(3) . . . . ?
C8 C8A C4A C4 179.8(2) . . . . ?
O2' C4 C4A C8A -177.58(18) . . . . ?
C3 C4 C4A C8A 3.2(3) . . . . ?
O2' C4 C4A C5 3.8(3) . . . . ?
C3 C4 C4A C5 -175.4(2) . . . . ?
O2' C4 C3 C2 170.80(19) . . . . ?
C4A C4 C3 C2 -10.1(3) . . . . ?
O2' C4 C3 C3' -3.9(3) . . . . ?
C4A C4 C3 C3' 175.15(19) . . . . ?
O1 C2 C3 C4 -167.3(2) . . . . ?
N1 C2 C3 C4 12.0(3) . . . . ?
O1 C2 C3 C3' 7.5(3) . . . . ?
N1 C2 C3 C3' -173.18(18) . . . . ?
C4' C3' C3 C4 -15.0(3) . . . . ?
C2' C3' C3 C4 -140.0(2) . . . . ?
C4' C3' C3 C2 170.31(19) . . . . ?
C2' C3' C3 C2 45.3(3) . . . . ?
C8A C4A C5 C6 1.6(3) . . . . ?
C4 C4A C5 C6 -179.8(2) . . . . ?
C3 C3' C2' C1' 73.9(2) . . . . ?
C4' C3' C2' C1' -50.4(2) . . . . ?
C3 C3' C2' Cl1' -162.99(15) . . . . ?
C4' C3' C2' Cl1' 72.75(19) . . . . ?
C3 C3' C4' C5' -77.1(2) . . . . ?
C2' C3' C4' C5' 50.3(2) . . . . ?
C3 C3' C4' C8' 47.5(2) . . . . ?
C2' C3' C4' C8' 174.85(18) . . . . ?
C3' C2' C1' O1' -63.6(2) . . . . ?
Cl1' C2' C1' O1' 175.25(14) . . . . ?
C3' C2' C1' C7' 175.38(19) . . . . ?
Cl1' C2' C1' C7' 54.2(2) . . . . ?
C3' C2' C1' C6' 51.9(2) . . . . ?
Cl1' C2' C1' C6' -69.3(2) . . . . ?
C4A C8A C8 C7 1.4(3) . . . . ?
N1 C8A C8 C7 179.2(2) . . . . ?
C4A C5 C6 C7 -1.3(4) . . . . ?
O1' C1' C6' C5' 59.6(3) . . . . ?
C7' C1' C6' C5' -178.3(2) . . . . ?
C2' C1' C6' C5' -54.3(3) . . . . ?
C4 O2' C8' C9' 166.0(2) . . . . ?
C4 O2' C8' C10' -76.8(2) . . . . ?
C4 O2' C8' C4' 45.6(3) . . . . ?
C5' C4' C8' O2' 61.0(3) . . . . ?
C3' C4' C8' O2' -63.4(2) . . . . ?
C5' C4' C8' C9' -53.9(3) . . . . ?
C3' C4' C8' C9' -178.4(2) . . . . ?
C5' C4' C8' C10' -179.0(2) . . . . ?
C3' C4' C8' C10' 56.6(3) . . . . ?
C1' C6' C5' C4' 57.3(3) . . . . ?
C8' C4' C5' C6' -177.9(2) . . . . ?
C3' C4' C5' C6' -54.8(3) . . . . ?
C8A C8 C7 C6 -1.2(4) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1' H1' OW1 0.82 2.01 2.803(3) 163.1 2_655 yes
C2' H2' O1 0.98 2.19 2.918(3) 129.6 . yes
C4' H4' Cl1' 0.98 2.94 3.815(2) 148.7 3_766 yes
OW1 HW1 O1 0.830(19) 2.02(3) 2.805(2) 157(4) . yes
OW1 HW2 O1 0.816(19) 2.08(2) 2.879(3) 167(4) 2_655 yes

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.092





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/H2O'
####################################################################### 
# 
# 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_compound_14
_database_code_depnum_ccdc_archive 'CCDC 1589036'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2096(3)
_cell_length_b                   12.8487(4)
_cell_length_c                   12.9425(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.010(4)
_cell_angle_gamma                90
_cell_volume                     1623.53(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15150
_cell_measurement_theta_min      3.4180
_cell_measurement_theta_max      29.8820

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Rigaku four-circle diffractometer'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku(Mo) X-ray Source'
_diffrn_radiation_monochromator  'Confocal MaxFlux double bounce optic'
_diffrn_measurement_device_type  'XtaLABPRO AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_reflns_number            38380
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.751
_diffrn_reflns_theta_max         29.951
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4453
_reflns_number_gt                3924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0609P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4453
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C2' C 0.28180(8) 0.23186(6) 0.59418(6) 0.01393(16) Uani 1 1 d . . . . .
C2 C 0.59416(8) 0.39801(6) 0.69697(6) 0.01442(16) Uani 1 1 d . . . . .
O1 O 0.68213(6) 0.33374(5) 0.74315(5) 0.02040(15) Uani 1 1 d . . . . .
C7' C 0.17473(8) 0.31766(6) 0.55446(7) 0.01421(16) Uani 1 1 d . . . . .
N1 N 0.62601(7) 0.50352(6) 0.69670(6) 0.01587(16) Uani 1 1 d . . . . .
C3 C 0.45418(8) 0.36857(6) 0.64056(6) 0.01331(16) Uani 1 1 d . . . . .
C1' C 0.41335(8) 0.25990(6) 0.63669(7) 0.01458(17) Uani 1 1 d . . . . .
H1' H 0.480660 0.207988 0.664633 0.017 Uiso 1 1 calc R U . . .
C4 C 0.36351(8) 0.43995(6) 0.58316(6) 0.01267(16) Uani 1 1 d . . . . .
C4' C 0.12686(9) 0.09933(7) 0.47857(7) 0.01964(18) Uani 1 1 d . . . . .
H4'A H 0.172459 0.102517 0.420846 0.024 Uiso 1 1 calc R U . . .
H4'B H 0.088740 0.028426 0.478144 0.024 Uiso 1 1 calc R U . . .
C5 C 0.30609(9) 0.62318(7) 0.52291(7) 0.01724(17) Uani 1 1 d . . . . .
H5 H 0.216964 0.602584 0.481141 0.021 Uiso 1 1 calc R U . . .
C5' C 0.00957(9) 0.17782(7) 0.45339(8) 0.02237(19) Uani 1 1 d . . . . .
H5'A H -0.038230 0.174288 0.509729 0.027 Uiso 1 1 calc R U . . .
H5'B H -0.057273 0.160845 0.382969 0.027 Uiso 1 1 calc R U . . .
C8 C 0.56863(9) 0.68420(7) 0.64532(7) 0.01921(18) Uani 1 1 d . . . . .
H8 H 0.657373 0.705939 0.686792 0.023 Uiso 1 1 calc R U . . .
C3' C 0.23429(9) 0.11838(6) 0.58832(7) 0.01621(17) Uani 1 1 d . . . . .
C6 C 0.34341(10) 0.72701(7) 0.52673(8) 0.02203(19) Uani 1 1 d . . . . .
H6 H 0.280550 0.777654 0.487496 0.026 Uiso 1 1 calc R U . . .
C6' C 0.06588(9) 0.28757(7) 0.44952(7) 0.01856(18) Uani 1 1 d . . . . .
H6'A H -0.010580 0.338055 0.435426 0.022 Uiso 1 1 calc R U . . .
H6'B H 0.106316 0.291954 0.388834 0.022 Uiso 1 1 calc R U . . .
C7 C 0.47442(10) 0.75653(7) 0.58885(8) 0.0226(2) Uani 1 1 d . . . . .
H7 H 0.499386 0.827953 0.592381 0.027 Uiso 1 1 calc R U . . .
C8' C 0.11206(10) 0.35330(7) 0.64268(8) 0.02173(19) Uani 1 1 d . . . . .
H8'A H 0.058099 0.416602 0.618943 0.033 Uiso 1 1 calc R U . . .
H8'B H 0.185423 0.367750 0.709256 0.033 Uiso 1 1 calc R U . . .
H8'C H 0.052597 0.298332 0.656225 0.033 Uiso 1 1 calc R U . . .
C9 C 0.76702(9) 0.53474(8) 0.75299(8) 0.0243(2) Uani 1 1 d . . . . .
H9A H 0.766596 0.584492 0.810286 0.037 Uiso 1 1 calc R U . . .
H9B H 0.808215 0.567349 0.701510 0.037 Uiso 1 1 calc R U . . .
H9C H 0.820486 0.473237 0.784805 0.037 Uiso 1 1 calc R U . . .
C10' C 0.35363(10) 0.04245(7) 0.59788(9) 0.0246(2) Uani 1 1 d . . . . .
H10D H 0.318259 -0.028834 0.586107 0.037 Uiso 1 1 calc R U . . .
H10E H 0.419019 0.047988 0.670152 0.037 Uiso 1 1 calc R U . . .
H10F H 0.399674 0.059807 0.543464 0.037 Uiso 1 1 calc R U . . .
C8A C 0.53249(8) 0.57825(6) 0.64112(6) 0.01442(17) Uani 1 1 d . . . . .
C4A C 0.39917(8) 0.54800(6) 0.58043(6) 0.01333(16) Uani 1 1 d . . . . .
O1' O 0.23647(6) 0.41180(5) 0.52246(5) 0.01553(14) Uani 1 1 d . . . . .
C9' C 0.17439(10) 0.09354(7) 0.68219(8) 0.0233(2) Uani 1 1 d . . . . .
H9'A H 0.150590 0.019538 0.680313 0.035 Uiso 1 1 calc R U . . .
H9'B H 0.092054 0.135608 0.674664 0.035 Uiso 1 1 calc R U . . .
H9'C H 0.242544 0.109731 0.751136 0.035 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
C2' C1' 1.3431(11) . ?
C2' C3' 1.5314(11) . ?
C2' C7' 1.5316(11) . ?
C2 O1 1.2377(10) . ?
C2 N1 1.3942(11) . ?
C2 C3 1.4519(11) . ?
C7' O1' 1.4781(10) . ?
C7' C6' 1.5317(11) . ?
C7' C8' 1.5329(12) . ?
N1 C8A 1.3961(11) . ?
N1 C9 1.4666(11) . ?
C3 C4 1.3593(11) . ?
C3 C1' 1.4538(11) . ?
C1' H1' 0.9500 . ?
C4 O1' 1.3542(9) . ?
C4 C4A 1.4383(11) . ?
C4' C5' 1.5261(13) . ?
C4' C3' 1.5392(12) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C5 C6 1.3843(12) . ?
C5 C4A 1.4058(12) . ?
C5 H5 0.9500 . ?
C5' C6' 1.5292(12) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C8 C7 1.3826(13) . ?
C8 C8A 1.4074(11) . ?
C8 H8 0.9500 . ?
C3' C10' 1.5373(12) . ?
C3' C9' 1.5448(12) . ?
C6 C7 1.3964(14) . ?
C6 H6 0.9500 . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C7 H7 0.9500 . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C8A C4A 1.4126(11) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 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
C1' C2' C3' 122.68(7) . . ?
C1' C2' C7' 118.32(7) . . ?
C3' C2' C7' 118.95(7) . . ?
O1 C2 N1 120.88(7) . . ?
O1 C2 C3 122.51(8) . . ?
N1 C2 C3 116.62(7) . . ?
O1' C7' C2' 111.22(6) . . ?
O1' C7' C6' 102.49(6) . . ?
C2' C7' C6' 112.17(7) . . ?
O1' C7' C8' 105.63(7) . . ?
C2' C7' C8' 112.18(7) . . ?
C6' C7' C8' 112.54(7) . . ?
C2 N1 C8A 123.04(7) . . ?
C2 N1 C9 117.42(7) . . ?
C8A N1 C9 119.46(7) . . ?
C4 C3 C2 120.78(7) . . ?
C4 C3 C1' 119.12(7) . . ?
C2 C3 C1' 119.85(7) . . ?
C2' C1' C3 120.93(7) . . ?
C2' C1' H1' 119.5 . . ?
C3 C1' H1' 119.5 . . ?
O1' C4 C3 121.36(7) . . ?
O1' C4 C4A 116.73(7) . . ?
C3 C4 C4A 121.86(7) . . ?
C5' C4' C3' 113.25(7) . . ?
C5' C4' H4'A 108.9 . . ?
C3' C4' H4'A 108.9 . . ?
C5' C4' H4'B 108.9 . . ?
C3' C4' H4'B 108.9 . . ?
H4'A C4' H4'B 107.7 . . ?
C6 C5 C4A 120.46(8) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C4' C5' C6' 109.72(7) . . ?
C4' C5' H5'A 109.7 . . ?
C6' C5' H5'A 109.7 . . ?
C4' C5' H5'B 109.7 . . ?
C6' C5' H5'B 109.7 . . ?
H5'A C5' H5'B 108.2 . . ?
C7 C8 C8A 119.72(8) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C2' C3' C10' 111.60(7) . . ?
C2' C3' C4' 109.09(7) . . ?
C10' C3' C4' 107.90(7) . . ?
C2' C3' C9' 110.50(7) . . ?
C10' C3' C9' 107.00(7) . . ?
C4' C3' C9' 110.72(7) . . ?
C5 C6 C7 119.31(8) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C5' C6' C7' 112.69(7) . . ?
C5' C6' H6'A 109.1 . . ?
C7' C6' H6'A 109.1 . . ?
C5' C6' H6'B 109.1 . . ?
C7' C6' H6'B 109.1 . . ?
H6'A C6' H6'B 107.8 . . ?
C8 C7 C6 121.52(8) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3' C10' H10D 109.5 . . ?
C3' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C3' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N1 C8A C8 120.89(8) . . ?
N1 C8A C4A 119.98(7) . . ?
C8 C8A C4A 119.12(8) . . ?
C5 C4A C8A 119.84(8) . . ?
C5 C4A C4 122.65(7) . . ?
C8A C4A C4 117.49(7) . . ?
C4 O1' C7' 118.07(6) . . ?
C3' C9' H9'A 109.5 . . ?
C3' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C3' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1' C2' C7' O1' 26.59(10) . . . . ?
C3' C2' C7' O1' -155.95(7) . . . . ?
C1' C2' C7' C6' 140.72(8) . . . . ?
C3' C2' C7' C6' -41.82(10) . . . . ?
C1' C2' C7' C8' -91.47(9) . . . . ?
C3' C2' C7' C8' 86.00(9) . . . . ?
O1 C2 N1 C8A 176.56(8) . . . . ?
C3 C2 N1 C8A -3.27(12) . . . . ?
O1 C2 N1 C9 0.01(12) . . . . ?
C3 C2 N1 C9 -179.83(7) . . . . ?
O1 C2 C3 C4 -174.43(8) . . . . ?
N1 C2 C3 C4 5.40(12) . . . . ?
O1 C2 C3 C1' -0.22(12) . . . . ?
N1 C2 C3 C1' 179.61(7) . . . . ?
C3' C2' C1' C3 179.92(7) . . . . ?
C7' C2' C1' C3 -2.72(12) . . . . ?
C4 C3 C1' C2' -12.16(12) . . . . ?
C2 C3 C1' C2' 173.53(8) . . . . ?
C2 C3 C4 O1' 174.08(7) . . . . ?
C1' C3 C4 O1' -0.17(12) . . . . ?
C2 C3 C4 C4A -3.46(12) . . . . ?
C1' C3 C4 C4A -177.71(7) . . . . ?
C3' C4' C5' C6' 60.73(10) . . . . ?
C1' C2' C3' C10' -19.99(11) . . . . ?
C7' C2' C3' C10' 162.67(8) . . . . ?
C1' C2' C3' C4' -139.12(8) . . . . ?
C7' C2' C3' C4' 43.54(10) . . . . ?
C1' C2' C3' C9' 98.94(9) . . . . ?
C7' C2' C3' C9' -78.40(9) . . . . ?
C5' C4' C3' C2' -52.35(9) . . . . ?
C5' C4' C3' C10' -173.76(7) . . . . ?
C5' C4' C3' C9' 69.46(9) . . . . ?
C4A C5 C6 C7 -0.34(14) . . . . ?
C4' C5' C6' C7' -56.99(10) . . . . ?
O1' C7' C6' C5' 166.44(7) . . . . ?
C2' C7' C6' C5' 47.05(10) . . . . ?
C8' C7' C6' C5' -80.57(9) . . . . ?
C8A C8 C7 C6 -0.33(14) . . . . ?
C5 C6 C7 C8 1.05(14) . . . . ?
C2 N1 C8A C8 178.56(8) . . . . ?
C9 N1 C8A C8 -4.95(12) . . . . ?
C2 N1 C8A C4A -0.86(12) . . . . ?
C9 N1 C8A C4A 175.63(8) . . . . ?
C7 C8 C8A N1 179.50(8) . . . . ?
C7 C8 C8A C4A -1.08(13) . . . . ?
C6 C5 C4A C8A -1.06(13) . . . . ?
C6 C5 C4A C4 177.08(8) . . . . ?
N1 C8A C4A C5 -178.81(7) . . . . ?
C8 C8A C4A C5 1.76(12) . . . . ?
N1 C8A C4A C4 2.96(12) . . . . ?
C8 C8A C4A C4 -176.47(7) . . . . ?
O1' C4 C4A C5 3.38(12) . . . . ?
C3 C4 C4A C5 -178.97(8) . . . . ?
O1' C4 C4A C8A -178.44(7) . . . . ?
C3 C4 C4A C8A -0.79(12) . . . . ?
C3 C4 O1' C7' 26.88(11) . . . . ?
C4A C4 O1' C7' -155.46(7) . . . . ?
C2' C7' O1' C4 -38.78(9) . . . . ?
C6' C7' O1' C4 -158.82(7) . . . . ?
C8' C7' O1' C4 83.17(8) . . . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 and CDCl3'
