# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_d19364
_database_code_depnum_ccdc_archive 'CCDC 1819135'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O'
_chemical_formula_sum            'C20 H19 N O'
_chemical_formula_weight         289.36

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.5578(12)
_cell_length_b                   20.653(2)
_cell_length_c                   8.4644(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.514(6)
_cell_angle_gamma                90.00
_cell_volume                     1584.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8229
_cell_measurement_theta_min      2.451
_cell_measurement_theta_max      24.853

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21837
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2789
_reflns_number_gt                2099
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0742P)²+1.9465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1904(3) 0.51912(13) 0.4632(4) 0.0394(7) Uani 1 1 d . . .
H1 H 0.0819 0.5173 0.4455 0.047 Uiso 1 1 calc R . .
C2 C 0.2152(3) 0.50112(13) 0.3025(3) 0.0386(7) Uani 1 1 d . . .
C3 C 0.1218(3) 0.46089(14) 0.1866(4) 0.0445(7) Uani 1 1 d . . .
H3 H 0.0361 0.4448 0.2074 0.053 Uiso 1 1 calc R . .
C4 C 0.1478(4) 0.44317(17) 0.0418(4) 0.0593(9) Uani 1 1 d . . .
H4 H 0.0817 0.4151 -0.0358 0.071 Uiso 1 1 calc R . .
C5 C 0.2726(4) 0.46706(18) 0.0110(4) 0.0626(10) Uani 1 1 d . . .
H5 H 0.2916 0.4556 -0.0889 0.075 Uiso 1 1 calc R . .
C6 C 0.3678(4) 0.50677(17) 0.1230(4) 0.0537(8) Uani 1 1 d . . .
H6 H 0.4535 0.5223 0.1013 0.064 Uiso 1 1 calc R . .
C7 C 0.3404(3) 0.52518(14) 0.2715(4) 0.0429(7) Uani 1 1 d . . .
C8 C 0.3975(3) 0.59545(13) 0.4948(4) 0.0438(7) Uani 1 1 d . . .
C9 C 0.4825(4) 0.63737(15) 0.6264(5) 0.0566(9) Uani 1 1 d . . .
C10 C 0.6289(4) 0.66333(17) 0.6327(6) 0.0774(13) Uani 1 1 d . . .
H10A H 0.7027 0.6288 0.6652 0.116 Uiso 1 1 calc R . .
H10B H 0.6565 0.6985 0.7143 0.116 Uiso 1 1 calc R . .
H10C H 0.6241 0.6799 0.5225 0.116 Uiso 1 1 calc R . .
C11 C 0.4077(4) 0.64557(15) 0.7389(4) 0.0601(10) Uani 1 1 d . . .
C12 C 0.4600(5) 0.6821(2) 0.8961(6) 0.0954(16) Uani 1 1 d . . .
H12A H 0.5522 0.7044 0.9026 0.143 Uiso 1 1 calc R . .
H12B H 0.4774 0.6522 0.9903 0.143 Uiso 1 1 calc R . .
H12C H 0.3854 0.7140 0.9000 0.143 Uiso 1 1 calc R . .
C13 C 0.2641(4) 0.61071(16) 0.6863(4) 0.0540(8) Uani 1 1 d . . .
H13A H 0.1832 0.6397 0.6917 0.065 Uiso 1 1 calc R . .
H13B H 0.2674 0.5727 0.7587 0.065 Uiso 1 1 calc R . .
C14 C 0.2416(3) 0.58925(13) 0.5049(3) 0.0393(7) Uani 1 1 d . . .
C15 C 0.1346(3) 0.63468(13) 0.3783(4) 0.0402(7) Uani 1 1 d . . .
C16 C 0.1756(3) 0.67138(14) 0.2635(4) 0.0483(8) Uani 1 1 d . . .
H16 H 0.2728 0.6673 0.2575 0.058 Uiso 1 1 calc R . .
C17 C 0.0784(3) 0.71380(15) 0.1576(4) 0.0543(8) Uani 1 1 d . . .
H17 H 0.1097 0.7390 0.0811 0.065 Uiso 1 1 calc R . .
C18 C -0.0639(4) 0.71973(16) 0.1624(4) 0.0553(8) Uani 1 1 d . . .
H18 H -0.1305 0.7493 0.0906 0.066 Uiso 1 1 calc R . .
C19 C -0.1085(3) 0.68249(15) 0.2720(4) 0.0492(8) Uani 1 1 d . . .
H19 H -0.2068 0.6859 0.2746 0.059 Uiso 1 1 calc R . .
C20 C -0.0110(3) 0.63994(14) 0.3787(4) 0.0419(7) Uani 1 1 d . . .
H20 H -0.0436 0.6141 0.4531 0.050 Uiso 1 1 calc R . .
N1 N 0.4436(2) 0.56618(11) 0.3868(3) 0.0407(6) Uani 1 1 d . . .
O1 O 0.2626(2) 0.47565(9) 0.5970(2) 0.0427(5) Uani 1 1 d . . .
H1' H 0.3476 0.4653 0.5817 0.051 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.438(3) . ?
C1 C2 1.500(4) . ?
C1 C14 1.534(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.376(4) . ?
C2 C7 1.395(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.361(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(4) . ?
C6 H6 0.9500 . ?
C7 N1 1.425(4) . ?
C8 N1 1.285(4) . ?
C8 C9 1.441(4) . ?
C8 C14 1.525(4) . ?
C9 C11 1.371(5) . ?
C9 C10 1.484(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.472(5) . ?
C11 C13 1.487(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.546(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.542(4) . ?
C15 C16 1.383(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O1 H1' 0.8885 . ?

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
O1 C1 C2 112.6(2) . . ?
O1 C1 C14 111.7(2) . . ?
C2 C1 C14 108.2(2) . . ?
O1 C1 H1 108.1 . . ?
C2 C1 H1 108.1 . . ?
C14 C1 H1 108.1 . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 122.8(3) . . ?
C7 C2 C1 118.3(3) . . ?
C4 C3 C2 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.9(3) . . ?
C2 C7 N1 122.1(3) . . ?
C6 C7 N1 119.0(3) . . ?
N1 C8 C9 126.7(3) . . ?
N1 C8 C14 124.2(3) . . ?
C9 C8 C14 109.1(3) . . ?
C11 C9 C8 108.7(3) . . ?
C11 C9 C10 128.7(3) . . ?
C8 C9 C10 122.6(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 126.0(4) . . ?
C9 C11 C13 111.6(3) . . ?
C12 C11 C13 122.3(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 105.1(3) . . ?
C11 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
C11 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C8 C14 C1 108.2(2) . . ?
C8 C14 C15 110.7(2) . . ?
C1 C14 C15 108.8(2) . . ?
C8 C14 C13 101.6(2) . . ?
C1 C14 C13 115.7(2) . . ?
C15 C14 C13 111.6(2) . . ?
C16 C15 C20 117.6(3) . . ?
C16 C15 C14 123.3(2) . . ?
C20 C15 C14 119.1(2) . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C8 N1 C7 116.6(2) . . ?
C1 O1 H1' 105.6 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_d19332
_database_code_depnum_ccdc_archive 'CCDC 1819136'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Br N O'
_chemical_formula_sum            'C18 H20 Br N O'
_chemical_formula_weight         346.26

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6388(10)
_cell_length_b                   11.2206(13)
_cell_length_c                   11.3511(13)
_cell_angle_alpha                116.079(3)
_cell_angle_beta                 109.218(4)
_cell_angle_gamma                91.505(4)
_cell_volume                     808.23(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      3.267
_cell_measurement_theta_max      25.06

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4078
_exptl_absorpt_correction_T_max  0.7017
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26621
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.07
_reflns_number_total             2830
_reflns_number_gt                2682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0304P)²+0.3720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2830
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4367(3) 0.81548(19) 0.7066(2) 0.0391(4) Uani 1 1 d . . .
C2 C 0.3160(3) 0.7474(2) 0.5659(2) 0.0414(4) Uani 1 1 d . . .
H2 H 0.2729 0.7958 0.5146 0.050 Uiso 1 1 calc R . .
C3 C 0.2584(3) 0.60867(19) 0.5005(2) 0.0365(4) Uani 1 1 d . . .
H3 H 0.1758 0.5625 0.4035 0.044 Uiso 1 1 calc R . .
C4 C 0.3178(2) 0.53357(18) 0.57245(18) 0.0311(4) Uani 1 1 d . . .
C5 C 0.4390(3) 0.6070(2) 0.7156(2) 0.0404(4) Uani 1 1 d . . .
H5 H 0.4816 0.5598 0.7682 0.049 Uiso 1 1 calc R . .
C6 C 0.4982(3) 0.7458(2) 0.7822(2) 0.0438(4) Uani 1 1 d . . .
H6 H 0.5805 0.7931 0.8792 0.053 Uiso 1 1 calc R . .
C7 C 0.2509(2) 0.38721(18) 0.49927(17) 0.0300(4) Uani 1 1 d . . .
C8 C 0.1050(2) 0.31130(18) 0.35028(17) 0.0335(4) Uani 1 1 d . . .
H8A H -0.0156 0.3434 0.3443 0.040 Uiso 1 1 calc R . .
H8B H 0.1501 0.3232 0.2830 0.040 Uiso 1 1 calc R . .
C9 C 0.0797(2) 0.16627(19) 0.31842(19) 0.0355(4) Uani 1 1 d . . .
C10 C -0.0481(3) 0.0543(2) 0.1771(2) 0.0504(5) Uani 1 1 d . . .
H10A H 0.0132 0.0344 0.1089 0.076 Uiso 1 1 calc R . .
H10B H -0.1674 0.0820 0.1440 0.076 Uiso 1 1 calc R . .
H10C H -0.0738 -0.0269 0.1857 0.076 Uiso 1 1 calc R . .
C11 C 0.1944(2) 0.15662(18) 0.43122(19) 0.0337(4) Uani 1 1 d . . .
C12 C 0.2222(3) 0.0320(2) 0.4467(2) 0.0447(5) Uani 1 1 d . . .
H12A H 0.1798 0.0353 0.5206 0.067 Uiso 1 1 calc R . .
H12B H 0.3566 0.0275 0.4732 0.067 Uiso 1 1 calc R . .
H12C H 0.1482 -0.0483 0.3566 0.067 Uiso 1 1 calc R . .
C13 C 0.3002(2) 0.29301(18) 0.54136(17) 0.0299(3) Uani 1 1 d . . .
C14 C 0.4258(2) 0.32036(17) 0.78305(18) 0.0313(4) Uani 1 1 d . . .
C15 C 0.2314(3) 0.3133(3) 0.7840(2) 0.0521(5) Uani 1 1 d . . .
C16 C 0.5801(3) 0.33299(18) 0.89617(18) 0.0352(4) Uani 1 1 d . . .
H16 H 0.5610 0.3418 0.9780 0.042 Uiso 1 1 calc R . .
C17 C 0.7660(3) 0.33357(18) 0.89697(19) 0.0371(4) Uani 1 1 d . . .
C18 C 0.9204(3) 0.3379(2) 1.0236(2) 0.0540(5) Uani 1 1 d . . .
Br1 Br 0.51708(3) 1.006202(19) 0.79707(2) 0.05111(10) Uani 1 1 d . . .
N1 N 0.4473(2) 0.31520(15) 0.66889(15) 0.0313(3) Uani 1 1 d . . .
O1 O 0.80812(18) 0.33011(16) 0.79873(14) 0.0474(3) Uani 1 1 d . . .
H1' H 0.5715 0.3242 0.6760 0.057 Uiso 1 1 d R . .
H15A H 0.1793 0.3808 0.7619 0.057 Uiso 1 1 d R . .
H15B H 0.1564 0.2327 0.7203 0.057 Uiso 1 1 d R . .
H15C H 0.2305 0.3391 0.8792 0.057 Uiso 1 1 d R . .
H18A H 1.0006 0.4269 1.0773 0.057 Uiso 1 1 d R . .
H18B H 0.9818 0.2575 0.9887 0.057 Uiso 1 1 d R . .
H18C H 0.8691 0.3308 1.0867 0.057 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C1 Br1 1.8961(19) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(3) . ?
C4 C7 1.458(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C13 1.354(2) . ?
C7 C8 1.507(2) . ?
C8 C9 1.495(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.345(3) . ?
C9 C10 1.496(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.465(2) . ?
C11 C12 1.496(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.421(2) . ?
C14 N1 1.336(2) . ?
C14 C16 1.376(2) . ?
C14 C15 1.489(3) . ?
C15 H15A 0.9549 . ?
C15 H15B 0.8910 . ?
C15 H15C 0.9907 . ?
C16 C17 1.417(3) . ?
C16 H16 0.9500 . ?
C17 O1 1.244(2) . ?
C17 C18 1.509(3) . ?
C18 H18A 0.9645 . ?
C18 H18B 1.0108 . ?
C18 H18C 0.9528 . ?
N1 H1' 0.9247 . ?

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 C1 C6 120.53(18) . . ?
C2 C1 Br1 119.63(14) . . ?
C6 C1 Br1 119.83(15) . . ?
C3 C2 C1 119.40(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 122.14(17) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 116.50(17) . . ?
C3 C4 C7 120.12(16) . . ?
C5 C4 C7 123.37(15) . . ?
C6 C5 C4 121.94(17) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.49(18) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C13 C7 C4 130.85(16) . . ?
C13 C7 C8 106.27(15) . . ?
C4 C7 C8 122.87(15) . . ?
C9 C8 C7 104.79(14) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C11 C9 C10 128.15(18) . . ?
C11 C9 C8 109.32(15) . . ?
C10 C9 C8 122.44(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C13 107.95(16) . . ?
C9 C11 C12 128.44(17) . . ?
C13 C11 C12 123.56(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 N1 126.50(16) . . ?
C7 C13 C11 111.65(15) . . ?
N1 C13 C11 121.59(15) . . ?
N1 C14 C16 120.42(16) . . ?
N1 C14 C15 118.03(16) . . ?
C16 C14 C15 121.55(16) . . ?
C14 C15 H15A 107.3 . . ?
C14 C15 H15B 112.4 . . ?
H15A C15 H15B 108.9 . . ?
C14 C15 H15C 112.9 . . ?
H15A C15 H15C 104.3 . . ?
H15B C15 H15C 110.7 . . ?
C14 C16 C17 123.39(16) . . ?
C14 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
O1 C17 C16 123.46(16) . . ?
O1 C17 C18 118.45(18) . . ?
C16 C17 C18 118.09(18) . . ?
C17 C18 H18A 107.9 . . ?
C17 C18 H18B 108.3 . . ?
H18A C18 H18B 117.6 . . ?
C17 C18 H18C 110.7 . . ?
H18A C18 H18C 104.5 . . ?
H18B C18 H18C 107.8 . . ?
C14 N1 C13 126.37(14) . . ?
C14 N1 H1' 114.2 . . ?
C13 N1 H1' 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_TWIN5
_database_code_depnum_ccdc_archive 'CCDC 1819138'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H39 Cl3 N2 O6'
_chemical_formula_weight         786.11

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'
Cl Cl 0.1484 0.1585 '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                   11.282(7)
_cell_length_b                   11.457(7)
_cell_length_c                   14.934(9)
_cell_angle_alpha                84.071(19)
_cell_angle_beta                 88.539(15)
_cell_angle_gamma                84.074(13)
_cell_volume                     1909(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6877
_cell_measurement_theta_min      2.2687
_cell_measurement_theta_max      25.0475

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.292
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8556
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6443
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.371
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             6443
_reflns_number_gt                4896
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component 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)+(0.0476P)²+0.1940P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6443
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.8091(3) 0.4161(2) 0.61655(17) 0.0149(6) Uani 1 1 d . . . . .
H1 H 0.7454 0.3789 0.6536 0.018 Uiso 1 1 calc R U . . .
C2 C 1.0340(3) 0.3893(2) 0.62267(17) 0.0150(6) Uani 1 1 d . . . . .
C3 C 1.1420(3) 0.3181(3) 0.63341(18) 0.0184(7) Uani 1 1 d . . . . .
H3 H 1.2152 0.3523 0.6256 0.022 Uiso 1 1 calc R U . . .
C4 C 1.1426(3) 0.1976(3) 0.65545(19) 0.0238(7) Uani 1 1 d . . . . .
H4 H 1.2162 0.1498 0.6634 0.029 Uiso 1 1 calc R U . . .
C5 C 1.0366(3) 0.1463(3) 0.66595(19) 0.0237(7) Uani 1 1 d . . . . .
H5 H 1.0375 0.0637 0.6811 0.028 Uiso 1 1 calc R U . . .
C6 C 0.9286(3) 0.2164(3) 0.65428(18) 0.0195(7) Uani 1 1 d . . . . .
H6 H 0.8561 0.1808 0.6612 0.023 Uiso 1 1 calc R U . . .
C7 C 0.9253(3) 0.3383(2) 0.63262(17) 0.0149(6) Uani 1 1 d . . . . .
C8 C 0.8239(2) 0.5360(2) 0.65168(17) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.7305(3) 0.6404(2) 0.61925(19) 0.0183(6) Uani 1 1 d . . . . .
H9A H 0.6905 0.6241 0.5643 0.022 Uiso 1 1 calc R U . . .
H9B H 0.6695 0.6552 0.6667 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8032(3) 0.7440(2) 0.59996(18) 0.0163(6) Uani 1 1 d . . . . .
C11 C 0.9185(3) 0.7053(2) 0.59377(17) 0.0160(6) Uani 1 1 d . . . . .
C12 C 0.9402(2) 0.5786(2) 0.61331(17) 0.0135(6) Uani 1 1 d . . . . .
C13 C 1.0952(3) 0.7868(2) 0.6226(2) 0.0189(7) Uani 1 1 d . . . . .
C14 C 1.1874(3) 0.8595(3) 0.5768(2) 0.0258(7) Uani 1 1 d . . . . .
H14A H 1.2401 0.8816 0.6220 0.039 Uiso 1 1 calc R U . . .
H14B H 1.1476 0.9310 0.5443 0.039 Uiso 1 1 calc R U . . .
H14C H 1.2345 0.8133 0.5342 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7494(3) 0.8689(3) 0.5881(2) 0.0269(7) Uani 1 1 d . . . . .
H15A H 0.8128 0.9216 0.5846 0.040 Uiso 1 1 calc R U . . .
H15B H 0.6964 0.8847 0.6394 0.040 Uiso 1 1 calc R U . . .
H15C H 0.7036 0.8824 0.5324 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8248(2) 0.5219(2) 0.75550(17) 0.0129(6) Uani 1 1 d . . . . .
C17 C 0.9217(3) 0.5472(2) 0.80432(18) 0.0159(6) Uani 1 1 d . . . . .
H17 H 0.9919 0.5696 0.7736 0.019 Uiso 1 1 calc R U . . .
C18 C 0.9153(3) 0.5394(3) 0.89771(19) 0.0198(7) Uani 1 1 d . . . . .
H18 H 0.9812 0.5575 0.9302 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8147(3) 0.5057(2) 0.94440(19) 0.0207(7) Uani 1 1 d . . . . .
H19 H 0.8114 0.5007 1.0083 0.025 Uiso 1 1 calc R U . . .
C20 C 0.7188(3) 0.4793(3) 0.89649(19) 0.0217(7) Uani 1 1 d . . . . .
H20 H 0.6498 0.4547 0.9277 0.026 Uiso 1 1 calc R U . . .
C21 C 0.7236(3) 0.4888(3) 0.80340(19) 0.0197(7) Uani 1 1 d . . . . .
H21 H 0.6565 0.4724 0.7714 0.024 Uiso 1 1 calc R U . . .
C22 C 0.5704(3) 0.2013(2) 0.88141(17) 0.0162(6) Uani 1 1 d . . . . .
H22 H 0.6051 0.2683 0.8453 0.019 Uiso 1 1 calc R U . . .
C23 C 0.6533(3) 0.0905(3) 0.87207(18) 0.0180(7) Uani 1 1 d . . . . .
C24 C 0.7742(3) 0.0932(3) 0.85277(19) 0.0231(7) Uani 1 1 d . . . . .
H24 H 0.8070 0.1668 0.8446 0.028 Uiso 1 1 calc R U . . .
C25 C 0.8475(3) -0.0103(3) 0.8453(2) 0.0277(8) Uani 1 1 d . . . . .
H25 H 0.9299 -0.0071 0.8316 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8010(3) -0.1188(3) 0.85763(19) 0.0259(7) Uani 1 1 d . . . . .
H26 H 0.8514 -0.1895 0.8523 0.031 Uiso 1 1 calc R U . . .
C27 C 0.6802(3) -0.1232(3) 0.87789(18) 0.0198(7) Uani 1 1 d . . . . .
H27 H 0.6485 -0.1971 0.8878 0.024 Uiso 1 1 calc R U . . .
C28 C 0.4120(2) 0.0670(2) 0.88158(17) 0.0132(6) Uani 1 1 d . . . . .
C29 C 0.2844(3) 0.0843(2) 0.89705(17) 0.0145(6) Uani 1 1 d . . . . .
C30 C 0.2410(3) 0.1975(3) 0.88423(18) 0.0174(6) Uani 1 1 d . . . . .
C31 C 0.3415(3) 0.2731(2) 0.86053(19) 0.0170(6) Uani 1 1 d . . . . .
H31A H 0.3587 0.3168 0.9117 0.020 Uiso 1 1 calc R U . . .
H31B H 0.3211 0.3304 0.8076 0.020 Uiso 1 1 calc R U . . .
C32 C 0.4503(3) 0.1851(2) 0.83892(17) 0.0147(6) Uani 1 1 d . . . . .
C33 C 0.1145(3) 0.2474(3) 0.8955(2) 0.0247(7) Uani 1 1 d . . . . .
H33A H 0.0639 0.1829 0.9081 0.037 Uiso 1 1 calc R U . . .
H33B H 0.0883 0.2956 0.8401 0.037 Uiso 1 1 calc R U . . .
H33C H 0.1082 0.2965 0.9458 0.037 Uiso 1 1 calc R U . . .
O6 O 0.21828(17) -0.00783(16) 0.93042(12) 0.0169(4) Uani 1 1 d . . . . .
C35 C 0.2042(2) -0.0905(2) 0.87274(19) 0.0151(6) Uani 1 1 d . . . . .
C36 C 0.4696(2) 0.1847(2) 0.73689(17) 0.0127(6) Uani 1 1 d . . . . .
C37 C 0.4974(3) 0.2884(3) 0.68614(18) 0.0184(7) Uani 1 1 d . . . . .
H37 H 0.5021 0.3576 0.7153 0.022 Uiso 1 1 calc R U . . .
C38 C 0.5183(3) 0.2915(3) 0.59376(19) 0.0226(7) Uani 1 1 d . . . . .
H38 H 0.5382 0.3623 0.5605 0.027 Uiso 1 1 calc R U . . .
C39 C 0.5102(3) 0.1921(3) 0.55043(19) 0.0220(7) Uani 1 1 d . . . . .
H39 H 0.5248 0.1936 0.4874 0.026 Uiso 1 1 calc R U . . .
C40 C 0.4804(3) 0.0896(3) 0.60012(18) 0.0203(7) Uani 1 1 d . . . . .
H40 H 0.4737 0.0211 0.5705 0.024 Uiso 1 1 calc R U . . .
C41 C 0.4604(3) 0.0859(2) 0.69226(18) 0.0160(6) Uani 1 1 d . . . . .
H41 H 0.4402 0.0150 0.7251 0.019 Uiso 1 1 calc R U . . .
C42 C 0.6058(2) -0.0191(2) 0.88361(17) 0.0149(6) Uani 1 1 d . . . . .
C43 C 0.3645(3) 0.6718(2) 0.75043(19) 0.0205(7) Uani 1 1 d . . . . .
H43 H 0.2846 0.7182 0.7535 0.025 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36972(9) 0.59082(7) 0.65624(6) 0.0378(2) Uani 1 1 d . . . . .
Cl2 Cl 0.38617(8) 0.57709(8) 0.85096(5) 0.0392(2) Uani 1 1 d . . . . .
Cl3 Cl 0.47550(7) 0.77029(7) 0.73925(6) 0.0373(2) Uani 1 1 d . . . . .
N1 N 1.0375(2) 0.5136(2) 0.59956(14) 0.0144(5) Uani 1 1 d . . . . .
N2 N 0.4816(2) -0.02757(19) 0.90259(14) 0.0135(5) Uani 1 1 d . . . . .
O1 O 1.00703(17) 0.77792(16) 0.56353(12) 0.0174(4) Uani 1 1 d . . . . .
O2 O 1.09590(19) 0.74173(19) 0.69872(13) 0.0265(5) Uani 1 1 d . . . . .
O3 O 0.77450(17) 0.42757(17) 0.52484(12) 0.0177(4) Uani 1 1 d . . . . .
H3A H 0.8332 0.4427 0.4915 0.027 Uiso 1 1 calc R U . . .
O4 O 0.55780(19) 0.22916(17) 0.97266(12) 0.0207(5) Uani 1 1 d . . . . .
H4A H 0.5566 0.1666 1.0073 0.031 Uiso 1 1 calc R U . . .
O5 O 0.23493(18) -0.07896(17) 0.79547(13) 0.0210(5) Uani 1 1 d . . . . .
C34 C 0.1463(3) -0.1920(3) 0.9203(2) 0.0232(7) Uani 1 1 d . . . . .
H34A H 0.1192 -0.2402 0.8758 0.035 Uiso 1 1 calc R U . . .
H34B H 0.0778 -0.1618 0.9559 0.035 Uiso 1 1 calc R U . . .
H34C H 0.2039 -0.2402 0.9602 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
C1 O3 1.423(3) . ?
C1 C7 1.517(4) . ?
C1 C8 1.546(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.398(4) . ?
C2 C7 1.411(4) . ?
C2 N1 1.434(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(4) . ?
C6 H6 0.9500 . ?
C8 C12 1.524(4) . ?
C8 C16 1.542(4) . ?
C8 C9 1.556(4) . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.335(4) . ?
C10 C15 1.490(4) . ?
C11 O1 1.402(3) . ?
C11 C12 1.447(4) . ?
C12 N1 1.286(4) . ?
C13 O2 1.199(3) . ?
C13 O1 1.365(3) . ?
C13 C14 1.506(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.397(4) . ?
C16 C17 1.400(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O4 1.432(3) . ?
C22 C23 1.513(4) . ?
C22 C32 1.546(4) . ?
C22 H22 1.0000 . ?
C23 C24 1.390(4) . ?
C23 C42 1.408(4) . ?
C24 C25 1.387(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(4) . ?
C26 H26 0.9500 . ?
C27 C42 1.395(4) . ?
C27 H27 0.9500 . ?
C28 N2 1.287(4) . ?
C28 C29 1.449(4) . ?
C28 C32 1.533(4) . ?
C29 C30 1.335(4) . ?
C29 O6 1.398(3) . ?
C30 C33 1.494(4) . ?
C30 C31 1.510(4) . ?
C31 C32 1.556(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C36 1.534(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O6 C35 1.368(3) . ?
C35 O5 1.194(3) . ?
C35 C34 1.498(4) . ?
C36 C41 1.386(4) . ?
C36 C37 1.401(4) . ?
C37 C38 1.391(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.379(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.389(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.386(4) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 N2 1.433(4) . ?
C43 Cl1 1.760(3) . ?
C43 Cl3 1.764(3) . ?
C43 Cl2 1.766(3) . ?
C43 H43 1.0000 . ?
O3 H3A 0.8400 . ?
O4 H4A 0.8400 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
O3 C1 C7 112.4(2) . . ?
O3 C1 C8 112.9(2) . . ?
C7 C1 C8 107.5(2) . . ?
O3 C1 H1 108.0 . . ?
C7 C1 H1 108.0 . . ?
C8 C1 H1 108.0 . . ?
C3 C2 C7 120.0(3) . . ?
C3 C2 N1 118.4(3) . . ?
C7 C2 N1 121.6(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 118.5(3) . . ?
C6 C7 C1 122.1(3) . . ?
C2 C7 C1 119.3(2) . . ?
C12 C8 C16 110.8(2) . . ?
C12 C8 C1 108.4(2) . . ?
C16 C8 C1 109.9(2) . . ?
C12 C8 C9 102.4(2) . . ?
C16 C8 C9 108.9(2) . . ?
C1 C8 C9 116.2(2) . . ?
C10 C9 C8 104.1(2) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C15 127.0(3) . . ?
C11 C10 C9 109.6(2) . . ?
C15 C10 C9 123.3(3) . . ?
C10 C11 O1 123.5(2) . . ?
C10 C11 C12 112.5(2) . . ?
O1 C11 C12 123.8(3) . . ?
N1 C12 C11 127.1(2) . . ?
N1 C12 C8 126.3(2) . . ?
C11 C12 C8 106.7(2) . . ?
O2 C13 O1 123.3(3) . . ?
O2 C13 C14 127.2(3) . . ?
O1 C13 C14 109.5(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.1(2) . . ?
C21 C16 C8 119.5(2) . . ?
C17 C16 C8 122.3(2) . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 121.4(3) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
O4 C22 C23 112.5(2) . . ?
O4 C22 C32 113.0(2) . . ?
C23 C22 C32 107.6(2) . . ?
O4 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
C32 C22 H22 107.8 . . ?
C24 C23 C42 119.1(3) . . ?
C24 C23 C22 122.4(3) . . ?
C42 C23 C22 118.5(3) . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C42 120.1(3) . . ?
C26 C27 H27 120.0 . . ?
C42 C27 H27 120.0 . . ?
N2 C28 C29 127.0(2) . . ?
N2 C28 C32 126.0(3) . . ?
C29 C28 C32 107.0(2) . . ?
C30 C29 O6 124.6(3) . . ?
C30 C29 C28 112.7(2) . . ?
O6 C29 C28 122.3(2) . . ?
C29 C30 C33 127.2(3) . . ?
C29 C30 C31 109.6(3) . . ?
C33 C30 C31 123.1(2) . . ?
C30 C31 C32 105.1(2) . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31B 110.7 . . ?
C32 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C28 C32 C36 111.4(2) . . ?
C28 C32 C22 107.0(2) . . ?
C36 C32 C22 108.4(2) . . ?
C28 C32 C31 102.2(2) . . ?
C36 C32 C31 110.8(2) . . ?
C22 C32 C31 116.9(2) . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 O6 C29 116.0(2) . . ?
O5 C35 O6 122.4(2) . . ?
O5 C35 C34 127.0(3) . . ?
O6 C35 C34 110.6(2) . . ?
C41 C36 C37 118.2(3) . . ?
C41 C36 C32 122.8(2) . . ?
C37 C36 C32 119.0(2) . . ?
C38 C37 C36 121.0(3) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C39 C38 C37 120.1(3) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C40 119.2(3) . . ?
C38 C39 H39 120.4 . . ?
C40 C39 H39 120.4 . . ?
C41 C40 C39 120.9(3) . . ?
C41 C40 H40 119.5 . . ?
C39 C40 H40 119.5 . . ?
C36 C41 C40 120.6(3) . . ?
C36 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C27 C42 C23 120.1(3) . . ?
C27 C42 N2 118.2(2) . . ?
C23 C42 N2 121.7(3) . . ?
Cl1 C43 Cl3 109.66(16) . . ?
Cl1 C43 Cl2 110.99(16) . . ?
Cl3 C43 Cl2 109.49(16) . . ?
Cl1 C43 H43 108.9 . . ?
Cl3 C43 H43 108.9 . . ?
Cl2 C43 H43 108.9 . . ?
C12 N1 C2 115.8(2) . . ?
C28 N2 C42 115.6(2) . . ?
C13 O1 C11 116.6(2) . . ?
C1 O3 H3A 109.5 . . ?
C22 O4 H4A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_180108lt_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1819137'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N O5'
_chemical_formula_weight         379.40

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/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                   11.8837(10)
_cell_length_b                   10.0611(7)
_cell_length_c                   19.6889(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.518(3)
_cell_angle_gamma                90
_cell_volume                     2244.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5404
_cell_measurement_theta_min      2.2966
_cell_measurement_theta_max      26.3697

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19526
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4606
_reflns_number_gt                3773
_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.
 
 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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0369P)²+2.4635P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4606
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.61448(19) 0.41058(19) 0.24943(10) 0.0240(4) Uani 1 1 d . . . . .
H1 H 0.6262 0.3228 0.2744 0.029 Uiso 1 1 calc R U . . .
C2 C 0.48773(19) 0.42997(18) 0.20845(11) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.3971(2) 0.3633(2) 0.22468(12) 0.0311(5) Uani 1 1 d . . . . .
H3 H 0.4148 0.3003 0.2624 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2811(2) 0.3881(2) 0.18625(14) 0.0376(6) Uani 1 1 d . . . . .
H4 H 0.2193 0.3411 0.1971 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2547(2) 0.4810(2) 0.13219(14) 0.0357(5) Uani 1 1 d . . . . .
H5 H 0.1747 0.4982 0.1062 0.043 Uiso 1 1 calc R U . . .
C6 C 0.34452(19) 0.5496(2) 0.11546(12) 0.0296(5) Uani 1 1 d . . . . .
H6 H 0.3261 0.6142 0.0786 0.035 Uiso 1 1 calc R U . . .
C7 C 0.46075(18) 0.52297(19) 0.15299(11) 0.0233(4) Uani 1 1 d . . . . .
C8 C 0.65542(17) 0.54660(18) 0.15517(10) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.75014(17) 0.62092(19) 0.13241(11) 0.0241(4) Uani 1 1 d . . . . .
C10 C 0.89514(18) 0.5245(2) 0.21522(12) 0.0274(5) Uani 1 1 d . . . . .
C11 C 0.82575(18) 0.4230(2) 0.24284(11) 0.0288(5) Uani 1 1 d . . . . .
H11A H 0.8339 0.4429 0.2933 0.035 Uiso 1 1 calc R U . . .
H11B H 0.8597 0.3337 0.2408 0.035 Uiso 1 1 calc R U . . .
C12 C 0.69236(17) 0.42066(18) 0.19980(10) 0.0206(4) Uani 1 1 d . . . . .
C13 C 1.0256(2) 0.5001(3) 0.23681(16) 0.0467(7) Uani 1 1 d . . . . .
H13A H 1.0411 0.4139 0.2183 0.070 Uiso 1 1 calc R U . . .
H13B H 1.0571 0.5000 0.2889 0.070 Uiso 1 1 calc R U . . .
H13C H 1.0639 0.5706 0.2174 0.070 Uiso 1 1 calc R U . . .
C14 C 0.7102(2) 0.6802(2) 0.05913(13) 0.0354(5) Uani 1 1 d . . . . .
H14A H 0.7760 0.7279 0.0499 0.053 Uiso 1 1 calc R U . . .
H14B H 0.6451 0.7422 0.0557 0.053 Uiso 1 1 calc R U . . .
H14C H 0.6834 0.6093 0.0239 0.053 Uiso 1 1 calc R U . . .
C15 C 0.66516(16) 0.29804(18) 0.15052(10) 0.0193(4) Uani 1 1 d . . . . .
C16 C 0.68655(18) 0.17135(19) 0.18059(11) 0.0243(4) Uani 1 1 d . . . . .
H16 H 0.7152 0.1625 0.2309 0.029 Uiso 1 1 calc R U . . .
C17 C 0.66679(19) 0.0586(2) 0.13855(12) 0.0283(5) Uani 1 1 d . . . . .
H17 H 0.6822 -0.0266 0.1601 0.034 Uiso 1 1 calc R U . . .
C18 C 0.62467(18) 0.0697(2) 0.06541(12) 0.0276(5) Uani 1 1 d . . . . .
H18 H 0.6120 -0.0078 0.0365 0.033 Uiso 1 1 calc R U . . .
C19 C 0.60083(18) 0.1944(2) 0.03413(11) 0.0251(4) Uani 1 1 d . . . . .
H19 H 0.5710 0.2025 -0.0162 0.030 Uiso 1 1 calc R U . . .
C20 C 0.62084(17) 0.30744(19) 0.07681(10) 0.0213(4) Uani 1 1 d . . . . .
H20 H 0.6039 0.3925 0.0552 0.026 Uiso 1 1 calc R U . . .
C21 C 0.6796(2) 0.4882(2) 0.36974(12) 0.0361(6) Uani 1 1 d . . . . .
C22 C 0.7020(3) 0.6092(2) 0.41568(12) 0.0430(6) Uani 1 1 d . . . . .
H22A H 0.7355 0.5829 0.4657 0.065 Uiso 1 1 calc R U . . .
H22B H 0.6277 0.6567 0.4095 0.065 Uiso 1 1 calc R U . . .
H22C H 0.7577 0.6674 0.4020 0.065 Uiso 1 1 calc R U . . .
N1 N 0.55089(14) 0.59267(15) 0.13373(9) 0.0219(3) Uani 1 1 d . . . . .
O1 O 0.64679(15) 0.51925(13) 0.30093(7) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.6915(3) 0.37604(18) 0.39091(9) 0.0763(8) Uani 1 1 d . . . . .
O3 O 0.79630(13) 0.72587(14) 0.18179(9) 0.0335(4) Uani 1 1 d . . . . .
O4 O 0.87473(16) 0.65507(15) 0.24190(9) 0.0442(4) Uani 1 1 d . . . . .
O5 O 0.84825(13) 0.53721(14) 0.14037(8) 0.0278(3) 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
C1 O1 1.462(2) . ?
C1 C2 1.492(3) . ?
C1 C12 1.538(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.385(3) . ?
C2 C7 1.400(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 N1 1.424(2) . ?
C8 N1 1.273(3) . ?
C8 C9 1.527(3) . ?
C8 C12 1.529(3) . ?
C9 O5 1.408(2) . ?
C9 O3 1.428(2) . ?
C9 C14 1.500(3) . ?
C10 O5 1.416(3) . ?
C10 O4 1.462(2) . ?
C10 C13 1.499(3) . ?
C10 C11 1.513(3) . ?
C11 C12 1.556(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C15 1.542(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.390(3) . ?
C15 C16 1.396(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 O2 1.196(3) . ?
C21 O1 1.329(3) . ?
C21 C22 1.492(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O3 O4 1.453(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
O1 C1 C2 106.80(16) . . ?
O1 C1 C12 107.99(15) . . ?
C2 C1 C12 110.51(16) . . ?
O1 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C12 C1 H1 110.5 . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 122.72(19) . . ?
C7 C2 C1 117.78(17) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 120.26(19) . . ?
C6 C7 N1 118.22(18) . . ?
C2 C7 N1 121.52(18) . . ?
N1 C8 C9 117.16(17) . . ?
N1 C8 C12 125.10(17) . . ?
C9 C8 C12 117.71(16) . . ?
O5 C9 O3 103.35(15) . . ?
O5 C9 C14 110.88(17) . . ?
O3 C9 C14 107.83(17) . . ?
O5 C9 C8 109.47(15) . . ?
O3 C9 C8 109.17(16) . . ?
C14 C9 C8 115.42(17) . . ?
O5 C10 O4 103.71(16) . . ?
O5 C10 C13 111.06(19) . . ?
O4 C10 C13 108.32(19) . . ?
O5 C10 C11 110.41(17) . . ?
O4 C10 C11 108.07(18) . . ?
C13 C10 C11 114.62(19) . . ?
C10 C11 C12 112.98(17) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C8 C12 C1 107.23(16) . . ?
C8 C12 C15 109.37(15) . . ?
C1 C12 C15 107.14(15) . . ?
C8 C12 C11 111.69(16) . . ?
C1 C12 C11 111.35(16) . . ?
C15 C12 C11 109.92(16) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 117.92(17) . . ?
C20 C15 C12 122.96(17) . . ?
C16 C15 C12 119.11(17) . . ?
C17 C16 C15 121.25(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 120.15(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.80(19) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.72(18) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 121.14(18) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
O2 C21 O1 123.0(2) . . ?
O2 C21 C22 125.3(2) . . ?
O1 C21 C22 111.72(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 N1 C7 118.01(16) . . ?
C21 O1 C1 117.81(16) . . ?
C9 O3 O4 102.28(13) . . ?
O3 O4 C10 106.44(15) . . ?
C9 O5 C10 102.88(15) . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6



