# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_p
_database_code_depnum_ccdc_archive 'CCDC 1007344'
_audit_update_record             
;
2014-10-19 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 B Br F2 N O'
_chemical_formula_weight         426.06

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   16.379(4)
_cell_length_b                   10.494(3)
_cell_length_c                   21.831(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3752.3(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    2.220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8085
_exptl_absorpt_correction_T_max  0.8085
_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  ?
_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            42408
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.31
_reflns_number_total             3409
_reflns_number_gt                2759
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1700P)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       0.0037(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3409
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.2134
_refine_ls_wR_factor_gt          0.1885
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.49714(14) 0.3286(2) 0.40023(12) 0.0487(6) Uani 1 1 d . . .
N1 N 0.37070(16) 0.3921(2) 0.34669(13) 0.0377(6) Uani 1 1 d . . .
B1 B 0.4291(2) 0.2793(3) 0.36431(19) 0.0429(9) Uani 1 1 d . . .
Br1 Br 0.21415(4) 0.11351(4) 0.18670(2) 0.0753(3) Uani 1 1 d . . .
F1 F 0.38698(14) 0.1918(2) 0.39792(13) 0.0683(7) Uani 1 1 d . . .
F2 F 0.46074(14) 0.2246(3) 0.31184(11) 0.0705(8) Uani 1 1 d . . .
C1 C 0.2163(2) 0.2467(4) 0.24553(18) 0.0503(9) Uani 1 1 d . . .
C2 C 0.1476(2) 0.3189(4) 0.2568(2) 0.0594(10) Uani 1 1 d . . .
H2A H 0.0991 0.3038 0.2358 0.071 Uiso 1 1 calc R . .
C3 C 0.1529(2) 0.4147(4) 0.3004(2) 0.0592(10) Uani 1 1 d . . .
H3A H 0.1067 0.4629 0.3092 0.071 Uiso 1 1 calc R . .
C4 C 0.2250(2) 0.4407(4) 0.33112(19) 0.0492(9) Uani 1 1 d . . .
H4A H 0.2275 0.5056 0.3601 0.059 Uiso 1 1 calc R . .
C5 C 0.2936(2) 0.3673(4) 0.31753(16) 0.0400(8) Uani 1 1 d . . .
C6 C 0.28941(19) 0.2692(3) 0.27493(17) 0.0432(8) Uani 1 1 d . . .
H6A H 0.3351 0.2197 0.2664 0.052 Uiso 1 1 calc R . .
C7 C 0.39308(18) 0.5105(3) 0.35729(15) 0.0388(7) Uani 1 1 d . . .
H7A H 0.3578 0.5754 0.3454 0.047 Uiso 1 1 calc R . .
C8 C 0.46704(19) 0.5448(3) 0.38552(15) 0.0378(7) Uani 1 1 d . . .
C9 C 0.48800(19) 0.6826(3) 0.38889(15) 0.0395(7) Uani 1 1 d . . .
C10 C 0.4491(2) 0.7628(4) 0.42953(17) 0.0531(9) Uani 1 1 d . . .
H10A H 0.4083 0.7315 0.4550 0.064 Uiso 1 1 calc R . .
C11 C 0.4710(3) 0.8901(4) 0.4323(2) 0.0637(12) Uani 1 1 d . . .
H11A H 0.4448 0.9438 0.4599 0.076 Uiso 1 1 calc R . .
C12 C 0.5311(3) 0.9382(4) 0.3947(2) 0.0664(12) Uani 1 1 d . . .
H12A H 0.5459 1.0237 0.3969 0.080 Uiso 1 1 calc R . .
C13 C 0.5681(3) 0.8594(4) 0.3548(2) 0.0689(12) Uani 1 1 d . . .
H13A H 0.6087 0.8913 0.3293 0.083 Uiso 1 1 calc R . .
C14 C 0.5473(2) 0.7326(4) 0.35099(19) 0.0551(10) Uani 1 1 d . . .
H14A H 0.5733 0.6803 0.3227 0.066 Uiso 1 1 calc R . .
C15 C 0.51780(19) 0.4492(3) 0.40569(14) 0.0381(7) Uani 1 1 d . . .
C16 C 0.59894(19) 0.4656(3) 0.43522(14) 0.0395(7) Uani 1 1 d . . .
C17 C 0.6184(2) 0.5668(4) 0.47391(16) 0.0470(8) Uani 1 1 d . . .
H17A H 0.5798 0.6295 0.4819 0.056 Uiso 1 1 calc R . .
C18 C 0.6948(3) 0.5743(5) 0.50039(19) 0.0621(11) Uani 1 1 d . . .
H18A H 0.7070 0.6406 0.5271 0.075 Uiso 1 1 calc R . .
C19 C 0.7538(3) 0.4818(5) 0.4870(2) 0.0724(13) Uani 1 1 d . . .
H19A H 0.8055 0.4866 0.5045 0.087 Uiso 1 1 calc R . .
C20 C 0.7349(3) 0.3853(5) 0.4484(3) 0.0717(14) Uani 1 1 d . . .
H20A H 0.7746 0.3250 0.4390 0.086 Uiso 1 1 calc R . .
C21 C 0.6588(2) 0.3744(4) 0.4228(2) 0.0540(10) Uani 1 1 d . . .
H21A H 0.6470 0.3062 0.3971 0.065 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 C15 1.315(4) . ?
O1 B1 1.458(4) . ?
N1 C7 1.316(4) . ?
N1 C5 1.438(4) . ?
N1 B1 1.570(4) . ?
B1 F1 1.363(4) . ?
B1 F2 1.382(5) . ?
Br1 C1 1.899(4) . ?
C1 C6 1.379(4) . ?
C1 C2 1.380(6) . ?
C2 C3 1.386(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.386(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.406(4) . ?
C7 H7A 0.9300 . ?
C8 C15 1.375(5) . ?
C8 C9 1.488(5) . ?
C9 C10 1.379(5) . ?
C9 C14 1.379(5) . ?
C10 C11 1.384(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.346(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(6) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.487(4) . ?
C16 C17 1.394(5) . ?
C16 C21 1.397(5) . ?
C17 C18 1.380(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.401(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.353(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.372(7) . ?
C20 H20A 0.9300 . ?
C21 H21A 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
C15 O1 B1 126.0(3) . . ?
C7 N1 C5 119.6(3) . . ?
C7 N1 B1 119.9(3) . . ?
C5 N1 B1 120.5(3) . . ?
F1 B1 F2 110.9(3) . . ?
F1 B1 O1 109.7(3) . . ?
F2 B1 O1 107.9(3) . . ?
F1 B1 N1 109.3(3) . . ?
F2 B1 N1 109.8(3) . . ?
O1 B1 N1 109.2(3) . . ?
C6 C1 C2 122.1(4) . . ?
C6 C1 Br1 117.2(3) . . ?
C2 C1 Br1 120.7(3) . . ?
C1 C2 C3 118.0(3) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 N1 118.3(3) . . ?
C4 C5 N1 120.9(3) . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
N1 C7 C8 124.0(3) . . ?
N1 C7 H7A 118.0 . . ?
C8 C7 H7A 118.0 . . ?
C15 C8 C7 118.3(3) . . ?
C15 C8 C9 123.6(3) . . ?
C7 C8 C9 118.0(3) . . ?
C10 C9 C14 118.6(3) . . ?
C10 C9 C8 121.2(3) . . ?
C14 C9 C8 120.2(3) . . ?
C9 C10 C11 119.9(4) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 118.8(4) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C13 C14 C9 120.4(4) . . ?
C13 C14 H14A 119.8 . . ?
C9 C14 H14A 119.8 . . ?
O1 C15 C8 121.1(3) . . ?
O1 C15 C16 112.3(3) . . ?
C8 C15 C16 126.5(3) . . ?
C17 C16 C21 118.6(3) . . ?
C17 C16 C15 123.7(3) . . ?
C21 C16 C15 117.7(3) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C19 C20 C21 121.6(5) . . ?
C19 C20 H20A 119.2 . . ?
C21 C20 H20A 119.2 . . ?
C20 C21 C16 120.1(4) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 O1 B1 F1 -134.2(3) . . . . ?
C15 O1 B1 F2 104.9(4) . . . . ?
C15 O1 B1 N1 -14.4(4) . . . . ?
C7 N1 B1 F1 129.2(3) . . . . ?
C5 N1 B1 F1 -52.4(4) . . . . ?
C7 N1 B1 F2 -108.9(3) . . . . ?
C5 N1 B1 F2 69.5(4) . . . . ?
C7 N1 B1 O1 9.2(4) . . . . ?
C5 N1 B1 O1 -172.4(3) . . . . ?
C6 C1 C2 C3 -1.6(6) . . . . ?
Br1 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C3 C4 C5 N1 178.3(4) . . . . ?
C7 N1 C5 C6 141.2(3) . . . . ?
B1 N1 C5 C6 -37.2(5) . . . . ?
C7 N1 C5 C4 -38.0(5) . . . . ?
B1 N1 C5 C4 143.6(4) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
Br1 C1 C6 C5 179.0(3) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
N1 C5 C6 C1 -178.3(3) . . . . ?
C5 N1 C7 C8 179.9(3) . . . . ?
B1 N1 C7 C8 -1.7(5) . . . . ?
N1 C7 C8 C15 -2.8(5) . . . . ?
N1 C7 C8 C9 174.0(3) . . . . ?
C15 C8 C9 C10 -109.0(4) . . . . ?
C7 C8 C9 C10 74.4(4) . . . . ?
C15 C8 C9 C14 71.0(4) . . . . ?
C7 C8 C9 C14 -105.6(4) . . . . ?
C14 C9 C10 C11 -1.2(5) . . . . ?
C8 C9 C10 C11 178.9(3) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -0.1(8) . . . . ?
C12 C13 C14 C9 -0.8(7) . . . . ?
C10 C9 C14 C13 1.4(6) . . . . ?
C8 C9 C14 C13 -178.6(4) . . . . ?
B1 O1 C15 C8 11.5(5) . . . . ?
B1 O1 C15 C16 -168.7(3) . . . . ?
C7 C8 C15 O1 -1.7(5) . . . . ?
C9 C8 C15 O1 -178.3(3) . . . . ?
C7 C8 C15 C16 178.5(3) . . . . ?
C9 C8 C15 C16 1.9(5) . . . . ?
O1 C15 C16 C17 -145.7(3) . . . . ?
C8 C15 C16 C17 34.1(5) . . . . ?
O1 C15 C16 C21 34.8(4) . . . . ?
C8 C15 C16 C21 -145.4(4) . . . . ?
C21 C16 C17 C18 -1.6(5) . . . . ?
C15 C16 C17 C18 179.0(3) . . . . ?
C16 C17 C18 C19 1.8(6) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C18 C19 C20 C21 -1.2(8) . . . . ?
C19 C20 C21 C16 1.4(7) . . . . ?
C17 C16 C21 C20 0.0(6) . . . . ?
C15 C16 C21 C20 179.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.550
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_140426f
_database_code_depnum_ccdc_archive 'CCDC 1007345'
_audit_update_record             
;
2014-10-19 deposited with the CCDC.
2014-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl N O'
_chemical_formula_weight         333.80

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   C2/c

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

_cell_length_a                   16.9201(15)
_cell_length_b                   10.0430(9)
_cell_length_c                   19.7402(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.841(2)
_cell_angle_gamma                90.00
_cell_volume                     3314.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1114
_cell_measurement_theta_min      2.366
_cell_measurement_theta_max      20.711

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9009
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6576
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2907
_reflns_number_gt                1231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0870P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.11060(8) 0.91251(17) 0.62350(6) 0.0892(6) Uani 1 1 d . . .
N1 N 0.1362(2) 0.8117(4) 0.33379(18) 0.0565(11) Uani 1 1 d . . .
H1A H 0.0917 0.7904 0.3088 0.068 Uiso 1 1 calc R . .
O1 O 0.06993(17) 0.7129(4) 0.21730(15) 0.0730(11) Uani 1 1 d . . .
C1 C 0.2011(3) 0.8124(5) 0.3028(2) 0.0550(13) Uani 1 1 d . . .
H1 H 0.2484 0.8428 0.3283 0.066 Uiso 1 1 calc R . .
C2 C 0.2045(2) 0.7729(5) 0.2377(2) 0.0485(12) Uani 1 1 d . . .
C3 C 0.2831(2) 0.7817(5) 0.21392(19) 0.0446(12) Uani 1 1 d . . .
C4 C 0.3220(3) 0.6707(5) 0.1943(2) 0.0570(13) Uani 1 1 d . . .
H4 H 0.2972 0.5880 0.1938 0.068 Uiso 1 1 calc R . .
C5 C 0.3961(3) 0.6800(6) 0.1758(2) 0.0637(14) Uani 1 1 d . . .
H5 H 0.4209 0.6035 0.1629 0.076 Uiso 1 1 calc R . .
C6 C 0.4340(3) 0.7977(6) 0.1757(2) 0.0681(16) Uani 1 1 d . . .
H6 H 0.4847 0.8027 0.1632 0.082 Uiso 1 1 calc R . .
C7 C 0.3970(3) 0.9097(6) 0.1943(2) 0.0684(15) Uani 1 1 d . . .
H7 H 0.4227 0.9917 0.1949 0.082 Uiso 1 1 calc R . .
C8 C 0.3224(3) 0.9013(5) 0.2121(2) 0.0573(13) Uani 1 1 d . . .
H8 H 0.2973 0.9788 0.2233 0.069 Uiso 1 1 calc R . .
C9 C 0.1353(3) 0.7183(5) 0.1960(2) 0.0525(13) Uani 1 1 d . . .
C10 C 0.1362(2) 0.6657(5) 0.1261(2) 0.0483(12) Uani 1 1 d . . .
C11 C 0.1007(3) 0.5447(6) 0.1115(2) 0.0635(14) Uani 1 1 d . . .
H11 H 0.0807 0.4970 0.1455 0.076 Uiso 1 1 calc R . .
C12 C 0.0947(3) 0.4938(7) 0.0465(3) 0.0827(18) Uani 1 1 d . . .
H12 H 0.0730 0.4094 0.0373 0.099 Uiso 1 1 calc R . .
C13 C 0.1198(3) 0.5642(8) -0.0044(3) 0.088(2) Uani 1 1 d . . .
H13 H 0.1134 0.5298 -0.0486 0.106 Uiso 1 1 calc R . .
C14 C 0.1542(3) 0.6844(8) 0.0089(3) 0.0806(19) Uani 1 1 d . . .
H14 H 0.1717 0.7327 -0.0262 0.097 Uiso 1 1 calc R . .
C15 C 0.1635(3) 0.7360(6) 0.0750(2) 0.0632(15) Uani 1 1 d . . .
H15 H 0.1882 0.8181 0.0844 0.076 Uiso 1 1 calc R . .
C16 C 0.1327(3) 0.8422(5) 0.4029(2) 0.0495(12) Uani 1 1 d . . .
C17 C 0.0605(3) 0.8258(5) 0.4253(2) 0.0600(14) Uani 1 1 d . . .
H17 H 0.0161 0.7977 0.3949 0.072 Uiso 1 1 calc R . .
C18 C 0.0537(3) 0.8508(5) 0.4930(2) 0.0648(15) Uani 1 1 d . . .
H18 H 0.0045 0.8407 0.5079 0.078 Uiso 1 1 calc R . .
C19 C 0.1182(3) 0.8899(5) 0.5377(2) 0.0571(13) Uani 1 1 d . . .
C20 C 0.1889(3) 0.9079(5) 0.5154(2) 0.0683(16) Uani 1 1 d . . .
H20 H 0.2333 0.9356 0.5459 0.082 Uiso 1 1 calc R . .
C21 C 0.1956(3) 0.8856(6) 0.4482(2) 0.0698(16) Uani 1 1 d . . .
H21 H 0.2444 0.9006 0.4334 0.084 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 C19 1.734(4) . ?
N1 C1 1.338(5) . ?
N1 C16 1.408(5) . ?
N1 H1A 0.8600 . ?
O1 C9 1.243(5) . ?
C1 C2 1.354(6) . ?
C1 H1 0.9300 . ?
C2 C9 1.433(6) . ?
C2 C3 1.479(6) . ?
C3 C8 1.376(6) . ?
C3 C4 1.380(6) . ?
C4 C5 1.363(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.345(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.479(6) . ?
C10 C11 1.366(7) . ?
C10 C15 1.369(6) . ?
C11 C12 1.369(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.350(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.354(6) . ?
C16 C17 1.371(6) . ?
C17 C18 1.382(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.351(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.349(6) . ?
C20 C21 1.367(6) . ?
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
C1 N1 C16 127.0(4) . . ?
C1 N1 H1A 116.5 . . ?
C16 N1 H1A 116.5 . . ?
N1 C1 C2 126.2(4) . . ?
N1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C1 C2 C9 120.5(4) . . ?
C1 C2 C3 117.0(4) . . ?
C9 C2 C3 122.4(4) . . ?
C8 C3 C4 116.4(4) . . ?
C8 C3 C2 121.5(4) . . ?
C4 C3 C2 122.1(4) . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.1(5) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 122.1(5) . . ?
C7 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
O1 C9 C2 120.9(4) . . ?
O1 C9 C10 115.9(4) . . ?
C2 C9 C10 123.2(4) . . ?
C11 C10 C15 119.3(4) . . ?
C11 C10 C9 116.6(4) . . ?
C15 C10 C9 123.8(5) . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 121.0(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 119.8(5) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C21 C16 C17 118.3(4) . . ?
C21 C16 N1 124.4(4) . . ?
C17 C16 N1 117.3(4) . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.6(4) . . ?
C20 C19 Cl1 120.2(4) . . ?
C18 C19 Cl1 120.1(3) . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 121.3(4) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N1 C1 C2 174.5(4) . . . . ?
N1 C1 C2 C9 -3.2(8) . . . . ?
N1 C1 C2 C3 -179.8(4) . . . . ?
C1 C2 C3 C8 -60.2(6) . . . . ?
C9 C2 C3 C8 123.2(5) . . . . ?
C1 C2 C3 C4 117.8(5) . . . . ?
C9 C2 C3 C4 -58.7(6) . . . . ?
C8 C3 C4 C5 1.4(6) . . . . ?
C2 C3 C4 C5 -176.8(4) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C6 C7 C8 C3 1.9(7) . . . . ?
C4 C3 C8 C7 -2.3(6) . . . . ?
C2 C3 C8 C7 175.9(4) . . . . ?
C1 C2 C9 O1 3.9(7) . . . . ?
C3 C2 C9 O1 -179.7(5) . . . . ?
C1 C2 C9 C10 -176.1(4) . . . . ?
C3 C2 C9 C10 0.3(7) . . . . ?
O1 C9 C10 C11 -47.0(6) . . . . ?
C2 C9 C10 C11 133.0(5) . . . . ?
O1 C9 C10 C15 126.8(5) . . . . ?
C2 C9 C10 C15 -53.2(6) . . . . ?
C15 C10 C11 C12 1.6(7) . . . . ?
C9 C10 C11 C12 175.8(4) . . . . ?
C10 C11 C12 C13 -3.2(8) . . . . ?
C11 C12 C13 C14 2.5(8) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C11 C10 C15 C14 0.6(7) . . . . ?
C9 C10 C15 C14 -173.1(4) . . . . ?
C13 C14 C15 C10 -1.3(7) . . . . ?
C1 N1 C16 C21 4.3(8) . . . . ?
C1 N1 C16 C17 -175.3(5) . . . . ?
C21 C16 C17 C18 -1.3(8) . . . . ?
N1 C16 C17 C18 178.4(4) . . . . ?
C16 C17 C18 C19 -0.9(8) . . . . ?
C17 C18 C19 C20 1.8(8) . . . . ?
C17 C18 C19 Cl1 -176.5(4) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
Cl1 C19 C20 C21 177.7(4) . . . . ?
C17 C16 C21 C20 2.5(8) . . . . ?
N1 C16 C21 C20 -177.1(5) . . . . ?
C19 C20 C21 C16 -1.6(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.150
