# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1439234'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N O2'
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.47

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           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   11.137(3)
_cell_length_b                   20.633(5)
_cell_length_c                   8.734(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2007.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8119
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      23.86

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8119
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         23.86
_reflns_number_total             2870
_reflns_number_gt                2023
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0778P)²+0.1730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1212(3) 0.42075(17) -0.3273(4) 0.0740(10) Uani 1 1 d . . .
O2 O 1.2427(3) 0.31373(19) 0.1498(4) 0.0728(10) Uani 1 1 d . . .
N1 N 0.8377(3) 0.36858(16) 0.0548(4) 0.0460(9) Uani 1 1 d . . .
C1 C 0.5233(6) 0.4808(3) 0.3938(7) 0.0839(18) Uani 1 1 d . . .
H1 H 0.4822 0.5068 0.4633 0.101 Uiso 1 1 calc R . .
C2 C 0.4695(4) 0.4283(3) 0.3331(7) 0.0797(17) Uani 1 1 d . . .
H2 H 0.3906 0.4189 0.3601 0.096 Uiso 1 1 calc R . .
C3 C 0.5286(4) 0.3881(2) 0.2319(6) 0.0609(13) Uani 1 1 d . . .
H3 H 0.4896 0.3524 0.1902 0.073 Uiso 1 1 calc R . .
C4 C 0.6474(4) 0.4016(2) 0.1927(5) 0.0449(11) Uani 1 1 d . . .
C5 C 0.7110(3) 0.3551(2) 0.0884(6) 0.0523(12) Uani 1 1 d . . .
H5A H 0.7060 0.3122 0.1335 0.063 Uiso 1 1 calc R . .
H5B H 0.6677 0.3537 -0.0079 0.063 Uiso 1 1 calc R . .
C6 C 0.8708(4) 0.40066(18) -0.0782(5) 0.0438(10) Uani 1 1 d . . .
C7 C 0.9808(4) 0.39158(18) -0.1396(5) 0.0422(10) Uani 1 1 d . . .
C8 C 1.0671(3) 0.34231(19) -0.0709(5) 0.0419(10) Uani 1 1 d . . .
H8 H 1.1486 0.3596 -0.0816 0.050 Uiso 1 1 calc R . .
C9 C 1.0628(3) 0.2766(2) -0.1539(5) 0.0452(10) Uani 1 1 d . . .
C10 C 0.9681(4) 0.2345(2) -0.1321(6) 0.0634(13) Uani 1 1 d . . .
H10 H 0.9062 0.2459 -0.0659 0.076 Uiso 1 1 calc R . .
C11 C 0.9643(5) 0.1758(2) -0.2077(8) 0.0867(19) Uani 1 1 d . . .
H11 H 0.8998 0.1479 -0.1921 0.104 Uiso 1 1 calc R . .
C12 C 1.0557(7) 0.1582(3) -0.3063(7) 0.0830(19) Uani 1 1 d . . .
H12 H 1.0531 0.1187 -0.3578 0.100 Uiso 1 1 calc R . .
C13 C 0.6998(4) 0.4560(2) 0.2521(6) 0.0577(13) Uani 1 1 d . . .
H13 H 0.7781 0.4665 0.2241 0.069 Uiso 1 1 calc R . .
C14 C 0.6389(5) 0.4959(3) 0.3528(7) 0.0737(15) Uani 1 1 d . . .
H14 H 0.6760 0.5326 0.3925 0.088 Uiso 1 1 calc R . .
C15 C 0.7834(4) 0.4499(2) -0.1416(5) 0.0546(12) Uani 1 1 d . . .
H15A H 0.7067 0.4289 -0.1590 0.066 Uiso 1 1 calc R . .
H15B H 0.7713 0.4838 -0.0662 0.066 Uiso 1 1 calc R . .
C16 C 0.8236(7) 0.4789(5) -0.2826(10) 0.193(6) Uani 1 1 d . . .
H16A H 0.7779 0.4582 -0.3636 0.232 Uiso 1 1 calc R . .
H16B H 0.7973 0.5237 -0.2795 0.232 Uiso 1 1 calc R . .
C17 C 0.9380(5) 0.4801(3) -0.3309(7) 0.0838(18) Uani 1 1 d . . .
H17A H 0.9715 0.5221 -0.3047 0.101 Uiso 1 1 calc R . .
H17B H 0.9376 0.4771 -0.4417 0.101 Uiso 1 1 calc R . .
C18 C 1.0207(5) 0.4293(2) -0.2709(5) 0.0555(12) Uani 1 1 d . . .
C19 C 1.0411(3) 0.33600(18) 0.0957(5) 0.0426(10) Uani 1 1 d . . .
C20 C 1.1412(4) 0.3206(2) 0.1974(5) 0.0536(12) Uani 1 1 d . . .
C21 C 1.1126(5) 0.3118(3) 0.3660(6) 0.0825(17) Uani 1 1 d . . .
H21A H 1.1625 0.2771 0.4058 0.099 Uiso 1 1 calc R . .
H21B H 1.1346 0.3512 0.4198 0.099 Uiso 1 1 calc R . .
C22 C 0.9890(6) 0.2971(4) 0.4007(7) 0.108(2) Uani 1 1 d . . .
H22A H 0.9760 0.3064 0.5082 0.130 Uiso 1 1 calc R . .
H22B H 0.9778 0.2508 0.3871 0.130 Uiso 1 1 calc R . .
C23 C 0.8955(4) 0.3302(2) 0.3135(5) 0.0621(13) Uani 1 1 d . . .
H23A H 0.8768 0.3709 0.3641 0.074 Uiso 1 1 calc R . .
H23B H 0.8234 0.3038 0.3149 0.074 Uiso 1 1 calc R . .
C24 C 0.9283(4) 0.34416(19) 0.1499(5) 0.0452(11) Uani 1 1 d . . .
C25 C 1.1492(6) 0.1994(3) -0.3265(6) 0.0786(17) Uani 1 1 d . . .
H25 H 1.2111 0.1879 -0.3926 0.094 Uiso 1 1 calc R . .
C26 C 1.1540(4) 0.2580(2) -0.2510(5) 0.0628(13) Uani 1 1 d . . .
H26 H 1.2195 0.2853 -0.2658 0.075 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.235(5) . ?
O2 C20 1.213(5) . ?
N1 C6 1.387(5) . ?
N1 C24 1.401(5) . ?
N1 C5 1.468(5) . ?
C1 C2 1.348(8) . ?
C1 C14 1.372(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(6) . ?
C3 H3 0.9300 . ?
C4 C13 1.369(6) . ?
C4 C5 1.501(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.350(6) . ?
C6 C15 1.512(6) . ?
C7 C18 1.456(6) . ?
C7 C8 1.522(5) . ?
C8 C19 1.489(6) . ?
C8 C9 1.538(6) . ?
C8 H8 0.9800 . ?
C9 C26 1.378(6) . ?
C9 C10 1.378(6) . ?
C10 C11 1.381(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(8) . ?
C11 H11 0.9300 . ?
C12 C25 1.356(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.440(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.343(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.490(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C24 1.353(6) . ?
C19 C20 1.461(6) . ?
C20 C21 1.517(7) . ?
C21 C22 1.442(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.460(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.503(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C26 1.380(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

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 N1 C24 118.5(3) . . ?
C6 N1 C5 120.9(3) . . ?
C24 N1 C5 120.4(3) . . ?
C2 C1 C14 119.8(5) . . ?
C2 C1 H1 120.1 . . ?
C14 C1 H1 120.1 . . ?
C1 C2 C3 121.6(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C13 C4 C3 118.3(4) . . ?
C13 C4 C5 123.6(4) . . ?
C3 C4 C5 118.0(4) . . ?
N1 C5 C4 117.0(3) . . ?
N1 C5 H5A 108.1 . . ?
C4 C5 H5A 108.1 . . ?
N1 C5 H5B 108.1 . . ?
C4 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 N1 120.5(4) . . ?
C7 C6 C15 122.2(4) . . ?
N1 C6 C15 117.1(4) . . ?
C6 C7 C18 121.0(4) . . ?
C6 C7 C8 120.6(4) . . ?
C18 C7 C8 118.4(4) . . ?
C19 C8 C7 108.7(3) . . ?
C19 C8 C9 112.2(3) . . ?
C7 C8 C9 112.6(3) . . ?
C19 C8 H8 107.7 . . ?
C7 C8 H8 107.7 . . ?
C9 C8 H8 107.7 . . ?
C26 C9 C10 118.3(4) . . ?
C26 C9 C8 120.8(4) . . ?
C10 C9 C8 120.9(4) . . ?
C9 C10 C11 120.7(5) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C25 C12 C11 118.8(5) . . ?
C25 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C4 C13 C14 121.4(5) . . ?
C4 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C1 C14 C13 119.5(5) . . ?
C1 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C6 113.1(4) . . ?
C16 C15 H15A 109.0 . . ?
C6 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C6 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 124.9(6) . . ?
C17 C16 H16A 106.1 . . ?
C15 C16 H16A 106.1 . . ?
C17 C16 H16B 106.1 . . ?
C15 C16 H16B 106.1 . . ?
H16A C16 H16B 106.3 . . ?
C16 C17 C18 117.5(5) . . ?
C16 C17 H17A 107.9 . . ?
C18 C17 H17A 107.9 . . ?
C16 C17 H17B 107.9 . . ?
C18 C17 H17B 107.9 . . ?
H17A C17 H17B 107.2 . . ?
O1 C18 C7 120.9(4) . . ?
O1 C18 C17 121.3(4) . . ?
C7 C18 C17 117.7(4) . . ?
C24 C19 C20 121.5(4) . . ?
C24 C19 C8 120.7(4) . . ?
C20 C19 C8 117.8(4) . . ?
O2 C20 C19 121.9(4) . . ?
O2 C20 C21 121.0(4) . . ?
C19 C20 C21 117.2(4) . . ?
C22 C21 C20 115.4(4) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 118.2(5) . . ?
C21 C22 H22A 107.8 . . ?
C23 C22 H22A 107.8 . . ?
C21 C22 H22B 107.8 . . ?
C23 C22 H22B 107.8 . . ?
H22A C22 H22B 107.1 . . ?
C22 C23 C24 114.3(4) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C19 C24 N1 120.4(4) . . ?
C19 C24 C23 122.4(4) . . ?
N1 C24 C23 117.2(4) . . ?
C12 C25 C26 121.2(5) . . ?
C12 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C9 C26 C25 120.6(5) . . ?
C9 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        23.86
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1439236'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Cl N O2'
_chemical_formula_sum            'C21 H22 Cl N O2'
_chemical_formula_weight         355.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/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                   7.1242(17)
_cell_length_b                   16.492(4)
_cell_length_c                   15.175(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.530(3)
_cell_angle_gamma                90.00
_cell_volume                     1781.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6620
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      22.70

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6620
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         22.70
_reflns_number_total             2259
_reflns_number_gt                1765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0586P)²+0.6186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2259
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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
Cl1 Cl 0.34736(15) 0.91906(5) 1.04102(5) 0.0798(4) Uani 1 1 d . . .
O1 O 0.2028(3) 0.79839(11) 0.61244(12) 0.0481(5) Uani 1 1 d . . .
O2 O 0.4300(3) 0.56556(10) 0.80088(13) 0.0528(6) Uani 1 1 d . . .
N1 N 0.8392(3) 0.73104(11) 0.64712(13) 0.0372(5) Uani 1 1 d . . .
H1 H 0.9543 0.7434 0.6387 0.045 Uiso 1 1 calc R . .
C1 C 0.9743(4) 0.55884(17) 0.85547(17) 0.0508(8) Uani 1 1 d . . .
H1A H 0.9022 0.6062 0.8685 0.076 Uiso 1 1 calc R . .
H1B H 1.1056 0.5720 0.8592 0.076 Uiso 1 1 calc R . .
H1C H 0.9492 0.5169 0.8972 0.076 Uiso 1 1 calc R . .
C2 C 0.9199(3) 0.52940(13) 0.76257(17) 0.0355(6) Uani 1 1 d . . .
C3 C 0.9482(3) 0.59705(14) 0.69527(17) 0.0369(6) Uani 1 1 d . . .
H3A H 1.0689 0.6225 0.7085 0.044 Uiso 1 1 calc R . .
H3B H 0.9524 0.5730 0.6371 0.044 Uiso 1 1 calc R . .
C4 C 0.7988(3) 0.66126(13) 0.69321(15) 0.0309(6) Uani 1 1 d . . .
C5 C 0.6288(3) 0.65161(13) 0.72635(15) 0.0296(6) Uani 1 1 d . . .
C6 C 0.4797(3) 0.71645(13) 0.71838(15) 0.0300(6) Uani 1 1 d . . .
H6 H 0.3607 0.6891 0.7028 0.036 Uiso 1 1 calc R . .
C7 C 0.4502(4) 0.76467(13) 0.80202(15) 0.0319(6) Uani 1 1 d . . .
C8 C 0.2742(4) 0.77057(15) 0.83606(18) 0.0431(7) Uani 1 1 d . . .
H8 H 0.1742 0.7427 0.8087 0.052 Uiso 1 1 calc R . .
C9 C 0.2434(5) 0.81693(17) 0.90978(19) 0.0536(8) Uani 1 1 d . . .
H9 H 0.1239 0.8199 0.9319 0.064 Uiso 1 1 calc R . .
C10 C 0.3891(5) 0.85843(16) 0.95001(18) 0.0496(8) Uani 1 1 d . . .
C11 C 0.5221(3) 0.77214(13) 0.64197(15) 0.0298(6) Uani 1 1 d . . .
C12 C 0.3672(4) 0.81259(13) 0.59558(15) 0.0325(6) Uani 1 1 d . . .
C13 C 0.4110(3) 0.87089(15) 0.52302(17) 0.0389(7) Uani 1 1 d . . .
H13A H 0.3199 0.9146 0.5221 0.047 Uiso 1 1 calc R . .
H13B H 0.3986 0.8429 0.4668 0.047 Uiso 1 1 calc R . .
C14 C 0.6061(3) 0.90634(14) 0.53363(17) 0.0385(7) Uani 1 1 d . . .
H14A H 0.6136 0.9416 0.5848 0.046 Uiso 1 1 calc R . .
H14B H 0.6324 0.9386 0.4821 0.046 Uiso 1 1 calc R . .
C15 C 0.7504(4) 0.83923(14) 0.54471(16) 0.0371(6) Uani 1 1 d . . .
H15A H 0.7598 0.8106 0.4892 0.044 Uiso 1 1 calc R . .
H15B H 0.8723 0.8626 0.5603 0.044 Uiso 1 1 calc R . .
C16 C 0.6982(3) 0.78080(13) 0.61469(15) 0.0306(6) Uani 1 1 d . . .
C17 C 0.5791(4) 0.57429(14) 0.76542(17) 0.0350(6) Uani 1 1 d . . .
C18 C 0.7132(3) 0.50483(14) 0.75635(19) 0.0432(7) Uani 1 1 d . . .
H18A H 0.6869 0.4787 0.6999 0.052 Uiso 1 1 calc R . .
H18B H 0.6910 0.4654 0.8021 0.052 Uiso 1 1 calc R . .
C19 C 1.0422(4) 0.45696(15) 0.7398(2) 0.0527(8) Uani 1 1 d . . .
H19A H 1.0201 0.4133 0.7799 0.079 Uiso 1 1 calc R . .
H19B H 1.1722 0.4724 0.7448 0.079 Uiso 1 1 calc R . .
H19C H 1.0111 0.4397 0.6806 0.079 Uiso 1 1 calc R . .
C20 C 0.5953(4) 0.80685(16) 0.84418(17) 0.0466(7) Uani 1 1 d . . .
H20 H 0.7153 0.8039 0.8226 0.056 Uiso 1 1 calc R . .
C21 C 0.5655(5) 0.85366(17) 0.91824(19) 0.0549(8) Uani 1 1 d . . .
H21 H 0.6647 0.8816 0.9461 0.066 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.741(3) . ?
O1 C12 1.232(3) . ?
O2 C17 1.220(3) . ?
N1 C16 1.372(3) . ?
N1 C4 1.384(3) . ?
N1 H1 0.8600 . ?
C1 C2 1.525(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C18 1.526(3) . ?
C2 C19 1.527(3) . ?
C2 C3 1.532(3) . ?
C3 C4 1.501(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.341(3) . ?
C5 C17 1.457(3) . ?
C5 C6 1.509(3) . ?
C6 C11 1.520(3) . ?
C6 C7 1.520(3) . ?
C6 H6 0.9800 . ?
C7 C20 1.380(4) . ?
C7 C8 1.380(4) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C21 1.368(4) . ?
C11 C16 1.346(3) . ?
C11 C12 1.446(3) . ?
C12 C13 1.505(3) . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.493(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.502(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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 N1 C4 120.9(2) . . ?
C16 N1 H1 119.5 . . ?
C4 N1 H1 119.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C18 110.3(2) . . ?
C1 C2 C19 109.5(2) . . ?
C18 C2 C19 109.7(2) . . ?
C1 C2 C3 110.4(2) . . ?
C18 C2 C3 107.9(2) . . ?
C19 C2 C3 109.0(2) . . ?
C4 C3 C2 114.43(19) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 N1 120.0(2) . . ?
C5 C4 C3 124.0(2) . . ?
N1 C4 C3 115.8(2) . . ?
C4 C5 C17 119.8(2) . . ?
C4 C5 C6 122.0(2) . . ?
C17 C5 C6 118.0(2) . . ?
C5 C6 C11 109.07(18) . . ?
C5 C6 C7 115.26(19) . . ?
C11 C6 C7 111.12(18) . . ?
C5 C6 H6 107.0 . . ?
C11 C6 H6 107.0 . . ?
C7 C6 H6 107.0 . . ?
C20 C7 C8 117.7(2) . . ?
C20 C7 C6 121.5(2) . . ?
C8 C7 C6 120.7(2) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C21 120.4(3) . . ?
C9 C10 Cl1 119.3(2) . . ?
C21 C10 Cl1 120.3(3) . . ?
C16 C11 C12 120.2(2) . . ?
C16 C11 C6 121.2(2) . . ?
C12 C11 C6 118.5(2) . . ?
O1 C12 C11 121.5(2) . . ?
O1 C12 C13 120.2(2) . . ?
C11 C12 C13 118.2(2) . . ?
C12 C13 C14 112.9(2) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 110.23(19) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 111.2(2) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C11 C16 N1 120.3(2) . . ?
C11 C16 C15 123.5(2) . . ?
N1 C16 C15 116.1(2) . . ?
O2 C17 C5 121.0(2) . . ?
O2 C17 C18 121.3(2) . . ?
C5 C17 C18 117.6(2) . . ?
C17 C18 C2 114.1(2) . . ?
C17 C18 H18A 108.7 . . ?
C2 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C2 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C20 C21 121.2(3) . . ?
C7 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C10 C21 C20 119.6(3) . . ?
C10 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        22.70
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
