# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a18191
_database_code_depnum_ccdc_archive 'CCDC 1510902'
_audit_update_record             
;
2016-10-20 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H28 N2 O3'
_chemical_formula_sum            'C26 H28 N2 O3'
_chemical_formula_weight         416.50

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   10.294(2)
_cell_length_b                   10.7033(19)
_cell_length_c                   12.376(2)
_cell_angle_alpha                69.312(6)
_cell_angle_beta                 79.586(8)
_cell_angle_gamma                66.460(6)
_cell_volume                     1168.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2418
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX2'
_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            10194
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4036
_reflns_number_gt                2297
_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)+(0.0381P)²+0.5566P] 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         4036
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1657(3) 0.6495(3) 1.1398(2) 0.0435(7) Uani 1 1 d . . .
C2 C 1.0710(3) 0.7375(3) 1.2007(2) 0.0516(8) Uani 1 1 d . . .
H2 H 0.9790 0.7925 1.1764 0.062 Uiso 1 1 calc R . .
C3 C 1.1140(3) 0.7435(3) 1.2983(3) 0.0605(9) Uani 1 1 d . . .
H3 H 1.0491 0.8025 1.3390 0.073 Uiso 1 1 calc R . .
C4 C 1.2499(4) 0.6646(3) 1.3372(3) 0.0580(8) Uani 1 1 d . . .
C5 C 1.2965(4) 0.6745(4) 1.4421(3) 0.0934(13) Uani 1 1 d . . .
H5A H 1.3937 0.6121 1.4553 0.140 Uiso 1 1 calc R . .
H5B H 1.2380 0.6462 1.5085 0.140 Uiso 1 1 calc R . .
H5C H 1.2875 0.7714 1.4290 0.140 Uiso 1 1 calc R . .
C6 C 1.3422(3) 0.5761(3) 1.2760(3) 0.0576(8) Uani 1 1 d . . .
H6 H 1.4343 0.5215 1.3000 0.069 Uiso 1 1 calc R . .
C7 C 1.3010(3) 0.5666(3) 1.1797(2) 0.0529(8) Uani 1 1 d . . .
H7 H 1.3647 0.5041 1.1414 0.063 Uiso 1 1 calc R . .
C8 C 1.1834(3) 0.7152(3) 0.9237(2) 0.0447(7) Uani 1 1 d . . .
C9 C 1.1764(3) 0.8625(3) 0.9182(3) 0.0572(8) Uani 1 1 d . . .
H9A H 1.2465 0.8510 0.9662 0.086 Uiso 1 1 calc R . .
H9B H 1.0838 0.9146 0.9451 0.086 Uiso 1 1 calc R . .
H9C H 1.1944 0.9146 0.8398 0.086 Uiso 1 1 calc R . .
C10 C 1.3332(3) 0.6211(3) 0.8961(3) 0.0643(9) Uani 1 1 d . . .
H10A H 1.3978 0.6156 0.9462 0.096 Uiso 1 1 calc R . .
H10B H 1.3603 0.6617 0.8171 0.096 Uiso 1 1 calc R . .
H10C H 1.3358 0.5265 0.9077 0.096 Uiso 1 1 calc R . .
C11 C 1.0752(3) 0.7297(3) 0.8492(2) 0.0434(7) Uani 1 1 d . . .
C12 C 0.9853(3) 0.7694(3) 0.6691(2) 0.0519(8) Uani 1 1 d . . .
C13 C 0.9003(4) 0.8963(4) 0.5980(3) 0.0679(9) Uani 1 1 d . . .
H13 H 0.9065 0.9824 0.5933 0.081 Uiso 1 1 calc R . .
C14 C 0.8057(4) 0.8948(4) 0.5335(3) 0.0895(12) Uani 1 1 d . . .
H14 H 0.7469 0.9810 0.4856 0.107 Uiso 1 1 calc R . .
C15 C 0.7963(5) 0.7673(5) 0.5385(3) 0.0933(13) Uani 1 1 d . . .
C16 C 0.6887(6) 0.7670(6) 0.4690(4) 0.175(3) Uani 1 1 d . . .
H16A H 0.6349 0.8638 0.4260 0.262 Uiso 1 1 calc R . .
H16B H 0.6259 0.7237 0.5205 0.262 Uiso 1 1 calc R . .
H16C H 0.7375 0.7132 0.4164 0.262 Uiso 1 1 calc R . .
C17 C 0.8854(4) 0.6420(4) 0.6083(3) 0.0836(12) Uani 1 1 d . . .
H17 H 0.8818 0.5554 0.6112 0.100 Uiso 1 1 calc R . .
C18 C 0.9805(4) 0.6410(4) 0.6743(3) 0.0657(9) Uani 1 1 d . . .
H18 H 1.0403 0.5550 0.7215 0.079 Uiso 1 1 calc R . .
C19 C 0.9499(3) 0.6992(3) 0.9210(2) 0.0442(7) Uani 1 1 d . . .
H19 H 0.9543 0.6043 0.9258 0.053 Uiso 1 1 calc R . .
C20 C 0.8041(3) 0.8091(3) 0.8895(2) 0.0422(7) Uani 1 1 d . . .
C21 C 0.7015(3) 0.7727(3) 0.8637(3) 0.0571(8) Uani 1 1 d . . .
H21 H 0.7235 0.6793 0.8645 0.069 Uiso 1 1 calc R . .
C22 C 0.5671(4) 0.8727(4) 0.8368(3) 0.0642(9) Uani 1 1 d . . .
H22 H 0.4995 0.8467 0.8188 0.077 Uiso 1 1 calc R . .
C23 C 0.5331(3) 1.0111(4) 0.8366(2) 0.0526(8) Uani 1 1 d . . .
C24 C 0.3548(4) 1.2439(4) 0.8136(3) 0.0817(11) Uani 1 1 d . . .
H24A H 0.2571 1.2961 0.7949 0.123 Uiso 1 1 calc R . .
H24B H 0.4129 1.2899 0.7578 0.123 Uiso 1 1 calc R . .
H24C H 0.3670 1.2421 0.8893 0.123 Uiso 1 1 calc R . .
C25 C 0.6336(3) 1.0495(3) 0.8612(2) 0.0550(8) Uani 1 1 d . . .
H25 H 0.6115 1.1428 0.8609 0.066 Uiso 1 1 calc R . .
C26 C 0.7682(3) 0.9485(3) 0.8865(2) 0.0529(8) Uani 1 1 d . . .
H26 H 0.8365 0.9756 0.9020 0.063 Uiso 1 1 calc R . .
N1 N 1.1315(2) 0.6334(2) 1.03888(19) 0.0441(6) Uani 1 1 d . . .
N2 N 1.0865(3) 0.7705(3) 0.7364(2) 0.0535(6) Uani 1 1 d . . .
O1 O 0.97615(19) 0.69869(19) 1.03223(15) 0.0493(5) Uani 1 1 d . . .
O2 O 1.1881(2) 0.8120(3) 0.67603(18) 0.0755(7) Uani 1 1 d . . .
O3 O 0.3953(2) 1.1017(3) 0.81162(19) 0.0738(7) 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 C2 1.382(4) . ?
C1 C7 1.387(4) . ?
C1 N1 1.439(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.379(4) . ?
C4 C5 1.513(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C11 1.499(3) . ?
C8 N1 1.517(3) . ?
C8 C10 1.524(4) . ?
C8 C9 1.526(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.306(3) . ?
C11 C19 1.508(4) . ?
C12 C13 1.367(4) . ?
C12 C18 1.373(4) . ?
C12 N2 1.453(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.368(5) . ?
C15 C16 1.522(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.447(3) . ?
C19 C20 1.505(4) . ?
C19 H19 0.9800 . ?
C20 C26 1.375(4) . ?
C20 C21 1.381(4) . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 C25 1.369(4) . ?
C23 O3 1.377(3) . ?
C24 O3 1.417(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.381(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 O1 1.472(3) . ?
N2 O2 1.305(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 C1 C7 118.7(3) . . ?
C2 C1 N1 124.1(3) . . ?
C7 C1 N1 117.2(2) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C6 C4 C3 117.2(3) . . ?
C6 C4 C5 121.0(3) . . ?
C3 C4 C5 121.9(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 121.5(3) . . ?
C4 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C1 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C1 C7 H7 119.6 . . ?
C11 C8 N1 98.4(2) . . ?
C11 C8 C10 113.0(2) . . ?
N1 C8 C10 108.3(2) . . ?
C11 C8 C9 110.7(2) . . ?
N1 C8 C9 114.1(2) . . ?
C10 C8 C9 111.6(2) . . ?
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 . . ?
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 . . ?
N2 C11 C8 123.5(2) . . ?
N2 C11 C19 125.1(2) . . ?
C8 C11 C19 111.3(2) . . ?
C13 C12 C18 121.2(3) . . ?
C13 C12 N2 119.2(3) . . ?
C18 C12 N2 119.6(3) . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C17 C15 C14 118.2(3) . . ?
C17 C15 C16 121.0(4) . . ?
C14 C15 C16 120.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 121.6(3) . . ?
C15 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C12 C18 C17 118.7(3) . . ?
C12 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
O1 C19 C20 107.1(2) . . ?
O1 C19 C11 100.75(19) . . ?
C20 C19 C11 117.8(2) . . ?
O1 C19 H19 110.2 . . ?
C20 C19 H19 110.2 . . ?
C11 C19 H19 110.2 . . ?
C26 C20 C21 117.8(3) . . ?
C26 C20 C19 121.2(2) . . ?
C21 C20 C19 121.0(3) . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C25 C23 O3 124.6(3) . . ?
C25 C23 C22 119.9(3) . . ?
O3 C23 C22 115.5(3) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 119.5(3) . . ?
C23 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C20 C26 C25 121.9(3) . . ?
C20 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C1 N1 O1 107.03(19) . . ?
C1 N1 C8 115.9(2) . . ?
O1 N1 C8 103.17(18) . . ?
O2 N2 C11 123.8(2) . . ?
O2 N2 C12 115.2(2) . . ?
C11 N2 C12 121.0(2) . . ?
C19 O1 N1 104.46(18) . . ?
C23 O3 C24 117.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_160334LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1507478'
_audit_update_record             
;
2016-09-30 deposited with the CCDC.
2017-05-24 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            'C16 H15 N O3'
_chemical_formula_weight         269.29

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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'

_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'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   13.9065(11)
_cell_length_b                   13.9065(11)
_cell_length_c                   6.0548(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1014.07(18)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2911
_cell_measurement_theta_min      2.9295
_cell_measurement_theta_max      26.0153

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             426
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8931
_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            7841
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         26.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2610
_reflns_number_gt                2439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX2 (Bruker AXS, 2010)'
_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    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0591P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(15)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2610
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_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 0.54771(17) 0.51656(16) 0.0443(3) 0.0205(5) Uani 1 1 d . . . . .
O2 O 0.49202(16) 0.74201(15) 0.4454(3) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.28068(16) 0.43457(15) 0.1672(3) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.2624 0.4432 0.0396 0.028 Uiso 1 1 calc R U . . .
N1 N 0.52614(19) 0.67418(18) 0.3761(3) 0.0139(5) Uani 1 1 d . . . . .
C1 C 0.4566(2) 0.2463(2) 0.6716(5) 0.0211(6) Uani 1 1 d . . . . .
H1 H 0.4468 0.1894 0.7712 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5138(2) 0.2607(2) 0.4742(5) 0.0203(6) Uani 1 1 d . . . . .
H3 H 0.5436 0.2142 0.4404 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5271(2) 0.3428(2) 0.3272(5) 0.0182(6) Uani 1 1 d . . . . .
H4 H 0.5651 0.3519 0.1917 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4844(2) 0.4125(2) 0.3787(4) 0.0153(6) Uani 1 1 d . . . . .
C5 C 0.5017(2) 0.5018(2) 0.2221(5) 0.0143(5) Uani 1 1 d . . . . .
C6 C 0.4585(2) 0.5778(2) 0.2931(4) 0.0142(5) Uani 1 1 d . . . . .
C7 C 0.6453(2) 0.7162(2) 0.3875(5) 0.0154(5) Uani 1 1 d . . . . .
C8 C 0.6900(2) 0.6924(2) 0.5692(5) 0.0195(6) Uani 1 1 d . . . . .
H10 H 0.6441 0.6493 0.6881 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8035(2) 0.7331(2) 0.5733(5) 0.0208(6) Uani 1 1 d . . . . .
H9 H 0.8353 0.7174 0.6972 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8721(2) 0.7963(2) 0.4006(5) 0.0196(6) Uani 1 1 d . . . . .
C11 C 0.9958(3) 0.8418(3) 0.4068(6) 0.0283(7) Uani 1 1 d . . . . .
H2 H 1.0333 0.9203 0.4490 0.042 Uiso 1 1 calc R U . . .
H5 H 1.0216 0.8344 0.2604 0.042 Uiso 1 1 calc R U . . .
H6 H 1.0130 0.8001 0.5150 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4138(2) 0.3147(2) 0.7232(5) 0.0199(6) Uani 1 1 d . . . . .
H15 H 0.3748 0.3045 0.8579 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4278(2) 0.3981(2) 0.5781(5) 0.0180(6) Uani 1 1 d . . . . .
H14 H 0.3990 0.4454 0.6142 0.022 Uiso 1 1 calc R U . . .
C14 C 0.8236(3) 0.8190(3) 0.2212(5) 0.0256(7) Uani 1 1 d . . . . .
H7 H 0.8692 0.8622 0.1020 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7108(2) 0.7801(2) 0.2132(5) 0.0214(6) Uani 1 1 d . . . . .
H8 H 0.6788 0.7966 0.0910 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3365(2) 0.5383(2) 0.2759(5) 0.0160(6) Uani 1 1 d . . . . .
H13 H 0.3050 0.5313 0.4256 0.019 Uiso 1 1 calc R U . . .
H12 H 0.3255 0.5934 0.1928 0.019 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 C5 1.216(3) . ?
O2 N1 1.318(3) . ?
O3 C16 1.414(3) . ?
O3 H11 0.8400 . ?
N1 C6 1.293(3) . ?
N1 C7 1.458(3) . ?
C1 C12 1.387(4) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(4) . ?
C2 H3 0.9500 . ?
C3 C4 1.402(4) . ?
C3 H4 0.9500 . ?
C4 C13 1.400(4) . ?
C4 C5 1.483(4) . ?
C5 C6 1.517(4) . ?
C6 C16 1.503(4) . ?
C7 C8 1.382(4) . ?
C7 C15 1.386(4) . ?
C8 C9 1.385(4) . ?
C8 H10 0.9500 . ?
C9 C10 1.392(4) . ?
C9 H9 0.9500 . ?
C10 C14 1.395(4) . ?
C10 C11 1.508(4) . ?
C11 H2 0.9800 . ?
C11 H5 0.9800 . ?
C11 H6 0.9800 . ?
C12 C13 1.389(4) . ?
C12 H15 0.9500 . ?
C13 H14 0.9500 . ?
C14 C15 1.381(4) . ?
C14 H7 0.9500 . ?
C15 H8 0.9500 . ?
C16 H13 0.9900 . ?
C16 H12 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 H11 109.5 . . ?
C6 N1 O2 121.9(2) . . ?
C6 N1 C7 121.8(2) . . ?
O2 N1 C7 116.2(2) . . ?
C12 C1 C2 120.3(3) . . ?
C12 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H3 120.0 . . ?
C1 C2 H3 120.0 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H4 120.0 . . ?
C4 C3 H4 120.0 . . ?
C13 C4 C3 119.7(3) . . ?
C13 C4 C5 121.1(2) . . ?
C3 C4 C5 119.3(2) . . ?
O1 C5 C4 124.0(2) . . ?
O1 C5 C6 119.5(2) . . ?
C4 C5 C6 116.5(2) . . ?
N1 C6 C16 120.6(2) . . ?
N1 C6 C5 119.7(2) . . ?
C16 C6 C5 119.6(2) . . ?
C8 C7 C15 121.9(3) . . ?
C8 C7 N1 119.9(2) . . ?
C15 C7 N1 118.2(2) . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 H10 120.9 . . ?
C9 C8 H10 120.9 . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C14 118.2(3) . . ?
C9 C10 C11 121.6(3) . . ?
C14 C10 C11 120.2(3) . . ?
C10 C11 H2 109.5 . . ?
C10 C11 H5 109.5 . . ?
H2 C11 H5 109.5 . . ?
C10 C11 H6 109.5 . . ?
H2 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
C1 C12 C13 120.1(3) . . ?
C1 C12 H15 120.0 . . ?
C13 C12 H15 120.0 . . ?
C12 C13 C4 119.9(3) . . ?
C12 C13 H14 120.0 . . ?
C4 C13 H14 120.0 . . ?
C15 C14 C10 121.4(3) . . ?
C15 C14 H7 119.3 . . ?
C10 C14 H7 119.3 . . ?
C14 C15 C7 118.6(3) . . ?
C14 C15 H8 120.7 . . ?
C7 C15 H8 120.7 . . ?
O3 C16 C6 110.4(2) . . ?
O3 C16 H13 109.6 . . ?
C6 C16 H13 109.6 . . ?
O3 C16 H12 109.6 . . ?
C6 C16 H12 109.6 . . ?
H13 C16 H12 108.1 . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.073

_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_d18485f
_database_code_depnum_ccdc_archive 'CCDC 1540299'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 Cl2 N2 O2'
_chemical_formula_sum            'C28 H24 Cl2 N2 O2'
_chemical_formula_weight         491.39

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'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   16.420(2)
_cell_length_b                   5.9044(8)
_cell_length_c                   25.212(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.487(4)
_cell_angle_gamma                90.00
_cell_volume                     2444.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9546
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.05

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9196
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   ?

_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            38821
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0773
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.46
_reflns_number_total             8777
_reflns_number_gt                6451
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_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)+(0.2000P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_number_reflns         8777
_refine_ls_number_parameters     296
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.2885
_refine_ls_R_factor_gt           0.2542
_refine_ls_wR_factor_ref         0.6117
_refine_ls_wR_factor_gt          0.5938
_refine_ls_goodness_of_fit_ref   2.629
_refine_ls_restrained_S_all      2.631
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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 0.7707(9) 0.101(3) -0.0590(6) 0.049(4) Uiso 1 1 d D . .
C2 C 0.8053(10) -0.105(4) -0.0795(7) 0.063(5) Uiso 1 1 d D . .
H2 H 0.8226 -0.2213 -0.0558 0.076 Uiso 1 1 calc R . .
C3 C 0.8132(13) -0.133(4) -0.1324(7) 0.099 Uiso 1 1 d D . .
H3 H 0.8366 -0.2703 -0.1450 0.119 Uiso 1 1 calc R . .
C4 C 0.7890(10) 0.026(3) -0.1688(7) 0.057(4) Uiso 1 1 d D . .
H4 H 0.7968 0.0016 -0.2057 0.068 Uiso 1 1 calc R . .
C5 C 0.7530(8) 0.225(3) -0.1508(5) 0.040(3) Uiso 1 1 d D . .
H5 H 0.7330 0.3387 -0.1743 0.048 Uiso 1 1 calc R . .
C6 C 0.7486(9) 0.245(3) -0.0958(6) 0.052(4) Uiso 1 1 d D . .
H6 H 0.7264 0.3837 -0.0832 0.062 Uiso 1 1 calc R . .
C7 C 0.6791(9) 0.268(3) 0.0540(5) 0.040(3) Uiso 1 1 d . . .
H7 H 0.7063 0.4139 0.0641 0.047 Uiso 1 1 calc R . .
C8 C 0.5807(8) 0.273(3) 0.0698(5) 0.035(3) Uiso 1 1 d D . .
C9 C 0.5576(8) 0.491(3) 0.0948(5) 0.038(3) Uiso 1 1 d D . .
H9 H 0.5941 0.6074 0.1055 0.045 Uiso 1 1 calc R . .
C10 C 0.4677(12) 0.496(4) 0.1001(7) 0.070(5) Uiso 1 1 d D . .
H10 H 0.4428 0.6255 0.1153 0.084 Uiso 1 1 calc R . .
C11 C 0.4237(12) 0.334(3) 0.0851(7) 0.059(4) Uiso 1 1 d D . .
H11 H 0.3667 0.3571 0.0886 0.071 Uiso 1 1 calc R . .
C12 C 0.4502(12) 0.095(4) 0.0610(7) 0.065(5) Uiso 1 1 d D . .
H12 H 0.4170 -0.0341 0.0546 0.078 Uiso 1 1 calc R . .
C13 C 0.5303(9) 0.119(3) 0.0519(5) 0.038(3) Uiso 1 1 d D . .
H13 H 0.5535 0.0087 0.0292 0.046 Uiso 1 1 calc R . .
C14 C 0.7210(12) 0.076(4) 0.0776(7) 0.063(5) Uiso 1 1 d . . .
C15 C 0.6770(7) 0.071(2) 0.1691(4) 0.027(3) Uiso 1 1 d D . .
C16 C 0.7145(8) 0.289(3) 0.1799(5) 0.036(3) Uiso 1 1 d D . .
H16 H 0.7581 0.3606 0.1618 0.043 Uiso 1 1 calc R . .
C17 C 0.6681(11) 0.374(4) 0.2262(7) 0.068(5) Uiso 1 1 d D . .
H17 H 0.6838 0.5236 0.2352 0.082 Uiso 1 1 calc R . .
C18 C 0.6172(9) 0.306(3) 0.2548(6) 0.045(4) Uiso 1 1 d D . .
H18 H 0.5995 0.3819 0.2859 0.054 Uiso 1 1 calc R . .
C19 C 0.5837(11) 0.079(4) 0.2348(7) 0.058(4) Uiso 1 1 d D . .
H19 H 0.5355 0.0230 0.2507 0.070 Uiso 1 1 calc R . .
C20 C 0.6215(12) -0.059(4) 0.1923(7) 0.067(5) Uiso 1 1 d D . .
H20 H 0.6084 -0.2115 0.1834 0.080 Uiso 1 1 calc R . .
C21 C 0.7666(8) -0.051(3) 0.0330(5) 0.031(3) Uiso 1 1 d . . .
H21 H 0.7374 -0.1881 0.0194 0.037 Uiso 1 1 calc R . .
C22 C 0.8565(8) -0.098(2) 0.0525(5) 0.032(3) Uiso 1 1 d . . .
C23 C 0.8910(9) -0.339(3) 0.0369(6) 0.042(3) Uiso 1 1 d . . .
H23 H 0.8603 -0.4592 0.0216 0.050 Uiso 1 1 calc R . .
C24 C 0.9794(11) -0.348(4) 0.0503(7) 0.060(5) Uiso 1 1 d . . .
H24 H 1.0094 -0.4790 0.0410 0.072 Uiso 1 1 calc R . .
C25 C 1.0171(10) -0.185(3) 0.0740(6) 0.048(4) Uiso 1 1 d . . .
H25 H 1.0715 -0.2201 0.0841 0.058 Uiso 1 1 calc R . .
C26 C 0.9935(13) 0.028(4) 0.0872(8) 0.069(5) Uiso 1 1 d . . .
H26 H 1.0294 0.1412 0.1005 0.082 Uiso 1 1 calc R . .
C27 C 0.8985(12) 0.065(4) 0.0776(7) 0.063(5) Uiso 1 1 d . . .
H27 H 0.8722 0.1994 0.0894 0.076 Uiso 1 1 calc R . .
C28 C 0.7750(8) 0.116(3) 0.4360(6) 0.040(3) Uiso 1 1 d D . .
C29 C 0.7531(8) -0.076(3) 0.4008(6) 0.044(3) Uiso 1 1 d D . .
H29 H 0.7283 -0.2111 0.4131 0.053 Uiso 1 1 calc R . .
C30 C 0.7711(13) -0.041(5) 0.3521(10) 0.097(7) Uiso 1 1 d D . .
H30 H 0.7638 -0.1617 0.3277 0.116 Uiso 1 1 calc R . .
C31 C 0.8005(9) 0.163(3) 0.3330(6) 0.045(4) Uiso 1 1 d D . .
H31 H 0.8017 0.1829 0.2956 0.054 Uiso 1 1 calc R . .
C32 C 0.8277(8) 0.337(3) 0.3633(5) 0.038(3) Uiso 1 1 d D . .
H32 H 0.8526 0.4683 0.3491 0.046 Uiso 1 1 calc R . .
C33 C 0.8152(8) 0.302(2) 0.4205(5) 0.031(3) Uiso 1 1 d D . .
H33 H 0.8350 0.4084 0.4458 0.038 Uiso 1 1 calc R . .
C34 C 0.7693(9) 0.254(3) 0.5286(5) 0.040(3) Uiso 1 1 d . . .
H34 H 0.7406 0.3850 0.5117 0.048 Uiso 1 1 calc R . .
C35 C 0.8537(9) 0.329(3) 0.5435(5) 0.041(3) Uiso 1 1 d D . .
C36 C 0.8932(9) 0.514(3) 0.5368(5) 0.041(3) Uiso 1 1 d D . .
H36 H 0.8642 0.6276 0.5177 0.049 Uiso 1 1 calc R . .
C37 C 0.9632(9) 0.570(3) 0.5510(5) 0.040(3) Uiso 1 1 d D . .
H37 H 0.9824 0.7185 0.5438 0.049 Uiso 1 1 calc R . .
C38 C 1.0122(12) 0.420(4) 0.5769(7) 0.063(5) Uiso 1 1 d D . .
H38 H 1.0663 0.4556 0.5877 0.075 Uiso 1 1 calc R . .
C39 C 0.9757(8) 0.204(3) 0.5865(5) 0.035(3) Uiso 1 1 d D . .
H39 H 1.0067 0.0928 0.6050 0.041 Uiso 1 1 calc R . .
C40 C 0.9007(8) 0.150(3) 0.5707(5) 0.036(3) Uiso 1 1 d D . .
H40 H 0.8785 0.0032 0.5766 0.043 Uiso 1 1 calc R . .
C41 C 0.7190(7) 0.173(2) 0.5724(5) 0.027(3) Uiso 1 1 d . . .
C42 C 0.6771(12) 0.138(4) 0.6614(7) 0.066(5) Uiso 1 1 d D . .
C43 C 0.6119(8) 0.216(3) 0.6945(5) 0.041(3) Uiso 1 1 d D . .
H43 H 0.5873 0.3572 0.6858 0.049 Uiso 1 1 calc R . .
C44 C 0.5798(14) 0.090(5) 0.7421(9) 0.082(6) Uiso 1 1 d D . .
H44 H 0.5366 0.1445 0.7634 0.099 Uiso 1 1 calc R . .
C45 C 0.6095(10) -0.062(4) 0.7492(7) 0.056(4) Uiso 1 1 d D . .
H45 H 0.5890 -0.1393 0.7793 0.067 Uiso 1 1 calc R . .
C46 C 0.6774(9) -0.190(3) 0.7230(6) 0.047(4) Uiso 1 1 d D . .
H46 H 0.6997 -0.3315 0.7336 0.057 Uiso 1 1 calc R . .
C47 C 0.7007(11) -0.058(3) 0.6802(6) 0.054(4) Uiso 1 1 d D . .
H47 H 0.7430 -0.1252 0.6600 0.065 Uiso 1 1 calc R . .
C48 C 0.6747(8) -0.055(3) 0.5587(5) 0.031(3) Uiso 1 1 d . . .
H48 H 0.7063 -0.1838 0.5745 0.037 Uiso 1 1 calc R . .
C49 C 0.5920(8) -0.094(3) 0.5663(5) 0.036(3) Uiso 1 1 d D . .
C50 C 0.5615(10) -0.255(3) 0.5902(5) 0.051(4) Uiso 1 1 d D . .
H50 H 0.5970 -0.3754 0.5995 0.061 Uiso 1 1 calc R . .
C51 C 0.4783(8) -0.279(3) 0.6053(5) 0.037(3) Uiso 1 1 d D . .
H51 H 0.4598 -0.4105 0.6231 0.045 Uiso 1 1 calc R . .
C52 C 0.4218(10) -0.091(3) 0.5922(6) 0.050(4) Uiso 1 1 d D . .
H52 H 0.3670 -0.0860 0.6041 0.060 Uiso 1 1 calc R . .
C53 C 0.4527(9) 0.059(3) 0.5642(5) 0.041(3) Uiso 1 1 d D . .
H53 H 0.4142 0.1552 0.5472 0.049 Uiso 1 1 calc R . .
C54 C 0.5400(10) 0.114(3) 0.5523(6) 0.047(4) Uiso 1 1 d D . .
H54 H 0.5597 0.2539 0.5386 0.057 Uiso 1 1 calc R . .
C55 C 1.1315(14) 0.251(4) 0.2476(8) 0.083 Uiso 1 1 d D . .
H55A H 1.1141 0.3264 0.2143 0.099 Uiso 1 1 calc R . .
H55B H 1.1904 0.2784 0.2532 0.099 Uiso 1 1 calc R . .
C56 C 0.9227(9) -0.347(3) 0.1939(6) 0.041(4) Uani 1 1 d . . .
H56A H 0.8912 -0.2936 0.1627 0.049 Uiso 1 1 calc R . .
H56B H 0.9781 -0.2825 0.1905 0.049 Uiso 1 1 calc R . .
N1 N 0.7689(7) 0.125(2) -0.0024(5) 0.043(3) Uiso 1 1 d . . .
N2 N 0.7014(8) -0.045(3) 0.1188(5) 0.048(3) Uiso 1 1 d . . .
N3 N 0.7636(7) 0.059(2) 0.4918(4) 0.034(3) Uiso 1 1 d . . .
N4 N 0.7175(6) 0.2559(19) 0.6229(4) 0.026(2) Uiso 1 1 d . . .
O1 O 0.6839(6) 0.234(2) 0.0041(4) 0.046(3) Uiso 1 1 d . . .
O2 O 0.7395(5) -0.2485(18) 0.1309(3) 0.034(2) Uiso 1 1 d . . .
O3 O 0.6875(5) -0.0533(17) 0.4988(3) 0.034(2) Uiso 1 1 d . . .
O4 O 0.7407(7) 0.462(2) 0.6303(5) 0.061(3) Uiso 1 1 d . . .
Cl1 Cl 1.0741(4) 0.3549(10) 0.3025(2) 0.0797(16) Uani 1 1 d D . .
Cl2 Cl 1.1108(4) -0.0445(12) 0.2446(2) 0.0849(18) Uani 1 1 d . . .
Cl3 Cl 0.8785(5) -0.2138(16) 0.2504(3) 0.120(3) Uani 1 1 d . . .
Cl4 Cl 0.9321(8) -0.604(2) 0.1871(5) 0.180(6) 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 C6 1.31(2) . ?
C1 N1 1.436(19) . ?
C1 C2 1.44(3) . ?
C2 C3 1.352(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.39(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.40(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.277(17) . ?
C7 C14 1.45(3) . ?
C7 C8 1.667(19) . ?
C7 H7 1.0000 . ?
C8 C13 1.31(2) . ?
C8 C9 1.48(2) . ?
C9 C10 1.48(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.25(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.60(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.35(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N2 1.30(2) . ?
C14 C21 1.55(2) . ?
C15 C20 1.33(2) . ?
C15 C16 1.45(2) . ?
C15 N2 1.498(17) . ?
C16 C17 1.48(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.18(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.53(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.49(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N1 1.369(19) . ?
C21 C22 1.578(18) . ?
C21 H21 1.0000 . ?
C22 C27 1.34(3) . ?
C22 C23 1.58(2) . ?
C23 C24 1.49(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.29(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.36(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.59(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.34(2) . ?
C28 N3 1.462(17) . ?
C28 C29 1.48(2) . ?
C29 C30 1.28(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.39(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.35(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.473(18) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 N3 1.48(2) . ?
C34 C41 1.463(19) . ?
C34 C35 1.50(2) . ?
C34 H34 1.0000 . ?
C35 C36 1.28(2) . ?
C35 C40 1.48(2) . ?
C36 C37 1.24(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.36(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.43(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.33(2) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 N4 1.366(15) . ?
C41 C48 1.568(19) . ?
C42 C47 1.31(3) . ?
C42 N4 1.37(2) . ?
C42 C43 1.44(2) . ?
C43 C44 1.51(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.04(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.50(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.39(2) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.393(19) . ?
C48 O3 1.526(14) . ?
C48 H48 1.0000 . ?
C49 C50 1.23(2) . ?
C49 C54 1.54(2) . ?
C50 C51 1.43(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.48(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.24(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.50(2) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 Cl2 1.78(3) . ?
C55 Cl1 1.791(16) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 Cl4 1.53(2) . ?
C56 Cl3 1.788(16) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
N1 O1 1.547(17) . ?
N2 O2 1.388(18) . ?
N3 O3 1.425(15) . ?
N4 O4 1.288(18) . ?

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
C6 C1 N1 129.1(17) . . ?
C6 C1 C2 113.9(15) . . ?
N1 C1 C2 116.9(15) . . ?
C3 C2 C1 120(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 123(2) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 118.9(18) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 114.9(15) . . ?
C6 C5 H5 122.5 . . ?
C4 C5 H5 122.6 . . ?
C1 C6 C5 129.2(18) . . ?
C1 C6 H6 115.3 . . ?
C5 C6 H6 115.5 . . ?
O1 C7 C14 104.3(14) . . ?
O1 C7 C8 107.9(11) . . ?
C14 C7 C8 111.7(13) . . ?
O1 C7 H7 110.9 . . ?
C14 C7 H7 110.9 . . ?
C8 C7 H7 110.9 . . ?
C13 C8 C9 125.8(13) . . ?
C13 C8 C7 121.3(13) . . ?
C9 C8 C7 111.5(12) . . ?
C10 C9 C8 108.3(14) . . ?
C10 C9 H9 125.8 . . ?
C8 C9 H9 125.9 . . ?
C11 C10 C9 122(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 129.0(18) . . ?
C10 C11 H11 115.4 . . ?
C12 C11 H11 115.6 . . ?
C13 C12 C11 104.0(17) . . ?
C13 C12 H12 128.1 . . ?
C11 C12 H12 127.9 . . ?
C12 C13 C8 129.2(16) . . ?
C12 C13 H13 115.3 . . ?
C8 C13 H13 115.5 . . ?
N2 C14 C7 129.5(17) . . ?
N2 C14 C21 115.8(17) . . ?
C7 C14 C21 108.1(14) . . ?
C20 C15 C16 136.0(14) . . ?
C20 C15 N2 107.3(14) . . ?
C16 C15 N2 116.7(11) . . ?
C15 C16 C17 103.1(13) . . ?
C15 C16 H16 128.5 . . ?
C17 C16 H16 128.4 . . ?
C18 C17 C16 138(2) . . ?
C18 C17 H17 111.1 . . ?
C16 C17 H17 111.2 . . ?
C17 C18 C19 110.3(17) . . ?
C17 C18 H18 124.9 . . ?
C19 C18 H18 124.8 . . ?
C20 C19 C18 124.6(16) . . ?
C20 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
C15 C20 C19 106.9(18) . . ?
C15 C20 H20 126.5 . . ?
C19 C20 H20 126.5 . . ?
N1 C21 C14 96.9(13) . . ?
N1 C21 C22 107.9(11) . . ?
C14 C21 C22 108.4(11) . . ?
N1 C21 H21 114.0 . . ?
C14 C21 H21 114.0 . . ?
C22 C21 H21 114.1 . . ?
C27 C22 C23 125.6(14) . . ?
C27 C22 C21 119.6(14) . . ?
C23 C22 C21 114.7(11) . . ?
C24 C23 C22 108.8(14) . . ?
C24 C23 H23 125.6 . . ?
C22 C23 H23 125.5 . . ?
C25 C24 C23 123.0(18) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C24 C25 C26 131.9(19) . . ?
C24 C25 H25 114.2 . . ?
C26 C25 H25 114.0 . . ?
C25 C26 C27 111.9(18) . . ?
C25 C26 H26 124.2 . . ?
C27 C26 H26 123.9 . . ?
C22 C27 C26 118.0(18) . . ?
C22 C27 H27 120.9 . . ?
C26 C27 H27 121.1 . . ?
C33 C28 N3 122.5(13) . . ?
C33 C28 C29 124.8(13) . . ?
N3 C28 C29 111.5(13) . . ?
C30 C29 C28 113(2) . . ?
C30 C29 H29 123.2 . . ?
C28 C29 H29 123.6 . . ?
C31 C30 C29 124(3) . . ?
C31 C30 H30 117.9 . . ?
C29 C30 H30 118.3 . . ?
C30 C31 C32 125.1(17) . . ?
C30 C31 H31 117.5 . . ?
C32 C31 H31 117.4 . . ?
C31 C32 C33 113.6(14) . . ?
C31 C32 H32 123.2 . . ?
C33 C32 H32 123.1 . . ?
C28 C33 C32 118.1(13) . . ?
C28 C33 H33 120.9 . . ?
C32 C33 H33 120.9 . . ?
N3 C34 C41 100.6(12) . . ?
N3 C34 C35 116.1(12) . . ?
C41 C34 C35 115.8(11) . . ?
N3 C34 H34 108.0 . . ?
C41 C34 H34 107.9 . . ?
C35 C34 H34 107.9 . . ?
C36 C35 C40 114.1(13) . . ?
C36 C35 C34 133.4(15) . . ?
C40 C35 C34 112.4(13) . . ?
C37 C36 C35 130.9(16) . . ?
C37 C36 H36 114.5 . . ?
C35 C36 H36 114.6 . . ?
C36 C37 C38 120.4(18) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C39 114.5(16) . . ?
C37 C38 H38 122.7 . . ?
C39 C38 H38 122.9 . . ?
C40 C39 C38 123.5(14) . . ?
C40 C39 H39 118.3 . . ?
C38 C39 H39 118.1 . . ?
C39 C40 C35 116.5(14) . . ?
C39 C40 H40 121.7 . . ?
C35 C40 H40 121.8 . . ?
N4 C41 C34 126.8(12) . . ?
N4 C41 C48 120.2(11) . . ?
C34 C41 C48 112.3(11) . . ?
C47 C42 N4 124.2(18) . . ?
C47 C42 C43 107.1(17) . . ?
N4 C42 C43 127.9(18) . . ?
C42 C43 C44 124.6(17) . . ?
C42 C43 H43 117.7 . . ?
C44 C43 H43 117.7 . . ?
C45 C44 C43 113(2) . . ?
C45 C44 H44 123.4 . . ?
C43 C44 H44 123.2 . . ?
C44 C45 C46 135(2) . . ?
C44 C45 H45 112.4 . . ?
C46 C45 H45 112.5 . . ?
C47 C46 C45 105.8(16) . . ?
C47 C46 H46 127.1 . . ?
C45 C46 H46 127.1 . . ?
C42 C47 C46 134.0(18) . . ?
C42 C47 H47 113.0 . . ?
C46 C47 H47 113.0 . . ?
C49 C48 O3 106.4(10) . . ?
C49 C48 C41 124.1(12) . . ?
O3 C48 C41 98.2(9) . . ?
C49 C48 H48 108.9 . . ?
O3 C48 H48 108.9 . . ?
C41 C48 H48 109.0 . . ?
C50 C49 C48 126.5(15) . . ?
C50 C49 C54 120.1(14) . . ?
C48 C49 C54 112.1(13) . . ?
C49 C50 C51 126.9(17) . . ?
C49 C50 H50 116.5 . . ?
C51 C50 H50 116.6 . . ?
C50 C51 C52 117.8(15) . . ?
C50 C51 H51 121.1 . . ?
C52 C51 H51 121.1 . . ?
C53 C52 C51 113.6(15) . . ?
C53 C52 H52 123.1 . . ?
C51 C52 H52 123.3 . . ?
C52 C53 C54 131.5(16) . . ?
C52 C53 H53 114.3 . . ?
C54 C53 H53 114.2 . . ?
C53 C54 C49 107.9(14) . . ?
C53 C54 H54 126.1 . . ?
C49 C54 H54 126.0 . . ?
Cl2 C55 Cl1 105.5(12) . . ?
Cl2 C55 H55A 110.8 . . ?
Cl1 C55 H55A 110.8 . . ?
Cl2 C55 H55B 110.5 . . ?
Cl1 C55 H55B 110.6 . . ?
H55A C55 H55B 108.7 . . ?
Cl4 C56 Cl3 124.5(12) . . ?
Cl4 C56 H56A 106.2 . . ?
Cl3 C56 H56A 106.2 . . ?
Cl4 C56 H56B 106.2 . . ?
Cl3 C56 H56B 106.2 . . ?
H56A C56 H56B 106.4 . . ?
C21 N1 C1 124.9(13) . . ?
C21 N1 O1 102.6(10) . . ?
C1 N1 O1 99.9(10) . . ?
C14 N2 O2 122.5(13) . . ?
C14 N2 C15 119.5(15) . . ?
O2 N2 C15 109.4(10) . . ?
O3 N3 C28 110.3(9) . . ?
O3 N3 C34 109.5(10) . . ?
C28 N3 C34 114.5(12) . . ?
O4 N4 C41 117.8(11) . . ?
O4 N4 C42 121.4(13) . . ?
C41 N4 C42 119.4(13) . . ?
C7 O1 N1 103.5(10) . . ?
N3 O3 C48 104.7(8) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.985
_refine_diff_density_min         -1.595
_refine_diff_density_rms         0.259
####################################################################### 
# 
# 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_a18125
_database_code_depnum_ccdc_archive 'CCDC 1507477'
_audit_update_record             
;
2016-09-30 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.32

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'

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

_cell_length_a                   8.480(7)
_cell_length_b                   5.698(4)
_cell_length_c                   15.656(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.20(5)
_cell_angle_gamma                90.00
_cell_volume                     755.3(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    901
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   ?

_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  'Bruker APEX2'
_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            4585
_diffrn_reflns_av_R_equivalents  0.3365
_diffrn_reflns_av_sigmaI/netI    0.2626
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.21
_reflns_number_total             2196
_reflns_number_gt                1103
_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)+(0.2000P)²+0.0000P] 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       0.08(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(9)
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     195
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.2549
_refine_ls_R_factor_gt           0.1803
_refine_ls_wR_factor_ref         0.4474
_refine_ls_wR_factor_gt          0.4062
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.015

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 0.724(2) 0.785(3) 0.0958(11) 0.051(5) Uani 1 1 d D . .
C2 C 0.822(2) 0.949(3) 0.0554(10) 0.068(5) Uani 1 1 d D . .
H2 H 0.8661 1.0797 0.0857 0.082 Uiso 1 1 calc R . .
C3 C 0.850(2) 0.912(3) -0.0264(12) 0.052(5) Uani 1 1 d D . .
H3 H 0.9133 1.0216 -0.0549 0.062 Uiso 1 1 calc R . .
C4 C 0.7879(19) 0.715(3) -0.0722(10) 0.046(4) Uani 1 1 d D . .
C5 C 0.781(3) 0.482(4) -0.2007(11) 0.073(6) Uani 1 1 d . . .
H5A H 0.8220 0.4841 -0.2579 0.110 Uiso 1 1 calc R . .
H5B H 0.6649 0.4800 -0.2059 0.110 Uiso 1 1 calc R . .
H5C H 0.8188 0.3416 -0.1699 0.110 Uiso 1 1 calc R . .
C6 C 0.693(2) 0.564(3) -0.0339(11) 0.052(5) Uani 1 1 d D . .
H6 H 0.6498 0.4334 -0.0648 0.063 Uiso 1 1 calc R . .
C7 C 0.658(3) 0.598(3) 0.0508(11) 0.068(5) Uani 1 1 d D . .
H7 H 0.5881 0.4940 0.0775 0.082 Uiso 1 1 calc R . .
C8 C 0.7474(19) 0.697(3) 0.2414(9) 0.044(4) Uani 1 1 d D . .
C9 C 0.846(2) 0.484(3) 0.2287(10) 0.055(5) Uani 1 1 d . . .
H9A H 0.9220 0.5089 0.1837 0.067 Uiso 1 1 calc R . .
H9B H 0.7807 0.3443 0.2145 0.067 Uiso 1 1 calc R . .
C10 C 0.732(3) 0.728(3) 0.3413(11) 0.066(6) Uani 1 1 d . . .
C11 C 0.823(3) 0.927(3) 0.3711(13) 0.064(5) Uani 1 1 d . . .
H11A H 0.9326 0.9091 0.3551 0.095 Uiso 1 1 calc R . .
H11B H 0.8208 0.9380 0.4335 0.095 Uiso 1 1 calc R . .
H11C H 0.7782 1.0703 0.3450 0.095 Uiso 1 1 calc R . .
C12 C 0.5530(17) 0.716(2) 0.3601(9) 0.032(3) Uani 1 1 d D . .
C13 C 0.461(2) 0.523(3) 0.3347(10) 0.070(7) Uani 1 1 d D . .
H13 H 0.5077 0.4011 0.3032 0.085 Uiso 1 1 calc R . .
C14 C 0.301(2) 0.504(3) 0.3544(11) 0.057(5) Uani 1 1 d D . .
H14 H 0.2343 0.3801 0.3338 0.069 Uiso 1 1 calc R . .
C15 C 0.250(3) 0.683(3) 0.4070(12) 0.065(6) Uani 1 1 d D . .
H15 H 0.1471 0.6663 0.4277 0.078 Uiso 1 1 calc R . .
C16 C 0.322(3) 0.859(3) 0.4289(11) 0.064(6) Uani 1 1 d D . .
H16 H 0.2690 0.9788 0.4579 0.076 Uiso 1 1 calc R . .
C17 C 0.490(2) 0.892(3) 0.4120(11) 0.051(5) Uani 1 1 d D . .
H17 H 0.5512 1.0204 0.4342 0.062 Uiso 1 1 calc R . .
N1 N 0.6869(16) 0.831(2) 0.1799(7) 0.039(3) Uani 1 1 d D . .
O1 O 0.6110(15) 1.0298(18) 0.1972(7) 0.048(3) Uani 1 1 d . . .
O2 O 0.8349(16) 0.694(3) -0.1531(7) 0.072(4) Uani 1 1 d . . .
O3 O 0.9293(10) 0.463(2) 0.3160(6) 0.044(3) Uani 1 1 d . . .
O4 O 0.7857(15) 0.507(2) 0.3673(7) 0.057(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 C7 1.38(3) . ?
C1 N1 1.40(2) . ?
C1 C2 1.42(2) . ?
C2 C3 1.33(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.42(2) . ?
C3 H3 0.9500 . ?
C4 C6 1.34(2) . ?
C4 O2 1.354(18) . ?
C5 O2 1.48(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.39(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.311(15) . ?
C8 C9 1.49(2) . ?
C8 C10 1.59(2) . ?
C9 O3 1.507(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O4 1.39(2) . ?
C10 C11 1.43(2) . ?
C10 C12 1.57(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.39(2) . ?
C12 C17 1.412(19) . ?
C13 C14 1.42(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.40(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.21(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.48(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 O1 1.338(15) . ?
O3 O4 1.516(14) . ?

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
C7 C1 N1 121.4(15) . . ?
C7 C1 C2 120.8(14) . . ?
N1 C1 C2 117.6(14) . . ?
C3 C2 C1 117.8(16) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.9(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C6 C4 O2 125.2(16) . . ?
C6 C4 C3 119.8(14) . . ?
O2 C4 C3 115.0(15) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 C7 120.2(17) . . ?
C4 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C1 C7 C6 119.5(16) . . ?
C1 C7 H7 120.3 . . ?
C6 C7 H7 120.2 . . ?
N1 C8 C9 125.2(14) . . ?
N1 C8 C10 127.4(15) . . ?
C9 C8 C10 107.4(12) . . ?
C8 C9 O3 100.4(12) . . ?
C8 C9 H9A 111.7 . . ?
O3 C9 H9A 111.7 . . ?
C8 C9 H9B 111.7 . . ?
O3 C9 H9B 111.7 . . ?
H9A C9 H9B 109.5 . . ?
O4 C10 C11 117.4(19) . . ?
O4 C10 C12 102.1(12) . . ?
C11 C10 C12 118.9(13) . . ?
O4 C10 C8 98.2(11) . . ?
C11 C10 C8 109.8(14) . . ?
C12 C10 C8 108.2(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.2(14) . . ?
C13 C12 C10 120.9(12) . . ?
C17 C12 C10 118.5(13) . . ?
C14 C13 C12 121.8(14) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 114.0(17) . . ?
C13 C14 H14 123.0 . . ?
C15 C14 H14 123.0 . . ?
C16 C15 C14 127(2) . . ?
C16 C15 H15 116.6 . . ?
C14 C15 H15 116.6 . . ?
C15 C16 C17 122.4(18) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C12 C17 C16 114.2(15) . . ?
C12 C17 H17 122.9 . . ?
C16 C17 H17 122.9 . . ?
C8 N1 O1 121.3(12) . . ?
C8 N1 C1 118.8(13) . . ?
O1 N1 C1 119.2(11) . . ?
C4 O2 C5 116.4(14) . . ?
C9 O3 O4 96.8(10) . . ?
C10 O4 O3 104.6(11) . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        25.21
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.130
